Structure

Physi-Chem Properties

Molecular Weight:  325.14
Volume:  326.564
LogP:  2.408
LogD:  2.674
LogS:  -3.762
# Rotatable Bonds:  4
TPSA:  68.62
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.626
Synthetic Accessibility Score:  2.935
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.884
MDCK Permeability:  1.900311508507002e-05
Pgp-inhibitor:  0.016
Pgp-substrate:  0.075
Human Intestinal Absorption (HIA):  0.486
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.039
Plasma Protein Binding (PPB):  94.8868179321289%
Volume Distribution (VD):  0.437
Pgp-substrate:  3.9579999446868896%

ADMET: Metabolism

CYP1A2-inhibitor:  0.92
CYP1A2-substrate:  0.972
CYP2C19-inhibitor:  0.761
CYP2C19-substrate:  0.753
CYP2C9-inhibitor:  0.86
CYP2C9-substrate:  0.819
CYP2D6-inhibitor:  0.102
CYP2D6-substrate:  0.205
CYP3A4-inhibitor:  0.542
CYP3A4-substrate:  0.344

ADMET: Excretion

Clearance (CL):  9.672
Half-life (T1/2):  0.697

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.525
Drug-inuced Liver Injury (DILI):  0.945
AMES Toxicity:  0.713
Rat Oral Acute Toxicity:  0.721
Maximum Recommended Daily Dose:  0.763
Skin Sensitization:  0.03
Carcinogencity:  0.941
Eye Corrosion:  0.003
Eye Irritation:  0.032
Respiratory Toxicity:  0.945

Download Data

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

  Natural Product: NPC472031

Natural Product ID:  NPC472031
Common Name*:   RSMUMQNBHXVAGW-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RSMUMQNBHXVAGW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H19N3O3/c1-9(2)7-12-19-15-16-13-10(5-6-21(12)16)8-11(23-3)17(24-4)14(13)20-18(15)22/h5-6,8-9H,7H2,1-4H3,(H,20,22)
SMILES:  COc1c(OC)cc2c3c1nc(O)c1c3n(cc2)c(n1)CC(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3334508
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0004331] Imidazoquinolines

*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
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. PMID[17716892]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. South China Sea n.a. PMID[25211032]
NPO27743 Aaptos aaptos Species Suberitidae 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
NPT111 Cell Line K562 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[484857]
NPT91 Cell Line KB Homo sapiens IC50 > 10.0 ug.mL-1 PMID[484857]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[484857]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[484857]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[484857]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10.0 ug.mL-1 PMID[484857]

☑ 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 NPC472031 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 NPC472067
1.0 High Similarity NPC472066
0.964 High Similarity NPC472068
0.8652 High Similarity NPC30540
0.807 Intermediate Similarity NPC173080
0.7739 Intermediate Similarity NPC162530
0.7639 Intermediate Similarity NPC473513
0.748 Intermediate Similarity NPC41501
0.7479 Intermediate Similarity NPC160666
0.7469 Intermediate Similarity NPC473183
0.7466 Intermediate Similarity NPC230805
0.7458 Intermediate Similarity NPC200888
0.7447 Intermediate Similarity NPC8022
0.7447 Intermediate Similarity NPC470799
0.7426 Intermediate Similarity NPC308906
0.7388 Intermediate Similarity NPC473184
0.738 Intermediate Similarity NPC66815
0.7371 Intermediate Similarity NPC18348
0.7358 Intermediate Similarity NPC295228
0.7347 Intermediate Similarity NPC473182
0.7339 Intermediate Similarity NPC469589
0.732 Intermediate Similarity NPC477795
0.732 Intermediate Similarity NPC477805
0.732 Intermediate Similarity NPC477796
0.732 Intermediate Similarity NPC477806
0.7284 Intermediate Similarity NPC473185
0.7283 Intermediate Similarity NPC56271
0.728 Intermediate Similarity NPC17565
0.7261 Intermediate Similarity NPC280272
0.7246 Intermediate Similarity NPC26679
0.7246 Intermediate Similarity NPC112206
0.7246 Intermediate Similarity NPC202605
0.7243 Intermediate Similarity NPC132631
0.7243 Intermediate Similarity NPC103687
0.7231 Intermediate Similarity NPC65277
0.7208 Intermediate Similarity NPC213530
0.7208 Intermediate Similarity NPC193267
0.7198 Intermediate Similarity NPC475774
0.7191 Intermediate Similarity NPC174758
0.7191 Intermediate Similarity NPC185782
0.7176 Intermediate Similarity NPC51854
0.7149 Intermediate Similarity NPC287208
0.7143 Intermediate Similarity NPC314573
0.7137 Intermediate Similarity NPC250178
0.7137 Intermediate Similarity NPC148409
0.7137 Intermediate Similarity NPC304183
0.7137 Intermediate Similarity NPC9729
0.7131 Intermediate Similarity NPC242923
0.7124 Intermediate Similarity NPC476138
0.7124 Intermediate Similarity NPC245816
0.7124 Intermediate Similarity NPC223427
0.7117 Intermediate Similarity NPC144114
0.7101 Intermediate Similarity NPC203168
0.7094 Intermediate Similarity NPC36229
0.7094 Intermediate Similarity NPC16452
0.7094 Intermediate Similarity NPC476581
0.7089 Intermediate Similarity NPC219664
0.7087 Intermediate Similarity NPC267928
0.7082 Intermediate Similarity NPC470678
0.7071 Intermediate Similarity NPC469592
0.7071 Intermediate Similarity NPC471080
0.7066 Intermediate Similarity NPC136924
0.7049 Intermediate Similarity NPC46970
0.7049 Intermediate Similarity NPC118121
0.7046 Intermediate Similarity NPC174672
0.7045 Intermediate Similarity NPC476997
0.7039 Intermediate Similarity NPC31930
0.7033 Intermediate Similarity NPC214980
0.7029 Intermediate Similarity NPC296482
0.7029 Intermediate Similarity NPC202768
0.7029 Intermediate Similarity NPC53069
0.7029 Intermediate Similarity NPC316981
0.7026 Intermediate Similarity NPC4071
0.7026 Intermediate Similarity NPC476582
0.7026 Intermediate Similarity NPC476578
0.7025 Intermediate Similarity NPC23614
0.7025 Intermediate Similarity NPC204446
0.7025 Intermediate Similarity NPC100079
0.7022 Intermediate Similarity NPC42591
0.7016 Intermediate Similarity NPC476998
0.7016 Intermediate Similarity NPC476996
0.7012 Intermediate Similarity NPC274982
0.7009 Intermediate Similarity NPC199277
0.7009 Intermediate Similarity NPC135887
0.7004 Intermediate Similarity NPC82548
0.7 Intermediate Similarity NPC149471
0.7 Intermediate Similarity NPC271215
0.6996 Remote Similarity NPC473179
0.6996 Remote Similarity NPC477019
0.6996 Remote Similarity NPC234197
0.6992 Remote Similarity NPC472111
0.6987 Remote Similarity NPC133140
0.6987 Remote Similarity NPC195268
0.6979 Remote Similarity NPC53144
0.6976 Remote Similarity NPC476994
0.6975 Remote Similarity NPC209769
0.6967 Remote Similarity NPC132642
0.6966 Remote Similarity NPC470586
0.6966 Remote Similarity NPC232727
0.6964 Remote Similarity NPC202503
0.6964 Remote Similarity NPC2497
0.6964 Remote Similarity NPC477891
0.6962 Remote Similarity NPC313189
0.696 Remote Similarity NPC101543
0.696 Remote Similarity NPC469554
0.6955 Remote Similarity NPC469594
0.6953 Remote Similarity NPC476167
0.6951 Remote Similarity NPC130570
0.693 Remote Similarity NPC110741
0.693 Remote Similarity NPC472289
0.6929 Remote Similarity NPC266931
0.6926 Remote Similarity NPC46451
0.6923 Remote Similarity NPC35761
0.6923 Remote Similarity NPC19872
0.692 Remote Similarity NPC475253
0.6914 Remote Similarity NPC12100
0.691 Remote Similarity NPC192315
0.6908 Remote Similarity NPC237978
0.6908 Remote Similarity NPC314954
0.6901 Remote Similarity NPC235076
0.6891 Remote Similarity NPC193777
0.6888 Remote Similarity NPC171409
0.6888 Remote Similarity NPC471603
0.6888 Remote Similarity NPC94157
0.6888 Remote Similarity NPC96405
0.6878 Remote Similarity NPC476686
0.6878 Remote Similarity NPC105758
0.6878 Remote Similarity NPC476688
0.6878 Remote Similarity NPC285558
0.6875 Remote Similarity NPC123976
0.6875 Remote Similarity NPC188420
0.6875 Remote Similarity NPC167860
0.687 Remote Similarity NPC310118
0.6867 Remote Similarity NPC474188
0.6864 Remote Similarity NPC295898
0.6862 Remote Similarity NPC470931
0.6862 Remote Similarity NPC475910
0.686 Remote Similarity NPC476287
0.6853 Remote Similarity NPC280638
0.6851 Remote Similarity NPC25897
0.6847 Remote Similarity NPC208060
0.6846 Remote Similarity NPC26543
0.6842 Remote Similarity NPC204385
0.6836 Remote Similarity NPC99891
0.6835 Remote Similarity NPC200836
0.682 Remote Similarity NPC135549
0.682 Remote Similarity NPC474595
0.6818 Remote Similarity NPC264176
0.6818 Remote Similarity NPC48353
0.6816 Remote Similarity NPC312872
0.6816 Remote Similarity NPC132385
0.6812 Remote Similarity NPC254762
0.6809 Remote Similarity NPC18487
0.6809 Remote Similarity NPC171393
0.6809 Remote Similarity NPC295452
0.6809 Remote Similarity NPC39092
0.6807 Remote Similarity NPC470930
0.6806 Remote Similarity NPC303374
0.6805 Remote Similarity NPC290689
0.6805 Remote Similarity NPC5145
0.6805 Remote Similarity NPC85273
0.6805 Remote Similarity NPC199667
0.6802 Remote Similarity NPC60621
0.68 Remote Similarity NPC187145
0.68 Remote Similarity NPC110151
0.6793 Remote Similarity NPC211813
0.6787 Remote Similarity NPC278874
0.6786 Remote Similarity NPC476451
0.6784 Remote Similarity NPC476995
0.678 Remote Similarity NPC329747
0.678 Remote Similarity NPC176538
0.678 Remote Similarity NPC315957
0.6773 Remote Similarity NPC471762
0.6769 Remote Similarity NPC471891
0.6763 Remote Similarity NPC473181
0.6761 Remote Similarity NPC174049
0.6749 Remote Similarity NPC251160
0.6748 Remote Similarity NPC467439
0.6748 Remote Similarity NPC473822
0.6743 Remote Similarity NPC270515
0.6737 Remote Similarity NPC287437
0.6736 Remote Similarity NPC475070
0.6736 Remote Similarity NPC11464
0.6734 Remote Similarity NPC17305
0.6732 Remote Similarity NPC141053
0.6732 Remote Similarity NPC172222
0.6732 Remote Similarity NPC477861
0.6721 Remote Similarity NPC474594
0.6719 Remote Similarity NPC472061
0.6718 Remote Similarity NPC316756
0.6708 Remote Similarity NPC475841
0.6708 Remote Similarity NPC474145
0.6707 Remote Similarity NPC122463
0.6706 Remote Similarity NPC208898
0.6695 Remote Similarity NPC239954
0.6695 Remote Similarity NPC79213
0.6694 Remote Similarity NPC128115
0.6692 Remote Similarity NPC472434
0.6681 Remote Similarity NPC472193
0.6681 Remote Similarity NPC84478

  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 NPC472031 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
0.7931 Intermediate Similarity NPD1954 Phase 1
0.7845 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.7819 Intermediate Similarity NPD7067 Approved
0.7819 Intermediate Similarity NPD7068 Approved
0.7637 Intermediate Similarity NPD5703 Discontinued
0.7635 Intermediate Similarity NPD4080 Discontinued
0.7623 Intermediate Similarity NPD5905 Phase 1
0.7617 Intermediate Similarity NPD3590 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD4996 Approved
0.7552 Intermediate Similarity NPD4995 Approved
0.7521 Intermediate Similarity NPD6643 Discontinued
0.751 Intermediate Similarity NPD4925 Approved
0.749 Intermediate Similarity NPD3255 Phase 1
0.749 Intermediate Similarity NPD3254 Phase 1
0.7466 Intermediate Similarity NPD9714 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD1273 Discontinued
0.745 Intermediate Similarity NPD6244 Phase 3
0.745 Intermediate Similarity NPD6243 Phase 3
0.741 Intermediate Similarity NPD5644 Phase 1
0.7391 Intermediate Similarity NPD6743 Phase 2
0.7391 Intermediate Similarity NPD6742 Phase 2
0.7388 Intermediate Similarity NPD3838 Phase 3
0.7371 Intermediate Similarity NPD5658 Approved
0.7366 Intermediate Similarity NPD1900 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD6230 Discontinued
0.7352 Intermediate Similarity NPD5875 Approved
0.7352 Intermediate Similarity NPD5878 Approved
0.735 Intermediate Similarity NPD4502 Phase 2
0.7344 Intermediate Similarity NPD4132 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD6572 Phase 2
0.732 Intermediate Similarity NPD7620 Phase 2
0.732 Intermediate Similarity NPD6573 Phase 3
0.732 Intermediate Similarity NPD4440 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD2757 Phase 2
0.7294 Intermediate Similarity NPD5539 Phase 2
0.7283 Intermediate Similarity NPD5008 Approved
0.728 Intermediate Similarity NPD5051 Phase 1
0.728 Intermediate Similarity NPD5873 Phase 3
0.728 Intermediate Similarity NPD4442 Phase 2
0.728 Intermediate Similarity NPD5874 Phase 3
0.728 Intermediate Similarity NPD5833 Phase 1
0.7266 Intermediate Similarity NPD8442 Discontinued
0.7253 Intermediate Similarity NPD7222 Phase 2
0.725 Intermediate Similarity NPD6856 Discontinued
0.7237 Intermediate Similarity NPD5911 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD983 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD6327 Phase 1
0.7213 Intermediate Similarity NPD6326 Phase 2
0.721 Intermediate Similarity NPD5530 Phase 1
0.7206 Intermediate Similarity NPD6223 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD5007 Approved
0.7202 Intermediate Similarity NPD3938 Phase 1
0.72 Intermediate Similarity NPD2410 Phase 2
0.719 Intermediate Similarity NPD1856 Discontinued
0.7176 Intermediate Similarity NPD6216 Approved
0.7171 Intermediate Similarity NPD8049 Phase 2
0.7165 Intermediate Similarity NPD5876 Phase 3
0.7165 Intermediate Similarity NPD5877 Phase 3
0.716 Intermediate Similarity NPD2414 Clinical (unspecified phase)
0.7137 Intermediate Similarity NPD6500 Approved
0.7137 Intermediate Similarity NPD2060 Approved
0.7137 Intermediate Similarity NPD6501 Approved
0.7131 Intermediate Similarity NPD4858 Phase 2
0.711 Intermediate Similarity NPD3343 Phase 3
0.7109 Intermediate Similarity NPD7588 Discontinued
0.7106 Intermediate Similarity NPD7452 Approved
0.7106 Intermediate Similarity NPD7453 Approved
0.7099 Intermediate Similarity NPD5870 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD5869 Phase 2
0.7092 Intermediate Similarity NPD6750 Phase 2
0.7088 Intermediate Similarity NPD6228 Discontinued
0.7083 Intermediate Similarity NPD7112 Discontinued
0.7078 Intermediate Similarity NPD7726 Phase 1
0.7076 Intermediate Similarity NPD5529 Phase 1
0.7076 Intermediate Similarity NPD5528 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD3886 Phase 1
0.7069 Intermediate Similarity NPD1838 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD6592 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD7051 Phase 3
0.7033 Intermediate Similarity NPD7050 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6202 Discontinued
0.7029 Intermediate Similarity NPD3816 Phase 1
0.7029 Intermediate Similarity NPD3815 Phase 1
0.7029 Intermediate Similarity NPD2794 Discontinued
0.7028 Intermediate Similarity NPD7705 Clinical (unspecified phase)
0.7028 Intermediate Similarity NPD8357 Approved
0.7024 Intermediate Similarity NPD6605 Phase 3
0.7024 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD4673 Phase 2
0.7008 Intermediate Similarity NPD6473 Phase 1
0.7008 Intermediate Similarity NPD5949 Phase 3
0.7008 Intermediate Similarity NPD4881 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6494 Phase 2
0.6996 Remote Similarity NPD7117 Phase 2
0.6996 Remote Similarity NPD4555 Clinical (unspecified phase)
0.6987 Remote Similarity NPD3924 Approved
0.6987 Remote Similarity NPD2540 Clinical (unspecified phase)
0.6987 Remote Similarity NPD3921 Approved
0.6987 Remote Similarity NPD3923 Approved
0.6987 Remote Similarity NPD4131 Phase 3
0.6987 Remote Similarity NPD3922 Approved
0.6972 Remote Similarity NPD6760 Discontinued
0.6957 Remote Similarity NPD6046 Clinical (unspecified phase)
0.6953 Remote Similarity NPD2177 Approved
0.6953 Remote Similarity NPD3541 Clinical (unspecified phase)
0.6953 Remote Similarity NPD2175 Phase 3
0.6953 Remote Similarity NPD2176 Approved
0.6951 Remote Similarity NPD5045 Phase 2
0.6951 Remote Similarity NPD3920 Phase 2
0.6949 Remote Similarity NPD6814 Phase 3
0.6946 Remote Similarity NPD4048 Approved
0.6946 Remote Similarity NPD5645 Phase 3
0.6942 Remote Similarity NPD6772 Clinical (unspecified phase)
0.694 Remote Similarity NPD5459 Phase 2
0.6937 Remote Similarity NPD6754 Phase 3
0.6932 Remote Similarity NPD7706 Clinical (unspecified phase)
0.6932 Remote Similarity NPD4306 Phase 1
0.6926 Remote Similarity NPD3763 Approved
0.6923 Remote Similarity NPD4403 Phase 3
0.6923 Remote Similarity NPD4401 Phase 2
0.692 Remote Similarity NPD1955 Discontinued
0.6908 Remote Similarity NPD1624 Phase 2
0.6908 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6901 Remote Similarity NPD6528 Phase 1
0.6898 Remote Similarity NPD5930 Phase 3
0.6894 Remote Similarity NPD5116 Phase 1
0.6891 Remote Similarity NPD6290 Phase 2
0.6878 Remote Similarity NPD4795 Phase 2
0.6867 Remote Similarity NPD5567 Approved
0.6863 Remote Similarity NPD6175 Phase 3
0.6863 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6857 Remote Similarity NPD3875 Discontinued
0.6846 Remote Similarity NPD5939 Approved
0.6846 Remote Similarity NPD5936 Approved
0.6842 Remote Similarity NPD2917 Approved
0.6836 Remote Similarity NPD6848 Phase 1
0.6834 Remote Similarity NPD7898 Clinical (unspecified phase)
0.6834 Remote Similarity NPD7897 Phase 3
0.6831 Remote Similarity NPD5903 Approved
0.6831 Remote Similarity NPD5902 Approved
0.6827 Remote Similarity NPD5018 Phase 3
0.6827 Remote Similarity NPD1603 Discontinued
0.6822 Remote Similarity NPD4511 Phase 1
0.682 Remote Similarity NPD1197 Approved
0.682 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4927 Discontinued
0.6813 Remote Similarity NPD6708 Discontinued
0.6811 Remote Similarity NPD4654 Phase 1
0.681 Remote Similarity NPD3403 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5999 Phase 2
0.6809 Remote Similarity NPD4548 Discontinued
0.6802 Remote Similarity NPD6589 Phase 1
0.6797 Remote Similarity NPD2929 Clinical (unspecified phase)
0.6792 Remote Similarity NPD5863 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4612 Discontinued
0.6789 Remote Similarity NPD537 Phase 2
0.6789 Remote Similarity NPD534 Phase 2
0.6787 Remote Similarity NPD5829 Phase 2
0.6787 Remote Similarity NPD4932 Clinical (unspecified phase)
0.6783 Remote Similarity NPD7592 Phase 2
0.6783 Remote Similarity NPD5802 Phase 2
0.6782 Remote Similarity NPD6482 Phase 1
0.678 Remote Similarity NPD1740 Approved
0.678 Remote Similarity NPD1739 Approved
0.6777 Remote Similarity NPD3939 Suspended
0.6777 Remote Similarity NPD949 Phase 1
0.6769 Remote Similarity NPD7758 Approved
0.6769 Remote Similarity NPD7757 Approved
0.6765 Remote Similarity NPD7682 Approved
0.6765 Remote Similarity NPD7684 Approved
0.6752 Remote Similarity NPD7198 Clinical (unspecified phase)
0.675 Remote Similarity NPD796 Phase 2
0.6748 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6744 Remote Similarity NPD6490 Phase 2
0.6744 Remote Similarity NPD6716 Phase 1
0.6737 Remote Similarity NPD3814 Phase 1
0.6736 Remote Similarity NPD5425 Phase 1
0.6732 Remote Similarity NPD2471 Approved
0.6732 Remote Similarity NPD8016 Phase 3
0.6732 Remote Similarity NPD2472 Approved
0.6732 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6732 Remote Similarity NPD6992 Phase 2
0.6731 Remote Similarity NPD5118 Phase 2
0.6728 Remote Similarity NPD5509 Phase 1
0.6725 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6725 Remote Similarity NPD2762 Phase 2
0.6721 Remote Similarity NPD7506 Discontinued
0.6721 Remote Similarity NPD4457 Phase 2
0.6721 Remote Similarity NPD3514 Clinical (unspecified phase)
0.672 Remote Similarity NPD4890 Phase 2
0.672 Remote Similarity NPD1258 Discontinued
0.6719 Remote Similarity NPD5139 Phase 1
0.6718 Remote Similarity NPD1941 Approved
0.6718 Remote Similarity NPD5998 Clinical (unspecified phase)
0.6709 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6708 Remote Similarity NPD3570 Phase 2
0.6707 Remote Similarity NPD7980 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4893 Phase 3
0.6707 Remote Similarity NPD4945 Discontinued

  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