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  3. (4S,5S)-4-[(5R,8R,9R,10R,13S,17S)-7-hydroxy-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-5-methoxyoxolan-2-one

SCS-C003041

(4S,5S)-4-[(5R,8R,9R,10R,13S,17S)-7-hydroxy-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-5-methoxyoxolan-2-one

Pathway: Terpenoids Superclass: Triterpenoids Class: Apotirucallane triterpenoids | Limonoids Glycoside
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Chemical Structure

Structure of (4S,5S)-4-[(5R,8R,9R,10R,13S,17S)-7-hydroxy-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-5-methoxyoxolan-2-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

Xylocarpus granatum (Mangrove)
Kingdom Viridiplantae Phylum Streptophyta Class Magnoliopsida Order Sapindales Family Meliaceae Genus Xylocarpus Species Xylocarpus granatum
Hainan Island
DOI: 10.1002/hlca.201400290  · Helvetica Chimica Acta

Drug-likeness (Lipinski Ro5)

Molecular Weight
442.6 Da
Threshold ≤ 500
ALogP
4.44
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C27H38O5
Molecular Weight:
442.5960 Da
SMILES:
CO[C@H]1OC(=O)C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)C=CC(=O)C(C)(C)[C@@H]3CC(O)[C@@]21C
InChIKey:
LZKUSLWZFKUZQS-FDHNPTHWSA-N
InChI:
InChI=1S/C27H38O5/c1-24(2)19-14-21(29)27(5)17-8-7-16(15-13-22(30)32-23(15)31-6)25(17,3)11-9-18(27)26(19,4)12-10-20(24)28/h8,10,12,15-16,18-19,21,23,29H,7,9,11,13-14H2,1-6H3/t15-,16-,18+,19-,21?,23-,25-,26+,27-/m0/s1
Calculated Properties
ALogP:
4.443 lipophilicity
TPSA:
72.83 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
5
Rotatable Bonds:
2
Ring Count:
5 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.7778 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003041
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Apotirucallane triterpenoids Limonoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD27101

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged