Compound details

Cycloartomunin

Compound ID	CDAMM00703
Common name	Cycloartomunin
IUPAC name	11,20-dihydroxy-19-methoxy-7,7-dimethyl-15-(2-methylprop-1-enyl)-2,8,16-trioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,10,17,19,21-octaen-13-one
Molecular formula	C₂₆H₂₄O₇

Experimental data

Retention time	9.25
Adduct	[M+H]+
Actual mz	449.155
Theoretical mz	449.159
Error	9.07
Ionizaton mode	Positive
Instrument type	LC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score	7.4867

Identifiers and class information

Inchi key	WQSBCGFYYIWXHK-UHFFFAOYNA-N
Smiles	O=C1C2=C(O)C=C3OC(C=CC3=C2OC=4C=5C=C(O)C(OC)=CC5OC(C=C(C)C)C14)(C)C
Superclass	Phenylpropanoids and polyketides
Class	Flavonoids

Plant source

Piper retrofractum Vahl

External sources

HMDB ID	HMDB0038878
KNApSAcK ID	C00004055
FooDB ID	FDB018324
DrugBank ID
ChEBI ID
Pubchem Compound ID	10456312
PlantCyc ID
UNPD ID	UNPD130446
Coconut ID	CNP0280503
LipidMAPS ID	LMPK12110916
NANPDB ID

Pharmacokinetic properties

Number of descriptor values(#stars)	1
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)	0
Predicted central nervous system activity (CNS)	-1
Molecular weight (mol_MW)	448.471
Computed dipole moment(dipole)	3.745
Total solvent accessible surface area (SASA)	725.19
Hydrophobic component of SASA (FOSA)	407.618
Hydrophilic component of SASA (FISA)	118.895
Pie component of the SASA (PISA)	198.677
Weakly polar component of the SASA (WPSA)	0
Total solvent accesible volume (volume)	1331.81
Number of hydrogen bond donors (donorHB)	1
Number of hydrogen bond acceptors (accptHB)	5.25
Free energy of solvation of dipole (dip^2/V)	0.010531
Index of cohesive interaction in solids (ACxDN^.5/SA)	0.0072395
Globularity descriptor (glob)	0.80725
Predicted polarizability in cubic angstroms (QPpolrz)	46.474
Predicted hexadecane/gas partition coefficient (QPlogPC16)	13.081
Predicted octanol/gas partition coefficient (QPlogPoct)	19.744
Predicted water/gas partition coefficient (QPlogPw)	9.378
Predicted octanol/water partition coefficient (QPlogPo/w)	4.858
Predicted aqueous solubility (QPlogS)	-6.882
Conformation-independent predicted aqueous solubility (CIQPlogS)	-7.432
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)	-5.598
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)	738.613
Predicted brain/blood partition coefficient (QPlogBB)	-0.894
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)	356.553
Predicted skin permeability, log Kp (QPlogKp)	-2.627
PM3 calculated ionization potential (IP(ev))	8.655
PM3 calculated electron affinity (EA(eV))	0.896
Number of likely metabolic reactions (#metab)	6
Prediction of binding to human serum albumin (QPlogKhsa)	1.039
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)	98.078
Number of nitrogen and oxygen atoms (#NandO)	7
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
P22303	ACHE	Acetylcholinesterase	T30082	SwissTargetPrediction
P30542	ADORA1	Adenosine A1 receptor	T92072	SwissTargetPrediction
P09874	PARP1	Poly [ADP-ribose] polymerase-1	T06273	SwissTargetPrediction
P0DMS8	ADORA3	Adenosine A3 receptor	T36059	SwissTargetPrediction
P19838	NFKB1	Nuclear factor NF-kappa-B p105 subunit	T83145	SwissTargetPrediction
P56524	HDAC4	Histone deacetylase 4	T63816	SwissTargetPrediction
P35354	PTGS2	Cyclooxygenase-2	T66665	SwissTargetPrediction
P11926	ODC1	Ornithine decarboxylase	T60366	SEA
P28845	HSD11B1	11-beta-hydroxysteroid dehydrogenase 1	T65200	SwissTargetPrediction
P08253	MMP2	Matrix metalloproteinase 2	T68251	SwissTargetPrediction
P14061	HSD17B1	Estradiol 17-beta-dehydrogenase 1	T44011	SwissTargetPrediction
P06276	BCHE	Butyrylcholinesterase	T99799	SwissTargetPrediction
P30291	WEE1	Serine/threonine-protein kinase WEE1	T69991	SwissTargetPrediction
P56817	BACE1	Beta-secretase 1	T79031	SwissTargetPrediction
O14965	AURKA	Serine/threonine-protein kinase Aurora-A	T87675	SwissTargetPrediction
P45452	MMP13	Matrix metalloproteinase 13	T34296	SwissTargetPrediction
P19838	NFKB1	Nuclear factor NF-kappa-B p105 subunit	T83145	SwissTargetPrediction and SEA
P41143	OPRD1	Delta opioid receptor	T58992	SwissTargetPrediction
P00742	F10	Thrombin and coagulation factor X	T84631	SwissTargetPrediction
P07900	HSP90AA1	Heat shock protein HSP 90-alpha	T18477	SwissTargetPrediction
P40763	STAT3	Signal transducer and activator of transcription 3	T29130	SwissTargetPrediction
P19793	RXRA	Retinoid X receptor alpha (by homology)	T13726	SwissTargetPrediction
Q9UNQ0	ABCG2	ATP-binding cassette sub-family G member 2	T56556	SwissTargetPrediction
Q16678	CYP1B1	Cytochrome P450 1B1	T92521	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
T06273	DI0006	Acquired cutaneous blood vessel malformation	[ICD-11: EF20]	P09874	PARP1
T06273	DI0143	Fallopian tube cancer	[ICD-11: 2C74]	P09874	PARP1
T06273	DI0321	Ovarian cancer	[ICD-11: 2C73]	P09874	PARP1
T06273	DI0334	Peritoneal cancer	[ICD-11: 2C51]	P09874	PARP1
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
T63816	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	P56524	HDAC4
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
T65200	DI0210	Influenza	[ICD-11: 1E30-1E32]	P28845	HSD11B1
T65200	DI0239	Lupus erythematosus	[ICD-11: 4A40]	P28845	HSD11B1
T65200	DI0417	Type 2 diabetes mellitus	[ICD-11: 5A11]	P28845	HSD11B1
T68251	DI0238	Lung cancer	[ICD-11: 2C25]	P08253	MMP2
T99799	DI0324	Pain	[ICD-11: MG30-MG3Z]	P06276	BCHE
T99799	DI0411	Tonus and reflex abnormality	[ICD-11: MB47]	P06276	BCHE
T69991	DI0321	Ovarian cancer	[ICD-11: 2C73]	P30291	WEE1
T69991	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	P30291	WEE1
T69991	DI0429	Uterine ligament/parametrium/uterine adnexa neoplasm	[ICD-11: 2C72]	P30291	WEE1
T79031	DI0025	Alzheimer disease	[ICD-11: 8A20]	P56817	BACE1
T87675	DI0009	Acute diabete complication	[ICD-11: 5A2Y]	O14965	AURKA
T87675	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	O14965	AURKA
T34296	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	P45452	MMP13
T83145	DI0218	Irritable bowel syndrome	[ICD-11: DD91]	P19838	NFKB1
T83145	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	P19838	NFKB1
T58992	DI0059	Bowel habit change	[ICD-11: ME05]	P41143	OPRD1
T58992	DI0218	Irritable bowel syndrome	[ICD-11: DD91]	P41143	OPRD1
T58992	DI0324	Pain	[ICD-11: MG30-MG3Z]	P41143	OPRD1
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
T18477	DI0015	Acute upper respiratory infection	[ICD-11: CA07]	P07900	HSP90AA1
T18477	DI0037	Asthma	[ICD-11: CA23]	P07900	HSP90AA1
T29130	DI0351	Psoriasis	[ICD-11: EA90]	P40763	STAT3
T13726	DI0225	Kaposi sarcoma	[ICD-11: 2B57]	P19793	RXRA
T13726	DI0283	Mycosis fungoides	[ICD-11: 2B01]	P19793	RXRA
T56556	DI0218	Irritable bowel syndrome	[ICD-11: DD91]	Q9UNQ0	ABCG2
T56556	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	Q9UNQ0	ABCG2