Methylenedioxyendiandric acid A - Compound Card

Methylenedioxyendiandric acid A

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Methylenedioxyendiandric acid A

Structure
Zoomed Structure
  • Family: Plantae - Lauraceae
  • Kingdom: Plantae
  • Class: Polycyclic
Canonical Smiles OC(=O)C[C@@H]1[C@H]2C=C[C@@H]3[C@@H]4[C@H]2[C@H]1C[C@H]4CC=C3c1ccc2c(c1)OCO2
InChI InChI=1S/C22H22O4/c23-20(24)9-16-15-5-4-14-13(3-1-12-7-17(16)22(15)21(12)14)11-2-6-18-19(8-11)26-10-25-18/h2-6,8,12,14-17,21-22H,1,7,9-10H2,(H,23,24)/t12-,14+,15-,16-,17+,21-,22-/m1/s1
InChIKey FVBUQBYJLMGLLA-JUDDEXIUSA-N
Formula C22H22O4
HBA 3
HBD 1
MW 350.41
Rotatable Bonds 3
TPSA 55.76
LogP 3.98
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 350.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Beilschmiedia louisii Lauraceae Plantae 88849

Showing of synonyms

  • Waleguele CC, Mba'ning BM, et al. (2020). Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae). Molecules. 2020, 25(12), 2862. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C12C3CC1C=CC4C2C(C3)CC=C4c(c5)ccc(c56)OCO6

Level: 1

Mol. Weight: 350.41 g/mol

Structure

SMILES: C12C3CC1C=CC4C2C(C3)CC=C4

Level: 0

Mol. Weight: 350.41 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 350.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.01
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.91
Plasma Protein Binding
88.14
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.72
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.21
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.69
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-9.34
Rat (Acute)
2.33
Rat (Chronic Oral)
1.97
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
465.8
Hydration Free Energy
-4.01
Log(D) at pH=7.4
2.66
Log(P)
5.11
Log S
-5.56
Log(Vapor Pressure)
-8.19
Melting Point
215.78
pKa Acid
5.82
pKa Basic
5.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9741
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.9437
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9148
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9021
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8962
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8926
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.8835
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8754
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8675
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8633
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8616
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8589
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.8582
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8523
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8508
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8492
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8434
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8350
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8304
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8265
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8233
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8229
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8209
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8191
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 4 0.8147
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8103
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8100
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8054
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8036
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7964
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7961
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7953
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7947
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7939
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 3 0.7932
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7885
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7852
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7845
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7841
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7796
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7768
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7730
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7711
Nucleoside diphosphate kinase Q5SLV5 NDK_THET8 Thermus thermophilus 2 0.7675
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7658
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7649
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7613
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7596
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7594
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7569
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 3 0.7529
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7523
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7514
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7490
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7483
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7481
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7469
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7453
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7443
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7435
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7429
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7421
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7397
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7393
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7392
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7391
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7385
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7355
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7353
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7344
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7341
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7339
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7333
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7333
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7293
Morphinone reductase Q51990 Q51990_PSEPU Pseudomonas putida 2 0.7291
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7290
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7276
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7265
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7246
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7238
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7230
PTS system glucose-specific EIIA component P69783 PTGA_ECOLI Escherichia coli 3 0.7225
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7220
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7220
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7205
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7201
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7201
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7199
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7197
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7196
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7184
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 2 0.7178
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7155
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7150
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7141
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7139
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7135
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7130
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7127
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7127
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7102
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7102
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7089
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7081
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7068
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7065
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7060
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7059
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7059
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7059
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7052
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7051
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7048
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7044
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7043
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7035
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7033
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7032
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7025
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7020
Fatty acid-binding protein 2, liver P81400 FABP2_AMBME Ambystoma mexicanum 2 0.7016
Eukaryotic translation initiation factor 2 subunit alpha P20459 IF2A_YEAST Saccharomyces cerevisiae 3 0.7015
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7012
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7009
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7005

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