Siphonol A

Details

• Internal ID: b56a4d61-c24d-4b16-9ebd-7f783736077f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,7,10-triacetyloxy-5-benzoyloxy-2-ethenyl-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=C)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=C)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/C40H46O13/c1-8-38(7)20-27(52-34(45)25-15-11-9-12-16-25)31-39(21-41)28(19-29(49-22(2)42)40(31,48)36(38)47)37(5,6)32(51-24(4)44)30(50-23(3)43)33(39)53-35(46)26-17-13-10-14-18-26/h8-18,27-33,41,48H,1,19-21H2,2-7H3/t27-,28+,29-,30+,31-,32-,33+,38+,39+,40+/m1/s1
• InChI Key: FGNRGTAPXIKBOC-HZYAOAIPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₆O₁₃
• Molecular Weight: 734.80 g/mol
• Exact Mass: 734.29384152 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 3.78
• H-Bond Acceptor: 13
• 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-ethenyl-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	+	0.9764	97.64%
Caco-2	-	0.8299	82.99%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8290	82.90%
OATP2B1 inhibitior	-	0.7215	72.15%
OATP1B1 inhibitior	+	0.8647	86.47%
OATP1B3 inhibitior	+	0.8274	82.74%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8457	84.57%
BSEP inhibitior	+	0.9955	99.55%
P-glycoprotein inhibitior	+	0.8554	85.54%
P-glycoprotein substrate	-	0.5506	55.06%
CYP3A4 substrate	+	0.6954	69.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8836	88.36%
CYP3A4 inhibition	+	0.6424	64.24%
CYP2C9 inhibition	-	0.7585	75.85%
CYP2C19 inhibition	-	0.7654	76.54%
CYP2D6 inhibition	-	0.9466	94.66%
CYP1A2 inhibition	-	0.6974	69.74%
CYP2C8 inhibition	+	0.6052	60.52%
CYP inhibitory promiscuity	-	0.8638	86.38%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6850	68.50%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8987	89.87%
Skin irritation	-	0.7504	75.04%
Skin corrosion	-	0.9663	96.63%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7176	71.76%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5973	59.73%
skin sensitisation	-	0.8466	84.66%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5887	58.87%
Acute Oral Toxicity (c)	III	0.6323	63.23%
Estrogen receptor binding	+	0.7875	78.75%
Androgen receptor binding	+	0.7078	70.78%
Thyroid receptor binding	+	0.6446	64.46%
Glucocorticoid receptor binding	+	0.7508	75.08%
Aromatase binding	+	0.6091	60.91%
PPAR gamma	+	0.7391	73.91%
Honey bee toxicity	-	0.7017	70.17%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.80%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.53%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	95.53%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.14%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.89%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	93.59%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.78%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.90%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.27%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.91%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.56%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.42%	91.07%
CHEMBL5028	O14672	ADAM10	84.85%	97.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.74%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.25%	95.89%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.57%	94.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.02%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.05%	93.00%

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: 10952715
• NPASS: NPC178177
• LOTUS: LTS0102849
• wikiData: Q104399608