Laccaic acid D-methyl ester - Compound Card

Laccaic acid D-methyl ester

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Laccaic acid D-methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COC(=O)c1c(O)cc2c(c1C)C(=O)c1c(C2=O)cc(cc1O)O
InChI InChI=1S/C17H12O7/c1-6-12-9(5-11(20)13(6)17(23)24-2)15(21)8-3-7(18)4-10(19)14(8)16(12)22/h3-5,18-20H,1-2H3
InChIKey NBIBEHMMFJQZQW-UHFFFAOYSA-N
Formula C17H12O7
HBA 7
HBD 3
MW 328.28
Rotatable Bonds 1
TPSA 121.13
LogP 1.67
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 328.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe dawei Asphodelaceae Plantae 1331517
2 Aloe secundiflora Asphodelaceae Plantae 1593107
3 Aloe berhana Asphodelaceae Plantae 1593069
4 Aloe saponaria Asphodelaceae Plantae 1155789
5 Aloe graminicola Liliaceae Plantae 330741
6 Aloe species Liliaceae Plantae 117795

Showing of synonyms

  • Yenesew A, Ogur JA, et al. (1993). (R)-Prechrysophanol from Aloe graminicola.. Phytochemistry,1993,34(5),1442-1444. [View] [PubMed]
  • Dagne E, Casser I, et al. (1992). Aloechrysone, a dihydroanthracenone from Aloe berhana.. Phytochemistry,1992,31(5),1791-1793. [View] [PubMed]
  • Dagne E, Yenesew A, et al. (1994). Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species.. Phytochemistry,1994,35(2),401-406. [View] [PubMed]
  • Abdissa N, Induli M, et al. (2014). Cytotoxic quinones from the roots of Aloe dawei. Molecules,2014,19(3),3264-3273. [View] [PubMed]
  • Induli M, Cheloti M, et al. (2012). Naphthoquinones from the roots of Aloe secundiflora. Phytochemistry Letters,2012,5(3),506-509. [View] [PubMed]
  • Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
Pubchem: 7330511
Nmrshiftdb2: 70005005

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 328.28 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.860
Plasma Protein Binding
61.06
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.810
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.640
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.750
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.780
Micronucleos
Toxic
NR-AhR
Toxic
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
4.420
Rat (Acute)
2.560
Rat (Chronic Oral)
3.490
Fathead Minnow
4.250
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
472.740
Hydration Free Energy
-9.440
Log(D) at pH=7.4
2.720
Log(P)
3.76
Log S
-6.63
Log(Vapor Pressure)
-7.6
Melting Point
254.57
pKa Acid
8.18
pKa Basic
4.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9306
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9306
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9211
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9211
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9040
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9040
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8868
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8868
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8801
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8801
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8766
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8766
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8727
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8727
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8668
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8668
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8574
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8574
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8564
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8564
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8563
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8563
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8393
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8393
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8380
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8380
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8279
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8279
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8237
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8237
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8194
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8194
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8172
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8172
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8126
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8126
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8076
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8076
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8063
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8063
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8020
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8020
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8013
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8013
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8004
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8004
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7980
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7980
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7955
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7955
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7906
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7906
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7850
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7850
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7802
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7802
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7798
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7798
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7659
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7659
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7656
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7656
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7651
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7651
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7633
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7633
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7577
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7577
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7527
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7527
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7521
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7521
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7491
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7491
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7480
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7480
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7378
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7378
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7350
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7350
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7223
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7223
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7177
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7177
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7171
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7171
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7171
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7171
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7123
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7123
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7106
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7106
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7104
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7104
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7096
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7096
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7091
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7091
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 3 0.7079
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 3 0.7079
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7075
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7075
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7054
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7054
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7050
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7050
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7010
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7010

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