Microphybenzimidazole - Compound Card

Microphybenzimidazole

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Microphybenzimidazole

Structure
Zoomed Structure
  • Family: Plantae - Thymelaeaceae
  • Kingdom: Plantae
  • Class: Benzimidazole
    • Subclass: Benzimidazole Glycoside
Canonical Smiles CCOC1[C@@H](O)CO[C@@H]([C@@H]1O)OC/C=C/c1nc2c([nH]1)cc(c(c2)OC)OC
InChI InChI=1S/C19H26N2O7/c1-4-26-18-13(22)10-28-19(17(18)23)27-7-5-6-16-20-11-8-14(24-2)15(25-3)9-12(11)21-16/h5-6,8-9,13,17-19,22-23H,4,7,10H2,1-3H3,(H,20,21)/b6-5+/t13-,17+,18?,19-/m0/s1
InChIKey SPRSDIPEWFIUIO-YHQFRHALSA-N
Formula C19H26N2O7
HBA 8
HBD 3
MW 394.42
Rotatable Bonds 8
TPSA 115.29
LogP 1.09
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 394.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Thymelaea microphylla Thymelaeaceae Plantae 224056

Showing of synonyms

  • Noman L, Oke-Altuntas F, et al. (2017). A novel benzimidazole and other constituents with antiproliferative and antioxidant properties from Thymelaea microphylla Coss. et Dur. Nat Prod Res,2017,(17),2032-2041. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC=Cc(n2)[nH]c(c23)cccc3

Level: 1

Mol. Weight: 394.42 g/mol

Structure

SMILES: n1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 394.42 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 394.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.98
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
39.46
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.42
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.87
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
-22.49
Rat (Acute)
1.93
Rat (Chronic Oral)
2.19
Fathead Minnow
5.36
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
479.15
Hydration Free Energy
-7.48
Log(D) at pH=7.4
2.18
Log(P)
0.51
Log S
-2.82
Log(Vapor Pressure)
-10.56
Melting Point
178.13
pKa Acid
9.6
pKa Basic
5.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9564
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9557
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9540
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9539
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9404
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9316
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9246
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9230
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9114
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9078
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.9073
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9049
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8997
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8984
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8971
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8969
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.8909
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.8858
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8813
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 4 0.8767
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8743
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8676
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8665
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8632
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8619
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8613
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8611
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8603
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8584
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8583
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8493
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8482
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8465
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8463
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8440
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.8355
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.8355
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8340
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 4 0.8328
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8313
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8229
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8204
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8203
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8202
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8190
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8172
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8151
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8088
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.8081
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8078
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.8067
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8060
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.8055
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8028
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8013
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7973
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7966
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7956
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7944
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7934
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7929
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7927
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7918
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7917
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7899
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7892
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7890
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7863
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7856
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7798
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7751
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7731
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7715
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7680
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7675
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7674
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7652
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7637
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7631
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7625
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7605
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7593
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7562
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7522
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7513
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7512
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7501
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7499
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7481
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7478
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7471
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7467
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7461
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7444
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7434
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7403
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7401
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7396
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7385
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7359
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7345
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7335
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7334
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7320
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7319
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7287
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7285
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7284
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 2 0.7284
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7282
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7258
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7257
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7256
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.7255
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7249
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7249
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7248
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7247
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7239
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7232
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7224
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7219
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7211
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7203
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7202
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 3 0.7192
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7187
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7180
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 3 0.7171
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7159
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7157
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7142
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7139
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7139
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7126
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7124
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7114
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7111
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 3 0.7108
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7103
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7091
Beta-1,4-galactosyltransferase 1 P08037 B4GT1_BOVIN Bos taurus 3 0.7088
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 3 0.7088
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7063
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7063
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7062
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7056
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7051
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7048
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7043
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7036
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7033
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7031
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7028
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7026
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7025
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7020
Ribosome biogenesis GTPase YqeH D0VWU7 D0VWU7_GEOSE Geobacillus stearothermophilus 3 0.7019
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7018

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