Aurafuron A

Details

• Internal ID: bda4693f-4aad-428e-a32d-531ff0e8675c
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohols
• IUPAC Name: 5-[(2S,3Z,5E,7R,8R,9E)-2,8-dihydroxy-7,9,12-trimethyltrideca-3,5,9-trienyl]-2-hydroxy-2,4-dimethylfuran-3-one
• SMILES (Canonical): CC1=C(OC(C1=O)(C)O)CC(C=CC=CC(C)C(C(=CCC(C)C)C)O)O
• SMILES (Isomeric): CC1=C(OC(C1=O)(C)O)C[C@@H](/C=C\C=C\[C@@H](C)[C@H](/C(=C/CC(C)C)/C)O)O
• InChI: InChI=1S/C22H34O5/c1-14(2)11-12-16(4)20(24)15(3)9-7-8-10-18(23)13-19-17(5)21(25)22(6,26)27-19/h7-10,12,14-15,18,20,23-24,26H,11,13H2,1-6H3/b9-7+,10-8-,16-12+/t15-,18-,20-,22?/m1/s1
• InChI Key: AQQYZHDRTDSOER-LYKBUVKOSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₅
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.24062418 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

• (-)-aurafuron A
• CHEBI:156298
• 5-[(2S,3Z,5E,7R,8R,9E)-2,8-Dihydroxy-7,9,12-trimethyltrideca-3,5,9-trienyl]-2-hydroxy-2,4-dimethylfuran-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9253	92.53%
Caco-2	-	0.5228	52.28%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5594	55.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8759	87.59%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8055	80.55%
P-glycoprotein inhibitior	-	0.6245	62.45%
P-glycoprotein substrate	-	0.7578	75.78%
CYP3A4 substrate	+	0.5951	59.51%
CYP2C9 substrate	-	0.8107	81.07%
CYP2D6 substrate	-	0.8609	86.09%
CYP3A4 inhibition	-	0.8723	87.23%
CYP2C9 inhibition	-	0.8574	85.74%
CYP2C19 inhibition	-	0.7406	74.06%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.8418	84.18%
CYP2C8 inhibition	-	0.7564	75.64%
CYP inhibitory promiscuity	-	0.8548	85.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9328	93.28%
Carcinogenicity (trinary)	Non-required	0.5185	51.85%
Eye corrosion	-	0.9743	97.43%
Eye irritation	-	0.9640	96.40%
Skin irritation	-	0.5173	51.73%
Skin corrosion	-	0.8933	89.33%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8565	85.65%
Micronuclear	-	0.7541	75.41%
Hepatotoxicity	+	0.5928	59.28%
skin sensitisation	-	0.6255	62.55%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5392	53.92%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6494	64.94%
Acute Oral Toxicity (c)	III	0.4608	46.08%
Estrogen receptor binding	+	0.6767	67.67%
Androgen receptor binding	-	0.5963	59.63%
Thyroid receptor binding	+	0.7632	76.32%
Glucocorticoid receptor binding	+	0.7246	72.46%
Aromatase binding	+	0.6627	66.27%
PPAR gamma	-	0.5541	55.41%
Honey bee toxicity	-	0.8665	86.65%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8886	88.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.13%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.13%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.42%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.43%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	87.24%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.13%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.73%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.21%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.83%	97.14%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11773355
• LOTUS: LTS0032438
• wikiData: Q75062033