Structure

Physi-Chem Properties

Molecular Weight:  412.08
Volume:  396.214
LogP:  2.818
LogD:  2.239
LogS:  -4.458
# Rotatable Bonds:  7
TPSA:  129.34
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.508
Synthetic Accessibility Score:  2.528
Fsp3:  0.143
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.789
MDCK Permeability:  6.339199171634391e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.086
20% Bioavailability (F20%):  0.146
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.066
Plasma Protein Binding (PPB):  81.6722640991211%
Volume Distribution (VD):  0.518
Pgp-substrate:  26.260725021362305%

ADMET: Metabolism

CYP1A2-inhibitor:  0.872
CYP1A2-substrate:  0.052
CYP2C19-inhibitor:  0.507
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.684
CYP2C9-substrate:  0.831
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.15
CYP3A4-inhibitor:  0.212
CYP3A4-substrate:  0.122

ADMET: Excretion

Clearance (CL):  0.933
Half-life (T1/2):  0.831

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.003
Drug-inuced Liver Injury (DILI):  0.957
AMES Toxicity:  0.308
Rat Oral Acute Toxicity:  0.804
Maximum Recommended Daily Dose:  0.75
Skin Sensitization:  0.926
Carcinogencity:  0.37
Eye Corrosion:  0.004
Eye Irritation:  0.381
Respiratory Toxicity:  0.208

Download Data

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

  Natural Product: NPC153758

Natural Product ID:  NPC153758
Common Name*:   3,7,4'-Tri-O-Acetyl Kaempferol
IUPAC Name:   [4-(3,7-diacetyloxy-5-hydroxy-4-oxochromen-2-yl)phenyl] acetate
Synonyms:  
Standard InCHIKey:  DJKUFDVJACBQPB-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H16O9/c1-10(22)27-14-6-4-13(5-7-14)20-21(29-12(3)24)19(26)18-16(25)8-15(28-11(2)23)9-17(18)30-20/h4-9,25H,1-3H3
SMILES:  CC(=O)Oc1ccc(cc1)c1oc2cc(OC(=O)C)cc(c2c(=O)c1OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL516683
PubChem CID:   44584293
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones

*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
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10843584]
NPO27252 Iochroma australe Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. antarctic n.a. PMID[15270575]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[15497934]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[30407007]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26453 Prunus lusitanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26952 Cineraria geifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26053 Pluchea suaveolens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26377 Amelanchier vulgaris Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26563 Alectoria japonica Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27377 Diaporthe helianthi Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26186 Stereocaulon leprocauloides Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26026 Vitis silvestris Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26884 Helichrysum davenportii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13781 Eremostachys moluccelloides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25741 Aster ageratoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7214 Bufotes viridis Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26430 Aplysina laevis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26754 Stevia connata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27252 Iochroma australe Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26244 Panax papyrifer Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26078 Mussaenda parviflora Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2344 Carlina acanthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26903 Plectranthus purpuratus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO137 Nepeta multifida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26135 Walsura tubulata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26213 Tephrosia vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25997 Senecio rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14466 Penicillium olsonii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26980 Halocarpus biformis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19823 Vicia benghalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25952 Lastrea thelypteris n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26109 Pilocarpus spicatus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25926 Tephrosia pumila Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25873 Thaminophyllum multiflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26625 Stichopus chloronotus Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24378 Osmanthus heterophyllus Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26727 Eremocarpus setiger n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26352 Heuchera cylindrica Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26678 Calea pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26408 Melanophryniscus moreirae Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26535 Balanus glandula Species Balanidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11845 Petrorhagia dubia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3346 Piper sanctum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18292 Guarea trichilioides Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25849 Streptomyces lomondensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26289 Lecidella chodati Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25793 Gremmeniella abietina Species Helotiaceae 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
NPT839 Cell Line L6 Rattus norvegicus Activity = 94.8 % PMID[503805]
NPT839 Cell Line L6 Rattus norvegicus Activity = 90.2 % PMID[503805]
NPT319 Cell Line B16 Mus musculus IC50 = 39800.0 nM PMID[503805]
NPT140 Organism Artemia Artemia LC50 = 2210000.0 nM PMID[503804]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity > 100.0 uM PMID[503805]
NPT634 Organism Leishmania amazonensis Leishmania amazonensis IC50 = 12270.0 nM PMID[503805]
NPT1225 Organism Plasmodium falciparum (isolate FcB1 / Columbia) Plasmodium falciparum FcB1/Columbia GI = 7.6 % PMID[503805]
NPT2229 Organism Trypanosoma brucei gambiense Trypanosoma brucei gambiense GI = 5.6 % PMID[503805]
NPT2229 Organism Trypanosoma brucei gambiense Trypanosoma brucei gambiense GI = 0.0 % PMID[503805]

☑ 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 NPC153758 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9714 High Similarity NPC470216
0.964 High Similarity NPC474037
0.9571 High Similarity NPC90582
0.9571 High Similarity NPC262094
0.95 High Similarity NPC146679
0.95 High Similarity NPC59951
0.95 High Similarity NPC103904
0.95 High Similarity NPC103342
0.95 High Similarity NPC230285
0.95 High Similarity NPC184536
0.9433 High Similarity NPC136840
0.9429 High Similarity NPC152042
0.9429 High Similarity NPC143799
0.9429 High Similarity NPC241838
0.9366 High Similarity NPC36181
0.9366 High Similarity NPC200694
0.9362 High Similarity NPC269652
0.9362 High Similarity NPC281207
0.9357 High Similarity NPC276905
0.9353 High Similarity NPC281917
0.9353 High Similarity NPC13408
0.9353 High Similarity NPC187432
0.9353 High Similarity NPC256042
0.9353 High Similarity NPC116775
0.9353 High Similarity NPC216361
0.9324 High Similarity NPC473241
0.9306 High Similarity NPC306488
0.9306 High Similarity NPC154217
0.9306 High Similarity NPC178343
0.9306 High Similarity NPC5820
0.9301 High Similarity NPC158874
0.9301 High Similarity NPC112791
0.9301 High Similarity NPC293053
0.9301 High Similarity NPC470296
0.9301 High Similarity NPC212932
0.9301 High Similarity NPC196459
0.9301 High Similarity NPC9117
0.9301 High Similarity NPC24821
0.9301 High Similarity NPC188632
0.9301 High Similarity NPC87609
0.9301 High Similarity NPC94794
0.9301 High Similarity NPC190637
0.9291 High Similarity NPC230902
0.9286 High Similarity NPC299379
0.9252 High Similarity NPC295650
0.9247 High Similarity NPC477941
0.9236 High Similarity NPC196137
0.9236 High Similarity NPC326500
0.9236 High Similarity NPC1886
0.9236 High Similarity NPC178627
0.9236 High Similarity NPC469935
0.9236 High Similarity NPC273538
0.9236 High Similarity NPC216538
0.9231 High Similarity NPC473042
0.9214 High Similarity NPC194281
0.9214 High Similarity NPC127447
0.9214 High Similarity NPC124784
0.9214 High Similarity NPC231772
0.9214 High Similarity NPC473887
0.9214 High Similarity NPC234133
0.9214 High Similarity NPC61546
0.9214 High Similarity NPC29353
0.9214 High Similarity NPC47815
0.9214 High Similarity NPC72452
0.9209 High Similarity NPC248872
0.9172 High Similarity NPC181388
0.9172 High Similarity NPC57470
0.9172 High Similarity NPC470322
0.9172 High Similarity NPC470458
0.9172 High Similarity NPC124729
0.9155 High Similarity NPC301217
0.9155 High Similarity NPC55018
0.9155 High Similarity NPC303633
0.9155 High Similarity NPC96565
0.9155 High Similarity NPC216978
0.9155 High Similarity NPC220062
0.9149 High Similarity NPC250266
0.9149 High Similarity NPC266597
0.9139 High Similarity NPC104677
0.9137 High Similarity NPC274121
0.9137 High Similarity NPC213216
0.9137 High Similarity NPC78540
0.9137 High Similarity NPC50898
0.9116 High Similarity NPC470461
0.911 High Similarity NPC180477
0.911 High Similarity NPC249942
0.911 High Similarity NPC14001
0.911 High Similarity NPC297886
0.911 High Similarity NPC259632
0.911 High Similarity NPC166757
0.911 High Similarity NPC140120
0.9103 High Similarity NPC71210
0.9103 High Similarity NPC469953
0.9091 High Similarity NPC241100
0.9091 High Similarity NPC270883
0.9091 High Similarity NPC261227
0.9091 High Similarity NPC172986
0.9091 High Similarity NPC159275
0.9085 High Similarity NPC201395
0.9071 High Similarity NPC172262
0.9065 High Similarity NPC128216
0.9065 High Similarity NPC10971
0.9054 High Similarity NPC474735
0.9054 High Similarity NPC177839
0.9048 High Similarity NPC161864
0.9048 High Similarity NPC296869
0.9048 High Similarity NPC470460
0.9048 High Similarity NPC469933
0.9048 High Similarity NPC244407
0.9048 High Similarity NPC208303
0.9041 High Similarity NPC220418
0.9028 High Similarity NPC282300
0.9028 High Similarity NPC205006
0.9028 High Similarity NPC110969
0.9028 High Similarity NPC310128
0.9028 High Similarity NPC147688
0.9028 High Similarity NPC64908
0.9028 High Similarity NPC156590
0.9028 High Similarity NPC118840
0.9021 High Similarity NPC217186
0.9021 High Similarity NPC78913
0.9021 High Similarity NPC18260
0.9021 High Similarity NPC53181
0.902 High Similarity NPC216496
0.902 High Similarity NPC48093
0.902 High Similarity NPC259957
0.902 High Similarity NPC129217
0.902 High Similarity NPC159579
0.902 High Similarity NPC85707
0.902 High Similarity NPC224530
0.9014 High Similarity NPC228661
0.9014 High Similarity NPC103001
0.9014 High Similarity NPC188879
0.9014 High Similarity NPC254841
0.9 High Similarity NPC57601
0.8993 High Similarity NPC474170
0.8993 High Similarity NPC76376
0.8993 High Similarity NPC290671
0.8993 High Similarity NPC113006
0.8993 High Similarity NPC236769
0.8993 High Similarity NPC472535
0.8993 High Similarity NPC474388
0.8986 High Similarity NPC19238
0.8986 High Similarity NPC469932
0.8986 High Similarity NPC269420
0.898 High Similarity NPC12305
0.898 High Similarity NPC472918
0.8966 High Similarity NPC471520
0.8966 High Similarity NPC62840
0.8966 High Similarity NPC226636
0.8966 High Similarity NPC59739
0.8966 High Similarity NPC299080
0.8966 High Similarity NPC11561
0.8966 High Similarity NPC293852
0.8966 High Similarity NPC78803
0.8966 High Similarity NPC214236
0.8966 High Similarity NPC217083
0.8961 High Similarity NPC27942
0.8961 High Similarity NPC471745
0.8958 High Similarity NPC221173
0.8958 High Similarity NPC305355
0.8958 High Similarity NPC235239
0.8958 High Similarity NPC129853
0.8958 High Similarity NPC6407
0.8958 High Similarity NPC110228
0.8958 High Similarity NPC76445
0.8958 High Similarity NPC475680
0.8958 High Similarity NPC150522
0.8958 High Similarity NPC69769
0.8958 High Similarity NPC188243
0.8958 High Similarity NPC284550
0.8951 High Similarity NPC188947
0.8951 High Similarity NPC99333
0.8951 High Similarity NPC124269
0.8951 High Similarity NPC280284
0.8944 High Similarity NPC240147
0.8944 High Similarity NPC121243
0.8944 High Similarity NPC240593
0.8929 High Similarity NPC473655
0.8929 High Similarity NPC101294
0.8926 High Similarity NPC151973
0.8926 High Similarity NPC149127
0.8926 High Similarity NPC286342
0.8926 High Similarity NPC219330
0.8926 High Similarity NPC188871
0.8926 High Similarity NPC50728
0.8926 High Similarity NPC295036
0.8926 High Similarity NPC166753
0.8926 High Similarity NPC61258
0.8921 High Similarity NPC5515
0.8921 High Similarity NPC137264
0.8921 High Similarity NPC270369
0.8919 High Similarity NPC211811
0.8912 High Similarity NPC329678
0.8904 High Similarity NPC11700
0.8904 High Similarity NPC66404
0.8904 High Similarity NPC95123
0.8904 High Similarity NPC219915
0.8904 High Similarity NPC38219
0.8903 High Similarity NPC121703

  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 NPC153758 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
0.9236 High Similarity NPD4378 Clinical (unspecified phase)
0.9034 High Similarity NPD6799 Approved
0.8947 High Similarity NPD7075 Discontinued
0.894 High Similarity NPD3817 Phase 2
0.8933 High Similarity NPD6801 Discontinued
0.8844 High Similarity NPD7410 Clinical (unspecified phase)
0.8784 High Similarity NPD1512 Approved
0.875 High Similarity NPD1550 Clinical (unspecified phase)
0.875 High Similarity NPD7096 Clinical (unspecified phase)
0.875 High Similarity NPD1552 Clinical (unspecified phase)
0.8742 High Similarity NPD7411 Suspended
0.8725 High Similarity NPD5403 Approved
0.869 High Similarity NPD1549 Phase 2
0.8675 High Similarity NPD6599 Discontinued
0.8649 High Similarity NPD1511 Approved
0.8611 High Similarity NPD1510 Phase 2
0.8592 High Similarity NPD1240 Approved
0.8591 High Similarity NPD5401 Approved
0.8571 High Similarity NPD3750 Approved
0.8552 High Similarity NPD2796 Approved
0.8506 High Similarity NPD7819 Suspended
0.8506 High Similarity NPD2801 Approved
0.8472 Intermediate Similarity NPD1607 Approved
0.8462 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD5402 Approved
0.8451 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8447 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8435 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD4380 Phase 2
0.8397 Intermediate Similarity NPD3882 Suspended
0.8387 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8357 Intermediate Similarity NPD1203 Approved
0.8354 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD3749 Approved
0.8344 Intermediate Similarity NPD6797 Phase 2
0.8333 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD1934 Approved
0.8299 Intermediate Similarity NPD1551 Phase 2
0.8293 Intermediate Similarity NPD7251 Discontinued
0.8261 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD6166 Phase 2
0.8261 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8255 Intermediate Similarity NPD1243 Approved
0.8255 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD7808 Phase 3
0.8231 Intermediate Similarity NPD3748 Approved
0.8201 Intermediate Similarity NPD422 Phase 1
0.8194 Intermediate Similarity NPD3268 Approved
0.8182 Intermediate Similarity NPD6832 Phase 2
0.8165 Intermediate Similarity NPD7768 Phase 2
0.8143 Intermediate Similarity NPD9717 Approved
0.8117 Intermediate Similarity NPD920 Approved
0.811 Intermediate Similarity NPD7054 Approved
0.8099 Intermediate Similarity NPD2797 Approved
0.8079 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8069 Intermediate Similarity NPD2313 Discontinued
0.8061 Intermediate Similarity NPD7472 Approved
0.8054 Intermediate Similarity NPD2935 Discontinued
0.805 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8049 Intermediate Similarity NPD3818 Discontinued
0.8028 Intermediate Similarity NPD3225 Approved
0.8025 Intermediate Similarity NPD6232 Discontinued
0.8013 Intermediate Similarity NPD2800 Approved
0.8013 Intermediate Similarity NPD3226 Approved
0.7988 Intermediate Similarity NPD7473 Discontinued
0.7987 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD2799 Discontinued
0.7974 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD6959 Discontinued
0.7952 Intermediate Similarity NPD7074 Phase 3
0.795 Intermediate Similarity NPD919 Approved
0.7904 Intermediate Similarity NPD5953 Discontinued
0.7892 Intermediate Similarity NPD7286 Phase 2
0.7871 Intermediate Similarity NPD2532 Approved
0.7871 Intermediate Similarity NPD2534 Approved
0.7871 Intermediate Similarity NPD2533 Approved
0.7867 Intermediate Similarity NPD7033 Discontinued
0.7867 Intermediate Similarity NPD4308 Phase 3
0.7852 Intermediate Similarity NPD6651 Approved
0.7847 Intermediate Similarity NPD3266 Approved
0.7847 Intermediate Similarity NPD3267 Approved
0.7812 Intermediate Similarity NPD1465 Phase 2
0.7798 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD2344 Approved
0.7751 Intermediate Similarity NPD6559 Discontinued
0.7727 Intermediate Similarity NPD4628 Phase 3
0.7711 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD1296 Phase 2
0.7703 Intermediate Similarity NPD6798 Discontinued
0.7679 Intermediate Similarity NPD5844 Phase 1
0.7671 Intermediate Similarity NPD2798 Approved
0.7667 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD447 Suspended
0.766 Intermediate Similarity NPD1548 Phase 1
0.7651 Intermediate Similarity NPD6233 Phase 2
0.7647 Intermediate Similarity NPD2346 Discontinued
0.7613 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD4307 Phase 2
0.7584 Intermediate Similarity NPD411 Approved
0.7582 Intermediate Similarity NPD6100 Approved
0.7582 Intermediate Similarity NPD6099 Approved
0.7576 Intermediate Similarity NPD5494 Approved
0.7564 Intermediate Similarity NPD2354 Approved
0.7564 Intermediate Similarity NPD2309 Approved
0.7551 Intermediate Similarity NPD1019 Discontinued
0.755 Intermediate Similarity NPD5124 Phase 1
0.755 Intermediate Similarity NPD1933 Approved
0.755 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD4288 Approved
0.7545 Intermediate Similarity NPD3926 Phase 2
0.7535 Intermediate Similarity NPD9545 Approved
0.753 Intermediate Similarity NPD1247 Approved
0.7518 Intermediate Similarity NPD9493 Approved
0.7517 Intermediate Similarity NPD1481 Phase 2
0.7517 Intermediate Similarity NPD1608 Approved
0.7483 Intermediate Similarity NPD943 Approved
0.7469 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD7390 Discontinued
0.7458 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD4908 Phase 1
0.7448 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD1535 Discovery
0.744 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD2654 Approved
0.7436 Intermediate Similarity NPD1652 Phase 2
0.7434 Intermediate Similarity NPD230 Phase 1
0.7434 Intermediate Similarity NPD6355 Discontinued
0.7419 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD2353 Approved
0.7403 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD5049 Phase 3
0.7351 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD3764 Approved
0.7345 Intermediate Similarity NPD4287 Approved
0.7342 Intermediate Similarity NPD3887 Approved
0.7342 Intermediate Similarity NPD6190 Approved
0.7329 Intermediate Similarity NPD1610 Phase 2
0.732 Intermediate Similarity NPD4340 Discontinued
0.7312 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD3751 Discontinued
0.731 Intermediate Similarity NPD17 Approved
0.7303 Intermediate Similarity NPD4062 Phase 3
0.729 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD3787 Discontinued
0.7278 Intermediate Similarity NPD5710 Approved
0.7278 Intermediate Similarity NPD4360 Phase 2
0.7278 Intermediate Similarity NPD4363 Phase 3
0.7278 Intermediate Similarity NPD5711 Approved
0.725 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD5535 Approved
0.7232 Intermediate Similarity NPD8434 Phase 2
0.7219 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7199 Phase 2
0.7197 Intermediate Similarity NPD1471 Phase 3
0.7195 Intermediate Similarity NPD6585 Discontinued
0.7193 Intermediate Similarity NPD2403 Approved
0.7188 Intermediate Similarity NPD7440 Discontinued
0.7178 Intermediate Similarity NPD1653 Approved
0.7176 Intermediate Similarity NPD7229 Phase 3
0.7172 Intermediate Similarity NPD1894 Discontinued
0.7171 Intermediate Similarity NPD7095 Approved
0.7162 Intermediate Similarity NPD3972 Approved
0.7152 Intermediate Similarity NPD5889 Approved
0.7152 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5890 Approved
0.7143 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4361 Phase 2
0.7143 Intermediate Similarity NPD6971 Discontinued
0.7143 Intermediate Similarity NPD4060 Phase 1
0.7134 Intermediate Similarity NPD5408 Approved
0.7134 Intermediate Similarity NPD7458 Discontinued
0.7134 Intermediate Similarity NPD5406 Approved
0.7134 Intermediate Similarity NPD5404 Approved
0.7134 Intermediate Similarity NPD5405 Approved
0.7133 Intermediate Similarity NPD1164 Approved
0.7089 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD74 Approved
0.7071 Intermediate Similarity NPD9266 Approved
0.7063 Intermediate Similarity NPD1241 Discontinued
0.7063 Intermediate Similarity NPD7003 Approved
0.7062 Intermediate Similarity NPD8312 Approved
0.7062 Intermediate Similarity NPD8313 Approved
0.7059 Intermediate Similarity NPD4625 Phase 3
0.7059 Intermediate Similarity NPD7435 Discontinued
0.7056 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7584 Approved
0.7032 Intermediate Similarity NPD1613 Approved
0.7032 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD1729 Discontinued
0.7024 Intermediate Similarity NPD2296 Approved
0.7006 Intermediate Similarity NPD6844 Discontinued
0.7006 Intermediate Similarity NPD37 Approved
0.7 Intermediate Similarity NPD9267 Approved
0.7 Intermediate Similarity NPD4749 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