Structure

Physi-Chem Properties

Molecular Weight:  622.41
Volume:  662.733
LogP:  3.913
LogD:  3.289
LogS:  -4.703
# Rotatable Bonds:  7
TPSA:  134.91
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.298
Synthetic Accessibility Score:  6.018
Fsp3:  0.743
Lipinski Rule-of-5:  Accepted
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:  -4.764
MDCK Permeability:  2.4827077140798792e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.977
Human Intestinal Absorption (HIA):  0.546
20% Bioavailability (F20%):  0.288
30% Bioavailability (F30%):  0.699

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  92.81449890136719%
Volume Distribution (VD):  2.26
Pgp-substrate:  6.278058052062988%

ADMET: Metabolism

CYP1A2-inhibitor:  0.021
CYP1A2-substrate:  0.438
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.927
CYP2C9-inhibitor:  0.067
CYP2C9-substrate:  0.097
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.26
CYP3A4-inhibitor:  0.899
CYP3A4-substrate:  0.641

ADMET: Excretion

Clearance (CL):  7.18
Half-life (T1/2):  0.259

ADMET: Toxicity

hERG Blockers:  0.32
Human Hepatotoxicity (H-HT):  0.844
Drug-inuced Liver Injury (DILI):  0.645
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.039
Maximum Recommended Daily Dose:  0.026
Skin Sensitization:  0.841
Carcinogencity:  0.075
Eye Corrosion:  0.004
Eye Irritation:  0.013
Respiratory Toxicity:  0.743

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

  Natural Product: NPC288350

Natural Product ID:  NPC288350
Common Name*:   Bafilomycin A1
IUPAC Name:   (3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-2,4-dihydroxy-5-methyl-6-propan-2-yloxan-2-yl]-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
Synonyms:   Bafilomycin A1
Standard InCHIKey:  XDHNQDDQEHDUTM-JQWOJBOSSA-N
Standard InCHI:  InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-/t22-,23+,24-,25-,26-,27+,28-,30-,31+,32+,33+,35+/m0/s1
SMILES:  CO[C@H]1/C=C/C=C(C)/C[C@H](C)[C@H](O)[C@@H](/C=C(/C=C(/C(=O)O[C@@H]1[C@H]([C@H]([C@@H]([C@@]1(O)C[C@@H](O)[C@@H]([C@H](O1)C(C)C)C)C)O)C)OC)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL290814
PubChem CID:   6436223
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000147] Macrolides and analogues

*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
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[18778099]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[18778099]
NPO33082 streptomyces spp. Species Streptomycetaceae Bacteria n.a. isolated from marine habitats n.a. PMID[20028134]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota Leaves n.a. n.a. PMID[24773071]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota stem-bark Pahang, Malaysia 2003-JUN PMID[25919190]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26918761]
NPO40536 Streptomyces albolongus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26933756]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[27077800]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[29319316]
NPO40737 Characella sp. Species n.a. n.a. n.a. n.a. n.a. PMID[29701963]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[30869890]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[32356659]
NPO40774 Xestospongia ingens Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[33549907]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9376 Tabernaemontana corymbosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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
NPT6625 Individual Protein Vacuolar ATP synthase subunit S1 Homo sapiens IC50 = 100.0 nM PMID[451626]
NPT6625 Individual Protein Vacuolar ATP synthase subunit S1 Homo sapiens Potency ratio = 1.0 n.a. PMID[451627]
NPT2891 Cell Line H4 Homo sapiens Activity = 71.96 % PMID[451628]
NPT2891 Cell Line H4 Homo sapiens Activity = 691.15 % PMID[451628]
NPT2891 Cell Line H4 Homo sapiens Activity = 1608.62 % PMID[451628]
NPT2891 Cell Line H4 Homo sapiens Activity = 4027.54 % PMID[451628]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 29.2 nM PMID[451631]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 31.5 nM PMID[451631]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 0.4 nM PMID[451631]
NPT397 Cell Line NCI-H460 Homo sapiens Activity = 100.0 % PMID[451634]
NPT81 Cell Line A549 Homo sapiens FC = 5.2 n.a. PMID[451638]
NPT81 Cell Line A549 Homo sapiens EC50 = 0.6 nM PMID[451638]
NPT218 Individual Protein Adenosine A3 receptor Homo sapiens Ki = 1080.0 nM PMID[451640]
NPT2675 Individual Protein P2X purinoceptor 3 Homo sapiens IC50 = 755.0 nM PMID[451640]
NPT279 Individual Protein Leukocyte elastase Homo sapiens Activity > 95.0 % PMID[451640]
NPT547 Cell Line BGC-823 Homo sapiens IC50 = 6470.0 nM PMID[451643]
NPT492 Cell Line Caco-2 Homo sapiens IC50 = 5490.0 nM PMID[451643]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 12410.0 nM PMID[451643]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 2030.0 nM PMID[451643]
NPT165 Cell Line HeLa Homo sapiens IC50 = 13000.0 nM PMID[451645]
NPT6647 Individual Protein Adenosinetriphosphatase Gallus gallus IC50 = 30.0 nM PMID[451625]
NPT22388 SINGLE PROTEIN Vacuolar H(+)-ATPase Bos taurus Potency ratio = 1.0 n.a. PMID[451627]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.2403 n.a. PMID[451636]
NPT2 Others Unspecified IC50 = 10.0 nM PMID[451640]
NPT2 Others Unspecified IC50 = 3.06 nM PMID[451640]
NPT35 Others n.a. permeability = 27.4 % PMID[451641]
NPT35 Others n.a. permeability = -1.5 % PMID[451641]
NPT35 Others n.a. permeability = 4.8 % PMID[451641]
NPT35 Others n.a. permeability = 90.5 % PMID[451641]
NPT35 Others n.a. permeability = 67.9 % PMID[451641]
NPT35 Others n.a. LogP = 4.736 n.a. PMID[451641]
NPT35 Others n.a. permeability = 11.0 % PMID[451641]
NPT35 Others n.a. permeability = 100.0 % PMID[451641]
NPT35 Others n.a. K = 20.7 10'-5/s PMID[451641]
NPT35 Others n.a. K = 3.25 10'-7/s PMID[451641]
NPT35 Others n.a. Ratio = 11.7 10'2No_unit PMID[451641]
NPT2 Others Unspecified IC50 = 4.0 nM PMID[451647]

☑ 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 NPC288350 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 NPC173329
0.89 High Similarity NPC133625
0.8646 High Similarity NPC120299
0.8557 High Similarity NPC475653
0.8542 High Similarity NPC255410
0.8454 Intermediate Similarity NPC475332
0.8438 Intermediate Similarity NPC300710
0.8427 Intermediate Similarity NPC184208
0.8427 Intermediate Similarity NPC8538
0.8421 Intermediate Similarity NPC238090
0.8421 Intermediate Similarity NPC472195
0.8421 Intermediate Similarity NPC472196
0.84 Intermediate Similarity NPC197736
0.837 Intermediate Similarity NPC311163
0.8367 Intermediate Similarity NPC203627
0.8333 Intermediate Similarity NPC256368
0.8333 Intermediate Similarity NPC159698
0.83 Intermediate Similarity NPC473596
0.828 Intermediate Similarity NPC316138
0.828 Intermediate Similarity NPC199382
0.828 Intermediate Similarity NPC313658
0.8261 Intermediate Similarity NPC471494
0.8222 Intermediate Similarity NPC315731
0.8211 Intermediate Similarity NPC177668
0.82 Intermediate Similarity NPC154132
0.82 Intermediate Similarity NPC2313
0.82 Intermediate Similarity NPC475157
0.82 Intermediate Similarity NPC475655
0.82 Intermediate Similarity NPC57586
0.82 Intermediate Similarity NPC471637
0.8125 Intermediate Similarity NPC476084
0.8125 Intermediate Similarity NPC114172
0.8125 Intermediate Similarity NPC476075
0.8125 Intermediate Similarity NPC471324
0.8125 Intermediate Similarity NPC206679
0.8105 Intermediate Similarity NPC133450
0.8058 Intermediate Similarity NPC315070
0.8041 Intermediate Similarity NPC189651
0.8041 Intermediate Similarity NPC475098
0.8041 Intermediate Similarity NPC109406
0.8041 Intermediate Similarity NPC159092
0.8021 Intermediate Similarity NPC3952
0.8 Intermediate Similarity NPC161855
0.8 Intermediate Similarity NPC139712
0.7979 Intermediate Similarity NPC208473
0.7961 Intermediate Similarity NPC472748
0.7957 Intermediate Similarity NPC266718
0.7905 Intermediate Similarity NPC473807
0.79 Intermediate Similarity NPC471490
0.7885 Intermediate Similarity NPC472751
0.7885 Intermediate Similarity NPC472749
0.7865 Intermediate Similarity NPC469880
0.7864 Intermediate Similarity NPC472747
0.7864 Intermediate Similarity NPC472750
0.7857 Intermediate Similarity NPC320552
0.7843 Intermediate Similarity NPC169365
0.7843 Intermediate Similarity NPC197447
0.7835 Intermediate Similarity NPC327253
0.7835 Intermediate Similarity NPC471569
0.7822 Intermediate Similarity NPC65700
0.78 Intermediate Similarity NPC473291
0.7789 Intermediate Similarity NPC186332
0.7789 Intermediate Similarity NPC47220
0.7789 Intermediate Similarity NPC61527
0.7766 Intermediate Similarity NPC473308
0.7742 Intermediate Similarity NPC251026
0.7736 Intermediate Similarity NPC193765
0.7723 Intermediate Similarity NPC2666
0.7717 Intermediate Similarity NPC470147
0.7717 Intermediate Similarity NPC133226
0.77 Intermediate Similarity NPC471492
0.7685 Intermediate Similarity NPC17791
0.767 Intermediate Similarity NPC219038
0.766 Intermediate Similarity NPC142111
0.766 Intermediate Similarity NPC473315
0.766 Intermediate Similarity NPC44261
0.7653 Intermediate Similarity NPC202886
0.7642 Intermediate Similarity NPC109376
0.7634 Intermediate Similarity NPC112868
0.7634 Intermediate Similarity NPC474894
0.7634 Intermediate Similarity NPC469469
0.7624 Intermediate Similarity NPC473333
0.7624 Intermediate Similarity NPC472995
0.7615 Intermediate Similarity NPC317460
0.7615 Intermediate Similarity NPC328074
0.7615 Intermediate Similarity NPC321272
0.7615 Intermediate Similarity NPC470025
0.7609 Intermediate Similarity NPC180725
0.7609 Intermediate Similarity NPC470148
0.7609 Intermediate Similarity NPC470149
0.76 Intermediate Similarity NPC472198
0.76 Intermediate Similarity NPC469491
0.7596 Intermediate Similarity NPC303653
0.7596 Intermediate Similarity NPC140591
0.7596 Intermediate Similarity NPC291500
0.7596 Intermediate Similarity NPC471599
0.7596 Intermediate Similarity NPC189609
0.7596 Intermediate Similarity NPC201191
0.7596 Intermediate Similarity NPC197835
0.7593 Intermediate Similarity NPC316708
0.7582 Intermediate Similarity NPC477203
0.7582 Intermediate Similarity NPC474026
0.7579 Intermediate Similarity NPC78673
0.7579 Intermediate Similarity NPC160517
0.7579 Intermediate Similarity NPC186155
0.7576 Intermediate Similarity NPC472197
0.7576 Intermediate Similarity NPC477749
0.7576 Intermediate Similarity NPC175842
0.7576 Intermediate Similarity NPC32494
0.7576 Intermediate Similarity NPC472199
0.7573 Intermediate Similarity NPC475053
0.7573 Intermediate Similarity NPC244878
0.757 Intermediate Similarity NPC224660
0.757 Intermediate Similarity NPC470024
0.7556 Intermediate Similarity NPC327041
0.7556 Intermediate Similarity NPC285840
0.7553 Intermediate Similarity NPC477385
0.7553 Intermediate Similarity NPC477390
0.7551 Intermediate Similarity NPC477748
0.7549 Intermediate Similarity NPC40812
0.7547 Intermediate Similarity NPC476738
0.7547 Intermediate Similarity NPC265502
0.7547 Intermediate Similarity NPC82251
0.7547 Intermediate Similarity NPC476740
0.7547 Intermediate Similarity NPC469960
0.7547 Intermediate Similarity NPC29389
0.7547 Intermediate Similarity NPC93026
0.7547 Intermediate Similarity NPC172867
0.7545 Intermediate Similarity NPC470027
0.7545 Intermediate Similarity NPC101400
0.7545 Intermediate Similarity NPC101965
0.7528 Intermediate Similarity NPC329914
0.7526 Intermediate Similarity NPC475186
0.7526 Intermediate Similarity NPC118077
0.7525 Intermediate Similarity NPC170204
0.7525 Intermediate Similarity NPC272050
0.7524 Intermediate Similarity NPC309398
0.7524 Intermediate Similarity NPC473816
0.7524 Intermediate Similarity NPC475367
0.7524 Intermediate Similarity NPC474581
0.7523 Intermediate Similarity NPC470026
0.75 Intermediate Similarity NPC478036
0.75 Intermediate Similarity NPC320089
0.75 Intermediate Similarity NPC471223
0.75 Intermediate Similarity NPC242233
0.75 Intermediate Similarity NPC20673
0.75 Intermediate Similarity NPC61201
0.75 Intermediate Similarity NPC38154
0.75 Intermediate Similarity NPC248775
0.75 Intermediate Similarity NPC198992
0.75 Intermediate Similarity NPC67081
0.75 Intermediate Similarity NPC59646
0.75 Intermediate Similarity NPC476049
0.75 Intermediate Similarity NPC478037
0.7477 Intermediate Similarity NPC469959
0.7477 Intermediate Similarity NPC108682
0.7477 Intermediate Similarity NPC472263
0.7477 Intermediate Similarity NPC469957
0.7476 Intermediate Similarity NPC255592
0.7476 Intermediate Similarity NPC261377
0.7476 Intermediate Similarity NPC308567
0.7476 Intermediate Similarity NPC151093
0.7475 Intermediate Similarity NPC473311
0.7473 Intermediate Similarity NPC477202
0.7455 Intermediate Similarity NPC313921
0.7455 Intermediate Similarity NPC98038
0.7451 Intermediate Similarity NPC472997
0.7451 Intermediate Similarity NPC472996
0.7449 Intermediate Similarity NPC260343
0.7449 Intermediate Similarity NPC60765
0.7449 Intermediate Similarity NPC470137
0.7444 Intermediate Similarity NPC107654
0.7431 Intermediate Similarity NPC89408
0.7431 Intermediate Similarity NPC472508
0.7429 Intermediate Similarity NPC472754
0.7426 Intermediate Similarity NPC71589
0.7426 Intermediate Similarity NPC470521
0.7419 Intermediate Similarity NPC1180
0.7419 Intermediate Similarity NPC471537
0.7407 Intermediate Similarity NPC472507
0.74 Intermediate Similarity NPC470373
0.74 Intermediate Similarity NPC470379
0.74 Intermediate Similarity NPC158061
0.7396 Intermediate Similarity NPC475035
0.7391 Intermediate Similarity NPC315394
0.7391 Intermediate Similarity NPC233071
0.7391 Intermediate Similarity NPC475711
0.7387 Intermediate Similarity NPC287075
0.7383 Intermediate Similarity NPC239961
0.7383 Intermediate Similarity NPC218158
0.7374 Intermediate Similarity NPC285588
0.7368 Intermediate Similarity NPC10080
0.7368 Intermediate Similarity NPC123908
0.7368 Intermediate Similarity NPC219656
0.7364 Intermediate Similarity NPC126897
0.7364 Intermediate Similarity NPC297945
0.7358 Intermediate Similarity NPC472755
0.7353 Intermediate Similarity NPC36954
0.7353 Intermediate Similarity NPC469583
0.7353 Intermediate Similarity NPC471141

  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 NPC288350 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
0.8602 High Similarity NPD7838 Discovery
0.8367 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7835 Intermediate Similarity NPD6698 Approved
0.7835 Intermediate Similarity NPD46 Approved
0.7404 Intermediate Similarity NPD6648 Approved
0.74 Intermediate Similarity NPD7983 Approved
0.7364 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5344 Discontinued
0.7248 Intermediate Similarity NPD6686 Approved
0.7241 Intermediate Similarity NPD7503 Approved
0.7156 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD7839 Suspended
0.6833 Remote Similarity NPD7830 Approved
0.6833 Remote Similarity NPD7829 Approved
0.6719 Remote Similarity NPD7966 Clinical (unspecified phase)
0.67 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4250 Approved
0.6667 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD8513 Phase 3
0.6667 Remote Similarity NPD4251 Approved
0.6667 Remote Similarity NPD5779 Approved
0.6667 Remote Similarity NPD8517 Approved
0.6667 Remote Similarity NPD8515 Approved
0.6667 Remote Similarity NPD8033 Approved
0.6667 Remote Similarity NPD8516 Approved
0.6604 Remote Similarity NPD5282 Discontinued
0.66 Remote Similarity NPD6110 Phase 1
0.66 Remote Similarity NPD7154 Phase 3
0.6583 Remote Similarity NPD8377 Approved
0.6583 Remote Similarity NPD8294 Approved
0.6569 Remote Similarity NPD4249 Approved
0.6555 Remote Similarity NPD7641 Discontinued
0.6555 Remote Similarity NPD7327 Approved
0.6555 Remote Similarity NPD7328 Approved
0.6529 Remote Similarity NPD8335 Approved
0.6529 Remote Similarity NPD8378 Approved
0.6529 Remote Similarity NPD8444 Approved
0.6529 Remote Similarity NPD8380 Approved
0.6529 Remote Similarity NPD8379 Approved
0.6529 Remote Similarity NPD8296 Approved
0.6522 Remote Similarity NPD6371 Approved
0.6514 Remote Similarity NPD4225 Approved
0.65 Remote Similarity NPD7516 Approved
0.6495 Remote Similarity NPD4756 Discovery
0.6471 Remote Similarity NPD7505 Discontinued
0.6457 Remote Similarity NPD7260 Phase 2
0.6452 Remote Similarity NPD8451 Approved
0.6446 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6415 Remote Similarity NPD7637 Suspended
0.641 Remote Similarity NPD6053 Discontinued
0.64 Remote Similarity NPD8074 Phase 3
0.64 Remote Similarity NPD8448 Approved
0.6381 Remote Similarity NPD6101 Approved
0.6381 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7638 Approved
0.6341 Remote Similarity NPD8080 Discontinued
0.6333 Remote Similarity NPD7500 Approved
0.633 Remote Similarity NPD4792 Clinical (unspecified phase)
0.632 Remote Similarity NPD8273 Phase 1
0.6306 Remote Similarity NPD7639 Approved
0.6306 Remote Similarity NPD7640 Approved
0.63 Remote Similarity NPD5790 Clinical (unspecified phase)
0.629 Remote Similarity NPD7642 Approved
0.629 Remote Similarity NPD8328 Phase 3
0.6271 Remote Similarity NPD8297 Approved
0.6262 Remote Similarity NPD6411 Approved
0.625 Remote Similarity NPD8390 Approved
0.625 Remote Similarity NPD8392 Approved
0.625 Remote Similarity NPD8391 Approved
0.624 Remote Similarity NPD8299 Approved
0.624 Remote Similarity NPD8342 Approved
0.624 Remote Similarity NPD8341 Approved
0.624 Remote Similarity NPD8340 Approved
0.6239 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6214 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6196 Remote Similarity NPD2685 Clinical (unspecified phase)
0.619 Remote Similarity NPD7524 Approved
0.619 Remote Similarity NPD7507 Approved
0.6186 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5785 Approved
0.6154 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6139 Remote Similarity NPD4822 Approved
0.6139 Remote Similarity NPD4820 Approved
0.6139 Remote Similarity NPD4819 Approved
0.6139 Remote Similarity NPD4821 Approved
0.6134 Remote Similarity NPD6882 Approved
0.6129 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6122 Remote Similarity NPD8039 Approved
0.6121 Remote Similarity NPD6412 Phase 2
0.6117 Remote Similarity NPD6695 Phase 3
0.6111 Remote Similarity NPD7492 Approved
0.6102 Remote Similarity NPD2067 Discontinued
0.61 Remote Similarity NPD4268 Approved
0.61 Remote Similarity NPD4271 Approved
0.6094 Remote Similarity NPD7736 Approved
0.6066 Remote Similarity NPD6009 Approved
0.6066 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6063 Remote Similarity NPD6616 Approved
0.6061 Remote Similarity NPD8415 Approved
0.6048 Remote Similarity NPD6054 Approved
0.6048 Remote Similarity NPD6319 Approved
0.6047 Remote Similarity NPD7319 Approved
0.6038 Remote Similarity NPD7750 Discontinued
0.6034 Remote Similarity NPD4211 Phase 1
0.6031 Remote Similarity NPD6845 Suspended
0.6019 Remote Similarity NPD5209 Approved
0.6016 Remote Similarity NPD7078 Approved
0.6015 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6 Remote Similarity NPD5363 Approved
0.598 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5962 Remote Similarity NPD5362 Discontinued
0.5952 Remote Similarity NPD6370 Approved
0.595 Remote Similarity NPD8133 Approved
0.5942 Remote Similarity NPD7266 Discontinued
0.5935 Remote Similarity NPD7115 Discovery
0.5935 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5932 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5932 Remote Similarity NPD6899 Approved
0.5932 Remote Similarity NPD6881 Approved
0.5926 Remote Similarity NPD1695 Approved
0.5917 Remote Similarity NPD6649 Approved
0.5917 Remote Similarity NPD6650 Approved
0.5917 Remote Similarity NPD8130 Phase 1
0.5914 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5891 Remote Similarity NPD8293 Discontinued
0.5882 Remote Similarity NPD6929 Approved
0.5882 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5873 Remote Similarity NPD6016 Approved
0.5873 Remote Similarity NPD6015 Approved
0.5872 Remote Similarity NPD3168 Discontinued
0.5872 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5868 Remote Similarity NPD969 Suspended
0.5865 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5865 Remote Similarity NPD6435 Approved
0.5862 Remote Similarity NPD1407 Approved
0.5847 Remote Similarity NPD5697 Approved
0.5841 Remote Similarity NPD6084 Phase 2
0.5841 Remote Similarity NPD6083 Phase 2
0.5833 Remote Similarity NPD7290 Approved
0.5833 Remote Similarity NPD7102 Approved
0.5833 Remote Similarity NPD6883 Approved
0.5833 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5827 Remote Similarity NPD5988 Approved
0.5825 Remote Similarity NPD6931 Approved
0.5825 Remote Similarity NPD7514 Phase 3
0.5825 Remote Similarity NPD6930 Phase 2
0.5825 Remote Similarity NPD7332 Phase 2
0.582 Remote Similarity NPD4632 Approved
0.581 Remote Similarity NPD5331 Approved
0.581 Remote Similarity NPD5332 Approved
0.58 Remote Similarity NPD8264 Approved
0.5794 Remote Similarity NPD6059 Approved
0.5785 Remote Similarity NPD6847 Approved
0.5785 Remote Similarity NPD6617 Approved
0.5785 Remote Similarity NPD6869 Approved
0.5784 Remote Similarity NPD7145 Approved
0.5781 Remote Similarity NPD7604 Phase 2
0.5776 Remote Similarity NPD7632 Discontinued
0.5769 Remote Similarity NPD4790 Discontinued
0.5769 Remote Similarity NPD6902 Approved
0.5763 Remote Similarity NPD5739 Approved
0.5763 Remote Similarity NPD7128 Approved
0.5763 Remote Similarity NPD6402 Approved
0.5763 Remote Similarity NPD6675 Approved
0.575 Remote Similarity NPD6014 Approved
0.575 Remote Similarity NPD6372 Approved
0.575 Remote Similarity NPD6012 Approved
0.575 Remote Similarity NPD6373 Approved
0.575 Remote Similarity NPD6013 Approved
0.5748 Remote Similarity NPD5983 Phase 2
0.5729 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5726 Remote Similarity NPD6647 Phase 2
0.5714 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6685 Approved
0.5714 Remote Similarity NPD4269 Approved
0.5714 Remote Similarity NPD4270 Approved
0.5703 Remote Similarity NPD5126 Approved
0.5703 Remote Similarity NPD7623 Phase 3
0.5703 Remote Similarity NPD5125 Phase 3
0.5703 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5702 Remote Similarity NPD6421 Discontinued
0.5701 Remote Similarity NPD1694 Approved
0.5692 Remote Similarity NPD6336 Discontinued
0.5686 Remote Similarity NPD5776 Phase 2
0.5686 Remote Similarity NPD6932 Approved
0.5686 Remote Similarity NPD6925 Approved
0.5683 Remote Similarity NPD8384 Approved
0.5676 Remote Similarity NPD7087 Discontinued
0.5673 Remote Similarity NPD5368 Approved
0.5667 Remote Similarity NPD7320 Approved
0.5667 Remote Similarity NPD6011 Approved
0.5664 Remote Similarity NPD5695 Phase 3
0.5649 Remote Similarity NPD7746 Phase 1
0.5649 Remote Similarity NPD7747 Phase 1
0.5648 Remote Similarity NPD5786 Approved
0.5636 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5631 Remote Similarity NPD5784 Clinical (unspecified phase)
0.563 Remote Similarity NPD6640 Phase 3

  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