(1R,6R,7S,8S,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol

Details

• Internal ID: b9028648-5320-43a8-95e1-69daafce0637
• Taxonomy: Organoheterocyclic compounds > Indolizidines
• IUPAC Name: (1R,6R,7S,8S,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol
• SMILES (Canonical): C1CN2CC(C(C(C2C1O)O)O)O
• SMILES (Isomeric): C1CN2C[C@H]([C@@H]([C@H]([C@@H]2[C@@H]1O)O)O)O
• InChI: InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m1/s1
• InChI Key: JDVVGAQPNNXQDW-HEIBUPTGSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.21 g/mol
• Exact Mass: 189.10010796 g/mol
• Topological Polar Surface Area (TPSA): 84.20 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.48
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

• SCHEMBL23845877

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7135	71.35%
Caco-2	-	0.8064	80.64%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4753	47.53%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.9684	96.84%
OATP1B3 inhibitior	+	0.9530	95.30%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9543	95.43%
P-glycoprotein inhibitior	-	0.9818	98.18%
P-glycoprotein substrate	-	0.8288	82.88%
CYP3A4 substrate	-	0.6017	60.17%
CYP2C9 substrate	+	0.5801	58.01%
CYP2D6 substrate	+	0.6011	60.11%
CYP3A4 inhibition	-	0.9974	99.74%
CYP2C9 inhibition	-	0.9406	94.06%
CYP2C19 inhibition	-	0.9390	93.90%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.8141	81.41%
CYP2C8 inhibition	-	0.9922	99.22%
CYP inhibitory promiscuity	-	0.9942	99.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6018	60.18%
Eye corrosion	-	0.9714	97.14%
Eye irritation	-	0.7694	76.94%
Skin irritation	-	0.6853	68.53%
Skin corrosion	-	0.8451	84.51%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5761	57.61%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.6681	66.81%
skin sensitisation	-	0.8664	86.64%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6230	62.30%
Acute Oral Toxicity (c)	III	0.5374	53.74%
Estrogen receptor binding	-	0.9051	90.51%
Androgen receptor binding	-	0.8084	80.84%
Thyroid receptor binding	-	0.8015	80.15%
Glucocorticoid receptor binding	-	0.7842	78.42%
Aromatase binding	-	0.8934	89.34%
PPAR gamma	-	0.8880	88.80%
Honey bee toxicity	-	0.8167	81.67%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.9671	96.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	95.75%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.02%	96.09%
CHEMBL3105	P09874	Poly [ADP-ribose] polymerase-1	85.94%	93.90%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	85.71%	98.46%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	84.14%	94.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.53%	95.89%
CHEMBL274	P51681	C-C chemokine receptor type 5	82.53%	98.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.06%	92.94%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	80.91%	95.58%
CHEMBL237	P41145	Kappa opioid receptor	80.32%	98.10%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	80.30%	95.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.27%	97.09%

Plants that contains it

• Castanospermum australe
• Clinopodium vulgare
• Commiphora sphaerocarpa
• Erythrina speciosa
• Helichrysum drakensbergense
• Piper divaricatum
• Prosopis africana
• Prunus prostrata
• Richteria pyrethroides
• Santolina pectinata

Cross-Links

• PubChem: 13959480
• NPASS: NPC95509
• LOTUS: LTS0194997
• wikiData: Q105125797