(Z)-2,5-dihydroxy-6-methyl-3-(pentadec-10’-enyl)-1,4-benzoquinone - Compound Card

(Z)-2,5-dihydroxy-6-methyl-3-(pentadec-10’-enyl)-1,4-benzoquinone

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(Z)-2,5-dihydroxy-6-methyl-3-(pentadec-10’-enyl)-1,4-benzoquinone

Structure
Zoomed Structure
  • Family: Plantae - Primulaceae
  • Kingdom: Plantae
  • Class: Benzoquinone
    • Subclass: Alkenyl Benzoquinone
Canonical Smiles CCCC/C=C\CCCCCC1=C(O)C(=O)C(=C(C1=O)O)C
InChI InChI=1S/C18H26O4/c1-3-4-5-6-7-8-9-10-11-12-14-17(21)15(19)13(2)16(20)18(14)22/h6-7,19,22H,3-5,8-12H2,1-2H3/b7-6-
InChIKey HGDPVSBGHXHFAK-SREVYHEPSA-N
Formula C18H26O4
HBA 4
HBD 2
MW 306.4
Rotatable Bonds 9
TPSA 74.6
LogP 4.48
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 306.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Maesa lanceolata Primulaceae Plantae 992730

Showing of synonyms

  • Seumo AS, Nanfack ARD, et al. (2022). Alkenylbenzoquinones and other compounds from the fruit of Maesa lanceolata exhibited potent cytotoxic, antibacterial, and antiradical scavenging activities.. Natural product research,2022, 36(17), 4379-4387. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(=O)C=C1

Level: 0

Mol. Weight: 306.4 g/mol

Antibacterial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.18
Plasma Protein Binding
42.33
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.21
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.47
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.0
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
4.78
Rat (Acute)
1.87
Rat (Chronic Oral)
2.67
Fathead Minnow
4.22
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
373.98
Hydration Free Energy
-10.2
Log(D) at pH=7.4
3.06
Log(P)
4.68
Log S
-4.03
Log(Vapor Pressure)
-7.23
Melting Point
64.4
pKa Acid
4.67
pKa Basic
4.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9582
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.8315
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8076
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8012
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7954
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7785
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7414
Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial Q5HZ00 SPS3_ARATH Arabidopsis thaliana 2 0.7366
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7324
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7314
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7289
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7278
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7218
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7179
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7164
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7143
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7137
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7082
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7078
Glutamate receptor 4 P19493 GRIA4_RAT Rattus norvegicus 2 0.7032
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7019
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7014

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