Siphonol E

Details

• Internal ID: c1bb93c1-77d9-4636-821b-749f5de5e442
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Oxosteroids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,7,10-triacetyloxy-5-benzoyloxy-2-formyl-10a-hydroxy-4b-(hydroxymethyl)-2,8,8-trimethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(CC3OC(=O)C4=CC=CC=C4)(C)C=O)O)CO)OC(=O)C5=CC=CC=C5)OC(=O)C)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@@]([C@@H]3[C@@]1(C(=O)[C@@](C[C@H]3OC(=O)C4=CC=CC=C4)(C)C=O)O)([C@H]([C@H]([C@H](C2(C)C)OC(=O)C)OC(=O)C)OC(=O)C5=CC=CC=C5)CO
• InChI: InChI=1S/C39H44O14/c1-21(42)49-28-17-27-36(4,5)31(51-23(3)44)29(50-22(2)43)32(53-34(46)25-15-11-8-12-16-25)38(27,20-41)30-26(52-33(45)24-13-9-7-10-14-24)18-37(6,19-40)35(47)39(28,30)48/h7-16,19,26-32,41,48H,17-18,20H2,1-6H3/t26-,27+,28-,29+,30-,31-,32+,37-,38+,39+/m1/s1
• InChI Key: GZGMTWJDIWUSBB-LCIFRFTDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₄O₁₄
• Molecular Weight: 736.80 g/mol
• Exact Mass: 736.27310607 g/mol
• Topological Polar Surface Area (TPSA): 206.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 14
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• [(2R,4R,4As,4bS,5R,6S,7S,8aS,10R,10aR)-6,7,10-triacetyloxy-5-benzoyloxy-2-formyl-10a-hydroxy-4b-(hydroxymethyl)-2,8,8-trimethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9728	97.28%
Caco-2	-	0.8199	81.99%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8792	87.92%
OATP2B1 inhibitior	-	0.7221	72.21%
OATP1B1 inhibitior	+	0.8474	84.74%
OATP1B3 inhibitior	+	0.8370	83.70%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	+	0.9946	99.46%
P-glycoprotein inhibitior	+	0.8823	88.23%
P-glycoprotein substrate	+	0.5068	50.68%
CYP3A4 substrate	+	0.6904	69.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.6345	63.45%
CYP2C9 inhibition	-	0.7583	75.83%
CYP2C19 inhibition	-	0.8352	83.52%
CYP2D6 inhibition	-	0.9610	96.10%
CYP1A2 inhibition	-	0.6405	64.05%
CYP2C8 inhibition	+	0.5930	59.30%
CYP inhibitory promiscuity	-	0.9007	90.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6661	66.61%
Eye corrosion	-	0.9946	99.46%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.8111	81.11%
Skin corrosion	-	0.9786	97.86%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7109	71.09%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6098	60.98%
skin sensitisation	-	0.9045	90.45%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.6066	60.66%
Acute Oral Toxicity (c)	III	0.6343	63.43%
Estrogen receptor binding	+	0.7976	79.76%
Androgen receptor binding	+	0.7098	70.98%
Thyroid receptor binding	+	0.6307	63.07%
Glucocorticoid receptor binding	+	0.7632	76.32%
Aromatase binding	+	0.6049	60.49%
PPAR gamma	+	0.7541	75.41%
Honey bee toxicity	-	0.7307	73.07%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.53%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.39%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.81%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.37%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	93.52%	90.17%
CHEMBL1951	P21397	Monoamine oxidase A	91.85%	91.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.18%	95.50%
CHEMBL5028	O14672	ADAM10	86.51%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.38%	94.08%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.83%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.82%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	81.99%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.31%	93.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.84%	82.69%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.83%	94.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.01%	100.00%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Celmisia petriei
• Cenchrus americanus
• Chlorophytum malayense
• Cirsium helenioides
• Clausena indica
• Clusia torresii
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Ferula assa-foetida
• Gentiana olivieri
• Handroanthus guayacan
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus
• Orthosiphon aristatus var. aristatus
• Oryza sativa
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Populus tremula
• Primula veris
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Senecio integerrimus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Ulmus laciniata
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 10963687
• NPASS: NPC121712
• LOTUS: LTS0221902
• wikiData: Q104399612