(+-)-Demethylgrossamide



Compound IDCDAMM02274
Common name(+-)-Demethylgrossamide
IUPAC name2-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[3-[2-(4-hydroxyphenyl)ethylamino]-3-oxoprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide
Molecular formulaC35H34N2O8

Experimental data

Retention time15.46
Adduct[M+H]+
Actual mz611.239
Theoretical mz611.239
Error1.11
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.5389

Identifiers and class information

Inchi keyYBUBLAJQIDHBCG-UJISWJIUNA-N
SmilesO=C(C=CC=1C=C(OC)C=2OC(C3=CC=C(O)C(O)=C3)C(C(=O)NCCC4=CC=C(O)C=C4)C2C1)NCCC5=CC=C(O)C=C5
SuperclassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)8
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)1
Number of rotatable bonds (#rotor)15
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)610.662
Computed dipole moment(dipole)8.286
Total solvent accessible surface area (SASA)1044.36
Hydrophobic component of SASA (FOSA)265.669
Hydrophilic component of SASA (FISA)297.315
Pie component of the SASA (PISA)481.372
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1891.23
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)9.5
Free energy of solvation of dipole (dip^2/V)0.0363072
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0222818
Globularity descriptor (glob)0.708185
Predicted polarizability in cubic angstroms (QPpolrz)64.499
Predicted hexadecane/gas partition coefficient (QPlogPC16)23.587
Predicted octanol/gas partition coefficient (QPlogPoct)36.571
Predicted water/gas partition coefficient (QPlogPw)24.061
Predicted octanol/water partition coefficient (QPlogPo/w)4.076
Predicted aqueous solubility (QPlogS)-7.651
Conformation-independent predicted aqueous solubility (CIQPlogS)-8.181
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.175
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)9.864
Predicted brain/blood partition coefficient (QPlogBB)-4.293
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)5.288
Predicted skin permeability, log Kp (QPlogKp)-3.863
PM3 calculated ionization potential (IP(ev))8.776
PM3 calculated electron affinity (EA(eV))0.644
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)0.466
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)42.688
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)22.914
Van der Waals surface area (PSA)180.55
Number of nitrogen and oxygen atoms (#NandO)10
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
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
Q8NER1TRPV1Vanilloid receptorT83193SEA
P06276BCHEButyrylcholinesteraseT99799SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
P11388TOP2ADNA topoisomerase II alphaT17048SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P08581METHepatocyte growth factor receptorT40474SEA
P35408PTGER4Prostanoid EP4 receptorT18876SEA
P34995PTGER1Prostanoid EP1 receptorT15497SEA
Q13258PTGDRProstanoid DP receptorT68782SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9NZQ8TRPM5Long transient receptor potential channel 5T85545SEA
P35270SPRSubstance-P receptorT47094SEA
Q8N183NDUFAF2HUMAN NADH:ubiquinone oxidoreductase complex assembly factor 2T01453SEA
Q9P0J0NDUFA13Mitochondrial complex IT82391SEA
Q9Y6M9NDUFB9HUMAN NADH:ubiquinone oxidoreductase subunit B9T01465SEA
Q8N183NDUFAF2HUMAN NADH:ubiquinone oxidoreductase complex assembly factor 2T01453SEA
P03897MT-ND3NADH dehydrogenaseT77195SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T38529DI0003Abortion[ICD-11: JA00]P43116PTGER2
T38529DI0102Coronary atherosclerosis[ICD-11: BA52]P43116PTGER2
T38529DI0121Diabetic foot ulcer[ICD-11: BD54]P43116PTGER2
T38529DI0166Glaucoma[ICD-11: 9C61]P43116PTGER2
T38529DI0356Pulmonary hypertension[ICD-11: BB01]P43116PTGER2
T38529DI0378Sexual dysfunction[ICD-11: HA00-HA01]P43116PTGER2
T38529DI0413Transplant rejection[ICD-11: NE84]P43116PTGER2
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
T18876DI0037Asthma[ICD-11: CA23]P35408PTGER4
T18876DI0175Heart failure[ICD-11: BD10-BD1Z]P35408PTGER4
T18876DI0264Migraine[ICD-11: 8A80]P35408PTGER4
T18876DI0303Non-small-cell lung cancer[ICD-11: 2C25]P35408PTGER4
T18876DI0324Pain[ICD-11: MG30-MG3Z]P35408PTGER4
T18876DI0360Rectum cancer[ICD-11: 2B92]P35408PTGER4
T18876DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35408PTGER4
T18876DI0414Transplanted organ/tissue[ICD-11: QB63]P35408PTGER4
T15497DI0405Thrombosis[ICD-11: DB61-GB90]P34995PTGER1
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
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
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
T82391DI0069Cardiomyopathy[ICD-11: BC43]Q9P0J0NDUFA13
T77195DI0331Parkinsonism[ICD-11: 8A00]P03897MT-ND3

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