Structure

Physi-Chem Properties

Molecular Weight:  168.06
Volume:  183.41
LogP:  3.941
LogD:  3.579
LogS:  -5.054
# Rotatable Bonds:  0
TPSA:  13.14
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.5
Synthetic Accessibility Score:  1.489
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.611
MDCK Permeability:  1.9532470105332322e-05
Pgp-inhibitor:  0.035
Pgp-substrate:  0.16
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.266
Plasma Protein Binding (PPB):  95.9889907836914%
Volume Distribution (VD):  1.03
Pgp-substrate:  4.382360935211182%

ADMET: Metabolism

CYP1A2-inhibitor:  0.995
CYP1A2-substrate:  0.648
CYP2C19-inhibitor:  0.825
CYP2C19-substrate:  0.388
CYP2C9-inhibitor:  0.361
CYP2C9-substrate:  0.868
CYP2D6-inhibitor:  0.433
CYP2D6-substrate:  0.906
CYP3A4-inhibitor:  0.113
CYP3A4-substrate:  0.242

ADMET: Excretion

Clearance (CL):  8.014
Half-life (T1/2):  0.221

ADMET: Toxicity

hERG Blockers:  0.093
Human Hepatotoxicity (H-HT):  0.154
Drug-inuced Liver Injury (DILI):  0.915
AMES Toxicity:  0.81
Rat Oral Acute Toxicity:  0.251
Maximum Recommended Daily Dose:  0.112
Skin Sensitization:  0.776
Carcinogencity:  0.87
Eye Corrosion:  0.434
Eye Irritation:  0.995
Respiratory Toxicity:  0.693

Download Data

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

  Natural Product: NPC246214

Natural Product ID:  NPC246214
Common Name*:   Dibenzofuran
IUPAC Name:   dibenzofuran
Synonyms:   Dibenzofuran
Standard InCHIKey:  TXCDCPKCNAJMEE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H
SMILES:  c1ccc2c(c1)oc1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL277497
PubChem CID:   568
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans
        • [CHEMONTID:0000015] Dibenzofurans

*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
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[20121210]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[28558206]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[32031796]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO389 Actaea heracleifolia Species Ranunculaceae 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
NPT155 Individual Protein Aryl hydrocarbon receptor Homo sapiens EC50 = 1000000.0 nM PMID[482952]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 8912.5 nM PMID[482956]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 54482.7 nM PMID[482956]
NPT35 Others n.a. Log S = -4.6 n.a. PMID[482951]
NPT3573 Organism Bovine viral diarrhea virus Bovine viral diarrhea virus 1 EC50 = 58000.0 nM PMID[482953]
NPT27 Others Unspecified CC50 > 100000.0 nM PMID[482953]
NPT27 Others Unspecified log Ks = 2.97 n.a. PMID[482954]
NPT35 Others n.a. LogP = 4.04 n.a. PMID[482955]
NPT35 Others n.a. LogP = 3.76 n.a. PMID[482958]
NPT2 Others Unspecified Potency n.a. 48557.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 22199.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 69567.3 nM PubChem BioAssay data set

☑ 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 NPC246214 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
0.9138 High Similarity NPC206007
0.8898 High Similarity NPC35744
0.8814 High Similarity NPC32298
0.8739 High Similarity NPC137710
0.8739 High Similarity NPC54243
0.8678 High Similarity NPC314329
0.8618 High Similarity NPC107846
0.855 High Similarity NPC62735
0.8548 High Similarity NPC83301
0.8538 High Similarity NPC163029
0.8492 Intermediate Similarity NPC50583
0.848 Intermediate Similarity NPC141059
0.843 Intermediate Similarity NPC201284
0.8387 Intermediate Similarity NPC93730
0.8387 Intermediate Similarity NPC11799
0.8387 Intermediate Similarity NPC141252
0.8385 Intermediate Similarity NPC324117
0.8346 Intermediate Similarity NPC112757
0.832 Intermediate Similarity NPC193805
0.8271 Intermediate Similarity NPC233707
0.8264 Intermediate Similarity NPC469954
0.8264 Intermediate Similarity NPC45104
0.8254 Intermediate Similarity NPC2771
0.8254 Intermediate Similarity NPC470858
0.8244 Intermediate Similarity NPC209858
0.8235 Intermediate Similarity NPC279916
0.8217 Intermediate Similarity NPC475092
0.8203 Intermediate Similarity NPC125887
0.8203 Intermediate Similarity NPC59502
0.8197 Intermediate Similarity NPC152159
0.8182 Intermediate Similarity NPC59035
0.8182 Intermediate Similarity NPC316062
0.8182 Intermediate Similarity NPC79202
0.8154 Intermediate Similarity NPC11173
0.8145 Intermediate Similarity NPC115859
0.8125 Intermediate Similarity NPC298884
0.8125 Intermediate Similarity NPC22783
0.8116 Intermediate Similarity NPC230943
0.811 Intermediate Similarity NPC224657
0.8102 Intermediate Similarity NPC53192
0.8099 Intermediate Similarity NPC205523
0.8095 Intermediate Similarity NPC472888
0.8077 Intermediate Similarity NPC278787
0.8067 Intermediate Similarity NPC23332
0.8062 Intermediate Similarity NPC196034
0.8049 Intermediate Similarity NPC171023
0.8047 Intermediate Similarity NPC237868
0.8043 Intermediate Similarity NPC302181
0.8043 Intermediate Similarity NPC17262
0.8043 Intermediate Similarity NPC225884
0.8033 Intermediate Similarity NPC470860
0.8031 Intermediate Similarity NPC471074
0.8031 Intermediate Similarity NPC473885
0.8031 Intermediate Similarity NPC56332
0.8015 Intermediate Similarity NPC301717
0.8015 Intermediate Similarity NPC141549
0.8015 Intermediate Similarity NPC279596
0.8 Intermediate Similarity NPC150215
0.8 Intermediate Similarity NPC265181
0.8 Intermediate Similarity NPC22678
0.8 Intermediate Similarity NPC170546
0.8 Intermediate Similarity NPC66246
0.8 Intermediate Similarity NPC939
0.7986 Intermediate Similarity NPC98926
0.7986 Intermediate Similarity NPC155144
0.7984 Intermediate Similarity NPC428300
0.7984 Intermediate Similarity NPC41721
0.7983 Intermediate Similarity NPC183648
0.797 Intermediate Similarity NPC265793
0.7969 Intermediate Similarity NPC88403
0.7967 Intermediate Similarity NPC312525
0.7967 Intermediate Similarity NPC217180
0.7953 Intermediate Similarity NPC178382
0.7953 Intermediate Similarity NPC118853
0.7949 Intermediate Similarity NPC42471
0.7943 Intermediate Similarity NPC135325
0.7939 Intermediate Similarity NPC183348
0.7939 Intermediate Similarity NPC7569
0.7939 Intermediate Similarity NPC282230
0.7939 Intermediate Similarity NPC228184
0.7934 Intermediate Similarity NPC53953
0.7929 Intermediate Similarity NPC51641
0.7929 Intermediate Similarity NPC210826
0.7929 Intermediate Similarity NPC300267
0.7926 Intermediate Similarity NPC29638
0.7926 Intermediate Similarity NPC130976
0.792 Intermediate Similarity NPC230951
0.792 Intermediate Similarity NPC168050
0.792 Intermediate Similarity NPC470092
0.7917 Intermediate Similarity NPC233238
0.7914 Intermediate Similarity NPC93241
0.7914 Intermediate Similarity NPC27798
0.7914 Intermediate Similarity NPC290038
0.7907 Intermediate Similarity NPC474264
0.7903 Intermediate Similarity NPC243704
0.7899 Intermediate Similarity NPC254010
0.7895 Intermediate Similarity NPC470406
0.7895 Intermediate Similarity NPC287533
0.7891 Intermediate Similarity NPC89630
0.7883 Intermediate Similarity NPC262635
0.7881 Intermediate Similarity NPC141523
0.7879 Intermediate Similarity NPC196979
0.7879 Intermediate Similarity NPC324488
0.7879 Intermediate Similarity NPC470977
0.7879 Intermediate Similarity NPC470976
0.7879 Intermediate Similarity NPC15083
0.7872 Intermediate Similarity NPC12148
0.7872 Intermediate Similarity NPC130581
0.7872 Intermediate Similarity NPC198427
0.7869 Intermediate Similarity NPC252004
0.7863 Intermediate Similarity NPC197425
0.7863 Intermediate Similarity NPC473019
0.7857 Intermediate Similarity NPC97566
0.7852 Intermediate Similarity NPC278832
0.7852 Intermediate Similarity NPC307401
0.7852 Intermediate Similarity NPC64157
0.7842 Intermediate Similarity NPC313036
0.7842 Intermediate Similarity NPC158871
0.7842 Intermediate Similarity NPC117674
0.784 Intermediate Similarity NPC264976
0.7836 Intermediate Similarity NPC292998
0.7832 Intermediate Similarity NPC472406
0.7832 Intermediate Similarity NPC13282
0.7829 Intermediate Similarity NPC165556
0.7823 Intermediate Similarity NPC217423
0.782 Intermediate Similarity NPC284424
0.782 Intermediate Similarity NPC470859
0.782 Intermediate Similarity NPC183103
0.7817 Intermediate Similarity NPC272194
0.7817 Intermediate Similarity NPC306788
0.7812 Intermediate Similarity NPC182646
0.7807 Intermediate Similarity NPC95755
0.7805 Intermediate Similarity NPC188907
0.7805 Intermediate Similarity NPC28054
0.7805 Intermediate Similarity NPC150895
0.7803 Intermediate Similarity NPC245395
0.7803 Intermediate Similarity NPC39753
0.7803 Intermediate Similarity NPC115998
0.7778 Intermediate Similarity NPC204592
0.7778 Intermediate Similarity NPC156244
0.7778 Intermediate Similarity NPC149085
0.7778 Intermediate Similarity NPC217914
0.7778 Intermediate Similarity NPC23668
0.7778 Intermediate Similarity NPC193976
0.7778 Intermediate Similarity NPC115324
0.7778 Intermediate Similarity NPC38209
0.777 Intermediate Similarity NPC27220
0.7769 Intermediate Similarity NPC474737
0.7769 Intermediate Similarity NPC177925
0.7762 Intermediate Similarity NPC296030
0.7762 Intermediate Similarity NPC39929
0.7762 Intermediate Similarity NPC37226
0.7762 Intermediate Similarity NPC226644
0.7762 Intermediate Similarity NPC221868
0.7762 Intermediate Similarity NPC37208
0.7761 Intermediate Similarity NPC477536
0.7754 Intermediate Similarity NPC473499
0.775 Intermediate Similarity NPC259554
0.7746 Intermediate Similarity NPC17816
0.7746 Intermediate Similarity NPC252208
0.7744 Intermediate Similarity NPC473982
0.7744 Intermediate Similarity NPC137264
0.7742 Intermediate Similarity NPC19290
0.7737 Intermediate Similarity NPC202260
0.7737 Intermediate Similarity NPC254841
0.7734 Intermediate Similarity NPC311219
0.773 Intermediate Similarity NPC478166
0.773 Intermediate Similarity NPC208584
0.7727 Intermediate Similarity NPC57552
0.7727 Intermediate Similarity NPC238309
0.7724 Intermediate Similarity NPC207624
0.7724 Intermediate Similarity NPC67654
0.7724 Intermediate Similarity NPC142308
0.7724 Intermediate Similarity NPC41326
0.7721 Intermediate Similarity NPC239495
0.7721 Intermediate Similarity NPC9985
0.7714 Intermediate Similarity NPC51146
0.7714 Intermediate Similarity NPC166858
0.7712 Intermediate Similarity NPC139891
0.7712 Intermediate Similarity NPC475269
0.771 Intermediate Similarity NPC37512
0.771 Intermediate Similarity NPC161322
0.7708 Intermediate Similarity NPC78335
0.7708 Intermediate Similarity NPC135303
0.7708 Intermediate Similarity NPC148423
0.7708 Intermediate Similarity NPC167576
0.7708 Intermediate Similarity NPC230713
0.7704 Intermediate Similarity NPC57601
0.7698 Intermediate Similarity NPC28337
0.7692 Intermediate Similarity NPC4164
0.7692 Intermediate Similarity NPC52035
0.7692 Intermediate Similarity NPC95526
0.7692 Intermediate Similarity NPC298224
0.7687 Intermediate Similarity NPC113006
0.7687 Intermediate Similarity NPC278556
0.7681 Intermediate Similarity NPC476191
0.768 Intermediate Similarity NPC227660
0.7676 Intermediate Similarity NPC281398
0.7676 Intermediate Similarity NPC190572
0.7671 Intermediate Similarity NPC1477

  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 NPC246214 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
0.8678 High Similarity NPD1547 Clinical (unspecified phase)
0.855 High Similarity NPD2344 Approved
0.8409 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.8296 Intermediate Similarity NPD2309 Approved
0.8235 Intermediate Similarity NPD1241 Discontinued
0.8047 Intermediate Similarity NPD2798 Approved
0.8031 Intermediate Similarity NPD1876 Approved
0.8016 Intermediate Similarity NPD3972 Approved
0.8 Intermediate Similarity NPD1471 Phase 3
0.7969 Intermediate Similarity NPD3266 Approved
0.7969 Intermediate Similarity NPD3267 Approved
0.7969 Intermediate Similarity NPD1203 Approved
0.7939 Intermediate Similarity NPD2313 Discontinued
0.7923 Intermediate Similarity NPD6832 Phase 2
0.7883 Intermediate Similarity NPD1243 Approved
0.7852 Intermediate Similarity NPD2799 Discontinued
0.7852 Intermediate Similarity NPD3748 Approved
0.7829 Intermediate Similarity NPD2797 Approved
0.782 Intermediate Similarity NPD4307 Phase 2
0.7778 Intermediate Similarity NPD17 Approved
0.7734 Intermediate Similarity NPD9717 Approved
0.7724 Intermediate Similarity NPD6279 Approved
0.7724 Intermediate Similarity NPD6280 Approved
0.7714 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD9697 Approved
0.7669 Intermediate Similarity NPD3268 Approved
0.7664 Intermediate Similarity NPD2796 Approved
0.7626 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD3873 Phase 3
0.7622 Intermediate Similarity NPD3869 Phase 3
0.7619 Intermediate Similarity NPD2296 Approved
0.7619 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD2346 Discontinued
0.7606 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD1608 Approved
0.7591 Intermediate Similarity NPD4308 Phase 3
0.7571 Intermediate Similarity NPD3750 Approved
0.7568 Intermediate Similarity NPD4947 Clinical (unspecified phase)
0.7559 Intermediate Similarity NPD1651 Approved
0.7556 Intermediate Similarity NPD1240 Approved
0.7554 Intermediate Similarity NPD1549 Phase 2
0.7517 Intermediate Similarity NPD3749 Approved
0.75 Intermediate Similarity NPD1933 Approved
0.75 Intermediate Similarity NPD1019 Discontinued
0.75 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD920 Approved
0.7482 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD1607 Approved
0.7407 Intermediate Similarity NPD3764 Approved
0.7385 Intermediate Similarity NPD1281 Approved
0.7357 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD2353 Approved
0.7344 Intermediate Similarity NPD1894 Discontinued
0.7339 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD1510 Phase 2
0.7328 Intermediate Similarity NPD1481 Phase 2
0.7324 Intermediate Similarity NPD7003 Approved
0.732 Intermediate Similarity NPD6808 Phase 2
0.7303 Intermediate Similarity NPD710 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD3140 Approved
0.7299 Intermediate Similarity NPD3142 Approved
0.7288 Intermediate Similarity NPD1238 Approved
0.7286 Intermediate Similarity NPD1551 Phase 2
0.728 Intermediate Similarity NPD5535 Approved
0.7279 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD6798 Discontinued
0.7273 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3926 Phase 2
0.7252 Intermediate Similarity NPD1535 Discovery
0.7252 Intermediate Similarity NPD1611 Approved
0.7246 Intermediate Similarity NPD4618 Approved
0.7246 Intermediate Similarity NPD4622 Approved
0.7246 Intermediate Similarity NPD6355 Discontinued
0.7241 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4661 Approved
0.7241 Intermediate Similarity NPD4662 Approved
0.7226 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD3225 Approved
0.7218 Intermediate Similarity NPD1283 Approved
0.7203 Intermediate Similarity NPD4628 Phase 3
0.7188 Intermediate Similarity NPD9493 Approved
0.7172 Intermediate Similarity NPD6799 Approved
0.7163 Intermediate Similarity NPD2935 Discontinued
0.7162 Intermediate Similarity NPD3226 Approved
0.7154 Intermediate Similarity NPD5585 Approved
0.7153 Intermediate Similarity NPD2354 Approved
0.7153 Intermediate Similarity NPD3887 Approved
0.7153 Intermediate Similarity NPD411 Approved
0.7153 Intermediate Similarity NPD1296 Phase 2
0.7143 Intermediate Similarity NPD5689 Approved
0.7143 Intermediate Similarity NPD5688 Approved
0.7134 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD919 Approved
0.7123 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD5401 Approved
0.7122 Intermediate Similarity NPD447 Suspended
0.7121 Intermediate Similarity NPD1201 Approved
0.712 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD6599 Discontinued
0.7109 Intermediate Similarity NPD2557 Approved
0.7107 Intermediate Similarity NPD9261 Approved
0.7101 Intermediate Similarity NPD8032 Phase 2
0.7097 Intermediate Similarity NPD5668 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD6273 Approved
0.7075 Intermediate Similarity NPD5049 Phase 3
0.7073 Intermediate Similarity NPD968 Approved
0.7067 Intermediate Similarity NPD7411 Suspended
0.7063 Intermediate Similarity NPD2897 Discontinued
0.7055 Intermediate Similarity NPD1511 Approved
0.7054 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD4477 Approved
0.7042 Intermediate Similarity NPD4476 Approved
0.7037 Intermediate Similarity NPD1470 Approved
0.7037 Intermediate Similarity NPD1164 Approved
0.7032 Intermediate Similarity NPD1247 Approved
0.7029 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD5403 Approved
0.7023 Intermediate Similarity NPD3445 Approved
0.7023 Intermediate Similarity NPD3443 Approved
0.7023 Intermediate Similarity NPD3444 Approved
0.7007 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1184 Approved
0.7 Intermediate Similarity NPD5536 Phase 2
0.6993 Remote Similarity NPD7768 Phase 2
0.6986 Remote Similarity NPD7440 Discontinued
0.6974 Remote Similarity NPD7819 Suspended
0.6968 Remote Similarity NPD5494 Approved
0.6959 Remote Similarity NPD1512 Approved
0.6947 Remote Similarity NPD9545 Approved
0.6935 Remote Similarity NPD3134 Approved
0.6933 Remote Similarity NPD2649 Approved
0.6933 Remote Similarity NPD2651 Approved
0.6929 Remote Similarity NPD2979 Phase 3
0.6928 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6913 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6913 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6911 Remote Similarity NPD1237 Approved
0.6908 Remote Similarity NPD7577 Discontinued
0.6905 Remote Similarity NPD5451 Approved
0.6899 Remote Similarity NPD690 Clinical (unspecified phase)
0.6897 Remote Similarity NPD2800 Approved
0.6894 Remote Similarity NPD5691 Approved
0.6894 Remote Similarity NPD3049 Approved
0.6889 Remote Similarity NPD4359 Approved
0.6887 Remote Similarity NPD6585 Discontinued
0.6883 Remote Similarity NPD3882 Suspended
0.688 Remote Similarity NPD1358 Approved
0.688 Remote Similarity NPD9264 Approved
0.688 Remote Similarity NPD9263 Approved
0.688 Remote Similarity NPD9267 Approved
0.688 Remote Similarity NPD290 Approved
0.6875 Remote Similarity NPD3050 Clinical (unspecified phase)
0.6866 Remote Similarity NPD422 Phase 1
0.6866 Remote Similarity NPD1610 Phase 2
0.6864 Remote Similarity NPD1202 Approved
0.6863 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6233 Phase 2
0.6853 Remote Similarity NPD7033 Discontinued
0.6852 Remote Similarity NPD6559 Discontinued
0.6846 Remote Similarity NPD6671 Approved
0.6846 Remote Similarity NPD709 Approved
0.6842 Remote Similarity NPD5890 Approved
0.6842 Remote Similarity NPD1778 Approved
0.6842 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5889 Approved
0.6825 Remote Similarity NPD2684 Approved
0.6825 Remote Similarity NPD9266 Approved
0.6825 Remote Similarity NPD74 Approved
0.6821 Remote Similarity NPD7458 Discontinued
0.6818 Remote Similarity NPD6581 Approved
0.6818 Remote Similarity NPD6580 Approved
0.6818 Remote Similarity NPD4288 Approved
0.6818 Remote Similarity NPD1548 Phase 1
0.6818 Remote Similarity NPD2486 Discontinued
0.6806 Remote Similarity NPD6099 Approved
0.6806 Remote Similarity NPD6100 Approved
0.6797 Remote Similarity NPD6844 Discontinued
0.6797 Remote Similarity NPD6801 Discontinued
0.6797 Remote Similarity NPD1934 Approved
0.6794 Remote Similarity NPD3596 Phase 2
0.6792 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6791 Remote Similarity NPD3496 Discontinued
0.6791 Remote Similarity NPD3847 Discontinued
0.6788 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6776 Remote Similarity NPD4380 Phase 2
0.6774 Remote Similarity NPD164 Approved
0.6767 Remote Similarity NPD6830 Clinical (unspecified phase)
0.6767 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6763 Remote Similarity NPD2614 Approved
0.6753 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6738 Remote Similarity NPD4062 Phase 3
0.6735 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6735 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6731 Remote Similarity NPD7075 Discontinued
0.6731 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6731 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6718 Remote Similarity NPD6387 Discontinued
0.6716 Remote Similarity NPD6516 Phase 2
0.6716 Remote Similarity NPD4626 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