Kansuiphorin B
PubChem CID
44576012
Structure
Molecular Formula
Synonyms
- Kansuiphorin B
- CHEBI:66139
- 6,7-Epoxy-13-hydroxyingenol-3-(2,3-dimethylbutanoate)-13-dodecanoate-20-hexadecanoate
- [(1aR,2R,2aR,3aS,5R,5aS,8S,8aS,9S,9aS)-8-[(2,3-dimethylbutanoyl)oxy]-3a-(dodecanoyloxy)-8a,9-dihydroxy-3,3,5,7-tetramethyl-10-oxo-2,2a,3,3a,4,5,8a,9-octahydro-1aH-2,5a-methanocyclopenta[4,5]cyclopropa[8,9]cyclodeca[1,2-b]oxiren-9a(8H)-yl]methyl hexadecanoate
- Hexadecanoic acid,(8-(2,3-dimethyl-1-oxobutoxy)- 1a,2,2a,3a,4,5,8a,9-octahydro-8a,9-dihydroxy-3,3,5,7- tetramethyl-10-oxo-3a-((1-oxododecyl)oxy)-3H-2,5a- methanocyclopenta(4,5)cyclopropa(8,9)cyclodec(1,2-b)oxiren- 9a(8H)-yl)methyl ester
Molecular Weight
899.3 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
- Create:2010-01-26
- Modify:2025-01-18
Description
Kansuiphorin B is a tetracyclic diterpenoid that is 6,7-epoxy-13-hydroxyingenol in which the hydroxy groups at positions 3, 13 and 20 are esterified by 2,3-dimethylbutyric acid, lauric acid and palmitic acid. Isolated from the roots of Euphorbia kansui, it exhibits anti-cancerous activity. It has a role as a metabolite and an antineoplastic agent. It is a cyclic terpene ketone, a fatty acid ester, a tetracyclic diterpenoid and a dodecanoate ester. It is functionally related to a 2,3-dimethylbutyric acid, an ingenol, a dodecanoic acid and a hexadecanoic acid.
Kansuiphorin B has been reported in Euphorbia kansui with data available.
Chemical Structure Depiction
Conformer generation is disallowed since too many atoms, too flexible
[(1S,4S,5S,6S,7S,9R,10R,11R,13S,15R)-4-(2,3-dimethylbutanoyloxy)-13-dodecanoyloxy-5,6-dihydroxy-3,12,12,15-tetramethyl-16-oxo-8-oxapentacyclo[8.5.1.01,5.07,9.011,13]hexadec-2-en-7-yl]methyl hexadecanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)
InChI=1S/C54H90O10/c1-10-12-14-16-18-20-21-22-23-25-26-28-30-32-41(55)61-36-52-47(64-52)43-44-50(8,9)53(44,63-42(56)33-31-29-27-24-19-17-15-13-11-2)35-39(6)51(45(43)57)34-38(5)46(54(51,60)49(52)59)62-48(58)40(7)37(3)4/h34,37,39-40,43-44,46-47,49,59-60H,10-33,35-36H2,1-9H3/t39-,40?,43+,44-,46+,47-,49-,51+,52-,53+,54-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
DQVMDPSQAAGKSN-LZYXWQDISA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
CCCCCCCCCCCCCCCC(=O)OC[C@]12[C@H](O1)[C@H]3[C@H]4[C@](C4(C)C)(C[C@H]([C@]5(C3=O)C=C([C@@H]([C@]5([C@@H]2O)O)OC(=O)C(C)C(C)C)C)C)OC(=O)CCCCCCCCCCC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C54H90O10
Computed by PubChem 2.1 (PubChem release 2021.05.07)
- 6,7-epoxy-13-hydroxyingenol-3-(2,3-dimethylbutanoate)-13-dodecanoate-20-hexadecanoate
- kansuiphorin B
- Kansuiphorin B
- CHEBI:66139
- 6,7-Epoxy-13-hydroxyingenol-3-(2,3-dimethylbutanoate)-13-dodecanoate-20-hexadecanoate
- [(1aR,2R,2aR,3aS,5R,5aS,8S,8aS,9S,9aS)-8-[(2,3-dimethylbutanoyl)oxy]-3a-(dodecanoyloxy)-8a,9-dihydroxy-3,3,5,7-tetramethyl-10-oxo-2,2a,3,3a,4,5,8a,9-octahydro-1aH-2,5a-methanocyclopenta[4,5]cyclopropa[8,9]cyclodeca[1,2-b]oxiren-9a(8H)-yl]methyl hexadecanoate
- Hexadecanoic acid,(8-(2,3-dimethyl-1-oxobutoxy)- 1a,2,2a,3a,4,5,8a,9-octahydro-8a,9-dihydroxy-3,3,5,7- tetramethyl-10-oxo-3a-((1-oxododecyl)oxy)-3H-2,5a- methanocyclopenta(4,5)cyclopropa(8,9)cyclodec(1,2-b)oxiren- 9a(8H)-yl)methyl ester
- ((1aR,2R,2aR,3aS,5R,5aS,8S,8aS,9S,9aS)-8-((2,3-dimethylbutanoyl)oxy)-3a-(dodecanoyloxy)-8a,9-dihydroxy-3,3,5,7-tetramethyl-10-oxo-2,2a,3,3a,4,5,8a,9-octahydro-1aH-2,5a-methanocyclopenta(4,5)cyclopropa(8,9)cyclodeca(1,2-b)oxiren-9a(8H)-yl)methyl hexadecanoate
- ((1S,4R,5R,6R,7R,9S,10S,11S,13R,15R)-4-(((2S)-2,3-dimethylbutanoyl)oxy)-13-(dodecanoyloxy)-5,6-dihydroxy-3,12,12,15-tetramethyl-16-oxo-8-oxapentacyclo(8.5.1.0,.0,.0,)hexadec-2-en-7-yl)methyl hexadecanoic acid
- ((1S,4S,5S,6S,7S,9R,10R,11R,13S,15R)-4-(2,3-dimethylbutanoyloxy)-13-dodecanoyloxy-5,6-dihydroxy-3,12,12,15-tetramethyl-16-oxo-8-oxapentacyclo(8.5.1.01,5.07,9.011,13)hexadec-2-en-7-yl)methyl hexadecanoate
- [(1S,4R,5R,6R,7R,9S,10S,11S,13R,15R)-4-{[(2S)-2,3-dimethylbutanoyl]oxy}-13-(dodecanoyloxy)-5,6-dihydroxy-3,12,12,15-tetramethyl-16-oxo-8-oxapentacyclo[8.5.1.0,.0,.0,]hexadec-2-en-7-yl]methyl hexadecanoic acid
- [(1S,4S,5S,6S,7S,9R,10R,11R,13S,15R)-4-(2,3-dimethylbutanoyloxy)-13-dodecanoyloxy-5,6-dihydroxy-3,12,12,15-tetramethyl-16-oxo-8-oxapentacyclo[8.5.1.01,5.07,9.011,13]hexadec-2-en-7-yl]methyl hexadecanoate
- CHEMBL454542
- Hexadecanoic acid,(8-(2,3-dimethyl-1-oxobutoxy)-1a,2,2a,3a,4,5,8a,9-octahydro-8a,9-dihydroxy-3,3,5,7-tetramethyl-10-oxo-3a-((1-oxododecyl)oxy)-3H-2,5a-methanocyclopenta(4,5)cyclopropa(8,9)cyclodec(1,2-b)oxiren-9a(8H)-yl)methyl ester
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
899.3 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
14.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
33
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
898.65339906 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
898.65339906 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
149 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
64
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1600
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
10
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
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 2019.01.04)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Kansuiphorin Bhttps://www.wikidata.org/wiki/Q104987207LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- Natural Product Activity and Species Source (NPASS)
- Metabolomics Workbench
- WikidataKansuiphorin Bhttps://www.wikidata.org/wiki/Q104987207
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlkansuiphorin Bhttps://www.ncbi.nlm.nih.gov/mesh/67071760
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
CONTENTS