1H-Pyrrolizine-1-carboxylic acid, hexahydro-6-hydroxy-, (1R,6R,7aR)-

Details

• Internal ID: c8f0baa3-c8fd-4d67-b411-2be21bbb4d6b
• Taxonomy: Organoheterocyclic compounds > Pyrrolizidines
• IUPAC Name: (1R,6R,8R)-6-hydroxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1-carboxylic acid
• SMILES (Canonical): C1CN2CC(CC2C1C(=O)O)O
• SMILES (Isomeric): C1CN2C[C@@H](C[C@@H]2[C@@H]1C(=O)O)O
• InChI: InChI=1S/C8H13NO3/c10-5-3-7-6(8(11)12)1-2-9(7)4-5/h5-7,10H,1-4H2,(H,11,12)/t5-,6-,7-/m1/s1
• InChI Key: TUHKEMPPAFZCIP-FSDSQADBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.19 g/mol
• Exact Mass: 171.08954328 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -0.47
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• (+)-amphorogynine D
• 1H-Pyrrolizine-1-carboxylic acid, hexahydro-6-hydroxy-, (1R,6R,7aR)-
• 215932-88-0
• InChI=1/C8H13NO3/c10-5-3-7-6(8(11)12)1-2-9(7)4-5/h5-7,10H,1-4H2,(H,11,12)/t5-,6-,7-/m1/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9684	96.84%
Caco-2	-	0.7292	72.92%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5575	55.75%
OATP2B1 inhibitior	-	0.8418	84.18%
OATP1B1 inhibitior	+	0.9693	96.93%
OATP1B3 inhibitior	+	0.9508	95.08%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9372	93.72%
P-glycoprotein inhibitior	-	0.9908	99.08%
P-glycoprotein substrate	-	0.8829	88.29%
CYP3A4 substrate	-	0.5826	58.26%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	+	0.4525	45.25%
CYP3A4 inhibition	-	0.9791	97.91%
CYP2C9 inhibition	-	0.9561	95.61%
CYP2C19 inhibition	-	0.9350	93.50%
CYP2D6 inhibition	-	0.9366	93.66%
CYP1A2 inhibition	-	0.7747	77.47%
CYP2C8 inhibition	-	0.9820	98.20%
CYP inhibitory promiscuity	-	0.9906	99.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5880	58.80%
Eye corrosion	-	0.9578	95.78%
Eye irritation	+	0.7506	75.06%
Skin irritation	-	0.6844	68.44%
Skin corrosion	-	0.8247	82.47%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8265	82.65%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.9000	90.00%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4523	45.23%
Acute Oral Toxicity (c)	III	0.5760	57.60%
Estrogen receptor binding	-	0.8800	88.00%
Androgen receptor binding	-	0.6030	60.30%
Thyroid receptor binding	-	0.9034	90.34%
Glucocorticoid receptor binding	-	0.6644	66.44%
Aromatase binding	-	0.9014	90.14%
PPAR gamma	-	0.8735	87.35%
Honey bee toxicity	-	0.9372	93.72%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.9401	94.01%

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	89.12%	96.09%
CHEMBL274	P51681	C-C chemokine receptor type 5	87.85%	98.77%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.50%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.80%	91.19%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	84.19%	96.03%
CHEMBL217	P14416	Dopamine D2 receptor	81.15%	95.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.82%	99.23%

Plants that contains it

• Amphorogyne spicata

Cross-Links

• PubChem: 5324491
• LOTUS: LTS0273169
• wikiData: Q105264777