Calenduloside C

Details

• Internal ID: 4c2015b6-e101-4c50-95a6-f1a42bd9be02
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)OC7C(C(C(C(O7)CO)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C2C1)C)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C48H78O18/c1-43(2)14-16-48(42(59)60)17-15-46(6)22(23(48)18-43)8-9-28-45(5)12-11-29(44(3,4)27(45)10-13-47(28,46)7)64-41-38(66-40-36(58)34(56)31(53)25(20-50)62-40)37(32(54)26(21-51)63-41)65-39-35(57)33(55)30(52)24(19-49)61-39/h8,23-41,49-58H,9-21H2,1-7H3,(H,59,60)/t23-,24+,25+,26+,27-,28+,29-,30-,31+,32+,33-,34-,35+,36+,37-,38+,39-,40-,41-,45-,46+,47+,48-/m0/s1
• InChI Key: OGKRHYLZKFTGGO-RHFDSUMBSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₈
• Molecular Weight: 943.10 g/mol
• Exact Mass: 942.51881563 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 0.71
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 10

Synonyms

• Arvensoside D
• Elateroside B
• Osteosaponin 1
• 2'',28-Dideglucosylosteosaponin 2
• UNII-K5B114517J
• K5B114517J
• 58231-97-3
• DTXSID80206967
• Olean-12-en-28-oic acid, 3-((o-beta-D-galactopyranosyl-(1->3)-O-(beta-D-glucopyranosyl-(1->2))-beta-D-glucopyranosyl)oxy)-, (3beta)-
• DTXCID10129458
• Q27281984
• OLEAN-12-EN-28-OIC ACID, 3-((O-.BETA.-D-GALACTOPYRANOSYL-(1->3)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->2))-.BETA.-D-GLUCOPYRANOSYL)OXY)-, (3.BETA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7499	74.99%
Caco-2	-	0.8874	88.74%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8758	87.58%
OATP2B1 inhibitior	-	0.8783	87.83%
OATP1B1 inhibitior	-	0.3302	33.02%
OATP1B3 inhibitior	-	0.5977	59.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	-	0.5433	54.33%
P-glycoprotein inhibitior	+	0.7540	75.40%
P-glycoprotein substrate	-	0.8951	89.51%
CYP3A4 substrate	+	0.7027	70.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9589	95.89%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.6160	61.60%
CYP inhibitory promiscuity	-	0.9423	94.23%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6313	63.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9064	90.64%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.9270	92.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3823	38.23%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.9572	95.72%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.7104	71.04%
Acute Oral Toxicity (c)	III	0.7822	78.22%
Estrogen receptor binding	+	0.7801	78.01%
Androgen receptor binding	+	0.7352	73.52%
Thyroid receptor binding	-	0.6212	62.12%
Glucocorticoid receptor binding	+	0.6283	62.83%
Aromatase binding	+	0.6237	62.37%
PPAR gamma	+	0.7505	75.05%
Honey bee toxicity	-	0.7398	73.98%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.9603	96.03%

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	95.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.10%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.35%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.97%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.06%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.26%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	86.36%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.50%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.98%	96.21%
CHEMBL2581	P07339	Cathepsin D	83.71%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.16%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.69%	86.33%

Plants that contains it

• Calendula arvensis
• Ecballium elaterium
• Osteospermum vaillantii
• Podophyllum sinense
• Pometia ridleyi

Cross-Links

• PubChem: 71587192
• NPASS: NPC140193
• LOTUS: LTS0005432
• wikiData: Q27281984