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Vaccaroside C

Family: Plantae - Caryophyllaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Oleanane-Type 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@@]23CCC(C[C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H]([C@@]2(C)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C60H96O30/c1-55(2)13-15-60(16-14-57(4)23(24(60)17-55)7-8-30-56(3)11-10-32(65)59(6,31(56)9-12-58(30,57)5)53(79)89-50-44(77)40(73)35(68)27(20-63)84-50)54(80)90-51-45(78)46(87-48-42(75)38(71)33(66)25(18-61)82-48)37(70)29(86-51)22-81-52-47(41(74)36(69)28(21-64)85-52)88-49-43(76)39(72)34(67)26(19-62)83-49/h7,24-52,61-78H,8-22H2,1-6H3/t24-,25+,26+,27+,28+,29+,30+,31+,32-,33+,34+,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,46-,47+,48-,49-,50-,51-,52+,56+,57+,58+,59-,60-/m0/s1
InChIKey	SHDCOAGAKQAHTD-QDZUSAFCSA-N
Formula	C₆₀H₉₆O₃₀
HBA	30
HBD	18
MW	1297.4
Rotatable Bonds	15
TPSA	490.58
LogP	-5.71
Number Rings	10
Number Aromatic Rings	0
Heavy Atom Count	90
Formal Charge	0
Fraction CSP3	0.93
Exact Mass	1296.6
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Gypsophila arabica	Caryophyllaceae	Plantae	2161765

Showing of synonyms

De Abreu MB, Dal Piaz F, et al. (2008). Gypsins A-D from Gypsophila arabica. Journal of Natural Products,2008,71(8),1336-1342. [View] [PubMed]

Pubchem: 102317031

Nmrshiftdb2: 60047735

No compound-protein relationship available.

SMILES: O1CCCCC1OC2C(OCCC2)OCC3CC(OC4CCCCO4)CC(O3)OC(=O)C56C(CCCC6)C=7C(CC5)C8C(CC7)C9C(CC8)C(CCC9)C(=O)OC1CCCCO1

Level: 5

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1OCC2CC(OC3CCCCO3)CC(O2)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)C(CCC8)C(=O)OC9CCCCO9

Level: 4

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OCC3CCCC(O3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)C(CCC8)C(=O)OC9CCCCO9

Level: 4

Mol. Weight: 1297.4 g/mol

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

Level: 4

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)C(CCC7)C(=O)OC8CCCCO8

Level: 3

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)C(CCC7)C(=O)OC8CCCCO8

Level: 3

Mol. Weight: 1297.4 g/mol

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

Level: 3

Mol. Weight: 1297.4 g/mol

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

Level: 3

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1OC(CCO2)CC2COC(OCCC3)C3OC4CCCCO4

Level: 3

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)C(CCC6)C(=O)OC7CCCCO7

Level: 2

Mol. Weight: 1297.4 g/mol

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

Level: 2

Mol. Weight: 1297.4 g/mol

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

Level: 2

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1OCC2CC(CCO2)OC3CCCCO3

Level: 2

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1COC(OCCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 1297.4 g/mol

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

Level: 1

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1OC(=O)C(CCC2)C(CC3)C2C(CC4)C3C(C=45)CCC6C5CCCC6

Level: 1

Mol. Weight: 1297.4 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1297.4 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1297.4 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1297.4 g/mol

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

Level: 0

Mol. Weight: 1297.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1297.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 163178719110.940
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 21325550597649.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.480
Plasma Protein Binding: 54.17
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: 1.350
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -495984031229.020
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -202516.410
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: -38704844953079936.000
Rat (Acute): 7.560
Rat (Chronic Oral): 83018498.270
Fathead Minnow: 48856647205000.000
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: 4353222222916266.500
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -2419957641.720
Log(P): -281712.9
Log S: -2.12
Log(Vapor Pressure): -143349432201920.1
Melting Point: -43554988.61
pKa Acid: -1044526630370.1
pKa Basic: -8403184005.21

No predicted protein targets found for this compound.

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