15-deoxypulic acid

ID: ALA4241124

PubChem CID: 38362201

Max Phase: Preclinical

Molecular Formula: C20H26O4

Molecular Weight: 330.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H](C)[C@@](C)(CCC2=CCOC2=O)C/C=C\C=C/1C(=O)O

Standard InChI:  InChI=1S/C20H26O4/c1-14-7-8-15(2)20(3,11-5-4-6-17(14)18(21)22)12-9-16-10-13-24-19(16)23/h4-6,10,15H,1,7-9,11-13H2,2-3H3,(H,21,22)/b5-4-,17-6+/t15-,20+/m0/s1

Standard InChI Key:  ONFWNHLCKGVKGW-PTVUHMQHSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   39.8594   -6.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8582   -7.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5663   -7.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5645   -5.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2731   -6.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2719   -7.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9781   -7.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6900   -7.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6912   -6.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9804   -5.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5679   -8.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8611   -8.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.2765   -8.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.9805   -5.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6882   -4.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6882   -3.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6838   -5.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3999   -5.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3507   -3.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0981   -2.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2809   -2.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.0285   -3.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2515   -3.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.9739   -6.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 11 13  2  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 10 17  1  1
  9 18  1  1
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 16  1  0
 22 23  2  0
  6 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4241124

   (1E,3Z,6S,7S)-6,7-dimethyl-10-methylidene-6-[2-(5-oxo-2H-furan-4-yl)ethyl]cyclodeca-1,3-diene-1-carboxylic acid

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: 330.42

Molecular Weight (Monoisotopic): 330.1831

AlogP: 4.20

#Rotatable Bonds: 4

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.63

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 1.74

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 2.66

References

1. Qiao Y, Zheng H, Li L, Zhang J, Li Y, Li S, Zhu R, Zhou J, Zhao S, Jiang Y, Lou H..  (2018)  Terpenoids with vasorelaxant effects from the Chinese liverwort Scapania carinthiaca.,  26  (14): [PMID:30049584] [10.1016/j.bmc.2018.07.035]

Source

Source(1):

• Scientific Literature