Retronecanol

Details

• Internal ID: 9007c09b-44ed-4ca1-8beb-a795d4d8a5a0
• Taxonomy: Organoheterocyclic compounds > Pyrrolizidines
• IUPAC Name: (1R,7S,8R)-7-methyl-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol
• SMILES (Canonical): CC1CCN2C1C(CC2)O
• SMILES (Isomeric): C[C@H]1CCN2[C@H]1[C@@H](CC2)O
• InChI: InChI=1S/C8H15NO/c1-6-2-4-9-5-3-7(10)8(6)9/h6-8,10H,2-5H2,1H3/t6-,7+,8+/m0/s1
• InChI Key: PGMBNUMLNAJSJR-XLPZGREQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.21 g/mol
• Exact Mass: 141.115364102 g/mol
• Topological Polar Surface Area (TPSA): 23.50 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.46
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 04U250A48R
• 567-39-5
• RETRONSCANOL
• 1H-Pyrrolizin-1-ol, hexahydro-7-methyl-, (1R-(1alpha,7alpha,7abeta))-
• NSC-62958
• (-)-RETRONECANOL
• UNII-04U250A48R
• 7.BETA.-HYDROXYHELIOTRIDANE
• NSC 62958
• 1H-Pyrrolizin-1-ol, hexahydro-7-methyl-, (1R,7S,7aR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9891	98.91%
Caco-2	+	0.7791	77.91%
Blood Brain Barrier	+	0.7879	78.79%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Lysosomes	0.8136	81.36%
OATP2B1 inhibitior	-	0.8427	84.27%
OATP1B1 inhibitior	+	0.9697	96.97%
OATP1B3 inhibitior	+	0.9445	94.45%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.9059	90.59%
P-glycoprotein inhibitior	-	0.9861	98.61%
P-glycoprotein substrate	-	0.8734	87.34%
CYP3A4 substrate	-	0.5924	59.24%
CYP2C9 substrate	-	0.8202	82.02%
CYP2D6 substrate	+	0.6234	62.34%
CYP3A4 inhibition	-	0.9772	97.72%
CYP2C9 inhibition	-	0.9317	93.17%
CYP2C19 inhibition	-	0.8792	87.92%
CYP2D6 inhibition	-	0.7769	77.69%
CYP1A2 inhibition	-	0.8769	87.69%
CYP2C8 inhibition	-	0.9917	99.17%
CYP inhibitory promiscuity	-	0.9867	98.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5068	50.68%
Eye corrosion	-	0.8970	89.70%
Eye irritation	+	0.7535	75.35%
Skin irritation	-	0.5665	56.65%
Skin corrosion	+	0.5546	55.46%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6920	69.20%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.8512	85.12%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6669	66.69%
Acute Oral Toxicity (c)	III	0.7081	70.81%
Estrogen receptor binding	-	0.9442	94.42%
Androgen receptor binding	-	0.8037	80.37%
Thyroid receptor binding	-	0.8907	89.07%
Glucocorticoid receptor binding	-	0.8945	89.45%
Aromatase binding	-	0.9382	93.82%
PPAR gamma	-	0.9375	93.75%
Honey bee toxicity	-	0.9171	91.71%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	-	0.9086	90.86%

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	96.89%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.16%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.47%	98.95%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	86.47%	98.46%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.22%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.91%	95.89%

Plants that contains it

• Jacobaea arnautorum

Cross-Links

• PubChem: 11815460
• LOTUS: LTS0124006
• wikiData: Q105208492