Fruticoside G

Details

• Internal ID: b5d1ea89-2e70-425f-92b8-5cb279af9f79
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: (Z,2R)-5-propan-2-yl-2-[(3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-3-[(2R,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]hept-5-enethioic S-acid
• SMILES (Canonical): CC=C(CCC(C1CCC2C1(CCC3C2=CCC4C3(CCC(C4C)OC5C(C(C(C(O5)C)O)O)O)C)C)C(=O)S)C(C)C
• SMILES (Isomeric): C/C=C(/CC[C@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC[C@@H]4[C@@]3(CC[C@@H]([C@H]4C)O[C@H]5[C@H]([C@@H]([C@H]([C@@H](O5)C)O)O)O)C)C)C(=O)S)\C(C)C
• InChI: InChI=1S/C36H58O6S/c1-8-22(19(2)3)9-10-24(33(40)43)27-14-13-26-23-11-12-25-20(4)29(42-34-32(39)31(38)30(37)21(5)41-34)16-18-35(25,6)28(23)15-17-36(26,27)7/h8,11,19-21,24-32,34,37-39H,9-10,12-18H2,1-7H3,(H,40,43)/b22-8-/t20-,21-,24+,25-,26-,27+,28-,29-,30-,31+,32-,34-,35-,36-/m0/s1
• InChI Key: AUQOSBIEPMUBCQ-TVZJVHHSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₆S
• Molecular Weight: 618.90 g/mol
• Exact Mass: 618.39541074 g/mol
• Topological Polar Surface Area (TPSA): 97.20 Ų
• XlogP: 7.00
• Atomic LogP (AlogP): 6.48
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• CHEBI:67590
• (3beta,4alpha,5alpha,24Z)-3-[(6-deoxy-alpha-L-glucopyranosyl)oxy]-4-methylstigmasta-7,24(28)-diene-21-thioic S-acid
• 4alpha-methyl-5alpha-stigmast-7,24(28)-diene-21-carbothioic acid-3beta-O-alpha-L-quinovopyranoside
• (3beta,4alpha,5alpha,24Z)-3-((6-deoxy-alpha-L-glucopyranosyl)oxy)-4-methylstigmasta-7,24(28)-diene-21-thioic S-acid
• (Z,2R)-5-propan-2-yl-2-((3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-3-((2R,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)hept-5-enethioic S-acid
• (Z,2R)-5-propan-2-yl-2-[(3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-3-[(2R,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]hept-5-enethioic S-acid
• RefChem:141568
• 4a-Methyl-5a-stigmast-7,24(28)-diene-21-carbothioate-3b-O-a-L-quinovopyranoside
• 4a-Methyl-5a-stigmast-7,24(28)-diene-21-carbothioic acid-3b-O-a-L-quinovopyranoside
• 4alpha-Methyl-5alpha-stigmast-7,24(28)-diene-21-carbothioate-3beta-O-alpha-L-quinovopyranoside
• CHEMBL1782596
• Q27136059

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9086	90.86%
Caco-2	-	0.8066	80.66%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7375	73.75%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8314	83.14%
OATP1B3 inhibitior	-	0.2887	28.87%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7636	76.36%
P-glycoprotein inhibitior	+	0.7062	70.62%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6994	69.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.8589	85.89%
CYP2C9 inhibition	-	0.7969	79.69%
CYP2C19 inhibition	-	0.7187	71.87%
CYP2D6 inhibition	-	0.9185	91.85%
CYP1A2 inhibition	-	0.7620	76.20%
CYP2C8 inhibition	+	0.4803	48.03%
CYP inhibitory promiscuity	-	0.8197	81.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6846	68.46%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9362	93.62%
Skin irritation	-	0.5407	54.07%
Skin corrosion	-	0.9321	93.21%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3698	36.98%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6015	60.15%
skin sensitisation	-	0.8290	82.90%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8675	86.75%
Acute Oral Toxicity (c)	III	0.4266	42.66%
Estrogen receptor binding	+	0.7267	72.67%
Androgen receptor binding	-	0.5418	54.18%
Thyroid receptor binding	-	0.5524	55.24%
Glucocorticoid receptor binding	+	0.6844	68.44%
Aromatase binding	+	0.6078	60.78%
PPAR gamma	+	0.5876	58.76%
Honey bee toxicity	-	0.6997	69.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	0.9950	99.50%

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	99.12%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.78%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.74%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.31%	90.17%
CHEMBL2581	P07339	Cathepsin D	95.55%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.93%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.20%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.45%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.20%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.55%	89.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.04%	89.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.93%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.82%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.06%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.69%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.66%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.95%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.83%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.22%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	84.76%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.43%	96.77%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.38%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.43%	92.50%

Plants that contains it

• Breynia fruticosa

Cross-Links

• PubChem: 54587064
• NPASS: NPC269466
• LOTUS: LTS0087725
• wikiData: Q27136059