Turneforcidine

Details

• Internal ID: 9d4923a7-fd05-456f-93ca-38d599385fb4
• Taxonomy: Organoheterocyclic compounds > Pyrrolizidines
• IUPAC Name: (1R,7R,8R)-7-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol
• SMILES (Canonical): C1CN2CCC(C2C1CO)O
• SMILES (Isomeric): C1CN2CC[C@H]([C@H]2[C@@H]1CO)O
• InChI: InChI=1S/C8H15NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h6-8,10-11H,1-5H2/t6-,7+,8+/m0/s1
• InChI Key: QWOXSTGOGUNUGF-XLPZGREQSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.21 g/mol
• Exact Mass: 157.110278721 g/mol
• Topological Polar Surface Area (TPSA): 43.70 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.57
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• Racemonecine
• (-)-Racemonecine
• (-)-Turneforcidine
• Dl-turneforcidine
• 21850-67-9
• 15RCF220B3
• (1R,7R,8R)-(-)-Turneforcidine
• (1R,7R,8R)-7-(Hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol
• UNII-15RCF220B3
• (1R,7R,7aR)-Hexahydro-7-hydroxy-1H-pyrrolizine-1-methanol
• 1H-Pyrrolizine-1-methanol, hexahydro-7-hydroxy-, (1R,7R,7aR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.5706	57.06%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Lysosomes	0.6293	62.93%
OATP2B1 inhibitior	-	0.8509	85.09%
OATP1B1 inhibitior	+	0.9669	96.69%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.8975	89.75%
P-glycoprotein inhibitior	-	0.9890	98.90%
P-glycoprotein substrate	-	0.8656	86.56%
CYP3A4 substrate	-	0.6419	64.19%
CYP2C9 substrate	-	0.6107	61.07%
CYP2D6 substrate	+	0.6537	65.37%
CYP3A4 inhibition	-	0.9849	98.49%
CYP2C9 inhibition	-	0.9360	93.60%
CYP2C19 inhibition	-	0.9253	92.53%
CYP2D6 inhibition	-	0.8637	86.37%
CYP1A2 inhibition	-	0.8233	82.33%
CYP2C8 inhibition	-	0.9903	99.03%
CYP inhibitory promiscuity	-	0.9685	96.85%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5516	55.16%
Eye corrosion	-	0.8873	88.73%
Eye irritation	+	0.7732	77.32%
Skin irritation	-	0.5913	59.13%
Skin corrosion	-	0.5692	56.92%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6054	60.54%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.8871	88.71%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5135	51.35%
Acute Oral Toxicity (c)	III	0.5876	58.76%
Estrogen receptor binding	-	0.9540	95.40%
Androgen receptor binding	-	0.8131	81.31%
Thyroid receptor binding	-	0.8649	86.49%
Glucocorticoid receptor binding	-	0.8154	81.54%
Aromatase binding	-	0.9023	90.23%
PPAR gamma	-	0.9019	90.19%
Honey bee toxicity	-	0.8878	88.78%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.9918	99.18%

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	99.54%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.50%	96.09%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	88.29%	98.46%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.84%	97.09%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	86.75%	96.03%
CHEMBL226	P30542	Adenosine A1 receptor	84.89%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.01%	95.89%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	83.73%	95.61%
CHEMBL2581	P07339	Cathepsin D	82.05%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.47%	95.83%
CHEMBL3105	P09874	Poly [ADP-ribose] polymerase-1	80.78%	93.90%

Plants that contains it

• Heliotropium angiospermum

Cross-Links

• PubChem: 11423723
• LOTUS: LTS0263289
• wikiData: Q105229318