Chrotacumine A



Compound IDCDAMM01224
Common nameChrotacumine A
IUPAC name(9-hydroxy-5,14-dimethyl-7-oxo-4,12-dioxa-14-azatetracyclo[11.3.1.02,11.03,8]heptadeca-2(11),3(8),5,9-tetraen-16-yl) benzoate
Molecular formulaC23H21NO6

Experimental data

Retention time0.44
Adduct[M+H]+
Actual mz408.139
Theoretical mz408.144
Error13.17
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8502

Identifiers and class information

Inchi keyPJWARXSHHFSDKD-RWKILVNUNA-N
SmilesO=C(OC1CN(C)C2OC3=CC(O)=C4C(=O)C=C(OC4=C3C1C2)C)C=5C=CC=CC5
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)1
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)3
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)1
Molecular weight (mol_MW)407.422
Computed dipole moment(dipole)8.132
Total solvent accessible surface area (SASA)662.514
Hydrophobic component of SASA (FOSA)261.916
Hydrophilic component of SASA (FISA)114.378
Pie component of the SASA (PISA)286.22
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1215.19
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)7
Free energy of solvation of dipole (dip^2/V)0.0544187
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.831254
Predicted polarizability in cubic angstroms (QPpolrz)43.285
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.329
Predicted octanol/gas partition coefficient (QPlogPoct)18.932
Predicted water/gas partition coefficient (QPlogPw)10.272
Predicted octanol/water partition coefficient (QPlogPo/w)2.831
Predicted aqueous solubility (QPlogS)-3.399
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.485
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.354
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)203.309
Predicted brain/blood partition coefficient (QPlogBB)-0.322
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)97.82
Predicted skin permeability, log Kp (QPlogKp)-4.394
PM3 calculated ionization potential (IP(ev))9.198
PM3 calculated electron affinity (EA(eV))0.545
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)0.146
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)84.831
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)100.408
Number of nitrogen and oxygen atoms (#NandO)7
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
Q96KS0EIT6HIF-prolyl hydroxylase 1T53904SwissTargetPrediction
P41594GRM5Metabotropic glutamate receptor 5T99347SwissTargetPrediction
P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
P21554CNR1Cannabinoid receptor 1 (by homology)T76685SwissTargetPrediction
P07949RETKinesin-1 heavy chain/ Tyrosine-protein kinase receptor RETT60631SwissTargetPrediction
P24864CCNE1Cyclin-dependent kinase 2/cyclin E1T10052SEA
P07339CTSDCathepsin DT67102SwissTargetPrediction
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P35462DRD3Dopamine D3 receptorT02551SwissTargetPrediction
P04626ERBB2Receptor protein-tyrosine kinase erbB-2T14597SwissTargetPrediction
P24941CDK2Cyclin-dependent kinase 2T70176SEA
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
O96017CHEK2Serine/threonine-protein kinase Chk2T28713SwissTargetPrediction
P47871GCGRGlucagon receptorT60182SwissTargetPrediction
P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SEA
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
P09619PDGFRBPlatelet-derived growth factor receptor betaT59102SwissTargetPrediction
Q07002CDK18Serine/threonine-protein kinase PCTAIRE-3T27577SEA
Q02127DHODHDihydroorotate dehydrogenaseT61400SwissTargetPrediction
O43614HCRTR2Orexin receptor 2T69485SwissTargetPrediction
O43613HCRTR1Orexin receptor 1T73482SwissTargetPrediction
P52209PGD6-phosphogluconate dehydrogenaseT76497SEA
P20248CCNA2CDK2/Cyclin AT58470SEA
Q14004CDK13Cyclin-dependent kinase 13T74839SEA
P32754HPD4-hydroxyphenylpyruvate dioxygenaseT07137SwissTargetPrediction
Q8N5S9CAMKK1CaM-kinase kinase alphaT38134SEA
Q09013DMPKMyotonin-protein kinaseT68766SEA
P06881CALCACalcitonin gene-related peptide 1T93509SwissTargetPrediction
P41586ADCYAP1R1Pituitary adenylate cyclase-activating polypeptide type I receptorT92185SwissTargetPrediction
P21860ERBB3Receptor tyrosine-protein kinase erbB-3T86350SEA
Q13705ACVR2BActivin receptor type-2BT80338SEA
P27037ACVR2AActivin receptor type IIAT47366SEA
P14635CCNB1G2/mitotic-specific cyclin B1T98459SEA
Q9C098DCLK3Doublecortin-like kinase 3T77061SEA
Q9GZT9EGLN1Egl nine homolog 1T32880SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T53904DI0010Acute disease anaemia[ICD-11: 3A90]Q96KS0EIT6
T99347DI0152Fragile X chromosome[ICD-11: LD55]P41594GRM5
T99347DI0331Parkinsonism[ICD-11: 8A00]P41594GRM5
T31391DI0009Acute diabete complication[ICD-11: 5A2Y]P27487DPP4
T31391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P27487DPP4
T76685DI0031Anorexia nervosa[ICD-11: 6B80]P21554CNR1
T76685DI0214Insomnia[ICD-11: 7A00-7A0Z]P21554CNR1
T76685DI0308Obesity[ICD-11: 5B80-5B81]P21554CNR1
T60631DI0095Colorectal cancer[ICD-11: 2B91]P07949RET
T60631DI0238Lung cancer[ICD-11: 2C25]P07949RET
T60631DI0250Mature B-cell lymphoma[ICD-11: 2A85]P07949RET
T60631DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P07949RET
T60631DI0403Thrombocytopenia[ICD-11: 3B64]P07949RET
T60631DI0407Thyroid cancer[ICD-11: 2D10]P07949RET
T67102DI0275Multiple sclerosis[ICD-11: 8A40]P07339CTSD
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
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
T02551DI0051Bipolar disorder[ICD-11: 6A60]P35462DRD3
T02551DI0331Parkinsonism[ICD-11: 8A00]P35462DRD3
T14597DI0062Breast cancer[ICD-11: 2C60-2C6Y]P04626ERBB2
T14597DI0238Lung cancer[ICD-11: 2C25]P04626ERBB2
T14597DI0346Prostate cancer[ICD-11: 2C82]P04626ERBB2
T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
T84133DI0079Choreiform disorder[ICD-11: 8A01]Q9Y233PDE10A
T84133DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q9Y233PDE10A
T84133DI0218Irritable bowel syndrome[ICD-11: DD91]Q9Y233PDE10A
T84133DI0370Schizophrenia[ICD-11: 6A20]Q9Y233PDE10A
T84133DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9Y233PDE10A
T84631DI0053Blood-forming organ disease[ICD-11: 3C0Z]P00742F10
T84631DI0080Christmas disease[ICD-11: 3B11]P00742F10
T84631DI0091Coagulation defect[ICD-11: 3B10]P00742F10
T84631DI0103Coronary thrombosis[ICD-11: BA43]P00742F10
T84631DI0114Deep vein thrombosis[ICD-11: BD71]P00742F10
T84631DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P00742F10
T84631DI0405Thrombosis[ICD-11: DB61-GB90]P00742F10
T84631DI0433Venous thromboembolism[ICD-11: BD72]P00742F10
T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
T28713DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O96017CHEK2
T60182DI0193Hypo-glycaemia[ICD-11: 5A41]P47871GCGR
T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T59102DI0009Acute diabete complication[ICD-11: 5A2Y]P09619PDGFRB
T59102DI0361Renal cell carcinoma[ICD-11: 2C90]P09619PDGFRB
T59102DI0403Thrombocytopenia[ICD-11: 3B64]P09619PDGFRB
T61400DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q02127DHODH
T61400DI0275Multiple sclerosis[ICD-11: 8A40]Q02127DHODH
T69485DI0214Insomnia[ICD-11: 7A00-7A0Z]O43614HCRTR2
T73482DI0117Depression[ICD-11: 6A70-6A7Z]O43613HCRTR1
T73482DI0214Insomnia[ICD-11: 7A00-7A0Z]O43613HCRTR1
T73482DI0317Opioid use disorder[ICD-11: 6C43]O43613HCRTR1
T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
T58470DI0363Retina cancer[ICD-11: 2D02]P20248CCNA2
T74839DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q14004CDK13
T07137DI0258Metabolism inborn error[ICD-11: 5C50]P32754HPD
T68766DI0288Myotonic disorder[ICD-11: 8C71]Q09013DMPK
T93509DI0163General pain disorder[ICD-11: 8E43]P06881CALCA
T92185DI0264Migraine[ICD-11: 8A80]P41586ADCYAP1R1
T86350DI0062Breast cancer[ICD-11: 2C60-2C6Y]P21860ERBB3
T86350DI0095Colorectal cancer[ICD-11: 2B91]P21860ERBB3
T86350DI0172Head and neck cancer[ICD-11: 2D42]P21860ERBB3
T86350DI0238Lung cancer[ICD-11: 2C25]P21860ERBB3
T86350DI0246Malignant mesenchymal neoplasm[ICD-11: 2B5D-2B5Y]P21860ERBB3
T86350DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]P21860ERBB3
T86350DI0326Pancreatic cancer[ICD-11: 2C10]P21860ERBB3
T86350DI0351Psoriasis[ICD-11: EA90]P21860ERBB3
T86350DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P21860ERBB3
T86350DI0393Squamous cell carcinoma[ICD-11: 2B60-2D01]P21860ERBB3
T80338DI0295Nervous system paraneoplastic/autoimmune disorder[ICD-11: 8E4A]Q13705ACVR2B
T47366DI0012Acute myeloid leukaemia[ICD-11: 2A60]P27037ACVR2A
T47366DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P27037ACVR2A

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