(2R,3R)-2,5-diacetoxy-7-methoxyspiro-[2H-1-benzopyran-3(4H),5'(6'H)-cyclobuta-[f][1,3]-benzodioxol]-4-one - Compound Card

(2R,3R)-2,5-diacetoxy-7-methoxyspiro-[2H-1-benzopyran-3(4H),5'(6'H)-cyclobuta-[f][1,3]-benzodioxol]-4-one

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(2R,3R)-2,5-diacetoxy-7-methoxyspiro-[2H-1-benzopyran-3(4H),5'(6'H)-cyclobuta-[f][1,3]-benzodioxol]-4-one

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Homoisoflavonoid
Canonical Smiles COc1cc2O[C@@H](OC(=O)C)[C@@]3(C(=O)c2c(c1)OC(=O)C)Cc1c3cc2c(c1)COC2
InChI InChI=1S/C23H20O8/c1-11(24)29-18-6-16(27-3)7-19-20(18)21(26)23(22(31-19)30-12(2)25)8-13-4-14-9-28-10-15(14)5-17(13)23/h4-7,22H,8-10H2,1-3H3/t22-,23+/m1/s1
InChIKey KJEFOELBVBFVNU-PKTZIBPZSA-N
Formula C23H20O8
HBA 8
HBD 0
MW 424.41
Rotatable Bonds 3
TPSA 97.36
LogP 2.61
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 424.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ledebouria ovatifolia Hyacinthaceae Plantae 1069013

Showing of synonyms

  • Waller CP, Thumser AE, et al. (2013). COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae). Phytochemistry, 2013, 95, 284–290. [View]
Pubchem: 73212713

No compound-protein relationship available.

Structure

SMILES: C1OCc(c2)c1cc(C3)c2C34C(=O)c5c(OC4)cccc5

Level: 0

Mol. Weight: 424.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.550
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
78.53
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.990
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.150
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.660
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.150
Micronucleos
Toxic
NR-AhR
Safe
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
-59.340
Rat (Acute)
3.210
Rat (Chronic Oral)
2.330
Fathead Minnow
5.230
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
476.620
Hydration Free Energy
-3.920
Log(D) at pH=7.4
2.500
Log(P)
2.29
Log S
-5.24
Log(Vapor Pressure)
-8.41
Melting Point
206.55
pKa Acid
8.67
pKa Basic
3.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9401
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9390
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.9368
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8857
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8786
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8768
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8672
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8669
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8473
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8473
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8472
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8327
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8320
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8288
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8247
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8213
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8181
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8180
Pyruvate kinase PKM P14618 KPYM_HUMAN Homo sapiens 3 0.8105
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8055
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8024
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7979
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7841
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7832
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7750
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7745
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7727
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7719
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7707
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7689
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7676
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7662
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7657
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7616
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7572
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7545
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7502
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7493
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7480
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7480
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7444
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7430
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7409
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7405
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7405
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 3 0.7393
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7388
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7378
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7328
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.7320
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7317
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7299
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7297
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7235
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7228
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7215
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7206
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7203
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7197
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7197
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7191
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7178
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7139
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7133
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7091
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7086
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7080
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7075
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7071
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7070
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7045
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7038
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7013

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