Cyclointegrin



Compound IDCDAMM01556
Common nameCyclointegrin
IUPAC name5,15-dihydroxy-17-methoxy-9,9-dimethyl-8,20-dioxatetracyclo[10.8.0.02,7.014,19]icosa-1(12),2(7),3,5,14,16,18-heptaen-13-one
Molecular formulaC21H20O6

Experimental data

Retention time11.63
Adduct[M+Na]+
Actual mz391.112
Theoretical mz391.115
Error7.21
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.4224

Identifiers and class information

Inchi keyLRBWGBCDUCRXLG-UHFFFAOYSA-N
SmilesO=C1C2=C(O)C=C(OC)C=C2OC=3C=4C=CC(O)=CC4OC(C)(C)CCC13
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

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)3
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)368.385
Computed dipole moment(dipole)1.774
Total solvent accessible surface area (SASA)604.09
Hydrophobic component of SASA (FOSA)274.58
Hydrophilic component of SASA (FISA)131.836
Pie component of the SASA (PISA)197.674
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1085.64
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)4.5
Free energy of solvation of dipole (dip^2/V)0.0028973
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0074492
Globularity descriptor (glob)0.845645
Predicted polarizability in cubic angstroms (QPpolrz)37.255
Predicted hexadecane/gas partition coefficient (QPlogPC16)10.86
Predicted octanol/gas partition coefficient (QPlogPoct)16.172
Predicted water/gas partition coefficient (QPlogPw)8.65
Predicted octanol/water partition coefficient (QPlogPo/w)3.536
Predicted aqueous solubility (QPlogS)-5.163
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.667
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.972
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)556.795
Predicted brain/blood partition coefficient (QPlogBB)-0.846
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)262.71
Predicted skin permeability, log Kp (QPlogKp)-2.965
PM3 calculated ionization potential (IP(ev))9.006
PM3 calculated electron affinity (EA(eV))0.407
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)0.577
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)96.792
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)90.801
Number of nitrogen and oxygen atoms (#NandO)6
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
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
P34903GABRA3GABA A receptor alpha-3/beta-2/gamma-2T62292SwissTargetPrediction
Q96KS0EIT6HIF-prolyl hydroxylase 1T53904SwissTargetPrediction
P21397MAOAMonoamine oxidase AT83875SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P22748CA4Carbonic anhydrase IVT53378SEA
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction and SEA
P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
P04626ERBB2Receptor protein-tyrosine kinase erbB-2T14597SwissTargetPrediction
P11474ESRRAEstrogen-related receptor alphaT72841SEA
O95718ESRRBEstrogen-related receptor betaT42025SEA
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
Q09472EP300Histone acetyltransferase p300T25956SwissTargetPrediction
P08238HSP90AB1Heat shock protein HSP 90-betaT96623SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P47871GCGRGlucagon receptorT60182SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
Q96EB6SIRT1NAD-dependent deacetylase sirtuin 1T14731SwissTargetPrediction
P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
P00749PLAUUrokinase-type plasminogen activatorT17758SwissTargetPrediction
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P14679TYRTyrosinaseT97035SEA
P00374DHFRDihydrofolate reductaseT17345SwissTargetPrediction
Q9NPH5NOX4NADPH oxidase 4T29741SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q14680MELKMaternal embryonic leucine zipper kinaseT96892SwissTargetPrediction
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
Q04760GLO1Glyoxalase IT88285SEA
P51679CCR4C-C chemokine receptor type 4T06955SwissTargetPrediction
P14625HSP90B1EndoplasminT81311SwissTargetPrediction
Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
Q15120PDK3Pyruvate dehydrogenase kinase isoform 3T99029SEA
P16885PLCG2Phospholipase C-gamma-2T93922SEA
Q9NQS5GPR84G-protein coupled receptor 84T98091SwissTargetPrediction
O75581LRP6Low-density lipoprotein receptor-related protein 6T49755SEA
Q15717ELAVL1ELAV-like protein 1T78349SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA
Q9GZT9EGLN1Egl nine homolog 1T32880SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T62292DI0216Intentional self-harm[ICD-11: PC91]P34903GABRA3
T53904DI0010Acute disease anaemia[ICD-11: 3A90]Q96KS0EIT6
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T14597DI0062Breast cancer[ICD-11: 2C60-2C6Y]P04626ERBB2
T14597DI0238Lung cancer[ICD-11: 2C25]P04626ERBB2
T14597DI0346Prostate cancer[ICD-11: 2C82]P04626ERBB2
T72841DI0366Rheumatoid arthritis[ICD-11: FA20]P11474ESRRA
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
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
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T96623DI0062Breast cancer[ICD-11: 2C60-2C6Y]P08238HSP90AB1
T96623DI0238Lung cancer[ICD-11: 2C25]P08238HSP90AB1
T96623DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P08238HSP90AB1
T96623DI0249Mature B-cell leukaemia[ICD-11: 2A82]P08238HSP90AB1
T96623DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P08238HSP90AB1
T96623DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P08238HSP90AB1
T96623DI0395Stomach cancer[ICD-11: 2B72]P08238HSP90AB1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T60182DI0193Hypo-glycaemia[ICD-11: 5A41]P47871GCGR
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T14731DI0366Rheumatoid arthritis[ICD-11: FA20]Q96EB6SIRT1
T14731DI0399Systemic sclerosis[ICD-11: 4A42]Q96EB6SIRT1
T14731DI0431Vasculitis[ICD-11: 4A44]Q96EB6SIRT1
T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T17758DI0211Inherited coagulation factor deficiency[ICD-11: 3B14]P00749PLAU
T17758DI0287Myocardial infarction[ICD-11: BA41-BA43]P00749PLAU
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T17345DI0207Indeterminate colitis[ICD-11: DD72]P00374DHFR
T17345DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00374DHFR
T17345DI0416Tuberculosis[ICD-11: 1B10-1B12]P00374DHFR
T17345DI0427Urinary tract infection[ICD-11: GC08]P00374DHFR
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T96892DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q14680MELK
T96892DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q14680MELK
T96892DI0249Mature B-cell leukaemia[ICD-11: 2A82]Q14680MELK
T96892DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q14680MELK
T96892DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q14680MELK
T96892DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q14680MELK
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T06955DI0283Mycosis fungoides[ICD-11: 2B01]P51679CCR4
T06955DI0379Sezary syndrome[ICD-11: 2B02]P51679CCR4
T81311DI0238Lung cancer[ICD-11: 2C25]P14625HSP90B1
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T98091DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q9NQS5GPR84
T98091DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NQS5GPR84
T49755DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O75581LRP6
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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