Lactobionic acid

Details

• Internal ID: 935082e9-055e-46fe-a47e-28fe3a513cf0
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid
• SMILES (Canonical): C(C1C(C(C(C(O1)OC(C(CO)O)C(C(C(=O)O)O)O)O)O)O)O
• SMILES (Isomeric): C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C(=O)O)O)O)O)O)O)O
• InChI: InChI=1S/C12H22O12/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h3-10,12-20H,1-2H2,(H,21,22)/t3-,4-,5+,6+,7-,8-,9-,10-,12+/m1/s1
• InChI Key: JYTUSYBCFIZPBE-AMTLMPIISA-N
• Popularity: 286 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₂O₁₂
• Molecular Weight: 358.30 g/mol
• Exact Mass: 358.11112613 g/mol
• Topological Polar Surface Area (TPSA): 218.00 Ų
• XlogP: -5.00
• Atomic LogP (AlogP): -5.67
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• 96-82-2
• 4-O-beta-D-Galactopyranosyl-D-gluconic acid
• 4-(beta-D-Galactosido)-D-gluconic acid
• UNII-65R938S4DV
• DTXSID3048861
• CHEBI:55481
• 65R938S4DV
• lactobionate
• EINECS 202-538-3
• (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid
• D-Gluconic acid, 4-O-.beta.-D-galactopyranosyl-
• DTXCID6028787
• MFCD00078147
• maltobionic-acid
• CAS-96-82-2
• NCGC00016356-01
• (2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanoic acid
• Prestwick_560
• C12H22O12
• Lactobionic acid, purum
• Lactobionic acid, 97%
• 110638-68-1
• Prestwick0_000452
• Prestwick1_000452
• Prestwick2_000452
• Prestwick3_000452
• D-Gluconic acid, 4-O-b-D-galactopyranosyl-
• SCHEMBL24870
• BSPBio_000524
• (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-hexanoic acid
• LACTOBIONIC ACID [II]
• LACTOBIONIC ACID [MI]
• SPBio_002463
• BPBio1_000578
• LACTOBIONIC ACID [INCI]
• CHEMBL3039602
• LACTOBIONIC ACID [MART.]
• JYTUSYBCFIZPBE-AMTLMPIISA-N
• LACTOBIONIC ACID [USP-RS]
• LACTOBIONIC ACID [WHO-DD]
• HMS1569K06
• HMS2096K06
• AMY32686
• HY-N7059
• Methyl (R)-(-)-2-Chloromandelate
• Tox21_113353
• s4964
• AKOS015896798
• AKOS015924795
• LACTOBIONIC ACID [EP IMPURITY]
• Tox21_113353_1
• CCG-214227
• CS-W011829
• LACTOBIONIC ACID [EP MONOGRAPH]
• Lactobionic acid, cell impermeant agent
• NCGC00179532-01
• NCGC00179532-03
• 4-O-beta-galactopyranosyl-d-gluconic acid
• AS-16070
• L0005
• D70310
• Q6138969
• D0229170-C0EC-40FC-A777-BF34018EED2A
• Lactobionic acid, European Pharmacopoeia (EP) Reference Standard
• (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)hexanoic acid
• 2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-hexanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9186	91.86%
Caco-2	-	0.9492	94.92%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7319	73.19%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.9239	92.39%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9528	95.28%
P-glycoprotein inhibitior	-	0.9188	91.88%
P-glycoprotein substrate	-	0.9617	96.17%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.9727	97.27%
CYP2C9 inhibition	-	0.9753	97.53%
CYP2C19 inhibition	-	0.9666	96.66%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.9707	97.07%
CYP2C8 inhibition	-	0.9240	92.40%
CYP inhibitory promiscuity	-	0.9768	97.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7437	74.37%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9663	96.63%
Skin irritation	-	0.8577	85.77%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6819	68.19%
Micronuclear	-	0.8141	81.41%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9299	92.99%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.7111	71.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6474	64.74%
Acute Oral Toxicity (c)	IV	0.6240	62.40%
Estrogen receptor binding	-	0.6096	60.96%
Androgen receptor binding	-	0.6857	68.57%
Thyroid receptor binding	+	0.5294	52.94%
Glucocorticoid receptor binding	-	0.6895	68.95%
Aromatase binding	-	0.5472	54.72%
PPAR gamma	-	0.5968	59.68%
Honey bee toxicity	-	0.8337	83.37%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.9100	91.00%
Fish aquatic toxicity	-	0.9267	92.67%

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	96.44%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.77%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.67%	86.92%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.15%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.09%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.50%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.03%	95.89%
CHEMBL2581	P07339	Cathepsin D	80.76%	98.95%

Plants that contains it

• Pogostemon cablin

Cross-Links

• PubChem: 7314
• NPASS: NPC32148