Isobutyric acid (9R,10R)-9-acetoxy-8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-10-yl ester

ID: ALA70302

PubChem CID: 10317265

Max Phase: Preclinical

Molecular Formula: C20H22O7

Molecular Weight: 374.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Seravshanin | Hyuganin D|[(9R,10R)-9-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] 2-methylpropanoate|SERAVSHANIN|CHEMBL70302|HY-N4022|AKOS032962681|CS-0024462

Canonical SMILES:  CC(=O)O[C@@H]1[C@H](OC(=O)C(C)C)c2c(ccc3ccc(=O)oc23)OC1(C)C

Standard InChI:  InChI=1S/C20H22O7/c1-10(2)19(23)26-17-15-13(27-20(4,5)18(17)24-11(3)21)8-6-12-7-9-14(22)25-16(12)15/h6-10,17-18H,1-5H3/t17-,18-/m1/s1

Standard InChI Key:  BUTUNJHEBGRWGK-QZTJIDSGSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.9558   -5.7043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432   -6.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5307   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432   -5.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301   -5.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5242   -4.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2434   -4.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8153   -4.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -5.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164   -5.7209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -5.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -4.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964   -4.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164   -5.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730   -6.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9512   -7.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432   -7.7647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -6.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582   -8.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582   -9.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -7.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8220   -7.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1078   -8.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336   -8.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6080   -7.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091   -9.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1  5  1  0
 24 26  1  0
  9 14  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA70302

   SERAVSHANIN

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: 374.39

Molecular Weight (Monoisotopic): 374.1366

AlogP: 3.14

#Rotatable Bonds: 3

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: 2.94

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: 2.24

References

1. Matsuda H, Murakami T, Kageura T, Ninomiya K, Toguchida I, Nishida N, Yoshikawa M..  (1998)  Hepatoprotective and nitric oxide production inhibitory activities of coumarin and polyacetylene constituents from the roots of Angelica furcijuga.,  8  (16): [PMID:9873511] [10.1016/s0960-894x(98)00391-6]

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

Source

Source(1):

• Scientific Literature