Microdontin A - Compound Card

Microdontin A

Select a section from the left sidebar

Microdontin A

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthrone
Canonical Smiles OCc1cc(O)c2c(c1)[C@@H]([C@@H]1O[C@H](COC(=O)/C=C/c3ccc(cc3)O)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1
InChI InChI=1S/C30H28O11/c31-12-15-10-18-23(17-2-1-3-19(33)24(17)27(37)25(18)20(34)11-15)30-29(39)28(38)26(36)21(41-30)13-40-22(35)9-6-14-4-7-16(32)8-5-14/h1-11,21,23,26,28-34,36,38-39H,12-13H2/b9-6+/t21-,23+,26-,28+,29-,30+/m1/s1
InChIKey OWGCMMINSKNONQ-IWTSKDHTSA-N
Formula C30H28O11
HBA 11
HBD 7
MW 564.54
Rotatable Bonds 6
TPSA 194.21
LogP 1.08
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 564.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe percrassa Asphodelaceae Plantae 1593100
2 Aloe calidophila Asphodelaceae Plantae 1813110
3 Aloe microdonta Asphodelaceae Plantae 3161253

Showing of synonyms

  • Geremedhin G, Bisrat D, et al. (2014). Isolation, characterization and in vivo antimalarial evaluation of anthrones from the leaf latex of Aloe percrassa Todaro. Journal of Natural Remedies,2014,14(2),1-7. [View] [PubMed]
  • Abeje F, Bisrat D, et al. (2014). Phytochemistry and antileishmanial activity of the leaf latex of Aloe calidophila Reynolds.. Phytotherapy Research,2014,28(12),1801-1805. [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: 101629131
Nmrshiftdb2: 60054699

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)C(c(c34)cccc4)c5c(C3=O)cccc5

Level: 2

Mol. Weight: 564.54 g/mol

Structure

SMILES: O1CCCCC1C(c(c23)cccc3)c4c(C2=O)cccc4

Level: 1

Mol. Weight: 564.54 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 564.54 g/mol

Structure

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 564.54 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 564.54 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 564.54 g/mol

Anti-leishmanial
Anti-plasmodial

Absorption

Caco-2 (logPapp)
-7.0
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.1
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
87.92
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
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.85
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.9
Micronucleos
Toxic
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
-7165.15
Rat (Acute)
2.56
Rat (Chronic Oral)
4.12
Fathead Minnow
18.72
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
531.1
Hydration Free Energy
-3.15
Log(D) at pH=7.4
1.64
Log(P)
2.81
Log S
-4.2
Log(Vapor Pressure)
-11.24
Melting Point
210.18
pKa Acid
4.84
pKa Basic
6.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9751
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9751
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9290
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9290
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9142
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9142
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8503
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8503
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8487
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8487
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8462
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8462
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8381
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8381
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8374
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8374
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8274
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8274
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8215
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8215
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8207
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8207
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8184
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8184
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8054
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8054
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8007
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8007
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8003
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8003
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7978
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7978
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7961
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7961
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7900
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7900
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7887
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7887
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7675
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7675
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7649
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7649
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7635
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7635
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7587
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7587
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7571
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7571
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7556
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7556
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7550
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7550
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7547
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7547
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7532
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7532
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7520
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7520
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7518
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7518
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7517
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7517
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7503
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7503
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7487
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7487
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7486
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7486
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7480
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7480
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7466
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7466
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7461
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7461
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7418
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7418
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7395
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7395
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7378
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7378
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7337
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7337
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7322
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7322
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7308
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7308
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7294
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7294
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7284
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7284
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7273
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7273
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7270
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7270
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7263
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7263
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7261
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7261
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7248
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7248
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7232
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7232
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7220
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7220
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7212
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7212
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7207
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7207
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7197
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7197
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7169
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7169
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7148
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7148
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7146
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7146
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7136
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7136
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7134
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7134
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7129
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7129
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.7128
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.7128
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7099
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7099
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7096
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7096
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7095
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7095
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7090
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7090
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7062
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7062
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7054
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7054
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7052
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7052
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7050
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7050
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7042
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7042
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7034
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7034
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7032
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7032
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7020
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7020
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7013
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7013
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7005
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7005
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7002
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7002

Download SDF