Methyl-2-epinuapapuanoate - Compound Card

Methyl-2-epinuapapuanoate

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Methyl-2-epinuapapuanoate

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cyclic Norterpene Peroxide
Canonical Smiles COC(=O)[C@@H](C1CC[C@@](OO1)(C)CCC1=C(C)CCCC1(C)C)C
InChI InChI=1S/C20H34O4/c1-14-8-7-11-19(3,4)16(14)9-12-20(5)13-10-17(23-24-20)15(2)18(21)22-6/h15,17H,7-13H2,1-6H3/t15-,17?,20-/m1/s1
InChIKey MRBQQESZUMBYBU-QMBUQHDCSA-N
Formula C20H34O4
HBA 4
HBD 0
MW 338.49
Rotatable Bonds 5
TPSA 44.76
LogP 4.97
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 338.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Diacarnus erythraenus Podospongiidae Animalia 283431

Showing of synonyms

  • Lefranc F, Nuzzo G, et al. (2013). In vitro pharmacological and toxicological effects of norterpene peroxides isolated from the Red Sea sponge Diacarnus erythraeanus on normal and cancer cells. Journal of Natural Products,2013,76(9),1541-1547. [View] [PubMed]
Pubchem: 162846392

No compound-protein relationship available.

Structure

SMILES: C1CCCC=C1CCC2CCCOO2

Level: 1

Mol. Weight: 338.49 g/mol

Structure

SMILES: C1CCOOC1

Level: 0

Mol. Weight: 338.49 g/mol

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 338.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.410
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.620
Plasma Protein Binding
56.93
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-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
7.810
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.080
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.530
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.310
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
-1.320
Rat (Acute)
1.910
Rat (Chronic Oral)
1.590
Fathead Minnow
4.110
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
345.790
Hydration Free Energy
-3.040
Log(D) at pH=7.4
3.640
Log(P)
5.84
Log S
-5.47
Log(Vapor Pressure)
-4.58
Melting Point
22.27
pKa Acid
11.1
pKa Basic
5.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8758
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8758
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8221
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8221
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8196
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8196
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8080
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8080
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7931
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7931
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7885
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7885
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7503
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7503
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7488
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7488
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7345
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7345
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7287
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7287
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7226
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7226
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7195
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7195
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7186
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7186
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7186
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7186
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7163
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7163
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7136
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7136
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7135
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7135
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7124
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7124
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7041
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7041
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7018
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7018
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7014
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7014
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7010
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7010

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