Citrusin F



Compound IDCDAMM00532
Common nameCitrusin F
IUPAC namemethyl 3-[3-hydroxy-4-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]propanoate
Molecular formulaC22H32O14

Experimental data

Retention time13.46
Adduct[M+NH4]+
Actual mz538.203
Theoretical mz538.213
Error17.32
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0781

Identifiers and class information

Inchi keyYLQXQJFWCRRNGA-UHFFFAOYNA-N
SmilesO=C(OC)CCC1=CC=C(OC2OC(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2O)C(O)=C1
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)10
    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)17
    Number of reactive functional groups (#rtvFG)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)520.486
    Computed dipole moment(dipole)4.269
    Total solvent accessible surface area (SASA)776.272
    Hydrophobic component of SASA (FOSA)341.161
    Hydrophilic component of SASA (FISA)365.963
    Pie component of the SASA (PISA)69.148
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1460.76
    Number of hydrogen bond donors (donorHB)8
    Number of hydrogen bond acceptors (accptHB)20.5
    Free energy of solvation of dipole (dip^2/V)0.0124775
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0746938
    Globularity descriptor (glob)0.802055
    Predicted polarizability in cubic angstroms (QPpolrz)42.05
    Predicted hexadecane/gas partition coefficient (QPlogPC16)16.693
    Predicted octanol/gas partition coefficient (QPlogPoct)37.238
    Predicted water/gas partition coefficient (QPlogPw)32.706
    Predicted octanol/water partition coefficient (QPlogPo/w)-2.696
    Predicted aqueous solubility (QPlogS)-1.68
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.134
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.065
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)3.353
    Predicted brain/blood partition coefficient (QPlogBB)-4.254
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.046
    Predicted skin permeability, log Kp (QPlogKp)-6.388
    PM3 calculated ionization potential (IP(ev))8.813
    PM3 calculated electron affinity (EA(eV))-0.278
    Number of likely metabolic reactions (#metab)10
    Prediction of binding to human serum albumin (QPlogKhsa)-1.585
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
    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)236.485
    Number of nitrogen and oxygen atoms (#NandO)14
    Number of violations of Lipinski’s rule of five (RuleOfFive)3
    Number of violations of Jorgensen’s rule of three (RuleOfThree)2

    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
    O43570CA12Carbonic anhydrase XIIT16987SEA
    Q16790CA9Carbonic anhydrase IXT64567SEA
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SEA
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
    Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SwissTargetPrediction
    P18405SRD5A1Steroid 5-alpha-reductase 1T70309SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SEA
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P16109SELPP-selectinT10965SEA
    P14151SELLLeukocyte adhesion molecule-1T60526SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction and SEA
    P60568IL2Interleukin-2T61698SEA
    Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
    P20916MAGMyelin-associated glycoprotein (by homology)T95286SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P63316TNNC1Troponin, cardiac muscleT12966SEA
    P09382LGALS1Galectin-1T09544SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q15391P2RY14Purinergic receptor P2Y14T16555SEA
    P05231IL6Interleukin-6T32578SEA
    P11717IGF2RInsulin-like growth factor II receptorT59550SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
    P19429TNNI3Cardiac troponin IT20186SEA
    P45379TNNT2Cardiac muscle troponin TT05887SEA

    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
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
    T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T70309DI0347Prostate disease[ICD-11: GA91]P18405SRD5A1
    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
    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
    T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
    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
    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
    T95286DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P20916MAG
    T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
    T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
    T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
    T59550DI0146Fibrosis[ICD-11: GA14-GC01]P11717IGF2R
    T59550DI0368Sarcoidosis[ICD-11: 4B20]P11717IGF2R
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

    Copyright © 2025