Structure

Physi-Chem Properties

Molecular Weight:  512.1
Volume:  486.495
LogP:  2.227
LogD:  1.849
LogS:  -4.942
# Rotatable Bonds:  11
TPSA:  161.71
# H-Bond Aceptor:  12
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.351
Synthetic Accessibility Score:  2.827
Fsp3:  0.2
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:  -4.976
MDCK Permeability:  2.5615963750169612e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.017
Human Intestinal Absorption (HIA):  0.845
20% Bioavailability (F20%):  0.904
30% Bioavailability (F30%):  0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.171
Plasma Protein Binding (PPB):  77.09251403808594%
Volume Distribution (VD):  0.633
Pgp-substrate:  27.18462371826172%

ADMET: Metabolism

CYP1A2-inhibitor:  0.384
CYP1A2-substrate:  0.019
CYP2C19-inhibitor:  0.252
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.784
CYP2C9-substrate:  0.578
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.098
CYP3A4-inhibitor:  0.132
CYP3A4-substrate:  0.108

ADMET: Excretion

Clearance (CL):  1.213
Half-life (T1/2):  0.856

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.0
Drug-inuced Liver Injury (DILI):  0.873
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.685
Maximum Recommended Daily Dose:  0.204
Skin Sensitization:  0.963
Carcinogencity:  0.055
Eye Corrosion:  0.043
Eye Irritation:  0.559
Respiratory Toxicity:  0.047

Download Data

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

  Natural Product: NPC177839

Natural Product ID:  NPC177839
Common Name*:   Pentaacetylquercetin
IUPAC Name:   [2-acetyloxy-4-(3,5,7-triacetyloxy-4-oxochromen-2-yl)phenyl] acetate
Synonyms:   NSC-115919
Standard InCHIKey:  JQUHMSXLZZWRHU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C25H20O12/c1-11(26)32-17-9-20(35-14(4)29)22-21(10-17)37-24(25(23(22)31)36-15(5)30)16-6-7-18(33-12(2)27)19(8-16)34-13(3)28/h6-10H,1-5H3
SMILES:  CC(=O)Oc1cc(c2c(c1)oc(c1ccc(c(c1)OC(=O)C)OC(=O)C)c(c2=O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL19074
PubChem CID:   14005
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
NPO28094 Consolida oliveriana Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[19489596]
NPO33509 byrsonima coccolobifolia Species Malpighiaceae Eukaryota leaves and stems cerrado at the Federal University of So Carlos (UFSCar), So Carlos, SP, Brazil 2011-Jul PMID[24521209]
NPO33118 Rhamnus Genus Rhamnaceae Eukaryota n.a. n.a. n.a. PMID[8350094]
NPO28094 Consolida oliveriana Species Ranunculaceae 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
NPT1558 Individual Protein Aflatoxin B1 aldehyde reductase Rattus norvegicus Inhibition = 6.7 % PMID[447765]
NPT1558 Individual Protein Aflatoxin B1 aldehyde reductase Rattus norvegicus Inhibition = 12.8 % PMID[447765]
NPT1558 Individual Protein Aflatoxin B1 aldehyde reductase Rattus norvegicus Inhibition = 18.0 % PMID[447765]
NPT1563 Individual Protein Phosphodiesterase 2A Rattus norvegicus IC50 = 275000.0 nM PMID[447766]
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Inhibition = 0.0 % PMID[447768]
NPT1597 Cell Line J774.2 IC50 = 109230.0 nM PMID[447771]
NPT1597 Cell Line J774.2 Ratio IC50 = 10.0 n.a. PMID[447771]
NPT1662 Individual Protein Arginase Leishmania amazonensis IC50 = 120800.0 nM PMID[447773]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activation = 7.1 % PMID[447765]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activation = 13.3 % PMID[447765]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activation = 25.0 % PMID[447765]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activation = 37.0 % PMID[447765]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 2.25 n.a. PMID[447765]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 4.75 n.a. PMID[447765]
NPT2 Others Unspecified IC50 = 355000.0 nM PMID[447766]
NPT2 Others Unspecified IC50 = 126000.0 nM PMID[447766]
NPT2 Others Unspecified Ratio = 0.46 n.a. PMID[447766]
NPT35 Others n.a. Solubility = 1100.0 nM PMID[447767]
NPT27 Others Unspecified Activity = 0.5 % PMID[447767]
NPT20967 CELL-LINE Platelet n.a. Activity = 2.4 % PMID[447770]
NPT20967 CELL-LINE Platelet n.a. Activity = 17.4 % PMID[447770]
NPT20967 CELL-LINE Platelet n.a. Activity = 89.2 % PMID[447770]
NPT1596 Organism Leishmania peruviana Leishmania peruviana IC50 = 11180.0 nM PMID[447771]
NPT1208 Organism Leishmania braziliensis Leishmania braziliensis IC50 = 46780.0 nM PMID[447771]
NPT1596 Organism Leishmania peruviana Leishmania peruviana Activity = 40.0 % PMID[447771]
NPT1596 Organism Leishmania peruviana Leishmania peruviana Activity = 72.0 % PMID[447771]
NPT1596 Organism Leishmania peruviana Leishmania peruviana Inhibition = 30.0 % PMID[447771]
NPT2 Others Unspecified IC50 = 6800.0 nM PMID[447772]
NPT2 Others Unspecified Inhibition = 90.0 % PMID[447772]

☑ 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 NPC177839 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
0.9931 High Similarity NPC474170
0.9931 High Similarity NPC474388
0.9931 High Similarity NPC472535
0.9728 High Similarity NPC122623
0.9728 High Similarity NPC241774
0.9728 High Similarity NPC34725
0.9728 High Similarity NPC276059
0.9662 High Similarity NPC257277
0.9595 High Similarity NPC471746
0.9583 High Similarity NPC310259
0.9517 High Similarity NPC299923
0.9456 High Similarity NPC259058
0.9456 High Similarity NPC201547
0.9388 High Similarity NPC181250
0.9388 High Similarity NPC474648
0.9388 High Similarity NPC69752
0.9375 High Similarity NPC70853
0.9375 High Similarity NPC9966
0.9371 High Similarity NPC474037
0.932 High Similarity NPC183236
0.932 High Similarity NPC261548
0.931 High Similarity NPC113089
0.9306 High Similarity NPC29536
0.9267 High Similarity NPC186507
0.9262 High Similarity NPC236769
0.9262 High Similarity NPC76376
0.9262 High Similarity NPC474663
0.9262 High Similarity NPC198615
0.9252 High Similarity NPC85233
0.9252 High Similarity NPC117463
0.9247 High Similarity NPC136278
0.9226 High Similarity NPC280893
0.9205 High Similarity NPC284353
0.92 High Similarity NPC134677
0.9195 High Similarity NPC166753
0.9195 High Similarity NPC219330
0.9195 High Similarity NPC50728
0.9195 High Similarity NPC29056
0.9184 High Similarity NPC283002
0.9184 High Similarity NPC302408
0.9184 High Similarity NPC106461
0.9184 High Similarity NPC14958
0.9184 High Similarity NPC215932
0.9184 High Similarity NPC40818
0.9184 High Similarity NPC110639
0.9167 High Similarity NPC475214
0.915 High Similarity NPC104459
0.915 High Similarity NPC257914
0.915 High Similarity NPC238405
0.9145 High Similarity NPC474983
0.9145 High Similarity NPC178854
0.9139 High Similarity NPC279930
0.9139 High Similarity NPC58382
0.9139 High Similarity NPC162351
0.9139 High Similarity NPC246204
0.9139 High Similarity NPC236223
0.9139 High Similarity NPC179126
0.9139 High Similarity NPC270620
0.9139 High Similarity NPC78326
0.9128 High Similarity NPC159103
0.9122 High Similarity NPC205522
0.9116 High Similarity NPC471590
0.9116 High Similarity NPC165512
0.9097 High Similarity NPC471745
0.9091 High Similarity NPC477164
0.9079 High Similarity NPC189960
0.9079 High Similarity NPC32557
0.9073 High Similarity NPC123886
0.9073 High Similarity NPC82325
0.9073 High Similarity NPC279989
0.906 High Similarity NPC195202
0.9054 High Similarity NPC153758
0.9051 High Similarity NPC476180
0.9051 High Similarity NPC280493
0.9048 High Similarity NPC293201
0.9048 High Similarity NPC23955
0.9032 High Similarity NPC112418
0.9026 High Similarity NPC115798
0.9026 High Similarity NPC22472
0.9026 High Similarity NPC143828
0.9026 High Similarity NPC18607
0.9026 High Similarity NPC288669
0.9026 High Similarity NPC204854
0.9026 High Similarity NPC7846
0.9026 High Similarity NPC19687
0.9026 High Similarity NPC152166
0.9026 High Similarity NPC4481
0.9026 High Similarity NPC105242
0.9026 High Similarity NPC25495
0.9026 High Similarity NPC261004
0.9026 High Similarity NPC191459
0.9026 High Similarity NPC130894
0.9026 High Similarity NPC18772
0.9026 High Similarity NPC176300
0.9026 High Similarity NPC253634
0.9026 High Similarity NPC300943
0.9026 High Similarity NPC9609
0.902 High Similarity NPC265511
0.902 High Similarity NPC100916
0.902 High Similarity NPC55619
0.902 High Similarity NPC200388
0.9013 High Similarity NPC475895
0.9013 High Similarity NPC473664
0.9013 High Similarity NPC476289
0.9013 High Similarity NPC86485
0.9007 High Similarity NPC133953
0.9007 High Similarity NPC200740
0.9007 High Similarity NPC125062
0.9007 High Similarity NPC252933
0.9007 High Similarity NPC54394
0.9007 High Similarity NPC28274
0.9007 High Similarity NPC50403
0.8994 High Similarity NPC475434
0.8993 High Similarity NPC12200
0.8993 High Similarity NPC33265
0.8993 High Similarity NPC62536
0.8974 High Similarity NPC414831
0.8968 High Similarity NPC131557
0.8968 High Similarity NPC471744
0.8961 High Similarity NPC108456
0.8961 High Similarity NPC78302
0.8961 High Similarity NPC7973
0.8961 High Similarity NPC227192
0.8961 High Similarity NPC110070
0.8961 High Similarity NPC305663
0.8961 High Similarity NPC93376
0.8961 High Similarity NPC224137
0.8961 High Similarity NPC163524
0.8961 High Similarity NPC29841
0.8961 High Similarity NPC189179
0.8961 High Similarity NPC101830
0.8961 High Similarity NPC472438
0.8961 High Similarity NPC176665
0.8961 High Similarity NPC203891
0.8961 High Similarity NPC235215
0.8961 High Similarity NPC287979
0.8961 High Similarity NPC75215
0.8958 High Similarity NPC72452
0.8958 High Similarity NPC61546
0.8947 High Similarity NPC301123
0.8947 High Similarity NPC55205
0.894 High Similarity NPC188871
0.894 High Similarity NPC149127
0.894 High Similarity NPC286342
0.8933 High Similarity NPC476342
0.8933 High Similarity NPC10304
0.8933 High Similarity NPC63256
0.8912 High Similarity NPC214919
0.8912 High Similarity NPC124467
0.8912 High Similarity NPC185607
0.891 High Similarity NPC216092
0.8903 High Similarity NPC193842
0.8897 High Similarity NPC103001
0.8897 High Similarity NPC44573
0.8896 High Similarity NPC43243
0.8896 High Similarity NPC245546
0.8896 High Similarity NPC292107
0.8896 High Similarity NPC49824
0.8896 High Similarity NPC266960
0.8896 High Similarity NPC474520
0.8896 High Similarity NPC268161
0.8896 High Similarity NPC98661
0.8896 High Similarity NPC247017
0.8882 High Similarity NPC208043
0.8882 High Similarity NPC308451
0.8882 High Similarity NPC226973
0.8882 High Similarity NPC260895
0.8874 High Similarity NPC238366
0.8874 High Similarity NPC328119
0.8874 High Similarity NPC87125
0.8874 High Similarity NPC177298
0.8874 High Similarity NPC287101
0.8874 High Similarity NPC52005
0.8874 High Similarity NPC223579
0.8874 High Similarity NPC137062
0.8874 High Similarity NPC183950
0.8874 High Similarity NPC270465
0.8874 High Similarity NPC48479
0.8867 High Similarity NPC470511
0.8861 High Similarity NPC475369
0.8859 High Similarity NPC287275
0.8854 High Similarity NPC302741
0.8854 High Similarity NPC475144
0.8846 High Similarity NPC130955
0.8846 High Similarity NPC269906
0.8846 High Similarity NPC243509
0.8839 High Similarity NPC174908
0.8839 High Similarity NPC471479
0.8839 High Similarity NPC471515
0.8831 High Similarity NPC183597
0.8831 High Similarity NPC133392
0.8831 High Similarity NPC163780
0.8831 High Similarity NPC214138
0.8831 High Similarity NPC92659
0.8831 High Similarity NPC26227
0.8831 High Similarity NPC80534
0.8831 High Similarity NPC50715
0.8831 High Similarity NPC201136
0.8831 High Similarity NPC128863
0.8831 High Similarity NPC44079

  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 NPC177839 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
0.9595 High Similarity NPD3817 Phase 2
0.88 High Similarity NPD1512 Approved
0.8792 High Similarity NPD6799 Approved
0.8782 High Similarity NPD919 Approved
0.8766 High Similarity NPD2801 Approved
0.8667 High Similarity NPD1511 Approved
0.8654 High Similarity NPD3882 Suspended
0.8598 High Similarity NPD4338 Clinical (unspecified phase)
0.8581 High Similarity NPD1934 Approved
0.8581 High Similarity NPD6801 Discontinued
0.8526 High Similarity NPD7096 Clinical (unspecified phase)
0.8509 High Similarity NPD6168 Clinical (unspecified phase)
0.8509 High Similarity NPD6166 Phase 2
0.8509 High Similarity NPD6167 Clinical (unspecified phase)
0.8487 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8485 Intermediate Similarity NPD7808 Phase 3
0.8481 Intermediate Similarity NPD7075 Discontinued
0.8476 Intermediate Similarity NPD6797 Phase 2
0.8471 Intermediate Similarity NPD5402 Approved
0.8452 Intermediate Similarity NPD6599 Discontinued
0.8446 Intermediate Similarity NPD2796 Approved
0.8424 Intermediate Similarity NPD7251 Discontinued
0.8408 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8377 Intermediate Similarity NPD5403 Approved
0.8377 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD5494 Approved
0.8366 Intermediate Similarity NPD5401 Approved
0.8354 Intermediate Similarity NPD7054 Approved
0.8333 Intermediate Similarity NPD3926 Phase 2
0.8323 Intermediate Similarity NPD1247 Approved
0.8303 Intermediate Similarity NPD7472 Approved
0.8293 Intermediate Similarity NPD3818 Discontinued
0.8291 Intermediate Similarity NPD7819 Suspended
0.8272 Intermediate Similarity NPD6232 Discontinued
0.8232 Intermediate Similarity NPD7473 Discontinued
0.8193 Intermediate Similarity NPD7074 Phase 3
0.8187 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8158 Intermediate Similarity NPD1243 Approved
0.8133 Intermediate Similarity NPD3748 Approved
0.8063 Intermediate Similarity NPD1465 Phase 2
0.8054 Intermediate Similarity NPD447 Suspended
0.8054 Intermediate Similarity NPD1933 Approved
0.805 Intermediate Similarity NPD7411 Suspended
0.8025 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD920 Approved
0.8024 Intermediate Similarity NPD5844 Phase 1
0.8024 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD4380 Phase 2
0.7974 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD6832 Phase 2
0.7929 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD1510 Phase 2
0.7892 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD3750 Approved
0.7857 Intermediate Similarity NPD1549 Phase 2
0.7852 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD1240 Approved
0.7738 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD3226 Approved
0.7697 Intermediate Similarity NPD3749 Approved
0.7683 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD7199 Phase 2
0.7647 Intermediate Similarity NPD1607 Approved
0.7635 Intermediate Similarity NPD3267 Approved
0.7635 Intermediate Similarity NPD3266 Approved
0.7633 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD2313 Discontinued
0.7613 Intermediate Similarity NPD2935 Discontinued
0.7613 Intermediate Similarity NPD1551 Phase 2
0.761 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD5242 Approved
0.7572 Intermediate Similarity NPD6559 Discontinued
0.756 Intermediate Similarity NPD6959 Discontinued
0.7548 Intermediate Similarity NPD2799 Discontinued
0.753 Intermediate Similarity NPD7768 Phase 2
0.7517 Intermediate Similarity NPD1203 Approved
0.7516 Intermediate Similarity NPD4307 Phase 2
0.7516 Intermediate Similarity NPD943 Approved
0.75 Intermediate Similarity NPD1296 Phase 2
0.75 Intermediate Similarity NPD3268 Approved
0.75 Intermediate Similarity NPD6385 Approved
0.75 Intermediate Similarity NPD6386 Approved
0.7484 Intermediate Similarity NPD6190 Approved
0.747 Intermediate Similarity NPD5353 Approved
0.7468 Intermediate Similarity NPD230 Phase 1
0.7466 Intermediate Similarity NPD17 Approved
0.7453 Intermediate Similarity NPD2533 Approved
0.7453 Intermediate Similarity NPD3146 Approved
0.7453 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD2534 Approved
0.7453 Intermediate Similarity NPD2532 Approved
0.7452 Intermediate Similarity NPD2346 Discontinued
0.7452 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD2353 Approved
0.7432 Intermediate Similarity NPD9717 Approved
0.7427 Intermediate Similarity NPD2403 Approved
0.7423 Intermediate Similarity NPD1653 Approved
0.7421 Intermediate Similarity NPD4628 Phase 3
0.7421 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD3787 Discontinued
0.74 Intermediate Similarity NPD2797 Approved
0.7386 Intermediate Similarity NPD6798 Discontinued
0.7375 Intermediate Similarity NPD3887 Approved
0.7368 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD422 Phase 1
0.7358 Intermediate Similarity NPD2800 Approved
0.7351 Intermediate Similarity NPD2798 Approved
0.7351 Intermediate Similarity NPD1019 Discontinued
0.7349 Intermediate Similarity NPD37 Approved
0.7341 Intermediate Similarity NPD3751 Discontinued
0.7338 Intermediate Similarity NPD6233 Phase 2
0.7333 Intermediate Similarity NPD3225 Approved
0.7325 Intermediate Similarity NPD4308 Phase 3
0.7325 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD4965 Approved
0.7321 Intermediate Similarity NPD4966 Approved
0.7321 Intermediate Similarity NPD4967 Phase 2
0.7315 Intermediate Similarity NPD1608 Approved
0.7314 Intermediate Similarity NPD5953 Discontinued
0.7303 Intermediate Similarity NPD3018 Phase 2
0.7303 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD411 Approved
0.7267 Intermediate Similarity NPD2354 Approved
0.726 Intermediate Similarity NPD5536 Phase 2
0.7255 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2654 Approved
0.7248 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD6355 Discontinued
0.7235 Intermediate Similarity NPD6234 Discontinued
0.7233 Intermediate Similarity NPD1471 Phase 3
0.7215 Intermediate Similarity NPD7033 Discontinued
0.7208 Intermediate Similarity NPD7095 Approved
0.7207 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD2981 Phase 2
0.72 Intermediate Similarity NPD7286 Phase 2
0.7179 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD1613 Approved
0.717 Intermediate Similarity NPD6099 Approved
0.717 Intermediate Similarity NPD6100 Approved
0.7167 Intermediate Similarity NPD8434 Phase 2
0.716 Intermediate Similarity NPD4288 Approved
0.7152 Intermediate Similarity NPD2982 Phase 2
0.7152 Intermediate Similarity NPD2983 Phase 2
0.7143 Intermediate Similarity NPD1652 Phase 2
0.7125 Intermediate Similarity NPD2344 Approved
0.7112 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3027 Phase 3
0.7091 Intermediate Similarity NPD5049 Phase 3
0.7089 Intermediate Similarity NPD6651 Approved
0.7079 Intermediate Similarity NPD7685 Pre-registration
0.7073 Intermediate Similarity NPD7390 Discontinued
0.7052 Intermediate Similarity NPD8127 Discontinued
0.7047 Intermediate Similarity NPD9268 Approved
0.7039 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD5535 Approved
0.703 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD4340 Discontinued
0.7024 Intermediate Similarity NPD6585 Discontinued
0.7011 Intermediate Similarity NPD7229 Phase 3
0.7006 Intermediate Similarity NPD4062 Phase 3
0.7 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7038 Approved
0.6983 Remote Similarity NPD7039 Approved
0.6982 Remote Similarity NPD5890 Approved
0.6982 Remote Similarity NPD5889 Approved
0.6977 Remote Similarity NPD6971 Discontinued
0.6974 Remote Similarity NPD3972 Approved
0.6974 Remote Similarity NPD9269 Phase 2
0.6962 Remote Similarity NPD4060 Phase 1
0.6951 Remote Similarity NPD2309 Approved
0.6949 Remote Similarity NPD2163 Approved
0.6949 Remote Similarity NPD7228 Approved
0.6947 Remote Similarity NPD5005 Approved
0.6947 Remote Similarity NPD5006 Approved
0.6944 Remote Similarity NPD7549 Discontinued
0.6928 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4972 Discontinued
0.6919 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6918 Remote Similarity NPD5124 Phase 1
0.6918 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6914 Remote Similarity NPD5710 Approved
0.6914 Remote Similarity NPD5711 Approved
0.6911 Remote Similarity NPD7435 Discontinued
0.6906 Remote Similarity NPD8313 Approved
0.6906 Remote Similarity NPD8312 Approved
0.6899 Remote Similarity NPD8032 Phase 2
0.689 Remote Similarity NPD4110 Phase 3

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data