Structure

Physi-Chem Properties

Molecular Weight:  390.18
Volume:  412.243
LogP:  6.757
LogD:  5.324
LogS:  -3.176
# Rotatable Bonds:  1
TPSA:  47.92
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.7
Synthetic Accessibility Score:  3.823
Fsp3:  0.36
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.06
MDCK Permeability:  1.871657332230825e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.064
20% Bioavailability (F20%):  0.786
30% Bioavailability (F30%):  0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.03
Plasma Protein Binding (PPB):  101.86436462402344%
Volume Distribution (VD):  1.383
Pgp-substrate:  0.9315727949142456%

ADMET: Metabolism

CYP1A2-inhibitor:  0.821
CYP1A2-substrate:  0.681
CYP2C19-inhibitor:  0.887
CYP2C19-substrate:  0.628
CYP2C9-inhibitor:  0.822
CYP2C9-substrate:  0.941
CYP2D6-inhibitor:  0.955
CYP2D6-substrate:  0.879
CYP3A4-inhibitor:  0.837
CYP3A4-substrate:  0.698

ADMET: Excretion

Clearance (CL):  2.228
Half-life (T1/2):  0.084

ADMET: Toxicity

hERG Blockers:  0.653
Human Hepatotoxicity (H-HT):  0.957
Drug-inuced Liver Injury (DILI):  0.193
AMES Toxicity:  0.057
Rat Oral Acute Toxicity:  0.885
Maximum Recommended Daily Dose:  0.922
Skin Sensitization:  0.854
Carcinogencity:  0.906
Eye Corrosion:  0.003
Eye Irritation:  0.111
Respiratory Toxicity:  0.884

Download Data

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

  Natural Product: NPC77196

Natural Product ID:  NPC77196
Common Name*:   Hispaglabridin B
IUPAC Name:   6-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]-2,2-dimethylchromen-5-ol
Synonyms:  
Standard InCHIKey:  CJUFYKORDZSOLF-INIZCTEOSA-N
Standard InCHI:  InChI=1S/C25H26O4/c1-24(2)11-9-18-20(28-24)8-6-17(22(18)26)16-13-15-5-7-21-19(23(15)27-14-16)10-12-25(3,4)29-21/h5-12,16,26H,13-14H2,1-4H3/t16-/m0/s1
SMILES:  Oc1c(ccc2c1C=CC(O2)(C)C)[C@@H]1COc2c(C1)ccc1c2C=CC(O1)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464582
PubChem CID:   15228661
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0003530] Pyranoisoflavonoids

*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
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
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]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO29384.1 Glycyrrhiza glabra var. typica Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis 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]
NPO29384.1 Glycyrrhiza glabra var. typica Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10026 Mitracarpus scaber Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7786 Lentinus tigrinus Species Lentinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra 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
NPT493 Individual Protein Neuraminidase Influenza A virus Ratio IC50 = 10.0 n.a. PMID[451278]
NPT616 Cell Line MDCK Canis lupus familiaris CC50 = 39200.0 nM PMID[451278]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 2850.0 nM PMID[451278]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 1200.0 nM PMID[451278]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 2310.0 nM PMID[451278]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 1110.0 nM PMID[451278]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 42.0 % PMID[451279]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 1.1 n.a. PMID[451279]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 10.5 % PMID[451279]
NPT65 Cell Line HepG2 Homo sapiens Inhibition = 45.9 % PMID[451279]
NPT81 Cell Line A549 Homo sapiens Inhibition = 34.3 % PMID[451279]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 38.3 % PMID[451279]
NPT660 Cell Line SW480 Homo sapiens Inhibition = 47.9 % PMID[451279]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 6.25 ug.mL-1 PMID[451277]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 3.12 ug.mL-1 PMID[451277]
NPT2 Others Unspecified IC50 = 170.0 nM PMID[451278]
NPT2 Others Unspecified IC50 = 4230.0 nM PMID[451278]
NPT35 Others n.a. Activity = 15.1 % PMID[451278]
NPT35 Others n.a. Activity = 0.05 % PMID[451278]
NPT742 Organism Influenza A virus Influenza A virus Inhibition = 31.2 % PMID[451278]
NPT742 Organism Influenza A virus Influenza A virus Inhibition = 48.4 % PMID[451278]
NPT741 Individual Protein Tyrosinase Homo sapiens Inhibition = 0.0 % PMID[451279]
NPT2 Others Unspecified Inhibition = 0.0 % PMID[451279]

☑ 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 NPC77196 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
0.9841 High Similarity NPC164804
0.9841 High Similarity NPC211413
0.9841 High Similarity NPC68205
0.9841 High Similarity NPC293203
0.9841 High Similarity NPC244888
0.9841 High Similarity NPC118683
0.9683 High Similarity NPC134360
0.9612 High Similarity NPC223008
0.9612 High Similarity NPC97834
0.9612 High Similarity NPC225696
0.9612 High Similarity NPC115335
0.9612 High Similarity NPC296915
0.9612 High Similarity NPC198154
0.9603 High Similarity NPC38664
0.9603 High Similarity NPC53986
0.9535 High Similarity NPC92805
0.9528 High Similarity NPC93962
0.9457 High Similarity NPC13005
0.9444 High Similarity NPC50315
0.9444 High Similarity NPC26879
0.9444 High Similarity NPC230479
0.9444 High Similarity NPC283049
0.938 High Similarity NPC129784
0.938 High Similarity NPC196765
0.938 High Similarity NPC300875
0.938 High Similarity NPC164574
0.938 High Similarity NPC207892
0.938 High Similarity NPC228369
0.938 High Similarity NPC236014
0.938 High Similarity NPC268917
0.938 High Similarity NPC150011
0.938 High Similarity NPC17343
0.938 High Similarity NPC129106
0.938 High Similarity NPC12875
0.938 High Similarity NPC280653
0.938 High Similarity NPC206224
0.938 High Similarity NPC476166
0.938 High Similarity NPC118114
0.937 High Similarity NPC149796
0.9318 High Similarity NPC262585
0.9318 High Similarity NPC20829
0.9318 High Similarity NPC18189
0.9302 High Similarity NPC27187
0.9302 High Similarity NPC470225
0.9297 High Similarity NPC274717
0.9237 High Similarity NPC85435
0.9231 High Similarity NPC181497
0.9231 High Similarity NPC271945
0.9213 High Similarity NPC102540
0.9213 High Similarity NPC188022
0.9213 High Similarity NPC17809
0.9213 High Similarity NPC285040
0.9213 High Similarity NPC103420
0.9185 High Similarity NPC5155
0.9179 High Similarity NPC475836
0.9173 High Similarity NPC471522
0.9167 High Similarity NPC124085
0.9167 High Similarity NPC473107
0.9167 High Similarity NPC117048
0.9147 High Similarity NPC47283
0.9147 High Similarity NPC39064
0.9141 High Similarity NPC276212
0.9134 High Similarity NPC246648
0.9134 High Similarity NPC86502
0.9134 High Similarity NPC134195
0.9134 High Similarity NPC106914
0.9134 High Similarity NPC197351
0.9118 High Similarity NPC59841
0.9118 High Similarity NPC204347
0.9118 High Similarity NPC475891
0.9118 High Similarity NPC2613
0.9104 High Similarity NPC474687
0.9104 High Similarity NPC470307
0.9104 High Similarity NPC470308
0.9084 High Similarity NPC162801
0.9084 High Similarity NPC103799
0.9055 High Similarity NPC38761
0.9055 High Similarity NPC76465
0.9048 High Similarity NPC54972
0.9048 High Similarity NPC193364
0.903 High Similarity NPC3049
0.9023 High Similarity NPC476617
0.9023 High Similarity NPC476615
0.9023 High Similarity NPC476616
0.9 High Similarity NPC87224
0.9 High Similarity NPC222572
0.8992 High Similarity NPC262573
0.8992 High Similarity NPC471215
0.8986 High Similarity NPC475492
0.8984 High Similarity NPC159132
0.8976 High Similarity NPC100099
0.8976 High Similarity NPC36016
0.8923 High Similarity NPC473134
0.8921 High Similarity NPC469557
0.8905 High Similarity NPC100482
0.8905 High Similarity NPC277331
0.8897 High Similarity NPC35501
0.8897 High Similarity NPC144512
0.8897 High Similarity NPC137262
0.8897 High Similarity NPC37428
0.8897 High Similarity NPC260741
0.8897 High Similarity NPC47040
0.8897 High Similarity NPC278600
0.8897 High Similarity NPC70682
0.8881 High Similarity NPC131950
0.8837 High Similarity NPC294156
0.8837 High Similarity NPC256015
0.8815 High Similarity NPC473413
0.8815 High Similarity NPC125579
0.881 High Similarity NPC295259
0.8797 High Similarity NPC472590
0.8797 High Similarity NPC160623
0.8794 High Similarity NPC21776
0.8794 High Similarity NPC16269
0.8788 High Similarity NPC96719
0.8788 High Similarity NPC222108
0.8786 High Similarity NPC43716
0.8786 High Similarity NPC101255
0.8786 High Similarity NPC475719
0.8779 High Similarity NPC46978
0.8769 High Similarity NPC81641
0.8768 High Similarity NPC35216
0.876 High Similarity NPC474160
0.8759 High Similarity NPC32630
0.875 High Similarity NPC162659
0.875 High Similarity NPC173660
0.875 High Similarity NPC265433
0.875 High Similarity NPC248727
0.875 High Similarity NPC476633
0.875 High Similarity NPC270456
0.874 High Similarity NPC8283
0.874 High Similarity NPC93398
0.874 High Similarity NPC258979
0.8731 High Similarity NPC472798
0.873 High Similarity NPC131118
0.873 High Similarity NPC74821
0.8723 High Similarity NPC233980
0.8714 High Similarity NPC473108
0.8696 High Similarity NPC259519
0.8692 High Similarity NPC270030
0.8682 High Similarity NPC150026
0.8676 High Similarity NPC151224
0.8676 High Similarity NPC195022
0.8667 High Similarity NPC469955
0.8667 High Similarity NPC469952
0.8667 High Similarity NPC215037
0.8667 High Similarity NPC469610
0.8667 High Similarity NPC11060
0.8661 High Similarity NPC172253
0.8661 High Similarity NPC59561
0.8647 High Similarity NPC472795
0.8647 High Similarity NPC16577
0.8647 High Similarity NPC472797
0.8647 High Similarity NPC472796
0.8633 High Similarity NPC265075
0.863 High Similarity NPC188578
0.863 High Similarity NPC80918
0.8626 High Similarity NPC278552
0.8626 High Similarity NPC207179
0.8626 High Similarity NPC167571
0.8623 High Similarity NPC245207
0.8623 High Similarity NPC319647
0.8623 High Similarity NPC25966
0.8623 High Similarity NPC127218
0.8623 High Similarity NPC471388
0.8613 High Similarity NPC234952
0.8613 High Similarity NPC230734
0.8613 High Similarity NPC470802
0.8613 High Similarity NPC474639
0.8613 High Similarity NPC141717
0.8613 High Similarity NPC472800
0.8613 High Similarity NPC227503
0.8605 High Similarity NPC97432
0.8605 High Similarity NPC190454
0.8603 High Similarity NPC317380
0.8593 High Similarity NPC469611
0.8592 High Similarity NPC102280
0.8592 High Similarity NPC248053
0.8592 High Similarity NPC155564
0.8582 High Similarity NPC12641
0.8582 High Similarity NPC280092
0.8582 High Similarity NPC45257
0.8582 High Similarity NPC32463
0.8582 High Similarity NPC93323
0.8582 High Similarity NPC254000
0.8571 High Similarity NPC229147
0.8571 High Similarity NPC38604
0.8571 High Similarity NPC211179
0.8571 High Similarity NPC54507
0.8571 High Similarity NPC85292
0.8561 High Similarity NPC27495
0.8561 High Similarity NPC309124
0.8561 High Similarity NPC184797
0.8552 High Similarity NPC471115
0.8552 High Similarity NPC29777
0.8551 High Similarity NPC477938
0.8551 High Similarity NPC211549
0.8551 High Similarity NPC276490
0.8542 High Similarity NPC211561
0.854 High Similarity NPC112246

  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 NPC77196 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
0.9453 High Similarity NPD4907 Clinical (unspecified phase)
0.9297 High Similarity NPD4908 Phase 1
0.9048 High Similarity NPD1610 Phase 2
0.873 High Similarity NPD1548 Phase 1
0.8647 High Similarity NPD4625 Phase 3
0.8529 High Similarity NPD5124 Phase 1
0.8529 High Similarity NPD5123 Clinical (unspecified phase)
0.8473 Intermediate Similarity NPD4749 Approved
0.8444 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8358 Intermediate Similarity NPD2861 Phase 2
0.8321 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD1613 Approved
0.8296 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8222 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8207 Intermediate Similarity NPD7447 Phase 1
0.8138 Intermediate Similarity NPD7212 Phase 2
0.8138 Intermediate Similarity NPD7213 Phase 3
0.8082 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7971 Intermediate Similarity NPD3027 Phase 3
0.7961 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD422 Phase 1
0.7862 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD4380 Phase 2
0.7808 Intermediate Similarity NPD7466 Approved
0.7808 Intermediate Similarity NPD3750 Approved
0.7801 Intermediate Similarity NPD4060 Phase 1
0.7794 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD6671 Approved
0.7778 Intermediate Similarity NPD6100 Approved
0.7778 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6099 Approved
0.7763 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7737 Intermediate Similarity NPD8651 Approved
0.7724 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD7768 Phase 2
0.7671 Intermediate Similarity NPD1549 Phase 2
0.7647 Intermediate Similarity NPD7411 Suspended
0.7639 Intermediate Similarity NPD4538 Approved
0.7639 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD4536 Approved
0.7595 Intermediate Similarity NPD6959 Discontinued
0.7586 Intermediate Similarity NPD1510 Phase 2
0.7562 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD2797 Approved
0.7548 Intermediate Similarity NPD7819 Suspended
0.7534 Intermediate Similarity NPD2796 Approved
0.7531 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD1091 Approved
0.7517 Intermediate Similarity NPD7097 Phase 1
0.7516 Intermediate Similarity NPD7075 Discontinued
0.7516 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD968 Approved
0.75 Intermediate Similarity NPD1652 Phase 2
0.7484 Intermediate Similarity NPD1934 Approved
0.7482 Intermediate Similarity NPD3225 Approved
0.7482 Intermediate Similarity NPD6696 Suspended
0.7467 Intermediate Similarity NPD5058 Phase 3
0.7466 Intermediate Similarity NPD7033 Discontinued
0.7466 Intermediate Similarity NPD5588 Approved
0.7466 Intermediate Similarity NPD5960 Phase 3
0.7466 Intermediate Similarity NPD3748 Approved
0.746 Intermediate Similarity NPD940 Approved
0.746 Intermediate Similarity NPD846 Approved
0.745 Intermediate Similarity NPD3892 Phase 2
0.7436 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD3268 Approved
0.741 Intermediate Similarity NPD6583 Phase 3
0.741 Intermediate Similarity NPD6582 Phase 2
0.7388 Intermediate Similarity NPD7157 Approved
0.7385 Intermediate Similarity NPD2684 Approved
0.7383 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD6674 Discontinued
0.7376 Intermediate Similarity NPD6584 Phase 3
0.7368 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD6666 Approved
0.7351 Intermediate Similarity NPD6667 Approved
0.7349 Intermediate Similarity NPD7549 Discontinued
0.7346 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD6166 Phase 2
0.7346 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7340 Approved
0.7329 Intermediate Similarity NPD7229 Phase 3
0.7328 Intermediate Similarity NPD4750 Phase 3
0.7325 Intermediate Similarity NPD8455 Phase 2
0.7325 Intermediate Similarity NPD2801 Approved
0.7324 Intermediate Similarity NPD3018 Phase 2
0.7317 Intermediate Similarity NPD5844 Phase 1
0.7315 Intermediate Similarity NPD2424 Discontinued
0.7312 Intermediate Similarity NPD5494 Approved
0.731 Intermediate Similarity NPD2238 Phase 2
0.731 Intermediate Similarity NPD1240 Approved
0.7308 Intermediate Similarity NPD6072 Discontinued
0.7303 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD7041 Phase 2
0.7303 Intermediate Similarity NPD1511 Approved
0.7302 Intermediate Similarity NPD3020 Approved
0.7293 Intermediate Similarity NPD7843 Approved
0.7293 Intermediate Similarity NPD5535 Approved
0.729 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD2200 Suspended
0.7261 Intermediate Similarity NPD6801 Discontinued
0.726 Intermediate Similarity NPD6355 Discontinued
0.7254 Intermediate Similarity NPD3690 Phase 2
0.7254 Intermediate Similarity NPD3691 Phase 2
0.7248 Intermediate Similarity NPD6005 Phase 3
0.7248 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD6004 Phase 3
0.7248 Intermediate Similarity NPD6002 Phase 3
0.7248 Intermediate Similarity NPD7030 Discontinued
0.7248 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD1398 Phase 1
0.7239 Intermediate Similarity NPD5283 Phase 1
0.7226 Intermediate Similarity NPD1653 Approved
0.7212 Intermediate Similarity NPD7054 Approved
0.7211 Intermediate Similarity NPD1607 Approved
0.7211 Intermediate Similarity NPD4097 Suspended
0.7208 Intermediate Similarity NPD1512 Approved
0.72 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD3749 Approved
0.7181 Intermediate Similarity NPD2935 Discontinued
0.7181 Intermediate Similarity NPD1551 Phase 2
0.7176 Intermediate Similarity NPD290 Approved
0.7172 Intermediate Similarity NPD6798 Discontinued
0.7169 Intermediate Similarity NPD7074 Phase 3
0.7169 Intermediate Similarity NPD7472 Approved
0.7163 Intermediate Similarity NPD2982 Phase 2
0.7163 Intermediate Similarity NPD5327 Phase 3
0.7163 Intermediate Similarity NPD2983 Phase 2
0.7161 Intermediate Similarity NPD5403 Approved
0.7152 Intermediate Similarity NPD7228 Approved
0.7152 Intermediate Similarity NPD37 Approved
0.7152 Intermediate Similarity NPD2800 Approved
0.7143 Intermediate Similarity NPD5735 Approved
0.7143 Intermediate Similarity NPD6234 Discontinued
0.7143 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6797 Phase 2
0.7125 Intermediate Similarity NPD4965 Approved
0.7125 Intermediate Similarity NPD4966 Approved
0.7125 Intermediate Similarity NPD4967 Phase 2
0.7122 Intermediate Similarity NPD5846 Approved
0.7122 Intermediate Similarity NPD4626 Approved
0.7122 Intermediate Similarity NPD6516 Phase 2
0.7122 Intermediate Similarity NPD2668 Approved
0.7122 Intermediate Similarity NPD2667 Approved
0.7114 Intermediate Similarity NPD4108 Discontinued
0.7114 Intermediate Similarity NPD2799 Discontinued
0.7109 Intermediate Similarity NPD1242 Phase 1
0.7107 Intermediate Similarity NPD5929 Approved
0.7105 Intermediate Similarity NPD4535 Phase 3
0.7103 Intermediate Similarity NPD7095 Approved
0.7101 Intermediate Similarity NPD7741 Discontinued
0.7095 Intermediate Similarity NPD6353 Approved
0.7092 Intermediate Similarity NPD1608 Approved
0.7092 Intermediate Similarity NPD2233 Approved
0.7092 Intermediate Similarity NPD2981 Phase 2
0.7092 Intermediate Similarity NPD2232 Approved
0.7092 Intermediate Similarity NPD2230 Approved
0.7086 Intermediate Similarity NPD7037 Approved
0.7083 Intermediate Similarity NPD7251 Discontinued
0.7083 Intermediate Similarity NPD6559 Discontinued
0.7078 Intermediate Similarity NPD6799 Approved
0.7075 Intermediate Similarity NPD4140 Approved
0.7071 Intermediate Similarity NPD3496 Discontinued
0.707 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD5451 Approved
0.7067 Intermediate Similarity NPD4476 Approved
0.7067 Intermediate Similarity NPD4477 Approved
0.7063 Intermediate Similarity NPD5402 Approved
0.7063 Intermediate Similarity NPD3267 Approved
0.7063 Intermediate Similarity NPD3266 Approved
0.7063 Intermediate Similarity NPD2859 Approved
0.7063 Intermediate Similarity NPD3817 Phase 2
0.7063 Intermediate Similarity NPD2860 Approved
0.7055 Intermediate Similarity NPD7199 Phase 2
0.705 Intermediate Similarity NPD3443 Approved
0.705 Intermediate Similarity NPD5691 Approved
0.705 Intermediate Similarity NPD3445 Approved
0.705 Intermediate Similarity NPD3444 Approved
0.7047 Intermediate Similarity NPD7119 Phase 2
0.7041 Intermediate Similarity NPD7808 Phase 3
0.7037 Intermediate Similarity NPD821 Approved
0.7034 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD2533 Approved
0.7032 Intermediate Similarity NPD5401 Approved
0.7032 Intermediate Similarity NPD2532 Approved
0.7032 Intermediate Similarity NPD2534 Approved
0.7029 Intermediate Similarity NPD4360 Phase 2
0.7029 Intermediate Similarity NPD4363 Phase 3
0.7027 Intermediate Similarity NPD4340 Discontinued
0.7025 Intermediate Similarity NPD6599 Discontinued
0.7021 Intermediate Similarity NPD1611 Approved
0.702 Intermediate Similarity NPD5762 Approved
0.702 Intermediate Similarity NPD5763 Approved
0.7019 Intermediate Similarity NPD3882 Suspended

  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