(7S,16R,17S)-7,16,17-trihydroxydocosa-4,8,10,12,14-pentaenoic acid

ID: ALA4752691

PubChem CID: 162653412

Max Phase: Preclinical

Molecular Formula: C22H34O5

Molecular Weight: 378.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)C/C=C\CCC(=O)O

Standard InChI:  InChI=1S/C22H34O5/c1-2-3-9-16-20(24)21(25)17-12-7-5-4-6-10-14-19(23)15-11-8-13-18-22(26)27/h4-8,10-12,14,17,19-21,23-25H,2-3,9,13,15-16,18H2,1H3,(H,26,27)/b6-4-,7-5+,11-8-,14-10+,17-12+/t19-,20+,21-/m1/s1

Standard InChI Key:  NHEQLDHOIDACCJ-YPOUZGMCSA-N

Molfile:  

 
     RDKit          2D

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   14.1027   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8104   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1027   -5.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8104   -5.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5182   -5.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5182   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8104   -3.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1027   -2.8519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5182   -2.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5182   -2.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2259   -1.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9336   -2.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6413   -1.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3490   -2.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3490   -2.8519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0567   -1.6261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2259   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9336   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6413   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3490   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6413   -3.2605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3490   -5.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0567   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7644   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4721   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4721   -3.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1798   -2.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  2  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  1
 20 22  1  6
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4752691

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.51

Molecular Weight (Monoisotopic): 378.2406

AlogP: 3.69

#Rotatable Bonds: 15

Polar Surface Area: 97.99

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.64

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: 0.89

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.20

Np Likeness Score: 2.07

References

1. Schoeder CT,Mahardhika AB,Drabczyńska A,Kieć-Kononowicz K,Müller CE.  (2020)  Discovery of Tricyclic Xanthines as Agonists of the Cannabinoid-Activated Orphan G-Protein-Coupled Receptor GPR18.,  11  (10): [PMID:33062188] [10.1021/acsmedchemlett.0c00208]

Source

Source(1):

• Scientific Literature