Daucoguaianolactone C - Compound Card

Daucoguaianolactone C

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Daucoguaianolactone C

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone Ester
Canonical Smiles CCC(=O)O[C@H]1CC(=C2[C@H]([C@H]3[C@@H]1[C@](C)(OC(=O)/C(=C\C)/C)C(=O)O3)C(=CC2=O)C)C
InChI InChI=1S/C23H28O7/c1-7-11(3)21(26)30-23(6)19-15(28-16(25)8-2)10-13(5)17-14(24)9-12(4)18(17)20(19)29-22(23)27/h7,9,15,18-20H,8,10H2,1-6H3/b11-7-/t15-,18+,19+,20-,23-/m0/s1
InChIKey AYWUJPCNTAUFOA-DFCGMIGISA-N
Formula C23H28O7
HBA 7
HBD 0
MW 416.47
Rotatable Bonds 4
TPSA 95.97
LogP 2.98
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 416.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Daucus glaber Apiaceae Plantae 4038

Showing of synonyms

  • Sallam AA, Hitotsuyanagi Y, et al. (2010). Sesquiterpene lactones from Daucus glaber. Helvetica Chimica Acta,2010,93,48-57. [View]
Pubchem: 102165830

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(C1=2)C3C(CC(=O)O3)CCC2

Level: 0

Mol. Weight: 416.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
73.4
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
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
9.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.16
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.7
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.92
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
-22.13
Rat (Acute)
2.8
Rat (Chronic Oral)
2.19
Fathead Minnow
4.2
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
401.37
Hydration Free Energy
-4.95
Log(D) at pH=7.4
2.41
Log(P)
3.23
Log S
-4.21
Log(Vapor Pressure)
-7.07
Melting Point
146.03
pKa Acid
8.07
pKa Basic
3.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7817
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7817
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7354
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7354
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7313
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7313
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7185
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7185
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7078
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7078

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