Oxosarcophylline



Compound IDCDAMM00494
Common nameOxosarcophylline
IUPAC name17-hydroxy-4,5-dimethoxy-2-oxa-11-azatetracyclo[8.7.1.03,8.014,18]octadeca-1(17),3(8),4,6,10,12,14(18),15-octaen-9-one
Molecular formulaC18H13NO5

Experimental data

Retention time6.13
Adduct[M+H]+
Actual mz324.082
Theoretical mz324.086
Error11.96
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.3672

Identifiers and class information

Inchi keyGNZFAFYCESGELU-UHFFFAOYSA-N
SmilesO=C1C2=NC=CC3=CC=C(O)C(OC4=C(OC)C(OC)=CC=C14)=C23
SuperclassOrganoheterocyclic compounds
ClassBenzoxepines

Plant source

  • Piper longum L.

    • 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)0
    Molecular weight (mol_MW)323.304
    Computed dipole moment(dipole)5.456
    Total solvent accessible surface area (SASA)524.013
    Hydrophobic component of SASA (FOSA)169.002
    Hydrophilic component of SASA (FISA)96.262
    Pie component of the SASA (PISA)258.749
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)936.907
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)5.75
    Free energy of solvation of dipole (dip^2/V)0.0317745
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.010973
    Globularity descriptor (glob)0.883665
    Predicted polarizability in cubic angstroms (QPpolrz)31.886
    Predicted hexadecane/gas partition coefficient (QPlogPC16)9.768
    Predicted octanol/gas partition coefficient (QPlogPoct)15.362
    Predicted water/gas partition coefficient (QPlogPw)9.862
    Predicted octanol/water partition coefficient (QPlogPo/w)2.431
    Predicted aqueous solubility (QPlogS)-3.343
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.461
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.648
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1210.72
    Predicted brain/blood partition coefficient (QPlogBB)-0.439
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)608.291
    Predicted skin permeability, log Kp (QPlogKp)-2.094
    PM3 calculated ionization potential (IP(ev))8.805
    PM3 calculated electron affinity (EA(eV))1.326
    Number of likely metabolic reactions (#metab)4
    Prediction of binding to human serum albumin (QPlogKhsa)-0.036
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)96.36
    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)81.986
    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
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P34903GABRA3GABA A receptor alpha-3/beta-2/gamma-2T62292SwissTargetPrediction
    Q96KS0EIT6HIF-prolyl hydroxylase 1T53904SwissTargetPrediction
    P21397MAOAMonoamine oxidase AT83875SEA
    P42336PIK3CAPI3-kinase p110-alpha subunitT80276SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    Q92731ESR2Estrogen receptor betaT80896SEA
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
    P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction
    P07858CTSBCathepsin (B and K)T61746SwissTargetPrediction
    O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
    Q96S37SLC22A12Solute carrier family 22 member 12T86057SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SwissTargetPrediction
    Q9BPW0PPP5CSerine/threonine-protein phosphataseT04123SwissTargetPrediction
    P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
    P48736PIK3CGPI3-kinase p110-gamma subunitT95913SwissTargetPrediction
    P17936IGFBP3Insulin-like growth factor binding protein 3T33455SwissTargetPrediction
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q9GZT9EGLN1Egl nine homolog 1T32880SwissTargetPrediction

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    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
    T80276DI0062Breast cancer[ICD-11: 2C60-2C6Y]P42336PIK3CA
    T80276DI0151Follicular lymphoma[ICD-11: 2A80]P42336PIK3CA
    T80276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P42336PIK3CA
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
    T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
    T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
    T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
    T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
    T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
    T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
    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
    T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
    T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
    T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
    T86057DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q96S37SLC22A12
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
    T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
    T95913DI0151Follicular lymphoma[ICD-11: 2A80]P48736PIK3CG
    T95913DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P48736PIK3CG
    T95913DI0249Mature B-cell leukaemia[ICD-11: 2A82]P48736PIK3CG
    T33455DI0115Dementia[ICD-11: 6D80-6D8Z]P17936IGFBP3
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2

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