Parasorbic acid

Details

• Internal ID: 433ad3be-6a7a-4e63-bebd-368ef67f91bb
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: (2S)-2-methyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1CC=CC(=O)O1
• SMILES (Isomeric): C[C@H]1CC=CC(=O)O1
• InChI: InChI=1S/C6H8O2/c1-5-3-2-4-6(7)8-5/h2,4-5H,3H2,1H3/t5-/m0/s1
• InChI Key: DYNKRGCMLGUEMN-YFKPBYRVSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.13 g/mol
• Exact Mass: 112.052429494 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.88
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Hexenollactone
• Parascorbic acid
• gamma-Hexenolactone
• 10048-32-5
• 2-Hexen-5,1-olide
• Kyselina paraskorbova
• PARASORBICACID
• (+)-Parasorbinsaeure
• (2S)-2-methyl-2,3-dihydropyran-6-one
• UNII-DCN48OUK3T
• DCN48OUK3T
• Kyselina paraskorbova [Czech]
• CHEBI:7926
• (+)-Parasorbinsaeure [German]
• (S)-(+)-5,6-Dihydro-6-methyl-2H-pyran-2-one
• 2H-Pyran-2-one, 5,6-dihydro-6-methyl-, (6S)-
• BRN 0080685
• 2-Hexenoic acid, 5-hydroxy-, delta-lactone
• 2H-Pyran-2-one, 5,6-dihydro-6-methyl-, (S)-
• 5-17-09-00130 (Beilstein Handbook Reference)
• (S)-parasorbic acid
• (s)-2-hexen-5-olide
• PARASORBIC ACID [MI]
• PARASORBIC ACID [IARC]
• SCHEMBL2686203
• CHEMBL2252704
• DTXSID10893607
• (S)-(+)-PARASORBIC ACID
• (+)-(6S)-PARASORBIC ACID
• AKOS006278774
• DB14121
• (S)-6-METHYL-5,6-DIHYDRO-2-PYRONE
• (6S)-5,6-Dihydro-6-methyl-2H-pyran-2-one
• (6S)-6-methyl-5,6-dihydro-2H-pyran-2-one
• C08502
• EN300-7587224
• Q27107618
• 2H-Pyran-2-one, 5,6-dihydro-6-methyl-, (S)-()-
• 2H-PYRAN-2-ONE, 5,6-DIHYDRO-6-METHYL-, (S)-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.8244	82.44%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5454	54.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9500	95.00%
OATP1B3 inhibitior	+	0.9783	97.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9533	95.33%
P-glycoprotein inhibitior	-	0.9879	98.79%
P-glycoprotein substrate	-	0.9591	95.91%
CYP3A4 substrate	-	0.6414	64.14%
CYP2C9 substrate	-	0.6339	63.39%
CYP2D6 substrate	-	0.8974	89.74%
CYP3A4 inhibition	-	0.9644	96.44%
CYP2C9 inhibition	-	0.9328	93.28%
CYP2C19 inhibition	-	0.7446	74.46%
CYP2D6 inhibition	-	0.9656	96.56%
CYP1A2 inhibition	-	0.7582	75.82%
CYP2C8 inhibition	-	0.9976	99.76%
CYP inhibitory promiscuity	-	0.9476	94.76%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7676	76.76%
Carcinogenicity (trinary)	Non-required	0.4805	48.05%
Eye corrosion	+	0.8615	86.15%
Eye irritation	+	0.9802	98.02%
Skin irritation	+	0.8501	85.01%
Skin corrosion	-	0.6870	68.70%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8170	81.70%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	+	0.6269	62.69%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.8000	80.00%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	+	0.4712	47.12%
Acute Oral Toxicity (c)	III	0.4795	47.95%
Estrogen receptor binding	-	0.9783	97.83%
Androgen receptor binding	-	0.8591	85.91%
Thyroid receptor binding	-	0.9292	92.92%
Glucocorticoid receptor binding	-	0.8860	88.60%
Aromatase binding	-	0.8730	87.30%
PPAR gamma	-	0.9280	92.80%
Honey bee toxicity	-	0.9534	95.34%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	-	0.6291	62.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.69%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.41%	86.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.12%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.90%	100.00%

Plants that contains it

• Bergenia pacumbis
• Chaptalia nutans
• Melochia chamaedrys
• Papaver somniferum
• Rauvolfia serpentina
• Sorbus aucuparia
• Sorbus tianschanica
• Vaccinium macrocarpon
• Zingiber officinale

Cross-Links

• PubChem: 441575
• NPASS: NPC275316
• LOTUS: LTS0143620
• wikiData: Q27107618