Paynantheine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	388697f4-6361-48e3-8716-b55b70ee8023
Taxonomy	Alkaloids and derivatives > Corynanthean-type alkaloids
IUPAC Name	methyl (E)-2-[(2S,3R,12bS)-3-ethenyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
SMILES (Canonical)	COC=C(C1CC2C3=C(CCN2CC1C=C)C4=C(N3)C=CC=C4OC)C(=O)OC
SMILES (Isomeric)	CO/C=C(\[C@H]1C[C@H]2C3=C(CCN2C[C@@H]1C=C)C4=C(N3)C=CC=C4OC)/C(=O)OC
InChI	InChI=1S/C23H28N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13+/t14-,16-,19-/m0/s1
InChI Key	JGZKIGWXPPFMRG-CYSPOEIOSA-N
Popularity	9 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₂₈N₂O₄
Molecular Weight	396.50 g/mol
Exact Mass	396.20490738 g/mol
Topological Polar Surface Area (TPSA)	63.80 Å²
XlogP	3.20
Atomic LogP (AlogP)	3.60
H-Bond Acceptor	5
H-Bond Donor	1
Rotatable Bonds	5

Synonyms

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4697-66-9

(+)-Paynantheine

PATULIN(RG)

1346-36-7

YLG43M4U5V

CHEMBL4848517

methyl (E)-2-[(2S,3R,12bS)-3-ethenyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Indolo(2,3-a)quinolizine, corynan-16-carboxylic acid deriv

17,18-Secoyohimban-16-carboxylic acid, 16,17,18,19-tetradehydro-9,17-dimethoxy-, methyl ester, (E)-

Indolo2,3-aquinolizine-2-acetic acid, 3-ethenyl-1,2,3,4,6,7,12,12b-octahydro-8-methoxy-.alpha.-(methoxymethylene)-, methyl ester, (.alpha.E,2S,3R,12bS)-

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9788	97.88%
Caco-2	+	0.6794	67.94%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7529	75.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9264	92.64%
OATP1B3 inhibitior	+	0.8466	84.66%
MATE1 inhibitior	-	0.8019	80.19%
OCT2 inhibitior	-	0.5639	56.39%
BSEP inhibitior	+	0.9621	96.21%
P-glycoprotein inhibitior	+	0.8513	85.13%
P-glycoprotein substrate	+	0.7062	70.62%
CYP3A4 substrate	+	0.6991	69.91%
CYP2C9 substrate	-	0.6070	60.70%
CYP2D6 substrate	+	0.3633	36.33%
CYP3A4 inhibition	-	0.5387	53.87%
CYP2C9 inhibition	-	0.7518	75.18%
CYP2C19 inhibition	-	0.8594	85.94%
CYP2D6 inhibition	-	0.5917	59.17%
CYP1A2 inhibition	+	0.8149	81.49%
CYP2C8 inhibition	+	0.5379	53.79%
CYP inhibitory promiscuity	+	0.5660	56.60%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5940	59.40%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9788	97.88%
Skin irritation	-	0.7589	75.89%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8566	85.66%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8712	87.12%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.8524	85.24%
Acute Oral Toxicity (c)	III	0.5886	58.86%
Estrogen receptor binding	+	0.5302	53.02%
Androgen receptor binding	+	0.7420	74.20%
Thyroid receptor binding	+	0.5542	55.42%
Glucocorticoid receptor binding	+	0.7854	78.54%
Aromatase binding	-	0.6244	62.44%
PPAR gamma	-	0.5185	51.85%
Honey bee toxicity	-	0.7679	76.79%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9718	97.18%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.21%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.73%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL2535	P11166	Glucose transporter	94.29%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.44%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.74%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.11%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.71%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.68%	97.25%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.21%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	83.92%	91.19%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.79%	93.03%
CHEMBL5028	O14672	ADAM10	83.54%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.63%	97.09%
CHEMBL4302	P08183	P-glycoprotein 1	81.62%	92.98%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.42%	95.89%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.36%	95.56%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.21%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.01%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.94%	89.62%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.63%	97.50%
CHEMBL1255126	O15151	Protein Mdm4	80.62%	90.20%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Penstemon gentianoides

Picris conyzoides