(24R)-24-ethyl-6beta-hydroperoxy-cholest-4-en-3-O-beta-D-glucopyranoside - Compound Card

(24R)-24-ethyl-6beta-hydroperoxy-cholest-4-en-3-O-beta-D-glucopyranoside

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(24R)-24-ethyl-6beta-hydroperoxy-cholest-4-en-3-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Hydroperoxy Sterol
Canonical Smiles CC[C@@H](C(C)C)CCC([C@H]1CCC2[C@]1(C)CCC1C2C[C@H](C2=C[C@H](CC[C@]12C)O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O)OO)C
InChI InChI=1S/C35H60O8/c1-7-21(19(2)3)9-8-20(4)24-10-11-25-23-17-28(43-40)27-16-22(12-14-35(27,6)26(23)13-15-34(24,25)5)41-33-32(39)31(38)30(37)29(18-36)42-33/h16,19-26,28-33,36-40H,7-15,17-18H2,1-6H3/t20?,21-,22+,23?,24-,25?,26?,28-,29?,30-,31?,32+,33-,34-,35-/m1/s1
InChIKey PAESJLPQEQVMTB-CDBMBUNZSA-N
Formula C35H60O8
HBA 8
HBD 5
MW 608.86
Rotatable Bonds 10
TPSA 128.84
LogP 5.32
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 608.43
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Galium brunneum Rubiaceae Plantae 25168

Showing of synonyms

  • Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 608.86 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 608.86 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 608.86 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
7.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.09
Plasma Protein Binding
98.31
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
2.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.03
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.07
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.37
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
-16890.01
Rat (Acute)
3.3
Rat (Chronic Oral)
3.39
Fathead Minnow
35.85
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
499.41
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.0
Log(P)
5.96
Log S
-4.46
Log(Vapor Pressure)
-13.31
Melting Point
184.92
pKa Acid
7.87
pKa Basic
6.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7452
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7110
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7070

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