Fruticoside C

Details

• Internal ID: abb83557-4948-490f-bf4e-87a3710fd06f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2R)-2-[(2R,3R,4S,5S,9R,10S,13R,14R,17R)-2-hydroxy-4,10,13-trimethyl-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
• SMILES (Canonical): CC1C2CC=C3C4CCC(C4(CCC3C2(CC(C1OC5C(C(C(C(O5)C)O)O)O)O)C)C)C(CCC(=C)C(C)C)C(=O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2CC=C3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(C[C@H]([C@@H]1O[C@H]5[C@H]([C@@H]([C@H]([C@@H](O5)C)O)O)O)O)C)C)[C@@H](CCC(=C)C(C)C)C(=O)O
• InChI: InChI=1S/C35H56O8/c1-17(2)18(3)8-9-22(32(40)41)25-13-12-24-21-10-11-23-19(4)31(43-33-30(39)29(38)28(37)20(5)42-33)27(36)16-35(23,7)26(21)14-15-34(24,25)6/h10,17,19-20,22-31,33,36-39H,3,8-9,11-16H2,1-2,4-7H3,(H,40,41)/t19-,20-,22+,23-,24-,25+,26-,27+,28-,29+,30-,31+,33-,34-,35-/m0/s1
• InChI Key: BFCFMIFGAHEHCB-YOIAMOGFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₆O₈
• Molecular Weight: 604.80 g/mol
• Exact Mass: 604.39751874 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.69
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• CHEBI:67586
• CHEMBL1782592
• DTXSID801110387
• Q27136054
• (2alpha,3beta,4alpha,5alpha)-3-[(6-deoxy-alpha-L-glucopyranosyl)oxy]-2-hydroxy-4-methylergosta-7,24(28)-dien-21-oic acid
• 1289417-63-5
• 4alpha-methyl-2alpha-hydroxy-5alpha-ergost-7,24(28)-dien-21-oic acid-3beta-O-alpha-L-quinovopyranoside
• Ergosta-7,24(28)-dien-21-oic acid, 3-[(6-deoxy-alpha-L-glucopyranosyl)oxy]-2-hydroxy-4-methyl-, (2alpha,3beta,4alpha,5alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9256	92.56%
Caco-2	-	0.8239	82.39%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7375	73.75%
OATP2B1 inhibitior	-	0.7200	72.00%
OATP1B1 inhibitior	+	0.8514	85.14%
OATP1B3 inhibitior	-	0.2927	29.27%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6372	63.72%
P-glycoprotein inhibitior	+	0.6456	64.56%
P-glycoprotein substrate	-	0.5223	52.23%
CYP3A4 substrate	+	0.6998	69.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.6694	66.94%
CYP2C9 inhibition	-	0.7852	78.52%
CYP2C19 inhibition	-	0.7825	78.25%
CYP2D6 inhibition	-	0.9311	93.11%
CYP1A2 inhibition	-	0.8266	82.66%
CYP2C8 inhibition	+	0.4662	46.62%
CYP inhibitory promiscuity	-	0.9028	90.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6979	69.79%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9267	92.67%
Skin irritation	+	0.5720	57.20%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5584	55.84%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5976	59.76%
skin sensitisation	-	0.8329	83.29%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7904	79.04%
Acute Oral Toxicity (c)	I	0.3898	38.98%
Estrogen receptor binding	+	0.7174	71.74%
Androgen receptor binding	+	0.5683	56.83%
Thyroid receptor binding	-	0.5412	54.12%
Glucocorticoid receptor binding	+	0.6302	63.02%
Aromatase binding	+	0.6393	63.93%
PPAR gamma	+	0.6218	62.18%
Honey bee toxicity	-	0.7559	75.59%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.9915	99.15%

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	99.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.38%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.66%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	96.10%	90.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.45%	97.36%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.73%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.09%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	89.72%	85.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.58%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.00%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.94%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.01%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.66%	96.38%
CHEMBL2581	P07339	Cathepsin D	85.45%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.47%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	83.46%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.40%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.19%	96.61%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.11%	83.57%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.97%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.71%	93.56%
CHEMBL5255	O00206	Toll-like receptor 4	81.84%	92.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.08%	94.45%

Plants that contains it

• Breynia fruticosa
• Forsythia suspensa

Cross-Links

• PubChem: 53355690
• NPASS: NPC250481
• LOTUS: LTS0086223
• wikiData: Q104959896