5,8-dihydroxy-1-tigloylmethylnaphtho[2,3-c]furan-4,9-dione - Compound Card

5,8-dihydroxy-1-tigloylmethylnaphtho[2,3-c]furan-4,9-dione

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5,8-dihydroxy-1-tigloylmethylnaphtho[2,3-c]furan-4,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
    • Subclass: Isofuranonaphthoquinone
Canonical Smiles C/C=C(/C(=O)Cc1occ2c1C(=O)c1c(C2=O)c(O)ccc1O)\C
InChI InChI=1S/C18H14O6/c1-3-8(2)12(21)6-13-14-9(7-24-13)17(22)15-10(19)4-5-11(20)16(15)18(14)23/h3-5,7,19-20H,6H2,1-2H3/b8-3+
InChIKey QIQLLGATTLVZMP-FPYGCLRLSA-N
Formula C18H14O6
HBA 6
HBD 2
MW 326.3
Rotatable Bonds 3
TPSA 104.81
LogP 2.54
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 326.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine capitata Asphodelaceae Plantae 576756

Showing of synonyms

  • Bezabih M, Abegaz BM, et al. (2001). Antiplasmodial and Antioxidant Isofuranonaphthoquinones from the Roots of Bulbine capitata. Planta medica, 2001, 67(4), 340–344. [View]
Pubchem: 136913001

No compound-protein relationship available.

Structure

SMILES: c1occ(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 326.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.91
Plasma Protein Binding
56.42
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-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
5.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.76
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.8
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.39
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
3.87
Rat (Acute)
2.84
Rat (Chronic Oral)
3.24
Fathead Minnow
4.87
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
447.95
Hydration Free Energy
-10.93
Log(D) at pH=7.4
2.19
Log(P)
3.49
Log S
-6.55
Log(Vapor Pressure)
-8.81
Melting Point
206.92
pKa Acid
5.95
pKa Basic
3.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9407
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9336
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9231
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9214
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.9084
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9004
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8874
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8848
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8794
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8759
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8736
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8692
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8623
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8597
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8372
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8317
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8315
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8296
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8267
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8240
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8219
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8211
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8193
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8138
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8045
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7999
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7990
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7915
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7908
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7900
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7897
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7880
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7874
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7870
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7854
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7824
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7807
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7778
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7760
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7754
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7753
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7750
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7715
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7712
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7708
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7688
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7686
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7678
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7678
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7677
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7653
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7648
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7644
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7623
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7622
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7606
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7593
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7584
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7554
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7550
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7526
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7518
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7498
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7488
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7470
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7470
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7458
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7434
Putative secreted protein C9Z6T8 C9Z6T8_STRSW Streptomyces scabiei 4 0.7412
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7399
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7397
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7395
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7382
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7362
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7356
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7346
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7346
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7344
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7342
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 4 0.7336
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7336
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7333
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7328
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7323
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7317
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7311
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7301
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7292
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7289
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7285
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7276
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7274
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7266
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7262
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7241
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7232
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7216
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7215
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7206
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7206
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7199
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7192
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7191
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7175
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7165
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7154
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7144
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7142
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7141
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7135
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7129
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7119
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7117
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7112
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7101
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7097
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 5 0.7094
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7093
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7088
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7083
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7081
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 2 0.7071
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7061
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7058
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7033
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7027
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7024
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7018
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7018

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