Structure

Physi-Chem Properties

Molecular Weight:  336.06
Volume:  323.411
LogP:  3.879
LogD:  3.309
LogS:  -6.86
# Rotatable Bonds:  2
TPSA:  71.04
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.516
Synthetic Accessibility Score:  2.579
Fsp3:  0.105
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.846
MDCK Permeability:  6.90783781465143e-05
Pgp-inhibitor:  0.167
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.43

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.02
Plasma Protein Binding (PPB):  94.76410675048828%
Volume Distribution (VD):  0.536
Pgp-substrate:  5.376017093658447%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.476
CYP2C19-inhibitor:  0.971
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.815
CYP2C9-substrate:  0.929
CYP2D6-inhibitor:  0.924
CYP2D6-substrate:  0.924
CYP3A4-inhibitor:  0.937
CYP3A4-substrate:  0.154

ADMET: Excretion

Clearance (CL):  11.336
Half-life (T1/2):  0.25

ADMET: Toxicity

hERG Blockers:  0.163
Human Hepatotoxicity (H-HT):  0.373
Drug-inuced Liver Injury (DILI):  0.951
AMES Toxicity:  0.06
Rat Oral Acute Toxicity:  0.16
Maximum Recommended Daily Dose:  0.917
Skin Sensitization:  0.153
Carcinogencity:  0.915
Eye Corrosion:  0.003
Eye Irritation:  0.308
Respiratory Toxicity:  0.43

Download Data

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

  Natural Product: NPC72455

Natural Product ID:  NPC72455
Common Name*:   Pachyrrizine
IUPAC Name:   6-(6-methoxy-1,3-benzodioxol-5-yl)furo[3,2-g]chromen-7-one
Synonyms:   Pachyrrizine
Standard InCHIKey:  PENSQRMNZZWMGV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H12O6/c1-21-16-8-18-17(23-9-24-18)6-12(16)13-5-11-4-10-2-3-22-14(10)7-15(11)25-19(13)20/h2-8H,9H2,1H3
SMILES:  COc1cc2OCOc2cc1c1cc2cc3ccoc3cc2oc1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479689
PubChem CID:   101277
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002819] Isoflav-3-enes
          • [CHEMONTID:0002820] Isoflav-3-enones

*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
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[12575075]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. stem n.a. PMID[12575075]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[15577255]
NPO24293 Neorautanenia mitis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16562843]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30188125]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota Tuber n.a. n.a. Database[FooDB]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13860 Solanum pubescens Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3392 Agastache rugosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24667 Pachyrrhizus erosus n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO19015 Begonia glabra Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24293 Neorautanenia mitis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3392 Agastache rugosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4333 Neorautanenia edulis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24667 Pachyrrhizus erosus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO19015 Begonia glabra Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13860 Solanum pubescens Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19015 Begonia glabra Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13860 Solanum pubescens Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24667 Pachyrrhizus erosus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4333 Neorautanenia edulis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24293 Neorautanenia mitis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19015 Begonia glabra Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13860 Solanum pubescens Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6470 Pachyrhizus erosus 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
NPT81 Cell Line A549 Homo sapiens IC50 > 5.0 ug.mL-1 PMID[454839]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 3.6 ug.mL-1 PMID[454839]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[454840]
NPT1226 Individual Protein Caspase-7 Homo sapiens Potency = 19952.6 nM PMID[454840]
NPT442 Individual Protein Ferritin light chain Equus caballus Potency = 50118.7 nM PMID[454840]
NPT277 Individual Protein Caspase-1 Homo sapiens Potency = 31622.8 nM PMID[454840]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 398.1 nM PMID[454840]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 15848.9 nM PMID[454840]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 50118.7 nM PMID[454840]
NPT2 Others Unspecified Potency = 31622.8 nM PMID[454840]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 121.35 % PMID[454841]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 139.6 % PMID[454841]
NPT2 Others Unspecified Potency n.a. 3162.3 nM PMID[454840]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[454842]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[454842]

☑ 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 NPC72455 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
0.9573 High Similarity NPC475964
0.9571 High Similarity NPC41853
0.9509 High Similarity NPC167479
0.9458 High Similarity NPC66804
0.9398 High Similarity NPC62640
0.9222 High Similarity NPC157522
0.9212 High Similarity NPC67450
0.9212 High Similarity NPC193881
0.9212 High Similarity NPC155264
0.9212 High Similarity NPC210460
0.9207 High Similarity NPC179464
0.9207 High Similarity NPC65846
0.9152 High Similarity NPC187923
0.9146 High Similarity NPC234536
0.9146 High Similarity NPC78612
0.9112 High Similarity NPC290304
0.9112 High Similarity NPC236327
0.9102 High Similarity NPC211309
0.903 High Similarity NPC273021
0.903 High Similarity NPC18284
0.9024 High Similarity NPC243509
0.9012 High Similarity NPC478238
0.9006 High Similarity NPC148497
0.9006 High Similarity NPC292460
0.9006 High Similarity NPC153008
0.8976 High Similarity NPC110257
0.897 High Similarity NPC216092
0.8963 High Similarity NPC33320
0.8957 High Similarity NPC261484
0.8951 High Similarity NPC478213
0.8951 High Similarity NPC244371
0.8951 High Similarity NPC186507
0.8941 High Similarity NPC233956
0.8935 High Similarity NPC144288
0.8909 High Similarity NPC131557
0.8902 High Similarity NPC76458
0.8902 High Similarity NPC258644
0.8902 High Similarity NPC310206
0.8902 High Similarity NPC82733
0.8896 High Similarity NPC233776
0.8889 High Similarity NPC68882
0.8855 High Similarity NPC264293
0.8855 High Similarity NPC34376
0.8848 High Similarity NPC15764
0.8848 High Similarity NPC113055
0.8841 High Similarity NPC155063
0.8837 High Similarity NPC107244
0.8834 High Similarity NPC57211
0.8827 High Similarity NPC279061
0.8824 High Similarity NPC190351
0.8824 High Similarity NPC281835
0.882 High Similarity NPC88445
0.881 High Similarity NPC179015
0.881 High Similarity NPC173149
0.8807 High Similarity NPC73703
0.8802 High Similarity NPC478199
0.8802 High Similarity NPC19948
0.8795 High Similarity NPC139876
0.8788 High Similarity NPC19097
0.8779 High Similarity NPC224165
0.8779 High Similarity NPC53917
0.8773 High Similarity NPC38361
0.8773 High Similarity NPC130015
0.8773 High Similarity NPC52623
0.8765 High Similarity NPC191104
0.8743 High Similarity NPC296540
0.8743 High Similarity NPC309335
0.8743 High Similarity NPC109238
0.8735 High Similarity NPC257914
0.8735 High Similarity NPC238405
0.8735 High Similarity NPC104459
0.8735 High Similarity NPC62518
0.8735 High Similarity NPC215375
0.872 High Similarity NPC279930
0.8696 High Similarity NPC304443
0.8696 High Similarity NPC74539
0.869 High Similarity NPC302741
0.8686 High Similarity NPC97523
0.8683 High Similarity NPC43971
0.8683 High Similarity NPC74749
0.8683 High Similarity NPC19554
0.8675 High Similarity NPC167595
0.8667 High Similarity NPC3273
0.8667 High Similarity NPC278010
0.8667 High Similarity NPC250769
0.8667 High Similarity NPC284353
0.8667 High Similarity NPC295608
0.8663 High Similarity NPC223375
0.8663 High Similarity NPC475825
0.865 High Similarity NPC135303
0.865 High Similarity NPC148423
0.865 High Similarity NPC474975
0.8631 High Similarity NPC94155
0.8631 High Similarity NPC260640
0.8631 High Similarity NPC295009
0.8629 High Similarity NPC183843
0.8614 High Similarity NPC261090
0.8614 High Similarity NPC45131
0.8614 High Similarity NPC301897
0.8613 High Similarity NPC261471
0.8613 High Similarity NPC310794
0.8606 High Similarity NPC472408
0.8606 High Similarity NPC131725
0.8606 High Similarity NPC128961
0.8605 High Similarity NPC131866
0.8605 High Similarity NPC51404
0.8598 High Similarity NPC198615
0.8598 High Similarity NPC474663
0.8596 High Similarity NPC320789
0.8596 High Similarity NPC247973
0.8588 High Similarity NPC38914
0.858 High Similarity NPC125991
0.858 High Similarity NPC469575
0.858 High Similarity NPC205522
0.8571 High Similarity NPC298093
0.8571 High Similarity NPC224687
0.8571 High Similarity NPC225624
0.8571 High Similarity NPC285973
0.8571 High Similarity NPC78944
0.8571 High Similarity NPC246903
0.8571 High Similarity NPC169
0.8554 High Similarity NPC276059
0.8554 High Similarity NPC241774
0.8554 High Similarity NPC34725
0.8554 High Similarity NPC122623
0.8547 High Similarity NPC477165
0.8547 High Similarity NPC471287
0.8545 High Similarity NPC144162
0.8545 High Similarity NPC166201
0.8538 High Similarity NPC113093
0.8538 High Similarity NPC277480
0.8537 High Similarity NPC29056
0.8529 High Similarity NPC470178
0.8529 High Similarity NPC15819
0.8528 High Similarity NPC306788
0.8528 High Similarity NPC10304
0.8528 High Similarity NPC266743
0.8528 High Similarity NPC63256
0.8521 High Similarity NPC14822
0.8521 High Similarity NPC162668
0.8521 High Similarity NPC188486
0.8521 High Similarity NPC15212
0.8521 High Similarity NPC99968
0.8519 High Similarity NPC14958
0.8519 High Similarity NPC231013
0.8519 High Similarity NPC110639
0.8519 High Similarity NPC216314
0.8519 High Similarity NPC40818
0.8519 High Similarity NPC215932
0.8519 High Similarity NPC120924
0.8519 High Similarity NPC106461
0.8519 High Similarity NPC195919
0.8514 High Similarity NPC156635
0.8514 High Similarity NPC325176
0.8514 High Similarity NPC164384
0.8512 High Similarity NPC250076
0.8512 High Similarity NPC16935
0.8512 High Similarity NPC125713
0.8512 High Similarity NPC196879
0.8512 High Similarity NPC50430
0.8503 High Similarity NPC180340
0.8503 High Similarity NPC257277
0.8503 High Similarity NPC470625
0.8497 Intermediate Similarity NPC78830
0.8497 Intermediate Similarity NPC218533
0.8494 Intermediate Similarity NPC41719
0.8488 Intermediate Similarity NPC86477
0.8488 Intermediate Similarity NPC241820
0.8488 Intermediate Similarity NPC135345
0.8488 Intermediate Similarity NPC471288
0.8485 Intermediate Similarity NPC472407
0.8485 Intermediate Similarity NPC98028
0.848 Intermediate Similarity NPC475369
0.848 Intermediate Similarity NPC37183
0.848 Intermediate Similarity NPC29411
0.8476 Intermediate Similarity NPC474648
0.8476 Intermediate Similarity NPC238366
0.8471 Intermediate Similarity NPC81679
0.8471 Intermediate Similarity NPC414831
0.8471 Intermediate Similarity NPC61141
0.8471 Intermediate Similarity NPC108767
0.8471 Intermediate Similarity NPC312056
0.8471 Intermediate Similarity NPC84515
0.8466 Intermediate Similarity NPC67302
0.8466 Intermediate Similarity NPC85233
0.8466 Intermediate Similarity NPC198427
0.8462 Intermediate Similarity NPC303210
0.8462 Intermediate Similarity NPC477164
0.8462 Intermediate Similarity NPC95472
0.8462 Intermediate Similarity NPC269906
0.8462 Intermediate Similarity NPC239270
0.8462 Intermediate Similarity NPC49009
0.8457 Intermediate Similarity NPC136278
0.8457 Intermediate Similarity NPC296575
0.8457 Intermediate Similarity NPC472607
0.8457 Intermediate Similarity NPC471590
0.8457 Intermediate Similarity NPC208584
0.8453 Intermediate Similarity NPC60848
0.8452 Intermediate Similarity NPC476981
0.8452 Intermediate Similarity NPC269495

  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 NPC72455 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
0.8963 High Similarity NPD919 Approved
0.8855 High Similarity NPD1247 Approved
0.8696 High Similarity NPD920 Approved
0.8571 High Similarity NPD5494 Approved
0.8571 High Similarity NPD642 Clinical (unspecified phase)
0.8447 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.84 Intermediate Similarity NPD6559 Discontinued
0.8382 Intermediate Similarity NPD3818 Discontinued
0.8354 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD1243 Approved
0.8225 Intermediate Similarity NPD3817 Phase 2
0.8166 Intermediate Similarity NPD2801 Approved
0.8146 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD5844 Phase 1
0.8103 Intermediate Similarity NPD3926 Phase 2
0.8 Intermediate Similarity NPD1934 Approved
0.7965 Intermediate Similarity NPD3882 Suspended
0.7953 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD6232 Discontinued
0.7921 Intermediate Similarity NPD7054 Approved
0.791 Intermediate Similarity NPD7473 Discontinued
0.7877 Intermediate Similarity NPD7074 Phase 3
0.7877 Intermediate Similarity NPD7472 Approved
0.7853 Intermediate Similarity NPD2796 Approved
0.7849 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD7819 Suspended
0.7816 Intermediate Similarity NPD3749 Approved
0.7816 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6801 Discontinued
0.7784 Intermediate Similarity NPD7199 Phase 2
0.7759 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7747 Intermediate Similarity NPD7808 Phase 3
0.7738 Intermediate Similarity NPD1511 Approved
0.7738 Intermediate Similarity NPD6799 Approved
0.7738 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD6797 Phase 2
0.7733 Intermediate Similarity NPD7411 Suspended
0.7716 Intermediate Similarity NPD1933 Approved
0.7714 Intermediate Similarity NPD7075 Discontinued
0.7701 Intermediate Similarity NPD5402 Approved
0.7697 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7251 Discontinued
0.7692 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD4965 Approved
0.7657 Intermediate Similarity NPD4966 Approved
0.7657 Intermediate Similarity NPD4967 Phase 2
0.7654 Intermediate Similarity NPD6166 Phase 2
0.7654 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1512 Approved
0.7624 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD6599 Discontinued
0.7572 Intermediate Similarity NPD4380 Phase 2
0.7571 Intermediate Similarity NPD6234 Discontinued
0.7543 Intermediate Similarity NPD1465 Phase 2
0.7486 Intermediate Similarity NPD37 Approved
0.7485 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD3748 Approved
0.747 Intermediate Similarity NPD1510 Phase 2
0.7459 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD7768 Phase 2
0.744 Intermediate Similarity NPD1549 Phase 2
0.7425 Intermediate Similarity NPD2935 Discontinued
0.7396 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD447 Suspended
0.7384 Intermediate Similarity NPD2534 Approved
0.7384 Intermediate Similarity NPD5401 Approved
0.7384 Intermediate Similarity NPD2533 Approved
0.7384 Intermediate Similarity NPD2532 Approved
0.7381 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD1653 Approved
0.7353 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1551 Phase 2
0.7317 Intermediate Similarity NPD2313 Discontinued
0.7314 Intermediate Similarity NPD3226 Approved
0.7303 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD8434 Phase 2
0.7299 Intermediate Similarity NPD5403 Approved
0.7293 Intermediate Similarity NPD6959 Discontinued
0.7289 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7228 Approved
0.7283 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2344 Approved
0.7259 Intermediate Similarity NPD5005 Approved
0.7259 Intermediate Similarity NPD5006 Approved
0.7251 Intermediate Similarity NPD3750 Approved
0.7235 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD1240 Approved
0.7213 Intermediate Similarity NPD5242 Approved
0.7195 Intermediate Similarity NPD6832 Phase 2
0.7193 Intermediate Similarity NPD2800 Approved
0.7189 Intermediate Similarity NPD3751 Discontinued
0.7176 Intermediate Similarity NPD2346 Discontinued
0.716 Intermediate Similarity NPD2799 Discontinued
0.7158 Intermediate Similarity NPD7229 Phase 3
0.7143 Intermediate Similarity NPD1607 Approved
0.7143 Intermediate Similarity NPD4420 Approved
0.7143 Intermediate Similarity NPD8313 Approved
0.7143 Intermediate Similarity NPD8312 Approved
0.7128 Intermediate Similarity NPD7240 Approved
0.711 Intermediate Similarity NPD2309 Approved
0.7108 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD230 Phase 1
0.7074 Intermediate Similarity NPD5953 Discontinued
0.7065 Intermediate Similarity NPD3787 Discontinued
0.7065 Intermediate Similarity NPD6808 Phase 2
0.7059 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7783 Phase 2
0.7059 Intermediate Similarity NPD7286 Phase 2
0.7044 Intermediate Similarity NPD8151 Discontinued
0.7039 Intermediate Similarity NPD6386 Approved
0.7039 Intermediate Similarity NPD6385 Approved
0.7037 Intermediate Similarity NPD7685 Pre-registration
0.7024 Intermediate Similarity NPD943 Approved
0.7022 Intermediate Similarity NPD7458 Discontinued
0.7017 Intermediate Similarity NPD5353 Approved
0.6977 Remote Similarity NPD1471 Phase 3
0.6965 Remote Similarity NPD7435 Discontinued
0.6961 Remote Similarity NPD8455 Phase 2
0.6959 Remote Similarity NPD4287 Approved
0.6954 Remote Similarity NPD4628 Phase 3
0.6949 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4307 Phase 2
0.6911 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6909 Remote Similarity NPD3267 Approved
0.6909 Remote Similarity NPD3266 Approved
0.6906 Remote Similarity NPD6280 Approved
0.6906 Remote Similarity NPD6279 Approved
0.69 Remote Similarity NPD6780 Approved
0.69 Remote Similarity NPD6781 Approved
0.69 Remote Similarity NPD6782 Approved
0.69 Remote Similarity NPD7501 Clinical (unspecified phase)
0.69 Remote Similarity NPD6776 Approved
0.69 Remote Similarity NPD6778 Approved
0.69 Remote Similarity NPD6779 Approved
0.69 Remote Similarity NPD6777 Approved
0.6882 Remote Similarity NPD5710 Approved
0.6882 Remote Similarity NPD5711 Approved
0.6871 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6867 Remote Similarity NPD1019 Discontinued
0.6867 Remote Similarity NPD2798 Approved
0.6847 Remote Similarity NPD7870 Phase 2
0.6847 Remote Similarity NPD7871 Phase 2
0.6839 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6834 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6823 Remote Similarity NPD7549 Discontinued
0.6809 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6809 Remote Similarity NPD2403 Approved
0.6807 Remote Similarity NPD1203 Approved
0.6805 Remote Similarity NPD1296 Phase 2
0.6798 Remote Similarity NPD7698 Approved
0.6798 Remote Similarity NPD7696 Phase 3
0.6798 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7697 Approved
0.678 Remote Similarity NPD7584 Approved
0.6776 Remote Similarity NPD5761 Phase 2
0.6776 Remote Similarity NPD5760 Phase 2
0.6763 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6763 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6763 Remote Similarity NPD7033 Discontinued
0.6763 Remote Similarity NPD4308 Phase 3
0.6763 Remote Similarity NPD7874 Approved
0.6758 Remote Similarity NPD5889 Approved
0.6758 Remote Similarity NPD5890 Approved
0.6748 Remote Similarity NPD17 Approved
0.6742 Remote Similarity NPD4846 Phase 2
0.674 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6738 Remote Similarity NPD8127 Discontinued
0.6727 Remote Similarity NPD9717 Approved
0.6726 Remote Similarity NPD9494 Approved
0.6725 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6725 Remote Similarity NPD1613 Approved
0.6723 Remote Similarity NPD6190 Approved
0.6716 Remote Similarity NPD7680 Approved
0.6706 Remote Similarity NPD3268 Approved
0.6705 Remote Similarity NPD2654 Approved
0.6703 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6699 Remote Similarity NPD7583 Approved
0.6686 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6683 Remote Similarity NPD8285 Discontinued
0.6667 Remote Similarity NPD6823 Phase 2
0.6667 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6233 Phase 2
0.6667 Remote Similarity NPD7701 Phase 2
0.6667 Remote Similarity NPD7585 Approved
0.6667 Remote Similarity NPD3705 Approved
0.6667 Remote Similarity NPD7615 Clinical (unspecified phase)
0.665 Remote Similarity NPD6535 Approved
0.665 Remote Similarity NPD6534 Approved
0.665 Remote Similarity NPD4107 Approved
0.6649 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6649 Remote Similarity NPD2163 Approved
0.6649 Remote Similarity NPD4288 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