[(7S)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl 2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate

Details

• Internal ID: 5d1f37af-f799-47c0-84e1-1afe232fd3da
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7S)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl 2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
• SMILES (Canonical): CC(C)C(C(C)O)(C(=O)OCC1=CC[N+]2(C1C(CC2)O)[O-])O
• SMILES (Isomeric): CC(C)C(C(C)O)(C(=O)OCC1=CC[N+]2(C1[C@H](CC2)O)[O-])O
• InChI: InChI=1S/C15H25NO6/c1-9(2)15(20,10(3)17)14(19)22-8-11-4-6-16(21)7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10?,12-,13?,15?,16?/m0/s1
• InChI Key: DNAWGBOKUFFVMB-ZOJNAIIQSA-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): 105.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.31
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6502	65.02%
Caco-2	-	0.5640	56.40%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4975	49.75%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.9055	90.55%
OATP1B3 inhibitior	+	0.9381	93.81%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7953	79.53%
P-glycoprotein inhibitior	-	0.9395	93.95%
P-glycoprotein substrate	-	0.6107	61.07%
CYP3A4 substrate	+	0.5762	57.62%
CYP2C9 substrate	-	0.7952	79.52%
CYP2D6 substrate	-	0.8451	84.51%
CYP3A4 inhibition	-	0.9666	96.66%
CYP2C9 inhibition	-	0.8430	84.30%
CYP2C19 inhibition	-	0.7966	79.66%
CYP2D6 inhibition	-	0.8151	81.51%
CYP1A2 inhibition	-	0.8255	82.55%
CYP2C8 inhibition	-	0.6535	65.35%
CYP inhibitory promiscuity	-	0.9715	97.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Danger	0.6063	60.63%
Eye corrosion	-	0.9769	97.69%
Eye irritation	-	0.9375	93.75%
Skin irritation	-	0.7561	75.61%
Skin corrosion	-	0.9162	91.62%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7461	74.61%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.8226	82.26%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6997	69.97%
Acute Oral Toxicity (c)	III	0.4945	49.45%
Estrogen receptor binding	+	0.6168	61.68%
Androgen receptor binding	+	0.6594	65.94%
Thyroid receptor binding	-	0.5366	53.66%
Glucocorticoid receptor binding	+	0.7372	73.72%
Aromatase binding	+	0.5310	53.10%
PPAR gamma	-	0.5398	53.98%
Honey bee toxicity	-	0.8700	87.00%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	-	0.4399	43.99%

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	98.70%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.61%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.38%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.46%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.99%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.79%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.18%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.29%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.81%	94.45%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	83.48%	94.97%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.86%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	81.56%	83.82%

Plants that contains it

• Heliotropium amplexicaule
• Heliotropium indicum

Cross-Links

• PubChem: 10018581
• NPASS: NPC284644