Structure

Physi-Chem Properties

Molecular Weight:  258.05
Volume:  250.527
LogP:  2.99
LogD:  2.123
LogS:  -3.452
# Rotatable Bonds:  1
TPSA:  90.9
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.461
Synthetic Accessibility Score:  2.727
Fsp3:  0.071
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.018
MDCK Permeability:  1.2012060324195772e-05
Pgp-inhibitor:  0.062
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.229
20% Bioavailability (F20%):  0.048
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  95.10094451904297%
Volume Distribution (VD):  0.574
Pgp-substrate:  10.643951416015625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.978
CYP1A2-substrate:  0.427
CYP2C19-inhibitor:  0.18
CYP2C19-substrate:  0.064
CYP2C9-inhibitor:  0.672
CYP2C9-substrate:  0.669
CYP2D6-inhibitor:  0.618
CYP2D6-substrate:  0.23
CYP3A4-inhibitor:  0.172
CYP3A4-substrate:  0.102

ADMET: Excretion

Clearance (CL):  4.565
Half-life (T1/2):  0.854

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.121
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.664
Rat Oral Acute Toxicity:  0.17
Maximum Recommended Daily Dose:  0.612
Skin Sensitization:  0.85
Carcinogencity:  0.669
Eye Corrosion:  0.004
Eye Irritation:  0.9
Respiratory Toxicity:  0.368

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Similar NPs/Drugs  

  Natural Product: NPC217602

Natural Product ID:  NPC217602
Common Name*:   (S)-5-Hydroxy-2-(1-Hydroxyethyl)Naphtho[2,3-B]Furan-4,9-Dione
IUPAC Name:   5-hydroxy-2-[(1S)-1-hydroxyethyl]benzo[f][1]benzofuran-4,9-dione
Synonyms:  
Standard InCHIKey:  XJGFVZBTNKODFQ-LURJTMIESA-N
Standard InCHI:  InChI=1S/C14H10O5/c1-6(15)10-5-8-12(17)11-7(3-2-4-9(11)16)13(18)14(8)19-10/h2-6,15-16H,1H3/t6-/m0/s1
SMILES:  C[C@@H](c1cc2C(=O)c3c(cccc3O)C(=O)c2o1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL392591
PubChem CID:   14159819
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO30968 Tabebuia impetiginosa Species Bignoniaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/P19910002323]
NPO31330 Tabebuia ochracea Species Bignoniaceae Eukaryota n.a. stem n.a. DOI[10.1076/phbi.35.4.227.13306]
NPO30050 Tabebuia incana Species Bignoniaceae Eukaryota n.a. bark n.a. DOI[10.1590/S0044-59672007000100011]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[17950604]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. bark n.a. PMID[17950604]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. Brazilian n.a. PMID[19674905]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[32044231]
NPO12083 Hydnellum zonatum Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3751 Orthantha lutea n.a. n.a. n.a. 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
NPT306 Cell Line PC-3 Homo sapiens EC50 = 140.0 nM PMID[537952]
NPT81 Cell Line A549 Homo sapiens EC50 = 960.0 nM PMID[537952]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 3500.0 nM PMID[537952]
NPT80 Cell Line Raji Homo sapiens Activity = 60.0 % PMID[537952]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[537952]
NPT306 Cell Line PC-3 Homo sapiens EC50 = 140.0 nM PMID[537953]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 510.0 nM PMID[537953]
NPT81 Cell Line A549 Homo sapiens EC50 = 780.0 nM PMID[537953]
NPT611 Cell Line Hepatocyte Homo sapiens EC50 = 11100.0 nM PMID[537953]
NPT80 Cell Line Raji Homo sapiens Activity = 60.0 % PMID[537953]
NPT38 Individual Protein Signal transducer and activator of transcription 3 Homo sapiens Inhibition = 100.0 % PMID[537954]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 410.0 nM PMID[537954]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 500.0 nM PMID[537954]
NPT81 Cell Line A549 Homo sapiens IC50 = 130.0 nM PMID[537954]
NPT1689 Individual Protein Tyrosine-protein kinase JAK1 Homo sapiens Inhibition = 94.8 % PMID[537954]
NPT3246 Individual Protein Tyrosine-protein kinase JAK2 Homo sapiens Inhibition = 80.6 % PMID[537954]
NPT38 Individual Protein Signal transducer and activator of transcription 3 Homo sapiens IC50 = 2000.0 nM PMID[537954]
NPT38 Individual Protein Signal transducer and activator of transcription 3 Homo sapiens Activity = 76.0 % PMID[537954]
NPT38 Individual Protein Signal transducer and activator of transcription 3 Homo sapiens Activity = 75.0 % PMID[537954]
NPT38 Individual Protein Signal transducer and activator of transcription 3 Homo sapiens Activity = 43.0 % PMID[537954]
NPT38 Individual Protein Signal transducer and activator of transcription 3 Homo sapiens Activity = 3.0 % PMID[537954]
NPT27 Others Unspecified EC50 = 11100.0 nM PMID[537952]
NPT27 Others Unspecified EC50 = 29700.0 nM PMID[537952]
NPT27 Others Unspecified EC50 = 54500.0 nM PMID[537952]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition = 0.0 % PMID[537952]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition = 4.4 % PMID[537952]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition = 16.9 % PMID[537952]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition = 50.0 % PMID[537952]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 IC50 = 33200.0 nM PMID[537952]
NPT2 Others Unspecified Activity = 67.0 % PMID[537953]
NPT2 Others Unspecified Activity = 7.0 % PMID[537953]
NPT2 Others Unspecified Activity = 47.0 % PMID[537953]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 0.78 ug.mL-1 PMID[537953]
NPT3658 Organism Bacillus mycoides Bacillus mycoides MIC = 0.78 ug.mL-1 PMID[537953]
NPT3657 Organism Cryptococcus albidus Cryptococcus albidus MIC = 1.56 ug.mL-1 PMID[537953]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 3.13 ug.mL-1 PMID[537953]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC = 3.13 ug.mL-1 PMID[537953]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC = 12.5 ug.mL-1 PMID[537953]
NPT20 Organism Candida albicans Candida albicans MIC = 25.0 ug.mL-1 PMID[537953]
NPT3086 Organism Penicillium expansum Penicillium expansum MIC = 25.0 ug.mL-1 PMID[537953]
NPT3656 Organism Paecilomyces variotii Paecilomyces variotii MIC = 25.0 ug.mL-1 PMID[537953]
NPT19 Organism Escherichia coli Escherichia coli MIC > 100.0 ug.mL-1 PMID[537953]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 100.0 ug.mL-1 PMID[537953]
NPT3608 Organism Salmonella enteritidis Salmonella enterica subsp. enterica serovar Enteritidis MIC > 100.0 ug.mL-1 PMID[537953]
NPT27 Others Unspecified EC50 = 3360.0 nM PMID[537953]
NPT27 Others Unspecified EC50 = 5510.0 nM PMID[537953]
NPT27 Others Unspecified EC50 = 11100.0 nM PMID[537953]
NPT27 Others Unspecified EC50 = 29700.0 nM PMID[537953]
NPT27 Others Unspecified EC50 = 54500.0 nM PMID[537953]
NPT2 Others Unspecified IC50 = 33200.0 nM PMID[537953]
NPT2 Others Unspecified Activity = 50.0 % PMID[537953]
NPT2 Others Unspecified Activity = 16.9 % PMID[537953]
NPT2 Others Unspecified Activity = 4.4 % PMID[537953]
NPT2 Others Unspecified Activity = 0.0 % PMID[537953]
NPT2 Others Unspecified Activity = 3.9 n.a. PMID[537953]
NPT2 Others Unspecified Activity = 68.0 % PMID[537954]
NPT2 Others Unspecified Activity = 78.0 % PMID[537954]
NPT2 Others Unspecified Activity = 21.0 % PMID[537954]
NPT2 Others Unspecified Activity = 35.0 % PMID[537954]

☑ 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 NPC217602 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 NPC473282
1.0 High Similarity NPC104380
0.9867 High Similarity NPC317900
0.9867 High Similarity NPC476404
0.9867 High Similarity NPC294300
0.9664 High Similarity NPC471613
0.953 High Similarity NPC226578
0.9333 High Similarity NPC280025
0.9267 High Similarity NPC252208
0.8931 High Similarity NPC269117
0.8792 High Similarity NPC265181
0.8773 High Similarity NPC186392
0.8688 High Similarity NPC228501
0.8659 High Similarity NPC95715
0.8659 High Similarity NPC44602
0.8645 High Similarity NPC469425
0.8625 High Similarity NPC10051
0.8625 High Similarity NPC299094
0.8608 High Similarity NPC275878
0.8571 High Similarity NPC469385
0.8562 High Similarity NPC478223
0.8554 High Similarity NPC28042
0.8554 High Similarity NPC315306
0.8554 High Similarity NPC313717
0.8553 High Similarity NPC88958
0.8553 High Similarity NPC158261
0.8553 High Similarity NPC42458
0.8553 High Similarity NPC290927
0.8529 High Similarity NPC475996
0.8519 High Similarity NPC472961
0.8519 High Similarity NPC472962
0.8485 Intermediate Similarity NPC53640
0.8476 Intermediate Similarity NPC472581
0.8466 Intermediate Similarity NPC478134
0.8466 Intermediate Similarity NPC472780
0.8466 Intermediate Similarity NPC472783
0.8466 Intermediate Similarity NPC24761
0.8452 Intermediate Similarity NPC277510
0.8452 Intermediate Similarity NPC477409
0.8438 Intermediate Similarity NPC179170
0.8438 Intermediate Similarity NPC84721
0.8428 Intermediate Similarity NPC115324
0.8415 Intermediate Similarity NPC219861
0.8415 Intermediate Similarity NPC193998
0.8412 Intermediate Similarity NPC5671
0.8411 Intermediate Similarity NPC141934
0.8405 Intermediate Similarity NPC472782
0.8405 Intermediate Similarity NPC472781
0.8405 Intermediate Similarity NPC470810
0.8405 Intermediate Similarity NPC313368
0.8395 Intermediate Similarity NPC96342
0.8395 Intermediate Similarity NPC164110
0.8395 Intermediate Similarity NPC246647
0.8395 Intermediate Similarity NPC212967
0.8385 Intermediate Similarity NPC148938
0.8385 Intermediate Similarity NPC268008
0.8383 Intermediate Similarity NPC202470
0.8375 Intermediate Similarity NPC60211
0.8375 Intermediate Similarity NPC207624
0.8373 Intermediate Similarity NPC191012
0.8372 Intermediate Similarity NPC228209
0.8366 Intermediate Similarity NPC477408
0.8366 Intermediate Similarity NPC114620
0.8366 Intermediate Similarity NPC103337
0.8364 Intermediate Similarity NPC1706
0.8364 Intermediate Similarity NPC39305
0.8364 Intermediate Similarity NPC109180
0.8364 Intermediate Similarity NPC59295
0.8364 Intermediate Similarity NPC1755
0.8364 Intermediate Similarity NPC263092
0.8354 Intermediate Similarity NPC96031
0.8354 Intermediate Similarity NPC45124
0.8354 Intermediate Similarity NPC74854
0.8354 Intermediate Similarity NPC218569
0.8354 Intermediate Similarity NPC30655
0.8344 Intermediate Similarity NPC476349
0.8344 Intermediate Similarity NPC477410
0.8344 Intermediate Similarity NPC476350
0.8344 Intermediate Similarity NPC471346
0.8343 Intermediate Similarity NPC30550
0.8333 Intermediate Similarity NPC180924
0.8323 Intermediate Similarity NPC476459
0.8323 Intermediate Similarity NPC235333
0.8313 Intermediate Similarity NPC314653
0.8313 Intermediate Similarity NPC474772
0.8313 Intermediate Similarity NPC58668
0.8313 Intermediate Similarity NPC193976
0.8313 Intermediate Similarity NPC175617
0.8313 Intermediate Similarity NPC472784
0.8313 Intermediate Similarity NPC136641
0.8313 Intermediate Similarity NPC156244
0.8313 Intermediate Similarity NPC106372
0.8313 Intermediate Similarity NPC472423
0.8313 Intermediate Similarity NPC23668
0.8313 Intermediate Similarity NPC316262
0.8313 Intermediate Similarity NPC145830
0.8313 Intermediate Similarity NPC302783
0.8313 Intermediate Similarity NPC472049
0.8313 Intermediate Similarity NPC473201
0.8313 Intermediate Similarity NPC474744
0.8303 Intermediate Similarity NPC272722
0.8303 Intermediate Similarity NPC238995
0.8302 Intermediate Similarity NPC478219
0.8294 Intermediate Similarity NPC289244
0.8293 Intermediate Similarity NPC304839
0.8293 Intermediate Similarity NPC220582
0.8291 Intermediate Similarity NPC21835
0.8284 Intermediate Similarity NPC91650
0.8282 Intermediate Similarity NPC477833
0.8282 Intermediate Similarity NPC201127
0.828 Intermediate Similarity NPC73416
0.828 Intermediate Similarity NPC98926
0.828 Intermediate Similarity NPC160777
0.8274 Intermediate Similarity NPC473096
0.8274 Intermediate Similarity NPC473095
0.8272 Intermediate Similarity NPC213936
0.8272 Intermediate Similarity NPC297531
0.8272 Intermediate Similarity NPC80489
0.8266 Intermediate Similarity NPC8927
0.8263 Intermediate Similarity NPC472895
0.8263 Intermediate Similarity NPC477517
0.8261 Intermediate Similarity NPC154683
0.8261 Intermediate Similarity NPC35567
0.8261 Intermediate Similarity NPC142308
0.8261 Intermediate Similarity NPC253872
0.8261 Intermediate Similarity NPC471347
0.8261 Intermediate Similarity NPC243171
0.8261 Intermediate Similarity NPC40356
0.8261 Intermediate Similarity NPC171651
0.8261 Intermediate Similarity NPC285623
0.8261 Intermediate Similarity NPC471349
0.8261 Intermediate Similarity NPC67654
0.8261 Intermediate Similarity NPC304954
0.8256 Intermediate Similarity NPC104682
0.8253 Intermediate Similarity NPC476931
0.8253 Intermediate Similarity NPC475779
0.8253 Intermediate Similarity NPC472582
0.825 Intermediate Similarity NPC202595
0.825 Intermediate Similarity NPC260582
0.825 Intermediate Similarity NPC267117
0.825 Intermediate Similarity NPC255641
0.825 Intermediate Similarity NPC290954
0.825 Intermediate Similarity NPC472421
0.8247 Intermediate Similarity NPC1268
0.8242 Intermediate Similarity NPC476929
0.8239 Intermediate Similarity NPC295436
0.8235 Intermediate Similarity NPC154986
0.8235 Intermediate Similarity NPC98776
0.8232 Intermediate Similarity NPC287559
0.8229 Intermediate Similarity NPC240808
0.8228 Intermediate Similarity NPC1940
0.8228 Intermediate Similarity NPC148011
0.8221 Intermediate Similarity NPC472461
0.8221 Intermediate Similarity NPC160015
0.8221 Intermediate Similarity NPC247677
0.8221 Intermediate Similarity NPC221992
0.8217 Intermediate Similarity NPC19896
0.8214 Intermediate Similarity NPC473094
0.8214 Intermediate Similarity NPC150131
0.8214 Intermediate Similarity NPC241820
0.8214 Intermediate Similarity NPC247973
0.821 Intermediate Similarity NPC189130
0.821 Intermediate Similarity NPC208806
0.821 Intermediate Similarity NPC303950
0.821 Intermediate Similarity NPC27532
0.821 Intermediate Similarity NPC301233
0.821 Intermediate Similarity NPC256346
0.821 Intermediate Similarity NPC472786
0.821 Intermediate Similarity NPC203080
0.821 Intermediate Similarity NPC474000
0.821 Intermediate Similarity NPC214632
0.821 Intermediate Similarity NPC293286
0.821 Intermediate Similarity NPC246328
0.821 Intermediate Similarity NPC325028
0.8204 Intermediate Similarity NPC45449
0.8204 Intermediate Similarity NPC36320
0.8199 Intermediate Similarity NPC262038
0.8199 Intermediate Similarity NPC470569
0.8199 Intermediate Similarity NPC132990
0.8199 Intermediate Similarity NPC319910
0.8199 Intermediate Similarity NPC230848
0.8199 Intermediate Similarity NPC262039
0.8199 Intermediate Similarity NPC170169
0.8199 Intermediate Similarity NPC254412
0.8199 Intermediate Similarity NPC472580
0.8199 Intermediate Similarity NPC278476
0.8199 Intermediate Similarity NPC46882
0.8199 Intermediate Similarity NPC471229
0.8198 Intermediate Similarity NPC23553
0.8198 Intermediate Similarity NPC77179
0.8194 Intermediate Similarity NPC477537
0.8193 Intermediate Similarity NPC212099
0.8193 Intermediate Similarity NPC278329
0.8193 Intermediate Similarity NPC101116
0.8193 Intermediate Similarity NPC478229
0.8193 Intermediate Similarity NPC211107
0.8193 Intermediate Similarity NPC472402
0.8193 Intermediate Similarity NPC146837
0.8192 Intermediate Similarity NPC60848
0.8187 Intermediate Similarity NPC296030

  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 NPC217602 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
0.8792 High Similarity NPD1471 Phase 3
0.8333 Intermediate Similarity NPD3882 Suspended
0.8301 Intermediate Similarity NPD2344 Approved
0.8187 Intermediate Similarity NPD3226 Approved
0.8089 Intermediate Similarity NPD2309 Approved
0.8061 Intermediate Similarity NPD7075 Discontinued
0.8024 Intermediate Similarity NPD1247 Approved
0.8 Intermediate Similarity NPD8434 Phase 2
0.7988 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD1934 Approved
0.7927 Intermediate Similarity NPD6801 Discontinued
0.7914 Intermediate Similarity NPD6599 Discontinued
0.7911 Intermediate Similarity NPD4628 Phase 3
0.7898 Intermediate Similarity NPD1549 Phase 2
0.7879 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD6799 Approved
0.7834 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD3926 Phase 2
0.7821 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD6559 Discontinued
0.7805 Intermediate Similarity NPD4380 Phase 2
0.7798 Intermediate Similarity NPD919 Approved
0.7791 Intermediate Similarity NPD3818 Discontinued
0.7778 Intermediate Similarity NPD1512 Approved
0.7778 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6166 Phase 2
0.7771 Intermediate Similarity NPD7819 Suspended
0.7738 Intermediate Similarity NPD3749 Approved
0.7736 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD5402 Approved
0.7725 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD2346 Discontinued
0.7707 Intermediate Similarity NPD1510 Phase 2
0.7692 Intermediate Similarity NPD1607 Approved
0.7688 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD3751 Discontinued
0.7682 Intermediate Similarity NPD1470 Approved
0.7677 Intermediate Similarity NPD1240 Approved
0.7665 Intermediate Similarity NPD2801 Approved
0.7654 Intermediate Similarity NPD1511 Approved
0.7647 Intermediate Similarity NPD5494 Approved
0.7644 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD5403 Approved
0.7619 Intermediate Similarity NPD3817 Phase 2
0.7607 Intermediate Similarity NPD2532 Approved
0.7607 Intermediate Similarity NPD5401 Approved
0.7607 Intermediate Similarity NPD2534 Approved
0.7607 Intermediate Similarity NPD2533 Approved
0.7602 Intermediate Similarity NPD6959 Discontinued
0.7588 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD6232 Discontinued
0.7557 Intermediate Similarity NPD6797 Phase 2
0.7547 Intermediate Similarity NPD2796 Approved
0.7545 Intermediate Similarity NPD7411 Suspended
0.7529 Intermediate Similarity NPD7473 Discontinued
0.7528 Intermediate Similarity NPD8313 Approved
0.7528 Intermediate Similarity NPD8312 Approved
0.7516 Intermediate Similarity NPD2800 Approved
0.7515 Intermediate Similarity NPD920 Approved
0.7515 Intermediate Similarity NPD2296 Approved
0.7514 Intermediate Similarity NPD7251 Discontinued
0.75 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD2163 Approved
0.7484 Intermediate Similarity NPD2799 Discontinued
0.7484 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD7808 Phase 3
0.7472 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD4060 Phase 1
0.7443 Intermediate Similarity NPD5844 Phase 1
0.7438 Intermediate Similarity NPD1551 Phase 2
0.7433 Intermediate Similarity NPD6779 Approved
0.7433 Intermediate Similarity NPD6780 Approved
0.7433 Intermediate Similarity NPD6781 Approved
0.7433 Intermediate Similarity NPD6777 Approved
0.7433 Intermediate Similarity NPD6782 Approved
0.7433 Intermediate Similarity NPD6776 Approved
0.7433 Intermediate Similarity NPD6778 Approved
0.7417 Intermediate Similarity NPD1201 Approved
0.7417 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD7435 Discontinued
0.7407 Intermediate Similarity NPD1243 Approved
0.7405 Intermediate Similarity NPD6355 Discontinued
0.7401 Intermediate Similarity NPD7074 Phase 3
0.7394 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD5762 Approved
0.7391 Intermediate Similarity NPD5763 Approved
0.7378 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD3750 Approved
0.7356 Intermediate Similarity NPD6808 Phase 2
0.7356 Intermediate Similarity NPD3787 Discontinued
0.7353 Intermediate Similarity NPD5761 Phase 2
0.7353 Intermediate Similarity NPD5760 Phase 2
0.7345 Intermediate Similarity NPD7054 Approved
0.7329 Intermediate Similarity NPD2935 Discontinued
0.7325 Intermediate Similarity NPD2313 Discontinued
0.7322 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD6765 Approved
0.7318 Intermediate Similarity NPD6764 Approved
0.7308 Intermediate Similarity NPD8150 Discontinued
0.7303 Intermediate Similarity NPD7472 Approved
0.7294 Intermediate Similarity NPD6279 Approved
0.7294 Intermediate Similarity NPD6280 Approved
0.7263 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD1608 Approved
0.7253 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD1465 Phase 2
0.7246 Intermediate Similarity NPD6273 Approved
0.7233 Intermediate Similarity NPD943 Approved
0.7226 Intermediate Similarity NPD1203 Approved
0.7225 Intermediate Similarity NPD7698 Approved
0.7225 Intermediate Similarity NPD7696 Phase 3
0.7225 Intermediate Similarity NPD7697 Approved
0.7219 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6798 Discontinued
0.7215 Intermediate Similarity NPD3764 Approved
0.7188 Intermediate Similarity NPD7871 Phase 2
0.7188 Intermediate Similarity NPD447 Suspended
0.7188 Intermediate Similarity NPD7870 Phase 2
0.7186 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7874 Approved
0.7179 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD7768 Phase 2
0.7166 Intermediate Similarity NPD6534 Approved
0.7166 Intermediate Similarity NPD6535 Approved
0.7165 Intermediate Similarity NPD7701 Phase 2
0.7161 Intermediate Similarity NPD1876 Approved
0.716 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7033 Discontinued
0.7158 Intermediate Similarity NPD6784 Approved
0.7158 Intermediate Similarity NPD6785 Approved
0.7134 Intermediate Similarity NPD9494 Approved
0.7133 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD2649 Approved
0.7118 Intermediate Similarity NPD2651 Approved
0.7108 Intermediate Similarity NPD2354 Approved
0.7088 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD9092 Discovery
0.7083 Intermediate Similarity NPD4661 Approved
0.7083 Intermediate Similarity NPD4662 Approved
0.7072 Intermediate Similarity NPD5953 Discontinued
0.707 Intermediate Similarity NPD2798 Approved
0.7068 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5710 Approved
0.7062 Intermediate Similarity NPD5711 Approved
0.7059 Intermediate Similarity NPD17 Approved
0.7056 Intermediate Similarity NPD7801 Approved
0.7055 Intermediate Similarity NPD3748 Approved
0.7053 Intermediate Similarity NPD7700 Phase 2
0.7053 Intermediate Similarity NPD7699 Phase 2
0.7032 Intermediate Similarity NPD3972 Approved
0.7032 Intermediate Similarity NPD9717 Approved
0.7024 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD7458 Discontinued
0.7012 Intermediate Similarity NPD6099 Approved
0.7012 Intermediate Similarity NPD6100 Approved
0.701 Intermediate Similarity NPD8319 Approved
0.701 Intermediate Similarity NPD8320 Phase 1
0.7006 Intermediate Similarity NPD7199 Phase 2
0.7006 Intermediate Similarity NPD3887 Approved
0.7006 Intermediate Similarity NPD6190 Approved
0.7 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD411 Approved
0.7 Intermediate Similarity NPD7177 Discontinued
0.7 Intermediate Similarity NPD3268 Approved
0.6995 Remote Similarity NPD3057 Approved
0.6994 Remote Similarity NPD37 Approved
0.6994 Remote Similarity NPD6844 Discontinued
0.6989 Remote Similarity NPD6234 Discontinued
0.6983 Remote Similarity NPD2403 Approved
0.6981 Remote Similarity NPD6832 Phase 2
0.6975 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6971 Remote Similarity NPD4967 Phase 2
0.6971 Remote Similarity NPD4966 Approved
0.6971 Remote Similarity NPD4965 Approved
0.6943 Remote Similarity NPD1283 Approved
0.6941 Remote Similarity NPD5049 Phase 3
0.6928 Remote Similarity NPD9545 Approved
0.6914 Remote Similarity NPD1613 Approved
0.6914 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6914 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6907 Remote Similarity NPD2972 Approved
0.6907 Remote Similarity NPD3533 Approved
0.6907 Remote Similarity NPD6823 Phase 2
0.6894 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6886 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6883 Remote Similarity NPD1651 Approved
0.6882 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6881 Remote Similarity NPD8404 Phase 2

  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