Brefeldin D

Details

• Internal ID: bfea0890-042d-470a-a045-fc9ea5448194
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,2R,3E,7S,9Z,11E,13S)-2-hydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,9,11-triene-5,15-dione
• SMILES (Canonical): CC1CC=CC=CC2CC(=O)CC2C(C=CC(=O)O1)O
• SMILES (Isomeric): C[C@H]1C/C=C\C=C\[C@@H]2CC(=O)C[C@H]2[C@@H](/C=C/C(=O)O1)O
• InChI: InChI=1S/C16H20O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h2-4,6-8,11-12,14-15,18H,5,9-10H2,1H3/b3-2-,6-4+,8-7+/t11-,12+,14+,15+/m0/s1
• InChI Key: FYDHFALTOZKRET-JNKDDRBLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.33 g/mol
• Exact Mass: 276.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.95
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9774	97.74%
Caco-2	-	0.6465	64.65%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6196	61.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8980	89.80%
OATP1B3 inhibitior	+	0.9647	96.47%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6921	69.21%
P-glycoprotein inhibitior	-	0.9430	94.30%
P-glycoprotein substrate	-	0.8260	82.60%
CYP3A4 substrate	+	0.5436	54.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8978	89.78%
CYP3A4 inhibition	-	0.9029	90.29%
CYP2C9 inhibition	-	0.9031	90.31%
CYP2C19 inhibition	-	0.9154	91.54%
CYP2D6 inhibition	-	0.9606	96.06%
CYP1A2 inhibition	-	0.7355	73.55%
CYP2C8 inhibition	-	0.9231	92.31%
CYP inhibitory promiscuity	-	0.9876	98.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9143	91.43%
Carcinogenicity (trinary)	Non-required	0.5278	52.78%
Eye corrosion	-	0.7799	77.99%
Eye irritation	-	0.9543	95.43%
Skin irritation	-	0.5346	53.46%
Skin corrosion	-	0.7324	73.24%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5322	53.22%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5428	54.28%
skin sensitisation	-	0.7790	77.90%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6014	60.14%
Acute Oral Toxicity (c)	III	0.5598	55.98%
Estrogen receptor binding	-	0.6607	66.07%
Androgen receptor binding	-	0.7001	70.01%
Thyroid receptor binding	-	0.7497	74.97%
Glucocorticoid receptor binding	+	0.6219	62.19%
Aromatase binding	-	0.6349	63.49%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7369	73.69%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.8686	86.86%

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	91.40%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.26%	91.11%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	88.20%	86.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.66%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.31%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.20%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.07%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.56%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	80.32%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139591668
• LOTUS: LTS0044008
• wikiData: Q105004430