Microdontin B - Compound Card

Microdontin B

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Microdontin B

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/C=C/c3ccc(cc3)O)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1
InChI InChI=1S/C30H30O10/c31-13-16-11-19-23(18-4-1-5-20(33)24(18)27(36)25(19)21(34)12-16)30-29(38)28(37)26(35)22(40-30)14-39-10-2-3-15-6-8-17(32)9-7-15/h1-9,11-12,22-23,26,28-35,37-38H,10,13-14H2/b3-2+/t22-,23-,26-,28+,29-,30+/m1/s1
InChIKey DDCAYMMIVGRVHF-QTTNIMKZSA-N
Formula C30H30O10
HBA 10
HBD 7
MW 550.56
Rotatable Bonds 7
TPSA 177.14
LogP 1.55
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 550.18
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe percrassa Asphodelaceae Plantae 1593100
2 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]
  • 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: 101629132
Nmrshiftdb2: 60054698

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CCOCC2CCCC(O2)C(c(c34)cccc4)c5c(C3=O)cccc5

Level: 2

Mol. Weight: 550.56 g/mol

Structure

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

Level: 1

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1ccccc1C=CCOCC2CCCCO2

Level: 1

Mol. Weight: 550.56 g/mol

Structure

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

Level: 0

Mol. Weight: 550.56 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 550.56 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-6.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.3
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
2.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
86.61
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
12.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.6
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.64
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
-4888.43
Rat (Acute)
2.59
Rat (Chronic Oral)
4.28
Fathead Minnow
14.61
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
525.86
Hydration Free Energy
-3.13
Log(D) at pH=7.4
1.67
Log(P)
2.82
Log S
-3.8
Log(Vapor Pressure)
-9.66
Melting Point
201.92
pKa Acid
5.46
pKa Basic
6.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9226
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9226
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.9091
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.9091
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8964
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8964
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8902
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8902
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8836
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8836
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8718
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8718
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8521
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8521
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8353
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8353
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8163
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8163
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8094
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8094
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7971
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7971
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7815
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7815
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7793
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7793
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7712
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7712
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7708
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7708
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7617
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7617
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7601
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7601
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7594
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7594
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7578
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7578
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7578
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7578
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7499
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7499
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7495
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7495
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7462
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7462
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7459
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7459
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7449
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7449
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7444
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7444
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7432
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7432
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7428
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7428
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 3 0.7422
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 3 0.7422
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7416
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7416
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7399
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7399
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7372
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7372
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7365
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7365
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7288
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7288
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7273
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7273
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7273
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7273
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7269
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7269
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7248
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7248
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7239
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7239
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7229
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7229
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7197
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7197
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7182
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7182
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7182
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7182
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7138
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7138
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7136
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7136
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7134
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7134
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7095
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7095
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7087
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7087
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7061
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7061
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7054
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7054
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7043
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7043
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7037
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7037
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7029
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7029
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7028
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7028

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