Heliotropamide

Details

• Internal ID: d415045f-2b45-470c-adfe-ff4160610e81
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Phenylpyrrolidines
• IUPAC Name: (2S,3S,4Z)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-N,1-bis[2-(4-hydroxyphenyl)ethyl]-5-oxopyrrolidine-3-carboxamide
• SMILES (Canonical): COC1=C(C=CC(=C1)C=C2C(C(N(C2=O)CCC3=CC=C(C=C3)O)C4=CC(=C(C=C4)O)OC)C(=O)NCCC5=CC=C(C=C5)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C\2/[C@@H]([C@H](N(C2=O)CCC3=CC=C(C=C3)O)C4=CC(=C(C=C4)O)OC)C(=O)NCCC5=CC=C(C=C5)O)O
• InChI: InChI=1S/C36H36N2O8/c1-45-31-20-24(7-13-29(31)41)19-28-33(35(43)37-17-15-22-3-9-26(39)10-4-22)34(25-8-14-30(42)32(21-25)46-2)38(36(28)44)18-16-23-5-11-27(40)12-6-23/h3-14,19-21,33-34,39-42H,15-18H2,1-2H3,(H,37,43)/b28-19-/t33-,34+/m0/s1
• InChI Key: VNFIQMCRAYEPSY-FXJSISFJSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₆N₂O₈
• Molecular Weight: 624.70 g/mol
• Exact Mass: 624.24716611 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.71
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

• CHEMBL451587
• (2S,3S,4Z)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-N,1-bis[2-(4-hydroxyphenyl)ethyl]-5-oxopyrrolidine-3-carboxamide
• 3-pyrrolidinecarboxamide, 2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methylene]-N,1-bis[2-(4-hydroxyphenyl)ethyl]-5-oxo-, (2S,3S,4Z)-
• 4-(4-Hydroxy-3-methoxy-benzylidene)-2-(4-hydroxy-3-methoxy-phenyl)-1-[2-(4-hydroxy-phenyl)-ethyl]-5-oxo-pyrrolidine-3-carboxylic acid [2-(4-hydroxy-phenyl)-ethyl]-amide
• InChI=1/C36H36N2O8/c1-45-31-20-24(7-13-29(31)41)19-28-33(35(43)37-17-15-22-3-9-26(39)10-4-22)34(25-8-14-30(42)32(21-25)46-2)38(36(28)44)18-16-23-5-11-27(40)12-6-23/h3-14,19-21,33-34,39-42H,15-18H2,1-2H3,(H,37,43)/b28-19-/t33-,34+/m0/s
• rel-(2R,3R,4Z)-4-(4-hydroxy-3-methoxybenzylidene)-2-(4-hydroxy-3-methoxyphenyl)-N,1-bis[2-(4-hydroxyphenyl)ethyl]-5-oxopyrrolidine-3-carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9534	95.34%
Caco-2	-	0.8349	83.49%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8238	82.38%
OATP2B1 inhibitior	+	0.5656	56.56%
OATP1B1 inhibitior	+	0.8644	86.44%
OATP1B3 inhibitior	+	0.9312	93.12%
MATE1 inhibitior	-	0.8254	82.54%
OCT2 inhibitior	-	0.7529	75.29%
BSEP inhibitior	+	0.9958	99.58%
P-glycoprotein inhibitior	+	0.9007	90.07%
P-glycoprotein substrate	+	0.7237	72.37%
CYP3A4 substrate	+	0.6777	67.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8118	81.18%
CYP3A4 inhibition	+	0.7136	71.36%
CYP2C9 inhibition	+	0.5467	54.67%
CYP2C19 inhibition	+	0.5753	57.53%
CYP2D6 inhibition	-	0.8523	85.23%
CYP1A2 inhibition	-	0.8277	82.77%
CYP2C8 inhibition	+	0.8040	80.40%
CYP inhibitory promiscuity	-	0.6409	64.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5841	58.41%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9397	93.97%
Skin irritation	-	0.7891	78.91%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6937	69.37%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6146	61.46%
skin sensitisation	-	0.8929	89.29%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9110	91.10%
Acute Oral Toxicity (c)	III	0.6699	66.99%
Estrogen receptor binding	+	0.7629	76.29%
Androgen receptor binding	+	0.7471	74.71%
Thyroid receptor binding	+	0.5929	59.29%
Glucocorticoid receptor binding	+	0.7890	78.90%
Aromatase binding	-	0.6070	60.70%
PPAR gamma	+	0.7689	76.89%
Honey bee toxicity	-	0.7838	78.38%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7973	79.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.10%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.15%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.72%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.71%	86.33%
CHEMBL233	P35372	Mu opioid receptor	92.24%	97.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.03%	85.14%
CHEMBL4208	P20618	Proteasome component C5	91.52%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.07%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.45%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.17%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.69%	89.00%
CHEMBL2535	P11166	Glucose transporter	87.39%	98.75%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	86.49%	83.65%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.93%	85.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.05%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.02%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.31%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.17%	85.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.62%	97.28%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.36%	94.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.82%	95.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.86%	97.21%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	80.40%	96.25%

Plants that contains it

• Euploca ovalifolia

Cross-Links

• PubChem: 637321
• LOTUS: LTS0002671
• wikiData: Q105289579