7-O-6'-O-malonylcachinesidic acid - Compound Card

7-O-6'-O-malonylcachinesidic acid

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7-O-6'-O-malonylcachinesidic acid

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles O=C1OC[C@H]2O[C@@H](O[C@H]3C4[C@@]([C@@H](OC(=O)C1)CC4C(=CO3)C(=O)O)(C)O)[C@@H]([C@H]([C@@H]2O)O)O
InChI InChI=1S/C19H24O13/c1-19(27)9-2-6-7(16(25)26)4-29-17(12(6)19)32-18-15(24)14(23)13(22)8(30-18)5-28-10(20)3-11(21)31-9/h4,6,8-9,12-15,17-18,22-24,27H,2-3,5H2,1H3,(H,25,26)/t6?,8-,9+,12?,13-,14+,15-,17+,18+,19+/m1/s1
InChIKey ZILVNWQDAWWXCU-FCCPFWGBSA-N
Formula C19H24O13
HBA 12
HBD 5
MW 460.39
Rotatable Bonds 1
TPSA 198.51
LogP -2.62
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 460.12
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ajuga pseudoiva Lamiaceae Plantae 2026104

Showing of synonyms

  • Chaari A, Jannet HB, et al. (2002). 7-O-6'-O-malonylcachinesidic acid, a new macrocyclic iridoid ester of malonic acid from the Tunisian plant Ajuga pseudoiva. Journal of Natural Products,2002,65(4),618-620. [View] [PubMed]
Pubchem: 163003024

No compound-protein relationship available.

Structure

SMILES: C1=COC(C2C13)OC4CCCC(O4)COC(=O)CC(=O)OC(C3)C2

Level: 0

Mol. Weight: 460.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.27
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.1
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
45.37
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.14
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.53
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.23
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
-55.18
Rat (Acute)
2.07
Rat (Chronic Oral)
2.92
Fathead Minnow
3.58
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
496.13
Hydration Free Energy
-4.19
Log(D) at pH=7.4
-1.51
Log(P)
-2.48
Log S
-1.44
Log(Vapor Pressure)
-15.97
Melting Point
190.93
pKa Acid
2.97
pKa Basic
4.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7434
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7434
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7076
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7076
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 3 0.7006
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 3 0.7006

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