Structure

Physi-Chem Properties

Molecular Weight:  136.1
Volume:  152.452
LogP:  1.621
LogD:  1.496
LogS:  -0.03
# Rotatable Bonds:  2
TPSA:  25.78
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.617
Synthetic Accessibility Score:  2.399
Fsp3:  0.5
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:  -4.337
MDCK Permeability:  3.184916204190813e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.144

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.81
Plasma Protein Binding (PPB):  36.52185821533203%
Volume Distribution (VD):  1.686
Pgp-substrate:  63.72825622558594%

ADMET: Metabolism

CYP1A2-inhibitor:  0.513
CYP1A2-substrate:  0.771
CYP2C19-inhibitor:  0.05
CYP2C19-substrate:  0.715
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.402
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.515
CYP3A4-inhibitor:  0.022
CYP3A4-substrate:  0.324

ADMET: Excretion

Clearance (CL):  5.59
Half-life (T1/2):  0.609

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.199
Drug-inuced Liver Injury (DILI):  0.745
AMES Toxicity:  0.036
Rat Oral Acute Toxicity:  0.589
Maximum Recommended Daily Dose:  0.686
Skin Sensitization:  0.757
Carcinogencity:  0.153
Eye Corrosion:  0.165
Eye Irritation:  0.983
Respiratory Toxicity:  0.924

Download Data

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

  Natural Product: NPC262236

Natural Product ID:  NPC262236
Common Name*:   2,3-Diethylpyrazine
IUPAC Name:   2,3-diethylpyrazine
Synonyms:   2,3-Diethyl-Pyrazine
Standard InCHIKey:  GZXXANJCCWGCSV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H12N2/c1-3-7-8(4-2)10-6-5-9-7/h5-6H,3-4H2,1-2H3
SMILES:  CCc1c(CC)nccn1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL327303
PubChem CID:   27458
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001346] Diazines
        • [CHEMONTID:0000067] Pyrazines

*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
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[22272932]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25320841]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8650 Perilla frutescens Species Lamiaceae 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 Log 1/C = 5.134 n.a. PMID[468678]
NPT2 Others Unspecified Potency n.a. 18869 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21171.4 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 NPC262236 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
0.9756 High Similarity NPC277608
0.9753 High Similarity NPC76536
0.8293 Intermediate Similarity NPC270637
0.8171 Intermediate Similarity NPC204104
0.8171 Intermediate Similarity NPC100312
0.6818 Remote Similarity NPC149621
0.6818 Remote Similarity NPC215597
0.679 Remote Similarity NPC284039
0.679 Remote Similarity NPC229
0.6759 Remote Similarity NPC231655
0.6543 Remote Similarity NPC158948
0.6262 Remote Similarity NPC187191
0.6262 Remote Similarity NPC326248
0.6204 Remote Similarity NPC83987
0.614 Remote Similarity NPC27802
0.6055 Remote Similarity NPC273327
0.6036 Remote Similarity NPC155498
0.6018 Remote Similarity NPC76540
0.6 Remote Similarity NPC317307
0.6 Remote Similarity NPC111132
0.5984 Remote Similarity NPC182570
0.5984 Remote Similarity NPC265605
0.5984 Remote Similarity NPC48564
0.5982 Remote Similarity NPC180417
0.5932 Remote Similarity NPC143156
0.5887 Remote Similarity NPC46358
0.5872 Remote Similarity NPC213774
0.587 Remote Similarity NPC470111
0.587 Remote Similarity NPC201380
0.587 Remote Similarity NPC179787
0.5827 Remote Similarity NPC321911
0.5825 Remote Similarity NPC14223
0.5797 Remote Similarity NPC63545
0.5785 Remote Similarity NPC297486
0.5785 Remote Similarity NPC240136
0.5785 Remote Similarity NPC471402
0.5763 Remote Similarity NPC235843
0.576 Remote Similarity NPC290094
0.5755 Remote Similarity NPC469811
0.5738 Remote Similarity NPC91958
0.5714 Remote Similarity NPC473901
0.5714 Remote Similarity NPC27740
0.5678 Remote Similarity NPC327613
0.5672 Remote Similarity NPC251722
0.5672 Remote Similarity NPC314102
0.5669 Remote Similarity NPC146373
0.5669 Remote Similarity NPC245244
0.5669 Remote Similarity NPC166424
0.5649 Remote Similarity NPC256893
0.5648 Remote Similarity NPC9639
0.5625 Remote Similarity NPC202957
0.5625 Remote Similarity NPC169625
0.562 Remote Similarity NPC84268
0.561 Remote Similarity NPC143603

  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 NPC262236 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
0.7449 Intermediate Similarity NPD9472 Phase 3
0.679 Remote Similarity NPD9394 Clinical (unspecified phase)
0.6759 Remote Similarity NPD9099 Clinical (unspecified phase)
0.6759 Remote Similarity NPD9098 Phase 3
0.6735 Remote Similarity NPD8835 Approved
0.6609 Remote Similarity NPD9392 Approved
0.6609 Remote Similarity NPD9396 Approved
0.6585 Remote Similarity NPD715 Phase 3
0.6471 Remote Similarity NPD9101 Discontinued
0.6387 Remote Similarity NPD9598 Discontinued
0.624 Remote Similarity NPD9305 Clinical (unspecified phase)
0.623 Remote Similarity NPD9357 Approved
0.6183 Remote Similarity NPD174 Discontinued
0.6174 Remote Similarity NPD4824 Approved
0.6174 Remote Similarity NPD4823 Approved
0.616 Remote Similarity NPD1095 Clinical (unspecified phase)
0.6129 Remote Similarity NPD9583 Approved
0.608 Remote Similarity NPD2119 Approved
0.608 Remote Similarity NPD2118 Approved
0.6017 Remote Similarity NPD269 Clinical (unspecified phase)
0.6016 Remote Similarity NPD803 Phase 1
0.6016 Remote Similarity NPD809 Discontinued
0.6 Remote Similarity NPD8861 Approved
0.6 Remote Similarity NPD8859 Approved
0.6 Remote Similarity NPD8862 Approved
0.6 Remote Similarity NPD1918 Clinical (unspecified phase)
0.5984 Remote Similarity NPD271 Approved
0.5984 Remote Similarity NPD270 Clinical (unspecified phase)
0.5984 Remote Similarity NPD268 Approved
0.5952 Remote Similarity NPD991 Phase 2
0.5952 Remote Similarity NPD992 Clinical (unspecified phase)
0.5938 Remote Similarity NPD3476 Approved
0.5938 Remote Similarity NPD3475 Approved
0.5897 Remote Similarity NPD757 Phase 3
0.5802 Remote Similarity NPD3944 Approved
0.5802 Remote Similarity NPD3942 Approved
0.5802 Remote Similarity NPD4030 Approved
0.5802 Remote Similarity NPD4029 Approved
0.5802 Remote Similarity NPD4028 Approved
0.5794 Remote Similarity NPD1807 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3576 Approved
0.5714 Remote Similarity NPD3575 Approved
0.568 Remote Similarity NPD5787 Discontinued
0.5645 Remote Similarity NPD4811 Discontinued
0.5643 Remote Similarity NPD1661 Suspended
0.5641 Remote Similarity NPD9082 Approved
0.56 Remote Similarity NPD1389 Clinical (unspecified phase)
0.56 Remote Similarity NPD1390 Phase 1
0.56 Remote Similarity NPD1388 Phase 1

  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