(2R,3R,4R,5S)-2-Hydroxymethyl-piperidine-3,4,5-triol

Details

• Internal ID: d215ce84-be33-4f5e-89dc-aa1fa3264b16
• Taxonomy: Organoheterocyclic compounds > Piperidines
• IUPAC Name: (2R,3R,4R,5S)-2-(hydroxymethyl)piperidin-1-ium-3,4,5-triol
• SMILES (Canonical): C1C(C(C(C([NH2+]1)CO)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H]([C@@H]([C@H]([NH2+]1)CO)O)O)O
• InChI: InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/p+1/t3-,4+,5-,6-/m1/s1
• InChI Key: LXBIFEVIBLOUGU-JGWLITMVSA-O
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₄NO₄+
• Molecular Weight: 164.18 g/mol
• Exact Mass: 164.09228293 g/mol
• Topological Polar Surface Area (TPSA): 97.50 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -3.99
• H-Bond Acceptor: 4
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• 2pwd
• 3gbe
• 3gxt
• 3qfz
• 4iid
• DNJ

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7747	77.47%
Caco-2	-	0.9638	96.38%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Lysosomes	0.6154	61.54%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.9549	95.49%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9703	97.03%
P-glycoprotein inhibitior	-	0.9809	98.09%
P-glycoprotein substrate	-	0.9403	94.03%
CYP3A4 substrate	-	0.6832	68.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7144	71.44%
CYP3A4 inhibition	-	0.9915	99.15%
CYP2C9 inhibition	-	0.9438	94.38%
CYP2C19 inhibition	-	0.9435	94.35%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	-	0.9294	92.94%
CYP2C8 inhibition	-	0.9895	98.95%
CYP inhibitory promiscuity	-	0.9934	99.34%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6723	67.23%
Eye corrosion	-	0.9588	95.88%
Eye irritation	-	0.9129	91.29%
Skin irritation	-	0.7427	74.27%
Skin corrosion	-	0.8472	84.72%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5594	55.94%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.8074	80.74%
skin sensitisation	-	0.8694	86.94%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.5659	56.59%
Acute Oral Toxicity (c)	III	0.7596	75.96%
Estrogen receptor binding	-	0.8814	88.14%
Androgen receptor binding	-	0.8849	88.49%
Thyroid receptor binding	-	0.7648	76.48%
Glucocorticoid receptor binding	-	0.7670	76.70%
Aromatase binding	-	0.8263	82.63%
PPAR gamma	-	0.8627	86.27%
Honey bee toxicity	-	0.8301	83.01%
Biodegradation	+	0.8500	85.00%
Crustacea aquatic toxicity	-	0.8300	83.00%
Fish aquatic toxicity	-	0.9947	99.47%

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	94.50%	83.82%
CHEMBL226	P30542	Adenosine A1 receptor	91.40%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.28%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.93%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.86%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.02%	97.25%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.86%	86.92%
CHEMBL3589	P55263	Adenosine kinase	80.99%	98.05%

Plants that contains it

• Morus alba
• Morus mongolica

Cross-Links

• PubChem: 21769099
• NPASS: NPC288458