8,8a-Dihydro-8-hydroxygambogenic acid;(-)-8,8a-Dihydro-8-hydroxygambogenic acid



Compound IDCDAMM02450
Common name8,8a-Dihydro-8-hydroxygambogenic acid;(-)-8,8a-Dihydro-8-hydroxygambogenic acid
IUPAC name4-[7-(3,7-dimethylocta-2,6-dienyl)-6,8,12-trihydroxy-17,17-dimethyl-5-(3-methylbut-2-enyl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8-trien-15-yl]-2-methylbut-2-enoic acid
Molecular formulaC38H48O9

Experimental data

Retention time4.86
Adduct[M+K]+
Actual mz687.293
Theoretical mz687.293
Error0.35
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.9301

Identifiers and class information

Inchi keyQYRPARUSUFWOPG-VPJKZDJZNA-N
SmilesO=C(O)C(=CCC12OC(C)(C)C3CC(C1=O)C(O)C4C(=O)C=5C(O)=C(C(O)=C(C5OC432)CC=C(C)C)CC=C(C)CCC=C(C)C)C
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

Pharmacokinetic properties

Number of descriptor values(#stars)5
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)1
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)13
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)648.792
Computed dipole moment(dipole)12.579
Total solvent accessible surface area (SASA)988.422
Hydrophobic component of SASA (FOSA)719.818
Hydrophilic component of SASA (FISA)224.515
Pie component of the SASA (PISA)44.089
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1958.55
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)8.7
Free energy of solvation of dipole (dip^2/V)0.0807923
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0124478
Globularity descriptor (glob)0.765913
Predicted polarizability in cubic angstroms (QPpolrz)64.301
Predicted hexadecane/gas partition coefficient (QPlogPC16)18.82
Predicted octanol/gas partition coefficient (QPlogPoct)30.283
Predicted water/gas partition coefficient (QPlogPw)12.556
Predicted octanol/water partition coefficient (QPlogPo/w)6.802
Predicted aqueous solubility (QPlogS)-8.717
Conformation-independent predicted aqueous solubility (CIQPlogS)-9.43
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.723
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)18.639
Predicted brain/blood partition coefficient (QPlogBB)-2.772
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)8.498
Predicted skin permeability, log Kp (QPlogKp)-4.254
PM3 calculated ionization potential (IP(ev))9.339
PM3 calculated electron affinity (EA(eV))0.696
Number of likely metabolic reactions (#metab)17
Prediction of binding to human serum albumin (QPlogKhsa)1.434
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)63.592
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
Van der Waals surface area (PSA)158.125
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)2
Number of violations of Jorgensen’s rule of three (RuleOfThree)3

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P11926ODC1Ornithine decarboxylaseT60366SEA
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
P10599TXNThioredoxinT85616SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
T85616DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P10599TXN

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