5,6-Epxoyphysalin B

Details

• Internal ID: 46c1d41a-5974-4867-bc85-7ae17355ed22
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Physalins and derivatives
• IUPAC Name: (1R,2R,4R,6S,11R,12S,15S,18S,19R,20S,21S,23R,26S)-15-hydroxy-11,18,21-trimethyl-5,17,24,28,29-pentaoxanonacyclo[17.9.1.11,20.02,12.04,6.06,11.015,19.018,23.021,26]triacont-8-ene-10,16,25,30-tetrone
• SMILES (Canonical): CC12CC3C4(C56C1C(=O)C(O5)(C7CC8C9(O8)CC=CC(=O)C9(C7CCC6(C(=O)O4)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]7C[C@@H]8[C@]9(O8)CC=CC(=O)[C@@]9([C@H]7CC[C@]6(C(=O)O4)O)C)OC[C@H]2C(=O)O3)C
• InChI: InChI=1S/C28H30O10/c1-22-10-17-24(3)28-18(22)19(30)27(38-28,34-11-14(22)20(31)35-17)13-9-16-26(36-16)7-4-5-15(29)23(26,2)12(13)6-8-25(28,33)21(32)37-24/h4-5,12-14,16-18,33H,6-11H2,1-3H3/t12-,13+,14-,16+,17+,18-,22+,23-,24-,25+,26+,27+,28-/m0/s1
• InChI Key: VSLWNSSUMFSGFF-DKOLRWHASA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₀O₁₀
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.18389715 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.77
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEBI:69019
• 5,6-Epxoyphysalin B
• 57423-71-9
• CHEMBL1215434
• BDBM50378033
• 5beta,6beta-epoxy-5,6-dihydrophysalin B
• Q27137363

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9757	97.57%
Caco-2	-	0.7078	70.78%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7692	76.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8088	80.88%
OATP1B3 inhibitior	+	0.9034	90.34%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6217	62.17%
BSEP inhibitior	+	0.8763	87.63%
P-glycoprotein inhibitior	+	0.6733	67.33%
P-glycoprotein substrate	+	0.6952	69.52%
CYP3A4 substrate	+	0.7318	73.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8946	89.46%
CYP3A4 inhibition	-	0.7058	70.58%
CYP2C9 inhibition	-	0.8787	87.87%
CYP2C19 inhibition	-	0.9175	91.75%
CYP2D6 inhibition	-	0.9582	95.82%
CYP1A2 inhibition	-	0.8530	85.30%
CYP2C8 inhibition	+	0.6204	62.04%
CYP inhibitory promiscuity	-	0.9874	98.74%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5776	57.76%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9105	91.05%
Skin irritation	-	0.5688	56.88%
Skin corrosion	-	0.9016	90.16%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5092	50.92%
skin sensitisation	-	0.8764	87.64%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6452	64.52%
Acute Oral Toxicity (c)	I	0.3370	33.70%
Estrogen receptor binding	+	0.8513	85.13%
Androgen receptor binding	+	0.7821	78.21%
Thyroid receptor binding	+	0.6626	66.26%
Glucocorticoid receptor binding	+	0.8064	80.64%
Aromatase binding	+	0.7776	77.76%
PPAR gamma	+	0.6304	63.04%
Honey bee toxicity	-	0.7033	70.33%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9657	96.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5461	P08151	Zinc finger protein GLI1	660 nM	IC50	PMID: 19309080

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.83%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.24%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.14%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.24%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.46%	97.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.04%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.48%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.84%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.15%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	87.10%	97.79%
CHEMBL259	P32245	Melanocortin receptor 4	86.86%	95.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.24%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.08%	95.56%
CHEMBL1871	P10275	Androgen Receptor	85.52%	96.43%
CHEMBL4208	P20618	Proteasome component C5	85.35%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.64%	86.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.40%	96.77%
CHEMBL1937	Q92769	Histone deacetylase 2	82.60%	94.75%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.92%	91.24%
CHEMBL2581	P07339	Cathepsin D	80.28%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	80.04%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	80.03%	91.19%

Plants that contains it

• Achillea millefolium
• Alcea nudiflora
• Alkekengi officinarum
• Alocasia macrorrhizos
• Anaphalis margaritacea
• Angelica sinensis
• Boronia lanceolata
• Campanula pendula
• Carissa spinarum
• Chloranthus holostegius
• Clerodendrum infortunatum
• Corydalis crystallina
• Eucalyptus campanulata
• Euphorbia cattimandoo
• Hemiphragma heterophyllum
• Lasianthus attenuatus var. attenuatus
• Lomandra hastilis
• Mercurialis leiocarpa
• Morisonia scabrida
• Neolitsea sericea
• Ochradenus baccatus
• Physalis angulata
• Physalis lagascae
• Plantago ovata
• Podocarpus sellowii
• Podophyllum pleianthum
• Primula denticulata
• Rubus niveus
• Spinacia oleracea
• Teucrium cossonii
• Thujopsis dolabrata
• Turnera ulmifolia
• Witheringia solanacea

Cross-Links

• PubChem: 49864133
• NPASS: NPC33378
• ChEMBL: CHEMBL1215434
• LOTUS: LTS0242357
• wikiData: Q27137363