Indole-3-acrylic acid



Compound IDCDAMM00051
Common nameIndole-3-acrylic acid
IUPAC name(E)-3-(1H-indol-3-yl)prop-2-enoic acid
Molecular formulaC11H9NO2

Experimental data

Retention time24.61
Adduct[M+H]+
Actual mz188.071
Theoretical mz188.071
Error2.65
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.4127

Identifiers and class information

Inchi keyPLVPPLCLBIEYEA-WAYWQWQTSA-N
SmilesC1=CC=C2C(=C1)C(=CN2)C=CC(=O)O
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)3
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)187.198
Computed dipole moment(dipole)7.772
Total solvent accessible surface area (SASA)405.602
Hydrophobic component of SASA (FOSA)20.038
Hydrophilic component of SASA (FISA)143.37
Pie component of the SASA (PISA)242.194
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)648.418
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)2
Free energy of solvation of dipole (dip^2/V)0.0931463
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0069734
Globularity descriptor (glob)0.893241
Predicted polarizability in cubic angstroms (QPpolrz)20.182
Predicted hexadecane/gas partition coefficient (QPlogPC16)7.395
Predicted octanol/gas partition coefficient (QPlogPoct)11.708
Predicted water/gas partition coefficient (QPlogPw)7.555
Predicted octanol/water partition coefficient (QPlogPo/w)2.068
Predicted aqueous solubility (QPlogS)-2.262
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.619
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.607
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)109.629
Predicted brain/blood partition coefficient (QPlogBB)-0.815
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)57.685
Predicted skin permeability, log Kp (QPlogKp)-3.021
PM3 calculated ionization potential (IP(ev))8.487
PM3 calculated electron affinity (EA(eV))0.647
Number of likely metabolic reactions (#metab)0
Prediction of binding to human serum albumin (QPlogKhsa)-0.39
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)75.565
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)65.625
Number of nitrogen and oxygen atoms (#NandO)3
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
P23280CA6Carbonic anhydrase VIT06569SEA
Q96RJ0TAAR1Trace amine-associated receptor 1 (by homology)T99524SEA
P28566HTR1ESerotonin 1e (5-HT1e) receptorT84117SEA
P11509CYP2A6Cytochrome P450 2A6T06455SEA
Q9UQL6HDAC5Histone deacetylase 5T07930SEA
Q8WUI4HDAC7Histone deacetylase 7T98698SEA
Q9UKV0HDAC9Histone deacetylase 9T03687SEA
Q92769HDAC2Histone deacetylase 2T51191SEA
P23141CES1Acyl coenzyme A:cholesterol acyltransferaseT76369SEA
P08253MMP2Matrix metalloproteinase 2T68251SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03372ESR1Estrogen receptor alphaT02506SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P35270SPRSubstance-P receptorT47094SEA
P07711CTSLCathepsin LT98691SEA
P32245MC4RMelanocortin receptor 4T72458SEA
P07858CTSBCathepsin (B and K)T61746SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
P13500CCL2C-C motif chemokine 2T89988SEA
P35408PTGER4Prostanoid EP4 receptorT18876SEA
P43115PTGER3Prostanoid EP3 receptorT85467SEA
P42892ECE1Endothelin-converting enzyme 1T50970SEA
P30872SSTR1Somatostatin receptor 1T16633SEA
P32745SSTR3Somatostatin receptor 3T13644SEA
P26010ITGB7Integrin alpha-4/beta-7T07403SEA
P13569CFTRCystic fibrosis transmembrane conductance regulatorT55654SEA
P19525EIF2AK2Interferon-induced, double-stranded RNA-activated protein kinaseT04831SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
P28336NMBRNeuromedin B receptorT68887SEA
Q96DB2HDAC11Histone deacetylase 11T97903SEA
P33032MC5RMelanocortin receptor 5T95302SEA
P28336NMBRNeuromedin B receptorT68887SEA
Q969S8HDAC10Histone deacetylase 10T94324SEA
P48775TDO2Tryptophan 2,3-dioxygenaseT44818SEA
Q9NQS5GPR84G-protein coupled receptor 84T98091SEA
Q12882DPYDDihydropyrimidine dehydrogenaseT75890SEA
Q06609RAD51DNA repair protein RAD51 homolog 1T63083SEA
P47870GABRB2GABA(A) receptor beta-2T80387SEA
Q96RG2PASKPAS domain-containing serine/threonine-protein kinaseT37371SEA
Q9NZ70TAK1TGF-beta-activated kinase 1T04361SEA

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
T99524DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q96RJ0TAAR1
T99524DI0149Focal/segmental autonomic disorder[ICD-11: 8D8A]Q96RJ0TAAR1
T99524DI0290Narcolepsy[ICD-11: 7A20]Q96RJ0TAAR1
T84117DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28566HTR1E
T06455DI0283Mycosis fungoides[ICD-11: 2B01]P11509CYP2A6
T06455DI0351Psoriasis[ICD-11: EA90]P11509CYP2A6
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
T76369DI0335Peroxisomal disease[ICD-11: 5C57]P23141CES1
T76369DI0398Synthesis disorder[ICD-11: 5C52-5C59]P23141CES1
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
T61746DI0023Alopecia[ICD-11: ED70]P07858CTSB
T61746DI0025Alzheimer disease[ICD-11: 8A20]P07858CTSB
T61746DI0037Asthma[ICD-11: CA23]P07858CTSB
T61746DI0055Bone cancer[ICD-11: 2B5Z]P07858CTSB
T61746DI0060Brain cancer[ICD-11: 2A00]P07858CTSB
T61746DI0067Cardiac arrest[ICD-11: MC82]P07858CTSB
T61746DI0074Cerebral ischaemic stroke[ICD-11: 8B11]P07858CTSB
T61746DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P07858CTSB
T61746DI0087Chronic pain[ICD-11: MG30]P07858CTSB
T61746DI0110Cystic fibrosis[ICD-11: CA25]P07858CTSB
T61746DI0124Digestive system disease[ICD-11: DE2Z]P07858CTSB
T61746DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P07858CTSB
T61746DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P07858CTSB
T61746DI0253Meningioma[ICD-11: 2A01]P07858CTSB
T61746DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P07858CTSB
T61746DI0275Multiple sclerosis[ICD-11: 8A40]P07858CTSB
T61746DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]P07858CTSB
T61746DI0320Osteoarthritis[ICD-11: FA00-FA05]P07858CTSB
T61746DI0351Psoriasis[ICD-11: EA90]P07858CTSB
T61746DI0366Rheumatoid arthritis[ICD-11: FA20]P07858CTSB
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
T89988DI0083Chronic kidney disease[ICD-11: GB61]P13500CCL2
T89988DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P13500CCL2
T89988DI0087Chronic pain[ICD-11: MG30]P13500CCL2
T89988DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P13500CCL2
T89988DI0252Melanoma[ICD-11: 2C30]P13500CCL2
T89988DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P13500CCL2
T89988DI0275Multiple sclerosis[ICD-11: 8A40]P13500CCL2
T89988DI0326Pancreatic cancer[ICD-11: 2C10]P13500CCL2
T89988DI0366Rheumatoid arthritis[ICD-11: FA20]P13500CCL2
T89988DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P13500CCL2
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
T85467DI0166Glaucoma[ICD-11: 9C61]P43115PTGER3
T85467DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P43115PTGER3
T85467DI0414Transplanted organ/tissue[ICD-11: QB63]P43115PTGER3
T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
T13644DI0108Cushing syndrome[ICD-11: 5A70]P32745SSTR3
T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
T55654DI0110Cystic fibrosis[ICD-11: CA25]P13569CFTR
T55654DI0217Intrathoracic organs injury[ICD-11: NB32]P13569CFTR
T55654DI0435Viral intestinal infection[ICD-11: 1A2Z]P13569CFTR
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T95302DI0005Acne vulgaris[ICD-11: ED80]P33032MC5R
T95302DI0371Sebaceous gland disorder[ICD-11: ED91]P33032MC5R
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T94324DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q969S8HDAC10
T44818DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P48775TDO2
T98091DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q9NQS5GPR84
T98091DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NQS5GPR84
T75890DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q12882DPYD
T63083DI0048B-cell lymphoma[ICD-11: 2A86]Q06609RAD51
T63083DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q06609RAD51
T80387DI0117Depression[ICD-11: 6A70-6A7Z]P47870GABRB2
T80387DI0214Insomnia[ICD-11: 7A00-7A0Z]P47870GABRB2
T80387DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P47870GABRB2
T80387DI0411Tonus and reflex abnormality[ICD-11: MB47]P47870GABRB2
T04361DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9NZ70TAK1

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