Aguerin A - Compound Card

Aguerin A

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Aguerin A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)C(=C)[C@H](C2)O)C
InChI InChI=1S/C19H24O5/c1-8(2)18(21)23-14-6-9(3)12-7-13(20)10(4)15(12)17-16(14)11(5)19(22)24-17/h8,12-17,20H,3-7H2,1-2H3/t12-,13-,14-,15-,16+,17+/m0/s1
InChIKey KCMNJMYYSFJSAZ-NQLMQOPMSA-N
Formula C19H24O5
HBA 5
HBD 1
MW 332.4
Rotatable Bonds 2
TPSA 72.83
LogP 2.17
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 332.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus sempervirens Asteraceae Plantae 65000
2 Cheirolophus mauritanicus Asteraceae Plantae 64998

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 13996677
Nmrshiftdb2: 60074565

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C

Level: 0

Mol. Weight: 332.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
60.57
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.13
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.03
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.76
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.69
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
-0.9
Rat (Acute)
3.64
Rat (Chronic Oral)
1.94
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
363.54
Hydration Free Energy
-6.43
Log(D) at pH=7.4
1.67
Log(P)
2.0
Log S
-3.48
Log(Vapor Pressure)
-7.11
Melting Point
147.72
pKa Acid
7.35
pKa Basic
3.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8417
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8417
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7460
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7460
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7120
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7120

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