Natural Product: NPC299405

Natural Product IDNPC299405
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Acetylshikonin
IUPAC Name [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL403516
PubChem CID 479501
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0000153] Naphthoquinones

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey WNFXUXZJJKTDOZ-OAHLLOKOSA-N
Standard InCHI InChI=1S/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3/t15-/m1/s1
SMILES CC(=O)O[C@@H](C1=CC(=O)c2c(C1=O)c(O)ccc2O)CC=C(C)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   330.11 Volume:   334.421
?
Van der Waals volume.
Dense:   0.987 LogP:   3.61
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.251
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.419
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   15.0
TPSA:   100.9
?
Topological Polar Surface Area.
 H-Bond Acceptor:   6.0
H-Bond Donor:   2.0 Rings:   2.0
Heavy Atoms:   6.0

MedChem Properties

QED Drug-Likeness Score:   0.5 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.403 Fsp3:   0.278
MCE-18:   48.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   1
Colloidal aggregators:   0.281 Fluc inhibitor:   0.672
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.84
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.411
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.467 Promiscuous compounds:   0.308

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.724 MDCK Permeability:   -4.555
Pgp-inhibitor:   0.002 Pgp-substrate:   0.013
PAMPA:   0.996
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.045
20% Bioavailability (F20%):   0.021 30% Bioavailability (F30%):   0.134
50% Bioavailability (F50%):   0.446

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.98
Plasma Protein Binding (PPB):   93.14% Volume Distribution (VD):   0.449
Fu: 6.878%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.882
OATP1B3 inhibitor:   0.989 BCRP inhibitor:   0.0
BSEP inhibitor:   0.033

ADMET: Metabolism

CYP1A2-inhibitor:   0.002 CYP1A2-substrate:   0.354
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.081
CYP2C9-inhibitor:   0.002 CYP2C9-substrate:   0.147
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.019
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.802
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.999
HLM stability:   0.977
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  12.04 Half-life (T1/2):  1.249

ADMET: Toxicity

hERG Blockers:  0.024 hERG Blockers (10um):  0.313
Human Hepatotoxicity (H-HT):  0.724 Drug-induced Liver Injury (DILI):  0.922
AMES Toxicity:  0.943 Rat Oral Acute Toxicity:  0.497
Maximum Recommended Daily Dose:  0.426 Skin Sensitization:  0.984
Carcinogencity:  0.758 Eye Corrosion:  0.001
Eye Irritation:  0.872 Respiratory Toxicity:  0.754
Drug-induced Neurotoxicity:  0.273 Ototoxicity:  0.359
Hematotoxicity:  0.766 Drug-induced Nephrotoxicity:  0.794
Genotoxicity:  0.982 RPMI-8226 Immunitoxicity:  0.274
A549 Cytotoxicity:  0.786 Hek293 Cytotoxicity:  0.311
BCF:   1.693
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   4.514
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.634
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.209
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. root n.a. DOI[10.1007/s11418-007-0221-0]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(83)80138-1]
NPO18713 Strychnos usambarensis Species Loganiaceae Eukaryota roots n.a. n.a. PMID[10217724]
NPO18713 Strychnos usambarensis Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[12398531]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[12502328]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[17157006]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[17488128]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[19217780]
NPO18713 Strychnos usambarensis Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[19534474]
NPO20181 Dracaena arborea Species Asparagaceae Eukaryota bark Yaound, village of Bangoua, near Bangangt 2007-APR PMID[20553003]
NPO17855 Onosma paniculata Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[22530779]
NPO5119.1 Pseudomonas chlororaphis subsp. aurantiaca Subspecies Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[31999458]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[3373224]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[7775984]
NPO17855 Onosma paniculata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14913 Robinia neomexicana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11300 Eucalyptus coccifera Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9209 Rhizomnium magnifolium Species Mniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18713 Strychnos usambarensis Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19871 Rubus arcticus Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18713 Strychnos usambarensis Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17855 Onosma paniculata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18713 Strychnos usambarensis Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19871 Rubus arcticus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18713 Strychnos usambarensis Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19789 Umbilicaria polyphylla Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18550 Teucrium gnaphalodes Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20181 Dracaena arborea Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9209 Rhizomnium magnifolium Species Mniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11300 Eucalyptus coccifera Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14913 Robinia neomexicana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17855 Onosma paniculata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5119.1 Pseudomonas chlororaphis subsp. aurantiaca Subspecies Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26982 Callyspongia siphonella Species Callyspongiidae 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 Organism Name 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

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT143 Individual protein DNA topoisomerase I Homo sapiens IC50 = 45000.0 nM PMID[7699697]
NPT144 Individual protein Telomerase reverse transcriptase Homo sapiens IC50 = 37300.0 nM PMID[11992780]
NPT1214 Individual protein Acyl coenzyme A:cholesterol acyltransferase 1 Homo sapiens IC50 = 128900.0 nM PMID[17157006]
NPT2584 Individual protein Acyl coenzyme A:cholesterol acyltransferase 2 Homo sapiens IC50 = 112200.0 nM PMID[17157006]
NPT2228 Individual protein Neuraminidase Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1)) IC50 = 41400.0 nM PMID[22300884]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition > 50.0 % PMID[38508325]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 41.7 % PMID[36651644]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 84.3 % PMID[36651644]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 IC50 = 3800.0 nM PMID[36651644]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 IC50 = 24300.0 nM PMID[36651644]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 IC50 = 350.0 nM PMID[38508325]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT111 Cell line K562 Homo sapiens IC50 = 29000.0 nM PMID[11992780]
NPT81 Cell line A549 Homo sapiens IC50 = 39000.0 nM PMID[11992780]
NPT515 Cell line SGC-7901 Homo sapiens IC50 = 290.0 nM PMID[11992780]
NPT181 Cell line Bel-7402 Homo sapiens IC50 = 68.0 nM PMID[11992780]
NPT83 Cell line MCF7 Homo sapiens IC50 = 31000.0 nM PMID[11992780]
NPT393 Cell line HCT-116 Homo sapiens IC50 = 450.0 nM PMID[17949858]
NPT65 Cell line HepG2 Homo sapiens IC50 = 380.0 nM PMID[17949858]
NPT404 Cell line CCRF-CEM Homo sapiens IC50 = 1000.0 nM PMID[22530779]
NPT82 Cell line MDA-MB-231 Homo sapiens IC50 = 11300.0 nM PMID[22530779]
NPT380 Cell line U-251 Homo sapiens IC50 = 15900.0 nM PMID[22530779]
NPT393 Cell line HCT-116 Homo sapiens IC50 = 9000.0 nM PMID[22530779]
NPT171 Cell line MRC5 Homo sapiens IC50 = 2600.0 nM PMID[22530779]
NPT171 Cell line MRC5 Homo sapiens Ratio IC50 = 6.0 n.a. PMID[22530779]
NPT2311 Cell line Calu-3 Homo sapiens CC50 > 100000.0 nM PMID[36651644]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 100000.0 nM PMID[36651644]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 13000.0 nM PMID[22530779]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 30700.0 nM PMID[22530779]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 23500.0 nM PMID[22530779]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 71500.0 nM PMID[22530779]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Ratio <= 2.0 n.a. PMID[12502328]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MBC = 6.25 ug ml-1 PMID[12502328]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 6.25 ug.mL-1 PMID[12502328]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MBC = 3.13 ug ml-1 PMID[12502328]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 3.13 ug.mL-1 PMID[12502328]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 1.56 ug ml-1 PMID[12502328]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 1.56 ug.mL-1 PMID[12502328]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis Ratio <= 2.0 n.a. PMID[12502328]
NPT1780 Organism Davidiella tassiana Davidiella tassiana IZ = 10.1 mm DOI[10.1584/jpestics.23.54]
NPT1780 Organism Davidiella tassiana Davidiella tassiana IZ = 13.0 mm DOI[10.1584/jpestics.23.54]
NPT1780 Organism Davidiella tassiana Davidiella tassiana IZ = 13.3 mm DOI[10.1584/jpestics.23.54]
NPT1780 Organism Davidiella tassiana Davidiella tassiana IZ = 13.4 mm DOI[10.1584/jpestics.23.54]
NPT2 Others Unspecified n.a. IC50 = 2200.0 nM PMID[17320246]
NPT2 Others Unspecified n.a. IC50 = 2000.0 nM PMID[17320246]
NPT1531 Organism Enterococcus faecium Enterococcus faecium MBC = 6.25 ug ml-1 PMID[12502328]
NPT1531 Organism Enterococcus faecium Enterococcus faecium MIC = 6.25 ug.mL-1 PMID[12502328]
NPT1531 Organism Enterococcus faecium Enterococcus faecium Ratio <= 2.0 n.a. PMID[12502328]
NPT2 Others Unspecified n.a. IC50 = 157800.0 nM PMID[22300884]
NPT2 Others Unspecified n.a. Ki = 1010.0 nM PMID[22300884]
NPT2 Others Unspecified n.a. IC50 = 2500.0 nM PMID[22300884]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 73.2 % DOI[10.1584/jpestics.23.54]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 78.7 % DOI[10.1584/jpestics.23.54]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC299405 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC216312
0.8889 High Similarity NPC256463
0.8511 High Similarity NPC111422
0.8511 High Similarity NPC241349
0.8511 High Similarity NPC306835
0.8511 High Similarity NPC37992
0.8511 High Similarity NPC29771
0.8333 Intermediate Similarity NPC32749
0.8333 Intermediate Similarity NPC42262
0.8163 Intermediate Similarity NPC147542
0.8163 Intermediate Similarity NPC220496
0.8163 Intermediate Similarity NPC327916
0.8163 Intermediate Similarity NPC257003
0.8163 Intermediate Similarity NPC476477
0.8 Intermediate Similarity NPC471602
0.717 Intermediate Similarity NPC89664
0.7143 Intermediate Similarity NPC474300
0.678 Remote Similarity NPC471444
0.6727 Remote Similarity NPC476473
0.6207 Remote Similarity NPC274085
0.597 Remote Similarity NPC474301
0.5294 Remote Similarity NPC246693
0.5294 Remote Similarity NPC242358
0.5294 Remote Similarity NPC306765
0.5294 Remote Similarity NPC110609
0.5217 Remote Similarity NPC609532

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC299405 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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