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Calendulagycoside C 6′-O-n-butyl ester

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Saponin

Canonical Smiles	CCCCOC(=O)[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)OC2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@H]1O[C@@H](CO)[C@H]([C@H]([C@@H]1O)O)O)O
InChI	InChI=1S/C52H84O19/c1-9-10-21-65-42(63)41-38(61)40(69-43-36(59)34(57)32(55)27(23-53)66-43)39(62)45(70-41)68-31-14-15-49(6)29(48(31,4)5)13-16-51(8)30(49)12-11-25-26-22-47(2,3)17-19-52(26,20-18-50(25,51)7)46(64)71-44-37(60)35(58)33(56)28(24-54)67-44/h11,26-41,43-45,53-62H,9-10,12-24H2,1-8H3/t26-,27-,28+,29-,30+,31-,32+,33+,34+,35-,36-,37+,38-,39+,40-,41-,43+,44?,45+,49-,50+,51+,52-/m0/s1
InChIKey	MGYFZCUYTCZBNN-ZINXSWEGSA-N
Formula	C₅₂H₈₄O₁₉
HBA	19
HBD	10
MW	1013.23
Rotatable Bonds	12
TPSA	301.05
LogP	1.49
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	71
Formal Charge	0
Fraction CSP3	0.92
Exact Mass	1012.56
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Calendula officinalis	Asteraceae	Plantae	41496

Showing of synonyms

Ukiya M, Akihisa T, et al. (2006). Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of Marigold (Calendula officinalis) flowers. Journal of Natural Products,2006,69,1692-1696. [View] [PubMed]

Pubchem: 162913955

Nmrshiftdb2: 70067434

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCC7)CC7OC8CCCCO8

Level: 3

Mol. Weight: 1013.23 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 1013.23 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCC6)CC6OC7CCCCO7

Level: 2

Mol. Weight: 1013.23 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 1013.23 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 1013.23 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1013.23 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 1013.23 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1013.23 g/mol

Anti-inflammatory

Antitumor promoting

Absorption

Caco-2 (logPapp): -6.31
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 30323.51
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 3963773.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.85
Plasma Protein Binding: 95.67
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 1.35
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -92182.99
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.71
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -7194056770.15
Rat (Acute): 3.64
Rat (Chronic Oral): 16.67
Fathead Minnow: 9080971.48
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 809127177.51
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -431.89
Log(P): 3.96
Log S: -3.14
Log(Vapor Pressure): -26643983.63
Melting Point: 256.03
pKa Acid: -194051.76
pKa Basic: -1545.03

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7636
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7636
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7088
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7088

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