Structure

Physi-Chem Properties

Molecular Weight:  324.14
Volume:  336.956
LogP:  5.266
LogD:  3.789
LogS:  -3.677
# Rotatable Bonds:  2
TPSA:  58.92
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.812
Synthetic Accessibility Score:  3.611
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.734
MDCK Permeability:  1.4415119039767887e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.896
30% Bioavailability (F30%):  0.386

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.064
Plasma Protein Binding (PPB):  99.10103607177734%
Volume Distribution (VD):  1.163
Pgp-substrate:  2.122667074203491%

ADMET: Metabolism

CYP1A2-inhibitor:  0.811
CYP1A2-substrate:  0.838
CYP2C19-inhibitor:  0.948
CYP2C19-substrate:  0.245
CYP2C9-inhibitor:  0.881
CYP2C9-substrate:  0.957
CYP2D6-inhibitor:  0.874
CYP2D6-substrate:  0.796
CYP3A4-inhibitor:  0.498
CYP3A4-substrate:  0.322

ADMET: Excretion

Clearance (CL):  14.245
Half-life (T1/2):  0.294

ADMET: Toxicity

hERG Blockers:  0.143
Human Hepatotoxicity (H-HT):  0.889
Drug-inuced Liver Injury (DILI):  0.453
AMES Toxicity:  0.626
Rat Oral Acute Toxicity:  0.339
Maximum Recommended Daily Dose:  0.876
Skin Sensitization:  0.927
Carcinogencity:  0.143
Eye Corrosion:  0.003
Eye Irritation:  0.649
Respiratory Toxicity:  0.644

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

  Natural Product: NPC164574

Natural Product ID:  NPC164574
Common Name*:   Phaseollidin
IUPAC Name:   (6aR,11aR)-10-(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
Synonyms:   Phaseolidin; Phaseollidin
Standard InCHIKey:  OFWYIUYVHYPQNX-JXFKEZNVSA-N
Standard InCHI:  InChI=1S/C20H20O4/c1-11(2)3-5-14-17(22)8-7-13-16-10-23-18-9-12(21)4-6-15(18)20(16)24-19(13)14/h3-4,6-9,16,20-22H,5,10H2,1-2H3/t16-,20-/m0/s1
SMILES:  CC(=CCc1c(ccc2[C@@H]3COc4cc(ccc4[C@@H]3Oc12)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508534
PubChem CID:   119268
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002617] Furanoisoflavonoids
          • [CHEMONTID:0001608] Pterocarpans

*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
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota stem bark n.a. n.a. PMID[17489632]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. stem n.a. PMID[18484536]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota stem bark Mukono, Uganda 2005-JUN PMID[19008110]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19102656]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO17039 Pharbitis nil Species Convolvulaceae Eukaryota Seeds n.a. n.a. PMID[19435339]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19836230]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[20337486]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21116437]
NPO40123 Erythrina burana Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[8277323]
NPO17794 Streptomyces violaceusniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8557611]
NPO4002 Lappula intermedia Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18560 Tripterospermum japonicum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17039 Pharbitis nil Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18560 Tripterospermum japonicum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4002 Lappula intermedia Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31286 Dolichos lablab Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17039 Pharbitis nil Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19587 Cordia rothii Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14323 Bossiella orbigniana Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17390 Dysidea robusta Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12920 Erimacrus isenbeckii Species Atelecyclidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10080 Teucrium betonicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19809 Streptomyces roseoviolaceus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19260 Zanthoxylum petiolare Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16356 Crocynia membranacea Species Crocyniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17794 Streptomyces violaceusniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14662 Lomatia longifolia Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16070 Indigofera oblongifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4002 Lappula intermedia Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9811 Macrotyloma uniflorum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18560 Tripterospermum japonicum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13146 Pertusaria albescens Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8526 Erythrina abyssinica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5160 Pandanus veitchi Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17039 Pharbitis nil Species Convolvulaceae 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
NPT168 Cell Line P388 Mus musculus IC50 > 10000.0 nM PMID[569145]
NPT1161 Cell Line CHO Cricetulus griseus IC50 = 4000.0 nM PMID[569145]
NPT1161 Cell Line CHO Cricetulus griseus IC50 = 7600.0 nM PMID[569145]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 > 30000.0 nM PMID[569148]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 30000.0 nM PMID[569148]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 30000.0 nM PMID[569148]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 500.0 ug ml-1 PMID[569145]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 > 1000.0 ug ml-1 PMID[569145]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 400.0 ug ml-1 PMID[569145]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 5500.0 ug ml-1 PMID[569145]
NPT771 Organism Penicillium crustosum Penicillium crustosum MIC > 100.0 ug.mL-1 PMID[569146]
NPT769 Organism Mucor mucedo Mucor mucedo MIC = 100.0 ug.mL-1 PMID[569146]
NPT767 Organism Pichia jadinii Cyberlindnera jadinii MIC > 100.0 ug.mL-1 PMID[569146]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC > 100.0 ug.mL-1 PMID[569146]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 100.0 ug.mL-1 PMID[569146]
NPT19 Organism Escherichia coli Escherichia coli MIC > 100.0 ug.mL-1 PMID[569146]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 25.0 ug.mL-1 PMID[569146]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 50.0 ug.mL-1 PMID[569146]
NPT2 Others Unspecified IC50 = 8700.0 nM PMID[569147]

☑ 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 NPC164574 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC228369
1.0 High Similarity NPC476166
1.0 High Similarity NPC17343
1.0 High Similarity NPC118114
1.0 High Similarity NPC129784
1.0 High Similarity NPC12875
1.0 High Similarity NPC196765
1.0 High Similarity NPC280653
1.0 High Similarity NPC206224
1.0 High Similarity NPC236014
1.0 High Similarity NPC300875
1.0 High Similarity NPC129106
1.0 High Similarity NPC268917
1.0 High Similarity NPC150011
1.0 High Similarity NPC207892
0.992 High Similarity NPC13005
0.9919 High Similarity NPC27187
0.9919 High Similarity NPC470225
0.984 High Similarity NPC181497
0.984 High Similarity NPC271945
0.9764 High Similarity NPC296915
0.9764 High Similarity NPC225696
0.9764 High Similarity NPC223008
0.9764 High Similarity NPC198154
0.9764 High Similarity NPC115335
0.9764 High Similarity NPC97834
0.9758 High Similarity NPC47283
0.9758 High Similarity NPC39064
0.9758 High Similarity NPC38664
0.9758 High Similarity NPC53986
0.9685 High Similarity NPC85435
0.968 High Similarity NPC93962
0.9609 High Similarity NPC117048
0.9609 High Similarity NPC124085
0.96 High Similarity NPC274717
0.9597 High Similarity NPC26879
0.9597 High Similarity NPC262573
0.9597 High Similarity NPC230479
0.9597 High Similarity NPC283049
0.9597 High Similarity NPC471215
0.9597 High Similarity NPC50315
0.9538 High Similarity NPC474687
0.9528 High Similarity NPC211413
0.9528 High Similarity NPC68205
0.9528 High Similarity NPC118683
0.9528 High Similarity NPC244888
0.9528 High Similarity NPC164804
0.9528 High Similarity NPC293203
0.9528 High Similarity NPC162801
0.9516 High Similarity NPC285040
0.9516 High Similarity NPC103420
0.9516 High Similarity NPC17809
0.9516 High Similarity NPC188022
0.9516 High Similarity NPC102540
0.9466 High Similarity NPC475836
0.9462 High Similarity NPC20829
0.9462 High Similarity NPC3049
0.9462 High Similarity NPC18189
0.9462 High Similarity NPC262585
0.944 High Similarity NPC276212
0.9435 High Similarity NPC256015
0.9435 High Similarity NPC246648
0.9435 High Similarity NPC197351
0.9435 High Similarity NPC106914
0.9435 High Similarity NPC86502
0.9435 High Similarity NPC294156
0.9435 High Similarity NPC134195
0.938 High Similarity NPC77196
0.9375 High Similarity NPC103799
0.936 High Similarity NPC81641
0.9355 High Similarity NPC76465
0.9355 High Similarity NPC38761
0.9323 High Similarity NPC5155
0.9308 High Similarity NPC473107
0.9274 High Similarity NPC150026
0.9274 High Similarity NPC36016
0.9274 High Similarity NPC100099
0.9237 High Similarity NPC125579
0.9231 High Similarity NPC92805
0.9219 High Similarity NPC134360
0.9213 High Similarity NPC149796
0.9194 High Similarity NPC193364
0.9194 High Similarity NPC54972
0.9167 High Similarity NPC471522
0.9141 High Similarity NPC87224
0.9141 High Similarity NPC222572
0.9118 High Similarity NPC12641
0.9118 High Similarity NPC280092
0.9118 High Similarity NPC93323
0.9118 High Similarity NPC45257
0.9104 High Similarity NPC184797
0.9104 High Similarity NPC27495
0.9104 High Similarity NPC309124
0.9098 High Similarity NPC470307
0.9098 High Similarity NPC470308
0.9098 High Similarity NPC477938
0.9091 High Similarity NPC473413
0.9084 High Similarity NPC215037
0.9051 High Similarity NPC469557
0.9044 High Similarity NPC85264
0.9044 High Similarity NPC102044
0.9044 High Similarity NPC47633
0.9037 High Similarity NPC87725
0.9037 High Similarity NPC263261
0.9032 High Similarity NPC93398
0.9032 High Similarity NPC8283
0.9032 High Similarity NPC258979
0.903 High Similarity NPC236306
0.903 High Similarity NPC32630
0.903 High Similarity NPC473739
0.903 High Similarity NPC232164
0.903 High Similarity NPC260741
0.903 High Similarity NPC70682
0.9023 High Similarity NPC141717
0.9015 High Similarity NPC476617
0.9015 High Similarity NPC476616
0.9015 High Similarity NPC476615
0.8978 High Similarity NPC63879
0.8971 High Similarity NPC107161
0.8952 High Similarity NPC172253
0.8952 High Similarity NPC59561
0.8947 High Similarity NPC11727
0.8947 High Similarity NPC15109
0.8939 High Similarity NPC11060
0.8921 High Similarity NPC16269
0.8921 High Similarity NPC21776
0.8906 High Similarity NPC167571
0.8906 High Similarity NPC207179
0.8906 High Similarity NPC278552
0.8897 High Similarity NPC100482
0.8897 High Similarity NPC35216
0.8897 High Similarity NPC277331
0.8897 High Similarity NPC265075
0.8897 High Similarity NPC247291
0.8889 High Similarity NPC476633
0.8889 High Similarity NPC471388
0.8881 High Similarity NPC234952
0.8881 High Similarity NPC270456
0.8881 High Similarity NPC126101
0.8881 High Similarity NPC78047
0.8881 High Similarity NPC248727
0.8881 High Similarity NPC173660
0.8881 High Similarity NPC162659
0.8881 High Similarity NPC265433
0.8881 High Similarity NPC470802
0.8871 High Similarity NPC131118
0.8864 High Similarity NPC472798
0.8849 High Similarity NPC260397
0.8841 High Similarity NPC475492
0.8841 High Similarity NPC473108
0.8832 High Similarity NPC2613
0.8832 High Similarity NPC475891
0.8832 High Similarity NPC204347
0.8832 High Similarity NPC59841
0.8828 High Similarity NPC159132
0.8824 High Similarity NPC160283
0.8824 High Similarity NPC259519
0.8824 High Similarity NPC254759
0.8824 High Similarity NPC174787
0.8824 High Similarity NPC182509
0.8824 High Similarity NPC213607
0.8806 High Similarity NPC94750
0.8806 High Similarity NPC195022
0.8806 High Similarity NPC474206
0.8806 High Similarity NPC112246
0.8806 High Similarity NPC112939
0.8806 High Similarity NPC151224
0.8806 High Similarity NPC121812
0.8806 High Similarity NPC470356
0.8806 High Similarity NPC61946
0.88 High Similarity NPC295259
0.8797 High Similarity NPC177712
0.8797 High Similarity NPC26394
0.8797 High Similarity NPC24913
0.8788 High Similarity NPC472590
0.8788 High Similarity NPC160623
0.8786 High Similarity NPC101376
0.8779 High Similarity NPC472795
0.8779 High Similarity NPC472796
0.8779 High Similarity NPC472797
0.8777 High Similarity NPC181615
0.8777 High Similarity NPC108994
0.8777 High Similarity NPC106126
0.8777 High Similarity NPC180953
0.8769 High Similarity NPC473134
0.8759 High Similarity NPC108674
0.8759 High Similarity NPC471389
0.875 High Similarity NPC127218
0.875 High Similarity NPC474160
0.875 High Similarity NPC319647
0.875 High Similarity NPC25966
0.875 High Similarity NPC292882
0.875 High Similarity NPC245207
0.8741 High Similarity NPC29799
0.8741 High Similarity NPC209985
0.8741 High Similarity NPC156502
0.8741 High Similarity NPC306441
0.8741 High Similarity NPC16435
0.8741 High Similarity NPC474639
0.8741 High Similarity NPC227503

  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 NPC164574 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
0.9449 High Similarity NPD4907 Clinical (unspecified phase)
0.9291 High Similarity NPD4908 Phase 1
0.9194 High Similarity NPD1610 Phase 2
0.8769 High Similarity NPD2861 Phase 2
0.872 High Similarity NPD1548 Phase 1
0.8636 High Similarity NPD4625 Phase 3
0.8582 High Similarity NPD1612 Clinical (unspecified phase)
0.8582 High Similarity NPD1613 Approved
0.8462 Intermediate Similarity NPD4749 Approved
0.8433 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8346 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8248 Intermediate Similarity NPD5124 Phase 1
0.8248 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.8222 Intermediate Similarity NPD3027 Phase 3
0.8099 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.8069 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8067 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8029 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7212 Phase 2
0.8 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7213 Phase 3
0.7987 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7958 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7958 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7945 Intermediate Similarity NPD7447 Phase 1
0.7943 Intermediate Similarity NPD5588 Approved
0.7917 Intermediate Similarity NPD7466 Approved
0.7914 Intermediate Similarity NPD4060 Phase 1
0.791 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7902 Intermediate Similarity NPD1549 Phase 2
0.7895 Intermediate Similarity NPD422 Phase 1
0.7872 Intermediate Similarity NPD4536 Approved
0.7872 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7872 Intermediate Similarity NPD4538 Approved
0.7868 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD8651 Approved
0.7808 Intermediate Similarity NPD5058 Phase 3
0.78 Intermediate Similarity NPD4380 Phase 2
0.7769 Intermediate Similarity NPD6671 Approved
0.7762 Intermediate Similarity NPD6099 Approved
0.7762 Intermediate Similarity NPD6100 Approved
0.7761 Intermediate Similarity NPD1091 Approved
0.7727 Intermediate Similarity NPD7075 Discontinued
0.7721 Intermediate Similarity NPD6696 Suspended
0.7708 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD6002 Phase 3
0.7708 Intermediate Similarity NPD6004 Phase 3
0.7708 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD6005 Phase 3
0.7697 Intermediate Similarity NPD1934 Approved
0.7692 Intermediate Similarity NPD5960 Phase 3
0.7671 Intermediate Similarity NPD3892 Phase 2
0.7671 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD3750 Approved
0.7662 Intermediate Similarity NPD7768 Phase 2
0.7647 Intermediate Similarity NPD7819 Suspended
0.7647 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD7229 Phase 3
0.7639 Intermediate Similarity NPD2796 Approved
0.7632 Intermediate Similarity NPD7411 Suspended
0.7628 Intermediate Similarity NPD5494 Approved
0.7619 Intermediate Similarity NPD968 Approved
0.7606 Intermediate Similarity NPD6355 Discontinued
0.7603 Intermediate Similarity NPD1652 Phase 2
0.7584 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD37 Approved
0.7581 Intermediate Similarity NPD940 Approved
0.7581 Intermediate Similarity NPD846 Approved
0.758 Intermediate Similarity NPD6959 Discontinued
0.7569 Intermediate Similarity NPD1510 Phase 2
0.7569 Intermediate Similarity NPD7033 Discontinued
0.7564 Intermediate Similarity NPD6234 Discontinued
0.7548 Intermediate Similarity NPD4966 Approved
0.7548 Intermediate Similarity NPD4967 Phase 2
0.7548 Intermediate Similarity NPD4965 Approved
0.7536 Intermediate Similarity NPD2797 Approved
0.7534 Intermediate Similarity NPD2424 Discontinued
0.7518 Intermediate Similarity NPD6583 Phase 3
0.7518 Intermediate Similarity NPD5327 Phase 3
0.7518 Intermediate Similarity NPD6582 Phase 2
0.75 Intermediate Similarity NPD7157 Approved
0.75 Intermediate Similarity NPD2684 Approved
0.75 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6559 Discontinued
0.7483 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD2800 Approved
0.7483 Intermediate Similarity NPD5735 Approved
0.7483 Intermediate Similarity NPD6674 Discontinued
0.7482 Intermediate Similarity NPD6584 Phase 3
0.745 Intermediate Similarity NPD6666 Approved
0.745 Intermediate Similarity NPD6667 Approved
0.7442 Intermediate Similarity NPD4750 Phase 3
0.7438 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD4097 Suspended
0.7429 Intermediate Similarity NPD3018 Phase 2
0.7422 Intermediate Similarity NPD290 Approved
0.7419 Intermediate Similarity NPD3020 Approved
0.7413 Intermediate Similarity NPD4140 Approved
0.7413 Intermediate Similarity NPD1240 Approved
0.7413 Intermediate Similarity NPD2238 Phase 2
0.7407 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD5844 Phase 1
0.7405 Intermediate Similarity NPD5535 Approved
0.7405 Intermediate Similarity NPD7843 Approved
0.74 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD7041 Phase 2
0.7394 Intermediate Similarity NPD6798 Discontinued
0.7394 Intermediate Similarity NPD3268 Approved
0.7379 Intermediate Similarity NPD2200 Suspended
0.7379 Intermediate Similarity NPD7097 Phase 1
0.7358 Intermediate Similarity NPD7199 Phase 2
0.7357 Intermediate Similarity NPD3691 Phase 2
0.7357 Intermediate Similarity NPD3690 Phase 2
0.7355 Intermediate Similarity NPD6801 Discontinued
0.7353 Intermediate Similarity NPD5125 Phase 3
0.7353 Intermediate Similarity NPD5126 Approved
0.7351 Intermediate Similarity NPD2533 Approved
0.7351 Intermediate Similarity NPD2532 Approved
0.7351 Intermediate Similarity NPD2534 Approved
0.7348 Intermediate Similarity NPD5283 Phase 1
0.7347 Intermediate Similarity NPD5762 Approved
0.7347 Intermediate Similarity NPD5763 Approved
0.7346 Intermediate Similarity NPD7228 Approved
0.7333 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7741 Discontinued
0.7329 Intermediate Similarity NPD3748 Approved
0.7329 Intermediate Similarity NPD6166 Phase 2
0.7329 Intermediate Similarity NPD3846 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD3882 Suspended
0.732 Intermediate Similarity NPD1653 Approved
0.7315 Intermediate Similarity NPD4535 Phase 3
0.7313 Intermediate Similarity NPD7340 Approved
0.731 Intermediate Similarity NPD6353 Approved
0.731 Intermediate Similarity NPD2157 Approved
0.731 Intermediate Similarity NPD1607 Approved
0.7308 Intermediate Similarity NPD2801 Approved
0.7308 Intermediate Similarity NPD8455 Phase 2
0.7297 Intermediate Similarity NPD7037 Approved
0.729 Intermediate Similarity NPD6072 Discontinued
0.7285 Intermediate Similarity NPD1511 Approved
0.7279 Intermediate Similarity NPD2935 Discontinued
0.7279 Intermediate Similarity NPD1551 Phase 2
0.7278 Intermediate Similarity NPD3749 Approved
0.7267 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD2982 Phase 2
0.7266 Intermediate Similarity NPD2983 Phase 2
0.7239 Intermediate Similarity NPD3818 Discontinued
0.7226 Intermediate Similarity NPD5846 Approved
0.7226 Intermediate Similarity NPD4626 Approved
0.7226 Intermediate Similarity NPD6516 Phase 2
0.7222 Intermediate Similarity NPD1242 Phase 1
0.7222 Intermediate Similarity NPD6233 Phase 2
0.7218 Intermediate Similarity NPD1398 Phase 1
0.7214 Intermediate Similarity NPD3225 Approved
0.7211 Intermediate Similarity NPD2799 Discontinued
0.7211 Intermediate Similarity NPD4108 Discontinued
0.72 Intermediate Similarity NPD6331 Phase 2
0.72 Intermediate Similarity NPD4628 Phase 3
0.7197 Intermediate Similarity NPD5929 Approved
0.7194 Intermediate Similarity NPD1608 Approved
0.7194 Intermediate Similarity NPD2231 Phase 2
0.7194 Intermediate Similarity NPD2981 Phase 2
0.7194 Intermediate Similarity NPD2235 Phase 2
0.719 Intermediate Similarity NPD1512 Approved
0.7181 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD2860 Approved
0.7177 Intermediate Similarity NPD2859 Approved
0.7176 Intermediate Similarity NPD5451 Approved
0.7174 Intermediate Similarity NPD3496 Discontinued
0.7172 Intermediate Similarity NPD3620 Phase 2
0.7172 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD6799 Approved
0.7163 Intermediate Similarity NPD3094 Phase 2
0.7162 Intermediate Similarity NPD4477 Approved
0.7162 Intermediate Similarity NPD4476 Approved
0.7161 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD3443 Approved
0.7153 Intermediate Similarity NPD3444 Approved
0.7153 Intermediate Similarity NPD5691 Approved
0.7153 Intermediate Similarity NPD3445 Approved
0.7152 Intermediate Similarity NPD7074 Phase 3
0.7143 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7119 Phase 2
0.7143 Intermediate Similarity NPD920 Approved
0.7143 Intermediate Similarity NPD3685 Discontinued
0.7143 Intermediate Similarity NPD821 Approved
0.7124 Intermediate Similarity NPD7020 Approved
0.7124 Intermediate Similarity NPD7019 Approved
0.7122 Intermediate Similarity NPD3705 Approved
0.7122 Intermediate Similarity NPD1611 Approved
0.7115 Intermediate Similarity NPD6599 Discontinued
0.7114 Intermediate Similarity NPD7030 Discontinued
0.7114 Intermediate Similarity NPD2029 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