Vaccaroside A - Compound Card

Vaccaroside A

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Vaccaroside A

Structure
Zoomed Structure
  • Family: Plantae - Caryophyllaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpene Saponin
Canonical Smiles OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O[C@@H]([C@H]2O)CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)O)OC(=O)[C@]23CC[C@@]4(C(=CC[C@H]5[C@@]4(C)CC[C@@H]4[C@]5(C)CC[C@@H]([C@@]4(C)C(=O)O)O)[C@@H]3CC(CC2)(C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C54H86O25/c1-49(2)13-15-54(16-14-51(4)22(23(54)17-49)7-8-28-50(3)11-10-30(58)53(6,47(69)70)29(50)9-12-52(28,51)5)48(71)79-45-40(68)41(77-43-38(66)35(63)31(59)24(18-55)73-43)34(62)27(76-45)21-72-46-42(37(65)33(61)26(20-57)75-46)78-44-39(67)36(64)32(60)25(19-56)74-44/h7,23-46,55-68H,8-21H2,1-6H3,(H,69,70)/t23-,24+,25+,26+,27+,28+,29+,30-,31+,32+,33+,34+,35-,36-,37-,38+,39+,40+,41-,42+,43-,44-,45-,46+,50+,51+,52+,53-,54-/m0/s1
InChIKey IVOKGTCMOJXNCF-FHEJOWGISA-N
Formula C54H86O25
HBA 24
HBD 15
MW 1135.26
Rotatable Bonds 13
TPSA 411.43
LogP -2.97
Number Rings 9
Number Aromatic Rings 0
Heavy Atom Count 79
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 1134.55
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Vaccaria pyramidata Caryophyllaceae Plantae 39387

Showing of synonyms

  • Said R, Hamed A, et al. (2019). Flavone C-glycosides from Vaccaria pyramidata: Structure elucidation by spectroscopy and theoretical calculations. Phytochemistry Letters, 2019, 29, 119-124. [View]
Pubchem: 45272283
Nmrshiftdb2: 60030353

No compound-protein relationship available.

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(O6)CC(OC7CCCCO7)CC6COC(OCCC8)C8OC9CCCCO9

Level: 4

Mol. Weight: 1135.26 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(O6)CCCC6COC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1135.26 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(O6)CC(OC7CCCCO7)CC6COC8CCCCO8

Level: 3

Mol. Weight: 1135.26 g/mol

Structure

SMILES: O1CCCCC1OC(CCO2)CC2COC(OCCC3)C3OC4CCCCO4

Level: 3

Mol. Weight: 1135.26 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(O6)CCCC6COC7CCCCO7

Level: 2

Mol. Weight: 1135.26 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CCCC7

Level: 2

Mol. Weight: 1135.26 g/mol

Structure

SMILES: O1CCCCC1OCC2CC(CCO2)OC3CCCCO3

Level: 2

Mol. Weight: 1135.26 g/mol

Structure

SMILES: O1CCCCC1COC(OCCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 1135.26 g/mol

Structure

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

Level: 1

Mol. Weight: 1135.26 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1135.26 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1135.26 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1135.26 g/mol

Structure

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

Level: 0

Mol. Weight: 1135.26 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1135.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.29
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
2387916.200
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
312073624.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
69.46
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
Non-Inhibitor

Excretion

Clearance
1.100
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-7258116.900
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-3.830
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
-566398605803.270
Rat (Acute)
3.430
Rat (Chronic Oral)
1214.940
Fathead Minnow
714958241.950
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
63704140025.530
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-35405.350
Log(P)
-3.98
Log S
-2.16
Log(Vapor Pressure)
-2097744473.77
Melting Point
136.36
pKa Acid
-15285292.44
pKa Basic
-122956.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7764
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7647

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