Structure

Physi-Chem Properties

Molecular Weight:  538.09
Volume:  521.816
LogP:  3.925
LogD:  2.577
LogS:  -5.841
# Rotatable Bonds:  3
TPSA:  173.98
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.16
Synthetic Accessibility Score:  3.267
Fsp3:  0.0
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.693
MDCK Permeability:  1.3149778169463389e-05
Pgp-inhibitor:  0.019
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.01
Plasma Protein Binding (PPB):  100.97022247314453%
Volume Distribution (VD):  0.187
Pgp-substrate:  1.252781629562378%

ADMET: Metabolism

CYP1A2-inhibitor:  0.928
CYP1A2-substrate:  0.063
CYP2C19-inhibitor:  0.812
CYP2C19-substrate:  0.033
CYP2C9-inhibitor:  0.649
CYP2C9-substrate:  0.514
CYP2D6-inhibitor:  0.123
CYP2D6-substrate:  0.126
CYP3A4-inhibitor:  0.172
CYP3A4-substrate:  0.065

ADMET: Excretion

Clearance (CL):  7.688
Half-life (T1/2):  0.858

ADMET: Toxicity

hERG Blockers:  0.047
Human Hepatotoxicity (H-HT):  0.394
Drug-inuced Liver Injury (DILI):  0.972
AMES Toxicity:  0.683
Rat Oral Acute Toxicity:  0.679
Maximum Recommended Daily Dose:  0.93
Skin Sensitization:  0.944
Carcinogencity:  0.65
Eye Corrosion:  0.003
Eye Irritation:  0.9
Respiratory Toxicity:  0.019

Download Data

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

  Natural Product: NPC231758

Natural Product ID:  NPC231758
Common Name*:   2,2'-[1,2-Bis(3,4-Dihydroxyphenyl)-1,2-Ethanedylidene]Bis[6-Hydroxy-3(2H)-Benzofuranone]
IUPAC Name:   (2Z)-2-[(2Z)-1,2-bis(3,4-dihydroxyphenyl)-2-(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)ethylidene]-6-hydroxy-1-benzofuran-3-one
Synonyms:  
Standard InCHIKey:  MZVYXDUSVXNKLC-IDDWGTJGSA-N
Standard InCHI:  InChI=1S/C30H18O10/c31-15-3-5-17-23(11-15)39-29(27(17)37)25(13-1-7-19(33)21(35)9-13)26(14-2-8-20(34)22(36)10-14)30-28(38)18-6-4-16(32)12-24(18)40-30/h1-12,31-36H/b29-25-,30-26-
SMILES:  c1cc(c(cc1/C(=C/1C(=O)c2ccc(cc2O1)O)/C(=C1/C(=O)c2ccc(cc2O1)O)/c1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL523383
PubChem CID:   10007411
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001631] Aurone flavonoids

*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
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota Whole plant n.a. n.a. PMID[11141121]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24559 Cotinus coggygria Species Anacardiaceae 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
NPT1 Others Radical scavenging activity IC50 = 9.7 ug.mL-1 PMID[465760]

☑ 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 NPC231758 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
0.9325 High Similarity NPC156955
0.9226 High Similarity NPC189130
0.9211 High Similarity NPC140840
0.9211 High Similarity NPC86847
0.915 High Similarity NPC19545
0.9051 High Similarity NPC185526
0.9051 High Similarity NPC112954
0.9038 High Similarity NPC304954
0.9032 High Similarity NPC260582
0.9006 High Similarity NPC472582
0.8974 High Similarity NPC260895
0.897 High Similarity NPC149846
0.8961 High Similarity NPC51443
0.8961 High Similarity NPC74881
0.8944 High Similarity NPC477841
0.8944 High Similarity NPC272722
0.8944 High Similarity NPC219927
0.8929 High Similarity NPC47883
0.8924 High Similarity NPC133392
0.8917 High Similarity NPC63187
0.8917 High Similarity NPC37684
0.8917 High Similarity NPC157784
0.891 High Similarity NPC188871
0.891 High Similarity NPC149127
0.891 High Similarity NPC286342
0.8909 High Similarity NPC476370
0.8902 High Similarity NPC107627
0.8896 High Similarity NPC179271
0.8896 High Similarity NPC169749
0.8896 High Similarity NPC20791
0.8882 High Similarity NPC34089
0.8882 High Similarity NPC196179
0.8875 High Similarity NPC195832
0.8875 High Similarity NPC154304
0.8875 High Similarity NPC190487
0.8868 High Similarity NPC471500
0.8868 High Similarity NPC472461
0.8868 High Similarity NPC265511
0.8861 High Similarity NPC58382
0.8861 High Similarity NPC270620
0.8861 High Similarity NPC141212
0.8861 High Similarity NPC179126
0.8861 High Similarity NPC78326
0.8861 High Similarity NPC162351
0.8861 High Similarity NPC236223
0.8855 High Similarity NPC216842
0.8855 High Similarity NPC476640
0.8855 High Similarity NPC82217
0.8855 High Similarity NPC476374
0.8855 High Similarity NPC117450
0.8854 High Similarity NPC205046
0.8854 High Similarity NPC304295
0.8854 High Similarity NPC154345
0.8854 High Similarity NPC59162
0.8848 High Similarity NPC102277
0.8848 High Similarity NPC279209
0.8846 High Similarity NPC270465
0.8846 High Similarity NPC105512
0.8846 High Similarity NPC87125
0.8841 High Similarity NPC470704
0.8841 High Similarity NPC260266
0.8839 High Similarity NPC95864
0.8834 High Similarity NPC36320
0.8834 High Similarity NPC7688
0.8834 High Similarity NPC36
0.8834 High Similarity NPC259757
0.8834 High Similarity NPC58223
0.8834 High Similarity NPC72787
0.8834 High Similarity NPC7154
0.8834 High Similarity NPC125039
0.8834 High Similarity NPC36916
0.8834 High Similarity NPC477840
0.8831 High Similarity NPC70136
0.882 High Similarity NPC188967
0.8812 High Similarity NPC183
0.8812 High Similarity NPC471515
0.8812 High Similarity NPC67876
0.8812 High Similarity NPC471479
0.8812 High Similarity NPC237418
0.8805 High Similarity NPC80534
0.8805 High Similarity NPC214138
0.8805 High Similarity NPC56786
0.8802 High Similarity NPC99591
0.8802 High Similarity NPC287243
0.8797 High Similarity NPC82325
0.8797 High Similarity NPC279989
0.8797 High Similarity NPC55205
0.8797 High Similarity NPC123886
0.8795 High Similarity NPC472454
0.8795 High Similarity NPC186847
0.8795 High Similarity NPC230619
0.8795 High Similarity NPC257667
0.8795 High Similarity NPC174700
0.8795 High Similarity NPC54098
0.879 High Similarity NPC77858
0.879 High Similarity NPC3825
0.879 High Similarity NPC88804
0.8788 High Similarity NPC280493
0.8782 High Similarity NPC196277
0.8782 High Similarity NPC43669
0.8782 High Similarity NPC272721
0.8782 High Similarity NPC3036
0.878 High Similarity NPC82330
0.878 High Similarity NPC224851
0.878 High Similarity NPC171985
0.878 High Similarity NPC320741
0.8773 High Similarity NPC272064
0.8772 High Similarity NPC226725
0.8766 High Similarity NPC279121
0.8765 High Similarity NPC112418
0.8765 High Similarity NPC142252
0.8765 High Similarity NPC289771
0.8765 High Similarity NPC158188
0.8758 High Similarity NPC476410
0.8758 High Similarity NPC143828
0.8758 High Similarity NPC115798
0.8758 High Similarity NPC7846
0.8758 High Similarity NPC300943
0.8758 High Similarity NPC191459
0.8758 High Similarity NPC288669
0.8758 High Similarity NPC25495
0.8758 High Similarity NPC253634
0.8758 High Similarity NPC261004
0.8758 High Similarity NPC19687
0.8758 High Similarity NPC4481
0.8758 High Similarity NPC18772
0.8758 High Similarity NPC18607
0.8758 High Similarity NPC193842
0.8758 High Similarity NPC176300
0.8758 High Similarity NPC9609
0.8758 High Similarity NPC22472
0.8758 High Similarity NPC172202
0.8758 High Similarity NPC105242
0.8758 High Similarity NPC284127
0.8758 High Similarity NPC204854
0.8758 High Similarity NPC152166
0.8758 High Similarity NPC130894
0.875 High Similarity NPC3980
0.875 High Similarity NPC296018
0.875 High Similarity NPC100916
0.875 High Similarity NPC137100
0.875 High Similarity NPC55619
0.875 High Similarity NPC474638
0.875 High Similarity NPC471841
0.875 High Similarity NPC200388
0.875 High Similarity NPC282307
0.875 High Similarity NPC153512
0.875 High Similarity NPC154741
0.875 High Similarity NPC8127
0.875 High Similarity NPC170026
0.875 High Similarity NPC49667
0.8742 High Similarity NPC33051
0.8742 High Similarity NPC49402
0.8742 High Similarity NPC325028
0.8742 High Similarity NPC170492
0.8742 High Similarity NPC246328
0.8742 High Similarity NPC27532
0.8742 High Similarity NPC273462
0.8742 High Similarity NPC227337
0.8742 High Similarity NPC256346
0.8742 High Similarity NPC70433
0.8735 High Similarity NPC476641
0.8735 High Similarity NPC476365
0.8734 High Similarity NPC200740
0.8734 High Similarity NPC133953
0.8734 High Similarity NPC236769
0.8734 High Similarity NPC54394
0.8734 High Similarity NPC76376
0.8734 High Similarity NPC50403
0.8734 High Similarity NPC28274
0.8734 High Similarity NPC125062
0.8734 High Similarity NPC252933
0.8727 High Similarity NPC50394
0.8727 High Similarity NPC48640
0.8727 High Similarity NPC149244
0.8726 High Similarity NPC1612
0.8726 High Similarity NPC183959
0.8726 High Similarity NPC195351
0.8721 High Similarity NPC248315
0.872 High Similarity NPC45449
0.872 High Similarity NPC300053
0.8718 High Similarity NPC77378
0.8718 High Similarity NPC168803
0.8718 High Similarity NPC108406
0.8713 High Similarity NPC154527
0.8712 High Similarity NPC471745
0.8712 High Similarity NPC476247
0.8704 High Similarity NPC471744
0.8704 High Similarity NPC328102
0.8701 High Similarity NPC175013
0.8701 High Similarity NPC471417
0.8698 High Similarity NPC98546
0.8698 High Similarity NPC297807
0.8698 High Similarity NPC475783
0.8698 High Similarity NPC476773
0.8696 High Similarity NPC29841
0.8696 High Similarity NPC75215
0.8696 High Similarity NPC63454
0.8696 High Similarity NPC78302
0.8696 High Similarity NPC110070

  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 NPC231758 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
0.8987 High Similarity NPD3882 Suspended
0.8896 High Similarity NPD1512 Approved
0.8834 High Similarity NPD6166 Phase 2
0.8834 High Similarity NPD6168 Clinical (unspecified phase)
0.8834 High Similarity NPD6167 Clinical (unspecified phase)
0.8766 High Similarity NPD1511 Approved
0.8625 High Similarity NPD2393 Clinical (unspecified phase)
0.8562 High Similarity NPD1934 Approved
0.8519 High Similarity NPD4868 Clinical (unspecified phase)
0.8509 High Similarity NPD2801 Approved
0.8503 High Similarity NPD3818 Discontinued
0.8471 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD3817 Phase 2
0.8354 Intermediate Similarity NPD7075 Discontinued
0.8354 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8353 Intermediate Similarity NPD6797 Phase 2
0.8304 Intermediate Similarity NPD7251 Discontinued
0.8256 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD3749 Approved
0.821 Intermediate Similarity NPD4380 Phase 2
0.8205 Intermediate Similarity NPD1549 Phase 2
0.8187 Intermediate Similarity NPD7074 Phase 3
0.8176 Intermediate Similarity NPD6799 Approved
0.8171 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD7411 Suspended
0.815 Intermediate Similarity NPD7808 Phase 3
0.8141 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8141 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD1510 Phase 2
0.8129 Intermediate Similarity NPD7054 Approved
0.8121 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.811 Intermediate Similarity NPD6801 Discontinued
0.8107 Intermediate Similarity NPD3926 Phase 2
0.8105 Intermediate Similarity NPD943 Approved
0.8095 Intermediate Similarity NPD6959 Discontinued
0.8081 Intermediate Similarity NPD7472 Approved
0.8059 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD5494 Approved
0.8025 Intermediate Similarity NPD5403 Approved
0.8012 Intermediate Similarity NPD5402 Approved
0.7988 Intermediate Similarity NPD6599 Discontinued
0.7987 Intermediate Similarity NPD1240 Approved
0.7964 Intermediate Similarity NPD7768 Phase 2
0.7962 Intermediate Similarity NPD2796 Approved
0.7952 Intermediate Similarity NPD1465 Phase 2
0.7952 Intermediate Similarity NPD7819 Suspended
0.7941 Intermediate Similarity NPD6232 Discontinued
0.7919 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD7473 Discontinued
0.7901 Intermediate Similarity NPD5401 Approved
0.7895 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD1607 Approved
0.7875 Intermediate Similarity NPD3750 Approved
0.787 Intermediate Similarity NPD919 Approved
0.7784 Intermediate Similarity NPD6559 Discontinued
0.7778 Intermediate Similarity NPD1247 Approved
0.7714 Intermediate Similarity NPD5844 Phase 1
0.7688 Intermediate Similarity NPD2344 Approved
0.7674 Intermediate Similarity NPD7199 Phase 2
0.7673 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD7390 Discontinued
0.7613 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD2800 Approved
0.7562 Intermediate Similarity NPD3748 Approved
0.7548 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD1551 Phase 2
0.7514 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2309 Approved
0.75 Intermediate Similarity NPD6190 Approved
0.7486 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1243 Approved
0.7458 Intermediate Similarity NPD3751 Discontinued
0.7457 Intermediate Similarity NPD6234 Discontinued
0.7433 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD3787 Discontinued
0.7421 Intermediate Similarity NPD1613 Approved
0.7421 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD2935 Discontinued
0.7405 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD3226 Approved
0.7375 Intermediate Similarity NPD230 Phase 1
0.7365 Intermediate Similarity NPD2533 Approved
0.7365 Intermediate Similarity NPD2534 Approved
0.7365 Intermediate Similarity NPD2532 Approved
0.7349 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD8313 Approved
0.7308 Intermediate Similarity NPD1203 Approved
0.7308 Intermediate Similarity NPD8312 Approved
0.7301 Intermediate Similarity NPD5404 Approved
0.7301 Intermediate Similarity NPD6100 Approved
0.7301 Intermediate Similarity NPD5405 Approved
0.7301 Intermediate Similarity NPD5406 Approved
0.7301 Intermediate Similarity NPD5408 Approved
0.7301 Intermediate Similarity NPD6099 Approved
0.7297 Intermediate Similarity NPD4287 Approved
0.7296 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD4908 Phase 1
0.7278 Intermediate Similarity NPD920 Approved
0.7267 Intermediate Similarity NPD447 Suspended
0.7263 Intermediate Similarity NPD7228 Approved
0.7262 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4967 Phase 2
0.7241 Intermediate Similarity NPD4966 Approved
0.7241 Intermediate Similarity NPD4965 Approved
0.7239 Intermediate Similarity NPD2799 Discontinued
0.7238 Intermediate Similarity NPD5953 Discontinued
0.7229 Intermediate Similarity NPD4628 Phase 3
0.7222 Intermediate Similarity NPD6651 Approved
0.7188 Intermediate Similarity NPD2313 Discontinued
0.7188 Intermediate Similarity NPD6798 Discontinued
0.7188 Intermediate Similarity NPD3764 Approved
0.7188 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1471 Phase 3
0.7135 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD3027 Phase 3
0.7097 Intermediate Similarity NPD8434 Phase 2
0.707 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD37 Approved
0.7063 Intermediate Similarity NPD6832 Phase 2
0.7056 Intermediate Similarity NPD2403 Approved
0.7055 Intermediate Similarity NPD1933 Approved
0.7051 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD2346 Discontinued
0.7047 Intermediate Similarity NPD6777 Approved
0.7047 Intermediate Similarity NPD6776 Approved
0.7047 Intermediate Similarity NPD6779 Approved
0.7047 Intermediate Similarity NPD6780 Approved
0.7047 Intermediate Similarity NPD6778 Approved
0.7047 Intermediate Similarity NPD6781 Approved
0.7047 Intermediate Similarity NPD6782 Approved
0.7044 Intermediate Similarity NPD2798 Approved
0.7035 Intermediate Similarity NPD1653 Approved
0.7033 Intermediate Similarity NPD7286 Phase 2
0.7026 Intermediate Similarity NPD7435 Discontinued
0.7006 Intermediate Similarity NPD9717 Approved
0.7006 Intermediate Similarity NPD9269 Phase 2
0.7 Intermediate Similarity NPD9494 Approved
0.6994 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6989 Remote Similarity NPD2296 Approved
0.6989 Remote Similarity NPD4288 Approved
0.6982 Remote Similarity NPD2354 Approved
0.6981 Remote Similarity NPD1470 Approved
0.6975 Remote Similarity NPD3268 Approved
0.6964 Remote Similarity NPD2654 Approved
0.6961 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6951 Remote Similarity NPD6355 Discontinued
0.6944 Remote Similarity NPD7229 Phase 3
0.6943 Remote Similarity NPD1201 Approved
0.6943 Remote Similarity NPD1610 Phase 2
0.6935 Remote Similarity NPD8151 Discontinued
0.6933 Remote Similarity NPD6233 Phase 2
0.6932 Remote Similarity NPD8455 Phase 2
0.6928 Remote Similarity NPD7033 Discontinued
0.6928 Remote Similarity NPD4308 Phase 3
0.6919 Remote Similarity NPD7685 Pre-registration
0.6918 Remote Similarity NPD3225 Approved
0.6915 Remote Similarity NPD8150 Discontinued
0.6914 Remote Similarity NPD7095 Approved
0.691 Remote Similarity NPD6971 Discontinued
0.6904 Remote Similarity NPD7870 Phase 2
0.6904 Remote Similarity NPD7871 Phase 2
0.6903 Remote Similarity NPD1548 Phase 1
0.6899 Remote Similarity NPD1608 Approved
0.6897 Remote Similarity NPD7458 Discontinued
0.6885 Remote Similarity NPD2163 Approved
0.6885 Remote Similarity NPD7177 Discontinued
0.6875 Remote Similarity NPD2797 Approved
0.6871 Remote Similarity NPD411 Approved
0.6853 Remote Similarity NPD7698 Approved
0.6853 Remote Similarity NPD7697 Approved
0.6853 Remote Similarity NPD7696 Phase 3
0.6851 Remote Similarity NPD5711 Approved
0.6851 Remote Similarity NPD5710 Approved
0.6848 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4361 Phase 2
0.6835 Remote Similarity NPD422 Phase 1
0.6828 Remote Similarity NPD7240 Approved
0.6824 Remote Similarity NPD8166 Discontinued
0.6824 Remote Similarity NPD7003 Approved
0.6821 Remote Similarity NPD5049 Phase 3
0.6821 Remote Similarity NPD6273 Approved
0.6816 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6816 Remote Similarity NPD7874 Approved
0.6811 Remote Similarity NPD1729 Discontinued
0.681 Remote Similarity NPD4625 Phase 3
0.68 Remote Similarity NPD7701 Phase 2
0.6796 Remote Similarity NPD8127 Discontinued

  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