Harmaline

Harmaline

SCHEMBL177545

COc1ccc2c3c([nH]c2c1)C(C)=NCC3.Cl.O.O

nearest known ligand 1.00 ✓ in ChEMBL — recovers established targets

Full drug profile on Sugi Atlas →

Known targets — ChEMBL curated mechanism

ABL1ACEACHEACVR1ADRA1AADRA1BADRA1DADRA2AADRA2BADRA2CADRB1ADRB2ADRB3AGTR1ALKAVPR1AAVPR2BCHEBCRCA2CACNA1ACACNA1BCACNA1CCACNA1DCACNA1ECACNA1FCACNA1GCACNA1HCACNA1ICACNA1SCACNA2D1CACNA2D2CACNA2D3CACNA2D4CACNB1CACNB2CACNB3CACNB4CACNG1CACNG2CACNG3CACNG4CACNG5CACNG6CACNG7CACNG8CALCRLCASRCCR5CDK4CDK6CFBCHRM1CHRM2CHRM3CHRM4CHRM5CHRNA1CHRNA3CHRNA7CHRNB1CHRNB4CHRNDCHRNECHRNGCOXFA4COXFA4L2CRBNCSF1RCUL4ACYP19A1DDB1DPP4DRD1DRD2DRD3DRD4EDNRAEGFREML4ERBB2ERBB4ESR1ESR2FGFR1FGFR3FLT1FLT3FLT4GAAGABRA1GABRA2GABRA3GABRA4GABRA5GABRA6GABRB1GABRB2GABRB3GABRDGABREGABRG1GABRG2GABRG3GABRPGABRQGHSRGLAGNRHRGPD2GRIN1GRIN2AGRIN2BGRIN2CGRIN2DGRIN3AGRIN3BGSTP1HCN4HCRTR1HCRTR2HDAC1HDAC10HDAC11HDAC2HDAC3HDAC4HDAC5HDAC6HDAC7HDAC8HDAC9HRH1HRH2HRH3HSD11B1HSP90AA1HSP90AB1HTR1AHTR1BHTR1DHTR1EHTR1FHTR2AHTR2BHTR2CHTR3AHTR3BHTR3CHTR3DHTR3EHTR4HTR5AHTR6HTR7IMPDH1IMPDH2ITGA2BITGB3ITKJAK1JAK2KCNA1KCNA10KCNA2KCNA3KCNA4KCNA5KCNA6KCNA7KCNB1KCNB2KCNC1KCNC2KCNC3KCNC4KCND1KCND2KCND3KCNF1KCNG1KCNG2KCNG3KCNG4KCNH1KCNH2KCNH3KCNH4KCNH5KCNH6KCNH7KCNH8KCNJ2KCNJ3KCNJ5KCNK3KCNK9KCNQ1KCNQ2KCNQ3KCNQ4KCNQ5KCNS1KCNS2KCNS3KCNV1KCNV2KDRKITKLKB1LCKMMAOAMAOBMAPK14METMMP1MMP13MMP7MMP8MT-ND1MT-ND2MT-ND3MT-ND4MT-ND4LMT-ND5MT-ND6NDUFA1NDUFA10NDUFA11NDUFA12NDUFA13NDUFA2NDUFA3NDUFA5NDUFA6NDUFA7NDUFA8NDUFA9NDUFAB1NDUFAF1NDUFAF2NDUFAF3NDUFAF4NDUFB1NDUFB10NDUFB11NDUFB2NDUFB3NDUFB4NDUFB5NDUFB6NDUFB7NDUFB8NDUFB9NDUFC1NDUFC2NDUFS1NDUFS2NDUFS3NDUFS4NDUFS5NDUFS6NDUFS7NDUFS8NDUFV1NDUFV2NDUFV3NR3C1NS5ANTRK1NTRK2NTRK3ODC1OPRD1OPRK1OPRM1P2RY12PAHPARP1PDE3APDE3BPDE4APDE4BPDE4CPDE4DPDE5APDE7APDE7BPDE8APDE8BPDGFRAPDGFRBPIK3CAPIK3CDPNPPOLA1POLA2POLD1POLD2POLD3POLD4POLEPOLE2POLE3PPARGPRIM1PRIM2PRKCAPRKCBPRKCDPRKCEPRKCGPRKCHPRKCIPRKCQPRKCZPRKD1PRKD3PTGS1PTGS2RBX1RENRETROCK1ROCK2RPE65RRM1RRM2RRM2BS1PR1S1PR2S1PR3S1PR4S1PR5SCN10ASCN11ASCN1ASCN2ASCN3ASCN4ASCN5ASCN7ASCN8ASCN9ASCNN1ASCNN1BSCNN1GSIGMAR1SLC18A2SLC6A1SLC6A2SLC6A3SLC6A4SLC9A3SRCTACR1TOP1TOP2ATOP2BTTRTYMPdacAdacBdacCembAfolAftsIgyrAgyrBmrcAmrcBmrdAparCparEpolrplArplBrplCrplDrplErplFrplIrplJrplKrplLrplMrplNrplOrplPrplQrplRrplSrplTrplUrplVrplWrplXrplYrpmArpmBrpmCrpmDrpmErpmE2rpmFrpmGrpmG1rpmG2rpmG3rpmHrpmIrpmJrpsArpsBrpsCrpsDrpsErpsFrpsGrpsHrpsIrpsJrpsKrpsLrpsMrpsNrpsOrpsPrpsQrpsRrpsSrpsTrpsUykgMykgO

The experimentally established mechanism targets of Harmaline. The predicted profile below is derived independently by chemical similarity — agreement is a validation signal, a miss is honest.

Predicted protein targets (top 20)

geneUniProtsupporting neighboursconfidence
GLA known ✓ P06280 2/20 1.00
HTR7 known ✓ P34969 6/20 0.95
HTR2C known ✓ P28335 4/20 0.95
HTR2A known ✓ P28223 3/20 0.95
HTR6 known ✓ P50406 3/20 0.95
GAA known ✓ P10253 2/20 0.95
MAOA known ✓ P21397 1/20 0.95
ACHE known ✓ P22303 1/20 0.95
ADRB2 known ✓ P07550 2/20 0.59
HTR1A known ✓ P08908 1/20 0.59
HTR5A known ✓ P47898 1/20 0.59
CHRM4 known ✓ P08173 2/20 0.52
DRD2 known ✓ P14416 2/20 0.52
PDE5A known ✓ O76074 1/20 0.52
ADRA2A known ✓ P08913 1/20 0.47
ADRA2B known ✓ P18089 1/20 0.47
ADRA2C known ✓ P18825 1/20 0.47
KDM4E B2RXH2 9/20 1.00
MEN1 O00255 7/20 1.00
KMT2A Q03164 7/20 1.00

Click a target to see other patent compounds predicted against it — the reverse direction, in place.

Similar compounds — the chemically nearest patent molecules

Nearest neighbours by Morgan-fingerprint cosine across the patent-compound collection, with each neighbour's top predicted target and the predicted targets it shares with this molecule.

Compoundsimilaritytop predictedshared targets
Harmaline SCHEMBL30055802 1.00 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL1360259 0.99 KDM4E (0.97) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL199260 0.97 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL29626541 0.97 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL31500129 0.88 KDM4E (0.83) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL9481244 0.87 KDM4E (0.80) KDM4EMEN1KMT2ACASP1CYP1A2
SCHEMBL3877767 0.86 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL28061967 0.86 KDM4E (0.78) KDM4EMEN1KMT2ACASP1CYP1A2
SCHEMBL1520427 0.83 KDM4E (0.74) KDM4EMEN1KMT2ACASP1CYP1A2
Harmalol SCHEMBL3759482 0.81 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2

Similarity is cosine over the 2,048-bit Morgan fingerprint (≈ Tanimoto). Identical fingerprints score 1.00.

Patent provenance — the patents this molecule appears in, and who filed them

Claimed or disclosed in 30 patents — showing the first 20. claimed = in the patent's claims; disclosed = body only.

PatentTitleAssigneePublishedPriorityFilingCountryStatus
EP-0743574-B1 Migration imaging members XEROX CORP (US) 2000-12-27 EP claimed
EP-0743573-B1 Method for obtaining image contrast migration imaging members XEROX CORP (US) 2000-09-06 EP claimed
EP-0743573-A2 Method for obtaining image contrast migration imaging members XEROX CORPORATION (US) 1996-11-20 EP claimed
EP-0743574-A2 Migration imaging members XEROX CORPORATION (US) 1996-11-20 EP claimed
US-5563014-A SOFTENABLE LAYER CONTAINIG PHOTOSENSITIVE MARKING MATERIAL; TRANSPARENTIZING AGENT XEROX CORPORATION (US) 1996-10-08 US claimed
US-5514505-A SELECTIVE TRANSPARENTIZATION OF PHOTOSENSITIVE MIGRATION MARKING PARTICLES EMBEDDED NEAR THE SURFACE OF A SOFTENABLE LAYER SUPPORTED BY AN ELECTROCONDUCTIVE SUBSTRATE XEROX CORPORATION (US) 1996-05-07 US claimed
US-9982260-B2 Identification of structurally similar small molecules that enhance therapeutic exon skipping THE REGENTS OF THE UNIVERSITY OF CALIFORNIA (US) 2018-05-29 US disclosed
US-20160257952-A1 IDENTIFICATION OF STRUCTURALLY SIMILAR SMALL MOLECULES THAT ENHANCE THERAPEUTIC EXON SKIPPING NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT 2016-09-08 US disclosed
EP-3052654-A1 IDENTIFICATION OF STRUCTURALLY SIMILAR SMALL MOLECULES THAT ENHANCE THERAPEUTIC EXON SKIPPING The Regents of the University of California (US) 2016-08-10 EP disclosed
US-9393221-B2 Methods and compounds for reducing intracellular lipid storage THE GENERAL HOSPITAL CORPORATION (US) 2016-07-19 US disclosed
WO-2015048792-A1 IDENTIFICATION OF STRUCTURALLY SIMILAR SMALL MOLECULES THAT ENHANCE THERAPEUTIC EXON SKIPPING THE REGENTS OF THE UNIVERSITY OF CALIFORNIA (US) 2015-04-02 WO disclosed
US-20130023488-A1 METHODS AND COMPOUNDS FOR REDUCING INTRACELLULAR LIPID STORAGE THE GENERAL HOSPITAL CORPORATION (US) 2013-01-24 US disclosed
EP-1910844-B1 CROSS-BETA STRUCTURE BINDING COMPOUNDS CROSSBETA BIOSCIENCES BV (NL) 2012-04-18 EP disclosed
US-5580689-A SOLFTENABLE LAYER OF SOFTENABLE MATERIAL, PIGMENT SENSITIVE TO INFRARED OR RED LIGHT ILLUMINATION, AND MIGRATION MARKING MATERIAL XEROX CORPORATION (US) 1996-12-03 US disclosed
EP-0743574-A2 Migration imaging members XEROX CORPORATION (US) 1996-11-20 EP disclosed
EP-0743573-A2 Method for obtaining image contrast migration imaging members XEROX CORPORATION (US) 1996-11-20 EP disclosed
US-5563014-A SOFTENABLE LAYER CONTAINIG PHOTOSENSITIVE MARKING MATERIAL; TRANSPARENTIZING AGENT XEROX CORPORATION (US) 1996-10-08 US disclosed
US-5534374-A Migration imaging members XEROX CORPORATION (US) 1996-07-09 US disclosed
US-5514505-A SELECTIVE TRANSPARENTIZATION OF PHOTOSENSITIVE MIGRATION MARKING PARTICLES EMBEDDED NEAR THE SURFACE OF A SOFTENABLE LAYER SUPPORTED BY AN ELECTROCONDUCTIVE SUBSTRATE XEROX CORPORATION (US) 1996-05-07 US disclosed
EP-0673782-A2 Recording sheets containing pyrrole, pyrrolidine, pyridine, piperidine, homopiperidine, quinoline, isoquinoline, quinuclidine, indole, and indazole compounds XEROX CORPORATION (US) 1995-09-27 EP disclosed