(23S)-isolimonexic acid - Compound Card

(23S)-isolimonexic acid

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(23S)-isolimonexic acid

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles O=C1OC[C@]23[C@H](C1)OC([C@@H]2CC(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2C1=CC(OC1=O)O)C)C)(C)C
InChI InChI=1S/C26H30O10/c1-22(2)13-8-14(27)24(4)12(25(13)10-32-16(28)9-15(25)35-22)5-6-23(3)18(11-7-17(29)33-20(11)30)34-21(31)19-26(23,24)36-19/h7,12-13,15,17-19,29H,5-6,8-10H2,1-4H3/t12-,13-,15-,17?,18-,19+,23-,24-,25+,26+/m0/s1
InChIKey DNNFETMOXYZICP-OKRPZFHJSA-N
Formula C26H30O10
HBA 10
HBD 1
MW 502.52
Rotatable Bonds 1
TPSA 137.96
LogP 0.97
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 502.18
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus × paradisi Rutaceae Plantae 37656

Showing of synonyms

  • Essombe Malolo FA, Bellier Tabekoueng G, et al. (2022). Chemical Constituents of the Stem Bark of the Hybrid Plant Citrus × paradisi Macfad. (Rutaceae).. Chemistry & biodiversity,2022, 19(7), e202101033. [View] [PubMed]
Pubchem: 5321282
Nmrshiftdb2: 60023976

No compound-protein relationship available.

Structure

SMILES: O=C1OCC=C1C(OC(=O)C(C234)O4)C3CCC5C67C(CC(=O)C25)COC6CC(=O)OC7

Level: 1

Mol. Weight: 502.52 g/mol

Structure

SMILES: C123C(O3)C(=O)OCC2CCC4C56C(CC(=O)C14)COC5CC(=O)OC6

Level: 0

Mol. Weight: 502.52 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 502.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.24
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.11
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.29
Plasma Protein Binding
38.33
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.41
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.63
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
-861.56
Rat (Acute)
5.66
Rat (Chronic Oral)
1.75
Fathead Minnow
4.05
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
525.2
Hydration Free Energy
-2.87
Log(D) at pH=7.4
0.57
Log(P)
0.48
Log S
-4.96
Log(Vapor Pressure)
-10.03
Melting Point
318.99
pKa Acid
3.78
pKa Basic
3.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7246

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