(1R,2S,5S,8S,9R,15S,17R,18R,21S,24R,26S,27S)-5,15-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.118,27.01,5.02,24.08,17.09,14.021,26]nonacosa-11,13-diene-4,10,22,29-tetrone

Details

• Internal ID: d28fafa7-5b0b-41bf-af7f-49eda1fe5310
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Physalins and derivatives
• IUPAC Name: (1R,2S,5S,8S,9R,15S,17R,18R,21S,24R,26S,27S)-5,15-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.118,27.01,5.02,24.08,17.09,14.021,26]nonacosa-11,13-diene-4,10,22,29-tetrone
• SMILES (Canonical): CC12CC3C4(C56C1C(=O)C(O5)(C7CC(C8=CC=CC(=O)C8(C7CCC6(C(=O)O4)O)C)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](C8=CC=CC(=O)[C@@]8([C@H]7CC[C@]6(C(=O)O4)O)C)O)OC[C@H]2C(=O)O3)C
• InChI: InChI=1S/C28H30O10/c1-23-10-18-25(3)28-19(23)20(31)27(38-28,35-11-15(23)21(32)36-18)14-9-16(29)13-5-4-6-17(30)24(13,2)12(14)7-8-26(28,34)22(33)37-25/h4-6,12,14-16,18-19,29,34H,7-11H2,1-3H3/t12-,14+,15-,16-,18+,19-,23+,24+,25-,26+,27+,28-/m0/s1
• InChI Key: CGVBSJOSWAZUIF-IOMVKLDJSA-N
• Popularity: 8 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): 146.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.53
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• CHEBI:69020
• CHEMBL1835434
• Q27137364

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	-	0.7496	74.96%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8383	83.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8221	82.21%
OATP1B3 inhibitior	+	0.9673	96.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6020	60.20%
BSEP inhibitior	+	0.6605	66.05%
P-glycoprotein inhibitior	+	0.6471	64.71%
P-glycoprotein substrate	+	0.6717	67.17%
CYP3A4 substrate	+	0.7340	73.40%
CYP2C9 substrate	-	0.8137	81.37%
CYP2D6 substrate	-	0.8986	89.86%
CYP3A4 inhibition	-	0.8167	81.67%
CYP2C9 inhibition	-	0.8860	88.60%
CYP2C19 inhibition	-	0.9634	96.34%
CYP2D6 inhibition	-	0.9589	95.89%
CYP1A2 inhibition	-	0.8804	88.04%
CYP2C8 inhibition	+	0.5925	59.25%
CYP inhibitory promiscuity	-	0.9778	97.78%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4427	44.27%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9263	92.63%
Skin irritation	+	0.6057	60.57%
Skin corrosion	-	0.9201	92.01%
Ames mutagenesis	-	0.6808	68.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.4777	47.77%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8907	89.07%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5230	52.30%
Acute Oral Toxicity (c)	III	0.3730	37.30%
Estrogen receptor binding	+	0.8072	80.72%
Androgen receptor binding	+	0.7842	78.42%
Thyroid receptor binding	+	0.6426	64.26%
Glucocorticoid receptor binding	+	0.8018	80.18%
Aromatase binding	+	0.7384	73.84%
PPAR gamma	+	0.5785	57.85%
Honey bee toxicity	-	0.6347	63.47%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9793	97.93%

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	97.93%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.28%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.21%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.09%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.87%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.63%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.79%	94.80%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.94%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.14%	96.77%
CHEMBL1871	P10275	Androgen Receptor	88.11%	96.43%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.94%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.85%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.04%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.93%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.53%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.07%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	82.71%	90.17%
CHEMBL220	P22303	Acetylcholinesterase	82.34%	94.45%
CHEMBL259	P32245	Melanocortin receptor 4	80.80%	95.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.71%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	80.43%	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
• Plantago ovata
• Podocarpus sellowii
• Podophyllum pleianthum
• Primula denticulata
• Rubus niveus
• Spinacia oleracea
• Teucrium cossonii
• Thujopsis dolabrata
• Turnera ulmifolia

Cross-Links

• PubChem: 56683730
• NPASS: NPC243014
• ChEMBL: CHEMBL1835434