Structure

Physi-Chem Properties

Molecular Weight:  243.1
Volume:  248.407
LogP:  -0.184
LogD:  0.441
LogS:  -1.926
# Rotatable Bonds:  4
TPSA:  74.85
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.846
Synthetic Accessibility Score:  2.505
Fsp3:  0.154
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:  -4.799
MDCK Permeability:  9.938724360836204e-06
Pgp-inhibitor:  0.002
Pgp-substrate:  0.031
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.139

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.835
Plasma Protein Binding (PPB):  16.754810333251953%
Volume Distribution (VD):  1.234
Pgp-substrate:  77.36725616455078%

ADMET: Metabolism

CYP1A2-inhibitor:  0.232
CYP1A2-substrate:  0.214
CYP2C19-inhibitor:  0.05
CYP2C19-substrate:  0.062
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.453
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.659
CYP3A4-inhibitor:  0.018
CYP3A4-substrate:  0.107

ADMET: Excretion

Clearance (CL):  3.294
Half-life (T1/2):  0.463

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.365
Drug-inuced Liver Injury (DILI):  0.755
AMES Toxicity:  0.047
Rat Oral Acute Toxicity:  0.041
Maximum Recommended Daily Dose:  0.275
Skin Sensitization:  0.199
Carcinogencity:  0.021
Eye Corrosion:  0.004
Eye Irritation:  0.031
Respiratory Toxicity:  0.597

Download Data

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

  Natural Product: NPC25899

Natural Product ID:  NPC25899
Common Name*:   Caerulomycin J
IUPAC Name:   N-[(4-oxo-6-pyridin-2-yl-1H-pyridin-2-yl)methyl]acetamide
Synonyms:   caerulomycin J
Standard InCHIKey:  IXDVQWRMMLGZLB-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H13N3O2/c1-9(17)15-8-10-6-11(18)7-13(16-10)12-4-2-3-5-14-12/h2-7H,8H2,1H3,(H,15,17)(H,16,18)
SMILES:  CC(=NCc1cc(O)cc(n1)c1ccccn1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1823035
PubChem CID:   53484027
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0000326] Bipyridines and oligopyridines

*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
NPO23850 Actinoalloteichus cyanogriseus Species Pseudonocardiaceae Bacteria isolated from marine sediments the seashore of Weihai, China n.a. PMID[21770434]
NPO23850 Actinoalloteichus cyanogriseus Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[21770434]
NPO23850 Actinoalloteichus cyanogriseus Species Pseudonocardiaceae Bacteria 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
NPT91 Cell Line KB Homo sapiens IC50 = 25700.0 nM PMID[466179]
NPT81 Cell Line A549 Homo sapiens IC50 > 50000.0 nM PMID[466179]
NPT111 Cell Line K562 Homo sapiens IC50 = 15000.0 nM PMID[466179]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 50000.0 nM PMID[466179]
NPT20 Organism Candida albicans Candida albicans MIC >= 100000.0 nM PMID[466179]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC >= 100000.0 nM PMID[466179]
NPT720 Organism Enterobacter aerogenes Enterobacter aerogenes MIC >= 100000.0 nM PMID[466179]
NPT19 Organism Escherichia coli Escherichia coli MIC >= 100000.0 nM PMID[466179]

☑ 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 NPC25899 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
0.9799 High Similarity NPC48192
0.9051 High Similarity NPC121658
0.9051 High Similarity NPC14651
0.9012 High Similarity NPC219963
0.9012 High Similarity NPC266551
0.9012 High Similarity NPC161887
0.8987 High Similarity NPC476518
0.8758 High Similarity NPC111624
0.8512 High Similarity NPC20249
0.8488 Intermediate Similarity NPC226202
0.8412 Intermediate Similarity NPC206251
0.8412 Intermediate Similarity NPC74382
0.815 Intermediate Similarity NPC224327
0.811 Intermediate Similarity NPC471178
0.8103 Intermediate Similarity NPC134079
0.8098 Intermediate Similarity NPC471177
0.8098 Intermediate Similarity NPC59779
0.8098 Intermediate Similarity NPC124542
0.8063 Intermediate Similarity NPC36168
0.7975 Intermediate Similarity NPC220523
0.791 Intermediate Similarity NPC324149
0.7869 Intermediate Similarity NPC200836
0.7857 Intermediate Similarity NPC314940
0.7857 Intermediate Similarity NPC473764
0.7831 Intermediate Similarity NPC97367
0.7831 Intermediate Similarity NPC473057
0.7785 Intermediate Similarity NPC151489
0.7772 Intermediate Similarity NPC53144
0.7771 Intermediate Similarity NPC79911
0.7747 Intermediate Similarity NPC476167
0.7735 Intermediate Similarity NPC267928
0.7717 Intermediate Similarity NPC211813
0.7712 Intermediate Similarity NPC174421
0.7711 Intermediate Similarity NPC120798
0.7706 Intermediate Similarity NPC252590
0.7692 Intermediate Similarity NPC192315
0.7673 Intermediate Similarity NPC470404
0.7673 Intermediate Similarity NPC470403
0.7673 Intermediate Similarity NPC470394
0.7667 Intermediate Similarity NPC329541
0.7665 Intermediate Similarity NPC177404
0.7634 Intermediate Similarity NPC475070
0.7634 Intermediate Similarity NPC470500
0.7628 Intermediate Similarity NPC328029
0.7584 Intermediate Similarity NPC46580
0.7578 Intermediate Similarity NPC470395
0.7577 Intermediate Similarity NPC213530
0.7577 Intermediate Similarity NPC193267
0.7571 Intermediate Similarity NPC314002
0.7547 Intermediate Similarity NPC318935
0.7545 Intermediate Similarity NPC84508
0.7542 Intermediate Similarity NPC472289
0.7529 Intermediate Similarity NPC108469
0.7526 Intermediate Similarity NPC5145
0.7526 Intermediate Similarity NPC85273
0.7514 Intermediate Similarity NPC204717
0.7514 Intermediate Similarity NPC19872
0.75 Intermediate Similarity NPC476121
0.75 Intermediate Similarity NPC476124
0.75 Intermediate Similarity NPC60553
0.7485 Intermediate Similarity NPC257142
0.7458 Intermediate Similarity NPC48938
0.7458 Intermediate Similarity NPC220765
0.743 Intermediate Similarity NPC171171
0.7429 Intermediate Similarity NPC96890
0.7429 Intermediate Similarity NPC184964
0.7423 Intermediate Similarity NPC161292
0.7414 Intermediate Similarity NPC95898
0.7396 Intermediate Similarity NPC285635
0.7385 Intermediate Similarity NPC476041
0.7385 Intermediate Similarity NPC304926
0.738 Intermediate Similarity NPC232727
0.7377 Intermediate Similarity NPC84853
0.7371 Intermediate Similarity NPC203754
0.7371 Intermediate Similarity NPC150048
0.7365 Intermediate Similarity NPC63562
0.7349 Intermediate Similarity NPC284348
0.7338 Intermediate Similarity NPC212125
0.7333 Intermediate Similarity NPC288445
0.7333 Intermediate Similarity NPC314573
0.7333 Intermediate Similarity NPC8022
0.7333 Intermediate Similarity NPC470799
0.733 Intermediate Similarity NPC287208
0.7326 Intermediate Similarity NPC315957
0.7326 Intermediate Similarity NPC176538
0.7322 Intermediate Similarity NPC99666
0.7312 Intermediate Similarity NPC212213
0.7297 Intermediate Similarity NPC242209
0.7294 Intermediate Similarity NPC63338
0.7294 Intermediate Similarity NPC324203
0.7294 Intermediate Similarity NPC131718
0.7294 Intermediate Similarity NPC322976
0.7292 Intermediate Similarity NPC174672
0.7278 Intermediate Similarity NPC132680
0.7278 Intermediate Similarity NPC269919
0.7273 Intermediate Similarity NPC187558
0.7263 Intermediate Similarity NPC264166
0.7263 Intermediate Similarity NPC274291
0.7263 Intermediate Similarity NPC47059
0.7263 Intermediate Similarity NPC472259
0.7263 Intermediate Similarity NPC118832
0.7263 Intermediate Similarity NPC165349
0.7263 Intermediate Similarity NPC329708
0.7258 Intermediate Similarity NPC90229
0.7254 Intermediate Similarity NPC167860
0.7254 Intermediate Similarity NPC123976
0.7246 Intermediate Similarity NPC153769
0.724 Intermediate Similarity NPC477111
0.7202 Intermediate Similarity NPC174758
0.7202 Intermediate Similarity NPC26872
0.72 Intermediate Similarity NPC253810
0.72 Intermediate Similarity NPC258773
0.7191 Intermediate Similarity NPC42979
0.7184 Intermediate Similarity NPC44161
0.7179 Intermediate Similarity NPC202605
0.7179 Intermediate Similarity NPC112206
0.7176 Intermediate Similarity NPC116573
0.7175 Intermediate Similarity NPC224764
0.7166 Intermediate Similarity NPC77555
0.716 Intermediate Similarity NPC280853
0.7158 Intermediate Similarity NPC32771
0.7152 Intermediate Similarity NPC256893
0.7151 Intermediate Similarity NPC222592
0.7151 Intermediate Similarity NPC168486
0.7151 Intermediate Similarity NPC326634
0.715 Intermediate Similarity NPC310118
0.715 Intermediate Similarity NPC60621
0.715 Intermediate Similarity NPC82548
0.7143 Intermediate Similarity NPC164664
0.7143 Intermediate Similarity NPC249040
0.7135 Intermediate Similarity NPC477113
0.7128 Intermediate Similarity NPC239954
0.7127 Intermediate Similarity NPC284678
0.7127 Intermediate Similarity NPC284559
0.7121 Intermediate Similarity NPC469727
0.7121 Intermediate Similarity NPC27041
0.712 Intermediate Similarity NPC476138
0.712 Intermediate Similarity NPC245816
0.7117 Intermediate Similarity NPC245657
0.7117 Intermediate Similarity NPC285016
0.7115 Intermediate Similarity NPC471313
0.7115 Intermediate Similarity NPC471311
0.7115 Intermediate Similarity NPC306397
0.7113 Intermediate Similarity NPC185782
0.711 Intermediate Similarity NPC102423
0.711 Intermediate Similarity NPC263439
0.711 Intermediate Similarity NPC211187
0.7107 Intermediate Similarity NPC237740
0.7099 Intermediate Similarity NPC471596
0.7097 Intermediate Similarity NPC106937
0.7097 Intermediate Similarity NPC198673
0.7095 Intermediate Similarity NPC72980
0.7092 Intermediate Similarity NPC471603
0.709 Intermediate Similarity NPC287437
0.7088 Intermediate Similarity NPC295158
0.7086 Intermediate Similarity NPC1527
0.7081 Intermediate Similarity NPC29702
0.7079 Intermediate Similarity NPC288943
0.7076 Intermediate Similarity NPC26850
0.7074 Intermediate Similarity NPC474188
0.7074 Intermediate Similarity NPC156704
0.7074 Intermediate Similarity NPC224928
0.7065 Intermediate Similarity NPC110741
0.7062 Intermediate Similarity NPC18348
0.7059 Intermediate Similarity NPC6215
0.7053 Intermediate Similarity NPC121772
0.7045 Intermediate Similarity NPC256828
0.7044 Intermediate Similarity NPC324611
0.7039 Intermediate Similarity NPC283152
0.7037 Intermediate Similarity NPC474916
0.703 Intermediate Similarity NPC470501
0.7027 Intermediate Similarity NPC3715
0.7006 Intermediate Similarity NPC165370
0.7005 Intermediate Similarity NPC307963
0.7005 Intermediate Similarity NPC26679
0.6995 Remote Similarity NPC16452
0.6995 Remote Similarity NPC476581
0.6995 Remote Similarity NPC36229
0.699 Remote Similarity NPC309845
0.6988 Remote Similarity NPC471323
0.6988 Remote Similarity NPC471598
0.6985 Remote Similarity NPC274982
0.6985 Remote Similarity NPC477110
0.698 Remote Similarity NPC470502
0.6976 Remote Similarity NPC110151
0.6967 Remote Similarity NPC477861
0.6966 Remote Similarity NPC474409
0.6966 Remote Similarity NPC313791
0.6964 Remote Similarity NPC470111
0.6963 Remote Similarity NPC315491
0.6963 Remote Similarity NPC45459
0.6961 Remote Similarity NPC478023
0.6959 Remote Similarity NPC323345
0.6959 Remote Similarity NPC470164
0.6957 Remote Similarity NPC476451
0.6947 Remote Similarity NPC168911
0.694 Remote Similarity NPC62069
0.6939 Remote Similarity NPC469589
0.6938 Remote Similarity NPC182222
0.6932 Remote Similarity NPC41717

  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 NPC25899 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
0.8199 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD424 Approved
0.8171 Intermediate Similarity NPD425 Approved
0.8 Intermediate Similarity NPD925 Approved
0.8 Intermediate Similarity NPD926 Approved
0.7867 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD1649 Discontinued
0.7758 Intermediate Similarity NPD5255 Approved
0.7647 Intermediate Similarity NPD715 Phase 3
0.7616 Intermediate Similarity NPD9690 Approved
0.7605 Intermediate Similarity NPD9705 Discontinued
0.7605 Intermediate Similarity NPD112 Approved
0.7588 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD2781 Approved
0.7471 Intermediate Similarity NPD2780 Approved
0.7471 Intermediate Similarity NPD2782 Approved
0.7412 Intermediate Similarity NPD861 Approved
0.7412 Intermediate Similarity NPD863 Approved
0.7412 Intermediate Similarity NPD862 Approved
0.7378 Intermediate Similarity NPD4703 Approved
0.7378 Intermediate Similarity NPD1661 Suspended
0.7378 Intermediate Similarity NPD4702 Approved
0.7377 Intermediate Similarity NPD9695 Approved
0.7351 Intermediate Similarity NPD1622 Discontinued
0.7349 Intermediate Similarity NPD2882 Phase 1
0.7346 Intermediate Similarity NPD3717 Discontinued
0.7338 Intermediate Similarity NPD9284 Approved
0.733 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD1740 Approved
0.7326 Intermediate Similarity NPD1739 Approved
0.7322 Intermediate Similarity NPD6569 Phase 2
0.7314 Intermediate Similarity NPD158 Discontinued
0.7308 Intermediate Similarity NPD4081 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD3813 Approved
0.7299 Intermediate Similarity NPD2123 Phase 3
0.7294 Intermediate Similarity NPD9398 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD9382 Approved
0.7278 Intermediate Similarity NPD9383 Approved
0.7273 Intermediate Similarity NPD5100 Phase 3
0.7263 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD4034 Approved
0.7263 Intermediate Similarity NPD4036 Approved
0.7263 Intermediate Similarity NPD32 Approved
0.7263 Intermediate Similarity NPD4035 Approved
0.7263 Intermediate Similarity NPD4122 Approved
0.7263 Intermediate Similarity NPD4039 Approved
0.7263 Intermediate Similarity NPD4038 Approved
0.7263 Intermediate Similarity NPD4037 Approved
0.7263 Intermediate Similarity NPD4033 Approved
0.7263 Intermediate Similarity NPD31 Approved
0.7249 Intermediate Similarity NPD3928 Approved
0.7249 Intermediate Similarity NPD3931 Approved
0.7238 Intermediate Similarity NPD4375 Approved
0.7235 Intermediate Similarity NPD3433 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD6159 Phase 2
0.7229 Intermediate Similarity NPD3575 Approved
0.7229 Intermediate Similarity NPD3576 Approved
0.7228 Intermediate Similarity NPD4372 Phase 1
0.7213 Intermediate Similarity NPD3321 Discontinued
0.7212 Intermediate Similarity NPD7469 Discontinued
0.7207 Intermediate Similarity NPD4204 Approved
0.7207 Intermediate Similarity NPD7867 Phase 1
0.7207 Intermediate Similarity NPD4203 Approved
0.7207 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD8823 Approved
0.7191 Intermediate Similarity NPD1620 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD1197 Approved
0.7179 Intermediate Similarity NPD5352 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD4795 Phase 2
0.7159 Intermediate Similarity NPD1599 Approved
0.7157 Intermediate Similarity NPD7112 Discontinued
0.7151 Intermediate Similarity NPD3396 Approved
0.7151 Intermediate Similarity NPD3395 Approved
0.7143 Intermediate Similarity NPD706 Phase 1
0.7143 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD1213 Phase 3
0.7115 Intermediate Similarity NPD9080 Approved
0.7114 Intermediate Similarity NPD1856 Discontinued
0.7112 Intermediate Similarity NPD3477 Phase 2
0.7112 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD1034 Phase 3
0.7099 Intermediate Similarity NPD9076 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD802 Phase 2
0.7091 Intermediate Similarity NPD1352 Discontinued
0.7088 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD3082 Discontinued
0.7076 Intermediate Similarity NPD2581 Approved
0.7076 Intermediate Similarity NPD2582 Approved
0.7074 Intermediate Similarity NPD2952 Discontinued
0.7074 Intermediate Similarity NPD7948 Phase 1
0.7045 Intermediate Similarity NPD5320 Approved
0.7045 Intermediate Similarity NPD5319 Approved
0.7043 Intermediate Similarity NPD5317 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD9689 Approved
0.7041 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD6158 Phase 2
0.7037 Intermediate Similarity NPD9506 Approved
0.7027 Intermediate Similarity NPD5316 Approved
0.7027 Intermediate Similarity NPD3439 Approved
0.7022 Intermediate Similarity NPD6492 Phase 2
0.7022 Intermediate Similarity NPD5065 Approved
0.7018 Intermediate Similarity NPD1274 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD3386 Phase 2
0.7005 Intermediate Similarity NPD4551 Phase 2
0.7005 Intermediate Similarity NPD3330 Phase 1
0.7005 Intermediate Similarity NPD1038 Approved
0.6995 Remote Similarity NPD2762 Phase 2
0.6995 Remote Similarity NPD4889 Approved
0.6994 Remote Similarity NPD852 Discontinued
0.6989 Remote Similarity NPD5862 Discovery
0.6989 Remote Similarity NPD6022 Clinical (unspecified phase)
0.6989 Remote Similarity NPD2334 Discontinued
0.6979 Remote Similarity NPD6975 Discontinued
0.6977 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6977 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6977 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1037 Clinical (unspecified phase)
0.6963 Remote Similarity NPD6389 Clinical (unspecified phase)
0.6963 Remote Similarity NPD484 Approved
0.6959 Remote Similarity NPD5530 Phase 1
0.6952 Remote Similarity NPD6887 Clinical (unspecified phase)
0.6949 Remote Similarity NPD565 Phase 2
0.6943 Remote Similarity NPD4886 Phase 2
0.6941 Remote Similarity NPD9595 Approved
0.6941 Remote Similarity NPD9596 Approved
0.6935 Remote Similarity NPD8063 Discontinued
0.6919 Remote Similarity NPD2383 Phase 1
0.6906 Remote Similarity NPD1503 Clinical (unspecified phase)
0.6895 Remote Similarity NPD1229 Phase 2
0.6888 Remote Similarity NPD2816 Clinical (unspecified phase)
0.6882 Remote Similarity NPD4021 Phase 2
0.6878 Remote Similarity NPD1602 Discontinued
0.6869 Remote Similarity NPD4131 Phase 3
0.6866 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6862 Remote Similarity NPD3924 Approved
0.6862 Remote Similarity NPD3923 Approved
0.6862 Remote Similarity NPD3921 Approved
0.6862 Remote Similarity NPD3922 Approved
0.6859 Remote Similarity NPD5885 Approved
0.6857 Remote Similarity NPD1684 Approved
0.6857 Remote Similarity NPD1685 Approved
0.6848 Remote Similarity NPD6178 Phase 3
0.6845 Remote Similarity NPD7603 Discontinued
0.6839 Remote Similarity NPD704 Clinical (unspecified phase)
0.6833 Remote Similarity NPD1923 Clinical (unspecified phase)
0.6831 Remote Similarity NPD8408 Discontinued
0.6825 Remote Similarity NPD1304 Clinical (unspecified phase)
0.6825 Remote Similarity NPD6361 Phase 2
0.6823 Remote Similarity NPD9687 Approved
0.6823 Remote Similarity NPD9688 Approved
0.6821 Remote Similarity NPD3500 Clinical (unspecified phase)
0.6806 Remote Similarity NPD2959 Phase 3
0.6803 Remote Similarity NPD9098 Phase 3
0.6803 Remote Similarity NPD9099 Clinical (unspecified phase)
0.6798 Remote Similarity NPD6501 Approved
0.6798 Remote Similarity NPD6500 Approved
0.6797 Remote Similarity NPD9396 Approved
0.6797 Remote Similarity NPD9392 Approved
0.6796 Remote Similarity NPD2751 Phase 1
0.6786 Remote Similarity NPD1918 Clinical (unspecified phase)
0.6784 Remote Similarity NPD3570 Phase 2
0.678 Remote Similarity NPD4945 Discontinued
0.678 Remote Similarity NPD8356 Approved
0.678 Remote Similarity NPD2720 Phase 1
0.678 Remote Similarity NPD2719 Clinical (unspecified phase)
0.6776 Remote Similarity NPD2600 Approved
0.6776 Remote Similarity NPD2599 Approved
0.6776 Remote Similarity NPD2601 Approved
0.6774 Remote Similarity NPD3039 Clinical (unspecified phase)
0.677 Remote Similarity NPD9206 Approved
0.677 Remote Similarity NPD9207 Approved
0.6769 Remote Similarity NPD4044 Discontinued
0.6758 Remote Similarity NPD4072 Approved
0.6758 Remote Similarity NPD1032 Phase 2
0.6758 Remote Similarity NPD4071 Approved
0.6751 Remote Similarity NPD1392 Approved
0.675 Remote Similarity NPD3816 Phase 1
0.675 Remote Similarity NPD3815 Phase 1
0.675 Remote Similarity NPD7069 Discontinued
0.6739 Remote Similarity NPD1570 Approved
0.6737 Remote Similarity NPD4526 Approved
0.6737 Remote Similarity NPD4529 Approved
0.6737 Remote Similarity NPD5428 Discontinued
0.6737 Remote Similarity NPD4528 Approved
0.6736 Remote Similarity NPD5999 Phase 2
0.6736 Remote Similarity NPD2177 Approved
0.6736 Remote Similarity NPD2176 Approved
0.6736 Remote Similarity NPD4548 Discontinued
0.6736 Remote Similarity NPD2175 Phase 3
0.6733 Remote Similarity NPD6803 Clinical (unspecified phase)
0.6732 Remote Similarity NPD4881 Clinical (unspecified phase)
0.6731 Remote Similarity NPD8430 Approved
0.6723 Remote Similarity NPD5925 Phase 1
0.6723 Remote Similarity NPD5138 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