(1R,12S)-12,15-dihydroxy-16-methoxy-21-methyl-6,8-dioxa-21-azapentacyclo[10.9.0.02,10.05,9.013,18]henicosa-2(10),3,5(9),13,15,17-hexaen-11-one

Details

• Internal ID: 39b6e425-d543-459c-befe-1941c6d03165
• Taxonomy: Organoheterocyclic compounds > Benzazepines
• IUPAC Name: (1R,12S)-12,15-dihydroxy-16-methoxy-21-methyl-6,8-dioxa-21-azapentacyclo[10.9.0.02,10.05,9.013,18]henicosa-2(10),3,5(9),13,15,17-hexaen-11-one
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C3(C1C4=C(C3=O)C5=C(C=C4)OCO5)O)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2[C@@]3([C@H]1C4=C(C3=O)C5=C(C=C4)OCO5)O)O)OC
• InChI: InChI=1S/C20H19NO6/c1-21-6-5-10-7-15(25-2)13(22)8-12(10)20(24)18(21)11-3-4-14-17(27-9-26-14)16(11)19(20)23/h3-4,7-8,18,22,24H,5-6,9H2,1-2H3/t18-,20+/m1/s1
• InChI Key: BJGPRDJBNLOGMI-QUCCMNQESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉NO₆
• Molecular Weight: 369.40 g/mol
• Exact Mass: 369.12123733 g/mol
• Topological Polar Surface Area (TPSA): 88.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.74
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7479	74.79%
Caco-2	+	0.7455	74.55%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Lysosomes	0.5246	52.46%
OATP2B1 inhibitior	-	0.7247	72.47%
OATP1B1 inhibitior	+	0.9238	92.38%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5965	59.65%
P-glycoprotein inhibitior	-	0.5957	59.57%
P-glycoprotein substrate	-	0.5914	59.14%
CYP3A4 substrate	+	0.6872	68.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3585	35.85%
CYP3A4 inhibition	-	0.5187	51.87%
CYP2C9 inhibition	-	0.6895	68.95%
CYP2C19 inhibition	-	0.5495	54.95%
CYP2D6 inhibition	-	0.7555	75.55%
CYP1A2 inhibition	-	0.8634	86.34%
CYP2C8 inhibition	-	0.7184	71.84%
CYP inhibitory promiscuity	-	0.6985	69.85%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5449	54.49%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.8919	89.19%
Skin irritation	-	0.7921	79.21%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6327	63.27%
Micronuclear	+	0.6074	60.74%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8529	85.29%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.5894	58.94%
Acute Oral Toxicity (c)	III	0.6427	64.27%
Estrogen receptor binding	+	0.7925	79.25%
Androgen receptor binding	+	0.6395	63.95%
Thyroid receptor binding	+	0.5684	56.84%
Glucocorticoid receptor binding	+	0.8285	82.85%
Aromatase binding	+	0.6162	61.62%
PPAR gamma	+	0.7509	75.09%
Honey bee toxicity	-	0.7681	76.81%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.8727	87.27%

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	98.36%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.09%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.91%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.70%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.68%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.11%	93.40%
CHEMBL2581	P07339	Cathepsin D	96.77%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.24%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.69%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.59%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.11%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.62%	92.62%
CHEMBL261	P00915	Carbonic anhydrase I	89.15%	96.76%
CHEMBL2056	P21728	Dopamine D1 receptor	88.83%	91.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.72%	93.99%
CHEMBL4208	P20618	Proteasome component C5	88.38%	90.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	88.09%	82.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.45%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.34%	94.00%
CHEMBL2535	P11166	Glucose transporter	86.28%	98.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.28%	82.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.10%	99.23%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	84.98%	90.95%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.34%	96.86%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.28%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.14%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.70%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.59%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.45%	100.00%

Plants that contains it

• Fumaria officinalis

Cross-Links

• PubChem: 162930739
• LOTUS: LTS0036093
• wikiData: Q104937085