Structure

Physi-Chem Properties

Molecular Weight:  322.12
Volume:  328.4
LogP:  4.903
LogD:  4.29
LogS:  -4.093
# Rotatable Bonds:  0
TPSA:  47.92
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.79
Synthetic Accessibility Score:  3.771
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:  -4.796
MDCK Permeability:  1.5040402104204986e-05
Pgp-inhibitor:  0.639
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.117
Plasma Protein Binding (PPB):  99.62653350830078%
Volume Distribution (VD):  0.788
Pgp-substrate:  1.088033676147461%

ADMET: Metabolism

CYP1A2-inhibitor:  0.853
CYP1A2-substrate:  0.812
CYP2C19-inhibitor:  0.932
CYP2C19-substrate:  0.684
CYP2C9-inhibitor:  0.903
CYP2C9-substrate:  0.941
CYP2D6-inhibitor:  0.949
CYP2D6-substrate:  0.858
CYP3A4-inhibitor:  0.836
CYP3A4-substrate:  0.604

ADMET: Excretion

Clearance (CL):  2.771
Half-life (T1/2):  0.192

ADMET: Toxicity

hERG Blockers:  0.536
Human Hepatotoxicity (H-HT):  0.944
Drug-inuced Liver Injury (DILI):  0.771
AMES Toxicity:  0.881
Rat Oral Acute Toxicity:  0.267
Maximum Recommended Daily Dose:  0.881
Skin Sensitization:  0.704
Carcinogencity:  0.719
Eye Corrosion:  0.003
Eye Irritation:  0.215
Respiratory Toxicity:  0.851

Download Data

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

  Natural Product: NPC225696

Natural Product ID:  NPC225696
Common Name*:   Phaseolin
IUPAC Name:   n.a.
Synonyms:   Phaseollin
Standard InCHIKey:  LWTDZKXXJRRKDG-KXBFYZLASA-N
Standard InCHI:  InChI=1S/C20H18O4/c1-20(2)8-7-14-16(24-20)6-5-12-15-10-22-17-9-11(21)3-4-13(17)19(15)23-18(12)14/h3-9,15,19,21H,10H2,1-2H3/t15-,19-/m0/s1
SMILES:  Oc1ccc2c(c1)OC[C@@H]1[C@H]2Oc2c1ccc1c2C=CC(O1)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL448350
PubChem CID:   91572
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
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/jf980687v]
NPO24618 Sophora moorcroftiana Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1248/cpb.36.2220]
NPO4240 Elephantopus tomentosus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[10075766]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO6673 Erythrina latissima Species Fabaceae Eukaryota n.a. stem wood n.a. PMID[15649516]
NPO4240 Elephantopus tomentosus Species Asteraceae Eukaryota n.a. stem n.a. PMID[18239317]
NPO4240 Elephantopus tomentosus Species Asteraceae Eukaryota n.a. root n.a. PMID[18239317]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19102656]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21174 Vigna unguiculata Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO21174 Vigna unguiculata Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO21174 Vigna unguiculata Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24618 Sophora moorcroftiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21174 Vigna unguiculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6673 Erythrina latissima Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4240 Elephantopus tomentosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21174 Vigna unguiculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6673 Erythrina latissima 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]
NPO24618 Sophora moorcroftiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4240 Elephantopus tomentosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24618 Sophora moorcroftiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10080 Teucrium betonicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4240 Elephantopus tomentosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4934 Phaseolus vulgaris Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21174 Vigna unguiculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24618 Sophora moorcroftiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11451 Lespedeza cyrtobotrya Species Fabaceae 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
NPT344 Individual Protein Sialidase Clostridium perfringens IC50 = 33550.0 nM PMID[508380]
NPT345 Individual Protein Sialidase Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961) IC50 = 31400.0 nM PMID[508380]
NPT344 Individual Protein Sialidase Clostridium perfringens Ki = 4840.0 nM PMID[508380]
NPT344 Individual Protein Sialidase Clostridium perfringens Inhibition = 91.0 % PMID[508380]
NPT344 Individual Protein Sialidase Clostridium perfringens Inhibition = 9.0 % PMID[508380]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 9.5 % PMID[508381]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 1.5 n.a. PMID[508381]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 2.6 % PMID[508381]
NPT65 Cell Line HepG2 Homo sapiens Inhibition = 0.0 % PMID[508381]
NPT81 Cell Line A549 Homo sapiens Inhibition = 34.7 % PMID[508381]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 6.8 % PMID[508381]
NPT660 Cell Line SW480 Homo sapiens Inhibition = 0.0 % PMID[508381]
NPT771 Organism Penicillium crustosum Penicillium crustosum MIC > 100.0 ug.mL-1 PMID[508378]
NPT769 Organism Mucor mucedo Mucor mucedo MIC = 12.5 ug.mL-1 PMID[508378]
NPT767 Organism Pichia jadinii Cyberlindnera jadinii MIC = 50.0 ug.mL-1 PMID[508378]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC = 25.0 ug.mL-1 PMID[508378]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 100.0 ug.mL-1 PMID[508378]
NPT19 Organism Escherichia coli Escherichia coli MIC > 100.0 ug.mL-1 PMID[508378]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 6.25 ug.mL-1 PMID[508378]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 12.5 ug.mL-1 PMID[508378]
NPT2 Others Unspecified IC50 = 7500.0 nM PMID[508379]
NPT741 Individual Protein Tyrosinase Homo sapiens Inhibition = 2.4 % PMID[508381]
NPT2 Others Unspecified Inhibition = 2.1 % PMID[508381]

☑ 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 NPC225696 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 NPC198154
1.0 High Similarity NPC115335
1.0 High Similarity NPC296915
1.0 High Similarity NPC223008
1.0 High Similarity NPC97834
0.9843 High Similarity NPC13005
0.9764 High Similarity NPC206224
0.9764 High Similarity NPC118114
0.9764 High Similarity NPC164804
0.9764 High Similarity NPC196765
0.9764 High Similarity NPC293203
0.9764 High Similarity NPC280653
0.9764 High Similarity NPC118683
0.9764 High Similarity NPC12875
0.9764 High Similarity NPC228369
0.9764 High Similarity NPC129106
0.9764 High Similarity NPC476166
0.9764 High Similarity NPC129784
0.9764 High Similarity NPC17343
0.9764 High Similarity NPC236014
0.9764 High Similarity NPC268917
0.9764 High Similarity NPC68205
0.9764 High Similarity NPC164574
0.9764 High Similarity NPC244888
0.9764 High Similarity NPC150011
0.9764 High Similarity NPC207892
0.9764 High Similarity NPC211413
0.9764 High Similarity NPC300875
0.9692 High Similarity NPC18189
0.9692 High Similarity NPC262585
0.9692 High Similarity NPC20829
0.9685 High Similarity NPC470225
0.9685 High Similarity NPC27187
0.9612 High Similarity NPC77196
0.9612 High Similarity NPC85435
0.9609 High Similarity NPC181497
0.9609 High Similarity NPC271945
0.9549 High Similarity NPC5155
0.9545 High Similarity NPC475836
0.9538 High Similarity NPC117048
0.9538 High Similarity NPC124085
0.9528 High Similarity NPC39064
0.9528 High Similarity NPC38664
0.9528 High Similarity NPC47283
0.9528 High Similarity NPC53986
0.947 High Similarity NPC474687
0.9462 High Similarity NPC92805
0.9457 High Similarity NPC162801
0.9453 High Similarity NPC134360
0.9453 High Similarity NPC93962
0.9449 High Similarity NPC149796
0.9394 High Similarity NPC3049
0.9375 High Similarity NPC274717
0.937 High Similarity NPC283049
0.937 High Similarity NPC471215
0.937 High Similarity NPC230479
0.937 High Similarity NPC262573
0.937 High Similarity NPC50315
0.937 High Similarity NPC26879
0.9291 High Similarity NPC188022
0.9291 High Similarity NPC17809
0.9291 High Similarity NPC102540
0.9291 High Similarity NPC285040
0.9291 High Similarity NPC103420
0.927 High Similarity NPC469557
0.9242 High Similarity NPC473107
0.9219 High Similarity NPC276212
0.9213 High Similarity NPC246648
0.9213 High Similarity NPC294156
0.9213 High Similarity NPC134195
0.9213 High Similarity NPC106914
0.9213 High Similarity NPC86502
0.9213 High Similarity NPC197351
0.9213 High Similarity NPC256015
0.9173 High Similarity NPC125579
0.916 High Similarity NPC103799
0.9141 High Similarity NPC81641
0.9137 High Similarity NPC21776
0.9137 High Similarity NPC16269
0.9134 High Similarity NPC76465
0.9134 High Similarity NPC38761
0.9104 High Similarity NPC471522
0.9077 High Similarity NPC222572
0.9077 High Similarity NPC87224
0.9055 High Similarity NPC150026
0.9055 High Similarity NPC36016
0.9055 High Similarity NPC100099
0.9051 High Similarity NPC59841
0.9051 High Similarity NPC475891
0.9051 High Similarity NPC2613
0.9051 High Similarity NPC204347
0.9037 High Similarity NPC470308
0.9037 High Similarity NPC470307
0.9023 High Similarity NPC215037
0.8976 High Similarity NPC54972
0.8976 High Similarity NPC193364
0.8963 High Similarity NPC141717
0.8955 High Similarity NPC476616
0.8955 High Similarity NPC476617
0.8955 High Similarity NPC476615
0.8921 High Similarity NPC45257
0.8921 High Similarity NPC12641
0.8921 High Similarity NPC93323
0.8921 High Similarity NPC475492
0.8921 High Similarity NPC280092
0.8915 High Similarity NPC159132
0.8905 High Similarity NPC309124
0.8905 High Similarity NPC184797
0.8905 High Similarity NPC27495
0.8897 High Similarity NPC477938
0.8889 High Similarity NPC15109
0.8889 High Similarity NPC11727
0.8889 High Similarity NPC473413
0.8865 High Similarity NPC101376
0.8857 High Similarity NPC106126
0.8857 High Similarity NPC108994
0.8855 High Similarity NPC473134
0.8849 High Similarity NPC102044
0.8849 High Similarity NPC85264
0.8849 High Similarity NPC47633
0.8841 High Similarity NPC87725
0.8841 High Similarity NPC263261
0.8841 High Similarity NPC277331
0.8841 High Similarity NPC100482
0.8832 High Similarity NPC236306
0.8832 High Similarity NPC260741
0.8832 High Similarity NPC232164
0.8832 High Similarity NPC70682
0.8832 High Similarity NPC473739
0.8832 High Similarity NPC32630
0.8824 High Similarity NPC126101
0.8819 High Similarity NPC93398
0.8819 High Similarity NPC160196
0.8819 High Similarity NPC258979
0.8819 High Similarity NPC8283
0.8815 High Similarity NPC131950
0.8806 High Similarity NPC472798
0.8794 High Similarity NPC233980
0.8786 High Similarity NPC63879
0.8786 High Similarity NPC473108
0.8777 High Similarity NPC107161
0.8777 High Similarity NPC472353
0.8768 High Similarity NPC213607
0.8768 High Similarity NPC182509
0.8768 High Similarity NPC174787
0.875 High Similarity NPC151224
0.8741 High Similarity NPC11060
0.874 High Similarity NPC59561
0.874 High Similarity NPC295259
0.874 High Similarity NPC172253
0.8731 High Similarity NPC472590
0.8731 High Similarity NPC160623
0.8723 High Similarity NPC43716
0.8723 High Similarity NPC101255
0.8723 High Similarity NPC475719
0.8722 High Similarity NPC472796
0.8722 High Similarity NPC96719
0.8722 High Similarity NPC472795
0.8722 High Similarity NPC472797
0.8722 High Similarity NPC222108
0.8712 High Similarity NPC46978
0.8705 High Similarity NPC247291
0.8705 High Similarity NPC108674
0.8705 High Similarity NPC265075
0.8705 High Similarity NPC35216
0.8702 High Similarity NPC167571
0.8702 High Similarity NPC278552
0.8702 High Similarity NPC207179
0.8699 High Similarity NPC188578
0.8699 High Similarity NPC80918
0.8699 High Similarity NPC159922
0.8696 High Similarity NPC144512
0.8696 High Similarity NPC471388
0.8696 High Similarity NPC137262
0.8696 High Similarity NPC35501
0.8696 High Similarity NPC37428
0.8696 High Similarity NPC47040
0.8696 High Similarity NPC278600
0.8692 High Similarity NPC474160
0.8686 High Similarity NPC265433
0.8686 High Similarity NPC234952
0.8686 High Similarity NPC230734
0.8686 High Similarity NPC470802
0.8686 High Similarity NPC227503
0.8686 High Similarity NPC270456
0.8686 High Similarity NPC248727
0.8686 High Similarity NPC474639
0.8686 High Similarity NPC472800
0.8686 High Similarity NPC173660
0.8686 High Similarity NPC78047
0.8686 High Similarity NPC162659
0.8686 High Similarity NPC327735
0.8682 High Similarity NPC476633
0.8671 High Similarity NPC227516
0.8671 High Similarity NPC20757
0.8662 High Similarity NPC260397
0.8662 High Similarity NPC14468
0.8661 High Similarity NPC74821
0.8661 High Similarity NPC131118
0.8647 High Similarity NPC211179

  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 NPC225696 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
0.938 High Similarity NPD4907 Clinical (unspecified phase)
0.9225 High Similarity NPD4908 Phase 1
0.8976 High Similarity NPD1610 Phase 2
0.8661 High Similarity NPD1548 Phase 1
0.8582 High Similarity NPD4625 Phase 3
0.8571 High Similarity NPD2861 Phase 2
0.8467 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD5124 Phase 1
0.8409 Intermediate Similarity NPD4749 Approved
0.8394 Intermediate Similarity NPD1613 Approved
0.8394 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8382 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8162 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8082 Intermediate Similarity NPD7212 Phase 2
0.8082 Intermediate Similarity NPD7213 Phase 3
0.8043 Intermediate Similarity NPD3027 Phase 3
0.8027 Intermediate Similarity NPD7447 Phase 1
0.8027 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7466 Approved
0.7931 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD4380 Phase 2
0.7857 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD422 Phase 1
0.7843 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5588 Approved
0.777 Intermediate Similarity NPD5058 Phase 3
0.7755 Intermediate Similarity NPD3750 Approved
0.7746 Intermediate Similarity NPD4060 Phase 1
0.774 Intermediate Similarity NPD1549 Phase 2
0.7737 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD6671 Approved
0.7724 Intermediate Similarity NPD6100 Approved
0.7724 Intermediate Similarity NPD6099 Approved
0.7708 Intermediate Similarity NPD4538 Approved
0.7708 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD4536 Approved
0.7698 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD8651 Approved
0.7681 Intermediate Similarity NPD6696 Suspended
0.7655 Intermediate Similarity NPD7033 Discontinued
0.7635 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD7768 Phase 2
0.7603 Intermediate Similarity NPD2796 Approved
0.7597 Intermediate Similarity NPD7411 Suspended
0.7595 Intermediate Similarity NPD5494 Approved
0.7591 Intermediate Similarity NPD1091 Approved
0.758 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD7075 Discontinued
0.7568 Intermediate Similarity NPD1652 Phase 2
0.7551 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD6002 Phase 3
0.7551 Intermediate Similarity NPD6005 Phase 3
0.7551 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD6004 Phase 3
0.755 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD1934 Approved
0.7547 Intermediate Similarity NPD6959 Discontinued
0.7534 Intermediate Similarity NPD5960 Phase 3
0.7534 Intermediate Similarity NPD1510 Phase 2
0.7517 Intermediate Similarity NPD3892 Phase 2
0.75 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7819 Suspended
0.75 Intermediate Similarity NPD7229 Phase 3
0.75 Intermediate Similarity NPD2797 Approved
0.75 Intermediate Similarity NPD2424 Discontinued
0.7485 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD7097 Phase 1
0.745 Intermediate Similarity NPD6674 Discontinued
0.7448 Intermediate Similarity NPD6355 Discontinued
0.7442 Intermediate Similarity NPD968 Approved
0.7436 Intermediate Similarity NPD37 Approved
0.7421 Intermediate Similarity NPD6234 Discontinued
0.7415 Intermediate Similarity NPD3748 Approved
0.7407 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD4967 Phase 2
0.7405 Intermediate Similarity NPD4965 Approved
0.7405 Intermediate Similarity NPD4966 Approved
0.7405 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD940 Approved
0.7402 Intermediate Similarity NPD846 Approved
0.7379 Intermediate Similarity NPD2238 Phase 2
0.7378 Intermediate Similarity NPD5844 Phase 1
0.7368 Intermediate Similarity NPD7041 Phase 2
0.7368 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD3268 Approved
0.7358 Intermediate Similarity NPD3749 Approved
0.7357 Intermediate Similarity NPD6582 Phase 2
0.7357 Intermediate Similarity NPD6583 Phase 3
0.7357 Intermediate Similarity NPD5327 Phase 3
0.7349 Intermediate Similarity NPD6559 Discontinued
0.7333 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2800 Approved
0.7333 Intermediate Similarity NPD7157 Approved
0.7329 Intermediate Similarity NPD5735 Approved
0.7328 Intermediate Similarity NPD2684 Approved
0.7325 Intermediate Similarity NPD6801 Discontinued
0.7324 Intermediate Similarity NPD6584 Phase 3
0.7317 Intermediate Similarity NPD7228 Approved
0.7305 Intermediate Similarity NPD3225 Approved
0.7305 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD6666 Approved
0.7303 Intermediate Similarity NPD6667 Approved
0.7301 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD6166 Phase 2
0.7301 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7741 Discontinued
0.729 Intermediate Similarity NPD1653 Approved
0.7279 Intermediate Similarity NPD4097 Suspended
0.7279 Intermediate Similarity NPD7340 Approved
0.7279 Intermediate Similarity NPD6353 Approved
0.7278 Intermediate Similarity NPD2801 Approved
0.7278 Intermediate Similarity NPD8455 Phase 2
0.7273 Intermediate Similarity NPD3018 Phase 2
0.7273 Intermediate Similarity NPD4750 Phase 3
0.7267 Intermediate Similarity NPD7037 Approved
0.7261 Intermediate Similarity NPD6072 Discontinued
0.726 Intermediate Similarity NPD4140 Approved
0.726 Intermediate Similarity NPD1240 Approved
0.7255 Intermediate Similarity NPD1511 Approved
0.7252 Intermediate Similarity NPD290 Approved
0.7244 Intermediate Similarity NPD3020 Approved
0.7244 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD6798 Discontinued
0.7239 Intermediate Similarity NPD5535 Approved
0.7239 Intermediate Similarity NPD7843 Approved
0.723 Intermediate Similarity NPD2200 Suspended
0.7222 Intermediate Similarity NPD7199 Phase 2
0.7212 Intermediate Similarity NPD3818 Discontinued
0.7208 Intermediate Similarity NPD2532 Approved
0.7208 Intermediate Similarity NPD2533 Approved
0.7208 Intermediate Similarity NPD2534 Approved
0.7203 Intermediate Similarity NPD3691 Phase 2
0.7203 Intermediate Similarity NPD3690 Phase 2
0.7202 Intermediate Similarity NPD7549 Discontinued
0.72 Intermediate Similarity NPD5762 Approved
0.72 Intermediate Similarity NPD5763 Approved
0.72 Intermediate Similarity NPD7030 Discontinued
0.7194 Intermediate Similarity NPD5126 Approved
0.7194 Intermediate Similarity NPD5125 Phase 3
0.7188 Intermediate Similarity NPD3882 Suspended
0.7185 Intermediate Similarity NPD5283 Phase 1
0.7185 Intermediate Similarity NPD1398 Phase 1
0.7181 Intermediate Similarity NPD3846 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD6331 Phase 2
0.7171 Intermediate Similarity NPD4535 Phase 3
0.717 Intermediate Similarity NPD5929 Approved
0.7169 Intermediate Similarity NPD7054 Approved
0.7162 Intermediate Similarity NPD1607 Approved
0.7162 Intermediate Similarity NPD2157 Approved
0.7161 Intermediate Similarity NPD1512 Approved
0.7152 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD1551 Phase 2
0.7133 Intermediate Similarity NPD2935 Discontinued
0.7126 Intermediate Similarity NPD7074 Phase 3
0.7126 Intermediate Similarity NPD7472 Approved
0.7115 Intermediate Similarity NPD5403 Approved
0.7115 Intermediate Similarity NPD920 Approved
0.7114 Intermediate Similarity NPD7119 Phase 2
0.7113 Intermediate Similarity NPD2983 Phase 2
0.7113 Intermediate Similarity NPD2982 Phase 2
0.7086 Intermediate Similarity NPD4360 Phase 2
0.7086 Intermediate Similarity NPD4363 Phase 3
0.7083 Intermediate Similarity NPD6797 Phase 2
0.7083 Intermediate Similarity NPD4624 Approved
0.7075 Intermediate Similarity NPD6233 Phase 2
0.7071 Intermediate Similarity NPD4626 Approved
0.7071 Intermediate Similarity NPD2667 Approved
0.7071 Intermediate Similarity NPD6516 Phase 2
0.7071 Intermediate Similarity NPD5846 Approved
0.7071 Intermediate Similarity NPD2668 Approved
0.7067 Intermediate Similarity NPD2799 Discontinued
0.7067 Intermediate Similarity NPD4108 Discontinued
0.7059 Intermediate Similarity NPD4628 Phase 3
0.7055 Intermediate Similarity NPD7095 Approved
0.7054 Intermediate Similarity NPD1242 Phase 1
0.7042 Intermediate Similarity NPD2981 Phase 2
0.7042 Intermediate Similarity NPD2231 Phase 2
0.7042 Intermediate Similarity NPD2235 Phase 2
0.7042 Intermediate Similarity NPD1608 Approved
0.7042 Intermediate Similarity NPD2232 Approved
0.7042 Intermediate Similarity NPD2230 Approved
0.7042 Intermediate Similarity NPD2233 Approved
0.7041 Intermediate Similarity NPD7251 Discontinued
0.7032 Intermediate Similarity NPD6799 Approved
0.7027 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD3620 Phase 2
0.7021 Intermediate Similarity NPD3496 Discontinued
0.702 Intermediate Similarity NPD4477 Approved
0.702 Intermediate Similarity NPD4476 Approved
0.7019 Intermediate Similarity NPD3817 Phase 2
0.7019 Intermediate Similarity NPD5402 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