Structure

Physi-Chem Properties

Molecular Weight:  720.13
Volume:  663.908
LogP:  3.676
LogD:  1.184
LogS:  -4.701
# Rotatable Bonds:  5
TPSA:  301.41
# H-Bond Aceptor:  17
# H-Bond Donor:  11
# Rings:  7
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.069
Synthetic Accessibility Score:  4.817
Fsp3:  0.2
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.434
MDCK Permeability:  4.9800387387222145e-06
Pgp-inhibitor:  0.421
Pgp-substrate:  0.917
Human Intestinal Absorption (HIA):  0.989
20% Bioavailability (F20%):  0.041
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  83.9456787109375%
Volume Distribution (VD):  0.552
Pgp-substrate:  33.713462829589844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.203
CYP1A2-substrate:  0.113
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.039
CYP2C9-inhibitor:  0.392
CYP2C9-substrate:  0.147
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.002

ADMET: Excretion

Clearance (CL):  2.726
Half-life (T1/2):  0.683

ADMET: Toxicity

hERG Blockers:  0.052
Human Hepatotoxicity (H-HT):  0.334
Drug-inuced Liver Injury (DILI):  0.995
AMES Toxicity:  0.408
Rat Oral Acute Toxicity:  0.012
Maximum Recommended Daily Dose:  0.085
Skin Sensitization:  0.804
Carcinogencity:  0.017
Eye Corrosion:  0.003
Eye Irritation:  0.628
Respiratory Toxicity:  0.009

Download Data

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

  Natural Product: NPC324742

Natural Product ID:  NPC324742
Common Name*:   Swertifrancheside
IUPAC Name:   2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-8-yl]-1,4,8-trihydroxy-6-methoxyxanthen-9-one
Synonyms:   Swertifrancheside
Standard InCHIKey:  JAANJQNFIJSRTK-KYRPIRIWSA-N
Standard InCHI:  InChI=1S/C35H28O17/c1-49-11-5-15(39)22-19(6-11)51-33-17(41)7-12(26(42)24(33)29(22)45)21-28(44)25(35-32(48)31(47)27(43)20(9-36)52-35)30(46)23-16(40)8-18(50-34(21)23)10-2-3-13(37)14(38)4-10/h2-8,20,27,31-32,35-39,41-44,46-48H,9H2,1H3/t20-,27-,31+,32-,35+/m1/s1
SMILES:  COC1=CC(=C2C(=C1)OC3=C(C=C(C(=C3C2=O)O)C4=C5C(=C(C(=C4O)C6C(C(C(C(O6)CO)O)O)O)O)C(=O)C=C(O5)C7=CC(=C(C=C7)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504840
PubChem CID:   5464386
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001737] Flavonoid C-glycosides

*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
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.bse.2004.02.008]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[7513747]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[7561895]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14685 Swertia franchetiana Species Gentianaceae 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
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 42900.0 nM PMID[556363]
NPT59 Individual Protein DNA polymerase beta Homo sapiens IC50 = 57700.0 nM PMID[556363]
NPT91 Cell Line KB Homo sapiens ED50 > 20.0 ug ml-1 PMID[556363]
NPT1034 Cell Line Lu1 Homo sapiens ED50 > 20.0 ug ml-1 PMID[556363]
NPT858 Cell Line LNCaP Homo sapiens ED50 > 20.0 ug ml-1 PMID[556363]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 > 20.0 ug ml-1 PMID[556363]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Ki = 6700.0 nM PMID[556363]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Ki = 7100.0 nM PMID[556363]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 98.0 % PMID[556363]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 89.0 % PMID[556363]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 82.0 % PMID[556363]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 99.8 % PMID[556364]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 ED50 = 30.9 ug ml-1 PMID[556364]
NPT2 Others Unspecified IC50 = 56600.0 nM PMID[556363]
NPT2 Others Unspecified IC50 = 81000.0 nM PMID[556363]
NPT2 Others Unspecified IC50 = 272000.0 nM PMID[556363]
NPT1514 Uncleic Acid DNA Bos taurus Inhibition = 71.0 % PMID[556363]

☑ 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 NPC324742 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
0.976 High Similarity NPC185275
0.9701 High Similarity NPC265380
0.9576 High Similarity NPC475212
0.9535 High Similarity NPC473618
0.9477 High Similarity NPC179947
0.9467 High Similarity NPC471789
0.9455 High Similarity NPC272560
0.9398 High Similarity NPC14662
0.9398 High Similarity NPC243877
0.9394 High Similarity NPC477840
0.936 High Similarity NPC49690
0.9345 High Similarity NPC472454
0.9345 High Similarity NPC257667
0.9345 High Similarity NPC186847
0.9337 High Similarity NPC224851
0.9337 High Similarity NPC320741
0.9337 High Similarity NPC171985
0.9302 High Similarity NPC132111
0.9302 High Similarity NPC150977
0.9281 High Similarity NPC295082
0.9277 High Similarity NPC259757
0.9273 High Similarity NPC219927
0.9273 High Similarity NPC477841
0.9235 High Similarity NPC99591
0.9231 High Similarity NPC81332
0.9231 High Similarity NPC262580
0.9231 High Similarity NPC289396
0.9231 High Similarity NPC212038
0.9231 High Similarity NPC271848
0.9226 High Similarity NPC177480
0.9226 High Similarity NPC107627
0.9222 High Similarity NPC120593
0.9217 High Similarity NPC272064
0.9212 High Similarity NPC26326
0.9212 High Similarity NPC305987
0.9212 High Similarity NPC113163
0.9212 High Similarity NPC142252
0.9212 High Similarity NPC84324
0.9212 High Similarity NPC288131
0.9212 High Similarity NPC165970
0.9212 High Similarity NPC66618
0.9181 High Similarity NPC216307
0.9172 High Similarity NPC103307
0.9167 High Similarity NPC477154
0.9167 High Similarity NPC6588
0.9167 High Similarity NPC260266
0.9167 High Similarity NPC117854
0.9162 High Similarity NPC36
0.9162 High Similarity NPC72787
0.9162 High Similarity NPC36916
0.9162 High Similarity NPC125039
0.9162 High Similarity NPC7154
0.9162 High Similarity NPC58223
0.9162 High Similarity NPC7688
0.9157 High Similarity NPC476247
0.9157 High Similarity NPC220912
0.9152 High Similarity NPC101731
0.9133 High Similarity NPC117668
0.9118 High Similarity NPC4200
0.9118 High Similarity NPC174700
0.9112 High Similarity NPC326877
0.9107 High Similarity NPC472449
0.9096 High Similarity NPC228383
0.9096 High Similarity NPC472632
0.9096 High Similarity NPC474038
0.9096 High Similarity NPC158188
0.9096 High Similarity NPC264302
0.9096 High Similarity NPC34089
0.9096 High Similarity NPC266314
0.9096 High Similarity NPC196179
0.9091 High Similarity NPC172202
0.9091 High Similarity NPC53545
0.9091 High Similarity NPC250214
0.9091 High Similarity NPC95936
0.9091 High Similarity NPC284127
0.9091 High Similarity NPC117418
0.9091 High Similarity NPC476410
0.908 High Similarity NPC476203
0.9064 High Similarity NPC310794
0.9059 High Similarity NPC279209
0.9059 High Similarity NPC476365
0.9059 High Similarity NPC74559
0.9059 High Similarity NPC102277
0.9053 High Similarity NPC8965
0.9048 High Similarity NPC224280
0.9048 High Similarity NPC239752
0.9048 High Similarity NPC275780
0.9048 High Similarity NPC62261
0.9048 High Similarity NPC472450
0.9048 High Similarity NPC470457
0.9048 High Similarity NPC50960
0.9042 High Similarity NPC474150
0.9042 High Similarity NPC474033
0.9042 High Similarity NPC472448
0.9042 High Similarity NPC474034
0.9042 High Similarity NPC474162
0.9042 High Similarity NPC83922
0.9036 High Similarity NPC204290
0.9036 High Similarity NPC475784
0.9036 High Similarity NPC118256
0.9036 High Similarity NPC188967
0.9036 High Similarity NPC174953
0.9036 High Similarity NPC119209
0.9036 High Similarity NPC192686
0.9034 High Similarity NPC139683
0.9034 High Similarity NPC73929
0.9034 High Similarity NPC47905
0.9034 High Similarity NPC64755
0.903 High Similarity NPC474208
0.903 High Similarity NPC156057
0.903 High Similarity NPC474055
0.903 High Similarity NPC470402
0.903 High Similarity NPC183851
0.903 High Similarity NPC474836
0.903 High Similarity NPC78225
0.903 High Similarity NPC475267
0.903 High Similarity NPC162869
0.903 High Similarity NPC63454
0.903 High Similarity NPC223787
0.903 High Similarity NPC48208
0.903 High Similarity NPC472598
0.9029 High Similarity NPC318119
0.9029 High Similarity NPC148710
0.9006 High Similarity NPC259152
0.9006 High Similarity NPC3583
0.9006 High Similarity NPC121333
0.9006 High Similarity NPC65333
0.9006 High Similarity NPC256760
0.9 High Similarity NPC188079
0.9 High Similarity NPC300307
0.8994 High Similarity NPC471213
0.8994 High Similarity NPC128293
0.8994 High Similarity NPC39091
0.8994 High Similarity NPC477082
0.8988 High Similarity NPC23298
0.8988 High Similarity NPC7483
0.8988 High Similarity NPC472625
0.8988 High Similarity NPC470459
0.8988 High Similarity NPC189473
0.8988 High Similarity NPC248638
0.8988 High Similarity NPC63438
0.8988 High Similarity NPC273959
0.8988 High Similarity NPC236521
0.8988 High Similarity NPC186686
0.8988 High Similarity NPC152659
0.8988 High Similarity NPC41301
0.8983 High Similarity NPC477083
0.8983 High Similarity NPC477081
0.8982 High Similarity NPC472634
0.8982 High Similarity NPC471499
0.8982 High Similarity NPC198829
0.8982 High Similarity NPC289771
0.8982 High Similarity NPC471212
0.8982 High Similarity NPC471211
0.8982 High Similarity NPC29876
0.8982 High Similarity NPC167678
0.8982 High Similarity NPC134783
0.8982 High Similarity NPC471210
0.8977 High Similarity NPC111490
0.8977 High Similarity NPC469650
0.8977 High Similarity NPC304322
0.8977 High Similarity NPC261623
0.8976 High Similarity NPC473990
0.8976 High Similarity NPC190487
0.8976 High Similarity NPC154304
0.8971 High Similarity NPC321916
0.897 High Similarity NPC195796
0.897 High Similarity NPC235165
0.897 High Similarity NPC35038
0.897 High Similarity NPC278778
0.897 High Similarity NPC255106
0.897 High Similarity NPC191146
0.897 High Similarity NPC68093
0.897 High Similarity NPC291878
0.896 High Similarity NPC169733
0.896 High Similarity NPC255799
0.8953 High Similarity NPC204693
0.8953 High Similarity NPC239549
0.8953 High Similarity NPC51774
0.8953 High Similarity NPC25724
0.8953 High Similarity NPC236191
0.8953 High Similarity NPC208668
0.8953 High Similarity NPC98583
0.8947 High Similarity NPC150767
0.8947 High Similarity NPC78734
0.8947 High Similarity NPC218488
0.8947 High Similarity NPC21190
0.8947 High Similarity NPC472276
0.8947 High Similarity NPC183357
0.8947 High Similarity NPC22195
0.8941 High Similarity NPC158761
0.8941 High Similarity NPC247973
0.8941 High Similarity NPC470456
0.8941 High Similarity NPC474024
0.8935 High Similarity NPC234052
0.8935 High Similarity NPC471788
0.8935 High Similarity NPC293319
0.8935 High Similarity NPC326520
0.8933 High Similarity NPC31208
0.8933 High Similarity NPC472724

  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 NPC324742 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
0.9162 High Similarity NPD6166 Phase 2
0.9162 High Similarity NPD6167 Clinical (unspecified phase)
0.9162 High Similarity NPD6168 Clinical (unspecified phase)
0.8848 High Similarity NPD2393 Clinical (unspecified phase)
0.8848 High Similarity NPD2801 Approved
0.8837 High Similarity NPD7472 Approved
0.8788 High Similarity NPD1934 Approved
0.8786 High Similarity NPD7993 Clinical (unspecified phase)
0.8779 High Similarity NPD7054 Approved
0.8757 High Similarity NPD6959 Discontinued
0.8728 High Similarity NPD7074 Phase 3
0.8698 High Similarity NPD5494 Approved
0.8686 High Similarity NPD7808 Phase 3
0.8678 High Similarity NPD6797 Phase 2
0.8629 High Similarity NPD7251 Discontinued
0.858 High Similarity NPD4338 Clinical (unspecified phase)
0.8563 High Similarity NPD5844 Phase 1
0.8554 High Similarity NPD4380 Phase 2
0.8521 High Similarity NPD4868 Clinical (unspecified phase)
0.8506 High Similarity NPD3818 Discontinued
0.8462 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8398 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8391 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8382 Intermediate Similarity NPD6232 Discontinued
0.8343 Intermediate Similarity NPD7473 Discontinued
0.8304 Intermediate Similarity NPD3882 Suspended
0.8303 Intermediate Similarity NPD1511 Approved
0.8256 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8246 Intermediate Similarity NPD3817 Phase 2
0.8204 Intermediate Similarity NPD1512 Approved
0.815 Intermediate Similarity NPD7075 Discontinued
0.8144 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8144 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8122 Intermediate Similarity NPD8312 Approved
0.8122 Intermediate Similarity NPD8313 Approved
0.8092 Intermediate Similarity NPD7768 Phase 2
0.8081 Intermediate Similarity NPD7819 Suspended
0.8081 Intermediate Similarity NPD1465 Phase 2
0.807 Intermediate Similarity NPD7411 Suspended
0.8035 Intermediate Similarity NPD5402 Approved
0.8023 Intermediate Similarity NPD6801 Discontinued
0.8011 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD6559 Discontinued
0.7977 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD1247 Approved
0.7892 Intermediate Similarity NPD1549 Phase 2
0.7874 Intermediate Similarity NPD8455 Phase 2
0.7857 Intermediate Similarity NPD8151 Discontinued
0.7771 Intermediate Similarity NPD2796 Approved
0.7765 Intermediate Similarity NPD7390 Discontinued
0.7765 Intermediate Similarity NPD3787 Discontinued
0.774 Intermediate Similarity NPD3749 Approved
0.7722 Intermediate Similarity NPD3926 Phase 2
0.7711 Intermediate Similarity NPD1510 Phase 2
0.7692 Intermediate Similarity NPD3751 Discontinued
0.7692 Intermediate Similarity NPD7228 Approved
0.7688 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7783 Phase 2
0.7647 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD5403 Approved
0.7629 Intermediate Similarity NPD6779 Approved
0.7629 Intermediate Similarity NPD6780 Approved
0.7629 Intermediate Similarity NPD6777 Approved
0.7629 Intermediate Similarity NPD6776 Approved
0.7629 Intermediate Similarity NPD6782 Approved
0.7629 Intermediate Similarity NPD6781 Approved
0.7629 Intermediate Similarity NPD6778 Approved
0.7616 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7698 Approved
0.7602 Intermediate Similarity NPD7696 Phase 3
0.7602 Intermediate Similarity NPD7697 Approved
0.7598 Intermediate Similarity NPD919 Approved
0.7576 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD1613 Approved
0.7563 Intermediate Similarity NPD7870 Phase 2
0.7563 Intermediate Similarity NPD7871 Phase 2
0.7558 Intermediate Similarity NPD6799 Approved
0.7538 Intermediate Similarity NPD7701 Phase 2
0.7514 Intermediate Similarity NPD5401 Approved
0.7514 Intermediate Similarity NPD7199 Phase 2
0.7513 Intermediate Similarity NPD8150 Discontinued
0.7513 Intermediate Similarity NPD7435 Discontinued
0.75 Intermediate Similarity NPD6234 Discontinued
0.75 Intermediate Similarity NPD6599 Discontinued
0.7486 Intermediate Similarity NPD1653 Approved
0.7474 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD1240 Approved
0.747 Intermediate Similarity NPD943 Approved
0.7456 Intermediate Similarity NPD2935 Discontinued
0.7449 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7699 Phase 2
0.7436 Intermediate Similarity NPD7700 Phase 2
0.7433 Intermediate Similarity NPD7685 Pre-registration
0.7429 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD2800 Approved
0.7427 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD37 Approved
0.7414 Intermediate Similarity NPD2532 Approved
0.7414 Intermediate Similarity NPD2534 Approved
0.7414 Intermediate Similarity NPD2533 Approved
0.7394 Intermediate Similarity NPD3027 Phase 3
0.7389 Intermediate Similarity NPD4966 Approved
0.7389 Intermediate Similarity NPD4965 Approved
0.7389 Intermediate Similarity NPD4967 Phase 2
0.7384 Intermediate Similarity NPD3750 Approved
0.7381 Intermediate Similarity NPD1607 Approved
0.7376 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD7874 Approved
0.7374 Intermediate Similarity NPD6823 Phase 2
0.7371 Intermediate Similarity NPD6534 Approved
0.7371 Intermediate Similarity NPD6535 Approved
0.7368 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD3226 Approved
0.7341 Intermediate Similarity NPD6190 Approved
0.734 Intermediate Similarity NPD7801 Approved
0.734 Intermediate Similarity NPD7240 Approved
0.7337 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD920 Approved
0.733 Intermediate Similarity NPD8434 Phase 2
0.7314 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD4628 Phase 3
0.7282 Intermediate Similarity NPD4363 Phase 3
0.7282 Intermediate Similarity NPD4360 Phase 2
0.7273 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD4908 Phase 1
0.7219 Intermediate Similarity NPD230 Phase 1
0.7216 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD2344 Approved
0.7196 Intermediate Similarity NPD5953 Discontinued
0.7193 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6212 Phase 3
0.7143 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7584 Approved
0.7143 Intermediate Similarity NPD6213 Phase 3
0.7135 Intermediate Similarity NPD8127 Discontinued
0.7129 Intermediate Similarity NPD8320 Phase 1
0.7129 Intermediate Similarity NPD8319 Approved
0.7127 Intermediate Similarity NPD6844 Discontinued
0.7126 Intermediate Similarity NPD1243 Approved
0.712 Intermediate Similarity NPD7549 Discontinued
0.7118 Intermediate Similarity NPD447 Suspended
0.711 Intermediate Similarity NPD2346 Discontinued
0.7109 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7229 Phase 3
0.7093 Intermediate Similarity NPD3748 Approved
0.7093 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD2799 Discontinued
0.709 Intermediate Similarity NPD7286 Phase 2
0.7086 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD7680 Approved
0.7076 Intermediate Similarity NPD6651 Approved
0.7056 Intermediate Similarity NPD7458 Discontinued
0.7052 Intermediate Similarity NPD5406 Approved
0.7052 Intermediate Similarity NPD6100 Approved
0.7052 Intermediate Similarity NPD5404 Approved
0.7052 Intermediate Similarity NPD6099 Approved
0.7052 Intermediate Similarity NPD5408 Approved
0.7052 Intermediate Similarity NPD1551 Phase 2
0.7052 Intermediate Similarity NPD5405 Approved
0.7045 Intermediate Similarity NPD2309 Approved
0.7041 Intermediate Similarity NPD2313 Discontinued
0.7041 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD5710 Approved
0.7005 Intermediate Similarity NPD5711 Approved
0.6965 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6964 Remote Similarity NPD9494 Approved
0.6948 Remote Similarity NPD7907 Approved
0.6947 Remote Similarity NPD7177 Discontinued
0.6919 Remote Similarity NPD5124 Phase 1
0.6919 Remote Similarity NPD1933 Approved
0.6919 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7266 Discontinued
0.6904 Remote Similarity NPD4287 Approved
0.6901 Remote Similarity NPD6233 Phase 2
0.69 Remote Similarity NPD4361 Phase 2
0.69 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7033 Discontinued
0.6893 Remote Similarity NPD8166 Discontinued
0.6893 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6893 Remote Similarity NPD7003 Approved
0.6885 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6882 Remote Similarity NPD4625 Phase 3
0.6881 Remote Similarity NPD8285 Discontinued
0.6878 Remote Similarity NPD5242 Approved
0.6875 Remote Similarity NPD2424 Discontinued
0.6872 Remote Similarity NPD8054 Approved
0.6872 Remote Similarity NPD8053 Approved
0.6866 Remote Similarity NPD8059 Phase 3
0.6866 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6864 Remote Similarity NPD2861 Phase 2
0.6854 Remote Similarity NPD4665 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