Structure

Physi-Chem Properties

Molecular Weight:  807.48
Volume:  809.749
LogP:  3.32
LogD:  3.057
LogS:  -3.022
# Rotatable Bonds:  8
TPSA:  224.7
# H-Bond Aceptor:  14
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.137
Synthetic Accessibility Score:  5.908
Fsp3:  0.907
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:  -5.465
MDCK Permeability:  7.038842795736855e-06
Pgp-inhibitor:  0.965
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.262
20% Bioavailability (F20%):  0.566
30% Bioavailability (F30%):  0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.049
Plasma Protein Binding (PPB):  76.99848937988281%
Volume Distribution (VD):  0.444
Pgp-substrate:  20.087820053100586%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.082
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.16
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.038
CYP2D6-inhibitor:  0.038
CYP2D6-substrate:  0.073
CYP3A4-inhibitor:  0.088
CYP3A4-substrate:  0.043

ADMET: Excretion

Clearance (CL):  0.806
Half-life (T1/2):  0.563

ADMET: Toxicity

hERG Blockers:  0.1
Human Hepatotoxicity (H-HT):  0.153
Drug-inuced Liver Injury (DILI):  0.04
AMES Toxicity:  0.289
Rat Oral Acute Toxicity:  0.2
Maximum Recommended Daily Dose:  0.991
Skin Sensitization:  0.153
Carcinogencity:  0.04
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.942

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

  Natural Product: NPC75318

Natural Product ID:  NPC75318
Common Name*:   3-O-[Alpha-L-Arabinopyranosyl(1_>6)]-2-Acetamido-2-Deoxy-Beta-D-Glucopyranosyl Echinocystic Acid
IUPAC Name:   (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-5-hydroxy-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:  LRMCXUYYLPHGOS-CJXDOCFZSA-N
Standard InCHI:  InChI=1S/C43H69NO13/c1-21(45)44-30-33(50)32(49)25(20-55-36-34(51)31(48)24(46)19-54-36)56-35(30)57-29-12-13-40(6)26(39(29,4)5)11-14-41(7)27(40)10-9-22-23-17-38(2,3)15-16-43(23,37(52)53)28(47)18-42(22,41)8/h9,23-36,46-51H,10-20H2,1-8H3,(H,44,45)(H,52,53)/t23-,24-,25+,26-,27+,28+,29-,30+,31-,32+,33+,34+,35-,36-,40-,41+,42+,43+/m0/s1
SMILES:  CC(=N[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)C[C@H]([C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)O)C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1765595
PubChem CID:   14217288
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
NPO17211 Albizia inundata Species Fabaceae Eukaryota n.a. aerial part n.a. PMID[21314099]
NPO17211 Albizia inundata Species Fabaceae Eukaryota aerial parts Primavera, Department Patino, Province of Formosa, Argentina (lat. 27S, long. 58W) 1999-AUG PMID[21314099]
NPO17211 Albizia inundata 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
NPT169 Cell Line B16-F10 Mus musculus IC50 = 5100.0 nM PMID[478032]
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 = 9200.0 nM PMID[478032]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2800.0 nM PMID[478032]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1800.0 nM PMID[478032]

☑ 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 NPC75318 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
0.9919 High Similarity NPC76999
0.9919 High Similarity NPC145899
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 NPC280941
0.968 High Similarity NPC235772
0.9609 High Similarity NPC82931
0.9609 High Similarity NPC210729
0.9609 High Similarity NPC172365
0.9462 High Similarity NPC475152
0.9462 High Similarity NPC475394
0.9462 High Similarity NPC475584
0.9389 High Similarity NPC475892
0.8849 High Similarity NPC265699
0.8849 High Similarity NPC475527
0.8846 High Similarity NPC477072
0.8786 High Similarity NPC187497
0.8786 High Similarity NPC475599
0.8786 High Similarity NPC174336
0.8786 High Similarity NPC100612
0.8786 High Similarity NPC113620
0.8657 High Similarity NPC302276
0.8657 High Similarity NPC180770
0.854 High Similarity NPC141669
0.8529 High Similarity NPC162910
0.8519 High Similarity NPC265908
0.8409 Intermediate Similarity NPC139585
0.8406 Intermediate Similarity NPC193579
0.8406 Intermediate Similarity NPC298469
0.8374 Intermediate Similarity NPC1046
0.8374 Intermediate Similarity NPC80843
0.8345 Intermediate Similarity NPC214821
0.8345 Intermediate Similarity NPC298067
0.8306 Intermediate Similarity NPC475208
0.8306 Intermediate Similarity NPC238935
0.8293 Intermediate Similarity NPC31839
0.824 Intermediate Similarity NPC164389
0.824 Intermediate Similarity NPC475486
0.8239 Intermediate Similarity NPC36463
0.8239 Intermediate Similarity NPC298005
0.8227 Intermediate Similarity NPC61717
0.8227 Intermediate Similarity NPC244380
0.8226 Intermediate Similarity NPC48249
0.8211 Intermediate Similarity NPC59804
0.8211 Intermediate Similarity NPC29069
0.8211 Intermediate Similarity NPC90856
0.8211 Intermediate Similarity NPC279554
0.8211 Intermediate Similarity NPC164194
0.8211 Intermediate Similarity NPC270667
0.8211 Intermediate Similarity NPC174679
0.8211 Intermediate Similarity NPC127056
0.8211 Intermediate Similarity NPC56713
0.8211 Intermediate Similarity NPC242611
0.8211 Intermediate Similarity NPC475296
0.8211 Intermediate Similarity NPC136877
0.8211 Intermediate Similarity NPC474589
0.8175 Intermediate Similarity NPC476992
0.8175 Intermediate Similarity NPC288205
0.8175 Intermediate Similarity NPC26626
0.8175 Intermediate Similarity NPC51465
0.8175 Intermediate Similarity NPC291903
0.8175 Intermediate Similarity NPC37134
0.8175 Intermediate Similarity NPC75287
0.8175 Intermediate Similarity NPC305267
0.8145 Intermediate Similarity NPC235841
0.8145 Intermediate Similarity NPC30397
0.8145 Intermediate Similarity NPC164419
0.8145 Intermediate Similarity NPC179434
0.8145 Intermediate Similarity NPC473481
0.8145 Intermediate Similarity NPC297208
0.8145 Intermediate Similarity NPC211798
0.8145 Intermediate Similarity NPC108748
0.8143 Intermediate Similarity NPC284625
0.8143 Intermediate Similarity NPC69176
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 NPC475119
0.811 Intermediate Similarity NPC475209
0.811 Intermediate Similarity NPC470876
0.811 Intermediate Similarity NPC33012
0.811 Intermediate Similarity NPC473452
0.811 Intermediate Similarity NPC220160
0.811 Intermediate Similarity NPC104137
0.811 Intermediate Similarity NPC8524
0.811 Intermediate Similarity NPC69811
0.811 Intermediate Similarity NPC473824
0.811 Intermediate Similarity NPC85154
0.811 Intermediate Similarity NPC286457
0.811 Intermediate Similarity NPC309223
0.811 Intermediate Similarity NPC123522
0.811 Intermediate Similarity NPC191827
0.811 Intermediate Similarity NPC323359
0.811 Intermediate Similarity NPC102505
0.811 Intermediate Similarity NPC475514
0.811 Intermediate Similarity NPC300419
0.808 Intermediate Similarity NPC475504
0.808 Intermediate Similarity NPC473383
0.808 Intermediate Similarity NPC128925
0.808 Intermediate Similarity NPC100383
0.808 Intermediate Similarity NPC473373
0.808 Intermediate Similarity NPC475516
0.808 Intermediate Similarity NPC471383
0.808 Intermediate Similarity NPC324875
0.808 Intermediate Similarity NPC102439
0.808 Intermediate Similarity NPC79718
0.808 Intermediate Similarity NPC101744
0.808 Intermediate Similarity NPC10320
0.808 Intermediate Similarity NPC256798
0.808 Intermediate Similarity NPC109079
0.808 Intermediate Similarity NPC276093
0.808 Intermediate Similarity NPC139044
0.808 Intermediate Similarity NPC139894
0.808 Intermediate Similarity NPC257468
0.808 Intermediate Similarity NPC104400
0.808 Intermediate Similarity NPC469946
0.808 Intermediate Similarity NPC292677
0.808 Intermediate Similarity NPC104071
0.8065 Intermediate Similarity NPC75747
0.8065 Intermediate Similarity NPC274507
0.8065 Intermediate Similarity NPC199457
0.8065 Intermediate Similarity NPC476880
0.8065 Intermediate Similarity NPC476885
0.8065 Intermediate Similarity NPC269095
0.8065 Intermediate Similarity NPC78046
0.8065 Intermediate Similarity NPC476883
0.8065 Intermediate Similarity NPC476882
0.8065 Intermediate Similarity NPC108709
0.8065 Intermediate Similarity NPC110139
0.8065 Intermediate Similarity NPC476884
0.8065 Intermediate Similarity NPC476881
0.8065 Intermediate Similarity NPC68419
0.8065 Intermediate Similarity NPC476886
0.8065 Intermediate Similarity NPC102914
0.8065 Intermediate Similarity NPC476887
0.8065 Intermediate Similarity NPC7870
0.8049 Intermediate Similarity NPC28198
0.8049 Intermediate Similarity NPC284807
0.8049 Intermediate Similarity NPC177246
0.8049 Intermediate Similarity NPC476123
0.8047 Intermediate Similarity NPC232237
0.8047 Intermediate Similarity NPC105800
0.8047 Intermediate Similarity NPC473459
0.8047 Intermediate Similarity NPC237191
0.8016 Intermediate Similarity NPC114304
0.8016 Intermediate Similarity NPC150400
0.8016 Intermediate Similarity NPC166422
0.8016 Intermediate Similarity NPC309714
0.8016 Intermediate Similarity NPC46665
0.8016 Intermediate Similarity NPC323341
0.8016 Intermediate Similarity NPC47063
0.8016 Intermediate Similarity NPC475287
0.8016 Intermediate Similarity NPC134835
0.8016 Intermediate Similarity NPC258885
0.8016 Intermediate Similarity NPC96641
0.8016 Intermediate Similarity NPC133818
0.8016 Intermediate Similarity NPC204458
0.8016 Intermediate Similarity NPC251263
0.8016 Intermediate Similarity NPC155410
0.8016 Intermediate Similarity NPC295823
0.8016 Intermediate Similarity NPC473826
0.8016 Intermediate Similarity NPC473343
0.8016 Intermediate Similarity NPC138334
0.8016 Intermediate Similarity NPC219180
0.8016 Intermediate Similarity NPC124296
0.8016 Intermediate Similarity NPC114287
0.8016 Intermediate Similarity NPC151543
0.8016 Intermediate Similarity NPC241909
0.8016 Intermediate Similarity NPC174720
0.8016 Intermediate Similarity NPC192600
0.8016 Intermediate Similarity NPC475467
0.8016 Intermediate Similarity NPC73318
0.8016 Intermediate Similarity NPC163183
0.8016 Intermediate Similarity NPC189884
0.8 Intermediate Similarity NPC191763
0.7984 Intermediate Similarity NPC114441
0.7984 Intermediate Similarity NPC471577
0.7984 Intermediate Similarity NPC473884
0.7984 Intermediate Similarity NPC208381
0.7984 Intermediate Similarity NPC39211
0.7984 Intermediate Similarity NPC214484
0.7984 Intermediate Similarity NPC135849
0.7984 Intermediate Similarity NPC35405
0.7984 Intermediate Similarity NPC51564
0.7984 Intermediate Similarity NPC157868
0.7984 Intermediate Similarity NPC309780
0.7984 Intermediate Similarity NPC207738
0.7984 Intermediate Similarity NPC469945
0.7984 Intermediate Similarity NPC472949
0.7984 Intermediate Similarity NPC11551
0.7984 Intermediate Similarity NPC25663
0.7984 Intermediate Similarity NPC180550
0.7984 Intermediate Similarity NPC137917
0.7984 Intermediate Similarity NPC127853
0.7984 Intermediate Similarity NPC475171

  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 NPC75318 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
0.7744 Intermediate Similarity NPD8328 Phase 3
0.7692 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD8133 Approved
0.7021 Intermediate Similarity NPD8336 Approved
0.7021 Intermediate Similarity NPD8337 Approved
0.6939 Remote Similarity NPD6333 Approved
0.6939 Remote Similarity NPD6334 Approved
0.6929 Remote Similarity NPD8299 Approved
0.6929 Remote Similarity NPD8341 Approved
0.6929 Remote Similarity NPD8340 Approved
0.6929 Remote Similarity NPD8342 Approved
0.6923 Remote Similarity NPD8392 Approved
0.6923 Remote Similarity NPD8391 Approved
0.6923 Remote Similarity NPD6914 Discontinued
0.6923 Remote Similarity NPD8390 Approved
0.6912 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6908 Remote Similarity NPD7625 Phase 1
0.6879 Remote Similarity NPD8451 Approved
0.687 Remote Similarity NPD6412 Phase 2
0.6853 Remote Similarity NPD7319 Approved
0.6831 Remote Similarity NPD8074 Phase 3
0.6831 Remote Similarity NPD8448 Approved
0.6828 Remote Similarity NPD8449 Approved
0.6828 Remote Similarity NPD8338 Approved
0.6818 Remote Similarity NPD8174 Phase 2
0.6818 Remote Similarity NPD6686 Approved
0.6803 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6783 Remote Similarity NPD7736 Approved
0.6781 Remote Similarity NPD8450 Suspended
0.6763 Remote Similarity NPD8377 Approved
0.6763 Remote Similarity NPD8294 Approved
0.6761 Remote Similarity NPD7507 Approved
0.6742 Remote Similarity NPD8307 Discontinued
0.6735 Remote Similarity NPD8415 Approved
0.6716 Remote Similarity NPD6421 Discontinued
0.6714 Remote Similarity NPD8380 Approved
0.6714 Remote Similarity NPD8335 Approved
0.6714 Remote Similarity NPD8517 Approved
0.6714 Remote Similarity NPD8033 Approved
0.6714 Remote Similarity NPD8379 Approved
0.6714 Remote Similarity NPD8513 Phase 3
0.6714 Remote Similarity NPD8378 Approved
0.6714 Remote Similarity NPD8515 Approved
0.6714 Remote Similarity NPD8516 Approved
0.6714 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6714 Remote Similarity NPD8296 Approved
0.6667 Remote Similarity NPD8080 Discontinued
0.6667 Remote Similarity NPD7748 Approved
0.6641 Remote Similarity NPD7902 Approved
0.662 Remote Similarity NPD7830 Approved
0.662 Remote Similarity NPD7829 Approved
0.6617 Remote Similarity NPD8140 Approved
0.6597 Remote Similarity NPD8293 Discontinued
0.6596 Remote Similarity NPD6921 Approved
0.6594 Remote Similarity NPD6940 Discontinued
0.6593 Remote Similarity NPD8087 Discontinued
0.6538 Remote Similarity NPD8418 Phase 2
0.6519 Remote Similarity NPD8306 Approved
0.6519 Remote Similarity NPD8305 Approved
0.6515 Remote Similarity NPD8276 Approved
0.6515 Remote Similarity NPD8275 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
0.6479 Remote Similarity NPD8444 Approved
0.6454 Remote Similarity NPD7516 Approved
0.6439 Remote Similarity NPD8083 Approved
0.6439 Remote Similarity NPD8138 Approved
0.6439 Remote Similarity NPD8085 Approved
0.6439 Remote Similarity NPD8086 Approved
0.6439 Remote Similarity NPD8139 Approved
0.6439 Remote Similarity NPD8084 Approved
0.6439 Remote Similarity NPD8082 Approved
0.6434 Remote Similarity NPD6370 Approved
0.6433 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6418 Remote Similarity NPD8393 Approved
0.6408 Remote Similarity NPD8347 Approved
0.6408 Remote Similarity NPD8345 Approved
0.6408 Remote Similarity NPD8346 Approved
0.6406 Remote Similarity NPD7900 Approved
0.6406 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7503 Approved
0.6345 Remote Similarity NPD7492 Approved
0.6343 Remote Similarity NPD8081 Approved
0.6316 Remote Similarity NPD7141 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7140 Approved
0.6316 Remote Similarity NPD7139 Approved
0.6301 Remote Similarity NPD6616 Approved
0.6294 Remote Similarity NPD6054 Approved
0.6294 Remote Similarity NPD6059 Approved
0.6294 Remote Similarity NPD6319 Approved
0.6277 Remote Similarity NPD6941 Approved
0.6276 Remote Similarity NPD7642 Approved
0.6259 Remote Similarity NPD6430 Approved
0.6259 Remote Similarity NPD6429 Approved
0.6259 Remote Similarity NPD7078 Approved
0.6258 Remote Similarity NPD8384 Approved
0.625 Remote Similarity NPD6908 Approved
0.625 Remote Similarity NPD6909 Approved
0.6222 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6204 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6202 Remote Similarity NPD1447 Phase 3
0.6202 Remote Similarity NPD1446 Phase 3
0.6176 Remote Similarity NPD5357 Phase 1
0.6172 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6143 Remote Similarity NPD8297 Approved
0.6143 Remote Similarity NPD6882 Approved
0.6138 Remote Similarity NPD6015 Approved
0.6138 Remote Similarity NPD6016 Approved
0.6129 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6124 Remote Similarity NPD8035 Phase 2
0.6124 Remote Similarity NPD8034 Phase 2
0.6111 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6096 Remote Similarity NPD5988 Approved
0.609 Remote Similarity NPD7638 Approved
0.609 Remote Similarity NPD2255 Approved
0.6084 Remote Similarity NPD6009 Approved
0.6084 Remote Similarity NPD7115 Discovery
0.6077 Remote Similarity NPD8435 Approved
0.6077 Remote Similarity NPD8361 Approved
0.6077 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6077 Remote Similarity NPD8360 Approved
0.6071 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6054 Remote Similarity NPD6067 Discontinued
0.6054 Remote Similarity NPD7604 Phase 2
0.6045 Remote Similarity NPD7639 Approved
0.6045 Remote Similarity NPD7640 Approved
0.6045 Remote Similarity NPD8368 Discontinued
0.6043 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6034 Remote Similarity NPD8407 Phase 2
0.6029 Remote Similarity NPD1407 Approved
0.6027 Remote Similarity NPD8268 Approved
0.6027 Remote Similarity NPD8267 Approved
0.6027 Remote Similarity NPD8269 Approved
0.6027 Remote Similarity NPD8266 Approved
0.6024 Remote Similarity NPD8417 Discontinued
0.6 Remote Similarity NPD6411 Approved
0.5986 Remote Similarity NPD4632 Approved
0.5986 Remote Similarity NPD8298 Phase 2
0.5973 Remote Similarity NPD8273 Phase 1
0.5968 Remote Similarity NPD8485 Approved
0.5967 Remote Similarity NPD8424 Clinical (unspecified phase)
0.5956 Remote Similarity NPD8300 Approved
0.5956 Remote Similarity NPD8301 Approved
0.5954 Remote Similarity NPD6399 Phase 3
0.5946 Remote Similarity NPD7122 Discontinued
0.5942 Remote Similarity NPD6402 Approved
0.5942 Remote Similarity NPD7128 Approved
0.5942 Remote Similarity NPD6675 Approved
0.5942 Remote Similarity NPD5739 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)
0.5906 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5904 Remote Similarity NPD7237 Clinical (unspecified phase)
0.5894 Remote Similarity NPD6033 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 NPD6436 Phase 3
0.5868 Remote Similarity NPD8414 Discontinued
0.5857 Remote Similarity NPD6899 Approved
0.5857 Remote Similarity NPD6881 Approved
0.5857 Remote Similarity NPD7320 Approved
0.5852 Remote Similarity NPD4225 Approved
0.5846 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5846 Remote Similarity NPD6101 Approved
0.5845 Remote Similarity NPD1719 Phase 1
0.5845 Remote Similarity NPD6649 Approved
0.5845 Remote Similarity NPD6650 Approved
0.5845 Remote Similarity NPD8130 Phase 1
0.5833 Remote Similarity NPD8319 Approved
0.5833 Remote Similarity NPD8320 Phase 1
0.5833 Remote Similarity NPD8171 Discontinued
0.5821 Remote Similarity NPD7839 Suspended
0.5786 Remote Similarity NPD5697 Approved
0.5786 Remote Similarity NPD5701 Approved
0.5779 Remote Similarity NPD7260 Phase 2
0.5775 Remote Similarity NPD7102 Approved
0.5775 Remote Similarity NPD4634 Approved
0.5775 Remote Similarity NPD6883 Approved
0.5775 Remote Similarity NPD7290 Approved
0.5769 Remote Similarity NPD4264 Clinical (unspecified phase)
0.5758 Remote Similarity NPD7983 Approved
0.5753 Remote Similarity NPD7500 Approved
0.5734 Remote Similarity NPD6847 Approved
0.5734 Remote Similarity NPD6617 Approved
0.5734 Remote Similarity NPD6869 Approved
0.5725 Remote Similarity NPD3716 Discontinued
0.5714 Remote Similarity NPD5779 Approved
0.5714 Remote Similarity NPD5778 Approved
0.5706 Remote Similarity NPD7749 Clinical (unspecified phase)
0.5705 Remote Similarity NPD5983 Phase 2
0.5704 Remote Similarity NPD6012 Approved
0.5704 Remote Similarity NPD6014 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