Compound Detail

CHEMBL66

(+)-TAXIFOLIN

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O=C1c2c(O)cc(O)cc2O[C@H](c2ccc(O)c(O)c2)[C@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL66
Name	(+)-TAXIFOLIN
Phase	Preclinical
Structure Type	MOL
InChI Key	CXQWRCVTCMQVQX-LSDHHAIUSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

304.2

MW (Da)

1.19

ALogP

HBA

HBD

127.5

PSA (Å²)

0.50

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C15H12O7
MW	304.25
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	2.30

Activity Summary

IC50 33 meas. best 5.99

EC50 7 meas. best 4.95

Ki 6 meas. best 7.5

Kd 1 meas. best 4.43

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	Ki	7.5	7.5	32.0	1
Carbonic anhydrase 12 CHEMBL3242	Ki	7.49	7.49	32.5	1
Carbonic anhydrase 7 CHEMBL2326	Ki	6.31	6.31	493.1	1
Unchecked CHEMBL612545	IC50	5.99	4.9057	1036.0	7
Pyruvate kinase PKM CHEMBL1075189	IC50	5.94	5.94	1160.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.85	5.235	1410.0	2
Macrophage metalloelastase CHEMBL4393	IC50	5.24	5.24	5750.0	1
Tyrosinase CHEMBL3318	Ki	5.07	4.765	8500.0	2
Carbonic anhydrase 4 CHEMBL3729	Ki	5.04	5.04	9098.2	1
No relevant target CHEMBL2362975	EC50	4.95	4.905	11300.0	2
Neutrophil CHEMBL613710	IC50	4.82	4.57	15300.0	4
Mast/stem cell growth factor receptor Kit CHEMBL1936	IC50	4.8	4.73	15700.0	2
72 kDa type IV collagenase CHEMBL333	IC50	4.65	4.65	22620.0	1
Tyrosinase CHEMBL3318	IC50	4.64	4.605	23000.0	2
Matrix metalloproteinase-9 CHEMBL321	IC50	4.5	4.5	32020.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	4.48	4.48	33000.0	1
Stromelysin-1 CHEMBL283	IC50	4.47	4.47	33910.0	1
No relevant target CHEMBL2362975	IC50	4.47	4.395	34000.0	2
Collagenase 3 CHEMBL280	IC50	4.46	4.46	34600.0	1
ATP-dependent translocase ABCB1 CHEMBL2573	Kd	4.43	4.43	37400.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	4.35	4.35	45000.0	1
Human immunodeficiency virus 1 CHEMBL378	IC50	4.35	4.35	45000.0	1
RAW264.7 CHEMBL612557	IC50	4.09	4.09	81600.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
KA	0.918	10'6L/mol	Agaricus bisporus
Ke	3070.0	nM	Homo sapiens
Ke	3820.0	nM	Homo sapiens
Ke	3280.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Receptor-type tyrosine-protein kinase FLT3	Ki	=	32.0	nM	7.5	Binding affinity to FLT3 (unknown origin) assessed as inhibition constant	38295689
Carbonic anhydrase 12	Ki	=	32.5	nM	7.49	Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a...	26498393
Carbonic anhydrase 7	Ki	=	493.1	nM	6.31	Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at...	26498393
Unchecked	IC50	=	1036.0	nM	5.99	Inhibition of beef heart mitochondrial NADH oxidase assessed per mg of protein	2959755
Pyruvate kinase PKM	IC50	=	1160.0	nM	5.94	Inhibition of recombinant PKM2 (unknown origin) Asp178, Asp177, Hie78, Lys367, A...	34726055
Pyruvate kinase PKM	IC50	=	1160.0	nM	5.94	Inhibition of PKM2 (unknown origin)	34355179
NON-PROTEIN TARGET	IC50	=	1410.0	nM	5.85	Antioxidant activity assessed as superoxide anion radical scavenging activity	17907781
Macrophage metalloelastase	IC50	=	5750.0	nM	5.24	Inhibition of human recombinant MMP12 catalytic domain incubated for 20 mins by ...	22658537
Unchecked	IC50	=	5900.0	nM	5.23	PUBCHEM_BIOASSAY: A biochemical assay using the ADP-Hunter methodology, purified...	-
Tyrosinase	Ki	=	8500.0	nM	5.07	Competitive type inhibition of monophenolase activity of mushroom tyrosinase ass...	30871862
Carbonic anhydrase 4	Ki	=	9098.2	nM	5.04	Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at...	26498393
Unchecked	IC50	=	9300.0	nM	5.03	Inhibition of Trichomonas vaginalis adenosine-guanosine preferring ribohydrolase...	26592812
No relevant target	EC50	=	11300.0	nM	4.95	Antioxidant activity assessed as H2O2 scavenging activity after 15 mins	25625705
Unchecked	IC50	=	12000.0	nM	4.92	Inhibition of NADPH oxidase in Homo sapiens (human) HUVEC cells	-
No relevant target	EC50	=	13900.0	nM	4.86	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins ...	26481151
Neutrophil	IC50	=	15300.0	nM	4.82	Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in...	23871908
Neutrophil	IC50	=	15500.0	nM	4.81	Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in...	23871908
Mast/stem cell growth factor receptor Kit	IC50	=	15700.0	nM	4.8	Inhibition of N-terminal GST-His-tagged c-KIT (544 to 976 amino acids) D816V mut...	26807861
Mast/stem cell growth factor receptor Kit	IC50	=	21900.0	nM	4.66	Inhibition of wild type His-tagged c-KIT (544 to 976 amino acids) (unknown origi...	26807861
72 kDa type IV collagenase	IC50	=	22620.0	nM	4.65	Inhibition of human recombinant MMP2 catalytic domain incubated for 20 mins by f...	22658537

Literature References

PubMed	DOI	Target Context	# Activities
30108751	10.1039/C6MD00496B	No relevant target	12
24963869	10.1021/np4009738	Unchecked	11
30871862	10.1016/j.bmc.2019.03.013	Tyrosinase	10
26517554	10.1021/acs.jnatprod.5b00075	ADMET	9
21824690	10.1016/j.ejmech.2011.07.031	HepG2	5
25625705	10.1021/np5007873	No relevant target	5
23871908	10.1016/j.ejmech.2013.06.019	Neutrophil	5
33530021	10.1016/j.bmc.2021.116043	Cytochrome c	5
26807861	10.1021/acs.jnatprod.5b00851	Mast/stem cell growth factor receptor Kit	4
20189399	10.1016/j.bmc.2010.01.046	Unchecked	4
12643908	10.1016/s0960-894x(03)00088-x	Mus musculus	4
32118424	10.1021/acs.jnatprod.9b01120	RAW264.7	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
30108751	10.1039/C6MD00496B	HEK293	4
19524443	10.1016/j.bmc.2009.05.059	Mus musculus	4
26592812	10.1016/j.bmcl.2015.10.030	Unchecked	3
19931462	10.1016/j.bmc.2009.10.063	Unchecked	3
26517554	10.1021/acs.jnatprod.5b00075	Unchecked	3
-	10.1016/S0960-894X(00)80422-9	Human immunodeficiency virus 1	3
19640715	10.1016/j.bmcl.2009.07.082	Unchecked	2

Data from ChEMBL 36 via Core Engine