Methyl 14-hydroxyabieta-8,11,13-trien-18-oate

ID: ALA3134060

PubChem CID: 24764296

Max Phase: Preclinical

Molecular Formula: C21H30O3

Molecular Weight: 330.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]1(C)CCC[C@]2(C)c3ccc(C(C)C)c(O)c3CC[C@@H]12

Standard InChI:  InChI=1S/C21H30O3/c1-13(2)14-7-9-16-15(18(14)22)8-10-17-20(16,3)11-6-12-21(17,4)19(23)24-5/h7,9,13,17,22H,6,8,10-12H2,1-5H3/t17-,20-,21-/m1/s1

Standard InChI Key:  YDAATSHQUAMAPZ-DUXKGJEZSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    3.2456   -5.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -5.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5970   -5.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336   -3.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336   -4.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2456   -3.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9577   -3.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -4.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631   -5.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799   -4.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6700   -3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3791   -3.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0934   -3.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0999   -2.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3861   -2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6747   -2.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047   -3.8319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8169   -2.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5290   -2.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8218   -1.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -2.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9462   -5.4589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1261   -6.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191   -5.8622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7705   -6.6088    0.0000 C   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
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3134060

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

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: 4.70

#Rotatable Bonds: 2

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: 10.22

CX Basic pKa: ┄

CX LogP: 5.59

CX LogD: 5.59

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: 2.14

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. Xu H, Liu L, Fan X, Zhang G, Li Y, Jiang B..  (2017)  Identification of a diverse synthetic abietane diterpenoid library for anticancer activity.,  27  (3): [PMID:28011223] [10.1016/j.bmcl.2016.12.032]

3. Hou W, Zhang G, Luo Z, Li D, Ruan H, Ruan BH, Su L, Xu H..  (2017)  Identification of a diverse synthetic abietane diterpenoid library and insight into the structure-activity relationships for antibacterial activity.,  27  (24): [PMID:29153424] [10.1016/j.bmcl.2017.11.014]

4. Martín-Escolano R,Guardia JJ,Martín-Escolano J,Cirauqui N,Fernández A,Rosales MJ,Chahboun R,Sánchez-Moreno M,Alvarez-Manzaneda E,Marín C.  (2020)  In Vivo Biological Evaluation of a Synthetic Royleanone Derivative as a Promising Fast-Acting Trypanocidal Agent by Inducing Mitochondrial-Dependent Necrosis.,  83  (12): [PMID:33253573] [10.1021/acs.jnatprod.0c00651]

5. 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