D-erythro-Hex-2-enonic acid, gamma-lactone

Details

• Internal ID: 6a09a61e-1de2-48c8-8dc6-d34263e83fb5
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: 2-(1,2-dihydroxyethyl)-3,4-dihydroxy-2H-furan-5-one
• SMILES (Canonical): C(C(C1C(=C(C(=O)O1)O)O)O)O
• SMILES (Isomeric): C(C(C1C(=C(C(=O)O1)O)O)O)O
• InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2
• InChI Key: CIWBSHSKHKDKBQ-UHFFFAOYSA-N
• Popularity: 23 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

• 62624-30-0
• L-Erythroascorbic acid
• D-erythro-Hex-2-enonic acid, gamma-lactone
• 89924-69-6
• 5-(1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
• L-Threoascorbic acid-1-13C
• NSC8117
• 2-(1,2-dihydroxyethyl)-3,4-dihydroxy-2H-furan-5-one
• 5-(1,2-dihydroxyethyl)-3,4-dihydroxy-2,5-dihydrofuran-2-one
• L-Ascorbic Acid-13C6
• L-Ascorbic Acid-6-13C
• Erycorbin
• 1129294-89-8
• 2-(1,2-dihydroxyethyl)-4,5-dihydroxy-3-furanone
• Neo-cebicure
• Ascorbyl radical
• NSC33832
• component of Cortalex
• component of Ferancee
• Xyloascorbic acid, L-
• D-ASCORBIC ACID, ISO
• SR-01000389660
• 1331939-77-5
• 2-(1,2-Dihydroxyethyl)-4,5-dihydroxyfuran-3-one
• ascorbyl
• NSC-8117
• MFCD00005378
• DL-Ascorbinsaure
• iso-Ascorbic acid
• 149153-08-2
• Prestwick_683
• EINECS 263-644-3
• Mercate '5'
• starbld0035980
• Araboascorbic acid, D-
• SCHEMBL786
• Oprea1_099167
• MLS006011447
• SCHEMBL332736
• CHEMBL1161421
• 5-(1,2-dihydroxyethyl)-3,4-dihydroxy-5-hydrofuran-2-one
• L-Ascorbic acid, iron(2+) salt
• HMS3370P18
• HMS3372D17
• HMS3651P22
• L-Threoascorbic acid,Antiscorbutic factor,Vitamin C;(R)-5-((S)-1,2-Dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
• WLN: T5OV EHJ CQ DQ EYQ1Q
• HSCI1_000271
• NSC218455
• AKOS000487668
• AKOS015915124
• AKOS016352178
• SB44719
• SB60900
• SMP2_000183
• Technetium-99 labeled ferrous ascorbate
• NCGC00094971-01
• NCGC00094971-02
• NCGC00248925-01
• NCI60_002981
• SMR003217638
• SY010444
• VS-01830
• FT-0624450
• FT-0627701
• FT-0652639
• L-threo-Hex-2-enonic acid, .gamma.-lactone
• (2R)-2-[(1S)-1,5-dihydroxyfuran-3-one
• EN300-18134
• A833894
• SR-01000389660-1
• SR-01000389660-3
• Z57201291
• 2-[1,2-bis(oxidanyl)ethyl]-4,5-bis(oxidanyl)furan-3-one
• 3,4-dihydroxy-5-(1',2'-dihydroxyethyl)-2(5H)-furanone
• 3,4-Dihydroxy-5-[(S)-1,2-dihydroxyethyl]furan-2(5H)-one
• 5-(1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one, AldrichCPR
• 2252244-20-3

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

• Capsicum annuum
• Peperomia blanda

Cross-Links

• PubChem: 54676860
• LOTUS: LTS0235712
• wikiData: Q104960561