Ajugarin-1 - Compound Card

Ajugarin-1

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Ajugarin-1

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)OC[C@@]12[C@@H](OC(=O)C)C[C@H]([C@]([C@H]1CCC[C@@]12CO1)(C)CCC1=CC(=O)OC1)C
InChI InChI=1S/C24H34O7/c1-15-10-20(31-17(3)26)24(14-29-16(2)25)19(6-5-8-23(24)13-30-23)22(15,4)9-7-18-11-21(27)28-12-18/h11,15,19-20H,5-10,12-14H2,1-4H3/t15-,19-,20+,22+,23+,24+/m1/s1
InChIKey RNYBNBANBCQZON-PGQNDPHJSA-N
Formula C24H34O7
HBA 7
HBD 0
MW 434.53
Rotatable Bonds 6
TPSA 91.43
LogP 3.35
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 434.23
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ajuga remota Lamiaceae Plantae 38595

Showing of synonyms

  • Kuria KA, Chepkwony H, et al. (2002). The antiplasmodial activity of isolates from Ajuga remota.. Journal of Natural Products,2002,65(5),789-793. [View] [PubMed]
Pubchem: 173866
Kegg Ligand: C09058
Chebi: 2527
Nmrshiftdb2: 60080528

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1CCC(CCC2)C(C2C34CO4)CCC3

Level: 1

Mol. Weight: 434.53 g/mol

Structure

SMILES: O1CC12C3C(CCC2)CCCC3

Level: 0

Mol. Weight: 434.53 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 434.53 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.22
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.01
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
42.07
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
12.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.14
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.19
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
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-55.53
Rat (Acute)
3.06
Rat (Chronic Oral)
1.85
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
463.07
Hydration Free Energy
-2.82
Log(D) at pH=7.4
2.55
Log(P)
1.05
Log S
-4.82
Log(Vapor Pressure)
-7.45
Melting Point
116.93
pKa Acid
7.48
pKa Basic
5.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7673
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7673
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7311
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7311

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