Structure

Physi-Chem Properties

Molecular Weight:  544.16
Volume:  514.52
LogP:  2.68
LogD:  1.78
LogS:  -3.078
# Rotatable Bonds:  4
TPSA:  195.6
# H-Bond Aceptor:  12
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.185
Synthetic Accessibility Score:  4.854
Fsp3:  0.37
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:  -6.308
MDCK Permeability:  1.094322851713514e-05
Pgp-inhibitor:  0.194
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.804
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.867

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.028
Plasma Protein Binding (PPB):  89.40785217285156%
Volume Distribution (VD):  0.969
Pgp-substrate:  19.741756439208984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.326
CYP1A2-substrate:  0.958
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.067
CYP2C9-inhibitor:  0.105
CYP2C9-substrate:  0.075
CYP2D6-inhibitor:  0.03
CYP2D6-substrate:  0.117
CYP3A4-inhibitor:  0.144
CYP3A4-substrate:  0.086

ADMET: Excretion

Clearance (CL):  1.805
Half-life (T1/2):  0.316

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.109
Drug-inuced Liver Injury (DILI):  0.977
AMES Toxicity:  0.702
Rat Oral Acute Toxicity:  0.011
Maximum Recommended Daily Dose:  0.019
Skin Sensitization:  0.852
Carcinogencity:  0.036
Eye Corrosion:  0.003
Eye Irritation:  0.094
Respiratory Toxicity:  0.32

Download Data

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

  Natural Product: NPC294501

Natural Product ID:  NPC294501
Common Name*:   Aranciamycin
IUPAC Name:   (2S,3S,4R)-4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy-2,5,7-trihydroxy-3-methoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trione
Synonyms:   Aranciamycin
Standard InCHIKey:  PGCZNTNNZCKKFG-LJUYJRHKSA-N
Standard InCHI:  InChI=1S/C27H28O12/c1-9-17(29)21(33)23(36-3)26(38-9)39-22-16-12(24(34)27(2,35)25(22)37-4)8-11-15(20(16)32)19(31)14-10(18(11)30)6-5-7-13(14)28/h5-9,17,21-23,25-26,28-29,32-33,35H,1-4H3/t9-,17-,21+,22+,23+,25-,26-,27+/m0/s1
SMILES:  CO[C@H]1[C@@H](O[C@H]([C@@H]([C@H]1O)O)C)O[C@@H]1c2c(O)c3c(cc2C(=O)[C@@]([C@H]1OC)(C)O)C(=O)c1c(C3=O)c(O)ccc1
Synthetic Gene Cluster:   BGC0000197;
ChEMBL Identifier:   CHEMBL1096602
PubChem CID:   15177995
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002106] Anthracyclines

*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
NPO41053 Streptomyces sp. Sp080513GE-26 Strain Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20192240]
NPO33681 Streptomyces sp. CMB-M0150 Species Streptomycetaceae Bacteria n.a. Sunshine Coast, Queensland, Australia 2007 PMID[25789410]
NPO2575 Psorothamnus fremontii Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26469557]
NPO2575 Psorothamnus fremontii Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[2681536]
NPO16616 Juniperus virginiana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16616 Juniperus virginiana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2575 Psorothamnus fremontii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16616 Juniperus virginiana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19843 Rohdea yunnanensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11362 Givotia madagascariensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12950 Squalus suckleyi Species Squalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17065 Streptomyces griseoflavus Species Streptomycetaceae 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 2700.0 nM PMID[509799]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 4100.0 nM PMID[509799]
NPT323 Cell Line SW-620 Homo sapiens IC50 > 30000.0 nM PMID[509800]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 18000.0 nM PMID[509800]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 > 30000.0 nM PMID[509800]
NPT1108 Organism Mycobacterium bovis BCG Mycobacterium bovis BCG MIC = 30000.0 nM PMID[509800]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 15000.0 nM PMID[509800]
NPT3145 Organism Bacillus subtilis subsp. spizizenii ATCC 6633 Bacillus subtilis subsp. spizizenii ATCC 6633 MIC = 15000.0 nM PMID[509800]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 30000.0 nM PMID[509800]
NPT19 Organism Escherichia coli Escherichia coli MIC > 30000.0 nM PMID[509800]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 30000.0 nM PMID[509800]
NPT20 Organism Candida albicans Candida albicans MIC > 30000.0 nM PMID[509800]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 30000.0 nM PMID[509800]
NPT1108 Organism Mycobacterium bovis BCG Mycobacterium bovis BCG IC50 = 1700.0 nM PMID[509800]
NPT79 Organism Bacillus subtilis Bacillus subtilis IC50 = 6000.0 nM PMID[509800]
NPT3145 Organism Bacillus subtilis subsp. spizizenii ATCC 6633 Bacillus subtilis subsp. spizizenii ATCC 6633 IC50 = 5800.0 nM PMID[509800]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 > 30000.0 nM PMID[509800]
NPT19 Organism Escherichia coli Escherichia coli IC50 > 30000.0 nM PMID[509800]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa IC50 > 30000.0 nM PMID[509800]
NPT20 Organism Candida albicans Candida albicans IC50 > 30000.0 nM PMID[509800]

☑ 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 NPC294501 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
0.9938 High Similarity NPC478021
0.9688 High Similarity NPC478022
0.9688 High Similarity NPC478020
0.9521 High Similarity NPC315221
0.9509 High Similarity NPC175477
0.9464 High Similarity NPC313452
0.9345 High Similarity NPC72783
0.9281 High Similarity NPC70862
0.9217 High Similarity NPC470580
0.9207 High Similarity NPC329647
0.9207 High Similarity NPC470735
0.9167 High Similarity NPC19056
0.9167 High Similarity NPC470583
0.9162 High Similarity NPC183441
0.9162 High Similarity NPC270027
0.9085 High Similarity NPC97637
0.9085 High Similarity NPC187934
0.9074 High Similarity NPC208651
0.9074 High Similarity NPC206641
0.9059 High Similarity NPC266513
0.9059 High Similarity NPC470582
0.9059 High Similarity NPC115447
0.9059 High Similarity NPC470581
0.9018 High Similarity NPC53139
0.9006 High Similarity NPC299149
0.9006 High Similarity NPC283980
0.9006 High Similarity NPC153578
0.9006 High Similarity NPC277710
0.9006 High Similarity NPC114257
0.9006 High Similarity NPC187441
0.9 High Similarity NPC475246
0.9 High Similarity NPC176246
0.8994 High Similarity NPC85368
0.8994 High Similarity NPC472054
0.8951 High Similarity NPC3449
0.8947 High Similarity NPC83331
0.8941 High Similarity NPC3718
0.8935 High Similarity NPC111536
0.8935 High Similarity NPC271385
0.8935 High Similarity NPC30432
0.8935 High Similarity NPC76128
0.8935 High Similarity NPC5029
0.8896 High Similarity NPC283480
0.8896 High Similarity NPC148323
0.8889 High Similarity NPC475233
0.8889 High Similarity NPC46958
0.8882 High Similarity NPC203751
0.8882 High Similarity NPC65118
0.8882 High Similarity NPC199357
0.8864 High Similarity NPC314672
0.8862 High Similarity NPC478026
0.8857 High Similarity NPC105591
0.8855 High Similarity NPC278329
0.8855 High Similarity NPC212099
0.8855 High Similarity NPC146837
0.8855 High Similarity NPC101116
0.8844 High Similarity NPC475161
0.8844 High Similarity NPC477860
0.8834 High Similarity NPC192219
0.8834 High Similarity NPC174599
0.8834 High Similarity NPC82190
0.883 High Similarity NPC186800
0.883 High Similarity NPC470667
0.883 High Similarity NPC68381
0.8817 High Similarity NPC222455
0.8807 High Similarity NPC205721
0.88 High Similarity NPC87583
0.8786 High Similarity NPC212290
0.8779 High Similarity NPC102053
0.8779 High Similarity NPC289876
0.8773 High Similarity NPC205172
0.8773 High Similarity NPC209393
0.8773 High Similarity NPC474621
0.8773 High Similarity NPC474622
0.8772 High Similarity NPC98776
0.875 High Similarity NPC178281
0.8735 High Similarity NPC284495
0.8722 High Similarity NPC109403
0.8722 High Similarity NPC261012
0.8722 High Similarity NPC314738
0.8721 High Similarity NPC474345
0.8721 High Similarity NPC146803
0.8713 High Similarity NPC473113
0.8688 High Similarity NPC285122
0.8678 High Similarity NPC58538
0.8667 High Similarity NPC474861
0.8667 High Similarity NPC478027
0.8663 High Similarity NPC470335
0.8663 High Similarity NPC470336
0.8659 High Similarity NPC470199
0.8659 High Similarity NPC314459
0.8655 High Similarity NPC298778
0.8647 High Similarity NPC63470
0.8647 High Similarity NPC107009
0.8642 High Similarity NPC280753
0.8642 High Similarity NPC44378
0.8631 High Similarity NPC216752
0.8629 High Similarity NPC197357
0.8629 High Similarity NPC85316
0.8621 High Similarity NPC470334
0.8619 High Similarity NPC313274
0.8614 High Similarity NPC29552
0.8611 High Similarity NPC316412
0.8611 High Similarity NPC315351
0.8598 High Similarity NPC474534
0.8598 High Similarity NPC474533
0.8596 High Similarity NPC259905
0.8588 High Similarity NPC178851
0.8564 High Similarity NPC470193
0.8564 High Similarity NPC470198
0.8564 High Similarity NPC470194
0.8564 High Similarity NPC470195
0.8564 High Similarity NPC470197
0.8564 High Similarity NPC470200
0.8564 High Similarity NPC282474
0.8564 High Similarity NPC316274
0.8564 High Similarity NPC470196
0.8564 High Similarity NPC42286
0.8562 High Similarity NPC79627
0.8555 High Similarity NPC213052
0.8545 High Similarity NPC474824
0.8545 High Similarity NPC470408
0.8545 High Similarity NPC182921
0.8545 High Similarity NPC218870
0.8538 High Similarity NPC103633
0.8533 High Similarity NPC314941
0.8531 High Similarity NPC292706
0.8531 High Similarity NPC224557
0.8525 High Similarity NPC131405
0.8523 High Similarity NPC208069
0.8514 High Similarity NPC47191
0.8509 High Similarity NPC170055
0.8506 High Similarity NPC108202
0.8494 Intermediate Similarity NPC266469
0.8488 Intermediate Similarity NPC246274
0.8488 Intermediate Similarity NPC137460
0.8488 Intermediate Similarity NPC191653
0.8485 Intermediate Similarity NPC478220
0.848 Intermediate Similarity NPC469419
0.8475 Intermediate Similarity NPC293227
0.8475 Intermediate Similarity NPC478001
0.8475 Intermediate Similarity NPC473631
0.8475 Intermediate Similarity NPC473717
0.8475 Intermediate Similarity NPC475662
0.8471 Intermediate Similarity NPC183672
0.8466 Intermediate Similarity NPC94781
0.8452 Intermediate Similarity NPC314795
0.8448 Intermediate Similarity NPC470438
0.8448 Intermediate Similarity NPC154986
0.8447 Intermediate Similarity NPC300684
0.8447 Intermediate Similarity NPC84568
0.8447 Intermediate Similarity NPC48130
0.8447 Intermediate Similarity NPC218866
0.8439 Intermediate Similarity NPC470272
0.843 Intermediate Similarity NPC470341
0.843 Intermediate Similarity NPC324522
0.843 Intermediate Similarity NPC105414
0.843 Intermediate Similarity NPC234497
0.843 Intermediate Similarity NPC473094
0.843 Intermediate Similarity NPC472058
0.8424 Intermediate Similarity NPC205918
0.8421 Intermediate Similarity NPC472049
0.8421 Intermediate Similarity NPC11608
0.8421 Intermediate Similarity NPC297404
0.8415 Intermediate Similarity NPC108487
0.8415 Intermediate Similarity NPC478219
0.8412 Intermediate Similarity NPC478229
0.8412 Intermediate Similarity NPC259834
0.8412 Intermediate Similarity NPC131745
0.8409 Intermediate Similarity NPC469418
0.84 Intermediate Similarity NPC294629
0.84 Intermediate Similarity NPC223735
0.84 Intermediate Similarity NPC470454
0.84 Intermediate Similarity NPC63105
0.84 Intermediate Similarity NPC307754
0.84 Intermediate Similarity NPC199533
0.8398 Intermediate Similarity NPC264302
0.8396 Intermediate Similarity NPC315889
0.8393 Intermediate Similarity NPC317580
0.8393 Intermediate Similarity NPC257309
0.8391 Intermediate Similarity NPC315619
0.8383 Intermediate Similarity NPC318270
0.8383 Intermediate Similarity NPC314257
0.8383 Intermediate Similarity NPC478133
0.8382 Intermediate Similarity NPC473095
0.8382 Intermediate Similarity NPC473096
0.8382 Intermediate Similarity NPC473202
0.8382 Intermediate Similarity NPC476017
0.838 Intermediate Similarity NPC221140
0.838 Intermediate Similarity NPC475352
0.838 Intermediate Similarity NPC475220
0.838 Intermediate Similarity NPC229817
0.838 Intermediate Similarity NPC473686
0.8364 Intermediate Similarity NPC315520
0.8363 Intermediate Similarity NPC66087
0.8363 Intermediate Similarity NPC278419
0.8363 Intermediate Similarity NPC179198
0.8362 Intermediate Similarity NPC245059
0.8362 Intermediate Similarity NPC84494
0.8353 Intermediate Similarity NPC477627

  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 NPC294501 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
0.9075 High Similarity NPD7879 Clinical (unspecified phase)
0.8864 High Similarity NPD6535 Approved
0.8864 High Similarity NPD6534 Approved
0.8722 High Similarity NPD6778 Approved
0.8722 High Similarity NPD6777 Approved
0.8722 High Similarity NPD6776 Approved
0.8722 High Similarity NPD6781 Approved
0.8722 High Similarity NPD6782 Approved
0.8722 High Similarity NPD6779 Approved
0.8722 High Similarity NPD6780 Approved
0.8715 High Similarity NPD7700 Phase 2
0.8715 High Similarity NPD7699 Phase 2
0.8579 High Similarity NPD7435 Discontinued
0.8533 High Similarity NPD8320 Phase 1
0.8533 High Similarity NPD8319 Approved
0.8478 Intermediate Similarity NPD7698 Approved
0.8478 Intermediate Similarity NPD7697 Approved
0.8478 Intermediate Similarity NPD7696 Phase 3
0.8432 Intermediate Similarity NPD7870 Phase 2
0.8432 Intermediate Similarity NPD7871 Phase 2
0.8418 Intermediate Similarity NPD8150 Discontinued
0.8396 Intermediate Similarity NPD7701 Phase 2
0.8352 Intermediate Similarity NPD8313 Approved
0.8352 Intermediate Similarity NPD8312 Approved
0.8307 Intermediate Similarity NPD7874 Approved
0.8307 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.8287 Intermediate Similarity NPD6213 Phase 3
0.8287 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.8287 Intermediate Similarity NPD6212 Phase 3
0.8276 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD7801 Approved
0.8191 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD6797 Phase 2
0.8176 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8136 Intermediate Similarity NPD7251 Discontinued
0.8128 Intermediate Similarity NPD6823 Phase 2
0.8125 Intermediate Similarity NPD7074 Phase 3
0.8114 Intermediate Similarity NPD3751 Discontinued
0.809 Intermediate Similarity NPD7808 Phase 3
0.8068 Intermediate Similarity NPD7054 Approved
0.8063 Intermediate Similarity NPD8151 Discontinued
0.8036 Intermediate Similarity NPD4380 Phase 2
0.8035 Intermediate Similarity NPD6959 Discontinued
0.8034 Intermediate Similarity NPD6559 Discontinued
0.8023 Intermediate Similarity NPD7472 Approved
0.8022 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD3818 Discontinued
0.8 Intermediate Similarity NPD6166 Phase 2
0.8 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD6232 Discontinued
0.7989 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD3787 Discontinued
0.7955 Intermediate Similarity NPD7473 Discontinued
0.7889 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD3226 Approved
0.7861 Intermediate Similarity NPD7075 Discontinued
0.7791 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7390 Discontinued
0.7765 Intermediate Similarity NPD5844 Phase 1
0.776 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7819 Suspended
0.768 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD7411 Suspended
0.763 Intermediate Similarity NPD1934 Approved
0.763 Intermediate Similarity NPD6801 Discontinued
0.7614 Intermediate Similarity NPD7783 Phase 2
0.7614 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD7228 Approved
0.76 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD6190 Approved
0.7558 Intermediate Similarity NPD7458 Discontinued
0.7543 Intermediate Similarity NPD5402 Approved
0.7529 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD8434 Phase 2
0.7524 Intermediate Similarity NPD8059 Phase 3
0.7524 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3882 Suspended
0.7472 Intermediate Similarity NPD5494 Approved
0.747 Intermediate Similarity NPD5405 Approved
0.747 Intermediate Similarity NPD5404 Approved
0.747 Intermediate Similarity NPD5408 Approved
0.747 Intermediate Similarity NPD5406 Approved
0.7443 Intermediate Similarity NPD3817 Phase 2
0.7429 Intermediate Similarity NPD37 Approved
0.7427 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD2532 Approved
0.7427 Intermediate Similarity NPD2534 Approved
0.7427 Intermediate Similarity NPD2533 Approved
0.7416 Intermediate Similarity NPD6234 Discontinued
0.7414 Intermediate Similarity NPD6599 Discontinued
0.7401 Intermediate Similarity NPD4966 Approved
0.7401 Intermediate Similarity NPD4965 Approved
0.7401 Intermediate Similarity NPD4967 Phase 2
0.7386 Intermediate Similarity NPD2801 Approved
0.7386 Intermediate Similarity NPD8455 Phase 2
0.7375 Intermediate Similarity NPD1470 Approved
0.7351 Intermediate Similarity NPD7685 Pre-registration
0.7341 Intermediate Similarity NPD5403 Approved
0.7322 Intermediate Similarity NPD7799 Discontinued
0.7321 Intermediate Similarity NPD7266 Discontinued
0.7321 Intermediate Similarity NPD2346 Discontinued
0.7283 Intermediate Similarity NPD1512 Approved
0.7278 Intermediate Similarity NPD1549 Phase 2
0.7267 Intermediate Similarity NPD6799 Approved
0.7263 Intermediate Similarity NPD3749 Approved
0.7258 Intermediate Similarity NPD7240 Approved
0.7257 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD8285 Discontinued
0.7225 Intermediate Similarity NPD5401 Approved
0.7219 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD7768 Phase 2
0.7202 Intermediate Similarity NPD1510 Phase 2
0.7202 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD4628 Phase 3
0.7191 Intermediate Similarity NPD1465 Phase 2
0.7186 Intermediate Similarity NPD1607 Approved
0.7169 Intermediate Similarity NPD943 Approved
0.7168 Intermediate Similarity NPD1511 Approved
0.716 Intermediate Similarity NPD2935 Discontinued
0.7158 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD7584 Approved
0.7143 Intermediate Similarity NPD7199 Phase 2
0.7143 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1201 Approved
0.711 Intermediate Similarity NPD3300 Phase 2
0.7083 Intermediate Similarity NPD8360 Approved
0.7083 Intermediate Similarity NPD8361 Approved
0.7076 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD8368 Discontinued
0.7066 Intermediate Similarity NPD1240 Approved
0.7059 Intermediate Similarity NPD2796 Approved
0.7049 Intermediate Similarity NPD1247 Approved
0.7048 Intermediate Similarity NPD3764 Approved
0.7035 Intermediate Similarity NPD6674 Discontinued
0.7029 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD230 Phase 1
0.702 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD5710 Approved
0.7011 Intermediate Similarity NPD5711 Approved
0.7005 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5035 Approved
0.6995 Remote Similarity NPD8435 Approved
0.6994 Remote Similarity NPD3750 Approved
0.6994 Remote Similarity NPD8166 Discontinued
0.6994 Remote Similarity NPD7003 Approved
0.699 Remote Similarity NPD7930 Approved
0.6988 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6973 Remote Similarity NPD3926 Phase 2
0.6971 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6963 Remote Similarity NPD8407 Phase 2
0.6954 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6919 Remote Similarity NPD1471 Phase 3
0.6901 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6884 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6869 Remote Similarity NPD8485 Approved
0.6862 Remote Similarity NPD7177 Discontinued
0.686 Remote Similarity NPD6099 Approved
0.686 Remote Similarity NPD6100 Approved
0.686 Remote Similarity NPD1551 Phase 2
0.6859 Remote Similarity NPD5028 Approved
0.6859 Remote Similarity NPD4955 Approved
0.6859 Remote Similarity NPD5034 Approved
0.6859 Remote Similarity NPD4954 Approved
0.6859 Remote Similarity NPD36 Approved
0.6859 Remote Similarity NPD5026 Approved
0.6848 Remote Similarity NPD919 Approved
0.6848 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5953 Discontinued
0.6832 Remote Similarity NPD7680 Approved
0.6818 Remote Similarity NPD7236 Approved
0.6816 Remote Similarity NPD1653 Approved
0.6816 Remote Similarity NPD7239 Suspended
0.6808 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6807 Remote Similarity NPD2798 Approved
0.6806 Remote Similarity NPD5030 Phase 2
0.6804 Remote Similarity NPD5037 Approved
0.6804 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6804 Remote Similarity NPD5038 Approved
0.6802 Remote Similarity NPD2799 Discontinued
0.68 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6798 Remote Similarity NPD6273 Approved
0.679 Remote Similarity NPD5125 Phase 3
0.679 Remote Similarity NPD5126 Approved
0.678 Remote Similarity NPD7585 Approved
0.6765 Remote Similarity NPD7999 Approved
0.6753 Remote Similarity NPD5036 Approved
0.6746 Remote Similarity NPD2313 Discontinued
0.6744 Remote Similarity NPD7097 Phase 1
0.6743 Remote Similarity NPD2800 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