Structure

Physi-Chem Properties

Molecular Weight:  923.52
Volume:  914.043
LogP:  3.152
LogD:  3.105
LogS:  -3.078
# Rotatable Bonds:  10
TPSA:  263.39
# H-Bond Aceptor:  17
# H-Bond Donor:  9
# Rings:  8
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.119
Synthetic Accessibility Score:  6.249
Fsp3:  0.917
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.678
MDCK Permeability:  1.0324189133825712e-05
Pgp-inhibitor:  0.967
Pgp-substrate:  0.028
Human Intestinal Absorption (HIA):  0.854
20% Bioavailability (F20%):  0.106
30% Bioavailability (F30%):  0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.051
Plasma Protein Binding (PPB):  78.53050994873047%
Volume Distribution (VD):  0.366
Pgp-substrate:  15.315872192382812%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.323
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.094
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.01
CYP2D6-inhibitor:  0.038
CYP2D6-substrate:  0.053
CYP3A4-inhibitor:  0.084
CYP3A4-substrate:  0.038

ADMET: Excretion

Clearance (CL):  0.723
Half-life (T1/2):  0.63

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.191
Drug-inuced Liver Injury (DILI):  0.018
AMES Toxicity:  0.166
Rat Oral Acute Toxicity:  0.062
Maximum Recommended Daily Dose:  0.904
Skin Sensitization:  0.029
Carcinogencity:  0.031
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.937

Download Data

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

  Natural Product: NPC280941

Natural Product ID:  NPC280941
Common Name*:   3-O-Alpha-L-Arabinopyranosyl(1->2)-Alpha-L-Arabinopyranosyl-(1->6)-2-Acetamido-2-Deoxy-Beta-D-Glucopyranosyloleanolic Acid
IUPAC Name:   (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:  
Standard InCHIKey:  ZHJLYHABGRSKOY-DJCYYABVSA-N
Standard InCHI:  InChI=1S/C48H77NO16/c1-23(50)49-32-36(56)35(55)28(22-62-41-38(34(54)27(52)21-61-41)65-40-37(57)33(53)26(51)20-60-40)63-39(32)64-31-12-13-45(6)29(44(31,4)5)11-14-47(8)30(45)10-9-24-25-19-43(2,3)15-17-48(25,42(58)59)18-16-46(24,47)7/h9,25-41,51-57H,10-22H2,1-8H3,(H,49,50)(H,58,59)/t25-,26-,27-,28+,29-,30+,31-,32+,33-,34-,35+,36+,37+,38+,39-,40-,41-,45-,46+,47+,48-/m0/s1
SMILES:  O[C@@H]1[C@@H](CO[C@@H]2OC[C@@H]([C@@H]([C@H]2O[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)O)O)O[C@H]([C@@H]([C@H]1O)N=C(O)C)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL449880
PubChem CID:   10701004
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene saponins

*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
NPO20805 Albizia subdimidiata Species Fabaceae Eukaryota n.a. Suriname rainforest n.a. PMID[11325245]
NPO32561 acacia tenuifolia Species Fabaceae Eukaryota n.a. suriname rainforest n.a. PMID[11858750]
NPO20805 Albizia subdimidiata Species Fabaceae 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
NPT179 Cell Line A2780 Homo sapiens IC50 = 0.8 ug.mL-1 PMID[509195]
NPT726 Cell Line M109 Mus musculus IC50 = 1.0 ug.mL-1 PMID[509196]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 25.0 ug ml-1 PMID[509195]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 40.0 ug ml-1 PMID[509195]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 30.0 ug ml-1 PMID[509195]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 45.0 ug ml-1 PMID[509195]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 45.0 ug ml-1 PMID[509196]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 30.0 ug ml-1 PMID[509196]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 40.0 ug ml-1 PMID[509196]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 25.0 ug ml-1 PMID[509196]

☑ 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 NPC280941 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC235772
0.9837 High Similarity NPC73829
0.9837 High Similarity NPC119794
0.9762 High Similarity NPC243680
0.9762 High Similarity NPC200788
0.9756 High Similarity NPC475472
0.968 High Similarity NPC75318
0.9609 High Similarity NPC82931
0.9609 High Similarity NPC210729
0.9609 High Similarity NPC172365
0.9603 High Similarity NPC145899
0.96 High Similarity NPC76999
0.9462 High Similarity NPC475152
0.9462 High Similarity NPC475394
0.9462 High Similarity NPC475584
0.9389 High Similarity NPC475892
0.8939 High Similarity NPC302276
0.8939 High Similarity NPC180770
0.8849 High Similarity NPC265699
0.8849 High Similarity NPC475527
0.8846 High Similarity NPC477072
0.8815 High Similarity NPC141669
0.8806 High Similarity NPC162910
0.8786 High Similarity NPC100612
0.8786 High Similarity NPC187497
0.8786 High Similarity NPC475599
0.8786 High Similarity NPC174336
0.8786 High Similarity NPC113620
0.8676 High Similarity NPC298469
0.8676 High Similarity NPC193579
0.8613 High Similarity NPC214821
0.8613 High Similarity NPC298067
0.8519 High Similarity NPC265908
0.85 High Similarity NPC298005
0.85 High Similarity NPC36463
0.8489 Intermediate Similarity NPC61717
0.8489 Intermediate Similarity NPC244380
0.8409 Intermediate Similarity NPC139585
0.8406 Intermediate Similarity NPC284625
0.8406 Intermediate Similarity NPC69176
0.8374 Intermediate Similarity NPC139044
0.8374 Intermediate Similarity NPC257468
0.8374 Intermediate Similarity NPC276093
0.8374 Intermediate Similarity NPC109079
0.8374 Intermediate Similarity NPC10320
0.8374 Intermediate Similarity NPC471383
0.8374 Intermediate Similarity NPC101744
0.8374 Intermediate Similarity NPC475504
0.8374 Intermediate Similarity NPC102439
0.8374 Intermediate Similarity NPC469946
0.8374 Intermediate Similarity NPC324875
0.8374 Intermediate Similarity NPC104400
0.8374 Intermediate Similarity NPC473373
0.8374 Intermediate Similarity NPC79718
0.8374 Intermediate Similarity NPC475516
0.8374 Intermediate Similarity NPC104071
0.8374 Intermediate Similarity NPC292677
0.8306 Intermediate Similarity NPC114304
0.8306 Intermediate Similarity NPC192600
0.8306 Intermediate Similarity NPC241909
0.8306 Intermediate Similarity NPC323341
0.8306 Intermediate Similarity NPC134835
0.8306 Intermediate Similarity NPC114287
0.8306 Intermediate Similarity NPC73318
0.8306 Intermediate Similarity NPC295823
0.8306 Intermediate Similarity NPC475287
0.8306 Intermediate Similarity NPC124296
0.8306 Intermediate Similarity NPC46665
0.8306 Intermediate Similarity NPC309714
0.8306 Intermediate Similarity NPC151543
0.8306 Intermediate Similarity NPC96641
0.8306 Intermediate Similarity NPC166422
0.8306 Intermediate Similarity NPC258885
0.8306 Intermediate Similarity NPC133818
0.8306 Intermediate Similarity NPC150400
0.8306 Intermediate Similarity NPC163183
0.8306 Intermediate Similarity NPC473826
0.8306 Intermediate Similarity NPC473343
0.8306 Intermediate Similarity NPC174720
0.8306 Intermediate Similarity NPC219180
0.8306 Intermediate Similarity NPC475467
0.8306 Intermediate Similarity NPC251263
0.8306 Intermediate Similarity NPC155410
0.8293 Intermediate Similarity NPC164419
0.824 Intermediate Similarity NPC476068
0.824 Intermediate Similarity NPC305981
0.824 Intermediate Similarity NPC309907
0.824 Intermediate Similarity NPC4328
0.824 Intermediate Similarity NPC79643
0.824 Intermediate Similarity NPC60557
0.824 Intermediate Similarity NPC471550
0.824 Intermediate Similarity NPC164389
0.824 Intermediate Similarity NPC293330
0.824 Intermediate Similarity NPC236638
0.824 Intermediate Similarity NPC100639
0.824 Intermediate Similarity NPC76972
0.824 Intermediate Similarity NPC71065
0.824 Intermediate Similarity NPC475486
0.824 Intermediate Similarity NPC294453
0.824 Intermediate Similarity NPC161717
0.824 Intermediate Similarity NPC261506
0.824 Intermediate Similarity NPC54636
0.824 Intermediate Similarity NPC298034
0.824 Intermediate Similarity NPC65105
0.824 Intermediate Similarity NPC204414
0.824 Intermediate Similarity NPC224381
0.824 Intermediate Similarity NPC70809
0.824 Intermediate Similarity NPC471385
0.824 Intermediate Similarity NPC475160
0.824 Intermediate Similarity NPC43550
0.824 Intermediate Similarity NPC123199
0.824 Intermediate Similarity NPC250247
0.824 Intermediate Similarity NPC227551
0.824 Intermediate Similarity NPC473714
0.824 Intermediate Similarity NPC119592
0.824 Intermediate Similarity NPC202828
0.824 Intermediate Similarity NPC469782
0.824 Intermediate Similarity NPC475140
0.824 Intermediate Similarity NPC57484
0.824 Intermediate Similarity NPC41061
0.824 Intermediate Similarity NPC67857
0.8226 Intermediate Similarity NPC473383
0.8226 Intermediate Similarity NPC139894
0.8211 Intermediate Similarity NPC59804
0.8211 Intermediate Similarity NPC474589
0.8211 Intermediate Similarity NPC270667
0.8211 Intermediate Similarity NPC164194
0.8211 Intermediate Similarity NPC279554
0.8211 Intermediate Similarity NPC127056
0.8211 Intermediate Similarity NPC90856
0.8211 Intermediate Similarity NPC56713
0.8211 Intermediate Similarity NPC136877
0.8211 Intermediate Similarity NPC29069
0.8211 Intermediate Similarity NPC475296
0.8211 Intermediate Similarity NPC174679
0.8175 Intermediate Similarity NPC476992
0.8175 Intermediate Similarity NPC161674
0.8175 Intermediate Similarity NPC288205
0.8175 Intermediate Similarity NPC160415
0.8175 Intermediate Similarity NPC26626
0.8175 Intermediate Similarity NPC58448
0.8175 Intermediate Similarity NPC51465
0.8175 Intermediate Similarity NPC291903
0.8175 Intermediate Similarity NPC37134
0.8175 Intermediate Similarity NPC471384
0.8175 Intermediate Similarity NPC75287
0.8175 Intermediate Similarity NPC305267
0.8145 Intermediate Similarity NPC235841
0.8145 Intermediate Similarity NPC30397
0.8145 Intermediate Similarity NPC179434
0.8145 Intermediate Similarity NPC108748
0.8145 Intermediate Similarity NPC297208
0.8145 Intermediate Similarity NPC211798
0.8145 Intermediate Similarity NPC473481
0.813 Intermediate Similarity NPC204407
0.813 Intermediate Similarity NPC237503
0.813 Intermediate Similarity NPC57362
0.813 Intermediate Similarity NPC167383
0.813 Intermediate Similarity NPC306746
0.811 Intermediate Similarity NPC68175
0.811 Intermediate Similarity NPC475119
0.811 Intermediate Similarity NPC148417
0.811 Intermediate Similarity NPC110633
0.811 Intermediate Similarity NPC470876
0.811 Intermediate Similarity NPC69811
0.811 Intermediate Similarity NPC471547
0.811 Intermediate Similarity NPC220160
0.811 Intermediate Similarity NPC33012
0.811 Intermediate Similarity NPC136768
0.811 Intermediate Similarity NPC473452
0.811 Intermediate Similarity NPC104137
0.811 Intermediate Similarity NPC8524
0.811 Intermediate Similarity NPC85154
0.811 Intermediate Similarity NPC286457
0.811 Intermediate Similarity NPC309223
0.811 Intermediate Similarity NPC475209
0.811 Intermediate Similarity NPC123522
0.811 Intermediate Similarity NPC473824
0.811 Intermediate Similarity NPC191827
0.811 Intermediate Similarity NPC323359
0.811 Intermediate Similarity NPC102505
0.811 Intermediate Similarity NPC185466
0.811 Intermediate Similarity NPC475514
0.811 Intermediate Similarity NPC300419
0.808 Intermediate Similarity NPC80843
0.808 Intermediate Similarity NPC128925
0.808 Intermediate Similarity NPC1046
0.808 Intermediate Similarity NPC256798
0.8065 Intermediate Similarity NPC75747
0.8065 Intermediate Similarity NPC274507
0.8065 Intermediate Similarity NPC476885
0.8065 Intermediate Similarity NPC269095
0.8065 Intermediate Similarity NPC476887
0.8065 Intermediate Similarity NPC199457
0.8065 Intermediate Similarity NPC78046
0.8065 Intermediate Similarity NPC476881
0.8065 Intermediate Similarity NPC476883
0.8065 Intermediate Similarity NPC108709
0.8065 Intermediate Similarity NPC110139
0.8065 Intermediate Similarity NPC476884

  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 NPC280941 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
0.7612 Intermediate Similarity NPD8328 Phase 3
0.7424 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD8133 Approved
0.7014 Intermediate Similarity NPD8450 Suspended
0.6944 Remote Similarity NPD8449 Approved
0.6908 Remote Similarity NPD7625 Phase 1
0.6884 Remote Similarity NPD8377 Approved
0.6884 Remote Similarity NPD8294 Approved
0.687 Remote Similarity NPD6412 Phase 2
0.6835 Remote Similarity NPD8296 Approved
0.6835 Remote Similarity NPD8335 Approved
0.6835 Remote Similarity NPD8378 Approved
0.6835 Remote Similarity NPD8380 Approved
0.6835 Remote Similarity NPD8379 Approved
0.6818 Remote Similarity NPD8174 Phase 2
0.6818 Remote Similarity NPD6686 Approved
0.6806 Remote Similarity NPD8392 Approved
0.6806 Remote Similarity NPD8391 Approved
0.6806 Remote Similarity NPD8390 Approved
0.6783 Remote Similarity NPD8336 Approved
0.6783 Remote Similarity NPD8337 Approved
0.6761 Remote Similarity NPD7507 Approved
0.6716 Remote Similarity NPD6421 Discontinued
0.6714 Remote Similarity NPD8033 Approved
0.6713 Remote Similarity NPD8448 Approved
0.6711 Remote Similarity NPD6333 Approved
0.6711 Remote Similarity NPD6334 Approved
0.669 Remote Similarity NPD8342 Approved
0.669 Remote Similarity NPD8340 Approved
0.669 Remote Similarity NPD8341 Approved
0.669 Remote Similarity NPD6914 Discontinued
0.669 Remote Similarity NPD8299 Approved
0.6667 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7748 Approved
0.6643 Remote Similarity NPD8451 Approved
0.6641 Remote Similarity NPD7902 Approved
0.6621 Remote Similarity NPD7319 Approved
0.6599 Remote Similarity NPD8338 Approved
0.6597 Remote Similarity NPD8074 Phase 3
0.6596 Remote Similarity NPD8515 Approved
0.6596 Remote Similarity NPD8517 Approved
0.6596 Remote Similarity NPD8516 Approved
0.6596 Remote Similarity NPD8513 Phase 3
0.6594 Remote Similarity NPD6940 Discontinued
0.6577 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7736 Approved
0.6538 Remote Similarity NPD8418 Phase 2
0.651 Remote Similarity NPD8415 Approved
0.6508 Remote Similarity NPD7515 Phase 2
0.65 Remote Similarity NPD7328 Approved
0.65 Remote Similarity NPD7327 Approved
0.65 Remote Similarity NPD7641 Discontinued
0.6496 Remote Similarity NPD6429 Approved
0.6496 Remote Similarity NPD6430 Approved
0.6493 Remote Similarity NPD8307 Discontinued
0.6479 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6454 Remote Similarity NPD7516 Approved
0.6434 Remote Similarity NPD8080 Discontinued
0.6433 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6406 Remote Similarity NPD7900 Approved
0.6406 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6389 Remote Similarity NPD7829 Approved
0.6389 Remote Similarity NPD7830 Approved
0.637 Remote Similarity NPD8293 Discontinued
0.637 Remote Similarity NPD8140 Approved
0.6364 Remote Similarity NPD8444 Approved
0.6364 Remote Similarity NPD6921 Approved
0.6364 Remote Similarity NPD7503 Approved
0.635 Remote Similarity NPD8087 Discontinued
0.6343 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7141 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7140 Approved
0.6316 Remote Similarity NPD7139 Approved
0.6296 Remote Similarity NPD8393 Approved
0.6294 Remote Similarity NPD8347 Approved
0.6294 Remote Similarity NPD8346 Approved
0.6294 Remote Similarity NPD8345 Approved
0.6277 Remote Similarity NPD8305 Approved
0.6277 Remote Similarity NPD8306 Approved
0.6269 Remote Similarity NPD8276 Approved
0.6269 Remote Similarity NPD8275 Approved
0.625 Remote Similarity NPD6909 Approved
0.625 Remote Similarity NPD6908 Approved
0.6207 Remote Similarity NPD6370 Approved
0.6194 Remote Similarity NPD8139 Approved
0.6194 Remote Similarity NPD8085 Approved
0.6194 Remote Similarity NPD8086 Approved
0.6194 Remote Similarity NPD8084 Approved
0.6194 Remote Similarity NPD8082 Approved
0.6194 Remote Similarity NPD8138 Approved
0.6194 Remote Similarity NPD8083 Approved
0.6187 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6176 Remote Similarity NPD5357 Phase 1
0.6172 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6159 Remote Similarity NPD6941 Approved
0.6143 Remote Similarity NPD8297 Approved
0.6143 Remote Similarity NPD6882 Approved
0.6124 Remote Similarity NPD8035 Phase 2
0.6124 Remote Similarity NPD8034 Phase 2
0.6122 Remote Similarity NPD7492 Approved
0.6103 Remote Similarity NPD8081 Approved
0.609 Remote Similarity NPD7638 Approved
0.6084 Remote Similarity NPD6009 Approved
0.6081 Remote Similarity NPD6616 Approved
0.6077 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6069 Remote Similarity NPD6059 Approved
0.6069 Remote Similarity NPD6054 Approved
0.6069 Remote Similarity NPD6319 Approved
0.6054 Remote Similarity NPD7604 Phase 2
0.6054 Remote Similarity NPD7642 Approved
0.6054 Remote Similarity NPD6067 Discontinued
0.6051 Remote Similarity NPD8384 Approved
0.6045 Remote Similarity NPD7639 Approved
0.6045 Remote Similarity NPD7640 Approved
0.6043 Remote Similarity NPD4061 Clinical (unspecified phase)
0.604 Remote Similarity NPD7078 Approved
0.6029 Remote Similarity NPD1407 Approved
0.6024 Remote Similarity NPD8417 Discontinued
0.5986 Remote Similarity NPD4632 Approved
0.5986 Remote Similarity NPD8298 Phase 2
0.5971 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5967 Remote Similarity NPD8424 Clinical (unspecified phase)
0.5957 Remote Similarity NPD8486 Clinical (unspecified phase)
0.5955 Remote Similarity NPD8368 Discontinued
0.5954 Remote Similarity NPD1447 Phase 3
0.5954 Remote Similarity NPD6399 Phase 3
0.5954 Remote Similarity NPD8171 Discontinued
0.5954 Remote Similarity NPD1446 Phase 3
0.5946 Remote Similarity NPD7122 Discontinued
0.5944 Remote Similarity NPD8407 Phase 2
0.5942 Remote Similarity NPD6402 Approved
0.5942 Remote Similarity NPD6675 Approved
0.5942 Remote Similarity NPD5739 Approved
0.5942 Remote Similarity NPD7128 Approved
0.594 Remote Similarity NPD5349 Clinical (unspecified phase)
0.594 Remote Similarity NPD6428 Approved
0.5935 Remote Similarity NPD7645 Phase 2
0.5929 Remote Similarity NPD6372 Approved
0.5929 Remote Similarity NPD6373 Approved
0.5926 Remote Similarity NPD7274 Clinical (unspecified phase)
0.5918 Remote Similarity NPD6015 Approved
0.5918 Remote Similarity NPD8267 Approved
0.5918 Remote Similarity NPD6016 Approved
0.5918 Remote Similarity NPD8268 Approved
0.5918 Remote Similarity NPD8269 Approved
0.5918 Remote Similarity NPD8266 Approved
0.5915 Remote Similarity NPD8389 Clinical (unspecified phase)
0.5906 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5904 Remote Similarity NPD7237 Clinical (unspecified phase)
0.5902 Remote Similarity NPD8360 Approved
0.5902 Remote Similarity NPD8361 Approved
0.5902 Remote Similarity NPD8435 Approved
0.5891 Remote Similarity NPD618 Clinical (unspecified phase)
0.5887 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5887 Remote Similarity NPD6420 Discontinued
0.5878 Remote Similarity NPD5988 Approved
0.5878 Remote Similarity NPD6436 Phase 3
0.5862 Remote Similarity NPD7115 Discovery
0.5857 Remote Similarity NPD6899 Approved
0.5857 Remote Similarity NPD7320 Approved
0.5857 Remote Similarity NPD6881 Approved
0.5852 Remote Similarity NPD2255 Approved
0.5845 Remote Similarity NPD6649 Approved
0.5845 Remote Similarity NPD6650 Approved
0.5845 Remote Similarity NPD8130 Phase 1
0.5798 Remote Similarity NPD8485 Approved
0.5786 Remote Similarity NPD5701 Approved
0.5786 Remote Similarity NPD5697 Approved
0.5779 Remote Similarity NPD7260 Phase 2
0.5775 Remote Similarity NPD7102 Approved
0.5775 Remote Similarity NPD6883 Approved
0.5775 Remote Similarity NPD7290 Approved
0.5762 Remote Similarity NPD8273 Phase 1
0.5758 Remote Similarity NPD6411 Approved
0.5751 Remote Similarity NPD8319 Approved
0.5751 Remote Similarity NPD8320 Phase 1
0.5734 Remote Similarity NPD6847 Approved
0.5734 Remote Similarity NPD6617 Approved
0.5734 Remote Similarity NPD6869 Approved
0.5725 Remote Similarity NPD8300 Approved
0.5725 Remote Similarity NPD8301 Approved
0.5725 Remote Similarity NPD3716 Discontinued
0.5705 Remote Similarity NPD5983 Phase 2
0.5704 Remote Similarity NPD6012 Approved
0.5704 Remote Similarity NPD6014 Approved
0.5704 Remote Similarity NPD6013 Approved
0.5694 Remote Similarity NPD8078 Approved
0.5694 Remote Similarity NPD8077 Approved
0.5686 Remote Similarity NPD6033 Approved
0.5685 Remote Similarity NPD7754 Approved
0.5685 Remote Similarity NPD7755 Approved
0.5683 Remote Similarity NPD8045 Clinical (unspecified phase)
0.5682 Remote Similarity NPD3168 Discontinued
0.5682 Remote Similarity NPD46 Approved
0.5682 Remote Similarity NPD6698 Approved
0.568 Remote Similarity NPD8414 Discontinued
0.5674 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5662 Remote Similarity NPD6083 Phase 2
0.5662 Remote Similarity NPD6084 Phase 2

  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