3beta,23-dihydroxyolean-13(18)-en-28-oic acid 28-O-beta-D-glucopyranoside-3,23-disulfate ester - Compound Card

3beta,23-dihydroxyolean-13(18)-en-28-oic acid 28-O-beta-D-glucopyranoside-3,23-disulfate ester

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3beta,23-dihydroxyolean-13(18)-en-28-oic acid 28-O-beta-D-glucopyranoside-3,23-disulfate ester

Structure
Zoomed Structure
  • Family: Plantae - Zygophyllaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene Glycoside
Canonical Smiles OC[C@@H]1O[C@H](OC(=O)[C@]23CC[C@@]4(C(=C3CC(CC2)(C)C)CCC2[C@@]4(C)CCC3[C@]2(C)CC[C@@H]([C@@]3(C)COS(=O)(=O)O)OS(=O)(=O)O)C)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C36H58O15S2/c1-31(2)13-15-36(30(41)50-29-28(40)27(39)26(38)22(18-37)49-29)16-14-34(5)20(21(36)17-31)7-8-24-32(3)11-10-25(51-53(45,46)47)33(4,19-48-52(42,43)44)23(32)9-12-35(24,34)6/h22-29,37-40H,7-19H2,1-6H3,(H,42,43,44)(H,45,46,47)/t22-,23?,24?,25-,26-,27+,28-,29+,32-,33-,34+,35+,36-/m0/s1
InChIKey UXAAKPMCRDHSMD-OAWUKTFVSA-N
Formula C36H58O15S2
HBA 13
HBD 6
MW 794.98
Rotatable Bonds 8
TPSA 243.65
LogP 3.26
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 53
Formal Charge 0
Fraction CSP3 0.92
Exact Mass 794.32
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Fagonia arabica Zygophyllaceae Plantae 291457

Showing of synonyms

  • Perrone A, Masullo M, et al. (2007). Sulfated Triterpene Derivatives from Fagonia arabica. J Nat Prod,2007,70(4),584-3. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)=C4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 794.98 g/mol

Structure

SMILES: C1CCCC(C1=C23)CCC2C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 794.98 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 794.98 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.14
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-3.770
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
355.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
82.37
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
0.480
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-7.190
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.320
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
-647003.740
Rat (Acute)
2.130
Rat (Chronic Oral)
3.650
Fathead Minnow
824.530
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
67364.490
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.130
Log(P)
-0.77
Log S
-2.03
Log(Vapor Pressure)
-2236.85
Melting Point
304.88
pKa Acid
0.07
pKa Basic
6.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7847

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