14-Hydroxyabieta-8,11,13-trien-18-oic acid

ID: ALA3134055

PubChem CID: 76329368

Max Phase: Preclinical

Molecular Formula: C20H28O3

Molecular Weight: 316.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc2c(c1O)CC[C@H]1[C@](C)(C(=O)O)CCC[C@]21C

Standard InChI:  InChI=1S/C20H28O3/c1-12(2)13-6-8-15-14(17(13)21)7-9-16-19(15,3)10-5-11-20(16,4)18(22)23/h6,8,12,16,21H,5,7,9-11H2,1-4H3,(H,22,23)/t16-,19-,20-/m1/s1

Standard InChI Key:  CXTCAUAJYKHFNC-NSISKUIASA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   11.2091   -4.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7973   -5.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5604   -5.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4970   -3.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4970   -4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2091   -3.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9211   -3.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9177   -4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6265   -4.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3435   -4.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6336   -3.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3427   -3.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0569   -3.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0634   -2.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3495   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6382   -2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7682   -3.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7803   -1.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4924   -2.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7853   -1.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9138   -2.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9096   -5.1131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0895   -6.1249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3826   -5.5164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  1  3  1  0
  4  5  1  0
  4  6  1  0
  5  1  1  0
  1  8  1  0
  7  6  1  0
  7  8  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 13 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
  7 21  1  1
  8 22  1  6
  3 23  2  0
  3 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3134055

   (1R,4aS,10aR)-8-hydroxy-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic 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: 316.44

Molecular Weight (Monoisotopic): 316.2038

AlogP: 4.61

#Rotatable Bonds: 2

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.31

CX Basic pKa: ┄

CX LogP: 5.45

CX LogD: 2.49

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: 2.25

References

1. Zapata B, Rojas M, Betancur-Galvis L, Mesa-Arango AC, Perez-Guaita D, Gonzalez MA.  (2013)  Cytotoxic, immunomodulatory, antimycotic, and antiviral activities of semisynthetic 14-hydroxyabietane derivatives and triptoquinone C-4 epimers,  4  (9): [10.1039/C3MD00151B]

2. González-Cardenete MA, Hamulić D, Miquel-Leal FJ, González-Zapata N, Jimenez-Jarava OJ, Brand YM, Restrepo-Mendez LC, Martinez-Gutierrez M, Betancur-Galvis LA, Marín ML..  (2022)  Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids.,  85  (8.0): [PMID:35969814] [10.1021/acs.jnatprod.2c00464]

Source

Source(1):

• Scientific Literature