Structure

Physi-Chem Properties

Molecular Weight:  276.1
Volume:  254.496
LogP:  -3.336
LogD:  -0.658
LogS:  -0.81
# Rotatable Bonds:  10
TPSA:  167.02
# H-Bond Aceptor:  9
# H-Bond Donor:  6
# Rings:  0
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.343
Synthetic Accessibility Score:  2.682
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.461
MDCK Permeability:  0.001963655464351177
Pgp-inhibitor:  0.0
Pgp-substrate:  0.135
Human Intestinal Absorption (HIA):  0.403
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.12

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.095
Plasma Protein Binding (PPB):  15.17445182800293%
Volume Distribution (VD):  0.427
Pgp-substrate:  72.66876983642578%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.007
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.026
CYP2C9-inhibitor:  0.039
CYP2C9-substrate:  0.556
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.104
CYP3A4-inhibitor:  0.014
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  2.081
Half-life (T1/2):  0.849

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.04
Drug-inuced Liver Injury (DILI):  0.017
AMES Toxicity:  0.027
Rat Oral Acute Toxicity:  0.001
Maximum Recommended Daily Dose:  0.009
Skin Sensitization:  0.065
Carcinogencity:  0.067
Eye Corrosion:  0.003
Eye Irritation:  0.066
Respiratory Toxicity:  0.022

Download Data

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

  Natural Product: NPC143722

Natural Product ID:  NPC143722
Common Name*:   Glu-Glu
IUPAC Name:   (2S)-2-[[(2S)-2-amino-4-carboxybutanoyl]amino]pentanedioic acid
Synonyms:   Glu(Glu); Glu-Glu
Standard InCHIKey:  KOSRFJWDECSPRO-WDSKDSINSA-N
Standard InCHI:  InChI=1S/C10H16N2O7/c11-5(1-3-7(13)14)9(17)12-6(10(18)19)2-4-8(15)16/h5-6H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
SMILES:  OC(=O)CC[C@@H](C(=O)O)N=C([C@H](CCC(=O)O)N)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL318315
PubChem CID:   439500
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000348] Peptides
            • [CHEMONTID:0004830] Dipeptides

*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
NPO30193 Mycoplasma genitalium Species Mycoplasmataceae Bacteria n.a. n.a. n.a. PMID[22817898]

☑ 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
NPT4644 Individual Protein Glutamate carboxypeptidase II Rattus norvegicus IC50 = 750.0 nM PMID[510246]
NPT1237 Individual Protein Oligopeptide transporter small intestine isoform Homo sapiens EC50 = 1000000.0 nM PMID[510247]
NPT1237 Individual Protein Oligopeptide transporter small intestine isoform Homo sapiens max activation = 111.0 % PMID[510247]
NPT1237 Individual Protein Oligopeptide transporter small intestine isoform Homo sapiens IC50 = 620000.0 nM PMID[510247]
NPT1237 Individual Protein Oligopeptide transporter small intestine isoform Homo sapiens Ratio = 110.0 n.a. PMID[510247]
NPT21154 SINGLE PROTEIN General amino-acid permease GAP1 Saccharomyces cerevisiae Inhibition < 15.0 % PMID[510248]

☑ 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 NPC143722 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
0.9464 High Similarity NPC321536
0.9273 High Similarity NPC325985
0.8929 High Similarity NPC38463
0.875 High Similarity NPC322573
0.8727 High Similarity NPC190184
0.8727 High Similarity NPC197087
0.8689 High Similarity NPC325597
0.8689 High Similarity NPC174304
0.8525 High Similarity NPC289691
0.8393 Intermediate Similarity NPC263065
0.8393 Intermediate Similarity NPC189178
0.8364 Intermediate Similarity NPC273330
0.8364 Intermediate Similarity NPC137958
0.8361 Intermediate Similarity NPC327252
0.8281 Intermediate Similarity NPC319046
0.8167 Intermediate Similarity NPC321468
0.8167 Intermediate Similarity NPC254541
0.8167 Intermediate Similarity NPC316826
0.8167 Intermediate Similarity NPC317143
0.8167 Intermediate Similarity NPC327748
0.8167 Intermediate Similarity NPC320598
0.8154 Intermediate Similarity NPC126779
0.8033 Intermediate Similarity NPC327170
0.8033 Intermediate Similarity NPC329564
0.8 Intermediate Similarity NPC189301
0.8 Intermediate Similarity NPC176164
0.7833 Intermediate Similarity NPC318260
0.7833 Intermediate Similarity NPC317147
0.7797 Intermediate Similarity NPC2801
0.7627 Intermediate Similarity NPC316889
0.7627 Intermediate Similarity NPC321118
0.7586 Intermediate Similarity NPC29950
0.7586 Intermediate Similarity NPC19576
0.75 Intermediate Similarity NPC327831
0.7424 Intermediate Similarity NPC325534
0.7414 Intermediate Similarity NPC327239
0.7321 Intermediate Similarity NPC297220
0.7313 Intermediate Similarity NPC118524
0.7143 Intermediate Similarity NPC327698
0.7143 Intermediate Similarity NPC329263
0.7143 Intermediate Similarity NPC118459
0.7069 Intermediate Similarity NPC140872
0.7069 Intermediate Similarity NPC153370
0.7069 Intermediate Similarity NPC93081
0.7042 Intermediate Similarity NPC315897
0.7 Intermediate Similarity NPC322946
0.6984 Remote Similarity NPC278209
0.6949 Remote Similarity NPC324825
0.6949 Remote Similarity NPC112890
0.6949 Remote Similarity NPC316231
0.6949 Remote Similarity NPC328378
0.6923 Remote Similarity NPC321419
0.6901 Remote Similarity NPC328457
0.6885 Remote Similarity NPC329495
0.6866 Remote Similarity NPC106216
0.6866 Remote Similarity NPC88898
0.6765 Remote Similarity NPC50047
0.6667 Remote Similarity NPC470108
0.6667 Remote Similarity NPC162620
0.6667 Remote Similarity NPC245027
0.6667 Remote Similarity NPC226027
0.6667 Remote Similarity NPC68974
0.6667 Remote Similarity NPC177191
0.6667 Remote Similarity NPC84636
0.6667 Remote Similarity NPC62045
0.6667 Remote Similarity NPC59867
0.6667 Remote Similarity NPC43204
0.6667 Remote Similarity NPC174246
0.662 Remote Similarity NPC472579
0.6618 Remote Similarity NPC315744
0.6571 Remote Similarity NPC222327
0.6571 Remote Similarity NPC188231
0.6571 Remote Similarity NPC470109
0.6557 Remote Similarity NPC125736
0.6557 Remote Similarity NPC319175
0.6508 Remote Similarity NPC279661
0.6508 Remote Similarity NPC183845
0.6486 Remote Similarity NPC476248
0.6479 Remote Similarity NPC470110
0.6429 Remote Similarity NPC168375
0.6429 Remote Similarity NPC121517
0.6429 Remote Similarity NPC326992
0.6364 Remote Similarity NPC18188
0.6351 Remote Similarity NPC55274
0.6329 Remote Similarity NPC475542
0.6324 Remote Similarity NPC118429
0.6286 Remote Similarity NPC278881
0.625 Remote Similarity NPC53858
0.625 Remote Similarity NPC81647
0.625 Remote Similarity NPC84128
0.623 Remote Similarity NPC227850
0.6207 Remote Similarity NPC167986
0.6207 Remote Similarity NPC291186
0.6207 Remote Similarity NPC276294
0.619 Remote Similarity NPC155156
0.619 Remote Similarity NPC200550
0.6182 Remote Similarity NPC69179
0.6164 Remote Similarity NPC133183
0.6154 Remote Similarity NPC37681
0.6143 Remote Similarity NPC57420
0.6143 Remote Similarity NPC103130
0.6143 Remote Similarity NPC226453
0.6125 Remote Similarity NPC314466
0.6119 Remote Similarity NPC11433
0.6119 Remote Similarity NPC245346
0.6119 Remote Similarity NPC302003
0.6102 Remote Similarity NPC132307
0.6102 Remote Similarity NPC126925
0.6102 Remote Similarity NPC323974
0.6102 Remote Similarity NPC325097
0.6098 Remote Similarity NPC95478
0.6098 Remote Similarity NPC155670
0.6098 Remote Similarity NPC145748
0.6087 Remote Similarity NPC477644
0.6081 Remote Similarity NPC478256
0.6066 Remote Similarity NPC136159
0.6047 Remote Similarity NPC477729
0.6032 Remote Similarity NPC319110
0.6032 Remote Similarity NPC329181
0.6032 Remote Similarity NPC50457
0.6029 Remote Similarity NPC276928
0.6029 Remote Similarity NPC64250
0.6029 Remote Similarity NPC268927
0.6024 Remote Similarity NPC227051
0.6 Remote Similarity NPC285322
0.6 Remote Similarity NPC208793
0.5972 Remote Similarity NPC327985
0.5949 Remote Similarity NPC314680
0.5949 Remote Similarity NPC191774
0.5949 Remote Similarity NPC316242
0.5938 Remote Similarity NPC202525
0.5915 Remote Similarity NPC145658
0.5902 Remote Similarity NPC185755
0.5902 Remote Similarity NPC49952
0.5902 Remote Similarity NPC213876
0.5902 Remote Similarity NPC136476
0.5882 Remote Similarity NPC190385
0.5875 Remote Similarity NPC315131
0.5875 Remote Similarity NPC478017
0.5875 Remote Similarity NPC315535
0.5873 Remote Similarity NPC80350
0.5873 Remote Similarity NPC17244
0.5867 Remote Similarity NPC477642
0.5867 Remote Similarity NPC476291
0.5867 Remote Similarity NPC476285
0.5862 Remote Similarity NPC53449
0.5862 Remote Similarity NPC237525
0.5862 Remote Similarity NPC66043
0.5862 Remote Similarity NPC326212
0.5846 Remote Similarity NPC245768
0.5833 Remote Similarity NPC198301
0.5833 Remote Similarity NPC262615
0.5823 Remote Similarity NPC472594
0.5806 Remote Similarity NPC101249
0.5797 Remote Similarity NPC473599
0.5781 Remote Similarity NPC315977
0.5758 Remote Similarity NPC322091
0.5758 Remote Similarity NPC60672
0.5733 Remote Similarity NPC474299
0.5733 Remote Similarity NPC322274
0.5733 Remote Similarity NPC474298
0.5733 Remote Similarity NPC473985
0.5733 Remote Similarity NPC475808
0.5733 Remote Similarity NPC28348
0.5714 Remote Similarity NPC87359
0.5714 Remote Similarity NPC327542
0.5714 Remote Similarity NPC477641
0.5714 Remote Similarity NPC141325
0.5714 Remote Similarity NPC180402
0.5714 Remote Similarity NPC116709
0.5714 Remote Similarity NPC320865
0.5714 Remote Similarity NPC272614
0.5714 Remote Similarity NPC477643
0.5714 Remote Similarity NPC21290
0.569 Remote Similarity NPC327250
0.5645 Remote Similarity NPC248970
0.5645 Remote Similarity NPC309658
0.5645 Remote Similarity NPC306238
0.5641 Remote Similarity NPC43219
0.5641 Remote Similarity NPC138435
0.5641 Remote Similarity NPC320221
0.5634 Remote Similarity NPC314510
0.5634 Remote Similarity NPC322206
0.5625 Remote Similarity NPC193989
0.5625 Remote Similarity NPC315780
0.5625 Remote Similarity NPC170739
0.5625 Remote Similarity NPC152451
0.5625 Remote Similarity NPC270805
0.5625 Remote Similarity NPC93888
0.5616 Remote Similarity NPC41429
0.5614 Remote Similarity NPC63621
0.561 Remote Similarity NPC157173
0.56 Remote Similarity NPC250953

  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 NPC143722 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
0.9286 High Similarity NPD9433 Approved
0.8727 High Similarity NPD8785 Approved
0.871 High Similarity NPD1429 Clinical (unspecified phase)
0.8689 High Similarity NPD348 Approved
0.85 High Similarity NPD574 Approved
0.8413 Intermediate Similarity NPD886 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD9204 Approved
0.8393 Intermediate Similarity NPD9205 Approved
0.8364 Intermediate Similarity NPD8871 Approved
0.8364 Intermediate Similarity NPD8872 Phase 3
0.8361 Intermediate Similarity NPD575 Clinical (unspecified phase)
0.8281 Intermediate Similarity NPD4241 Registered
0.8281 Intermediate Similarity NPD337 Discontinued
0.8154 Intermediate Similarity NPD4242 Approved
0.807 Intermediate Similarity NPD8851 Phase 1
0.791 Intermediate Similarity NPD2262 Clinical (unspecified phase)
0.7794 Intermediate Similarity NPD6944 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD8847 Approved
0.7586 Intermediate Similarity NPD61 Approved
0.7586 Intermediate Similarity NPD8846 Approved
0.7536 Intermediate Similarity NPD1147 Phase 2
0.7424 Intermediate Similarity NPD8952 Approved
0.7069 Intermediate Similarity NPD8809 Approved
0.7069 Intermediate Similarity NPD8808 Approved
0.7069 Intermediate Similarity NPD8614 Approved
0.7042 Intermediate Similarity NPD1825 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD7643 Phase 1
0.7 Intermediate Similarity NPD9441 Phase 2
0.6949 Remote Similarity NPD9044 Approved
0.6944 Remote Similarity NPD366 Approved
0.6883 Remote Similarity NPD1125 Discovery
0.6812 Remote Similarity NPD9421 Phase 1
0.68 Remote Similarity NPD3160 Suspended
0.6714 Remote Similarity NPD9451 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9018 Approved
0.6667 Remote Similarity NPD9016 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9017 Approved
0.6552 Remote Similarity NPD9658 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8623 Phase 1
0.6324 Remote Similarity NPD9014 Approved
0.6322 Remote Similarity NPD573 Clinical (unspecified phase)
0.629 Remote Similarity NPD329 Discontinued
0.6267 Remote Similarity NPD9109 Discontinued
0.6207 Remote Similarity NPD8805 Approved
0.6207 Remote Similarity NPD8804 Approved
0.6154 Remote Similarity NPD8971 Approved
0.6145 Remote Similarity NPD7759 Phase 2
0.6145 Remote Similarity NPD7760 Phase 2
0.6143 Remote Similarity NPD9046 Phase 3
0.6143 Remote Similarity NPD9047 Approved
0.6143 Remote Similarity NPD9045 Approved
0.6143 Remote Similarity NPD9048 Approved
0.6119 Remote Similarity NPD8865 Approved
0.6111 Remote Similarity NPD9233 Phase 3
0.6111 Remote Similarity NPD2263 Discontinued
0.6111 Remote Similarity NPD842 Phase 3
0.6111 Remote Similarity NPD9232 Phase 2
0.6111 Remote Similarity NPD8842 Clinical (unspecified phase)
0.6111 Remote Similarity NPD9231 Phase 3
0.6102 Remote Similarity NPD9019 Approved
0.6102 Remote Similarity NPD8798 Approved
0.6061 Remote Similarity NPD8981 Clinical (unspecified phase)
0.6061 Remote Similarity NPD9454 Approved
0.6061 Remote Similarity NPD8980 Approved
0.6061 Remote Similarity NPD8979 Approved
0.6 Remote Similarity NPD8610 Approved
0.6 Remote Similarity NPD9419 Clinical (unspecified phase)
0.5976 Remote Similarity NPD4829 Discontinued
0.5949 Remote Similarity NPD4278 Clinical (unspecified phase)
0.5946 Remote Similarity NPD3724 Clinical (unspecified phase)
0.5904 Remote Similarity NPD3733 Clinical (unspecified phase)
0.5902 Remote Similarity NPD8982 Approved
0.5882 Remote Similarity NPD9023 Clinical (unspecified phase)
0.5875 Remote Similarity NPD7917 Clinical (unspecified phase)
0.5875 Remote Similarity NPD7918 Clinical (unspecified phase)
0.5873 Remote Similarity NPD9230 Discontinued
0.5862 Remote Similarity NPD3716 Discontinued
0.5833 Remote Similarity NPD6437 Approved
0.5833 Remote Similarity NPD6438 Approved
0.5824 Remote Similarity NPD6428 Approved
0.5811 Remote Similarity NPD322 Phase 1
0.5811 Remote Similarity NPD9452 Clinical (unspecified phase)
0.5806 Remote Similarity NPD8867 Approved
0.5806 Remote Similarity NPD8866 Approved
0.5806 Remote Similarity NPD8850 Approved
0.5789 Remote Similarity NPD5382 Phase 2
0.5761 Remote Similarity NPD8038 Phase 2
0.5735 Remote Similarity NPD9425 Approved
0.5714 Remote Similarity NPD362 Phase 1
0.5714 Remote Similarity NPD8211 Approved
0.5714 Remote Similarity NPD2256 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8210 Phase 3
0.5663 Remote Similarity NPD1448 Clinical (unspecified phase)
0.5645 Remote Similarity NPD8801 Approved
0.5645 Remote Similarity NPD8870 Approved
0.5625 Remote Similarity NPD8947 Approved
0.5625 Remote Similarity NPD8803 Clinical (unspecified phase)
0.5625 Remote Similarity NPD8624 Approved
0.5625 Remote Similarity NPD8946 Approved
0.5625 Remote Similarity NPD9021 Approved
0.5625 Remote Similarity NPD8802 Approved
0.5618 Remote Similarity NPD4261 Phase 1
0.5604 Remote Similarity NPD8394 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