jiosephlee/chembl-endpoint-pair-clean-labels huggingface dataset:
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Cytotoxicity against human HepG2 cells after 72 hrs by MTT assay
- Assay organism: Homo sapiens
- Assay cell type: HepG2
- Target name: HepG2
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CC(C)C[C@H](NC(=O)CC(NC(=O)c1ccc2ccccc2c1)c1cccc(F)c1)B(O)O
- Properties:
- ChEMBL ID: CHEMBL1632677
- Molecule type: Small molecule
- Molecular weight: 450.32
- Heavy atoms: 33
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 4
- TPSA: 98.66
- LogP: 3.38
- Rotatable bonds: 9
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.28
- QED: 0.38

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 5.16
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 6990; units nM; pChEMBL 5.16

## Query Molecule B
- Canonical SMILES: CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)c1cnccn1)B(O)O
- Properties:
- ChEMBL ID: CHEMBL325041
- Preferred name: BORTEZOMIB
- Molecule type: Small molecule
- Max clinical phase: 3
- Molecular weight: 384.25
- Heavy atoms: 28
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 6
- TPSA: 124.44
- LogP: 0.36
- Rotatable bonds: 9
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.37
- QED: 0.46

## Molecule Similarity
- Weighted Tanimoto: 0.35

Answer: 7.6
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Antiviral activity against pseudovirus HIV-1 HXB-2 subtype A pseudotyped Env 1006_11.C3.1601 infected in human U87.CD4.CXCR4 cells assessed as reduction in viral infection measured after 3 days by luciferase based assay
- Assay organism: Human immunodeficiency virus 1
- Assay cell type: U87.CD4.CXCR4
- Target name: Human immunodeficiency virus 1
- Target type: ORGANISM
- Target organism: Human immunodeficiency virus 1

## Reference Molecule A
- Canonical SMILES: NC[C@@H](NC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)[nH]1)c1ncc(CO)s1
- Properties:
- ChEMBL ID: CHEMBL4547005
- Molecule type: Unknown
- Molecular weight: 410.42
- Heavy atoms: 28
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 5
- TPSA: 104.03
- LogP: 3.08
- Rotatable bonds: 6
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.22
- QED: 0.5

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 6.24
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 580; units nM; pChEMBL 6.24

## Query Molecule B
- Canonical SMILES: NC[C@H](NC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2F)[nH]1)c1nc(CCO)cs1
- Properties:
- ChEMBL ID: CHEMBL5278363
- Molecular weight: 442.44
- Heavy atoms: 30
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 5
- TPSA: 104.03
- LogP: 3.26
- Rotatable bonds: 7
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.26
- QED: 0.42

## Molecule Similarity
- Weighted Tanimoto: 0.53

Answer: 6.87
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Agonist activity at human TRPV1 channel expressed in human HEK293 cells assessed as elevation in intracellular calcium flux
- Assay organism: Homo sapiens
- Assay cell type: HEK293
- Target name: Transient receptor potential cation channel subfamily V member 1
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CC(C)Cn1nnc(Cc2ccc(-c3ccccc3)cc2)n1
- Properties:
- ChEMBL ID: CHEMBL255904
- Molecule type: Small molecule
- Molecular weight: 292.39
- Heavy atoms: 22
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 3
- TPSA: 43.6
- LogP: 3.59
- Rotatable bonds: 5
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.28
- QED: 0.72

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 5
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 10000; units nM; pChEMBL 5

## Query Molecule B
- Canonical SMILES: COC(=O)Cn1nnnc1CNC(=O)c1ccc(-c2ccccc2)cc1
- Properties:
- ChEMBL ID: CHEMBL257548
- Molecule type: Small molecule
- Molecular weight: 351.37
- Heavy atoms: 26
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 6
- TPSA: 99
- LogP: 1.44
- Rotatable bonds: 6
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.17
- QED: 0.67

## Molecule Similarity
- Weighted Tanimoto: 0.29

Answer: 4.53
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of PFKFB3 in human A549 cells assessed as decrease in lactate secretion after 4 hrs
- Assay organism: Homo sapiens
- Assay cell type: A549
- Target name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CC(C)Cn1cc(C#N)c2cc(Sc3ccc(NC(=O)[C@@H]4CCCN4)cc3)ccc21
- Properties:
- ChEMBL ID: CHEMBL3421734
- Molecule type: Small molecule
- Molecular weight: 418.57
- Heavy atoms: 30
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 4
- TPSA: 69.85
- LogP: 5.01
- Rotatable bonds: 6
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.33
- QED: 0.59

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.85
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 14000; units nM; pChEMBL 4.85

## Query Molecule B
- Canonical SMILES: CC(C)Cn1c(N)c(C#N)c2cc(Oc3ccc(NC(=O)CN)cc3)ccc21
- Properties:
- ChEMBL ID: CHEMBL3422657
- Molecule type: Small molecule
- Molecular weight: 377.45
- Heavy atoms: 28
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 5
- TPSA: 119.09
- LogP: 3.44
- Rotatable bonds: 6
- Ring count: 3
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.24
- QED: 0.61

## Molecule Similarity
- Weighted Tanimoto: 0.37

Answer: 4.79
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibitory concentration against MMP-1
- Assay organism: Homo sapiens
- Target name: Interstitial collagenase
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1c(Br)ccc2oc(C(=O)Nc3ccc(-c4ccc(S(=O)(=O)N[C@H](C(=O)O)C(C)C)cc4)cc3)c(C)c12
- Properties:
- ChEMBL ID: CHEMBL198262
- Molecule type: Small molecule
- Molecular weight: 615.5
- Heavy atoms: 39
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 6
- TPSA: 134.94
- LogP: 5.82
- Rotatable bonds: 9
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.21
- QED: 0.22

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 4.52
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 30000; units nM; pChEMBL 4.52

## Query Molecule B
- Canonical SMILES: CCc1ccc2oc(C(=O)Nc3ccc(-c4ccc(S(=O)(=O)N[C@H](C(=O)O)C(C)C)cc4)cc3)c(C)c2c1OC
- Properties:
- ChEMBL ID: CHEMBL194377
- Molecule type: Small molecule
- Molecular weight: 564.66
- Heavy atoms: 40
- Hydrogen bond donors: 3
- Hydrogen bond acceptors: 6
- TPSA: 134.94
- LogP: 5.62
- Rotatable bonds: 10
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.27
- QED: 0.23

## Molecule Similarity
- Weighted Tanimoto: 0.81

Answer: 4.55
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Antitrypanosomal activity against Trypanosoma cruzi MHOM/Pe/2011/Arequipa DTU 5 trypamastigotes infected in Balb/c mouse assessed as reduction in splenomegaly at 100 mg/kg, po once daily for 5 consecutive days starting from day 75 post infection measured on day 127 post infection relative to control
- Assay organism: Trypanosoma cruzi
- Target name: Trypanosoma cruzi
- Target type: ORGANISM
- Target organism: Trypanosoma cruzi

## Reference Molecule A
- Canonical SMILES: COc1ccc(C(=O)CCN2CCN(c3ccc([N+](=O)[O-])cc3)CC2)cc1
- Properties:
- ChEMBL ID: CHEMBL4128846
- Molecule type: Small molecule
- Molecular weight: 369.42
- Heavy atoms: 27
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 6
- TPSA: 75.92
- LogP: 3
- Rotatable bonds: 7
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.35
- QED: 0.42

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 1
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Activity; comment Active

## Query Molecule B
- Canonical SMILES: COc1ccc(C(=O)CCN2CCN(c3ccc(F)cc3)CC2)cc1
- Properties:
- ChEMBL ID: CHEMBL4129006
- Molecule type: Small molecule
- Molecular weight: 342.41
- Heavy atoms: 25
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 4
- TPSA: 32.78
- LogP: 3.23
- Rotatable bonds: 6
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.35
- QED: 0.75

## Molecule Similarity
- Weighted Tanimoto: 0.71

Answer: 1
## Endpoint to Predict
- Endpoint scope: target
- Measurement type: NE
- Label type: binary
- Binary semantics: activity
- Target name: P2Y purinoceptor 1
- Target type: SINGLE PROTEIN
- Target organism: Meleagris gallopavo

## Reference Molecule A
- Canonical SMILES: Nc1ncnc2c1ncn2[C@H]1[C@H](O)[C@H](O)[C@@]2(COP(=O)(O)O)C[C@H]12
- Properties:
- ChEMBL ID: CHEMBL2367747
- Molecule type: Small molecule
- Molecular weight: 357.26
- Heavy atoms: 24
- Hydrogen bond donors: 5
- Hydrogen bond acceptors: 8
- TPSA: 176.84
- LogP: -1.2
- Rotatable bonds: 4
- Ring count: 4
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.58
- QED: 0.42

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 0
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type NE; comment Not Active

## Query Molecule B
- Canonical SMILES: CNc1nc(Cl)nc2c1ncn2CC(=O)N(CCOP(=O)(O)O)CCOP(=O)(O)O
- Properties:
- ChEMBL ID: CHEMBL350108
- Molecule type: Small molecule
- Molecular weight: 488.72
- Heavy atoms: 30
- Hydrogen bond donors: 5
- Hydrogen bond acceptors: 9
- TPSA: 209.46
- LogP: -0.43
- Rotatable bonds: 11
- Ring count: 2
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.5
- QED: 0.2

## Molecule Similarity
- Weighted Tanimoto: 0.27

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Induction of apoptosis in human A375 cells expressing p53 wild type assessed as increase release of cytochrome c from mitochondria to cytosol at 0.5 uM after 24 hrs by immunofluorescence analysis
- Assay organism: Homo sapiens
- Assay cell type: A-375
- Target name: A-375
- Target type: CELL-LINE
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: COc1cc2c(cc1OCCCCCOc1cc(OC)c(OC)c(OC)c1)N=C[C@@H]1CCCN1C2=O
- Properties:
- ChEMBL ID: CHEMBL3765230
- Molecule type: Small molecule
- Molecular weight: 498.58
- Heavy atoms: 36
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 8
- TPSA: 88.05
- LogP: 4.67
- Rotatable bonds: 12
- Ring count: 4
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.48
- QED: 0.39

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 1
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Activity; comment Active

## Query Molecule B
- Canonical SMILES: COc1cc2c(cc1OCCCCOc1cc(OC)c(OC)c(OC)c1)N=C[C@@H]1CCCN1C2=O
- Properties:
- ChEMBL ID: CHEMBL3764892
- Molecule type: Small molecule
- Molecular weight: 484.55
- Heavy atoms: 35
- Hydrogen bond donors: 0
- Hydrogen bond acceptors: 8
- TPSA: 88.05
- LogP: 4.28
- Rotatable bonds: 11
- Ring count: 4
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.46
- QED: 0.44

## Molecule Similarity
- Weighted Tanimoto: 0.99

Answer: 1
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: EC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Activation of human GCCR expressed in human HEK293 cells assessed as luminescence signal incubated for 16 hrs at 37C measured by CRE-driven luciferase reporter assay
- Assay organism: Homo sapiens
- Assay cell type: HEK293
- Target name: Glucocorticoid receptor
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CC(C)C[C@@H](CN(CC(=O)N[C@H](C(N)=O)[C@@H](C)O)S(=O)(=O)CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCCNC(=O)COCCOCCNC(=O)COCCOCCNC(=O)CCC(NC(=O)CCCCCCCCCCCCCCCCC(=O)O)C(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)C(C)(C)NC(=O)[C@@H](N)Cc1cnc[nH]1)[C@@H](C)O)[C@@H](C)O)C(C)C
- Properties:
- ChEMBL ID: CHEMBL5070843
- Molecule type: Unknown
- Molecular weight: 4213.83
- Heavy atoms: 297
- Hydrogen bond donors: 58
- Hydrogen bond acceptors: 59
- TPSA: 1700.34
- LogP: -12.6
- Rotatable bonds: 153
- Ring count: 7
- Aromatic rings: 7
- Formal charge: 0
- Fraction Csp3: 0.6
- QED: 0.01

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 7.11
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type EC50; relation =; value 77.78; units nM; pChEMBL 7.11

## Query Molecule B
- Canonical SMILES: CC(C)C[C@@H](CN(CC(=O)N[C@H](C(N)=O)[C@@H](C)O)S(=O)(=O)CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)C(C)(C)NC(=O)[C@@H](N)Cc1cnc[nH]1)[C@@H](C)O)[C@@H](C)O)C(C)C
- Properties:
- ChEMBL ID: CHEMBL5090987
- Molecule type: Unknown
- Molecular weight: 3497.9
- Heavy atoms: 247
- Hydrogen bond donors: 53
- Hydrogen bond acceptors: 50
- TPSA: 1515.51
- LogP: -16.6
- Rotatable bonds: 113
- Ring count: 7
- Aromatic rings: 7
- Formal charge: 0
- Fraction Csp3: 0.54
- QED: 0.01

## Molecule Similarity
- Weighted Tanimoto: 0.87

Answer: 9.07
## Endpoint to Predict
- Endpoint scope: target
- Measurement type: Emax
- Label type: binary
- Binary semantics: activity
- Target name: D(3) dopamine receptor
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: Cc1cccc(NC(=O)CN2CCN(c3cccc4ccccc34)CC2)c1
- Properties:
- ChEMBL ID: CHEMBL4473652
- Molecule type: Unknown
- Molecular weight: 359.47
- Heavy atoms: 27
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 3
- TPSA: 35.58
- LogP: 3.91
- Rotatable bonds: 4
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.26
- QED: 0.77

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 0
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Emax; comment Not Active

## Query Molecule B
- Canonical SMILES: Cc1ccc(C2CCN(CC(=O)Nc3cccc(C)c3)CC2)cc1
- Properties:
- ChEMBL ID: CHEMBL4473792
- Molecule type: Unknown
- Molecular weight: 322.45
- Heavy atoms: 24
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 2
- TPSA: 32.34
- LogP: 4.12
- Rotatable bonds: 4
- Ring count: 3
- Aromatic rings: 2
- Formal charge: 0
- Fraction Csp3: 0.38
- QED: 0.92

## Molecule Similarity
- Weighted Tanimoto: 0.57

Answer: 0
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Kd
- Label type: continuous
- Binary semantics: pchembl
- Assay description: Inhibition of SOS1 Nucleotide Exchange Activity: The purpose of this assay was to characterize the inhibitory activity of compounds on SOS1 nucleotide exchange of KRAS. Data was reported as IC50 values based on the TR-FRET signal.Notethe Following Protocol Describes a Procedure for Monitoring the Inhibition of SOS1 Nucleotide Exchange Activity of Wild-Type KRAS in Response to a Compound of the Invention. Other KRAS Mutants and RAS Isoforms May be Employed.In assay buffer containing 20 mM HEPES, pH 7.5, 150 mM NaCl, 5 mM MgCl2, 0.05% Tween-20, 0.1% BSA, 1 mM DTT, concentration series of test compounds were generated spanning 100 μM to 1.7 nM over eleven 3-fold serial dilutions in a 384-well assay plate at a volume of 20 μL. The purified tagless catalytic domain of SOS1 (residues 564-1049) was first diluted in assay buffer at a concentration of 100 nM, and then 20 μL of the SOS1 containing solution was directly dispensed into compound plates. The SOS1/compound mixture was incubated at room temperature with constant mixing on an orbital shaker for 20 minutes to allow the reaction to reach equilibrium. A KRAS mixture was prepared by diluting 66.7 nM avi-tagged KRAS (residue 1-169), 3.33 nM Streptavidin-Tb and 333 nM EDA-GTP-DY-647P1 in assay buffer. This mixture was prepared immediately before addition to the SOS1/compound mixture to prevent intrinsic nucleotide exchange. Then 5 μL of the pre-incubated SOS1/compound mixture and 7.5 μL of the KRAS mixture were added sequentially in a 384-well low volume black round bottom plate and incubated at room temperature with constant shaking for 30 minutes. Time-resolved fluorescence was measured on a PerkinElmer Envision plate reader. DMSO and 10 μM of compound (i) were used as negative and positive controls, respectively.
- Target name: Son of sevenless homolog 1
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: C[C@@H](Nc1ncnc2c1cc(C1=CCN(CC(F)(F)F)CC1)c(=O)n2C)c1cccc(C(F)F)c1F
- Properties:
- ChEMBL ID: CHEMBL5987855
- Molecular weight: 511.47
- Heavy atoms: 36
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 5
- TPSA: 63.05
- LogP: 5.23
- Rotatable bonds: 6
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.38
- QED: 0.46

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 7.31
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Kd; relation =; value 48.6; units nM; pChEMBL 7.31; comment 1108463

## Query Molecule B
- Canonical SMILES: COC1(c2cc3c(N[C@H](C)c4cccc(C(F)F)c4F)ncnc3n(C)c2=O)CCS(=O)(=O)CC1
- Properties:
- ChEMBL ID: CHEMBL5952300
- Molecular weight: 510.54
- Heavy atoms: 35
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 7
- TPSA: 103.18
- LogP: 3.63
- Rotatable bonds: 6
- Ring count: 4
- Aromatic rings: 3
- Formal charge: 0
- Fraction Csp3: 0.43
- QED: 0.54

## Molecule Similarity
- Weighted Tanimoto: 0.54

Answer: 7.4
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: IC50
- Label type: continuous
- Binary semantics: pchembl
- Assay description: luminescent kinase assay: Inhibition of TgCDPK1 and CpCDPK1 was determined using a luminescent kinase assay which measures ATP depletion in the presence of the Syntide 2 peptide substrate (KinaseGlo). (U.S. Provisional Patent Application No. 61/299,286, and reference 9) Similar to TgCDPK1, exogenous calcium was necessary for CpCDPK1 to possess maximum catalytic activity (data not shown). Notably, both kinases were tested at the same ATP concentration which allows direct comparison of inhibitor potencies due to these enzymes possessing similar Kms for this cofactor. (20)Encouraged by the similar potency of inhibitor 3 against TgCDPK1 (IC50=150±20 nM) and CpCDPK1 (IC50=130±40 nM), pyrazolopyrimidine analogues that contain a naphthylmethylene group at the 3-position and various alkyl substituents at the 1-position were tested for their ability to inhibit both kinases.
- Assay organism: Homo sapiens
- Target name: Tyrosine-protein kinase ABL1
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: CC(C)(C)n1nc(-c2ccc3ccccc3c2)c2c(N)ncnc21
- Properties:
- ChEMBL ID: CHEMBL1231371
- Molecule type: Small molecule
- Molecular weight: 317.4
- Heavy atoms: 24
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 4
- TPSA: 69.62
- LogP: 3.98
- Rotatable bonds: 1
- Ring count: 4
- Aromatic rings: 4
- Formal charge: 0
- Fraction Csp3: 0.21
- QED: 0.58

## Known Reference Result on This Endpoint
- Molecule A clean result: median pChEMBL = 5.22
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type IC50; relation =; value 6000; units nM; pChEMBL 5.22; comment 860623

## Query Molecule B
- Canonical SMILES: CC(Oc1ccc2cc(-c3nn(C(C)C)c4ncnc(N)c34)ccc2c1)c1ccccc1
- Properties:
- ChEMBL ID: CHEMBL5767089
- Molecular weight: 423.52
- Heavy atoms: 32
- Hydrogen bond donors: 1
- Hydrogen bond acceptors: 5
- TPSA: 78.85
- LogP: 5.95
- Rotatable bonds: 5
- Ring count: 5
- Aromatic rings: 5
- Formal charge: 0
- Fraction Csp3: 0.19
- QED: 0.38

## Molecule Similarity
- Weighted Tanimoto: 0.53

Answer: 5.91
## Endpoint to Predict
- Endpoint scope: assay
- Measurement type: Activity
- Label type: binary
- Binary semantics: activity
- Assay description: Stimulation of MMP9 activity in CB1 receptor knockout HUVEC assessed as increase in enzyme activity at 10 nM relative to control
- Assay organism: Homo sapiens
- Assay cell type: HUVEC
- Target name: Matrix metalloproteinase-9
- Target type: SINGLE PROTEIN
- Target organism: Homo sapiens

## Reference Molecule A
- Canonical SMILES: C[C@H](CO)NC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCOC(=O)c1cc(I)ccc1N=[N+]=[N-]
- Properties:
- ChEMBL ID: CHEMBL208548
- Molecule type: Small molecule
- Molecular weight: 606.5
- Heavy atoms: 36
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 5
- TPSA: 124.39
- LogP: 6.84
- Rotatable bonds: 17
- Ring count: 1
- Aromatic rings: 1
- Formal charge: 0
- Fraction Csp3: 0.41
- QED: 0.04

## Known Reference Result on This Endpoint
- Molecule A clean result: activity label = 0
- This result is provided as context for predicting Molecule B on the same endpoint.

## Reference Molecule A Other ChEMBL Evidence
- type Activity; comment Not Active

## Query Molecule B
- Canonical SMILES: C[C@H](CO)NC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCOC(=O)c1cccc2c1OC(C)(C(C)(C)C)O2
- Properties:
- ChEMBL ID: CHEMBL513597
- Molecule type: Small molecule
- Molecular weight: 553.74
- Heavy atoms: 40
- Hydrogen bond donors: 2
- Hydrogen bond acceptors: 6
- TPSA: 94.09
- LogP: 6.83
- Rotatable bonds: 16
- Ring count: 2
- Aromatic rings: 1
- Formal charge: 0
- Fraction Csp3: 0.52
- QED: 0.13

## Molecule Similarity
- Weighted Tanimoto: 0.53

Answer: 0