Daucoguaianolactone A - Compound Card

Daucoguaianolactone A

Select a section from the left sidebar

Daucoguaianolactone A

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone Ester
Canonical Smiles C/C=C(\C(=O)O[C@]1(C)C(=O)O[C@@H]2[C@H]1[C@@H](OC(=O)CC(C)C)CC(=C1[C@H]2C(=CC1=O)C)C)/C
InChI InChI=1S/C25H32O7/c1-8-13(4)23(28)32-25(7)21-17(30-18(27)9-12(2)3)11-15(6)19-16(26)10-14(5)20(19)22(21)31-24(25)29/h8,10,12,17,20-22H,9,11H2,1-7H3/b13-8-/t17-,20+,21+,22-,25-/m0/s1
InChIKey MXOILUJUCPTKGJ-NXVPVDKWSA-N
Formula C25H32O7
HBA 7
HBD 0
MW 444.52
Rotatable Bonds 5
TPSA 95.97
LogP 3.62
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 444.21
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: 102165828

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 444.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
82.95
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.23
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.55
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.16
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
-43.93
Rat (Acute)
3.06
Rat (Chronic Oral)
2.34
Fathead Minnow
4.27
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
413.47
Hydration Free Energy
-3.27
Log(D) at pH=7.4
3.23
Log(P)
3.91
Log S
-4.71
Log(Vapor Pressure)
-7.14
Melting Point
133.9
pKa Acid
8.71
pKa Basic
3.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7840
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7840
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7759
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7759
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7577
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7577
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7378
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7378
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7356
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7356
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7276
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7276
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7228
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7228
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7223
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7223
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7185
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7185
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7134
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7134
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7098
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7098

Download SDF