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

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

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

Structure
Zoomed Structure
  • Family: Asphodelaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
    • Subclass: Isofuranonaphthoquinone
Canonical Smiles OCc1occ2c1C(=O)c1c(C2=O)c(O)ccc1O
InChI InChI=1S/C13H8O6/c14-3-8-9-5(4-19-8)12(17)10-6(15)1-2-7(16)11(10)13(9)18/h1-2,4,14-16H,3H2
InChIKey VTNVITVPYSHXGH-UHFFFAOYSA-N
Formula C13H8O6
HBA 6
HBD 3
MW 260.2
Rotatable Bonds 1
TPSA 107.97
LogP 0.96
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.08
Exact Mass 260.03
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: 135453894
Nmrshiftdb2: 60063495

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 198.18 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
49.48
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.26
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.57
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.81
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.41
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
3.74
Rat (Acute)
2.47
Rat (Chronic Oral)
3.29
Fathead Minnow
4.06
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
420.46
Hydration Free Energy
-12.26
Log(D) at pH=7.4
1.06
Log(P)
2.02
Log S
-4.57
Log(Vapor Pressure)
-8.64
Melting Point
232.48
pKa Acid
5.54
pKa Basic
3.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9219
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9179
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8955
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8899
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8878
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8790
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8775
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8664
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8481
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8464
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.8386
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8374
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8338
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8331
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8258
Cytochrome P450 2D6 P10635 CP2D6_HUMAN Homo sapiens 3 0.8173
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8136
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8117
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8111
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8025
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7966
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7924
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7898
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7894
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7878
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7808
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7754
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7710
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7621
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7608
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7602
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7523
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7518
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7476
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7472
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7424
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7381
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7379
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7326
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7305
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7294
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7257
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7253
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7249
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7235
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7221
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7219
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7219
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7207
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7204
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7201
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7185
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7163
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7158
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7152
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7149
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7147
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7146
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7141
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7133
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7108
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7107
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7084
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7082
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7074
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7073
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7050
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7044
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7042
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7028
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7018

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