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

1-acetoxymethyl-5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione

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1-acetoxymethyl-5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
    • Subclass: Isofuranonaphthoquinone
Canonical Smiles CC(=O)OCc1occ2c1C(=O)c1c(C2=O)c(O)ccc1O
InChI InChI=1S/C15H10O7/c1-6(16)21-5-10-11-7(4-22-10)14(19)12-8(17)2-3-9(18)13(12)15(11)20/h2-4,17-18H,5H2,1H3
InChIKey RKIYQYGTCGESFC-UHFFFAOYSA-N
Formula C15H10O7
HBA 7
HBD 2
MW 302.24
Rotatable Bonds 2
TPSA 114.04
LogP 1.53
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 302.04
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: 136658961
Nmrshiftdb2: 70030867

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 302.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
45.31
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
8.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.94
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.81
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
4.0
Rat (Acute)
2.67
Rat (Chronic Oral)
3.08
Fathead Minnow
4.35
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
432.26
Hydration Free Energy
-11.25
Log(D) at pH=7.4
1.73
Log(P)
2.73
Log S
-5.02
Log(Vapor Pressure)
-8.16
Melting Point
199.64
pKa Acid
5.52
pKa Basic
4.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9368
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9210
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9106
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9080
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9051
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8964
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8925
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8838
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8809
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8740
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8737
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8736
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8720
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8718
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8643
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8625
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8549
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8476
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8446
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8396
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8374
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8363
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8228
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8213
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8164
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8155
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8144
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8090
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8082
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8077
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 4 0.8007
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7985
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7932
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7931
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7877
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7870
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7868
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7836
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7784
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7750
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7739
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7736
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7723
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7710
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7699
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7682
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7652
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7652
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7642
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7620
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7617
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7617
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7607
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7607
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7590
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7580
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7541
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7539
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7515
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7500
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7488
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7485
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7480
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7473
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7449
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7444
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7443
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7410
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7382
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7375
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7374
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7345
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7344
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7340
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7338
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7325
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7317
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7306
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7255
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7252
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7251
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7247
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7246
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7245
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7242
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7241
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7235
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7224
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7220
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7217
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7216
Metallophosphoesterase MPPED2 B1WBP0 MPPD2_RAT Rattus norvegicus 3 0.7210
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7200
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7193
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7188
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7180
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7175
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7163
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7161
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.7148
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7143
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7139
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7138
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7135
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7128
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7126
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7123
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7119
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7116
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7116
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7112
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7109
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7105
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7101
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7093
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7089
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7086
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7071
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7065
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7058
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7056
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7047
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 2 0.7041
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7031
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 4 0.7027
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7024
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7015
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7008

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