Guayulin A



Compound IDCDAMM02728
Common nameGuayulin A
IUPAC name(4,8,11,11-tetramethyl-2-bicyclo[8.1.0]undeca-4,8-dienyl) 3-phenylprop-2-enoate
Molecular formulaC24H30O2

Experimental data

Retention time6.89
Adduct[M+H]+
Actual mz351.231
Theoretical mz351.232
Error4.49
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9802

Identifiers and class information

Inchi keyJYEVPOCBZDNGDL-REJAXYODNA-N
SmilesO=C(OC1CC(=CCCC(=CC2C1C2(C)C)C)C)C=CC=3C=CC=CC3
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)3
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)4
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)1
Molecular weight (mol_MW)350.5
Computed dipole moment(dipole)2.894
Total solvent accessible surface area (SASA)711.231
Hydrophobic component of SASA (FOSA)447.576
Hydrophilic component of SASA (FISA)28.431
Pie component of the SASA (PISA)235.224
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1273.06
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)2
Free energy of solvation of dipole (dip^2/V)0.0065783
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.798706
Predicted polarizability in cubic angstroms (QPpolrz)44.472
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.948
Predicted octanol/gas partition coefficient (QPlogPoct)15.333
Predicted water/gas partition coefficient (QPlogPw)4.312
Predicted octanol/water partition coefficient (QPlogPo/w)6.705
Predicted aqueous solubility (QPlogS)-7.997
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.495
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.911
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)5324.63
Predicted brain/blood partition coefficient (QPlogBB)0.025
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3015.66
Predicted skin permeability, log Kp (QPlogKp)-0.831
PM3 calculated ionization potential (IP(ev))9.032
PM3 calculated electron affinity (EA(eV))0.801
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)1.609
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
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)27.869
Number of nitrogen and oxygen atoms (#NandO)2
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
Q12809KCNH2HERGT20251SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P41594GRM5Metabotropic glutamate receptor 5T99347SwissTargetPrediction
P11940PABPC1Polyadenylate-binding protein 1T58679SwissTargetPrediction
Q96RI1NR1H4Bile acid receptor FXRT51426SEA
P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
P07949RETKinesin-1 heavy chain/ Tyrosine-protein kinase receptor RETT60631SwissTargetPrediction
Q01959SLC6A3Dopamine transporterT55959SwissTargetPrediction
Q14416GRM2Metabotropic glutamate receptor 2T62820SwissTargetPrediction
P10145CXCL8Interleukin-8T22658SwissTargetPrediction
O75762TRPA1Transient receptor potential cation channel subfamily A member 1T84040SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P35367HRH1Histamine H1 receptorT77913SwissTargetPrediction
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
Q9UM73ALKALK tyrosine kinase receptorT56418SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SEA
P10828THRBThyroid hormone receptor beta-1T98933SwissTargetPrediction
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P37288AVPR1AVasopressin V1a receptor (by homology)T79232SwissTargetPrediction
P30518AVPR2Vasopressin V2 receptor (by homology)T66237SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
Q99572P2RX7P2X purinoceptor 7T63414SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
P34998CRHR1Corticotropin releasing factor receptor 1 (by homology)T45262SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P48067SLC6A9Glycine transporter 1T69685SwissTargetPrediction
P28074PSMB5Proteasome Macropain subunit MB1T49031SwissTargetPrediction
P30536TSPOTranslocator protein (by homology)T75440SwissTargetPrediction
O43614HCRTR2Orexin receptor 2T69485SwissTargetPrediction
Q9Y2T6GPR55G-protein coupled receptor 55T87670SwissTargetPrediction
O76083PDE9APhosphodiesterase 9AT17852SwissTargetPrediction
O75884RBBP9Putative hydrolase RBBP9T12084SEA
Q01064PDE1BPhosphodiesterase 1BT77613SwissTargetPrediction
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T99347DI0152Fragile X chromosome[ICD-11: LD55]P41594GRM5
T99347DI0331Parkinsonism[ICD-11: 8A00]P41594GRM5
T58679DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11940PABPC1
T51426DI0043Autoimmune liver disease[ICD-11: DB96]Q96RI1NR1H4
T51426DI0077Cholelithiasis[ICD-11: DC11]Q96RI1NR1H4
T51426DI0320Osteoarthritis[ICD-11: FA00-FA05]Q96RI1NR1H4
T27812DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P31645SLC6A4
T27812DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P31645SLC6A4
T27812DI0087Chronic pain[ICD-11: MG30]P31645SLC6A4
T27812DI0096concerning food/fluid intake symptom[ICD-11: MG43]P31645SLC6A4
T27812DI0101Corneal disease[ICD-11: 9A76-9A78]P31645SLC6A4
T27812DI0105Cough[ICD-11: MD12]P31645SLC6A4
T27812DI0117Depression[ICD-11: 6A70-6A7Z]P31645SLC6A4
T27812DI0264Migraine[ICD-11: 8A80]P31645SLC6A4
T27812DI0301Nicotine use disorder[ICD-11: 6C4A]P31645SLC6A4
T27812DI0308Obesity[ICD-11: 5B80-5B81]P31645SLC6A4
T27812DI0324Pain[ICD-11: MG30-MG3Z]P31645SLC6A4
T60631DI0095Colorectal cancer[ICD-11: 2B91]P07949RET
T60631DI0238Lung cancer[ICD-11: 2C25]P07949RET
T60631DI0250Mature B-cell lymphoma[ICD-11: 2A85]P07949RET
T60631DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P07949RET
T60631DI0403Thrombocytopenia[ICD-11: 3B64]P07949RET
T60631DI0407Thyroid cancer[ICD-11: 2D10]P07949RET
T55959DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q01959SLC6A3
T55959DI0051Bipolar disorder[ICD-11: 6A60]Q01959SLC6A3
T55959DI0101Corneal disease[ICD-11: 9A76-9A78]Q01959SLC6A3
T55959DI0290Narcolepsy[ICD-11: 7A20]Q01959SLC6A3
T55959DI0308Obesity[ICD-11: 5B80-5B81]Q01959SLC6A3
T55959DI0331Parkinsonism[ICD-11: 8A00]Q01959SLC6A3
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
T22658DI0324Pain[ICD-11: MG30-MG3Z]P10145CXCL8
T84040DI0422Upper respiratory tract disorder[ICD-11: CA0Z]O75762TRPA1
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
T77913DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P35367HRH1
T77913DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P35367HRH1
T77913DI0063Breathing abnormality[ICD-11: MD11]P35367HRH1
T77913DI0099Conjunctiva disorder[ICD-11: 9A60]P35367HRH1
T77913DI0105Cough[ICD-11: MD12]P35367HRH1
T77913DI0117Depression[ICD-11: 6A70-6A7Z]P35367HRH1
T77913DI0136Episodic vestibular syndrome[ICD-11: AB31]P35367HRH1
T77913DI0173Headache[ICD-11: 8A80-8A84]P35367HRH1
T77913DI0214Insomnia[ICD-11: 7A00-7A0Z]P35367HRH1
T77913DI0272Morning sickness disorder[ICD-11: SC00]P35367HRH1
T77913DI0292Nasopharyngitis[ICD-11: CA00]P35367HRH1
T77913DI0293Nausea/vomiting[ICD-11: MD90]P35367HRH1
T77913DI0331Parkinsonism[ICD-11: 8A00]P35367HRH1
T77913DI0349Pruritus[ICD-11: EC90]P35367HRH1
T77913DI0366Rheumatoid arthritis[ICD-11: FA20]P35367HRH1
T77913DI0388Sleep-wake disorder[ICD-11: 7A00-7B2Z]P35367HRH1
T77913DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P35367HRH1
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T56418DI0238Lung cancer[ICD-11: 2C25]Q9UM73ALK
T56418DI0251Mature T-cell lymphoma[ICD-11: 2A90]Q9UM73ALK
T56418DI0303Non-small-cell lung cancer[ICD-11: 2C25]Q9UM73ALK
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T98933DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10828THRB
T84133DI0079Choreiform disorder[ICD-11: 8A01]Q9Y233PDE10A
T84133DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q9Y233PDE10A
T84133DI0218Irritable bowel syndrome[ICD-11: DD91]Q9Y233PDE10A
T84133DI0370Schizophrenia[ICD-11: 6A20]Q9Y233PDE10A
T84133DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9Y233PDE10A
T79232DI0009Acute diabete complication[ICD-11: 5A2Y]P37288AVPR1A
T79232DI0041Autism spectrum disorder[ICD-11: 6A02]P37288AVPR1A
T79232DI0190Hypertension[ICD-11: BA00-BA04]P37288AVPR1A
T79232DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P37288AVPR1A
T79232DI0236Localisation[ICD-11: N.A.]P37288AVPR1A
T66237DI0009Acute diabete complication[ICD-11: 5A2Y]P30518AVPR2
T66237DI0041Autism spectrum disorder[ICD-11: 6A02]P30518AVPR2
T66237DI0131Enuresis[ICD-11: 6C00]P30518AVPR2
T66237DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P30518AVPR2
T66237DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30518AVPR2
T66237DI0338Polyuria[ICD-11: MF55]P30518AVPR2
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T02001DI0411Tonus and reflex abnormality[ICD-11: MB47]Q08499PDE4D
T63414DI0224Joint pain[ICD-11: ME82]Q99572P2RX7
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T45262DI0394Staphylococcal/streptococcal disease[ICD-11: 1B5Y]P34998CRHR1
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T69685DI0370Schizophrenia[ICD-11: 6A20]P48067SLC6A9
T75440DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P30536TSPO
T75440DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P30536TSPO
T75440DI0214Insomnia[ICD-11: 7A00-7A0Z]P30536TSPO
T75440DI0216Intentional self-harm[ICD-11: PC91]P30536TSPO
T75440DI0271Mood/affect symptom[ICD-11: MB24]P30536TSPO
T75440DI0411Tonus and reflex abnormality[ICD-11: MB47]P30536TSPO
T69485DI0214Insomnia[ICD-11: 7A00-7A0Z]O43614HCRTR2
T87670DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q9Y2T6GPR55
T17852DI0025Alzheimer disease[ICD-11: 8A20]O76083PDE9A
T17852DI0115Dementia[ICD-11: 6D80-6D8Z]O76083PDE9A
T17852DI0165Genitourinary disease[ICD-11: GA0Z-GC8Z]O76083PDE9A
T17852DI0175Heart failure[ICD-11: BD10-BD1Z]O76083PDE9A
T17852DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]O76083PDE9A
T17852DI0331Parkinsonism[ICD-11: 8A00]O76083PDE9A
T17852DI0370Schizophrenia[ICD-11: 6A20]O76083PDE9A
T17852DI0381Sickle-cell disorder[ICD-11: 3A51]O76083PDE9A
T77613DI0265Mild neurocognitive disorder[ICD-11: 6D71]Q01064PDE1B

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