Structure

Physi-Chem Properties

Molecular Weight:  174.03
Volume:  174.955
LogP:  0.959
LogD:  1.076
LogS:  -3.604
# Rotatable Bonds:  0
TPSA:  51.21
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.436
Synthetic Accessibility Score:  2.133
Fsp3:  0.1
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.527
MDCK Permeability:  2.9579716283478774e-05
Pgp-inhibitor:  0.073
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.724
Plasma Protein Binding (PPB):  72.26123046875%
Volume Distribution (VD):  0.405
Pgp-substrate:  20.0046329498291%

ADMET: Metabolism

CYP1A2-inhibitor:  0.933
CYP1A2-substrate:  0.107
CYP2C19-inhibitor:  0.355
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.237
CYP2C9-substrate:  0.383
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.208
CYP3A4-inhibitor:  0.042
CYP3A4-substrate:  0.162

ADMET: Excretion

Clearance (CL):  6.788
Half-life (T1/2):  0.339

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.058
Drug-inuced Liver Injury (DILI):  0.935
AMES Toxicity:  0.804
Rat Oral Acute Toxicity:  0.335
Maximum Recommended Daily Dose:  0.024
Skin Sensitization:  0.843
Carcinogencity:  0.621
Eye Corrosion:  0.585
Eye Irritation:  0.987
Respiratory Toxicity:  0.497

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

  Natural Product: NPC156021

Natural Product ID:  NPC156021
Common Name*:   Lawsone
IUPAC Name:   n.a.
Synonyms:   2-Hydroxynaphthoquinone; Lawsone; NSC-8625
Standard InCHIKey:  CSFWPUWCSPOLJW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H
SMILES:  O=C1C=C(O)C(=O)c2c1cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL240963
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0000153] Naphthoquinones

*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
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. aerial part n.a. PMID[12033510]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. PMID[28165740]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota Pericarp n.a. n.a. PMID[9748380]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11196 Impatiens balsamina Species Balsaminaceae 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
NPT4312 Individual Protein Human rhinovirus A protease Human rhinovirus sp. IC50 > 150000.0 nM PMID[572139]
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 > 100000.0 nM PMID[572140]
NPT609 Individual Protein Human immunodeficiency virus type 1 protease Human immunodeficiency virus 1 IC50 > 100000.0 nM PMID[572140]
NPT201 Individual Protein Papain Carica papaya Inhibition = 82.0 % PMID[572141]
NPT1078 Individual Protein Indoleamine 2,3-dioxygenase Homo sapiens IC50 = 675000.0 nM PMID[572143]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 31622.8 nM PMID[572145]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 25118.9 nM PMID[572146]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 8912.5 nM PMID[572146]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 17782.8 nM PMID[572145]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 79432.8 nM PMID[572145]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 11220.2 nM PMID[572145]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 31.6 nM PMID[572146]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 15811.4 nM PMID[572145]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 15811.4 nM PMID[572146]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 28183.8 nM PMID[572146]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 25118.9 nM PMID[572146]
NPT569 Individual Protein Matrix metalloproteinase 8 Homo sapiens Inhibition = 86.0 % PMID[572147]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens Inhibition = 85.0 % PMID[572147]
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens Inhibition = 84.0 % PMID[572147]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens Inhibition = 84.0 % PMID[572147]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 69.0 % PMID[572147]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = 100.0 % PMID[572147]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Inhibition = 100.0 % PMID[572147]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 8912.5 nM PMID[572145]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 17782.8 nM PMID[572146]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 35481.3 nM PMID[572146]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 50118.7 nM PMID[572146]
NPT804 Cell Line HT-22 Mus musculus TC50 > 100000.0 nM PMID[572151]
NPT804 Cell Line HT-22 Mus musculus PD50 = 1005.0 nM PMID[572151]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 23109.3 nM PMID[572146]
NPT114 Cell Line LoVo Homo sapiens IC50 > 100000.0 nM PMID[572154]
NPT306 Cell Line PC-3 Homo sapiens IC50 > 100000.0 nM PMID[572154]
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 > 100000.0 nM PMID[572154]
NPT81 Cell Line A549 Homo sapiens IC50 = 58000.0 nM PMID[572154]
NPT3997 Individual Protein Hematopoietic cell protein-tyrosine phosphatase 70Z-PEP Homo sapiens IC50 = 5600.0 nM PMID[572155]
NPT165 Cell Line HeLa Homo sapiens IC50 > 100000.0 nM PMID[572156]
NPT2393 Cell Line SAS Homo sapiens IC50 > 100000.0 nM PMID[572156]
NPT993 Cell Line Hepatocyte Mus musculus CC50 > 500000.0 nM PMID[572158]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 213740.0 nM PMID[572158]
NPT134 Cell Line SK-BR-3 Homo sapiens IC50 > 50000.0 nM PMID[572162]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 50000.0 nM PMID[572162]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 50000.0 nM PMID[572162]
NPT1385 Individual Protein Histone-lysine N-methyltransferase SETD7 Homo sapiens IC50 > 200000.0 nM PMID[572163]
NPT32 Organism Mus musculus Mus musculus Lysis = 76.0 % PMID[572136]
NPT2 Others Unspecified ED25 = 33.0 mg kg-1 PMID[572137]
NPT2 Others Unspecified ED25 = 0.19 mM kg-1 PMID[572137]
NPT32 Organism Mus musculus Mus musculus Optimal dose = 104.0 % PMID[572137]
NPT32 Organism Mus musculus Mus musculus LD50 = 100.0 mg.kg-1 PMID[572137]
NPT35 Others n.a. Solubility = 255.0 ug.mL-1 PMID[572137]
NPT35 Others n.a. LogP = 1.07 n.a. PMID[572137]
NPT2 Others Unspecified IC50 = 100000.0 nM PMID[572138]
NPT32 Organism Mus musculus Mus musculus Activity = 23.0 % PMID[572142]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis Activity = 27.0 % PMID[572144]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis Activity = 49.0 % PMID[572144]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis Activity = 79.0 % PMID[572144]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis Activity = 86.0 % PMID[572144]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis Activity = 92.0 % PMID[572144]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis Activity = 100.0 % PMID[572144]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis Activity = 103.0 % PMID[572144]
NPT878 Organism Streptococcus mutans Streptococcus mutans Activity = 180.0 uM PMID[572144]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 15848.9 nM PMID[572145]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 39810.7 nM PMID[572146]
NPT69 Individual Protein Matrix metalloproteinase-1 Homo sapiens Inhibition = 86.0 % PMID[572147]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 2500000.0 nM PMID[572148]
NPT1499 Organism Erwinia amylovora Erwinia amylovora MIC = 2500000.0 nM PMID[572149]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 2500000.0 nM PMID[572150]
NPT27 Others Unspecified TI = 100.0 n.a. PMID[572151]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 99.76 % PMID[572152]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 101.6 % PMID[572152]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 31000.0 nM PMID[572154]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[572154]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 12.0 mm PMID[572156]
NPT20 Organism Candida albicans Candida albicans IZ = 14.0 mm PMID[572156]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 125.0 ug.mL-1 PMID[572156]
NPT20 Organism Candida albicans Candida albicans MIC = 250.0 ug.mL-1 PMID[572156]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 100000.0 nM PMID[572158]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 89050.0 nM PMID[572158]
NPT27 Others Unspecified Ratio CC50/IC50 = 2.39 n.a. PMID[572158]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC90 > 100000.0 nM PMID[572158]
NPT25570 SINGLE PROTEIN Dihydroorotate dehydrogenase (quinone), mitochondrial Schistosoma mansoni Activity = 9.7 % PMID[572159]
NPT25570 SINGLE PROTEIN Dihydroorotate dehydrogenase (quinone), mitochondrial Schistosoma mansoni IC50 = 29000.0 nM PMID[572159]
NPT21772 PROTEIN COMPLEX GroEL/GroES Escherichia coli Inhibition = 51.0 % PMID[572160]
NPT21772 PROTEIN COMPLEX GroEL/GroES Escherichia coli Inhibition = 84.0 % PMID[572160]
NPT2 Others Unspecified IC50 > 50000.0 nM PMID[572162]
NPT28243 SINGLE PROTEIN P2X purinoceptor 7 Mus musculus IC50 = 75480.0 nM PMID[572157]

☑ 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 NPC156021 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
0.9574 High Similarity NPC222390
0.9574 High Similarity NPC244427
0.9474 High Similarity NPC274443
0.9278 High Similarity NPC172483
0.9062 High Similarity NPC112552
0.8969 High Similarity NPC320891
0.8889 High Similarity NPC134120
0.8817 High Similarity NPC110704
0.8738 High Similarity NPC292834
0.8556 High Similarity NPC215008
0.8529 High Similarity NPC470391
0.8476 Intermediate Similarity NPC143768
0.8447 Intermediate Similarity NPC192577
0.8438 Intermediate Similarity NPC34243
0.8381 Intermediate Similarity NPC186128
0.8298 Intermediate Similarity NPC477704
0.8298 Intermediate Similarity NPC477693
0.8286 Intermediate Similarity NPC137315
0.8286 Intermediate Similarity NPC291799
0.8252 Intermediate Similarity NPC100767
0.8235 Intermediate Similarity NPC329282
0.8191 Intermediate Similarity NPC43945
0.8182 Intermediate Similarity NPC318173
0.8173 Intermediate Similarity NPC203732
0.8165 Intermediate Similarity NPC469843
0.8137 Intermediate Similarity NPC247976
0.8119 Intermediate Similarity NPC282895
0.8108 Intermediate Similarity NPC204784
0.8105 Intermediate Similarity NPC157778
0.81 Intermediate Similarity NPC229242
0.8091 Intermediate Similarity NPC323440
0.8091 Intermediate Similarity NPC222968
0.8091 Intermediate Similarity NPC80605
0.8058 Intermediate Similarity NPC249067
0.8056 Intermediate Similarity NPC241851
0.8056 Intermediate Similarity NPC326664
0.8041 Intermediate Similarity NPC476484
0.8039 Intermediate Similarity NPC284477
0.8036 Intermediate Similarity NPC105709
0.8 Intermediate Similarity NPC211439
0.7982 Intermediate Similarity NPC470764
0.7979 Intermediate Similarity NPC95965
0.7961 Intermediate Similarity NPC255676
0.7961 Intermediate Similarity NPC329556
0.7944 Intermediate Similarity NPC474057
0.7938 Intermediate Similarity NPC173413
0.79 Intermediate Similarity NPC12695
0.789 Intermediate Similarity NPC196673
0.7857 Intermediate Similarity NPC284475
0.7838 Intermediate Similarity NPC108288
0.7826 Intermediate Similarity NPC65627
0.7822 Intermediate Similarity NPC240042
0.7778 Intermediate Similarity NPC1682
0.7778 Intermediate Similarity NPC155232
0.7778 Intermediate Similarity NPC188844
0.7766 Intermediate Similarity NPC285773
0.7759 Intermediate Similarity NPC328107
0.7759 Intermediate Similarity NPC318067
0.7755 Intermediate Similarity NPC19256
0.7755 Intermediate Similarity NPC62765
0.7745 Intermediate Similarity NPC145052
0.7727 Intermediate Similarity NPC471721
0.7727 Intermediate Similarity NPC67377
0.7717 Intermediate Similarity NPC300205
0.7714 Intermediate Similarity NPC114594
0.7706 Intermediate Similarity NPC212415
0.7706 Intermediate Similarity NPC212718
0.7706 Intermediate Similarity NPC218855
0.77 Intermediate Similarity NPC238219
0.7692 Intermediate Similarity NPC245966
0.7692 Intermediate Similarity NPC310540
0.7692 Intermediate Similarity NPC295664
0.7692 Intermediate Similarity NPC25458
0.7679 Intermediate Similarity NPC158157
0.7677 Intermediate Similarity NPC133461
0.7664 Intermediate Similarity NPC226699
0.7664 Intermediate Similarity NPC141523
0.7658 Intermediate Similarity NPC93181
0.7653 Intermediate Similarity NPC418308
0.7647 Intermediate Similarity NPC103048
0.7647 Intermediate Similarity NPC289201
0.7642 Intermediate Similarity NPC209632
0.7636 Intermediate Similarity NPC471481
0.7636 Intermediate Similarity NPC470253
0.7636 Intermediate Similarity NPC231717
0.7634 Intermediate Similarity NPC71664
0.7634 Intermediate Similarity NPC164086
0.7629 Intermediate Similarity NPC194326
0.7629 Intermediate Similarity NPC322387
0.7627 Intermediate Similarity NPC236405
0.7624 Intermediate Similarity NPC172925
0.7619 Intermediate Similarity NPC60679
0.7615 Intermediate Similarity NPC265513
0.7609 Intermediate Similarity NPC36342
0.7609 Intermediate Similarity NPC2785
0.7609 Intermediate Similarity NPC285470
0.76 Intermediate Similarity NPC153885
0.76 Intermediate Similarity NPC59677
0.7593 Intermediate Similarity NPC17525
0.7593 Intermediate Similarity NPC318327
0.7593 Intermediate Similarity NPC85493
0.7589 Intermediate Similarity NPC62138
0.7579 Intermediate Similarity NPC273758
0.7576 Intermediate Similarity NPC303967
0.7576 Intermediate Similarity NPC110420
0.7576 Intermediate Similarity NPC67585
0.7573 Intermediate Similarity NPC329387
0.7573 Intermediate Similarity NPC317280
0.757 Intermediate Similarity NPC6984
0.757 Intermediate Similarity NPC37914
0.757 Intermediate Similarity NPC83409
0.757 Intermediate Similarity NPC185763
0.7568 Intermediate Similarity NPC234637
0.7568 Intermediate Similarity NPC477411
0.7568 Intermediate Similarity NPC11824
0.7568 Intermediate Similarity NPC196075
0.7568 Intermediate Similarity NPC130591
0.7565 Intermediate Similarity NPC285829
0.7565 Intermediate Similarity NPC206778
0.7563 Intermediate Similarity NPC81135
0.7563 Intermediate Similarity NPC231774
0.7563 Intermediate Similarity NPC51037
0.7553 Intermediate Similarity NPC273033
0.7553 Intermediate Similarity NPC12936
0.7553 Intermediate Similarity NPC73978
0.7551 Intermediate Similarity NPC267262
0.7549 Intermediate Similarity NPC61944
0.7526 Intermediate Similarity NPC318107
0.7526 Intermediate Similarity NPC160339
0.7526 Intermediate Similarity NPC307
0.7525 Intermediate Similarity NPC289883
0.7524 Intermediate Similarity NPC304873
0.7524 Intermediate Similarity NPC45613
0.7523 Intermediate Similarity NPC95172
0.75 Intermediate Similarity NPC54647
0.75 Intermediate Similarity NPC34715
0.75 Intermediate Similarity NPC112903
0.75 Intermediate Similarity NPC317645
0.75 Intermediate Similarity NPC217621
0.75 Intermediate Similarity NPC228435
0.7478 Intermediate Similarity NPC476645
0.7478 Intermediate Similarity NPC232178
0.7477 Intermediate Similarity NPC105899
0.7477 Intermediate Similarity NPC272524
0.7477 Intermediate Similarity NPC13784
0.7477 Intermediate Similarity NPC93287
0.7476 Intermediate Similarity NPC253423
0.7475 Intermediate Similarity NPC113307
0.7456 Intermediate Similarity NPC471553
0.7455 Intermediate Similarity NPC21162
0.7455 Intermediate Similarity NPC260818
0.7455 Intermediate Similarity NPC116842
0.7455 Intermediate Similarity NPC210089
0.7451 Intermediate Similarity NPC260233
0.7447 Intermediate Similarity NPC190567
0.7447 Intermediate Similarity NPC127343
0.7438 Intermediate Similarity NPC237225
0.7438 Intermediate Similarity NPC165257
0.7436 Intermediate Similarity NPC120545
0.7434 Intermediate Similarity NPC322197
0.7434 Intermediate Similarity NPC226093
0.7431 Intermediate Similarity NPC269023
0.7431 Intermediate Similarity NPC224584
0.7431 Intermediate Similarity NPC99846
0.7417 Intermediate Similarity NPC15837
0.7407 Intermediate Similarity NPC37622
0.7407 Intermediate Similarity NPC30594
0.7404 Intermediate Similarity NPC134882
0.7404 Intermediate Similarity NPC75724
0.7404 Intermediate Similarity NPC49994
0.74 Intermediate Similarity NPC86670
0.74 Intermediate Similarity NPC274455
0.74 Intermediate Similarity NPC277277
0.74 Intermediate Similarity NPC70940
0.7396 Intermediate Similarity NPC39600
0.7395 Intermediate Similarity NPC164014
0.7387 Intermediate Similarity NPC321852
0.7387 Intermediate Similarity NPC114682
0.7387 Intermediate Similarity NPC66208
0.7387 Intermediate Similarity NPC268388
0.7383 Intermediate Similarity NPC31786
0.7374 Intermediate Similarity NPC329064
0.7373 Intermediate Similarity NPC91478
0.7373 Intermediate Similarity NPC307174
0.7368 Intermediate Similarity NPC145053
0.7353 Intermediate Similarity NPC261181
0.735 Intermediate Similarity NPC472981
0.7345 Intermediate Similarity NPC274839
0.7345 Intermediate Similarity NPC215419
0.7345 Intermediate Similarity NPC306740
0.7345 Intermediate Similarity NPC474685
0.7345 Intermediate Similarity NPC228936
0.7345 Intermediate Similarity NPC186933
0.7345 Intermediate Similarity NPC476357
0.7345 Intermediate Similarity NPC474408
0.7345 Intermediate Similarity NPC217111
0.7333 Intermediate Similarity NPC123506
0.7317 Intermediate Similarity NPC27659
0.7308 Intermediate Similarity NPC265220
0.7308 Intermediate Similarity NPC239185

  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 NPC156021 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
0.8191 Intermediate Similarity NPD650 Approved
0.8058 Intermediate Similarity NPD1237 Approved
0.7965 Intermediate Similarity NPD4879 Approved
0.7961 Intermediate Similarity NPD1929 Approved
0.7961 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD1930 Approved
0.7864 Intermediate Similarity NPD1932 Approved
0.7857 Intermediate Similarity NPD7609 Phase 3
0.7843 Intermediate Similarity NPD2066 Phase 3
0.7838 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7631 Approved
0.7766 Intermediate Similarity NPD9491 Approved
0.7755 Intermediate Similarity NPD9258 Approved
0.7755 Intermediate Similarity NPD9256 Approved
0.7706 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.77 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD1508 Approved
0.7553 Intermediate Similarity NPD942 Approved
0.7527 Intermediate Similarity NPD9490 Approved
0.7526 Intermediate Similarity NPD9257 Approved
0.7526 Intermediate Similarity NPD9259 Approved
0.75 Intermediate Similarity NPD1239 Approved
0.7451 Intermediate Similarity NPD1693 Approved
0.7431 Intermediate Similarity NPD2329 Discontinued
0.7431 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD1090 Approved
0.74 Intermediate Similarity NPD1086 Approved
0.74 Intermediate Similarity NPD1089 Approved
0.7383 Intermediate Similarity NPD164 Approved
0.7379 Intermediate Similarity NPD1843 Approved
0.7373 Intermediate Similarity NPD4878 Approved
0.7368 Intermediate Similarity NPD226 Approved
0.7353 Intermediate Similarity NPD1202 Approved
0.7308 Intermediate Similarity NPD3495 Discontinued
0.73 Intermediate Similarity NPD800 Approved
0.7255 Intermediate Similarity NPD1088 Approved
0.7238 Intermediate Similarity NPD9495 Approved
0.7193 Intermediate Similarity NPD5951 Approved
0.7182 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1565 Approved
0.7143 Intermediate Similarity NPD1566 Phase 3
0.7143 Intermediate Similarity NPD1564 Approved
0.7117 Intermediate Similarity NPD2182 Approved
0.71 Intermediate Similarity NPD1087 Approved
0.7083 Intermediate Similarity NPD1507 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD1317 Discontinued
0.7053 Intermediate Similarity NPD225 Approved
0.7053 Intermediate Similarity NPD227 Approved
0.7049 Intermediate Similarity NPD1470 Approved
0.7043 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD9264 Approved
0.7027 Intermediate Similarity NPD9267 Approved
0.7027 Intermediate Similarity NPD9263 Approved
0.7009 Intermediate Similarity NPD1238 Approved
0.7 Intermediate Similarity NPD1201 Approved
0.6991 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6975 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6964 Remote Similarity NPD9266 Approved
0.6964 Remote Similarity NPD74 Approved
0.6952 Remote Similarity NPD9260 Approved
0.6949 Remote Similarity NPD7009 Phase 2
0.6931 Remote Similarity NPD506 Clinical (unspecified phase)
0.6931 Remote Similarity NPD4793 Discontinued
0.6903 Remote Similarity NPD664 Approved
0.6897 Remote Similarity NPD1246 Approved
0.6891 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6864 Remote Similarity NPD7610 Discontinued
0.6857 Remote Similarity NPD1563 Approved
0.6833 Remote Similarity NPD2345 Approved
0.6833 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6818 Remote Similarity NPD9261 Approved
0.6796 Remote Similarity NPD5346 Phase 2
0.6796 Remote Similarity NPD5347 Phase 2
0.6757 Remote Similarity NPD5909 Discontinued
0.675 Remote Similarity NPD1245 Approved
0.6729 Remote Similarity NPD1989 Approved
0.6694 Remote Similarity NPD1876 Approved
0.6667 Remote Similarity NPD6647 Phase 2
0.6667 Remote Similarity NPD1241 Discontinued
0.6667 Remote Similarity NPD9545 Approved
0.6639 Remote Similarity NPD9493 Approved
0.6638 Remote Similarity NPD9508 Approved
0.661 Remote Similarity NPD9281 Approved
0.6591 Remote Similarity NPD651 Clinical (unspecified phase)
0.6581 Remote Similarity NPD5277 Phase 2
0.6574 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6557 Remote Similarity NPD2932 Approved
0.6549 Remote Similarity NPD1018 Approved
0.6535 Remote Similarity NPD3971 Phase 1
0.6532 Remote Similarity NPD3972 Approved
0.6512 Remote Similarity NPD3764 Approved
0.6508 Remote Similarity NPD1164 Approved
0.6504 Remote Similarity NPD7457 Clinical (unspecified phase)
0.648 Remote Similarity NPD5159 Phase 2
0.648 Remote Similarity NPD5157 Phase 1
0.648 Remote Similarity NPD5158 Clinical (unspecified phase)
0.648 Remote Similarity NPD182 Clinical (unspecified phase)
0.6471 Remote Similarity NPD2629 Approved
0.6466 Remote Similarity NPD2067 Discontinued
0.6466 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6462 Remote Similarity NPD7961 Discontinued
0.6457 Remote Similarity NPD4980 Approved
0.6457 Remote Similarity NPD2798 Approved
0.6457 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6455 Remote Similarity NPD253 Approved
0.6434 Remote Similarity NPD7008 Discontinued
0.6434 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6429 Remote Similarity NPD1574 Approved
0.6423 Remote Similarity NPD3019 Approved
0.6415 Remote Similarity NPD3673 Approved
0.6415 Remote Similarity NPD3672 Approved
0.6392 Remote Similarity NPD9716 Approved
0.6378 Remote Similarity NPD1593 Approved
0.6377 Remote Similarity NPD3300 Phase 2
0.637 Remote Similarity NPD1471 Phase 3
0.6364 Remote Similarity NPD1100 Approved
0.6364 Remote Similarity NPD1099 Approved
0.6364 Remote Similarity NPD9566 Approved
0.6341 Remote Similarity NPD4102 Approved
0.6341 Remote Similarity NPD4105 Approved
0.632 Remote Similarity NPD518 Clinical (unspecified phase)
0.632 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6858 Approved
0.6303 Remote Similarity NPD7094 Approved
0.629 Remote Similarity NPD5305 Approved
0.629 Remote Similarity NPD5306 Approved
0.6288 Remote Similarity NPD1240 Approved
0.6288 Remote Similarity NPD943 Approved
0.6283 Remote Similarity NPD2648 Phase 3
0.6283 Remote Similarity NPD2193 Phase 2
0.6283 Remote Similarity NPD2171 Approved
0.627 Remote Similarity NPD9717 Approved
0.6263 Remote Similarity NPD9294 Approved
0.6261 Remote Similarity NPD999 Phase 2
0.626 Remote Similarity NPD2313 Discontinued
0.6259 Remote Similarity NPD7236 Approved
0.625 Remote Similarity NPD2346 Discontinued
0.625 Remote Similarity NPD1203 Approved
0.625 Remote Similarity NPD2652 Approved
0.625 Remote Similarity NPD2650 Approved
0.625 Remote Similarity NPD2344 Approved
0.625 Remote Similarity NPD3097 Clinical (unspecified phase)
0.624 Remote Similarity NPD4136 Approved
0.624 Remote Similarity NPD4135 Approved
0.624 Remote Similarity NPD4106 Approved
0.6239 Remote Similarity NPD719 Approved
0.6239 Remote Similarity NPD720 Approved
0.6232 Remote Similarity NPD3750 Approved
0.6228 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6228 Remote Similarity NPD3357 Discontinued
0.6226 Remote Similarity NPD1101 Approved
0.6222 Remote Similarity NPD3299 Clinical (unspecified phase)
0.622 Remote Similarity NPD1755 Approved
0.621 Remote Similarity NPD9268 Approved
0.6195 Remote Similarity NPD3135 Clinical (unspecified phase)
0.6194 Remote Similarity NPD1607 Approved
0.619 Remote Similarity NPD4807 Approved
0.619 Remote Similarity NPD4806 Approved
0.619 Remote Similarity NPD6287 Discontinued
0.6182 Remote Similarity NPD2934 Approved
0.6182 Remote Similarity NPD2933 Approved
0.6176 Remote Similarity NPD5405 Approved
0.6176 Remote Similarity NPD5406 Approved
0.6176 Remote Similarity NPD5408 Approved
0.6176 Remote Similarity NPD5404 Approved
0.6174 Remote Similarity NPD2577 Clinical (unspecified phase)
0.6172 Remote Similarity NPD1283 Approved
0.6165 Remote Similarity NPD4452 Approved
0.6165 Remote Similarity NPD4453 Approved
0.6165 Remote Similarity NPD4445 Approved
0.616 Remote Similarity NPD1362 Clinical (unspecified phase)
0.616 Remote Similarity NPD1104 Approved
0.6147 Remote Similarity NPD752 Approved
0.6142 Remote Similarity NPD9269 Phase 2
0.6142 Remote Similarity NPD1608 Approved
0.614 Remote Similarity NPD2196 Discontinued
0.6136 Remote Similarity NPD5422 Clinical (unspecified phase)
0.6132 Remote Similarity NPD9538 Approved
0.6131 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6126 Remote Similarity NPD2859 Approved
0.6126 Remote Similarity NPD2860 Approved
0.6121 Remote Similarity NPD5048 Discontinued
0.6121 Remote Similarity NPD1040 Phase 2
0.6116 Remote Similarity NPD1280 Clinical (unspecified phase)
0.6116 Remote Similarity NPD3598 Phase 3
0.6111 Remote Similarity NPD3023 Approved
0.6111 Remote Similarity NPD3026 Approved
0.6106 Remote Similarity NPD3020 Approved
0.6106 Remote Similarity NPD7798 Approved
0.6103 Remote Similarity NPD2799 Discontinued
0.6103 Remote Similarity NPD1510 Phase 2
0.6103 Remote Similarity NPD3748 Approved
0.6098 Remote Similarity NPD3797 Approved
0.6091 Remote Similarity NPD1066 Discontinued
0.6091 Remote Similarity NPD845 Approved
0.6087 Remote Similarity NPD5765 Approved
0.608 Remote Similarity NPD3025 Approved
0.608 Remote Similarity NPD1651 Approved

  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