Structure

Physi-Chem Properties

Molecular Weight:  134.09
Volume:  138.703
LogP:  -0.251
LogD:  0.05
LogS:  0.956
# Rotatable Bonds:  6
TPSA:  38.69
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.521
Synthetic Accessibility Score:  2.045
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.214
MDCK Permeability:  4.722001904156059e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.264
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.538
Plasma Protein Binding (PPB):  12.318638801574707%
Volume Distribution (VD):  0.796
Pgp-substrate:  78.54757690429688%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.166
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.393
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.044
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.088
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.146

ADMET: Excretion

Clearance (CL):  5.652
Half-life (T1/2):  0.8

ADMET: Toxicity

hERG Blockers:  0.25
Human Hepatotoxicity (H-HT):  0.03
Drug-inuced Liver Injury (DILI):  0.018
AMES Toxicity:  0.104
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.005
Skin Sensitization:  0.501
Carcinogencity:  0.464
Eye Corrosion:  0.137
Eye Irritation:  0.981
Respiratory Toxicity:  0.013

Download Data

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

  Natural Product: NPC237965

Natural Product ID:  NPC237965
Common Name*:   Diethylene Glycol Monoethyl Ether
IUPAC Name:   2-(2-ethoxyethoxy)ethanol
Synonyms:   Diethylene Glycol Monoethyl Ether
Standard InCHIKey:  XXJWXESWEXIICW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H14O3/c1-2-8-5-6-9-4-3-7/h7H,2-6H2,1H3
SMILES:  CCOCCOCCO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1230841
PubChem CID:   8146
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000254] Ethers
          • [CHEMONTID:0001167] Dialkyl ethers

*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
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota root n.a. n.a. PMID[15921428]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[17689080]
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota flowers n.a. n.a. PMID[19374389]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[23872723]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[32996318]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7317 Citrus aurantium Species Rutaceae 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
NPT2 Others Unspecified Potency n.a. 356.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24336.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 63398.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 49894 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48966.2 nM PubChem BioAssay data set

☑ 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 NPC237965 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
1.0 High Similarity NPC318912
0.9565 High Similarity NPC304786
0.9167 High Similarity NPC317724
0.9167 High Similarity NPC128335
0.88 High Similarity NPC272307
0.8462 Intermediate Similarity NPC238135
0.84 Intermediate Similarity NPC329496
0.84 Intermediate Similarity NPC230452
0.8182 Intermediate Similarity NPC43196
0.7308 Intermediate Similarity NPC140389
0.7273 Intermediate Similarity NPC149567
0.7083 Intermediate Similarity NPC321400
0.6923 Remote Similarity NPC114270
0.6667 Remote Similarity NPC313405
0.6667 Remote Similarity NPC103612
0.6667 Remote Similarity NPC24967
0.6562 Remote Similarity NPC227267
0.64 Remote Similarity NPC294703
0.6364 Remote Similarity NPC325165
0.6364 Remote Similarity NPC2724
0.6296 Remote Similarity NPC94144
0.6296 Remote Similarity NPC157340
0.6296 Remote Similarity NPC87529
0.6286 Remote Similarity NPC197039
0.625 Remote Similarity NPC311000
0.6207 Remote Similarity NPC320326
0.6154 Remote Similarity NPC299484
0.6154 Remote Similarity NPC88839
0.6154 Remote Similarity NPC219266
0.6154 Remote Similarity NPC110344
0.6071 Remote Similarity NPC88887
0.6 Remote Similarity NPC163707
0.6 Remote Similarity NPC316272
0.6 Remote Similarity NPC301586
0.6 Remote Similarity NPC33415
0.6 Remote Similarity NPC236761
0.6 Remote Similarity NPC88135
0.5946 Remote Similarity NPC152008
0.5926 Remote Similarity NPC52403
0.5926 Remote Similarity NPC23508
0.5926 Remote Similarity NPC39977
0.5833 Remote Similarity NPC473991
0.5806 Remote Similarity NPC232172
0.5769 Remote Similarity NPC61373
0.5714 Remote Similarity NPC110107
0.5714 Remote Similarity NPC23071
0.5714 Remote Similarity NPC245688
0.5714 Remote Similarity NPC199270
0.5714 Remote Similarity NPC184593
0.5714 Remote Similarity NPC256186

  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 NPC237965 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
0.7273 Intermediate Similarity NPD7374 Approved
0.6923 Remote Similarity NPD8225 Phase 3
0.6818 Remote Similarity NPD8547 Phase 2
0.6296 Remote Similarity NPD8226 Approved
0.625 Remote Similarity NPD8223 Approved
0.6 Remote Similarity NPD8224 Approved
0.6 Remote Similarity NPD8549 Clinical (unspecified phase)
0.5946 Remote Similarity NPD7536 Approved
0.5789 Remote Similarity NPD8967 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