Structure

Physi-Chem Properties

Molecular Weight:  198.08
Volume:  205.404
LogP:  1.533
LogD:  1.452
LogS:  -3.21
# Rotatable Bonds:  0
TPSA:  48.65
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.572
Synthetic Accessibility Score:  2.784
Fsp3:  0.083
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.948
MDCK Permeability:  7.245324468385661e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.726
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.687
30% Bioavailability (F30%):  0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.787
Plasma Protein Binding (PPB):  74.28522491455078%
Volume Distribution (VD):  1.0
Pgp-substrate:  17.941516876220703%

ADMET: Metabolism

CYP1A2-inhibitor:  0.987
CYP1A2-substrate:  0.947
CYP2C19-inhibitor:  0.698
CYP2C19-substrate:  0.083
CYP2C9-inhibitor:  0.233
CYP2C9-substrate:  0.783
CYP2D6-inhibitor:  0.786
CYP2D6-substrate:  0.865
CYP3A4-inhibitor:  0.522
CYP3A4-substrate:  0.215

ADMET: Excretion

Clearance (CL):  5.826
Half-life (T1/2):  0.622

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.734
Drug-inuced Liver Injury (DILI):  0.931
AMES Toxicity:  0.824
Rat Oral Acute Toxicity:  0.948
Maximum Recommended Daily Dose:  0.902
Skin Sensitization:  0.903
Carcinogencity:  0.49
Eye Corrosion:  0.037
Eye Irritation:  0.966
Respiratory Toxicity:  0.982

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC291389

Natural Product ID:  NPC291389
Common Name*:   Harmol
IUPAC Name:   1-methyl-2,9-dihydropyrido[3,4-b]indol-7-one
Synonyms:   Harmol
Standard InCHIKey:  LBBJNGFCXDOYMQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H10N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-6,13-14H,1H3
SMILES:  O=c1ccc2c(c1)[nH]c1c2cc[nH]c1C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL486817
PubChem CID:   68094
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001140] Harmala alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota Fruits n.a. n.a. PMID[11141122]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. fruit n.a. PMID[16417304]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. branch n.a. PMID[17202693]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. PMID[2026709]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. PMID[21608987]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota Seeds n.a. n.a. PMID[28128938]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. PMID[6736972]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO18460 Trema dielsiana Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7780 Thalictrum foetidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3808 Elaeagnus angustifolia Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO18460 Trema dielsiana Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7780 Thalictrum foetidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3808 Elaeagnus angustifolia Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3808 Elaeagnus angustifolia Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3808 Elaeagnus angustifolia Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1085 Peganum harmala Species Nitrariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18460 Trema dielsiana Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7780 Thalictrum foetidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Ki = 65000.0 nM PMID[547052]
NPT91 Cell Line KB Homo sapiens ED50 = 4.4 ug ml-1 PMID[547053]
NPT81 Cell Line A549 Homo sapiens ED50 = 6.5 ug ml-1 PMID[547053]
NPT308 Cell Line CAKI-1 Homo sapiens ED50 = 9.2 ug ml-1 PMID[547053]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 9.2 ug ml-1 PMID[547053]
NPT309 Cell Line 1A9 Homo sapiens ED50 = 3.8 ug ml-1 PMID[547053]
NPT1535 Cell Line U-87 MG Homo sapiens ED50 = 4.2 ug ml-1 PMID[547053]
NPT3240 Individual Protein Cyclin-dependent kinase 5 Homo sapiens Inhibition = 72.0 % PMID[547054]
NPT1371 Individual Protein Cyclin-dependent kinase 2 Homo sapiens Inhibition = 69.0 % PMID[547054]
NPT759 Cell Line H9 Homo sapiens IC50 = 108100.0 nM PMID[547055]
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 7.9 nM PMID[547056]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[547057]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 35481.3 nM PMID[547057]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 28183.8 nM PMID[547056]
NPT1038 Individual Protein Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 8912.5 nM PMID[547056]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 25118.9 nM PMID[547058]
NPT442 Individual Protein Ferritin light chain Equus caballus Potency = 28183.8 nM PMID[547056]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 12589.3 nM PMID[547058]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 35481.3 nM PMID[547057]
NPT501 Individual Protein Alpha-galactosidase A Homo sapiens Potency = 39810.7 nM PMID[547056]
NPT501 Individual Protein Alpha-galactosidase A Homo sapiens Potency = 44668.4 nM PMID[547057]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[547058]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 25118.9 nM PMID[547057]
NPT59 Individual Protein DNA polymerase beta Homo sapiens Potency = 28183.8 nM PMID[547056]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 39810.7 nM PMID[547057]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 15848.9 nM PMID[547058]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 15848.9 nM PMID[547058]
NPT61 Individual Protein Beta-glucocerebrosidase Homo sapiens Potency n.a. 19952.6 nM PMID[547056]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 8199.5 nM PMID[547056]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 5802.4 nM PMID[547056]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 50118.7 nM PMID[547056]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 17782.8 nM PMID[547056]
NPT1078 Individual Protein Indoleamine 2,3-dioxygenase Homo sapiens IC50 = 2000000.0 nM PMID[547059]
NPT4093 Individual Protein Serine/threonine-protein kinase haspin Homo sapiens IC50 = 770.0 nM PMID[547060]
NPT3399 Individual Protein Dual-specificity tyrosine-phosphorylation regulated kinase 2 Homo sapiens IC50 = 1500.0 nM PMID[547060]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 29092.9 nM PMID[547056]
NPT1852 Individual Protein Rac GTPase-activating protein 1 Homo sapiens IC50 n.a. 44910.0 nM PMID[547056]
NPT5016 Individual Protein DNA repair and recombination protein RAD54-like Homo sapiens AC50 n.a. 23890.0 nM PMID[547056]
NPT1417 Individual Protein Transcriptional regulator ERG Homo sapiens Potency n.a. 112201.8 nM PMID[547056]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PMID[547056]
NPT1417 Individual Protein Transcriptional regulator ERG Homo sapiens Potency n.a. 44668.4 nM PMID[547056]
NPT1043 Individual Protein Glycoprotein hormones alpha chain Homo sapiens Potency n.a. 1584.9 nM PMID[547056]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 13335.9 nM PMID[547061]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 14581.0 nM PMID[547056]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 20596.2 nM PMID[547056]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 23715.0 nM PMID[547061]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 28183.8 nM PMID[547056]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 35481.3 nM PMID[547057]
NPT3575 Individual Protein Chitinase Onchocerca volvulus IC50 = 7080.0 nM PMID[547062]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 11100.0 nM PMID[547055]
NPT27 Others Unspecified Ratio IC50/EC50 = 9.7 uM PMID[547055]
NPT2 Others Unspecified Potency = 10000.0 nM PMID[547057]
NPT536 Uncleic Acid microRNA 21 Homo sapiens Potency = 13091.8 nM PMID[547056]
NPT791 Individual Protein Cruzipain Trypanosoma cruzi Potency = 39810.7 nM PMID[547057]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 31622.8 nM PMID[547056]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 31622.8 nM PMID[547057]
NPT2 Others Unspecified Potency = 794.3 nM PMID[547057]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[547056]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 5623.4 nM PMID[547057]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 10417.9 nM PMID[547056]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 39810.7 nM PMID[547056]
NPT84 Individual Protein Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus AC50 = 298.0 nM PMID[547056]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 13115.4 nM PMID[547056]
NPT2 Others Unspecified Potency n.a. 7079.5 nM PMID[547056]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 25118.9 nM PMID[547056]
NPT2 Others Unspecified IC50 n.a. 61920.0 nM PMID[547056]
NPT2 Others Unspecified Potency n.a. 16360.1 nM PMID[547056]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 8199.5 nM PMID[547056]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[547056]
NPT2 Others Unspecified AC50 = 22110.0 nM PMID[547056]
NPT2 Others Unspecified Potency n.a. 25118.9 nM PMID[547061]
NPT3576 Organism Onchocerca volvulus Onchocerca volvulus Inhibition = 61.0 % PMID[547062]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC291389 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.7292 Intermediate Similarity NPC471655
0.6918 Remote Similarity NPC100726
0.6887 Remote Similarity NPC474492
0.6842 Remote Similarity NPC470680
0.6842 Remote Similarity NPC100104
0.6812 Remote Similarity NPC22079
0.6781 Remote Similarity NPC467188
0.6752 Remote Similarity NPC262338
0.6738 Remote Similarity NPC291517
0.6689 Remote Similarity NPC105811
0.6667 Remote Similarity NPC470440
0.6644 Remote Similarity NPC123906
0.6644 Remote Similarity NPC190296
0.6643 Remote Similarity NPC125746
0.6573 Remote Similarity NPC325252
0.6554 Remote Similarity NPC314372
0.6533 Remote Similarity NPC102664
0.6528 Remote Similarity NPC84911
0.6513 Remote Similarity NPC251391
0.6513 Remote Similarity NPC281094
0.6503 Remote Similarity NPC79777
0.6503 Remote Similarity NPC198988
0.6497 Remote Similarity NPC233380
0.649 Remote Similarity NPC473878
0.6483 Remote Similarity NPC104049
0.6481 Remote Similarity NPC284775
0.6471 Remote Similarity NPC75135
0.6471 Remote Similarity NPC209362
0.646 Remote Similarity NPC186068
0.6458 Remote Similarity NPC261195
0.6458 Remote Similarity NPC29886
0.6458 Remote Similarity NPC96102
0.6447 Remote Similarity NPC70406
0.6443 Remote Similarity NPC159856
0.6438 Remote Similarity NPC110126
0.6438 Remote Similarity NPC73767
0.6433 Remote Similarity NPC274981
0.6429 Remote Similarity NPC169586
0.6424 Remote Similarity NPC37548
0.6414 Remote Similarity NPC105127
0.6402 Remote Similarity NPC234403
0.64 Remote Similarity NPC143872
0.6395 Remote Similarity NPC469768
0.6395 Remote Similarity NPC238499
0.6395 Remote Similarity NPC469783
0.6395 Remote Similarity NPC469779
0.6395 Remote Similarity NPC469784
0.6395 Remote Similarity NPC469780
0.6395 Remote Similarity NPC469767
0.6395 Remote Similarity NPC469761
0.6392 Remote Similarity NPC115232
0.6389 Remote Similarity NPC23215
0.6387 Remote Similarity NPC213914
0.6382 Remote Similarity NPC24678
0.6382 Remote Similarity NPC105818
0.6376 Remote Similarity NPC242556
0.6369 Remote Similarity NPC282231
0.6364 Remote Similarity NPC229055
0.6358 Remote Similarity NPC471957
0.6351 Remote Similarity NPC469766
0.635 Remote Similarity NPC41174
0.6345 Remote Similarity NPC218268
0.634 Remote Similarity NPC217021
0.634 Remote Similarity NPC470679
0.6329 Remote Similarity NPC271797
0.6329 Remote Similarity NPC21174
0.6323 Remote Similarity NPC74357
0.6316 Remote Similarity NPC187951
0.6306 Remote Similarity NPC279918
0.6303 Remote Similarity NPC477042
0.6299 Remote Similarity NPC200214
0.6299 Remote Similarity NPC469765
0.6299 Remote Similarity NPC469760
0.6299 Remote Similarity NPC469763
0.6299 Remote Similarity NPC469786
0.6299 Remote Similarity NPC259644
0.6299 Remote Similarity NPC73952
0.6299 Remote Similarity NPC25008
0.6294 Remote Similarity NPC82295
0.6289 Remote Similarity NPC42372
0.6286 Remote Similarity NPC250361
0.6284 Remote Similarity NPC115611
0.6284 Remote Similarity NPC2949
0.6284 Remote Similarity NPC279081
0.6284 Remote Similarity NPC59084
0.6275 Remote Similarity NPC313889
0.6273 Remote Similarity NPC471943
0.6272 Remote Similarity NPC474259
0.6272 Remote Similarity NPC23476
0.6272 Remote Similarity NPC477415
0.6268 Remote Similarity NPC473587
0.6265 Remote Similarity NPC191415
0.6259 Remote Similarity NPC27740
0.6258 Remote Similarity NPC70922
0.6258 Remote Similarity NPC212376
0.6258 Remote Similarity NPC211572
0.6258 Remote Similarity NPC293216
0.6258 Remote Similarity NPC75540
0.6258 Remote Similarity NPC80597
0.6258 Remote Similarity NPC470507
0.6258 Remote Similarity NPC38736
0.625 Remote Similarity NPC49954
0.625 Remote Similarity NPC474561
0.6242 Remote Similarity NPC63157
0.6242 Remote Similarity NPC473868
0.6235 Remote Similarity NPC6982
0.6235 Remote Similarity NPC470498
0.6224 Remote Similarity NPC475428
0.6221 Remote Similarity NPC47190
0.6218 Remote Similarity NPC285469
0.6216 Remote Similarity NPC88097
0.6209 Remote Similarity NPC321911
0.6209 Remote Similarity NPC124005
0.6205 Remote Similarity NPC182940
0.6198 Remote Similarity NPC196580
0.6197 Remote Similarity NPC473762
0.619 Remote Similarity NPC477003
0.6188 Remote Similarity NPC2414
0.6184 Remote Similarity NPC129042
0.6184 Remote Similarity NPC288838
0.6182 Remote Similarity NPC473380
0.6182 Remote Similarity NPC240088
0.6181 Remote Similarity NPC179365
0.6181 Remote Similarity NPC475450
0.6178 Remote Similarity NPC299594
0.6176 Remote Similarity NPC473946
0.6174 Remote Similarity NPC230002
0.6173 Remote Similarity NPC194411
0.6169 Remote Similarity NPC53947
0.6164 Remote Similarity NPC214106
0.6154 Remote Similarity NPC471458
0.6154 Remote Similarity NPC477815
0.6154 Remote Similarity NPC280290
0.6149 Remote Similarity NPC54988
0.6148 Remote Similarity NPC476566
0.6145 Remote Similarity NPC11126
0.6145 Remote Similarity NPC265710
0.6144 Remote Similarity NPC179787
0.6144 Remote Similarity NPC469811
0.6144 Remote Similarity NPC201380
0.6139 Remote Similarity NPC135141
0.6139 Remote Similarity NPC92796
0.6139 Remote Similarity NPC318065
0.6139 Remote Similarity NPC206819
0.6133 Remote Similarity NPC114033
0.6133 Remote Similarity NPC277157
0.6133 Remote Similarity NPC101130
0.6133 Remote Similarity NPC58268
0.6133 Remote Similarity NPC129412
0.6129 Remote Similarity NPC216713
0.6125 Remote Similarity NPC311276
0.6125 Remote Similarity NPC194640
0.6125 Remote Similarity NPC478184
0.6122 Remote Similarity NPC292434
0.6122 Remote Similarity NPC200397
0.6122 Remote Similarity NPC167200
0.6122 Remote Similarity NPC64661
0.6122 Remote Similarity NPC14448
0.6122 Remote Similarity NPC195704
0.6122 Remote Similarity NPC138596
0.6122 Remote Similarity NPC98156
0.6121 Remote Similarity NPC151635
0.6118 Remote Similarity NPC204141
0.6115 Remote Similarity NPC469785
0.6115 Remote Similarity NPC141353
0.6114 Remote Similarity NPC472293
0.6111 Remote Similarity NPC63751
0.6108 Remote Similarity NPC16659
0.6105 Remote Similarity NPC324091
0.6105 Remote Similarity NPC475874
0.6095 Remote Similarity NPC21429
0.6092 Remote Similarity NPC473821
0.609 Remote Similarity NPC232798
0.6087 Remote Similarity NPC71132
0.608 Remote Similarity NPC74153
0.608 Remote Similarity NPC167710
0.6078 Remote Similarity NPC478186
0.6078 Remote Similarity NPC63545
0.6076 Remote Similarity NPC286427
0.6076 Remote Similarity NPC469762
0.6076 Remote Similarity NPC76982
0.6074 Remote Similarity NPC65080
0.6071 Remote Similarity NPC470677
0.6069 Remote Similarity NPC476460
0.6065 Remote Similarity NPC148592
0.6062 Remote Similarity NPC16667
0.6061 Remote Similarity NPC37423
0.6061 Remote Similarity NPC275305
0.6059 Remote Similarity NPC133003
0.6059 Remote Similarity NPC474258
0.6057 Remote Similarity NPC157828
0.6057 Remote Similarity NPC195239
0.6057 Remote Similarity NPC202812
0.6051 Remote Similarity NPC207726
0.6048 Remote Similarity NPC233050
0.6048 Remote Similarity NPC276540
0.6047 Remote Similarity NPC473628
0.6039 Remote Similarity NPC21605
0.6038 Remote Similarity NPC475990
0.6038 Remote Similarity NPC293487

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC291389 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.6458 Remote Similarity NPD198 Clinical (unspecified phase)
0.6438 Remote Similarity NPD786 Approved
0.6424 Remote Similarity NPD3100 Discontinued
0.6382 Remote Similarity NPD4463 Approved
0.6382 Remote Similarity NPD4462 Approved
0.6351 Remote Similarity NPD1722 Approved
0.6346 Remote Similarity NPD2214 Approved
0.6346 Remote Similarity NPD2213 Approved
0.6335 Remote Similarity NPD3347 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4374 Clinical (unspecified phase)
0.6316 Remote Similarity NPD269 Clinical (unspecified phase)
0.6303 Remote Similarity NPD1291 Clinical (unspecified phase)
0.6287 Remote Similarity NPD3607 Clinical (unspecified phase)
0.6284 Remote Similarity NPD3943 Clinical (unspecified phase)
0.6242 Remote Similarity NPD5020 Approved
0.622 Remote Similarity NPD4075 Phase 2
0.6174 Remote Similarity NPD9599 Approved
0.6159 Remote Similarity NPD5254 Discontinued
0.6138 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6133 Remote Similarity NPD3834 Clinical (unspecified phase)
0.6108 Remote Similarity NPD5473 Discontinued
0.6107 Remote Similarity NPD569 Clinical (unspecified phase)
0.6103 Remote Similarity NPD9392 Approved
0.6103 Remote Similarity NPD9396 Approved
0.6065 Remote Similarity NPD2172 Phase 1
0.6036 Remote Similarity NPD3318 Approved
0.6036 Remote Similarity NPD3320 Approved
0.6036 Remote Similarity NPD3319 Phase 1
0.6026 Remote Similarity NPD1592 Phase 3
0.6023 Remote Similarity NPD4426 Clinical (unspecified phase)
0.6014 Remote Similarity NPD992 Clinical (unspecified phase)
0.6014 Remote Similarity NPD991 Phase 2
0.5988 Remote Similarity NPD3506 Approved
0.5988 Remote Similarity NPD3505 Approved
0.5987 Remote Similarity NPD4637 Clinical (unspecified phase)
0.5977 Remote Similarity NPD6180 Clinical (unspecified phase)
0.5973 Remote Similarity NPD1262 Discovery
0.5964 Remote Similarity NPD4128 Approved
0.5952 Remote Similarity NPD4076 Approved
0.5952 Remote Similarity NPD4079 Approved
0.5946 Remote Similarity NPD272 Approved
0.5935 Remote Similarity NPD1270 Approved
0.593 Remote Similarity NPD6217 Discontinued
0.5929 Remote Similarity NPD268 Approved
0.5929 Remote Similarity NPD271 Approved
0.5929 Remote Similarity NPD9598 Discontinued
0.5929 Remote Similarity NPD270 Clinical (unspecified phase)
0.5928 Remote Similarity NPD749 Clinical (unspecified phase)
0.5915 Remote Similarity NPD9357 Approved
0.5915 Remote Similarity NPD5069 Clinical (unspecified phase)
0.5912 Remote Similarity NPD276 Clinical (unspecified phase)
0.5901 Remote Similarity NPD1404 Approved
0.5901 Remote Similarity NPD1403 Approved
0.5896 Remote Similarity NPD3961 Discontinued
0.5894 Remote Similarity NPD768 Clinical (unspecified phase)
0.589 Remote Similarity NPD3476 Approved
0.589 Remote Similarity NPD3475 Approved
0.589 Remote Similarity NPD2915 Discontinued
0.589 Remote Similarity NPD5744 Clinical (unspecified phase)
0.5887 Remote Similarity NPD5787 Discontinued
0.5886 Remote Similarity NPD2837 Discontinued
0.5879 Remote Similarity NPD1326 Approved
0.5879 Remote Similarity NPD1325 Approved
0.5879 Remote Similarity NPD4184 Clinical (unspecified phase)
0.5871 Remote Similarity NPD1683 Approved
0.5868 Remote Similarity NPD482 Approved
0.5867 Remote Similarity NPD200 Phase 2
0.5867 Remote Similarity NPD201 Phase 2
0.5862 Remote Similarity NPD1031 Discontinued
0.586 Remote Similarity NPD3835 Phase 3
0.586 Remote Similarity NPD3833 Phase 3
0.5857 Remote Similarity NPD4811 Discontinued
0.585 Remote Similarity NPD803 Phase 1
0.5833 Remote Similarity NPD9583 Approved
0.5828 Remote Similarity NPD5140 Approved
0.5828 Remote Similarity NPD5138 Approved
0.5828 Remote Similarity NPD3323 Discontinued
0.5822 Remote Similarity NPD3654 Approved
0.5818 Remote Similarity NPD2641 Approved
0.5818 Remote Similarity NPD2640 Approved
0.5811 Remote Similarity NPD9100 Approved
0.5806 Remote Similarity NPD175 Clinical (unspecified phase)
0.5805 Remote Similarity NPD3246 Discontinued
0.58 Remote Similarity NPD206 Clinical (unspecified phase)
0.58 Remote Similarity NPD490 Clinical (unspecified phase)
0.5793 Remote Similarity NPD2118 Approved
0.5793 Remote Similarity NPD2119 Approved
0.5779 Remote Similarity NPD2007 Clinical (unspecified phase)
0.5774 Remote Similarity NPD2928 Phase 2
0.5774 Remote Similarity NPD5065 Approved
0.5772 Remote Similarity NPD3385 Approved
0.5758 Remote Similarity NPD2639 Approved
0.5758 Remote Similarity NPD4643 Clinical (unspecified phase)
0.5758 Remote Similarity NPD2642 Approved
0.5756 Remote Similarity NPD5728 Clinical (unspecified phase)
0.5754 Remote Similarity NPD4848 Phase 1
0.574 Remote Similarity NPD7402 Clinical (unspecified phase)
0.5733 Remote Similarity NPD4880 Discontinued
0.5731 Remote Similarity NPD2479 Phase 3
0.5731 Remote Similarity NPD6595 Phase 3
0.5731 Remote Similarity NPD2481 Approved
0.573 Remote Similarity NPD460 Discontinued
0.5723 Remote Similarity NPD1343 Approved
0.5723 Remote Similarity NPD2185 Clinical (unspecified phase)
0.5714 Remote Similarity NPD4524 Discontinued
0.5714 Remote Similarity NPD4112 Clinical (unspecified phase)
0.5706 Remote Similarity NPD4181 Approved
0.5706 Remote Similarity NPD6203 Clinical (unspecified phase)
0.5706 Remote Similarity NPD2144 Approved
0.5706 Remote Similarity NPD5592 Clinical (unspecified phase)
0.5698 Remote Similarity NPD3178 Discontinued
0.5686 Remote Similarity NPD680 Discontinued
0.568 Remote Similarity NPD4736 Clinical (unspecified phase)
0.5677 Remote Similarity NPD4047 Discontinued
0.5674 Remote Similarity NPD4922 Phase 2
0.5671 Remote Similarity NPD5400 Approved
0.5671 Remote Similarity NPD1853 Clinical (unspecified phase)
0.5667 Remote Similarity NPD4030 Approved
0.5667 Remote Similarity NPD4028 Approved
0.5667 Remote Similarity NPD4029 Approved
0.5665 Remote Similarity NPD2095 Phase 2
0.5665 Remote Similarity NPD2094 Phase 2
0.5665 Remote Similarity NPD2092 Phase 2
0.5664 Remote Similarity NPD748 Clinical (unspecified phase)
0.5664 Remote Similarity NPD1561 Phase 2
0.5655 Remote Similarity NPD3610 Approved
0.5655 Remote Similarity NPD6828 Phase 2
0.5655 Remote Similarity NPD3609 Approved
0.5655 Remote Similarity NPD6827 Clinical (unspecified phase)
0.5652 Remote Similarity NPD2061 Approved
0.565 Remote Similarity NPD4499 Approved
0.565 Remote Similarity NPD5685 Approved
0.565 Remote Similarity NPD5686 Approved
0.5649 Remote Similarity NPD1395 Clinical (unspecified phase)
0.5647 Remote Similarity NPD5104 Approved
0.5645 Remote Similarity NPD2008 Discontinued
0.5644 Remote Similarity NPD1630 Approved
0.5642 Remote Similarity NPD1304 Clinical (unspecified phase)
0.5641 Remote Similarity NPD751 Clinical (unspecified phase)
0.564 Remote Similarity NPD1643 Phase 3
0.5638 Remote Similarity NPD9726 Discontinued
0.5636 Remote Similarity NPD3583 Phase 2
0.5633 Remote Similarity NPD4702 Approved
0.5633 Remote Similarity NPD4703 Approved
0.5632 Remote Similarity NPD2096 Phase 2
0.5632 Remote Similarity NPD2091 Phase 2
0.5629 Remote Similarity NPD5021 Discontinued
0.5629 Remote Similarity NPD2844 Phase 3
0.5628 Remote Similarity NPD8248 Clinical (unspecified phase)
0.5625 Remote Similarity NPD9343 Clinical (unspecified phase)
0.5625 Remote Similarity NPD5590 Clinical (unspecified phase)
0.5625 Remote Similarity NPD3486 Clinical (unspecified phase)
0.5622 Remote Similarity NPD6176 Phase 1
0.5621 Remote Similarity NPD750 Phase 2
0.5615 Remote Similarity NPD708 Approved
0.5607 Remote Similarity NPD3038 Discontinued
0.5602 Remote Similarity NPD1568 Clinical (unspecified phase)
0.56 Remote Similarity NPD6610 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data