Structure

Physi-Chem Properties

Molecular Weight:  294.09
Volume:  305.648
LogP:  3.475
LogD:  2.953
LogS:  -3.786
# Rotatable Bonds:  3
TPSA:  55.76
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.882
Synthetic Accessibility Score:  2.369
Fsp3:  0.056
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:  -4.856
MDCK Permeability:  1.9200089809601195e-05
Pgp-inhibitor:  0.513
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.861
30% Bioavailability (F30%):  0.133

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.071
Plasma Protein Binding (PPB):  98.76143646240234%
Volume Distribution (VD):  0.446
Pgp-substrate:  1.5355528593063354%

ADMET: Metabolism

CYP1A2-inhibitor:  0.96
CYP1A2-substrate:  0.237
CYP2C19-inhibitor:  0.933
CYP2C19-substrate:  0.09
CYP2C9-inhibitor:  0.791
CYP2C9-substrate:  0.492
CYP2D6-inhibitor:  0.529
CYP2D6-substrate:  0.512
CYP3A4-inhibitor:  0.79
CYP3A4-substrate:  0.183

ADMET: Excretion

Clearance (CL):  5.377
Half-life (T1/2):  0.768

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.97
Drug-inuced Liver Injury (DILI):  0.874
AMES Toxicity:  0.915
Rat Oral Acute Toxicity:  0.692
Maximum Recommended Daily Dose:  0.385
Skin Sensitization:  0.834
Carcinogencity:  0.855
Eye Corrosion:  0.005
Eye Irritation:  0.039
Respiratory Toxicity:  0.222

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

  Natural Product: NPC296526

Natural Product ID:  NPC296526
Common Name*:   Rubrolide F
IUPAC Name:   (5Z)-4-(4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one
Synonyms:   Rubrolide F
Standard InCHIKey:  CNUDKAZLLHGKCY-YVLHZVERSA-N
Standard InCHI:  InChI=1S/C18H14O4/c1-21-15-8-2-12(3-9-15)10-17-16(11-18(20)22-17)13-4-6-14(19)7-5-13/h2-11,19H,1H3/b17-10-
SMILES:  COc1ccc(cc1)/C=C/1OC(=O)C=C1c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2152637
PubChem CID:   15071722
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002341] Phenol ethers
        • [CHEMONTID:0000138] Anisoles

*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
NPO33145 synoicum tunicate Species Polyclinidae Eukaryota n.a. South african n.a. PMID[23030848]

☑ 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 1006000.0 nM PMID[572900]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis IC50 = 79000.0 nM PMID[572900]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis GI = 47.0 % PMID[572900]
NPT19 Organism Escherichia coli Escherichia coli GI = 15.0 % PMID[572900]

☑ 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 NPC296526 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
0.9439 High Similarity NPC79543
0.9 High Similarity NPC183700
0.8991 High Similarity NPC206341
0.8917 High Similarity NPC78061
0.8917 High Similarity NPC122359
0.8917 High Similarity NPC159987
0.8889 High Similarity NPC127676
0.886 High Similarity NPC128249
0.8843 High Similarity NPC219923
0.8807 High Similarity NPC113457
0.8796 High Similarity NPC109637
0.8796 High Similarity NPC2518
0.8727 High Similarity NPC260952
0.8707 High Similarity NPC311091
0.8707 High Similarity NPC471033
0.8699 High Similarity NPC11449
0.8696 High Similarity NPC19290
0.8678 High Similarity NPC120225
0.8678 High Similarity NPC213552
0.8632 High Similarity NPC264976
0.8609 High Similarity NPC51345
0.8595 High Similarity NPC289459
0.8583 High Similarity NPC473942
0.8545 High Similarity NPC227255
0.8537 High Similarity NPC2596
0.8532 High Similarity NPC179686
0.8532 High Similarity NPC304638
0.8519 High Similarity NPC253746
0.8512 High Similarity NPC246704
0.8509 High Similarity NPC17693
0.8509 High Similarity NPC199462
0.8496 Intermediate Similarity NPC63345
0.8482 Intermediate Similarity NPC201959
0.8482 Intermediate Similarity NPC75440
0.8468 Intermediate Similarity NPC326447
0.8468 Intermediate Similarity NPC83062
0.8455 Intermediate Similarity NPC474603
0.8455 Intermediate Similarity NPC12987
0.843 Intermediate Similarity NPC14141
0.8426 Intermediate Similarity NPC171843
0.8417 Intermediate Similarity NPC251259
0.8417 Intermediate Similarity NPC7830
0.8407 Intermediate Similarity NPC234639
0.8407 Intermediate Similarity NPC474272
0.8403 Intermediate Similarity NPC2058
0.8393 Intermediate Similarity NPC151530
0.8393 Intermediate Similarity NPC157473
0.839 Intermediate Similarity NPC275519
0.839 Intermediate Similarity NPC293424
0.8378 Intermediate Similarity NPC128730
0.8378 Intermediate Similarity NPC473855
0.8378 Intermediate Similarity NPC288760
0.8374 Intermediate Similarity NPC474476
0.8362 Intermediate Similarity NPC235250
0.8361 Intermediate Similarity NPC89630
0.8361 Intermediate Similarity NPC20443
0.8361 Intermediate Similarity NPC146886
0.8361 Intermediate Similarity NPC60517
0.8347 Intermediate Similarity NPC296202
0.8333 Intermediate Similarity NPC470849
0.8333 Intermediate Similarity NPC473809
0.8333 Intermediate Similarity NPC470848
0.8333 Intermediate Similarity NPC131868
0.8319 Intermediate Similarity NPC263386
0.8319 Intermediate Similarity NPC141791
0.8305 Intermediate Similarity NPC263754
0.8305 Intermediate Similarity NPC183154
0.8304 Intermediate Similarity NPC176971
0.8293 Intermediate Similarity NPC168259
0.8288 Intermediate Similarity NPC283546
0.8279 Intermediate Similarity NPC212541
0.8276 Intermediate Similarity NPC141003
0.8276 Intermediate Similarity NPC35344
0.8273 Intermediate Similarity NPC307425
0.8264 Intermediate Similarity NPC187868
0.8264 Intermediate Similarity NPC52247
0.8261 Intermediate Similarity NPC139946
0.8257 Intermediate Similarity NPC100870
0.8254 Intermediate Similarity NPC32463
0.825 Intermediate Similarity NPC193193
0.825 Intermediate Similarity NPC202474
0.825 Intermediate Similarity NPC31314
0.8246 Intermediate Similarity NPC471954
0.8246 Intermediate Similarity NPC75272
0.824 Intermediate Similarity NPC478215
0.824 Intermediate Similarity NPC110313
0.8235 Intermediate Similarity NPC137537
0.8235 Intermediate Similarity NPC107588
0.8235 Intermediate Similarity NPC277460
0.8235 Intermediate Similarity NPC70744
0.8235 Intermediate Similarity NPC164706
0.8235 Intermediate Similarity NPC272471
0.822 Intermediate Similarity NPC33717
0.8214 Intermediate Similarity NPC470393
0.8214 Intermediate Similarity NPC238115
0.8211 Intermediate Similarity NPC213414
0.8211 Intermediate Similarity NPC288945
0.8205 Intermediate Similarity NPC294941
0.8189 Intermediate Similarity NPC250727
0.8182 Intermediate Similarity NPC269843
0.8182 Intermediate Similarity NPC109083
0.8182 Intermediate Similarity NPC60962
0.8182 Intermediate Similarity NPC224814
0.8182 Intermediate Similarity NPC189844
0.8182 Intermediate Similarity NPC14007
0.8182 Intermediate Similarity NPC204466
0.8182 Intermediate Similarity NPC107101
0.8174 Intermediate Similarity NPC25067
0.8174 Intermediate Similarity NPC141068
0.8174 Intermediate Similarity NPC88868
0.8174 Intermediate Similarity NPC231251
0.8165 Intermediate Similarity NPC175298
0.8158 Intermediate Similarity NPC291837
0.8154 Intermediate Similarity NPC90431
0.8154 Intermediate Similarity NPC223616
0.8151 Intermediate Similarity NPC280001
0.8151 Intermediate Similarity NPC122117
0.8145 Intermediate Similarity NPC88403
0.8145 Intermediate Similarity NPC4164
0.8142 Intermediate Similarity NPC135464
0.8142 Intermediate Similarity NPC92623
0.8142 Intermediate Similarity NPC1065
0.814 Intermediate Similarity NPC135127
0.8136 Intermediate Similarity NPC464
0.8136 Intermediate Similarity NPC185541
0.813 Intermediate Similarity NPC315807
0.8125 Intermediate Similarity NPC108875
0.8125 Intermediate Similarity NPC38079
0.812 Intermediate Similarity NPC109241
0.8115 Intermediate Similarity NPC70752
0.8115 Intermediate Similarity NPC147654
0.8108 Intermediate Similarity NPC94343
0.8108 Intermediate Similarity NPC300166
0.8103 Intermediate Similarity NPC266932
0.8099 Intermediate Similarity NPC474874
0.8095 Intermediate Similarity NPC217431
0.8091 Intermediate Similarity NPC130193
0.8083 Intermediate Similarity NPC124916
0.8083 Intermediate Similarity NPC470626
0.8083 Intermediate Similarity NPC309434
0.8083 Intermediate Similarity NPC203124
0.808 Intermediate Similarity NPC84076
0.808 Intermediate Similarity NPC303680
0.808 Intermediate Similarity NPC90128
0.8077 Intermediate Similarity NPC477301
0.8067 Intermediate Similarity NPC229147
0.8067 Intermediate Similarity NPC54507
0.8067 Intermediate Similarity NPC85292
0.8065 Intermediate Similarity NPC140521
0.8056 Intermediate Similarity NPC32977
0.8056 Intermediate Similarity NPC81010
0.8053 Intermediate Similarity NPC154899
0.8053 Intermediate Similarity NPC473393
0.8053 Intermediate Similarity NPC233396
0.8037 Intermediate Similarity NPC321956
0.8036 Intermediate Similarity NPC192596
0.8036 Intermediate Similarity NPC135784
0.8036 Intermediate Similarity NPC305205
0.8034 Intermediate Similarity NPC131530
0.8033 Intermediate Similarity NPC302107
0.8031 Intermediate Similarity NPC241354
0.8018 Intermediate Similarity NPC13755
0.8017 Intermediate Similarity NPC61779
0.8017 Intermediate Similarity NPC37858
0.8016 Intermediate Similarity NPC243688
0.8016 Intermediate Similarity NPC123722
0.8016 Intermediate Similarity NPC473993
0.8016 Intermediate Similarity NPC276466
0.8016 Intermediate Similarity NPC121740
0.8016 Intermediate Similarity NPC151167
0.8016 Intermediate Similarity NPC123228
0.8016 Intermediate Similarity NPC258567
0.8016 Intermediate Similarity NPC224774
0.8016 Intermediate Similarity NPC5018
0.8015 Intermediate Similarity NPC120852
0.8 Intermediate Similarity NPC68779
0.8 Intermediate Similarity NPC610
0.8 Intermediate Similarity NPC473054
0.8 Intermediate Similarity NPC87113
0.8 Intermediate Similarity NPC175799
0.8 Intermediate Similarity NPC249836
0.8 Intermediate Similarity NPC65791
0.8 Intermediate Similarity NPC280767
0.8 Intermediate Similarity NPC176814
0.8 Intermediate Similarity NPC5310
0.8 Intermediate Similarity NPC31274
0.8 Intermediate Similarity NPC200988
0.8 Intermediate Similarity NPC300776
0.8 Intermediate Similarity NPC201967
0.8 Intermediate Similarity NPC93219
0.8 Intermediate Similarity NPC293619
0.8 Intermediate Similarity NPC145023
0.8 Intermediate Similarity NPC67247
0.8 Intermediate Similarity NPC4982
0.8 Intermediate Similarity NPC244495
0.8 Intermediate Similarity NPC131950
0.8 Intermediate Similarity NPC474933
0.7984 Intermediate Similarity NPC106659
0.7984 Intermediate Similarity NPC245120
0.7984 Intermediate Similarity NPC18984

  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 NPC296526 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
0.8509 High Similarity NPD5535 Approved
0.8468 Intermediate Similarity NPD3134 Approved
0.8393 Intermediate Similarity NPD1358 Approved
0.8333 Intermediate Similarity NPD3847 Discontinued
0.8264 Intermediate Similarity NPD422 Phase 1
0.8264 Intermediate Similarity NPD1535 Discovery
0.8235 Intermediate Similarity NPD1894 Discontinued
0.8197 Intermediate Similarity NPD1481 Phase 2
0.8142 Intermediate Similarity NPD968 Approved
0.8099 Intermediate Similarity NPD4626 Approved
0.8056 Intermediate Similarity NPD2933 Approved
0.8056 Intermediate Similarity NPD2934 Approved
0.8033 Intermediate Similarity NPD3496 Discontinued
0.8 Intermediate Similarity NPD2797 Approved
0.7984 Intermediate Similarity NPD4060 Phase 1
0.7984 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7982 Intermediate Similarity NPD2860 Approved
0.7982 Intermediate Similarity NPD2859 Approved
0.792 Intermediate Similarity NPD3225 Approved
0.7895 Intermediate Similarity NPD9697 Approved
0.7869 Intermediate Similarity NPD5691 Approved
0.7857 Intermediate Similarity NPD1203 Approved
0.7845 Intermediate Similarity NPD2684 Approved
0.7829 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD3268 Approved
0.7829 Intermediate Similarity NPD6798 Discontinued
0.782 Intermediate Similarity NPD2935 Discontinued
0.7815 Intermediate Similarity NPD1241 Discontinued
0.7797 Intermediate Similarity NPD228 Approved
0.7787 Intermediate Similarity NPD1548 Phase 1
0.7787 Intermediate Similarity NPD9545 Approved
0.7786 Intermediate Similarity NPD6355 Discontinued
0.7786 Intermediate Similarity NPD4340 Discontinued
0.7778 Intermediate Similarity NPD1283 Approved
0.7778 Intermediate Similarity NPD5451 Approved
0.7769 Intermediate Similarity NPD6233 Phase 2
0.7769 Intermediate Similarity NPD4062 Phase 3
0.7768 Intermediate Similarity NPD3020 Approved
0.7752 Intermediate Similarity NPD7095 Approved
0.7752 Intermediate Similarity NPD5163 Phase 2
0.7731 Intermediate Similarity NPD7843 Approved
0.7705 Intermediate Similarity NPD5536 Phase 2
0.7698 Intermediate Similarity NPD6582 Phase 2
0.7698 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD6583 Phase 3
0.7692 Intermediate Similarity NPD3764 Approved
0.7681 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD5283 Phase 1
0.7647 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD1608 Approved
0.7619 Intermediate Similarity NPD9717 Approved
0.7612 Intermediate Similarity NPD2799 Discontinued
0.7591 Intermediate Similarity NPD4628 Phase 3
0.7583 Intermediate Similarity NPD821 Approved
0.7581 Intermediate Similarity NPD5585 Approved
0.7578 Intermediate Similarity NPD3266 Approved
0.7578 Intermediate Similarity NPD3267 Approved
0.7576 Intermediate Similarity NPD4140 Approved
0.7541 Intermediate Similarity NPD6671 Approved
0.7541 Intermediate Similarity NPD7157 Approved
0.754 Intermediate Similarity NPD1281 Approved
0.754 Intermediate Similarity NPD1610 Phase 2
0.7538 Intermediate Similarity NPD6832 Phase 2
0.7538 Intermediate Similarity NPD4908 Phase 1
0.7538 Intermediate Similarity NPD2614 Approved
0.7519 Intermediate Similarity NPD6584 Phase 3
0.75 Intermediate Similarity NPD1876 Approved
0.7481 Intermediate Similarity NPD7033 Discontinued
0.7481 Intermediate Similarity NPD4308 Phase 3
0.748 Intermediate Similarity NPD9493 Approved
0.748 Intermediate Similarity NPD3972 Approved
0.7464 Intermediate Similarity NPD3750 Approved
0.7462 Intermediate Similarity NPD2861 Phase 2
0.7458 Intermediate Similarity NPD290 Approved
0.7444 Intermediate Similarity NPD1240 Approved
0.7424 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD2313 Discontinued
0.7407 Intermediate Similarity NPD7097 Phase 1
0.7402 Intermediate Similarity NPD1611 Approved
0.7388 Intermediate Similarity NPD5124 Phase 1
0.7388 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD111 Approved
0.7381 Intermediate Similarity NPD1778 Approved
0.7381 Intermediate Similarity NPD6516 Phase 2
0.7381 Intermediate Similarity NPD2667 Approved
0.7381 Intermediate Similarity NPD2668 Approved
0.7381 Intermediate Similarity NPD5846 Approved
0.7381 Intermediate Similarity NPD17 Approved
0.7372 Intermediate Similarity NPD2344 Approved
0.7357 Intermediate Similarity NPD7440 Discontinued
0.7348 Intermediate Similarity NPD3027 Phase 3
0.7339 Intermediate Similarity NPD3596 Phase 2
0.7338 Intermediate Similarity NPD7003 Approved
0.7333 Intermediate Similarity NPD1607 Approved
0.7333 Intermediate Similarity NPD3021 Approved
0.7333 Intermediate Similarity NPD3022 Approved
0.7319 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD2979 Phase 3
0.7308 Intermediate Similarity NPD6362 Approved
0.7308 Intermediate Similarity NPD987 Approved
0.7302 Intermediate Similarity NPD1651 Approved
0.7299 Intermediate Similarity NPD4476 Approved
0.7299 Intermediate Similarity NPD1537 Approved
0.7299 Intermediate Similarity NPD1519 Approved
0.7299 Intermediate Similarity NPD1551 Phase 2
0.7299 Intermediate Similarity NPD4477 Approved
0.7299 Intermediate Similarity NPD1538 Phase 1
0.7293 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD3685 Discontinued
0.7287 Intermediate Similarity NPD4359 Approved
0.7286 Intermediate Similarity NPD2354 Approved
0.7273 Intermediate Similarity NPD9295 Approved
0.7273 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD709 Approved
0.7257 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD3536 Discontinued
0.7252 Intermediate Similarity NPD5647 Approved
0.7252 Intermediate Similarity NPD2798 Approved
0.7246 Intermediate Similarity NPD7266 Discontinued
0.7246 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD3028 Approved
0.7239 Intermediate Similarity NPD3058 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD5745 Approved
0.7231 Intermediate Similarity NPD196 Phase 1
0.7226 Intermediate Similarity NPD1510 Phase 2
0.7222 Intermediate Similarity NPD6581 Approved
0.7222 Intermediate Similarity NPD6580 Approved
0.7222 Intermediate Similarity NPD1182 Approved
0.7214 Intermediate Similarity NPD4110 Phase 3
0.7214 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD6653 Approved
0.7203 Intermediate Similarity NPD5909 Discontinued
0.7203 Intermediate Similarity NPD6273 Approved
0.72 Intermediate Similarity NPD694 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD454 Approved
0.7197 Intermediate Similarity NPD5736 Approved
0.7194 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD1549 Phase 2
0.7194 Intermediate Similarity NPD4534 Discontinued
0.7194 Intermediate Similarity NPD5958 Discontinued
0.7185 Intermediate Similarity NPD4307 Phase 2
0.7183 Intermediate Similarity NPD6799 Approved
0.7177 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD6032 Approved
0.7174 Intermediate Similarity NPD1523 Approved
0.7174 Intermediate Similarity NPD1522 Approved
0.7167 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD1357 Approved
0.7165 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD2309 Approved
0.7153 Intermediate Similarity NPD1536 Approved
0.7143 Intermediate Similarity NPD1652 Phase 2
0.7143 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD1933 Approved
0.7122 Intermediate Similarity NPD5865 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD5762 Approved
0.7122 Intermediate Similarity NPD2353 Approved
0.7122 Intermediate Similarity NPD2346 Discontinued
0.7122 Intermediate Similarity NPD6800 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD5763 Approved
0.7121 Intermediate Similarity NPD4624 Approved
0.712 Intermediate Similarity NPD2557 Approved
0.712 Intermediate Similarity NPD6387 Discontinued
0.7113 Intermediate Similarity NPD6666 Approved
0.7113 Intermediate Similarity NPD6667 Approved
0.7111 Intermediate Similarity NPD8032 Phase 2
0.7101 Intermediate Similarity NPD3748 Approved
0.7094 Intermediate Similarity NPD1242 Phase 1
0.7092 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD5746 Approved
0.708 Intermediate Similarity NPD3052 Approved
0.708 Intermediate Similarity NPD3054 Approved
0.7077 Intermediate Similarity NPD2232 Approved
0.7077 Intermediate Similarity NPD2230 Approved
0.7077 Intermediate Similarity NPD2235 Phase 2
0.7077 Intermediate Similarity NPD2233 Approved
0.7077 Intermediate Similarity NPD2231 Phase 2
0.7077 Intermediate Similarity NPD1840 Phase 2
0.7075 Intermediate Similarity NPD7411 Suspended
0.7073 Intermediate Similarity NPD969 Suspended
0.7071 Intermediate Similarity NPD2424 Discontinued
0.7068 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD9494 Approved
0.7059 Intermediate Similarity NPD1613 Approved
0.7059 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7458 Discontinued
0.705 Intermediate Similarity NPD2531 Phase 2
0.705 Intermediate Similarity NPD2438 Suspended
0.7042 Intermediate Similarity NPD3887 Approved
0.7037 Intermediate Similarity NPD1048 Approved
0.7037 Intermediate Similarity NPD411 Approved
0.7037 Intermediate Similarity NPD1296 Phase 2

  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