Structure

Physi-Chem Properties

Molecular Weight:  282.09
Volume:  290.988
LogP:  3.246
LogD:  3.194
LogS:  -3.349
# Rotatable Bonds:  3
TPSA:  73.83
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.685
Synthetic Accessibility Score:  2.404
Fsp3:  0.059
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.788
MDCK Permeability:  1.2249666724528652e-05
Pgp-inhibitor:  0.022
Pgp-substrate:  0.041
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.62
30% Bioavailability (F30%):  0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.05
Plasma Protein Binding (PPB):  99.73639678955078%
Volume Distribution (VD):  0.588
Pgp-substrate:  0.73110431432724%

ADMET: Metabolism

CYP1A2-inhibitor:  0.848
CYP1A2-substrate:  0.072
CYP2C19-inhibitor:  0.709
CYP2C19-substrate:  0.05
CYP2C9-inhibitor:  0.695
CYP2C9-substrate:  0.915
CYP2D6-inhibitor:  0.869
CYP2D6-substrate:  0.857
CYP3A4-inhibitor:  0.651
CYP3A4-substrate:  0.26

ADMET: Excretion

Clearance (CL):  13.808
Half-life (T1/2):  0.903

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.166
Drug-inuced Liver Injury (DILI):  0.921
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.47
Maximum Recommended Daily Dose:  0.021
Skin Sensitization:  0.26
Carcinogencity:  0.58
Eye Corrosion:  0.003
Eye Irritation:  0.283
Respiratory Toxicity:  0.078

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

  Natural Product: NPC128249

Natural Product ID:  NPC128249
Common Name*:   Eutypoid B
IUPAC Name:   4-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2H-furan-5-one
Synonyms:   Eutypoid B
Standard InCHIKey:  ULAOSFXVLZDDJW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H14O4/c18-14-5-1-11(2-6-14)9-13-10-21-17(20)16(13)12-3-7-15(19)8-4-12/h1-8,18-19H,9-10H2
SMILES:  c1cc(ccc1CC1=C(c2ccc(cc2)O)C(=O)OC1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1669585
PubChem CID:   50993749
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
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10479323]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12350167]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[14640527]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota Axinella verrucosa Mediterranean n.a. PMID[14738391]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15043411]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Sussex Inlet, New South Wales, Australia n.a. PMID[15104517]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15332862]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Berkeley Pit lake n.a. PMID[17970594]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. New Zealand n.a. PMID[19323568]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19326880]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20452770]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. North Sea n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Limonium tubiflorum n.a. PMID[21146414]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21916432]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22148349]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22458669]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23360521]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23477451]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23603293]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23972215]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24437979]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31433188]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9392888]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]

☑ 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
NPT591 Individual Protein Glycogen synthase kinase-3 beta Homo sapiens IC50 = 780.0 nM PMID[464230]

☑ 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 NPC128249 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
0.9464 High Similarity NPC311091
0.9464 High Similarity NPC471033
0.9273 High Similarity NPC17693
0.9231 High Similarity NPC288945
0.9174 High Similarity NPC79543
0.9091 High Similarity NPC183700
0.8983 High Similarity NPC14141
0.8926 High Similarity NPC79332
0.8909 High Similarity NPC206341
0.886 High Similarity NPC296526
0.8818 High Similarity NPC260952
0.8739 High Similarity NPC31274
0.8727 High Similarity NPC70843
0.8618 High Similarity NPC217431
0.8618 High Similarity NPC2596
0.8611 High Similarity NPC52472
0.8584 High Similarity NPC21162
0.8559 High Similarity NPC95178
0.8559 High Similarity NPC264976
0.8559 High Similarity NPC29989
0.8559 High Similarity NPC69332
0.8548 High Similarity NPC214246
0.8547 High Similarity NPC76308
0.8547 High Similarity NPC325295
0.8534 High Similarity NPC51345
0.8534 High Similarity NPC23402
0.8525 High Similarity NPC137416
0.8519 High Similarity NPC245561
0.8512 High Similarity NPC473942
0.8504 High Similarity NPC248150
0.8496 Intermediate Similarity NPC88141
0.8487 Intermediate Similarity NPC233282
0.8482 Intermediate Similarity NPC156648
0.8475 Intermediate Similarity NPC293424
0.8475 Intermediate Similarity NPC27633
0.8475 Intermediate Similarity NPC94298
0.8468 Intermediate Similarity NPC13495
0.8468 Intermediate Similarity NPC127676
0.8462 Intermediate Similarity NPC19290
0.8455 Intermediate Similarity NPC304638
0.8455 Intermediate Similarity NPC474476
0.8448 Intermediate Similarity NPC285350
0.8421 Intermediate Similarity NPC63345
0.8413 Intermediate Similarity NPC318799
0.8407 Intermediate Similarity NPC281604
0.8403 Intermediate Similarity NPC263386
0.8403 Intermediate Similarity NPC141791
0.8393 Intermediate Similarity NPC188677
0.8378 Intermediate Similarity NPC120693
0.8378 Intermediate Similarity NPC261573
0.8378 Intermediate Similarity NPC8931
0.8349 Intermediate Similarity NPC171843
0.8348 Intermediate Similarity NPC177576
0.8347 Intermediate Similarity NPC472271
0.8346 Intermediate Similarity NPC173034
0.8333 Intermediate Similarity NPC326187
0.8333 Intermediate Similarity NPC270654
0.8333 Intermediate Similarity NPC234639
0.8319 Intermediate Similarity NPC275519
0.8306 Intermediate Similarity NPC110211
0.8306 Intermediate Similarity NPC204579
0.8305 Intermediate Similarity NPC131192
0.8293 Intermediate Similarity NPC85565
0.8281 Intermediate Similarity NPC202743
0.8276 Intermediate Similarity NPC48525
0.8273 Intermediate Similarity NPC253746
0.8268 Intermediate Similarity NPC198388
0.8268 Intermediate Similarity NPC108553
0.8264 Intermediate Similarity NPC470848
0.8264 Intermediate Similarity NPC470849
0.8261 Intermediate Similarity NPC252544
0.8261 Intermediate Similarity NPC116842
0.8261 Intermediate Similarity NPC321252
0.8246 Intermediate Similarity NPC17525
0.8226 Intermediate Similarity NPC4164
0.8226 Intermediate Similarity NPC88403
0.8203 Intermediate Similarity NPC18074
0.8203 Intermediate Similarity NPC25581
0.8203 Intermediate Similarity NPC61
0.8203 Intermediate Similarity NPC5419
0.8197 Intermediate Similarity NPC147654
0.8197 Intermediate Similarity NPC7830
0.819 Intermediate Similarity NPC139946
0.8189 Intermediate Similarity NPC30390
0.8182 Intermediate Similarity NPC280869
0.8167 Intermediate Similarity NPC94637
0.8167 Intermediate Similarity NPC249435
0.8158 Intermediate Similarity NPC141523
0.8145 Intermediate Similarity NPC89630
0.8145 Intermediate Similarity NPC184219
0.814 Intermediate Similarity NPC168799
0.814 Intermediate Similarity NPC155209
0.8136 Intermediate Similarity NPC81808
0.813 Intermediate Similarity NPC68167
0.813 Intermediate Similarity NPC477151
0.813 Intermediate Similarity NPC296202
0.813 Intermediate Similarity NPC132518
0.8125 Intermediate Similarity NPC13426
0.8125 Intermediate Similarity NPC68269
0.811 Intermediate Similarity NPC194979
0.811 Intermediate Similarity NPC241354
0.8099 Intermediate Similarity NPC90522
0.8099 Intermediate Similarity NPC328459
0.8092 Intermediate Similarity NPC223616
0.8092 Intermediate Similarity NPC90431
0.8092 Intermediate Similarity NPC471345
0.8091 Intermediate Similarity NPC260000
0.8083 Intermediate Similarity NPC122117
0.808 Intermediate Similarity NPC49938
0.8077 Intermediate Similarity NPC106406
0.807 Intermediate Similarity NPC135464
0.807 Intermediate Similarity NPC92623
0.807 Intermediate Similarity NPC1065
0.8067 Intermediate Similarity NPC322197
0.8065 Intermediate Similarity NPC236981
0.8065 Intermediate Similarity NPC212541
0.8053 Intermediate Similarity NPC269644
0.8051 Intermediate Similarity NPC87069
0.8051 Intermediate Similarity NPC148969
0.8051 Intermediate Similarity NPC11824
0.8051 Intermediate Similarity NPC109241
0.8049 Intermediate Similarity NPC198336
0.8034 Intermediate Similarity NPC268388
0.8034 Intermediate Similarity NPC212718
0.8034 Intermediate Similarity NPC114682
0.8034 Intermediate Similarity NPC158282
0.8033 Intermediate Similarity NPC72977
0.8031 Intermediate Similarity NPC219923
0.8018 Intermediate Similarity NPC130193
0.8017 Intermediate Similarity NPC471954
0.8017 Intermediate Similarity NPC184527
0.8017 Intermediate Similarity NPC75272
0.8017 Intermediate Similarity NPC309434
0.8017 Intermediate Similarity NPC203124
0.8015 Intermediate Similarity NPC311742
0.8 Intermediate Similarity NPC128825
0.8 Intermediate Similarity NPC221798
0.8 Intermediate Similarity NPC29883
0.8 Intermediate Similarity NPC299252
0.8 Intermediate Similarity NPC61062
0.8 Intermediate Similarity NPC213414
0.8 Intermediate Similarity NPC325646
0.8 Intermediate Similarity NPC28951
0.8 Intermediate Similarity NPC226699
0.8 Intermediate Similarity NPC472591
0.8 Intermediate Similarity NPC277394
0.7985 Intermediate Similarity NPC9218
0.7984 Intermediate Similarity NPC283514
0.7984 Intermediate Similarity NPC69403
0.7984 Intermediate Similarity NPC469927
0.7984 Intermediate Similarity NPC291189
0.7984 Intermediate Similarity NPC67300
0.7982 Intermediate Similarity NPC154899
0.7982 Intermediate Similarity NPC233396
0.7982 Intermediate Similarity NPC32977
0.7982 Intermediate Similarity NPC81010
0.797 Intermediate Similarity NPC284409
0.7969 Intermediate Similarity NPC94810
0.7969 Intermediate Similarity NPC477300
0.7969 Intermediate Similarity NPC131684
0.7969 Intermediate Similarity NPC238309
0.7967 Intermediate Similarity NPC216216
0.7965 Intermediate Similarity NPC135784
0.7953 Intermediate Similarity NPC78061
0.7953 Intermediate Similarity NPC159987
0.7953 Intermediate Similarity NPC122359
0.7951 Intermediate Similarity NPC61779
0.7949 Intermediate Similarity NPC222084
0.7946 Intermediate Similarity NPC42211
0.7939 Intermediate Similarity NPC300776
0.7939 Intermediate Similarity NPC5310
0.7939 Intermediate Similarity NPC4982
0.7939 Intermediate Similarity NPC194970
0.7939 Intermediate Similarity NPC176814
0.7939 Intermediate Similarity NPC68779
0.7937 Intermediate Similarity NPC280767
0.7934 Intermediate Similarity NPC610
0.7934 Intermediate Similarity NPC65791
0.7934 Intermediate Similarity NPC145023
0.7934 Intermediate Similarity NPC200988
0.7934 Intermediate Similarity NPC175799
0.7934 Intermediate Similarity NPC45104
0.7931 Intermediate Similarity NPC317305
0.7928 Intermediate Similarity NPC201967
0.7923 Intermediate Similarity NPC327204
0.7923 Intermediate Similarity NPC323379
0.7923 Intermediate Similarity NPC307289
0.7923 Intermediate Similarity NPC76453
0.7923 Intermediate Similarity NPC302844
0.792 Intermediate Similarity NPC477152
0.7913 Intermediate Similarity NPC317592
0.7913 Intermediate Similarity NPC184658
0.7913 Intermediate Similarity NPC6984
0.791 Intermediate Similarity NPC19622
0.791 Intermediate Similarity NPC112789
0.7907 Intermediate Similarity NPC469929
0.7907 Intermediate Similarity NPC12694
0.7903 Intermediate Similarity NPC322332
0.7903 Intermediate Similarity NPC295034
0.7899 Intermediate Similarity NPC95381

  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 NPC128249 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
0.8475 Intermediate Similarity NPD9545 Approved
0.8333 Intermediate Similarity NPD3764 Approved
0.8319 Intermediate Similarity NPD1894 Discontinued
0.8279 Intermediate Similarity NPD1481 Phase 2
0.8197 Intermediate Similarity NPD1535 Discovery
0.8 Intermediate Similarity NPD9493 Approved
0.8 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD1203 Approved
0.7899 Intermediate Similarity NPD1241 Discontinued
0.7857 Intermediate Similarity NPD1238 Approved
0.7823 Intermediate Similarity NPD3847 Discontinued
0.7818 Intermediate Similarity NPD2933 Approved
0.7818 Intermediate Similarity NPD2934 Approved
0.7795 Intermediate Similarity NPD2797 Approved
0.7769 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD6798 Discontinued
0.7761 Intermediate Similarity NPD2935 Discontinued
0.7748 Intermediate Similarity NPD2859 Approved
0.7748 Intermediate Similarity NPD2860 Approved
0.7727 Intermediate Similarity NPD6355 Discontinued
0.7721 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD1283 Approved
0.771 Intermediate Similarity NPD4062 Phase 3
0.771 Intermediate Similarity NPD6233 Phase 2
0.7664 Intermediate Similarity NPD4628 Phase 3
0.7656 Intermediate Similarity NPD1164 Approved
0.7634 Intermediate Similarity NPD3268 Approved
0.7627 Intermediate Similarity NPD9266 Approved
0.7627 Intermediate Similarity NPD74 Approved
0.7626 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD6832 Phase 2
0.7607 Intermediate Similarity NPD3134 Approved
0.7586 Intermediate Similarity NPD5909 Discontinued
0.7578 Intermediate Similarity NPD3225 Approved
0.7576 Intermediate Similarity NPD6663 Approved
0.7559 Intermediate Similarity NPD1608 Approved
0.7559 Intermediate Similarity NPD9717 Approved
0.7556 Intermediate Similarity NPD2799 Discontinued
0.7554 Intermediate Similarity NPD7440 Discontinued
0.7544 Intermediate Similarity NPD3020 Approved
0.7542 Intermediate Similarity NPD9264 Approved
0.7542 Intermediate Similarity NPD1358 Approved
0.7542 Intermediate Similarity NPD9267 Approved
0.7542 Intermediate Similarity NPD9263 Approved
0.7541 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD5736 Approved
0.7536 Intermediate Similarity NPD8166 Discontinued
0.7536 Intermediate Similarity NPD3750 Approved
0.7521 Intermediate Similarity NPD5535 Approved
0.75 Intermediate Similarity NPD1551 Phase 2
0.75 Intermediate Similarity NPD2313 Discontinued
0.7482 Intermediate Similarity NPD6190 Approved
0.7481 Intermediate Similarity NPD2614 Approved
0.748 Intermediate Similarity NPD1281 Approved
0.748 Intermediate Similarity NPD256 Approved
0.748 Intermediate Similarity NPD255 Approved
0.7464 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD230 Phase 1
0.7458 Intermediate Similarity NPD968 Approved
0.7456 Intermediate Similarity NPD9495 Approved
0.7445 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD1876 Approved
0.7436 Intermediate Similarity NPD1237 Approved
0.7426 Intermediate Similarity NPD4308 Phase 3
0.7426 Intermediate Similarity NPD1510 Phase 2
0.7422 Intermediate Similarity NPD3972 Approved
0.7419 Intermediate Similarity NPD9568 Approved
0.7417 Intermediate Similarity NPD2067 Discontinued
0.7411 Intermediate Similarity NPD1202 Approved
0.7405 Intermediate Similarity NPD454 Approved
0.7391 Intermediate Similarity NPD1549 Phase 2
0.7388 Intermediate Similarity NPD1240 Approved
0.7388 Intermediate Similarity NPD2979 Phase 3
0.7385 Intermediate Similarity NPD3267 Approved
0.7385 Intermediate Similarity NPD3266 Approved
0.7372 Intermediate Similarity NPD4477 Approved
0.7372 Intermediate Similarity NPD4476 Approved
0.7364 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD3455 Phase 2
0.7355 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD422 Phase 1
0.7344 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2182 Approved
0.7323 Intermediate Similarity NPD3019 Approved
0.7323 Intermediate Similarity NPD17 Approved
0.7323 Intermediate Similarity NPD2932 Approved
0.7319 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD2344 Approved
0.7313 Intermediate Similarity NPD520 Approved
0.7299 Intermediate Similarity NPD7033 Discontinued
0.7297 Intermediate Similarity NPD9258 Approved
0.7297 Intermediate Similarity NPD9256 Approved
0.7293 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD7003 Approved
0.7279 Intermediate Similarity NPD1607 Approved
0.7273 Intermediate Similarity NPD6273 Approved
0.7266 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD3496 Discontinued
0.7266 Intermediate Similarity NPD5958 Discontinued
0.7259 Intermediate Similarity NPD4060 Phase 1
0.7258 Intermediate Similarity NPD2629 Approved
0.7258 Intermediate Similarity NPD9281 Approved
0.7254 Intermediate Similarity NPD6799 Approved
0.7246 Intermediate Similarity NPD1519 Approved
0.7246 Intermediate Similarity NPD1537 Approved
0.7246 Intermediate Similarity NPD1538 Phase 1
0.7244 Intermediate Similarity NPD5585 Approved
0.7234 Intermediate Similarity NPD2354 Approved
0.7222 Intermediate Similarity NPD2347 Approved
0.7209 Intermediate Similarity NPD1201 Approved
0.7206 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD4340 Discontinued
0.7203 Intermediate Similarity NPD9261 Approved
0.7203 Intermediate Similarity NPD6647 Phase 2
0.7197 Intermediate Similarity NPD2798 Approved
0.7197 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD5647 Approved
0.7194 Intermediate Similarity NPD7266 Discontinued
0.719 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4626 Approved
0.7176 Intermediate Similarity NPD196 Phase 1
0.7174 Intermediate Similarity NPD3748 Approved
0.7165 Intermediate Similarity NPD1548 Phase 1
0.7165 Intermediate Similarity NPD1759 Phase 1
0.7164 Intermediate Similarity NPD7095 Approved
0.7164 Intermediate Similarity NPD5163 Phase 2
0.7163 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD4110 Phase 3
0.7156 Intermediate Similarity NPD111 Approved
0.7143 Intermediate Similarity NPD164 Approved
0.7143 Intermediate Similarity NPD4534 Discontinued
0.7143 Intermediate Similarity NPD9494 Approved
0.7143 Intermediate Similarity NPD7411 Suspended
0.7143 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD4307 Phase 2
0.7132 Intermediate Similarity NPD826 Approved
0.7132 Intermediate Similarity NPD825 Approved
0.7131 Intermediate Similarity NPD3021 Approved
0.7131 Intermediate Similarity NPD3022 Approved
0.713 Intermediate Similarity NPD9491 Approved
0.713 Intermediate Similarity NPD1989 Approved
0.7123 Intermediate Similarity NPD7458 Discontinued
0.7122 Intermediate Similarity NPD1522 Approved
0.7122 Intermediate Similarity NPD5405 Approved
0.7122 Intermediate Similarity NPD2531 Phase 2
0.7122 Intermediate Similarity NPD2438 Suspended
0.7122 Intermediate Similarity NPD1523 Approved
0.7122 Intermediate Similarity NPD5406 Approved
0.7122 Intermediate Similarity NPD5404 Approved
0.7122 Intermediate Similarity NPD5408 Approved
0.7121 Intermediate Similarity NPD1470 Approved
0.7113 Intermediate Similarity NPD3887 Approved
0.7113 Intermediate Similarity NPD2309 Approved
0.7109 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD1651 Approved
0.7109 Intermediate Similarity NPD5691 Approved
0.7101 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1536 Approved
0.7094 Intermediate Similarity NPD2066 Phase 3
0.7087 Intermediate Similarity NPD5536 Phase 2
0.7087 Intermediate Similarity NPD1758 Phase 1
0.7083 Intermediate Similarity NPD9697 Approved
0.7083 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD1933 Approved
0.708 Intermediate Similarity NPD1239 Approved
0.708 Intermediate Similarity NPD555 Phase 2
0.7071 Intermediate Similarity NPD2346 Discontinued
0.7071 Intermediate Similarity NPD2353 Approved
0.7071 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD6800 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD1019 Discontinued
0.7067 Intermediate Similarity NPD7768 Phase 2
0.7059 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1929 Approved
0.7059 Intermediate Similarity NPD1930 Approved
0.7054 Intermediate Similarity NPD1778 Approved
0.7049 Intermediate Similarity NPD2684 Approved
0.7043 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD1242 Phase 1
0.7034 Intermediate Similarity NPD3028 Approved
0.7023 Intermediate Similarity NPD9269 Phase 2
0.702 Intermediate Similarity NPD7075 Discontinued
0.7016 Intermediate Similarity NPD969 Suspended
0.7008 Intermediate Similarity NPD694 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD943 Approved
0.7007 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1501 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4136 Approved
0.7 Intermediate Similarity NPD4106 Approved
0.7 Intermediate Similarity NPD4135 Approved
0.6992 Remote Similarity NPD6362 Approved
0.6986 Remote Similarity NPD5403 Approved
0.6985 Remote Similarity NPD1296 Phase 2
0.6985 Remote Similarity NPD411 Approved
0.6984 Remote Similarity NPD5951 Approved
0.6978 Remote Similarity NPD1520 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