Structure

Physi-Chem Properties

Molecular Weight:  390.2
Volume:  408.878
LogP:  2.929
LogD:  2.064
LogS:  -4.01
# Rotatable Bonds:  10
TPSA:  93.06
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.357
Synthetic Accessibility Score:  4.321
Fsp3:  0.545
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:  -4.677
MDCK Permeability:  2.6078932933160104e-05
Pgp-inhibitor:  0.996
Pgp-substrate:  0.013
Human Intestinal Absorption (HIA):  0.037
20% Bioavailability (F20%):  0.976
30% Bioavailability (F30%):  0.427

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.191
Plasma Protein Binding (PPB):  89.36800384521484%
Volume Distribution (VD):  2.599
Pgp-substrate:  9.58265209197998%

ADMET: Metabolism

CYP1A2-inhibitor:  0.977
CYP1A2-substrate:  0.686
CYP2C19-inhibitor:  0.831
CYP2C19-substrate:  0.799
CYP2C9-inhibitor:  0.654
CYP2C9-substrate:  0.05
CYP2D6-inhibitor:  0.318
CYP2D6-substrate:  0.011
CYP3A4-inhibitor:  0.95
CYP3A4-substrate:  0.802

ADMET: Excretion

Clearance (CL):  2.803
Half-life (T1/2):  0.783

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.446
Drug-inuced Liver Injury (DILI):  0.59
AMES Toxicity:  0.473
Rat Oral Acute Toxicity:  0.842
Maximum Recommended Daily Dose:  0.681
Skin Sensitization:  0.89
Carcinogencity:  0.921
Eye Corrosion:  0.003
Eye Irritation:  0.024
Respiratory Toxicity:  0.869

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

  Natural Product: NPC51345

Natural Product ID:  NPC51345
Common Name*:   Apteniol A
IUPAC Name:   3-[4-[4-(2-carboxyethyl)phenoxy]phenyl]propanoic acid
Synonyms:  
Standard InCHIKey:  UKCHMOVWJBXLBX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H18O5/c19-17(20)11-5-13-1-7-15(8-2-13)23-16-9-3-14(4-10-16)6-12-18(21)22/h1-4,7-10H,5-6,11-12H2,(H,19,20)(H,21,22)
SMILES:  c1cc(ccc1CCC(=O)O)Oc1ccc(cc1)CCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2269135
PubChem CID:   11645332
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0004155] Diphenylethers

*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
NPO6723 Globularia cordifolia Species Plantaginaceae Eukaryota n.a. leaf n.a. PMID[16124783]
NPO19574 Potentilla kleiniana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19574 Potentilla kleiniana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19574 Potentilla kleiniana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19574 Potentilla kleiniana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17765 Mycale parishi Species Mycalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14744 Lonchocarpus violaceus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6723 Globularia cordifolia Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19633 Polylepis racemosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18264 Campanula kemulariae Species Campanulaceae 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
NPT364 Organism Lactuca sativa Lactuca sativa Activity = 40.0 % PMID[450893]
NPT364 Organism Lactuca sativa Lactuca sativa Activity = 25.0 % PMID[450893]

☑ 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 NPC51345 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 NPC264976
0.8983 High Similarity NPC89630
0.8909 High Similarity NPC234639
0.8909 High Similarity NPC259554
0.877 High Similarity NPC241354
0.8718 High Similarity NPC474874
0.8707 High Similarity NPC293424
0.8696 High Similarity NPC19290
0.8636 High Similarity NPC1065
0.8609 High Similarity NPC296526
0.8596 High Similarity NPC109241
0.8584 High Similarity NPC233238
0.8583 High Similarity NPC473942
0.8547 High Similarity NPC471033
0.8547 High Similarity NPC311091
0.8545 High Similarity NPC473855
0.8537 High Similarity NPC2596
0.8534 High Similarity NPC128249
0.8525 High Similarity NPC474476
0.8443 Intermediate Similarity NPC88403
0.8443 Intermediate Similarity NPC3221
0.844 Intermediate Similarity NPC307425
0.8407 Intermediate Similarity NPC79543
0.84 Intermediate Similarity NPC2989
0.84 Intermediate Similarity NPC475102
0.839 Intermediate Similarity NPC205502
0.8387 Intermediate Similarity NPC226661
0.8378 Intermediate Similarity NPC473393
0.8378 Intermediate Similarity NPC470393
0.8376 Intermediate Similarity NPC33717
0.8364 Intermediate Similarity NPC298224
0.8361 Intermediate Similarity NPC221798
0.8349 Intermediate Similarity NPC107101
0.8333 Intermediate Similarity NPC183700
0.832 Intermediate Similarity NPC238309
0.8319 Intermediate Similarity NPC31274
0.8304 Intermediate Similarity NPC113457
0.8304 Intermediate Similarity NPC188677
0.8304 Intermediate Similarity NPC70843
0.8293 Intermediate Similarity NPC280767
0.8288 Intermediate Similarity NPC261573
0.8288 Intermediate Similarity NPC283546
0.8288 Intermediate Similarity NPC108875
0.8288 Intermediate Similarity NPC120693
0.8288 Intermediate Similarity NPC8931
0.8288 Intermediate Similarity NPC38079
0.8288 Intermediate Similarity NPC38209
0.8268 Intermediate Similarity NPC307289
0.8257 Intermediate Similarity NPC245561
0.825 Intermediate Similarity NPC31314
0.825 Intermediate Similarity NPC193193
0.8246 Intermediate Similarity NPC474272
0.823 Intermediate Similarity NPC151530
0.823 Intermediate Similarity NPC157473
0.822 Intermediate Similarity NPC470860
0.8211 Intermediate Similarity NPC111088
0.8211 Intermediate Similarity NPC229113
0.8205 Intermediate Similarity NPC235250
0.8197 Intermediate Similarity NPC69403
0.8197 Intermediate Similarity NPC291189
0.819 Intermediate Similarity NPC17693
0.8189 Intermediate Similarity NPC470392
0.8182 Intermediate Similarity NPC52472
0.8174 Intermediate Similarity NPC88868
0.8174 Intermediate Similarity NPC25067
0.8174 Intermediate Similarity NPC231251
0.8167 Intermediate Similarity NPC234956
0.816 Intermediate Similarity NPC223807
0.8158 Intermediate Similarity NPC206341
0.8158 Intermediate Similarity NPC291837
0.8154 Intermediate Similarity NPC223616
0.8151 Intermediate Similarity NPC469954
0.8151 Intermediate Similarity NPC263754
0.8151 Intermediate Similarity NPC183154
0.8145 Intermediate Similarity NPC257589
0.8145 Intermediate Similarity NPC53305
0.8142 Intermediate Similarity NPC29989
0.8142 Intermediate Similarity NPC95178
0.8142 Intermediate Similarity NPC176971
0.8142 Intermediate Similarity NPC69332
0.814 Intermediate Similarity NPC300776
0.814 Intermediate Similarity NPC5310
0.814 Intermediate Similarity NPC4982
0.814 Intermediate Similarity NPC176814
0.814 Intermediate Similarity NPC68779
0.8136 Intermediate Similarity NPC322358
0.813 Intermediate Similarity NPC14141
0.8125 Intermediate Similarity NPC109637
0.8115 Intermediate Similarity NPC194416
0.8115 Intermediate Similarity NPC177291
0.811 Intermediate Similarity NPC86774
0.811 Intermediate Similarity NPC327457
0.8106 Intermediate Similarity NPC71903
0.8087 Intermediate Similarity NPC88141
0.808 Intermediate Similarity NPC84076
0.808 Intermediate Similarity NPC303680
0.808 Intermediate Similarity NPC90128
0.808 Intermediate Similarity NPC127937
0.808 Intermediate Similarity NPC475236
0.808 Intermediate Similarity NPC92207
0.807 Intermediate Similarity NPC260952
0.8065 Intermediate Similarity NPC140521
0.8053 Intermediate Similarity NPC238115
0.8053 Intermediate Similarity NPC13495
0.8053 Intermediate Similarity NPC128730
0.8049 Intermediate Similarity NPC311219
0.8045 Intermediate Similarity NPC170812
0.8045 Intermediate Similarity NPC183642
0.8045 Intermediate Similarity NPC310370
0.8036 Intermediate Similarity NPC192596
0.8031 Intermediate Similarity NPC474289
0.8031 Intermediate Similarity NPC473019
0.8017 Intermediate Similarity NPC61779
0.8017 Intermediate Similarity NPC141068
0.8017 Intermediate Similarity NPC54243
0.8017 Intermediate Similarity NPC63345
0.8016 Intermediate Similarity NPC276466
0.8016 Intermediate Similarity NPC123722
0.8016 Intermediate Similarity NPC151167
0.8016 Intermediate Similarity NPC22783
0.8016 Intermediate Similarity NPC123228
0.8016 Intermediate Similarity NPC5018
0.8015 Intermediate Similarity NPC90431
0.8 Intermediate Similarity NPC86947
0.8 Intermediate Similarity NPC249836
0.8 Intermediate Similarity NPC325295
0.8 Intermediate Similarity NPC75440
0.8 Intermediate Similarity NPC201959
0.8 Intermediate Similarity NPC76308
0.8 Intermediate Similarity NPC168259
0.8 Intermediate Similarity NPC4164
0.8 Intermediate Similarity NPC45104
0.7984 Intermediate Similarity NPC279379
0.7984 Intermediate Similarity NPC93730
0.7984 Intermediate Similarity NPC470887
0.7982 Intermediate Similarity NPC326447
0.7969 Intermediate Similarity NPC32463
0.7969 Intermediate Similarity NPC109778
0.7967 Intermediate Similarity NPC472271
0.7965 Intermediate Similarity NPC2518
0.7955 Intermediate Similarity NPC317741
0.7955 Intermediate Similarity NPC471069
0.7955 Intermediate Similarity NPC282087
0.7955 Intermediate Similarity NPC241086
0.7955 Intermediate Similarity NPC318984
0.7955 Intermediate Similarity NPC328137
0.7955 Intermediate Similarity NPC259800
0.7955 Intermediate Similarity NPC318028
0.7955 Intermediate Similarity NPC471068
0.7953 Intermediate Similarity NPC2401
0.7951 Intermediate Similarity NPC168050
0.7949 Intermediate Similarity NPC266932
0.7949 Intermediate Similarity NPC177576
0.7946 Intermediate Similarity NPC51633
0.7939 Intermediate Similarity NPC61499
0.7939 Intermediate Similarity NPC113295
0.7937 Intermediate Similarity NPC179777
0.7937 Intermediate Similarity NPC213552
0.7937 Intermediate Similarity NPC120225
0.7934 Intermediate Similarity NPC32298
0.7934 Intermediate Similarity NPC159916
0.7928 Intermediate Similarity NPC100870
0.7923 Intermediate Similarity NPC287533
0.792 Intermediate Similarity NPC288945
0.792 Intermediate Similarity NPC78446
0.792 Intermediate Similarity NPC474237
0.792 Intermediate Similarity NPC193805
0.792 Intermediate Similarity NPC107846
0.791 Intermediate Similarity NPC155552
0.7899 Intermediate Similarity NPC114144
0.7895 Intermediate Similarity NPC471070
0.7895 Intermediate Similarity NPC73078
0.7895 Intermediate Similarity NPC319870
0.7895 Intermediate Similarity NPC148738
0.7895 Intermediate Similarity NPC284409
0.7895 Intermediate Similarity NPC327612
0.7895 Intermediate Similarity NPC265335
0.7895 Intermediate Similarity NPC8302
0.7895 Intermediate Similarity NPC127676
0.7895 Intermediate Similarity NPC471072
0.7895 Intermediate Similarity NPC471071
0.7895 Intermediate Similarity NPC139891
0.7891 Intermediate Similarity NPC304622
0.7881 Intermediate Similarity NPC199462
0.7879 Intermediate Similarity NPC246177
0.7879 Intermediate Similarity NPC317045
0.7876 Intermediate Similarity NPC179686
0.7874 Intermediate Similarity NPC161322
0.7874 Intermediate Similarity NPC95034
0.7874 Intermediate Similarity NPC142087
0.7874 Intermediate Similarity NPC121104
0.7874 Intermediate Similarity NPC37512
0.7869 Intermediate Similarity NPC35744
0.7868 Intermediate Similarity NPC160378
0.7868 Intermediate Similarity NPC473090
0.7863 Intermediate Similarity NPC21162
0.7863 Intermediate Similarity NPC321252
0.7863 Intermediate Similarity NPC252544
0.7863 Intermediate Similarity NPC473809
0.7863 Intermediate Similarity NPC34456

  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 NPC51345 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
0.9204 High Similarity NPD1894 Discontinued
0.9052 High Similarity NPD1535 Discovery
0.8974 High Similarity NPD1481 Phase 2
0.8839 High Similarity NPD5535 Approved
0.8699 High Similarity NPD6798 Discontinued
0.8699 High Similarity NPD6859 Clinical (unspecified phase)
0.8689 High Similarity NPD2614 Approved
0.8644 High Similarity NPD3847 Discontinued
0.8629 High Similarity NPD4062 Phase 3
0.8629 High Similarity NPD6233 Phase 2
0.8595 High Similarity NPD2797 Approved
0.85 High Similarity NPD1608 Approved
0.8492 Intermediate Similarity NPD6355 Discontinued
0.84 Intermediate Similarity NPD3268 Approved
0.832 Intermediate Similarity NPD7095 Approved
0.8295 Intermediate Similarity NPD2799 Discontinued
0.8293 Intermediate Similarity NPD1203 Approved
0.8276 Intermediate Similarity NPD1241 Discontinued
0.825 Intermediate Similarity NPD17 Approved
0.8211 Intermediate Similarity NPD1283 Approved
0.8211 Intermediate Similarity NPD3225 Approved
0.8167 Intermediate Similarity NPD5585 Approved
0.8145 Intermediate Similarity NPD3266 Approved
0.8145 Intermediate Similarity NPD3267 Approved
0.811 Intermediate Similarity NPD2313 Discontinued
0.8106 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD6832 Phase 2
0.8092 Intermediate Similarity NPD4476 Approved
0.8092 Intermediate Similarity NPD4477 Approved
0.8077 Intermediate Similarity NPD1536 Approved
0.8049 Intermediate Similarity NPD9717 Approved
0.8045 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8045 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.8031 Intermediate Similarity NPD5163 Phase 2
0.8016 Intermediate Similarity NPD454 Approved
0.8 Intermediate Similarity NPD2684 Approved
0.7985 Intermediate Similarity NPD4628 Phase 3
0.7982 Intermediate Similarity NPD3134 Approved
0.7982 Intermediate Similarity NPD968 Approved
0.797 Intermediate Similarity NPD5958 Discontinued
0.797 Intermediate Similarity NPD4534 Discontinued
0.7967 Intermediate Similarity NPD1281 Approved
0.7955 Intermediate Similarity NPD1538 Phase 1
0.7955 Intermediate Similarity NPD1519 Approved
0.7955 Intermediate Similarity NPD1537 Approved
0.7951 Intermediate Similarity NPD1778 Approved
0.7939 Intermediate Similarity NPD1521 Approved
0.7939 Intermediate Similarity NPD1520 Approved
0.7913 Intermediate Similarity NPD1358 Approved
0.7907 Intermediate Similarity NPD8032 Phase 2
0.7895 Intermediate Similarity NPD6800 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD9697 Approved
0.7881 Intermediate Similarity NPD7843 Approved
0.7879 Intermediate Similarity NPD7033 Discontinued
0.7879 Intermediate Similarity NPD4308 Phase 3
0.7869 Intermediate Similarity NPD1651 Approved
0.7868 Intermediate Similarity NPD7440 Discontinued
0.7852 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD4110 Phase 3
0.7852 Intermediate Similarity NPD3750 Approved
0.7846 Intermediate Similarity NPD4060 Phase 1
0.7846 Intermediate Similarity NPD2979 Phase 3
0.784 Intermediate Similarity NPD4359 Approved
0.7823 Intermediate Similarity NPD422 Phase 1
0.782 Intermediate Similarity NPD2935 Discontinued
0.782 Intermediate Similarity NPD1523 Approved
0.782 Intermediate Similarity NPD1522 Approved
0.7803 Intermediate Similarity NPD7097 Phase 1
0.7795 Intermediate Similarity NPD5647 Approved
0.7794 Intermediate Similarity NPD2354 Approved
0.7786 Intermediate Similarity NPD1184 Approved
0.7778 Intermediate Similarity NPD196 Phase 1
0.776 Intermediate Similarity NPD3972 Approved
0.7744 Intermediate Similarity NPD3748 Approved
0.7742 Intermediate Similarity NPD3496 Discontinued
0.7731 Intermediate Similarity NPD821 Approved
0.7727 Intermediate Similarity NPD2933 Approved
0.7727 Intermediate Similarity NPD2934 Approved
0.7717 Intermediate Similarity NPD6362 Approved
0.771 Intermediate Similarity NPD4307 Phase 2
0.7692 Intermediate Similarity NPD1296 Phase 2
0.7692 Intermediate Similarity NPD3764 Approved
0.7687 Intermediate Similarity NPD2239 Approved
0.7687 Intermediate Similarity NPD2240 Approved
0.7686 Intermediate Similarity NPD7157 Approved
0.7681 Intermediate Similarity NPD6799 Approved
0.768 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD6516 Phase 2
0.7661 Intermediate Similarity NPD5846 Approved
0.7658 Intermediate Similarity NPD2859 Approved
0.7658 Intermediate Similarity NPD2860 Approved
0.7656 Intermediate Similarity NPD2798 Approved
0.7652 Intermediate Similarity NPD4618 Approved
0.7652 Intermediate Similarity NPD4622 Approved
0.7652 Intermediate Similarity NPD4340 Discontinued
0.7642 Intermediate Similarity NPD9545 Approved
0.7642 Intermediate Similarity NPD1548 Phase 1
0.763 Intermediate Similarity NPD2346 Discontinued
0.763 Intermediate Similarity NPD2353 Approved
0.763 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD5451 Approved
0.7589 Intermediate Similarity NPD2370 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD987 Approved
0.7576 Intermediate Similarity NPD4140 Approved
0.7571 Intermediate Similarity NPD5049 Phase 3
0.7571 Intermediate Similarity NPD6273 Approved
0.7561 Intermediate Similarity NPD5536 Phase 2
0.7559 Intermediate Similarity NPD6582 Phase 2
0.7559 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7559 Intermediate Similarity NPD6583 Phase 3
0.7556 Intermediate Similarity NPD1551 Phase 2
0.7556 Intermediate Similarity NPD2531 Phase 2
0.7556 Intermediate Similarity NPD6032 Approved
0.7556 Intermediate Similarity NPD1501 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD2438 Suspended
0.7554 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7541 Intermediate Similarity NPD6671 Approved
0.754 Intermediate Similarity NPD1611 Approved
0.7537 Intermediate Similarity NPD5689 Approved
0.7537 Intermediate Similarity NPD5688 Approved
0.7536 Intermediate Similarity NPD3887 Approved
0.7521 Intermediate Similarity NPD5283 Phase 1
0.752 Intermediate Similarity NPD4626 Approved
0.7519 Intermediate Similarity NPD1933 Approved
0.7519 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD7427 Discontinued
0.75 Intermediate Similarity NPD4870 Approved
0.75 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2344 Approved
0.75 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1876 Approved
0.75 Intermediate Similarity NPD5909 Discontinued
0.7483 Intermediate Similarity NPD6502 Phase 2
0.748 Intermediate Similarity NPD3596 Phase 2
0.7464 Intermediate Similarity NPD7003 Approved
0.7463 Intermediate Similarity NPD6653 Approved
0.7458 Intermediate Similarity NPD290 Approved
0.7456 Intermediate Similarity NPD3020 Approved
0.7445 Intermediate Similarity NPD1549 Phase 2
0.744 Intermediate Similarity NPD5691 Approved
0.7431 Intermediate Similarity NPD7411 Suspended
0.7431 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD411 Approved
0.7422 Intermediate Similarity NPD3685 Discontinued
0.7405 Intermediate Similarity NPD4908 Phase 1
0.7402 Intermediate Similarity NPD1610 Phase 2
0.7394 Intermediate Similarity NPD8012 Clinical (unspecified phase)
0.7388 Intermediate Similarity NPD447 Suspended
0.7385 Intermediate Similarity NPD6584 Phase 3
0.7385 Intermediate Similarity NPD1019 Discontinued
0.7376 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD6002 Phase 3
0.7372 Intermediate Similarity NPD6005 Phase 3
0.7372 Intermediate Similarity NPD6004 Phase 3
0.7368 Intermediate Similarity NPD5745 Approved
0.7361 Intermediate Similarity NPD6599 Discontinued
0.736 Intermediate Similarity NPD6581 Approved
0.736 Intermediate Similarity NPD6580 Approved
0.7339 Intermediate Similarity NPD9493 Approved
0.7338 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD7819 Suspended
0.7329 Intermediate Similarity NPD8455 Phase 2
0.7329 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD2861 Phase 2
0.7319 Intermediate Similarity NPD2897 Discontinued
0.7313 Intermediate Similarity NPD3142 Approved
0.7313 Intermediate Similarity NPD1240 Approved
0.7313 Intermediate Similarity NPD3140 Approved
0.7311 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD1238 Approved
0.7302 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD2796 Approved
0.7299 Intermediate Similarity NPD2862 Discontinued
0.7293 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD2309 Approved
0.7273 Intermediate Similarity NPD5403 Approved
0.7273 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD2557 Approved
0.7258 Intermediate Similarity NPD256 Approved
0.7258 Intermediate Similarity NPD255 Approved
0.7254 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD5401 Approved
0.7246 Intermediate Similarity NPD5865 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2668 Approved
0.7244 Intermediate Similarity NPD2667 Approved
0.7244 Intermediate Similarity NPD2107 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD3028 Approved
0.7234 Intermediate Similarity NPD6667 Approved
0.7234 Intermediate Similarity NPD6666 Approved
0.723 Intermediate Similarity NPD7768 Phase 2
0.7226 Intermediate Similarity NPD1510 Phase 2
0.7222 Intermediate Similarity NPD1182 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