Lithosenine

Details

• Internal ID: d90b12e5-e21e-4bb4-b3f9-85ec7626f3f9
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7R,8R)-7-(3-hydroxy-3-methylbutanoyl)oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2,3-dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
• SMILES (Canonical): CC(C(C(=O)OCC1=CCN2C1C(CC2)OC(=O)CC(C)(C)O)(C(C)(C)O)O)O
• SMILES (Isomeric): C[C@@H]([C@@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)CC(C)(C)O)(C(C)(C)O)O)O
• InChI: InChI=1S/C20H33NO8/c1-12(22)20(27,19(4,5)26)17(24)28-11-13-6-8-21-9-7-14(16(13)21)29-15(23)10-18(2,3)25/h6,12,14,16,22,25-27H,7-11H2,1-5H3/t12-,14+,16+,20+/m0/s1
• InChI Key: MOXWDXAGEVGLLJ-WMHAJJRKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₃NO₈
• Molecular Weight: 415.50 g/mol
• Exact Mass: 415.22061701 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -0.50
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6852	68.52%
Caco-2	-	0.5274	52.74%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6628	66.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8941	89.41%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5713	57.13%
P-glycoprotein inhibitior	-	0.7319	73.19%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6307	63.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7202	72.02%
CYP3A4 inhibition	-	0.9805	98.05%
CYP2C9 inhibition	-	0.8824	88.24%
CYP2C19 inhibition	-	0.8646	86.46%
CYP2D6 inhibition	-	0.8130	81.30%
CYP1A2 inhibition	-	0.8869	88.69%
CYP2C8 inhibition	-	0.6569	65.69%
CYP inhibitory promiscuity	-	0.9685	96.85%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.6938	69.38%
Eye corrosion	-	0.9807	98.07%
Eye irritation	-	0.9544	95.44%
Skin irritation	-	0.7383	73.83%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5410	54.10%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.9750	97.50%
skin sensitisation	-	0.8102	81.02%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5091	50.91%
Acute Oral Toxicity (c)	II	0.4078	40.78%
Estrogen receptor binding	+	0.5563	55.63%
Androgen receptor binding	+	0.5893	58.93%
Thyroid receptor binding	+	0.5965	59.65%
Glucocorticoid receptor binding	+	0.6967	69.67%
Aromatase binding	+	0.5327	53.27%
PPAR gamma	-	0.5637	56.37%
Honey bee toxicity	-	0.8346	83.46%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.4456	44.56%

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	99.08%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.34%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.31%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.08%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.14%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.25%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.14%	99.17%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	83.48%	94.97%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.25%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.60%	95.56%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.33%	90.24%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.21%	100.00%
CHEMBL5028	O14672	ADAM10	80.03%	97.50%

Plants that contains it

• Lithospermum officinale

Cross-Links

• PubChem: 101674026
• LOTUS: LTS0171380
• wikiData: Q105169232