Natural Product: NPC166040

Natural Product IDNPC166040
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Vanilloloside
IUPAC Name (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxane-3,4,5-triol
Synonyms Vanilloloside
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL468568
PubChem CID 44577222
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic glycosides

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 SIMPNXWTAVEOTO-RKQHYHRCSA-N
Standard InCHI InChI=1S/C14H20O8/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-4,10-19H,5-6H2,1H3/t10-,11-,12+,13-,14-/m1/s1
SMILES COc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)CO

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   316.12 Volume:   296.0
?
Van der Waals volume.
Dense:   1.068 LogP:   -0.896
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   -0.358
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -0.897
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   12.0
TPSA:   128.84
?
Topological Polar Surface Area.
 H-Bond Acceptor:   8.0
H-Bond Donor:   5.0 Rings:   2.0
Heavy Atoms:   8.0

MedChem Properties

QED Drug-Likeness Score:   0.438 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.405 Fsp3:   0.571
MCE-18:   48.364
?
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:   0
Colloidal aggregators:   0.425 Fluc inhibitor:   0.014
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.049
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.057
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.241 Promiscuous compounds:   0.014

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.852 MDCK Permeability:   -5.032
Pgp-inhibitor:   0.001 Pgp-substrate:   0.084
PAMPA:   0.68
?
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):   0.861
20% Bioavailability (F20%):   0.185 30% Bioavailability (F30%):   0.977
50% Bioavailability (F50%):   0.814

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.232 MRP1:   0.039
Plasma Protein Binding (PPB):   56.988% Volume Distribution (VD):   -0.322
Fu: 42.568%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.049
BSEP inhibitor:   0.002

ADMET: Metabolism

CYP1A2-inhibitor:   0.014 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.274 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   0.035 CYP3A4-substrate:   0.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.777
HLM stability:   0.001
?
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):  2.819 Half-life (T1/2):  3.345

ADMET: Toxicity

hERG Blockers:  0.021 hERG Blockers (10um):  0.097
Human Hepatotoxicity (H-HT):  0.642 Drug-induced Liver Injury (DILI):  0.658
AMES Toxicity:  0.838 Rat Oral Acute Toxicity:  0.012
Maximum Recommended Daily Dose:  0.011 Skin Sensitization:  0.978
Carcinogencity:  0.347 Eye Corrosion:  0.001
Eye Irritation:  0.559 Respiratory Toxicity:  0.027
Drug-induced Neurotoxicity:  0.047 Ototoxicity:  0.9
Hematotoxicity:  0.319 Drug-induced Nephrotoxicity:  0.642
Genotoxicity:  0.404 RPMI-8226 Immunitoxicity:  0.075
A549 Cytotoxicity:  0.07 Hek293 Cytotoxicity:  0.09
BCF:   0.204
?
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:   2.126
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   3.586
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   2.779
?
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
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[11520233]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[12932145]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. bulb n.a. PMID[14994197]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[15844951]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota tubers n.a. n.a. PMID[16792409]
NPO9317 Itoa orientalis Species Salicaceae Eukaryota bark, twigs, and leaves n.a. n.a. PMID[18412396]
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]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[23627123]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. kernel n.a. PMID[7092570]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26538 Phellodendron chinese Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17757 Plectranthus saccatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5016 Glossogyne tenuifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16210 Androcymbium palaestinum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18071 Euryops pedunculatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9317 Itoa orientalis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12630 Senecio oxyodontus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15594 Aplidiopsis confluata n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO15954 Pyrenula japonica Species Pyrenulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15954 Pyrenula japonica Species Pyrenulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16326 Scopolia parviflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26538 Phellodendron chinese Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14001 Ceroplastes pseudoceriferus Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5016 Glossogyne tenuifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15740 Garcinia purpurea Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14507.1 Quercus ithaburensis subsp. macrolepis Subspecies Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16049 Cryptocarya pleurosperma Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16210 Androcymbium palaestinum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18071 Euryops pedunculatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17917 Thamnophis sirtalis Species Colubridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11755 Banisteriopsis caapi Species Malpighiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17600 Gnathotrichus sulcatus Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15594 Aplidiopsis confluata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16326 Scopolia parviflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17444 Gleichenia japonica Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15954 Pyrenula japonica Species Pyrenulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12630 Senecio oxyodontus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17757 Plectranthus saccatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10751 Bothriocline laxa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11280 Aphanoascus terreus Species Onygenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO619 Ankistrodesmus braunii Species Selenastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17141 Lonchocarpus longistylus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9317 Itoa orientalis Species Salicaceae 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
NPT31 Individual protein Cyclooxygenase-2 Homo sapiens Inhibition = 41.0 % PMID[18412396]
NPT204 Individual protein Acetylcholinesterase Homo sapiens IC50 = 4550.0 nM PMID[35028560]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT393 Cell line HCT-116 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[22032697]
NPT492 Cell line Caco-2 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[22032697]

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 NPC166040 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
0.7347 Intermediate Similarity NPC299144
0.717 Intermediate Similarity NPC472024
0.717 Intermediate Similarity NPC270849
0.7083 Intermediate Similarity NPC269242
0.7037 Intermediate Similarity NPC26653
0.7037 Intermediate Similarity NPC80600
0.6909 Remote Similarity NPC248355
0.6786 Remote Similarity NPC55040
0.6739 Remote Similarity NPC228907
0.6667 Remote Similarity NPC302378
0.6481 Remote Similarity NPC9912
0.6471 Remote Similarity NPC25817
0.6441 Remote Similarity NPC276753
0.6441 Remote Similarity NPC205796
0.6333 Remote Similarity NPC37468
0.6333 Remote Similarity NPC246947
0.6333 Remote Similarity NPC604095
0.6316 Remote Similarity NPC479029
0.6226 Remote Similarity NPC226712
0.619 Remote Similarity NPC25821
0.6129 Remote Similarity NPC111785
0.5965 Remote Similarity NPC479028
0.5965 Remote Similarity NPC479031
0.5962 Remote Similarity NPC153149
0.5882 Remote Similarity NPC276195
0.5882 Remote Similarity NPC212729
0.5882 Remote Similarity NPC604498
0.5818 Remote Similarity NPC69513
0.5769 Remote Similarity NPC217854
0.5758 Remote Similarity NPC158635
0.5758 Remote Similarity NPC229882
0.5741 Remote Similarity NPC609376
0.5714 Remote Similarity NPC48863
0.5714 Remote Similarity NPC251981
0.5714 Remote Similarity NPC13745
0.5672 Remote Similarity NPC327032
0.5672 Remote Similarity NPC286235
0.566 Remote Similarity NPC294470
0.5636 Remote Similarity NPC608788
0.5614 Remote Similarity NPC215833
0.5593 Remote Similarity NPC210478
0.5588 Remote Similarity NPC38041
0.5588 Remote Similarity NPC227902
0.5588 Remote Similarity NPC18979
0.5588 Remote Similarity NPC22150
0.5588 Remote Similarity NPC279298
0.5556 Remote Similarity NPC152722
0.5536 Remote Similarity NPC145900
0.5517 Remote Similarity NPC218685
0.5517 Remote Similarity NPC49074
0.5507 Remote Similarity NPC471063
0.5455 Remote Similarity NPC60589
0.5455 Remote Similarity NPC469708
0.5455 Remote Similarity NPC605700
0.5439 Remote Similarity NPC166168
0.5424 Remote Similarity NPC162093
0.541 Remote Similarity NPC104167
0.5397 Remote Similarity NPC294166
0.5397 Remote Similarity NPC115022
0.537 Remote Similarity NPC192810
0.5357 Remote Similarity NPC200092
0.5345 Remote Similarity NPC40377
0.5323 Remote Similarity NPC247146
0.5312 Remote Similarity NPC479030
0.5312 Remote Similarity NPC610808
0.5294 Remote Similarity NPC160780
0.5294 Remote Similarity NPC606202
0.5283 Remote Similarity NPC142319
0.5278 Remote Similarity NPC93924
0.5278 Remote Similarity NPC217635
0.5263 Remote Similarity NPC221090
0.5263 Remote Similarity NPC80098
0.5224 Remote Similarity NPC148273
0.5217 Remote Similarity NPC61594
0.5205 Remote Similarity NPC43508
0.5172 Remote Similarity NPC95292
0.5167 Remote Similarity NPC205054
0.5167 Remote Similarity NPC23084
0.5167 Remote Similarity NPC604356
0.5161 Remote Similarity NPC95392
0.5161 Remote Similarity NPC84013
0.5161 Remote Similarity NPC55715
0.5161 Remote Similarity NPC35877
0.5152 Remote Similarity NPC210192
0.5152 Remote Similarity NPC475096
0.5152 Remote Similarity NPC475084
0.5143 Remote Similarity NPC56735
0.5135 Remote Similarity NPC299706
0.5135 Remote Similarity NPC245615
0.5135 Remote Similarity NPC186316
0.5135 Remote Similarity NPC115466
0.5135 Remote Similarity NPC39657
0.5135 Remote Similarity NPC61604
0.5088 Remote Similarity NPC12308
0.5085 Remote Similarity NPC310661
0.5079 Remote Similarity NPC232673
0.5077 Remote Similarity NPC486107
0.5072 Remote Similarity NPC212099

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC166040 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
0.6226 Remote Similarity NPD1091 Pre-clinical

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