Allolithocholic acid



Compound IDCDAMM00828
Common nameAllolithocholic acid
IUPAC name4-(3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
Molecular formulaC24H40O3

Experimental data

Retention time13.81
Adduct[M+Na]+
Actual mz399.282
Theoretical mz399.287
Error13.32
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2338

Identifiers and class information

Inchi keySMEROWZSTRWXGI-IBUNROKMSA-N
SmilesO=C(O)CCC(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)2
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)1
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)5
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)376.578
Computed dipole moment(dipole)4.889
Total solvent accessible surface area (SASA)656.288
Hydrophobic component of SASA (FOSA)499.277
Hydrophilic component of SASA (FISA)157.011
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1243.96
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)3.7
Free energy of solvation of dipole (dip^2/V)0.0192163
Index of cohesive interaction in solids (ACxDN^.5/SA)0.007973
Globularity descriptor (glob)0.852329
Predicted polarizability in cubic angstroms (QPpolrz)40.419
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.331
Predicted octanol/gas partition coefficient (QPlogPoct)18.346
Predicted water/gas partition coefficient (QPlogPw)7.837
Predicted octanol/water partition coefficient (QPlogPo/w)4.792
Predicted aqueous solubility (QPlogS)-5.896
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.2
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.114
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)81.389
Predicted brain/blood partition coefficient (QPlogBB)-1.179
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)41.806
Predicted skin permeability, log Kp (QPlogKp)-3.933
PM3 calculated ionization potential (IP(ev))10.715
PM3 calculated electron affinity (EA(eV))-1.117
Number of likely metabolic reactions (#metab)2
Prediction of binding to human serum albumin (QPlogKhsa)0.842
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)89.197
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)73.348
Number of nitrogen and oxygen atoms (#NandO)3
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P47869GABRA2GABA A receptor alpha-2/beta-2/gamma-2T51452SwissTargetPrediction
O75899GABBR2GABA-B receptorT42446SwissTargetPrediction
P54289CACNA2D1Voltage-gated calcium channel alpha2/delta subunit 1 (by homology)T84316SwissTargetPrediction
P41594GRM5Metabotropic glutamate receptor 5T99347SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SEA
P00918CA2Carbonic anhydrase IIT20401SEA
Q4U2R8SLC22A6Solute carrier family 22 member 6 (by homology)T70680SwissTargetPrediction
Q96RI1NR1H4Bile acid receptor FXRT51426SwissTargetPrediction and SEA
P31213SRD5A2Steroid 5-alpha-reductase 2T71390SEA
Q05586GRIN1Glutamate NMDA receptor; GRIN1/GRIN2BT62276SEA
P14867GABRA1GABA-A receptor; alpha-1/beta-2/gamma-2T51487SEA
P00747PLGPlasminogenT89034SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SEA
P48065SLC6A12Betaine transporterT08446SwissTargetPrediction
P10275ARAndrogen ReceptorT11211SwissTargetPrediction and SEA
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
P08185SERPINA6Corticosteroid binding globulinT88452SwissTargetPrediction and SEA
Q14994NR1I3Nuclear receptor subfamily 1 group I member 3 (by homology)T69506SwissTargetPrediction
P18405SRD5A1Steroid 5-alpha-reductase 1T70309SEA
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
Q9UHC9NPC1L1Niemann-Pick C1-like protein 1T33901SwissTargetPrediction and SEA
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P15090FABP4Fatty acid binding protein adipocyteT07217SwissTargetPrediction
Q07869PPARAPeroxisome proliferator-activated receptor alphaT86591SwissTargetPrediction
Q01469FABP5Fatty acid binding protein epidermalT21507SwissTargetPrediction
Q03181PPARDPeroxisome proliferator-activated receptor deltaT36557SwissTargetPrediction
O14842FFAR1Free fatty acid receptor 1T25608SwissTargetPrediction
P08575PTPRCLeukocyte common antigenT43115SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction and SEA
P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
P11473VDRVitamin D receptorT34234SwissTargetPrediction and SEA
Q8TDU6GPBAR1G-protein coupled bile acid receptor 1T86273SwissTargetPrediction and SEA
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
P16662UGT2B7UDP-glucuronosyltransferase 2B7T62815SwissTargetPrediction and SEA
P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
Q13133NR1H3LXR-alphaT52297SwissTargetPrediction and SEA
P21731TBXA2RThromboxane A2 receptorT76198SwissTargetPrediction
P10827THRAThyroid hormone receptor alphaT79591SwissTargetPrediction
P10828THRBThyroid hormone receptor beta-1T98933SwissTargetPrediction
P43116PTGER2Prostanoid EP2 receptorT38529SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P80365HSD11B211-beta-hydroxysteroid dehydrogenase 2T43721SwissTargetPrediction
P11413G6PDGlucose-6-phosphate 1-dehydrogenaseT63484SwissTargetPrediction and SEA
P05093CYP17A1Cytochrome P450 17A1T89041SEA
P41229KDM5CLysine-specific demethylase 5CT85540SwissTargetPrediction
Q9NR96TLR9Toll-like receptor (TLR7/TLR9)T11451SwissTargetPrediction
P05230FGF1Acidic fibroblast growth factorT18639SEA
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction and SEA
Q9Y2K7KDM2ALysine-specific demethylase 2AT71949SwissTargetPrediction
Q12908SLC10A2Ileal bile acid transporterT24982SEA
Q13258PTGDRProstanoid DP receptorT68782SwissTargetPrediction
P43088PTGFRProstanoid FP receptorT75797SwissTargetPrediction
P35398RORANuclear receptor ROR-alphaT43206SEA
P60842EIF4A1Eukaryotic initiation factor 4A-IT86805SEA
Q13224GRIN2BGlutamate [NMDA] receptor subunit epsilon 2T76414SEA
Q13822ENPP2AutotaxinT63512SEA
Q9UPP1PHF8Histone lysine demethylase PHF8T00933SwissTargetPrediction
P54756EPHA5Ephrin type-A receptor 5T18474SEA
P54764EPHA4Ephrin type-A receptor 4T70234SEA
P54753EPHB3Ephrin type-B receptor 3T56121SEA
O15399GRIN2DGlutamate [NMDA] receptor subunit epsilon 4T56588SEA
Q14973SLC10A1Bile acid transporterT99189SEA
P18507GABRG2GABA-A receptor; alpha-6/beta-3/gamma-2T08910SwissTargetPrediction and SEA
P38571LIPALysosomal acid lipase/cholesteryl ester hydrolaseT24373SEA
P29322EPHA8Ephrin type-A receptor 8T58266SEA
Q15375EPHA7Ephrin type-A receptor 7T57006SEA
Q9UJM8HAO1Hydroxyacid oxidase 1T63170SwissTargetPrediction
Q04609FOLH1Glutamate carboxypeptidase IIT97071SEA
P47870GABRB2GABA(A) receptor beta-2T80387SwissTargetPrediction and SEA
O15439ABCC4Multidrug resistance protein 4T39919SEA
Q14957GRIN2CGlutamate receptor ionotropic NMDA 2CT72595SEA
O14764GABRDGABA(A) receptor deltaT27376SEA
P01730CD4T-cell surface glycoprotein CD4T10191SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T51452DI0216Intentional self-harm[ICD-11: PC91]P47869GABRA2
T42446DI0117Depression[ICD-11: 6A70-6A7Z]O75899GABBR2
T42446DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]O75899GABBR2
T42446DI0275Multiple sclerosis[ICD-11: 8A40]O75899GABBR2
T42446DI0290Narcolepsy[ICD-11: 7A20]O75899GABBR2
T84316DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P54289CACNA2D1
T84316DI0190Hypertension[ICD-11: BA00-BA04]P54289CACNA2D1
T99347DI0152Fragile X chromosome[ICD-11: LD55]P41594GRM5
T99347DI0331Parkinsonism[ICD-11: 8A00]P41594GRM5
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T70680DI0167Gout[ICD-11: FA25]Q4U2R8SLC22A6
T70680DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q4U2R8SLC22A6
T70680DI0310Ocular disease[ICD-11: N.A.]Q4U2R8SLC22A6
T51426DI0043Autoimmune liver disease[ICD-11: DB96]Q96RI1NR1H4
T51426DI0077Cholelithiasis[ICD-11: DC11]Q96RI1NR1H4
T51426DI0320Osteoarthritis[ICD-11: FA00-FA05]Q96RI1NR1H4
T71390DI0348Prostate hyperplasia[ICD-11: GA90]P31213SRD5A2
T62276DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q05586GRIN1
T62276DI0182HIV-infected patients with tuberculosis[ICD-11: 1B10-1B14]Q05586GRIN1
T51487DI0014Acute respiratory distress syndrome[ICD-11: CB00]P14867GABRA1
T51487DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P14867GABRA1
T51487DI0082Chronic insomnia[ICD-11: 7A00]P14867GABRA1
T51487DI0087Chronic pain[ICD-11: MG30]P14867GABRA1
T51487DI0101Corneal disease[ICD-11: 9A76-9A78]P14867GABRA1
T51487DI0112Cystitis[ICD-11: GC00]P14867GABRA1
T51487DI0117Depression[ICD-11: 6A70-6A7Z]P14867GABRA1
T51487DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P14867GABRA1
T51487DI0173Headache[ICD-11: 8A80-8A84]P14867GABRA1
T51487DI0214Insomnia[ICD-11: 7A00-7A0Z]P14867GABRA1
T51487DI0243Malaria[ICD-11: 1F40-1F45]P14867GABRA1
T51487DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P14867GABRA1
T51487DI0411Tonus and reflex abnormality[ICD-11: MB47]P14867GABRA1
T89034DI0030Angina pectoris[ICD-11: BA40]P00747PLG
T89034DI0052Bleeding disorder[ICD-11: GA20-GA21]P00747PLG
T89034DI0254Menopausal disorder[ICD-11: GA30]P00747PLG
T89034DI0287Myocardial infarction[ICD-11: BA41-BA43]P00747PLG
T89034DI0345Procedure injury[ICD-11: NE81]P00747PLG
T89034DI0357Pulmonary thromboembolism[ICD-11: BB00]P00747PLG
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T11211DI0005Acne vulgaris[ICD-11: ED80]P10275AR
T11211DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10275AR
T11211DI0021Alcoholic liver disease[ICD-11: DB94]P10275AR
T11211DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10275AR
T11211DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P10275AR
T11211DI0145Female pelvic pain[ICD-11: GA34]P10275AR
T11211DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P10275AR
T11211DI0237Low bone mass disorder[ICD-11: FB83]P10275AR
T11211DI0247Mammary tumour[ICD-11: 2C60-2C6Z]P10275AR
T11211DI0346Prostate cancer[ICD-11: 2C82]P10275AR
T11211DI0401Testicular dysfunction[ICD-11: 5A81]P10275AR
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
T88452DI0037Asthma[ICD-11: CA23]P08185SERPINA6
T88452DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P08185SERPINA6
T88452DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08185SERPINA6
T69506DI0126Dizziness and giddiness[ICD-11: MB48]Q14994NR1I3
T70309DI0347Prostate disease[ICD-11: GA91]P18405SRD5A1
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T33901DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q9UHC9NPC1L1
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T86591DI0187Hyperlipidemia[ICD-11: 5C80]Q07869PPARA
T86591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q07869PPARA
T86591DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q07869PPARA
T36557DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]Q03181PPARD
T36557DI0308Obesity[ICD-11: 5B80-5B81]Q03181PPARD
T25608DI0417Type 2 diabetes mellitus[ICD-11: 5A11]O14842FFAR1
T43115DI0012Acute myeloid leukaemia[ICD-11: 2A60]P08575PTPRC
T43115DI0414Transplanted organ/tissue[ICD-11: QB63]P08575PTPRC
T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
T34234DI0083Chronic kidney disease[ICD-11: GB61]P11473VDR
T34234DI0171Hair/hair growth developmental defect[ICD-11: LC30]P11473VDR
T34234DI0189Hyper-parathyroidism[ICD-11: 5A51]P11473VDR
T34234DI0195Hypo-parathyroidism[ICD-11: 5A50]P11473VDR
T34234DI0266Mineral deficiency[ICD-11: 5B5K]P11473VDR
T34234DI0351Psoriasis[ICD-11: EA90]P11473VDR
T34234DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]P11473VDR
T86273DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q8TDU6GPBAR1
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T52297DI0117Depression[ICD-11: 6A70-6A7Z]Q13133NR1H3
T76198DI0102Coronary atherosclerosis[ICD-11: BA52]P21731TBXA2R
T76198DI0121Diabetic foot ulcer[ICD-11: BD54]P21731TBXA2R
T76198DI0287Myocardial infarction[ICD-11: BA41-BA43]P21731TBXA2R
T76198DI0378Sexual dysfunction[ICD-11: HA00-HA01]P21731TBXA2R
T79591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10827THRA
T79591DI0197Hypo-thyroidism[ICD-11: 5A00]P10827THRA
T98933DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10828THRB
T38529DI0003Abortion[ICD-11: JA00]P43116PTGER2
T38529DI0102Coronary atherosclerosis[ICD-11: BA52]P43116PTGER2
T38529DI0121Diabetic foot ulcer[ICD-11: BD54]P43116PTGER2
T38529DI0166Glaucoma[ICD-11: 9C61]P43116PTGER2
T38529DI0356Pulmonary hypertension[ICD-11: BB01]P43116PTGER2
T38529DI0378Sexual dysfunction[ICD-11: HA00-HA01]P43116PTGER2
T38529DI0413Transplant rejection[ICD-11: NE84]P43116PTGER2
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T43721DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P80365HSD11B2
T63484DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P11413G6PD
T89041DI0346Prostate cancer[ICD-11: 2C82]P05093CYP17A1
T11451DI0095Colorectal cancer[ICD-11: 2B91]Q9NR96TLR9
T11451DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]Q9NR96TLR9
T11451DI0252Melanoma[ICD-11: 2C30]Q9NR96TLR9
T11451DI0346Prostate cancer[ICD-11: 2C82]Q9NR96TLR9
T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
T24982DI0349Pruritus[ICD-11: EC90]Q12908SLC10A2
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T75797DI0003Abortion[ICD-11: JA00]P43088PTGFR
T75797DI0102Coronary atherosclerosis[ICD-11: BA52]P43088PTGFR
T75797DI0166Glaucoma[ICD-11: 9C61]P43088PTGFR
T43206DI0235Liver cancer[ICD-11: 2C12]P35398RORA
T43206DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P35398RORA
T86805DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P60842EIF4A1
T76414DI0024Alpha-1-antitrypsin deficiency[ICD-11: 5C5A]Q13224GRIN2B
T63512DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q13822ENPP2
T70234DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P54764EPHA4
T56588DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]O15399GRIN2D
T99189DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]Q14973SLC10A1
T08910DI0117Depression[ICD-11: 6A70-6A7Z]P18507GABRG2
T08910DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P18507GABRG2
T08910DI0411Tonus and reflex abnormality[ICD-11: MB47]P18507GABRG2
T24373DI0132Enzyme deficiency[ICD-11: 5C51-5C57]P38571LIPA
T63170DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]Q9UJM8HAO1
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T80387DI0117Depression[ICD-11: 6A70-6A7Z]P47870GABRB2
T80387DI0214Insomnia[ICD-11: 7A00-7A0Z]P47870GABRB2
T80387DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P47870GABRB2
T80387DI0411Tonus and reflex abnormality[ICD-11: MB47]P47870GABRB2
T72595DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]Q14957GRIN2C
T27376DI0117Depression[ICD-11: 6A70-6A7Z]O14764GABRD
T27376DI0214Insomnia[ICD-11: 7A00-7A0Z]O14764GABRD
T27376DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]O14764GABRD
T10191DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P01730CD4

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