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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
    • Subclass: Isofuranonaphthoquinone
Canonical Smiles O=C1c2cccc(c2C(=O)c2c1coc2C)O
InChI InChI=1S/C13H8O4/c1-6-10-8(5-17-6)12(15)7-3-2-4-9(14)11(7)13(10)16/h2-5,14H,1H3
InChIKey GBXTYRYFKWXLAP-UHFFFAOYSA-N
Formula C13H8O4
HBA 4
HBD 1
MW 228.2
Rotatable Bonds 0
TPSA 67.51
LogP 2.07
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.08
Exact Mass 228.04
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: 11390536
Nmrshiftdb2: 60063499

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 228.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.430
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.010
Plasma Protein Binding
45.38
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
Non-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
7.410
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.370
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.920
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.930
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
4.480
Rat (Acute)
2.700
Rat (Chronic Oral)
2.880
Fathead Minnow
4.330
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
376.510
Hydration Free Energy
-10.170
Log(D) at pH=7.4
2.020
Log(P)
3.19
Log S
-5.12
Log(Vapor Pressure)
-7.82
Melting Point
190.47
pKa Acid
5.38
pKa Basic
4.41
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 0.9632
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.9594
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9420
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9394
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.9375
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.9357
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.9326
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9237
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9234
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9178
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9169
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.9162
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9152
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.9151
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9016
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.9002
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8916
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8899
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8867
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8814
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8786
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8720
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8619
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8610
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8606
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8595
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8575
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8420
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8324
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8290
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8226
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8222
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.8181
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8169
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8151
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8102
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8033
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8033
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8010
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.8001
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7995
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7988
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7985
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7965
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7949
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.7937
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7899
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7841
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7829
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7779
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7776
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7771
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7765
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7728
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7691
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7678
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7671
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7660
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7656
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7655
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7651
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7638
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7614
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7608
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7577
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7576
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7575
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7550
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7548
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7539
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7524
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7519
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7507
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7503
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7494
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7451
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7445
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7440
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7437
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7419
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7414
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7410
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7408
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7398
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7397
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7397
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7393
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7390
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.7378
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7371
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7370
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7366
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7348
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7340
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7334
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7327
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7326
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7319
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7318
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7292
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7277
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7267
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7256
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7222
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7206
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7198
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7191
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7190
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7185
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7173
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7169
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7169
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7167
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7163
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7156
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7142
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7138
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7134
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7131
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7127
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7126
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7115
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7114
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7102
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7102
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7084
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7082
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7078
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7078
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7069
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7066
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7059
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7048
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7047
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7040
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7031
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7025
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7023
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7011
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7005
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7004

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