Picrocrocinic acid

Details

• Internal ID: d14d9ff2-5242-4468-b58c-3882d320f2af
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carboxylic acid
• SMILES (Canonical): CC1=C(C(CC(C1)OC2C(C(C(C(O2)CO)O)O)O)(C)C)C(=O)O
• SMILES (Isomeric): CC1=C(C(C[C@@H](C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)(C)C)C(=O)O
• InChI: InChI=1S/C16H26O8/c1-7-4-8(5-16(2,3)10(7)14(21)22)23-15-13(20)12(19)11(18)9(6-17)24-15/h8-9,11-13,15,17-20H,4-6H2,1-3H3,(H,21,22)/t8-,9-,11-,12+,13-,15-/m1/s1
• InChI Key: LBTAFDHXNSPZSZ-QLDIZCGWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₈
• Molecular Weight: 346.37 g/mol
• Exact Mass: 346.16276778 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.61
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 62218-53-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4890	48.90%
Caco-2	-	0.6782	67.82%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8587	85.87%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8391	83.91%
OATP1B3 inhibitior	+	0.8614	86.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7091	70.91%
P-glycoprotein inhibitior	-	0.9190	91.90%
P-glycoprotein substrate	-	0.9307	93.07%
CYP3A4 substrate	+	0.5549	55.49%
CYP2C9 substrate	-	0.6003	60.03%
CYP2D6 substrate	-	0.8957	89.57%
CYP3A4 inhibition	-	0.9357	93.57%
CYP2C9 inhibition	-	0.7499	74.99%
CYP2C19 inhibition	-	0.7975	79.75%
CYP2D6 inhibition	-	0.9346	93.46%
CYP1A2 inhibition	-	0.8302	83.02%
CYP2C8 inhibition	-	0.8124	81.24%
CYP inhibitory promiscuity	-	0.8167	81.67%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6788	67.88%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9314	93.14%
Skin irritation	-	0.8017	80.17%
Skin corrosion	-	0.9643	96.43%
Ames mutagenesis	-	0.7684	76.84%
Human Ether-a-go-go-Related Gene inhibition	-	0.7260	72.60%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8167	81.67%
skin sensitisation	-	0.7948	79.48%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.5858	58.58%
Acute Oral Toxicity (c)	III	0.6810	68.10%
Estrogen receptor binding	-	0.7180	71.80%
Androgen receptor binding	-	0.6451	64.51%
Thyroid receptor binding	+	0.6484	64.84%
Glucocorticoid receptor binding	+	0.5595	55.95%
Aromatase binding	+	0.6049	60.49%
PPAR gamma	+	0.5317	53.17%
Honey bee toxicity	-	0.8453	84.53%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7350	73.50%
Fish aquatic toxicity	+	0.8977	89.77%

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	96.91%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.69%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.95%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.60%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.76%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.72%	96.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.77%	85.14%
CHEMBL2581	P07339	Cathepsin D	81.39%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.50%	93.56%

Plants that contains it

• Ayapana amygdalina
• Crocus sativus
• Gardenia jasminoides

Cross-Links

• PubChem: 5320582
• NPASS: NPC186738
• LOTUS: LTS0013210
• wikiData: Q104951513