Dimethyl 2,3-bis-[5-(3,7-dimethylocta-2,6-dienyl)-3,6-dioxocyclohexa-1,4-dienyl]-succinate - Compound Card

Dimethyl 2,3-bis-[5-(3,7-dimethylocta-2,6-dienyl)-3,6-dioxocyclohexa-1,4-dienyl]-succinate

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Dimethyl 2,3-bis-[5-(3,7-dimethylocta-2,6-dienyl)-3,6-dioxocyclohexa-1,4-dienyl]-succinate

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Geranylbenzoquinonoid
Canonical Smiles COC(=O)C(C1=CC(=O)C=C(C1=O)C/C=C(/CCC=C(C)C)\C)C(C1=CC(=O)C=C(C1=O)C/C=C(/CCC=C(C)C)\C)C(=O)OC
InChI InChI=1S/C38H46O8/c1-23(2)11-9-13-25(5)15-17-27-19-29(39)21-31(35(27)41)33(37(43)45-7)34(38(44)46-8)32-22-30(40)20-28(36(32)42)18-16-26(6)14-10-12-24(3)4/h11-12,15-16,19-22,33-34H,9-10,13-14,17-18H2,1-8H3/b25-15+,26-16+
InChIKey HWCOBRZEMVYVFD-RYQLWAFASA-N
Formula C38H46O8
HBA 8
HBD 0
MW 630.78
Rotatable Bonds 15
TPSA 120.88
LogP 6.74
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 46
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 630.32
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Lettowianthus stellatus Annonaceae Plantae 489335

Showing of synonyms

  • Makangara JJ, Nkunya MH, et al. (2010). Geranylbenzoquinonoids from Lettowianthus stellatus fruits. Natural Product Research,2010,24(8),710-717. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(=O)C=C1CCC2=CC(=O)C=CC2=O

Level: 1

Mol. Weight: 630.78 g/mol

Structure

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

Level: 0

Mol. Weight: 630.78 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
8.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.480
Plasma Protein Binding
43.55
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
3.520
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.120
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.550
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
9.040
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-22842.720
Rat (Acute)
1.920
Rat (Chronic Oral)
3.310
Fathead Minnow
56.480
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
202.960
Hydration Free Energy
-2.920
Log(D) at pH=7.4
4.820
Log(P)
8.33
Log S
-6.46
Log(Vapor Pressure)
-9.59
Melting Point
152.01
pKa Acid
10.72
pKa Basic
1.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9508
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9508
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8955
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8955
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8821
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8821
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8795
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8795
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8601
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8601
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8598
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8598
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8543
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8543
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8453
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8453
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8381
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8381
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8354
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8354
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8172
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8172
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8041
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8041
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8023
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8023
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7852
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7852
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7824
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7824
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7817
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7817
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7804
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7804
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7801
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7801
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7800
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7800
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7782
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7782
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7779
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7779
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7767
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7767
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7763
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7763
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7756
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7756
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7755
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7755
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7752
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7752
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7721
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7721
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7705
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7705
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7704
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7704
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7701
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7701
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7698
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7698
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7678
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7678
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7651
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7651
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7644
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7644
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7640
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7640
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7613
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7613
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7544
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7544
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7509
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7509
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7501
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7501
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7496
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7496
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7393
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7393
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7384
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7384
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7355
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7355
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7295
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7295
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7277
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7277
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7271
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7271
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7255
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7255
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7253
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7253
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7245
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7245
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7244
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7244
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7240
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7240
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7233
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7233
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7192
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7192
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7191
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7191
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7190
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7190
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7152
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7152
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 2 0.7091
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 2 0.7091
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7070
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7070
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7061
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7061
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7054
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7054
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7040
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7040
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7009
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7009

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