Structure

Physi-Chem Properties

Molecular Weight:  866.4
Volume:  866.594
LogP:  1.376
LogD:  1.557
LogS:  -3.707
# Rotatable Bonds:  8
TPSA:  227.96
# H-Bond Aceptor:  18
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.247
Synthetic Accessibility Score:  5.531
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.803
MDCK Permeability:  6.772983851988101e-06
Pgp-inhibitor:  0.751
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.469
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.724

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.104
Plasma Protein Binding (PPB):  73.06805419921875%
Volume Distribution (VD):  0.26
Pgp-substrate:  34.23579406738281%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.024
CYP2C19-inhibitor:  0.116
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.671
CYP2C9-substrate:  0.079
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.163
CYP3A4-inhibitor:  0.844
CYP3A4-substrate:  0.07

ADMET: Excretion

Clearance (CL):  3.544
Half-life (T1/2):  0.551

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.985
Drug-inuced Liver Injury (DILI):  0.989
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.941
Maximum Recommended Daily Dose:  0.907
Skin Sensitization:  0.087
Carcinogencity:  0.05
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.256

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

  Natural Product: NPC186351

Natural Product ID:  NPC186351
Common Name*:   Pristinamycin 1A
IUPAC Name:   n.a.
Synonyms:   Pristinamycin
Standard InCHIKey:  YGXCETJZBDTKRY-DZCVGBHJSA-N
Standard InCHI:  InChI=1S/C45H54N8O10/c1-6-31-42(59)52-22-11-14-32(52)43(60)51(5)34(24-27-16-18-29(19-17-27)50(3)4)44(61)53-23-20-30(54)25-33(53)39(56)49-37(28-12-8-7-9-13-28)45(62)63-26(2)36(40(57)47-31)48-41(58)38-35(55)15-10-21-46-38/h7-10,12-13,15-19,21,26,31-34,36-37,55H,6,11,14,20,22-25H2,1-5H3,(H,47,57)(H,48,58)(H,49,56)/t26-,31-,32+,33+,34+,36+,37+/m1/s1
SMILES:  CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](Cc2ccc(cc2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=N[C@@H](c2ccccc2)C(=O)O[C@H](C)[C@@H](C(=N1)O)N=C(c1c(cccn1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1256399
PubChem CID:   11136668
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0001961] Depsipeptides
          • [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO8948 Streptomyces pristinaespiralis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25708513]
NPO8948 Streptomyces pristinaespiralis Species Streptomycetaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 2.0 ug.mL-1 PMID[515690]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 8.0 ug.mL-1 PMID[515690]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 1.0 ug.mL-1 PMID[515690]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 128.0 ug.mL-1 PMID[515690]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 4.0 ug.mL-1 PMID[515690]
NPT19 Organism Escherichia coli Escherichia coli MIC = 64.0 ug.mL-1 PMID[515690]
NPT19 Organism Escherichia coli Escherichia coli MIC = 4.0 ug.mL-1 PMID[515690]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 32.0 ug.mL-1 PMID[515690]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Inhibition = 55.0 % PMID[515691]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (moderate) = 0.0 n.a. PMID[515692]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (moderate) = 0.0 % PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (acute) = 1.0 n.a. PMID[515692]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (acute) = 0.0 % PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (cytolytic) = 1.0 n.a. PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (choleostasis) = 0.0 n.a. PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (severe hepatitis) = 0.0 n.a. PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (chronic liver disease) = 0.0 n.a. PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (cirrhosis) = 0.0 n.a. PMID[515692]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (granulomatous hepatitis) = 0.0 n.a. PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (association with vascular disease) = 0.0 n.a. PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (steatosis) = 0.0 n.a. PMID[515692]
NPT2 Others Unspecified Hepatotoxicity (malignant tumour) = 0.0 n.a. PMID[515692]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (benign tumour) = 0.0 n.a. PMID[515692]

☑ 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 NPC186351 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
0.9268 High Similarity NPC315804
0.9268 High Similarity NPC313804
0.8732 High Similarity NPC316403
0.8009 Intermediate Similarity NPC220852
0.7982 Intermediate Similarity NPC285343
0.7982 Intermediate Similarity NPC24370
0.7982 Intermediate Similarity NPC319232
0.7909 Intermediate Similarity NPC314270
0.7851 Intermediate Similarity NPC323752
0.7773 Intermediate Similarity NPC314882
0.7748 Intermediate Similarity NPC281049
0.7689 Intermediate Similarity NPC313587
0.7689 Intermediate Similarity NPC316110
0.7689 Intermediate Similarity NPC315893
0.7672 Intermediate Similarity NPC28945
0.766 Intermediate Similarity NPC316224
0.7645 Intermediate Similarity NPC478006
0.7632 Intermediate Similarity NPC244536
0.7602 Intermediate Similarity NPC315467
0.7571 Intermediate Similarity NPC478009
0.7571 Intermediate Similarity NPC478010
0.7565 Intermediate Similarity NPC326363
0.7534 Intermediate Similarity NPC478157
0.75 Intermediate Similarity NPC477516
0.749 Intermediate Similarity NPC161801
0.7467 Intermediate Similarity NPC125597
0.7466 Intermediate Similarity NPC478158
0.7456 Intermediate Similarity NPC478141
0.7443 Intermediate Similarity NPC472259
0.7436 Intermediate Similarity NPC325976
0.7421 Intermediate Similarity NPC478012
0.7421 Intermediate Similarity NPC478011
0.7419 Intermediate Similarity NPC314056
0.7414 Intermediate Similarity NPC322135
0.7403 Intermediate Similarity NPC34580
0.7403 Intermediate Similarity NPC124920
0.7403 Intermediate Similarity NPC118559
0.7403 Intermediate Similarity NPC304307
0.7393 Intermediate Similarity NPC284888
0.7391 Intermediate Similarity NPC314176
0.7373 Intermediate Similarity NPC313421
0.7371 Intermediate Similarity NPC100547
0.7348 Intermediate Similarity NPC64216
0.7339 Intermediate Similarity NPC223409
0.7339 Intermediate Similarity NPC95240
0.7336 Intermediate Similarity NPC473317
0.7331 Intermediate Similarity NPC478013
0.7328 Intermediate Similarity NPC261251
0.7319 Intermediate Similarity NPC323198
0.7311 Intermediate Similarity NPC477586
0.7311 Intermediate Similarity NPC477588
0.7311 Intermediate Similarity NPC477590
0.7311 Intermediate Similarity NPC477585
0.7308 Intermediate Similarity NPC14288
0.729 Intermediate Similarity NPC473763
0.729 Intermediate Similarity NPC117244
0.7288 Intermediate Similarity NPC182222
0.7284 Intermediate Similarity NPC214142
0.7277 Intermediate Similarity NPC321592
0.7277 Intermediate Similarity NPC54803
0.7257 Intermediate Similarity NPC317752
0.7257 Intermediate Similarity NPC477549
0.7256 Intermediate Similarity NPC471448
0.725 Intermediate Similarity NPC473312
0.7236 Intermediate Similarity NPC472435
0.7234 Intermediate Similarity NPC477112
0.7227 Intermediate Similarity NPC477589
0.7227 Intermediate Similarity NPC477587
0.7227 Intermediate Similarity NPC184225
0.7224 Intermediate Similarity NPC153400
0.7218 Intermediate Similarity NPC472436
0.7215 Intermediate Similarity NPC33064
0.7215 Intermediate Similarity NPC245055
0.7212 Intermediate Similarity NPC318299
0.7207 Intermediate Similarity NPC214827
0.7207 Intermediate Similarity NPC314930
0.7197 Intermediate Similarity NPC82472
0.7195 Intermediate Similarity NPC476874
0.719 Intermediate Similarity NPC271792
0.717 Intermediate Similarity NPC294951
0.7163 Intermediate Similarity NPC469938
0.7163 Intermediate Similarity NPC279871
0.7156 Intermediate Similarity NPC162860
0.7131 Intermediate Similarity NPC89987
0.7115 Intermediate Similarity NPC137627
0.7111 Intermediate Similarity NPC475024
0.7105 Intermediate Similarity NPC74562
0.7105 Intermediate Similarity NPC151781
0.7105 Intermediate Similarity NPC316181
0.7101 Intermediate Similarity NPC141053
0.7098 Intermediate Similarity NPC472286
0.7098 Intermediate Similarity NPC472287
0.7091 Intermediate Similarity NPC472284
0.7083 Intermediate Similarity NPC3715
0.7082 Intermediate Similarity NPC216612
0.7067 Intermediate Similarity NPC54420
0.7062 Intermediate Similarity NPC269750
0.7062 Intermediate Similarity NPC194671
0.7061 Intermediate Similarity NPC251036
0.7061 Intermediate Similarity NPC75634
0.7056 Intermediate Similarity NPC295158
0.7054 Intermediate Similarity NPC41679
0.7054 Intermediate Similarity NPC474183
0.7049 Intermediate Similarity NPC472434
0.7045 Intermediate Similarity NPC181081
0.704 Intermediate Similarity NPC182507
0.704 Intermediate Similarity NPC57398
0.7035 Intermediate Similarity NPC477111
0.7035 Intermediate Similarity NPC287208
0.7031 Intermediate Similarity NPC54744
0.7031 Intermediate Similarity NPC250448
0.7027 Intermediate Similarity NPC315491
0.7027 Intermediate Similarity NPC45459
0.7013 Intermediate Similarity NPC27041
0.7012 Intermediate Similarity NPC15801
0.7009 Intermediate Similarity NPC320394
0.7009 Intermediate Similarity NPC476098
0.7009 Intermediate Similarity NPC207851
0.7008 Intermediate Similarity NPC75179
0.7005 Intermediate Similarity NPC163961
0.7005 Intermediate Similarity NPC473305
0.7004 Intermediate Similarity NPC33949
0.7 Intermediate Similarity NPC237740
0.6987 Remote Similarity NPC472098
0.6987 Remote Similarity NPC328924
0.6986 Remote Similarity NPC230403
0.6986 Remote Similarity NPC253810
0.6985 Remote Similarity NPC196449
0.6985 Remote Similarity NPC314222
0.6982 Remote Similarity NPC160127
0.6982 Remote Similarity NPC123395
0.6982 Remote Similarity NPC50997
0.697 Remote Similarity NPC74969
0.697 Remote Similarity NPC469928
0.697 Remote Similarity NPC322064
0.6968 Remote Similarity NPC473814
0.6968 Remote Similarity NPC78767
0.6962 Remote Similarity NPC476491
0.6962 Remote Similarity NPC323244
0.6955 Remote Similarity NPC93390
0.6953 Remote Similarity NPC269270
0.6947 Remote Similarity NPC317373
0.6946 Remote Similarity NPC476451
0.6944 Remote Similarity NPC94752
0.6942 Remote Similarity NPC59779
0.6942 Remote Similarity NPC184680
0.6942 Remote Similarity NPC471177
0.6942 Remote Similarity NPC124542
0.6937 Remote Similarity NPC212213
0.6937 Remote Similarity NPC474916
0.6933 Remote Similarity NPC317572
0.6931 Remote Similarity NPC284348
0.693 Remote Similarity NPC145178
0.693 Remote Similarity NPC475350
0.693 Remote Similarity NPC14877
0.6923 Remote Similarity NPC41717
0.6923 Remote Similarity NPC14686
0.6923 Remote Similarity NPC54066
0.6923 Remote Similarity NPC471891
0.6919 Remote Similarity NPC159767
0.6919 Remote Similarity NPC26108
0.6919 Remote Similarity NPC155506
0.6916 Remote Similarity NPC53344
0.6914 Remote Similarity NPC470784
0.6914 Remote Similarity NPC470785
0.6913 Remote Similarity NPC111732
0.691 Remote Similarity NPC49195
0.6905 Remote Similarity NPC230611
0.6903 Remote Similarity NPC470500
0.6903 Remote Similarity NPC47059
0.6903 Remote Similarity NPC165349
0.6903 Remote Similarity NPC329708
0.6903 Remote Similarity NPC118832
0.6903 Remote Similarity NPC274291
0.6903 Remote Similarity NPC264166
0.6903 Remote Similarity NPC327592
0.6902 Remote Similarity NPC152620
0.6901 Remote Similarity NPC272549
0.69 Remote Similarity NPC5145
0.6898 Remote Similarity NPC72905
0.6897 Remote Similarity NPC330009
0.6897 Remote Similarity NPC477110
0.6892 Remote Similarity NPC90229
0.6889 Remote Similarity NPC193761
0.6889 Remote Similarity NPC328318
0.6889 Remote Similarity NPC328596
0.6889 Remote Similarity NPC211813
0.6887 Remote Similarity NPC203754
0.6887 Remote Similarity NPC150048
0.6884 Remote Similarity NPC143533
0.6878 Remote Similarity NPC135950
0.6878 Remote Similarity NPC289299
0.6878 Remote Similarity NPC57994
0.6878 Remote Similarity NPC116573
0.6875 Remote Similarity NPC475969
0.6875 Remote Similarity NPC471178
0.6875 Remote Similarity NPC475859
0.6872 Remote Similarity NPC477113
0.6872 Remote Similarity NPC306804
0.6867 Remote Similarity NPC469727

  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 NPC186351 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
1.0 High Similarity NPD8430 Approved
0.9801 High Similarity NPD8356 Approved
0.7924 Intermediate Similarity NPD8370 Discontinued
0.7822 Intermediate Similarity NPD7603 Discontinued
0.7713 Intermediate Similarity NPD7203 Clinical (unspecified phase)
0.7668 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD4086 Phase 1
0.7588 Intermediate Similarity NPD5640 Discontinued
0.7523 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7522 Intermediate Similarity NPD8479 Phase 2
0.7455 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD8289 Discontinued
0.7434 Intermediate Similarity NPD6568 Discontinued
0.7389 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD7944 Discontinued
0.7321 Intermediate Similarity NPD3779 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD7886 Phase 2
0.7311 Intermediate Similarity NPD7885 Phase 2
0.7306 Intermediate Similarity NPD8247 Approved
0.7306 Intermediate Similarity NPD8246 Approved
0.7304 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD7923 Phase 2
0.7257 Intermediate Similarity NPD7853 Phase 2
0.7256 Intermediate Similarity NPD6665 Discontinued
0.7256 Intermediate Similarity NPD5317 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD5316 Approved
0.7234 Intermediate Similarity NPD7284 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD6393 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD4958 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD7807 Clinical (unspecified phase)
0.721 Intermediate Similarity NPD7426 Phase 1
0.7198 Intermediate Similarity NPD7547 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD8463 Approved
0.7186 Intermediate Similarity NPD7726 Phase 1
0.7176 Intermediate Similarity NPD4372 Phase 1
0.7171 Intermediate Similarity NPD4174 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD7470 Discontinued
0.7163 Intermediate Similarity NPD8063 Discontinued
0.7143 Intermediate Similarity NPD7180 Phase 3
0.7137 Intermediate Similarity NPD7069 Discontinued
0.713 Intermediate Similarity NPD3947 Discontinued
0.7124 Intermediate Similarity NPD6753 Phase 1
0.7124 Intermediate Similarity NPD6752 Phase 1
0.7111 Intermediate Similarity NPD6366 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7467 Discontinued
0.7111 Intermediate Similarity NPD7666 Phase 3
0.7111 Intermediate Similarity NPD7665 Phase 2
0.7098 Intermediate Similarity NPD7001 Phase 3
0.7097 Intermediate Similarity NPD6569 Phase 2
0.7095 Intermediate Similarity NPD6159 Phase 2
0.7094 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD7482 Phase 2
0.7089 Intermediate Similarity NPD7483 Phase 2
0.7083 Intermediate Similarity NPD1213 Phase 3
0.7083 Intermediate Similarity NPD3321 Discontinued
0.7078 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD3477 Phase 2
0.7074 Intermediate Similarity NPD4897 Phase 2
0.7073 Intermediate Similarity NPD8101 Phase 3
0.707 Intermediate Similarity NPD5922 Phase 3
0.7064 Intermediate Similarity NPD4528 Approved
0.7064 Intermediate Similarity NPD4526 Approved
0.7064 Intermediate Similarity NPD3263 Phase 3
0.7064 Intermediate Similarity NPD4529 Approved
0.7061 Intermediate Similarity NPD8093 Discontinued
0.7059 Intermediate Similarity NPD7031 Phase 1
0.7049 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7234 Approved
0.7037 Intermediate Similarity NPD7233 Approved
0.7029 Intermediate Similarity NPD6223 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD484 Approved
0.7027 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD6974 Phase 3
0.7018 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD8106 Phase 2
0.701 Intermediate Similarity NPD5255 Approved
0.7009 Intermediate Similarity NPD6209 Approved
0.7005 Intermediate Similarity NPD4081 Clinical (unspecified phase)
0.6996 Remote Similarity NPD7576 Discontinued
0.6987 Remote Similarity NPD7797 Approved
0.6987 Remote Similarity NPD7594 Clinical (unspecified phase)
0.6987 Remote Similarity NPD5866 Approved
0.6987 Remote Similarity NPD7796 Approved
0.6983 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6983 Remote Similarity NPD5948 Phase 2
0.6975 Remote Similarity NPD1659 Phase 1
0.6975 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6971 Remote Similarity NPD5862 Discovery
0.697 Remote Similarity NPD3389 Approved
0.697 Remote Similarity NPD3393 Approved
0.697 Remote Similarity NPD2433 Clinical (unspecified phase)
0.697 Remote Similarity NPD3394 Approved
0.6967 Remote Similarity NPD6716 Phase 1
0.6962 Remote Similarity NPD7268 Clinical (unspecified phase)
0.696 Remote Similarity NPD6376 Discontinued
0.6955 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6951 Remote Similarity NPD8100 Phase 3
0.695 Remote Similarity NPD7655 Discontinued
0.6943 Remote Similarity NPD7703 Clinical (unspecified phase)
0.694 Remote Similarity NPD8406 Clinical (unspecified phase)
0.694 Remote Similarity NPD8325 Phase 3
0.694 Remote Similarity NPD8327 Clinical (unspecified phase)
0.694 Remote Similarity NPD8326 Phase 3
0.694 Remote Similarity NPD4989 Phase 2
0.6937 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6935 Remote Similarity NPD5482 Discontinued
0.6935 Remote Similarity NPD3809 Discontinued
0.693 Remote Similarity NPD1096 Discontinued
0.6926 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7996 Phase 2
0.6923 Remote Similarity NPD5512 Phase 3
0.6923 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7660 Clinical (unspecified phase)
0.6913 Remote Similarity NPD3330 Phase 1
0.6912 Remote Similarity NPD1034 Phase 3
0.6912 Remote Similarity NPD1033 Clinical (unspecified phase)
0.691 Remote Similarity NPD4429 Discontinued
0.6907 Remote Similarity NPD6173 Approved
0.6905 Remote Similarity NPD2123 Phase 3
0.6904 Remote Similarity NPD5022 Discontinued
0.6904 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6903 Remote Similarity NPD32 Approved
0.6903 Remote Similarity NPD31 Approved
0.6903 Remote Similarity NPD4039 Approved
0.6903 Remote Similarity NPD4038 Approved
0.6903 Remote Similarity NPD4122 Approved
0.6903 Remote Similarity NPD4034 Approved
0.6903 Remote Similarity NPD4035 Approved
0.6903 Remote Similarity NPD4036 Approved
0.6903 Remote Similarity NPD4033 Approved
0.6903 Remote Similarity NPD4037 Approved
0.69 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6894 Remote Similarity NPD5507 Approved
0.6894 Remote Similarity NPD5506 Approved
0.6892 Remote Similarity NPD7948 Phase 1
0.6889 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6889 Remote Similarity NPD2779 Approved
0.6888 Remote Similarity NPD7790 Approved
0.6888 Remote Similarity NPD7789 Approved
0.6888 Remote Similarity NPD7952 Approved
0.6888 Remote Similarity NPD7791 Approved
0.6888 Remote Similarity NPD7953 Approved
0.6888 Remote Similarity NPD7951 Approved
0.6888 Remote Similarity NPD7950 Approved
0.6887 Remote Similarity NPD7924 Phase 2
0.6887 Remote Similarity NPD7925 Phase 2
0.6883 Remote Similarity NPD3945 Discontinued
0.6881 Remote Similarity NPD6965 Clinical (unspecified phase)
0.6878 Remote Similarity NPD4602 Approved
0.6875 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6864 Remote Similarity NPD5505 Discontinued
0.6862 Remote Similarity NPD5559 Phase 2
0.6861 Remote Similarity NPD7778 Approved
0.6861 Remote Similarity NPD53 Approved
0.6861 Remote Similarity NPD7777 Approved
0.6857 Remote Similarity NPD6790 Phase 1
0.6853 Remote Similarity NPD6252 Clinical (unspecified phase)
0.6853 Remote Similarity NPD5532 Phase 2
0.6851 Remote Similarity NPD5850 Phase 3
0.685 Remote Similarity NPD8310 Clinical (unspecified phase)
0.6837 Remote Similarity NPD8408 Discontinued
0.6835 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6833 Remote Similarity NPD5801 Clinical (unspecified phase)
0.683 Remote Similarity NPD6661 Clinical (unspecified phase)
0.683 Remote Similarity NPD7000 Clinical (unspecified phase)
0.683 Remote Similarity NPD6999 Discontinued
0.6828 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6828 Remote Similarity NPD4905 Approved
0.6828 Remote Similarity NPD8115 Approved
0.6828 Remote Similarity NPD4903 Approved
0.6828 Remote Similarity NPD8114 Approved
0.6828 Remote Similarity NPD4906 Approved
0.6826 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6822 Remote Similarity NPD4881 Clinical (unspecified phase)
0.6822 Remote Similarity NPD4923 Phase 1
0.682 Remote Similarity NPD3082 Discontinued
0.682 Remote Similarity NPD7731 Approved
0.682 Remote Similarity NPD8292 Phase 2
0.682 Remote Similarity NPD4889 Approved
0.682 Remote Similarity NPD7994 Phase 2
0.682 Remote Similarity NPD7730 Approved
0.6816 Remote Similarity NPD8016 Phase 3
0.6816 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6816 Remote Similarity NPD7117 Phase 2
0.6816 Remote Similarity NPD1229 Phase 2
0.6815 Remote Similarity NPD8468 Phase 2
0.681 Remote Similarity NPD8094 Discontinued
0.6804 Remote Similarity NPD4334 Discontinued
0.6803 Remote Similarity NPD4368 Phase 2
0.6802 Remote Similarity NPD7619 Phase 3
0.6802 Remote Similarity NPD7618 Phase 3
0.6798 Remote Similarity NPD4904 Approved
0.6798 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6798 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6797 Remote Similarity NPD5416 Discontinued
0.6795 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6795 Remote Similarity NPD3326 Clinical (unspecified phase)

  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