(1R,4Z,6R,7S,11Z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6,14-dimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

Details

• Internal ID: 48a08c5f-3a06-416b-b63b-961cb3d9ea48
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,4Z,6R,7S,11Z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6,14-dimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
• SMILES (Canonical): CC=C1CC(C(C(=O)OCC2=CCN(CCC(C2=O)OC1=O)C)(CO)O)C
• SMILES (Isomeric): C/C=C\1/C[C@H]([C@@](C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC1=O)C)(CO)O)C
• InChI: InChI=1S/C19H27NO7/c1-4-13-9-12(2)19(25,11-21)18(24)26-10-14-5-7-20(3)8-6-15(16(14)22)27-17(13)23/h4-5,12,15,21,25H,6-11H2,1-3H3/b13-4-,14-5-/t12-,15-,19-/m1/s1
• InChI Key: FKDPVQYTQVJUGD-HUCHPOGGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₇NO₇
• Molecular Weight: 381.40 g/mol
• Exact Mass: 381.17875220 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.02
• H-Bond Acceptor: 8
• 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	+	0.7883	78.83%
Caco-2	+	0.5842	58.42%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5157	51.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9110	91.10%
OATP1B3 inhibitior	+	0.9228	92.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8021	80.21%
BSEP inhibitior	+	0.6408	64.08%
P-glycoprotein inhibitior	-	0.6860	68.60%
P-glycoprotein substrate	-	0.5348	53.48%
CYP3A4 substrate	+	0.6342	63.42%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	-	0.8459	84.59%
CYP3A4 inhibition	-	0.7660	76.60%
CYP2C9 inhibition	-	0.8689	86.89%
CYP2C19 inhibition	-	0.8962	89.62%
CYP2D6 inhibition	-	0.9475	94.75%
CYP1A2 inhibition	-	0.8754	87.54%
CYP2C8 inhibition	-	0.8701	87.01%
CYP inhibitory promiscuity	-	1.0000	100.00%
UGT catelyzed	-	0.9000	90.00%
Carcinogenicity (binary)	-	0.7700	77.00%
Carcinogenicity (trinary)	Danger	0.7477	74.77%
Eye corrosion	-	0.9802	98.02%
Eye irritation	-	0.9794	97.94%
Skin irritation	-	0.7248	72.48%
Skin corrosion	-	0.9205	92.05%
Ames mutagenesis	+	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5415	54.15%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8322	83.22%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.7155	71.55%
Acute Oral Toxicity (c)	III	0.3506	35.06%
Estrogen receptor binding	-	0.5960	59.60%
Androgen receptor binding	-	0.5073	50.73%
Thyroid receptor binding	-	0.6918	69.18%
Glucocorticoid receptor binding	+	0.6131	61.31%
Aromatase binding	-	0.5768	57.68%
PPAR gamma	-	0.6192	61.92%
Honey bee toxicity	-	0.8553	85.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.32%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.96%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.92%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.52%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.94%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.55%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.84%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.63%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.73%	97.25%

Plants that contains it

• Crotalaria laburnifolia
• Tephroseris integrifolia

Cross-Links

• PubChem: 12041879
• LOTUS: LTS0007004
• wikiData: Q104996529