quianhucoumarin D

ID: ALA512733

PubChem CID: 10450303

Max Phase: Preclinical

Molecular Formula: C18H18O7

Molecular Weight: 346.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Quianhucoumarin D | quianhucoumarin D|CHEMBL512733

Canonical SMILES:  CC(=O)O[C@@H]1c2c(ccc3ccc(=O)oc23)OC(C)(C)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C18H18O7/c1-9(19)22-16-14-12(25-18(3,4)17(16)23-10(2)20)7-5-11-6-8-13(21)24-15(11)14/h5-8,16-17H,1-4H3/t16-,17-/m1/s1

Standard InChI Key:  YJOWXMGENDGFDH-IAGOWNOFSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    3.9548   -6.1354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9548   -6.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -7.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799   -6.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -5.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804   -6.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3863   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6672   -4.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0952   -4.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0852   -5.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7941   -6.1520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5176   -5.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5277   -4.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8142   -4.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2270   -6.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2377   -6.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594   -7.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -8.1956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0900   -7.3761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9523   -8.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9523   -9.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2374   -8.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0885   -8.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8029   -8.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3769   -8.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  2  3  1  0
 12 15  2  0
  5  8  1  0
  2 16  1  0
  6 10  1  0
  2 17  1  0
  9  7  1  0
  3 18  1  1
  7  8  2  0
  4 19  1  1
  9 10  2  0
 18 20  1  0
  3  4  1  0
 20 21  1  0
  4  6  1  0
 20 22  2  0
  5  6  2  0
 19 23  1  0
 23 24  1  0
  1  2  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA512733

   QUIANHUCOUMARIN D

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: 346.34

Molecular Weight (Monoisotopic): 346.1053

AlogP: 2.50

#Rotatable Bonds: 2

Polar Surface Area: 92.04

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.70

CX LogD: 1.70

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: 2.17

References

1. Valencia-Islas N, Abbas H, Bye R, Toscano R, Mata R..  (2002)  Phytotoxic compounds from Prionosciadium watsoni.,  65  (6): [PMID:12088423] [10.1021/np010448t]

2. Domínguez-Mendoza EA, Cornejo-Garrido J, Burgueño-Tapia E, Ordaz-Pichardo C..  (2016)  Antidiabetic effect, antioxidant activity, and toxicity of 3',4'-Di-O-acetyl-cis-khellactone in Streptozotocin-induced diabetic rats.,  26  (16): [PMID:27397496] [10.1016/j.bmcl.2016.06.071]

Source

Source(1):

• Scientific Literature