Structure

Physi-Chem Properties

Molecular Weight:  136.05
Volume:  145.402
LogP:  2.215
LogD:  2.372
LogS:  -2.236
# Rotatable Bonds:  2
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.546
Synthetic Accessibility Score:  1.092
Fsp3:  0.125
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:  -4.281
MDCK Permeability:  3.2647807529428974e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.749
Plasma Protein Binding (PPB):  85.7992935180664%
Volume Distribution (VD):  1.465
Pgp-substrate:  11.788017272949219%

ADMET: Metabolism

CYP1A2-inhibitor:  0.966
CYP1A2-substrate:  0.819
CYP2C19-inhibitor:  0.741
CYP2C19-substrate:  0.476
CYP2C9-inhibitor:  0.178
CYP2C9-substrate:  0.72
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.313
CYP3A4-inhibitor:  0.022
CYP3A4-substrate:  0.246

ADMET: Excretion

Clearance (CL):  10.228
Half-life (T1/2):  0.863

ADMET: Toxicity

hERG Blockers:  0.067
Human Hepatotoxicity (H-HT):  0.032
Drug-inuced Liver Injury (DILI):  0.666
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.01
Maximum Recommended Daily Dose:  0.011
Skin Sensitization:  0.499
Carcinogencity:  0.06
Eye Corrosion:  0.189
Eye Irritation:  0.992
Respiratory Toxicity:  0.089

Download Data

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

  Natural Product: NPC130398

Natural Product ID:  NPC130398
Common Name*:   Methyl Benzoate
IUPAC Name:   methyl benzoate
Synonyms:   Benzoic acid methyl ester; Methyl benzoate
Standard InCHIKey:  QPJVMBTYPHYUOC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3
SMILES:  COC(=O)c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL16435
PubChem CID:   7150
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters

*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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12350137]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota rhizome n.a. n.a. PMID[12617587]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[12932131]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[20460582]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota leaves n.a. n.a. PMID[20584613]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota roots n.a. n.a. PMID[22381047]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[23153397]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. leaf n.a. PMID[23901173]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[25172746]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[28068085]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[8910532]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9584408]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome Essent. Oil n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO310 Flos mume Species Lycaenidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO310 Flos mume Species Lycaenidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12468 Asarum heterotropoides Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12468 Asarum heterotropoides Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29078 Asiasarum sieboldii n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4659 Asiasarum heterotropoides n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12468 Asarum heterotropoides Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29078 Asiasarum sieboldii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4659 Asiasarum heterotropoides n.a. n.a. n.a. 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
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 12589.3 nM PMID[507692]
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 39810.7 nM PMID[507692]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 31622.8 nM PMID[507692]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 44668.4 nM PMID[507692]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 74978.0 nM PMID[507692]
NPT102 Individual Protein Interleukin-8 Homo sapiens Potency n.a. 74978.0 nM PMID[507692]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 1778.3 nM PMID[507692]
NPT2 Others Unspecified Potency n.a. 3889.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21872.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 67892.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 95901 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43641.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61057 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48064.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54417.1 nM PubChem BioAssay data set
NPT35 Others n.a. Log S = -1.85 n.a. PMID[507689]
NPT35 Others n.a. Log PNalk = 2.13 n.a. PMID[507690]
NPT27 Others Unspecified log Ks = 2.5 n.a. PMID[507691]
NPT2 Others Unspecified Potency = 316.2 nM PMID[507692]
NPT1280 Organism Thrips tabaci Thrips tabaci Ratio = 6.6 n.a. PMID[507693]
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 50.5 n.a. PMID[507693]
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 49.1 n.a. PMID[507693]
NPT35 Others n.a. LogD = 1.9 n.a. PMID[507694]
NPT35 Others n.a. LogP = 2.1 n.a. PMID[507694]
NPT35 Others n.a. LogP = 2.27 n.a. PMID[507695]

☑ 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 NPC130398 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
0.9778 High Similarity NPC276775
0.9778 High Similarity NPC249912
0.9778 High Similarity NPC92754
0.967 High Similarity NPC35448
0.967 High Similarity NPC225060
0.967 High Similarity NPC78701
0.9565 High Similarity NPC203925
0.9565 High Similarity NPC146351
0.9462 High Similarity NPC70624
0.9362 High Similarity NPC188895
0.9355 High Similarity NPC325497
0.9355 High Similarity NPC118343
0.9263 High Similarity NPC474365
0.9263 High Similarity NPC301943
0.9255 High Similarity NPC42211
0.9167 High Similarity NPC31786
0.9091 High Similarity NPC318107
0.9 High Similarity NPC173443
0.898 High Similarity NPC119271
0.8889 High Similarity NPC56493
0.8878 High Similarity NPC269457
0.8878 High Similarity NPC209632
0.8866 High Similarity NPC89886
0.8866 High Similarity NPC60679
0.8817 High Similarity NPC261181
0.88 High Similarity NPC17417
0.88 High Similarity NPC469636
0.88 High Similarity NPC10251
0.88 High Similarity NPC474364
0.88 High Similarity NPC83628
0.88 High Similarity NPC85493
0.88 High Similarity NPC265407
0.8788 High Similarity NPC30594
0.8788 High Similarity NPC37622
0.8778 High Similarity NPC89377
0.8776 High Similarity NPC114594
0.8763 High Similarity NPC45613
0.8737 High Similarity NPC253423
0.8713 High Similarity NPC93084
0.8713 High Similarity NPC174099
0.8713 High Similarity NPC214067
0.8713 High Similarity NPC196246
0.8713 High Similarity NPC251854
0.8696 High Similarity NPC62765
0.8646 High Similarity NPC229242
0.8627 High Similarity NPC476003
0.8627 High Similarity NPC260818
0.8627 High Similarity NPC210089
0.8627 High Similarity NPC305912
0.8627 High Similarity NPC474157
0.8627 High Similarity NPC1082
0.8614 High Similarity NPC99846
0.8614 High Similarity NPC269023
0.8587 High Similarity NPC220893
0.8557 High Similarity NPC217621
0.8556 High Similarity NPC58616
0.8544 High Similarity NPC270699
0.8544 High Similarity NPC321852
0.8544 High Similarity NPC82899
0.8539 High Similarity NPC288903
0.8462 Intermediate Similarity NPC161611
0.8462 Intermediate Similarity NPC272524
0.8462 Intermediate Similarity NPC128368
0.8447 Intermediate Similarity NPC167504
0.8438 Intermediate Similarity NPC61944
0.8404 Intermediate Similarity NPC119631
0.8384 Intermediate Similarity NPC25458
0.8384 Intermediate Similarity NPC304873
0.8381 Intermediate Similarity NPC474363
0.8381 Intermediate Similarity NPC153053
0.8381 Intermediate Similarity NPC308744
0.8381 Intermediate Similarity NPC307651
0.8365 Intermediate Similarity NPC474314
0.8365 Intermediate Similarity NPC79496
0.8365 Intermediate Similarity NPC158282
0.8352 Intermediate Similarity NPC294134
0.8351 Intermediate Similarity NPC270654
0.8302 Intermediate Similarity NPC81808
0.8302 Intermediate Similarity NPC210092
0.8302 Intermediate Similarity NPC474685
0.8286 Intermediate Similarity NPC474176
0.828 Intermediate Similarity NPC304760
0.8224 Intermediate Similarity NPC188907
0.8224 Intermediate Similarity NPC149691
0.8224 Intermediate Similarity NPC220540
0.82 Intermediate Similarity NPC284477
0.8182 Intermediate Similarity NPC228435
0.8148 Intermediate Similarity NPC128825
0.8148 Intermediate Similarity NPC131192
0.8137 Intermediate Similarity NPC105899
0.8131 Intermediate Similarity NPC306740
0.8119 Intermediate Similarity NPC255676
0.81 Intermediate Similarity NPC282895
0.8095 Intermediate Similarity NPC243355
0.8073 Intermediate Similarity NPC45104
0.8073 Intermediate Similarity NPC240664
0.8073 Intermediate Similarity NPC217423
0.8068 Intermediate Similarity NPC287790
0.8068 Intermediate Similarity NPC3672
0.8058 Intermediate Similarity NPC1065
0.8056 Intermediate Similarity NPC100353
0.8037 Intermediate Similarity NPC237366
0.8021 Intermediate Similarity NPC110704
0.8019 Intermediate Similarity NPC23332
0.8 Intermediate Similarity NPC94637
0.8 Intermediate Similarity NPC27633
0.8 Intermediate Similarity NPC94298
0.7981 Intermediate Similarity NPC249811
0.7935 Intermediate Similarity NPC285773
0.7928 Intermediate Similarity NPC90522
0.7928 Intermediate Similarity NPC61779
0.7928 Intermediate Similarity NPC328459
0.7925 Intermediate Similarity NPC183648
0.7921 Intermediate Similarity NPC473325
0.7917 Intermediate Similarity NPC213156
0.7917 Intermediate Similarity NPC240108
0.7909 Intermediate Similarity NPC469574
0.7889 Intermediate Similarity NPC167577
0.7889 Intermediate Similarity NPC78517
0.787 Intermediate Similarity NPC196075
0.787 Intermediate Similarity NPC53953
0.787 Intermediate Similarity NPC477411
0.7857 Intermediate Similarity NPC230951
0.7857 Intermediate Similarity NPC72977
0.7857 Intermediate Similarity NPC473243
0.785 Intermediate Similarity NPC54626
0.785 Intermediate Similarity NPC212415
0.785 Intermediate Similarity NPC57879
0.783 Intermediate Similarity NPC234639
0.7826 Intermediate Similarity NPC323103
0.7826 Intermediate Similarity NPC106313
0.7822 Intermediate Similarity NPC98911
0.7822 Intermediate Similarity NPC472318
0.7818 Intermediate Similarity NPC470860
0.7812 Intermediate Similarity NPC9822
0.781 Intermediate Similarity NPC470391
0.7802 Intermediate Similarity NPC121800
0.7789 Intermediate Similarity NPC322387
0.7789 Intermediate Similarity NPC96625
0.7788 Intermediate Similarity NPC50872
0.7778 Intermediate Similarity NPC13784
0.7778 Intermediate Similarity NPC5472
0.7778 Intermediate Similarity NPC176228
0.7767 Intermediate Similarity NPC234305
0.7767 Intermediate Similarity NPC160382
0.7767 Intermediate Similarity NPC291426
0.7755 Intermediate Similarity NPC77273
0.7748 Intermediate Similarity NPC228318
0.7742 Intermediate Similarity NPC270507
0.7736 Intermediate Similarity NPC318327
0.7736 Intermediate Similarity NPC281604
0.7732 Intermediate Similarity NPC185501
0.7727 Intermediate Similarity NPC226093
0.7723 Intermediate Similarity NPC210529
0.7723 Intermediate Similarity NPC160548
0.7723 Intermediate Similarity NPC175852
0.7719 Intermediate Similarity NPC26285
0.7717 Intermediate Similarity NPC303245
0.7717 Intermediate Similarity NPC89950
0.7708 Intermediate Similarity NPC329064
0.7699 Intermediate Similarity NPC233282
0.7692 Intermediate Similarity NPC324786
0.7692 Intermediate Similarity NPC300205
0.7692 Intermediate Similarity NPC85977
0.7692 Intermediate Similarity NPC269644
0.7692 Intermediate Similarity NPC38209
0.7692 Intermediate Similarity NPC170484
0.7692 Intermediate Similarity NPC249067
0.7685 Intermediate Similarity NPC66208
0.7652 Intermediate Similarity NPC67300
0.7652 Intermediate Similarity NPC472703
0.7652 Intermediate Similarity NPC291189
0.7652 Intermediate Similarity NPC69403
0.7652 Intermediate Similarity NPC223351
0.7636 Intermediate Similarity NPC474095
0.7636 Intermediate Similarity NPC228936
0.7636 Intermediate Similarity NPC252004
0.7634 Intermediate Similarity NPC103387
0.7624 Intermediate Similarity NPC325499
0.7619 Intermediate Similarity NPC227255
0.7615 Intermediate Similarity NPC17693
0.7609 Intermediate Similarity NPC164086
0.7609 Intermediate Similarity NPC127343
0.7596 Intermediate Similarity NPC329556
0.7596 Intermediate Similarity NPC179686
0.7596 Intermediate Similarity NPC298224
0.7589 Intermediate Similarity NPC469954
0.7586 Intermediate Similarity NPC226794
0.7586 Intermediate Similarity NPC472704
0.7582 Intermediate Similarity NPC36342
0.7582 Intermediate Similarity NPC285470
0.7582 Intermediate Similarity NPC2785
0.7573 Intermediate Similarity NPC253746
0.7573 Intermediate Similarity NPC112552
0.7568 Intermediate Similarity NPC135730
0.7556 Intermediate Similarity NPC175393
0.7553 Intermediate Similarity NPC308619
0.7553 Intermediate Similarity NPC324835
0.7553 Intermediate Similarity NPC127491
0.7551 Intermediate Similarity NPC274455

  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 NPC130398 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
0.9355 High Similarity NPD1238 Approved
0.9167 High Similarity NPD164 Approved
0.9091 High Similarity NPD9259 Approved
0.9091 High Similarity NPD9257 Approved
0.8817 High Similarity NPD1202 Approved
0.88 High Similarity NPD2182 Approved
0.8696 High Similarity NPD9258 Approved
0.8696 High Similarity NPD9256 Approved
0.8627 High Similarity NPD2181 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD9260 Approved
0.8148 Intermediate Similarity NPD9493 Approved
0.809 Intermediate Similarity NPD9490 Approved
0.8 Intermediate Similarity NPD9545 Approved
0.7935 Intermediate Similarity NPD9491 Approved
0.7905 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.785 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7789 Intermediate Similarity NPD1087 Approved
0.7778 Intermediate Similarity NPD225 Approved
0.7778 Intermediate Similarity NPD227 Approved
0.7767 Intermediate Similarity NPD9261 Approved
0.7723 Intermediate Similarity NPD9495 Approved
0.7719 Intermediate Similarity NPD518 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD6287 Discontinued
0.7692 Intermediate Similarity NPD1237 Approved
0.7629 Intermediate Similarity NPD800 Approved
0.7615 Intermediate Similarity NPD5277 Phase 2
0.7596 Intermediate Similarity NPD1930 Approved
0.7596 Intermediate Similarity NPD1929 Approved
0.7596 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD1089 Approved
0.7551 Intermediate Similarity NPD1086 Approved
0.7551 Intermediate Similarity NPD1090 Approved
0.7545 Intermediate Similarity NPD1241 Discontinued
0.7527 Intermediate Similarity NPD226 Approved
0.7525 Intermediate Similarity NPD1989 Approved
0.7523 Intermediate Similarity NPD9508 Approved
0.7521 Intermediate Similarity NPD2199 Approved
0.7521 Intermediate Similarity NPD2198 Approved
0.75 Intermediate Similarity NPD9717 Approved
0.75 Intermediate Similarity NPD2067 Discontinued
0.7477 Intermediate Similarity NPD5951 Approved
0.7477 Intermediate Similarity NPD9267 Approved
0.7477 Intermediate Similarity NPD9263 Approved
0.7477 Intermediate Similarity NPD9264 Approved
0.7477 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD2066 Phase 3
0.7458 Intermediate Similarity NPD9567 Approved
0.7458 Intermediate Similarity NPD552 Approved
0.7458 Intermediate Similarity NPD553 Approved
0.7423 Intermediate Similarity NPD1282 Approved
0.7407 Intermediate Similarity NPD74 Approved
0.7407 Intermediate Similarity NPD9266 Approved
0.74 Intermediate Similarity NPD1088 Approved
0.7395 Intermediate Similarity NPD1019 Discontinued
0.7383 Intermediate Similarity NPD3134 Approved
0.7374 Intermediate Similarity NPD3673 Approved
0.7374 Intermediate Similarity NPD3672 Approved
0.7358 Intermediate Similarity NPD5909 Discontinued
0.7327 Intermediate Similarity NPD1563 Approved
0.7315 Intermediate Similarity NPD1358 Approved
0.73 Intermediate Similarity NPD1239 Approved
0.7273 Intermediate Similarity NPD6832 Phase 2
0.7255 Intermediate Similarity NPD1693 Approved
0.7253 Intermediate Similarity NPD9716 Approved
0.7213 Intermediate Similarity NPD7008 Discontinued
0.7213 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD3972 Approved
0.717 Intermediate Similarity NPD1932 Approved
0.7167 Intermediate Similarity NPD1203 Approved
0.7158 Intermediate Similarity NPD942 Approved
0.7157 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD2347 Approved
0.713 Intermediate Similarity NPD9697 Approved
0.7119 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD1566 Phase 3
0.7115 Intermediate Similarity NPD1564 Approved
0.7115 Intermediate Similarity NPD1565 Approved
0.7103 Intermediate Similarity NPD6647 Phase 2
0.71 Intermediate Similarity NPD5346 Phase 2
0.71 Intermediate Similarity NPD5347 Phase 2
0.7094 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD1362 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD1104 Approved
0.7094 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1876 Approved
0.7071 Intermediate Similarity NPD650 Approved
0.7071 Intermediate Similarity NPD4793 Discontinued
0.7048 Intermediate Similarity NPD5926 Approved
0.704 Intermediate Similarity NPD3373 Approved
0.7018 Intermediate Similarity NPD9281 Approved
0.7018 Intermediate Similarity NPD2629 Approved
0.6984 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6984 Remote Similarity NPD1933 Approved
0.6975 Remote Similarity NPD1281 Approved
0.6967 Remote Similarity NPD2798 Approved
0.6949 Remote Similarity NPD17 Approved
0.6937 Remote Similarity NPD2329 Discontinued
0.6931 Remote Similarity NPD689 Discontinued
0.6929 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1894 Discontinued
0.6915 Remote Similarity NPD9294 Approved
0.6905 Remote Similarity NPD4307 Phase 2
0.6903 Remote Similarity NPD969 Suspended
0.69 Remote Similarity NPD506 Clinical (unspecified phase)
0.6891 Remote Similarity NPD1889 Phase 1
0.688 Remote Similarity NPD9471 Clinical (unspecified phase)
0.688 Remote Similarity NPD2313 Discontinued
0.688 Remote Similarity NPD411 Approved
0.688 Remote Similarity NPD3764 Approved
0.6875 Remote Similarity NPD1317 Discontinued
0.6875 Remote Similarity NPD5240 Approved
0.6875 Remote Similarity NPD2569 Approved
0.6875 Remote Similarity NPD2670 Approved
0.6875 Remote Similarity NPD5236 Approved
0.6875 Remote Similarity NPD2567 Approved
0.6875 Remote Similarity NPD5235 Approved
0.6875 Remote Similarity NPD5237 Approved
0.6875 Remote Similarity NPD5239 Approved
0.687 Remote Similarity NPD1246 Approved
0.686 Remote Similarity NPD182 Clinical (unspecified phase)
0.685 Remote Similarity NPD447 Suspended
0.685 Remote Similarity NPD230 Phase 1
0.6829 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6822 Remote Similarity NPD1109 Approved
0.6822 Remote Similarity NPD3170 Approved
0.6822 Remote Similarity NPD1110 Approved
0.6814 Remote Similarity NPD2201 Approved
0.6803 Remote Similarity NPD1283 Approved
0.6803 Remote Similarity NPD5667 Approved
0.68 Remote Similarity NPD6039 Approved
0.6797 Remote Similarity NPD1654 Clinical (unspecified phase)
0.6796 Remote Similarity NPD7609 Phase 3
0.6777 Remote Similarity NPD1608 Approved
0.6774 Remote Similarity NPD9494 Approved
0.6769 Remote Similarity NPD2935 Discontinued
0.6748 Remote Similarity NPD3266 Approved
0.6748 Remote Similarity NPD3267 Approved
0.6748 Remote Similarity NPD2797 Approved
0.6731 Remote Similarity NPD7631 Approved
0.6726 Remote Similarity NPD4234 Approved
0.6726 Remote Similarity NPD1756 Approved
0.6726 Remote Similarity NPD4233 Approved
0.6726 Remote Similarity NPD1752 Approved
0.6723 Remote Similarity NPD5585 Approved
0.6718 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6718 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6701 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6693 Remote Similarity NPD7713 Phase 3
0.6692 Remote Similarity NPD2799 Discontinued
0.6692 Remote Similarity NPD4308 Phase 3
0.6667 Remote Similarity NPD5305 Approved
0.6667 Remote Similarity NPD3971 Phase 1
0.6667 Remote Similarity NPD1888 Phase 1
0.6667 Remote Similarity NPD4198 Discontinued
0.6667 Remote Similarity NPD6414 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9272 Approved
0.6667 Remote Similarity NPD1778 Approved
0.6667 Remote Similarity NPD5306 Approved
0.6667 Remote Similarity NPD7798 Approved
0.6641 Remote Similarity NPD1240 Approved
0.6641 Remote Similarity NPD1551 Phase 2
0.6641 Remote Similarity NPD3142 Approved
0.6641 Remote Similarity NPD3140 Approved
0.6639 Remote Similarity NPD1481 Phase 2
0.6633 Remote Similarity NPD9250 Approved
0.6617 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6613 Remote Similarity NPD1164 Approved
0.6612 Remote Similarity NPD4135 Approved
0.6612 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6612 Remote Similarity NPD4106 Approved
0.6612 Remote Similarity NPD4136 Approved
0.6612 Remote Similarity NPD3847 Discontinued
0.661 Remote Similarity NPD694 Clinical (unspecified phase)
0.661 Remote Similarity NPD405 Clinical (unspecified phase)
0.6591 Remote Similarity NPD2353 Approved
0.6591 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6591 Remote Similarity NPD2346 Discontinued
0.6591 Remote Similarity NPD7611 Approved
0.6585 Remote Similarity NPD5159 Phase 2
0.6585 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6585 Remote Similarity NPD5157 Phase 1
0.6583 Remote Similarity NPD1245 Approved
0.6583 Remote Similarity NPD4102 Approved
0.6583 Remote Similarity NPD1651 Approved
0.6583 Remote Similarity NPD4105 Approved
0.6583 Remote Similarity NPD5691 Approved
0.6583 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6579 Remote Similarity NPD3646 Clinical (unspecified phase)
0.6571 Remote Similarity NPD1508 Approved
0.6567 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6567 Remote Similarity NPD7003 Approved
0.6567 Remote Similarity NPD4628 Phase 3
0.6565 Remote Similarity NPD3748 Approved
0.6562 Remote Similarity NPD520 Approved
0.656 Remote Similarity NPD6085 Phase 2
0.656 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6557 Remote Similarity NPD4807 Approved
0.6557 Remote Similarity NPD1535 Discovery

  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