2-[(1S,2R,5S,8S,10R,11R,15R)-8-hydroxy-11-methyl-15-[(1Z,2S)-1-(4-methyl-5-oxofuran-2-ylidene)propan-2-yl]-6,13-dioxo-14,16-dioxatetracyclo[8.6.0.02,8.011,15]hexadecan-5-yl]propan-2-yl acetate

Details

• Internal ID: 48afad6a-9543-4dab-bf8d-f0afecbf348f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: 2-[(1S,2R,5S,8S,10R,11R,15R)-8-hydroxy-11-methyl-15-[(1Z,2S)-1-(4-methyl-5-oxofuran-2-ylidene)propan-2-yl]-6,13-dioxo-14,16-dioxatetracyclo[8.6.0.02,8.011,15]hexadecan-5-yl]propan-2-yl acetate
• SMILES (Canonical): CC1=CC(=CC(C)C23C(CC(=O)O2)(C4CC5(CC(=O)C(CCC5C4O3)C(C)(C)OC(=O)C)O)C)OC1=O
• SMILES (Isomeric): CC1=C/C(=C/[C@H](C)[C@]23[C@](CC(=O)O2)([C@H]4C[C@@]5(CC(=O)[C@@H](CC[C@@H]5[C@H]4O3)C(C)(C)OC(=O)C)O)C)/OC1=O
• InChI: InChI=1S/C28H36O9/c1-14-9-17(34-24(14)32)10-15(2)28-26(6,13-22(31)36-28)20-11-27(33)12-21(30)18(25(4,5)35-16(3)29)7-8-19(27)23(20)37-28/h9-10,15,18-20,23,33H,7-8,11-13H2,1-6H3/b17-10-/t15-,18+,19+,20-,23+,26+,27-,28-/m0/s1
• InChI Key: IQTICRCDMUVTLN-IKDYPBKISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₉
• Molecular Weight: 516.60 g/mol
• Exact Mass: 516.23593272 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9846	98.46%
Caco-2	-	0.6715	67.15%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7076	70.76%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.8273	82.73%
OATP1B3 inhibitior	-	0.2194	21.94%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	+	0.9723	97.23%
P-glycoprotein inhibitior	+	0.7395	73.95%
P-glycoprotein substrate	+	0.5472	54.72%
CYP3A4 substrate	+	0.7255	72.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8931	89.31%
CYP3A4 inhibition	-	0.6687	66.87%
CYP2C9 inhibition	-	0.5822	58.22%
CYP2C19 inhibition	-	0.7556	75.56%
CYP2D6 inhibition	-	0.9537	95.37%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.6212	62.12%
CYP inhibitory promiscuity	-	0.9462	94.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5382	53.82%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9308	93.08%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9032	90.32%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5876	58.76%
skin sensitisation	-	0.7883	78.83%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6308	63.08%
Acute Oral Toxicity (c)	II	0.3972	39.72%
Estrogen receptor binding	+	0.7991	79.91%
Androgen receptor binding	+	0.7270	72.70%
Thyroid receptor binding	+	0.5380	53.80%
Glucocorticoid receptor binding	+	0.8220	82.20%
Aromatase binding	+	0.7128	71.28%
PPAR gamma	+	0.6405	64.05%
Honey bee toxicity	-	0.7130	71.30%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.10%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.55%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.43%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.10%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.65%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.86%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.64%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.18%	93.56%
CHEMBL1937	Q92769	Histone deacetylase 2	89.83%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.56%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.32%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.16%	99.23%
CHEMBL1902	P62942	FK506-binding protein 1A	85.86%	97.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.82%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.01%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.60%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.37%	90.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.31%	97.09%
CHEMBL325	Q13547	Histone deacetylase 1	84.22%	95.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.69%	96.61%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.67%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.67%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.22%	91.19%
CHEMBL299	P17252	Protein kinase C alpha	81.99%	98.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.26%	82.69%
CHEMBL2996	Q05655	Protein kinase C delta	80.22%	97.79%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.18%	96.90%

Plants that contains it

• Cassipourea madagascariensis
• Elaeodendron croceum
• Flourensia heterolepis
• Gymnosporia emarginata
• Microtropis fokienensis
• Nuxia sphaerocephala
• Salacia chinensis
• Schisandra lancifolia

Cross-Links

• PubChem: 44473750
• LOTUS: LTS0010200
• wikiData: Q105383494