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

SCS-C002671

(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2E,4E)-5-phenylpenta-2,4-dienoyl]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-[(2E,4E)-5-phenylpenta-2,4-dienoyl]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
532.5 Da
Threshold ≤ 500
ALogP
0.73
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
10
Threshold ≤ 10
1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:
C27H32O11
Molecular Weight:
532.5420 Da
SMILES:
C[C@]1(O)CC[C@@H]2C(C(=O)O)=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)/C=C/C=C/c3ccccc3)[C@@H]21
InChIKey:
PQFVDHZYKOWDQI-NUMTYSQJSA-N
InChI:
InChI=1S/C27H32O11/c1-27(34)12-11-16-17(24(32)33)14-35-25(20(16)27)38-26-23(22(31)21(30)18(13-28)36-26)37-19(29)10-6-5-9-15-7-3-2-4-8-15/h2-10,14,16,18,20-23,25-26,28,30-31,34H,11-13H2,1H3,(H,32,33)/b9-5+,10-6+/t16-,18-,20-,21-,22+,23-,25+,26+,27+/m1/s1
Calculated Properties
ALogP:
0.725 lipophilicity
TPSA:
172.21 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
10
Rotatable Bonds:
8
Ring Count:
4 (1 aromatic)
Chiral Centers:
9
Fsp³:
0.4815 fraction sp³ carbon

Database Information

Compound ID:
SCS-C002671
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: CMNPD16527

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged