Structure

Physi-Chem Properties

Molecular Weight:  768.48
Volume:  837.221
LogP:  2.036
LogD:  2.631
LogS:  -1.839
# Rotatable Bonds:  32
TPSA:  151.98
# H-Bond Aceptor:  10
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.032
Synthetic Accessibility Score:  5.295
Fsp3:  0.556
Lipinski Rule-of-5:  Accepted
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:  -5.233
MDCK Permeability:  9.568545647198334e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.229
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  101.53907775878906%
Volume Distribution (VD):  1.776
Pgp-substrate:  2.0711052417755127%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.076
CYP2C19-inhibitor:  0.051
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.162
CYP2C9-substrate:  0.98
CYP2D6-inhibitor:  0.33
CYP2D6-substrate:  0.944
CYP3A4-inhibitor:  0.929
CYP3A4-substrate:  0.106

ADMET: Excretion

Clearance (CL):  1.446
Half-life (T1/2):  0.983

ADMET: Toxicity

hERG Blockers:  0.309
Human Hepatotoxicity (H-HT):  0.085
Drug-inuced Liver Injury (DILI):  0.0
AMES Toxicity:  0.933
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.246
Skin Sensitization:  0.981
Carcinogencity:  0.891
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.739

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

  Natural Product: NPC133377

Natural Product ID:  NPC133377
Common Name*:   (2S)-1-O-3,6,9,12,15-Octadecapentaenoyl-2-O-6,9,12,15-Octadecatetraenoyl-3-O-Beta-D-Galactopyranosylsn-Glycerol
IUPAC Name:   [(2S)-1-[(3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl] (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate
Synonyms:  
Standard InCHIKey:  UORRAKMCELTARB-SQKRHONHSA-N
Standard InCHI:  InChI=1S/C45H68O10/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(47)52-36-38(37-53-45-44(51)43(50)42(49)39(35-46)55-45)54-41(48)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29,31,38-39,42-46,49-51H,3-4,9-10,15-16,21-22,27-28,30,32-37H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-/t38-,39-,42+,43+,44-,45-/m1/s1
SMILES:  CC/C=CC/C=CC/C=CC/C=CC/C=CCC(=O)OC[C@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)OC(=O)CCCC/C=CC/C=CC/C=CC/C=CCC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL451300
PubChem CID:   44593525
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000175] Glycerolipids
        • [CHEMONTID:0000637] Glycosylglycerols
          • [CHEMONTID:0003822] Glycosyldiradylglycerols
            • [CHEMONTID:0003067] Glycosyldiacylglycerols
              • [CHEMONTID:0003259] 1,2-diacyl-3-O-beta-D-galactosyl-sn-glycerols

*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
NPO22576 Heterocapsa circularisquama Species Heterocapsaceae Eukaryota n.a. n.a. n.a. PMID[12398551]
NPO22992 Himerometra magnipinna Species Himerometridae Eukaryota n.a. n.a. n.a. PMID[17428090]
NPO14064 Phaeodactylum tricornutum Species Phaeodactylaceae Eukaryota n.a. n.a. n.a. PMID[18570469]
NPO22992 Himerometra magnipinna Species Himerometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23129 Alphitonia zizyphoides Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22451 Phalaenopsis sanderiana Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11767 Vernonia marginata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5726 Agaricus silvicola Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22576 Heterocapsa circularisquama Species Heterocapsaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14064 Phaeodactylum tricornutum Species Phaeodactylaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21932 Piptadeniastrum africanum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21873 Lactarius picinus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20670 Guatteria discolor Species Annonaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 18.0 % PMID[496307]
NPT2 Others Unspecified Activity = 14.0 % PMID[496307]

☑ 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 NPC133377 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
0.9861 High Similarity NPC110813
0.9342 High Similarity NPC236649
0.9342 High Similarity NPC21693
0.9103 High Similarity NPC473500
0.9103 High Similarity NPC38295
0.9103 High Similarity NPC470313
0.9103 High Similarity NPC156089
0.8333 Intermediate Similarity NPC470137
0.8272 Intermediate Similarity NPC251026
0.8256 Intermediate Similarity NPC472197
0.825 Intermediate Similarity NPC163362
0.825 Intermediate Similarity NPC127295
0.8194 Intermediate Similarity NPC13143
0.8194 Intermediate Similarity NPC294813
0.8171 Intermediate Similarity NPC473315
0.8171 Intermediate Similarity NPC142111
0.8148 Intermediate Similarity NPC280367
0.8148 Intermediate Similarity NPC469469
0.814 Intermediate Similarity NPC473311
0.8072 Intermediate Similarity NPC473308
0.8052 Intermediate Similarity NPC55652
0.8046 Intermediate Similarity NPC472199
0.7975 Intermediate Similarity NPC326661
0.7955 Intermediate Similarity NPC320089
0.7907 Intermediate Similarity NPC137368
0.7882 Intermediate Similarity NPC208473
0.7865 Intermediate Similarity NPC472198
0.7838 Intermediate Similarity NPC76881
0.7838 Intermediate Similarity NPC12040
0.7802 Intermediate Similarity NPC476612
0.7802 Intermediate Similarity NPC476613
0.7791 Intermediate Similarity NPC475186
0.7791 Intermediate Similarity NPC118077
0.7778 Intermediate Similarity NPC81896
0.7778 Intermediate Similarity NPC321919
0.7765 Intermediate Similarity NPC470124
0.7765 Intermediate Similarity NPC477747
0.7765 Intermediate Similarity NPC477746
0.7763 Intermediate Similarity NPC324981
0.7763 Intermediate Similarity NPC141481
0.7763 Intermediate Similarity NPC473559
0.7763 Intermediate Similarity NPC48218
0.7753 Intermediate Similarity NPC61201
0.7722 Intermediate Similarity NPC472174
0.7667 Intermediate Similarity NPC294293
0.7662 Intermediate Similarity NPC211428
0.7647 Intermediate Similarity NPC266718
0.7647 Intermediate Similarity NPC475035
0.764 Intermediate Similarity NPC9447
0.7632 Intermediate Similarity NPC104537
0.7632 Intermediate Similarity NPC148192
0.7632 Intermediate Similarity NPC22101
0.7632 Intermediate Similarity NPC473829
0.7632 Intermediate Similarity NPC127091
0.7632 Intermediate Similarity NPC206601
0.7632 Intermediate Similarity NPC271921
0.7632 Intermediate Similarity NPC330426
0.7632 Intermediate Similarity NPC475443
0.7614 Intermediate Similarity NPC285588
0.7595 Intermediate Similarity NPC132938
0.7586 Intermediate Similarity NPC475037
0.7564 Intermediate Similarity NPC476660
0.7564 Intermediate Similarity NPC474078
0.7561 Intermediate Similarity NPC317263
0.7556 Intermediate Similarity NPC238090
0.7556 Intermediate Similarity NPC472196
0.7556 Intermediate Similarity NPC320552
0.7556 Intermediate Similarity NPC472195
0.7553 Intermediate Similarity NPC476611
0.7532 Intermediate Similarity NPC97736
0.7532 Intermediate Similarity NPC50228
0.7532 Intermediate Similarity NPC250619
0.7528 Intermediate Similarity NPC303451
0.7528 Intermediate Similarity NPC118078
0.7528 Intermediate Similarity NPC6414
0.75 Intermediate Similarity NPC472173
0.75 Intermediate Similarity NPC54731
0.75 Intermediate Similarity NPC471755
0.75 Intermediate Similarity NPC476656
0.75 Intermediate Similarity NPC476659
0.75 Intermediate Similarity NPC471756
0.75 Intermediate Similarity NPC306041
0.7473 Intermediate Similarity NPC159698
0.747 Intermediate Similarity NPC321728
0.747 Intermediate Similarity NPC469747
0.747 Intermediate Similarity NPC263574
0.7444 Intermediate Similarity NPC110072
0.7442 Intermediate Similarity NPC288471
0.7436 Intermediate Similarity NPC241265
0.7436 Intermediate Similarity NPC473772
0.7436 Intermediate Similarity NPC285003
0.7419 Intermediate Similarity NPC472290
0.7407 Intermediate Similarity NPC473948
0.7391 Intermediate Similarity NPC469543
0.7391 Intermediate Similarity NPC170204
0.7381 Intermediate Similarity NPC470147
0.7381 Intermediate Similarity NPC133226
0.7375 Intermediate Similarity NPC39266
0.7375 Intermediate Similarity NPC9763
0.7375 Intermediate Similarity NPC225748
0.7375 Intermediate Similarity NPC291228
0.7375 Intermediate Similarity NPC308096
0.7375 Intermediate Similarity NPC206823
0.7375 Intermediate Similarity NPC169085
0.7368 Intermediate Similarity NPC476654
0.7368 Intermediate Similarity NPC476657
0.7368 Intermediate Similarity NPC476655
0.7368 Intermediate Similarity NPC147292
0.7363 Intermediate Similarity NPC478037
0.7363 Intermediate Similarity NPC478036
0.7361 Intermediate Similarity NPC323436
0.7356 Intermediate Similarity NPC475034
0.7333 Intermediate Similarity NPC277570
0.7333 Intermediate Similarity NPC117596
0.7333 Intermediate Similarity NPC327253
0.7333 Intermediate Similarity NPC325773
0.7317 Intermediate Similarity NPC229655
0.7312 Intermediate Similarity NPC241911
0.7312 Intermediate Similarity NPC256230
0.7297 Intermediate Similarity NPC155457
0.7292 Intermediate Similarity NPC222062
0.7292 Intermediate Similarity NPC13171
0.7292 Intermediate Similarity NPC195510
0.7273 Intermediate Similarity NPC47937
0.7263 Intermediate Similarity NPC306344
0.7263 Intermediate Similarity NPC469871
0.7263 Intermediate Similarity NPC22149
0.7263 Intermediate Similarity NPC469870
0.7263 Intermediate Similarity NPC255677
0.7262 Intermediate Similarity NPC470149
0.7262 Intermediate Similarity NPC470148
0.7262 Intermediate Similarity NPC180725
0.7253 Intermediate Similarity NPC472124
0.7253 Intermediate Similarity NPC469410
0.7253 Intermediate Similarity NPC472125
0.7253 Intermediate Similarity NPC472126
0.725 Intermediate Similarity NPC184550
0.725 Intermediate Similarity NPC185419
0.7237 Intermediate Similarity NPC476658
0.7234 Intermediate Similarity NPC474194
0.7234 Intermediate Similarity NPC278506
0.7229 Intermediate Similarity NPC474026
0.7216 Intermediate Similarity NPC197541
0.7216 Intermediate Similarity NPC234304
0.7216 Intermediate Similarity NPC118761
0.7216 Intermediate Similarity NPC284929
0.7216 Intermediate Similarity NPC267869
0.72 Intermediate Similarity NPC321838
0.7188 Intermediate Similarity NPC28304
0.7188 Intermediate Similarity NPC298255
0.7179 Intermediate Similarity NPC25298
0.7179 Intermediate Similarity NPC478100
0.7174 Intermediate Similarity NPC473561
0.7174 Intermediate Similarity NPC473723
0.7174 Intermediate Similarity NPC473663
0.7174 Intermediate Similarity NPC475173
0.716 Intermediate Similarity NPC163812
0.7159 Intermediate Similarity NPC182383
0.7158 Intermediate Similarity NPC198422
0.7158 Intermediate Similarity NPC40182
0.7143 Intermediate Similarity NPC471761
0.7143 Intermediate Similarity NPC471760
0.7143 Intermediate Similarity NPC190418
0.7143 Intermediate Similarity NPC248775
0.7143 Intermediate Similarity NPC86095
0.7143 Intermediate Similarity NPC231271
0.7143 Intermediate Similarity NPC470519
0.7143 Intermediate Similarity NPC473904
0.7143 Intermediate Similarity NPC307699
0.7143 Intermediate Similarity NPC469869
0.7125 Intermediate Similarity NPC42526
0.7113 Intermediate Similarity NPC310804
0.7113 Intermediate Similarity NPC261117
0.7111 Intermediate Similarity NPC280621
0.7111 Intermediate Similarity NPC40376
0.7111 Intermediate Similarity NPC233551
0.7111 Intermediate Similarity NPC21208
0.7111 Intermediate Similarity NPC48338
0.7111 Intermediate Similarity NPC20339
0.7108 Intermediate Similarity NPC477350
0.7108 Intermediate Similarity NPC49392
0.7108 Intermediate Similarity NPC190400
0.7105 Intermediate Similarity NPC54925
0.7097 Intermediate Similarity NPC2003
0.7097 Intermediate Similarity NPC25701
0.7089 Intermediate Similarity NPC209327
0.7089 Intermediate Similarity NPC273508
0.7083 Intermediate Similarity NPC324667
0.7083 Intermediate Similarity NPC473146
0.7073 Intermediate Similarity NPC474321
0.7071 Intermediate Similarity NPC201128
0.7065 Intermediate Similarity NPC477749
0.7065 Intermediate Similarity NPC473707
0.7065 Intermediate Similarity NPC477349
0.7059 Intermediate Similarity NPC179933
0.7051 Intermediate Similarity NPC478101
0.7041 Intermediate Similarity NPC309398
0.7033 Intermediate Similarity NPC139418
0.7033 Intermediate Similarity NPC477748
0.703 Intermediate Similarity NPC118225

  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 NPC133377 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
0.7143 Intermediate Similarity NPD46 Approved
0.7143 Intermediate Similarity NPD6698 Approved
0.7065 Intermediate Similarity NPD7983 Approved
0.6962 Remote Similarity NPD896 Approved
0.6962 Remote Similarity NPD897 Approved
0.6962 Remote Similarity NPD898 Approved
0.6962 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6804 Remote Similarity NPD8029 Clinical (unspecified phase)
0.68 Remote Similarity NPD6109 Phase 1
0.6795 Remote Similarity NPD3197 Phase 1
0.6774 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6686 Approved
0.6731 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7329 Approved
0.6667 Remote Similarity NPD2269 Approved
0.6598 Remote Similarity NPD7839 Suspended
0.6596 Remote Similarity NPD7838 Discovery
0.6548 Remote Similarity NPD3181 Approved
0.6528 Remote Similarity NPD905 Approved
0.6528 Remote Similarity NPD904 Phase 3
0.6514 Remote Similarity NPD7641 Discontinued
0.6486 Remote Similarity NPD8513 Phase 3
0.6486 Remote Similarity NPD8515 Approved
0.6486 Remote Similarity NPD8444 Approved
0.6486 Remote Similarity NPD8516 Approved
0.6486 Remote Similarity NPD8517 Approved
0.641 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6381 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6372 Remote Similarity NPD7829 Approved
0.6372 Remote Similarity NPD7830 Approved
0.6351 Remote Similarity NPD889 Approved
0.6351 Remote Similarity NPD890 Clinical (unspecified phase)
0.6351 Remote Similarity NPD893 Approved
0.6351 Remote Similarity NPD892 Phase 3
0.6351 Remote Similarity NPD894 Approved
0.6351 Remote Similarity NPD888 Phase 3
0.6351 Remote Similarity NPD891 Phase 3
0.6351 Remote Similarity NPD895 Approved
0.6351 Remote Similarity NPD887 Approved
0.6346 Remote Similarity NPD6412 Phase 2
0.6316 Remote Similarity NPD8342 Approved
0.6316 Remote Similarity NPD8340 Approved
0.6316 Remote Similarity NPD8341 Approved
0.6316 Remote Similarity NPD8299 Approved
0.6277 Remote Similarity NPD4250 Approved
0.6277 Remote Similarity NPD4251 Approved
0.6261 Remote Similarity NPD8451 Approved
0.625 Remote Similarity NPD8961 Approved
0.625 Remote Similarity NPD3173 Approved
0.6222 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6207 Remote Similarity NPD8448 Approved
0.6203 Remote Similarity NPD6123 Approved
0.617 Remote Similarity NPD4249 Approved
0.6126 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6126 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6111 Remote Similarity NPD5343 Approved
0.6087 Remote Similarity NPD7642 Approved
0.6087 Remote Similarity NPD8328 Phase 3
0.6087 Remote Similarity NPD6435 Approved
0.6053 Remote Similarity NPD3196 Approved
0.6053 Remote Similarity NPD3194 Approved
0.6053 Remote Similarity NPD3728 Approved
0.6053 Remote Similarity NPD3195 Phase 2
0.6053 Remote Similarity NPD3730 Approved
0.6053 Remote Similarity NPD4266 Approved
0.605 Remote Similarity NPD8390 Approved
0.605 Remote Similarity NPD8392 Approved
0.605 Remote Similarity NPD8391 Approved
0.6022 Remote Similarity NPD7154 Phase 3
0.6019 Remote Similarity NPD6421 Discontinued
0.6 Remote Similarity NPD4268 Approved
0.6 Remote Similarity NPD8133 Approved
0.6 Remote Similarity NPD4271 Approved
0.5979 Remote Similarity NPD6101 Approved
0.5979 Remote Similarity NPD5764 Clinical (unspecified phase)
0.596 Remote Similarity NPD5779 Approved
0.596 Remote Similarity NPD5778 Approved
0.5932 Remote Similarity NPD8074 Phase 3
0.5921 Remote Similarity NPD3172 Approved
0.5913 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5905 Remote Similarity NPD1407 Approved
0.5897 Remote Similarity NPD2267 Suspended
0.5888 Remote Similarity NPD7899 Clinical (unspecified phase)
0.587 Remote Similarity NPD4821 Approved
0.587 Remote Similarity NPD4819 Approved
0.587 Remote Similarity NPD4820 Approved
0.587 Remote Similarity NPD4822 Approved
0.587 Remote Similarity NPD5368 Approved
0.5862 Remote Similarity NPD8080 Discontinued
0.5859 Remote Similarity NPD6411 Approved
0.5851 Remote Similarity NPD6110 Phase 1
0.5847 Remote Similarity NPD7507 Approved
0.5844 Remote Similarity NPD7346 Approved
0.5833 Remote Similarity NPD39 Approved
0.5833 Remote Similarity NPD8997 Approved
0.5833 Remote Similarity NPD4222 Approved
0.5833 Remote Similarity NPD9000 Phase 3
0.5833 Remote Similarity NPD8998 Phase 2
0.5833 Remote Similarity NPD8999 Phase 3
0.5833 Remote Similarity NPD3174 Discontinued
0.5833 Remote Similarity NPD8993 Phase 1
0.5823 Remote Similarity NPD8959 Approved
0.5806 Remote Similarity NPD5369 Approved
0.5789 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5776 Remote Similarity NPD8033 Approved
0.5714 Remote Similarity NPD5344 Discontinued
0.5702 Remote Similarity NPD7319 Approved
0.57 Remote Similarity NPD7637 Suspended
0.5699 Remote Similarity NPD4252 Approved
0.5694 Remote Similarity NPD6096 Approved
0.5694 Remote Similarity NPD6097 Approved
0.569 Remote Similarity NPD8294 Approved
0.569 Remote Similarity NPD8377 Approved
0.5684 Remote Similarity NPD5362 Discontinued
0.5676 Remote Similarity NPD8966 Approved
0.5676 Remote Similarity NPD8965 Approved
0.5663 Remote Similarity NPD847 Phase 1
0.5658 Remote Similarity NPD28 Approved
0.5658 Remote Similarity NPD29 Approved
0.5652 Remote Similarity NPD7328 Approved
0.5652 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5652 Remote Similarity NPD7327 Approved
0.5641 Remote Similarity NPD8379 Approved
0.5641 Remote Similarity NPD7503 Approved
0.5641 Remote Similarity NPD8335 Approved
0.5641 Remote Similarity NPD8378 Approved
0.5641 Remote Similarity NPD8296 Approved
0.5641 Remote Similarity NPD8380 Approved
0.562 Remote Similarity NPD7736 Approved
0.5603 Remote Similarity NPD7516 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