3-O-(beta-D-glucopyranosyl)presenegenin 28-{O-beta-D-galactopyranosyl-(1→4)-O-[beta-D-glucopyranosyl-(1→3)]-O-beta-D-xylopyranosyl-(1→4)-O-alpha-L-rhamnopyranosyl-(1→2)-{4-O-[(E)-3,4-dimethoxycinnamoyl]}-beta-D-fucopyranosyl} ester - Compound Card

3-O-(beta-D-glucopyranosyl)presenegenin 28-{O-beta-D-galactopyranosyl-(1→4)-O-[beta-D-glucopyranosyl-(1→3)]-O-beta-D-xylopyranosyl-(1→4)-O-alpha-L-rhamnopyranosyl-(1→2)-{4-O-[(E)-3,4-dimethoxycinnamoyl]}-beta-D-fucopyranosyl} ester

Select a section from the left sidebar

3-O-(beta-D-glucopyranosyl)presenegenin 28-{O-beta-D-galactopyranosyl-(1→4)-O-[beta-D-glucopyranosyl-(1→3)]-O-beta-D-xylopyranosyl-(1→4)-O-alpha-L-rhamnopyranosyl-(1→2)-{4-O-[(E)-3,4-dimethoxycinnamoyl]}-beta-D-fucopyranosyl} ester

Structure
Zoomed Structure
  • Family: Plantae - Polygalaceae
  • Kingdom: Plantae
  • Class: Terpene
Canonical Smiles OCC1OC(OC2C(COC(C2O)OC2C(C)OC(C(C2O)O)OC2C(OC(C(C2O)OC(=O)/C=C/c2ccc(c(c2)OC)OC)C)OC(=O)[C@@]23CCC(CC3C3=CCC4[C@@]([C@@]3(C[C@H]2O)CO)(C)CCC2[C@]4(C)C[C@@H]([C@@H](C2(C)C)OC2OC(CO)C(C(C2O)O)O)O)(C)C)OC2OC(CO)C(C(C2O)O)O)C(C(C1O)O)O
InChI InChI=1S/C76H116O36/c1-30-59(108-64-58(96)61(109-67-54(92)50(88)47(85)39(26-78)104-67)41(28-100-64)106-66-53(91)49(87)46(84)38(25-77)103-66)52(90)56(94)65(101-30)110-62-57(95)60(107-45(83)16-12-32-11-14-36(98-9)37(21-32)99-10)31(2)102-69(62)112-70(97)76-20-19-71(3,4)22-34(76)33-13-15-43-73(7)23-35(81)63(111-68-55(93)51(89)48(86)40(27-79)105-68)72(5,6)42(73)17-18-74(43,8)75(33,29-80)24-44(76)82/h11-14,16,21,30-31,34-35,38-44,46-69,77-82,84-96H,15,17-20,22-29H2,1-10H3/b16-12+/t30?,31?,34?,35-,38?,39?,40?,41?,42?,43?,44+,46?,47?,48?,49?,50?,51?,52?,53?,54?,55?,56?,57?,58?,59?,60?,61?,62?,63-,64?,65?,66?,67?,68?,69?,73-,74+,75-,76+/m0/s1
InChIKey FTAGSXIITLHUNW-MXYKXWDSSA-N
Formula C76H116O36
HBA 36
HBD 19
MW 1605.73
Rotatable Bonds 21
TPSA 556.96
LogP -4.5
Number Rings 12
Number Aromatic Rings 1
Heavy Atom Count 112
Formal Charge 0
Fraction CSP3 0.84
Exact Mass 1604.72
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Polygala arenaria Polygalaceae Plantae 3090470

Showing of synonyms

  • Peroni E, Fernández RF, et al. (2016). Natural Triterpene Glycosides for Antibody Recognition. Planta Medica Letters 2016; 3(01): e2-e7. [View]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(CC2)CC(CC3)C2C(CC4)C3C(CC5)C=4C(CCCC6)C56C(=O)OC(OCC(C7)OC(=O)C=Cc8ccccc8)C7OC(OC9)CCC9OC(C1)OCC(OC2CCCCO2)C1OC1CCCCO1

Level: 7

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCC(OC3)OC4C(OCC(C4)OC(=O)C=Cc5ccccc5)OC(=O)C67C(CCCC7)C=8C(CC6)C9C(CC8)C1C(CC9)CC(CC1)OC1CCCCO1

Level: 6

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4C(OCC(C4)OC(=O)C=Cc5ccccc5)OC(=O)C67C(CCCC7)C=8C(CC6)C9C(CC8)C1C(CC9)CC(CC1)OC1CCCCO1

Level: 6

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCC(C6)OC(=O)C=Cc7ccccc7)C6OC(OC8)CCC8OC(C9)OCC(OC1CCCCO1)C9OC1CCCCO1

Level: 6

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC(CC2)CC(CC3)C2C(CC4)C3C(CC5)C=4C(CCCC6)C56C(=O)OC(OCCC7)C7OC(OC8)CCC8OC(C9)OCC(OC1CCCCO1)C9OC1CCCCO1

Level: 6

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC(OC3)CCC3OC4CCCCO4)OC(=O)C56C(CCCC6)C=7C(CC5)C8C(CC7)C9C(CC8)CC(CC9)OC1CCCCO1

Level: 5

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCC(C6)OC(=O)C=Cc7ccccc7)C6OC(OC8)CCC8OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCC(C6)OC(=O)C=Cc7ccccc7)C6OC(OC8)CCC8OC(OC9)CCC9OC1CCCCO1

Level: 5

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC(CC2)CC(CC3)C2C(CC4)C3C(CC5)C=4C(CCCC6)C56C(=O)OC(OCCC7)C7OC(OC8)CCC8OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC(CC2)CC(CC3)C2C(CC4)C3C(CC5)C=4C(CCCC6)C56C(=O)OC(OCCC7)C7OC(OC8)CCC8OC(OC9)CCC9OC1CCCCO1

Level: 5

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OC7)CCC7OC(C8)OCC(OC9CCCCO9)C8OC1CCCCO1

Level: 5

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC(OC3)CCC3OC(C4)OCC(OC5CCCCO5)C4OC6CCCCO6

Level: 5

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC3CCCCO3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CC(CC8)OC9CCCCO9

Level: 4

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC(OC3)CCC3OC4CCCCO4)OC(=O)C56C(CCCC6)C=7C(CC5)C8C(CC7)C9C(CC8)CCCC9

Level: 4

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3C(OCCC3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CC(CC8)OC9CCCCO9

Level: 4

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OC7)CCC7OC(OCC8)CC8OC9CCCCO9

Level: 4

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 4

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC(OC3)CCC3OC(OCC4)CC4OC5CCCCO5

Level: 4

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC(OC3)CCC3OC(OC4)CCC4OC5CCCCO5

Level: 4

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4CCC(OC4)OC5CCCOC5

Level: 4

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC8CCCCO8

Level: 3

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC3CCCCO3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CCCC8

Level: 3

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2C(OCCC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC8CCCCO8

Level: 3

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4CCCOC4

Level: 3

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4CCCOC4

Level: 3

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CCCC7

Level: 2

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2C(OCCC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CCCC7

Level: 2

Mol. Weight: 1605.73 g/mol

Structure

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

Level: 2

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC3CCCCO3

Level: 2

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1605.73 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1605.73 g/mol

Structure

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

Level: 1

Mol. Weight: 1605.73 g/mol

Structure

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

Level: 1

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1605.73 g/mol

Structure

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

Level: 0

Mol. Weight: 1605.73 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1605.73 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1605.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.04
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
1304785786219523500000000
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
170520080505948800000000000

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.41
Plasma Protein Binding
3.74
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
1.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-3965911197499078000000000
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1619328544118338600
Liver Injury II
Safe
hERG Blockers
Toxic
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
-309485713073196400000000000000
Rat (Acute)
249587421347397.7
Rat (Chronic Oral)
663819862947545400000
Fathead Minnow
390659705601899060000000000
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
34808563122927863000000000000
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-19350089062321690000000
Log(P)
-2252578436645150700
Log S
-3.36
Log(Vapor Pressure)
-1146228479439872100000000000
Melting Point
-348297714803311640000
pKa Acid
-8352080696830048000000000
pKa Basic
-67192263607720964000000

No predicted protein targets found for this compound.

Download SDF