18,19-epoxyxenic-19-methoxy-18-hydroxy-4-acetoxy-6,9,13-triene - Compound Card

18,19-epoxyxenic-19-methoxy-18-hydroxy-4-acetoxy-6,9,13-triene

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18,19-epoxyxenic-19-methoxy-18-hydroxy-4-acetoxy-6,9,13-triene

Structure
Zoomed Structure
  • Family: Plantae - Dictyotaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC1OC(C2/C/1=C\C/C=C(/CC(C2C(CCC=C(C)C)C)OC(=O)C)\C)O
InChI InChI=1S/C23H36O5/c1-14(2)9-7-11-16(4)20-19(27-17(5)24)13-15(3)10-8-12-18-21(20)22(25)28-23(18)26-6/h9-10,12,16,19-23,25H,7-8,11,13H2,1-6H3/b15-10+,18-12+
InChIKey YQRVRXGVKYSYLV-XSDUGUOQSA-N
Formula C23H36O5
HBA 5
HBD 1
MW 392.54
Rotatable Bonds 6
TPSA 64.99
LogP 4.52
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 392.26
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Padina pavonia Dictyotaceae Plantae 82389

Showing of synonyms

  • Awad NE, Selim MA, et al. (2008). Cytotoxic xenicane diterpenes from the brown alga Padina pavonia (L.) Gaill. Phytotherapy Research,2008,22,1610-1613. [View] [PubMed]
CPRiL: 276156
Structure

SMILES: C1OCC(C1=2)CCCC=CCC2

Level: 0

Mol. Weight: 392.54 g/mol

Antitumor

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.600
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
32.05
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.480
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.890
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.930
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.370
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
-3.270
Rat (Acute)
2.500
Rat (Chronic Oral)
2.040
Fathead Minnow
5.150
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
379.370
Hydration Free Energy
-4.930
Log(D) at pH=7.4
3.690
Log(P)
5.37
Log S
-4.85
Log(Vapor Pressure)
-6.04
Melting Point
62.86
pKa Acid
9.22
pKa Basic
4.35
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9485
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9485
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7945
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7945
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7908
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7908
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7876
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7876
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7827
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7827
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7695
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7695
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7618
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7618
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7600
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7600
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7591
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7591
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7560
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7560
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7484
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7484
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7362
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7362
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7342
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7342
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7310
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7310
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7197
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7197
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7186
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7186
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7122
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7122
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7083
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7083
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7064
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7064
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7063
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7063

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