Structure

Physi-Chem Properties

Molecular Weight:  362.17
Volume:  356.526
LogP:  1.552
LogD:  1.332
LogS:  -3.789
# Rotatable Bonds:  0
TPSA:  93.06
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.382
Synthetic Accessibility Score:  6.568
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.364
MDCK Permeability:  1.448826787964208e-05
Pgp-inhibitor:  0.035
Pgp-substrate:  0.929
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.023
30% Bioavailability (F30%):  0.641

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.574
Plasma Protein Binding (PPB):  59.12434387207031%
Volume Distribution (VD):  1.751
Pgp-substrate:  51.14824295043945%

ADMET: Metabolism

CYP1A2-inhibitor:  0.01
CYP1A2-substrate:  0.164
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.686
CYP2C9-inhibitor:  0.018
CYP2C9-substrate:  0.052
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.157
CYP3A4-inhibitor:  0.144
CYP3A4-substrate:  0.197

ADMET: Excretion

Clearance (CL):  6.4
Half-life (T1/2):  0.266

ADMET: Toxicity

hERG Blockers:  0.435
Human Hepatotoxicity (H-HT):  0.098
Drug-inuced Liver Injury (DILI):  0.058
AMES Toxicity:  0.517
Rat Oral Acute Toxicity:  0.922
Maximum Recommended Daily Dose:  0.977
Skin Sensitization:  0.435
Carcinogencity:  0.639
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.981

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

  Natural Product: NPC61071

Natural Product ID:  NPC61071
Common Name*:   Enemin
IUPAC Name:   n.a.
Synonyms:   Enemin; Enmein
Standard InCHIKey:  MQOJPNKACWKUGI-CDKPERABSA-N
Standard InCHI:  InChI=1S/C20H26O6/c1-9-10-4-5-11-19(7-10,15(9)22)17(24)26-13-6-12(21)18(2,3)14-16(23)25-8-20(11,13)14/h10-14,16,21,23H,1,4-8H2,2-3H3/t10-,11-,12+,13+,14-,16-,19+,20-/m1/s1
SMILES:  C=C1[C@@H]2CC[C@@H]3[C@@](C2)(C1=O)C(=O)O[C@H]1C[C@@H](C(C)(C)[C@H]2[C@H](O)OC[C@@]312)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL453801
PubChem CID:   352542
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[17020288]
NPO21139 Daphniphyllum calycinum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. PMID[19099464]
NPO19475 Isodon sculponeatus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19697926]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[20949916]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota aerial parts n.a. n.a. PMID[20949916]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[22624550]
NPO8991 Carcinus maenas Species Carcinidae Eukaryota n.a. n.a. n.a. PMID[2421673]
NPO19475 Isodon sculponeatus Species Lamiaceae Eukaryota aerial parts Muli County, Sichuan Province, China 2011-AUG PMID[24219809]
NPO26123 Isodon serra Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[32993289]
NPO21139 Daphniphyllum calycinum Species Daphniphyllaceae Eukaryota n.a. leaf n.a. PMID[9599286]
NPO28268 Enhydra fluctuans Species Mustelidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14541 Isodon oresbia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8333 Isodon trichocarpa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21482 Crotalaria laburnifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16019 Isodon japonica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14541 Isodon oresbia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16019 Isodon japonica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8333 Isodon trichocarpa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21482 Crotalaria laburnifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28268 Enhydra fluctuans Species Mustelidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21139 Daphniphyllum calycinum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26123 Isodon serra Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31425 Lsodon oresbia n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31127 Lsodon japonica n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21482 Crotalaria laburnifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21614 Urceolaria scruposa Species Trichodinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17240 Crematogaster brevis Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17508 Danae racemosa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19768 Xylosalsola arbuscula Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20115 Melampodium argophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19475 Isodon sculponeatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19889 Cereus stellatus Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20336 Arctotheca calendula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26123 Isodon serra Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19763 Meloidogyne incognita Species Meloidogynidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8991 Carcinus maenas Species Carcinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20470 Elaeagnus orientalis Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16409 Quercus pedunculata Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1558 Ozothamnus obcordatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16021 Boletus bovinus Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21139 Daphniphyllum calycinum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20543 Psydrax livida Species Rubiaceae 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
NPT111 Cell Line K562 Homo sapiens IC50 = 1620.0 nM PMID[516836]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[516836]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 2020.0 nM PMID[516836]
NPT660 Cell Line SW480 Homo sapiens IC50 > 40000.0 nM PMID[516837]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 40000.0 nM PMID[516837]
NPT81 Cell Line A549 Homo sapiens IC50 > 40000.0 nM PMID[516837]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 40000.0 nM PMID[516837]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 40000.0 nM PMID[516837]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 14180.0 nM PMID[516838]
NPT515 Cell Line SGC-7901 Homo sapiens IC50 = 26230.0 nM PMID[516838]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 19520.0 nM PMID[516838]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 19350.0 nM PMID[516838]
NPT81 Cell Line A549 Homo sapiens IC50 = 12070.0 nM PMID[516838]
NPT111 Cell Line K562 Homo sapiens IC50 = 2760.0 nM PMID[516838]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 114.6 n.a. PMID[516835]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 33.6 n.a. PMID[516835]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 103.6 n.a. PMID[516835]
NPT2 Others Unspecified Ratio = 3.41 n.a. PMID[516835]
NPT2 Others Unspecified Ratio = 1.62 n.a. PMID[516835]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 186.0 n.a. PMID[516835]
NPT21742 CELL-LINE L02 Homo sapiens IC50 = 25470.0 nM PMID[516838]

☑ 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 NPC61071 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
0.9798 High Similarity NPC96333
0.9798 High Similarity NPC88833
0.9796 High Similarity NPC101842
0.951 High Similarity NPC98069
0.951 High Similarity NPC49730
0.95 High Similarity NPC164600
0.95 High Similarity NPC103172
0.9412 High Similarity NPC469983
0.9314 High Similarity NPC232133
0.9208 High Similarity NPC244247
0.9192 High Similarity NPC267921
0.9118 High Similarity NPC285927
0.9109 High Similarity NPC139347
0.91 High Similarity NPC236585
0.9091 High Similarity NPC474793
0.8952 High Similarity NPC255655
0.8952 High Similarity NPC124053
0.8922 High Similarity NPC96217
0.8911 High Similarity NPC148279
0.8911 High Similarity NPC46848
0.8911 High Similarity NPC14634
0.8868 High Similarity NPC329953
0.8857 High Similarity NPC471250
0.8846 High Similarity NPC469746
0.8835 High Similarity NPC202793
0.8835 High Similarity NPC13149
0.8824 High Similarity NPC275990
0.8788 High Similarity NPC470232
0.8774 High Similarity NPC98633
0.8774 High Similarity NPC85391
0.8774 High Similarity NPC130302
0.8762 High Similarity NPC469733
0.8762 High Similarity NPC473410
0.8762 High Similarity NPC471094
0.8762 High Similarity NPC469984
0.8762 High Similarity NPC469729
0.8762 High Similarity NPC63841
0.875 High Similarity NPC12823
0.8725 High Similarity NPC471790
0.8713 High Similarity NPC89099
0.8713 High Similarity NPC38296
0.8713 High Similarity NPC162459
0.8713 High Similarity NPC26270
0.8713 High Similarity NPC38471
0.8713 High Similarity NPC20479
0.8713 High Similarity NPC98837
0.8713 High Similarity NPC471038
0.8713 High Similarity NPC28864
0.8704 High Similarity NPC285086
0.8704 High Similarity NPC132668
0.87 High Similarity NPC329910
0.87 High Similarity NPC193785
0.8692 High Similarity NPC471251
0.8687 High Similarity NPC475118
0.8687 High Similarity NPC41649
0.8687 High Similarity NPC470385
0.8687 High Similarity NPC470386
0.8679 High Similarity NPC469744
0.8667 High Similarity NPC186054
0.8667 High Similarity NPC471474
0.8641 High Similarity NPC475803
0.8641 High Similarity NPC214946
0.8641 High Similarity NPC286519
0.8641 High Similarity NPC148628
0.8641 High Similarity NPC88203
0.8641 High Similarity NPC76866
0.8641 High Similarity NPC304832
0.8641 High Similarity NPC309388
0.8641 High Similarity NPC246736
0.8627 High Similarity NPC293866
0.8614 High Similarity NPC10864
0.86 High Similarity NPC470229
0.8598 High Similarity NPC473324
0.8598 High Similarity NPC320383
0.8598 High Similarity NPC137104
0.8598 High Similarity NPC474786
0.8598 High Similarity NPC471093
0.8598 High Similarity NPC471476
0.8571 High Similarity NPC200957
0.8571 High Similarity NPC138908
0.8571 High Similarity NPC307660
0.8571 High Similarity NPC4115
0.8571 High Similarity NPC130511
0.8571 High Similarity NPC56656
0.8558 High Similarity NPC87927
0.8545 High Similarity NPC229752
0.8545 High Similarity NPC88945
0.8544 High Similarity NPC39683
0.8544 High Similarity NPC289148
0.8544 High Similarity NPC52899
0.8544 High Similarity NPC163963
0.8519 High Similarity NPC29505
0.8519 High Similarity NPC122339
0.8519 High Similarity NPC213320
0.8519 High Similarity NPC63244
0.8515 High Similarity NPC470387
0.8515 High Similarity NPC29410
0.8515 High Similarity NPC200054
0.8505 High Similarity NPC102741
0.8505 High Similarity NPC131903
0.8505 High Similarity NPC274827
0.85 High Similarity NPC47853
0.8491 Intermediate Similarity NPC166993
0.8491 Intermediate Similarity NPC201908
0.8491 Intermediate Similarity NPC176949
0.8485 Intermediate Similarity NPC198242
0.8485 Intermediate Similarity NPC211403
0.8476 Intermediate Similarity NPC84928
0.8476 Intermediate Similarity NPC474558
0.8468 Intermediate Similarity NPC473304
0.8468 Intermediate Similarity NPC78836
0.8462 Intermediate Similarity NPC124544
0.8447 Intermediate Similarity NPC470388
0.8447 Intermediate Similarity NPC287676
0.844 Intermediate Similarity NPC471244
0.844 Intermediate Similarity NPC473352
0.844 Intermediate Similarity NPC473303
0.844 Intermediate Similarity NPC471245
0.844 Intermediate Similarity NPC473397
0.844 Intermediate Similarity NPC474927
0.8431 Intermediate Similarity NPC96839
0.8431 Intermediate Similarity NPC253586
0.8426 Intermediate Similarity NPC42776
0.8416 Intermediate Similarity NPC98639
0.8411 Intermediate Similarity NPC112895
0.8411 Intermediate Similarity NPC273155
0.8411 Intermediate Similarity NPC189663
0.8411 Intermediate Similarity NPC55973
0.8411 Intermediate Similarity NPC469845
0.8411 Intermediate Similarity NPC89860
0.8411 Intermediate Similarity NPC231278
0.8411 Intermediate Similarity NPC218123
0.8381 Intermediate Similarity NPC122811
0.8381 Intermediate Similarity NPC277074
0.8381 Intermediate Similarity NPC216114
0.8381 Intermediate Similarity NPC209298
0.8367 Intermediate Similarity NPC56413
0.8364 Intermediate Similarity NPC471252
0.8364 Intermediate Similarity NPC73986
0.8364 Intermediate Similarity NPC94141
0.835 Intermediate Similarity NPC78427
0.835 Intermediate Similarity NPC16911
0.8349 Intermediate Similarity NPC270586
0.8349 Intermediate Similarity NPC272242
0.8333 Intermediate Similarity NPC252679
0.8333 Intermediate Similarity NPC118721
0.8333 Intermediate Similarity NPC13949
0.8318 Intermediate Similarity NPC471461
0.8318 Intermediate Similarity NPC67745
0.8302 Intermediate Similarity NPC301787
0.8302 Intermediate Similarity NPC98603
0.8302 Intermediate Similarity NPC88469
0.83 Intermediate Similarity NPC250753
0.83 Intermediate Similarity NPC470230
0.8288 Intermediate Similarity NPC243354
0.8288 Intermediate Similarity NPC17165
0.8273 Intermediate Similarity NPC145625
0.8273 Intermediate Similarity NPC157929
0.8269 Intermediate Similarity NPC108371
0.8269 Intermediate Similarity NPC94906
0.8224 Intermediate Similarity NPC295366
0.8224 Intermediate Similarity NPC37600
0.8224 Intermediate Similarity NPC222833
0.8218 Intermediate Similarity NPC294263
0.8208 Intermediate Similarity NPC159442
0.8198 Intermediate Similarity NPC194273
0.8198 Intermediate Similarity NPC102619
0.819 Intermediate Similarity NPC252614
0.819 Intermediate Similarity NPC253886
0.819 Intermediate Similarity NPC121218
0.819 Intermediate Similarity NPC71706
0.8182 Intermediate Similarity NPC471243
0.8173 Intermediate Similarity NPC472028
0.8137 Intermediate Similarity NPC29247
0.8137 Intermediate Similarity NPC129004
0.8137 Intermediate Similarity NPC101233
0.8137 Intermediate Similarity NPC289539
0.8137 Intermediate Similarity NPC153775
0.8137 Intermediate Similarity NPC91772
0.8137 Intermediate Similarity NPC111524
0.8137 Intermediate Similarity NPC261333
0.8137 Intermediate Similarity NPC292374
0.8137 Intermediate Similarity NPC215271
0.8137 Intermediate Similarity NPC104371
0.8131 Intermediate Similarity NPC96268
0.8119 Intermediate Similarity NPC476934
0.8113 Intermediate Similarity NPC164551
0.8113 Intermediate Similarity NPC170615
0.8108 Intermediate Similarity NPC476964
0.81 Intermediate Similarity NPC471043
0.81 Intermediate Similarity NPC200580
0.8095 Intermediate Similarity NPC180733
0.8095 Intermediate Similarity NPC41971
0.8095 Intermediate Similarity NPC293890
0.8095 Intermediate Similarity NPC37047
0.8081 Intermediate Similarity NPC259009
0.8077 Intermediate Similarity NPC111187
0.8077 Intermediate Similarity NPC469810
0.8077 Intermediate Similarity NPC190080
0.8073 Intermediate Similarity NPC224414

  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 NPC61071 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
0.7949 Intermediate Similarity NPD6370 Approved
0.7917 Intermediate Similarity NPD7736 Approved
0.7833 Intermediate Similarity NPD8293 Discontinued
0.7815 Intermediate Similarity NPD7492 Approved
0.7778 Intermediate Similarity NPD6054 Approved
0.775 Intermediate Similarity NPD6616 Approved
0.7712 Intermediate Similarity NPD6016 Approved
0.7712 Intermediate Similarity NPD6015 Approved
0.7705 Intermediate Similarity NPD7319 Approved
0.7686 Intermediate Similarity NPD7078 Approved
0.7647 Intermediate Similarity NPD5988 Approved
0.7627 Intermediate Similarity NPD6059 Approved
0.75 Intermediate Similarity NPD5697 Approved
0.7479 Intermediate Similarity NPD6319 Approved
0.7478 Intermediate Similarity NPD6882 Approved
0.7459 Intermediate Similarity NPD7507 Approved
0.7438 Intermediate Similarity NPD8328 Phase 3
0.7434 Intermediate Similarity NPD6881 Approved
0.7434 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD7320 Approved
0.7434 Intermediate Similarity NPD6899 Approved
0.7414 Intermediate Similarity NPD8133 Approved
0.7411 Intermediate Similarity NPD6008 Approved
0.7411 Intermediate Similarity NPD7128 Approved
0.7411 Intermediate Similarity NPD5739 Approved
0.7411 Intermediate Similarity NPD6675 Approved
0.7411 Intermediate Similarity NPD6402 Approved
0.7373 Intermediate Similarity NPD6009 Approved
0.7368 Intermediate Similarity NPD6013 Approved
0.7368 Intermediate Similarity NPD6012 Approved
0.7368 Intermediate Similarity NPD6014 Approved
0.7345 Intermediate Similarity NPD6412 Phase 2
0.7345 Intermediate Similarity NPD5701 Approved
0.7304 Intermediate Similarity NPD7102 Approved
0.7304 Intermediate Similarity NPD7290 Approved
0.7304 Intermediate Similarity NPD6883 Approved
0.7281 Intermediate Similarity NPD6011 Approved
0.7281 Intermediate Similarity NPD6686 Approved
0.7265 Intermediate Similarity NPD4632 Approved
0.7264 Intermediate Similarity NPD8034 Phase 2
0.7264 Intermediate Similarity NPD8035 Phase 2
0.7241 Intermediate Similarity NPD8130 Phase 1
0.7241 Intermediate Similarity NPD6847 Approved
0.7241 Intermediate Similarity NPD6650 Approved
0.7241 Intermediate Similarity NPD6649 Approved
0.7241 Intermediate Similarity NPD6869 Approved
0.7241 Intermediate Similarity NPD6617 Approved
0.7227 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD6372 Approved
0.7217 Intermediate Similarity NPD6373 Approved
0.7184 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD8297 Approved
0.7168 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD4634 Approved
0.7117 Intermediate Similarity NPD5285 Approved
0.7117 Intermediate Similarity NPD4696 Approved
0.7117 Intermediate Similarity NPD5286 Approved
0.7103 Intermediate Similarity NPD6079 Approved
0.7091 Intermediate Similarity NPD4755 Approved
0.7075 Intermediate Similarity NPD5328 Approved
0.7063 Intermediate Similarity NPD6033 Approved
0.7037 Intermediate Similarity NPD6399 Phase 3
0.7027 Intermediate Similarity NPD7638 Approved
0.7025 Intermediate Similarity NPD7327 Approved
0.7025 Intermediate Similarity NPD7328 Approved
0.7 Intermediate Similarity NPD5222 Approved
0.7 Intermediate Similarity NPD6274 Approved
0.7 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5221 Approved
0.6992 Remote Similarity NPD5983 Phase 2
0.6991 Remote Similarity NPD4633 Approved
0.6991 Remote Similarity NPD5224 Approved
0.6991 Remote Similarity NPD5226 Approved
0.6991 Remote Similarity NPD5211 Phase 2
0.6991 Remote Similarity NPD5225 Approved
0.6967 Remote Similarity NPD7516 Approved
0.6964 Remote Similarity NPD4700 Approved
0.6964 Remote Similarity NPD7640 Approved
0.6964 Remote Similarity NPD7639 Approved
0.6949 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6937 Remote Similarity NPD5173 Approved
0.693 Remote Similarity NPD5175 Approved
0.693 Remote Similarity NPD5174 Approved
0.6903 Remote Similarity NPD5223 Approved
0.688 Remote Similarity NPD6067 Discontinued
0.688 Remote Similarity NPD7604 Phase 2
0.687 Remote Similarity NPD5141 Approved
0.6855 Remote Similarity NPD8378 Approved
0.6855 Remote Similarity NPD8335 Approved
0.6855 Remote Similarity NPD8380 Approved
0.6855 Remote Similarity NPD8379 Approved
0.6855 Remote Similarity NPD8296 Approved
0.6855 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6847 Remote Similarity NPD4697 Phase 3
0.6832 Remote Similarity NPD6697 Approved
0.6832 Remote Similarity NPD6118 Approved
0.6832 Remote Similarity NPD6114 Approved
0.6832 Remote Similarity NPD6115 Approved
0.6829 Remote Similarity NPD7101 Approved
0.6829 Remote Similarity NPD7100 Approved
0.6818 Remote Similarity NPD7748 Approved
0.6803 Remote Similarity NPD6317 Approved
0.6803 Remote Similarity NPD7115 Discovery
0.6792 Remote Similarity NPD3618 Phase 1
0.6789 Remote Similarity NPD6411 Approved
0.6789 Remote Similarity NPD7515 Phase 2
0.6786 Remote Similarity NPD6084 Phase 2
0.6786 Remote Similarity NPD7902 Approved
0.6786 Remote Similarity NPD6083 Phase 2
0.678 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6774 Remote Similarity NPD8377 Approved
0.6774 Remote Similarity NPD8294 Approved
0.6772 Remote Similarity NPD6336 Discontinued
0.6748 Remote Similarity NPD6335 Approved
0.6748 Remote Similarity NPD6314 Approved
0.6748 Remote Similarity NPD6313 Approved
0.6733 Remote Similarity NPD6116 Phase 1
0.6729 Remote Similarity NPD3573 Approved
0.6727 Remote Similarity NPD4202 Approved
0.6726 Remote Similarity NPD4225 Approved
0.6721 Remote Similarity NPD6868 Approved
0.672 Remote Similarity NPD8033 Approved
0.672 Remote Similarity NPD6921 Approved
0.67 Remote Similarity NPD3703 Phase 2
0.6695 Remote Similarity NPD4729 Approved
0.6695 Remote Similarity NPD5128 Approved
0.6695 Remote Similarity NPD4730 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6667 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD4768 Approved
0.6638 Remote Similarity NPD4754 Approved
0.6634 Remote Similarity NPD6117 Approved
0.6609 Remote Similarity NPD1700 Approved
0.6607 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5695 Phase 3
0.6607 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6101 Approved
0.6606 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6604 Remote Similarity NPD4786 Approved
0.6593 Remote Similarity NPD6334 Approved
0.6593 Remote Similarity NPD6333 Approved
0.6587 Remote Similarity NPD7503 Approved
0.6587 Remote Similarity NPD8516 Approved
0.6587 Remote Similarity NPD6908 Approved
0.6587 Remote Similarity NPD8515 Approved
0.6587 Remote Similarity NPD8517 Approved
0.6587 Remote Similarity NPD6909 Approved
0.6587 Remote Similarity NPD8513 Phase 3
0.6583 Remote Similarity NPD5251 Approved
0.6583 Remote Similarity NPD5247 Approved
0.6583 Remote Similarity NPD5248 Approved
0.6583 Remote Similarity NPD5249 Phase 3
0.6583 Remote Similarity NPD5250 Approved
0.6583 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6579 Remote Similarity NPD5696 Approved
0.6571 Remote Similarity NPD3667 Approved
0.6565 Remote Similarity NPD5956 Approved
0.6552 Remote Similarity NPD7632 Discontinued
0.6529 Remote Similarity NPD5216 Approved
0.6529 Remote Similarity NPD5215 Approved
0.6529 Remote Similarity NPD5217 Approved
0.6518 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6518 Remote Similarity NPD5282 Discontinued
0.6518 Remote Similarity NPD7900 Approved
0.6514 Remote Similarity NPD6672 Approved
0.6514 Remote Similarity NPD6903 Approved
0.6514 Remote Similarity NPD5737 Approved
0.6486 Remote Similarity NPD7637 Suspended
0.6481 Remote Similarity NPD7521 Approved
0.6481 Remote Similarity NPD7334 Approved
0.6481 Remote Similarity NPD5330 Approved
0.6481 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6481 Remote Similarity NPD6409 Approved
0.6481 Remote Similarity NPD7146 Approved
0.6481 Remote Similarity NPD6684 Approved
0.6475 Remote Similarity NPD6053 Discontinued
0.6455 Remote Similarity NPD4753 Phase 2
0.6449 Remote Similarity NPD3133 Approved
0.6449 Remote Similarity NPD3666 Approved
0.6449 Remote Similarity NPD3665 Phase 1
0.6446 Remote Similarity NPD5135 Approved
0.6446 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6446 Remote Similarity NPD5169 Approved
0.6436 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5779 Approved
0.6429 Remote Similarity NPD5778 Approved
0.6417 Remote Similarity NPD5168 Approved
0.6393 Remote Similarity NPD5127 Approved
0.6381 Remote Similarity NPD6928 Phase 2
0.6373 Remote Similarity NPD3702 Approved
0.6372 Remote Similarity NPD6001 Approved
0.6364 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6343 Remote Similarity NPD8338 Approved
0.6333 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5210 Approved
0.6316 Remote Similarity NPD4629 Approved
0.6288 Remote Similarity NPD8336 Approved
0.6288 Remote Similarity NPD8337 Approved
0.6283 Remote Similarity NPD8171 Discontinued

  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