Compound ID	CDAMM02155
Common name	Rotenonic acid
IUPAC name	9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one
Molecular formula	C₂₃H₂₄O₆

Experimental data

Retention time	13.53
Adduct	[M+H]+
Actual mz	397.164
Theoretical mz	397.164
Error	0.31
Ionizaton mode	Positive
Instrument type	LC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score	5.1263

Identifiers and class information

Inchi key	GBVCHRDRVDOMQV-UHFFFAOYNA-N
Smiles	O=C1C2=CC=C(O)C(=C2OC3COC4=CC(OC)=C(OC)C=C4C13)CC=C(C)C
Superclass	Phenylpropanoids and polyketides
Class	Isoflavonoids

Plant source

Asparagus racemosus Willd.

External sources

HMDB ID
KNApSAcK ID	C00009574
FooDB ID
DrugBank ID
ChEBI ID	CHEBI:92599
Pubchem Compound ID	4303568
PlantCyc ID	CPD-9534
UNPD ID	UNPD4748
Coconut ID	CNP0164696
LipidMAPS ID	LMPK12060018
NANPDB ID

Pharmacokinetic properties

Number of descriptor values(#stars)	0
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)	5
Number of reactive functional groups (#rtvFG)	0
Predicted central nervous system activity (CNS)	0
Molecular weight (mol_MW)	396.439
Computed dipole moment(dipole)	2.989
Total solvent accessible surface area (SASA)	655.536
Hydrophobic component of SASA (FOSA)	424.307
Hydrophilic component of SASA (FISA)	76.329
Pie component of the SASA (PISA)	154.9
Weakly polar component of the SASA (WPSA)	0
Total solvent accesible volume (volume)	1206.82
Number of hydrogen bond donors (donorHB)	1
Number of hydrogen bond acceptors (accptHB)	5.75
Free energy of solvation of dipole (dip^2/V)	0.0074022
Index of cohesive interaction in solids (ACxDN^.5/SA)	0.0087714
Globularity descriptor (glob)	0.836237
Predicted polarizability in cubic angstroms (QPpolrz)	40.412
Predicted hexadecane/gas partition coefficient (QPlogPC16)	11.285
Predicted octanol/gas partition coefficient (QPlogPoct)	17.608
Predicted water/gas partition coefficient (QPlogPw)	8.895
Predicted octanol/water partition coefficient (QPlogPo/w)	4.11
Predicted aqueous solubility (QPlogS)	-5.29
Conformation-independent predicted aqueous solubility (CIQPlogS)	-5.859
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)	-4.921
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)	1870.99
Predicted brain/blood partition coefficient (QPlogBB)	-0.466
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)	973.707
Predicted skin permeability, log Kp (QPlogKp)	-1.901
PM3 calculated ionization potential (IP(ev))	8.538
PM3 calculated electron affinity (EA(eV))	0.517
Number of likely metabolic reactions (#metab)	7
Prediction of binding to human serum albumin (QPlogKhsa)	0.567
Predicted qualitative human oral absorption (HumanOralAbsorption)	3
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)	76.591
Number of nitrogen and oxygen atoms (#NandO)	6
Number of violations of Lipinski’s rule of five (RuleOfFive)	0
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
P08913	ADRA2A	Alpha-2a adrenergic receptor	T11448	SEA
P11926	ODC1	Ornithine decarboxylase	T60366	SEA
P18031	PTPN1	Protein-tyrosine phosphatase 1B	T16347	SEA
P18825	ADRA2C	Adrenergic receptor alpha-2	T01777	SEA
P14679	TYR	Tyrosinase	T97035	SEA

Target associated diseases

TTD_ID	Disease_ID	Disease name	ICD_11	Uniprot ID	Gene names
T11448	DI0040	Attention deficit hyperactivity disorder	[ICD-11: 6A05]	P08913	ADRA2A
T11448	DI0317	Opioid use disorder	[ICD-11: 6C43]	P08913	ADRA2A
T11448	DI0396	Substance abuse	[ICD-11: 6C40]	P08913	ADRA2A
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
T01777	DI0166	Glaucoma	[ICD-11: 9C61]	P18825	ADRA2C
T01777	DI0190	Hypertension	[ICD-11: BA00-BA04]	P18825	ADRA2C
T01777	DI0196	Hypotension	[ICD-11: BA20-BA21]	P18825	ADRA2C
T01777	DI0308	Obesity	[ICD-11: 5B80-5B81]	P18825	ADRA2C
T01777	DI0310	Ocular disease	[ICD-11: N.A.]	P18825	ADRA2C
T01777	DI0396	Substance abuse	[ICD-11: 6C40]	P18825	ADRA2C
T97035	DI0007	Acquired hypermelanosis	[ICD-11: ED60]	P14679	TYR
T97035	DI0008	Acquired hypomelanotic disorder	[ICD-11: ED63]	P14679	TYR