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  3. (3S,5R,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-17-[(E,2R)-5-methylhex-3-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one

SCS-C004166

(3S,5R,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-17-[(E,2R)-5-methylhex-3-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one

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

Structure of (3S,5R,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-17-[(E,2R)-5-methylhex-3-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-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

Menella kanisa (gorgonian coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Plexauridae Genus Menella Species Menella kanisa
Beihai
DOI: 10.1016/j.steroids.2013.05.019  · Steroids

Drug-likeness (Lipinski Ro5)

Molecular Weight
402.6 Da
Threshold ≤ 500
ALogP
5.15
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C26H42O3
Molecular Weight:
402.6190 Da
SMILES:
CC(C)/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC(=O)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey:
ZCGQXKHIMLRISN-HCYOZZGASA-N
InChI:
InChI=1S/C26H42O3/c1-16(2)6-7-17(3)20-8-9-21-19-14-23(28)26(29)15-18(27)10-13-25(26,5)22(19)11-12-24(20,21)4/h6-7,16-22,27,29H,8-15H2,1-5H3/b7-6+/t17-,18+,19+,20-,21+,22+,24-,25-,26+/m1/s1
Calculated Properties
ALogP:
5.148 lipophilicity
TPSA:
57.53 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
3
Ring Count:
4 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.8846 fraction sp³ carbon

Database Information

Compound ID:
SCS-C004166
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 CMNPD: CMNPD24162

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged