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15-keto Bimatoprost

PubChem CID
35028392
Structure
15-keto Bimatoprost_small.png
15-keto Bimatoprost_3D_Structure.png
Molecular Formula
Synonyms
  • 15-keto Bimatoprost
  • 1163135-96-3
  • Bimatoprost impurity B
  • 15-Ketobimatoprost
  • UNII-P14259CVZG
Molecular Weight
413.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2009-05-29
  • Modify:
    2025-01-11
Description
15-ketobimatoprost is a prostanoid.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
15-keto Bimatoprost.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C25H35NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,21-24,28-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t21-,22-,23+,24-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

OZCBJWOYRKMMPF-QWPROEHNSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/C(=O)CCC2=CC=CC=C2)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C25H35NO4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 DSSTox Substance ID

2.3.6 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
413.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
413.25660860 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
413.25660860 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
86.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
580
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
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)

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

NIST Number
1217160
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
414.2639
Total Peaks
52
m/z Top Peak
396.3
m/z 2nd Highest
378.3
m/z 3rd Highest
370.4
Thumbnail
Thumbnail

6 Chemical Vendors

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 GHS Classification

Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H340 (100%): May cause genetic defects [Danger Germ cell mutagenicity]

H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Precautionary Statement Codes

P203, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P405, and P501

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

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

8.3 Chemical Co-Occurrences in Patents

8.4 Chemical-Disease Co-Occurrences in Patents

9 Classification

9.1 ChEBI Ontology

9.2 ChemIDplus

9.3 UN GHS Classification

9.4 EPA DSSTox Classification

9.5 MolGenie Organic Chemistry Ontology

10 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide
    https://commonchemistry.cas.org/detail?cas_rn=1163135-96-3
  2. ChemIDplus
    7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E)-3-oxo-5-phenyl-1-penten-1-yl)cyclopentyl)-N-ethyl-5-heptenamide, (5Z)-
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=1163135963
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide
    https://comptox.epa.gov/dashboard/DTXSID501109753
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
    5-Heptenamide, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl, (5Z)
    https://echa.europa.eu/substance-information/-/substanceinfo/100.238.239
    5-Heptenamide, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl, (5Z) (EC: 810-194-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/247592
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
    7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E)-3-OXO-5-PHENYL-1-PENTEN-1-YL)CYCLOPENTYL)-N-ETHYL-5-HEPTENAMIDE, (5Z)-
    https://gsrs.ncats.nih.gov/ginas/app/beta/substances/P14259CVZG
  6. ChEBI
  7. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  8. Wikidata
    (5Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E)-3-oxo-5-phenyl-1-penten-1-yl)cyclopentyl)-N-ethyl-5-heptenamide
    https://www.wikidata.org/wiki/Q27285988
  9. PubChem
  10. GHS Classification (UNECE)
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  12. PATENTSCOPE (WIPO)
CONTENTS