8-hydroxy-5-methoxy-1-methylnaphtho-[2,3-c]-furan-4,9-dione - Compound Card

8-hydroxy-5-methoxy-1-methylnaphtho-[2,3-c]-furan-4,9-dione

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8-hydroxy-5-methoxy-1-methylnaphtho-[2,3-c]-furan-4,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
    • Subclass: Isofuranonaphthoquinone
Canonical Smiles COc1ccc(c2c1C(=O)c1coc(c1C2=O)C)O
InChI InChI=1S/C14H10O5/c1-6-10-7(5-19-6)13(16)12-9(18-2)4-3-8(15)11(12)14(10)17/h3-5,15H,1-2H3
InChIKey QRJSQPCKVDNLNN-UHFFFAOYSA-N
Formula C14H10O5
HBA 5
HBD 1
MW 258.23
Rotatable Bonds 1
TPSA 76.74
LogP 2.08
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.14
Exact Mass 258.05
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: 11425395
Nmrshiftdb2: 70030866

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 258.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.380
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.890
Plasma Protein Binding
40.97
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
Substrate
CYP 2C9 Inhibitor
Non-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
6.250
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.380
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.030
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.580
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
4.660
Rat (Acute)
2.830
Rat (Chronic Oral)
2.810
Fathead Minnow
4.510
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
392.690
Hydration Free Energy
-10.340
Log(D) at pH=7.4
2.160
Log(P)
2.96
Log S
-5.38
Log(Vapor Pressure)
-7.16
Melting Point
191.13
pKa Acid
5.8
pKa Basic
4.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.9414
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9400
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.9230
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9183
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.9164
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9161
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9155
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.9145
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9072
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.9009
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.8986
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8958
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8939
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8936
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8867
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8839
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8836
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8789
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8768
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8714
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8661
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8659
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8500
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8454
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8397
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8395
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8387
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8302
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8228
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8189
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8180
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8178
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8117
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8090
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8032
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7969
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7962
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7945
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7934
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7926
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7896
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7884
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7849
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7830
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7815
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7812
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7779
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7766
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7718
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7708
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7705
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7699
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7695
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.7691
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7689
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7679
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7677
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7675
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7660
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7602
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7595
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7559
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7549
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7536
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7507
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7506
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7500
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7496
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7494
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7490
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7473
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7472
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7466
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7460
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7450
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7443
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7434
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7419
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7418
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7410
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7410
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7401
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7395
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7388
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7373
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7358
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7357
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7355
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7344
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.7339
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7334
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7330
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7328
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7324
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7321
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7290
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7253
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7242
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7229
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7204
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7202
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7200
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7194
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7193
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7173
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7166
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7166
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7162
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7155
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7142
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7123
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7121
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7112
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7088
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7085
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 2 0.7080
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7079
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7067
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7040
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7022
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7020
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7015
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7015
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7010
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7009
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7001

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