Sphinxolide B

Details

• Internal ID: 258d9539-b8b0-49c6-a7da-c9b47e97ae72
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: N-[(E,4R,5R,9S,10S,11S)-11-[(3R,5Z,7E,11S,12S,13E,15R,17S,18S,19E,21S,23S,24R,25S,29S)-17,29-dihydroxy-3,15,21,23-tetramethoxy-5,12,18,24-tetramethyl-9,27-dioxo-10,26-dioxabicyclo[23.3.1]nonacosa-1(28),5,7,13,19-pentaen-11-yl]-4,10-dimethoxy-5,9-dimethyl-6-oxododec-1-enyl]-N-methylformamide
• SMILES (Canonical): CC1C=CC(CC(C(C2C(C(=CC(=O)O2)CC(CC(=CC=CC(=O)OC(C(C=CC(CC1O)OC)C)C(C)C(C(C)CCC(=O)C(C)C(CC=CN(C)C=O)OC)OC)C)OC)O)C)OC)OC
• SMILES (Isomeric): C[C@H]1/C=C/[C@H](C[C@@H]([C@H]([C@H]2[C@H](C(=CC(=O)O2)C[C@@H](C/C(=C\C=C\C(=O)O[C@@H]([C@H](/C=C/[C@@H](C[C@@H]1O)OC)C)[C@@H](C)[C@H]([C@@H](C)CCC(=O)[C@H](C)[C@@H](C/C=C/N(C)C=O)OC)OC)/C)OC)O)C)OC)OC
• InChI: InChI=1S/C53H85NO14/c1-33-17-15-19-48(58)67-52(39(7)51(66-14)35(3)22-25-44(56)37(5)46(64-12)18-16-26-54(8)32-55)36(4)21-24-41(61-9)30-45(57)34(2)20-23-42(62-10)31-47(65-13)38(6)53-50(60)40(29-49(59)68-53)28-43(27-33)63-11/h15-17,19-21,23-24,26,29,32,34-39,41-43,45-47,50-53,57,60H,18,22,25,27-28,30-31H2,1-14H3/b19-15+,23-20+,24-21+,26-16+,33-17-/t34-,35-,36-,37-,38+,39-,41-,42+,43+,45-,46+,47-,50-,51-,52-,53-/m0/s1
• InChI Key: MINVLQAHLUCDIO-GLLDUQGXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₅NO₁₄
• Molecular Weight: 960.20 g/mol
• Exact Mass: 959.59700639 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 6.91
• H-Bond Acceptor: 14
• H-Bond Donor: 2
• Rotatable Bonds: 18

Synonyms

• CHEMBL1615234
• DB04783
• Q27095521

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8072	80.72%
Caco-2	-	0.8602	86.02%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6838	68.38%
OATP2B1 inhibitior	-	0.7218	72.18%
OATP1B1 inhibitior	+	0.7993	79.93%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9072	90.72%
BSEP inhibitior	+	0.9868	98.68%
P-glycoprotein inhibitior	+	0.7624	76.24%
P-glycoprotein substrate	+	0.8199	81.99%
CYP3A4 substrate	+	0.7458	74.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8905	89.05%
CYP3A4 inhibition	-	0.7350	73.50%
CYP2C9 inhibition	-	0.8450	84.50%
CYP2C19 inhibition	-	0.8477	84.77%
CYP2D6 inhibition	-	0.9096	90.96%
CYP1A2 inhibition	-	0.8209	82.09%
CYP2C8 inhibition	+	0.7447	74.47%
CYP inhibitory promiscuity	-	0.9642	96.42%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5495	54.95%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.9054	90.54%
Skin irritation	-	0.7192	71.92%
Skin corrosion	-	0.9217	92.17%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7422	74.22%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5611	56.11%
skin sensitisation	-	0.8639	86.39%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7855	78.55%
Acute Oral Toxicity (c)	III	0.5663	56.63%
Estrogen receptor binding	+	0.7378	73.78%
Androgen receptor binding	+	0.7248	72.48%
Thyroid receptor binding	+	0.5987	59.87%
Glucocorticoid receptor binding	+	0.7602	76.02%
Aromatase binding	-	0.5251	52.51%
PPAR gamma	+	0.7792	77.92%
Honey bee toxicity	-	0.5655	56.55%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.6991	69.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.35%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.30%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.81%	95.56%
CHEMBL2179	P04062	Beta-glucocerebrosidase	93.89%	85.31%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.02%	90.08%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.67%	96.77%
CHEMBL2581	P07339	Cathepsin D	91.64%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.00%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.74%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.18%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.18%	97.25%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.10%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.72%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.71%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.65%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.15%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.49%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.08%	89.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.56%	82.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.42%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	86.37%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.16%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	85.87%	94.73%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.32%	97.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.79%	85.14%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.79%	98.75%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.75%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.87%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.35%	100.00%
CHEMBL1871	P10275	Androgen Receptor	80.97%	96.43%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.85%	96.47%

Plants that contains it

• Phyllanthus urinaria

Cross-Links

• PubChem: 46937020
• LOTUS: LTS0140291
• wikiData: Q105140818