3-O-(beta-D-glucopyranosyl) etioline - Compound Card

3-O-(beta-D-glucopyranosyl) etioline

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3-O-(beta-D-glucopyranosyl) etioline

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Steroid Alkaloid
Canonical Smiles OC[C@H]1OC(O[C@H]2CC[C@]3(C(=CCC4C3CC[C@]3(C4C[C@H](C3[C@@H](C3=NCC(CC3)C)C)O)C)C2)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C33H53NO7/c1-17-5-8-24(34-15-17)18(2)27-25(36)14-23-21-7-6-19-13-20(9-11-32(19,3)22(21)10-12-33(23,27)4)40-31-30(39)29(38)28(37)26(16-35)41-31/h6,17-18,20-23,25-31,35-39H,5,7-16H2,1-4H3/t17?,18-,20+,21?,22?,23?,25-,26-,27?,28-,29+,30-,31?,32+,33+/m1/s1
InChIKey TVYPZWCCOPYBIW-PXBXDMGUSA-N
Formula C33H53NO7
HBA 8
HBD 5
MW 575.79
Rotatable Bonds 5
TPSA 131.97
LogP 3.23
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.91
Exact Mass 575.38
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Solanum diphyllum Solanaceae Plantae 693386

Showing of synonyms

  • El-Sayed MA, Mohamed Ael-H, et al. (2009). Cytotoxicity of 3-O-(beta-D-glucopyranosyl) etioline, a steroidal alkaloid from Solanum diphyllum L.. Zeitschrift für Naturforschung C,2009,64(9-10),644-649. [View] [PubMed]
Pubchem: 163025299

No compound-protein relationship available.

Structure

SMILES: C1CCCN=C1CC2CCC(C23)C4C(CC3)C5C(=CC4)CC(CC5)OC6CCCCO6

Level: 2

Mol. Weight: 575.79 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 575.79 g/mol

Structure

SMILES: C1CCCN=C1CC2CCC(C23)C4C(CC3)C5C(=CC4)CCCC5

Level: 1

Mol. Weight: 575.79 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 575.79 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 575.79 g/mol

Structure

SMILES: C1=NCCCC1

Level: 0

Mol. Weight: 575.79 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.99
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.96
Plasma Protein Binding
84.31
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
1.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.73
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.59
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.56
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-8898.47
Rat (Acute)
3.47
Rat (Chronic Oral)
2.82
Fathead Minnow
22.85
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
377.02
Hydration Free Energy
-2.96
Log(D) at pH=7.4
4.4
Log(P)
3.76
Log S
-3.97
Log(Vapor Pressure)
-13.37
Melting Point
210.11
pKa Acid
8.76
pKa Basic
7.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7764
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7764
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7743
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7743
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7220
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7141
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7141
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7021
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7021
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7001
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7001

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