Erythro-canabisine H

Details

• Internal ID: ecb30505-b4cd-40ae-9795-1400151c5efe
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (E)-3-[4-[(1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)NCCC2=CC=C(C=C2)O)OC(CO)C(C3=CC(=C(C=C3)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)NCCC2=CC=C(C=C2)O)O[C@@H](CO)[C@H](C3=CC(=C(C=C3)O)OC)O
• InChI: InChI=1S/C28H31NO8/c1-35-24-16-20(7-10-22(24)32)28(34)26(17-30)37-23-11-5-19(15-25(23)36-2)6-12-27(33)29-14-13-18-3-8-21(31)9-4-18/h3-12,15-16,26,28,30-32,34H,13-14,17H2,1-2H3,(H,29,33)/b12-6+/t26-,28-/m0/s1
• InChI Key: PJAFJMNWVUKNOR-MGBVTPAKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₁NO₈
• Molecular Weight: 509.50 g/mol
• Exact Mass: 509.20496695 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.96
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 12

Synonyms

• Cannabisin H
• (E)-3-[4-[(1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
• 403647-08-5
• AKOS040763580
• FS-8124
• 2-propenamide, 3-[4-[[(1S,2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl]oxy]-3-methoxyphenyl]-N-[2-(4-hydroxyphenyl)ethyl]-, (2E)-
• 3-{4-[2-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-1-hydroxymethyl-ethoxy]-3-methoxy-phenyl}-N-[2-(4-hydroxy-phenyl)-ethyl]-acrylamide
• Erythro-1-(4-hydroxy-3-methoxyphenyl)-2-{4-{2-[N-2-(4-hydroxyphenyl)ethyl]carbamoylethenyl-2-methoxyphenoxyl}}-1,3-propanodiol
• InChI=1/C28H31NO8/c1-35-24-16-20(7-10-22(24)32)28(34)26(17-30)37-23-11-5-19(15-25(23)36-2)6-12-27(33)29-14-13-18-3-8-21(31)9-4-18/h3-12,15-16,26,28,30-32,34H,13-14,17H2,1-2H3,(H,29,33)/b12-6+/t26-,28-/m0/s
• rel-(2E)-3-(4-{[(1R,2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl]oxy}-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]acrylamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	-	0.7917	79.17%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6357	63.57%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8807	88.07%
OATP1B3 inhibitior	+	0.9513	95.13%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	+	0.8873	88.73%
P-glycoprotein inhibitior	+	0.8099	80.99%
P-glycoprotein substrate	+	0.7801	78.01%
CYP3A4 substrate	+	0.6207	62.07%
CYP2C9 substrate	-	0.8088	80.88%
CYP2D6 substrate	-	0.8051	80.51%
CYP3A4 inhibition	+	0.5441	54.41%
CYP2C9 inhibition	-	0.7510	75.10%
CYP2C19 inhibition	-	0.8892	88.92%
CYP2D6 inhibition	-	0.6634	66.34%
CYP1A2 inhibition	-	0.6185	61.85%
CYP2C8 inhibition	+	0.7988	79.88%
CYP inhibitory promiscuity	-	0.7193	71.93%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.8528	85.28%
Carcinogenicity (trinary)	Non-required	0.7501	75.01%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9422	94.22%
Skin irritation	-	0.7638	76.38%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8526	85.26%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6573	65.73%
skin sensitisation	-	0.8825	88.25%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9505	95.05%
Acute Oral Toxicity (c)	III	0.7899	78.99%
Estrogen receptor binding	+	0.7510	75.10%
Androgen receptor binding	+	0.8037	80.37%
Thyroid receptor binding	+	0.6425	64.25%
Glucocorticoid receptor binding	+	0.7634	76.34%
Aromatase binding	-	0.5745	57.45%
PPAR gamma	+	0.6672	66.72%
Honey bee toxicity	-	0.8005	80.05%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.6402	64.02%

Targets

Proven Targets:

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	99.05%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.61%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.80%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.67%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	95.44%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.08%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.64%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.42%	94.45%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	93.16%	89.33%
CHEMBL2535	P11166	Glucose transporter	93.06%	98.75%
CHEMBL4208	P20618	Proteasome component C5	91.58%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.77%	89.00%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	88.22%	96.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.45%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.25%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.18%	95.89%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	86.96%	97.03%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.44%	89.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.21%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.15%	85.14%
CHEMBL1914	P06276	Butyrylcholinesterase	85.21%	95.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.59%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.36%	96.95%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.79%	85.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.72%	97.21%
CHEMBL268	P43235	Cathepsin K	80.42%	96.85%

Plants that contains it

• Hibiscus cannabinus

Cross-Links

• PubChem: 636543
• LOTUS: LTS0018014
• wikiData: Q104399916