5,7-dihydroxy-3', 4'-dimethoxyspiro-{2H-1-benzopyran-7'-bicyclo[4.2.0]octa[1,3,5]-trien}-4-one - Compound Card

5,7-dihydroxy-3', 4'-dimethoxyspiro-{2H-1-benzopyran-7'-bicyclo[4.2.0]octa[1,3,5]-trien}-4-one

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5,7-dihydroxy-3', 4'-dimethoxyspiro-{2H-1-benzopyran-7'-bicyclo[4.2.0]octa[1,3,5]-trien}-4-one

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Homoisoflavonoid
Canonical Smiles COc1cc2C[C@]3(c2cc1OC)COc1c(C3=O)c(O)cc(c1)O
InChI InChI=1S/C18H16O6/c1-22-13-3-9-7-18(11(9)6-14(13)23-2)8-24-15-5-10(19)4-12(20)16(15)17(18)21/h3-6,19-20H,7-8H2,1-2H3/t18-/m1/s1
InChIKey MKPGLCWEMPNQKG-GOSISDBHSA-N
Formula C18H16O6
HBA 6
HBD 2
MW 328.32
Rotatable Bonds 2
TPSA 85.22
LogP 2.18
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 328.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ledebouria graminifolia Hyacinthaceae Plantae 2826844

Showing of synonyms

  • Mutanyatta J, Matapa BG, et al. (2003). Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids. Phytochemistry, 2003, 62(5), 797–804. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2)c1C23C(=O)c4c(OC3)cccc4

Level: 0

Mol. Weight: 328.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.800
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.090
Plasma Protein Binding
74.8
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.500
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.530
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.000
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.470
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
Toxic
T. Pyriformis
2.560
Rat (Acute)
2.030
Rat (Chronic Oral)
2.750
Fathead Minnow
4.570
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
435.810
Hydration Free Energy
-9.500
Log(D) at pH=7.4
2.480
Log(P)
2.46
Log S
-5.68
Log(Vapor Pressure)
-7.6
Melting Point
215.93
pKa Acid
7.11
pKa Basic
4.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9527
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9507
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9478
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9368
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9310
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9259
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9236
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9225
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.9199
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9136
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.9092
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.9068
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9063
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.9058
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8998
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8969
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8950
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8884
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.8851
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8837
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8794
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8787
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8740
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8557
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8550
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8423
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8420
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8406
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8369
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8351
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8337
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8320
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8283
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.8249
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8249
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8240
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8206
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8172
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8124
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.8122
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8120
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8100
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8072
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8048
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7993
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7928
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7861
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7820
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7812
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7798
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7793
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7786
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7779
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7740
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7727
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7716
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7714
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7696
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7675
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7665
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7663
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7654
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7635
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7607
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7585
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7582
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7578
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7577
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7561
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7486
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7481
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7477
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7473
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7462
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7446
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7435
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7434
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7430
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7424
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7402
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7396
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7378
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7378
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7374
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7373
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7373
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7369
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7351
Ephrin type-A receptor 4 Q03137 EPHA4_MOUSE Mus musculus 4 0.7343
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7326
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7314
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7312
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7310
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7309
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7309
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7307
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7297
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7296
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7292
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7285
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7280
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7270
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7264
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7251
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7241
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7220
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7210
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7198
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7182
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7180
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7178
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7176
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7175
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7167
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7161
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7159
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7155
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7145
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7139
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7139
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7137
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7124
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7123
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7113
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7107
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7106
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7098
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7095
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7091
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7088
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7084
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7079
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7078
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7068
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7065
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7064
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7060
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7058
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7057
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7048
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7042
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7042
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7038
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7036
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7031
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7030
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7022
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7016
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7014
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7012
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7009
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7006
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7005

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