2-Amino-2-deoxy-D-gluconic acid

Details

• Internal ID: 624649ae-a778-455e-9c5c-b537b6289840
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids > D-alpha-amino acids
• IUPAC Name: (2R,3R,4S,5R)-2-amino-3,4,5,6-tetrahydroxyhexanoic acid
• SMILES (Canonical): C(C(C(C(C(C(=O)O)N)O)O)O)O
• SMILES (Isomeric): C([C@H]([C@H]([C@@H]([C@H](C(=O)O)N)O)O)O)O
• InChI: InChI=1S/C6H13NO6/c7-3(6(12)13)5(11)4(10)2(9)1-8/h2-5,8-11H,1,7H2,(H,12,13)/t2-,3-,4-,5-/m1/s1
• InChI Key: UFYKDFXCZBTLOO-TXICZTDVSA-N
• Popularity: 65 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₃NO₆
• Molecular Weight: 195.17 g/mol
• Exact Mass: 195.07428713 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: -5.90
• Atomic LogP (AlogP): -3.53
• H-Bond Acceptor: 6
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 3646-68-2
• Glucosaminic acid
• D-Glucosamic acid
• 2-Amino-2-deoxy-D-gluconic acid
• Glucosaminate
• 2-Amino-2-deoxygluconic acid
• D-Glucosaminate
• D-Gluconic acid, 2-amino-2-deoxy-
• (2R,3R,4S,5R)-2-amino-3,4,5,6-tetrahydroxyhexanoic acid
• D-?Glucosamic acid
• Gluconic acid, 2-amino-2-deoxy-
• 2-Amino-2-deoxy-D-gluconate
• 6165-14-6
• CHEMBL3039035
• CHEBI:17784
• (2R,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxy-hexanoic acid
• D-lucosamic acid
• EINECS 222-879-1
• MFCD00037764
• NSC 37779
• NSC 404265
• Gluconic acid, 2-amino-2-deoxy-, D-
• (3R,4S,5R)-3,4,5,6-tetrahydroxynorleucine
• Spectrum_001231
• SpecPlus_000455
• AI3-51894
• Spectrum2_001910
• Spectrum3_001347
• Spectrum4_001866
• Spectrum5_000432
• bmse000440
• BSPBio_003133
• KBioGR_002334
• KBioSS_001711
• SPECTRUM310298
• DivK1c_006551
• SCHEMBL396940
• SPBio_001880
• D-Glucosaminic acid, >=98%
• KBio1_001495
• KBio2_001711
• KBio2_004279
• KBio2_006847
• KBio3_002353
• DTXSID60878848
• BDBM50442917
• CCG-38481
• AKOS006238367
• SDCCGMLS-0066564.P001
• NCGC00178247-01
• AS-56887
• HY-128745
• CS-0102537
• G0042
• C03752
• T72366
• (3R,4S,5R)-3,4,5,6-tetrahydroxy-D-norleucine
• A823258
• SR-05000002429
• SR-05000002429-1
• W-202514
• Q27102608
• 6BA699D8-74A0-43AF-82A9-F68E6BFA0B50
• (2R,3R,4S,5R)-2-amino-3,4,5,6-tetrahydroxyhexanoicacid
• (2R,3R,4S,5R)-2-azanyl-3,4,5,6-tetrakis(oxidanyl)hexanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5480	54.80%
Caco-2	-	0.9935	99.35%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Lysosomes	0.4760	47.60%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9723	97.23%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9851	98.51%
P-glycoprotein inhibitior	-	0.9877	98.77%
P-glycoprotein substrate	-	0.9708	97.08%
CYP3A4 substrate	-	0.7513	75.13%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.7952	79.52%
CYP3A4 inhibition	-	0.9183	91.83%
CYP2C9 inhibition	-	0.9077	90.77%
CYP2C19 inhibition	-	0.9199	91.99%
CYP2D6 inhibition	-	0.8883	88.83%
CYP1A2 inhibition	-	0.8512	85.12%
CYP2C8 inhibition	-	0.9899	98.99%
CYP inhibitory promiscuity	-	0.9849	98.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7310	73.10%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9651	96.51%
Skin irritation	-	0.8392	83.92%
Skin corrosion	-	0.9685	96.85%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8105	81.05%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9554	95.54%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	-	0.7667	76.67%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6866	68.66%
Acute Oral Toxicity (c)	IV	0.5919	59.19%
Estrogen receptor binding	-	0.8812	88.12%
Androgen receptor binding	-	0.8426	84.26%
Thyroid receptor binding	-	0.6202	62.02%
Glucocorticoid receptor binding	-	0.4887	48.87%
Aromatase binding	-	0.9068	90.68%
PPAR gamma	-	0.8042	80.42%
Honey bee toxicity	-	0.9748	97.48%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	-	0.9800	98.00%
Fish aquatic toxicity	-	0.9815	98.15%

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	98.58%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.84%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.33%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.59%	96.95%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.28%	97.29%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.02%	100.00%

Plants that contains it

• Medicago sativa

Cross-Links

• PubChem: 73563
• LOTUS: LTS0263729
• wikiData: Q27102608