(25 R)-5alpha spirostane-3beta, 6alpha, 23-triol 3,6-di-O-beta-D-glucopyranoside - Compound Card

(25 R)-5alpha spirostane-3beta, 6alpha, 23-triol 3,6-di-O-beta-D-glucopyranoside

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(25 R)-5alpha spirostane-3beta, 6alpha, 23-triol 3,6-di-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Agavaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Monodesmosidic Spirostanol Saponin
Canonical Smiles OCC1O[C@@H](O[C@H]2CC3C([C@@]4(C2C[C@H](CC4)O[C@@H]2OC(CO)[C@H](C([C@@H]2O)O)O)C)CC[C@]2(C3CC3C2[C@@H](C2(O3)OC[C@@H](C[C@@H]2O)C)C)C)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C39H64O15/c1-16-9-27(42)39(49-15-16)17(2)28-24(54-39)12-21-19-11-23(51-36-34(48)32(46)30(44)26(14-41)53-36)22-10-18(5-7-37(22,3)20(19)6-8-38(21,28)4)50-35-33(47)31(45)29(43)25(13-40)52-35/h16-36,40-48H,5-15H2,1-4H3/t16-,17+,18+,19?,20?,21?,22?,23+,24?,25?,26?,27+,28?,29-,30-,31?,32?,33+,34+,35-,36-,37-,38+,39?/m1/s1
InChIKey JLLFUINRPWOBGS-XGHCGZTASA-N
Formula C39H64O15
HBA 15
HBD 9
MW 772.93
Rotatable Bonds 6
TPSA 237.45
LogP -0.62
Number Rings 8
Number Aromatic Rings 0
Heavy Atom Count 54
Formal Charge 0
Fraction CSP3 1.0
Exact Mass 772.42
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Agave macroacantha Agavaceae Plantae 382123

Showing of synonyms

  • Eskander J, Lavaud C and Harakat D. (2010). Steroidal saponins from the leaves of Agave macroacantha. Fitoterapia,2010,81,371-374. [View] [PubMed]
Pubchem: 162987203

No compound-protein relationship available.

Structure

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(C(C5)OC7CCCCO7)CC(CC6)OC8CCCCO8

Level: 2

Mol. Weight: 772.93 g/mol

Structure

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CCCC6)C(C5)OC7CCCCO7

Level: 1

Mol. Weight: 772.93 g/mol

Structure

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 772.93 g/mol

Structure

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CC5)CCCC6

Level: 0

Mol. Weight: 772.93 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 772.93 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.43
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
17.09
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2985.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
75.46
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.43
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-73.74
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.09
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
8.65
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-5418875.15
Rat (Acute)
3.84
Rat (Chronic Oral)
4.35
Fathead Minnow
6847.35
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
606624.3
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.83
Log(P)
0.59
Log S
-2.97
Log(Vapor Pressure)
-19851.4
Melting Point
278.54
pKa Acid
-94.22
pKa Basic
5.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7787
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7787
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7748
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7748
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7431
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7431
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7088
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7088

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