(1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3,4,5,6,9,11,13,14,14a,14b-decahydro-3,6-dihydroxy-3-((1R)-1-hydroxyethyl)-5,6-dimethyl-, (3R,5R,6S,14aR,14bR)-

Details

• Internal ID: bd2f34e0-a2bf-4b58-8245-c88d45839910
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,4R,6R,7S,17R)-4,7-dihydroxy-4-[(1R)-1-hydroxyethyl]-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
• SMILES (Canonical): CC1CC(C(=O)OC2CCN3C2C(=CC3)COC(=O)C1(C)O)(C(C)O)O
• SMILES (Isomeric): C[C@@H]1C[C@](C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@@]1(C)O)([C@@H](C)O)O
• InChI: InChI=1S/C18H27NO7/c1-10-8-18(24,11(2)20)16(22)26-13-5-7-19-6-4-12(14(13)19)9-25-15(21)17(10,3)23/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17+,18-/m1/s1
• InChI Key: FMWJEBGSMAOQNN-MCCFIOHQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₇NO₇
• Molecular Weight: 369.40 g/mol
• Exact Mass: 369.17875220 g/mol
• Topological Polar Surface Area (TPSA): 117.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.64
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• Jacoline
• USC51AR5V5
• 480-76-2
• (1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3,4,5,6,9,11,13,14,14a,14b-decahydro-3,6-dihydroxy-3-((1R)-1-hydroxyethyl)-5,6-dimethyl-, (3R,5R,6S,14aR,14bR)-
• (1R,4R,6R,7S,17R)-4,7-dihydroxy-4-[(1R)-1-hydroxyethyl]-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
• (15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione
• A902555
• Q27291244
• SENECIONAN-11,16-DIONE, 15,20-DIHYDRO-12,15,20-TRIHYDROXY-, (15.ALPHA.,20R)-
• Senecionan-11,16-dione, 15,20-dihydro-12,15,20-trihydroxy-, (15alpha,20R)-
• (4aR,7S,9R,10R,13bR)-7,10-Dihydroxy-7-((R)-1-hydroxy-ethyl)-9,10-dimethyl-2,3,4,4a,7,8,9,10,13,13b-decahydro-5,12-dioxa-2a-aza-cyclododeca[cd]pentalene-6,11-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8685	86.85%
Caco-2	+	0.5553	55.53%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5454	54.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9427	94.27%
OATP1B3 inhibitior	+	0.9408	94.08%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6789	67.89%
P-glycoprotein inhibitior	-	0.9075	90.75%
P-glycoprotein substrate	+	0.5545	55.45%
CYP3A4 substrate	+	0.5883	58.83%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.6669	66.69%
CYP3A4 inhibition	-	0.8910	89.10%
CYP2C9 inhibition	-	0.9222	92.22%
CYP2C19 inhibition	-	0.9193	91.93%
CYP2D6 inhibition	-	0.9329	93.29%
CYP1A2 inhibition	-	0.9156	91.56%
CYP2C8 inhibition	-	0.9204	92.04%
CYP inhibitory promiscuity	-	0.9941	99.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Danger	0.8010	80.10%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.9831	98.31%
Skin irritation	-	0.7105	71.05%
Skin corrosion	-	0.9176	91.76%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8379	83.79%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5616	56.16%
Acute Oral Toxicity (c)	II	0.4932	49.32%
Estrogen receptor binding	+	0.6424	64.24%
Androgen receptor binding	+	0.5387	53.87%
Thyroid receptor binding	+	0.5233	52.33%
Glucocorticoid receptor binding	+	0.6785	67.85%
Aromatase binding	-	0.5135	51.35%
PPAR gamma	-	0.7636	76.36%
Honey bee toxicity	-	0.8621	86.21%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7768	77.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.23%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.07%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.86%	97.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.49%	93.40%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	89.94%	86.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.33%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.18%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.98%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.86%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.47%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.67%	91.11%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.22%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.46%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.25%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.92%	98.95%
CHEMBL4208	P20618	Proteasome component C5	85.39%	90.00%
CHEMBL240	Q12809	HERG	85.20%	89.76%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	84.19%	98.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.57%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.91%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.82%	89.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.36%	96.47%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.76%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.55%	96.77%

Plants that contains it

• Crassocephalum crepidioides
• Crotalaria micans
• Jacobaea vulgaris
• Senecio vulgaris

Cross-Links

• PubChem: 12096664
• LOTUS: LTS0196510
• wikiData: Q27291244