Structure

Physi-Chem Properties

Molecular Weight:  334.21
Volume:  356.058
LogP:  3.543
LogD:  3.392
LogS:  -4.257
# Rotatable Bonds:  4
TPSA:  70.67
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.87
Synthetic Accessibility Score:  4.516
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.698
MDCK Permeability:  2.3425558538292535e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.401

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.535
Plasma Protein Binding (PPB):  96.25333404541016%
Volume Distribution (VD):  1.564
Pgp-substrate:  4.709396839141846%

ADMET: Metabolism

CYP1A2-inhibitor:  0.042
CYP1A2-substrate:  0.394
CYP2C19-inhibitor:  0.095
CYP2C19-substrate:  0.507
CYP2C9-inhibitor:  0.462
CYP2C9-substrate:  0.843
CYP2D6-inhibitor:  0.031
CYP2D6-substrate:  0.702
CYP3A4-inhibitor:  0.123
CYP3A4-substrate:  0.241

ADMET: Excretion

Clearance (CL):  15.135
Half-life (T1/2):  0.345

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.238
Drug-inuced Liver Injury (DILI):  0.057
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.6
Maximum Recommended Daily Dose:  0.293
Skin Sensitization:  0.346
Carcinogencity:  0.761
Eye Corrosion:  0.047
Eye Irritation:  0.135
Respiratory Toxicity:  0.971

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

  Natural Product: NPC475099

Natural Product ID:  NPC475099
Common Name*:   Chapecoderin B
IUPAC Name:   4-[2-[(1R,2R,3aS,7aS)-2-acetyl-1-hydroxy-4,4,7a-trimethyl-2,3,3a,5,6,7-hexahydroinden-1-yl]ethyl]-2H-furan-5-one
Synonyms:  
Standard InCHIKey:  MMTLIVZZWXTXFX-CPLUKWAASA-N
Standard InCHI:  InChI=1S/C20H30O4/c1-13(21)15-12-16-18(2,3)8-5-9-19(16,4)20(15,23)10-6-14-7-11-24-17(14)22/h7,15-16,23H,5-6,8-12H2,1-4H3/t15-,16-,19-,20+/m0/s1
SMILES:  CC(=O)C1CC2C(CCCC2(C1(CCC3=CCOC3=O)O)C)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL497721
PubChem CID:   10382251
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones

*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
NPO23381 Echinodorus macrophyllus Species Alismataceae Eukaryota n.a. n.a. n.a. PMID[10757722]
NPO23381 Echinodorus macrophyllus Species Alismataceae 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
NPT137 Cell Line L1210 Mus musculus IC50 = 7.2 ug.mL-1 PMID[488396]

☑ 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 NPC475099 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
0.8673 High Similarity NPC477949
0.8654 High Similarity NPC179642
0.85 High Similarity NPC280963
0.8438 Intermediate Similarity NPC51486
0.8426 Intermediate Similarity NPC72772
0.8426 Intermediate Similarity NPC469794
0.8416 Intermediate Similarity NPC477950
0.8416 Intermediate Similarity NPC116139
0.8384 Intermediate Similarity NPC29952
0.8384 Intermediate Similarity NPC118159
0.8367 Intermediate Similarity NPC90453
0.8351 Intermediate Similarity NPC472705
0.8351 Intermediate Similarity NPC221282
0.8351 Intermediate Similarity NPC290651
0.8333 Intermediate Similarity NPC66110
0.8317 Intermediate Similarity NPC471413
0.8317 Intermediate Similarity NPC54705
0.83 Intermediate Similarity NPC170143
0.83 Intermediate Similarity NPC108475
0.83 Intermediate Similarity NPC213947
0.8252 Intermediate Similarity NPC474775
0.8235 Intermediate Similarity NPC171759
0.8235 Intermediate Similarity NPC471412
0.8235 Intermediate Similarity NPC62670
0.8218 Intermediate Similarity NPC244411
0.8218 Intermediate Similarity NPC222011
0.8208 Intermediate Similarity NPC474901
0.8208 Intermediate Similarity NPC475941
0.8191 Intermediate Similarity NPC475100
0.8182 Intermediate Similarity NPC239273
0.8155 Intermediate Similarity NPC162973
0.8144 Intermediate Similarity NPC5509
0.8142 Intermediate Similarity NPC470419
0.8137 Intermediate Similarity NPC306856
0.8131 Intermediate Similarity NPC206595
0.8125 Intermediate Similarity NPC472004
0.8119 Intermediate Similarity NPC47834
0.8119 Intermediate Similarity NPC69385
0.8113 Intermediate Similarity NPC472825
0.8108 Intermediate Similarity NPC470420
0.8105 Intermediate Similarity NPC65661
0.81 Intermediate Similarity NPC209355
0.81 Intermediate Similarity NPC37408
0.8091 Intermediate Similarity NPC196931
0.8091 Intermediate Similarity NPC190286
0.8073 Intermediate Similarity NPC312017
0.8073 Intermediate Similarity NPC9848
0.807 Intermediate Similarity NPC472768
0.8058 Intermediate Similarity NPC472924
0.8053 Intermediate Similarity NPC46570
0.8053 Intermediate Similarity NPC470418
0.8039 Intermediate Similarity NPC471932
0.802 Intermediate Similarity NPC126156
0.802 Intermediate Similarity NPC9812
0.8017 Intermediate Similarity NPC287423
0.8 Intermediate Similarity NPC178289
0.8 Intermediate Similarity NPC470953
0.8 Intermediate Similarity NPC13385
0.8 Intermediate Similarity NPC53685
0.8 Intermediate Similarity NPC474181
0.8 Intermediate Similarity NPC149869
0.7982 Intermediate Similarity NPC475970
0.7982 Intermediate Similarity NPC107493
0.7981 Intermediate Similarity NPC475320
0.7981 Intermediate Similarity NPC475750
0.798 Intermediate Similarity NPC177037
0.798 Intermediate Similarity NPC472814
0.798 Intermediate Similarity NPC472953
0.7965 Intermediate Similarity NPC474585
0.7961 Intermediate Similarity NPC117685
0.7946 Intermediate Similarity NPC475372
0.7946 Intermediate Similarity NPC153440
0.7944 Intermediate Similarity NPC61411
0.7928 Intermediate Similarity NPC148458
0.7928 Intermediate Similarity NPC138372
0.7928 Intermediate Similarity NPC106228
0.7925 Intermediate Similarity NPC472935
0.7921 Intermediate Similarity NPC476488
0.7921 Intermediate Similarity NPC67584
0.7921 Intermediate Similarity NPC469873
0.7921 Intermediate Similarity NPC476487
0.7917 Intermediate Similarity NPC86316
0.7917 Intermediate Similarity NPC106416
0.7917 Intermediate Similarity NPC189311
0.7913 Intermediate Similarity NPC204812
0.7905 Intermediate Similarity NPC180204
0.7905 Intermediate Similarity NPC112009
0.79 Intermediate Similarity NPC475657
0.79 Intermediate Similarity NPC473263
0.79 Intermediate Similarity NPC153590
0.79 Intermediate Similarity NPC473234
0.79 Intermediate Similarity NPC115021
0.79 Intermediate Similarity NPC473273
0.79 Intermediate Similarity NPC60386
0.79 Intermediate Similarity NPC200237
0.79 Intermediate Similarity NPC308656
0.7895 Intermediate Similarity NPC471999
0.7895 Intermediate Similarity NPC472001
0.7895 Intermediate Similarity NPC472000
0.7885 Intermediate Similarity NPC295110
0.7885 Intermediate Similarity NPC268829
0.7885 Intermediate Similarity NPC304738
0.7885 Intermediate Similarity NPC247701
0.7885 Intermediate Similarity NPC222875
0.7885 Intermediate Similarity NPC195192
0.7885 Intermediate Similarity NPC206079
0.7885 Intermediate Similarity NPC25177
0.7881 Intermediate Similarity NPC231529
0.7879 Intermediate Similarity NPC301969
0.7879 Intermediate Similarity NPC37607
0.7879 Intermediate Similarity NPC77337
0.7876 Intermediate Similarity NPC5292
0.7876 Intermediate Similarity NPC312536
0.787 Intermediate Similarity NPC304495
0.7864 Intermediate Similarity NPC64742
0.7864 Intermediate Similarity NPC23364
0.7864 Intermediate Similarity NPC197386
0.7864 Intermediate Similarity NPC271387
0.7864 Intermediate Similarity NPC153792
0.785 Intermediate Similarity NPC475294
0.7845 Intermediate Similarity NPC32868
0.7845 Intermediate Similarity NPC241456
0.7843 Intermediate Similarity NPC242848
0.7843 Intermediate Similarity NPC142529
0.7843 Intermediate Similarity NPC213078
0.7843 Intermediate Similarity NPC134072
0.7843 Intermediate Similarity NPC91771
0.7843 Intermediate Similarity NPC184065
0.7843 Intermediate Similarity NPC234993
0.7843 Intermediate Similarity NPC42042
0.7835 Intermediate Similarity NPC469676
0.7835 Intermediate Similarity NPC474045
0.7835 Intermediate Similarity NPC261253
0.783 Intermediate Similarity NPC309190
0.7826 Intermediate Similarity NPC269642
0.7822 Intermediate Similarity NPC476415
0.7822 Intermediate Similarity NPC148463
0.7818 Intermediate Similarity NPC100267
0.7818 Intermediate Similarity NPC475524
0.7818 Intermediate Similarity NPC191620
0.7818 Intermediate Similarity NPC221144
0.781 Intermediate Similarity NPC22388
0.781 Intermediate Similarity NPC476769
0.7807 Intermediate Similarity NPC143755
0.7807 Intermediate Similarity NPC79579
0.7807 Intermediate Similarity NPC476962
0.7797 Intermediate Similarity NPC311534
0.7789 Intermediate Similarity NPC200513
0.7788 Intermediate Similarity NPC218383
0.7788 Intermediate Similarity NPC471041
0.7788 Intermediate Similarity NPC476274
0.7788 Intermediate Similarity NPC476767
0.7788 Intermediate Similarity NPC241221
0.7788 Intermediate Similarity NPC288679
0.7788 Intermediate Similarity NPC201406
0.7778 Intermediate Similarity NPC232747
0.7778 Intermediate Similarity NPC295312
0.7778 Intermediate Similarity NPC174342
0.7778 Intermediate Similarity NPC220155
0.7768 Intermediate Similarity NPC476963
0.7768 Intermediate Similarity NPC176840
0.7768 Intermediate Similarity NPC266728
0.7768 Intermediate Similarity NPC49492
0.7767 Intermediate Similarity NPC475709
0.7767 Intermediate Similarity NPC161493
0.7767 Intermediate Similarity NPC476253
0.7767 Intermediate Similarity NPC474343
0.7766 Intermediate Similarity NPC47747
0.7759 Intermediate Similarity NPC129992
0.7759 Intermediate Similarity NPC55602
0.7759 Intermediate Similarity NPC120724
0.7759 Intermediate Similarity NPC473979
0.7757 Intermediate Similarity NPC190867
0.7757 Intermediate Similarity NPC470975
0.7757 Intermediate Similarity NPC103088
0.7757 Intermediate Similarity NPC96377
0.7757 Intermediate Similarity NPC470979
0.7755 Intermediate Similarity NPC45957
0.7755 Intermediate Similarity NPC471657
0.7748 Intermediate Similarity NPC472926
0.7748 Intermediate Similarity NPC962
0.7748 Intermediate Similarity NPC52634
0.7745 Intermediate Similarity NPC329435
0.7745 Intermediate Similarity NPC470978
0.7745 Intermediate Similarity NPC171395
0.7745 Intermediate Similarity NPC52044
0.7745 Intermediate Similarity NPC293052
0.7745 Intermediate Similarity NPC470974
0.7736 Intermediate Similarity NPC140723
0.7736 Intermediate Similarity NPC474330
0.7736 Intermediate Similarity NPC187302
0.7736 Intermediate Similarity NPC110989
0.7736 Intermediate Similarity NPC472821
0.7736 Intermediate Similarity NPC470954
0.7736 Intermediate Similarity NPC189588
0.7736 Intermediate Similarity NPC97487
0.7736 Intermediate Similarity NPC10232
0.7736 Intermediate Similarity NPC160583
0.7736 Intermediate Similarity NPC159442
0.7736 Intermediate Similarity NPC196471

  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 NPC475099 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
0.7789 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7745 Intermediate Similarity NPD5695 Phase 3
0.77 Intermediate Similarity NPD5785 Approved
0.7692 Intermediate Similarity NPD7638 Approved
0.7658 Intermediate Similarity NPD6053 Discontinued
0.7624 Intermediate Similarity NPD5693 Phase 1
0.7619 Intermediate Similarity NPD7640 Approved
0.7619 Intermediate Similarity NPD7639 Approved
0.7596 Intermediate Similarity NPD6083 Phase 2
0.7596 Intermediate Similarity NPD6084 Phase 2
0.7593 Intermediate Similarity NPD6008 Approved
0.7583 Intermediate Similarity NPD7319 Approved
0.7524 Intermediate Similarity NPD5696 Approved
0.7523 Intermediate Similarity NPD5697 Approved
0.75 Intermediate Similarity NPD6319 Approved
0.7479 Intermediate Similarity NPD7507 Approved
0.7477 Intermediate Similarity NPD6371 Approved
0.7455 Intermediate Similarity NPD7320 Approved
0.7455 Intermediate Similarity NPD6011 Approved
0.7455 Intermediate Similarity NPD6899 Approved
0.7455 Intermediate Similarity NPD6881 Approved
0.7434 Intermediate Similarity NPD4632 Approved
0.7431 Intermediate Similarity NPD6402 Approved
0.7431 Intermediate Similarity NPD5739 Approved
0.7431 Intermediate Similarity NPD6675 Approved
0.7431 Intermediate Similarity NPD7128 Approved
0.7404 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD7492 Approved
0.7387 Intermediate Similarity NPD6013 Approved
0.7387 Intermediate Similarity NPD6012 Approved
0.7387 Intermediate Similarity NPD6014 Approved
0.7364 Intermediate Similarity NPD5701 Approved
0.7364 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.735 Intermediate Similarity NPD6054 Approved
0.7333 Intermediate Similarity NPD6616 Approved
0.7327 Intermediate Similarity NPD6903 Approved
0.7321 Intermediate Similarity NPD7102 Approved
0.7321 Intermediate Similarity NPD7290 Approved
0.7321 Intermediate Similarity NPD6883 Approved
0.73 Intermediate Similarity NPD6684 Approved
0.73 Intermediate Similarity NPD7334 Approved
0.73 Intermediate Similarity NPD7146 Approved
0.73 Intermediate Similarity NPD7521 Approved
0.73 Intermediate Similarity NPD6409 Approved
0.73 Intermediate Similarity NPD5330 Approved
0.7297 Intermediate Similarity NPD6686 Approved
0.7288 Intermediate Similarity NPD6016 Approved
0.7288 Intermediate Similarity NPD6015 Approved
0.7282 Intermediate Similarity NPD5281 Approved
0.7282 Intermediate Similarity NPD5284 Approved
0.7273 Intermediate Similarity NPD7078 Approved
0.7257 Intermediate Similarity NPD6650 Approved
0.7257 Intermediate Similarity NPD8130 Phase 1
0.7257 Intermediate Similarity NPD6617 Approved
0.7257 Intermediate Similarity NPD6869 Approved
0.7257 Intermediate Similarity NPD6649 Approved
0.7257 Intermediate Similarity NPD6847 Approved
0.7255 Intermediate Similarity NPD4753 Phase 2
0.7255 Intermediate Similarity NPD6904 Approved
0.7255 Intermediate Similarity NPD6673 Approved
0.7255 Intermediate Similarity NPD6080 Approved
0.7245 Intermediate Similarity NPD4221 Approved
0.7245 Intermediate Similarity NPD4223 Phase 3
0.7241 Intermediate Similarity NPD6009 Approved
0.7241 Intermediate Similarity NPD7115 Discovery
0.7238 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD6373 Approved
0.7232 Intermediate Similarity NPD6372 Approved
0.7227 Intermediate Similarity NPD6370 Approved
0.7227 Intermediate Similarity NPD5988 Approved
0.7213 Intermediate Similarity NPD7736 Approved
0.7203 Intermediate Similarity NPD6059 Approved
0.72 Intermediate Similarity NPD5363 Approved
0.7193 Intermediate Similarity NPD8297 Approved
0.7193 Intermediate Similarity NPD6882 Approved
0.7184 Intermediate Similarity NPD5692 Phase 3
0.7184 Intermediate Similarity NPD5207 Approved
0.7168 Intermediate Similarity NPD4634 Approved
0.7157 Intermediate Similarity NPD5737 Approved
0.7157 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD6672 Approved
0.7157 Intermediate Similarity NPD5208 Approved
0.7156 Intermediate Similarity NPD5211 Phase 2
0.7143 Intermediate Similarity NPD5983 Phase 2
0.7131 Intermediate Similarity NPD8293 Discontinued
0.713 Intermediate Similarity NPD5286 Approved
0.713 Intermediate Similarity NPD4696 Approved
0.713 Intermediate Similarity NPD5285 Approved
0.7129 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD5690 Phase 2
0.7129 Intermediate Similarity NPD5786 Approved
0.7115 Intermediate Similarity NPD6050 Approved
0.7115 Intermediate Similarity NPD5694 Approved
0.7105 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4755 Approved
0.71 Intermediate Similarity NPD4197 Approved
0.71 Intermediate Similarity NPD3665 Phase 1
0.71 Intermediate Similarity NPD3133 Approved
0.71 Intermediate Similarity NPD3666 Approved
0.7075 Intermediate Similarity NPD4629 Approved
0.7075 Intermediate Similarity NPD5210 Approved
0.7064 Intermediate Similarity NPD5223 Approved
0.7048 Intermediate Similarity NPD6399 Phase 3
0.7037 Intermediate Similarity NPD4225 Approved
0.703 Intermediate Similarity NPD5329 Approved
0.7027 Intermediate Similarity NPD5141 Approved
0.7025 Intermediate Similarity NPD7604 Phase 2
0.7009 Intermediate Similarity NPD6274 Approved
0.7 Intermediate Similarity NPD5362 Discontinued
0.7 Intermediate Similarity NPD5226 Approved
0.7 Intermediate Similarity NPD5225 Approved
0.7 Intermediate Similarity NPD4633 Approved
0.7 Intermediate Similarity NPD7632 Discontinued
0.7 Intermediate Similarity NPD5224 Approved
0.6981 Remote Similarity NPD5282 Discontinued
0.6981 Remote Similarity NPD6001 Approved
0.6972 Remote Similarity NPD4700 Approved
0.697 Remote Similarity NPD5369 Approved
0.6961 Remote Similarity NPD5205 Approved
0.6961 Remote Similarity NPD4694 Approved
0.6961 Remote Similarity NPD4688 Approved
0.6961 Remote Similarity NPD6098 Approved
0.6961 Remote Similarity NPD5280 Approved
0.6961 Remote Similarity NPD4138 Approved
0.6961 Remote Similarity NPD4693 Phase 3
0.6961 Remote Similarity NPD4690 Approved
0.6961 Remote Similarity NPD4689 Approved
0.6952 Remote Similarity NPD7637 Suspended
0.6952 Remote Similarity NPD6079 Approved
0.6949 Remote Similarity NPD6317 Approved
0.6937 Remote Similarity NPD5174 Approved
0.6937 Remote Similarity NPD5175 Approved
0.6923 Remote Similarity NPD6051 Approved
0.6923 Remote Similarity NPD1695 Approved
0.6923 Remote Similarity NPD5328 Approved
0.6911 Remote Similarity NPD6336 Discontinued
0.6903 Remote Similarity NPD6412 Phase 2
0.69 Remote Similarity NPD4269 Approved
0.69 Remote Similarity NPD6435 Approved
0.69 Remote Similarity NPD5209 Approved
0.69 Remote Similarity NPD4270 Approved
0.6891 Remote Similarity NPD6335 Approved
0.6891 Remote Similarity NPD7327 Approved
0.6891 Remote Similarity NPD6314 Approved
0.6891 Remote Similarity NPD6313 Approved
0.6891 Remote Similarity NPD7328 Approved
0.6887 Remote Similarity NPD4202 Approved
0.6887 Remote Similarity NPD5778 Approved
0.6887 Remote Similarity NPD5779 Approved
0.6863 Remote Similarity NPD1694 Approved
0.6863 Remote Similarity NPD6082 Clinical (unspecified phase)
0.686 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5221 Approved
0.6852 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5222 Approved
0.6837 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6833 Remote Similarity NPD7101 Approved
0.6833 Remote Similarity NPD7100 Approved
0.6833 Remote Similarity NPD7516 Approved
0.6832 Remote Similarity NPD4788 Approved
0.68 Remote Similarity NPD6033 Approved
0.6796 Remote Similarity NPD5279 Phase 3
0.6789 Remote Similarity NPD5173 Approved
0.6786 Remote Similarity NPD4754 Approved
0.6783 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6777 Remote Similarity NPD8294 Approved
0.6777 Remote Similarity NPD8377 Approved
0.6768 Remote Similarity NPD4195 Approved
0.6759 Remote Similarity NPD5654 Approved
0.6731 Remote Similarity NPD3573 Approved
0.6724 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6721 Remote Similarity NPD8379 Approved
0.6721 Remote Similarity NPD8033 Approved
0.6721 Remote Similarity NPD8296 Approved
0.6721 Remote Similarity NPD8378 Approved
0.6721 Remote Similarity NPD8380 Approved
0.6721 Remote Similarity NPD8335 Approved
0.6718 Remote Similarity NPD6334 Approved
0.6718 Remote Similarity NPD6333 Approved
0.67 Remote Similarity NPD5368 Approved
0.67 Remote Similarity NPD4252 Approved
0.6698 Remote Similarity NPD46 Approved
0.6698 Remote Similarity NPD6698 Approved
0.6698 Remote Similarity NPD4096 Approved
0.6697 Remote Similarity NPD4697 Phase 3
0.6696 Remote Similarity NPD4730 Approved
0.6696 Remote Similarity NPD4729 Approved
0.6696 Remote Similarity NPD5128 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6667 Remote Similarity NPD4768 Approved
0.6667 Remote Similarity NPD7748 Approved
0.6637 Remote Similarity NPD6052 Approved
0.6636 Remote Similarity NPD6411 Approved
0.6636 Remote Similarity NPD5959 Approved
0.6635 Remote Similarity NPD3618 Phase 1
0.6635 Remote Similarity NPD4249 Approved
0.6602 Remote Similarity NPD4786 Approved
0.6585 Remote Similarity NPD7503 Approved
0.6585 Remote Similarity NPD6908 Approved
0.6585 Remote Similarity NPD6909 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