(R)-3′,5-dihydroxy-4′,7-dimethoxyspiro [2H-1-benzopyran-3(4H),7′-bicyclo[4.2.0]-octa[1,3,5]-trien]-4-one - Compound Card

(R)-3′,5-dihydroxy-4′,7-dimethoxyspiro [2H-1-benzopyran-3(4H),7′-bicyclo[4.2.0]-octa[1,3,5]-trien]-4-one

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(R)-3′,5-dihydroxy-4′,7-dimethoxyspiro [2H-1-benzopyran-3(4H),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)O)OC
InChI InChI=1S/C18H16O6/c1-22-10-4-13(20)16-15(5-10)24-8-18(17(16)21)7-9-3-12(19)14(23-2)6-11(9)18/h3-6,19-20H,7-8H2,1-2H3/t18-/m0/s1
InChIKey ZUCALEAIJCKIMQ-SFHVURJKSA-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 Drimiopsis maculata, Eucomis schiffii, Urginea epigea, Drimia altissima Hyacinthaceae Plantae —

Showing of synonyms

  • Fusi F, Ferrara A, et al. (2008). Vascular myorelaxing activity of isolates from South African Hyacinthaceae partly mediated by activation of soluble guanylyl cyclase in rat aortic ring preparations. Journal of pharmacy and pharmacology, 2008, 60(4), 489–497. [View]
Pubchem: 162984745
Nmrshiftdb2: 70027586

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)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.070
Plasma Protein Binding
68.81
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
11.410
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.190
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.650
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.140
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
Safe
T. Pyriformis
2.370
Rat (Acute)
2.040
Rat (Chronic Oral)
2.580
Fathead Minnow
4.500
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
428.850
Hydration Free Energy
-8.140
Log(D) at pH=7.4
2.480
Log(P)
2.45
Log S
-5.18
Log(Vapor Pressure)
-7.72
Melting Point
211.19
pKa Acid
7.56
pKa Basic
3.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9564
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9563
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.9547
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9521
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9449
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9166
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9090
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9065
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8919
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8847
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8839
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8803
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8760
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8756
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8728
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8709
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8707
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8665
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8619
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8607
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8562
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8547
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8528
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8487
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8434
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8418
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8401
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8380
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8380
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8376
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8368
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8332
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.8311
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8268
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8232
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8208
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8205
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8188
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8185
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8173
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8173
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8171
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8151
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8144
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.8118
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8115
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8115
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8106
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.8093
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8083
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8083
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8071
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8051
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8046
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7961
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7945
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7931
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7931
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7926
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7924
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7911
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7902
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7859
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7849
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7842
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7838
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7829
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7817
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7798
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7785
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7785
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7783
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7782
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7733
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7702
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7699
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7694
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7688
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7675
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7668
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7637
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7617
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7610
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7607
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7600
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7585
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7584
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7558
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7552
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7549
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7549
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7531
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7531
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7515
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7492
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7488
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7485
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7482
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7478
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7448
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7430
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7414
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7396
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7395
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7389
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7374
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7369
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7364
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7362
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7361
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7353
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7349
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7348
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7342
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7331
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7328
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7305
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7293
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7289
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7289
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7287
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7285
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7273
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7248
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7237
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7223
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7219
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7198
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7180
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 3 0.7179
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7171
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7170
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7159
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7159
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7155
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7145
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7141
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7112
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7109
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7098
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7089
Beta-adrenergic receptor kinase 1 P25098 ARBK1_HUMAN Homo sapiens 3 0.7088
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7086
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7086
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7081
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7075
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7070
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7061
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7040
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7040
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7030
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7021
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7005
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7003
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7000

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