Natural Product: NPC122828

Natural Product IDNPC122828
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (2R,3R)-Alpinone
IUPAC Name (2R,3R)-3,5-dihydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms (2R,3R)-Alpinone
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1081328
PubChem CID 46883390
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002592] 7-O-methylated flavonoids

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 QPOCKDYYXFOBCM-JKSUJKDBSA-N
Standard InCHI InChI=1S/C16H14O5/c1-20-10-7-11(17)13-12(8-10)21-16(15(19)14(13)18)9-5-3-2-4-6-9/h2-8,15-17,19H,1H3/t15-,16+/m0/s1
SMILES COc1cc(c2c(c1)O[C@H](c1ccccc1)[C@H](C2=O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   286.08 Volume:   285.119
?
Van der Waals volume.
Dense:   1.003 LogP:   2.433
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.255
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.3
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   18.0
TPSA:   75.99
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   2.0 Rings:   3.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.884 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.977 Fsp3:   0.188
MCE-18:   54.579
?
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:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.433 Fluc inhibitor:   0.614
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.239
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.282
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.332 Promiscuous compounds:   0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.326 MDCK Permeability:   -4.688
Pgp-inhibitor:   0.99 Pgp-substrate:   0.033
PAMPA:   0.041
?
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):   0.012
20% Bioavailability (F20%):   0.003 30% Bioavailability (F30%):   0.443
50% Bioavailability (F50%):   0.735

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.249 MRP1:   0.431
Plasma Protein Binding (PPB):   96.965% Volume Distribution (VD):   0.142
Fu: 2.583%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.722
BSEP inhibitor:   0.897

ADMET: Metabolism

CYP1A2-inhibitor:   1.0 CYP1A2-substrate:   0.438
CYP2C19-inhibitor:   0.002 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.896 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.014 CYP2D6-substrate:   0.011
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.153
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.245
HLM stability:   0.006
?
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):  7.852 Half-life (T1/2):  1.789

ADMET: Toxicity

hERG Blockers:  0.125 hERG Blockers (10um):  0.452
Human Hepatotoxicity (H-HT):  0.661 Drug-induced Liver Injury (DILI):  0.626
AMES Toxicity:  0.608 Rat Oral Acute Toxicity:  0.27
Maximum Recommended Daily Dose:  0.373 Skin Sensitization:  0.798
Carcinogencity:  0.228 Eye Corrosion:  0.011
Eye Irritation:  0.917 Respiratory Toxicity:  0.721
Drug-induced Neurotoxicity:  0.463 Ototoxicity:  0.477
Hematotoxicity:  0.379 Drug-induced Nephrotoxicity:  0.703
Genotoxicity:  0.849 RPMI-8226 Immunitoxicity:  0.146
A549 Cytotoxicity:  0.26 Hek293 Cytotoxicity:  0.332
BCF:   1.223
?
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:   3.799
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.019
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.328
?
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
NPO17520 Erythrina subumbrans Species Fabaceae Eukaryota n.a. stem n.a. PMID[17055201]
NPO17520 Erythrina subumbrans Species Fabaceae Eukaryota n.a. bark n.a. PMID[17055201]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. PMID[17548953]
NPO17520 Erythrina subumbrans Species Fabaceae Eukaryota Barks n.a. n.a. PMID[18171023]
NPO13784 Dalbergia candenatensis Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[19653666]
NPO13379 Schizanthus tricolor Species Solanaceae Eukaryota Aerial parts n.a. n.a. PMID[20166702]
NPO40884 Mexican propolis Species n.a. n.a. n.a. n.a. n.a. PMID[20307087]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. exocarp n.a. PMID[21114277]
NPO13379 Schizanthus tricolor Species Solanaceae Eukaryota n.a. aerial part n.a. PMID[21171571]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. bark n.a. PMID[22032697]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota bark n.a. n.a. PMID[22032697]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. PMID[24675423]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Bako, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Enemore, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Gedo, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Holleta, Ethiopia PMID[24926420]
NPO14561 Walsura yunnanensis Species Meliaceae Eukaryota Leaves; Twigs n.a. n.a. PMID[25075875]
NPO3013 Clathria basilana Species Microcionidae Eukaryota n.a. n.a. n.a. PMID[29094598]
NPO13784 Dalbergia candenatensis Species Fabaceae Eukaryota n.a. Thai n.a. PMID[3430167]
NPO14169 Acrocarpia paniculata Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13473 Anodendron affine Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13876 Cedrela salvadorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3013 Clathria basilana Species Microcionidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13669 Hertia cheirifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9569 Licaria chrysophylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13178 Ornithoglossum viride Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4700 Pertusaria truncata Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11842 Petasites laevigatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14369 Pocillopora eydouxi Species Pocilloporidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14470 Polypodium decumanum Species Polypodiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5280 Rubia tetragona Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13379 Schizanthus tricolor Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12521 Sphaeranthus confertifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17918 Pinus clausa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2924 Pinus excelsa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21693 Pinus morrisonicola Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO40884 Mexican propolis Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14960 Angelica pancicii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17069 Argemone aenea Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14804 Celastrus kusanoi Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9131 Cryptostylis fulva Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17520 Erythrina subumbrans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16998 Nannizzia gypsea Species Arthrodermataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13537 Piper rugosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11371 Psychotria leiocarpa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9946 Roemeria hybrida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17299 Stephania discolor Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5022 Viguiera arenaria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14561 Walsura yunnanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13784 Dalbergia candenatensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2924 Pinus excelsa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13473 Anodendron affine Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11842 Petasites laevigatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17299 Stephania discolor Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13473 Anodendron affine Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14561 Walsura yunnanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11842 Petasites laevigatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17299 Stephania discolor Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2924 Pinus excelsa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5280 Rubia tetragona Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14369 Pocillopora eydouxi Species Pocilloporidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17299 Stephania discolor Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4700 Pertusaria truncata Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12521 Sphaeranthus confertifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3013 Clathria basilana Species Microcionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11371 Psychotria leiocarpa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11842 Petasites laevigatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14470 Polypodium decumanum Species Polypodiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14169 Acrocarpia paniculata Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13178 Ornithoglossum viride Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13876 Cedrela salvadorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13473 Anodendron affine Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9569 Licaria chrysophylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14960 Angelica pancicii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13784 Dalbergia candenatensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13379 Schizanthus tricolor Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13537 Piper rugosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14804 Celastrus kusanoi Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9131 Cryptostylis fulva Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13669 Hertia cheirifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17069 Argemone aenea Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21693 Pinus morrisonicola Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16998 Nannizzia gypsea Species Arthrodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17520 Erythrina subumbrans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9946 Roemeria hybrida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17918 Pinus clausa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2924 Pinus excelsa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14561 Walsura yunnanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5022 Viguiera arenaria Species Asteraceae 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

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT139 Cell line HT-29 Homo sapiens IC50 = 46500.0 nM PMID[19653666]
NPT91 Cell line KB Homo sapiens IC50 = 73800.0 nM PMID[19653666]
NPT83 Cell line MCF7 Homo sapiens IC50 = 49300.0 nM PMID[19653666]
NPT165 Cell line HeLa Homo sapiens IC50 = 79000.0 nM PMID[19653666]
NPT461 Cell line PANC-1 Homo sapiens PC50 = 74.2 uM PMID[20307087]

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 NPC122828 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
0.8125 Intermediate Similarity NPC176869
0.8125 Intermediate Similarity NPC3779
0.7 Intermediate Similarity NPC4152
0.6735 Remote Similarity NPC31704
0.6731 Remote Similarity NPC263449
0.6471 Remote Similarity NPC476182
0.6415 Remote Similarity NPC308992
0.6415 Remote Similarity NPC44721
0.6415 Remote Similarity NPC211466
0.6415 Remote Similarity NPC605332
0.6154 Remote Similarity NPC148011
0.6111 Remote Similarity NPC481903
0.6071 Remote Similarity NPC42892
0.6038 Remote Similarity NPC150648
0.5741 Remote Similarity NPC62290
0.5741 Remote Similarity NPC142731
0.5741 Remote Similarity NPC326506
0.5517 Remote Similarity NPC320825
0.5455 Remote Similarity NPC105136
0.5439 Remote Similarity NPC250922
0.5333 Remote Similarity NPC326037
0.5333 Remote Similarity NPC13858
0.5273 Remote Similarity NPC21835
0.5263 Remote Similarity NPC471500
0.5263 Remote Similarity NPC306607
0.5254 Remote Similarity NPC6802
0.5185 Remote Similarity NPC1940
0.5172 Remote Similarity NPC36835
0.5172 Remote Similarity NPC246162
0.5172 Remote Similarity NPC9743
0.5172 Remote Similarity NPC260491
0.5172 Remote Similarity NPC61506
0.5172 Remote Similarity NPC240476
0.5147 Remote Similarity NPC163191
0.5088 Remote Similarity NPC201837
0.5088 Remote Similarity NPC19721
0.5085 Remote Similarity NPC471479

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC122828 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