(2S,3S,4S,5S)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol

Details

• Internal ID: 656fa3a3-f3cb-4b5a-be82-fb4def0b63b1
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines
• IUPAC Name: (2S,3S,4S,5S)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• SMILES (Canonical): C(C1C(C(C(N1)CO)O)O)O
• SMILES (Isomeric): C([C@H]1[C@@H]([C@H]([C@@H](N1)CO)O)O)O
• InChI: InChI=1S/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/t3-,4-,5-,6-/m0/s1
• InChI Key: PFYHYHZGDNWFIF-BXKVDMCESA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₃NO₄
• Molecular Weight: 163.17 g/mol
• Exact Mass: 163.08445790 g/mol
• Topological Polar Surface Area (TPSA): 93.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.97
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• 219562-44-4
• (2S,3S,4S,5S)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• SCHEMBL2434435
• 2,5-dideoxy-2,5-imino-L-mannitol
• BDBM50375510
• DB02172
• PD008160
• Q27093230

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7735	77.35%
Caco-2	-	0.9586	95.86%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4073	40.73%
OATP2B1 inhibitior	-	0.8512	85.12%
OATP1B1 inhibitior	+	0.9691	96.91%
OATP1B3 inhibitior	+	0.9372	93.72%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9534	95.34%
P-glycoprotein inhibitior	-	0.9802	98.02%
P-glycoprotein substrate	-	0.9618	96.18%
CYP3A4 substrate	-	0.7648	76.48%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	+	0.4032	40.32%
CYP3A4 inhibition	-	0.9856	98.56%
CYP2C9 inhibition	-	0.9260	92.60%
CYP2C19 inhibition	-	0.9548	95.48%
CYP2D6 inhibition	-	0.9163	91.63%
CYP1A2 inhibition	-	0.8774	87.74%
CYP2C8 inhibition	-	0.9804	98.04%
CYP inhibitory promiscuity	-	0.9727	97.27%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7210	72.10%
Eye corrosion	-	0.9744	97.44%
Eye irritation	-	0.7879	78.79%
Skin irritation	-	0.7176	71.76%
Skin corrosion	-	0.8255	82.55%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5867	58.67%
Micronuclear	+	0.6174	61.74%
Hepatotoxicity	-	0.6410	64.10%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4810	48.10%
Acute Oral Toxicity (c)	III	0.5518	55.18%
Estrogen receptor binding	-	0.8711	87.11%
Androgen receptor binding	-	0.7787	77.87%
Thyroid receptor binding	-	0.7807	78.07%
Glucocorticoid receptor binding	-	0.7622	76.22%
Aromatase binding	-	0.7498	74.98%
PPAR gamma	-	0.7770	77.70%
Honey bee toxicity	-	0.9033	90.33%
Biodegradation	+	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	-	0.9763	97.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2524	P06280	Alpha-galactosidase A	500 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.89%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.51%	97.09%
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	84.22%	94.55%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.17%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	80.19%	95.93%
CHEMBL2996	Q05655	Protein kinase C delta	80.08%	97.79%

Plants that contains it

• Derris elliptica

Cross-Links

• PubChem: 11073745
• LOTUS: LTS0176241
• wikiData: Q27093230