Structure

Physi-Chem Properties

Molecular Weight:  416.14
Volume:  412.845
LogP:  5.163
LogD:  4.244
LogS:  -5.701
# Rotatable Bonds:  3
TPSA:  61.83
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.624
Synthetic Accessibility Score:  5.314
Fsp3:  0.478
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.735
MDCK Permeability:  1.080827132682316e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.062
Plasma Protein Binding (PPB):  82.77605438232422%
Volume Distribution (VD):  2.722
Pgp-substrate:  11.72517204284668%

ADMET: Metabolism

CYP1A2-inhibitor:  0.956
CYP1A2-substrate:  0.367
CYP2C19-inhibitor:  0.959
CYP2C19-substrate:  0.601
CYP2C9-inhibitor:  0.926
CYP2C9-substrate:  0.027
CYP2D6-inhibitor:  0.921
CYP2D6-substrate:  0.018
CYP3A4-inhibitor:  0.957
CYP3A4-substrate:  0.677

ADMET: Excretion

Clearance (CL):  3.855
Half-life (T1/2):  0.062

ADMET: Toxicity

hERG Blockers:  0.047
Human Hepatotoxicity (H-HT):  0.956
Drug-inuced Liver Injury (DILI):  0.931
AMES Toxicity:  0.208
Rat Oral Acute Toxicity:  0.874
Maximum Recommended Daily Dose:  0.908
Skin Sensitization:  0.94
Carcinogencity:  0.849
Eye Corrosion:  0.013
Eye Irritation:  0.044
Respiratory Toxicity:  0.984

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

  Natural Product: NPC272528

Natural Product ID:  NPC272528
Common Name*:   PQCNMEKFPHIIHE-QESWSWRDSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  PQCNMEKFPHIIHE-QESWSWRDSA-N
Standard InCHI:  InChI=1S/C23H25ClO5/c1-6-11(2)7-8-14-9-15-16(10-27-14)18-17-20(12(3)13(4)28-22(17)26)29-23(18,5)21(25)19(15)24/h7-13,18H,6H2,1-5H3/b8-7+/t11-,12+,13+,18+,23-/m0/s1
SMILES:  CC[C@@H](/C=C/C1=CC2=C(Cl)C(=O)[C@@]3([C@H](C2=CO1)C1=C(O3)[C@@H]([C@H](OC1=O)C)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3621758
PubChem CID:   25141203
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000086] Pyrans
        • [CHEMONTID:0000481] Pyranones and derivatives
          • [CHEMONTID:0001211] Dihydropyranones

*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 Ginkgo biloba n.a. n.a. PMID[19246197]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. 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. mycelium n.a. PMID[21548578]
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. 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
NPT71 Cell Line HEK293 Homo sapiens Survival = 82.8 % PMID[528124]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 99.3 % PMID[528124]
NPT113 Cell Line RAW264.7 Mus musculus Survival = 28.5 % PMID[528124]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1900.0 nM PMID[528124]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 20700.0 nM PMID[528124]
NPT2 Others Unspecified Inhibition = 97.7 % PMID[528124]
NPT2 Others Unspecified IC50 = 5100.0 nM PMID[528124]

☑ 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 NPC272528 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
0.8624 High Similarity NPC243298
0.8485 Intermediate Similarity NPC143210
0.8468 Intermediate Similarity NPC245320
0.84 Intermediate Similarity NPC12727
0.8393 Intermediate Similarity NPC473145
0.8393 Intermediate Similarity NPC31641
0.8367 Intermediate Similarity NPC224270
0.823 Intermediate Similarity NPC476815
0.8131 Intermediate Similarity NPC232969
0.8131 Intermediate Similarity NPC199107
0.8077 Intermediate Similarity NPC185253
0.8077 Intermediate Similarity NPC215253
0.8058 Intermediate Similarity NPC134083
0.8019 Intermediate Similarity NPC271059
0.8019 Intermediate Similarity NPC25666
0.7981 Intermediate Similarity NPC166770
0.785 Intermediate Similarity NPC297281
0.785 Intermediate Similarity NPC473144
0.783 Intermediate Similarity NPC224172
0.7788 Intermediate Similarity NPC318082
0.7677 Intermediate Similarity NPC281172
0.7664 Intermediate Similarity NPC469851
0.76 Intermediate Similarity NPC291712
0.7573 Intermediate Similarity NPC32944
0.7573 Intermediate Similarity NPC193396
0.7573 Intermediate Similarity NPC166110
0.7549 Intermediate Similarity NPC95364
0.7549 Intermediate Similarity NPC142159
0.7524 Intermediate Similarity NPC31021
0.75 Intermediate Similarity NPC248193
0.7404 Intermediate Similarity NPC32552
0.7387 Intermediate Similarity NPC469852
0.7339 Intermediate Similarity NPC471699
0.7321 Intermediate Similarity NPC469853
0.7196 Intermediate Similarity NPC471698
0.7143 Intermediate Similarity NPC469372
0.7105 Intermediate Similarity NPC327106
0.7094 Intermediate Similarity NPC321496
0.7043 Intermediate Similarity NPC137911
0.7043 Intermediate Similarity NPC228477
0.7041 Intermediate Similarity NPC471225
0.7037 Intermediate Similarity NPC295347
0.7009 Intermediate Similarity NPC66108
0.7009 Intermediate Similarity NPC476598
0.7009 Intermediate Similarity NPC1108
0.7009 Intermediate Similarity NPC476597
0.6981 Remote Similarity NPC471818
0.6981 Remote Similarity NPC220454
0.6981 Remote Similarity NPC212679
0.6981 Remote Similarity NPC469595
0.6972 Remote Similarity NPC301596
0.6972 Remote Similarity NPC172998
0.6972 Remote Similarity NPC299396
0.6949 Remote Similarity NPC326264
0.6944 Remote Similarity NPC476596
0.6923 Remote Similarity NPC203795
0.6909 Remote Similarity NPC208094
0.6909 Remote Similarity NPC84335
0.6909 Remote Similarity NPC38530
0.6897 Remote Similarity NPC23497
0.6887 Remote Similarity NPC284561
0.6881 Remote Similarity NPC273197
0.6881 Remote Similarity NPC234339
0.6875 Remote Similarity NPC244456
0.6875 Remote Similarity NPC469657
0.6852 Remote Similarity NPC165383
0.6852 Remote Similarity NPC282644
0.6852 Remote Similarity NPC29798
0.6827 Remote Similarity NPC471060
0.6814 Remote Similarity NPC235369
0.6807 Remote Similarity NPC474271
0.6796 Remote Similarity NPC288281
0.6792 Remote Similarity NPC471057
0.6792 Remote Similarity NPC471058
0.6792 Remote Similarity NPC475902
0.6792 Remote Similarity NPC472302
0.6789 Remote Similarity NPC477129
0.6789 Remote Similarity NPC477130
0.6789 Remote Similarity NPC38830
0.6783 Remote Similarity NPC477125
0.6783 Remote Similarity NPC472645
0.6765 Remote Similarity NPC42470
0.6733 Remote Similarity NPC178277
0.6729 Remote Similarity NPC280833
0.6729 Remote Similarity NPC471054
0.6726 Remote Similarity NPC168319
0.6726 Remote Similarity NPC194028
0.6726 Remote Similarity NPC472643
0.6726 Remote Similarity NPC473384
0.6724 Remote Similarity NPC133422
0.67 Remote Similarity NPC473825
0.6699 Remote Similarity NPC268122
0.6699 Remote Similarity NPC471326
0.6699 Remote Similarity NPC173609
0.6699 Remote Similarity NPC221231
0.6696 Remote Similarity NPC54843
0.6696 Remote Similarity NPC474898
0.6695 Remote Similarity NPC206595
0.6667 Remote Similarity NPC112654
0.6667 Remote Similarity NPC264819
0.6667 Remote Similarity NPC260796
0.6667 Remote Similarity NPC273005
0.6667 Remote Similarity NPC189609
0.6667 Remote Similarity NPC140591
0.6667 Remote Similarity NPC303653
0.6667 Remote Similarity NPC130030
0.6667 Remote Similarity NPC291500
0.6667 Remote Similarity NPC469606
0.6667 Remote Similarity NPC197835
0.6667 Remote Similarity NPC31058
0.6639 Remote Similarity NPC179798
0.6639 Remote Similarity NPC304180
0.6638 Remote Similarity NPC266570
0.6638 Remote Similarity NPC478052
0.6638 Remote Similarity NPC34768
0.6638 Remote Similarity NPC469607
0.6637 Remote Similarity NPC110897
0.6636 Remote Similarity NPC473658
0.6636 Remote Similarity NPC26078
0.6635 Remote Similarity NPC474703
0.6635 Remote Similarity NPC193198
0.6635 Remote Similarity NPC118423
0.661 Remote Similarity NPC469370
0.6609 Remote Similarity NPC471364
0.6609 Remote Similarity NPC320294
0.6609 Remote Similarity NPC471365
0.6609 Remote Similarity NPC132395
0.6607 Remote Similarity NPC110937
0.6604 Remote Similarity NPC220478
0.6604 Remote Similarity NPC279859
0.6604 Remote Similarity NPC168248
0.6604 Remote Similarity NPC38576
0.6602 Remote Similarity NPC471325
0.6602 Remote Similarity NPC275507
0.6583 Remote Similarity NPC147180
0.6583 Remote Similarity NPC221144
0.6583 Remote Similarity NPC264634
0.6581 Remote Similarity NPC266514
0.6577 Remote Similarity NPC470978
0.6577 Remote Similarity NPC470974
0.6577 Remote Similarity NPC474947
0.6574 Remote Similarity NPC307092
0.6574 Remote Similarity NPC474844
0.6574 Remote Similarity NPC51358
0.6571 Remote Similarity NPC474359
0.6571 Remote Similarity NPC149869
0.6571 Remote Similarity NPC30486
0.6571 Remote Similarity NPC159635
0.6569 Remote Similarity NPC270126
0.6566 Remote Similarity NPC294434
0.6566 Remote Similarity NPC259599
0.6566 Remote Similarity NPC15499
0.6566 Remote Similarity NPC474758
0.6566 Remote Similarity NPC117746
0.6562 Remote Similarity NPC476008
0.6557 Remote Similarity NPC270478
0.6555 Remote Similarity NPC89408
0.6552 Remote Similarity NPC476001
0.6552 Remote Similarity NPC189616
0.6549 Remote Similarity NPC35717
0.6542 Remote Similarity NPC241054
0.6538 Remote Similarity NPC10080
0.6538 Remote Similarity NPC123908
0.6535 Remote Similarity NPC68156
0.6535 Remote Similarity NPC57744
0.6532 Remote Similarity NPC158963
0.6531 Remote Similarity NPC133098
0.6529 Remote Similarity NPC469454
0.6529 Remote Similarity NPC469496
0.6529 Remote Similarity NPC56448
0.6529 Remote Similarity NPC469463
0.6529 Remote Similarity NPC159333
0.6514 Remote Similarity NPC213636
0.6514 Remote Similarity NPC329857
0.6514 Remote Similarity NPC253177
0.6514 Remote Similarity NPC280592
0.6514 Remote Similarity NPC469718
0.6509 Remote Similarity NPC67081
0.6509 Remote Similarity NPC189311
0.6509 Remote Similarity NPC471223
0.65 Remote Similarity NPC43775
0.65 Remote Similarity NPC474315
0.6496 Remote Similarity NPC85529
0.6496 Remote Similarity NPC32006
0.6496 Remote Similarity NPC478208
0.6495 Remote Similarity NPC470693
0.6491 Remote Similarity NPC474012
0.6491 Remote Similarity NPC472644
0.6491 Remote Similarity NPC54705
0.6491 Remote Similarity NPC476299
0.6486 Remote Similarity NPC56525
0.6486 Remote Similarity NPC84893
0.6486 Remote Similarity NPC470697
0.6484 Remote Similarity NPC477745
0.6481 Remote Similarity NPC469628
0.6481 Remote Similarity NPC478261
0.6481 Remote Similarity NPC471047
0.6481 Remote Similarity NPC478259
0.6481 Remote Similarity NPC226863
0.6481 Remote Similarity NPC469653

  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 NPC272528 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
0.6581 Remote Similarity NPD6614 Approved
0.6577 Remote Similarity NPD5654 Approved
0.646 Remote Similarity NPD5959 Approved
0.6452 Remote Similarity NPD6335 Approved
0.6452 Remote Similarity NPD6314 Approved
0.6452 Remote Similarity NPD6313 Approved
0.6446 Remote Similarity NPD6053 Discontinued
0.6404 Remote Similarity NPD5696 Approved
0.64 Remote Similarity NPD7101 Approved
0.64 Remote Similarity NPD7100 Approved
0.6306 Remote Similarity NPD5693 Phase 1
0.6306 Remote Similarity NPD5694 Approved
0.6303 Remote Similarity NPD5697 Approved
0.625 Remote Similarity NPD6881 Approved
0.625 Remote Similarity NPD6899 Approved
0.623 Remote Similarity NPD6649 Approved
0.623 Remote Similarity NPD6650 Approved
0.6226 Remote Similarity NPD5209 Approved
0.6218 Remote Similarity NPD6675 Approved
0.6218 Remote Similarity NPD7128 Approved
0.6218 Remote Similarity NPD5739 Approved
0.6218 Remote Similarity NPD6402 Approved
0.6216 Remote Similarity NPD5692 Phase 3
0.6204 Remote Similarity NPD1694 Approved
0.6198 Remote Similarity NPD6372 Approved
0.6198 Remote Similarity NPD6013 Approved
0.6198 Remote Similarity NPD6014 Approved
0.6198 Remote Similarity NPD6373 Approved
0.6198 Remote Similarity NPD6012 Approved
0.6182 Remote Similarity NPD6672 Approved
0.6182 Remote Similarity NPD5737 Approved
0.6167 Remote Similarity NPD5701 Approved
0.6161 Remote Similarity NPD6050 Approved
0.616 Remote Similarity NPD6868 Approved
0.6148 Remote Similarity NPD6883 Approved
0.6148 Remote Similarity NPD7102 Approved
0.6148 Remote Similarity NPD7290 Approved
0.614 Remote Similarity NPD5695 Phase 3
0.6119 Remote Similarity NPD7260 Phase 2
0.6116 Remote Similarity NPD6011 Approved
0.6116 Remote Similarity NPD7320 Approved
0.6111 Remote Similarity NPD7115 Discovery
0.6098 Remote Similarity NPD6617 Approved
0.6098 Remote Similarity NPD8130 Phase 1
0.6098 Remote Similarity NPD6847 Approved
0.6098 Remote Similarity NPD6869 Approved
0.6075 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6058 Remote Similarity NPD4756 Discovery
0.6048 Remote Similarity NPD6882 Approved
0.6048 Remote Similarity NPD8297 Approved
0.6047 Remote Similarity NPD5983 Phase 2
0.6034 Remote Similarity NPD6084 Phase 2
0.6034 Remote Similarity NPD6083 Phase 2
0.6016 Remote Similarity NPD2067 Discontinued
0.6016 Remote Similarity NPD5169 Approved
0.5985 Remote Similarity NPD6336 Discontinued
0.5984 Remote Similarity NPD5128 Approved
0.5982 Remote Similarity NPD6080 Approved
0.5982 Remote Similarity NPD6904 Approved
0.5982 Remote Similarity NPD6673 Approved
0.5968 Remote Similarity NPD5216 Approved
0.5968 Remote Similarity NPD5217 Approved
0.5968 Remote Similarity NPD5215 Approved
0.5968 Remote Similarity NPD5127 Approved
0.5966 Remote Similarity NPD5091 Approved
0.5965 Remote Similarity NPD6399 Phase 3
0.595 Remote Similarity NPD6008 Approved
0.5929 Remote Similarity NPD5207 Approved
0.5923 Remote Similarity NPD8513 Phase 3
0.5913 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5913 Remote Similarity NPD5282 Discontinued
0.5913 Remote Similarity NPD7900 Approved
0.5902 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5877 Remote Similarity NPD5284 Approved
0.5877 Remote Similarity NPD5281 Approved
0.5873 Remote Similarity NPD4632 Approved
0.5872 Remote Similarity NPD6110 Phase 1
0.5862 Remote Similarity NPD4629 Approved
0.5862 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5862 Remote Similarity NPD5210 Approved
0.5859 Remote Similarity NPD6009 Approved
0.5856 Remote Similarity NPD5330 Approved
0.5856 Remote Similarity NPD7146 Approved
0.5856 Remote Similarity NPD7521 Approved
0.5856 Remote Similarity NPD6409 Approved
0.5856 Remote Similarity NPD7334 Approved
0.5856 Remote Similarity NPD6684 Approved
0.5841 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5841 Remote Similarity NPD6101 Approved
0.584 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5211 Phase 2
0.5827 Remote Similarity NPD5167 Approved
0.5826 Remote Similarity NPD5778 Approved
0.5826 Remote Similarity NPD5779 Approved
0.5804 Remote Similarity NPD3573 Approved
0.5802 Remote Similarity NPD8517 Approved
0.5802 Remote Similarity NPD8515 Approved
0.5802 Remote Similarity NPD8516 Approved
0.5798 Remote Similarity NPD5286 Approved
0.5798 Remote Similarity NPD4696 Approved
0.5798 Remote Similarity NPD5285 Approved
0.5781 Remote Similarity NPD6274 Approved
0.5763 Remote Similarity NPD7902 Approved
0.5763 Remote Similarity NPD4755 Approved
0.576 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5752 Remote Similarity NPD6903 Approved
0.5752 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5739 Remote Similarity NPD6411 Approved
0.5738 Remote Similarity NPD5141 Approved
0.5736 Remote Similarity NPD6317 Approved
0.5727 Remote Similarity NPD7154 Phase 3
0.5726 Remote Similarity NPD5168 Approved
0.5725 Remote Similarity NPD6319 Approved
0.5725 Remote Similarity NPD6845 Suspended
0.5714 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6098 Approved
0.5714 Remote Similarity NPD8039 Approved
0.5714 Remote Similarity NPD4225 Approved
0.5714 Remote Similarity NPD7638 Approved
0.5714 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5702 Remote Similarity NPD4633 Approved
0.5702 Remote Similarity NPD5224 Approved
0.5702 Remote Similarity NPD5225 Approved
0.5702 Remote Similarity NPD5226 Approved
0.5702 Remote Similarity NPD7285 Clinical (unspecified phase)
0.569 Remote Similarity NPD5133 Approved
0.568 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5678 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5676 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5667 Remote Similarity NPD7639 Approved
0.5667 Remote Similarity NPD4700 Approved
0.5667 Remote Similarity NPD7640 Approved
0.5662 Remote Similarity NPD6033 Approved
0.5656 Remote Similarity NPD5175 Approved
0.5656 Remote Similarity NPD5174 Approved
0.5652 Remote Similarity NPD46 Approved
0.5652 Remote Similarity NPD5785 Approved
0.5652 Remote Similarity NPD6698 Approved
0.5645 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5641 Remote Similarity NPD7748 Approved
0.5625 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5625 Remote Similarity NPD1696 Phase 3
0.562 Remote Similarity NPD5223 Approved
0.56 Remote Similarity NPD6686 Approved
0.56 Remote Similarity NPD2685 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