domoric acid

ID: ALA482097

Cas Number: 133005-85-3

PubChem CID: 44568340

Max Phase: Preclinical

Molecular Formula: C15H21NO6

Molecular Weight: 311.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Domoric Acid | ISODOMOIC ACID E|domoric acid|133005-85-3|CHEMBL482097|(2S,3S,4S)-4-[(2E,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid|(-)-domoic acid|E,E-Isodomoic acid|ISODOMOICACIDE|(-)-Isodomoic acid E|SCHEMBL13319904|(2S,3S,4S)-2-CARBOXY-4-[(1Z,3E,5R)-5-CARBOXY-1-METHYL-1,3-HEXADIENYL]-3-PYRROLIDINEACETIC ACID|BDBM50252103|PD119713

Canonical SMILES:  C/C(=C\C=C\[C@@H](C)C(=O)O)[C@H]1CN[C@H](C(=O)O)[C@H]1CC(=O)O

Standard InChI:  InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4+/t9-,10+,11-,13+/m1/s1

Standard InChI Key:  VZFRNCSOCOPNDB-JIUSADRUSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    7.7517   -6.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1959   -5.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6796   -5.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9093   -5.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9516   -6.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0182   -5.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2334   -6.7451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5992   -5.3626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026   -5.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168   -5.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152   -4.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7498   -4.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5030   -4.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2448   -4.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5174   -3.2227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7883   -5.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737   -5.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3593   -5.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6447   -5.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3596   -4.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0742   -3.8121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453   -3.8117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0
  2  6  1  1
  9 10  2  0
 10 11  1  0
  4 10  1  6
 13 14  2  0
 13 15  1  0
 12 13  1  0
  3 12  1  6
  9 16  1  0
  1  2  1  0
 16 17  2  0
  2  3  1  0
 17 18  1  0
  3  4  1  0
 18 19  1  1
  4  5  1  0
 18 20  1  0
  1  5  1  0
  6  7  2  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA482097

   DOMORIC ACID

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: 311.33

Molecular Weight (Monoisotopic): 311.1369

AlogP: 0.97

#Rotatable Bonds: 7

Polar Surface Area: 123.93

Molecular Species: ZWITTERION

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.68

CX Basic pKa: 11.59

CX LogP: -1.79

CX LogD: -7.30

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.52

Np Likeness Score: 2.15

References

1. Sagot E, Pickering DS, Pu X, Umberti M, Stensbøl TB, Nielsen B, Chapelet M, Bolte J, Gefflaut T, Bunch L..  (2008)  Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7.,  51  (14): [PMID:18578478] [10.1021/jm800092x]

Source

Source(1):

• Scientific Literature