Benzoylecgonine

Details

• Internal ID: 293d98e4-5b70-4727-bc15-4674e8e7ba4b
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters
• IUPAC Name: (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• SMILES (Canonical): CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)O
• SMILES (Isomeric): CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)O
• InChI: InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1
• InChI Key: GVGYEFKIHJTNQZ-RFQIPJPRSA-N
• Popularity: 1,956 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₉NO₄
• Molecular Weight: 289.33 g/mol
• Exact Mass: 289.13140809 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 1.78
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• O-Benzoylecgonine
• Ecgonine benzoate
• (-)-Benzoylecgonine
• o-Benzoyl-(-)-ecgonine
• 519-09-5
• benzoyl ecgonine
• 3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• CHEBI:41001
• UNII-5353I8I6YS
• DTXSID7046758
• 5353I8I6YS
• EINECS 208-263-5
• (1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• DTXCID5026758
• Benzoylecgonine hydrate
• BEG
• CAS-519-09-5
• (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• Theracys
• Cocaine metabolite
• 3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID
• NCGC00168248-01
• NCGC00168248-02
• Benzoylecgonine (BECG)
• Epitope ID:158630
• BENZOYLECGONINE [MI]
• SCHEMBL116803
• CHEMBL1231248
• Ecgonine, benzoate (6CI,7CI)
• 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, (1R,2R,3S,5S)-
• GVGYEFKIHJTNQZ-RFQIPJPRSA-N
• ECGONINE BENZOATE [WHO-DD]
• Benzoylecgonine, 1mg/ml in Methanol
• Tox21_112607
• Tox21_112853
• AKOS030254449
• Benzoylecgonine 0.1 mg/ml in Methanol
• Benzoylecgonine 1.0 mg/ml in Methanol
• DB01515
• Q2499888
• 3beta-HYDROXY-1alphaH,5alphaH-TROPANE-2beta-CARBOXYLIC ACID BENZOATE
• (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• 1alphaH,5alphaH-Tropane-2beta-carboxylic acid, 3beta-hydroxy-, benzoate (ester) (8CI)
• 3-beta-hydroxy-1-alpha-H,-5-alpha-H-tropane-2-beta-carboxylic acid benzoate
• 3.BETA.-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLIC ACID BENZOATE
• 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, (1R,2R,3S,5S)- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8617	86.17%
Caco-2	+	0.7441	74.41%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5359	53.59%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.9339	93.39%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.9011	90.11%
P-glycoprotein inhibitior	-	0.8674	86.74%
P-glycoprotein substrate	+	0.5913	59.13%
CYP3A4 substrate	+	0.6297	62.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6939	69.39%
CYP3A4 inhibition	-	0.9550	95.50%
CYP2C9 inhibition	-	0.9445	94.45%
CYP2C19 inhibition	-	0.9540	95.40%
CYP2D6 inhibition	-	0.8493	84.93%
CYP1A2 inhibition	-	0.8832	88.32%
CYP2C8 inhibition	-	0.8550	85.50%
CYP inhibitory promiscuity	-	0.9730	97.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6248	62.48%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9414	94.14%
Skin irritation	-	0.7992	79.92%
Skin corrosion	-	0.9502	95.02%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7259	72.59%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.9309	93.09%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5729	57.29%
Acute Oral Toxicity (c)	III	0.6428	64.28%
Estrogen receptor binding	-	0.7079	70.79%
Androgen receptor binding	-	0.8523	85.23%
Thyroid receptor binding	-	0.7881	78.81%
Glucocorticoid receptor binding	-	0.8391	83.91%
Aromatase binding	-	0.6720	67.20%
PPAR gamma	-	0.7054	70.54%
Honey bee toxicity	-	0.9504	95.04%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5345	53.45%
Fish aquatic toxicity	+	0.8283	82.83%

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	95.75%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.49%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.34%	97.21%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	91.53%	94.23%
CHEMBL221	P23219	Cyclooxygenase-1	90.82%	90.17%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	90.10%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.05%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.20%	86.33%
CHEMBL238	Q01959	Dopamine transporter	88.10%	95.88%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	87.90%	97.53%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.74%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.26%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.81%	94.62%
CHEMBL4208	P20618	Proteasome component C5	82.48%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.84%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	81.83%	91.49%
CHEMBL5028	O14672	ADAM10	81.32%	97.50%
CHEMBL2535	P11166	Glucose transporter	81.22%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.19%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.99%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.67%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.39%	83.00%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.29%	91.43%

Plants that contains it

• Erythroxylum coca

Cross-Links

• PubChem: 448223
• LOTUS: LTS0050319
• wikiData: Q2499888