methyl 4-O-coumaroylquinate



Compound IDCDAMM02708
Common namemethyl 4-O-coumaroylquinate
IUPAC namemethyl 1,3,5-trihydroxy-4-[3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohexane-1-carboxylate
Molecular formulaC17H20O8

Experimental data

Retention time17.4
Adduct[M+H]+
Actual mz353.121
Theoretical mz353.123
Error6.16
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.907

Identifiers and class information

Inchi keyHDSDPFJFNJWIDZ-RAQIVURDNA-N
SmilesO=C(OC1C(O)CC(O)(C(=O)OC)CC1O)C=CC2=CC=C(O)C=C2
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)0
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)9
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)352.34
Computed dipole moment(dipole)5.276
Total solvent accessible surface area (SASA)637.922
Hydrophobic component of SASA (FOSA)219.381
Hydrophilic component of SASA (FISA)235.078
Pie component of the SASA (PISA)183.463
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1104.06
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)8.9
Free energy of solvation of dipole (dip^2/V)0.0252144
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0279031
Globularity descriptor (glob)0.809825
Predicted polarizability in cubic angstroms (QPpolrz)34.004
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.309
Predicted octanol/gas partition coefficient (QPlogPoct)22.238
Predicted water/gas partition coefficient (QPlogPw)16.741
Predicted octanol/water partition coefficient (QPlogPo/w)0.79
Predicted aqueous solubility (QPlogS)-3.363
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.173
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.484
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)58.432
Predicted brain/blood partition coefficient (QPlogBB)-2.369
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)22.974
Predicted skin permeability, log Kp (QPlogKp)-4.342
PM3 calculated ionization potential (IP(ev))9.225
PM3 calculated electron affinity (EA(eV))0.906
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)-0.469
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)63.189
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)148.49
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P27338MAOBMonoamine oxidase BT83011SEA
P15121AKR1B1Aldose reductaseT26623SEA
Q92769HDAC2Histone deacetylase 2T51191SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P03372ESR1Estrogen receptor alphaT02506SEA
P13726F3Coagulation factor VII/tissue factorT72702SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P56817BACE1Beta-secretase 1T79031SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P11388TOP2ADNA topoisomerase II alphaT17048SEA
Q9NR96TLR9Toll-like receptor (TLR7/TLR9)T11451SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
P32249EBI2EBV-induced G-protein coupled receptor 2T59577SEA
P01100FOSProto-oncogene c-FosT28025SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T11451DI0095Colorectal cancer[ICD-11: 2B91]Q9NR96TLR9
T11451DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]Q9NR96TLR9
T11451DI0252Melanoma[ICD-11: 2C30]Q9NR96TLR9
T11451DI0346Prostate cancer[ICD-11: 2C82]Q9NR96TLR9
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2

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