Structure

Physi-Chem Properties

Molecular Weight:  241.07
Volume:  243.943
LogP:  3.758
LogD:  3.412
LogS:  -4.165
# Rotatable Bonds:  2
TPSA:  62.32
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.644
Synthetic Accessibility Score:  2.007
Fsp3:  0.071
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.98
MDCK Permeability:  1.440021787857404e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.724

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.71
Plasma Protein Binding (PPB):  94.78874969482422%
Volume Distribution (VD):  0.526
Pgp-substrate:  4.587469100952148%

ADMET: Metabolism

CYP1A2-inhibitor:  0.988
CYP1A2-substrate:  0.883
CYP2C19-inhibitor:  0.751
CYP2C19-substrate:  0.093
CYP2C9-inhibitor:  0.461
CYP2C9-substrate:  0.927
CYP2D6-inhibitor:  0.727
CYP2D6-substrate:  0.866
CYP3A4-inhibitor:  0.532
CYP3A4-substrate:  0.141

ADMET: Excretion

Clearance (CL):  6.693
Half-life (T1/2):  0.652

ADMET: Toxicity

hERG Blockers:  0.038
Human Hepatotoxicity (H-HT):  0.343
Drug-inuced Liver Injury (DILI):  0.865
AMES Toxicity:  0.509
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.895
Skin Sensitization:  0.807
Carcinogencity:  0.267
Eye Corrosion:  0.009
Eye Irritation:  0.959
Respiratory Toxicity:  0.903

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

  Natural Product: NPC3207

Natural Product ID:  NPC3207
Common Name*:   Mukonidine
IUPAC Name:   methyl 2-hydroxy-9H-carbazole-3-carboxylate
Synonyms:   Mukonidine
Standard InCHIKey:  SJVKEEPWQLIYIJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H11NO3/c1-18-14(17)10-6-9-8-4-2-3-5-11(8)15-12(9)7-13(10)16/h2-7,15-16H,1H3
SMILES:  COC(=O)c1cc2c3ccccc3[nH]c2cc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1088190
PubChem CID:   10999153
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*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
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11720530]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724858]
NPO29161 Hyptis urticoides Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19265396]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. Guam Island, Pacific Ocean n.a. PMID[21774474]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22050382]
NPO18135 Clausena vestita Species Rutaceae Eukaryota whole plants Yunnan Province, China 2008-JAN PMID[22093759]
NPO4806 Clausena wallichii Species Rutaceae Eukaryota Roots n.a. n.a. PMID[22482432]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. Guam Island, Pacific Ocean n.a. PMID[23164710]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26203536]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota Seeds n.a. n.a. PMID[28951079]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18135 Clausena vestita Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29070 Bulbine asphodeloides Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28544 Podocalyx loranthoides Species Picrodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4806 Clausena wallichii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23710 Otholobium pubescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29161 Hyptis urticoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29321 Octopus octopodia Species Octopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28943 Daldinia vernicosa Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29028 Cicer cuneatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24890 Iris sanguinea Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25073 Saccharina latissima Species Laminariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27603 Populus candicans Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29497 Delphinium speciosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28735 Helicia erratica Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28427 Gutenbergia marginata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29461 Sarcophyton infundibuliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27349 Rhododendron edgeworthii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29387 Eudendrium racemosum Species Eudendriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25248 Gloydius blomhoffii Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28639 Trixis grisebachii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29073 Ipomoea carnea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29035 Pseudomonas cichorii Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29518 Nardia scalaris Species Solenostomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28500 Griselinia scandens Species Griseliniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29180 Monachosorum maximowiczii Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29095 Yucca elata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28993 Streptomyces venezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO28961 Croton hutchinsonianus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens IC50 > 160000.0 nM PMID[465099]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 204800.0 nM PMID[465100]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 134200.0 nM PMID[465100]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 64.0 ug.mL-1 PMID[465100]
NPT19 Organism Escherichia coli Escherichia coli MIC = 128.0 ug.mL-1 PMID[465100]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC = 32.0 ug.mL-1 PMID[465100]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC90 = 23300.0 nM PMID[465101]

☑ 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 NPC3207 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
0.9694 High Similarity NPC174760
0.9634 High Similarity NPC39679
0.9538 High Similarity NPC116238
0.9442 High Similarity NPC169402
0.9394 High Similarity NPC247803
0.9385 High Similarity NPC87413
0.933 High Similarity NPC86834
0.933 High Similarity NPC210828
0.93 High Similarity NPC150239
0.9286 High Similarity NPC23294
0.9235 High Similarity NPC303951
0.9179 High Similarity NPC4687
0.9141 High Similarity NPC310211
0.9141 High Similarity NPC308137
0.8916 High Similarity NPC46561
0.8889 High Similarity NPC249583
0.8786 High Similarity NPC198503
0.8768 High Similarity NPC118228
0.8692 High Similarity NPC6786
0.866 High Similarity NPC179287
0.865 High Similarity NPC300156
0.8639 High Similarity NPC160381
0.8612 High Similarity NPC51388
0.8551 High Similarity NPC184408
0.8528 High Similarity NPC70956
0.8528 High Similarity NPC243834
0.8482 Intermediate Similarity NPC212535
0.8472 Intermediate Similarity NPC473187
0.8439 Intermediate Similarity NPC9894
0.8421 Intermediate Similarity NPC208084
0.8394 Intermediate Similarity NPC94943
0.8392 Intermediate Similarity NPC306376
0.8374 Intermediate Similarity NPC45190
0.8372 Intermediate Similarity NPC474701
0.8357 Intermediate Similarity NPC39500
0.8342 Intermediate Similarity NPC190007
0.8279 Intermediate Similarity NPC274640
0.8276 Intermediate Similarity NPC134848
0.8255 Intermediate Similarity NPC280799
0.8244 Intermediate Similarity NPC283117
0.8227 Intermediate Similarity NPC291535
0.8227 Intermediate Similarity NPC475085
0.8227 Intermediate Similarity NPC475112
0.8216 Intermediate Similarity NPC144452
0.819 Intermediate Similarity NPC330009
0.8173 Intermediate Similarity NPC294375
0.8155 Intermediate Similarity NPC193777
0.8155 Intermediate Similarity NPC321428
0.8152 Intermediate Similarity NPC293151
0.815 Intermediate Similarity NPC131017
0.8086 Intermediate Similarity NPC187501
0.8069 Intermediate Similarity NPC153042
0.803 Intermediate Similarity NPC72211
0.8021 Intermediate Similarity NPC474409
0.8019 Intermediate Similarity NPC476106
0.8017 Intermediate Similarity NPC89549
0.799 Intermediate Similarity NPC325297
0.7955 Intermediate Similarity NPC474688
0.7953 Intermediate Similarity NPC225279
0.7944 Intermediate Similarity NPC473041
0.7931 Intermediate Similarity NPC70259
0.7917 Intermediate Similarity NPC60621
0.7911 Intermediate Similarity NPC475844
0.7895 Intermediate Similarity NPC183777
0.789 Intermediate Similarity NPC97746
0.7882 Intermediate Similarity NPC205934
0.7882 Intermediate Similarity NPC276517
0.7882 Intermediate Similarity NPC43787
0.7877 Intermediate Similarity NPC12344
0.7877 Intermediate Similarity NPC48353
0.7857 Intermediate Similarity NPC72980
0.7857 Intermediate Similarity NPC88363
0.785 Intermediate Similarity NPC148183
0.785 Intermediate Similarity NPC152768
0.7838 Intermediate Similarity NPC132329
0.7837 Intermediate Similarity NPC162484
0.7824 Intermediate Similarity NPC74360
0.78 Intermediate Similarity NPC194040
0.7788 Intermediate Similarity NPC199277
0.7788 Intermediate Similarity NPC135887
0.7783 Intermediate Similarity NPC194740
0.7778 Intermediate Similarity NPC264285
0.7773 Intermediate Similarity NPC469734
0.7772 Intermediate Similarity NPC83111
0.7767 Intermediate Similarity NPC469928
0.7757 Intermediate Similarity NPC89508
0.7751 Intermediate Similarity NPC165599
0.7742 Intermediate Similarity NPC473179
0.7723 Intermediate Similarity NPC246700
0.7718 Intermediate Similarity NPC141454
0.7716 Intermediate Similarity NPC473188
0.77 Intermediate Similarity NPC84478
0.7696 Intermediate Similarity NPC303658
0.7692 Intermediate Similarity NPC213308
0.7685 Intermediate Similarity NPC74969
0.7671 Intermediate Similarity NPC477532
0.7667 Intermediate Similarity NPC476098
0.7667 Intermediate Similarity NPC317572
0.7661 Intermediate Similarity NPC298436
0.7656 Intermediate Similarity NPC267423
0.7656 Intermediate Similarity NPC476044
0.7653 Intermediate Similarity NPC209769
0.765 Intermediate Similarity NPC312645
0.7647 Intermediate Similarity NPC21638
0.7644 Intermediate Similarity NPC128823
0.7644 Intermediate Similarity NPC473105
0.7644 Intermediate Similarity NPC280714
0.7642 Intermediate Similarity NPC270918
0.7634 Intermediate Similarity NPC260434
0.763 Intermediate Similarity NPC132539
0.7629 Intermediate Similarity NPC91868
0.7629 Intermediate Similarity NPC63971
0.7623 Intermediate Similarity NPC471762
0.7621 Intermediate Similarity NPC15801
0.7602 Intermediate Similarity NPC122436
0.7581 Intermediate Similarity NPC146418
0.7576 Intermediate Similarity NPC84347
0.757 Intermediate Similarity NPC201697
0.7559 Intermediate Similarity NPC244741
0.7557 Intermediate Similarity NPC220851
0.7557 Intermediate Similarity NPC16352
0.7549 Intermediate Similarity NPC128751
0.7543 Intermediate Similarity NPC475666
0.7535 Intermediate Similarity NPC11464
0.7535 Intermediate Similarity NPC269367
0.7534 Intermediate Similarity NPC96321
0.7525 Intermediate Similarity NPC303225
0.7512 Intermediate Similarity NPC469497
0.7512 Intermediate Similarity NPC106833
0.751 Intermediate Similarity NPC315634
0.751 Intermediate Similarity NPC100734
0.751 Intermediate Similarity NPC88923
0.75 Intermediate Similarity NPC78609
0.75 Intermediate Similarity NPC46580
0.75 Intermediate Similarity NPC473185
0.75 Intermediate Similarity NPC160898
0.75 Intermediate Similarity NPC81939
0.75 Intermediate Similarity NPC220337
0.7489 Intermediate Similarity NPC305984
0.7488 Intermediate Similarity NPC230403
0.7467 Intermediate Similarity NPC252251
0.7467 Intermediate Similarity NPC66777
0.7465 Intermediate Similarity NPC470930
0.7463 Intermediate Similarity NPC242928
0.7456 Intermediate Similarity NPC39370
0.7448 Intermediate Similarity NPC284685
0.7445 Intermediate Similarity NPC473186
0.7443 Intermediate Similarity NPC322064
0.7442 Intermediate Similarity NPC470931
0.7442 Intermediate Similarity NPC475910
0.7441 Intermediate Similarity NPC329747
0.7441 Intermediate Similarity NPC315491
0.7441 Intermediate Similarity NPC45459
0.7418 Intermediate Similarity NPC223427
0.7401 Intermediate Similarity NPC14288
0.7401 Intermediate Similarity NPC477531
0.7397 Intermediate Similarity NPC16066
0.7395 Intermediate Similarity NPC88008
0.7393 Intermediate Similarity NPC178858
0.7391 Intermediate Similarity NPC138370
0.7391 Intermediate Similarity NPC235685
0.7387 Intermediate Similarity NPC276657
0.7385 Intermediate Similarity NPC219087
0.738 Intermediate Similarity NPC182222
0.7378 Intermediate Similarity NPC319232
0.7378 Intermediate Similarity NPC24370
0.7373 Intermediate Similarity NPC309845
0.7368 Intermediate Similarity NPC475720
0.7368 Intermediate Similarity NPC474192
0.7364 Intermediate Similarity NPC472589
0.7361 Intermediate Similarity NPC171787
0.7359 Intermediate Similarity NPC101350
0.7359 Intermediate Similarity NPC470784
0.7357 Intermediate Similarity NPC209174
0.7357 Intermediate Similarity NPC322135
0.7356 Intermediate Similarity NPC55493
0.7353 Intermediate Similarity NPC472588
0.7353 Intermediate Similarity NPC62069
0.7345 Intermediate Similarity NPC124920
0.7345 Intermediate Similarity NPC304307
0.7345 Intermediate Similarity NPC261251
0.7345 Intermediate Similarity NPC34580
0.7345 Intermediate Similarity NPC118559
0.7344 Intermediate Similarity NPC191489
0.7342 Intermediate Similarity NPC67401
0.7336 Intermediate Similarity NPC473182
0.7336 Intermediate Similarity NPC284888
0.7324 Intermediate Similarity NPC232600
0.7324 Intermediate Similarity NPC471944
0.732 Intermediate Similarity NPC76982
0.7316 Intermediate Similarity NPC184680
0.7315 Intermediate Similarity NPC315545
0.7315 Intermediate Similarity NPC314297
0.7313 Intermediate Similarity NPC100547
0.7311 Intermediate Similarity NPC241024
0.7309 Intermediate Similarity NPC323969
0.7309 Intermediate Similarity NPC195788
0.7309 Intermediate Similarity NPC237901
0.7306 Intermediate Similarity NPC118940
0.7306 Intermediate Similarity NPC294620

  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 NPC3207 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
0.7963 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7944 Intermediate Similarity NPD5632 Approved
0.7805 Intermediate Similarity NPD5003 Discontinued
0.7799 Intermediate Similarity NPD6138 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD5901 Discontinued
0.7783 Intermediate Similarity NPD648 Clinical (unspecified phase)
0.7773 Intermediate Similarity NPD5488 Discontinued
0.7721 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7685 Intermediate Similarity NPD2565 Phase 2
0.7685 Intermediate Similarity NPD2564 Approved
0.7598 Intermediate Similarity NPD6790 Phase 1
0.7555 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7523 Intermediate Similarity NPD2916 Discontinued
0.7511 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.751 Intermediate Similarity NPD7803 Approved
0.75 Intermediate Similarity NPD3258 Approved
0.75 Intermediate Similarity NPD3259 Approved
0.7489 Intermediate Similarity NPD4373 Phase 2
0.7478 Intermediate Similarity NPD6962 Phase 2
0.7448 Intermediate Similarity NPD7956 Approved
0.7448 Intermediate Similarity NPD7955 Approved
0.7441 Intermediate Similarity NPD484 Approved
0.7434 Intermediate Similarity NPD4952 Phase 3
0.7415 Intermediate Similarity NPD4948 Discontinued
0.7411 Intermediate Similarity NPD3925 Approved
0.7397 Intermediate Similarity NPD3257 Approved
0.7373 Intermediate Similarity NPD5482 Discontinued
0.7371 Intermediate Similarity NPD7417 Discontinued
0.7356 Intermediate Similarity NPD5937 Approved
0.7349 Intermediate Similarity NPD3003 Approved
0.7344 Intermediate Similarity NPD7708 Approved
0.7339 Intermediate Similarity NPD5416 Discontinued
0.7333 Intermediate Similarity NPD5512 Phase 3
0.7323 Intermediate Similarity NPD2844 Phase 3
0.7309 Intermediate Similarity NPD6242 Discontinued
0.7309 Intermediate Similarity NPD8466 Approved
0.7309 Intermediate Similarity NPD8465 Approved
0.7309 Intermediate Similarity NPD8429 Approved
0.7309 Intermediate Similarity NPD8467 Approved
0.7309 Intermediate Similarity NPD8428 Approved
0.7309 Intermediate Similarity NPD8427 Approved
0.73 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD3986 Discontinued
0.7277 Intermediate Similarity NPD4601 Approved
0.7277 Intermediate Similarity NPD4600 Approved
0.7276 Intermediate Similarity NPD8363 Approved
0.7276 Intermediate Similarity NPD8364 Approved
0.7269 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7269 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD2920 Discontinued
0.7248 Intermediate Similarity NPD4506 Discontinued
0.7227 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.722 Intermediate Similarity NPD7395 Discontinued
0.7218 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD5658 Approved
0.72 Intermediate Similarity NPD1326 Approved
0.72 Intermediate Similarity NPD1325 Approved
0.7194 Intermediate Similarity NPD8460 Approved
0.7194 Intermediate Similarity NPD8426 Approved
0.7194 Intermediate Similarity NPD8459 Approved
0.7194 Intermediate Similarity NPD8425 Approved
0.7193 Intermediate Similarity NPD4328 Approved
0.7189 Intermediate Similarity NPD2715 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4312 Approved
0.7168 Intermediate Similarity NPD6995 Phase 1
0.7156 Intermediate Similarity NPD5429 Discontinued
0.715 Intermediate Similarity NPD1768 Approved
0.7149 Intermediate Similarity NPD7689 Approved
0.7149 Intermediate Similarity NPD7069 Discontinued
0.7143 Intermediate Similarity NPD2721 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD1534 Approved
0.7123 Intermediate Similarity NPD6376 Discontinued
0.7117 Intermediate Similarity NPD3243 Approved
0.7104 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4668 Phase 2
0.71 Intermediate Similarity NPD1867 Approved
0.7098 Intermediate Similarity NPD5164 Discontinued
0.7097 Intermediate Similarity NPD6176 Phase 1
0.7094 Intermediate Similarity NPD5805 Approved
0.7085 Intermediate Similarity NPD5902 Approved
0.7085 Intermediate Similarity NPD5903 Approved
0.7085 Intermediate Similarity NPD955 Approved
0.7083 Intermediate Similarity NPD4511 Phase 1
0.7069 Intermediate Similarity NPD3746 Discontinued
0.7067 Intermediate Similarity NPD7878 Phase 2
0.7067 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD3947 Discontinued
0.7061 Intermediate Similarity NPD6531 Approved
0.7061 Intermediate Similarity NPD6530 Approved
0.7056 Intermediate Similarity NPD7948 Phase 1
0.7046 Intermediate Similarity NPD6716 Phase 1
0.7045 Intermediate Similarity NPD2510 Approved
0.7045 Intermediate Similarity NPD2509 Approved
0.7042 Intermediate Similarity NPD4418 Discontinued
0.7039 Intermediate Similarity NPD5445 Approved
0.7039 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6770 Approved
0.7027 Intermediate Similarity NPD7470 Discontinued
0.7026 Intermediate Similarity NPD1505 Phase 2
0.7023 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD5450 Discontinued
0.7 Intermediate Similarity NPD8358 Approved
0.6996 Remote Similarity NPD5866 Approved
0.6996 Remote Similarity NPD4885 Approved
0.6995 Remote Similarity NPD802 Phase 2
0.6995 Remote Similarity NPD4539 Phase 1
0.6995 Remote Similarity NPD1038 Approved
0.6991 Remote Similarity NPD4118 Clinical (unspecified phase)
0.6991 Remote Similarity NPD1926 Approved
0.699 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6986 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6983 Remote Similarity NPD5479 Discontinued
0.6979 Remote Similarity NPD7853 Phase 2
0.697 Remote Similarity NPD7994 Phase 2
0.696 Remote Similarity NPD6974 Phase 3
0.6959 Remote Similarity NPD4500 Approved
0.6959 Remote Similarity NPD4501 Approved
0.6953 Remote Similarity NPD7688 Phase 1
0.6951 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7946 Pre-registration
0.6943 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6934 Remote Similarity NPD4499 Approved
0.6923 Remote Similarity NPD1392 Approved
0.6916 Remote Similarity NPD6985 Discontinued
0.6916 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6916 Remote Similarity NPD3354 Phase 2
0.6914 Remote Similarity NPD7181 Phase 3
0.6913 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6911 Remote Similarity NPD75 Approved
0.6911 Remote Similarity NPD9277 Approved
0.6911 Remote Similarity NPD8091 Phase 3
0.6909 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6909 Remote Similarity NPD6987 Phase 1
0.6903 Remote Similarity NPD5612 Discontinued
0.6903 Remote Similarity NPD2433 Clinical (unspecified phase)
0.6903 Remote Similarity NPD8160 Phase 2
0.6897 Remote Similarity NPD4845 Discontinued
0.6894 Remote Similarity NPD7558 Phase 2
0.6894 Remote Similarity NPD8489 Phase 1
0.6893 Remote Similarity NPD749 Clinical (unspecified phase)
0.689 Remote Similarity NPD6709 Phase 3
0.6889 Remote Similarity NPD3794 Approved
0.6889 Remote Similarity NPD3795 Approved
0.6889 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6859 Remote Similarity NPD9274 Approved
0.6859 Remote Similarity NPD9278 Suspended
0.6859 Remote Similarity NPD9276 Approved
0.6859 Remote Similarity NPD9275 Approved
0.6858 Remote Similarity NPD5293 Phase 2
0.6858 Remote Similarity NPD4897 Phase 2
0.6858 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6854 Remote Similarity NPD5928 Phase 1
0.6853 Remote Similarity NPD3263 Phase 3
0.6851 Remote Similarity NPD5151 Clinical (unspecified phase)
0.6845 Remote Similarity NPD482 Approved
0.6837 Remote Similarity NPD1304 Clinical (unspecified phase)
0.6833 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6833 Remote Similarity NPD1483 Discontinued
0.683 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6828 Remote Similarity NPD3393 Approved
0.6828 Remote Similarity NPD3389 Approved
0.6828 Remote Similarity NPD3394 Approved
0.6826 Remote Similarity NPD5507 Approved
0.6826 Remote Similarity NPD5506 Approved
0.682 Remote Similarity NPD4561 Discontinued
0.682 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6818 Remote Similarity NPD2779 Approved
0.6812 Remote Similarity NPD7194 Discontinued
0.6809 Remote Similarity NPD1466 Phase 3
0.6809 Remote Similarity NPD1467 Approved
0.6806 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6789 Remote Similarity NPD6252 Clinical (unspecified phase)
0.6789 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6789 Remote Similarity NPD8463 Approved
0.6789 Remote Similarity NPD7777 Approved
0.6789 Remote Similarity NPD7778 Approved
0.6789 Remote Similarity NPD5532 Phase 2
0.6789 Remote Similarity NPD53 Approved
0.6781 Remote Similarity NPD7603 Discontinued
0.6779 Remote Similarity NPD6641 Approved
0.6779 Remote Similarity NPD6642 Approved
0.6771 Remote Similarity NPD7453 Approved
0.6771 Remote Similarity NPD7222 Phase 2
0.6771 Remote Similarity NPD7452 Approved
0.6769 Remote Similarity NPD4429 Discontinued
0.6762 Remote Similarity NPD8102 Discontinued
0.6762 Remote Similarity NPD3178 Discontinued
0.6758 Remote Similarity NPD8395 Approved
0.6758 Remote Similarity NPD8396 Approved
0.6758 Remote Similarity NPD3814 Phase 1
0.6757 Remote Similarity NPD56 Approved
0.6757 Remote Similarity NPD8282 Approved
0.6757 Remote Similarity NPD8283 Approved
0.6756 Remote Similarity NPD1166 Clinical (unspecified phase)
0.6749 Remote Similarity NPD1631 Approved
0.6746 Remote Similarity NPD1503 Clinical (unspecified phase)
0.6744 Remote Similarity NPD5913 Phase 3
0.6744 Remote Similarity NPD5912 Clinical (unspecified phase)

  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