4-[6,7-dihydroxy-5-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-3-yl]butane-1,2,4-triol

Details

• Internal ID: 0d37d836-c7ad-49ba-97b7-7d0251ea5c3a
• Taxonomy: Organoheterocyclic compounds > Pyrrolizidines
• IUPAC Name: 4-[6,7-dihydroxy-5-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-3-yl]butane-1,2,4-triol
• SMILES (Canonical): C1CC(N2C1C(C(C2CO)O)O)C(CC(CO)O)O
• SMILES (Isomeric): C1CC(N2C1C(C(C2CO)O)O)C(CC(CO)O)O
• InChI: InChI=1S/C12H23NO6/c14-4-6(16)3-10(17)7-1-2-8-11(18)12(19)9(5-15)13(7)8/h6-12,14-19H,1-5H2
• InChI Key: HFTWYUZUQUCVPO-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₃NO₆
• Molecular Weight: 277.31 g/mol
• Exact Mass: 277.15253745 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.98
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8228	82.28%
Caco-2	-	0.8856	88.56%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Lysosomes	0.4396	43.96%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.9590	95.90%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.9389	93.89%
P-glycoprotein inhibitior	-	0.9556	95.56%
P-glycoprotein substrate	-	0.7819	78.19%
CYP3A4 substrate	-	0.5163	51.63%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	+	0.5956	59.56%
CYP3A4 inhibition	-	0.9836	98.36%
CYP2C9 inhibition	-	0.9144	91.44%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.8285	82.85%
CYP2C8 inhibition	-	0.9421	94.21%
CYP inhibitory promiscuity	-	0.9825	98.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5887	58.87%
Eye corrosion	-	0.9728	97.28%
Eye irritation	-	0.9179	91.79%
Skin irritation	-	0.7335	73.35%
Skin corrosion	-	0.8910	89.10%
Ames mutagenesis	-	0.7654	76.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5736	57.36%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5468	54.68%
skin sensitisation	-	0.8908	89.08%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5350	53.50%
Acute Oral Toxicity (c)	III	0.5227	52.27%
Estrogen receptor binding	-	0.8033	80.33%
Androgen receptor binding	-	0.5720	57.20%
Thyroid receptor binding	-	0.5141	51.41%
Glucocorticoid receptor binding	-	0.6066	60.66%
Aromatase binding	-	0.6409	64.09%
PPAR gamma	-	0.7813	78.13%
Honey bee toxicity	-	0.6512	65.12%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.9688	96.88%

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	96.67%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.02%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.48%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	90.27%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.78%	97.09%
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	88.16%	97.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.31%	95.89%
CHEMBL237	P41145	Kappa opioid receptor	85.81%	98.10%
CHEMBL2094135	Q96BI3	Gamma-secretase	83.72%	98.05%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.52%	97.47%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.28%	97.29%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	80.04%	95.61%

Plants that contains it

• Scilla peruviana

Cross-Links

• PubChem: 72978987
• LOTUS: LTS0249876
• wikiData: Q105027543