(1'S,2S,4R)-10-methoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohex-2-ene]-1',11-diol

Details

• Internal ID: ab75c3e9-9b6a-4980-8f9c-a6981870d8c9
• Taxonomy: Alkaloids and derivatives > Proaporphines
• IUPAC Name: (1'S,2S,4R)-10-methoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohex-2-ene]-1',11-diol
• SMILES (Canonical): CN1CCC2=CC(=C(C3=C2C1CC34CCC(C=C4)O)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C3=C2[C@H]1C[C@]34CC[C@@H](C=C4)O)O)OC
• InChI: InChI=1S/C18H23NO3/c1-19-8-5-11-9-14(22-2)17(21)16-15(11)13(19)10-18(16)6-3-12(20)4-7-18/h3,6,9,12-13,20-21H,4-5,7-8,10H2,1-2H3/t12-,13-,18+/m1/s1
• InChI Key: XXPUHUHGYZFFIO-VFVRVIDISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.40 g/mol
• Exact Mass: 301.16779360 g/mol
• Topological Polar Surface Area (TPSA): 52.90 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 4
• 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	+	0.9902	99.02%
Caco-2	+	0.6760	67.60%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5771	57.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9115	91.15%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.4583	45.83%
P-glycoprotein inhibitior	-	0.9058	90.58%
P-glycoprotein substrate	+	0.6214	62.14%
CYP3A4 substrate	+	0.6917	69.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6703	67.03%
CYP3A4 inhibition	-	0.8711	87.11%
CYP2C9 inhibition	-	0.8468	84.68%
CYP2C19 inhibition	-	0.7098	70.98%
CYP2D6 inhibition	+	0.6994	69.94%
CYP1A2 inhibition	-	0.6706	67.06%
CYP2C8 inhibition	-	0.7277	72.77%
CYP inhibitory promiscuity	-	0.9146	91.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6509	65.09%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9800	98.00%
Skin irritation	-	0.7359	73.59%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5548	55.48%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.7651	76.51%
skin sensitisation	-	0.8461	84.61%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.9340	93.40%
Acute Oral Toxicity (c)	III	0.4524	45.24%
Estrogen receptor binding	+	0.6732	67.32%
Androgen receptor binding	-	0.5148	51.48%
Thyroid receptor binding	+	0.5741	57.41%
Glucocorticoid receptor binding	+	0.6596	65.96%
Aromatase binding	-	0.6661	66.61%
PPAR gamma	-	0.5245	52.45%
Honey bee toxicity	-	0.8271	82.71%
Biodegradation	-	1.0000	100.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.8206	82.06%

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	99.60%	96.09%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	95.66%	91.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.46%	85.14%
CHEMBL2056	P21728	Dopamine D1 receptor	94.81%	91.00%
CHEMBL217	P14416	Dopamine D2 receptor	94.04%	95.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.84%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.69%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	91.86%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.76%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.21%	92.94%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.32%	93.40%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	89.05%	91.79%
CHEMBL5203	P33316	dUTP pyrophosphatase	88.31%	99.18%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.79%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.61%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.03%	94.00%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	84.98%	95.34%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.38%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.35%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.67%	97.25%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.65%	93.04%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.59%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.52%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.49%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.32%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.31%	90.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.05%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.24%	86.33%
CHEMBL3474	P14555	Phospholipase A2 group IIA	80.64%	94.05%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.31%	82.38%

Plants that contains it

• Andira surinamensis
• Aralia hispida
• Baeckea frutescens
• Balanophora polyandra
• Boeberastrum anthemidifolium
• Chenopodiastrum murale
• Chenopodium quinoa
• Citrus medica
• Coprosma foetidissima
• Cryptocarya chinensis
• Davidsonia pruriens
• Echinochloa crus-galli
• Eriocephalus kingesii
• Geranium collinum
• Girgensohnia oppositiflora
• Harpullia cupanioides
• Isodon eriocalyx
• Lilium pomponium
• Lychnophora pinaster
• Marrubium parviflorum
• Microglossa pyrifolia
• Parthenium confertum
• Polygonatum orientale
• Psathyrotes ramosissima
• Scleropyrum pentandrum
• Selliguea hastata
• Trifolium diffusum
• Veronica stricta
• Youngia japonica
• Zanthoxylum acuminatum subsp. juniperinum

Cross-Links

• PubChem: 10870351
• NPASS: NPC293933
• LOTUS: LTS0174918
• wikiData: Q105344147