6'-O-acetylgeniposide

ID: ALA1079151

PubChem CID: 44253991

Max Phase: Preclinical

Molecular Formula: C19H26O11

Molecular Weight: 430.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 6'-O-Acetylgeniposide | 6'-O-acetylgeniposide|CHEMBL1079151

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

Standard InChI:  InChI=1S/C19H26O11/c1-8(21)27-7-12-14(22)15(23)16(24)19(29-12)30-18-13-9(5-20)3-4-10(13)11(6-28-18)17(25)26-2/h3,6,10,12-16,18-20,22-24H,4-5,7H2,1-2H3/t10-,12-,13-,14-,15+,16-,18+,19+/m1/s1

Standard InChI Key:  RANJFIZSJJZWRL-BZDYRZRUSA-N

Molfile:  

     RDKit          2D

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   14.5938    0.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.4602   -1.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1528    1.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3036   -5.7165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8165   -0.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.7846   -1.1658    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
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  3  1  2  0
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 28 30  1  0
 32 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1079151

   6'-O-acetylgeniposide

Molecule Features

Natural Product: Yes

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: 430.41

Molecular Weight (Monoisotopic): 430.1475

AlogP: -1.66

#Rotatable Bonds: 6

Polar Surface Area: 161.21

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: -1.77

CX LogD: -1.77

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: 2.69

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