SCS-C003768
[(2S,3R,4S,5R)-2-[[(3S,4S,5R,8S,9S,10R,13R,14S,17R)-17-ethenyl-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl]oxy]-3,5-dihydroxyoxan-4-yl] acetate
Pathway: Terpenoids
Superclass: Steroids
Class: Pregnane steroids
Glycoside
Chemical Structure
![Structure of [(2S,3R,4S,5R)-2-[[(3S,4S,5R,8S,9S,10R,13R,14S,17R)-17-ethenyl-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl]oxy]-3,5-dihydroxyoxan-4-yl] acetate](/scsmarinenp/static/images/structures/SCS-C003768.png)
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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.
Source Information
Lobophytum sp.
(soft coral)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Alcyoniidae
Genus
Lobophytum
Species
NA
Sanya Bay
Records of Natural Products, 2015, 9, 271-275. || Natural Product Communications, 2013, 8, 67-68. || Chemistry of Natural Compounds, 2013, 49, 653-656. || Natural Product Communications, 2013, 8, 1069-1070. || Acta Chimica Sinica / Acta Chim. Sin, 2001. || Natural Product Communications, 2013, 8, 1127-1128. || Chemical Journal of Chinese Universities, 2007. || Acta Chimica Sinica, 2002. || Turkish Journal of Chemistry, 1999, 23(3), 339-344. || Chinese Journal of Organic Chemistry, 2002. || Chinese Journal of Chemistry, 2013, 31, 100-104. || Marine Drugs, 2068. || Helvetica Chimica Acta, 2013, 96, 1188-1196. || Liu Qing || Li Ruisheng. Study on chemical constituents of Chinese soft coral. (37) Structure of a novel polyhydroxylated steroid / 《() --》. || The Journal of Antibiotics, 2013, 66, 327-331. || Indian Journal of Chemistry, Section B, 2002. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 2002. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1999. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1998, 37(3), 82-85. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1987. || Chinese Journal of Organic Chemistry, 2007. || Natural Product Communications, 2015, 10, 1033-1037. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 2001. || Chemical Research in Chinese Universities, 1998, 14(4), 426-427. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1986. || Phytochemistry Letters, 2013, 6, 392-396. || Natural Product Reports, 1997. || Chinese Journal of Organic Chemistry, 2001. || Journal of Natural Products, 2013. || Chinese Journal of Marine Drugs, 1998, 17(1), 1-3. || Chemical Journal of Chinese Universities, 2021. || Chinese Journal of Marine Drugs, 2003, 22, 28-30. || Natural Product Communications, 2015, 10, 1203-1208. || Archives of Pharmacal Research, 2013, 36, 739-744. || Steroids, 2013, 78, 396-400.
Drug-likeness (Lipinski Ro5)
Molecular Weight
492.7 Da
Threshold ≤ 500
ALogP
3.20
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C28H44O7
Molecular Weight:
492.6530 Da
SMILES:
C=C[C@H]1CC[C@H]2[C@@H]3CC[C@H]4[C@H](O[C@@H]5OC[C@@H](O)[C@H](OC(C)=O)[C@H]5O)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey:
ZRYDTLONLITJHL-JVXDHCMUSA-N
InChI:
InChI=1S/C28H44O7/c1-5-16-6-8-18-17-7-9-20-24(35-26-23(32)25(34-15(2)29)22(31)14-33-26)21(30)11-13-28(20,4)19(17)10-12-27(16,18)3/h5,16-26,30-32H,1,6-14H2,2-4H3/t16-,17-,18-,19-,20-,21-,22+,23+,24-,25-,26-,27+,28+/m0/s1
Calculated Properties
ALogP:
3.197 lipophilicity
TPSA:
105.45 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
7
Rotatable Bonds:
4
Ring Count:
5
(0 aromatic)
Chiral Centers:
13
Fsp³:
0.8929 fraction sp³ carbon
Database Information
Compound ID:
SCS-C003768
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Pregnane steroids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.