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(1R,4aS,10aR)-6-hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

ID: ALA523920

PubChem CID: 13370050

Max Phase: Preclinical

Molecular Formula: C20H28O3

Molecular Weight: 316.44

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Synonyms: 12-Hydroxydehydroabietic Acid | 12-Hydroxydehydroabietic Acid|CHEMBL523920

Canonical SMILES:  CC(C)c1cc2c(cc1O)[C@@]1(C)CCC[C@@](C)(C(=O)O)[C@@H]1CC2

Standard InChI:  InChI=1S/C20H28O3/c1-12(2)14-10-13-6-7-17-19(3,15(13)11-16(14)21)8-5-9-20(17,4)18(22)23/h10-12,17,21H,5-9H2,1-4H3,(H,22,23)/t17-,19-,20-/m1/s1

Standard InChI Key:  AYDJDNNMKHXZOQ-MISYRCLQSA-N

Molfile:  

     RDKit          2D

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   13.5284  -23.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5284  -24.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2421  -24.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2421  -23.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9603  -23.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9568  -24.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6687  -24.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3887  -24.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6757  -23.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3891  -23.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1062  -23.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1111  -22.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3930  -21.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6788  -22.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9522  -22.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6455  -25.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9522  -25.1066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8215  -25.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9974  -25.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8264  -21.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5384  -22.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8298  -20.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2253  -26.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3945  -20.9873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  1  2  1  0
 12 13  1  0
  1  4  1  0
 13 14  2  0
 14  9  1  0
  2  3  1  0
  5 15  1  1
  5  9  1  0
  3 16  1  1
  6  7  1  0
  6 17  1  6
  7  8  1  0
  3 18  1  0
  8 10  1  0
 18 19  1  0
  3  6  1  0
 12 20  1  0
  5  4  1  0
 20 21  1  0
  9 10  2  0
 20 22  1  0
  5  6  1  0
 18 23  2  0
 10 11  1  0
 13 24  1  0
M  END

Alternative Forms

Associated Targets(Human)

Raji (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNMA1 Tclin Calcium-activated potassium channel subunit alpha-1 (435 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LoVo (4724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRA1 Tclin GABA-A receptor; alpha-1/beta-2/gamma-2 (1171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
J774 (3120 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania amazonensis (3813 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania guyanensis (94 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania donovani (89745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania infantum (5912 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
Human alphaherpesvirus 1 (11089 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chikungunya virus (1339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Zika virus (1028 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

Calculated Properties

Molecular Weight: 316.44Molecular Weight (Monoisotopic): 316.2038AlogP: 4.61#Rotatable Bonds: 2
Polar Surface Area: 57.53Molecular Species: ACIDHBA: 2HBD: 2
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 4.30CX Basic pKa: CX LogP: 5.45CX LogD: 2.48
Aromatic Rings: 1Heavy Atoms: 23QED Weighted: 0.84Np Likeness Score: 2.33

References

1. Cui YM, Yasutomi E, Otani Y, Yoshinaga T, Ido K, Sawada K, Ohwada T..  (2008)  Novel BK channel openers containing dehydroabietic acid skeleton: structure-activity relationship for peripheral substituents on ring C.,  18  (19): [PMID:18789860] [10.1016/j.bmcl.2008.08.078]
2. Kinouchi Y, Ohtsu H, Tokuda H, Nishino H, Matsunaga S, Tanaka R..  (2000)  Potential antitumor-promoting diterpenoids from the stem bark of Picea glehni.,  63  (6): [PMID:10869208] [10.1021/np0000217]
3. Wada S, Yasui Y, Tokuda H, Tanaka R..  (2009)  Anti-tumor-initiating effects of phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis.,  17  (17): [PMID:19646881] [10.1016/j.bmc.2009.07.016]
4. Yang XW, Feng L, Li SM, Liu XH, Li YL, Wu L, Shen YH, Tian JM, Zhang X, Liu XR, Wang N, Liu Y, Zhang WD..  (2010)  Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr.,  18  (2): [PMID:20022253] [10.1016/j.bmc.2009.11.055]
5. Hamulić D, Stadler M, Hering S, Padrón JM, Padrón JM, Bassett R, Rivas F, Loza-Mejía MA, Dea-Ayuela MA, González-Cardenete MA..  (2019)  Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies.,  82  (4): [PMID:30840453] [10.1021/acs.jnatprod.8b00884]
6. 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