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

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

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(R)-3′,5,7-trihydroxy-4′-methoxyspiro [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 COc1cc2c(cc1O)C[C@@]12COc2c(C1=O)c(O)cc(c2)O
InChI InChI=1S/C17H14O6/c1-22-13-5-10-8(2-11(13)19)6-17(10)7-23-14-4-9(18)3-12(20)15(14)16(17)21/h2-5,18-20H,6-7H2,1H3/t17-/m0/s1
InChIKey CIUPXTYTXDYKRQ-KRWDZBQOSA-N
Formula C17H14O6
HBA 6
HBD 3
MW 314.29
Rotatable Bonds 1
TPSA 96.22
LogP 1.88
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 314.08
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: 122182400
Nmrshiftdb2: 70027587

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 314.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.020
Plasma Protein Binding
75.12
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
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
11.180
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.260
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.280
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.130
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
3.220
Rat (Acute)
2.190
Rat (Chronic Oral)
2.990
Fathead Minnow
4.290
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
444.640
Hydration Free Energy
-10.020
Log(D) at pH=7.4
2.340
Log(P)
2.07
Log S
-5.49
Log(Vapor Pressure)
-7.76
Melting Point
251.79
pKa Acid
6.34
pKa Basic
4.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9564
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9505
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.9461
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9434
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9376
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9364
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.9329
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.9290
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9216
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.9200
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9180
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9025
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9019
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.8884
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8879
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8814
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8809
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8779
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8764
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8739
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8718
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8689
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8688
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8623
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8611
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8548
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8527
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.8523
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.8517
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8491
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8467
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8379
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8359
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.8338
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8308
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8294
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8201
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.8159
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8157
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8156
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8133
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8112
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8107
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8106
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8087
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8048
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8044
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8043
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8034
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.8015
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8002
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7996
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7986
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7977
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7977
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7974
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7935
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7931
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7919
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7899
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7895
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7887
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7886
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7883
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7869
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7857
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7835
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7823
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7814
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7805
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7783
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7782
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7757
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7757
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7677
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7653
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7649
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7646
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7643
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7629
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7623
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7596
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 3 0.7593
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7586
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7586
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7580
Ephrin type-A receptor 4 Q03137 EPHA4_MOUSE Mus musculus 4 0.7568
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7565
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7538
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7536
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7532
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7532
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7531
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7524
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7523
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7510
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7507
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7485
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7463
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7440
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7436
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7434
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7425
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7414
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7414
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7405
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7385
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7383
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7376
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7376
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7349
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7344
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7282
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7269
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7267
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7253
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7244
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7238
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7219
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7218
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7214
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7203
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7202
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7182
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7175
Pyruvate kinase PKM P14618 KPYM_HUMAN Homo sapiens 3 0.7175
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7167
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7166
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7154
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7110
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7105
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7101
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7087
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7087
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7086
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7084
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7081
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7078
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7077
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7076
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7071
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7064
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7051
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7051
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7039
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7037
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7018
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7011
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7002

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