Structure

Physi-Chem Properties

Molecular Weight:  432.13
Volume:  427.556
LogP:  3.936
LogD:  2.579
LogS:  -4.828
# Rotatable Bonds:  6
TPSA:  89.9
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.509
Synthetic Accessibility Score:  5.073
Fsp3:  0.435
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.76
MDCK Permeability:  1.927803532453254e-05
Pgp-inhibitor:  0.361
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.056
20% Bioavailability (F20%):  0.906
30% Bioavailability (F30%):  0.9

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.186
Plasma Protein Binding (PPB):  80.5150146484375%
Volume Distribution (VD):  2.269
Pgp-substrate:  9.466207504272461%

ADMET: Metabolism

CYP1A2-inhibitor:  0.952
CYP1A2-substrate:  0.688
CYP2C19-inhibitor:  0.935
CYP2C19-substrate:  0.571
CYP2C9-inhibitor:  0.914
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.94
CYP2D6-substrate:  0.013
CYP3A4-inhibitor:  0.961
CYP3A4-substrate:  0.302

ADMET: Excretion

Clearance (CL):  2.065
Half-life (T1/2):  0.156

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.941
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.483
Rat Oral Acute Toxicity:  0.771
Maximum Recommended Daily Dose:  0.889
Skin Sensitization:  0.921
Carcinogencity:  0.931
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.951

Download Data

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

  Natural Product: NPC232969

Natural Product ID:  NPC232969
Common Name*:   (6As)-5-Chloro-9-[(2R,3R)-3-Hydroxy-2-Methylbutanoyl]-6A-Methyl-3-[(E,3S)-3-Methylpent-1-Enyl]Furo[2,3-H]Isochromene-6,8-Dione
IUPAC Name:   (6aS)-5-chloro-9-[(2R,3R)-3-hydroxy-2-methylbutanoyl]-6a-methyl-3-[(E,3S)-3-methylpent-1-enyl]furo[2,3-h]isochromene-6,8-dione
Synonyms:   4'-Epichaetoviridin A
Standard InCHIKey:  HWSQVPGTQUYLEQ-LYUOGRNPSA-N
Standard InCHI:  InChI=1S/C23H25ClO6/c1-6-11(2)7-8-14-9-15-16(10-29-14)18-17(20(26)12(3)13(4)25)22(28)30-23(18,5)21(27)19(15)24/h7-13,25H,6H2,1-5H3/b8-7+/t11-,12+,13+,23-/m0/s1
SMILES:  CC[C@@H](/C=C/C1=CC2=C(Cl)C(=O)[C@@]3(C(=C(C(=O)O3)C(=O)[C@@H]([C@H](O)C)C)C2=CO1)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1306556
PubChem CID:   23641105
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003487] Cyclic ketones
              • [CHEMONTID:0004325] Cyclohexenones

*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
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[12357398]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[12483566]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[15497948]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[15921417]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[16209910]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[16499339]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[16872138]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[16904330]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[17125234]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[17827664]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[19246197]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota Ginkgo biloba n.a. n.a. PMID[19246197]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[19427327]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[20225834]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[20814854]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[21548578]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota isolated from the leaves of Viguiera robusta n.a. n.a. PMID[21548578]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. mycelium n.a. PMID[21548578]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[21640594]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[21854043]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[22112725]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[22593034]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[23072467]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. Xichang of Sichuan Province, China n.a. PMID[26125976]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[26343828]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[5066072]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[7116505]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[CiteXplore Id]
NPO24171 Chaetomium globosum Species Chaetomiaceae 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
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 56234.1 nM PMID[479882]
NPT4 Individual Protein Large T antigen Simian virus 40 EC50 > 50000.0 nM PMID[479882]
NPT4 Individual Protein Large T antigen Simian virus 40 IC50 n.a. 43960.0 nM PMID[479882]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 19952.6 nM PMID[479882]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 50118.7 nM PMID[479882]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 56234.1 nM PMID[479882]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 11220.2 nM PMID[479882]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 11220.2 nM PMID[479882]
NPT2971 Individual Protein DNA dC->dU-editing enzyme APOBEC-3F Homo sapiens Potency n.a. 19952.6 nM PMID[479882]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 25929.0 nM PMID[479882]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 11917.3 nM PMID[479882]
NPT159 Individual Protein Aberrant vpr protein Human immunodeficiency virus 1 Potency n.a. 35481.3 nM PMID[479882]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 11220.2 nM PMID[479882]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 18356.4 nM PMID[479882]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[479882]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 35300.0 nM PMID[479884]
NPT161 Individual Protein Rap guanine nucleotide exchange factor 4 Homo sapiens Potency n.a. 50118.7 nM PMID[479882]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 50118.7 nM PMID[479882]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 25118.9 nM PMID[479882]
NPT446 Individual Protein Rap guanine nucleotide exchange factor 3 Homo sapiens Potency n.a. 50118.7 nM PMID[479882]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 112201.8 nM PMID[479882]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 70794.6 nM PMID[479882]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 25118.9 nM PMID[479882]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 19952.6 nM PMID[479882]
NPT698 Individual Protein Regulator of G-protein signaling 4 Homo sapiens Potency n.a. 17782.8 nM PMID[479882]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 17782.8 nM PMID[479882]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[479882]
NPT918 Individual Protein Heat shock protein HSP 90-alpha Homo sapiens AC50 = 7412.0 nM PMID[479882]
NPT919 Individual Protein HSP90 Plasmodium falciparum 3D7 AC50 = 15189.0 nM PMID[479882]
NPT821 Individual Protein Werner syndrome ATP-dependent helicase Homo sapiens Potency n.a. 50118.7 nM PMID[479882]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 50118.7 nM PMID[479882]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens Potency n.a. 5972.8 nM PMID[479882]
NPT2 Others Unspecified Potency n.a. 22387.2 nM PMID[479882]
NPT2 Others Unspecified Potency n.a. 17782.8 nM PMID[479882]

☑ 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 NPC232969 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
1.0 High Similarity NPC199107
0.8878 High Similarity NPC143210
0.8788 High Similarity NPC12727
0.8407 Intermediate Similarity NPC476815
0.8384 Intermediate Similarity NPC224270
0.8365 Intermediate Similarity NPC224172
0.8365 Intermediate Similarity NPC469851
0.8364 Intermediate Similarity NPC321496
0.83 Intermediate Similarity NPC32552
0.8224 Intermediate Similarity NPC469852
0.8131 Intermediate Similarity NPC272528
0.8087 Intermediate Similarity NPC31641
0.8061 Intermediate Similarity NPC281172
0.8 Intermediate Similarity NPC245320
0.798 Intermediate Similarity NPC291712
0.7941 Intermediate Similarity NPC32944
0.7941 Intermediate Similarity NPC193396
0.7941 Intermediate Similarity NPC166110
0.7931 Intermediate Similarity NPC473145
0.7921 Intermediate Similarity NPC95364
0.7921 Intermediate Similarity NPC142159
0.787 Intermediate Similarity NPC297281
0.787 Intermediate Similarity NPC473144
0.7864 Intermediate Similarity NPC282644
0.7864 Intermediate Similarity NPC29798
0.7864 Intermediate Similarity NPC248193
0.7757 Intermediate Similarity NPC215253
0.7757 Intermediate Similarity NPC185253
0.7672 Intermediate Similarity NPC243298
0.7664 Intermediate Similarity NPC166770
0.7658 Intermediate Similarity NPC469853
0.7589 Intermediate Similarity NPC327106
0.757 Intermediate Similarity NPC134083
0.757 Intermediate Similarity NPC245521
0.7565 Intermediate Similarity NPC326264
0.7525 Intermediate Similarity NPC67081
0.7525 Intermediate Similarity NPC471223
0.75 Intermediate Similarity NPC274075
0.7478 Intermediate Similarity NPC66108
0.7387 Intermediate Similarity NPC271059
0.7387 Intermediate Similarity NPC25666
0.7383 Intermediate Similarity NPC471698
0.7368 Intermediate Similarity NPC38154
0.7273 Intermediate Similarity NPC54705
0.7217 Intermediate Similarity NPC23497
0.7193 Intermediate Similarity NPC266514
0.7172 Intermediate Similarity NPC264391
0.717 Intermediate Similarity NPC316228
0.717 Intermediate Similarity NPC473455
0.7157 Intermediate Similarity NPC16488
0.7156 Intermediate Similarity NPC318082
0.7143 Intermediate Similarity NPC197835
0.7143 Intermediate Similarity NPC235369
0.7143 Intermediate Similarity NPC303653
0.7143 Intermediate Similarity NPC291500
0.7143 Intermediate Similarity NPC189609
0.7143 Intermediate Similarity NPC140591
0.7094 Intermediate Similarity NPC324683
0.7091 Intermediate Similarity NPC208094
0.708 Intermediate Similarity NPC320294
0.7075 Intermediate Similarity NPC87306
0.7064 Intermediate Similarity NPC31021
0.7064 Intermediate Similarity NPC214694
0.7064 Intermediate Similarity NPC295347
0.7054 Intermediate Similarity NPC472753
0.7048 Intermediate Similarity NPC113370
0.7048 Intermediate Similarity NPC476079
0.7048 Intermediate Similarity NPC473248
0.7048 Intermediate Similarity NPC103743
0.7027 Intermediate Similarity NPC35717
0.7027 Intermediate Similarity NPC300584
0.7025 Intermediate Similarity NPC21326
0.7019 Intermediate Similarity NPC307112
0.7009 Intermediate Similarity NPC89408
0.7009 Intermediate Similarity NPC475879
0.7 Intermediate Similarity NPC473291
0.6991 Remote Similarity NPC472754
0.699 Remote Similarity NPC475083
0.6983 Remote Similarity NPC264819
0.6983 Remote Similarity NPC322903
0.6981 Remote Similarity NPC153570
0.6972 Remote Similarity NPC477241
0.6972 Remote Similarity NPC469632
0.6957 Remote Similarity NPC469607
0.6952 Remote Similarity NPC47220
0.6952 Remote Similarity NPC261721
0.6952 Remote Similarity NPC315395
0.6952 Remote Similarity NPC186332
0.6952 Remote Similarity NPC316426
0.6937 Remote Similarity NPC239895
0.6937 Remote Similarity NPC20066
0.693 Remote Similarity NPC475945
0.693 Remote Similarity NPC475871
0.693 Remote Similarity NPC104161
0.693 Remote Similarity NPC469980
0.693 Remote Similarity NPC118902
0.6923 Remote Similarity NPC474251
0.6923 Remote Similarity NPC469884
0.6903 Remote Similarity NPC474742
0.69 Remote Similarity NPC471225
0.6897 Remote Similarity NPC254538
0.6897 Remote Similarity NPC474285
0.6881 Remote Similarity NPC476049
0.6875 Remote Similarity NPC221414
0.6875 Remote Similarity NPC471144
0.6875 Remote Similarity NPC161855
0.6864 Remote Similarity NPC478209
0.6864 Remote Similarity NPC206595
0.6857 Remote Similarity NPC155873
0.6852 Remote Similarity NPC131864
0.685 Remote Similarity NPC476008
0.6847 Remote Similarity NPC172998
0.6847 Remote Similarity NPC301596
0.6847 Remote Similarity NPC299396
0.6842 Remote Similarity NPC273005
0.6842 Remote Similarity NPC474747
0.6842 Remote Similarity NPC31058
0.6842 Remote Similarity NPC149371
0.6842 Remote Similarity NPC469606
0.6838 Remote Similarity NPC473807
0.6838 Remote Similarity NPC89171
0.6838 Remote Similarity NPC472507
0.6838 Remote Similarity NPC476802
0.6833 Remote Similarity NPC469463
0.6833 Remote Similarity NPC469454
0.6833 Remote Similarity NPC474271
0.6833 Remote Similarity NPC469496
0.6822 Remote Similarity NPC472008
0.6822 Remote Similarity NPC475902
0.6818 Remote Similarity NPC475832
0.6818 Remote Similarity NPC475927
0.6814 Remote Similarity NPC472972
0.6814 Remote Similarity NPC475949
0.6814 Remote Similarity NPC469551
0.681 Remote Similarity NPC478208
0.6807 Remote Similarity NPC317107
0.6807 Remote Similarity NPC179798
0.6807 Remote Similarity NPC304180
0.6803 Remote Similarity NPC471145
0.6792 Remote Similarity NPC122502
0.6792 Remote Similarity NPC164393
0.6789 Remote Similarity NPC327760
0.6789 Remote Similarity NPC142838
0.6789 Remote Similarity NPC45579
0.6789 Remote Similarity NPC472705
0.6789 Remote Similarity NPC303230
0.6789 Remote Similarity NPC20713
0.6789 Remote Similarity NPC6099
0.6789 Remote Similarity NPC114345
0.6786 Remote Similarity NPC53844
0.6783 Remote Similarity NPC472755
0.6783 Remote Similarity NPC472750
0.6783 Remote Similarity NPC472747
0.678 Remote Similarity NPC137911
0.678 Remote Similarity NPC20192
0.678 Remote Similarity NPC228477
0.6772 Remote Similarity NPC477745
0.6768 Remote Similarity NPC470686
0.6762 Remote Similarity NPC38569
0.6762 Remote Similarity NPC163615
0.6762 Remote Similarity NPC219966
0.6759 Remote Similarity NPC295312
0.6759 Remote Similarity NPC51358
0.6759 Remote Similarity NPC307092
0.6759 Remote Similarity NPC78008
0.6757 Remote Similarity NPC209355
0.6757 Remote Similarity NPC272050
0.6757 Remote Similarity NPC273197
0.6757 Remote Similarity NPC234339
0.6754 Remote Similarity NPC47880
0.6754 Remote Similarity NPC471412
0.6754 Remote Similarity NPC244456
0.6754 Remote Similarity NPC469657
0.6754 Remote Similarity NPC201718
0.6754 Remote Similarity NPC472643
0.6754 Remote Similarity NPC471699
0.675 Remote Similarity NPC317687
0.6748 Remote Similarity NPC284707
0.6748 Remote Similarity NPC315974
0.6746 Remote Similarity NPC120724
0.6729 Remote Similarity NPC160138
0.6729 Remote Similarity NPC86005
0.6729 Remote Similarity NPC471738
0.6729 Remote Similarity NPC477959
0.6726 Remote Similarity NPC264378
0.6724 Remote Similarity NPC474741
0.6724 Remote Similarity NPC472756
0.6724 Remote Similarity NPC472748
0.6723 Remote Similarity NPC472508
0.6723 Remote Similarity NPC5103
0.6721 Remote Similarity NPC478216
0.672 Remote Similarity NPC472000
0.672 Remote Similarity NPC471999
0.6698 Remote Similarity NPC242233
0.6697 Remote Similarity NPC265856
0.6697 Remote Similarity NPC71533
0.6697 Remote Similarity NPC106510
0.6697 Remote Similarity NPC166554
0.6696 Remote Similarity NPC135576
0.6696 Remote Similarity NPC93271

  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 NPC232969 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
0.6727 Remote Similarity NPD5778 Approved
0.6727 Remote Similarity NPD5779 Approved
0.6612 Remote Similarity NPD6053 Discontinued
0.6509 Remote Similarity NPD6110 Phase 1
0.6486 Remote Similarity NPD7983 Approved
0.648 Remote Similarity NPD6335 Approved
0.648 Remote Similarity NPD6313 Approved
0.648 Remote Similarity NPD6314 Approved
0.6457 Remote Similarity NPD8513 Phase 3
0.6457 Remote Similarity NPD5983 Phase 2
0.6408 Remote Similarity NPD4756 Discovery
0.6385 Remote Similarity NPD6336 Discontinued
0.6372 Remote Similarity NPD5282 Discontinued
0.6328 Remote Similarity NPD8516 Approved
0.6328 Remote Similarity NPD8517 Approved
0.6328 Remote Similarity NPD8515 Approved
0.632 Remote Similarity NPD6868 Approved
0.6306 Remote Similarity NPD6101 Approved
0.6306 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6299 Remote Similarity NPD7100 Approved
0.6299 Remote Similarity NPD7101 Approved
0.6293 Remote Similarity NPD8029 Clinical (unspecified phase)
0.629 Remote Similarity NPD4632 Approved
0.6288 Remote Similarity NPD6033 Approved
0.627 Remote Similarity NPD6009 Approved
0.6262 Remote Similarity NPD5209 Approved
0.6261 Remote Similarity NPD7839 Suspended
0.625 Remote Similarity NPD6319 Approved
0.625 Remote Similarity NPD6698 Approved
0.625 Remote Similarity NPD46 Approved
0.6198 Remote Similarity NPD5697 Approved
0.6195 Remote Similarity NPD7637 Suspended
0.6195 Remote Similarity NPD6411 Approved
0.6174 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7638 Approved
0.6148 Remote Similarity NPD6899 Approved
0.6148 Remote Similarity NPD6881 Approved
0.6148 Remote Similarity NPD6011 Approved
0.6142 Remote Similarity NPD7115 Discovery
0.6116 Remote Similarity NPD7128 Approved
0.6116 Remote Similarity NPD6675 Approved
0.6116 Remote Similarity NPD6402 Approved
0.6116 Remote Similarity NPD5739 Approved
0.6106 Remote Similarity NPD7838 Discovery
0.6106 Remote Similarity NPD5785 Approved
0.6102 Remote Similarity NPD7639 Approved
0.6102 Remote Similarity NPD7640 Approved
0.6098 Remote Similarity NPD6012 Approved
0.6098 Remote Similarity NPD6013 Approved
0.6098 Remote Similarity NPD6014 Approved
0.609 Remote Similarity NPD8074 Phase 3
0.6075 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6066 Remote Similarity NPD5701 Approved
0.6066 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6061 Remote Similarity NPD7492 Approved
0.6055 Remote Similarity NPD7154 Phase 3
0.6048 Remote Similarity NPD7290 Approved
0.6048 Remote Similarity NPD6883 Approved
0.6048 Remote Similarity NPD5169 Approved
0.6048 Remote Similarity NPD7102 Approved
0.6036 Remote Similarity NPD4249 Approved
0.6036 Remote Similarity NPD5786 Approved
0.6034 Remote Similarity NPD5654 Approved
0.6029 Remote Similarity NPD7260 Phase 2
0.6016 Remote Similarity NPD7320 Approved
0.6015 Remote Similarity NPD6616 Approved
0.6 Remote Similarity NPD6869 Approved
0.6 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6 Remote Similarity NPD8130 Phase 1
0.6 Remote Similarity NPD6617 Approved
0.6 Remote Similarity NPD6650 Approved
0.6 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6 Remote Similarity NPD6649 Approved
0.6 Remote Similarity NPD5127 Approved
0.6 Remote Similarity NPD6054 Approved
0.6 Remote Similarity NPD6847 Approved
0.5983 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5982 Remote Similarity NPD4251 Approved
0.5982 Remote Similarity NPD4250 Approved
0.597 Remote Similarity NPD7078 Approved
0.5968 Remote Similarity NPD6373 Approved
0.5968 Remote Similarity NPD6372 Approved
0.5954 Remote Similarity NPD6016 Approved
0.5954 Remote Similarity NPD6015 Approved
0.5952 Remote Similarity NPD8297 Approved
0.5952 Remote Similarity NPD6882 Approved
0.5946 Remote Similarity NPD5363 Approved
0.5932 Remote Similarity NPD6083 Phase 2
0.5932 Remote Similarity NPD6084 Phase 2
0.5932 Remote Similarity NPD5959 Approved
0.5926 Remote Similarity NPD4252 Approved
0.5926 Remote Similarity NPD7736 Approved
0.592 Remote Similarity NPD6371 Approved
0.5909 Remote Similarity NPD6370 Approved
0.5909 Remote Similarity NPD5988 Approved
0.5897 Remote Similarity NPD5695 Phase 3
0.5887 Remote Similarity NPD5168 Approved
0.5887 Remote Similarity NPD5128 Approved
0.5887 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4225 Approved
0.5878 Remote Similarity NPD6059 Approved
0.5873 Remote Similarity NPD1719 Phase 1
0.5873 Remote Similarity NPD5216 Approved
0.5873 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5873 Remote Similarity NPD5215 Approved
0.5873 Remote Similarity NPD5217 Approved
0.5872 Remote Similarity NPD5369 Approved
0.5865 Remote Similarity NPD7604 Phase 2
0.5859 Remote Similarity NPD5167 Approved
0.5852 Remote Similarity NPD8293 Discontinued
0.584 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5839 Remote Similarity NPD5956 Approved
0.5818 Remote Similarity NPD4269 Approved
0.5818 Remote Similarity NPD4270 Approved
0.5816 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5804 Remote Similarity NPD1696 Phase 3
0.5804 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5804 Remote Similarity NPD1694 Approved
0.5794 Remote Similarity NPD4634 Approved
0.5789 Remote Similarity NPD8080 Discontinued
0.5776 Remote Similarity NPD5693 Phase 1
0.5776 Remote Similarity NPD5694 Approved
0.5769 Remote Similarity NPD6317 Approved
0.5766 Remote Similarity NPD7319 Approved
0.576 Remote Similarity NPD6686 Approved
0.575 Remote Similarity NPD5696 Approved
0.5746 Remote Similarity NPD7829 Approved
0.5746 Remote Similarity NPD8328 Phase 3
0.5746 Remote Similarity NPD7830 Approved
0.5743 Remote Similarity NPD3704 Approved
0.5738 Remote Similarity NPD5211 Phase 2
0.5726 Remote Similarity NPD5048 Discontinued
0.5726 Remote Similarity NPD6008 Approved
0.5714 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8444 Approved
0.5714 Remote Similarity NPD5222 Approved
0.5714 Remote Similarity NPD5221 Approved
0.5714 Remote Similarity NPD7503 Approved
0.5702 Remote Similarity NPD5285 Approved
0.5702 Remote Similarity NPD5286 Approved
0.5702 Remote Similarity NPD4696 Approved
0.5702 Remote Similarity NPD6648 Approved
0.5692 Remote Similarity NPD6274 Approved
0.569 Remote Similarity NPD5692 Phase 3
0.5682 Remote Similarity NPD4522 Approved
0.568 Remote Similarity NPD6614 Approved
0.5676 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5676 Remote Similarity NPD6435 Approved
0.5669 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5669 Remote Similarity NPD2067 Discontinued
0.5667 Remote Similarity NPD4755 Approved
0.5667 Remote Similarity NPD5173 Approved
0.5662 Remote Similarity NPD7507 Approved
0.5656 Remote Similarity NPD5223 Approved
0.5656 Remote Similarity NPD5344 Discontinued
0.5652 Remote Similarity NPD6672 Approved
0.5652 Remote Similarity NPD5737 Approved
0.5645 Remote Similarity NPD5141 Approved
0.5643 Remote Similarity NPD6845 Suspended
0.5641 Remote Similarity NPD6050 Approved
0.5641 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5636 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5625 Remote Similarity NPD5362 Discontinued
0.5614 Remote Similarity NPD5279 Phase 3
0.561 Remote Similarity NPD5225 Approved
0.561 Remote Similarity NPD5224 Approved
0.561 Remote Similarity NPD5226 Approved
0.561 Remote Similarity NPD7632 Discontinued
0.561 Remote Similarity NPD4633 Approved
0.5607 Remote Similarity NPD8039 Approved
0.5603 Remote Similarity NPD5370 Suspended
0.5603 Remote Similarity NPD7285 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