1-O-alpha-L-rhamnopyranosyl-(1→2)-[alpha-L-rhamnopyranosyl-(1→4)]-beta-D-glucopyranosyl-26-O-beta-D-glucopyranosyl-22-O-methylfurosta-5,25(27)-diene-1beta,3beta,22,26-tetraol - Compound Card

1-O-alpha-L-rhamnopyranosyl-(1→2)-[alpha-L-rhamnopyranosyl-(1→4)]-beta-D-glucopyranosyl-26-O-beta-D-glucopyranosyl-22-O-methylfurosta-5,25(27)-diene-1beta,3beta,22,26-tetraol

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1-O-alpha-L-rhamnopyranosyl-(1→2)-[alpha-L-rhamnopyranosyl-(1→4)]-beta-D-glucopyranosyl-26-O-beta-D-glucopyranosyl-22-O-methylfurosta-5,25(27)-diene-1beta,3beta,22,26-tetraol

Structure
Zoomed Structure
  • Family: Plantae - Agavaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Furostanol Saponin
Canonical Smiles OCC1O[C@@H](OCC23CCC(CC2=CCC2C3CCC3(C2CC2C3C(C)C(O2)(OC)CCC(=C)CO[C@@H]2OC(CO)[C@H](C([C@@H]2O)O)O)C)O)[C@H](C([C@H]1OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)O)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O
InChI InChI=1S/C52H84O23/c1-21(19-67-46-40(62)39(61)36(58)31(17-53)71-46)9-14-52(66-6)22(2)33-30(75-52)16-29-27-8-7-25-15-26(55)10-13-51(25,28(27)11-12-50(29,33)5)20-68-49-45(74-48-42(64)38(60)35(57)24(4)70-48)43(65)44(32(18-54)72-49)73-47-41(63)37(59)34(56)23(3)69-47/h7,22-24,26-49,53-65H,1,8-20H2,2-6H3/t22?,23-,24-,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?/m1/s1
InChIKey ATHICKWSAHTNIX-WUUBJLDQSA-N
Formula C52H84O23
HBA 23
HBD 13
MW 1077.22
Rotatable Bonds 16
TPSA 355.29
LogP -2.43
Number Rings 9
Number Aromatic Rings 0
Heavy Atom Count 75
Formal Charge 0
Fraction CSP3 0.92
Exact Mass 1076.54
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Agave decipiens Agavaceae Plantae 2695036

Showing of synonyms

  • Abdel-Gawad MM, El-Sayed MM and Abdel-Hameed ES. (1999). Molluscicidal steroidal saponins and lipid content of Agave decipiens. Fitoterapia,1999,70,371-381. [View]
Pubchem: 162817612
Nmrshiftdb2: 60019331

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC(=C)CCC(C2)OC(C3)C2C(CCC45)C3C5CC=C(CCCC6)C46COC(C7OC8CCCCO8)OCC(C7)OC9CCCCO9

Level: 4

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OCC(=C)CCC(C2)OC(C3)C2C(CCC45)C3C5CC=C(CCCC6)C46COC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OCC(=C)CCC(C2)OC(C3)C2C(CCC45)C3C5CC=C(CCCC6)C46COC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OC(C2)COC(C2OC3CCCCO3)OCC45C(CCCC5)=CCC6C7C(CCC46)C8C(C7)OCC8

Level: 3

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OCC(=C)CCC(C2)OC(C3)C2C(CCC45)C3C5CC=C(CCCC6)C46COC7CCCCO7

Level: 2

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OCC34C(CCCC4)=CCC5C6C(CCC35)C7C(C6)OCC7

Level: 2

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OC2C(OCCC2)OCC34C(CCCC4)=CCC5C6C(CCC35)C7C(C6)OCC7

Level: 2

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OC2CC(COC2)OC3CCCCO3

Level: 2

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OCC(=C)CCC(C2)OC3CC(C4C23)C5C(CC4)C6C(=CC5)CCCC6

Level: 1

Mol. Weight: 1077.22 g/mol

Structure

SMILES: O1CCCCC1OCC23C(CCCC3)=CCC4C5C(CCC24)C6C(C5)OCC6

Level: 1

Mol. Weight: 1077.22 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1077.22 g/mol

Structure

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(=CC4)CCCC5

Level: 0

Mol. Weight: 1077.22 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1077.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
465464.42
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
60831554.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.71
Plasma Protein Binding
31.56
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
2.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-1414798.22
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.7
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
-110406333238.95
Rat (Acute)
4.0
Rat (Chronic Oral)
237.26
Fathead Minnow
139364452.85
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
12417648224.06
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-6893.47
Log(P)
-1.48
Log S
-2.36
Log(Vapor Pressure)
-408906652.21
Melting Point
222.92
pKa Acid
-2979431.43
pKa Basic
-23959.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Regucalcin Q64374 RGN_MOUSE Mus musculus 3 0.7385
Regucalcin Q64374 RGN_MOUSE Mus musculus 3 0.7385
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7049
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7049

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