(25R)-3beta-{O-beta-D-glucopyranosyloxy}-22alphaN-spirosol-5-ene - Compound Card

(25R)-3beta-{O-beta-D-glucopyranosyloxy}-22alphaN-spirosol-5-ene

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(25R)-3beta-{O-beta-D-glucopyranosyloxy}-22alphaN-spirosol-5-ene

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Glycosidic Steroidal Alkaloid
Canonical Smiles OC[C@H]1OC(OC2CCC3(C(=CCC4C3CCC3(C4CC4C3C(C)C3(O4)CCC(CN3)C)C)C2)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C33H53NO7/c1-17-7-12-33(34-15-17)18(2)26-24(41-33)14-23-21-6-5-19-13-20(8-10-31(19,3)22(21)9-11-32(23,26)4)39-30-29(38)28(37)27(36)25(16-35)40-30/h5,17-18,20-30,34-38H,6-16H2,1-4H3/t17?,18?,20?,21?,22?,23?,24?,25-,26?,27-,28+,29-,30?,31?,32?,33?/m1/s1
InChIKey XMLLJGHZPHTUKK-ZOYZCTNRSA-N
Formula C33H53NO7
HBA 8
HBD 5
MW 575.79
Rotatable Bonds 3
TPSA 120.64
LogP 3.11
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 575.38
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Solanum aculeastrum Solanaceae Plantae 329759

Showing of synonyms

  • Wanyonyi AW, Tarus PK, et al. (2003). A novel glycosidic steroidal alkaloid from Solanum aculeastrum. Bulletin of the Chemical Society of Ethiopia,2003,17(1),61-66. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: N1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 575.79 g/mol

Structure

SMILES: N1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(=CC5)CCCC6

Level: 0

Mol. Weight: 575.79 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 575.79 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.94
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
5.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.91
Plasma Protein Binding
45.09
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
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
1.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.98
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.78
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.14
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
-12261.68
Rat (Acute)
3.25
Rat (Chronic Oral)
2.79
Fathead Minnow
27.69
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
412.5
Hydration Free Energy
-2.92
Log(D) at pH=7.4
4.56
Log(P)
3.53
Log S
-4.32
Log(Vapor Pressure)
-12.19
Melting Point
241.15
pKa Acid
9.2
pKa Basic
8.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8294
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8294
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7867
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7867
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7765
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7765
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7487
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7487
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7211
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7211
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7129
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7129
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7078
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7078

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