SCS-C002905

(2R,3S,4R,5S,6S)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-ethenyl-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: Pregnane steroids Glycoside

Chemical Structure

Structure of (2R,3S,4R,5S,6S)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-ethenyl-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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Source Information

Cladiella krempfi (soft coral)

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Cladiellidae Genus Cladiella Species Cladiella krempfi

Hainan Island

DOI: 10.1039/b701534h · Natural Product Reports

Drug-likeness (Lipinski Ro5)

Molecular Weight

446.6 Da

Threshold ≤ 500

ALogP

3.96

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H42O5

Molecular Weight:

446.6280 Da

SMILES:

C=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:

                        DCRGJPXYYYQEFH-YWBCEQLFSA-N
                        
                    

InChI:

InChI=1S/C27H42O5/c1-5-16-7-9-20-19-8-6-17-14-18(32-25-24(30)23(29)22(28)15(2)31-25)10-12-27(17,4)21(19)11-13-26(16,20)3/h5-6,15-16,18-25,28-30H,1,7-14H2,2-4H3/t15-,16-,18-,19-,20-,21-,22+,23+,24-,25-,26+,27-/m0/s1

Calculated Properties

ALogP:

3.964 lipophilicity

TPSA:

79.15 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (0 aromatic)

Chiral Centers:

Fsp³:

0.8519 fraction sp³ carbon

Database Information

Compound ID:

SCS-C002905

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Steroids

NPClassifier Class:

Pregnane steroids

Glycoside:

Yes

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD16391

Biological Activity Data

No bioactivity data available for this compound.

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