ent-7alpha-Hydroxykaur-16-en-19-oic acid



Compound IDCDAMM02644
Common nameent-7alpha-Hydroxykaur-16-en-19-oic acid
IUPAC name2-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
Molecular formulaC20H30O3

Experimental data

Retention time3.69
Adduct[M+H]+
Actual mz319.231
Theoretical mz319.226
Error14.8
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.1449

Identifiers and class information

Inchi keyKMLXVEXJZSTMBV-RAFHMICINA-N
SmilesO=C(O)C1(C)CCCC2(C)C3CCC4C(=C)CC3(C4)C(O)CC12
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)2
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)318.455
Computed dipole moment(dipole)4.917
Total solvent accessible surface area (SASA)529.718
Hydrophobic component of SASA (FOSA)392.961
Hydrophilic component of SASA (FISA)107.509
Pie component of the SASA (PISA)29.248
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1003.96
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)3.7
Free energy of solvation of dipole (dip^2/V)0.0240812
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0098781
Globularity descriptor (glob)0.91537
Predicted polarizability in cubic angstroms (QPpolrz)33.019
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.238
Predicted octanol/gas partition coefficient (QPlogPoct)15.835
Predicted water/gas partition coefficient (QPlogPw)8.057
Predicted octanol/water partition coefficient (QPlogPo/w)3.606
Predicted aqueous solubility (QPlogS)-4.226
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.098
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.233
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)239.879
Predicted brain/blood partition coefficient (QPlogBB)-0.412
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)134.472
Predicted skin permeability, log Kp (QPlogKp)-3.206
PM3 calculated ionization potential (IP(ev))9.877
PM3 calculated electron affinity (EA(eV))-1.032
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)0.356
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)90.659
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)62.953
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)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q07820MCL1Induced myeloid leukemia cell differentiation protein Mcl-1T14912SwissTargetPrediction
Q96RI1NR1H4Bile acid receptor FXRT51426SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
P10275ARAndrogen ReceptorT11211SwissTargetPrediction
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
P11473VDRVitamin D receptorT34234SwissTargetPrediction
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
P16662UGT2B7UDP-glucuronosyltransferase 2B7T62815SwissTargetPrediction
Q13133NR1H3LXR-alphaT52297SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SwissTargetPrediction
P11388TOP2ADNA topoisomerase II alphaT17048SwissTargetPrediction
O43174CYP26A1Cytochrome P450 26A1T84634SwissTargetPrediction
Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
P04637TP53Tumour suppressor p53/oncoprotein Mdm2T15739SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T14912DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q07820MCL1
T14912DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q07820MCL1
T14912DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q07820MCL1
T14912DI0252Melanoma[ICD-11: 2C30]Q07820MCL1
T14912DI0274Multiple myeloma[ICD-11: 2A83]Q07820MCL1
T14912DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q07820MCL1
T51426DI0043Autoimmune liver disease[ICD-11: DB96]Q96RI1NR1H4
T51426DI0077Cholelithiasis[ICD-11: DC11]Q96RI1NR1H4
T51426DI0320Osteoarthritis[ICD-11: FA00-FA05]Q96RI1NR1H4
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
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
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
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
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T52297DI0117Depression[ICD-11: 6A70-6A7Z]Q13133NR1H3
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T84634DI0314Oesophagitis[ICD-11: DA24]O43174CYP26A1
T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
T15739DI0233Lip/oral cavity/pharynx neoplasm[ICD-11: 2B6E]P04637TP53
T15739DI0323Ovarian dysfunction[ICD-11: 5A80]P04637TP53
T15739DI0413Transplant rejection[ICD-11: NE84]P04637TP53

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