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Cytochalasin E

PubChem CID
5458385
Structure
Cytochalasin E_small.png
Cytochalasin E_3D_Structure.png
Molecular Formula
Synonyms
  • cytochalasin e
  • 36011-19-5
  • HSDB 3548
  • EINECS 252-835-7
  • MFCD00005178
Molecular Weight
495.6 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2006-02-27
  • Modify:
    2025-01-11
Description
Cytochalasin E is a cytochalasan alkaloid. It has a role as a metabolite.
Cytochalasin e has been reported in Mariannaea elegans, Mycotypha, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cytochalasin E.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,5E,7R,9S,11E,13S,14S,16R,17S,18S,19S)-19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-5,11-diene-3,8,21-trione
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+/t16-,17-,19-,20-,21-,23-,26+,27+,28+/m0/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

LAJXCUNOQSHRJO-ZYGJITOWSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C[C@H]1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4[C@]2(C(=O)N[C@H]4CC5=CC=CC=C5)OC(=O)O/C=C/[C@@](C1=O)(C)O)C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C28H33NO7
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 Metabolomics Workbench ID

2.3.7 NSC Number

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

cytochalasin E

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
495.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
3.5
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
495.22570239 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
495.22570239 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
114 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
36
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
986
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
9
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid; [HSDB] White solid; [MSDSonline]

3.2.2 Color / Form

CRYSTALS FROM ACETONE-HEXANE
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 266

3.2.3 Melting Point

206-208 °C WITH DECOMP
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 266

3.2.4 Solubility

SOL IN DICHLOROMETHANE, CHLOROFORM, ACETONE, & METHANOL; SPARINGLY SOL IN WATER
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 266

3.2.5 Stability / Shelf Life

UNSTABLE IN CHLOROFORM SOLN & UNDER ACIDIC CONDITIONS.
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 266

3.2.6 Optical Rotation

SPECIFIC OPTICAL ROTATION: -25.6 DEG @ 25 °C/D (IN METHANOL); WEAK ABSORPTIONS BETWEEN 240 & 300 NM DUE IN PART TO THE PI BOND TO PI BOND* TRANSITION OF THE MONOSUBSTITUTED AROMATIC RING
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 266

3.2.7 Other Experimental Properties

THE CYTOCHALASINS GENERALLY CAN BE DESCRIBED AS A PHENYLALANINE OR TRYPTOPHAN MOIETY LINKED TO PERHYDROISOINDOLE MOIETY WHICH IS IN TURN LINKED TO A C16-C18 POLYKETIDE RING SYSTEM CONTAINING A CARBOCYCLIC (CYTOCHALASIN C), A LACTONE (CYTOCHALASIN A), OR A CYCLIC CARBONATE (CYTOCHALASIN E) MOIETY /CYTOCHALASINS/
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 264

3.3 Chemical Classes

Biological Agents -> Mycotoxins

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Therapeutic Uses

Angiogenesis Inhibitors
National Library of Medicine's Medical Subject Headings online file (MeSH, 2001)

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Angiogenesis Inhibitors
Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)

8.2 Mechanism of Action

MAJOR BIOLOGICAL EFFECTS ARE THE BLOCKAGE OF CYTOPLASMIC CLEAVAGE RESULTING IN MULTINUCLEATE CELL FORMATION, THE INHIBITION OF CELL MOVEMENT, & THE INDUCTION OF NUCLEAR EXTRUSION... OTHER REPORTED EFFECTS INCLUDE THE INHIBITION OF GLUCOSE TRANSPORT, OF THYROID SECRETION, OF GROWTH HORMONE RELEASE, OF PHAGOCYTOSIS, & OF PLATELET AGGREGATION & CLOT CONTRACTION. /CYTOCHALASINS/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 365
THE INFLUENCE OF CYTOCHALASIN B & E ON INTESTINAL DIGESTION OF MALTOSE & SUCROSE, & THEIR DIGESTION PRODUCTS AS GLUCOSE & FRUCTOSE WAS INVESTIGATED IN THE MOUSE IN VITRO. NEITHER DIGESTION OF MALTOSE OR SUCROSE NOR ACTIVITIES OF MALTASE OR SUCRASE IN EVERTED SACS OF MOUSE JEJUNUM WAS AFFECTED BY CYTOCHALASIN B OR E AT 5.0 & 10.0 MUG/ML AFTER 60 MIN INCUBATION. HOWEVER, ABSORPTION OF GLUCOSE DERIVED FROM MALTOSE OR SUCROSE DIGESTION WAS INHIBITED BY 68.5 & 65.9% DUE TO CYTOCHALASIN E (5.0 MUG/ML) & BY 29.5 & 13.1% DUE TO CYTOCHALASIN B AT THE SAME CONCN. CYTOCHALASINS B & E SEEMED TO STIMULATE ABSORPTION OF FRUCTOSE DERIVED FROM SUCROSE DIGESTION IN MOUSE JEJUNUM.
GLINSUKON T ET AL; INFLUENCE OF CYTOCHALASINS B AND E ON INTESTINAL ABSORPTION OF MALTOSE AND SUCROSE-DIGESTION PRODUCTS IN THE MOUSE; NUTR REP INT 27(1) 137 (1983)
THE INHIBITORY EFFECT OF CYTOCHALASIN E ON GALACTOSE ABSORPTION IN EVERTED SACS OF MOUSE JEJUNUM WAS STUDIED. CYTOCHALASIN B HAD THE HIGHEST POTENCY ON THE INHIBITION OF GALACTOSE ABSORPTION WHEN IT WAS ADDED IN THE MUCOSAL SOLN FOLLOWED BY CYTOCHALASIN E, A, C, & D, RESPECTIVELY.
GLINSUKON T ET AL; INHIBITORY EFFECT OF CYTOCHALASIN E ON GALACTOSE ABSORPTION IN THE MOUSE IN VITRO; RES COMMUN CHEM PATHOL PHARMACOL 38(2) 247 (1982)
IN MICE Y-1 ADRENAL TUMOR CELLS, CYTOCHALASINS E, D, B, & H2B, INHIBITED STEROIDOGENESIS & PRODUCED ROUNDING OF CELLS BY INTERFERING WITH POLYMERIZATION OF ACTIN & NOT AS THE RESULT OF EFFECTS UNRELATED TO BINDING TO ACTIN.
HALL PF ET AL; THE ACTIONS OF VARIOUS CYTOCHALASINS ON MOUSE ADRENAL TUMOR CELLS IN RELATION TO TROPHIC STIMULATION OF STEROIDOGENESIS; BIOCHIM BIOPHYS ACTA 676(3) 338 (1981)
For more Mechanism of Action (Complete) data for CYTOCHALASIN E (10 total), please visit the HSDB record page.

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Cytochalasins are a group of mold metabolites having various effects on animal cells; More than twenty cytochalasins have been isolated from different mold species; Used in cytological research and in studying the polymerization properties of actin; Most studied is cytochalasin B; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
MEDICATION
TOOL IN CYTOLOGICAL RESEARCH
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 366

9.2 Methods of Manufacturing

ISOLATION & STRUCTURE OF CYTOCHALASINS E & F: ALDRIDGE ET AL, CHEM COMMUN 1972, 148. /CYTOCHALASINS/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 365

10 Identification

10.1 Analytic Laboratory Methods

TLC DATA; DETECTION: H2SO4 SPRAYING & HEAT. GLINSUKON T ET AL; TOXICOL APPL PHARMACOL 32: 135 (1975). TLC DATA; DETECTION: A DARK PURPLE FLUORESCENT SPOT UNDER UV LIGHT AFTER SPRAYING WITH 50% ETHANOLIC H2SO4 & HEATING. WELLS JM ET AL; CAN J MICROBIOL 22: 1137 (1976).
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 267

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Health Hazard
Signal
Danger
GHS Hazard Statements

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]

H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Precautionary Statement Codes

P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Acute Tox. 2 (100%)

Acute Tox. 2 (100%)

Acute Tox. 2 (100%)

Repr. 2 (100%)

11.1.3 Hazards Summary

Causes ataxia, cyanosis, and coma at lethal doses in rats; [RTECS] Cause inhibitory effects on cell processes; No reports of chronic effects or carcinogenicity in humans; [HSDB] See Cytochalasin B.

11.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Aspergillus clavatus: HSNO Approval: HSR006810 Approved with controls

12 Toxicity

12.1 Toxicological Information

12.1.1 Acute Effects

12.1.2 Human Toxicity Excerpts

IN PURIFIED HUMAN PERIPHERAL BLOOD LYMPHOCYTES, LOW (0.01-10 MUMOL) CONCN OF CYTOCHALASINS A, B, E, & D PRODUCED MARKED AUGMENTATION OF TRANSPORT & METABOLIC RESPONSES TO PHYTOHEMAGGLUTININ (PHA) & CONCANAVALIN A (CON A), INCLUDING EFFECTS ON DNA SYNTHESIS, CYCLIC AMP ACCUMULATION, PHOSPHATIDYLINOSITOL TURNOVER, & SODIUM-DEPENDENT AMINO ACID TRANSPORT.
GREENE WC ET AL; CYTOCHALASIN SENSITIVE STRUCTURES AND LYMPHOCYTE ACTIVATION; EXP CELL RES 103(1) 109 (1976)
TREATMENT OF HUMAN POLYMORPHONUCLEAR LEUKOCYTES (PMNS) WITH CYTOCHALASIN E (CE), CYTOCHALASIN D (CD), CYTOCHALASIN B (CB), AND DIHYDROCYTOCHALASIN D (H2CB) RESULTS IN ALTERATION OF CELL MORPHOLOGY & INHIBITION OF CELL MOTILITY. MORPHOLOGICAL CHANGES ARE SIMILAR TO THOSE REPORTED FOR NONAMEBOID FIBROBLASTS: ROUNDING, ZEIOSIS, & ARBORIZATION. MEAN CELL VELOCITY OF PMNS, AS MEASURED BY QUANTITATIVE ANALYSIS OF TIME-LAPSE VIDEOTAPE RECORDINGS, WAS REDUCED TO 0.1 MUM/MIN (CONTROL, 7.3 MUM/MIN). PHAGOCYTOSIS BY PMNS, AS MEASURED BY PHAGOCYTOSIS OF LATEX BEADS, WAS INHIBITED BY 75%.
HOWARD TH ET AL; CORRELATION OF THE BIOLOGIC EFFECTS AND BINDING OF CYTOCHALASINS TO HUMAN POLYMORPHONUCLEAR LEUKOCYTES; BLOOD 57(3) 399 (1981)
THERE HAS BEEN NO REPORT ON CHRONIC TOXICITY & CARCINOGENICITY OF CYTOCHALASINS... ALTHOUGH MANY CYTOLOGICAL STUDIES HAVE BEEN DONE, THE VARIETY OF EFFECTS THUS FAR OBSERVED INDICATE THE IMPORTANCE OF THE COMPOUNDS FOR ANIMAL & HUMAN HEALTH. ...STRONG ACUTE TOXICITIES EXHIBITED BY SOME CYTOCHALASINS & THE WIDE NATURAL OCCURRENCE OF THE FUNGI THAT PRODUCE CYTOCHALASINS SHOULD BE CONSIDERED IN FUTURE STUDIES ON MYCOTOXINS. /CYTOCHALASINS/
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 578

12.1.3 Non-Human Toxicity Excerpts

EFFECTS OF CYTOCHALASINS ON MAMMALIAN CELLS: AMONG THE MORE PROMINENT EFFECTS ARE SEVERAL WHICH ARE CHARACTERIZED AS MORPHOLOGICAL IN NATURE, SUCH AS CYTOSKELETAL VARIATION, MULTINUCLEATION, DIFFUSE ORGANELLE ALTERATION, NUCLEAR EXTRUSION, & SURFACE PHENOMENA SUCH AS DIMINISHED MEMBRANE RUFFLING. OTHER EFFECTS ARE DESCRIBED AS FUNCTIONAL OR PHYSIOLOGICAL, & INCLUDE INHIBITION OF CELL MOTILITY, MITOTIC REPRODUCTION, & PHAGOCYTOSIS & PINOCYTOSIS; ALTERATION OF SURFACE ADHESION PROPERTIES & MICROFILAMENTS; DEPRESSION OF SYNTHESIS; & UPTAKE OF MEMBRANE COMPONENTS. THESE STUDIES WERE PERFORMED MAINLY WITH CYTOCHALASIN B & OCCASIONALLY WITH CYTOCHALASIN A, D (ZYGOSPORING A), & E.
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 574
CYTOCHALASIN E RARELY PRODUCES NUCLEAR EXTRUSION TYPICAL OF OTHER CYTOCHALASINS; HOWEVER, IT PRODUCES A UNIQUE HALO AROUND THE NUCLEI.
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 267
...THE REDUCTION IN /LD50/ TOXICITY OF CYTOCHALASIN E BY THE ORAL ROUTE OF ADMIN IS IMPORTANT WHEN CONSIDERING THE ROLE OF THE COMPOUND AS A FOOD-BORNE TOXIN. RATS DIE IN SUDDEN COMA WITH ACCUMULATION OF LARGE VOLUMES OF FLUID AT THE /IP/ INJECTION SITE. HISTOPATHOLOGICAL EXAM REVEALED CONGESTIVE DEGENERATIVE CHANGES, NECROSIS OF THE LIVER, KIDNEY, SPLEEN, PANCREAS & SMALL INTESTINE, BRAIN EDEMA, PULMONARY HEMORRHAGES, & INJURY TO VASCULAR WALLS.
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 577
...THE EFFECTS OF CYTOCHALASIN E ON FLUID BALANCE IN THE RAT WAS STUDIED TO CLARIFY FURTHER THE CAUSE OF DEATH. A SINGLE LETHAL DOSE OF CYTOCHALASIN E BY IP ADMIN INDUCED A RAPID DECREASE IN PLASMA PROTEIN CONCENTRATION. PLASMA CONCENTRATIONS OF ALBUMIN & GLOBUMIN WERE REDUCED WITHIN 20 MINUTES WITHOUT SIGNIFICANT CHANGE IN PLASMA FIBRINOGEN CONCENTRATION. DECREASE IN MEAN ARTERIAL PRESSURE WAS ALSO OBSERVED. CYTOCHALASIN E APPEARS TO ACT DIRECTLY ON THE WALLS OF BLOOD CAPILLARIES PERMITTING EXTRAVASCULAR EFFUSION OF PLASMA FLUID, ALBUMIN, & GLOBULIN & THE CAUSE OF DEATH IS APPARENTLY DUE TO SHOCK.
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 577
For more Non-Human Toxicity Excerpts (Complete) data for CYTOCHALASIN E (8 total), please visit the HSDB record page.

12.2 Ecological Information

12.2.1 Natural Pollution Sources

A CLASS OF MOLD METABOLITES EXHIBITING INHIBITORY EFFECTS ON CELL PROCESSES. SIX CYTOCHALASINS HAVE BEEN ISOLATED: CYTOCHALASINS A, B & F FROM HELMINTHOSPORIUM DEMATIOIDEUM; C & D FROM METARRHIZIUM ANISOPLIAE; E FROM ROSELLINIA NECATRIX. /CYTOCHALASINS/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 365
FUNGAL SOURCE: ROSELLINIA NECUTRIX & ASPERGILLUS CLAVATUS.
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 266

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Chemical Co-Occurrences in Literature

13.5 Chemical-Gene Co-Occurrences in Literature

13.6 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 ChemIDplus

17.4 ChEMBL Target Tree

17.5 UN GHS Classification

17.6 EPA DSSTox Classification

17.7 The Natural Products Atlas Classification

17.8 LOTUS Tree

17.9 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
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  3. DTP/NCI
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    https://www.cancer.gov/policies/copyright-reuse
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    21,23-Dioxa[13]cytochalasa-13,19-diene-1,17,22-trione, 6,7-epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E)-
    https://echa.europa.eu/substance-information/-/substanceinfo/100.048.018
    21,23-Dioxa[13]cytochalasa-13,19-diene-1,17,22-trione, 6,7-epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E)- (EC: 252-835-7)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/6308
  6. Hazardous Substances Data Bank (HSDB)
  7. New Zealand Environmental Protection Authority (EPA)
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    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  8. ChEBI
  9. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  10. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
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    https://haz-map.com/About
  12. Natural Product Activity and Species Source (NPASS)
  13. Metabolomics Workbench
  14. SpectraBase
  15. Springer Nature
  16. Wikidata
  17. Wikipedia
  18. PubChem
  19. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  20. GHS Classification (UNECE)
  21. The Natural Products Atlas
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    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
CONTENTS