6'-O-trans-sinapoylgeniposide

ID: ALA1078909

PubChem CID: 46883088

Max Phase: Preclinical

Molecular Formula: C28H34O14

Molecular Weight: 594.57

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/c3cc(OC)c(O)c(OC)c3)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2C(CO)=CC[C@H]12

Standard InChI:  InChI=1S/C28H34O14/c1-36-17-8-13(9-18(37-2)22(17)31)4-7-20(30)39-12-19-23(32)24(33)25(34)28(41-19)42-27-21-14(10-29)5-6-15(21)16(11-40-27)26(35)38-3/h4-5,7-9,11,15,19,21,23-25,27-29,31-34H,6,10,12H2,1-3H3/b7-4+/t15-,19-,21-,23-,24+,25-,27+,28+/m1/s1

Standard InChI Key:  YOFHAHMLGOFXAB-OBCDOPQVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1078909

   NCGC00384993-01_C28H34O14_Methyl (1S,4aS,7aS)-1-({6-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-propenoyl]-beta-D-glucopyranosyl}oxy)-7-(hydroxymethyl)-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: 594.57

Molecular Weight (Monoisotopic): 594.1949

AlogP: -0.24

#Rotatable Bonds: 10

Polar Surface Area: 199.90

Molecular Species: NEUTRAL

HBA: 14

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.29

CX Basic pKa: ┄

CX LogP: 0.20

CX LogD: 0.19

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.13

Np Likeness Score: 2.06

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