Structure

Physi-Chem Properties

Molecular Weight:  896.47
Volume:  916.62
LogP:  3.953
LogD:  3.808
LogS:  -4.469
# Rotatable Bonds:  12
TPSA:  217.46
# H-Bond Aceptor:  16
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.229
Synthetic Accessibility Score:  5.688
Fsp3:  0.587
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.636
MDCK Permeability:  3.641299554146826e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.985
Human Intestinal Absorption (HIA):  0.063
20% Bioavailability (F20%):  0.177
30% Bioavailability (F30%):  0.901

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  86.43383026123047%
Volume Distribution (VD):  0.554
Pgp-substrate:  3.1620397567749023%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.02
CYP2C19-inhibitor:  0.054
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.205
CYP2C9-substrate:  0.038
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.053
CYP3A4-inhibitor:  0.915
CYP3A4-substrate:  0.572

ADMET: Excretion

Clearance (CL):  3.036
Half-life (T1/2):  0.2

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.982
Drug-inuced Liver Injury (DILI):  0.973
AMES Toxicity:  0.005
Rat Oral Acute Toxicity:  0.42
Maximum Recommended Daily Dose:  0.916
Skin Sensitization:  0.037
Carcinogencity:  0.021
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.018

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

  Natural Product: NPC286551

Natural Product ID:  NPC286551
Common Name*:   Carriebowmide Sulfone
IUPAC Name:   (2R,5R,8S,11S,14S,17S,20R,21S)-5,11-dibenzyl-4,13,17,21-tetramethyl-14-(2-methylpropyl)-8-(2-methylsulfonylethyl)-2-propan-2-yl-20-propyl-1-oxa-4,7,10,13,16,19-hexazacyclodocosane-3,6,9,12,15,18,22-heptone
Synonyms:   Carriebowmide Sulfone
Standard InCHIKey:  KSNLKLIQGHRTKX-ARSHIWEASA-N
Standard InCHI:  InChI=1S/C46H68N6O10S/c1-11-18-34-30(6)46(59)62-39(29(4)5)45(58)52(9)38(27-33-21-16-13-17-22-33)43(56)49-35(23-24-63(10,60)61)41(54)50-36(26-32-19-14-12-15-20-32)44(57)51(8)37(25-28(2)3)42(55)47-31(7)40(53)48-34/h12-17,19-22,28-31,34-39H,11,18,23-27H2,1-10H3,(H,47,55)(H,48,53)(H,49,56)(H,50,54)/t30-,31-,34+,35-,36-,37-,38+,39+/m0/s1
SMILES:  CCC[C@H]1N=C(O)[C@H](C)N=C(O)[C@H](CC(C)C)N(C)C(=O)[C@H](Cc2ccccc2)N=C([C@@H](N=C([C@H](N(C(=O)[C@H](OC(=O)[C@H]1C)C(C)C)C)Cc1ccccc1)O)CCS(=O)(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1078519
PubChem CID:   46883528
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0001961] Depsipeptides
          • [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10514329]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10654420]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10691708]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. palauan n.a. PMID[10691729]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10843570]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10924172]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10978206]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076571]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076573]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076574]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11277744]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11389621]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11430000]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11473443]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11922791]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12762816]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[12828459]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[14575437]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[1517734]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[16643028]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17125217]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17441769]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18444683]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Singapore n.a. PMID[19093843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19489598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. eastern Caribbean n.a. PMID[19739598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19839606]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20030365]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. panamanian n.a. PMID[20158242]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Floridian n.a. PMID[20166701]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20936843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21138309]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[2128518]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21341718]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21539315]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21806011]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21999614]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[22035372]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[29792428]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[3924698]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[7623050]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[8699186]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9584405]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599278]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599279]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9784156]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria 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 IC50 > 50000.0 nM PMID[473008]

☑ 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 NPC286551 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
0.9714 High Similarity NPC105717
0.8699 High Similarity NPC209509
0.8571 High Similarity NPC322878
0.8562 High Similarity NPC139326
0.85 High Similarity NPC318930
0.85 High Similarity NPC317362
0.85 High Similarity NPC317725
0.85 High Similarity NPC326407
0.8493 Intermediate Similarity NPC263493
0.8493 Intermediate Similarity NPC269398
0.8414 Intermediate Similarity NPC471264
0.8414 Intermediate Similarity NPC471265
0.8356 Intermediate Similarity NPC470884
0.8356 Intermediate Similarity NPC92784
0.8356 Intermediate Similarity NPC178662
0.8356 Intermediate Similarity NPC98424
0.8356 Intermediate Similarity NPC476133
0.82 Intermediate Similarity NPC5620
0.8188 Intermediate Similarity NPC161069
0.8176 Intermediate Similarity NPC46098
0.8176 Intermediate Similarity NPC268841
0.8176 Intermediate Similarity NPC307357
0.8163 Intermediate Similarity NPC127741
0.8163 Intermediate Similarity NPC68865
0.7987 Intermediate Similarity NPC129666
0.7986 Intermediate Similarity NPC152850
0.7986 Intermediate Similarity NPC71933
0.7986 Intermediate Similarity NPC239990
0.7986 Intermediate Similarity NPC89923
0.7986 Intermediate Similarity NPC105114
0.7974 Intermediate Similarity NPC138775
0.7974 Intermediate Similarity NPC329761
0.7974 Intermediate Similarity NPC225648
0.7947 Intermediate Similarity NPC197682
0.7933 Intermediate Similarity NPC239762
0.7933 Intermediate Similarity NPC163392
0.7922 Intermediate Similarity NPC240848
0.7917 Intermediate Similarity NPC136453
0.7895 Intermediate Similarity NPC476978
0.7885 Intermediate Similarity NPC162104
0.7881 Intermediate Similarity NPC168113
0.7877 Intermediate Similarity NPC300315
0.7871 Intermediate Similarity NPC283783
0.7857 Intermediate Similarity NPC470546
0.7857 Intermediate Similarity NPC145113
0.7829 Intermediate Similarity NPC176226
0.7823 Intermediate Similarity NPC157311
0.7806 Intermediate Similarity NPC471821
0.7806 Intermediate Similarity NPC471820
0.7792 Intermediate Similarity NPC262077
0.7786 Intermediate Similarity NPC470545
0.777 Intermediate Similarity NPC8761
0.777 Intermediate Similarity NPC44805
0.7763 Intermediate Similarity NPC469426
0.7763 Intermediate Similarity NPC469427
0.775 Intermediate Similarity NPC297145
0.775 Intermediate Similarity NPC197743
0.7722 Intermediate Similarity NPC122590
0.7714 Intermediate Similarity NPC470544
0.7697 Intermediate Similarity NPC476259
0.7669 Intermediate Similarity NPC471053
0.7669 Intermediate Similarity NPC471051
0.7669 Intermediate Similarity NPC471052
0.7667 Intermediate Similarity NPC248283
0.766 Intermediate Similarity NPC169328
0.7632 Intermediate Similarity NPC132636
0.7628 Intermediate Similarity NPC135121
0.7619 Intermediate Similarity NPC319766
0.7613 Intermediate Similarity NPC477217
0.7613 Intermediate Similarity NPC201244
0.7606 Intermediate Similarity NPC310467
0.7603 Intermediate Similarity NPC47667
0.7584 Intermediate Similarity NPC255447
0.7568 Intermediate Similarity NPC473322
0.7548 Intermediate Similarity NPC52748
0.7546 Intermediate Similarity NPC471527
0.7533 Intermediate Similarity NPC246079
0.7532 Intermediate Similarity NPC2501
0.75 Intermediate Similarity NPC45777
0.75 Intermediate Similarity NPC477061
0.75 Intermediate Similarity NPC313867
0.75 Intermediate Similarity NPC316008
0.7452 Intermediate Similarity NPC314358
0.745 Intermediate Similarity NPC111428
0.7436 Intermediate Similarity NPC314388
0.7436 Intermediate Similarity NPC315283
0.7425 Intermediate Similarity NPC473502
0.7416 Intermediate Similarity NPC165538
0.7391 Intermediate Similarity NPC473341
0.7379 Intermediate Similarity NPC200964
0.7368 Intermediate Similarity NPC287401
0.7365 Intermediate Similarity NPC101719
0.7361 Intermediate Similarity NPC237420
0.7347 Intermediate Similarity NPC46427
0.7347 Intermediate Similarity NPC6975
0.7338 Intermediate Similarity NPC43755
0.7329 Intermediate Similarity NPC71684
0.7303 Intermediate Similarity NPC122427
0.7303 Intermediate Similarity NPC329961
0.7297 Intermediate Similarity NPC222466
0.7292 Intermediate Similarity NPC254088
0.729 Intermediate Similarity NPC89489
0.7285 Intermediate Similarity NPC200589
0.7279 Intermediate Similarity NPC252878
0.7278 Intermediate Similarity NPC471680
0.7267 Intermediate Similarity NPC7817
0.7267 Intermediate Similarity NPC475168
0.7261 Intermediate Similarity NPC468984
0.7237 Intermediate Similarity NPC130309
0.7235 Intermediate Similarity NPC196091
0.7235 Intermediate Similarity NPC40234
0.7211 Intermediate Similarity NPC202521
0.7209 Intermediate Similarity NPC476227
0.7209 Intermediate Similarity NPC477462
0.7203 Intermediate Similarity NPC33742
0.7202 Intermediate Similarity NPC210377
0.7202 Intermediate Similarity NPC22883
0.7202 Intermediate Similarity NPC5719
0.7202 Intermediate Similarity NPC217804
0.717 Intermediate Similarity NPC315266
0.7169 Intermediate Similarity NPC62104
0.7169 Intermediate Similarity NPC1390
0.7167 Intermediate Similarity NPC477526
0.716 Intermediate Similarity NPC15068
0.7151 Intermediate Similarity NPC306804
0.7151 Intermediate Similarity NPC137627
0.7143 Intermediate Similarity NPC478014
0.7143 Intermediate Similarity NPC476990
0.7143 Intermediate Similarity NPC478015
0.7143 Intermediate Similarity NPC478016
0.7143 Intermediate Similarity NPC190663
0.7134 Intermediate Similarity NPC470902
0.7133 Intermediate Similarity NPC276949
0.7133 Intermediate Similarity NPC35850
0.7125 Intermediate Similarity NPC81026
0.712 Intermediate Similarity NPC477527
0.7118 Intermediate Similarity NPC107938
0.7118 Intermediate Similarity NPC63040
0.7118 Intermediate Similarity NPC294516
0.7114 Intermediate Similarity NPC175726
0.7114 Intermediate Similarity NPC35996
0.7114 Intermediate Similarity NPC474082
0.711 Intermediate Similarity NPC159767
0.711 Intermediate Similarity NPC155506
0.711 Intermediate Similarity NPC279871
0.711 Intermediate Similarity NPC26108
0.7103 Intermediate Similarity NPC239357
0.7095 Intermediate Similarity NPC4910
0.7063 Intermediate Similarity NPC266741
0.7052 Intermediate Similarity NPC248670
0.7047 Intermediate Similarity NPC160493
0.7045 Intermediate Similarity NPC153554
0.7027 Intermediate Similarity NPC302169
0.7022 Intermediate Similarity NPC471048
0.7022 Intermediate Similarity NPC471049
0.7022 Intermediate Similarity NPC471050
0.7011 Intermediate Similarity NPC471165
0.7 Intermediate Similarity NPC63931
0.7 Intermediate Similarity NPC329731
0.6995 Remote Similarity NPC251036
0.6994 Remote Similarity NPC89831
0.6994 Remote Similarity NPC13470
0.6994 Remote Similarity NPC230611
0.6989 Remote Similarity NPC269750
0.6989 Remote Similarity NPC475421
0.6989 Remote Similarity NPC194671
0.6988 Remote Similarity NPC469903
0.6975 Remote Similarity NPC16188
0.6974 Remote Similarity NPC477937
0.6971 Remote Similarity NPC50016
0.6957 Remote Similarity NPC184933
0.6957 Remote Similarity NPC59827
0.6954 Remote Similarity NPC273755
0.6954 Remote Similarity NPC22746
0.6944 Remote Similarity NPC474584
0.6936 Remote Similarity NPC475123
0.6936 Remote Similarity NPC475204
0.6928 Remote Similarity NPC39431
0.6927 Remote Similarity NPC14877
0.6927 Remote Similarity NPC475350
0.6927 Remote Similarity NPC145178
0.6923 Remote Similarity NPC469243
0.6918 Remote Similarity NPC197470
0.6914 Remote Similarity NPC473354
0.6914 Remote Similarity NPC158277
0.6914 Remote Similarity NPC473402
0.6913 Remote Similarity NPC80150
0.691 Remote Similarity NPC476321
0.6909 Remote Similarity NPC233702
0.6908 Remote Similarity NPC4974
0.6901 Remote Similarity NPC472923
0.6883 Remote Similarity NPC469666
0.6879 Remote Similarity NPC186617
0.6872 Remote Similarity NPC470112
0.6872 Remote Similarity NPC167763
0.6872 Remote Similarity NPC161143
0.6872 Remote Similarity NPC470903
0.6872 Remote Similarity NPC471526
0.6871 Remote Similarity NPC285926
0.6871 Remote Similarity NPC315276

  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 NPC286551 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
0.8056 Intermediate Similarity NPD7828 Discontinued
0.7877 Intermediate Similarity NPD4125 Approved
0.7862 Intermediate Similarity NPD7749 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6119 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD8323 Discontinued
0.7682 Intermediate Similarity NPD8173 Phase 2
0.7682 Intermediate Similarity NPD8172 Phase 2
0.7628 Intermediate Similarity NPD6552 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD3608 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD3561 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD7892 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8643 Discontinued
0.7483 Intermediate Similarity NPD5367 Discontinued
0.7466 Intermediate Similarity NPD2584 Suspended
0.7456 Intermediate Similarity NPD7964 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD7965 Phase 2
0.7434 Intermediate Similarity NPD8416 Discontinued
0.7434 Intermediate Similarity NPD8265 Approved
0.7432 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6852 Discontinued
0.7372 Intermediate Similarity NPD2022 Approved
0.7362 Intermediate Similarity NPD8417 Discontinued
0.7355 Intermediate Similarity NPD6865 Phase 2
0.7355 Intermediate Similarity NPD6864 Phase 2
0.7355 Intermediate Similarity NPD3480 Approved
0.7353 Intermediate Similarity NPD8126 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD8124 Phase 3
0.7351 Intermediate Similarity NPD2043 Approved
0.7351 Intermediate Similarity NPD2044 Approved
0.7351 Intermediate Similarity NPD2049 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD2045 Approved
0.7351 Intermediate Similarity NPD2050 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD2051 Approved
0.7351 Intermediate Similarity NPD21 Approved
0.7351 Intermediate Similarity NPD2046 Approved
0.7351 Intermediate Similarity NPD2047 Approved
0.7351 Intermediate Similarity NPD2048 Approved
0.7346 Intermediate Similarity NPD4646 Approved
0.7346 Intermediate Similarity NPD4647 Approved
0.7346 Intermediate Similarity NPD4648 Approved
0.7342 Intermediate Similarity NPD5298 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4557 Approved
0.7325 Intermediate Similarity NPD2437 Approved
0.7325 Intermediate Similarity NPD2436 Approved
0.7321 Intermediate Similarity NPD4508 Discontinued
0.732 Intermediate Similarity NPD5323 Approved
0.7278 Intermediate Similarity NPD6304 Approved
0.7278 Intermediate Similarity NPD6303 Approved
0.7278 Intermediate Similarity NPD5264 Approved
0.7278 Intermediate Similarity NPD5265 Approved
0.7261 Intermediate Similarity NPD2087 Approved
0.7261 Intermediate Similarity NPD2088 Approved
0.7222 Intermediate Similarity NPD7613 Discontinued
0.7222 Intermediate Similarity NPD5230 Approved
0.7222 Intermediate Similarity NPD7303 Discontinued
0.7222 Intermediate Similarity NPD5229 Approved
0.7208 Intermediate Similarity NPD6623 Phase 3
0.7205 Intermediate Similarity NPD5613 Approved
0.7205 Intermediate Similarity NPD5614 Approved
0.7192 Intermediate Similarity NPD4504 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD7908 Discontinued
0.719 Intermediate Similarity NPD5299 Approved
0.7152 Intermediate Similarity NPD2891 Approved
0.7152 Intermediate Similarity NPD8076 Discontinued
0.7134 Intermediate Similarity NPD3648 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD4566 Approved
0.7126 Intermediate Similarity NPD4567 Approved
0.7117 Intermediate Similarity NPD5638 Approved
0.7115 Intermediate Similarity NPD6073 Approved
0.7107 Intermediate Similarity NPD5341 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD6088 Approved
0.7099 Intermediate Similarity NPD3988 Approved
0.7099 Intermediate Similarity NPD3987 Approved
0.7075 Intermediate Similarity NPD4209 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD6295 Approved
0.707 Intermediate Similarity NPD6901 Phase 3
0.707 Intermediate Similarity NPD6294 Approved
0.7063 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD4432 Discontinued
0.7039 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.6994 Remote Similarity NPD2014 Approved
0.6994 Remote Similarity NPD2013 Approved
0.6994 Remote Similarity NPD2016 Approved
0.6993 Remote Similarity NPD4177 Approved
0.6993 Remote Similarity NPD4175 Approved
0.6987 Remote Similarity NPD4153 Approved
0.6962 Remote Similarity NPD4126 Approved
0.6954 Remote Similarity NPD4677 Discontinued
0.6928 Remote Similarity NPD8315 Phase 1
0.6928 Remote Similarity NPD3604 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1348 Approved
0.6918 Remote Similarity NPD7728 Clinical (unspecified phase)
0.6906 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6899 Remote Similarity NPD5725 Approved
0.6894 Remote Similarity NPD6681 Discovery
0.6883 Remote Similarity NPD3626 Phase 3
0.6868 Remote Similarity NPD5852 Approved
0.6868 Remote Similarity NPD5851 Approved
0.6846 Remote Similarity NPD5981 Approved
0.6832 Remote Similarity NPD7720 Phase 2
0.6826 Remote Similarity NPD7745 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7599 Phase 2
0.6821 Remote Similarity NPD4480 Approved
0.6807 Remote Similarity NPD6390 Discontinued
0.6806 Remote Similarity NPD3643 Approved
0.6806 Remote Similarity NPD3644 Approved
0.6806 Remote Similarity NPD3642 Approved
0.6805 Remote Similarity NPD6679 Phase 3
0.6805 Remote Similarity NPD6680 Clinical (unspecified phase)
0.6805 Remote Similarity NPD6678 Phase 3
0.6798 Remote Similarity NPD5484 Approved
0.6798 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6798 Remote Similarity NPD5485 Approved
0.6792 Remote Similarity NPD5004 Approved
0.6784 Remote Similarity NPD7600 Phase 2
0.6779 Remote Similarity NPD2217 Approved
0.6779 Remote Similarity NPD2218 Phase 2
0.6772 Remote Similarity NPD5296 Approved
0.6766 Remote Similarity NPD7131 Phase 3
0.6752 Remote Similarity NPD5581 Approved
0.6731 Remote Similarity NPD5263 Approved
0.6728 Remote Similarity NPD4152 Approved
0.6711 Remote Similarity NPD4706 Clinical (unspecified phase)
0.6709 Remote Similarity NPD5747 Discontinued
0.6709 Remote Similarity NPD7634 Clinical (unspecified phase)
0.6708 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6708 Remote Similarity NPD6866 Clinical (unspecified phase)
0.6708 Remote Similarity NPD5301 Clinical (unspecified phase)
0.6705 Remote Similarity NPD5633 Discontinued
0.6688 Remote Similarity NPD6792 Phase 3
0.6688 Remote Similarity NPD4738 Phase 2
0.6687 Remote Similarity NPD1581 Approved
0.6687 Remote Similarity NPD1582 Approved
0.6686 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6686 Remote Similarity NPD2097 Approved
0.6686 Remote Similarity NPD7744 Clinical (unspecified phase)
0.6684 Remote Similarity NPD8339 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3040 Approved
0.6667 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7740 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3071 Approved
0.6667 Remote Similarity NPD3073 Approved
0.6667 Remote Similarity NPD3072 Approved
0.6667 Remote Similarity NPD6093 Discontinued
0.6648 Remote Similarity NPD4652 Approved
0.6648 Remote Similarity NPD7968 Clinical (unspecified phase)
0.6647 Remote Similarity NPD8351 Phase 2
0.6644 Remote Similarity NPD4574 Approved
0.6644 Remote Similarity NPD4576 Approved
0.6625 Remote Similarity NPD7733 Phase 2
0.6624 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6609 Remote Similarity NPD2098 Approved
0.6608 Remote Similarity NPD7105 Phase 1
0.6608 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6601 Remote Similarity NPD4762 Approved
0.6601 Remote Similarity NPD4761 Approved
0.66 Remote Similarity NPD6360 Discontinued
0.6591 Remote Similarity NPD7485 Phase 3
0.6591 Remote Similarity NPD6839 Clinical (unspecified phase)
0.6591 Remote Similarity NPD7484 Phase 3
0.659 Remote Similarity NPD6646 Discontinued
0.6584 Remote Similarity NPD4782 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7602 Clinical (unspecified phase)
0.6564 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6564 Remote Similarity NPD7512 Approved
0.6564 Remote Similarity NPD7511 Approved
0.6562 Remote Similarity NPD4791 Clinical (unspecified phase)
0.6561 Remote Similarity NPD5204 Approved
0.6556 Remote Similarity NPD8362 Clinical (unspecified phase)
0.6554 Remote Similarity NPD7608 Discontinued
0.655 Remote Similarity NPD7267 Clinical (unspecified phase)
0.6548 Remote Similarity NPD5942 Approved
0.6548 Remote Similarity NPD5941 Approved
0.6541 Remote Similarity NPD4621 Approved
0.6541 Remote Similarity NPD4619 Approved
0.6538 Remote Similarity NPD6302 Clinical (unspecified phase)
0.6529 Remote Similarity NPD7836 Clinical (unspecified phase)
0.6528 Remote Similarity NPD7130 Phase 3
0.6527 Remote Similarity NPD3509 Approved
0.6527 Remote Similarity NPD3510 Approved
0.6527 Remote Similarity NPD8290 Clinical (unspecified phase)
0.6519 Remote Similarity NPD7979 Clinical (unspecified phase)
0.6519 Remote Similarity NPD4620 Approved
0.6519 Remote Similarity NPD5201 Approved
0.6519 Remote Similarity NPD5203 Approved
0.6519 Remote Similarity NPD4676 Approved
0.6519 Remote Similarity NPD2613 Approved
0.6519 Remote Similarity NPD4617 Approved
0.6506 Remote Similarity NPD1967 Approved
0.6506 Remote Similarity NPD1968 Approved
0.65 Remote Similarity NPD4746 Phase 3
0.65 Remote Similarity NPD3090 Approved
0.65 Remote Similarity NPD2571 Approved
0.65 Remote Similarity NPD3087 Approved
0.65 Remote Similarity NPD3615 Approved
0.65 Remote Similarity NPD3089 Approved
0.65 Remote Similarity NPD2572 Clinical (unspecified phase)
0.65 Remote Similarity NPD3614 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