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  3. (3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one

SCS-C006407

(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one

Pathway: Terpenoids Superclass: Steroids Class: Cholestane steroids
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Chemical Structure

Structure of (3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

Source Information

Lobophytum pauciflorum (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Alcyoniidae Genus Lobophytum Species Lobophytum pauciflorum
South China Sea
DOI: 10.3762/bjoc.18.42  · Beilstein Journal of Organic Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight
400.6 Da
Threshold ≤ 500
ALogP
6.57
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C27H44O2
Molecular Weight:
400.6470 Da
SMILES:
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey:
YIKKMWSQVKJCOP-ABXCMAEBSA-N
InChI:
InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1
Calculated Properties
ALogP:
6.568 lipophilicity
TPSA:
37.30 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
2
Rotatable Bonds:
5
Ring Count:
4 (0 aromatic)
Chiral Centers:
8
Fsp³:
0.8889 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006407
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged