(25R)-5alpha-spirostane-3beta,6alpha-diyl bis beta-D-glucopyranoside - Compound Card

(25R)-5alpha-spirostane-3beta,6alpha-diyl bis beta-D-glucopyranoside

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(25R)-5alpha-spirostane-3beta,6alpha-diyl bis beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Agavaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Steroidal Saponin
Canonical Smiles OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@@H]([C@@]4([C@@H]2C[C@H](CC4)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)CC[C@]2([C@H]3C[C@H]3[C@@H]2[C@@H]([C@]2(O3)CC[C@H](CO2)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C39H64O14/c1-17-5-10-39(48-16-17)18(2)28-25(53-39)13-22-20-12-24(50-36-34(47)32(45)30(43)27(15-41)52-36)23-11-19(6-8-37(23,3)21(20)7-9-38(22,28)4)49-35-33(46)31(44)29(42)26(14-40)51-35/h17-36,40-47H,5-16H2,1-4H3/t17-,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 AAVRFXAMWONIOE-ZCFMUJEJSA-N
Formula C39H64O14
HBA 14
HBD 8
MW 756.93
Rotatable Bonds 6
TPSA 217.22
LogP 0.41
Number Rings 8
Number Aromatic Rings 0
Heavy Atom Count 53
Formal Charge 0
Fraction CSP3 1.0
Exact Mass 756.43
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Furcraea tuberosa Agavaceae Plantae 39538

Showing of synonyms

  • Tapondjoua LA, Jenett-Siems K, et al. (2017). Flavonol glycosides and cytotoxic steroidal saponins from Furcraea tuberosa (Agavaceae). Natural Product Communications, 2017, 12(3), 347-350. [View] [PubMed]
Pubchem: 162942849

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 756.93 g/mol

Structure

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

Level: 1

Mol. Weight: 756.93 g/mol

Structure

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

Level: 1

Mol. Weight: 756.93 g/mol

Structure

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

Level: 0

Mol. Weight: 756.93 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 756.93 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
9.890
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2039.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.830
Plasma Protein Binding
93.22
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
-0.240
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-49.950
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.980
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
8.070
Micronucleos
Safe
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
-3700202.900
Rat (Acute)
3.730
Rat (Chronic Oral)
4.210
Fathead Minnow
4675.860
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
413447.190
Hydration Free Energy
-2.920
Log(D) at pH=7.4
3.570
Log(P)
1.4
Log S
-3.26
Log(Vapor Pressure)
-13472.6
Melting Point
258.55
pKa Acid
-51.79
pKa Basic
5.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8226
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8226
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7618
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7618
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7144
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7144

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