5′,6′-dihydroxy- 2′-(4-hydroxy-2-oxo-2H-pyran-6-yl)-5-[(E)-2-(4-hydroxy-phenyl) ethenyl]-3H-spiro[furan-2,1′-inden]-3-one - Compound Card

5′,6′-dihydroxy- 2′-(4-hydroxy-2-oxo-2H-pyran-6-yl)-5-[(E)-2-(4-hydroxy-phenyl) ethenyl]-3H-spiro[furan-2,1′-inden]-3-one

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5′,6′-dihydroxy- 2′-(4-hydroxy-2-oxo-2H-pyran-6-yl)-5-[(E)-2-(4-hydroxy-phenyl) ethenyl]-3H-spiro[furan-2,1′-inden]-3-one

Structure
Zoomed Structure
  • Family: Fungi - Hymenochaetaceae
  • Kingdom: Fungi
  • Class: Phenolic
    • Subclass: Oxygenated Spiro [Furan-2,1′-Indine]-3-One Derivative
Canonical Smiles Oc1cc(=O)oc(c1)C1=Cc2c(C31OC(=CC3=O)/C=C/c1ccc(c(c1)O)O)cc(c(c2)O)O
InChI InChI=1S/C25H16O9/c26-14-8-22(33-24(32)9-14)17-6-13-7-20(29)21(30)11-16(13)25(17)23(31)10-15(34-25)3-1-12-2-4-18(27)19(28)5-12/h1-11,26-30H/b3-1+
InChIKey RDVPXUNRTSAXLN-HNQUOIGGSA-N
Formula C25H16O9
HBA 9
HBD 5
MW 460.39
Rotatable Bonds 3
TPSA 157.66
LogP 3.11
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.04
Exact Mass 460.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sanghuangporus sp. Hymenochaetaceae Fungi 2267874

Showing of synonyms

  • Chepkirui C, Cheng T, et al. (2018). An unprecedented spiro [furan-2,1’-indene]-3-one derivative and other nematicidal and antimicrobial metabolites from Sanghuangporus sp. (Hymenochaetaceae, Basidiomycota) collected in Kenya. Phytochemistry Letters,2018,25,141-146.. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(O2)=CC(=O)C23c4c(cccc4)C=C3c5cccc(=O)o5

Level: 2

Mol. Weight: 460.39 g/mol

Structure

SMILES: c1ccccc1C=CC(O2)=CC(=O)C23c4c(C=C3)cccc4

Level: 1

Mol. Weight: 460.39 g/mol

Structure

SMILES: O1C=CC(=O)C12c3c(cccc3)C=C2c4cccc(=O)o4

Level: 1

Mol. Weight: 460.39 g/mol

Structure

SMILES: O1C=CC(=O)C12c3c(C=C2)cccc3

Level: 0

Mol. Weight: 460.39 g/mol

Structure

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 460.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 460.39 g/mol

Antimicrobial
Nematicidal

Absorption

Caco-2 (logPapp)
-6.53
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.08
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.1
Plasma Protein Binding
70.05
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
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
9.69
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.31
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
-279.96
Rat (Acute)
2.43
Rat (Chronic Oral)
3.12
Fathead Minnow
5.75
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
627.42
Hydration Free Energy
-3.5
Log(D) at pH=7.4
1.45
Log(P)
1.88
Log S
-4.77
Log(Vapor Pressure)
-12.99
Melting Point
370.28
pKa Acid
6.62
pKa Basic
5.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9536
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9536
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9356
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9356
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9038
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9038
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8867
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8867
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8857
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8857
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8751
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8751
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8727
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8727
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8679
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8679
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8626
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8626
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8578
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8578
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8521
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8521
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8457
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8457
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8444
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8444
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8396
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8396
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8366
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8366
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8331
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8331
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8314
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8314
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.8219
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.8219
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8182
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8182
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8134
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8134
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8074
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.8026
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.8026
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8022
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8022
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8003
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8003
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7958
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7958
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7911
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7911
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7908
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7908
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7883
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7883
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7875
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7875
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7823
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7823
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7806
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7806
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7777
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7777
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7691
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7691
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7657
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7657
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7643
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7643
Chromosome-associated kinesin KIF4 P33174 KIF4_MOUSE Mus musculus 3 0.7630
Chromosome-associated kinesin KIF4 P33174 KIF4_MOUSE Mus musculus 3 0.7630
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7619
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7619
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7591
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7591
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7521
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7521
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7504
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7504
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7495
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7495
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7493
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7493
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7490
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7490
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7405
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7405
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7378
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7378
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7319
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7319
Decapping and exoribonuclease protein O70348 DXO_MOUSE Mus musculus 3 0.7286
Decapping and exoribonuclease protein O70348 DXO_MOUSE Mus musculus 3 0.7286
Cyclic GMP-AMP synthase Q8C6L5 CGAS_MOUSE Mus musculus 3 0.7245
Cyclic GMP-AMP synthase Q8C6L5 CGAS_MOUSE Mus musculus 3 0.7245
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7242
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7242
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7240
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7240
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7232
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7232
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7222
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7222
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7158
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7158
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7151
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7151
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7148
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7148
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7136
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7136
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7127
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7127
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7126
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7126
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7125
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7125
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7122
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7122
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7114
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7114
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7106
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7106
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7094
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7094
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7072
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7072
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7065
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7065
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7062
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7062
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7058
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7058
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7055
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7055
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7054
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7054
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7048
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7048
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7032
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7032
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7025
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7025
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7022
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7022
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7008
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7008

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