Structure

Physi-Chem Properties

Molecular Weight:  188.08
Volume:  203.394
LogP:  3.703
LogD:  3.785
LogS:  -3.292
# Rotatable Bonds:  2
TPSA:  33.37
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.781
Synthetic Accessibility Score:  2.864
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.667
MDCK Permeability:  2.3468808649340644e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.189
Plasma Protein Binding (PPB):  97.89098358154297%
Volume Distribution (VD):  1.0
Pgp-substrate:  3.3311941623687744%

ADMET: Metabolism

CYP1A2-inhibitor:  0.937
CYP1A2-substrate:  0.815
CYP2C19-inhibitor:  0.203
CYP2C19-substrate:  0.326
CYP2C9-inhibitor:  0.285
CYP2C9-substrate:  0.874
CYP2D6-inhibitor:  0.326
CYP2D6-substrate:  0.905
CYP3A4-inhibitor:  0.061
CYP3A4-substrate:  0.145

ADMET: Excretion

Clearance (CL):  10.155
Half-life (T1/2):  0.759

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.694
Drug-inuced Liver Injury (DILI):  0.947
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.351
Maximum Recommended Daily Dose:  0.514
Skin Sensitization:  0.921
Carcinogencity:  0.882
Eye Corrosion:  0.194
Eye Irritation:  0.863
Respiratory Toxicity:  0.828

Download Data

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

  Natural Product: NPC37622

Natural Product ID:  NPC37622
Common Name*:   (E)-Butylidenephthalide
IUPAC Name:   (3E)-3-butylidene-2-benzofuran-1-one
Synonyms:   (Z)-3-Butylidenephthalide
Standard InCHIKey:  WMBOCUXXNSOQHM-DHZHZOJOSA-N
Standard InCHI:  InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8+
SMILES:  CCC/C=C1/OC(=O)c2c1cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1765390
PubChem CID:   5352899
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0004191] Isocoumarans
        • [CHEMONTID:0003409] Isobenzofuranones

*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]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. sclerotium n.a. PMID[21250700]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22834 Rhizoma chuanxiong n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO29438 Radix chuanxiong Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2154 Ligusticum tenuissimum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae 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]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25369 Levisticum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae 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
NPO25369 NPC37622 Other Root 84.4 15.3 153.5 mg/100g Database [DUKE]

☑ 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
NPT526 Individual Protein Alpha-glucosidase MAL62 Saccharomyces cerevisiae IC50 = 2350000.0 nM PMID[481022]
NPT526 Individual Protein Alpha-glucosidase MAL62 Saccharomyces cerevisiae Ki = 4860000.0 nM PMID[481022]
NPT1648 Individual Protein Oligo-1,6-glucosidase Saccharomyces cerevisiae S288c Ki = 4860.0 nM PMID[481024]
NPT1648 Individual Protein Oligo-1,6-glucosidase Saccharomyces cerevisiae S288c IC50 = 2350000.0 nM PMID[481024]
NPT496 Individual Protein Alpha-L-fucosidase 1 Bos taurus IC50 = 82000.0 nM PMID[481025]
NPT32 Organism Mus musculus Mus musculus Activity = -9.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -24.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -41.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -42.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 20.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -6.9 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -18.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -23.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 35.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 27.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 12.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 3.5 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 3.3 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -5.2 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 1.5 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -0.3 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -12.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -7.4 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -9.1 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = -21.7 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 41.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 23.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 19.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 7.6 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 16.0 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 2.5 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 6.7 % PMID[481022]
NPT32 Organism Mus musculus Mus musculus Activity = 6.4 % PMID[481022]
NPT2524 Organism Tyrophagus putrescentiae Tyrophagus putrescentiae RatioLC50 = 0.64 n.a. PMID[481023]
NPT2524 Organism Tyrophagus putrescentiae Tyrophagus putrescentiae LC50 = 25.56 microg/cm2 PMID[481023]
NPT2524 Organism Tyrophagus putrescentiae Tyrophagus putrescentiae mortality = 12.3 % PMID[481023]
NPT2524 Organism Tyrophagus putrescentiae Tyrophagus putrescentiae mortality = 33.0 % PMID[481023]
NPT2524 Organism Tyrophagus putrescentiae Tyrophagus putrescentiae mortality = 52.9 % PMID[481023]
NPT2524 Organism Tyrophagus putrescentiae Tyrophagus putrescentiae mortality = 57.2 % PMID[481023]
NPT2525 Organism Dermatophagoides farinae Dermatophagoides farinae RatioLC50 = 2.78 n.a. PMID[481023]
NPT2525 Organism Dermatophagoides farinae Dermatophagoides farinae LC50 = 4.67 microg/cm2 PMID[481023]
NPT2525 Organism Dermatophagoides farinae Dermatophagoides farinae mortality = 12.2 % PMID[481023]
NPT2525 Organism Dermatophagoides farinae Dermatophagoides farinae mortality = 51.6 % PMID[481023]
NPT2525 Organism Dermatophagoides farinae Dermatophagoides farinae mortality = 94.7 % PMID[481023]
NPT2525 Organism Dermatophagoides farinae Dermatophagoides farinae mortality = 100.0 % PMID[481023]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster LD50 = 0.94 ug PMID[481023]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster RatioLC50 = 0.01 n.a. PMID[481023]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster LC50 = 2070000.0 nM PMID[481023]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster Ratio = 3.91 n.a. PMID[481023]
NPT2 Others Unspecified Ki = 4860.0 nM PMID[481025]
NPT2 Others Unspecified IC50 = 7150.0 nM PMID[481025]
NPT24816 SINGLE PROTEIN Alpha-mannosidase Canavalia ensiformis IC50 = 41000.0 nM PMID[481025]

☑ 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 NPC37622 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
1.0 High Similarity NPC30594
0.95 High Similarity NPC209632
0.9412 High Similarity NPC265407
0.9412 High Similarity NPC83628
0.94 High Similarity NPC114594
0.9394 High Similarity NPC45613
0.93 High Similarity NPC89886
0.9223 High Similarity NPC99846
0.9223 High Similarity NPC269023
0.9048 High Similarity NPC474157
0.9029 High Similarity NPC119271
0.902 High Similarity NPC31786
0.8972 High Similarity NPC307651
0.8942 High Similarity NPC56493
0.8922 High Similarity NPC60679
0.8879 High Similarity NPC272524
0.8857 High Similarity NPC17417
0.8857 High Similarity NPC10251
0.8812 High Similarity NPC325497
0.8807 High Similarity NPC149691
0.88 High Similarity NPC92754
0.88 High Similarity NPC276775
0.88 High Similarity NPC249912
0.8796 High Similarity NPC308744
0.8788 High Similarity NPC130398
0.8774 High Similarity NPC93084
0.8774 High Similarity NPC174099
0.8774 High Similarity NPC251854
0.8774 High Similarity NPC214067
0.8774 High Similarity NPC196246
0.8716 High Similarity NPC210092
0.8716 High Similarity NPC474685
0.8713 High Similarity NPC225060
0.8713 High Similarity NPC35448
0.8713 High Similarity NPC78701
0.8692 High Similarity NPC210089
0.8692 High Similarity NPC260818
0.8692 High Similarity NPC305912
0.8692 High Similarity NPC1082
0.8692 High Similarity NPC243355
0.8679 High Similarity NPC85493
0.8679 High Similarity NPC474364
0.8627 High Similarity NPC146351
0.8624 High Similarity NPC477411
0.8611 High Similarity NPC321852
0.8611 High Similarity NPC82899
0.8611 High Similarity NPC212415
0.8611 High Similarity NPC270699
0.8558 High Similarity NPC474365
0.8558 High Similarity NPC301943
0.8544 High Similarity NPC42211
0.8544 High Similarity NPC70624
0.8529 High Similarity NPC229242
0.8468 Intermediate Similarity NPC226093
0.8455 Intermediate Similarity NPC196075
0.8455 Intermediate Similarity NPC153053
0.8455 Intermediate Similarity NPC237366
0.8447 Intermediate Similarity NPC203925
0.8447 Intermediate Similarity NPC118343
0.8376 Intermediate Similarity NPC246166
0.8364 Intermediate Similarity NPC161611
0.8349 Intermediate Similarity NPC167504
0.8333 Intermediate Similarity NPC469636
0.8305 Intermediate Similarity NPC121272
0.8286 Intermediate Similarity NPC188895
0.8273 Intermediate Similarity NPC79496
0.8273 Intermediate Similarity NPC474314
0.8241 Intermediate Similarity NPC470391
0.8235 Intermediate Similarity NPC51292
0.8205 Intermediate Similarity NPC46634
0.8198 Intermediate Similarity NPC13784
0.8198 Intermediate Similarity NPC128368
0.8198 Intermediate Similarity NPC474176
0.819 Intermediate Similarity NPC282895
0.8163 Intermediate Similarity NPC318107
0.8142 Intermediate Similarity NPC135730
0.8142 Intermediate Similarity NPC100353
0.8113 Intermediate Similarity NPC284477
0.8103 Intermediate Similarity NPC232958
0.81 Intermediate Similarity NPC173443
0.8056 Intermediate Similarity NPC269457
0.8053 Intermediate Similarity NPC306740
0.8053 Intermediate Similarity NPC228936
0.8037 Intermediate Similarity NPC255676
0.8034 Intermediate Similarity NPC144547
0.8019 Intermediate Similarity NPC473325
0.8018 Intermediate Similarity NPC291799
0.8018 Intermediate Similarity NPC476003
0.7965 Intermediate Similarity NPC474363
0.7963 Intermediate Similarity NPC269644
0.7961 Intermediate Similarity NPC261181
0.7949 Intermediate Similarity NPC289432
0.7949 Intermediate Similarity NPC988
0.7946 Intermediate Similarity NPC158282
0.7944 Intermediate Similarity NPC304873
0.7944 Intermediate Similarity NPC25458
0.7925 Intermediate Similarity NPC217621
0.7913 Intermediate Similarity NPC470860
0.7905 Intermediate Similarity NPC270654
0.7905 Intermediate Similarity NPC253423
0.79 Intermediate Similarity NPC89377
0.7895 Intermediate Similarity NPC470764
0.7895 Intermediate Similarity NPC81808
0.7881 Intermediate Similarity NPC50872
0.785 Intermediate Similarity NPC112552
0.7845 Intermediate Similarity NPC217423
0.7845 Intermediate Similarity NPC240664
0.7845 Intermediate Similarity NPC45104
0.7845 Intermediate Similarity NPC228318
0.7843 Intermediate Similarity NPC62765
0.7838 Intermediate Similarity NPC281604
0.7826 Intermediate Similarity NPC188907
0.7826 Intermediate Similarity NPC220540
0.7822 Intermediate Similarity NPC304760
0.7818 Intermediate Similarity NPC1065
0.7797 Intermediate Similarity NPC238861
0.7797 Intermediate Similarity NPC77000
0.7797 Intermediate Similarity NPC473243
0.7788 Intermediate Similarity NPC23332
0.7769 Intermediate Similarity NPC91475
0.7769 Intermediate Similarity NPC265910
0.7769 Intermediate Similarity NPC295664
0.7769 Intermediate Similarity NPC107846
0.7768 Intermediate Similarity NPC273837
0.7759 Intermediate Similarity NPC190298
0.775 Intermediate Similarity NPC223351
0.7748 Intermediate Similarity NPC249811
0.7748 Intermediate Similarity NPC156648
0.7745 Intermediate Similarity NPC220893
0.7739 Intermediate Similarity NPC474095
0.7739 Intermediate Similarity NPC474408
0.7727 Intermediate Similarity NPC105899
0.7723 Intermediate Similarity NPC96625
0.7719 Intermediate Similarity NPC17693
0.7712 Intermediate Similarity NPC204784
0.7706 Intermediate Similarity NPC234305
0.7705 Intermediate Similarity NPC476599
0.77 Intermediate Similarity NPC294134
0.77 Intermediate Similarity NPC58616
0.7699 Intermediate Similarity NPC183648
0.7679 Intermediate Similarity NPC318327
0.7677 Intermediate Similarity NPC288903
0.7647 Intermediate Similarity NPC230951
0.7642 Intermediate Similarity NPC61944
0.7632 Intermediate Similarity NPC66208
0.7632 Intermediate Similarity NPC54626
0.7627 Intermediate Similarity NPC27633
0.7627 Intermediate Similarity NPC94298
0.7627 Intermediate Similarity NPC293424
0.7627 Intermediate Similarity NPC94637
0.7623 Intermediate Similarity NPC470162
0.7623 Intermediate Similarity NPC470163
0.7619 Intermediate Similarity NPC7012
0.7611 Intermediate Similarity NPC259554
0.7611 Intermediate Similarity NPC234639
0.7607 Intermediate Similarity NPC131192
0.7607 Intermediate Similarity NPC128825
0.7603 Intermediate Similarity NPC472703
0.76 Intermediate Similarity NPC471832
0.7596 Intermediate Similarity NPC119631
0.7596 Intermediate Similarity NPC110704
0.7589 Intermediate Similarity NPC211439
0.7586 Intermediate Similarity NPC186933
0.7586 Intermediate Similarity NPC476357
0.7581 Intermediate Similarity NPC181715
0.7563 Intermediate Similarity NPC137710
0.7563 Intermediate Similarity NPC90522
0.7563 Intermediate Similarity NPC328459
0.7563 Intermediate Similarity NPC61779
0.7547 Intermediate Similarity NPC5472
0.7545 Intermediate Similarity NPC82426
0.7545 Intermediate Similarity NPC91820
0.7544 Intermediate Similarity NPC474057
0.7541 Intermediate Similarity NPC228739
0.7541 Intermediate Similarity NPC51079
0.7541 Intermediate Similarity NPC182646
0.7541 Intermediate Similarity NPC472704
0.754 Intermediate Similarity NPC470278
0.7522 Intermediate Similarity NPC192577
0.7521 Intermediate Similarity NPC216387
0.7521 Intermediate Similarity NPC26285
0.75 Intermediate Similarity NPC87069
0.75 Intermediate Similarity NPC72977
0.75 Intermediate Similarity NPC53953
0.75 Intermediate Similarity NPC246214
0.75 Intermediate Similarity NPC169913
0.75 Intermediate Similarity NPC84288
0.75 Intermediate Similarity NPC109241
0.75 Intermediate Similarity NPC241851
0.7478 Intermediate Similarity NPC57879
0.7477 Intermediate Similarity NPC38209
0.746 Intermediate Similarity NPC147561
0.746 Intermediate Similarity NPC66246
0.746 Intermediate Similarity NPC170546
0.7459 Intermediate Similarity NPC475692
0.7459 Intermediate Similarity NPC291189
0.7459 Intermediate Similarity NPC69403
0.7459 Intermediate Similarity NPC311219
0.7459 Intermediate Similarity NPC474283
0.7459 Intermediate Similarity NPC217756

  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 NPC37622 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
0.9231 High Similarity NPD2181 Clinical (unspecified phase)
0.902 High Similarity NPD164 Approved
0.8857 High Similarity NPD2182 Approved
0.8611 High Similarity NPD1609 Clinical (unspecified phase)
0.8447 Intermediate Similarity NPD1238 Approved
0.8214 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD9257 Approved
0.8163 Intermediate Similarity NPD9259 Approved
0.7961 Intermediate Similarity NPD1202 Approved
0.7843 Intermediate Similarity NPD9258 Approved
0.7843 Intermediate Similarity NPD9256 Approved
0.7797 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7768 Intermediate Similarity NPD2067 Discontinued
0.768 Intermediate Similarity NPD3764 Approved
0.7667 Intermediate Similarity NPD518 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD5909 Discontinued
0.7627 Intermediate Similarity NPD9545 Approved
0.7607 Intermediate Similarity NPD9493 Approved
0.76 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD9260 Approved
0.7522 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1241 Discontinued
0.748 Intermediate Similarity NPD1876 Approved
0.7459 Intermediate Similarity NPD9717 Approved
0.7449 Intermediate Similarity NPD9490 Approved
0.7436 Intermediate Similarity NPD5951 Approved
0.7387 Intermediate Similarity NPD1929 Approved
0.7387 Intermediate Similarity NPD9261 Approved
0.7387 Intermediate Similarity NPD1930 Approved
0.7387 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD1087 Approved
0.7377 Intermediate Similarity NPD6287 Discontinued
0.7327 Intermediate Similarity NPD9491 Approved
0.7273 Intermediate Similarity NPD2066 Phase 3
0.7244 Intermediate Similarity NPD6832 Phase 2
0.7236 Intermediate Similarity NPD1281 Approved
0.7222 Intermediate Similarity NPD1693 Approved
0.7222 Intermediate Similarity NPD1019 Discontinued
0.7222 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD2346 Discontinued
0.7213 Intermediate Similarity NPD17 Approved
0.7212 Intermediate Similarity NPD1282 Approved
0.7212 Intermediate Similarity NPD650 Approved
0.7193 Intermediate Similarity NPD3134 Approved
0.7188 Intermediate Similarity NPD7008 Discontinued
0.7182 Intermediate Similarity NPD9495 Approved
0.7177 Intermediate Similarity NPD3972 Approved
0.7172 Intermediate Similarity NPD225 Approved
0.7172 Intermediate Similarity NPD227 Approved
0.717 Intermediate Similarity NPD1090 Approved
0.717 Intermediate Similarity NPD1089 Approved
0.717 Intermediate Similarity NPD1086 Approved
0.7168 Intermediate Similarity NPD1237 Approved
0.7156 Intermediate Similarity NPD1989 Approved
0.7143 Intermediate Similarity NPD1203 Approved
0.7143 Intermediate Similarity NPD1932 Approved
0.7132 Intermediate Similarity NPD2313 Discontinued
0.713 Intermediate Similarity NPD9267 Approved
0.713 Intermediate Similarity NPD9264 Approved
0.713 Intermediate Similarity NPD1358 Approved
0.713 Intermediate Similarity NPD9263 Approved
0.713 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD9697 Approved
0.7097 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD1471 Phase 3
0.7087 Intermediate Similarity NPD2798 Approved
0.708 Intermediate Similarity NPD6647 Phase 2
0.7075 Intermediate Similarity NPD800 Approved
0.7073 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD9266 Approved
0.7069 Intermediate Similarity NPD74 Approved
0.7068 Intermediate Similarity NPD2799 Discontinued
0.7068 Intermediate Similarity NPD3748 Approved
0.7064 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD2199 Approved
0.7063 Intermediate Similarity NPD2198 Approved
0.7063 Intermediate Similarity NPD1283 Approved
0.704 Intermediate Similarity NPD1608 Approved
0.7037 Intermediate Similarity NPD1088 Approved
0.7025 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD4307 Phase 2
0.7009 Intermediate Similarity NPD3673 Approved
0.7009 Intermediate Similarity NPD3672 Approved
0.7008 Intermediate Similarity NPD3266 Approved
0.7008 Intermediate Similarity NPD2797 Approved
0.7008 Intermediate Similarity NPD3267 Approved
0.6992 Remote Similarity NPD5691 Approved
0.6975 Remote Similarity NPD5277 Phase 2
0.6972 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6972 Remote Similarity NPD1563 Approved
0.697 Remote Similarity NPD447 Suspended
0.6961 Remote Similarity NPD226 Approved
0.6944 Remote Similarity NPD1239 Approved
0.6944 Remote Similarity NPD7609 Phase 3
0.6923 Remote Similarity NPD2329 Discontinued
0.6911 Remote Similarity NPD1894 Discontinued
0.6905 Remote Similarity NPD1877 Discontinued
0.6891 Remote Similarity NPD9508 Approved
0.6891 Remote Similarity NPD969 Suspended
0.6881 Remote Similarity NPD7631 Approved
0.6881 Remote Similarity NPD1508 Approved
0.688 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6875 Remote Similarity NPD553 Approved
0.6875 Remote Similarity NPD552 Approved
0.6875 Remote Similarity NPD9567 Approved
0.687 Remote Similarity NPD411 Approved
0.6866 Remote Similarity NPD2569 Approved
0.6866 Remote Similarity NPD2567 Approved
0.6864 Remote Similarity NPD5235 Approved
0.6864 Remote Similarity NPD5237 Approved
0.6864 Remote Similarity NPD5239 Approved
0.6864 Remote Similarity NPD5236 Approved
0.6864 Remote Similarity NPD5240 Approved
0.686 Remote Similarity NPD1246 Approved
0.6855 Remote Similarity NPD1651 Approved
0.685 Remote Similarity NPD182 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1933 Approved
0.6838 Remote Similarity NPD2344 Approved
0.6829 Remote Similarity NPD2347 Approved
0.6818 Remote Similarity NPD8032 Phase 2
0.6815 Remote Similarity NPD4308 Phase 3
0.6812 Remote Similarity NPD7003 Approved
0.6812 Remote Similarity NPD3750 Approved
0.6809 Remote Similarity NPD6273 Approved
0.6807 Remote Similarity NPD2201 Approved
0.68 Remote Similarity NPD4626 Approved
0.6796 Remote Similarity NPD942 Approved
0.6788 Remote Similarity NPD970 Clinical (unspecified phase)
0.6786 Remote Similarity NPD1565 Approved
0.6786 Remote Similarity NPD1566 Phase 3
0.6786 Remote Similarity NPD1564 Approved
0.6772 Remote Similarity NPD1481 Phase 2
0.6772 Remote Similarity NPD4878 Approved
0.6767 Remote Similarity NPD2979 Phase 3
0.6748 Remote Similarity NPD694 Clinical (unspecified phase)
0.6742 Remote Similarity NPD3268 Approved
0.6739 Remote Similarity NPD1243 Approved
0.6723 Remote Similarity NPD1317 Discontinued
0.6721 Remote Similarity NPD9281 Approved
0.6721 Remote Similarity NPD2629 Approved
0.672 Remote Similarity NPD1245 Approved
0.672 Remote Similarity NPD5585 Approved
0.6716 Remote Similarity NPD230 Phase 1
0.6715 Remote Similarity NPD2353 Approved
0.6715 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6696 Remote Similarity NPD1843 Approved
0.6694 Remote Similarity NPD5535 Approved
0.6693 Remote Similarity NPD1535 Discovery
0.6692 Remote Similarity NPD2788 Approved
0.6691 Remote Similarity NPD4628 Phase 3
0.6667 Remote Similarity NPD3971 Phase 1
0.6667 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3226 Approved
0.6667 Remote Similarity NPD5667 Approved
0.6667 Remote Similarity NPD1654 Clinical (unspecified phase)
0.6643 Remote Similarity NPD2309 Approved
0.6642 Remote Similarity NPD3140 Approved
0.6642 Remote Similarity NPD3373 Approved
0.6642 Remote Similarity NPD3142 Approved
0.6642 Remote Similarity NPD2935 Discontinued
0.6641 Remote Similarity NPD9494 Approved
0.6641 Remote Similarity NPD6637 Approved
0.6637 Remote Similarity NPD3495 Discontinued
0.662 Remote Similarity NPD2534 Approved
0.662 Remote Similarity NPD2533 Approved
0.662 Remote Similarity NPD2532 Approved
0.6619 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6615 Remote Similarity NPD1164 Approved
0.6615 Remote Similarity NPD1470 Approved
0.6606 Remote Similarity NPD5346 Phase 2
0.6606 Remote Similarity NPD5347 Phase 2
0.6596 Remote Similarity NPD7236 Approved
0.6594 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6594 Remote Similarity NPD7611 Approved
0.6593 Remote Similarity NPD4618 Approved
0.6593 Remote Similarity NPD4622 Approved
0.6587 Remote Similarity NPD4105 Approved
0.6587 Remote Similarity NPD4102 Approved
0.6587 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6583 Remote Similarity NPD4233 Approved
0.6583 Remote Similarity NPD4234 Approved
0.6579 Remote Similarity NPD5926 Approved
0.6574 Remote Similarity NPD506 Clinical (unspecified phase)
0.6574 Remote Similarity NPD4793 Discontinued
0.6571 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6567 Remote Similarity NPD7713 Phase 3
0.6565 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6565 Remote Similarity NPD5647 Approved
0.6565 Remote Similarity NPD6085 Phase 2
0.6562 Remote Similarity NPD1201 Approved
0.6562 Remote Similarity NPD1611 Approved
0.6557 Remote Similarity NPD6858 Approved
0.6557 Remote Similarity NPD7094 Approved
0.6544 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6541 Remote Similarity NPD6039 Approved
0.6535 Remote Similarity NPD5306 Approved
0.6535 Remote Similarity NPD1362 Clinical (unspecified phase)
0.6535 Remote Similarity NPD1104 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