Narbonolide

Details

• Internal ID: 4e31103c-cfb4-47f1-a924-753ba82e2e12
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (3R,5R,6S,7S,9R,11E,13R,14R)-14-ethyl-6-hydroxy-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione
• InChI: InChI=1S/C20H32O5/c1-7-17-11(2)8-9-16(21)12(3)10-13(4)18(22)14(5)19(23)15(6)20(24)25-17/h8-9,11-15,17-18,22H,7,10H2,1-6H3/b9-8+/t11-,12-,13+,14-,15-,17-,18+/m1/s1
• InChI Key: YFFOFFWSBYZSOI-HQWJGCFGSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.50 g/mol
• Exact Mass: 352.22497412 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• (3R,5R,6S,7S,9R,11E,13R,14R)-14-ethyl-6-hydroxy-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione
• CHEBI:29650
• DTXSID001043712
• 32885-75-9
• RefChem:164827
• GlyTouCan:G19604IW
• DTXCID301526151
• G19604IW
• C11997
• AC1NQZE6
• Q27110204
• (3R,5R,6S,7S,9R,11E,13R,14R)-14-ethyl-6-hydroxy-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
• (3R,5R,6S,7S,9R,13R,14R,E)-14-Ethyl-6-hydroxy-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9852	98.52%
Caco-2	+	0.5117	51.17%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5558	55.58%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.8876	88.76%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8386	83.86%
P-glycoprotein inhibitior	-	0.6765	67.65%
P-glycoprotein substrate	-	0.6662	66.62%
CYP3A4 substrate	+	0.5582	55.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8981	89.81%
CYP3A4 inhibition	-	0.7577	75.77%
CYP2C9 inhibition	-	0.9142	91.42%
CYP2C19 inhibition	-	0.8794	87.94%
CYP2D6 inhibition	-	0.9592	95.92%
CYP1A2 inhibition	-	0.8676	86.76%
CYP2C8 inhibition	-	0.9052	90.52%
CYP inhibitory promiscuity	-	0.9708	97.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6148	61.48%
Eye corrosion	-	0.9402	94.02%
Eye irritation	-	0.9671	96.71%
Skin irritation	-	0.5951	59.51%
Skin corrosion	-	0.8500	85.00%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4433	44.33%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5676	56.76%
skin sensitisation	-	0.6822	68.22%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	-	0.5508	55.08%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6431	64.31%
Acute Oral Toxicity (c)	III	0.5031	50.31%
Estrogen receptor binding	+	0.7738	77.38%
Androgen receptor binding	+	0.6120	61.20%
Thyroid receptor binding	+	0.5739	57.39%
Glucocorticoid receptor binding	+	0.5855	58.55%
Aromatase binding	-	0.6643	66.43%
PPAR gamma	+	0.5183	51.83%
Honey bee toxicity	-	0.8153	81.53%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9334	93.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.24%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.04%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.89%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.12%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.10%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.58%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.20%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.51%	89.00%

Plants that contains it

• Lessingianthus linearis

Cross-Links

• PubChem: 5282035
• LOTUS: LTS0276158
• wikiData: Q105026372