Structure

Physi-Chem Properties

Molecular Weight:  296.07
Volume:  297.142
LogP:  2.663
LogD:  2.033
LogS:  -3.712
# Rotatable Bonds:  2
TPSA:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.505
Synthetic Accessibility Score:  2.928
Fsp3:  0.059
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.886
MDCK Permeability:  1.941984191944357e-05
Pgp-inhibitor:  0.102
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.95
30% Bioavailability (F30%):  0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.043
Plasma Protein Binding (PPB):  92.6236801147461%
Volume Distribution (VD):  0.378
Pgp-substrate:  15.577815055847168%

ADMET: Metabolism

CYP1A2-inhibitor:  0.689
CYP1A2-substrate:  0.086
CYP2C19-inhibitor:  0.727
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.607
CYP2C9-substrate:  0.953
CYP2D6-inhibitor:  0.105
CYP2D6-substrate:  0.376
CYP3A4-inhibitor:  0.765
CYP3A4-substrate:  0.244

ADMET: Excretion

Clearance (CL):  7.047
Half-life (T1/2):  0.764

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.141
Drug-inuced Liver Injury (DILI):  0.711
AMES Toxicity:  0.137
Rat Oral Acute Toxicity:  0.373
Maximum Recommended Daily Dose:  0.194
Skin Sensitization:  0.585
Carcinogencity:  0.243
Eye Corrosion:  0.004
Eye Irritation:  0.125
Respiratory Toxicity:  0.149

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

  Natural Product: NPC311091

Natural Product ID:  NPC311091
Common Name*:   Aspulvinone E
IUPAC Name:   (5Z)-4-hydroxy-3-(4-hydroxyphenyl)-5-[(4-hydroxyphenyl)methylidene]furan-2-one
Synonyms:   Aspulvinone E
Standard InCHIKey:  BNNVVTQUWNGKPH-ZROIWOOFSA-N
Standard InCHI:  InChI=1S/C17H12O5/c18-12-5-1-10(2-6-12)9-14-16(20)15(17(21)22-14)11-3-7-13(19)8-4-11/h1-9,18-20H/b14-9-
SMILES:  c1cc(ccc1/C=C1/C(=C(c2ccc(cc2)O)C(=O)O1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2337339
PubChem CID:   54675753
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO33208 aspergillus terreus gwq-48 Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23411074]
NPO41081 Aspergillus sp. CPCC 400735 Strain Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[29016131]

☑ 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
NPT616 Cell Line MDCK Canis lupus familiaris CC50 > 250.0 ug.mL-1 PMID[524422]
NPT81 Cell Line A549 Homo sapiens CC50 > 250.0 ug.mL-1 PMID[524422]
NPT5403 Individual Protein Glucose-6-phosphate translocase Homo sapiens IC50 = 200000.0 nM PMID[524423]
NPT1453 Organism Influenza A virus (A/PR/8/34(H1N1)) Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 = 56.9 ug.mL-1 PMID[524422]
NPT2 Others Unspecified IC50 = 2700.0 nM PMID[524424]
NPT20648 PROTEIN FAMILY Alpha glucosidase Homo sapiens IC50 > 400000.0 nM PMID[524426]
NPT35 Others n.a. IC50 = 106000.0 nM PMID[524426]

☑ 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 NPC311091 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 NPC471033
0.9464 High Similarity NPC128249
0.9182 High Similarity NPC79543
0.9153 High Similarity NPC14141
0.9107 High Similarity NPC17693
0.9076 High Similarity NPC288945
0.9 High Similarity NPC156648
0.878 High Similarity NPC217431
0.875 High Similarity NPC281604
0.8707 High Similarity NPC296526
0.8689 High Similarity NPC88403
0.8596 High Similarity NPC183700
0.8571 High Similarity NPC264976
0.8571 High Similarity NPC70843
0.8547 High Similarity NPC51345
0.848 Intermediate Similarity NPC79332
0.8455 Intermediate Similarity NPC52472
0.8438 Intermediate Similarity NPC202743
0.8435 Intermediate Similarity NPC21162
0.8421 Intermediate Similarity NPC206341
0.8407 Intermediate Similarity NPC95178
0.8407 Intermediate Similarity NPC29989
0.8407 Intermediate Similarity NPC69332
0.8393 Intermediate Similarity NPC269644
0.8374 Intermediate Similarity NPC212541
0.8374 Intermediate Similarity NPC473942
0.8372 Intermediate Similarity NPC248150
0.8364 Intermediate Similarity NPC245561
0.8359 Intermediate Similarity NPC173034
0.8348 Intermediate Similarity NPC88141
0.8333 Intermediate Similarity NPC2596
0.8333 Intermediate Similarity NPC260952
0.8319 Intermediate Similarity NPC127676
0.8319 Intermediate Similarity NPC19290
0.8319 Intermediate Similarity NPC13495
0.8291 Intermediate Similarity NPC48525
0.8281 Intermediate Similarity NPC108553
0.8281 Intermediate Similarity NPC198388
0.8281 Intermediate Similarity NPC318799
0.8268 Intermediate Similarity NPC241354
0.8264 Intermediate Similarity NPC263386
0.8264 Intermediate Similarity NPC141791
0.8261 Intermediate Similarity NPC31274
0.8246 Intermediate Similarity NPC188677
0.8244 Intermediate Similarity NPC90431
0.823 Intermediate Similarity NPC8931
0.823 Intermediate Similarity NPC261573
0.823 Intermediate Similarity NPC120693
0.8217 Intermediate Similarity NPC25581
0.8217 Intermediate Similarity NPC5419
0.8217 Intermediate Similarity NPC61
0.8217 Intermediate Similarity NPC18074
0.8211 Intermediate Similarity NPC7830
0.8211 Intermediate Similarity NPC472271
0.8203 Intermediate Similarity NPC30390
0.819 Intermediate Similarity NPC234639
0.819 Intermediate Similarity NPC326187
0.8182 Intermediate Similarity NPC293424
0.8182 Intermediate Similarity NPC275519
0.8175 Intermediate Similarity NPC90128
0.8175 Intermediate Similarity NPC303680
0.8175 Intermediate Similarity NPC84076
0.8175 Intermediate Similarity NPC474476
0.8168 Intermediate Similarity NPC311742
0.8167 Intermediate Similarity NPC277394
0.8167 Intermediate Similarity NPC61062
0.8167 Intermediate Similarity NPC299252
0.816 Intermediate Similarity NPC89630
0.816 Intermediate Similarity NPC85565
0.8154 Intermediate Similarity NPC168799
0.8154 Intermediate Similarity NPC155209
0.8145 Intermediate Similarity NPC296202
0.8136 Intermediate Similarity NPC131530
0.813 Intermediate Similarity NPC470849
0.813 Intermediate Similarity NPC470848
0.8125 Intermediate Similarity NPC477300
0.8125 Intermediate Similarity NPC94810
0.8125 Intermediate Similarity NPC214246
0.812 Intermediate Similarity NPC116842
0.812 Intermediate Similarity NPC86087
0.812 Intermediate Similarity NPC284409
0.812 Intermediate Similarity NPC222084
0.811 Intermediate Similarity NPC123722
0.811 Intermediate Similarity NPC151167
0.811 Intermediate Similarity NPC276466
0.811 Intermediate Similarity NPC5018
0.811 Intermediate Similarity NPC123228
0.8106 Intermediate Similarity NPC471345
0.8103 Intermediate Similarity NPC17525
0.8099 Intermediate Similarity NPC325295
0.8099 Intermediate Similarity NPC76308
0.8095 Intermediate Similarity NPC280767
0.8095 Intermediate Similarity NPC197832
0.8095 Intermediate Similarity NPC137416
0.8092 Intermediate Similarity NPC300776
0.8092 Intermediate Similarity NPC176814
0.8092 Intermediate Similarity NPC5310
0.8092 Intermediate Similarity NPC4982
0.8092 Intermediate Similarity NPC68779
0.8083 Intermediate Similarity NPC23402
0.808 Intermediate Similarity NPC306100
0.808 Intermediate Similarity NPC285345
0.8067 Intermediate Similarity NPC148969
0.8065 Intermediate Similarity NPC194416
0.8065 Intermediate Similarity NPC177291
0.8065 Intermediate Similarity NPC147654
0.8051 Intermediate Similarity NPC474314
0.8051 Intermediate Similarity NPC158282
0.8049 Intermediate Similarity NPC233282
0.8047 Intermediate Similarity NPC167463
0.8045 Intermediate Similarity NPC62907
0.8036 Intermediate Similarity NPC280869
0.8033 Intermediate Similarity NPC94298
0.8033 Intermediate Similarity NPC27633
0.8031 Intermediate Similarity NPC120225
0.8031 Intermediate Similarity NPC179777
0.8031 Intermediate Similarity NPC213552
0.8017 Intermediate Similarity NPC141523
0.8017 Intermediate Similarity NPC131192
0.8016 Intermediate Similarity NPC213414
0.8 Intermediate Similarity NPC285350
0.8 Intermediate Similarity NPC139171
0.8 Intermediate Similarity NPC469927
0.8 Intermediate Similarity NPC68167
0.8 Intermediate Similarity NPC9218
0.7984 Intermediate Similarity NPC294361
0.7984 Intermediate Similarity NPC64111
0.7984 Intermediate Similarity NPC304622
0.7984 Intermediate Similarity NPC236520
0.7982 Intermediate Similarity NPC304638
0.7982 Intermediate Similarity NPC68269
0.7982 Intermediate Similarity NPC13426
0.797 Intermediate Similarity NPC223616
0.7966 Intermediate Similarity NPC63345
0.7965 Intermediate Similarity NPC253746
0.7955 Intermediate Similarity NPC106406
0.7953 Intermediate Similarity NPC3221
0.7953 Intermediate Similarity NPC4164
0.7953 Intermediate Similarity NPC257589
0.7953 Intermediate Similarity NPC53305
0.7953 Intermediate Similarity NPC289459
0.7953 Intermediate Similarity NPC67951
0.7951 Intermediate Similarity NPC65791
0.7946 Intermediate Similarity NPC260000
0.7941 Intermediate Similarity NPC182475
0.7939 Intermediate Similarity NPC307289
0.7939 Intermediate Similarity NPC302844
0.7939 Intermediate Similarity NPC76453
0.7937 Intermediate Similarity NPC236981
0.7934 Intermediate Similarity NPC322197
0.7934 Intermediate Similarity NPC4665
0.7931 Intermediate Similarity NPC1065
0.7926 Intermediate Similarity NPC191280
0.7926 Intermediate Similarity NPC289690
0.7926 Intermediate Similarity NPC288452
0.7923 Intermediate Similarity NPC285361
0.7923 Intermediate Similarity NPC66905
0.792 Intermediate Similarity NPC198336
0.7917 Intermediate Similarity NPC109241
0.791 Intermediate Similarity NPC279676
0.791 Intermediate Similarity NPC67349
0.7907 Intermediate Similarity NPC46192
0.7907 Intermediate Similarity NPC226661
0.7903 Intermediate Similarity NPC280827
0.7903 Intermediate Similarity NPC243059
0.7903 Intermediate Similarity NPC474874
0.7899 Intermediate Similarity NPC470355
0.7899 Intermediate Similarity NPC177576
0.7899 Intermediate Similarity NPC268388
0.7895 Intermediate Similarity NPC477301
0.7891 Intermediate Similarity NPC110211
0.7891 Intermediate Similarity NPC92207
0.7891 Intermediate Similarity NPC204579
0.7891 Intermediate Similarity NPC118584
0.7891 Intermediate Similarity NPC127937
0.7886 Intermediate Similarity NPC309434
0.7886 Intermediate Similarity NPC203124
0.7886 Intermediate Similarity NPC205502
0.7883 Intermediate Similarity NPC478250
0.7879 Intermediate Similarity NPC477281
0.7879 Intermediate Similarity NPC477280
0.7879 Intermediate Similarity NPC19719
0.7879 Intermediate Similarity NPC475468
0.7876 Intermediate Similarity NPC171843
0.7876 Intermediate Similarity NPC130193
0.7874 Intermediate Similarity NPC246704
0.7869 Intermediate Similarity NPC325646
0.7869 Intermediate Similarity NPC28951
0.7868 Intermediate Similarity NPC290664
0.7868 Intermediate Similarity NPC326065
0.7863 Intermediate Similarity NPC226699
0.7863 Intermediate Similarity NPC29883
0.7857 Intermediate Similarity NPC46634
0.7857 Intermediate Similarity NPC270654
0.7857 Intermediate Similarity NPC283514
0.7851 Intermediate Similarity NPC81808
0.7851 Intermediate Similarity NPC217472
0.7851 Intermediate Similarity NPC221870
0.7846 Intermediate Similarity NPC208536
0.7846 Intermediate Similarity NPC83062

  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 NPC311091 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
0.8293 Intermediate Similarity NPD1481 Phase 2
0.8211 Intermediate Similarity NPD1535 Discovery
0.8203 Intermediate Similarity NPD3764 Approved
0.8033 Intermediate Similarity NPD9545 Approved
0.8033 Intermediate Similarity NPD1894 Discontinued
0.8 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD1203 Approved
0.7923 Intermediate Similarity NPD6798 Discontinued
0.7879 Intermediate Similarity NPD6355 Discontinued
0.7863 Intermediate Similarity NPD4062 Phase 3
0.7863 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7863 Intermediate Similarity NPD6233 Phase 2
0.7812 Intermediate Similarity NPD2797 Approved
0.781 Intermediate Similarity NPD4628 Phase 3
0.777 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD9493 Approved
0.7698 Intermediate Similarity NPD3847 Discontinued
0.7679 Intermediate Similarity NPD2933 Approved
0.7679 Intermediate Similarity NPD2934 Approved
0.7656 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7652 Intermediate Similarity NPD3268 Approved
0.7647 Intermediate Similarity NPD2935 Discontinued
0.7626 Intermediate Similarity NPD2354 Approved
0.7623 Intermediate Similarity NPD1241 Discontinued
0.7611 Intermediate Similarity NPD2859 Approved
0.7611 Intermediate Similarity NPD2860 Approved
0.7607 Intermediate Similarity NPD5909 Discontinued
0.7597 Intermediate Similarity NPD1283 Approved
0.7597 Intermediate Similarity NPD3225 Approved
0.7578 Intermediate Similarity NPD9717 Approved
0.7578 Intermediate Similarity NPD1608 Approved
0.7576 Intermediate Similarity NPD7095 Approved
0.7574 Intermediate Similarity NPD2799 Discontinued
0.7563 Intermediate Similarity NPD1358 Approved
0.7554 Intermediate Similarity NPD3750 Approved
0.7541 Intermediate Similarity NPD5535 Approved
0.7538 Intermediate Similarity NPD1164 Approved
0.7519 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD2313 Discontinued
0.75 Intermediate Similarity NPD6190 Approved
0.75 Intermediate Similarity NPD2614 Approved
0.75 Intermediate Similarity NPD74 Approved
0.75 Intermediate Similarity NPD9266 Approved
0.7482 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD4308 Phase 3
0.7438 Intermediate Similarity NPD2067 Discontinued
0.7429 Intermediate Similarity NPD8166 Discontinued
0.7417 Intermediate Similarity NPD9263 Approved
0.7417 Intermediate Similarity NPD9267 Approved
0.7417 Intermediate Similarity NPD9264 Approved
0.7414 Intermediate Similarity NPD1238 Approved
0.7414 Intermediate Similarity NPD3020 Approved
0.741 Intermediate Similarity NPD5958 Discontinued
0.7407 Intermediate Similarity NPD4060 Phase 1
0.7405 Intermediate Similarity NPD3266 Approved
0.7405 Intermediate Similarity NPD3267 Approved
0.7394 Intermediate Similarity NPD6799 Approved
0.7379 Intermediate Similarity NPD3455 Phase 2
0.7368 Intermediate Similarity NPD6832 Phase 2
0.7364 Intermediate Similarity NPD422 Phase 1
0.7364 Intermediate Similarity NPD1281 Approved
0.736 Intermediate Similarity NPD256 Approved
0.736 Intermediate Similarity NPD255 Approved
0.7353 Intermediate Similarity NPD230 Phase 1
0.7353 Intermediate Similarity NPD4340 Discontinued
0.7348 Intermediate Similarity NPD5647 Approved
0.7344 Intermediate Similarity NPD17 Approved
0.7338 Intermediate Similarity NPD2344 Approved
0.7338 Intermediate Similarity NPD2353 Approved
0.7338 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3134 Approved
0.7328 Intermediate Similarity NPD9495 Approved
0.7328 Intermediate Similarity NPD1876 Approved
0.7324 Intermediate Similarity NPD7440 Discontinued
0.7308 Intermediate Similarity NPD3972 Approved
0.7302 Intermediate Similarity NPD9568 Approved
0.7295 Intermediate Similarity NPD3021 Approved
0.7295 Intermediate Similarity NPD3022 Approved
0.7293 Intermediate Similarity NPD9494 Approved
0.7292 Intermediate Similarity NPD5049 Phase 3
0.7286 Intermediate Similarity NPD4534 Discontinued
0.7281 Intermediate Similarity NPD1202 Approved
0.728 Intermediate Similarity NPD2629 Approved
0.7279 Intermediate Similarity NPD1240 Approved
0.7266 Intermediate Similarity NPD1537 Approved
0.7266 Intermediate Similarity NPD1538 Phase 1
0.7266 Intermediate Similarity NPD1551 Phase 2
0.7266 Intermediate Similarity NPD1519 Approved
0.7244 Intermediate Similarity NPD5536 Phase 2
0.7234 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD447 Suspended
0.7226 Intermediate Similarity NPD1933 Approved
0.7218 Intermediate Similarity NPD2798 Approved
0.7214 Intermediate Similarity NPD7266 Discontinued
0.7214 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD2684 Approved
0.7209 Intermediate Similarity NPD2932 Approved
0.7209 Intermediate Similarity NPD3019 Approved
0.7206 Intermediate Similarity NPD6663 Approved
0.7194 Intermediate Similarity NPD3748 Approved
0.7194 Intermediate Similarity NPD1510 Phase 2
0.719 Intermediate Similarity NPD968 Approved
0.7185 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD7003 Approved
0.7183 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD4110 Phase 3
0.7177 Intermediate Similarity NPD228 Approved
0.7176 Intermediate Similarity NPD9269 Phase 2
0.7174 Intermediate Similarity NPD1607 Approved
0.7168 Intermediate Similarity NPD9256 Approved
0.7168 Intermediate Similarity NPD9258 Approved
0.7165 Intermediate Similarity NPD694 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD5736 Approved
0.7164 Intermediate Similarity NPD454 Approved
0.7163 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD1549 Phase 2
0.7153 Intermediate Similarity NPD943 Approved
0.7153 Intermediate Similarity NPD2979 Phase 3
0.7153 Intermediate Similarity NPD4307 Phase 2
0.7153 Intermediate Similarity NPD1511 Approved
0.7152 Intermediate Similarity NPD7075 Discontinued
0.7143 Intermediate Similarity NPD1522 Approved
0.7143 Intermediate Similarity NPD4476 Approved
0.7143 Intermediate Similarity NPD2438 Suspended
0.7143 Intermediate Similarity NPD1501 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1523 Approved
0.7143 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD9281 Approved
0.7143 Intermediate Similarity NPD4477 Approved
0.7133 Intermediate Similarity NPD2309 Approved
0.7133 Intermediate Similarity NPD3887 Approved
0.7132 Intermediate Similarity NPD4105 Approved
0.7132 Intermediate Similarity NPD4102 Approved
0.7123 Intermediate Similarity NPD5403 Approved
0.7122 Intermediate Similarity NPD1536 Approved
0.712 Intermediate Similarity NPD7843 Approved
0.7107 Intermediate Similarity NPD9697 Approved
0.7103 Intermediate Similarity NPD5401 Approved
0.7099 Intermediate Similarity NPD1201 Approved
0.7099 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD4380 Phase 2
0.7095 Intermediate Similarity NPD6599 Discontinued
0.7092 Intermediate Similarity NPD2346 Discontinued
0.7092 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD257 Approved
0.709 Intermediate Similarity NPD258 Approved
0.7086 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD9261 Approved
0.7077 Intermediate Similarity NPD4626 Approved
0.7073 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD7033 Discontinued
0.7068 Intermediate Similarity NPD196 Phase 1
0.7067 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD1512 Approved
0.7055 Intermediate Similarity NPD6273 Approved
0.7054 Intermediate Similarity NPD1759 Phase 1
0.705 Intermediate Similarity NPD6653 Approved
0.7042 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD969 Suspended
0.7037 Intermediate Similarity NPD9569 Approved
0.7031 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD826 Approved
0.7029 Intermediate Similarity NPD825 Approved
0.7027 Intermediate Similarity NPD111 Approved
0.7025 Intermediate Similarity NPD1237 Approved
0.7023 Intermediate Similarity NPD4136 Approved
0.7023 Intermediate Similarity NPD4135 Approved
0.7023 Intermediate Similarity NPD3496 Discontinued
0.7023 Intermediate Similarity NPD4106 Approved
0.7021 Intermediate Similarity NPD5406 Approved
0.7021 Intermediate Similarity NPD5405 Approved
0.7021 Intermediate Similarity NPD5408 Approved
0.7021 Intermediate Similarity NPD2239 Approved
0.7021 Intermediate Similarity NPD5404 Approved
0.7021 Intermediate Similarity NPD2240 Approved
0.7015 Intermediate Similarity NPD1470 Approved
0.7015 Intermediate Similarity NPD987 Approved
0.7007 Intermediate Similarity NPD1296 Phase 2
0.7007 Intermediate Similarity NPD411 Approved
0.7 Intermediate Similarity NPD9491 Approved
0.7 Intermediate Similarity NPD1521 Approved
0.7 Intermediate Similarity NPD9268 Approved
0.7 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7097 Phase 1
0.7 Intermediate Similarity NPD1520 Approved
0.7 Intermediate Similarity NPD6801 Discontinued
0.7 Intermediate Similarity NPD5585 Approved
0.7 Intermediate Similarity NPD1934 Approved
0.7 Intermediate Similarity NPD1651 Approved
0.6986 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6978 Remote Similarity NPD555 Phase 2
0.6978 Remote Similarity NPD1184 Approved
0.6978 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6977 Remote Similarity NPD1758 Phase 1
0.6975 Remote Similarity NPD2066 Phase 3
0.6974 Remote Similarity NPD3882 Suspended
0.6963 Remote Similarity NPD6007 Clinical (unspecified phase)
0.696 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6959 Remote Similarity NPD2370 Clinical (unspecified phase)

  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