Dehydroascorbic acid

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	81f28f92-da64-44e8-ab3c-597022657f01
Taxonomy	Organoheterocyclic compounds > Lactones > Gamma butyrolactones
IUPAC Name	(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
SMILES (Canonical)	C(C(C1C(=O)C(=O)C(=O)O1)O)O
SMILES (Isomeric)	C([C@@H]([C@@H]1C(=O)C(=O)C(=O)O1)O)O
InChI	InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1
InChI Key	SBJKKFFYIZUCET-JLAZNSOCSA-N
Popularity	3,629 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₆H₆O₆
Molecular Weight	174.11 g/mol
Exact Mass	174.01643791 g/mol
Topological Polar Surface Area (TPSA)	101.00 Å²
XlogP	-1.00
Atomic LogP (AlogP)	-2.60
H-Bond Acceptor	6
H-Bond Donor	2
Rotatable Bonds	2

Synonyms

Top

490-83-5

L-Dehydroascorbic acid

DHAA

dehydroascorbate

Dehydro-L-ascorbic acid

L-Dehydroascorbate

L-Threo-hexo-2,3-diulosono-1,4-lactone

(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione

(L)-Dehydroascorbic acid

(R)-5-((S)-1,2-dihydroxyethyl)furan-2,3,4(5H)-trione

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7506	75.06%
Caco-2	-	0.9703	97.03%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7051	70.51%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.9596	95.96%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9813	98.13%
P-glycoprotein inhibitior	-	0.9639	96.39%
P-glycoprotein substrate	-	0.9780	97.80%
CYP3A4 substrate	-	0.6854	68.54%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8596	85.96%
CYP3A4 inhibition	-	0.9769	97.69%
CYP2C9 inhibition	-	0.9737	97.37%
CYP2C19 inhibition	-	0.9683	96.83%
CYP2D6 inhibition	-	0.9608	96.08%
CYP1A2 inhibition	-	0.9302	93.02%
CYP2C8 inhibition	-	0.9925	99.25%
CYP inhibitory promiscuity	-	0.9906	99.06%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7447	74.47%
Eye corrosion	-	0.9347	93.47%
Eye irritation	+	0.7271	72.71%
Skin irritation	-	0.7207	72.07%
Skin corrosion	-	0.8161	81.61%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7608	76.08%
Micronuclear	-	0.6667	66.67%
Hepatotoxicity	-	0.7967	79.67%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.8875	88.75%
Nephrotoxicity	-	0.6154	61.54%
Acute Oral Toxicity (c)	IV	0.5265	52.65%
Estrogen receptor binding	-	0.7464	74.64%
Androgen receptor binding	-	0.6816	68.16%
Thyroid receptor binding	-	0.7099	70.99%
Glucocorticoid receptor binding	-	0.8317	83.17%
Aromatase binding	-	0.8685	86.85%
PPAR gamma	-	0.8554	85.54%
Honey bee toxicity	-	0.8999	89.99%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.8469	84.69%

Targets

Top

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.54%	97.25%
CHEMBL2581	P07339	Cathepsin D	88.22%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.79%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.63%	96.09%

Plants that contains it

Top

Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Arabidopsis thaliana

Foeniculum vulgare

Lotus corniculatus subsp. corniculatus