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  3. (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

SCS-C002672

(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Pathway: Terpenoids Superclass: Monoterpenoids Class: Iridoids monoterpenoids Glycoside
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Chemical Structure

Structure of (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
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Source Information

Avicennia marina (mangrove fruit)
Kingdom Viridiplantae Phylum Streptophyta Class Magnoliopsida Order Lamiales Family Acanthaceae Genus Avicennia Species Avicennia marina
Wenchang
DOI: 10.1002/cbdv.200690082  · Chemistry & Biodiversity

Drug-likeness (Lipinski Ro5)

Molecular Weight
536.5 Da
Threshold ≤ 500
ALogP
0.18
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
11
Threshold ≤ 10
2 violations (MW, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C26H32O12
Molecular Weight:
536.5300 Da
SMILES:
COc1ccc(/C=C/C(=O)O[C@H]2[C@H](O[C@@H]3OC=C(C(=O)O)[C@H]4CC[C@](C)(O)[C@@H]34)O[C@H](CO)[C@@H](O)[C@@H]2O)cc1
InChIKey:
CGQHDMQVSGXNLP-ZGEATZQDSA-N
InChI:
InChI=1S/C26H32O12/c1-26(33)10-9-15-16(23(31)32)12-35-24(19(15)26)38-25-22(21(30)20(29)17(11-27)36-25)37-18(28)8-5-13-3-6-14(34-2)7-4-13/h3-8,12,15,17,19-22,24-25,27,29-30,33H,9-11H2,1-2H3,(H,31,32)/b8-5+/t15-,17-,19-,20-,21+,22-,24+,25+,26+/m1/s1
Calculated Properties
ALogP:
0.178 lipophilicity
TPSA:
181.44 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
11
Rotatable Bonds:
8
Ring Count:
4 (1 aromatic)
Chiral Centers:
9
Fsp³:
0.5385 fraction sp³ carbon

Database Information

Compound ID:
SCS-C002672
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Monoterpenoids
NPClassifier Class:
Iridoids monoterpenoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD16528

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged