Citrusin C



Compound IDCDAMM01481
Common nameCitrusin C
IUPAC name2-(hydroxymethyl)-6-(2-methoxy-4-prop-2-enylphenoxy)oxane-3,4,5-triol
Molecular formulaC16H22O7

Experimental data

Retention time10.12
Adduct[M+K]+
Actual mz365.095
Theoretical mz365.1
Error14.13
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.5197

Identifiers and class information

Inchi keyVADSVXSGIFBZLI-UHFFFAOYNA-N
SmilesOCC1OC(OC2=CC=C(C=C2OC)CC=C)C(O)C(O)C1O
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

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)10
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)326.346
Computed dipole moment(dipole)4.525
Total solvent accessible surface area (SASA)576.74
Hydrophobic component of SASA (FOSA)319.279
Hydrophilic component of SASA (FISA)154.408
Pie component of the SASA (PISA)103.053
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1038.28
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)10
Free energy of solvation of dipole (dip^2/V)0.0197205
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0346777
Globularity descriptor (glob)0.859796
Predicted polarizability in cubic angstroms (QPpolrz)29.961
Predicted hexadecane/gas partition coefficient (QPlogPC16)10.622
Predicted octanol/gas partition coefficient (QPlogPoct)20.938
Predicted water/gas partition coefficient (QPlogPw)16.361
Predicted octanol/water partition coefficient (QPlogPo/w)0.59
Predicted aqueous solubility (QPlogS)-2.142
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.44
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.292
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)340.134
Predicted brain/blood partition coefficient (QPlogBB)-1.432
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)154.212
Predicted skin permeability, log Kp (QPlogKp)-3.042
PM3 calculated ionization potential (IP(ev))8.549
PM3 calculated electron affinity (EA(eV))-0.471
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.702
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)75.709
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)106.959
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
P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction and SEA
P00734F2ThrombinT94033SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction and SEA
P10253GAALysosomal alpha-glucosidase (by homology)T31514SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
P00491PNPPurine nucleoside phosphorylaseT78198SwissTargetPrediction
P14920DAOD-amino-acid oxidaseT33124SwissTargetPrediction
P04183TK1Thymidine kinase, cytosolicT30081SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
Q7Z2W7TRPM8Transient receptor potential cation channel subfamily M member 8T41955SEA
Q13547HDAC1Histone deacetylase 1T68547SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q9HC97GPR35G-protein coupled receptor 35T56143SwissTargetPrediction
P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
Q16831UPP1Uridine phosphorylase 1 (by homology)T97388SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P78536ADAM17ADAM17T82393SwissTargetPrediction
P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
P53779MAPK10c-Jun N-terminal kinase 3T85421SwissTargetPrediction
P09211GSTP1Glutathione S-transferase PiT21669SwissTargetPrediction
P32320CDACytidine deaminase (by homology)T79027SwissTargetPrediction
P00813ADAAdenosine deaminaseT03661SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
P28482MAPK1MAP kinase ERK2T58970SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction and SEA
P52789HK2Hexokinase type IIT96685SwissTargetPrediction
P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction and SEA
P23526AHCYAdenosylhomocysteinaseT68698SwissTargetPrediction
Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction and SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SEA
P19971TYMPThymidine phosphorylaseT59929SwissTargetPrediction
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
P63316TNNC1Troponin, cardiac muscleT12966SEA
P06865HEXABeta-hexosaminidase subunit alphaT63196SEA
P07686HEXBBeta-N-acetyl-D-hexosaminidase-A/BT63197SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
P19429TNNI3Cardiac troponin IT20186SEA
P45379TNNT2Cardiac muscle troponin TT05887SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T94033DI0052Bleeding disorder[ICD-11: GA20-GA21]P00734F2
T94033DI0091Coagulation defect[ICD-11: 3B10]P00734F2
T94033DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P00734F2
T94033DI0275Multiple sclerosis[ICD-11: 8A40]P00734F2
T94033DI0287Myocardial infarction[ICD-11: BA41-BA43]P00734F2
T94033DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00734F2
T94033DI0403Thrombocytopenia[ICD-11: 3B64]P00734F2
T94033DI0405Thrombosis[ICD-11: DB61-GB90]P00734F2
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T31514DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P10253GAA
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T78198DI0120Diabetes mellitus[ICD-11: 5A10]P00491PNP
T78198DI0167Gout[ICD-11: FA25]P00491PNP
T78198DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00491PNP
T78198DI0283Mycosis fungoides[ICD-11: 2B01]P00491PNP
T78198DI0351Psoriasis[ICD-11: EA90]P00491PNP
T33124DI0038Ataxic disorder[ICD-11: 8A03]P14920DAO
T33124DI0370Schizophrenia[ICD-11: 6A20]P14920DAO
T30081DI0012Acute myeloid leukaemia[ICD-11: 2A60]P04183TK1
T30081DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P04183TK1
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
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
T41955DI0422Upper respiratory tract disorder[ICD-11: CA0Z]Q7Z2W7TRPM8
T68547DI0274Multiple myeloma[ICD-11: 2A83]Q13547HDAC1
T68547DI0283Mycosis fungoides[ICD-11: 2B01]Q13547HDAC1
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
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
T97388DI0292Nasopharyngitis[ICD-11: CA00]Q16831UPP1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
T85421DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]P53779MAPK10
T21669DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P09211GSTP1
T79027DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P32320CDA
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T58970DI0036Arteries/arterioles disorder[ICD-11: BD52]P28482MAPK1
T58970DI0252Melanoma[ICD-11: 2C30]P28482MAPK1
T58970DI0326Pancreatic cancer[ICD-11: 2C10]P28482MAPK1
T58970DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28482MAPK1
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T49898DI0062Breast cancer[ICD-11: 2C60-2C6Y]P06493CDK1
T49898DI0238Lung cancer[ICD-11: 2C25]P06493CDK1
T49898DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P06493CDK1
T49898DI0250Mature B-cell lymphoma[ICD-11: 2A85]P06493CDK1
T49898DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06493CDK1
T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
T60526DI0037Asthma[ICD-11: CA23]P14151SELL
T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
T59929DI0117Depression[ICD-11: 6A70-6A7Z]P19971TYMP
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
T63196DI0242Lysosomal disease[ICD-11: 5C56]P06865HEXA
T63197DI0242Lysosomal disease[ICD-11: 5C56]P07686HEXB
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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