Calendulagycoside A 6′-O-n-methyl ester - Compound Card

Calendulagycoside A 6′-O-n-methyl ester

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Calendulagycoside A 6′-O-n-methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Saponin
Canonical Smiles COC(=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[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C55H88O24/c1-50(2)15-17-55(49(70)79-47-39(67)36(64)33(61)27(22-58)74-47)18-16-53(6)23(24(55)19-50)9-10-29-52(5)13-12-30(51(3,4)28(52)11-14-54(29,53)7)75-48-43(78-46-38(66)35(63)32(60)26(21-57)73-46)41(40(68)42(77-48)44(69)71-8)76-45-37(65)34(62)31(59)25(20-56)72-45/h9,24-43,45-48,56-68H,10-22H2,1-8H3/t24-,25-,26+,27+,28-,29+,30-,31+,32+,33+,34+,35-,36-,37-,38+,39+,40-,41-,42-,43+,45+,46-,47?,48+,52-,53+,54+,55-/m0/s1
InChIKey DQGMAYONHHBQRD-ANHKKOIRSA-N
Formula C55H88O24
HBA 24
HBD 13
MW 1133.29
Rotatable Bonds 12
TPSA 380.2
LogP -1.85
Number Rings 9
Number Aromatic Rings 0
Heavy Atom Count 79
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 1132.57
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: 162905380
Nmrshiftdb2: 70067432

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC7OCCC(OC8CCCCO8)C7OC9CCCCO9

Level: 4

Mol. Weight: 1133.29 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1133.29 g/mol

Structure

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

Level: 3

Mol. Weight: 1133.29 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6OCCC(OC7CCCCO7)C6OC8CCCCO8

Level: 3

Mol. Weight: 1133.29 g/mol

Structure

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

Level: 2

Mol. Weight: 1133.29 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 1133.29 g/mol

Structure

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

Level: 2

Mol. Weight: 1133.29 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1133.29 g/mol

Structure

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

Level: 1

Mol. Weight: 1133.29 g/mol

Structure

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

Level: 1

Mol. Weight: 1133.29 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1133.29 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1133.29 g/mol

Structure

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

Level: 0

Mol. Weight: 1133.29 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1133.29 g/mol

Anti-inflammatory
Antitumor promoting

Absorption

Caco-2 (logPapp)
-6.5
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
2937638.110
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
383915876.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.740
Plasma Protein Binding
73.76
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.280
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-8929005.060
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-4.180
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
4.050
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
-696788826589.360
Rat (Acute)
3.870
Rat (Chronic Oral)
1494.920
Fathead Minnow
879547175.520
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
78369411499.970
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-43552.890
Log(P)
-3.77
Log S
-2.35
Log(Vapor Pressure)
-2580665239.96
Melting Point
116.2
pKa Acid
-18804119.54
pKa Basic
-151268.53

No predicted protein targets found for this compound.

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