Erythorbic Acid

Details

• Internal ID: c75907ab-8245-4444-b044-6e766327d585
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
• InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1
• InChI Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N
• Popularity: 542 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₈O₆
• Molecular Weight: 176.12 g/mol
• Exact Mass: 176.03208797 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.41
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 89-65-6
• Isoascorbic acid
• D-Araboascorbic acid
• D-Isoascorbic acid
• D-Erythorbic acid
• Araboascorbic acid
• Isovitamin C
• Erycorbin
• Glucosaccharonic acid
• Saccharosonic acid
• Neo-cebicure
• Mercate 5
• FEMA No. 2410
• FEMA Number: 2410
• 2,3-Didehydro-D-erythro-hexono-1,4-lactone
• D-erythro-3-Oxohexonic acid lactone
• D-erythro-3-Ketohexonic acid lactone
• DTXSID6026537
• (2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
• 3-Keto-D-erythro-hexonic acid gamma-lactone
• 311332OII1
• DTXCID306537
• INS NO.315
• CHEBI:51438
• INS-315
• (5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
• NSC-8117
• E-315
• NSC8117
• (5R)-5-((1R)-1,2-DIHYDROXYETHYL)-3,4-DIHYDROXYFURAN-2(5H)-ONE
• erythroascorbic acid
• (2R)-2-((1R)-1,2-dihydroxyethyl)-3,4-dihydroxy-2H-furan-5-one
• RefChem:137724
• GlyTouCan:G12164VD
• G12164VD
• (5R)-5-((1R)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one;D-erythro-hex-2-enono-1,4-lactone
• 201-928-0
• D-erythro-ascorbic acid
• D-(-)-Isoascorbic acid
• (R)-5-((R)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
• MFCD00005378
• D-erythro-Hex-2-enonic acid, g-lactone
• D-erythro-hex-2-enonic acid gamma-lactone
• D-ASCORBIC ACID, ISO
• D-erythro-hex-2-enono-1,4-lactone
• D(-)-Isoascorbic Acid (Erythorbic Acid)
• Erythroascorbic acid, D-
• (5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
• CCRIS 6568
• HSDB 584
• D(-?)?-?Isoascorbic Acid (Erythorbic Acid)
• Erythorbic acid [NF]
• NSC 8117
• EINECS 201-928-0
• 3-Oxohexonic acid lactone, D-erythro-
• BRN 0084271
• Ascorbic Acid EP Impurity F
• Hex-2-enonic acid gamma-lactone, D-erythro-
• UNII-311332OII1
• D-soascorbic acid
• (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (D-Isoascorbic Acid)
• (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (D-Isoascorbic Acid); Ascorbic Acid Impurity F; Sodium Ascorbate Impurity F
• d-iso-ascorbic acid
• ERYTHORBATE
• ISOASCORBIC-ACID
• d(-)-isoascorbic acid
• 1f9g
• E315
• D-Erythro-hex-2-enonic acid, gamma-lactone,
• EC 201-928-0
• Erythorbic acid (Standard)
• SCHEMBL18678
• ERYTHORBIC ACID [II]
• 5-18-05-00026 (Beilstein Handbook Reference)
• ERYTHORBIC ACID [FCC]
• ISOASCORBIC ACID [MI]
• ERYTHORBIC ACID [FHFI]
• ERYTHORBIC ACID [HSDB]
• CHEMBL486293
• SCHEMBL3700961
• Sodium Ascorbate EP Impurity F
• ERYTHORBIC ACID [MART.]
• HY-N7079R
• ERYTHORBIC ACID [USP-RS]
• MSK2311
• D-(-)-Isoascorbic acid, 98%
• HY-N7079
• Tox21_201111
• AC8021
• SBB017515
• AKOS015856346
• D-erythro-hex-2-enoic acid ?-lactone
• EBC-146034
• FI09585
• CAS-89-65-6
• NCGC00258663-01
• D-erythro-Hex-2-enoic acid gamma-lactone
• D-erythro-Hex-2-enonic acid, |A-lactone
• D-Isoascorbic acid, >=99%, FCC, FG
• SY010444
• D-erythro-Hex-2-enonic acid gamma lactone
• A0520
• CS-0014152
• NS00079026
• ASCORBIC ACID IMPURITY F [EP IMPURITY]
• C20364
• EN300-251979
• F600911
• Q424531
• D-Isoascorbic acid 1000 microg/mL in Acetonitrile
• Z1255372411
• 7179C406-7CCF-4C07-9125-AA71E28FB983
• (5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxy-5-hydrofuran-2-one
• Erythorbic acid, United States Pharmacopeia (USP) Reference Standard
• (5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (non-preferred name)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6225	62.25%
Caco-2	-	0.9755	97.55%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6194	61.94%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9584	95.84%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9869	98.69%
P-glycoprotein inhibitior	-	0.9715	97.15%
P-glycoprotein substrate	-	0.9682	96.82%
CYP3A4 substrate	-	0.6422	64.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8789	87.89%
CYP3A4 inhibition	-	0.9662	96.62%
CYP2C9 inhibition	-	0.9478	94.78%
CYP2C19 inhibition	-	0.9383	93.83%
CYP2D6 inhibition	-	0.9347	93.47%
CYP1A2 inhibition	-	0.8958	89.58%
CYP2C8 inhibition	-	0.9809	98.09%
CYP inhibitory promiscuity	-	0.9249	92.49%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7591	75.91%
Eye corrosion	-	0.9803	98.03%
Eye irritation	-	0.5691	56.91%
Skin irritation	-	0.7081	70.81%
Skin corrosion	-	0.8700	87.00%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7840	78.40%
Micronuclear	-	0.7041	70.41%
Hepatotoxicity	-	0.9625	96.25%
skin sensitisation	-	0.9058	90.58%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.5868	58.68%
Acute Oral Toxicity (c)	IV	0.5871	58.71%
Estrogen receptor binding	-	0.7862	78.62%
Androgen receptor binding	-	0.8180	81.80%
Thyroid receptor binding	-	0.6156	61.56%
Glucocorticoid receptor binding	-	0.5967	59.67%
Aromatase binding	-	0.7855	78.55%
PPAR gamma	-	0.7342	73.42%
Honey bee toxicity	-	0.8878	88.78%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.7280	72.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	0.5 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.17%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.62%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.47%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.78%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.16%	96.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54675810
• LOTUS: LTS0039487
• wikiData: Q424531