11-(6-O-trans-sinapoylglucopyranosyl)gardendiol

ID: ALA1078907

PubChem CID: 44255333

Max Phase: Preclinical

Molecular Formula: C27H34O13

Molecular Weight: 566.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)OC[C@H]2O[C@@H](OC[C@H]3C(=O)OC[C@@H]4C(CO)=CC[C@@H]43)[C@H](O)[C@@H](O)[C@@H]2O)cc(OC)c1O

Standard InChI:  InChI=1S/C27H34O13/c1-35-18-7-13(8-19(36-2)22(18)30)3-6-21(29)37-12-20-23(31)24(32)25(33)27(40-20)39-11-17-15-5-4-14(9-28)16(15)10-38-26(17)34/h3-4,6-8,15-17,20,23-25,27-28,30-33H,5,9-12H2,1-2H3/b6-3+/t15-,16+,17+,20+,23+,24-,25+,27+/m0/s1

Standard InChI Key:  MRSXXJYRGDMBIT-BFKATWTQSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1078907

   [(2R,3S,4S,5R,6R)-6-[[(4S,4aS,7aS)-7-(hydroxymethyl)-3-oxo-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-4-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

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: 566.56

Molecular Weight (Monoisotopic): 566.1999

AlogP: -0.48

#Rotatable Bonds: 10

Polar Surface Area: 190.67

Molecular Species: NEUTRAL

HBA: 13

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.29

CX Basic pKa: ┄

CX LogP: -0.27

CX LogD: -0.27

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.14

Np Likeness Score: 2.14

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