Compound details

Heterophyllin

Compound ID	CDAMM00444
Common name	Heterophyllin
IUPAC name	5-hydroxy-2,2-dimethyl-7,10-bis(3-methylbut-2-enyl)-8-(2,4,5-trihydroxyphenyl)pyrano[3,2-g]chromen-6-one
Molecular formula	C₃₀H₃₂O₇

Experimental data

Retention time	0.31
Adduct	[M+Na]+
Actual mz	527.199
Theoretical mz	527.204
Error	9.9
Ionizaton mode	Positive
Instrument type	LC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score	8.1715

Identifiers and class information

Inchi key	CBYLXVCMCVXUQQ-UHFFFAOYSA-N
Smiles	O=C1C2=C(O)C=3C=CC(OC3C(=C2OC(C=4C=C(O)C(O)=CC4O)=C1CC=C(C)C)CC=C(C)C)(C)C
Superclass	Phenylpropanoids and polyketides
Class	Flavonoids

Plant source

Centella asiatica (L.) Urban

External sources

HMDB ID	HMDB0034660
KNApSAcK ID	C00013460
FooDB ID	FDB013184
DrugBank ID
ChEBI ID
Pubchem Compound ID	14557105
PlantCyc ID
UNPD ID	UNPD149924
Coconut ID	CNP0279586
LipidMAPS ID	LMPK12110929
NANPDB ID

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)	0
Number of non-conjugated amide groups (#amide)	0
Number of rotatable bonds (#rotor)	8
Number of reactive functional groups (#rtvFG)	0
Predicted central nervous system activity (CNS)	-2
Molecular weight (mol_MW)	504.579
Computed dipole moment(dipole)	6.221
Total solvent accessible surface area (SASA)	814.9
Hydrophobic component of SASA (FOSA)	451.491
Hydrophilic component of SASA (FISA)	181.754
Pie component of the SASA (PISA)	181.655
Weakly polar component of the SASA (WPSA)	0
Total solvent accesible volume (volume)	1551.77
Number of hydrogen bond donors (donorHB)	3
Number of hydrogen bond acceptors (accptHB)	5.25
Free energy of solvation of dipole (dip^2/V)	0.0249366
Index of cohesive interaction in solids (ACxDN^.5/SA)	0.0111588
Globularity descriptor (glob)	0.79545
Predicted polarizability in cubic angstroms (QPpolrz)	52.546
Predicted hexadecane/gas partition coefficient (QPlogPC16)	15.901
Predicted octanol/gas partition coefficient (QPlogPoct)	25.155
Predicted water/gas partition coefficient (QPlogPw)	11.953
Predicted octanol/water partition coefficient (QPlogPo/w)	5.412
Predicted aqueous solubility (QPlogS)	-7.519
Conformation-independent predicted aqueous solubility (CIQPlogS)	-8.311
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)	-5.708
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)	187.207
Predicted brain/blood partition coefficient (QPlogBB)	-1.834
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)	80.875
Predicted skin permeability, log Kp (QPlogKp)	-3.461
PM3 calculated ionization potential (IP(ev))	8.705
PM3 calculated electron affinity (EA(eV))	0.439
Number of likely metabolic reactions (#metab)	10
Prediction of binding to human serum albumin (QPlogKhsa)	1.308
Predicted qualitative human oral absorption (HumanOralAbsorption)	1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)	73.389
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)	119.714
Number of nitrogen and oxygen atoms (#NandO)	7
Number of violations of Lipinski’s rule of five (RuleOfFive)	2
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
P22303	ACHE	Acetylcholinesterase	T30082	SwissTargetPrediction
P30542	ADORA1	Adenosine A1 receptor	T92072	SwissTargetPrediction
P0DMS8	ADORA3	Adenosine A3 receptor	T36059	SwissTargetPrediction
P19838	NFKB1	Nuclear factor NF-kappa-B p105 subunit	T83145	SwissTargetPrediction and SEA
O60341	KDM1A	Lysine-specific histone demethylase 1	T16739	SwissTargetPrediction
P35354	PTGS2	Cyclooxygenase-2	T66665	SwissTargetPrediction
P11926	ODC1	Ornithine decarboxylase	T60366	SEA
P18031	PTPN1	Protein-tyrosine phosphatase 1B	T16347	SwissTargetPrediction
Q14534	SQLE	Squalene monooxygenase (by homology)	T93344	SwissTargetPrediction
P06276	BCHE	Butyrylcholinesterase	T99799	SwissTargetPrediction
P56817	BACE1	Beta-secretase 1	T79031	SwissTargetPrediction
P49327	FASN	Fatty acid synthase	T16514	SwissTargetPrediction
P19838	NFKB1	Nuclear factor NF-kappa-B p105 subunit	T83145	SwissTargetPrediction and SEA
P00742	F10	Thrombin and coagulation factor X	T84631	SwissTargetPrediction
P10276	RARA	Retinoic acid receptor alpha	T94085	SEA
P07900	HSP90AA1	Heat shock protein HSP 90-alpha	T18477	SwissTargetPrediction
P05771	PRKCB	Protein kinase C beta	T40276	SwissTargetPrediction
Q02156	PRKCE	Protein kinase C epsilon	T00895	SwissTargetPrediction
Q05655	PRKCD	Protein kinase C delta	T44861	SwissTargetPrediction
P25025	CXCR2	Interleukin-8 receptor B	T56923	SwissTargetPrediction
Q9UNQ0	ABCG2	ATP-binding cassette sub-family G member 2	T56556	SwissTargetPrediction and SEA
Q16678	CYP1B1	Cytochrome P450 1B1	T92521	SwissTargetPrediction
P14625	HSP90B1	Endoplasmin	T81311	SwissTargetPrediction
O60911	CTSV	Cathepsin (V and K)	T93653	SEA
P10599	TXN	Thioredoxin	T85616	SEA

Target associated diseases

TTD_ID	Disease_ID	Disease name	ICD_11	Uniprot ID	Gene names
T30082	DI0025	Alzheimer disease	[ICD-11: 8A20]	P22303	ACHE
T30082	DI0166	Glaucoma	[ICD-11: 9C61]	P22303	ACHE
T30082	DI0282	Myasthenia gravis	[ICD-11: 8C6Y]	P22303	ACHE
T30082	DI0313	Oesophageal/gastroduodenal disorder	[ICD-11: DD90]	P22303	ACHE
T30082	DI0332	Pediculosis	[ICD-11: 1G00]	P22303	ACHE
T30082	DI0421	Unspecific substance harmful effect	[ICD-11: NE6Z]	P22303	ACHE
T92072	DI0319	Orthostatic hypotension	[ICD-11: BA21]	P30542	ADORA1
T36059	DI0351	Psoriasis	[ICD-11: EA90]	P0DMS8	ADORA3
T36059	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	P0DMS8	ADORA3
T83145	DI0218	Irritable bowel syndrome	[ICD-11: DD91]	P19838	NFKB1
T83145	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	P19838	NFKB1
T16739	DI0012	Acute myeloid leukaemia	[ICD-11: 2A60]	O60341	KDM1A
T16739	DI0025	Alzheimer disease	[ICD-11: 8A20]	O60341	KDM1A
T16739	DI0138	Ewing sarcoma	[ICD-11: 2B52]	O60341	KDM1A
T16739	DI0238	Lung cancer	[ICD-11: 2C25]	O60341	KDM1A
T16739	DI0241	Lymphoma	[ICD-11: 2A80-2A86]	O60341	KDM1A
T16739	DI0245	Malignant haematopoietic neoplasm	[ICD-11: 2B33]	O60341	KDM1A
T16739	DI0284	Myelodysplastic syndrome	[ICD-11: 2A37]	O60341	KDM1A
T16739	DI0286	Myeloproliferative neoplasm	[ICD-11: 2A20]	O60341	KDM1A
T16739	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	O60341	KDM1A
T66665	DI0087	Chronic pain	[ICD-11: MG30]	P35354	PTGS2
T66665	DI0145	Female pelvic pain	[ICD-11: GA34]	P35354	PTGS2
T66665	DI0188	Hyper-lipoproteinaemia	[ICD-11: 5C80]	P35354	PTGS2
T66665	DI0207	Indeterminate colitis	[ICD-11: DD72]	P35354	PTGS2
T66665	DI0227	Knee osteoarthritis	[ICD-11: FA01]	P35354	PTGS2
T66665	DI0320	Osteoarthritis	[ICD-11: FA00-FA05]	P35354	PTGS2
T66665	DI0324	Pain	[ICD-11: MG30-MG3Z]	P35354	PTGS2
T66665	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	P35354	PTGS2
T66665	DI0416	Tuberculosis	[ICD-11: 1B10-1B12]	P35354	PTGS2
T60366	DI0020	African trypanosomiasis	[ICD-11: 1F51]	P11926	ODC1
T16347	DI0009	Acute diabete complication	[ICD-11: 5A2Y]	P18031	PTPN1
T16347	DI0062	Breast cancer	[ICD-11: 2C60-2C6Y]	P18031	PTPN1
T16347	DI0308	Obesity	[ICD-11: 5B80-5B81]	P18031	PTPN1
T16347	DI0417	Type 2 diabetes mellitus	[ICD-11: 5A11]	P18031	PTPN1
T93344	DI0118	Dermatophytosis	[ICD-11: 1F28]	Q14534	SQLE
T93344	DI0385	Skin fungal infection disorder	[ICD-11: EA60]	Q14534	SQLE
T99799	DI0324	Pain	[ICD-11: MG30-MG3Z]	P06276	BCHE
T99799	DI0411	Tonus and reflex abnormality	[ICD-11: MB47]	P06276	BCHE
T79031	DI0025	Alzheimer disease	[ICD-11: 8A20]	P56817	BACE1
T16514	DI0096	concerning food/fluid intake symptom	[ICD-11: MG43]	P49327	FASN
T83145	DI0218	Irritable bowel syndrome	[ICD-11: DD91]	P19838	NFKB1
T83145	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	P19838	NFKB1
T84631	DI0053	Blood-forming organ disease	[ICD-11: 3C0Z]	P00742	F10
T84631	DI0080	Christmas disease	[ICD-11: 3B11]	P00742	F10
T84631	DI0091	Coagulation defect	[ICD-11: 3B10]	P00742	F10
T84631	DI0103	Coronary thrombosis	[ICD-11: BA43]	P00742	F10
T84631	DI0114	Deep vein thrombosis	[ICD-11: BD71]	P00742	F10
T84631	DI0397	Supraventricular tachyarrhythmia	[ICD-11: BC81]	P00742	F10
T84631	DI0405	Thrombosis	[ICD-11: DB61-GB90]	P00742	F10
T84631	DI0433	Venous thromboembolism	[ICD-11: BD72]	P00742	F10
T94085	DI0025	Alzheimer disease	[ICD-11: 8A20]	P10276	RARA
T94085	DI0251	Mature T-cell lymphoma	[ICD-11: 2A90]	P10276	RARA
T18477	DI0015	Acute upper respiratory infection	[ICD-11: CA07]	P07900	HSP90AA1
T18477	DI0037	Asthma	[ICD-11: CA23]	P07900	HSP90AA1
T40276	DI0123	Diffuse large B-cell lymphoma	[ICD-11: 2A81]	P05771	PRKCB
T40276	DI0241	Lymphoma	[ICD-11: 2A80-2A86]	P05771	PRKCB
T40276	DI0245	Malignant haematopoietic neoplasm	[ICD-11: 2B33]	P05771	PRKCB
T00895	DI0033	Anxiety disorder	[ICD-11: 6B00-6B0Z]	Q02156	PRKCE
T00895	DI0243	Malaria	[ICD-11: 1F40-1F45]	Q02156	PRKCE
T44861	DI0287	Myocardial infarction	[ICD-11: BA41-BA43]	Q05655	PRKCD
T56923	DI0155	Fungal infection	[ICD-11: 1F29-1F2F]	P25025	CXCR2
T56923	DI0324	Pain	[ICD-11: MG30-MG3Z]	P25025	CXCR2
T56556	DI0218	Irritable bowel syndrome	[ICD-11: DD91]	Q9UNQ0	ABCG2
T56556	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	Q9UNQ0	ABCG2
T81311	DI0238	Lung cancer	[ICD-11: 2C25]	P14625	HSP90B1
T93653	DI0055	Bone cancer	[ICD-11: 2B5Z]	O60911	CTSV
T93653	DI0087	Chronic pain	[ICD-11: MG30]	O60911	CTSV
T85616	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	P10599	TXN