Structure

Physi-Chem Properties

Molecular Weight:  348.1
Volume:  349.213
LogP:  4.649
LogD:  3.956
LogS:  -4.841
# Rotatable Bonds:  1
TPSA:  57.9
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.653
Synthetic Accessibility Score:  2.787
Fsp3:  0.19
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.873
MDCK Permeability:  2.717489405767992e-05
Pgp-inhibitor:  0.996
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.072
30% Bioavailability (F30%):  0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.014
Plasma Protein Binding (PPB):  99.41095733642578%
Volume Distribution (VD):  0.454
Pgp-substrate:  2.0691866874694824%

ADMET: Metabolism

CYP1A2-inhibitor:  0.974
CYP1A2-substrate:  0.162
CYP2C19-inhibitor:  0.96
CYP2C19-substrate:  0.071
CYP2C9-inhibitor:  0.875
CYP2C9-substrate:  0.896
CYP2D6-inhibitor:  0.933
CYP2D6-substrate:  0.881
CYP3A4-inhibitor:  0.936
CYP3A4-substrate:  0.17

ADMET: Excretion

Clearance (CL):  7.725
Half-life (T1/2):  0.125

ADMET: Toxicity

hERG Blockers:  0.079
Human Hepatotoxicity (H-HT):  0.897
Drug-inuced Liver Injury (DILI):  0.893
AMES Toxicity:  0.232
Rat Oral Acute Toxicity:  0.111
Maximum Recommended Daily Dose:  0.716
Skin Sensitization:  0.251
Carcinogencity:  0.943
Eye Corrosion:  0.003
Eye Irritation:  0.027
Respiratory Toxicity:  0.935

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

  Natural Product: NPC113055

Natural Product ID:  NPC113055
Common Name*:   3-(1,3-Benzodioxol-5-Yl)-8,8-Dimethylpyrano[2,3-F]Chromen-4-One
IUPAC Name:   3-(1,3-benzodioxol-5-yl)-8,8-dimethylpyrano[2,3-f]chromen-4-one
Synonyms:  
Standard InCHIKey:  WVHJQUXAKZCXEP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H16O5/c1-21(2)8-7-13-16(26-21)6-4-14-19(22)15(10-23-20(13)14)12-3-5-17-18(9-12)25-11-24-17/h3-10H,11H2,1-2H3
SMILES:  CC1(C)C=Cc2c(ccc3c(=O)c(coc23)c2ccc3c(c2)OCO3)O1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3311043
PubChem CID:   182342
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0003530] Pyranoisoflavonoids

*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
NPO29483 Swartzia schomburgkii Species Fabaceae Eukaryota n.a. suriname rainforest n.a. PMID[11087583]
NPO28682 Jatropha multifida Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19036584]
NPO28682 Jatropha multifida Species Euphorbiaceae Eukaryota stems Botanical Garden, Osmania University, Hyderabad, Andhra Pradesh 2006-AUG PMID[21534583]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25590529]
NPO29252 Moneses uniflora Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[8984155]
NPO29132 Agaricus campestris Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28711 Artabotrys hexapetalus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28711 Artabotrys hexapetalus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29132 Agaricus campestris Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28711 Artabotrys hexapetalus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29132 Agaricus campestris Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28767 Siparuna apiosyce Species Siparunaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29164 Lophostemon confertus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29132 Agaricus campestris Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29483 Swartzia schomburgkii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29393 Hapalopilus rutilans Species Phanerochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29288 Diplorhynchus condylocarpon Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29339 Didemnum moseleyi Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29269 Celsia roripifolia Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28664 Hydrangea arborescens Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28728 Scutellaria planipes Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28699 Vincetoxicum nigrum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28798 Calophyllum macrocarpum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29022 Sarcococca wallichii Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29252 Moneses uniflora Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28711 Artabotrys hexapetalus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28910 Dacus cucumis Species Tephritidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28682 Jatropha multifida Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28606 Lemaireocereus thurberi Species Cactaceae 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
NPT737 Cell Line HUVEC Homo sapiens IC50 > 10000.0 nM PMID[536869]
NPT319 Cell Line B16 Mus musculus IC50 > 10000.0 nM PMID[536869]
NPT380 Cell Line U-251 Homo sapiens IC50 > 10000.0 nM PMID[536869]
NPT1083 Cell Line A-375 Homo sapiens IC50 > 10000.0 nM PMID[536869]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10000.0 nM PMID[536869]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[536869]

☑ 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 NPC113055 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
0.9739 High Similarity NPC34376
0.9675 High Similarity NPC18284
0.9675 High Similarity NPC302741
0.9675 High Similarity NPC273021
0.9671 High Similarity NPC310206
0.9667 High Similarity NPC68882
0.9533 High Similarity NPC5840
0.9533 High Similarity NPC189270
0.9484 High Similarity NPC94155
0.9477 High Similarity NPC155063
0.929 High Similarity NPC19097
0.9286 High Similarity NPC284353
0.9286 High Similarity NPC478238
0.9281 High Similarity NPC144162
0.9281 High Similarity NPC40033
0.9221 High Similarity NPC128961
0.9221 High Similarity NPC478213
0.9221 High Similarity NPC279930
0.9221 High Similarity NPC472408
0.92 High Similarity NPC296575
0.92 High Similarity NPC471590
0.9182 High Similarity NPC470773
0.9177 High Similarity NPC125991
0.9167 High Similarity NPC78071
0.9167 High Similarity NPC258644
0.9156 High Similarity NPC153008
0.9156 High Similarity NPC148497
0.9156 High Similarity NPC292460
0.9136 High Similarity NPC475825
0.9136 High Similarity NPC223375
0.9108 High Similarity NPC187792
0.9108 High Similarity NPC74178
0.9108 High Similarity NPC184755
0.9103 High Similarity NPC180340
0.9097 High Similarity NPC244371
0.9097 High Similarity NPC57211
0.9091 High Similarity NPC279061
0.9073 High Similarity NPC224687
0.9067 High Similarity NPC476054
0.9057 High Similarity NPC478199
0.9032 High Similarity NPC35544
0.9032 High Similarity NPC166201
0.9032 High Similarity NPC52623
0.9032 High Similarity NPC104728
0.902 High Similarity NPC476342
0.9018 High Similarity NPC235575
0.9012 High Similarity NPC41853
0.9012 High Similarity NPC471287
0.9007 High Similarity NPC113089
0.9007 High Similarity NPC293201
0.9 High Similarity NPC185607
0.9 High Similarity NPC470772
0.8994 High Similarity NPC470756
0.8987 High Similarity NPC257914
0.8987 High Similarity NPC104459
0.8987 High Similarity NPC238405
0.8981 High Similarity NPC282307
0.8981 High Similarity NPC170026
0.897 High Similarity NPC156635
0.8954 High Similarity NPC470511
0.8951 High Similarity NPC167479
0.8947 High Similarity NPC136278
0.894 High Similarity NPC9966
0.894 High Similarity NPC70853
0.8931 High Similarity NPC19554
0.8931 High Similarity NPC74749
0.8931 High Similarity NPC269906
0.8931 High Similarity NPC298093
0.8931 High Similarity NPC43971
0.8931 High Similarity NPC328102
0.8924 High Similarity NPC52889
0.8924 High Similarity NPC284820
0.8924 High Similarity NPC473272
0.8917 High Similarity NPC234255
0.8916 High Similarity NPC67302
0.8903 High Similarity NPC234152
0.8896 High Similarity NPC477165
0.8889 High Similarity NPC113093
0.8875 High Similarity NPC182045
0.8875 High Similarity NPC471290
0.8875 High Similarity NPC165549
0.8874 High Similarity NPC29536
0.8868 High Similarity NPC215375
0.8868 High Similarity NPC204879
0.8868 High Similarity NPC62518
0.8861 High Similarity NPC248299
0.8861 High Similarity NPC472455
0.8861 High Similarity NPC471985
0.8854 High Similarity NPC186507
0.8854 High Similarity NPC121910
0.8854 High Similarity NPC168805
0.8848 High Similarity NPC72455
0.8848 High Similarity NPC62640
0.8841 High Similarity NPC212748
0.8834 High Similarity NPC471288
0.8834 High Similarity NPC135345
0.8834 High Similarity NPC229729
0.8831 High Similarity NPC117463
0.8831 High Similarity NPC205522
0.8831 High Similarity NPC299923
0.8827 High Similarity NPC475369
0.8827 High Similarity NPC303174
0.8824 High Similarity NPC179970
0.882 High Similarity NPC261470
0.882 High Similarity NPC414831
0.8812 High Similarity NPC131557
0.8812 High Similarity NPC472624
0.8812 High Similarity NPC119209
0.8812 High Similarity NPC118256
0.8812 High Similarity NPC477164
0.8812 High Similarity NPC192686
0.8812 High Similarity NPC110349
0.8812 High Similarity NPC28241
0.8812 High Similarity NPC475784
0.8805 High Similarity NPC167595
0.8805 High Similarity NPC474681
0.8805 High Similarity NPC476981
0.8805 High Similarity NPC218313
0.88 High Similarity NPC17848
0.8797 High Similarity NPC472280
0.8795 High Similarity NPC472607
0.8795 High Similarity NPC469601
0.879 High Similarity NPC237994
0.8788 High Similarity NPC261254
0.8788 High Similarity NPC256760
0.878 High Similarity NPC288813
0.878 High Similarity NPC165456
0.8774 High Similarity NPC10304
0.8774 High Similarity NPC63256
0.8773 High Similarity NPC173292
0.8766 High Similarity NPC40818
0.8766 High Similarity NPC110639
0.8766 High Similarity NPC195919
0.8766 High Similarity NPC14958
0.8766 High Similarity NPC106461
0.8766 High Similarity NPC215932
0.8766 High Similarity NPC216314
0.8766 High Similarity NPC120924
0.8766 High Similarity NPC310259
0.8765 High Similarity NPC65846
0.8765 High Similarity NPC124038
0.8765 High Similarity NPC243930
0.8765 High Similarity NPC88023
0.8765 High Similarity NPC309025
0.8758 High Similarity NPC40037
0.8758 High Similarity NPC216092
0.8758 High Similarity NPC260640
0.8758 High Similarity NPC259456
0.8758 High Similarity NPC474038
0.8758 High Similarity NPC59522
0.8758 High Similarity NPC295009
0.8757 High Similarity NPC473883
0.875 High Similarity NPC50430
0.8742 High Similarity NPC133970
0.8742 High Similarity NPC6633
0.8742 High Similarity NPC5322
0.8742 High Similarity NPC301897
0.8742 High Similarity NPC474983
0.8735 High Similarity NPC208668
0.8734 High Similarity NPC170492
0.8733 High Similarity NPC157855
0.8733 High Similarity NPC44573
0.8727 High Similarity NPC78734
0.8727 High Similarity NPC51326
0.8727 High Similarity NPC231194
0.8727 High Similarity NPC150767
0.8727 High Similarity NPC105511
0.8726 High Similarity NPC471291
0.8726 High Similarity NPC256406
0.8726 High Similarity NPC318424
0.8726 High Similarity NPC154345
0.872 High Similarity NPC150131
0.872 High Similarity NPC477502
0.8718 High Similarity NPC474648
0.8718 High Similarity NPC238366
0.8718 High Similarity NPC164299
0.8712 High Similarity NPC108433
0.8712 High Similarity NPC475366
0.8712 High Similarity NPC311830
0.8712 High Similarity NPC22832
0.8712 High Similarity NPC475497
0.8712 High Similarity NPC284277
0.8712 High Similarity NPC50960
0.8712 High Similarity NPC300053
0.871 High Similarity NPC79469
0.871 High Similarity NPC104406
0.871 High Similarity NPC97716
0.871 High Similarity NPC237635
0.871 High Similarity NPC474999
0.871 High Similarity NPC85233
0.871 High Similarity NPC24673
0.871 High Similarity NPC201731
0.8704 High Similarity NPC469575
0.8704 High Similarity NPC472635
0.8704 High Similarity NPC474162
0.8704 High Similarity NPC474150
0.8704 High Similarity NPC83922
0.8704 High Similarity NPC474034
0.8704 High Similarity NPC474033
0.8704 High Similarity NPC475144

  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 NPC113055 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
0.8931 High Similarity NPD5494 Approved
0.8834 High Similarity NPD3818 Discontinued
0.871 High Similarity NPD6980 Clinical (unspecified phase)
0.8634 High Similarity NPD919 Approved
0.8562 High Similarity NPD3817 Phase 2
0.8554 High Similarity NPD7054 Approved
0.8543 High Similarity NPD2796 Approved
0.8509 High Similarity NPD3882 Suspended
0.8503 High Similarity NPD7472 Approved
0.8503 High Similarity NPD7074 Phase 3
0.85 High Similarity NPD2393 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8438 Intermediate Similarity NPD1934 Approved
0.8415 Intermediate Similarity NPD1247 Approved
0.8385 Intermediate Similarity NPD2801 Approved
0.8353 Intermediate Similarity NPD7808 Phase 3
0.8343 Intermediate Similarity NPD6797 Phase 2
0.8294 Intermediate Similarity NPD7251 Discontinued
0.8272 Intermediate Similarity NPD7819 Suspended
0.8272 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8246 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8225 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD6801 Discontinued
0.8204 Intermediate Similarity NPD3926 Phase 2
0.8199 Intermediate Similarity NPD4380 Phase 2
0.8187 Intermediate Similarity NPD6559 Discontinued
0.8165 Intermediate Similarity NPD6799 Approved
0.8165 Intermediate Similarity NPD1511 Approved
0.8155 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD6166 Phase 2
0.8148 Intermediate Similarity NPD7411 Suspended
0.8141 Intermediate Similarity NPD1243 Approved
0.8125 Intermediate Similarity NPD920 Approved
0.8121 Intermediate Similarity NPD7075 Discontinued
0.8101 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD1512 Approved
0.8039 Intermediate Similarity NPD1933 Approved
0.8012 Intermediate Similarity NPD5844 Phase 1
0.8 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1510 Phase 2
0.7976 Intermediate Similarity NPD7199 Phase 2
0.7975 Intermediate Similarity NPD6599 Discontinued
0.7962 Intermediate Similarity NPD1549 Phase 2
0.7952 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD6232 Discontinued
0.7901 Intermediate Similarity NPD5403 Approved
0.7898 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD7473 Discontinued
0.7892 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD5402 Approved
0.7888 Intermediate Similarity NPD5401 Approved
0.7885 Intermediate Similarity NPD3748 Approved
0.7882 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD1240 Approved
0.7738 Intermediate Similarity NPD7768 Phase 2
0.7733 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD3749 Approved
0.7688 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD37 Approved
0.7661 Intermediate Similarity NPD6959 Discontinued
0.7643 Intermediate Similarity NPD1607 Approved
0.764 Intermediate Similarity NPD3750 Approved
0.7633 Intermediate Similarity NPD4965 Approved
0.7633 Intermediate Similarity NPD4967 Phase 2
0.7633 Intermediate Similarity NPD4966 Approved
0.7561 Intermediate Similarity NPD2534 Approved
0.7561 Intermediate Similarity NPD2532 Approved
0.7561 Intermediate Similarity NPD2533 Approved
0.7544 Intermediate Similarity NPD6234 Discontinued
0.7531 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD1465 Phase 2
0.7514 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2935 Discontinued
0.7486 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7458 Discontinued
0.7484 Intermediate Similarity NPD6832 Phase 2
0.7473 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD2800 Approved
0.7468 Intermediate Similarity NPD2798 Approved
0.7443 Intermediate Similarity NPD3751 Discontinued
0.7438 Intermediate Similarity NPD2799 Discontinued
0.743 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD3787 Discontinued
0.7405 Intermediate Similarity NPD943 Approved
0.7391 Intermediate Similarity NPD1551 Phase 2
0.7389 Intermediate Similarity NPD2313 Discontinued
0.7374 Intermediate Similarity NPD7685 Pre-registration
0.7371 Intermediate Similarity NPD5242 Approved
0.7368 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD447 Suspended
0.7345 Intermediate Similarity NPD7228 Approved
0.7344 Intermediate Similarity NPD7584 Approved
0.733 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1653 Approved
0.7318 Intermediate Similarity NPD5953 Discontinued
0.7317 Intermediate Similarity NPD4628 Phase 3
0.7302 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD8312 Approved
0.7293 Intermediate Similarity NPD8313 Approved
0.7278 Intermediate Similarity NPD3226 Approved
0.7256 Intermediate Similarity NPD2654 Approved
0.7239 Intermediate Similarity NPD2346 Discontinued
0.7239 Intermediate Similarity NPD2344 Approved
0.7235 Intermediate Similarity NPD7028 Phase 2
0.7232 Intermediate Similarity NPD2403 Approved
0.7225 Intermediate Similarity NPD5006 Approved
0.7225 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD5005 Approved
0.7222 Intermediate Similarity NPD7033 Discontinued
0.7211 Intermediate Similarity NPD6777 Approved
0.7211 Intermediate Similarity NPD6782 Approved
0.7211 Intermediate Similarity NPD6780 Approved
0.7211 Intermediate Similarity NPD6776 Approved
0.7211 Intermediate Similarity NPD6779 Approved
0.7211 Intermediate Similarity NPD6781 Approved
0.7211 Intermediate Similarity NPD6778 Approved
0.7207 Intermediate Similarity NPD7286 Phase 2
0.7193 Intermediate Similarity NPD5890 Approved
0.7193 Intermediate Similarity NPD5889 Approved
0.7193 Intermediate Similarity NPD6386 Approved
0.7193 Intermediate Similarity NPD6385 Approved
0.7188 Intermediate Similarity NPD4307 Phase 2
0.7182 Intermediate Similarity NPD7240 Approved
0.7168 Intermediate Similarity NPD5353 Approved
0.7152 Intermediate Similarity NPD5536 Phase 2
0.7151 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5124 Phase 1
0.7143 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3705 Approved
0.7143 Intermediate Similarity NPD230 Phase 1
0.7135 Intermediate Similarity NPD6585 Discontinued
0.7134 Intermediate Similarity NPD1471 Phase 3
0.7119 Intermediate Similarity NPD7229 Phase 3
0.7117 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD8455 Phase 2
0.7108 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4420 Approved
0.7099 Intermediate Similarity NPD6651 Approved
0.7098 Intermediate Similarity NPD7435 Discontinued
0.7098 Intermediate Similarity NPD7698 Approved
0.7098 Intermediate Similarity NPD7697 Approved
0.7098 Intermediate Similarity NPD7696 Phase 3
0.7092 Intermediate Similarity NPD8151 Discontinued
0.7081 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD1613 Approved
0.7081 Intermediate Similarity NPD8434 Phase 2
0.7073 Intermediate Similarity NPD6099 Approved
0.7073 Intermediate Similarity NPD6100 Approved
0.707 Intermediate Similarity NPD3266 Approved
0.707 Intermediate Similarity NPD3267 Approved
0.7066 Intermediate Similarity NPD2309 Approved
0.7066 Intermediate Similarity NPD3887 Approved
0.7063 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7871 Phase 2
0.7062 Intermediate Similarity NPD7870 Phase 2
0.7044 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD5710 Approved
0.7022 Intermediate Similarity NPD5711 Approved
0.7013 Intermediate Similarity NPD17 Approved
0.7012 Intermediate Similarity NPD4308 Phase 3
0.7 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4361 Phase 2
0.7 Intermediate Similarity NPD3027 Phase 3
0.699 Remote Similarity NPD7583 Approved
0.6987 Remote Similarity NPD3972 Approved
0.6982 Remote Similarity NPD7390 Discontinued
0.6981 Remote Similarity NPD3018 Phase 2
0.6981 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6977 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6971 Remote Similarity NPD4288 Approved
0.6966 Remote Similarity NPD8127 Discontinued
0.6962 Remote Similarity NPD1203 Approved
0.6959 Remote Similarity NPD6823 Phase 2
0.6957 Remote Similarity NPD1296 Phase 2
0.6957 Remote Similarity NPD3268 Approved
0.6954 Remote Similarity NPD7701 Phase 2
0.6954 Remote Similarity NPD6279 Approved
0.6954 Remote Similarity NPD7585 Approved
0.6954 Remote Similarity NPD6280 Approved
0.6947 Remote Similarity NPD4360 Phase 2
0.6947 Remote Similarity NPD4363 Phase 3
0.6947 Remote Similarity NPD6534 Approved
0.6947 Remote Similarity NPD6535 Approved
0.6946 Remote Similarity NPD6674 Discontinued
0.6937 Remote Similarity NPD4908 Phase 1
0.6935 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7783 Phase 2
0.6928 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2355 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