Radicamine B

Details

• Internal ID: a2e4cec5-1c00-426b-b6a6-3057ce6def78
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Phenylpyrrolidines
• IUPAC Name: (2R,3R,4R,5R)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidine-3,4-diol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C(C(N2)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H]([C@@H]([C@H](N2)CO)O)O)O
• InChI: InChI=1S/C11H15NO4/c13-5-8-10(15)11(16)9(12-8)6-1-3-7(14)4-2-6/h1-4,8-16H,5H2/t8-,9-,10-,11-/m1/s1
• InChI Key: BRPXIQPSCKPBLH-GWOFURMSSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₅NO₄
• Molecular Weight: 225.24 g/mol
• Exact Mass: 225.10010796 g/mol
• Topological Polar Surface Area (TPSA): 93.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.88
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• 431981-75-8
• (2R,3R,4R,5R)-2-(Hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidine-3,4-diol
• CHEMBL466791
• SCHEMBL13848027
• XR175854
• 7E79EEAE-B5A3-481B-A039-B6DA9C270415
• 3,4-Pyrrolidinediol,2-(hydroxymethyl)-5-(4-hydroxyphenyl)-,(2S,3S,4S,5S)-(9ci)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9373	93.73%
Caco-2	-	0.8488	84.88%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4699	46.99%
OATP2B1 inhibitior	-	0.8622	86.22%
OATP1B1 inhibitior	+	0.8862	88.62%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9841	98.41%
P-glycoprotein inhibitior	-	0.9795	97.95%
P-glycoprotein substrate	-	0.8546	85.46%
CYP3A4 substrate	-	0.6302	63.02%
CYP2C9 substrate	-	0.8380	83.80%
CYP2D6 substrate	+	0.4430	44.30%
CYP3A4 inhibition	-	0.9477	94.77%
CYP2C9 inhibition	-	0.8956	89.56%
CYP2C19 inhibition	-	0.9292	92.92%
CYP2D6 inhibition	-	0.8003	80.03%
CYP1A2 inhibition	-	0.7608	76.08%
CYP2C8 inhibition	-	0.5701	57.01%
CYP inhibitory promiscuity	-	0.8091	80.91%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7231	72.31%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8739	87.39%
Skin irritation	-	0.7340	73.40%
Skin corrosion	-	0.8851	88.51%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6378	63.78%
Micronuclear	+	0.7474	74.74%
Hepatotoxicity	-	0.6905	69.05%
skin sensitisation	-	0.7629	76.29%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5186	51.86%
Acute Oral Toxicity (c)	III	0.6807	68.07%
Estrogen receptor binding	-	0.8266	82.66%
Androgen receptor binding	+	0.5355	53.55%
Thyroid receptor binding	-	0.6070	60.70%
Glucocorticoid receptor binding	-	0.7821	78.21%
Aromatase binding	-	0.7698	76.98%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9388	93.88%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.8772	87.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	94.96%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.49%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.29%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	86.21%	97.79%
CHEMBL2581	P07339	Cathepsin D	86.02%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.77%	94.45%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.56%	89.67%
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	82.86%	94.55%
CHEMBL242	Q92731	Estrogen receptor beta	82.09%	98.35%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	81.55%	97.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.80%	91.71%

Plants that contains it

• Lobelia chinensis

Cross-Links

• PubChem: 15953621
• NPASS: NPC208757
• ChEMBL: CHEMBL466791
• LOTUS: LTS0205973
• wikiData: Q104944958