Nomilin glucoside

Details

• Internal ID: 78ab783c-4bf2-4f0f-b57d-f82e5422f92c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: (1R,2'R,5aR,7aR,9S,11aR,11bR)-1-acetyloxy-9-[furan-3-yl-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxospiro[2,5a,6,10,11,11a-hexahydro-1H-naphtho[2,1-c]oxepine-8,3'-oxirane]-2'-carboxylic acid
• SMILES (Canonical): CC(=O)OC1CC(=O)OC(C2C1(C3CCC(C4(C3(C(=O)C2)C)C(O4)C(=O)O)(C)C(C5=COC=C5)OC6C(C(C(C(O6)CO)O)O)O)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1CC(=O)OC([C@H]2[C@]1([C@H]3CC[C@@](C4([C@@]3(C(=O)C2)C)[C@@H](O4)C(=O)O)(C)C(C5=COC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)(C)C
• InChI: InChI=1S/C34H46O15/c1-15(36)45-21-12-22(38)48-30(2,3)19-11-20(37)33(6)18(32(19,21)5)7-9-31(4,34(33)27(49-34)28(42)43)26(16-8-10-44-14-16)47-29-25(41)24(40)23(39)17(13-35)46-29/h8,10,14,17-19,21,23-27,29,35,39-41H,7,9,11-13H2,1-6H3,(H,42,43)/t17-,18-,19+,21-,23-,24+,25-,26?,27+,29+,31+,32-,33+,34?/m1/s1
• InChI Key: GIVMXHQLQAIYEX-OJVPXVCRSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₆O₁₅
• Molecular Weight: 694.70 g/mol
• Exact Mass: 694.28367076 g/mol
• Topological Polar Surface Area (TPSA): 232.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• CCRIS 6987
• 123564-62-5
• Nomilin 17-O-beta-D-glucopyranoside
• (1R,3'R,5aR,7aR,9S,11aR,11bR)-1-acetoxy-9-(furan-3-yl(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-5,5,7a,9,11b-pentamethyl-3,7-dioxododecahydro-5H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid
• DTXSID40924539
• C34H46O15
• C34-H46-O15
• 1-(Acetyloxy)-9-[(furan-3-yl)(hexopyranosyloxy)methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxododecahydro-5H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid
• Limonoic acid, 1-(acetyloxy)-1,4-deepoxy-19-deoxy-O17-beta-D-glucopyranosyl-4-hydroxy-, epsilon-lactone
• Spiro(naphth(2,1-c)oxepin-8(5H),2'-oxirane)-3'-carboxylic acid, 1-(acetyloxy)-9-((S)-3-furanyl(beta-D-glucopyranosyloxy)methyl)dodecahydro-5,5,7a,9,11b-pentamethyl-3,7-dioxo-, (1R,2'R,3R,5aR,7aR,9S,11aR,11bR)-
• Spiro(naphth(2,1-c)oxepin-8(5H),2'-oxirane)-3'-carboxylic acid, 1-(acetyloxy)-9-((S)-3-furanyl(beta-D-glucopyranosyloxy)methyl)dodecahydro-5,5,7a,9,11b-pentamethyl-3,7-dioxo-, (1R,3'R,5aR,7aR,8R,9S,11aR,11bR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6723	67.23%
Caco-2	-	0.8604	86.04%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7547	75.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7690	76.90%
OATP1B3 inhibitior	+	0.9061	90.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.7372	73.72%
P-glycoprotein substrate	+	0.5619	56.19%
CYP3A4 substrate	+	0.7103	71.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8712	87.12%
CYP3A4 inhibition	-	0.6523	65.23%
CYP2C9 inhibition	-	0.7277	72.77%
CYP2C19 inhibition	-	0.8323	83.23%
CYP2D6 inhibition	-	0.9381	93.81%
CYP1A2 inhibition	-	0.8339	83.39%
CYP2C8 inhibition	+	0.6934	69.34%
CYP inhibitory promiscuity	-	0.9194	91.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6606	66.06%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9043	90.43%
Skin irritation	-	0.7231	72.31%
Skin corrosion	-	0.9273	92.73%
Ames mutagenesis	-	0.7240	72.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.7211	72.11%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8946	89.46%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7358	73.58%
Acute Oral Toxicity (c)	I	0.3895	38.95%
Estrogen receptor binding	+	0.7616	76.16%
Androgen receptor binding	+	0.7857	78.57%
Thyroid receptor binding	-	0.4918	49.18%
Glucocorticoid receptor binding	+	0.7587	75.87%
Aromatase binding	+	0.6905	69.05%
PPAR gamma	+	0.7522	75.22%
Honey bee toxicity	-	0.6919	69.19%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6550	65.50%
Fish aquatic toxicity	+	0.9513	95.13%

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	98.20%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.00%	85.14%
CHEMBL2581	P07339	Cathepsin D	97.60%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.82%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.94%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.73%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.36%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.25%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.96%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.94%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	87.52%	90.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.95%	95.83%
CHEMBL4040	P28482	MAP kinase ERK2	84.58%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.07%	94.00%
CHEMBL5028	O14672	ADAM10	82.93%	97.50%
CHEMBL220	P22303	Acetylcholinesterase	82.49%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.34%	96.00%
CHEMBL3524	P56524	Histone deacetylase 4	82.22%	92.97%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.54%	93.04%
CHEMBL1937	Q92769	Histone deacetylase 2	80.55%	94.75%

Plants that contains it

• Citrus × aurantium
• Citrus maxima
• Citrus medica

Cross-Links

• PubChem: 3083017
• NPASS: NPC202865
• LOTUS: LTS0107449
• wikiData: Q82898731