(1R,2S,5R,8S,9R,14S,16R,17S,18R,21R,24R,26S,27R)-5,14,16-trihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.118,27.01,5.02,24.08,17.09,14.021,26]nonacos-11-ene-4,10,22,29-tetrone

Details

• Internal ID: c52394de-f1ce-4a32-827b-ea735e9b2cf3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Physalins and derivatives
• IUPAC Name: (1R,2S,5R,8S,9R,14S,16R,17S,18R,21R,24R,26S,27R)-5,14,16-trihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.118,27.01,5.02,24.08,17.09,14.021,26]nonacos-11-ene-4,10,22,29-tetrone
• SMILES (Canonical): CC12CC3C4(C56C1C(=O)C(O5)(C7C(CCC6(C(=O)O4)O)C8(C(=O)C=CCC8(CC7O)O)C)OCC2C(=O)O3)C
• SMILES (Isomeric): C[C@]12C[C@@H]3[C@]4([C@]56[C@@H]1C(=O)[C@](O5)([C@H]7[C@H](CC[C@@]6(C(=O)O4)O)[C@]8(C(=O)C=CC[C@@]8(C[C@H]7O)O)C)OC[C@@H]2C(=O)O3)C
• InChI: InChI=1S/C28H32O11/c1-22-10-16-24(3)28-18(22)19(31)27(39-28,36-11-13(22)20(32)37-16)17-12(6-8-26(28,35)21(33)38-24)23(2)15(30)5-4-7-25(23,34)9-14(17)29/h4-5,12-14,16-18,29,34-35H,6-11H2,1-3H3/t12-,13+,14+,16+,17-,18+,22+,23-,24-,25-,26-,27+,28-/m0/s1
• InChI Key: YFLAVJCREXGADP-CCLDXJELSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₁
• Molecular Weight: 544.50 g/mol
• Exact Mass: 544.19446183 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.28
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8950	89.50%
Caco-2	-	0.7440	74.40%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7425	74.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8138	81.38%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6717	67.17%
BSEP inhibitior	+	0.9280	92.80%
P-glycoprotein inhibitior	+	0.6305	63.05%
P-glycoprotein substrate	+	0.6481	64.81%
CYP3A4 substrate	+	0.7387	73.87%
CYP2C9 substrate	-	0.8137	81.37%
CYP2D6 substrate	-	0.8986	89.86%
CYP3A4 inhibition	-	0.8763	87.63%
CYP2C9 inhibition	-	0.9218	92.18%
CYP2C19 inhibition	-	0.9378	93.78%
CYP2D6 inhibition	-	0.9650	96.50%
CYP1A2 inhibition	-	0.9131	91.31%
CYP2C8 inhibition	+	0.5948	59.48%
CYP inhibitory promiscuity	-	0.9787	97.87%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5419	54.19%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9256	92.56%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9147	91.47%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9146	91.46%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5357	53.57%
Acute Oral Toxicity (c)	I	0.4713	47.13%
Estrogen receptor binding	+	0.8586	85.86%
Androgen receptor binding	+	0.7816	78.16%
Thyroid receptor binding	+	0.6212	62.12%
Glucocorticoid receptor binding	+	0.7945	79.45%
Aromatase binding	+	0.7820	78.20%
PPAR gamma	+	0.5952	59.52%
Honey bee toxicity	-	0.7295	72.95%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9641	96.41%

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	98.17%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.82%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.55%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.17%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.33%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.79%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.32%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.78%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.41%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.74%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.50%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.80%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.70%	95.56%
CHEMBL1871	P10275	Androgen Receptor	85.70%	96.43%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.55%	94.80%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.49%	82.69%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.23%	96.39%
CHEMBL4208	P20618	Proteasome component C5	82.99%	90.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.31%	91.24%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.25%	96.77%

Plants that contains it

• Alkekengi officinarum

Cross-Links

• PubChem: 101586381
• NPASS: NPC95389