Structure

Physi-Chem Properties

Molecular Weight:  73.09
Volume:  88.737
LogP:  0.696
LogD:  -0.035
LogS:  0.996
# Rotatable Bonds:  2
TPSA:  12.03
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.505
Synthetic Accessibility Score:  2.145
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:  -4.584
MDCK Permeability:  3.99543387175072e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.527
Plasma Protein Binding (PPB):  13.433162689208984%
Volume Distribution (VD):  1.951
Pgp-substrate:  89.26875305175781%

ADMET: Metabolism

CYP1A2-inhibitor:  0.115
CYP1A2-substrate:  0.474
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.818
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.268
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.872
CYP3A4-inhibitor:  0.003
CYP3A4-substrate:  0.222

ADMET: Excretion

Clearance (CL):  9.056
Half-life (T1/2):  0.603

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.098
Drug-inuced Liver Injury (DILI):  0.02
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.639
Maximum Recommended Daily Dose:  0.058
Skin Sensitization:  0.477
Carcinogencity:  0.043
Eye Corrosion:  0.976
Eye Irritation:  0.882
Respiratory Toxicity:  0.972

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

  Natural Product: NPC119368

Natural Product ID:  NPC119368
Common Name*:   Diethylamine
IUPAC Name:   n.a.
Synonyms:   Diethyl-Amine; Diethylamine
Standard InCHIKey:  HPNMFZURTQLUMO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3
SMILES:  CCNCC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004707] Organic nitrogen compounds
      • [CHEMONTID:0000278] Organonitrogen compounds
        • [CHEMONTID:0002449] Amines
          • [CHEMONTID:0002451] Secondary amines
            • [CHEMONTID:0002228] Dialkylamines

*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
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. DOI[10.1021/jf970571j]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[18270436]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[23793896]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. fruit n.a. PMID[240326]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. seed n.a. PMID[24967651]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Pollen Or Spore n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. Database[USDA]

☑ 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
NPO16230 NPC119368 Raw Fruit 0.3 0.3 0.3 mg/100g Database [DUKE]
NPO22132 NPC119368 Other Seed 0.57 0.57 0.57 mg/100g Database [DUKE]

☑ 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
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 7.9 nM PMID[522251]
NPT102 Individual Protein Interleukin-8 Homo sapiens Potency n.a. 66824.2 nM PMID[522251]
NPT2 Others Unspecified Potency n.a. 71951.2 nM PubChem BioAssay data set
NPT27 Others Unspecified log Ks = 1.36 n.a. PMID[522250]

☑ 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 NPC119368 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
0.8077 Intermediate Similarity NPC270175
0.7692 Intermediate Similarity NPC27675
0.7407 Intermediate Similarity NPC232311
0.7407 Intermediate Similarity NPC193536
0.7407 Intermediate Similarity NPC152949
0.7391 Intermediate Similarity NPC27869
0.6897 Remote Similarity NPC21157
0.6897 Remote Similarity NPC95589
0.6667 Remote Similarity NPC28081
0.6667 Remote Similarity NPC309330
0.6667 Remote Similarity NPC320889
0.6667 Remote Similarity NPC258096
0.6538 Remote Similarity NPC125872
0.6538 Remote Similarity NPC83032
0.6364 Remote Similarity NPC203203
0.625 Remote Similarity NPC309715
0.625 Remote Similarity NPC328729
0.619 Remote Similarity NPC226340
0.6154 Remote Similarity NPC306277
0.6154 Remote Similarity NPC318947
0.6 Remote Similarity NPC329501
0.6 Remote Similarity NPC473035
0.5882 Remote Similarity NPC74599
0.5833 Remote Similarity NPC167301
0.5714 Remote Similarity NPC263968
0.5676 Remote Similarity NPC321202
0.5667 Remote Similarity NPC313882

  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 NPC119368 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
0.7692 Intermediate Similarity NPD9063 Approved
0.7692 Intermediate Similarity NPD9064 Approved
0.7407 Intermediate Similarity NPD8544 Approved
0.7407 Intermediate Similarity NPD9465 Approved
0.7241 Intermediate Similarity NPD1156 Clinical (unspecified phase)
0.6897 Remote Similarity NPD401 Approved
0.6818 Remote Similarity NPD8816 Approved
0.6667 Remote Similarity NPD8560 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7383 Phase 3
0.625 Remote Similarity NPD8556 Phase 3
0.6 Remote Similarity NPD2707 Clinical (unspecified phase)
0.5938 Remote Similarity NPD2276 Clinical (unspecified phase)
0.5714 Remote Similarity NPD9059 Approved
0.5676 Remote Similarity NPD2273 Clinical (unspecified phase)
0.5676 Remote Similarity NPD1463 Clinical (unspecified phase)

  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