Structure

Physi-Chem Properties

Molecular Weight:  276.12
Volume:  269.73
LogP:  1.395
LogD:  0.761
LogS:  -1.462
# Rotatable Bonds:  11
TPSA:  99.13
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.499
Synthetic Accessibility Score:  2.415
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.575
MDCK Permeability:  0.0002064174332190305
Pgp-inhibitor:  0.141
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.894
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.946
Plasma Protein Binding (PPB):  15.412297248840332%
Volume Distribution (VD):  0.373
Pgp-substrate:  68.73526763916016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.746
CYP1A2-substrate:  0.107
CYP2C19-inhibitor:  0.689
CYP2C19-substrate:  0.421
CYP2C9-inhibitor:  0.099
CYP2C9-substrate:  0.117
CYP2D6-inhibitor:  0.026
CYP2D6-substrate:  0.107
CYP3A4-inhibitor:  0.026
CYP3A4-substrate:  0.347

ADMET: Excretion

Clearance (CL):  8.641
Half-life (T1/2):  0.633

ADMET: Toxicity

hERG Blockers:  0.175
Human Hepatotoxicity (H-HT):  0.016
Drug-inuced Liver Injury (DILI):  0.756
AMES Toxicity:  0.04
Rat Oral Acute Toxicity:  0.001
Maximum Recommended Daily Dose:  0.021
Skin Sensitization:  0.051
Carcinogencity:  0.029
Eye Corrosion:  0.741
Eye Irritation:  0.863
Respiratory Toxicity:  0.01

Download Data

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

  Natural Product: NPC179624

Natural Product ID:  NPC179624
Common Name*:   Triethyl Citrate
IUPAC Name:   triethyl 2-hydroxypropane-1,2,3-tricarboxylate
Synonyms:   E1505; Triethyl Citrate
Standard InCHIKey:  DOOTYTYQINUNNV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H20O7/c1-4-17-9(13)7-12(16,11(15)19-6-3)8-10(14)18-5-2/h16H,4-8H2,1-3H3
SMILES:  CCOC(=O)C(CC(=O)OCC)(CC(=O)OCC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464988
PubChem CID:   6506
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO7611 Sclerotium poriae cocos Species Typhulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7611 Sclerotium poriae cocos Species Typhulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 43277.1 nM PubChem BioAssay data set
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens Activity = 18.0 % PMID[569855]
NPT2 Others Unspecified Potency n.a. 38570.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT32 Organism Mus musculus Mus musculus Activity = -13.6 % PMID[569854]

☑ 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 NPC179624 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
0.963 High Similarity NPC198377
0.9444 High Similarity NPC68743
0.9444 High Similarity NPC60830
0.9074 High Similarity NPC65985
0.8448 Intermediate Similarity NPC61567
0.8333 Intermediate Similarity NPC293378
0.8246 Intermediate Similarity NPC6883
0.807 Intermediate Similarity NPC19676
0.807 Intermediate Similarity NPC323401
0.7222 Intermediate Similarity NPC310220
0.7164 Intermediate Similarity NPC241949
0.7143 Intermediate Similarity NPC133771
0.7069 Intermediate Similarity NPC46254
0.6984 Remote Similarity NPC293692
0.6984 Remote Similarity NPC220922
0.6964 Remote Similarity NPC242655
0.6964 Remote Similarity NPC38891
0.6812 Remote Similarity NPC32148
0.6812 Remote Similarity NPC469925
0.6721 Remote Similarity NPC277878
0.6613 Remote Similarity NPC196612
0.6545 Remote Similarity NPC240109
0.6486 Remote Similarity NPC125164
0.6471 Remote Similarity NPC258690
0.6471 Remote Similarity NPC317651
0.6452 Remote Similarity NPC317680
0.6447 Remote Similarity NPC474003
0.6438 Remote Similarity NPC96322
0.6429 Remote Similarity NPC100742
0.6429 Remote Similarity NPC192402
0.6429 Remote Similarity NPC97444
0.6429 Remote Similarity NPC24751
0.6429 Remote Similarity NPC121018
0.6429 Remote Similarity NPC35661
0.6429 Remote Similarity NPC19044
0.6379 Remote Similarity NPC270088
0.6364 Remote Similarity NPC320032
0.6338 Remote Similarity NPC286842
0.6333 Remote Similarity NPC172086
0.6333 Remote Similarity NPC247546
0.6324 Remote Similarity NPC469923
0.6316 Remote Similarity NPC313565
0.6316 Remote Similarity NPC228782
0.6316 Remote Similarity NPC259982
0.6296 Remote Similarity NPC206924
0.6269 Remote Similarity NPC17935
0.6235 Remote Similarity NPC65359
0.6232 Remote Similarity NPC268243
0.6207 Remote Similarity NPC319680
0.6184 Remote Similarity NPC228411
0.6182 Remote Similarity NPC128713
0.6163 Remote Similarity NPC469627
0.6154 Remote Similarity NPC470014
0.6119 Remote Similarity NPC322855
0.6056 Remote Similarity NPC469926
0.6029 Remote Similarity NPC323945
0.6029 Remote Similarity NPC475821
0.6029 Remote Similarity NPC470363
0.6027 Remote Similarity NPC82315
0.6026 Remote Similarity NPC108014
0.6 Remote Similarity NPC328180
0.6 Remote Similarity NPC325773
0.6 Remote Similarity NPC320588
0.6 Remote Similarity NPC53463
0.6 Remote Similarity NPC278028
0.6 Remote Similarity NPC235788
0.6 Remote Similarity NPC23155
0.6 Remote Similarity NPC469937
0.5965 Remote Similarity NPC320331
0.5949 Remote Similarity NPC475616
0.5946 Remote Similarity NPC28526
0.5942 Remote Similarity NPC320296
0.5921 Remote Similarity NPC473699
0.5921 Remote Similarity NPC475232
0.5921 Remote Similarity NPC51249
0.5921 Remote Similarity NPC474100
0.5921 Remote Similarity NPC473775
0.5921 Remote Similarity NPC475260
0.5893 Remote Similarity NPC325454
0.589 Remote Similarity NPC57788
0.589 Remote Similarity NPC53879
0.5857 Remote Similarity NPC10659
0.5833 Remote Similarity NPC51267
0.5833 Remote Similarity NPC12040
0.5833 Remote Similarity NPC76881
0.5833 Remote Similarity NPC476330
0.5823 Remote Similarity NPC83108
0.5823 Remote Similarity NPC214030
0.5814 Remote Similarity NPC53158
0.5797 Remote Similarity NPC469924
0.5789 Remote Similarity NPC222792
0.5789 Remote Similarity NPC316217
0.5783 Remote Similarity NPC320936
0.5778 Remote Similarity NPC470191
0.5778 Remote Similarity NPC475900
0.5775 Remote Similarity NPC474552
0.5765 Remote Similarity NPC475491
0.5765 Remote Similarity NPC469626
0.5765 Remote Similarity NPC476717
0.573 Remote Similarity NPC475788
0.5714 Remote Similarity NPC158416
0.5714 Remote Similarity NPC476009
0.5714 Remote Similarity NPC317945
0.5714 Remote Similarity NPC76862
0.5714 Remote Similarity NPC469921
0.5714 Remote Similarity NPC115995
0.5714 Remote Similarity NPC470883
0.5714 Remote Similarity NPC328954
0.5714 Remote Similarity NPC39859
0.5699 Remote Similarity NPC324667
0.5698 Remote Similarity NPC314364
0.5696 Remote Similarity NPC472594
0.5682 Remote Similarity NPC316228
0.5676 Remote Similarity NPC206601
0.5667 Remote Similarity NPC247877
0.5667 Remote Similarity NPC309127
0.5647 Remote Similarity NPC478111
0.5641 Remote Similarity NPC215030
0.5641 Remote Similarity NPC317212
0.5641 Remote Similarity NPC472595
0.5634 Remote Similarity NPC469922
0.5632 Remote Similarity NPC119740
0.5632 Remote Similarity NPC150063
0.5614 Remote Similarity NPC38930
0.5604 Remote Similarity NPC322188
0.56 Remote Similarity NPC97736
0.56 Remote Similarity NPC250619
0.56 Remote Similarity NPC50228

  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 NPC179624 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
0.8333 Intermediate Similarity NPD71 Approved
0.8333 Intermediate Similarity NPD9126 Approved
0.8333 Intermediate Similarity NPD9129 Approved
0.8148 Intermediate Similarity NPD9130 Phase 3
0.8148 Intermediate Similarity NPD9125 Approved
0.8148 Intermediate Similarity NPD109 Approved
0.8148 Intermediate Similarity NPD9124 Approved
0.8148 Intermediate Similarity NPD9128 Approved
0.8148 Intermediate Similarity NPD9123 Approved
0.8148 Intermediate Similarity NPD9127 Approved
0.8148 Intermediate Similarity NPD9122 Approved
0.8148 Intermediate Similarity NPD70 Approved
0.8148 Intermediate Similarity NPD9121 Approved
0.8148 Intermediate Similarity NPD108 Approved
0.6984 Remote Similarity NPD8959 Approved
0.6812 Remote Similarity NPD896 Approved
0.6812 Remote Similarity NPD897 Approved
0.6812 Remote Similarity NPD898 Approved
0.6721 Remote Similarity NPD9011 Approved
0.6721 Remote Similarity NPD9009 Approved
0.6721 Remote Similarity NPD72 Approved
0.6721 Remote Similarity NPD9007 Approved
0.6721 Remote Similarity NPD9010 Approved
0.6721 Remote Similarity NPD8960 Approved
0.6721 Remote Similarity NPD64 Approved
0.6721 Remote Similarity NPD65 Approved
0.6721 Remote Similarity NPD9008 Approved
0.6721 Remote Similarity NPD66 Approved
0.6471 Remote Similarity NPD8961 Approved
0.6429 Remote Similarity NPD8605 Approved
0.6429 Remote Similarity NPD8600 Approved
0.6429 Remote Similarity NPD8598 Approved
0.6429 Remote Similarity NPD8604 Approved
0.6429 Remote Similarity NPD8599 Approved
0.6429 Remote Similarity NPD8602 Approved
0.6429 Remote Similarity NPD8603 Approved
0.6429 Remote Similarity NPD8601 Approved
0.64 Remote Similarity NPD376 Approved
0.64 Remote Similarity NPD11 Approved
0.6333 Remote Similarity NPD9003 Clinical (unspecified phase)
0.6333 Remote Similarity NPD9004 Approved
0.6333 Remote Similarity NPD9005 Phase 3
0.6308 Remote Similarity NPD73 Approved
0.6076 Remote Similarity NPD7329 Approved
0.6032 Remote Similarity NPD9001 Clinical (unspecified phase)
0.6032 Remote Similarity NPD9002 Approved
0.6 Remote Similarity NPD3728 Approved
0.6 Remote Similarity NPD3730 Approved
0.5974 Remote Similarity NPD1453 Phase 1
0.5921 Remote Similarity NPD3181 Approved
0.5897 Remote Similarity NPD2689 Clinical (unspecified phase)
0.5806 Remote Similarity NPD2266 Phase 2
0.5741 Remote Similarity NPD900 Approved
0.5694 Remote Similarity NPD7909 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