4-Hydroxyretinoic Acid methylester

ID: ALA1908017

Cas Number: 38030-59-0

PubChem CID: 11174913

Max Phase: Preclinical

Molecular Formula: C21H30O3

Molecular Weight: 330.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-Hydroxyretinoic Acid Methylester | 4-Hydroxyretinoic Acid Methylester|SCHEMBL5361434|CHEMBL1908017|DTXSID001280603|Retinoic acid, 4-hydroxy-, methyl ester|38030-59-0

Canonical SMILES:  COC(=O)/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C(O)CCC1(C)C

Standard InChI:  InChI=1S/C21H30O3/c1-15(8-7-9-16(2)14-20(23)24-6)10-11-18-17(3)19(22)12-13-21(18,4)5/h7-11,14,19,22H,12-13H2,1-6H3/b9-7+,11-10+,15-8+,16-14+

Standard InChI Key:  RLAYPMFOLMBAIN-XPSLGPGOSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
  -12.7482    2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0337    2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0337    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7482    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4627    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4627    2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3316    4.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1649    4.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7482    1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3193    2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3193    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6048    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8903    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1759    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8903    5.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4614    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7469    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0324    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3180    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8890    3.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    5.0089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0324    5.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1746    4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  4  7  1  0
  4  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1908017

   4-Hydroxyretinoic Acid Methylester

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: 330.47

Molecular Weight (Monoisotopic): 330.2195

AlogP: 4.66

#Rotatable Bonds: 5

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.45

Np Likeness Score: 2.48

References

1. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

Source

Source(1):

• Scientific Literature