(1R,6R,7S,17S)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

Details

• Internal ID: c3de9259-6704-47d1-b580-069419f7c15c
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,6R,7S,17S)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
• SMILES (Canonical): CC=C1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(CO)O)C
• SMILES (Isomeric): CC=C1C[C@H]([C@@](C(=O)OCC2=CCN3[C@@H]2[C@@H](CC3)OC1=O)(CO)O)C
• InChI: InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/t11-,14-,15+,18-/m1/s1
• InChI Key: BCJMNZRQJAVDLD-ZKRNXSKHSA-N
• Popularity: 47 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.40 g/mol
• Exact Mass: 351.16818752 g/mol
• Topological Polar Surface Area (TPSA): 96.30 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.17
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8976	89.76%
Caco-2	+	0.6154	61.54%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5590	55.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9129	91.29%
OATP1B3 inhibitior	+	0.9429	94.29%
MATE1 inhibitior	-	0.9009	90.09%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4711	47.11%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6115	61.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8070	80.70%
CYP3A4 inhibition	-	0.9263	92.63%
CYP2C9 inhibition	-	0.9233	92.33%
CYP2C19 inhibition	-	0.9220	92.20%
CYP2D6 inhibition	-	0.9264	92.64%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8568	85.68%
CYP inhibitory promiscuity	-	0.9922	99.22%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.7918	79.18%
Eye corrosion	-	0.9831	98.31%
Eye irritation	-	0.9920	99.20%
Skin irritation	-	0.7134	71.34%
Skin corrosion	-	0.9154	91.54%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4536	45.36%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8412	84.12%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.7058	70.58%
Acute Oral Toxicity (c)	I	0.7755	77.55%
Estrogen receptor binding	-	0.7174	71.74%
Androgen receptor binding	+	0.5202	52.02%
Thyroid receptor binding	-	0.6409	64.09%
Glucocorticoid receptor binding	+	0.6512	65.12%
Aromatase binding	-	0.6137	61.37%
PPAR gamma	-	0.7595	75.95%
Honey bee toxicity	-	0.8546	85.46%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.6718	67.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.13%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.64%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.51%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.89%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.68%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.90%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.47%	85.14%
CHEMBL2581	P07339	Cathepsin D	86.41%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.52%	93.40%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.29%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.94%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.88%	99.23%
CHEMBL4588	P22894	Matrix metalloproteinase 8	81.82%	94.66%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.16%	97.14%

Plants that contains it

• Crotalaria trichotoma
• Jacobaea maritima subsp. maritima
• Jacobaea vulgaris
• Osyris alba
• Packera anonyma
• Packera candidissima
• Packera coahuilensis
• Senecio brasiliensis
• Senecio ceratophylloides
• Senecio covasii
• Senecio deferens
• Senecio flaccidus var. douglasii
• Senecio gilliesianus
• Senecio glaucus
• Senecio grisebachii
• Senecio inaequidens
• Senecio isatideus
• Senecio leptolobus
• Senecio nevadensis subsp. malacitanus
• Senecio oxyphyllus
• Senecio prionopterus
• Senecio retrorsus
• Senecio riddellii
• Senecio selloi
• Senecio subulatus
• Senecio triangularis
• Senecio uspallatensis
• Senecio vernalis
• Senecio vulgaris
• Werneria nubigena

Cross-Links

• PubChem: 126968828
• LOTUS: LTS0140521
• wikiData: Q104250414