Siphonol B

Details

• Internal ID: 99f26226-81f9-48f7-b348-26d1f3f44818
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,7-diacetyloxy-5-benzoyloxy-2-ethenyl-10,10a-dihydroxy-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)OC1C(C(C2CC(C3(C(C2(C1OC(=O)C4=CC=CC=C4)CO)C(CC(C3=O)(C)C=C)OC(=O)C5=CC=CC=C5)O)O)(C)C)OC(=O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]([C@]2([C@@H](C[C@H]([C@@]3([C@@H]2[C@@H](C[C@](C3=O)(C)C=C)OC(=O)C4=CC=CC=C4)O)O)C([C@@H]1OC(=O)C)(C)C)CO)OC(=O)C5=CC=CC=C5
• InChI: InChI=1S/C38H44O12/c1-7-36(6)19-25(49-32(43)23-14-10-8-11-15-23)29-37(20-39)26(18-27(42)38(29,46)34(36)45)35(4,5)30(48-22(3)41)28(47-21(2)40)31(37)50-33(44)24-16-12-9-13-17-24/h7-17,25-31,39,42,46H,1,18-20H2,2-6H3/t25-,26+,27-,28+,29-,30-,31+,36+,37+,38+/m1/s1
• InChI Key: XYELSYGEQPFQMP-OFUWLHILSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₄O₁₂
• Molecular Weight: 692.70 g/mol
• Exact Mass: 692.28327683 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9699	96.99%
Caco-2	-	0.8308	83.08%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8332	83.32%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8665	86.65%
OATP1B3 inhibitior	+	0.8550	85.50%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9949	99.49%
P-glycoprotein inhibitior	+	0.8368	83.68%
P-glycoprotein substrate	-	0.5453	54.53%
CYP3A4 substrate	+	0.6928	69.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	+	0.7201	72.01%
CYP2C9 inhibition	-	0.8166	81.66%
CYP2C19 inhibition	-	0.7917	79.17%
CYP2D6 inhibition	-	0.9442	94.42%
CYP1A2 inhibition	-	0.6724	67.24%
CYP2C8 inhibition	+	0.5679	56.79%
CYP inhibitory promiscuity	-	0.9479	94.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7101	71.01%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.9037	90.37%
Skin irritation	-	0.7202	72.02%
Skin corrosion	-	0.9588	95.88%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8289	82.89%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5473	54.73%
skin sensitisation	-	0.8336	83.36%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4763	47.63%
Acute Oral Toxicity (c)	III	0.6225	62.25%
Estrogen receptor binding	+	0.7926	79.26%
Androgen receptor binding	+	0.7158	71.58%
Thyroid receptor binding	+	0.6482	64.82%
Glucocorticoid receptor binding	+	0.7524	75.24%
Aromatase binding	+	0.5982	59.82%
PPAR gamma	+	0.7097	70.97%
Honey bee toxicity	-	0.6957	69.57%
Biodegradation	-	0.7750	77.50%
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
CHEMBL1951	P21397	Monoamine oxidase A	98.20%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	96.43%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.07%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.01%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.93%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.56%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.22%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.89%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.81%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	89.09%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.04%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.22%	91.07%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.62%	95.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.39%	94.08%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.58%	97.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.52%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.19%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.34%	100.00%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Cenchrus americanus
• Chlorophytum malayense
• Clausena indica
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Gentiana olivieri
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus var. aristatus
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 11017910
• NPASS: NPC261969
• LOTUS: LTS0195837
• wikiData: Q104399609