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

SCS-C005212

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

Pathway: Terpenoids Superclass: Steroids Class: Cholestane steroids | Ergostane steroids Glycoside
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Chemical Structure

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

Bugula neritina (marine bryozoan)
Kingdom Metazoa Phylum Bryozoa Class Gymnolaemata Order Cheilostomatida Family Bugulidae Genus Bugula Species Bugula neritina
Daya Bay
DOI: 10.1016/j.phytol.2014.03.010  · Phytochemistry Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight
544.8 Da
Threshold ≤ 500
ALogP
6.26
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C34H56O5
Molecular Weight:
544.8170 Da
SMILES:
CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey:
KEWBRRAQJHKIEP-SNGHGGBBSA-N
InChI:
InChI=1S/C34H56O5/c1-19(2)20(3)8-9-21(4)26-12-13-27-25-11-10-23-18-24(39-32-31(37)30(36)29(35)22(5)38-32)14-16-33(23,6)28(25)15-17-34(26,27)7/h8-10,19-22,24-32,35-37H,11-18H2,1-7H3/b9-8+/t20-,21+,22-,24-,25-,26+,27-,28-,29-,30+,31+,32-,33-,34+/m0/s1
Calculated Properties
ALogP:
6.263 lipophilicity
TPSA:
79.15 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
6
Ring Count:
5 (0 aromatic)
Chiral Centers:
14
Fsp³:
0.8824 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005212
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids Ergostane steroids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD25592

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged