Structure

Physi-Chem Properties

Molecular Weight:  272.0
Volume:  204.387
LogP:  -1.82
LogD:  -1.777
LogS:  0.099
# Rotatable Bonds:  4
TPSA:  146.79
# H-Bond Aceptor:  9
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.605
Synthetic Accessibility Score:  4.974
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.321
MDCK Permeability:  0.005781812127679586
Pgp-inhibitor:  0.0
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  1.0
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.368
Plasma Protein Binding (PPB):  21.360876083374023%
Volume Distribution (VD):  0.503
Pgp-substrate:  83.23877716064453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.146
CYP2C19-inhibitor:  0.053
CYP2C19-substrate:  0.029
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.36
CYP2D6-inhibitor:  0.033
CYP2D6-substrate:  0.045
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.016

ADMET: Excretion

Clearance (CL):  1.341
Half-life (T1/2):  0.254

ADMET: Toxicity

hERG Blockers:  0.024
Human Hepatotoxicity (H-HT):  0.629
Drug-inuced Liver Injury (DILI):  0.655
AMES Toxicity:  0.064
Rat Oral Acute Toxicity:  0.002
Maximum Recommended Daily Dose:  0.973
Skin Sensitization:  0.832
Carcinogencity:  0.069
Eye Corrosion:  0.963
Eye Irritation:  0.99
Respiratory Toxicity:  0.761

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC478721

Natural Product ID:  NPC478721
Common Name*:   XRASPMIURGNCCH-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  XRASPMIURGNCCH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C5H10N2O7P2/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14)
SMILES:  c1cn(CC(O)(P(=O)(O)O)P(=O)(O)O)cn1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   68740
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000419] Organic phosphonic acids and derivatives
        • [CHEMONTID:0000327] Bisphosphonates

*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
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. DOI[10.1078/0176-1617-00195]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[10757735]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[14735439]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. callus n.a. PMID[15715262]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[18220354]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[28445039]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota Roots n.a. n.a. PMID[30024167]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4391 Hypericum perforatum Species Hypericaceae 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
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens ED50 = 0.00007 mg.kg-1 PMID[12825934]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 0.2399 nM PMID[12825934]
NPT91 Cell Line KB Homo sapiens LD50 = 63.7 uM PMID[14695831]
NPT5931 Individual Protein Farnesyl pyrophosphate synthase Leishmania donovani IC50 = 110.0 nM PMID[14695831]
NPT5931 Individual Protein Farnesyl pyrophosphate synthase Leishmania donovani Ki = 11.0 nM PMID[15828834]
NPT859 Cell Line HFF Homo sapiens IC50 = 790.0 nM PMID[15857119]
NPT91 Cell Line KB Homo sapiens LD50 = 63.7 uM PMID[15857119]
NPT859 Cell Line HFF Homo sapiens IC50 = 7800.0 nM PMID[15857119]
NPT859 Cell Line HFF Homo sapiens IC50 = 8300.0 nM PMID[15857119]
NPT5932 Individual Protein Vacuolar-type proton translocating pyrophosphatase 1 Trypanosoma brucei IC50 = 226700.0 nM PMID[16162013]
NPT91 Cell Line KB Homo sapiens ED50 = 63.7 uM PMID[16162013]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 27700.0 nM PMID[16970405]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 11700.0 nM PMID[16970405]
NPT395 Cell Line SF-268 Homo sapiens IC50 = 14300.0 nM PMID[16970405]
NPT1495 Individual Protein Geranylgeranyl pyrophosphate synthetase Homo sapiens IC50 = 97000.0 nM PMID[17535895]
NPT1495 Individual Protein Geranylgeranyl pyrophosphate synthetase Homo sapiens Ki = 2700.0 nM PMID[17535895]
NPT1495 Individual Protein Geranylgeranyl pyrophosphate synthetase Homo sapiens IC50 > 100000.0 nM PMID[17905588]
NPT1495 Individual Protein Geranylgeranyl pyrophosphate synthetase Homo sapiens Activity = 100.0 uM PMID[17905588]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 475.3 nM PMID[18327899]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens Ki = 85.9 nM PMID[18327899]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 4.1 nM PMID[18327899]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens Ki = 0.07 nM PMID[18327899]
NPT1495 Individual Protein Geranylgeranyl pyrophosphate synthetase Homo sapiens IC50 = 100000.0 nM PMID[18800762]
NPT708 Cell Line HuT78 Homo sapiens Activity = 24.0 % PMID[18937434]
NPT111 Cell Line K562 Homo sapiens Activity = 16.0 % PMID[18937434]
NPT404 Cell Line CCRF-CEM Homo sapiens Activity = 20.0 % PMID[18937434]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 4.1 nM PMID[18937434]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 4.1 nM PMID[22390415]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens Inhibition > 80.0 % PMID[22390415]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 475.0 nM PMID[22390415]
NPT1495 Individual Protein Geranylgeranyl pyrophosphate synthetase Homo sapiens IC50 > 100000.0 nM PMID[22390415]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 3.0 nM PMID[21780776]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 100.0 nM PMID[23610597]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 130.0 nM PMID[23610597]
NPT4015 Individual Protein Matrix metalloproteinase 14 Homo sapiens IC50 = 12600.0 nM PMID[24071448]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens IC50 = 52000.0 nM PMID[24071448]
NPT569 Individual Protein Matrix metalloproteinase 8 Homo sapiens IC50 = 17600.0 nM PMID[24071448]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens IC50 = 7000.0 nM PMID[24071448]
NPT389 Cell Line RPMI-8226 Homo sapiens EC50 = 11000.0 nM PMID[23998921]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens IC50 = 62.0 nM PMID[24650641]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens IC50 = 62.0 nM PMID[24813742]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens IC50 = 7000.0 nM PMID[24813742]
NPT1886 Cell Line J774 Mus musculus IC50 = 7800.0 nM PMID[24813742]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 23000.0 nM PMID[24928399]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 3.0 nM PMID[24911527]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens Ratio = 0.006 n.a. PMID[24911527]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 4.1 nM PMID[25630225]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 200.0 nM PMID[25815158]
NPT612 Individual Protein Canalicular multispecific organic anion transporter 1 Homo sapiens IC50 > 133000.0 nM PMID[23956101]
NPT1249 Individual Protein Canalicular multispecific organic anion transporter 2 Homo sapiens IC50 > 133000.0 nM PMID[23956101]
NPT1028 Individual Protein Multidrug resistance-associated protein 4 Homo sapiens IC50 > 133000.0 nM PMID[23956101]
NPT737 Cell Line HUVEC Homo sapiens Activity = 67.0 % PMID[30024167]
NPT1182 Cell Line J774.A1 Mus musculus Activity = -60.66 % PMID[30216851]
NPT113 Cell Line RAW264.7 Mus musculus Activity = -54.52 % PMID[30216851]
NPT2351 Cell Line MG-63 Homo sapiens Activity = -27.9 % PMID[30216851]
NPT306 Cell Line PC-3 Homo sapiens Activity = -28.41 % PMID[30216851]
NPT1495 Individual Protein Geranylgeranyl pyrophosphate synthetase Homo sapiens Inhibition = 38.0 % PMID[30216851]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens Inhibition = 91.1 % PMID[30216851]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 60.0 nM PMID[30216851]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 3.0 nM PMID[31699606]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 2.0 nM PMID[31577901]
NPT389 Cell Line RPMI-8226 Homo sapiens EC50 = 11000.0 nM PMID[30016091]
NPT389 Cell Line RPMI-8226 Homo sapiens Activity = 85.9 % PMID[30016091]
NPT389 Cell Line RPMI-8226 Homo sapiens Activity = 2.55 % PMID[30016091]
NPT389 Cell Line RPMI-8226 Homo sapiens Activity = 6.53 % PMID[30016091]
NPT389 Cell Line RPMI-8226 Homo sapiens Activity = 5.04 % PMID[30016091]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 100.0 nM PMID[31725297]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 170.0 nM PMID[31725297]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens Ratio IC50 = 1.7 n.a. PMID[31725297]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 140.0 nM PMID[31725297]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 220.0 nM PMID[31725297]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 2000.0 nM PMID[31725297]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 173.0 nM PMID[31725297]
NPT461 Cell Line PANC-1 Homo sapiens EC50 = 16100.0 nM PMID[31725297]
NPT783 Cell Line MIA PaCa-2 Homo sapiens EC50 = 13400.0 nM PMID[31725297]
NPT461 Cell Line PANC-1 Homo sapiens Activity = 0.0 % PMID[31725297]
NPT461 Cell Line PANC-1 Homo sapiens Activity = 1.91 % PMID[31725297]
NPT461 Cell Line PANC-1 Homo sapiens Activity = 4.02 % PMID[31725297]
NPT461 Cell Line PANC-1 Homo sapiens Activity = 94.1 % PMID[31725297]
NPT1384 Individual Protein Farnesyl diphosphate synthase Homo sapiens IC50 = 250.0 nM PMID[30730737]
NPT1495 Individual Protein Geranylgeranyl pyrophosphate synthetase Homo sapiens IC50 = 100000.0 nM PMID[30730737]
NPT1081 Cell Line BXPC-3 Homo sapiens IC50 = 10000.0 nM PMID[33132173]
NPT2316 Cell Line CFPAC-1 Homo sapiens IC50 = 10000.0 nM PMID[33132173]
NPT461 Cell Line PANC-1 Homo sapiens IC50 = 10000.0 nM PMID[33132173]
NPT165 Cell Line HeLa Homo sapiens IC50 = 10000.0 nM PMID[33132173]
NPT2245 Cell Line SiHa Homo sapiens IC50 = 10000.0 nM PMID[33132173]
NPT2306 Cell Line Ca-Ski Homo sapiens IC50 = 10000.0 nM PMID[33132173]
NPT114 Cell Line LoVo Homo sapiens IC50 = 34914.0 nM PMID[31785819]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 61582.0 nM PMID[31785819]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 100000.0 nM PMID[31785819]
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 12000.0 nM PMID[14695831]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 167000.0 nM PMID[14695831]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED50 = 0.00007 mg.kg-1 PMID[12166945]
NPT32 Organism Mus musculus Mus musculus IC50 = 2.0 nM PMID[12166945]
NPT32 Organism Mus musculus Mus musculus IC50 = 30000.0 nM PMID[12166945]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED50 = 0.0017 mg.kg-1 PMID[12166945]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED50 = 0.000071 mg.kg-1 PMID[12166945]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED50 = 0.00017 mg.kg-1 PMID[12166945]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED50 = 0.0011 mg.kg-1 PMID[12166945]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED100 = 38.0 ug kg-1 PMID[12166945]
NPT2 Others Unspecified Ratio = 15000.0 n.a. PMID[12166945]
NPT5128 Organism Dictyostelium discoideum Dictyostelium discoideum IC50 = 2900.0 nM PMID[15828834]
NPT2 Others Unspecified EC50 = 5400.0 nM PMID[15828834]
NPT32 Organism Mus musculus Mus musculus IC50 = 34.0 nM PMID[15828834]
NPT19 Organism Escherichia coli Escherichia coli IZ = 0.0 mm PMID[17149863]
NPT26594 SINGLE PROTEIN Geranylgeranyl pyrophosphate synthase Saccharomyces cerevisiae S288c IC50 = 660.0 nM PMID[17535895]
NPT26594 SINGLE PROTEIN Geranylgeranyl pyrophosphate synthase Saccharomyces cerevisiae S288c Ki = 260.0 nM PMID[17535895]
NPT2 Others Unspecified IC50 = 90.0 nM PMID[17535895]
NPT2 Others Unspecified IC50 = 38.0 nM PMID[17535895]
NPT2 Others Unspecified Activity = 0.1 uM PMID[18937434]
NPT2 Others Unspecified Activity = 22.0 % PMID[18937434]
NPT27 Others Unspecified Activity = 18.0 % PMID[18937434]
NPT2 Others Unspecified IC50 = 790.0 nM PMID[19053772]
NPT2 Others Unspecified IC50 = 794.33 nM PMID[19053772]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 170000.0 nM PMID[19053772]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 158489.32 nM PMID[19053772]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 167000.0 nM PMID[20185316]
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 12000.0 nM PMID[20185316]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 9400.0 nM PMID[22390415]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 10500.0 nM PMID[22390415]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 6400.0 nM PMID[22390415]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 400000.0 nM PMID[23610597]
NPT2 Others Unspecified IC50 = 170000.0 nM PMID[23610597]
NPT2 Others Unspecified IC50 = 130.0 nM PMID[23610597]
NPT23182 MACROMOLECULE Hydroxyapatite Homo sapiens Activity = 82.0 % PMID[23748153]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 60000.0 nM PMID[24607589]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 80.0 % PMID[24607589]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 72.0 % PMID[24607589]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 54.0 % PMID[24607589]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens IC50 > 10000.0 nM PMID[24650641]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens IC50 = 5323.0 nM PMID[24650641]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens IC50 = 316.0 nM PMID[24650641]
NPT954 Individual Protein Carbonic anhydrase XIV Homo sapiens IC50 = 92.0 nM PMID[24650641]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens IC50 > 10000.0 nM PMID[24813742]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens IC50 = 5323.0 nM PMID[24813742]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens IC50 = 316.0 nM PMID[24813742]
NPT954 Individual Protein Carbonic anhydrase XIV Homo sapiens IC50 = 92.0 nM PMID[24813742]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 92400.0 nM PMID[24928399]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 595800.0 nM PMID[24928399]
NPT27 Others Unspecified Activity = 60.0 % PMID[24911527]
NPT713 Individual Protein Bile salt export pump Homo sapiens IC50 > 135000.0 nM PMID[20829430]
NPT713 Individual Protein Bile salt export pump Homo sapiens IC50 > 133000.0 nM PMID[23956101]
NPT26693 SINGLE PROTEIN Butyrophilin subfamily 3 member A1 Homo sapiens EC50 = 486.6 nM PMID[29457898]
NPT26693 SINGLE PROTEIN Butyrophilin subfamily 3 member A1 Homo sapiens ED50 > 100.0 uM PMID[29457898]
NPT26693 SINGLE PROTEIN Butyrophilin subfamily 3 member A1 Homo sapiens Activity = 39.2 % PMID[29457898]
NPT23182 MACROMOLECULE Hydroxyapatite Homo sapiens Activity > 95.0 % PMID[30216851]
NPT21723 CELL-LINE Bone marrow cell n.a. Activity = 20.0 % PMID[30216851]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -7.59 % DOI[10.21203/rs.3.rs-23951/v1]
NPT26693 SINGLE PROTEIN Butyrophilin subfamily 3 member A1 Homo sapiens EC50 > 100000.0 nM PMID[31531198]
NPT26693 SINGLE PROTEIN Butyrophilin subfamily 3 member A1 Homo sapiens EC50 = 79000.0 nM PMID[31531198]
NPT26693 SINGLE PROTEIN Butyrophilin subfamily 3 member A1 Homo sapiens EC50 = 23000.0 nM PMID[31531198]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 26.1 % DOI[10.6019/CHEMBL4495564]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 8.204 % DOI[10.6019/CHEMBL4495564]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.02 % DOI[10.6019/CHEMBL4495565]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.03 % DOI[10.6019/CHEMBL4495565]
NPT26693 SINGLE PROTEIN Butyrophilin subfamily 3 member A1 Homo sapiens EC50 = 3060.0 nM PMID[32930595]
NPT32 Organism Mus musculus Mus musculus Activity = 26.19 % PMID[33175535]
NPT32 Organism Mus musculus Mus musculus Activity = 44.78 uM PMID[33175535]
NPT32 Organism Mus musculus Mus musculus Activity = 5.92 /millimeter PMID[33175535]
NPT32 Organism Mus musculus Mus musculus Activity = 132.16 um PMID[33175535]
NPT32 Organism Mus musculus Mus musculus Activity = 43.96 % PMID[33175535]
NPT32 Organism Mus musculus Mus musculus Activity = -35.61 micrometer/day PMID[33175535]
NPT32 Organism Mus musculus Mus musculus Activity = 189.5 um PMID[33175535]
NPT32 Organism Mus musculus Mus musculus Activity = 73.18 % PMID[33175535]
NPT27 Others Unspecified Activity = 0.54 /millimeter PMID[33175535]
NPT27 Others Unspecified Activity = 0.52 % PMID[33175535]
NPT27 Others Unspecified Activity = 8.51 % PMID[33175535]
NPT27 Others Unspecified Activity = 1.11 micrometer/day PMID[33175535]
NPT27 Others Unspecified Activity = 34.28 um3/um2/yr PMID[33175535]
NPT27 Others Unspecified Activity = 42.55 % PMID[33175535]
NPT27928 SINGLE PROTEIN Geranyltranstransferase Escherichia coli K-12 IC50 = 1100.0 nM PMID[17149863]
NPT27367 SINGLE PROTEIN Farnesyl pyrophosphate synthase Leishmania major Ki = 10.0 nM PMID[32979487]

☑ 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 NPC478721 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

  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 NPC478721 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

  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