Leptanthine

Details

• Internal ID: 23cb749d-c790-4bfb-8bc0-671339b04925
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate
• SMILES (Canonical): CC(C(C(=O)OCC1=CCN2C1C(CC2)O)(C(C)(C)O)O)O
• SMILES (Isomeric): C[C@H]([C@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)(C(C)(C)O)O)O
• InChI: InChI=1S/C15H25NO6/c1-9(17)15(21,14(2,3)20)13(19)22-8-10-4-6-16-7-5-11(18)12(10)16/h4,9,11-12,17-18,20-21H,5-8H2,1-3H3/t9-,11-,12-,15+/m1/s1
• InChI Key: GXIRVRAYFXJIRQ-CGEWXTDFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₅NO₆
• Molecular Weight: 315.36 g/mol
• Exact Mass: 315.16818752 g/mol
• Topological Polar Surface Area (TPSA): 111.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.21
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8001	80.01%
Caco-2	-	0.5675	56.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6611	66.11%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9049	90.49%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5944	59.44%
P-glycoprotein inhibitior	-	0.9531	95.31%
P-glycoprotein substrate	-	0.6058	60.58%
CYP3A4 substrate	+	0.5891	58.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3600	36.00%
CYP3A4 inhibition	-	0.9901	99.01%
CYP2C9 inhibition	-	0.8852	88.52%
CYP2C19 inhibition	-	0.8938	89.38%
CYP2D6 inhibition	-	0.7441	74.41%
CYP1A2 inhibition	-	0.8751	87.51%
CYP2C8 inhibition	-	0.7971	79.71%
CYP inhibitory promiscuity	-	0.9595	95.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.6383	63.83%
Eye corrosion	-	0.9816	98.16%
Eye irritation	-	0.9758	97.58%
Skin irritation	-	0.7516	75.16%
Skin corrosion	-	0.9177	91.77%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6366	63.66%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8142	81.42%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6285	62.85%
Acute Oral Toxicity (c)	II	0.4189	41.89%
Estrogen receptor binding	+	0.5358	53.58%
Androgen receptor binding	+	0.5689	56.89%
Thyroid receptor binding	-	0.5457	54.57%
Glucocorticoid receptor binding	+	0.7223	72.23%
Aromatase binding	+	0.5406	54.06%
PPAR gamma	-	0.5229	52.29%
Honey bee toxicity	-	0.8658	86.58%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.6544	65.44%

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	99.10%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.93%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.87%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.47%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.30%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.27%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.64%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.32%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.09%	95.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.75%	100.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.42%	90.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.01%	95.89%

Plants that contains it

• Echium vulgare
• Onosma leptantha

Cross-Links

• PubChem: 12085705
• LOTUS: LTS0141128
• wikiData: Q105023082