Mecambrine

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	aa12f1c1-2cc2-45aa-aebf-e5870b17b2e1
Taxonomy	Alkaloids and derivatives > Proaporphines
IUPAC Name	(12S)-11-methylspiro[3,5-dioxa-11-azatetracyclo[6.6.1.02,6.012,15]pentadeca-1(15),2(6),7-triene-14,4'-cyclohexa-2,5-diene]-1'-one
SMILES (Canonical)	CN1CCC2=CC3=C(C4=C2C1CC45C=CC(=O)C=C5)OCO3
SMILES (Isomeric)	CN1CCC2=CC3=C(C4=C2[C@@H]1CC45C=CC(=O)C=C5)OCO3
InChI	InChI=1S/C18H17NO3/c1-19-7-4-11-8-14-17(22-10-21-14)16-15(11)13(19)9-18(16)5-2-12(20)3-6-18/h2-3,5-6,8,13H,4,7,9-10H2,1H3/t13-/m0/s1
InChI Key	NMVDXQMYKKNYFO-ZDUSSCGKSA-N
Popularity	19 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₈H₁₇NO₃
Molecular Weight	295.30 g/mol
Exact Mass	295.12084340 g/mol
Topological Polar Surface Area (TPSA)	38.80 Å²
XlogP	2.40
Atomic LogP (AlogP)	2.28
H-Bond Acceptor	4
H-Bond Donor	0
Rotatable Bonds	0

Synonyms

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Fugapavine

(-)-Mecambrine

1093-07-8

C09588

CHEBI:6705

DTXSID90911090

LS-89391

Q27107306

(12S)-11-methylspiro[3,5-dioxa-11-azatetracyclo[6.6.1.02,6.012,15]pentadeca-1(15),2(6),7-triene-14,4'-cyclohexa-2,5-diene]-1'-one

3'-Methyl-2'a,3',4',5'-tetrahydro-2'H,8'H-spiro[cyclohexa-2,5-diene-1,1'-cyclopenta[ij][1,3]dioxolo[4,5-g]isoquinolin]-4-one

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	+	0.9929	99.29%
Caco-2	+	0.7651	76.51%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4621	46.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9474	94.74%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7007	70.07%
P-glycoprotein inhibitior	-	0.8257	82.57%
P-glycoprotein substrate	-	0.7099	70.99%
CYP3A4 substrate	+	0.6431	64.31%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.7112	71.12%
CYP3A4 inhibition	+	0.5211	52.11%
CYP2C9 inhibition	-	0.9220	92.20%
CYP2C19 inhibition	-	0.7000	70.00%
CYP2D6 inhibition	+	0.7844	78.44%
CYP1A2 inhibition	+	0.5321	53.21%
CYP2C8 inhibition	-	0.8910	89.10%
CYP inhibitory promiscuity	-	0.6294	62.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5790	57.90%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9742	97.42%
Skin irritation	-	0.7764	77.64%
Skin corrosion	-	0.9257	92.57%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4892	48.92%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.6571	65.71%
skin sensitisation	-	0.7895	78.95%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6640	66.40%
Acute Oral Toxicity (c)	III	0.6611	66.11%
Estrogen receptor binding	+	0.6158	61.58%
Androgen receptor binding	+	0.6255	62.55%
Thyroid receptor binding	-	0.6515	65.15%
Glucocorticoid receptor binding	-	0.5928	59.28%
Aromatase binding	-	0.5277	52.77%
PPAR gamma	+	0.5526	55.26%
Honey bee toxicity	-	0.8057	80.57%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9291	92.91%

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
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	99.49%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	98.23%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.39%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.17%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.41%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.80%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.63%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.05%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.31%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	86.00%	91.49%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.96%	90.71%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.69%	91.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.62%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.12%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.08%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.06%	92.62%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.63%	96.38%
CHEMBL230	P35354	Cyclooxygenase-2	83.41%	89.63%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.41%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.03%	93.04%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.74%	97.25%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.22%	90.24%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.09%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.79%	99.23%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.63%	82.38%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.11%	86.00%

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.