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  3. (6S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5,6-dimethylhept-3-en-2-yl]-6-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

SCS-C003066

(6S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5,6-dimethylhept-3-en-2-yl]-6-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

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

Structure of (6S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5,6-dimethylhept-3-en-2-yl]-6-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-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

Iotrochota birotulata (NA)
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Poecilosclerida Family Iotrochotidae Genus Iotrochota Species Iotrochota birotulata
Hainan Island
DOI: 10.1021/np050080q  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
412.7 Da
Threshold ≤ 500
ALogP
6.59
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C28H44O2
Molecular Weight:
412.6580 Da
SMILES:
CC(C)[C@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey:
MLAIIMMDMSUHSS-KFFZTEKKSA-N
InChI:
InChI=1S/C28H44O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-16-26(30)25-15-20(29)11-13-28(25,6)24(21)12-14-27(22,23)5/h7-8,15,17-19,21-24,26,30H,9-14,16H2,1-6H3/b8-7+/t18-,19-,21+,22-,23+,24+,26+,27-,28-/m1/s1
Calculated Properties
ALogP:
6.590 lipophilicity
TPSA:
37.30 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
2
Rotatable Bonds:
4
Ring Count:
4 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.8214 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003066
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Ergostane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD15216

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged