Antifungal macrolide

Details

• Internal ID: 40c600ec-2cad-4f29-aef9-7094cb87eb8c
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,2R,5R,7R,10S,14S,16S)-5,14-diethyl-2,11-dimethyl-4,13,19,20-tetraoxatricyclo[14.2.1.17,10]icosane-3,12-dione
• SMILES (Canonical): CCC1CC2CCC(O2)C(C(=O)OC(CC3CCC(O3)C(C(=O)O1)C)CC)C
• SMILES (Isomeric): CC[C@@H]1C[C@H]2CC[C@H](O2)C(C(=O)O[C@H](C[C@@H]3CC[C@@H](O3)[C@H](C(=O)O1)C)CC)C
• InChI: InChI=1S/C22H36O6/c1-5-15-11-17-7-9-20(25-17)14(4)22(24)28-16(6-2)12-18-8-10-19(26-18)13(3)21(23)27-15/h13-20H,5-12H2,1-4H3/t13-,14?,15-,16+,17-,18+,19-,20+/m1/s1
• InChI Key: VYGSEJPMQXVTNW-UPOFUFPUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₆
• Molecular Weight: 396.50 g/mol
• Exact Mass: 396.25118886 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• CHEBI:189215
• (1R,2R,5R,7R,10S,14S,16S)-5,14-diethyl-2,11-dimethyl-4,13,19,20-tetraoxatricyclo[14.2.1.17,10]icosane-3,12-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9749	97.49%
Caco-2	+	0.5632	56.32%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6422	64.22%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9313	93.13%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5831	58.31%
P-glycoprotein inhibitior	+	0.6238	62.38%
P-glycoprotein substrate	-	0.7274	72.74%
CYP3A4 substrate	-	0.5542	55.42%
CYP2C9 substrate	+	0.6107	61.07%
CYP2D6 substrate	-	0.8638	86.38%
CYP3A4 inhibition	-	0.8735	87.35%
CYP2C9 inhibition	-	0.8859	88.59%
CYP2C19 inhibition	-	0.8259	82.59%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.8237	82.37%
CYP2C8 inhibition	-	0.9506	95.06%
CYP inhibitory promiscuity	-	0.9741	97.41%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9373	93.73%
Eye irritation	-	0.7634	76.34%
Skin irritation	-	0.6343	63.43%
Skin corrosion	-	0.8303	83.03%
Ames mutagenesis	-	0.6464	64.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6387	63.87%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.8177	81.77%
skin sensitisation	-	0.9068	90.68%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.6100	61.00%
Acute Oral Toxicity (c)	III	0.8084	80.84%
Estrogen receptor binding	+	0.8699	86.99%
Androgen receptor binding	+	0.5487	54.87%
Thyroid receptor binding	+	0.5421	54.21%
Glucocorticoid receptor binding	+	0.6292	62.92%
Aromatase binding	+	0.5431	54.31%
PPAR gamma	+	0.6657	66.57%
Honey bee toxicity	-	0.9021	90.21%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9259	92.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.97%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.52%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.93%	94.80%
CHEMBL3401	O75469	Pregnane X receptor	88.14%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.70%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.43%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.76%	91.11%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139583904
• LOTUS: LTS0118395
• wikiData: Q75069044