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

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

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5-hydroxy-3',4',7-trimethoxyspiro-{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 COc1cc(O)c2c(c1)OC[C@]1(C2=O)Cc2c1cc(c(c2)OC)OC
InChI InChI=1S/C19H18O6/c1-22-11-5-13(20)17-16(6-11)25-9-19(18(17)21)8-10-4-14(23-2)15(24-3)7-12(10)19/h4-7,20H,8-9H2,1-3H3/t19-/m1/s1
InChIKey GTARHKGCDCSIQV-LJQANCHMSA-N
Formula C19H18O6
HBA 6
HBD 1
MW 342.35
Rotatable Bonds 3
TPSA 74.22
LogP 2.49
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 342.11
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: 342.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.070
Plasma Protein Binding
69.37
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
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
10.250
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.390
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.460
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.640
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
1.050
Rat (Acute)
2.270
Rat (Chronic Oral)
2.250
Fathead Minnow
4.700
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
428.700
Hydration Free Energy
-8.160
Log(D) at pH=7.4
2.760
Log(P)
2.85
Log S
-4.96
Log(Vapor Pressure)
-7.33
Melting Point
184.76
pKa Acid
7.71
pKa Basic
3.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9694
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9535
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9514
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9320
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9275
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.9216
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.9170
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9165
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9102
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9042
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8973
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8968
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8834
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8784
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8653
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8642
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8572
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8562
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8508
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8491
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8473
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8467
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8390
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8285
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8235
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8225
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8197
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8179
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8170
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8143
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.8130
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.8084
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8015
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8007
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7949
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7948
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7942
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7941
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7941
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7906
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7895
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7848
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7833
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7825
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7821
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7820
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7806
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7784
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7781
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7760
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7742
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7742
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7741
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7738
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7699
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7676
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7659
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7648
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7623
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7619
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7618
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7577
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7576
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7557
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7556
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7535
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7519
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7507
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7500
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7494
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7491
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7481
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7477
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7475
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7472
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7455
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1 Q15750 TAB1_HUMAN Homo sapiens 3 0.7451
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7450
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7440
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7434
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7429
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7421
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7417
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7416
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7408
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7406
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7401
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7395
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7377
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7361
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7353
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7339
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7322
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7321
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7321
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7311
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7310
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7309
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7307
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7304
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7301
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7294
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7289
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7284
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7273
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7270
Transthyretin P02766 TTHY_HUMAN Homo sapiens 3 0.7256
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7240
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7237
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7230
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7212
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7206
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7199
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7199
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7182
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7181
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7172
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7166
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7160
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7153
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7140
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7137
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7135
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7134
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7124
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7118
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7112
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7111
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7108
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7108
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7105
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7097
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7084
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7083
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7082
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7080
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7079
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7058
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7048
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7040
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7032
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7005
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7004
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7002

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