[(1R,3R,5S,6S,7R)-3,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: d4b626f1-f208-464f-a739-39b9860be2cd
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1R,3R,5S,6S,7R)-3,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2CC(CC(C1O)N2C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@@H]2C[C@@H](C[C@H]([C@H]1O)N2C)O
• InChI: InChI=1S/C13H21NO4/c1-4-7(2)13(17)18-12-10-6-8(15)5-9(11(12)16)14(10)3/h4,8-12,15-16H,5-6H2,1-3H3/b7-4+/t8-,9-,10+,11-,12+/m1/s1
• InChI Key: QYQKPLMVSBIKQI-BFWODJAFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₁NO₄
• Molecular Weight: 255.31 g/mol
• Exact Mass: 255.14705815 g/mol
• Topological Polar Surface Area (TPSA): 70.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.06
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9002	90.02%
Caco-2	+	0.7794	77.94%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4667	46.67%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.9339	93.39%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9184	91.84%
P-glycoprotein inhibitior	-	0.9589	95.89%
P-glycoprotein substrate	-	0.8185	81.85%
CYP3A4 substrate	+	0.5212	52.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7487	74.87%
CYP3A4 inhibition	-	0.9859	98.59%
CYP2C9 inhibition	-	0.8932	89.32%
CYP2C19 inhibition	-	0.8616	86.16%
CYP2D6 inhibition	-	0.8444	84.44%
CYP1A2 inhibition	-	0.8375	83.75%
CYP2C8 inhibition	-	0.9858	98.58%
CYP inhibitory promiscuity	-	0.9556	95.56%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9407	94.07%
Carcinogenicity (trinary)	Non-required	0.5914	59.14%
Eye corrosion	-	0.9831	98.31%
Eye irritation	-	0.9823	98.23%
Skin irritation	-	0.7615	76.15%
Skin corrosion	-	0.9364	93.64%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6439	64.39%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.5573	55.73%
skin sensitisation	-	0.8677	86.77%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6553	65.53%
Acute Oral Toxicity (c)	III	0.5334	53.34%
Estrogen receptor binding	-	0.7893	78.93%
Androgen receptor binding	-	0.7209	72.09%
Thyroid receptor binding	+	0.5295	52.95%
Glucocorticoid receptor binding	-	0.6461	64.61%
Aromatase binding	-	0.8316	83.16%
PPAR gamma	-	0.8171	81.71%
Honey bee toxicity	-	0.6586	65.86%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7155	71.55%
Fish aquatic toxicity	-	0.5281	52.81%

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	97.30%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.48%	97.21%
CHEMBL2581	P07339	Cathepsin D	88.50%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	87.81%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.27%	97.25%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.87%	97.47%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.99%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.59%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.98%	90.17%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.12%	98.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.01%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.86%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.09%	95.89%

Plants that contains it

• Brugmansia suaveolens
• Chenopodium album

Cross-Links

• PubChem: 21770005
• NPASS: NPC109862
• LOTUS: LTS0134513
• wikiData: Q105230335