Structure

Physi-Chem Properties

Molecular Weight:  255.98
Volume:  218.581
LogP:  3.505
LogD:  3.1
LogS:  -3.696
# Rotatable Bonds:  2
TPSA:  58.93
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.655
Synthetic Accessibility Score:  2.743
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.451
MDCK Permeability:  5.302726640366018e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.769
Plasma Protein Binding (PPB):  98.68815612792969%
Volume Distribution (VD):  1.052
Pgp-substrate:  1.5722280740737915%

ADMET: Metabolism

CYP1A2-inhibitor:  0.983
CYP1A2-substrate:  0.143
CYP2C19-inhibitor:  0.978
CYP2C19-substrate:  0.111
CYP2C9-inhibitor:  0.899
CYP2C9-substrate:  0.845
CYP2D6-inhibitor:  0.828
CYP2D6-substrate:  0.103
CYP3A4-inhibitor:  0.952
CYP3A4-substrate:  0.299

ADMET: Excretion

Clearance (CL):  9.613
Half-life (T1/2):  0.562

ADMET: Toxicity

hERG Blockers:  0.251
Human Hepatotoxicity (H-HT):  0.169
Drug-inuced Liver Injury (DILI):  0.87
AMES Toxicity:  0.59
Rat Oral Acute Toxicity:  0.139
Maximum Recommended Daily Dose:  0.895
Skin Sensitization:  0.777
Carcinogencity:  0.045
Eye Corrosion:  0.015
Eye Irritation:  0.781
Respiratory Toxicity:  0.555

Download Data

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

  Natural Product: NPC115049

Natural Product ID:  NPC115049
Common Name*:   Pyrrolnitrin
IUPAC Name:   3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
Synonyms:   52230; Pyrrolnitrin
Standard InCHIKey:  QJBZDBLBQWFTPZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H
SMILES:  c1cc(c2c[nH]cc2Cl)c(c(c1)Cl)N(=O)=O
Synthetic Gene Cluster:   BGC0000924;
ChEMBL Identifier:   CHEMBL97972
PubChem CID:   13916
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000090] Pyrroles
        • [CHEMONTID:0002257] Substituted pyrroles
          • [CHEMONTID:0002334] Phenylpyrroles

*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
NPO8493 Capraria biflora Species Scrophulariaceae Eukaryota n.a. n.a. n.a. PMID[11087595]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[23149469]
NPO8881 Centipeda minima Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23189738]
NPO18104 Acinetobacter haemolyticus Species Moraxellaceae Bacteria n.a. n.a. n.a. PMID[23990066]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25679537]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25901993]
NPO17226 Burkholderia pyrrocinia Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[4955234]
NPO8881 Centipeda minima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21339 Upuna borneensis Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11075 Aglaia tomentosa Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8881 Centipeda minima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8881 Centipeda minima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8881 Centipeda minima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21339 Upuna borneensis Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8881 Centipeda minima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11075 Aglaia tomentosa Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8239 Mentha timija Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18405 Trichoderma avellaneum Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10032 Backhousia citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8493 Capraria biflora Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17226 Burkholderia pyrrocinia Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18104 Acinetobacter haemolyticus Species Moraxellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO1807 Senecio macrocephalus 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
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 21313.8 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 26603.2 nM PubChem BioAssay data set
NPT189 Cell Line Vero Chlorocebus aethiops MTD50 = 8.0 ug ml-1 PMID[504810]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 12589.3 nM PMID[504811]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 31622.8 nM PMID[504811]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 3548.1 nM PMID[504811]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 39810.7 nM PMID[504811]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 21136.0 nM PMID[504811]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 14963.1 nM PMID[504812]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 21136.0 nM PMID[504812]
NPT2 Others Unspecified Potency n.a. 33491.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 23914.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 26603.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4771.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2984.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 29849.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6682.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21313.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3010.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 26832.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 23710.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1333.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 18833.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10590.9 nM PubChem BioAssay data set
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 4.0 ug.mL-1 PMID[504810]
NPT1513 Organism Mycobacterium avium Mycobacterium avium MIC = 8.0 ug.mL-1 PMID[504810]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 16.0 ug.mL-1 PMID[504810]
NPT4071 Organism Mycobacterium gordonae Mycobacterium gordonae MIC > 16.0 ug.mL-1 PMID[504810]
NPT1830 Organism Mycobacterium marinum Mycobacterium marinum MIC > 16.0 ug.mL-1 PMID[504810]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 300.0 ug.mL-1 PMID[504813]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[504814]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[504814]

☑ 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 NPC115049 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
0.7778 Intermediate Similarity NPC96102
0.7727 Intermediate Similarity NPC84911
0.7727 Intermediate Similarity NPC105127
0.7662 Intermediate Similarity NPC29886
0.7662 Intermediate Similarity NPC261195
0.7632 Intermediate Similarity NPC82295
0.7628 Intermediate Similarity NPC110126
0.7628 Intermediate Similarity NPC73767
0.7595 Intermediate Similarity NPC190296
0.758 Intermediate Similarity NPC279081
0.758 Intermediate Similarity NPC469767
0.758 Intermediate Similarity NPC230002
0.758 Intermediate Similarity NPC469784
0.758 Intermediate Similarity NPC469768
0.758 Intermediate Similarity NPC469779
0.758 Intermediate Similarity NPC469783
0.758 Intermediate Similarity NPC469761
0.758 Intermediate Similarity NPC469780
0.7572 Intermediate Similarity NPC314919
0.7532 Intermediate Similarity NPC476454
0.7532 Intermediate Similarity NPC469766
0.7515 Intermediate Similarity NPC236711
0.75 Intermediate Similarity NPC314372
0.75 Intermediate Similarity NPC159856
0.7407 Intermediate Similarity NPC471957
0.7365 Intermediate Similarity NPC477591
0.7346 Intermediate Similarity NPC143872
0.7346 Intermediate Similarity NPC288838
0.7317 Intermediate Similarity NPC105818
0.7317 Intermediate Similarity NPC24678
0.7301 Intermediate Similarity NPC469811
0.7288 Intermediate Similarity NPC83381
0.7273 Intermediate Similarity NPC216713
0.7256 Intermediate Similarity NPC321911
0.7239 Intermediate Similarity NPC63545
0.7229 Intermediate Similarity NPC469786
0.7229 Intermediate Similarity NPC469763
0.7229 Intermediate Similarity NPC469760
0.7229 Intermediate Similarity NPC73952
0.7229 Intermediate Similarity NPC259644
0.7229 Intermediate Similarity NPC469765
0.7229 Intermediate Similarity NPC200214
0.7229 Intermediate Similarity NPC25008
0.7212 Intermediate Similarity NPC53947
0.7202 Intermediate Similarity NPC469762
0.7195 Intermediate Similarity NPC201380
0.7195 Intermediate Similarity NPC179787
0.7186 Intermediate Similarity NPC75540
0.7186 Intermediate Similarity NPC211572
0.7186 Intermediate Similarity NPC80597
0.7186 Intermediate Similarity NPC212376
0.7186 Intermediate Similarity NPC70922
0.7169 Intermediate Similarity NPC470823
0.7158 Intermediate Similarity NPC315617
0.7158 Intermediate Similarity NPC316359
0.7143 Intermediate Similarity NPC476464
0.7143 Intermediate Similarity NPC469785
0.7126 Intermediate Similarity NPC325903
0.7126 Intermediate Similarity NPC141926
0.7118 Intermediate Similarity NPC279918
0.7083 Intermediate Similarity NPC34844
0.7081 Intermediate Similarity NPC315348
0.7081 Intermediate Similarity NPC32002
0.7076 Intermediate Similarity NPC282231
0.7073 Intermediate Similarity NPC285731
0.7065 Intermediate Similarity NPC316018
0.7065 Intermediate Similarity NPC314058
0.7059 Intermediate Similarity NPC135141
0.7059 Intermediate Similarity NPC92796
0.7035 Intermediate Similarity NPC311276
0.7035 Intermediate Similarity NPC194640
0.703 Intermediate Similarity NPC316069
0.7018 Intermediate Similarity NPC131718
0.7006 Intermediate Similarity NPC22079
0.7 Intermediate Similarity NPC216643
0.7 Intermediate Similarity NPC325252
0.7 Intermediate Similarity NPC286427
0.7 Intermediate Similarity NPC218268
0.6988 Remote Similarity NPC470111
0.6977 Remote Similarity NPC225018
0.6959 Remote Similarity NPC318065
0.6959 Remote Similarity NPC56765
0.6959 Remote Similarity NPC206819
0.6959 Remote Similarity NPC230869
0.6959 Remote Similarity NPC41257
0.6957 Remote Similarity NPC150259
0.6954 Remote Similarity NPC54988
0.6954 Remote Similarity NPC474561
0.6954 Remote Similarity NPC160105
0.6954 Remote Similarity NPC49954
0.6948 Remote Similarity NPC27740
0.6937 Remote Similarity NPC198988
0.6936 Remote Similarity NPC40779
0.6919 Remote Similarity NPC122141
0.6919 Remote Similarity NPC470204
0.6914 Remote Similarity NPC63751
0.6883 Remote Similarity NPC46358
0.6879 Remote Similarity NPC470203
0.6864 Remote Similarity NPC470233
0.6859 Remote Similarity NPC250361
0.6857 Remote Similarity NPC49217
0.6852 Remote Similarity NPC125746
0.6839 Remote Similarity NPC90723
0.6839 Remote Similarity NPC317105
0.6839 Remote Similarity NPC102423
0.6836 Remote Similarity NPC470498
0.6821 Remote Similarity NPC215584
0.6821 Remote Similarity NPC44773
0.6818 Remote Similarity NPC41174
0.6818 Remote Similarity NPC78020
0.68 Remote Similarity NPC17751
0.68 Remote Similarity NPC42372
0.68 Remote Similarity NPC280864
0.6798 Remote Similarity NPC314603
0.6792 Remote Similarity NPC282398
0.678 Remote Similarity NPC194411
0.6776 Remote Similarity NPC91958
0.6776 Remote Similarity NPC165495
0.6772 Remote Similarity NPC473762
0.6772 Remote Similarity NPC89490
0.6768 Remote Similarity NPC88097
0.676 Remote Similarity NPC110500
0.676 Remote Similarity NPC203468
0.676 Remote Similarity NPC149155
0.6744 Remote Similarity NPC51054
0.6743 Remote Similarity NPC149265
0.673 Remote Similarity NPC475090
0.673 Remote Similarity NPC473587
0.673 Remote Similarity NPC475105
0.673 Remote Similarity NPC329896
0.6727 Remote Similarity NPC2949
0.6727 Remote Similarity NPC115611
0.6727 Remote Similarity NPC59084
0.6723 Remote Similarity NPC201700
0.6722 Remote Similarity NPC267885
0.6705 Remote Similarity NPC274229
0.6688 Remote Similarity NPC166424
0.6688 Remote Similarity NPC146373
0.6688 Remote Similarity NPC245244
0.6687 Remote Similarity NPC473868
0.6687 Remote Similarity NPC475428
0.6687 Remote Similarity NPC63157
0.6685 Remote Similarity NPC248454
0.6685 Remote Similarity NPC84827
0.6685 Remote Similarity NPC59269
0.6685 Remote Similarity NPC145885
0.6685 Remote Similarity NPC32534
0.6685 Remote Similarity NPC14113
0.6685 Remote Similarity NPC68354
0.6667 Remote Similarity NPC204141
0.6667 Remote Similarity NPC37423
0.6667 Remote Similarity NPC290094
0.6667 Remote Similarity NPC470440
0.6667 Remote Similarity NPC275305
0.6667 Remote Similarity NPC470677
0.6667 Remote Similarity NPC143603
0.6648 Remote Similarity NPC11126
0.6648 Remote Similarity NPC248041
0.6648 Remote Similarity NPC283219
0.6648 Remote Similarity NPC126709
0.6647 Remote Similarity NPC161550
0.6646 Remote Similarity NPC314102
0.6646 Remote Similarity NPC179365
0.6646 Remote Similarity NPC475450
0.6646 Remote Similarity NPC101165
0.6646 Remote Similarity NPC251722
0.6645 Remote Similarity NPC182570
0.6645 Remote Similarity NPC48564
0.6645 Remote Similarity NPC265605
0.6628 Remote Similarity NPC138842
0.6611 Remote Similarity NPC313791
0.6611 Remote Similarity NPC477611
0.6605 Remote Similarity NPC473930
0.6593 Remote Similarity NPC240088
0.6593 Remote Similarity NPC284775
0.6593 Remote Similarity NPC473380
0.6593 Remote Similarity NPC111275
0.6592 Remote Similarity NPC116961
0.6592 Remote Similarity NPC97343
0.6591 Remote Similarity NPC242116
0.6576 Remote Similarity NPC233936
0.6575 Remote Similarity NPC293216
0.6557 Remote Similarity NPC276540
0.6557 Remote Similarity NPC55772
0.6557 Remote Similarity NPC213468
0.6557 Remote Similarity NPC176199
0.6557 Remote Similarity NPC233050
0.6557 Remote Similarity NPC265710
0.6557 Remote Similarity NPC215795
0.6556 Remote Similarity NPC82331
0.655 Remote Similarity NPC2272
0.655 Remote Similarity NPC187951
0.655 Remote Similarity NPC37548
0.6545 Remote Similarity NPC471312
0.6541 Remote Similarity NPC163055
0.6541 Remote Similarity NPC169625
0.6541 Remote Similarity NPC202957
0.6538 Remote Similarity NPC474958
0.6522 Remote Similarity NPC16659
0.6512 Remote Similarity NPC40070

  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 NPC115049 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
0.7778 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD1248 Discontinued
0.7628 Intermediate Similarity NPD786 Approved
0.7532 Intermediate Similarity NPD1722 Approved
0.7516 Intermediate Similarity NPD768 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD473 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD3100 Discontinued
0.7256 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD3339 Approved
0.7212 Intermediate Similarity NPD2172 Phase 1
0.7207 Intermediate Similarity NPD1227 Phase 2
0.7202 Intermediate Similarity NPD2865 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2165 Phase 1
0.7167 Intermediate Similarity NPD6217 Discontinued
0.7143 Intermediate Similarity NPD3115 Approved
0.7143 Intermediate Similarity NPD3112 Approved
0.7143 Intermediate Similarity NPD3114 Approved
0.7143 Intermediate Similarity NPD3113 Approved
0.7143 Intermediate Similarity NPD7185 Discontinued
0.7118 Intermediate Similarity NPD1404 Approved
0.7118 Intermediate Similarity NPD1403 Approved
0.711 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD2072 Approved
0.7081 Intermediate Similarity NPD2073 Approved
0.7081 Intermediate Similarity NPD2074 Approved
0.7081 Intermediate Similarity NPD2075 Approved
0.7069 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD2837 Discontinued
0.6977 Remote Similarity NPD972 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2642 Approved
0.6954 Remote Similarity NPD2639 Approved
0.6923 Remote Similarity NPD2012 Clinical (unspecified phase)
0.6914 Remote Similarity NPD2641 Approved
0.6914 Remote Similarity NPD2640 Approved
0.6914 Remote Similarity NPD2185 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4463 Approved
0.6905 Remote Similarity NPD4462 Approved
0.6851 Remote Similarity NPD4891 Phase 2
0.6839 Remote Similarity NPD3323 Discontinued
0.6836 Remote Similarity NPD3117 Approved
0.6836 Remote Similarity NPD3116 Approved
0.6829 Remote Similarity NPD165 Phase 2
0.6815 Remote Similarity NPD992 Clinical (unspecified phase)
0.6815 Remote Similarity NPD991 Phase 2
0.6782 Remote Similarity NPD1853 Clinical (unspecified phase)
0.6776 Remote Similarity NPD5892 Approved
0.6768 Remote Similarity NPD945 Clinical (unspecified phase)
0.6763 Remote Similarity NPD1554 Clinical (unspecified phase)
0.676 Remote Similarity NPD482 Approved
0.6727 Remote Similarity NPD3943 Clinical (unspecified phase)
0.6722 Remote Similarity NPD749 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6497 Approved
0.6704 Remote Similarity NPD4112 Clinical (unspecified phase)
0.6687 Remote Similarity NPD3476 Approved
0.6687 Remote Similarity NPD3475 Approved
0.6686 Remote Similarity NPD4384 Clinical (unspecified phase)
0.6685 Remote Similarity NPD3505 Approved
0.6685 Remote Similarity NPD3506 Approved
0.6685 Remote Similarity NPD2144 Approved
0.6684 Remote Similarity NPD4848 Phase 1
0.6667 Remote Similarity NPD4128 Approved
0.6667 Remote Similarity NPD5065 Approved
0.6649 Remote Similarity NPD2868 Clinical (unspecified phase)
0.6648 Remote Similarity NPD4079 Approved
0.6648 Remote Similarity NPD3609 Approved
0.6648 Remote Similarity NPD4076 Approved
0.6648 Remote Similarity NPD3610 Approved
0.6645 Remote Similarity NPD271 Approved
0.6645 Remote Similarity NPD270 Clinical (unspecified phase)
0.6645 Remote Similarity NPD268 Approved
0.663 Remote Similarity NPD4075 Phase 2
0.6625 Remote Similarity NPD3654 Approved
0.6612 Remote Similarity NPD6595 Phase 3
0.6612 Remote Similarity NPD6277 Clinical (unspecified phase)
0.6609 Remote Similarity NPD1192 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5254 Discontinued
0.6604 Remote Similarity NPD2118 Approved
0.6604 Remote Similarity NPD2119 Approved
0.6603 Remote Similarity NPD748 Clinical (unspecified phase)
0.6596 Remote Similarity NPD6133 Discontinued
0.6593 Remote Similarity NPD6203 Clinical (unspecified phase)
0.6593 Remote Similarity NPD4181 Approved
0.6592 Remote Similarity NPD4973 Approved
0.6588 Remote Similarity NPD4547 Phase 3
0.6584 Remote Similarity NPD6803 Clinical (unspecified phase)
0.6576 Remote Similarity NPD3038 Discontinued
0.6573 Remote Similarity NPD3929 Clinical (unspecified phase)
0.6561 Remote Similarity NPD4699 Discontinued
0.655 Remote Similarity NPD5538 Clinical (unspecified phase)
0.655 Remote Similarity NPD2430 Phase 2
0.6548 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6548 Remote Similarity NPD4637 Clinical (unspecified phase)
0.6548 Remote Similarity NPD2006 Phase 2
0.6545 Remote Similarity NPD1262 Discovery
0.6541 Remote Similarity NPD5105 Approved
0.6541 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6541 Remote Similarity NPD2092 Phase 2
0.6541 Remote Similarity NPD2095 Phase 2
0.6541 Remote Similarity NPD2094 Phase 2
0.6541 Remote Similarity NPD9583 Approved
0.6541 Remote Similarity NPD5106 Approved
0.6538 Remote Similarity NPD2771 Approved
0.6536 Remote Similarity NPD4779 Clinical (unspecified phase)
0.6519 Remote Similarity NPD409 Clinical (unspecified phase)
0.651 Remote Similarity NPD2316 Clinical (unspecified phase)
0.6505 Remote Similarity NPD2096 Phase 2
0.6505 Remote Similarity NPD2091 Phase 2
0.65 Remote Similarity NPD1598 Discontinued
0.6497 Remote Similarity NPD2385 Clinical (unspecified phase)
0.6471 Remote Similarity NPD269 Clinical (unspecified phase)
0.6463 Remote Similarity NPD3385 Approved
0.6463 Remote Similarity NPD4029 Approved
0.6463 Remote Similarity NPD4028 Approved
0.6463 Remote Similarity NPD4030 Approved
0.6457 Remote Similarity NPD2580 Discontinued
0.6453 Remote Similarity NPD3852 Clinical (unspecified phase)
0.6443 Remote Similarity NPD3230 Clinical (unspecified phase)
0.6442 Remote Similarity NPD803 Phase 1
0.6433 Remote Similarity NPD1683 Approved
0.6432 Remote Similarity NPD4913 Phase 3
0.6429 Remote Similarity NPD7217 Approved
0.6429 Remote Similarity NPD7216 Approved
0.6429 Remote Similarity NPD750 Phase 2
0.642 Remote Similarity NPD5541 Clinical (unspecified phase)
0.6417 Remote Similarity NPD3607 Clinical (unspecified phase)
0.6415 Remote Similarity NPD9357 Approved
0.6409 Remote Similarity NPD5436 Phase 1
0.6402 Remote Similarity NPD8431 Approved
0.6402 Remote Similarity NPD5590 Clinical (unspecified phase)
0.6402 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6402 Remote Similarity NPD2310 Clinical (unspecified phase)
0.6402 Remote Similarity NPD3961 Discontinued
0.6398 Remote Similarity NPD1707 Approved
0.6398 Remote Similarity NPD1708 Approved
0.6398 Remote Similarity NPD1895 Discontinued
0.6383 Remote Similarity NPD6610 Clinical (unspecified phase)
0.6369 Remote Similarity NPD1902 Approved
0.6369 Remote Similarity NPD1904 Approved
0.6368 Remote Similarity NPD8110 Clinical (unspecified phase)
0.6368 Remote Similarity NPD2728 Approved
0.6368 Remote Similarity NPD2729 Approved
0.6368 Remote Similarity NPD2730 Approved
0.6364 Remote Similarity NPD2748 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3944 Approved
0.6364 Remote Similarity NPD4912 Phase 3
0.6364 Remote Similarity NPD3942 Approved
0.6364 Remote Similarity NPD1332 Clinical (unspecified phase)
0.6359 Remote Similarity NPD6471 Clinical (unspecified phase)
0.6349 Remote Similarity NPD4426 Clinical (unspecified phase)
0.6344 Remote Similarity NPD3927 Phase 2
0.6341 Remote Similarity NPD9726 Discontinued
0.634 Remote Similarity NPD1851 Clinical (unspecified phase)
0.6335 Remote Similarity NPD1905 Clinical (unspecified phase)
0.6333 Remote Similarity NPD1002 Clinical (unspecified phase)
0.6332 Remote Similarity NPD6288 Clinical (unspecified phase)
0.6325 Remote Similarity NPD4880 Discontinued
0.6324 Remote Similarity NPD1322 Clinical (unspecified phase)
0.631 Remote Similarity NPD4011 Clinical (unspecified phase)
0.6307 Remote Similarity NPD976 Approved
0.6307 Remote Similarity NPD975 Approved
0.6307 Remote Similarity NPD977 Approved
0.6302 Remote Similarity NPD6180 Clinical (unspecified phase)
0.6301 Remote Similarity NPD1661 Suspended
0.6301 Remote Similarity NPD2110 Approved
0.6296 Remote Similarity NPD3771 Phase 3
0.6294 Remote Similarity NPD1382 Phase 2
0.6294 Remote Similarity NPD1383 Phase 3
0.6283 Remote Similarity NPD1534 Approved
0.6282 Remote Similarity NPD9392 Approved
0.6282 Remote Similarity NPD9396 Approved
0.628 Remote Similarity NPD715 Phase 3
0.6272 Remote Similarity NPD680 Discontinued
0.6268 Remote Similarity NPD6615 Clinical (unspecified phase)
0.6264 Remote Similarity NPD4640 Approved
0.6264 Remote Similarity NPD4639 Approved
0.6264 Remote Similarity NPD4638 Approved
0.6257 Remote Similarity NPD6454 Clinical (unspecified phase)
0.625 Remote Similarity NPD2938 Approved
0.625 Remote Similarity NPD2940 Approved
0.6237 Remote Similarity NPD1038 Approved
0.6237 Remote Similarity NPD802 Phase 2
0.6236 Remote Similarity NPD2145 Clinical (unspecified phase)
0.6226 Remote Similarity NPD9598 Discontinued
0.6222 Remote Similarity NPD5315 Discontinued
0.6211 Remote Similarity NPD1937 Approved
0.6207 Remote Similarity NPD4702 Approved
0.6207 Remote Similarity NPD4703 Approved
0.6205 Remote Similarity NPD7619 Phase 3
0.6205 Remote Similarity NPD7618 Phase 3
0.6199 Remote Similarity NPD1592 Phase 3
0.619 Remote Similarity NPD490 Clinical (unspecified phase)
0.6186 Remote Similarity NPD4615 Phase 2
0.6186 Remote Similarity NPD4922 Phase 2
0.6176 Remote Similarity NPD2070 Approved
0.6176 Remote Similarity NPD2069 Approved
0.6176 Remote Similarity NPD2071 Approved
0.6176 Remote Similarity NPD2068 Approved
0.6171 Remote Similarity NPD1204 Discontinued
0.6171 Remote Similarity NPD1183 Approved
0.6166 Remote Similarity NPD1213 Phase 3

  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