6'-O-trans-p-coumaroylgeniposide

ID: ALA1078425

PubChem CID: 44255238

Max Phase: Preclinical

Molecular Formula: C26H30O12

Molecular Weight: 534.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(=O)/C=C/c3ccc(O)cc3)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2C(CO)=CC[C@H]12

Standard InChI:  InChI=1S/C26H30O12/c1-34-24(33)17-11-36-25(20-14(10-27)5-8-16(17)20)38-26-23(32)22(31)21(30)18(37-26)12-35-19(29)9-4-13-2-6-15(28)7-3-13/h2-7,9,11,16,18,20-23,25-28,30-32H,8,10,12H2,1H3/b9-4+/t16-,18-,20-,21-,22+,23-,25+,26+/m1/s1

Standard InChI Key:  IVYAOUHUAWZJDB-UZOBGTHZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1078425

   methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 534.51

Molecular Weight (Monoisotopic): 534.1737

AlogP: -0.26

#Rotatable Bonds: 8

Polar Surface Area: 181.44

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.40

CX Basic pKa: ┄

CX LogP: 0.52

CX LogD: 0.51

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.17

Np Likeness Score: 2.23

References

1. Yu Y, Xie ZL, Gao H, Ma WW, Dai Y, Wang Y, Zhong Y, Yao XS..  (2009)  Bioactive iridoid glucosides from the fruit of Gardenia jasminoides.,  72  (8): [PMID:19650637] [10.1021/np900176q]

Source

Source(1):

• Scientific Literature