Abieta-8,11,13-trien-14,18-diol

ID: ALA3134056

PubChem CID: 76336622

Max Phase: Preclinical

Molecular Formula: C20H30O2

Molecular Weight: 302.46

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(18(14)22)7-9-17-19(3,12-21)10-5-11-20(16,17)4/h6,8,13,17,21-22H,5,7,9-12H2,1-4H3/t17-,19-,20+/m0/s1

Standard InChI Key:  ZGQGBEGMJCXLOB-YSIASYRMSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   18.4883   -6.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0766   -7.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9016   -7.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7763   -5.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7763   -5.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4883   -4.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2004   -5.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1969   -5.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9057   -6.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6225   -5.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9127   -4.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6217   -5.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3361   -4.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3425   -3.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6287   -3.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9173   -3.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0473   -5.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0595   -3.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7715   -3.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0644   -2.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1930   -4.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1889   -6.7254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4899   -7.7420    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  1  0
M  END

Associated Targets(Human)

HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Jurkat (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus niger (16508 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus terreus (892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus fumigatus (16427 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus flavus (8875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human alphaherpesvirus 1 (11089 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero C1008 (1716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BHK-21 (725 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Zika virus (1028 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chikungunya virus (1339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
dengue virus type 2 (2400 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 302.46Molecular Weight (Monoisotopic): 302.2246AlogP: 4.52#Rotatable Bonds: 2
Polar Surface Area: 40.46Molecular Species: NEUTRALHBA: 2HBD: 2
#RO5 Violations: HBA (Lipinski): 2HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 10.79CX Basic pKa: CX LogP: 4.97CX LogD: 4.97
Aromatic Rings: 1Heavy Atoms: 22QED Weighted: 0.84Np Likeness Score: 2.33

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,  (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