(+)-Shikimic acid

Details

• Internal ID: 3e4aeffd-94e3-477f-b11f-b0aa7f0227dc
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Shikimic acids and derivatves
• IUPAC Name: (3S,4R,5S)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
• SMILES (Canonical): C1C(C(C(C=C1C(=O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H]([C@H](C=C1C(=O)O)O)O)O
• InChI: InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m0/s1
• InChI Key: JXOHGGNKMLTUBP-ZLUOBGJFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.15 g/mol
• Exact Mass: 174.05282342 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.52
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 10191-00-1
• (3S,4R,5S)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
• SCHEMBL8943144
• (3S,4R,5S)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
• (3S,4R,5S)-3,4,5-Trihydroxycyclohex-1-enecarboxylicacid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7866	78.66%
Caco-2	-	0.9343	93.43%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7120	71.20%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.9507	95.07%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	-	0.9860	98.60%
P-glycoprotein inhibitior	-	0.9837	98.37%
P-glycoprotein substrate	-	0.9760	97.60%
CYP3A4 substrate	-	0.7137	71.37%
CYP2C9 substrate	-	0.7723	77.23%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.9563	95.63%
CYP2C9 inhibition	-	0.9372	93.72%
CYP2C19 inhibition	-	0.9487	94.87%
CYP2D6 inhibition	-	0.9366	93.66%
CYP1A2 inhibition	-	0.9499	94.99%
CYP2C8 inhibition	-	0.9810	98.10%
CYP inhibitory promiscuity	-	0.9662	96.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6723	67.23%
Eye corrosion	-	0.9714	97.14%
Eye irritation	+	0.7389	73.89%
Skin irritation	+	0.5051	50.51%
Skin corrosion	-	0.9010	90.10%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7895	78.95%
Micronuclear	+	0.5659	56.59%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	+	0.4766	47.66%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.4628	46.28%
Acute Oral Toxicity (c)	IV	0.4690	46.90%
Estrogen receptor binding	-	0.8876	88.76%
Androgen receptor binding	-	0.7785	77.85%
Thyroid receptor binding	-	0.8108	81.08%
Glucocorticoid receptor binding	-	0.8006	80.06%
Aromatase binding	-	0.8835	88.35%
PPAR gamma	-	0.8418	84.18%
Honey bee toxicity	-	0.9141	91.41%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.7319	73.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.81%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.91%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	84.32%	83.82%
CHEMBL2581	P07339	Cathepsin D	82.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.98%	95.56%
CHEMBL1811	P34995	Prostanoid EP1 receptor	81.22%	95.71%

Plants that contains it

• Cichorium intybus
• Cichorium pumilum
• Cyclopia subternata
• Gardenia jasminoides
• Ginkgo biloba
• Hypericum perforatum
• Illicium verum
• Pogostemon cablin
• Selaginella pulvinata
• Selaginella tamariscina
• Smilax china
• Smilax glabra
• Tara spinosa

Cross-Links

• PubChem: 10986763
• NPASS: NPC267649
• LOTUS: LTS0188772
• wikiData: Q105136690