Calendulaglycoside A - Compound Card

Calendulaglycoside A

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Calendulaglycoside A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene Glycoside
Canonical Smiles OCC1OC(OC2C(OC(C(C2OC2OC(CO)C(C(C2O)O)O)O)C(=O)O)O[C@H]2CCC3(C(C2(C)C)CCC2(C3CC=C3[C@@]2(C)CCC2(C3CC(C)(C)CC2)C(=O)OC2OC(CO)C(C(C2O)O)O)C)C)C(C(C1O)O)O
InChI InChI=1S/C54H86O24/c1-49(2)14-16-54(48(70)78-46-38(66)35(63)32(60)26(21-57)73-46)17-15-52(6)22(23(54)18-49)8-9-28-51(5)12-11-29(50(3,4)27(51)10-13-53(28,52)7)74-47-42(77-45-37(65)34(62)31(59)25(20-56)72-45)40(39(67)41(76-47)43(68)69)75-44-36(64)33(61)30(58)24(19-55)71-44/h8,23-42,44-47,55-67H,9-21H2,1-7H3,(H,68,69)/t23?,24?,25?,26?,27?,28?,29-,30?,31?,32?,33?,34?,35?,36?,37?,38?,39?,40?,41?,42?,44?,45?,46?,47?,51?,52+,53?,54?/m0/s1
InChIKey YSCJAYPKBYRXEZ-LKXHCCTGSA-N
Formula C54H86O24
HBA 23
HBD 14
MW 1119.26
Rotatable Bonds 12
TPSA 391.2
LogP -1.94
Number Rings 9
Number Aromatic Rings 0
Heavy Atom Count 78
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 1118.55
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Calendula stellata Asteraceae Plantae 1565984

Showing of synonyms

  • Lehbili M, Alabdul Magid A, et al. (2017). Oleanane-type triterpene saponins from Calendula stellata. Phytochemistry, 2017, 144, 33-42. [View] [PubMed]
Pubchem: 24204441

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: 1119.26 g/mol

Structure

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

Level: 3

Mol. Weight: 1119.26 g/mol

Structure

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

Level: 3

Mol. Weight: 1119.26 g/mol

Structure

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

Level: 3

Mol. Weight: 1119.26 g/mol

Structure

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

Level: 2

Mol. Weight: 1119.26 g/mol

Structure

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

Level: 2

Mol. Weight: 1119.26 g/mol

Structure

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

Level: 2

Mol. Weight: 1119.26 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1119.26 g/mol

Structure

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

Level: 1

Mol. Weight: 1119.26 g/mol

Structure

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

Level: 1

Mol. Weight: 1119.26 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1119.26 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1119.26 g/mol

Structure

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

Level: 0

Mol. Weight: 1119.26 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1119.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.24
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
963601.55
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
125932259.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.83
Plasma Protein Binding
-2.13
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
1.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-2928892.34
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.96
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
-228560962206.31
Rat (Acute)
3.45
Rat (Chronic Oral)
490.23
Fathead Minnow
288509814.49
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
25706764297.23
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-14283.31
Log(P)
-0.57
Log S
-2.07
Log(Vapor Pressure)
-846510572.72
Melting Point
225.08
pKa Acid
-6168074.16
pKa Basic
-49611.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7177

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