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COCONUT Compound

7alpha-hydroxydehydroabieticacid

CNP0121998.3 · C20H28O3 · View on COCONUT ↗

2D Structure

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Identifiers

Name7alpha-hydroxydehydroabieticacid
IUPAC Name(1~{R},4~{a}~{S},9~{R},10~{a}~{R})-9-hydroxy-7-isopropyl-1,4~{a}-dimethyl-2,3,4,9,10,10~{a}-hexahydrophenanthrene-1-carboxylic acid
COCONUT IDCNP0121998.3
InChIKeyGPFVBJYXFRIOFB-HNBVOPMISA-N
InChIInChI=1S/C20H28O3/c1-12(2)13-6-7-15-14(10-13)16(21)11-17-19(15,3)8-5-9-20(17,4)18(22)23/h6-7,10,12,16-17,21H,5,8-9,11H2,1-4H3,(H,22,23)/t16-,17-,19-,20-/m1/s1
SMILESCC(C)C1=CC=C2C(=C1)[C@H](O)C[C@H]1[C@](C)(C(=O)O)CCC[C@]21C

Properties

Molecular FormulaC20H28O3
Molecular Weight316.44
Exact Mass316.20384
Log P (ALogP)4.40
TPSA57.53
H-Bond Donors / Acceptors2 / 2
Rotatable Bonds2
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.85
NP-likeness2.17

Classification

NP PathwayTerpenoids
NP SuperclassDiterpenoids
NP ClassPodocarpane diterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassDiterpenoids

Reported in GR-MAPs Plants

Callicarpa macrophylla as “Callicarpa macrophylla” in COCONUT

References (6)

  1. 10.1016/J.PHYTOCHEM.2010.06.008
  2. 10.1016/S0031-9422(97)84396-8
  3. 10.1016/j.bmc.2009.11.055
  4. 10.1021/ACS.JNATPROD.5B00018
  5. 10.1021/acs.jnatprod.5b00018
  6. 10.1021/acs.jnatprod.5b01053

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.