3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid



Compound IDCDAMM01404
Common name3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
IUPAC name3-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaenyl)-4-hydroxy-5-methoxybenzoic acid
Molecular formulaC38H56O4

Experimental data

Retention time15.21
Adduct[M+Na]+
Actual mz599.414
Theoretical mz599.407
Error11.98
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.5347

Identifiers and class information

Inchi keyYSZSVGFMAJXGMQ-FRICUITQSA-N
SmilesO=C(O)C1=CC(OC)=C(O)C(=C1)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)6
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)20
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)576.858
Computed dipole moment(dipole)4.724
Total solvent accessible surface area (SASA)972.845
Hydrophobic component of SASA (FOSA)816.643
Hydrophilic component of SASA (FISA)85.238
Pie component of the SASA (PISA)70.964
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1959.55
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)3.5
Free energy of solvation of dipole (dip^2/V)0.011388
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0050879
Globularity descriptor (glob)0.77844
Predicted polarizability in cubic angstroms (QPpolrz)60.103
Predicted hexadecane/gas partition coefficient (QPlogPC16)17.884
Predicted octanol/gas partition coefficient (QPlogPoct)24.252
Predicted water/gas partition coefficient (QPlogPw)5.088
Predicted octanol/water partition coefficient (QPlogPo/w)10.009
Predicted aqueous solubility (QPlogS)-9.269
Conformation-independent predicted aqueous solubility (CIQPlogS)-9.858
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.648
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)390.111
Predicted brain/blood partition coefficient (QPlogBB)-1.58
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)227.463
Predicted skin permeability, log Kp (QPlogKp)-0.92
PM3 calculated ionization potential (IP(ev))9.157
PM3 calculated electron affinity (EA(eV))0.469
Number of likely metabolic reactions (#metab)20
Prediction of binding to human serum albumin (QPlogKhsa)2.211
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
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)72.931
Number of nitrogen and oxygen atoms (#NandO)4
Number of violations of Lipinski’s rule of five (RuleOfFive)2
Number of violations of Jorgensen’s rule of three (RuleOfThree)2

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P23280CA6Carbonic anhydrase VIT06569SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
O14684PTGESProstaglandin E synthaseT02562SEA
P29350PTPN6Protein-tyrosine phosphatase 1CT98264SEA
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
Q14534SQLESqualene monooxygenase (by homology)T93344SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P49356FNTBFarnesyl protein transferaseT13127SEA
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
P49356FNTBFarnesyl protein transferaseT13127SEA
O95749GGPS1GeranyltranstransferaseT86528SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T86528DI0057Bone paget disease[ICD-11: FB85]O95749GGPS1
T86528DI0237Low bone mass disorder[ICD-11: FB83]O95749GGPS1
T86528DI0267Mineral excesses[ICD-11: 5B91]O95749GGPS1
T86528DI0281Musculoskeletal disorder[ICD-11: FA00-FC0Z]O95749GGPS1

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