Structure

Physi-Chem Properties

Molecular Weight:  162.13
Volume:  173.295
LogP:  0.727
LogD:  0.795
LogS:  0.449
# Rotatable Bonds:  8
TPSA:  38.69
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.537
Synthetic Accessibility Score:  1.996
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:  -4.163
MDCK Permeability:  3.415114770177752e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.561
30% Bioavailability (F30%):  0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.579
Plasma Protein Binding (PPB):  17.686843872070312%
Volume Distribution (VD):  0.939
Pgp-substrate:  68.21249389648438%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.138
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.428
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.046
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.07
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.148

ADMET: Excretion

Clearance (CL):  7.606
Half-life (T1/2):  0.788

ADMET: Toxicity

hERG Blockers:  0.267
Human Hepatotoxicity (H-HT):  0.027
Drug-inuced Liver Injury (DILI):  0.014
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.052
Maximum Recommended Daily Dose:  0.006
Skin Sensitization:  0.676
Carcinogencity:  0.531
Eye Corrosion:  0.517
Eye Irritation:  0.988
Respiratory Toxicity:  0.015

Download Data

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

  Natural Product: NPC238135

Natural Product ID:  NPC238135
Common Name*:   2-(2-Butoxyethoxy)Ethanol
IUPAC Name:   2-(2-butoxyethoxy)ethanol
Synonyms:  
Standard InCHIKey:  OAYXUHPQHDHDDZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H18O3/c1-2-3-5-10-7-8-11-6-4-9/h9H,2-8H2,1H3
SMILES:  CCCCOCCOCCO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1904721
PubChem CID:   8177
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
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[14600382]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[25894905]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[28358502]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26327 Chaenomeles sinensis Species Rosaceae 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
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 28183.8 nM PMID[530490]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 19577.3 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 2452.9 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 61908.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6190.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30762.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48942.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61068.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21667.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61614.6 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 NPC238135 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
0.9231 High Similarity NPC128335
0.8846 High Similarity NPC304786
0.8519 High Similarity NPC329496
0.8519 High Similarity NPC230452
0.8519 High Similarity NPC317724
0.8462 Intermediate Similarity NPC318912
0.8462 Intermediate Similarity NPC237965
0.8214 Intermediate Similarity NPC272307
0.7429 Intermediate Similarity NPC197039
0.7308 Intermediate Similarity NPC61373
0.7027 Intermediate Similarity NPC152008
0.6944 Remote Similarity NPC473991
0.6923 Remote Similarity NPC43196
0.6897 Remote Similarity NPC140389
0.6765 Remote Similarity NPC227267
0.6667 Remote Similarity NPC294703
0.6552 Remote Similarity NPC114270
0.6452 Remote Similarity NPC320326
0.6429 Remote Similarity NPC219266
0.6389 Remote Similarity NPC313405
0.6389 Remote Similarity NPC24967
0.6389 Remote Similarity NPC103612
0.6333 Remote Similarity NPC88887
0.6286 Remote Similarity NPC140229
0.625 Remote Similarity NPC301586
0.625 Remote Similarity NPC33415
0.6207 Remote Similarity NPC52403
0.6154 Remote Similarity NPC149567
0.6111 Remote Similarity NPC325165
0.6071 Remote Similarity NPC321400
0.6047 Remote Similarity NPC8597
0.6 Remote Similarity NPC23071
0.6 Remote Similarity NPC157340
0.6 Remote Similarity NPC87529
0.6 Remote Similarity NPC94144
0.6 Remote Similarity NPC256186
0.6 Remote Similarity NPC199270
0.6 Remote Similarity NPC245688
0.5952 Remote Similarity NPC62014
0.5926 Remote Similarity NPC311000
0.5882 Remote Similarity NPC236797
0.5882 Remote Similarity NPC112242
0.5882 Remote Similarity NPC225783
0.5882 Remote Similarity NPC185041
0.5882 Remote Similarity NPC24506
0.5882 Remote Similarity NPC163556
0.5882 Remote Similarity NPC147096
0.5862 Remote Similarity NPC110344
0.5862 Remote Similarity NPC88839
0.5862 Remote Similarity NPC299484
0.5854 Remote Similarity NPC144829
0.5854 Remote Similarity NPC31121
0.5806 Remote Similarity NPC232554
0.5806 Remote Similarity NPC213764
0.5806 Remote Similarity NPC275462
0.5806 Remote Similarity NPC3693
0.5778 Remote Similarity NPC26253
0.5778 Remote Similarity NPC82512
0.5758 Remote Similarity NPC159845
0.5758 Remote Similarity NPC279895
0.5758 Remote Similarity NPC88135
0.5758 Remote Similarity NPC223195
0.575 Remote Similarity NPC266553
0.5714 Remote Similarity NPC236761
0.5714 Remote Similarity NPC327092
0.5714 Remote Similarity NPC197207
0.5714 Remote Similarity NPC163707
0.5714 Remote Similarity NPC182541
0.5714 Remote Similarity NPC149070
0.5714 Remote Similarity NPC127074
0.5714 Remote Similarity NPC281883
0.5714 Remote Similarity NPC122962
0.5714 Remote Similarity NPC126915
0.5714 Remote Similarity NPC12904
0.5714 Remote Similarity NPC40965
0.5714 Remote Similarity NPC187058
0.5667 Remote Similarity NPC39977
0.5625 Remote Similarity NPC166804
0.5625 Remote Similarity NPC560

  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 NPC238135 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
0.7027 Intermediate Similarity NPD7536 Approved
0.6552 Remote Similarity NPD8225 Phase 3
0.625 Remote Similarity NPD8549 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7374 Approved
0.6 Remote Similarity NPD8226 Approved
0.5926 Remote Similarity NPD8223 Approved
0.5882 Remote Similarity NPD901 Approved
0.5769 Remote Similarity NPD8547 Phase 2
0.5714 Remote Similarity NPD8814 Phase 3
0.5714 Remote Similarity NPD8224 Approved
0.5714 Remote Similarity NPD9636 Phase 2
0.561 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