bohemamine C

Details

• Internal ID: 9f6b14b2-a7a8-4192-9b83-254715bb957d
• Taxonomy: Organoheterocyclic compounds > Pyrrolizines
• IUPAC Name: N-[(5S,7R,8S)-7-hydroxy-5,8-dimethyl-1-oxo-6,7-dihydro-5H-pyrrolizin-3-yl]-3-methylbut-2-enamide
• SMILES (Canonical): CC1CC(C2(N1C(=CC2=O)NC(=O)C=C(C)C)C)O
• SMILES (Isomeric): C[C@H]1C[C@H]([C@@]2(N1C(=CC2=O)NC(=O)C=C(C)C)C)O
• InChI: InChI=1S/C14H20N2O3/c1-8(2)5-13(19)15-12-7-11(18)14(4)10(17)6-9(3)16(12)14/h5,7,9-10,17H,6H2,1-4H3,(H,15,19)/t9-,10+,14-/m0/s1
• InChI Key: ZZUUBNUUMJZTMI-RBZYPMLTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₀N₂O₃
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.14739250 g/mol
• Topological Polar Surface Area (TPSA): 69.60 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.71
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CHEMBL513287
• N-[(5S,7R,8S)-7-hydroxy-5,8-dimethyl-1-oxo-6,7-dihydro-5H-pyrrolizin-3-yl]-3-methylbut-2-enamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9816	98.16%
Caco-2	+	0.7455	74.55%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4686	46.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9260	92.60%
OATP1B3 inhibitior	+	0.9374	93.74%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4875	48.75%
P-glycoprotein inhibitior	-	0.9399	93.99%
P-glycoprotein substrate	-	0.5535	55.35%
CYP3A4 substrate	+	0.5450	54.50%
CYP2C9 substrate	-	0.5983	59.83%
CYP2D6 substrate	-	0.8602	86.02%
CYP3A4 inhibition	-	0.9612	96.12%
CYP2C9 inhibition	-	0.6563	65.63%
CYP2C19 inhibition	-	0.7029	70.29%
CYP2D6 inhibition	-	0.9063	90.63%
CYP1A2 inhibition	-	0.7116	71.16%
CYP2C8 inhibition	-	0.9173	91.73%
CYP inhibitory promiscuity	-	0.8073	80.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5015	50.15%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9700	97.00%
Skin irritation	-	0.7560	75.60%
Skin corrosion	-	0.8980	89.80%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6565	65.65%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.6658	66.58%
skin sensitisation	-	0.8379	83.79%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4927	49.27%
Acute Oral Toxicity (c)	III	0.5146	51.46%
Estrogen receptor binding	+	0.7580	75.80%
Androgen receptor binding	+	0.6923	69.23%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5129	51.29%
Aromatase binding	-	0.6112	61.12%
PPAR gamma	+	0.6466	64.66%
Honey bee toxicity	-	0.8790	87.90%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.6451	64.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.94%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.40%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.78%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.90%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.42%	91.19%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.62%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.57%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.34%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.04%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.52%	94.45%
CHEMBL2581	P07339	Cathepsin D	83.50%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.02%	93.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11994821
• LOTUS: LTS0110018
• wikiData: Q105387098