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  3. (3S,5S,10R,13R,17R)-17-[(2R,5S)-5-ethyl-6-methylhept-6-en-2-yl]-5-hydroperoxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol

SCS-C005776

(3S,5S,10R,13R,17R)-17-[(2R,5S)-5-ethyl-6-methylhept-6-en-2-yl]-5-hydroperoxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol

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

Structure of (3S,5S,10R,13R,17R)-17-[(2R,5S)-5-ethyl-6-methylhept-6-en-2-yl]-5-hydroperoxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
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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

Codium arabicum (NA)
Kingdom Viridiplantae Phylum Chlorophyta Class Ulvophyceae Order Bryopsidales Family Codiaceae Genus Codium Species Codium arabicum
Penghu Islands
DOI: 10.1039/np9971400259  · Natural Product Reports

Drug-likeness (Lipinski Ro5)

Molecular Weight
444.7 Da
Threshold ≤ 500
ALogP
7.41
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C29H48O3
Molecular Weight:
444.7000 Da
SMILES:
C=C(C)[C@@H](CC)CC[C@@H](C)[C@H]1CCC2C3C=C[C@@]4(OO)C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C
InChIKey:
MUKFLVKMTBSLHF-FEGUWOJXSA-N
InChI:
InChI=1S/C29H48O3/c1-7-21(19(2)3)9-8-20(4)24-10-11-25-23-13-17-29(32-31)18-22(30)12-16-28(29,6)26(23)14-15-27(24,25)5/h13,17,20-26,30-31H,2,7-12,14-16,18H2,1,3-6H3/t20-,21+,22+,23?,24-,25?,26?,27-,28-,29-/m1/s1
Calculated Properties
ALogP:
7.413 lipophilicity
TPSA:
49.69 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
7
Ring Count:
4 (0 aromatic)
Chiral Centers:
10
Fsp³:
0.8621 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005776
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids Stigmastane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD7307

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged