Structure

Physi-Chem Properties

Molecular Weight:  848.51
Volume:  871.189
LogP:  2.977
LogD:  1.991
LogS:  -3.455
# Rotatable Bonds:  27
TPSA:  273.36
# H-Bond Aceptor:  16
# H-Bond Donor:  10
# Rings:  1
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.046
Synthetic Accessibility Score:  6.231
Fsp3:  0.814
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.08
MDCK Permeability:  0.0002857779327314347
Pgp-inhibitor:  0.998
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  84.33234405517578%
Volume Distribution (VD):  0.571
Pgp-substrate:  5.15009069442749%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.029
CYP2C19-inhibitor:  0.004
CYP2C19-substrate:  0.353
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.018
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.012
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.121

ADMET: Excretion

Clearance (CL):  1.898
Half-life (T1/2):  0.717

ADMET: Toxicity

hERG Blockers:  0.044
Human Hepatotoxicity (H-HT):  0.982
Drug-inuced Liver Injury (DILI):  0.972
AMES Toxicity:  0.064
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.953
Skin Sensitization:  0.134
Carcinogencity:  0.008
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.352

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

  Natural Product: NPC159698

Natural Product ID:  NPC159698
Common Name*:   [(2R,3R,4R,5R)-2,3,4,5,6-Pentahydroxyhexyl] (2E,4S,5S,6E,8S,9S,10E,12S,13R,14S,16S,18S)-13-[(2R,3S,4S,5S,6R)-6-(Acetyloxymethyl)-3,4,5-Trihydroxyoxan-2-Yl]Oxy-5,9-Dihydroxy-2,4,6,8,10,12,14,16,18-Nonamethylicosa-2,6,10-Trienoate
IUPAC Name:   [(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] (2E,4S,5S,6E,8S,9S,10E,12S,13R,14S,16S,18S)-13-[(2R,3S,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate
Synonyms:  
Standard InCHIKey:  IQGUPVKWTFQNJP-MTJAMWMFSA-N
Standard InCHI:  InChI=1S/C43H76O16/c1-12-21(2)13-22(3)14-27(8)41(59-43-40(54)39(53)38(52)33(58-43)20-56-30(11)45)28(9)16-25(6)34(48)23(4)15-24(5)35(49)26(7)17-29(10)42(55)57-19-32(47)37(51)36(50)31(46)18-44/h15-17,21-23,26-28,31-41,43-44,46-54H,12-14,18-20H2,1-11H3/b24-15+,25-16+,29-17+/t21-,22-,23-,26-,27-,28-,31+,32+,33+,34-,35+,36+,37+,38+,39-,40-,41+,43-/m0/s1
SMILES:  CC[C@H](C)C[C@H](C)C[C@H](C)[C@H]([C@@H](C)/C=C(C)/[C@H]([C@@H](C)/C=C(C)/[C@H]([C@@H](C)/C=C(C)/C(=O)OC[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](COC(=O)C)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3344125
PubChem CID:   10557516
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001552] Sesterterpenoids

*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
NPO33169 bionectria ochroleuca Species Bionectriaceae Eukaryota n.a. n.a. n.a. PMID[25302529]

☑ 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
NPT20 Organism Candida albicans Candida albicans IC50 = 36300.0 nM PMID[464439]
NPT20 Organism Candida albicans Candida albicans IC50 = 1500.0 nM PMID[464439]
NPT20 Organism Candida albicans Candida albicans Ratio = 0.25 n.a. PMID[464439]
NPT20 Organism Candida albicans Candida albicans MIC=>80 = 50.0 uM PMID[464439]
NPT20 Organism Candida albicans Candida albicans MIC=>80 = 1.25 uM PMID[464439]
NPT20 Organism Candida albicans Candida albicans Ratio = 0.03 n.a. PMID[464439]
NPT20 Organism Candida albicans Candida albicans FICI = 0.28 n.a. PMID[464439]

☑ 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 NPC159698 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
0.9885 High Similarity NPC238090
0.9885 High Similarity NPC472196
0.9885 High Similarity NPC472195
0.8913 High Similarity NPC472198
0.8901 High Similarity NPC472197
0.8901 High Similarity NPC472199
0.8854 High Similarity NPC201191
0.8804 High Similarity NPC320089
0.875 High Similarity NPC471637
0.875 High Similarity NPC2313
0.875 High Similarity NPC57586
0.875 High Similarity NPC475157
0.875 High Similarity NPC154132
0.875 High Similarity NPC475655
0.875 High Similarity NPC266718
0.8696 High Similarity NPC477749
0.8652 High Similarity NPC471494
0.8587 High Similarity NPC202886
0.8586 High Similarity NPC315070
0.8571 High Similarity NPC197736
0.8556 High Similarity NPC311163
0.8556 High Similarity NPC208473
0.8542 High Similarity NPC203627
0.8539 High Similarity NPC475035
0.8511 High Similarity NPC256368
0.8478 Intermediate Similarity NPC477748
0.8462 Intermediate Similarity NPC475037
0.8409 Intermediate Similarity NPC469469
0.8333 Intermediate Similarity NPC473308
0.8333 Intermediate Similarity NPC173329
0.8333 Intermediate Similarity NPC288350
0.8333 Intermediate Similarity NPC306041
0.8261 Intermediate Similarity NPC118077
0.8261 Intermediate Similarity NPC475186
0.8261 Intermediate Similarity NPC316138
0.8261 Intermediate Similarity NPC313658
0.8247 Intermediate Similarity NPC475332
0.8242 Intermediate Similarity NPC475034
0.8242 Intermediate Similarity NPC470124
0.8222 Intermediate Similarity NPC142111
0.8222 Intermediate Similarity NPC473315
0.8191 Intermediate Similarity NPC3952
0.8191 Intermediate Similarity NPC118078
0.8191 Intermediate Similarity NPC177668
0.8182 Intermediate Similarity NPC198992
0.8172 Intermediate Similarity NPC470137
0.8163 Intermediate Similarity NPC475653
0.8163 Intermediate Similarity NPC472015
0.8155 Intermediate Similarity NPC133625
0.8144 Intermediate Similarity NPC472995
0.8144 Intermediate Similarity NPC255410
0.8144 Intermediate Similarity NPC54731
0.8111 Intermediate Similarity NPC251026
0.809 Intermediate Similarity NPC133226
0.809 Intermediate Similarity NPC163362
0.809 Intermediate Similarity NPC127295
0.809 Intermediate Similarity NPC470147
0.8085 Intermediate Similarity NPC133450
0.8085 Intermediate Similarity NPC285588
0.8061 Intermediate Similarity NPC120299
0.8061 Intermediate Similarity NPC476612
0.8061 Intermediate Similarity NPC476613
0.8058 Intermediate Similarity NPC177524
0.8058 Intermediate Similarity NPC219900
0.8058 Intermediate Similarity NPC392
0.8046 Intermediate Similarity NPC469880
0.8041 Intermediate Similarity NPC300710
0.8041 Intermediate Similarity NPC469543
0.8039 Intermediate Similarity NPC476740
0.8039 Intermediate Similarity NPC239961
0.8039 Intermediate Similarity NPC476738
0.8021 Intermediate Similarity NPC61201
0.8021 Intermediate Similarity NPC109406
0.8021 Intermediate Similarity NPC320552
0.8021 Intermediate Similarity NPC159092
0.8019 Intermediate Similarity NPC264153
0.8019 Intermediate Similarity NPC473159
0.8 Intermediate Similarity NPC327253
0.8 Intermediate Similarity NPC8538
0.8 Intermediate Similarity NPC6414
0.8 Intermediate Similarity NPC184208
0.8 Intermediate Similarity NPC473311
0.8 Intermediate Similarity NPC303451
0.8 Intermediate Similarity NPC315731
0.8 Intermediate Similarity NPC476611
0.7979 Intermediate Similarity NPC137368
0.7978 Intermediate Similarity NPC180725
0.7978 Intermediate Similarity NPC139712
0.7978 Intermediate Similarity NPC470149
0.7978 Intermediate Similarity NPC470148
0.7959 Intermediate Similarity NPC143446
0.7938 Intermediate Similarity NPC477345
0.7938 Intermediate Similarity NPC477348
0.7938 Intermediate Similarity NPC238264
0.7925 Intermediate Similarity NPC470025
0.7925 Intermediate Similarity NPC328074
0.7925 Intermediate Similarity NPC317460
0.7925 Intermediate Similarity NPC321272
0.7921 Intermediate Similarity NPC121423
0.7921 Intermediate Similarity NPC473596
0.7917 Intermediate Similarity NPC9447
0.7917 Intermediate Similarity NPC110072
0.7917 Intermediate Similarity NPC206679
0.7917 Intermediate Similarity NPC476084
0.7917 Intermediate Similarity NPC114172
0.7917 Intermediate Similarity NPC476075
0.7917 Intermediate Similarity NPC471324
0.79 Intermediate Similarity NPC130792
0.79 Intermediate Similarity NPC255677
0.79 Intermediate Similarity NPC306344
0.79 Intermediate Similarity NPC22149
0.7885 Intermediate Similarity NPC193765
0.7879 Intermediate Similarity NPC40812
0.7872 Intermediate Similarity NPC199382
0.7865 Intermediate Similarity NPC248775
0.7864 Intermediate Similarity NPC82251
0.7857 Intermediate Similarity NPC36954
0.785 Intermediate Similarity NPC470027
0.7849 Intermediate Similarity NPC477747
0.7849 Intermediate Similarity NPC477746
0.7843 Intermediate Similarity NPC475367
0.7843 Intermediate Similarity NPC197541
0.7843 Intermediate Similarity NPC118761
0.7843 Intermediate Similarity NPC474581
0.7843 Intermediate Similarity NPC309398
0.7843 Intermediate Similarity NPC267869
0.7843 Intermediate Similarity NPC284929
0.7843 Intermediate Similarity NPC234304
0.7843 Intermediate Similarity NPC473816
0.7841 Intermediate Similarity NPC326661
0.7835 Intermediate Similarity NPC471483
0.783 Intermediate Similarity NPC17791
0.7826 Intermediate Similarity NPC44261
0.7822 Intermediate Similarity NPC20673
0.7822 Intermediate Similarity NPC298255
0.7822 Intermediate Similarity NPC219038
0.7822 Intermediate Similarity NPC28304
0.7818 Intermediate Similarity NPC470914
0.7812 Intermediate Similarity NPC473904
0.78 Intermediate Similarity NPC187268
0.7789 Intermediate Similarity NPC248312
0.7788 Intermediate Similarity NPC472390
0.7778 Intermediate Similarity NPC473765
0.7778 Intermediate Similarity NPC475525
0.7778 Intermediate Similarity NPC475540
0.7778 Intermediate Similarity NPC475375
0.7778 Intermediate Similarity NPC472996
0.7778 Intermediate Similarity NPC475241
0.7778 Intermediate Similarity NPC472997
0.7778 Intermediate Similarity NPC475164
0.7778 Intermediate Similarity NPC86971
0.7778 Intermediate Similarity NPC476066
0.7778 Intermediate Similarity NPC475593
0.7778 Intermediate Similarity NPC473605
0.7778 Intermediate Similarity NPC321728
0.7767 Intermediate Similarity NPC470768
0.7767 Intermediate Similarity NPC86095
0.7766 Intermediate Similarity NPC47937
0.7766 Intermediate Similarity NPC186332
0.7766 Intermediate Similarity NPC47220
0.7755 Intermediate Similarity NPC294293
0.7755 Intermediate Similarity NPC71589
0.7753 Intermediate Similarity NPC474026
0.7753 Intermediate Similarity NPC477203
0.7753 Intermediate Similarity NPC475711
0.7748 Intermediate Similarity NPC48692
0.7745 Intermediate Similarity NPC471599
0.7745 Intermediate Similarity NPC13171
0.7745 Intermediate Similarity NPC195510
0.7745 Intermediate Similarity NPC222062
0.7742 Intermediate Similarity NPC160517
0.7742 Intermediate Similarity NPC78673
0.7742 Intermediate Similarity NPC288471
0.7742 Intermediate Similarity NPC186155
0.7736 Intermediate Similarity NPC83005
0.7736 Intermediate Similarity NPC316708
0.7732 Intermediate Similarity NPC158061
0.7732 Intermediate Similarity NPC477349
0.7727 Intermediate Similarity NPC470515
0.7727 Intermediate Similarity NPC475309
0.7723 Intermediate Similarity NPC244878
0.7714 Intermediate Similarity NPC470024
0.7708 Intermediate Similarity NPC139418
0.7706 Intermediate Similarity NPC207637
0.7701 Intermediate Similarity NPC477085
0.77 Intermediate Similarity NPC474182
0.77 Intermediate Similarity NPC96597
0.77 Intermediate Similarity NPC239547
0.77 Intermediate Similarity NPC91197
0.77 Intermediate Similarity NPC309503
0.77 Intermediate Similarity NPC155319
0.77 Intermediate Similarity NPC472290
0.77 Intermediate Similarity NPC125551
0.7692 Intermediate Similarity NPC472749
0.7692 Intermediate Similarity NPC472751
0.7692 Intermediate Similarity NPC85670
0.7677 Intermediate Similarity NPC170204
0.7677 Intermediate Similarity NPC471141
0.7677 Intermediate Similarity NPC469583
0.7664 Intermediate Similarity NPC470026

  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 NPC159698 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
0.8542 High Similarity NPD8029 Clinical (unspecified phase)
0.8387 Intermediate Similarity NPD6698 Approved
0.8387 Intermediate Similarity NPD7838 Discovery
0.8387 Intermediate Similarity NPD46 Approved
0.8058 Intermediate Similarity NPD6686 Approved
0.7551 Intermediate Similarity NPD7983 Approved
0.75 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD5344 Discontinued
0.7368 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7829 Approved
0.7241 Intermediate Similarity NPD7830 Approved
0.7217 Intermediate Similarity NPD8513 Phase 3
0.7217 Intermediate Similarity NPD8033 Approved
0.7217 Intermediate Similarity NPD8516 Approved
0.7217 Intermediate Similarity NPD8517 Approved
0.7217 Intermediate Similarity NPD8515 Approved
0.713 Intermediate Similarity NPD8294 Approved
0.713 Intermediate Similarity NPD8377 Approved
0.713 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD7328 Approved
0.7105 Intermediate Similarity NPD7327 Approved
0.7087 Intermediate Similarity NPD7839 Suspended
0.7069 Intermediate Similarity NPD8444 Approved
0.7069 Intermediate Similarity NPD8380 Approved
0.7069 Intermediate Similarity NPD8296 Approved
0.7069 Intermediate Similarity NPD8335 Approved
0.7069 Intermediate Similarity NPD8378 Approved
0.7069 Intermediate Similarity NPD8379 Approved
0.7069 Intermediate Similarity NPD7503 Approved
0.7048 Intermediate Similarity NPD6648 Approved
0.7043 Intermediate Similarity NPD7516 Approved
0.6957 Remote Similarity NPD7641 Discontinued
0.6952 Remote Similarity NPD4225 Approved
0.6949 Remote Similarity NPD7642 Approved
0.6937 Remote Similarity NPD6371 Approved
0.6833 Remote Similarity NPD7507 Approved
0.6818 Remote Similarity NPD6412 Phase 2
0.6777 Remote Similarity NPD8448 Approved
0.6754 Remote Similarity NPD8133 Approved
0.6694 Remote Similarity NPD8451 Approved
0.6667 Remote Similarity NPD7319 Approved
0.6667 Remote Similarity NPD8328 Phase 3
0.6639 Remote Similarity NPD8074 Phase 3
0.6634 Remote Similarity NPD4250 Approved
0.6634 Remote Similarity NPD4251 Approved
0.6612 Remote Similarity NPD8299 Approved
0.6612 Remote Similarity NPD8342 Approved
0.6612 Remote Similarity NPD8341 Approved
0.6612 Remote Similarity NPD8340 Approved
0.6602 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6574 Remote Similarity NPD7639 Approved
0.6574 Remote Similarity NPD7640 Approved
0.6566 Remote Similarity NPD7154 Phase 3
0.6549 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6535 Remote Similarity NPD4249 Approved
0.6481 Remote Similarity NPD7638 Approved
0.648 Remote Similarity NPD8390 Approved
0.648 Remote Similarity NPD8392 Approved
0.648 Remote Similarity NPD8391 Approved
0.6476 Remote Similarity NPD5778 Approved
0.6476 Remote Similarity NPD5779 Approved
0.6442 Remote Similarity NPD5785 Approved
0.6436 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6436 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4822 Approved
0.6429 Remote Similarity NPD4820 Approved
0.6429 Remote Similarity NPD4821 Approved
0.6429 Remote Similarity NPD4819 Approved
0.64 Remote Similarity NPD6110 Phase 1
0.6392 Remote Similarity NPD4268 Approved
0.6392 Remote Similarity NPD4271 Approved
0.6381 Remote Similarity NPD7637 Suspended
0.6333 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6311 Remote Similarity NPD8080 Discontinued
0.6308 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7505 Discontinued
0.6303 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7500 Approved
0.6303 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6293 Remote Similarity NPD7116 Clinical (unspecified phase)
0.629 Remote Similarity NPD8273 Phase 1
0.6275 Remote Similarity NPD5363 Approved
0.6239 Remote Similarity NPD6053 Discontinued
0.6238 Remote Similarity NPD5362 Discontinued
0.6204 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6167 Remote Similarity NPD7115 Discovery
0.6154 Remote Similarity NPD7524 Approved
0.6147 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6121 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6098 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6078 Remote Similarity NPD5332 Approved
0.6078 Remote Similarity NPD5331 Approved
0.6068 Remote Similarity NPD6421 Discontinued
0.6063 Remote Similarity NPD7736 Approved
0.604 Remote Similarity NPD4790 Discontinued
0.6038 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6038 Remote Similarity NPD6101 Approved
0.6038 Remote Similarity NPD1695 Approved
0.6029 Remote Similarity NPD7266 Discontinued
0.6019 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6018 Remote Similarity NPD7632 Discontinued
0.6 Remote Similarity NPD4211 Phase 1
0.6 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5985 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5984 Remote Similarity NPD8293 Discontinued
0.598 Remote Similarity NPD4752 Clinical (unspecified phase)
0.598 Remote Similarity NPD6435 Approved
0.598 Remote Similarity NPD4270 Approved
0.598 Remote Similarity NPD4269 Approved
0.5965 Remote Similarity NPD1407 Approved
0.5963 Remote Similarity NPD5282 Discontinued
0.5932 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5926 Remote Similarity NPD6411 Approved
0.5922 Remote Similarity NPD6695 Phase 3
0.592 Remote Similarity NPD6370 Approved
0.5918 Remote Similarity NPD8039 Approved
0.5905 Remote Similarity NPD5786 Approved
0.59 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5849 Remote Similarity NPD7750 Discontinued
0.5833 Remote Similarity NPD3168 Discontinued
0.5833 Remote Similarity NPD6430 Approved
0.5833 Remote Similarity NPD8297 Approved
0.5833 Remote Similarity NPD6882 Approved
0.5833 Remote Similarity NPD6429 Approved
0.5827 Remote Similarity NPD7492 Approved
0.5825 Remote Similarity NPD5209 Approved
0.5814 Remote Similarity NPD8336 Approved
0.5814 Remote Similarity NPD8337 Approved
0.5802 Remote Similarity NPD7260 Phase 2
0.58 Remote Similarity NPD4756 Discovery
0.5794 Remote Similarity NPD7623 Phase 3
0.5794 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5789 Remote Similarity NPD8415 Approved
0.5784 Remote Similarity NPD4252 Approved
0.5784 Remote Similarity NPD5368 Approved
0.5781 Remote Similarity NPD6616 Approved
0.5772 Remote Similarity NPD6009 Approved
0.5763 Remote Similarity NPD5345 Clinical (unspecified phase)
0.576 Remote Similarity NPD6054 Approved
0.576 Remote Similarity NPD6319 Approved
0.576 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5736 Remote Similarity NPD7747 Phase 1
0.5736 Remote Similarity NPD7746 Phase 1
0.5736 Remote Similarity NPD7078 Approved
0.5734 Remote Similarity NPD8389 Clinical (unspecified phase)
0.5728 Remote Similarity NPD5369 Approved
0.5726 Remote Similarity NPD6640 Phase 3
0.5714 Remote Similarity NPD8269 Approved
0.5714 Remote Similarity NPD8267 Approved
0.5714 Remote Similarity NPD8268 Approved
0.5714 Remote Similarity NPD8266 Approved
0.5702 Remote Similarity NPD969 Suspended
0.569 Remote Similarity NPD6647 Phase 2
0.5686 Remote Similarity NPD6929 Approved
0.5684 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5678 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5676 Remote Similarity NPD7748 Approved
0.5674 Remote Similarity NPD7625 Phase 1
0.5664 Remote Similarity NPD7902 Approved
0.566 Remote Similarity NPD1694 Approved
0.5656 Remote Similarity NPD4632 Approved
0.5652 Remote Similarity NPD368 Approved
0.5644 Remote Similarity NPD6925 Approved
0.5644 Remote Similarity NPD5776 Phase 2
0.5639 Remote Similarity NPD8338 Approved
0.5636 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5635 Remote Similarity NPD6059 Approved
0.5631 Remote Similarity NPD6931 Approved
0.5631 Remote Similarity NPD7514 Phase 3
0.5631 Remote Similarity NPD7332 Phase 2
0.5631 Remote Similarity NPD6930 Phase 2
0.5625 Remote Similarity NPD6067 Discontinued
0.5619 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5619 Remote Similarity NPD3669 Approved
0.5607 Remote Similarity NPD6422 Discontinued
0.5603 Remote Similarity NPD8084 Approved
0.5603 Remote Similarity NPD8086 Approved
0.5603 Remote Similarity NPD8083 Approved
0.5603 Remote Similarity NPD8082 Approved
0.5603 Remote Similarity NPD8085 Approved
0.5603 Remote Similarity NPD8139 Approved
0.5603 Remote Similarity NPD8138 Approved
0.56 Remote Similarity NPD8264 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