Annoglabasin B



Compound IDCDAMM02727
Common nameAnnoglabasin B
IUPAC name5-(acetyloxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-14-carboxylic acid
Molecular formulaC22H34O4

Experimental data

Retention time2.72
Adduct[M+H]+
Actual mz363.251
Theoretical mz363.253
Error5.16
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0893

Identifiers and class information

Inchi keyZKXLEDOCSSUHKY-UHFFFAOYNA-N
SmilesO=C(OCC1(C)CCCC2(C)C1CCC34CC(C(=O)O)C(CCC32)C4)C
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

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)3
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)362.508
Computed dipole moment(dipole)7.987
Total solvent accessible surface area (SASA)619.829
Hydrophobic component of SASA (FOSA)468.297
Hydrophilic component of SASA (FISA)151.531
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1168.42
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)4
Free energy of solvation of dipole (dip^2/V)0.0545939
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0064534
Globularity descriptor (glob)0.86555
Predicted polarizability in cubic angstroms (QPpolrz)38.68
Predicted hexadecane/gas partition coefficient (QPlogPC16)10.404
Predicted octanol/gas partition coefficient (QPlogPoct)16.988
Predicted water/gas partition coefficient (QPlogPw)6.984
Predicted octanol/water partition coefficient (QPlogPo/w)4.423
Predicted aqueous solubility (QPlogS)-5.624
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.903
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.9
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)91.733
Predicted brain/blood partition coefficient (QPlogBB)-0.966
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)47.578
Predicted skin permeability, log Kp (QPlogKp)-4.024
PM3 calculated ionization potential (IP(ev))10.725
PM3 calculated electron affinity (EA(eV))-0.993
Number of likely metabolic reactions (#metab)1
Prediction of binding to human serum albumin (QPlogKhsa)0.747
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)87.97
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)85.68
Number of nitrogen and oxygen atoms (#NandO)4
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
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
Q12809KCNH2HERGT20251SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
Q8IXJ6SIRT2NAD-dependent deacetylase sirtuin 2T83904SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
Q14416GRM2Metabotropic glutamate receptor 2T62820SwissTargetPrediction
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
O75762TRPA1Transient receptor potential cation channel subfamily A member 1T84040SwissTargetPrediction
P18405SRD5A1Steroid 5-alpha-reductase 1T70309SwissTargetPrediction
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
P11473VDRVitamin D receptorT34234SwissTargetPrediction
Q8TDU6GPBAR1G-protein coupled bile acid receptor 1T86273SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
Q7Z2W7TRPM8Transient receptor potential cation channel subfamily M member 8T41955SwissTargetPrediction
P16662UGT2B7UDP-glucuronosyltransferase 2B7T62815SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction
P23946CMA1ChymaseT05114SwissTargetPrediction
Q9HAN5TRP1Cationic trypsinogenT27602SwissTargetPrediction
P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SwissTargetPrediction
Q96S37SLC22A12Solute carrier family 22 member 12T86057SwissTargetPrediction
Q9Y5Y4PTGDR2G protein-coupled receptor 44T61722SwissTargetPrediction
P04035HMGCRHMG-CoA reductaseT53585SwissTargetPrediction
Q15722LTB4RLeukotriene B4 receptor 1T59626SwissTargetPrediction
P53779MAPK10c-Jun N-terminal kinase 3T85421SwissTargetPrediction
P47712PLA2G4ACytosolic phospholipase A2T14834SwissTargetPrediction
P35408PTGER4Prostanoid EP4 receptorT18876SwissTargetPrediction
P43115PTGER3Prostanoid EP3 receptorT85467SwissTargetPrediction
P06756ITGAVVitronectin receptor alphaT67103SwissTargetPrediction
Q9BYF1ACE2Angiotensin-converting enzyme 2T27889SwissTargetPrediction
P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
P15085CPA1Carboxypeptidase A1T33966SwissTargetPrediction
Q99895CTRCChymotrypsin CT10118SwissTargetPrediction
Q13258PTGDRProstanoid DP receptorT68782SwissTargetPrediction
P24557TBXAS1Thromboxane-A synthaseT78356SwissTargetPrediction
P32239CCKBRCholecystokinin B receptor (by homology)T05849SwissTargetPrediction
Q8TDS5OXER1Oxoeicosanoid receptor 1T68834SwissTargetPrediction
P30989NTSR1Neurotensin receptor 1T02728SwissTargetPrediction
Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
P19793RXRARetinoid X receptor alpha (by homology)T13726SwissTargetPrediction
P53671LIMK2LIM domain kinase 2T09133SwissTargetPrediction
O60760HPGDSHematopoietic prostaglandin D synthaseT19433SwissTargetPrediction
Q13822ENPP2AutotaxinT63512SwissTargetPrediction
Q9Y478PRKAB1AMP-activated protein kinase, beta-1 subunitT38875SwissTargetPrediction
P13631RARGRetinoic acid receptor gammaT82146SwissTargetPrediction
P48443RXRGRetinoid X receptor gammaT46456SwissTargetPrediction
P10826RARBRetinoic acid receptor betaT61657SwissTargetPrediction
Q14145KEAP1Kelch-like ECH-associated protein 1T83198SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
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
T83904DI0365Retinopathy[ICD-11: 9B71]Q8IXJ6SIRT2
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T62820DI0025Alzheimer disease[ICD-11: 8A20]Q14416GRM2
T62820DI0051Bipolar disorder[ICD-11: 6A60]Q14416GRM2
T62820DI0116Dengue fever[ICD-11: 1D2Z]Q14416GRM2
T62820DI0117Depression[ICD-11: 6A70-6A7Z]Q14416GRM2
T62820DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]Q14416GRM2
T62820DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]Q14416GRM2
T62820DI0308Obesity[ICD-11: 5B80-5B81]Q14416GRM2
T62820DI0354Psychotic disorder[ICD-11: 6A20-6A25]Q14416GRM2
T62820DI0370Schizophrenia[ICD-11: 6A20]Q14416GRM2
T80975DI0062Breast cancer[ICD-11: 2C60-2C6Y]P35968KDR
T80975DI0095Colorectal cancer[ICD-11: 2B91]P35968KDR
T80975DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P35968KDR
T80975DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P35968KDR
T80975DI0361Renal cell carcinoma[ICD-11: 2C90]P35968KDR
T80975DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35968KDR
T80975DI0395Stomach cancer[ICD-11: 2B72]P35968KDR
T80975DI0403Thrombocytopenia[ICD-11: 3B64]P35968KDR
T80975DI0407Thyroid cancer[ICD-11: 2D10]P35968KDR
T84040DI0422Upper respiratory tract disorder[ICD-11: CA0Z]O75762TRPA1
T70309DI0347Prostate disease[ICD-11: GA91]P18405SRD5A1
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
T86273DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q8TDU6GPBAR1
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
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
T41955DI0422Upper respiratory tract disorder[ICD-11: CA0Z]Q7Z2W7TRPM8
T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T05114DI0039Atopic eczema[ICD-11: EA80]P23946CMA1
T05114DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P23946CMA1
T05114DI0169Gram-positive bacterial infection[ICD-11: 1B74-1F40]P23946CMA1
T05114DI0175Heart failure[ICD-11: BD10-BD1Z]P23946CMA1
T05114DI0229Left ventricular failure[ICD-11: BD11]P23946CMA1
T05114DI0287Myocardial infarction[ICD-11: BA41-BA43]P23946CMA1
T27602DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9HAN5TRP1
T27602DI0274Multiple myeloma[ICD-11: 2A83]Q9HAN5TRP1
T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
T86057DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q96S37SLC22A12
T61722DI0102Coronary atherosclerosis[ICD-11: BA52]Q9Y5Y4PTGDR2
T53585DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P04035HMGCR
T53585DI0102Coronary atherosclerosis[ICD-11: BA52]P04035HMGCR
T53585DI0128Dyslipidemia[ICD-11: 5C80-5C81]P04035HMGCR
T53585DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P04035HMGCR
T53585DI0275Multiple sclerosis[ICD-11: 8A40]P04035HMGCR
T53585DI0287Myocardial infarction[ICD-11: BA41-BA43]P04035HMGCR
T53585DI0324Pain[ICD-11: MG30-MG3Z]P04035HMGCR
T59626DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]Q15722LTB4R
T59626DI0355Pulmonary disease[ICD-11: 1B10-1F85]Q15722LTB4R
T59626DI0361Renal cell carcinoma[ICD-11: 2C90]Q15722LTB4R
T85421DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]P53779MAPK10
T14834DI0039Atopic eczema[ICD-11: EA80]P47712PLA2G4A
T18876DI0037Asthma[ICD-11: CA23]P35408PTGER4
T18876DI0175Heart failure[ICD-11: BD10-BD1Z]P35408PTGER4
T18876DI0264Migraine[ICD-11: 8A80]P35408PTGER4
T18876DI0303Non-small-cell lung cancer[ICD-11: 2C25]P35408PTGER4
T18876DI0324Pain[ICD-11: MG30-MG3Z]P35408PTGER4
T18876DI0360Rectum cancer[ICD-11: 2B92]P35408PTGER4
T18876DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35408PTGER4
T18876DI0414Transplanted organ/tissue[ICD-11: QB63]P35408PTGER4
T85467DI0166Glaucoma[ICD-11: 9C61]P43115PTGER3
T85467DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P43115PTGER3
T85467DI0414Transplanted organ/tissue[ICD-11: QB63]P43115PTGER3
T67103DI0095Colorectal cancer[ICD-11: 2B91]P06756ITGAV
T67103DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06756ITGAV
T27889DI0009Acute diabete complication[ICD-11: 5A2Y]Q9BYF1ACE2
T27889DI0217Intrathoracic organs injury[ICD-11: NB32]Q9BYF1ACE2
T27889DI0356Pulmonary hypertension[ICD-11: BB01]Q9BYF1ACE2
T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T78356DI0030Angina pectoris[ICD-11: BA40]P24557TBXAS1
T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
T02728DI0207Indeterminate colitis[ICD-11: DD72]P30989NTSR1
T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
T13726DI0225Kaposi sarcoma[ICD-11: 2B57]P19793RXRA
T13726DI0283Mycosis fungoides[ICD-11: 2B01]P19793RXRA
T19433DI0148Flatworm infection[ICD-11: 1F70-1F86]O60760HPGDS
T63512DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q13822ENPP2
T38875DI0009Acute diabete complication[ICD-11: 5A2Y]Q9Y478PRKAB1
T82146DI0005Acne vulgaris[ICD-11: ED80]P13631RARG
T82146DI0012Acute myeloid leukaemia[ICD-11: 2A60]P13631RARG
T82146DI0225Kaposi sarcoma[ICD-11: 2B57]P13631RARG
T82146DI0277Muscle calcification/ossification[ICD-11: FB31]P13631RARG
T82146DI0351Psoriasis[ICD-11: EA90]P13631RARG
T46456DI0225Kaposi sarcoma[ICD-11: 2B57]P48443RXRG
T46456DI0232Light sensitivity impairment[ICD-11: 9D45]P48443RXRG
T61657DI0225Kaposi sarcoma[ICD-11: 2B57]P10826RARB
T83198DI0356Pulmonary hypertension[ICD-11: BB01]Q14145KEAP1
T83198DI0425Urinary system clinical symptom[ICD-11: MF8Y]Q14145KEAP1

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