(3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-4,6,12-trihydroxy-3,5,7,9,11,13-hexamethyl-14-propyl-oxacyclotetradecane-2,10-dione

Details

• Internal ID: dbe3b95d-f4a1-46b4-a23f-59a7db591a9c
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-4,6,12-trihydroxy-3,5,7,9,11,13-hexamethyl-14-propyl-oxacyclotetradecane-2,10-dione
• SMILES (Canonical): CCCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)O)C)O)C)C)C)O)C
• SMILES (Isomeric): CCC[C@@H]1[C@@H]([C@@H]([C@H](C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O)C)O)C)C)C)O)C
• InChI: InChI=1S/C22H40O6/c1-8-9-17-13(4)20(25)14(5)18(23)11(2)10-12(3)19(24)15(6)21(26)16(7)22(27)28-17/h11-17,19-21,24-26H,8-10H2,1-7H3/t11-,12+,13+,14+,15-,16-,17-,19+,20+,21+/m1/s1
• InChI Key: CAFPEYWNLASVHQ-JKNGSDSYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₄₀O₆
• Molecular Weight: 400.50 g/mol
• Exact Mass: 400.28248899 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8112	81.12%
Caco-2	-	0.5399	53.99%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6486	64.86%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.9129	91.29%
OATP1B3 inhibitior	+	0.9413	94.13%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8521	85.21%
P-glycoprotein inhibitior	-	0.6315	63.15%
P-glycoprotein substrate	-	0.6964	69.64%
CYP3A4 substrate	+	0.5183	51.83%
CYP2C9 substrate	-	0.7874	78.74%
CYP2D6 substrate	-	0.8433	84.33%
CYP3A4 inhibition	+	0.5945	59.45%
CYP2C9 inhibition	-	0.8795	87.95%
CYP2C19 inhibition	-	0.8140	81.40%
CYP2D6 inhibition	-	0.9328	93.28%
CYP1A2 inhibition	-	0.8113	81.13%
CYP2C8 inhibition	-	0.9372	93.72%
CYP inhibitory promiscuity	-	0.9485	94.85%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7111	71.11%
Eye corrosion	-	0.9687	96.87%
Eye irritation	-	0.9399	93.99%
Skin irritation	-	0.6506	65.06%
Skin corrosion	-	0.7311	73.11%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5856	58.56%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5533	55.33%
skin sensitisation	-	0.8558	85.58%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5159	51.59%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5666	56.66%
Acute Oral Toxicity (c)	III	0.5641	56.41%
Estrogen receptor binding	+	0.7242	72.42%
Androgen receptor binding	-	0.5087	50.87%
Thyroid receptor binding	+	0.5619	56.19%
Glucocorticoid receptor binding	-	0.6086	60.86%
Aromatase binding	-	0.6336	63.36%
PPAR gamma	+	0.5361	53.61%
Honey bee toxicity	-	0.8846	88.46%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5432	54.32%
Fish aquatic toxicity	+	0.7989	79.89%

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	95.47%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.80%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.57%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.74%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.70%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.66%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.24%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.98%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.87%	95.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10408709
• LOTUS: LTS0063495
• wikiData: Q104951127