Daucovirgolide A - Compound Card

Daucovirgolide A

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Daucovirgolide A

Structure
Zoomed Structure
  • Family: Plantae - Umbelliferae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpenoid
Canonical Smiles C/C=C(\C(=O)O[C@H]1/C=C(\C)/CC[C@H]2[C@@](C[C@H]3[C@H]1[C@](C)(O)C(=O)O3)(C)O2)/C
InChI InChI=1S/C20H28O6/c1-6-12(3)17(21)24-13-9-11(2)7-8-15-19(4,26-15)10-14-16(13)20(5,23)18(22)25-14/h6,9,13-16,23H,7-8,10H2,1-5H3/b11-9+,12-6-/t13-,14-,15-,16-,19-,20-/m0/s1
InChIKey IEUHJMOSXFVRJV-RYSWWKMMSA-N
Formula C20H28O6
HBA 6
HBD 1
MW 364.44
Rotatable Bonds 2
TPSA 85.36
LogP 2.44
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 364.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Daucus virgatus Umbelliferae Plantae 1869349

Showing of synonyms

  • Sirignano C, Snene A, et al. (2017). Angeloylated Germacranolides from Daucus virgatus and Their Plasmodium Transmission Blocking Activity. J Nat Prod,2017,80(10),2787-2794. [View] [PubMed]
Pubchem: 145952073

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC=CCC3C(C1)OC(=O)C3

Level: 0

Mol. Weight: 364.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
32.17
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.58
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.03
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.02
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
-7.84
Rat (Acute)
3.59
Rat (Chronic Oral)
1.8
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
369.49
Hydration Free Energy
-6.01
Log(D) at pH=7.4
1.99
Log(P)
2.82
Log S
-3.35
Log(Vapor Pressure)
-6.28
Melting Point
100.61
pKa Acid
6.6
pKa Basic
2.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7954
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7653
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7623
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7553
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7213
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7134
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7105
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7060
Alanine aminotransferase Q9P9M8 Q9P9M8_9EURY Pyrococcus furiosus 2 0.7034
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7008

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