Daucovirgolide K - Compound Card

Daucovirgolide K

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Daucovirgolide K

Structure
Zoomed Structure
  • Family: Plantae - Umbelliferae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OO[C@H]1CC/C(=C/[C@@H]([C@H]2[C@H](CC1=C)OC(=O)[C@@]2(C)O)OC(=O)/C(=C\C)/C)/C
InChI InChI=1S/C20H28O7/c1-6-12(3)18(21)25-15-9-11(2)7-8-14(27-24)13(4)10-16-17(15)20(5,23)19(22)26-16/h6,9,14-17,23-24H,4,7-8,10H2,1-3,5H3/b11-9+,12-6-/t14-,15-,16-,17-,20-/m0/s1
InChIKey GGGOFSMCBXZZFE-ZMGLNZLYSA-N
Formula C20H28O7
HBA 7
HBD 2
MW 380.44
Rotatable Bonds 3
TPSA 102.29
LogP 2.7
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 380.18
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. (2019). Daucovirgolides I-L, four congeners of the antimalarial daucovirgolide G from Daucus virgatus. Fitoterapia,2019,137,104188. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)CC(=C)CCCC=CC2

Level: 0

Mol. Weight: 380.44 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.510
Plasma Protein Binding
64.83
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
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
6.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.200
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.360
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.550
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
-8.650
Rat (Acute)
3.040
Rat (Chronic Oral)
2.120
Fathead Minnow
4.010
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
355.450
Hydration Free Energy
-8.950
Log(D) at pH=7.4
1.750
Log(P)
2.87
Log S
-3.35
Log(Vapor Pressure)
-7.2
Melting Point
136.15
pKa Acid
7.76
pKa Basic
2.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8723
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7986
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7922
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7854
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7554
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7474
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7449
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7427
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7408
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7385
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7322
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7313
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7295
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7293
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7221
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7208
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7203
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7202
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7193
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7126
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7098
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7089
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7080
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7013

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