Versicolactone D



Compound IDCDAMM02542
Common nameVersicolactone D
IUPAC name7,11,19-trimethyl-16-propan-2-yl-24,26-dioxapentacyclo[13.7.2.12,13.13,13.01,14]hexacosa-3(25),6,10,19-tetraen-23-one
Molecular formulaC30H42O3

Experimental data

Retention time3.67
Adduct[M+H]+
Actual mz451.325
Theoretical mz451.32
Error10.91
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.6097

Identifiers and class information

Inchi keyRHFOIVCXBQDVCO-ZUITVLSZNA-N
SmilesO=C1OC2C(CCC(=CCCC13C4OC5(C=C4CCC=C(C)CCC=C(C)C5)C23)C)C(C)C
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)4
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)1
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)1
Molecular weight (mol_MW)450.66
Computed dipole moment(dipole)4.481
Total solvent accessible surface area (SASA)716.624
Hydrophobic component of SASA (FOSA)647.42
Hydrophilic component of SASA (FISA)38.752
Pie component of the SASA (PISA)30.452
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1428.28
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)3.75
Free energy of solvation of dipole (dip^2/V)0.0140582
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.855885
Predicted polarizability in cubic angstroms (QPpolrz)50.654
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.862
Predicted octanol/gas partition coefficient (QPlogPoct)18.673
Predicted water/gas partition coefficient (QPlogPw)5.388
Predicted octanol/water partition coefficient (QPlogPo/w)6.554
Predicted aqueous solubility (QPlogS)-7.671
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.532
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.009
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4250.25
Predicted brain/blood partition coefficient (QPlogBB)0.151
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2363.7
Predicted skin permeability, log Kp (QPlogKp)-2.03
PM3 calculated ionization potential (IP(ev))9.414
PM3 calculated electron affinity (EA(eV))-0.622
Number of likely metabolic reactions (#metab)12
Prediction of binding to human serum albumin (QPlogKhsa)1.719
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)40.796
Number of nitrogen and oxygen atoms (#NandO)3
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
P14555PLA2G2APhospholipase A2 group IIAT19160SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
Q07817BCL2L1Apoptosis regulator Bcl-XT56510SwissTargetPrediction
P07711CTSLCathepsin LT98691SwissTargetPrediction
Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P04035HMGCRHMG-CoA reductaseT53585SwissTargetPrediction
Q02156PRKCEProtein kinase C epsilonT00895SwissTargetPrediction
O15111CHUKInhibitor of NF-kappa-B kinase (IKK)T78429SwissTargetPrediction
P25774CTSSCathepsin ST68290SwissTargetPrediction
Q9NR96TLR9Toll-like receptor (TLR7/TLR9)T11451SwissTargetPrediction
Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
P25024CXCR1Interleukin-8 receptor AT00884SwissTargetPrediction
P53609PGGT1BGeranylgeranyl transferase type IT76396SwissTargetPrediction
P01584IL1BInterleukin-1 betaT42000SwissTargetPrediction
Q16549PCSK7Subtilisin/kexin type 7T33211SwissTargetPrediction
P41252IARSIsoleucyl-tRNA synthetaseT46515SwissTargetPrediction

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
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T19160DI0062Breast cancer[ICD-11: 2C60-2C6Y]P14555PLA2G2A
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T56510DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q07817BCL2L1
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T02001DI0411Tonus and reflex abnormality[ICD-11: MB47]Q08499PDE4D
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
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
T00895DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]Q02156PRKCE
T00895DI0243Malaria[ICD-11: 1F40-1F45]Q02156PRKCE
T78429DI0250Mature B-cell lymphoma[ICD-11: 2A85]O15111CHUK
T68290DI0042Autoimmune disease[ICD-11: 4A40-4A45]P25774CTSS
T68290DI0092Coeliac disease[ICD-11: DA95]P25774CTSS
T68290DI0107Crohn disease[ICD-11: DD70]P25774CTSS
T68290DI0120Diabetes mellitus[ICD-11: 5A10]P25774CTSS
T68290DI0163General pain disorder[ICD-11: 8E43]P25774CTSS
T68290DI0324Pain[ICD-11: MG30-MG3Z]P25774CTSS
T68290DI0382Sjogren syndrome[ICD-11: 4A43]P25774CTSS
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
T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
T00884DI0324Pain[ICD-11: MG30-MG3Z]P25024CXCR1
T76396DI0241Lymphoma[ICD-11: 2A80-2A86]P53609PGGT1B
T42000DI0267Mineral excesses[ICD-11: 5B91]P01584IL1B
T42000DI0269Monogenic autoinflammatory syndrome[ICD-11: 4A60]P01584IL1B
T42000DI0320Osteoarthritis[ICD-11: FA00-FA05]P01584IL1B
T42000DI0366Rheumatoid arthritis[ICD-11: FA20]P01584IL1B

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