Structure

Physi-Chem Properties

Molecular Weight:  174.12
Volume:  193.147
LogP:  1.943
LogD:  1.531
LogS:  -1.178
# Rotatable Bonds:  2
TPSA:  19.03
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.739
Synthetic Accessibility Score:  1.837
Fsp3:  0.273
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:  -4.44
MDCK Permeability:  1.1245942005189136e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  26.952922821044922%
Volume Distribution (VD):  2.704
Pgp-substrate:  67.87498474121094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.446
CYP1A2-substrate:  0.95
CYP2C19-inhibitor:  0.049
CYP2C19-substrate:  0.936
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.648
CYP2D6-inhibitor:  0.963
CYP2D6-substrate:  0.93
CYP3A4-inhibitor:  0.012
CYP3A4-substrate:  0.291

ADMET: Excretion

Clearance (CL):  10.459
Half-life (T1/2):  0.76

ADMET: Toxicity

hERG Blockers:  0.082
Human Hepatotoxicity (H-HT):  0.433
Drug-inuced Liver Injury (DILI):  0.822
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.944
Maximum Recommended Daily Dose:  0.869
Skin Sensitization:  0.862
Carcinogencity:  0.059
Eye Corrosion:  0.757
Eye Irritation:  0.382
Respiratory Toxicity:  0.98

Download Data

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Similar NPs/Drugs  

  Natural Product: NPC110126

Natural Product ID:  NPC110126
Common Name*:   Gramine
IUPAC Name:   1-(1H-indol-3-yl)-N,N-dimethylmethanamine
Synonyms:   Gramine
Standard InCHIKey:  OCDGBSUVYYVKQZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3/p+1
SMILES:  CN(C)CC1=C[NH2+]c2ccccc12
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL254348
PubChem CID:   6890
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002497] Indoles
          • [CHEMONTID:0004196] 3-alkylindoles

*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
NPO24195 Stylissa carteri Species Axinellidae Eukaryota n.a. n.a. n.a. PMID[15043426]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. PMID[15516765]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[18270436]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. PMID[20973550]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21574561]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota Stems n.a. n.a. PMID[22079755]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. PMID[23700450]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23747095]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[23793896]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. leaf n.a. PMID[23849114]
NPO3866 Pistia stratiotes Species Araceae Eukaryota n.a. n.a. n.a. PMID[24258601]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. PMID[24310066]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. seed n.a. PMID[24967651]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. seed n.a. PMID[25433632]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. seed n.a. PMID[26860358]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29192771]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. PMID[31861466]
NPO24195 Stylissa carteri Species Axinellidae Eukaryota n.a. indopacific n.a. PMID[9917317]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Shoot Essent. Oil n.a. n.a. Database[FooDB]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO8541 Oryza sativa Species Poaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8541 Oryza sativa Species Poaceae Eukaryota Petiole n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8541 Oryza sativa Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8541 Oryza sativa Species Poaceae Eukaryota Protoplast n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8541 Oryza sativa Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8541 Oryza sativa Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21685 Magnolia coco Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19287 Phalaris arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. seed n.a. Database[MetaboLights]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21685 Magnolia coco Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19287 Phalaris arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21685 Magnolia coco Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19287 Phalaris arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8541 Oryza sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24195 Stylissa carteri Species Axinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2502 Lupinus mexicanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19287 Phalaris arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12511 Leplaea thompsonii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16529 Plagiodera versicolora Species Chrysomelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3866 Pistia stratiotes Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21685 Magnolia coco Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21102 Thalictrum wangii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21982 Erechtites hieraciifolius Species Asteraceae 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
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[515614]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 31622.8 nM PMID[515614]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 15848.9 nM PMID[515615]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 31622.8 nM PMID[515615]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 31622.8 nM PMID[515615]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[515615]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 15848.9 nM PMID[515614]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 10000.0 nM PMID[515615]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 3162.3 nM PMID[515616]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 158.5 nM PMID[515616]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 6513.1 nM PMID[515617]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 707.9 nM PMID[515617]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 3162.28 nM PMID[515616]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens AC50 = 158.49 nM PMID[515616]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 15.3 % PMID[515618]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 74.5 ug.mL-1 PMID[515619]
NPT547 Cell Line BGC-823 Homo sapiens IC50 = 62.8 ug.mL-1 PMID[515619]
NPT515 Cell Line SGC-7901 Homo sapiens IC50 = 77.3 ug.mL-1 PMID[515619]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 100.0 ug.mL-1 PMID[515619]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 12995.3 nM PMID[515620]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 11582.1 nM PMID[515620]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29855.4 nM PMID[515621]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 10322.5 nM PMID[515617]
NPT519 Cell Line SH-SY5Y Homo sapiens Activity = 45.0 % PMID[515622]
NPT530 Organism Caenorhabditis elegans Caenorhabditis elegans Activity = 2.0 % PMID[515613]
NPT530 Organism Caenorhabditis elegans Caenorhabditis elegans Activity = 3.0 % PMID[515613]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[515614]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 39810.7 nM PMID[515614]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 15848.9 nM PMID[515616]
NPT2 Others Unspecified Potency = 2238.7 nM PMID[515614]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9285.0 nM PMID[515617]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[515617]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 8275.3 nM PMID[515617]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 10.59 % PMID[515618]
NPT4902 Protein Complex Voltage-gated calcium channel Homo sapiens Inhibition = 25.0 % PMID[515622]
NPT2 Others Unspecified Activity = 80.0 % PMID[515622]
NPT2 Others Unspecified Activity = 76.0 % PMID[515622]
NPT21789 CELL-LINE Cortical neurones n.a. Activity = 0.0 % PMID[515622]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[515623]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[515623]

☑ 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 NPC110126 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
0.9848 High Similarity NPC73767
0.9847 High Similarity NPC105127
0.9847 High Similarity NPC84911
0.9771 High Similarity NPC96102
0.9771 High Similarity NPC261195
0.9771 High Similarity NPC29886
0.9627 High Similarity NPC469779
0.9627 High Similarity NPC469767
0.9627 High Similarity NPC469780
0.9627 High Similarity NPC469784
0.9627 High Similarity NPC469761
0.9627 High Similarity NPC469783
0.9627 High Similarity NPC469768
0.9556 High Similarity NPC469766
0.9485 High Similarity NPC190296
0.9481 High Similarity NPC279081
0.9466 High Similarity NPC82295
0.9348 High Similarity NPC314372
0.9338 High Similarity NPC230002
0.9214 High Similarity NPC471957
0.9209 High Similarity NPC159856
0.9149 High Similarity NPC321911
0.9143 High Similarity NPC143872
0.9143 High Similarity NPC288838
0.9091 High Similarity NPC200214
0.9085 High Similarity NPC24678
0.9085 High Similarity NPC105818
0.9085 High Similarity NPC53947
0.9078 High Similarity NPC469811
0.9078 High Similarity NPC201380
0.9078 High Similarity NPC179787
0.9028 High Similarity NPC34844
0.9021 High Similarity NPC470823
0.9007 High Similarity NPC63545
0.8971 High Similarity NPC198988
0.8958 High Similarity NPC25008
0.8958 High Similarity NPC73952
0.8958 High Similarity NPC141926
0.8958 High Similarity NPC469760
0.8958 High Similarity NPC469763
0.8958 High Similarity NPC469765
0.8958 High Similarity NPC259644
0.8958 High Similarity NPC469786
0.8955 High Similarity NPC22079
0.8905 High Similarity NPC325252
0.8897 High Similarity NPC75540
0.8897 High Similarity NPC211572
0.8897 High Similarity NPC70922
0.8897 High Similarity NPC80597
0.8897 High Similarity NPC212376
0.8889 High Similarity NPC216713
0.8844 High Similarity NPC318065
0.8844 High Similarity NPC56765
0.8844 High Similarity NPC206819
0.8841 High Similarity NPC150259
0.8828 High Similarity NPC325903
0.8786 High Similarity NPC59084
0.8779 High Similarity NPC41174
0.8776 High Similarity NPC286427
0.8768 High Similarity NPC218268
0.8759 High Similarity NPC470233
0.8723 High Similarity NPC473868
0.8723 High Similarity NPC63157
0.8716 High Similarity NPC41257
0.8707 High Similarity NPC469785
0.8667 High Similarity NPC90723
0.8657 High Similarity NPC250361
0.8652 High Similarity NPC2949
0.8652 High Similarity NPC115611
0.8649 High Similarity NPC216643
0.8649 High Similarity NPC236711
0.8649 High Similarity NPC469762
0.8611 High Similarity NPC316069
0.8603 High Similarity NPC473587
0.86 High Similarity NPC282231
0.8591 High Similarity NPC92796
0.8591 High Similarity NPC135141
0.8582 High Similarity NPC88097
0.8571 High Similarity NPC125746
0.8553 High Similarity NPC49217
0.8543 High Similarity NPC149265
0.8543 High Similarity NPC311276
0.8543 High Similarity NPC317105
0.854 High Similarity NPC475428
0.8533 High Similarity NPC215584
0.8533 High Similarity NPC470204
0.8533 High Similarity NPC44773
0.8533 High Similarity NPC279918
0.8533 High Similarity NPC122141
0.8533 High Similarity NPC131718
0.8529 High Similarity NPC473762
0.8507 High Similarity NPC27740
0.8478 Intermediate Similarity NPC475450
0.8478 Intermediate Similarity NPC179365
0.8477 Intermediate Similarity NPC470203
0.8467 Intermediate Similarity NPC230869
0.8442 Intermediate Similarity NPC194411
0.844 Intermediate Similarity NPC314102
0.844 Intermediate Similarity NPC251722
0.8433 Intermediate Similarity NPC46358
0.8431 Intermediate Similarity NPC49954
0.8431 Intermediate Similarity NPC160105
0.8431 Intermediate Similarity NPC474561
0.8425 Intermediate Similarity NPC21605
0.8421 Intermediate Similarity NPC40779
0.8414 Intermediate Similarity NPC285731
0.8414 Intermediate Similarity NPC470440
0.8387 Intermediate Similarity NPC82331
0.8366 Intermediate Similarity NPC17751
0.8366 Intermediate Similarity NPC280864
0.8312 Intermediate Similarity NPC54988
0.8311 Intermediate Similarity NPC40070
0.8301 Intermediate Similarity NPC102423
0.8288 Intermediate Similarity NPC204141
0.8286 Intermediate Similarity NPC473930
0.8284 Intermediate Similarity NPC182570
0.8284 Intermediate Similarity NPC48564
0.8284 Intermediate Similarity NPC265605
0.828 Intermediate Similarity NPC275305
0.828 Intermediate Similarity NPC37423
0.8269 Intermediate Similarity NPC470498
0.8258 Intermediate Similarity NPC201700
0.8258 Intermediate Similarity NPC63751
0.8247 Intermediate Similarity NPC274229
0.8243 Intermediate Similarity NPC2272
0.8228 Intermediate Similarity NPC474958
0.8217 Intermediate Similarity NPC477611
0.8217 Intermediate Similarity NPC314603
0.8188 Intermediate Similarity NPC33421
0.8182 Intermediate Similarity NPC194640
0.8176 Intermediate Similarity NPC14113
0.8176 Intermediate Similarity NPC473380
0.8176 Intermediate Similarity NPC240088
0.8176 Intermediate Similarity NPC470111
0.8176 Intermediate Similarity NPC145885
0.8176 Intermediate Similarity NPC84827
0.8176 Intermediate Similarity NPC68354
0.8175 Intermediate Similarity NPC146373
0.8175 Intermediate Similarity NPC245244
0.8175 Intermediate Similarity NPC166424
0.8143 Intermediate Similarity NPC282398
0.8141 Intermediate Similarity NPC78020
0.8137 Intermediate Similarity NPC233936
0.8129 Intermediate Similarity NPC42372
0.8125 Intermediate Similarity NPC176199
0.8125 Intermediate Similarity NPC265710
0.8125 Intermediate Similarity NPC215795
0.8125 Intermediate Similarity NPC11126
0.8113 Intermediate Similarity NPC267885
0.8113 Intermediate Similarity NPC280852
0.8101 Intermediate Similarity NPC313791
0.8092 Intermediate Similarity NPC476464
0.8089 Intermediate Similarity NPC97343
0.8075 Intermediate Similarity NPC16659
0.8075 Intermediate Similarity NPC314919
0.8067 Intermediate Similarity NPC148592
0.8063 Intermediate Similarity NPC248454
0.806 Intermediate Similarity NPC91958
0.805 Intermediate Similarity NPC293216
0.805 Intermediate Similarity NPC110500
0.805 Intermediate Similarity NPC203468
0.805 Intermediate Similarity NPC149155
0.8026 Intermediate Similarity NPC476297
0.8026 Intermediate Similarity NPC476219
0.8014 Intermediate Similarity NPC284635
0.8012 Intermediate Similarity NPC248041
0.8012 Intermediate Similarity NPC126709
0.8 Intermediate Similarity NPC225018
0.8 Intermediate Similarity NPC169433
0.8 Intermediate Similarity NPC37548
0.7987 Intermediate Similarity NPC221786
0.7987 Intermediate Similarity NPC475990
0.7987 Intermediate Similarity NPC474880
0.7974 Intermediate Similarity NPC51054
0.7973 Intermediate Similarity NPC242556
0.7963 Intermediate Similarity NPC164228
0.7958 Intermediate Similarity NPC101165
0.795 Intermediate Similarity NPC151939
0.795 Intermediate Similarity NPC59269
0.795 Intermediate Similarity NPC284775
0.7949 Intermediate Similarity NPC478184
0.7945 Intermediate Similarity NPC312092
0.7945 Intermediate Similarity NPC104483
0.7937 Intermediate Similarity NPC280297
0.7927 Intermediate Similarity NPC228835
0.791 Intermediate Similarity NPC148140
0.7905 Intermediate Similarity NPC20144
0.7901 Intermediate Similarity NPC233050
0.7901 Intermediate Similarity NPC276540
0.7901 Intermediate Similarity NPC213468
0.7901 Intermediate Similarity NPC283219
0.7871 Intermediate Similarity NPC477591
0.7866 Intermediate Similarity NPC163055
0.7853 Intermediate Similarity NPC300688
0.7852 Intermediate Similarity NPC81561
0.7843 Intermediate Similarity NPC232798
0.784 Intermediate Similarity NPC111275
0.7838 Intermediate Similarity NPC476454
0.7831 Intermediate Similarity NPC474707
0.7831 Intermediate Similarity NPC94752

  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 NPC110126 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
0.9771 High Similarity NPD198 Clinical (unspecified phase)
0.9699 High Similarity NPD786 Approved
0.9412 High Similarity NPD1722 Approved
0.9286 High Similarity NPD3100 Discontinued
0.9085 High Similarity NPD2172 Phase 1
0.9014 High Similarity NPD4374 Clinical (unspecified phase)
0.8958 High Similarity NPD2837 Discontinued
0.8784 High Similarity NPD1403 Approved
0.8784 High Similarity NPD1404 Approved
0.8667 High Similarity NPD3323 Discontinued
0.8652 High Similarity NPD3943 Clinical (unspecified phase)
0.8603 High Similarity NPD3654 Approved
0.8593 High Similarity NPD992 Clinical (unspecified phase)
0.8593 High Similarity NPD991 Phase 2
0.8553 High Similarity NPD2642 Approved
0.8553 High Similarity NPD2639 Approved
0.8531 High Similarity NPD4637 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD2640 Approved
0.8497 Intermediate Similarity NPD2641 Approved
0.8497 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.8477 Intermediate Similarity NPD1853 Clinical (unspecified phase)
0.8472 Intermediate Similarity NPD5254 Discontinued
0.8425 Intermediate Similarity NPD4547 Phase 3
0.8406 Intermediate Similarity NPD3475 Approved
0.8406 Intermediate Similarity NPD3476 Approved
0.8387 Intermediate Similarity NPD3609 Approved
0.8387 Intermediate Similarity NPD3610 Approved
0.8377 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.8357 Intermediate Similarity NPD3385 Approved
0.8344 Intermediate Similarity NPD4075 Phase 2
0.8323 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD2118 Approved
0.8321 Intermediate Similarity NPD2119 Approved
0.8284 Intermediate Similarity NPD271 Approved
0.8284 Intermediate Similarity NPD268 Approved
0.8284 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD4128 Approved
0.828 Intermediate Similarity NPD5065 Approved
0.8276 Intermediate Similarity NPD2006 Phase 2
0.8243 Intermediate Similarity NPD2430 Phase 2
0.8231 Intermediate Similarity NPD1683 Approved
0.8212 Intermediate Similarity NPD473 Clinical (unspecified phase)
0.8212 Intermediate Similarity NPD2580 Discontinued
0.8188 Intermediate Similarity NPD4462 Approved
0.8188 Intermediate Similarity NPD4463 Approved
0.8182 Intermediate Similarity NPD1262 Discovery
0.8176 Intermediate Similarity NPD3505 Approved
0.8176 Intermediate Similarity NPD3506 Approved
0.8176 Intermediate Similarity NPD2144 Approved
0.8176 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD4181 Approved
0.8158 Intermediate Similarity NPD1192 Clinical (unspecified phase)
0.8158 Intermediate Similarity NPD2865 Clinical (unspecified phase)
0.8146 Intermediate Similarity NPD2165 Phase 1
0.8125 Intermediate Similarity NPD4079 Approved
0.8125 Intermediate Similarity NPD4076 Approved
0.812 Intermediate Similarity NPD9392 Approved
0.812 Intermediate Similarity NPD9396 Approved
0.8116 Intermediate Similarity NPD9583 Approved
0.8113 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD4029 Approved
0.8099 Intermediate Similarity NPD4030 Approved
0.8099 Intermediate Similarity NPD4028 Approved
0.8092 Intermediate Similarity NPD3114 Approved
0.8092 Intermediate Similarity NPD3112 Approved
0.8092 Intermediate Similarity NPD3115 Approved
0.8092 Intermediate Similarity NPD3113 Approved
0.8077 Intermediate Similarity NPD1248 Discontinued
0.805 Intermediate Similarity NPD482 Approved
0.8027 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD3038 Discontinued
0.8025 Intermediate Similarity NPD1707 Approved
0.8025 Intermediate Similarity NPD1708 Approved
0.8025 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD1256 Approved
0.7986 Intermediate Similarity NPD1255 Approved
0.7986 Intermediate Similarity NPD1254 Approved
0.7986 Intermediate Similarity NPD1253 Approved
0.7975 Intermediate Similarity NPD5105 Approved
0.7975 Intermediate Similarity NPD1332 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD5106 Approved
0.7972 Intermediate Similarity NPD3944 Approved
0.7972 Intermediate Similarity NPD3942 Approved
0.7971 Intermediate Similarity NPD9357 Approved
0.797 Intermediate Similarity NPD269 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD6595 Phase 3
0.7958 Intermediate Similarity NPD803 Phase 1
0.7927 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD3961 Discontinued
0.7887 Intermediate Similarity NPD715 Phase 3
0.7885 Intermediate Similarity NPD2385 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD750 Phase 2
0.7862 Intermediate Similarity NPD5436 Phase 1
0.7831 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD6217 Discontinued
0.7826 Intermediate Similarity NPD748 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD768 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD1895 Discontinued
0.7801 Intermediate Similarity NPD1598 Discontinued
0.7792 Intermediate Similarity NPD977 Approved
0.7792 Intermediate Similarity NPD976 Approved
0.7792 Intermediate Similarity NPD975 Approved
0.7784 Intermediate Similarity NPD5590 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD5315 Discontinued
0.7758 Intermediate Similarity NPD2095 Phase 2
0.7758 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD2094 Phase 2
0.7758 Intermediate Similarity NPD2092 Phase 2
0.7754 Intermediate Similarity NPD9598 Discontinued
0.7742 Intermediate Similarity NPD2150 Discontinued
0.7711 Intermediate Similarity NPD2096 Phase 2
0.7711 Intermediate Similarity NPD2091 Phase 2
0.7703 Intermediate Similarity NPD2072 Approved
0.7703 Intermediate Similarity NPD2068 Approved
0.7703 Intermediate Similarity NPD2073 Approved
0.7703 Intermediate Similarity NPD2069 Approved
0.7703 Intermediate Similarity NPD2075 Approved
0.7703 Intermediate Similarity NPD2071 Approved
0.7703 Intermediate Similarity NPD2070 Approved
0.7703 Intermediate Similarity NPD2074 Approved
0.7692 Intermediate Similarity NPD5145 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD947 Approved
0.7687 Intermediate Similarity NPD45 Approved
0.7687 Intermediate Similarity NPD6554 Approved
0.7679 Intermediate Similarity NPD8431 Approved
0.7673 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD1528 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD1918 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7619 Phase 3
0.7616 Intermediate Similarity NPD7618 Phase 3
0.76 Intermediate Similarity NPD1592 Phase 3
0.7593 Intermediate Similarity NPD1567 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD3117 Approved
0.7593 Intermediate Similarity NPD3116 Approved
0.7582 Intermediate Similarity NPD4702 Approved
0.7582 Intermediate Similarity NPD4703 Approved
0.7578 Intermediate Similarity NPD4640 Approved
0.7578 Intermediate Similarity NPD4639 Approved
0.7578 Intermediate Similarity NPD4638 Approved
0.7574 Intermediate Similarity NPD2310 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD2960 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD802 Phase 2
0.755 Intermediate Similarity NPD4047 Discontinued
0.7544 Intermediate Similarity NPD6180 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD1326 Approved
0.7531 Intermediate Similarity NPD1325 Approved
0.7529 Intermediate Similarity NPD6664 Approved
0.75 Intermediate Similarity NPD490 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3339 Approved
0.7485 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD4649 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6828 Phase 2
0.7485 Intermediate Similarity NPD6827 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3833 Phase 3
0.7484 Intermediate Similarity NPD3835 Phase 3
0.747 Intermediate Similarity NPD3341 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD5021 Discontinued
0.7469 Intermediate Similarity NPD2390 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD1661 Suspended
0.7467 Intermediate Similarity NPD680 Discontinued
0.7466 Intermediate Similarity NPD1251 Discontinued
0.7457 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD1038 Approved
0.7457 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD1313 Approved
0.745 Intermediate Similarity NPD200 Phase 2
0.745 Intermediate Similarity NPD201 Phase 2
0.7439 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD4880 Discontinued
0.7415 Intermediate Similarity NPD1995 Approved
0.7415 Intermediate Similarity NPD1994 Approved
0.7415 Intermediate Similarity NPD1993 Approved
0.7405 Intermediate Similarity NPD2748 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD4615 Phase 2
0.7396 Intermediate Similarity NPD7564 Discontinued
0.7389 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD6278 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD9098 Phase 3
0.7353 Intermediate Similarity NPD1227 Phase 2
0.7349 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD5995 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6771 Discontinued
0.7308 Intermediate Similarity NPD1183 Approved
0.7305 Intermediate Similarity NPD7111 Discontinued
0.729 Intermediate Similarity NPD7469 Discontinued
0.7284 Intermediate Similarity NPD5138 Approved
0.7284 Intermediate Similarity NPD5140 Approved
0.7273 Intermediate Similarity NPD3401 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD2930 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD1029 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD1030 Approved
0.7261 Intermediate Similarity NPD1027 Approved
0.725 Intermediate Similarity NPD4326 Phase 2

  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