Harmaline

Harmaline

SCHEMBL1360259

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

nearest known ligand 0.97

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 0.97
HTR7 known ✓ P34969 6/20 0.97
HTR2C known ✓ P28335 4/20 0.97
HTR2A known ✓ P28223 3/20 0.97
HTR6 known ✓ P50406 3/20 0.97
GAA known ✓ P10253 2/20 0.97
MAOA known ✓ P21397 1/20 0.97
ACHE known ✓ P22303 1/20 0.97
ADRB2 known ✓ P07550 1/20 0.61
HTR1A known ✓ P08908 1/20 0.61
HTR5A known ✓ P47898 1/20 0.61
CHRM4 known ✓ P08173 2/20 0.53
DRD2 known ✓ P14416 2/20 0.53
PDE5A known ✓ O76074 1/20 0.53
ADRA2A known ✓ P08913 1/20 0.48
ADRA2B known ✓ P18089 1/20 0.48
ADRA2C known ✓ P18825 1/20 0.48
KDM4E B2RXH2 8/20 0.97
MEN1 O00255 7/20 0.97
KMT2A Q03164 7/20 0.97

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 SCHEMBL177545 0.99 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL30055802 0.99 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL29626541 0.99 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL199260 0.99 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL31500129 0.90 KDM4E (0.83) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL9481244 0.88 KDM4E (0.80) KDM4EMEN1KMT2ACASP1CYP1A2
SCHEMBL3877767 0.88 KDM4E (1.00) KDM4EMEN1KMT2ACASP1CYP1A2
Harmaline SCHEMBL28061967 0.87 KDM4E (0.78) KDM4EMEN1KMT2ACASP1CYP1A2
SCHEMBL1520427 0.84 KDM4E (0.74) KDM4EMEN1KMT2ACASP1CYP1A2
SCHEMBL28871756 0.82 KDM4E (0.70) 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 40 patents — showing the first 20. claimed = in the patent's claims; disclosed = body only.

PatentTitleAssigneePublishedPriorityFilingCountryStatus
US-20110224141-A1 METHODS AND RELATED COMPOSITIONS FOR THE TREATMENT OF CANCER STC.UNM (US) 2011-09-15 US claimed
WO-2009148623-A2 METHODS AND RELATED COMPOSITIONS FOR THE TREATMENT OF CANCER STC.UNM (US) 2009-12-10 WO claimed
US-12592370-B2 Screening with mass spectrometry for mycobacteria prior to cardiothoracic surgery IMPERIAL COLLEGE INNOVATIONS LIMITED (GB) 2026-03-31 US disclosed
US-12545944-B2 Method of detection IMPERIAL COLLEGE INNOVATIONS LIMITED (GB) 2026-02-10 US disclosed
WO-2024254645-A1 COMPOSITION AND METHOD TO TREAT, AMELIORATE OR PREVENT A PSYCHOLOGICAL, NEUROLOGICAL OR INFLAMMATORY DISORDER, AND METHOD FOR PREPARING COMPOSITION Psychae Therapeutics Pty Ltd (AU) 2024-12-19 WO disclosed
US-20230135821-A1 SCREENING WITH MASS SPECTROMETRY FOR MYCOBACTERIA PRIOR TO CARDIOTHORACIC SURGERY IMPERIAL COLLEGE INNOVATIONS LIMITED (GB) 2023-05-04 US disclosed
EP-4038392-A1 SCREENING WITH MASS SPECTROMETRY FOR MYCOBACTERIA PRIOR TO CARDIOTHORACIC SURGERY Imperial College Innovations Limited (GB) 2022-08-10 EP disclosed
EP-3589742-B1 METHOD OF DETECTION IMPERIAL COLLEGE INNOVATIONS LTD (GB) 2021-08-04 EP disclosed
WO-2021064426-A1 SCREENING WITH MASS SPECTROMETRY FOR MYCOBACTERIA PRIOR TO CARDIOTHORACIC SURGERY IMPERIAL COLLEGE INNOVATIONS LIMITED (GB) 2021-04-08 WO disclosed
US-10188633-B2 Identification of small molecules that facilitate therapeutic exon skipping THE REGENTS OF THE UNIVERSITY OF CALIFORNIA (US) 2019-01-29 US disclosed
EP-2750715-B1 IDENTIFICATION OF SMALL MOLECULES THAT ENHANCE THERAPEUTIC EXON SKIPPING UNIV CALIFORNIA (US) 2018-10-31 EP disclosed
US-20050288234-A1 Novel use of peptide compounds for treating essential tremor and other tremor syndromes SCHWARZ PHARMA AG (DE) 2005-12-29 US disclosed
US-6601010-B1 Force plate actometer THE UNIVERSITY OF KANSAS 2003-07-29 US disclosed
US-20030124320-A1 Recording sheets containing pyrrole, pyrrolidine, pyridine, piperidine, homopiperidine, quinoline, isoquinoline, quinuclidine, indole, and indazole compounds XEROX CORPORATION 2003-07-03 US disclosed
EP-0859610-A4 IBOGAMINE CONGENERS ALBANY MEDICAL COLLEGE (US) 2002-05-15 EP disclosed
CN-1063966-C Harmel preparation and preparing method thereof WANG SHIYU (CN) 2001-04-04 CN disclosed
US-6211360-B1 DRUG ABRUSE THERAPY; PLANT EXTRACTS ALBANY MEDICAL COLLEGE 2001-04-03 US disclosed
EP-0859610-A1 IBOGAMINE CONGENERS ALBANY MEDICAL COLLEGE (US) 1998-08-26 EP disclosed
WO-1997005869-A1 IBOGAMINE CONGENERS ALBANY MEDICAL COLLEGE (US) 1997-02-20 WO disclosed
US-5591738-A Method of treating chemical dependency using β-carboline alkaloids, derivatives and salts thereof NDA INTERNATIONAL, INC. (US) 1997-01-07 US disclosed

Patent text — is the patent's own abstract consistent with the prediction?

For each of this compound's patents that has machine-readable text (4 of them — usually the abstract, not the full specification), we ask MedCPT which protein the text reads most about, and where the chemistry-predicted target lands among 4885 human targets. A high rank means the patent's own wording is consistent with the prediction — a weak, independent signal, not proof of activity.

PatentTitleText reads most aboutPredicted target · text-rank
US-20050288234-A1 Novel use of peptide compounds for treating essential tremor and other tremor syndromes VIP, PRSS12, GAP43 GLA 3867/4885HTR7 1764/4885HTR2C 2017/4885
US-10188633-B2 Identification of small molecules that facilitate therapeutic exon skipping RBM17, SMN1; SMN2, SNRPA1 GLA 2490/4885HTR7 3984/4885HTR2C 4601/4885
US-12592370-B2 Screening with mass spectrometry for mycobacteria prior to cardiothoracic surgery FABP3, ACADM, TST GLA 1871/4885HTR7 3620/4885HTR2C 3434/4885
US-12545944-B2 Method of detection PHOSPHO1, NAAA, LIPA GLA 1012/4885HTR7 2096/4885HTR2C 2355/4885

“Text reads most about” is the patent abstract's nearest protein in MedCPT space (background-debiased). Only ~1.4% of patents have machine-readable text, so most compounds won't have this panel.