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

SCS-C004160

(1R,3S,5R,8S,9S,10S,13R,14S,17R)-1,3,5-trihydroxy-10,13-dimethyl-17-[(E,2R)-6-methylhept-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 (1R,3S,5R,8S,9S,10S,13R,14S,17R)-1,3,5-trihydroxy-10,13-dimethyl-17-[(E,2R)-6-methylhept-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.
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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
432.6 Da
Threshold ≤ 500
ALogP
4.51
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C27H44O4
Molecular Weight:
432.6450 Da
SMILES:
CC(C)C/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC(=O)[C@@]4(O)C[C@@H](O)C[C@@H](O)[C@]4(C)[C@H]3CC[C@]12C
InChIKey:
DZECUSKDCWYJLV-GIVCTHQWSA-N
InChI:
InChI=1S/C27H44O4/c1-16(2)7-6-8-17(3)20-9-10-21-19-14-24(30)27(31)15-18(28)13-23(29)26(27,5)22(19)11-12-25(20,21)4/h6,8,16-23,28-29,31H,7,9-15H2,1-5H3/b8-6+/t17-,18+,19+,20-,21+,22+,23-,25-,26+,27+/m1/s1
Calculated Properties
ALogP:
4.509 lipophilicity
TPSA:
77.76 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
4
Rotatable Bonds:
4
Ring Count:
4 (0 aromatic)
Chiral Centers:
10
Fsp³:
0.8889 fraction sp³ carbon

Database Information

Compound ID:
SCS-C004160
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: CMNPD24165

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged