Nudicaucin C

Details

• Internal ID: 04912bd9-d853-44fb-a1d3-881478c73044
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)C)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O
• InChI: InChI=1S/C53H86O21/c1-23-32(57)35(60)38(63)43(68-23)73-42-41(72-44-39(64)36(61)33(58)27(20-54)69-44)26(56)22-67-46(42)71-31-12-13-50(6)29(49(31,4)5)11-14-52(8)30(50)10-9-24-25-19-48(2,3)15-17-53(25,18-16-51(24,52)7)47(66)74-45-40(65)37(62)34(59)28(21-55)70-45/h9,23,25-46,54-65H,10-22H2,1-8H3/t23-,25-,26-,27+,28+,29-,30+,31-,32-,33+,34+,35+,36-,37-,38+,39+,40+,41-,42+,43-,44-,45-,46-,50-,51+,52+,53-/m0/s1
• InChI Key: ULSOTXJNUTYKRK-DFRCHCFDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₁
• Molecular Weight: 1059.20 g/mol
• Exact Mass: 1058.56615975 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 21
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

• Ilekudinoside A
• 211815-98-4
• Olean-12-en-28-oic acid, 3-[(O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl)oxy]-, beta-D-glucopyranosyl ester, (3beta)-
• CHEMBL444740
• SCHEMBL15377283
• DTXSID401101699
• beta-D-Glucopyranosyl (3beta)-3-[(O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8866	88.66%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7242	72.42%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8093	80.93%
P-glycoprotein inhibitior	+	0.7492	74.92%
P-glycoprotein substrate	-	0.7181	71.81%
CYP3A4 substrate	+	0.7297	72.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.6753	67.53%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9028	90.28%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7169	71.69%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9875	98.75%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9258	92.58%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7942	79.42%
Androgen receptor binding	+	0.7311	73.11%
Thyroid receptor binding	-	0.5240	52.40%
Glucocorticoid receptor binding	+	0.7409	74.09%
Aromatase binding	+	0.6524	65.24%
PPAR gamma	+	0.7966	79.66%
Honey bee toxicity	-	0.6600	66.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	0.9411	94.11%

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	98.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.04%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.51%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.08%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.74%	97.36%
CHEMBL2581	P07339	Cathepsin D	91.41%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.89%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.36%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.64%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.97%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.81%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.27%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	82.95%	95.93%
CHEMBL5255	O00206	Toll-like receptor 4	81.57%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.41%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.60%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.17%	95.50%

Plants that contains it

• Debia ovatifolia
• Guaiacum officinale
• Ilex kaushue
• Ilex latifolia
• Ilex paraguariensis
• Larrea tridentata

Cross-Links

• PubChem: 21635821
• NPASS: NPC46665
• LOTUS: LTS0126351
• wikiData: Q104400365