Macrophyllin - Compound Card

Macrophyllin

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Macrophyllin

Structure
Zoomed Structure
  • Family: Plantae - Myrsinaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Benzoquinone
Canonical Smiles C=CCC1=C[C@]2(OC)C(=O)C([C@@H]1O)[C@@H]([C@H]2C)c1cc(OC)c(c(c1)OC)OC
InChI InChI=1S/C22H28O6/c1-7-8-13-11-22(28-6)12(2)17(18(19(13)23)21(22)24)14-9-15(25-3)20(27-5)16(10-14)26-4/h7,9-12,17-19,23H,1,8H2,2-6H3/t12-,17+,18?,19-,22-/m1/s1
InChIKey NWXSUVZITFIXOL-FXNKJGLGSA-N
Formula C22H28O6
HBA 6
HBD 1
MW 388.46
Rotatable Bonds 7
TPSA 74.22
LogP 2.89
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 388.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Maesa lanceolata Myrsinaceae Plantae 992730

Showing of synonyms

  • Midiwo JO, Arot LM, et al. (1988). Distribution of benzoquinone pigments in Kenyan Myrsinaceae.. Bulletin of the Chemical Society of Ethiopia,1988,2(2),83-85. [View] [PubMed]
Pubchem: 45487148
Nmrshiftdb2: 70119645
Bindingdb: 50303144

No compound-protein relationship available.

Structure

SMILES: C1C=CC(C(=O)C12)CC2c3ccccc3

Level: 1

Mol. Weight: 388.46 g/mol

Structure

SMILES: C12C(=O)C(CC1)CC=C2

Level: 0

Mol. Weight: 388.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 388.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.69
Plasma Protein Binding
64.19
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.82
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.73
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-10.29
Rat (Acute)
3.04
Rat (Chronic Oral)
2.37
Fathead Minnow
4.46
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
401.96
Hydration Free Energy
-6.84
Log(D) at pH=7.4
2.48
Log(P)
2.05
Log S
-3.01
Log(Vapor Pressure)
-7.3
Melting Point
119.47
pKa Acid
6.46
pKa Basic
2.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9334
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9334
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9203
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9203
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8216
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8216
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7686
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7686
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7604
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7604
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7588
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7588
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7535
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7535
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7510
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7510
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7351
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7351
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 3 0.7301
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 3 0.7301
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7278
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7278
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7265
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7265
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7259
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7259
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7255
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7255
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7169
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7169
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7169
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7169
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7162
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7162
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7129
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7129
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7115
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7115
Lipoyl synthase 2 Q8DLC2 LIPA2_THEEB Thermosynechococcus vestitus 4 0.7099
Lipoyl synthase 2 Q8DLC2 LIPA2_THEEB Thermosynechococcus vestitus 4 0.7099
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7094
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7094
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7011
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7011
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7004
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7004

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