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

18,19-epoxyxenic-18,19-dimethoxy-4-hydroxy-6,9,13-triene

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18,19-epoxyxenic-18,19-dimethoxy-4-hydroxy-6,9,13-triene

Structure
Zoomed Structure
  • Family: Plantae - Dictyotaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC1OC(/C/2=C/C/C=C(/CC(C(C12)C(CCC=C(C)C)C)O)\C)OC
InChI InChI=1S/C22H36O4/c1-14(2)9-7-11-16(4)19-18(23)13-15(3)10-8-12-17-20(19)22(25-6)26-21(17)24-5/h9-10,12,16,18-23H,7-8,11,13H2,1-6H3/b15-10+,17-12+
InChIKey HHOTZDHXDANUOI-OUBCGSOKSA-N
Formula C22H36O4
HBA 4
HBD 1
MW 364.53
Rotatable Bonds 6
TPSA 47.92
LogP 4.6
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 364.26
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: 276157
Structure

SMILES: C1OCC(C1=2)CCCC=CCC2

Level: 0

Mol. Weight: 364.53 g/mol

Antitumor

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.720
Plasma Protein Binding
28.96
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.750
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.360
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.210
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.560
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.350
Rat (Acute)
2.280
Rat (Chronic Oral)
1.820
Fathead Minnow
5.160
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
359.060
Hydration Free Energy
-5.150
Log(D) at pH=7.4
3.850
Log(P)
5.54
Log S
-4.34
Log(Vapor Pressure)
-5.46
Melting Point
57.44
pKa Acid
9.6
pKa Basic
4.59
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 0.8993
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8993
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8855
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8855
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8709
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8709
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8703
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8703
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8268
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8268
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8185
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8185
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8050
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8050
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7980
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7980
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7865
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7865
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7773
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7773
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7673
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7673
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7655
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7655
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7641
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7641
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7581
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7581
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7512
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7512
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7477
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7477
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7457
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7457
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7454
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7454
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7453
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7453
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7428
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7428
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7417
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7417
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7405
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7405
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7342
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7342
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7254
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7254
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7227
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7227
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7200
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7200
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7195
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7195
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7074
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7074
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7067
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7067

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