Structure

Physi-Chem Properties

Molecular Weight:  480.29
Volume:  512.786
LogP:  4.64
LogD:  3.439
LogS:  -5.037
# Rotatable Bonds:  2
TPSA:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.36
Synthetic Accessibility Score:  4.766
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.252
MDCK Permeability:  2.004106863751076e-05
Pgp-inhibitor:  0.733
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.264
30% Bioavailability (F30%):  0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.02
Plasma Protein Binding (PPB):  99.36723327636719%
Volume Distribution (VD):  0.677
Pgp-substrate:  3.7523481845855713%

ADMET: Metabolism

CYP1A2-inhibitor:  0.053
CYP1A2-substrate:  0.962
CYP2C19-inhibitor:  0.063
CYP2C19-substrate:  0.839
CYP2C9-inhibitor:  0.225
CYP2C9-substrate:  0.272
CYP2D6-inhibitor:  0.262
CYP2D6-substrate:  0.063
CYP3A4-inhibitor:  0.836
CYP3A4-substrate:  0.92

ADMET: Excretion

Clearance (CL):  8.043
Half-life (T1/2):  0.513

ADMET: Toxicity

hERG Blockers:  0.073
Human Hepatotoxicity (H-HT):  0.606
Drug-inuced Liver Injury (DILI):  0.08
AMES Toxicity:  0.098
Rat Oral Acute Toxicity:  0.113
Maximum Recommended Daily Dose:  0.579
Skin Sensitization:  0.094
Carcinogencity:  0.736
Eye Corrosion:  0.003
Eye Irritation:  0.078
Respiratory Toxicity:  0.951

Download Data

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

  Natural Product: NPC184935

Natural Product ID:  NPC184935
Common Name*:   6-Oxopristimerol
IUPAC Name:   methyl (2R,4aS,6aR,6aS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate
Synonyms:   6-Oxo-Pristimerol; 6-Oxopristimerol
Standard InCHIKey:  QHONUEZGTQYXKH-NLVUKCNFSA-N
Standard InCHI:  InChI=1S/C30H40O5/c1-17-23-18(14-20(32)24(17)33)28(4)11-13-30(6)22-16-27(3,25(34)35-7)9-8-26(22,2)10-12-29(30,5)21(28)15-19(23)31/h14-15,22,32-33H,8-13,16H2,1-7H3/t22-,26-,27-,28+,29-,30+/m1/s1
SMILES:  COC(=O)[C@]1(C)CC[C@]2([C@@H](C1)[C@]1(C)CC[C@@]3(C(=CC(=O)c4c3cc(O)c(c4C)O)[C@]1(CC2)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL254102
PubChem CID:   11754914
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[11112781]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota n.a. Tanzania n.a. PMID[11430019]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota root bark n.a. n.a. PMID[12027753]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota leaves n.a. n.a. PMID[12502337]
NPO28607 Reissantia buchananii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[14640511]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[153409]
NPO8106 Kadsura heteroclita Species Schisandraceae Eukaryota n.a. stem n.a. PMID[16557460]
NPO40563 Maytenus ilicifolia Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17555350]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota n.a. root n.a. PMID[17960072]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota n.a. leaf n.a. PMID[17960072]
NPO14544 Maytenus chuchuhuasca Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18164197]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[21673922]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[23265519]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[23317005]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[23488669]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota seeds n.a. n.a. PMID[26221771]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[27524650]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[29115831]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[31287310]
NPO40563 Maytenus ilicifolia Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7714534]
NPO14544 Maytenus chuchuhuasca Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7714534]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO62 Tetracera asiatica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8106 Kadsura heteroclita Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14544 Maytenus chuchuhuasca Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15601 Pyrus x bretschneideri Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO62 Tetracera asiatica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20434 Tolypocladium ophioglossoides Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28607 Reissantia buchananii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8278 Perenniporia ochroleuca Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24527 Plazia daphnoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25151 Euphorbia cheiradenia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6313 Phormidium sp Species Oscillatoriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15601 Pyrus x bretschneideri Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15769 Solidago chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20434 Tolypocladium ophioglossoides Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5923 Bidens cernua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8408 Symphonia globulifera Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3835 Reticulitermes flavipes Species Termitoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2642 Maytenus apurimacensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11536 Xanthocephalum benthamianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6076 Pentzia calva Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8518 Colchicum luteum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2309 Achillea micrantha Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO62 Tetracera asiatica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1019 Citrus hybr Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10749 Capnella thyrsoidea Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3588 Crucianella maritima Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO783 Pholiota squarrosa Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1358 Iris pallida Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8106 Kadsura heteroclita Species Schisandraceae 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
NPT81 Cell Line A549 Homo sapiens ED50 = 16.4 ug ml-1 PMID[506281]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 12.8 ug ml-1 PMID[506281]
NPT180 Cell Line HCT-8 Homo sapiens ED50 = 14.1 ug ml-1 PMID[506281]
NPT91 Cell Line KB Homo sapiens ED50 = 14.5 ug ml-1 PMID[506281]
NPT306 Cell Line PC-3 Homo sapiens ED50 > 20.0 ug ml-1 PMID[506281]
NPT309 Cell Line 1A9 Homo sapiens ED50 = 11.7 ug ml-1 PMID[506281]
NPT310 Cell Line 1A9/ptx-10 Homo sapiens ED50 = 12.4 ug ml-1 PMID[506281]
NPT309 Cell Line 1A9 Homo sapiens ED50 = 10.7 ug ml-1 PMID[506281]
NPT310 Cell Line 1A9/ptx-10 Homo sapiens ED50 = 7.1 ug ml-1 PMID[506281]
NPT137 Cell Line L1210 Mus musculus IC50 = 2.8 ug.mL-1 PMID[506282]
NPT168 Cell Line P388 Mus musculus IC50 = 1.5 ug.mL-1 PMID[506282]
NPT91 Cell Line KB Homo sapiens IC50 = 2.8 ug.mL-1 PMID[506282]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 16.6 ug ml-1 PMID[506281]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 20.0 ug ml-1 PMID[506281]

☑ 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 NPC184935 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
0.964 High Similarity NPC470038
0.963 High Similarity NPC277559
0.9562 High Similarity NPC470035
0.9485 High Similarity NPC49911
0.9366 High Similarity NPC10842
0.9333 High Similarity NPC476282
0.9306 High Similarity NPC470037
0.9185 High Similarity NPC243305
0.8958 High Similarity NPC75295
0.8958 High Similarity NPC258856
0.8951 High Similarity NPC199936
0.894 High Similarity NPC185617
0.8913 High Similarity NPC138472
0.8913 High Similarity NPC111845
0.8844 High Similarity NPC142654
0.8786 High Similarity NPC43353
0.8786 High Similarity NPC153088
0.8741 High Similarity NPC471853
0.8732 High Similarity NPC469680
0.8732 High Similarity NPC471974
0.8732 High Similarity NPC230811
0.8732 High Similarity NPC469681
0.8714 High Similarity NPC293454
0.8662 High Similarity NPC471152
0.8652 High Similarity NPC103082
0.8643 High Similarity NPC4170
0.8621 High Similarity NPC248068
0.8621 High Similarity NPC477873
0.8621 High Similarity NPC469447
0.8611 High Similarity NPC476534
0.86 High Similarity NPC124842
0.8592 High Similarity NPC7464
0.8503 High Similarity NPC53520
0.8503 High Similarity NPC309169
0.8503 High Similarity NPC196941
0.85 High Similarity NPC18798
0.85 High Similarity NPC291001
0.8487 Intermediate Similarity NPC62051
0.8478 Intermediate Similarity NPC72667
0.8478 Intermediate Similarity NPC176130
0.8478 Intermediate Similarity NPC78364
0.8478 Intermediate Similarity NPC84672
0.8478 Intermediate Similarity NPC69424
0.8472 Intermediate Similarity NPC469857
0.8472 Intermediate Similarity NPC51531
0.8472 Intermediate Similarity NPC23667
0.8472 Intermediate Similarity NPC46242
0.8472 Intermediate Similarity NPC157284
0.8472 Intermediate Similarity NPC473779
0.8472 Intermediate Similarity NPC165191
0.8472 Intermediate Similarity NPC473479
0.8472 Intermediate Similarity NPC289358
0.8472 Intermediate Similarity NPC42384
0.8472 Intermediate Similarity NPC114333
0.8472 Intermediate Similarity NPC5014
0.8472 Intermediate Similarity NPC297797
0.8472 Intermediate Similarity NPC50615
0.8472 Intermediate Similarity NPC28592
0.8472 Intermediate Similarity NPC149773
0.8472 Intermediate Similarity NPC91887
0.8472 Intermediate Similarity NPC477849
0.8472 Intermediate Similarity NPC245760
0.8456 Intermediate Similarity NPC52692
0.8451 Intermediate Similarity NPC202225
0.8429 Intermediate Similarity NPC108129
0.8414 Intermediate Similarity NPC294330
0.8406 Intermediate Similarity NPC254492
0.8397 Intermediate Similarity NPC266365
0.8394 Intermediate Similarity NPC199273
0.8389 Intermediate Similarity NPC474991
0.8378 Intermediate Similarity NPC294679
0.8378 Intermediate Similarity NPC126707
0.8378 Intermediate Similarity NPC144247
0.8378 Intermediate Similarity NPC469375
0.8378 Intermediate Similarity NPC145301
0.8378 Intermediate Similarity NPC8493
0.8369 Intermediate Similarity NPC471851
0.8367 Intermediate Similarity NPC471971
0.8367 Intermediate Similarity NPC469855
0.8367 Intermediate Similarity NPC30846
0.8367 Intermediate Similarity NPC471972
0.8357 Intermediate Similarity NPC303910
0.8357 Intermediate Similarity NPC171460
0.8357 Intermediate Similarity NPC276238
0.8357 Intermediate Similarity NPC117899
0.8356 Intermediate Similarity NPC473527
0.8333 Intermediate Similarity NPC470757
0.8322 Intermediate Similarity NPC84786
0.8322 Intermediate Similarity NPC66894
0.8322 Intermediate Similarity NPC8102
0.8299 Intermediate Similarity NPC272907
0.8299 Intermediate Similarity NPC2681
0.8289 Intermediate Similarity NPC475454
0.8289 Intermediate Similarity NPC473680
0.8289 Intermediate Similarity NPC475311
0.8289 Intermediate Similarity NPC473579
0.8286 Intermediate Similarity NPC193203
0.8286 Intermediate Similarity NPC234175
0.8286 Intermediate Similarity NPC229894
0.8278 Intermediate Similarity NPC46549
0.8278 Intermediate Similarity NPC264229
0.8276 Intermediate Similarity NPC475957
0.8267 Intermediate Similarity NPC246229
0.8267 Intermediate Similarity NPC471970
0.8267 Intermediate Similarity NPC273798
0.8267 Intermediate Similarity NPC191899
0.8267 Intermediate Similarity NPC58752
0.8264 Intermediate Similarity NPC258502
0.8264 Intermediate Similarity NPC477596
0.8255 Intermediate Similarity NPC469854
0.8255 Intermediate Similarity NPC469856
0.8252 Intermediate Similarity NPC475457
0.8252 Intermediate Similarity NPC49742
0.8252 Intermediate Similarity NPC78307
0.8252 Intermediate Similarity NPC294226
0.8252 Intermediate Similarity NPC475627
0.8252 Intermediate Similarity NPC475346
0.8252 Intermediate Similarity NPC18982
0.8252 Intermediate Similarity NPC477139
0.8243 Intermediate Similarity NPC176030
0.8243 Intermediate Similarity NPC192597
0.8243 Intermediate Similarity NPC229218
0.8243 Intermediate Similarity NPC169214
0.8243 Intermediate Similarity NPC477209
0.8243 Intermediate Similarity NPC141817
0.8231 Intermediate Similarity NPC27518
0.8231 Intermediate Similarity NPC304110
0.8231 Intermediate Similarity NPC3218
0.8224 Intermediate Similarity NPC327962
0.8224 Intermediate Similarity NPC303989
0.8219 Intermediate Similarity NPC416
0.8219 Intermediate Similarity NPC182249
0.8219 Intermediate Similarity NPC61398
0.8212 Intermediate Similarity NPC127046
0.8212 Intermediate Similarity NPC5568
0.8207 Intermediate Similarity NPC472308
0.82 Intermediate Similarity NPC225351
0.8194 Intermediate Similarity NPC204582
0.8194 Intermediate Similarity NPC477594
0.8188 Intermediate Similarity NPC477207
0.8188 Intermediate Similarity NPC25491
0.8188 Intermediate Similarity NPC100242
0.8175 Intermediate Similarity NPC249340
0.8175 Intermediate Similarity NPC162935
0.8175 Intermediate Similarity NPC154696
0.817 Intermediate Similarity NPC118033
0.8169 Intermediate Similarity NPC117609
0.8163 Intermediate Similarity NPC155192
0.8163 Intermediate Similarity NPC473591
0.8163 Intermediate Similarity NPC271494
0.8158 Intermediate Similarity NPC132810
0.8156 Intermediate Similarity NPC96024
0.8156 Intermediate Similarity NPC3009
0.8151 Intermediate Similarity NPC477592
0.8151 Intermediate Similarity NPC264022
0.8146 Intermediate Similarity NPC143685
0.8141 Intermediate Similarity NPC471968
0.8138 Intermediate Similarity NPC477874
0.8138 Intermediate Similarity NPC173569
0.8129 Intermediate Similarity NPC15127
0.8125 Intermediate Similarity NPC239855
0.8121 Intermediate Similarity NPC11314
0.8117 Intermediate Similarity NPC473773
0.8117 Intermediate Similarity NPC475579
0.8117 Intermediate Similarity NPC472838
0.8117 Intermediate Similarity NPC144283
0.8117 Intermediate Similarity NPC306011
0.8117 Intermediate Similarity NPC221249
0.8116 Intermediate Similarity NPC282577
0.8116 Intermediate Similarity NPC121168
0.8108 Intermediate Similarity NPC327187
0.8108 Intermediate Similarity NPC172311
0.8105 Intermediate Similarity NPC237441
0.8095 Intermediate Similarity NPC477593
0.8092 Intermediate Similarity NPC325032
0.8092 Intermediate Similarity NPC477483
0.8085 Intermediate Similarity NPC324209
0.8082 Intermediate Similarity NPC326847
0.8082 Intermediate Similarity NPC249817
0.8079 Intermediate Similarity NPC68441
0.8075 Intermediate Similarity NPC200726
0.8071 Intermediate Similarity NPC137750
0.8058 Intermediate Similarity NPC275145
0.8054 Intermediate Similarity NPC92079
0.8054 Intermediate Similarity NPC477595
0.8052 Intermediate Similarity NPC48949
0.8038 Intermediate Similarity NPC471750
0.8029 Intermediate Similarity NPC478121
0.8027 Intermediate Similarity NPC198621
0.8027 Intermediate Similarity NPC53001
0.8027 Intermediate Similarity NPC216940
0.8027 Intermediate Similarity NPC36868
0.8027 Intermediate Similarity NPC147418
0.8027 Intermediate Similarity NPC475482
0.8027 Intermediate Similarity NPC22676
0.8026 Intermediate Similarity NPC477208
0.8026 Intermediate Similarity NPC476535
0.8025 Intermediate Similarity NPC177362
0.8014 Intermediate Similarity NPC72918
0.8014 Intermediate Similarity NPC15837

  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 NPC184935 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
0.8681 High Similarity NPD8166 Discontinued
0.8079 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD7458 Discontinued
0.7933 Intermediate Similarity NPD7003 Approved
0.7744 Intermediate Similarity NPD7473 Discontinued
0.7667 Intermediate Similarity NPD5406 Approved
0.7667 Intermediate Similarity NPD5404 Approved
0.7667 Intermediate Similarity NPD5408 Approved
0.7667 Intermediate Similarity NPD5405 Approved
0.7662 Intermediate Similarity NPD7390 Discontinued
0.7643 Intermediate Similarity NPD3019 Approved
0.7643 Intermediate Similarity NPD2932 Approved
0.7619 Intermediate Similarity NPD6663 Approved
0.7616 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD5736 Approved
0.7561 Intermediate Similarity NPD6232 Discontinued
0.745 Intermediate Similarity NPD943 Approved
0.7448 Intermediate Similarity NPD1470 Approved
0.7447 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD1201 Approved
0.7372 Intermediate Similarity NPD3300 Phase 2
0.7362 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD6273 Approved
0.7299 Intermediate Similarity NPD8150 Discontinued
0.7285 Intermediate Similarity NPD230 Phase 1
0.7255 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD9269 Phase 2
0.7239 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD1465 Phase 2
0.7235 Intermediate Similarity NPD5844 Phase 1
0.7222 Intermediate Similarity NPD3026 Approved
0.7222 Intermediate Similarity NPD3023 Approved
0.7214 Intermediate Similarity NPD5951 Approved
0.7208 Intermediate Similarity NPD2935 Discontinued
0.7203 Intermediate Similarity NPD3025 Approved
0.7203 Intermediate Similarity NPD3024 Approved
0.72 Intermediate Similarity NPD3764 Approved
0.7186 Intermediate Similarity NPD6959 Discontinued
0.7179 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD2346 Discontinued
0.7153 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1283 Approved
0.7143 Intermediate Similarity NPD2799 Discontinued
0.7143 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7819 Suspended
0.7134 Intermediate Similarity NPD4628 Phase 3
0.7115 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD3022 Approved
0.7101 Intermediate Similarity NPD3021 Approved
0.7099 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD3226 Approved
0.7091 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD6190 Approved
0.7083 Intermediate Similarity NPD8127 Discontinued
0.7076 Intermediate Similarity NPD7228 Approved
0.7066 Intermediate Similarity NPD6234 Discontinued
0.7063 Intermediate Similarity NPD2532 Approved
0.7063 Intermediate Similarity NPD2533 Approved
0.7063 Intermediate Similarity NPD2534 Approved
0.7055 Intermediate Similarity NPD7028 Phase 2
0.7044 Intermediate Similarity NPD7236 Approved
0.7039 Intermediate Similarity NPD8032 Phase 2
0.7039 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD4626 Approved
0.7034 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD2801 Approved
0.7029 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD8313 Approved
0.7029 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD8312 Approved
0.7025 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD3750 Approved
0.702 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD7008 Discontinued
0.7 Intermediate Similarity NPD9494 Approved
0.7 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.6993 Remote Similarity NPD4060 Phase 1
0.6993 Remote Similarity NPD3620 Phase 2
0.6993 Remote Similarity NPD3619 Clinical (unspecified phase)
0.698 Remote Similarity NPD1164 Approved
0.697 Remote Similarity NPD37 Approved
0.697 Remote Similarity NPD1934 Approved
0.6966 Remote Similarity NPD9268 Approved
0.6959 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6166 Phase 2
0.6939 Remote Similarity NPD1281 Approved
0.6939 Remote Similarity NPD3092 Approved
0.6905 Remote Similarity NPD7075 Discontinued
0.6903 Remote Similarity NPD6651 Approved
0.6897 Remote Similarity NPD3091 Approved
0.6897 Remote Similarity NPD7074 Phase 3
0.6894 Remote Similarity NPD1511 Approved
0.6892 Remote Similarity NPD3972 Approved
0.6886 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6100 Approved
0.6879 Remote Similarity NPD6099 Approved
0.6867 Remote Similarity NPD3094 Phase 2
0.686 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6852 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6846 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6845 Remote Similarity NPD4965 Approved
0.6845 Remote Similarity NPD4967 Phase 2
0.6845 Remote Similarity NPD7768 Phase 2
0.6845 Remote Similarity NPD4966 Approved
0.6845 Remote Similarity NPD3882 Suspended
0.6839 Remote Similarity NPD7054 Approved
0.6829 Remote Similarity NPD7239 Suspended
0.6826 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6813 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6813 Remote Similarity NPD4110 Phase 3
0.681 Remote Similarity NPD1512 Approved
0.6807 Remote Similarity NPD6873 Phase 2
0.6807 Remote Similarity NPD7411 Suspended
0.68 Remote Similarity NPD7472 Approved
0.6797 Remote Similarity NPD7095 Approved
0.6788 Remote Similarity NPD3455 Phase 2
0.6786 Remote Similarity NPD3817 Phase 2
0.6782 Remote Similarity NPD7177 Discontinued
0.6781 Remote Similarity NPD9545 Approved
0.6774 Remote Similarity NPD826 Approved
0.6774 Remote Similarity NPD2979 Phase 3
0.6774 Remote Similarity NPD825 Approved
0.6768 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6753 Remote Similarity NPD2313 Discontinued
0.6753 Remote Similarity NPD3268 Approved
0.675 Remote Similarity NPD2800 Approved
0.6748 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6748 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6747 Remote Similarity NPD4380 Phase 2
0.6747 Remote Similarity NPD6599 Discontinued
0.6736 Remote Similarity NPD2629 Approved
0.6735 Remote Similarity NPD5691 Approved
0.6735 Remote Similarity NPD1651 Approved
0.6731 Remote Similarity NPD6355 Discontinued
0.673 Remote Similarity NPD7266 Discontinued
0.6725 Remote Similarity NPD5494 Approved
0.6723 Remote Similarity NPD7251 Discontinued
0.6723 Remote Similarity NPD7685 Pre-registration
0.6722 Remote Similarity NPD8434 Phase 2
0.672 Remote Similarity NPD8319 Approved
0.672 Remote Similarity NPD8320 Phase 1
0.6714 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6713 Remote Similarity NPD7635 Approved
0.6711 Remote Similarity NPD2798 Approved
0.6711 Remote Similarity NPD258 Approved
0.6711 Remote Similarity NPD257 Approved
0.671 Remote Similarity NPD7961 Discontinued
0.6709 Remote Similarity NPD3748 Approved
0.6706 Remote Similarity NPD3749 Approved
0.6689 Remote Similarity NPD3095 Discontinued
0.6689 Remote Similarity NPD4059 Approved
0.6686 Remote Similarity NPD7199 Phase 2
0.6686 Remote Similarity NPD3818 Discontinued
0.6685 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4140 Approved
0.6667 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7435 Discontinued
0.6667 Remote Similarity NPD2438 Suspended
0.6667 Remote Similarity NPD6797 Phase 2
0.6667 Remote Similarity NPD4878 Approved
0.6667 Remote Similarity NPD6801 Discontinued
0.6667 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8151 Discontinued
0.6646 Remote Similarity NPD7097 Phase 1
0.6646 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6645 Remote Similarity NPD2797 Approved
0.6645 Remote Similarity NPD6798 Discontinued
0.6644 Remote Similarity NPD9493 Approved
0.6629 Remote Similarity NPD7240 Approved
0.6625 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6625 Remote Similarity NPD2344 Approved
0.6624 Remote Similarity NPD447 Suspended
0.6623 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6604 Remote Similarity NPD1510 Phase 2
0.6603 Remote Similarity NPD259 Phase 1
0.6599 Remote Similarity NPD7610 Discontinued
0.6596 Remote Similarity NPD2342 Discontinued
0.6595 Remote Similarity NPD6534 Approved
0.6595 Remote Similarity NPD6535 Approved
0.6592 Remote Similarity NPD4954 Approved
0.6592 Remote Similarity NPD5034 Approved
0.6592 Remote Similarity NPD4955 Approved
0.6592 Remote Similarity NPD5028 Approved
0.6592 Remote Similarity NPD36 Approved
0.6592 Remote Similarity NPD7808 Phase 3
0.6592 Remote Similarity NPD5026 Approved
0.6582 Remote Similarity NPD1607 Approved
0.6579 Remote Similarity NPD1876 Approved
0.6578 Remote Similarity NPD7699 Phase 2
0.6578 Remote Similarity NPD7700 Phase 2
0.6573 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6562 Remote Similarity NPD2531 Phase 2
0.6562 Remote Similarity NPD4476 Approved
0.6562 Remote Similarity NPD4477 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