(1R,2R,4R,5R,8S,11R,13S,14S,15R,16S,19S,22S,23R,25S)-2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.15,14.15,15.01,23.04,22.08,13.011,16.015,19]hentriacont-28-ene-9,18,24,31-tetrone

Details

• Internal ID: 4b02710a-852d-4f73-bd0e-f5ad5f2de556
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Physalins and derivatives
• IUPAC Name: (1R,2R,4R,5R,8S,11R,13S,14S,15R,16S,19S,22S,23R,25S)-2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.15,14.15,15.01,23.04,22.08,13.011,16.015,19]hentriacont-28-ene-9,18,24,31-tetrone
• SMILES (Canonical): CC12CC3C4(C56C1C(=O)C(O5)(C7CC(C89C=CC(C(=O)C8(C7CCC6(C(=O)O4)O)C)OO9)O)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]([C@@]89C=C[C@@H](C(=O)[C@@]8([C@H]7CC[C@]6(C(=O)O4)O)C)OO9)O)OC[C@H]2C(=O)O3)C
• InChI: InChI=1S/C28H30O12/c1-22-9-16-24(3)28-17(22)19(31)27(39-28,35-10-13(22)20(32)36-16)12-8-15(29)26-7-5-14(38-40-26)18(30)23(26,2)11(12)4-6-25(28,34)21(33)37-24/h5,7,11-17,29,34H,4,6,8-10H2,1-3H3/t11-,12+,13-,14-,15+,16+,17-,22+,23-,24-,25+,26-,27+,28-/m0/s1
• InChI Key: IRYOOASWRCIZCK-GDRGPWMWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₀O₁₂
• Molecular Weight: 558.50 g/mol
• Exact Mass: 558.17372639 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.33
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9672	96.72%
Caco-2	-	0.7705	77.05%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7520	75.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8169	81.69%
OATP1B3 inhibitior	+	0.9267	92.67%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6967	69.67%
BSEP inhibitior	+	0.6816	68.16%
P-glycoprotein inhibitior	+	0.6449	64.49%
P-glycoprotein substrate	+	0.6594	65.94%
CYP3A4 substrate	+	0.7392	73.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8679	86.79%
CYP3A4 inhibition	-	0.8067	80.67%
CYP2C9 inhibition	-	0.9132	91.32%
CYP2C19 inhibition	-	0.9331	93.31%
CYP2D6 inhibition	-	0.9599	95.99%
CYP1A2 inhibition	-	0.8043	80.43%
CYP2C8 inhibition	+	0.5719	57.19%
CYP inhibitory promiscuity	-	0.9862	98.62%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5174	51.74%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9121	91.21%
Skin irritation	-	0.5714	57.14%
Skin corrosion	-	0.9029	90.29%
Ames mutagenesis	-	0.6240	62.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.6380	63.80%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5533	55.33%
skin sensitisation	-	0.8909	89.09%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4888	48.88%
Acute Oral Toxicity (c)	I	0.3711	37.11%
Estrogen receptor binding	+	0.8232	82.32%
Androgen receptor binding	+	0.7846	78.46%
Thyroid receptor binding	+	0.6013	60.13%
Glucocorticoid receptor binding	+	0.7704	77.04%
Aromatase binding	+	0.7483	74.83%
PPAR gamma	+	0.6101	61.01%
Honey bee toxicity	-	0.6905	69.05%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9738	97.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.91%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.37%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.88%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.58%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.97%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.44%	94.45%
CHEMBL1871	P10275	Androgen Receptor	92.03%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.33%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.88%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.90%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.86%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.81%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.57%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.53%	94.80%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.31%	96.61%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.79%	97.14%
CHEMBL299	P17252	Protein kinase C alpha	84.84%	98.03%
CHEMBL259	P32245	Melanocortin receptor 4	81.68%	95.38%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.00%	82.69%

Plants that contains it

• Achillea millefolium
• Alcea nudiflora
• 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 minima
• Plantago ovata
• Podocarpus sellowii
• Podophyllum pleianthum
• Primula denticulata
• Rubus niveus
• Spinacia oleracea
• Teucrium cossonii
• Thujopsis dolabrata
• Turnera ulmifolia

Cross-Links

• PubChem: 21633629
• NPASS: NPC227952
• LOTUS: LTS0018029
• wikiData: Q105119306