UCSF

ZINC00537964

Substance Information

In ZINC since Heavy atoms Benign functionality
October 5th, 2005 26 Yes

CAS Numbers: 51773-92-3 , 53230-10-7 , 58560-52-4

Other Names:

(+)-(11R,2'S)-erythro-Mefloquine

(+)-erythro-4-Quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-

(+)-Mefloquine

(+)-threo-4-Quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-, (11S, 2'S)-

(+)-Threo-Mefloquine

(+/-)-erythro-4-Quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-

(+/-)-threo-4-Quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-

(-)-(11S,2'R)-erythro-Mefloquine

(-)-Mefloquine

(-)-threo-4-Quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-, (11R, 2'R)-

(-)-Threo-Mefloquine

(DL-erythro-alpha-2-Piperidyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol

(R)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2R)-piperidin-2-yl]methanol

(R)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2S)-piperidin-2-yl]methanol

(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2R)-piperidin-2-yl]methanol

(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2S)-piperidin-2-yl]methanol

(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2R)-piperidin-2-yl]methanol

4-Quinolinemethanol, .alpha.-(2R)-2-piperidinyl-2,8-bis(trifluoromethyl)-, (.alpha.S)-

4-Quinolinemethanol, .alpha.-(2S)-2-piperidinyl-2,8-bis(trifluoromethyl)-, (.alpha.R)-

4-Quinolinemethanol, .alpha.-2-piperidinyl-2,8-bis(trifluoromethyl)-, (R*,S*)-(.+/-.)-

4-quinolinemethanol, a-2-piperidinyl-2,8-bis(trifluoromethyl)-

4-Quinolinemethanol, alpha-(2R)-2-piperidinyl-2,8-bis(trifluoromethyl)-, (alphaS)-

4-Quinolinemethanol, alpha-(2R)-2-piperidinyl-2,8-bis(trifluoromethyl)-, (alphaS)-rel-

4-Quinolinemethanol, alpha-(2S)-2-piperidinyl-2,8-bis(trifluoromethyl)-, (alphaR)-

4-Quinolinemethanol, alpha-2-piperidinyl-2,8-bis(trifluoromethyl)-

4-Quinolinemethanol, alpha-2-piperidinyl-2,8-bis(trifluoromethyl)-, (R*,S*)-(+-)-

4-Quinolinemethanol, alpha-2-piperidinyl-2,8-bis(trifluoromethyl)-, (R*,S*)-(+/-)-

49752-90-1

51688-68-7

51742-87-1

51744-84-4

51744-85-5

51773-92-3; D00831; Lariam (TN); Mefloquine hydrochloride (JP16/USP)

51773-92-3; Mefloquine hydrochloride; Prestwick_538

53230-10-7

53230-10-7; C07633; Mefloquine

53230-10-7; D04895; Mefloquine (USAN/INN)

68682-27-9

AB00052310

AC1L1HAJ

AC1L249S

AC1L9UO6

AC1MHD7J

AC1MHD7O

AC1Q4K1I

alpha-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol

alpha-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol; alpha-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol

alpha-2-Piperidyl-2,8-bis(trifluoromethyl)quinoline-4-methanol

AR-1G4597

BIDD:GT0596

BIDD:PXR0166

BPBio1_000190

BRD-A89585551-003-03-4

BSPBio_000172

C07633

C17H16F6N2O

CAS-51773-92-3

CHEBI:151162

CHEBI:403542

CHEMBL411329

CHEMBL411685

CHEMBL411686

CHEMBL416956

CID3000506

CID3000516

CID4046

CID40692

CID456309

D04895

DAP001310

DB00358

DivK1c_000790

EINECS 256-468-3

Erthro-.alpha.-[2-piperidyl]-2,8-bis[trifluoromethyl]-4-quinolinemethanol

GNF-PF-5544

GNF-Pf-5544; Ro-215998; WR-142490; Ro-215998001

HMS1922C09

HMS502H12

HSDB 6853

IDI1_000790

INN

KBio1_000790

KBio2_001792

KBio2_004360

KBio2_006928

KBio3_002046

KBioGR_001392

KBioSS_001792

Lariam

Lariam (Hydrochloride)

LS-142023

LS-187797

Mefloquin

Mefloquina

Mefloquina [INN-Spanish]

Mefloquine (BAN

Mefloquine (USAN/INN)

Mefloquine HCL

Mefloquine hydrochloride

Mefloquine Hydrochloride (FDA

Mefloquine [USAN:INN:BAN]

mefloquinehcl

Mefloquinone

Mefloquinum

Mefloquinum [INN-Latin]

Mephloquine

MolPort-003-981-155

MQ

NCGC00016864-01

NCGC00094994-01

NCGC00094994-02

NCGC00094994-03

NCGC00094994-04

NCGC00161831-01

NCGC00161831-02

nchembio.215-comp3

nchembio.87-comp20

NINDS_000790

NSC157387

Prestwick0_000126

Prestwick1_000126

Prestwick2_000126

Prestwick3_000126

Racemic mefloquine

RO 13-7224

RO 13-7225

Ro 21-5998

Ro 21-5998 (Hydrochloride)

Ro 215998

Ro-21-5998-001

RTI1169-1-1

RTI1172-1-1

RTI1173-1-1

RTI1174-1-1

RTI1188-1-1

RTI1189-1-1

SPB-80406

SPBio_001591

SPBio_002111

SPECTRUM1503070

Spectrum2_001516

Spectrum3_000953

Spectrum4_001066

Spectrum5_001122

Spectrum_001312

UNII-TML814419R

USAN

USAN)

USAN); Mefloquine HCl (FDA

USP)

USP); Mefloquine (BAN

WR 142490

WR-142,490

WR-142490

WR-177,602

[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol

[2,8-bis(trifluoromethyl)quinolin-4-yl]-piperidin-2-ylmethanol

Download: MOL2 SDF SMILES Flexibase

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 4.24 6.7 -52.23 3 3 1 50 379.324 4

Vendor Notes

Note Type Comments Provided By
ALOGPS_SOLUBILITY 3.80e-02 g/l DrugBank-approved
Therapy antimalarial SMDC MicroSource
PUBCHEM_PATENT_ID EP0001796A1; EP0077551A2; EP0108147A1; EP0154491A2; EP0169618A2; EP0169618B2; EP0222839A1; EP0286316A1; EP0286316B1; EP0290959A2; EP0316440B1; EP0332657A1; EP0335717A2; EP0338532A2; EP0361894A2; EP0361894B1; EP0362810A1; EP0362810B1; EP0364559A1; EP036455 IBM Patent Data
PUBCHEM_PATENT_ID EP0966285A1; WO1999026627A1; WO2000013682A2 IBM Patent Data

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
AA1R-2-E Adenosine A1 Receptor (cluster #2 Of 4), Eukaryotic Eukaryotes 1221 0.32 Binding ≤ 10μM
AA2AR-2-E Adenosine A2a Receptor (cluster #2 Of 4), Eukaryotic Eukaryotes 124 0.37 Binding ≤ 10μM
KCNH2-5-E HERG (cluster #5 Of 5), Eukaryotic Eukaryotes 5623 0.28 Binding ≤ 10μM
Z102013-2-O Plasmodium Malariae (cluster #2 Of 2), Other Other 47 0.39 Functional ≤ 10μM
Z102015-1-O Plasmodium Vivax (cluster #1 Of 1), Other Other 9 0.43 Functional ≤ 10μM
Z50417-3-O Leishmania Infantum (cluster #3 Of 4), Other Other 7000 0.28 Functional ≤ 10μM
Z50425-3-O Plasmodium Falciparum (cluster #3 Of 22), Other Other 91 0.38 Functional ≤ 10μM
Z50426-6-O Plasmodium Falciparum (isolate K1 / Thailand) (cluster #6 Of 9), Other Other 8 0.44 Functional ≤ 10μM
Z80211-1-O LoVo (Colon Adenocarcinoma Cells) (cluster #1 Of 5), Other Other 7900 0.27 Functional ≤ 10μM
Z80418-1-O RAW264.7 (Monocytic-macrophage Leukemia Cells) (cluster #1 Of 2), Other Other 6500 0.28 ADME/T ≤ 10μM
Z81135-3-O L6 (Skeletal Muscle Myoblast Cells) (cluster #3 Of 6), Other Other 4760 0.29 ADME/T ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
AA2AR_HUMAN P29274 Adenosine A2a Receptor, Human 124 0.37 Binding ≤ 1μM
AA1R_HUMAN P30542 Adenosine A1 Receptor, Human 1221 0.32 Binding ≤ 10μM
AA2AR_HUMAN P29274 Adenosine A2a Receptor, Human 124 0.37 Binding ≤ 10μM
KCNH2_HUMAN Q12809 HERG, Human 2600 0.30 Binding ≤ 10μM
Z50417 Z50417 Leishmania Infantum 7000 0.28 Functional ≤ 10μM
Z80211 Z80211 LoVo (Colon Adenocarcinoma Cells) 7900 0.27 Functional ≤ 10μM
Z50425 Z50425 Plasmodium Falciparum 0.31 0.51 Functional ≤ 10μM
Z50426 Z50426 Plasmodium Falciparum (isolate K1 / Thailand) 12 0.43 Functional ≤ 10μM
Z102013 Z102013 Plasmodium Malariae 36.8 0.40 Functional ≤ 10μM
Z102015 Z102015 Plasmodium Vivax 10.2 0.43 Functional ≤ 10μM
Z81135 Z81135 L6 (Skeletal Muscle Myoblast Cells) 4760 0.29 ADME/T ≤ 10μM
Z80418 Z80418 RAW264.7 (Monocytic-macrophage Leukemia Cells) 6500 0.28 ADME/T ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
Adenosine P1 receptors
G alpha (i) signalling events
G alpha (s) signalling events
NGF-independant TRKA activation
Voltage gated Potassium channels

Analogs ( Draw Identity 99% 90% 80% 70% )