Natural Product: NPC190385

Natural Product IDNPC190385
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 4-Hydroxy Isoleucine
IUPAC Name (2S,3R,4S)-2-amino-4-hydroxy-3-methylpentanoic acid
Synonyms 4-Hydroxy Isoleucine
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL508094
PubChem CID 6918732
40561613
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:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids and derivatives
              • [CHEMONTID:0004330] Isoleucine and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey OSCCDBFHNMXNME-YUPRTTJUSA-N
Standard InCHI InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4-,5-/m0/s1
SMILES C[C@@H]([C@@H]([C@@H](C(=O)O)N)C)O

  Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11599360]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. seed n.a. PMID[21381697]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[37120447]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7639 Senecio isatideus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14100 Persea kusanoi Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2263 Croton megistocarpus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8075 Cacospongia scalaris Species Thorectidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7639 Senecio isatideus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8075 Cacospongia scalaris Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2263 Croton megistocarpus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14100 Persea kusanoi Species Lauraceae 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 Organism Name 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

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 26.4 % DOI[10.6019/CHEMBL4495564]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.1154 % DOI[10.6019/CHEMBL4495564]
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = -7.36 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = 21.36 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 11.94 % DOI[10.21203/rs.3.rs-23951/v1]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.0 % DOI[10.6019/CHEMBL4495565]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.19 % DOI[10.6019/CHEMBL4495565]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 33.0 % PMID[16246556]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 22.0 % PMID[16246556]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 8.7 % PMID[16246556]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 14.0 % PMID[16246556]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 4.9 % PMID[16246556]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Ratio = 39.0 % PMID[16246556]
NPT2 Others Unspecified n.a. Activity = 45.0 pg/hr PMID[18621529]
NPT2 Others Unspecified n.a. Activity = 100.0 pg/hr PMID[18621529]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC190385 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.6818 Remote Similarity NPC270805
0.6818 Remote Similarity NPC93888
0.6667 Remote Similarity NPC132307
0.6667 Remote Similarity NPC126925
0.6 Remote Similarity NPC116709
0.6 Remote Similarity NPC21290
0.6 Remote Similarity NPC272614
0.5833 Remote Similarity NPC84636
0.5833 Remote Similarity NPC226027
0.5833 Remote Similarity NPC174246
0.5833 Remote Similarity NPC43204
0.5652 Remote Similarity NPC226265
0.5652 Remote Similarity NPC219143
0.5652 Remote Similarity NPC254482
0.5652 Remote Similarity NPC110533
0.5417 Remote Similarity NPC317691
0.5217 Remote Similarity NPC63621
0.5217 Remote Similarity NPC326992
0.5217 Remote Similarity NPC121517
0.5217 Remote Similarity NPC168375
0.5217 Remote Similarity NPC600066
0.52 Remote Similarity NPC245027
0.52 Remote Similarity NPC43169
0.52 Remote Similarity NPC162620
0.52 Remote Similarity NPC327895
0.52 Remote Similarity NPC62045
0.52 Remote Similarity NPC112224

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC190385 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
1.0 High Similarity NPD9023 Clinical (unspecified phase)
0.6818 Remote Similarity NPD8624 Phase 2
0.6667 Remote Similarity NPD8798 Phase 2
0.6087 Remote Similarity NPD8801 Phase 4
0.6 Remote Similarity NPD8210 Phase 3
0.6 Remote Similarity NPD8211 Approved
0.5833 Remote Similarity NPD9017 Phase 2
0.5652 Remote Similarity NPD8215 Phase 4
0.5652 Remote Similarity NPD8216 Phase 3
0.5652 Remote Similarity NPD8217 Phase 3
0.5417 Remote Similarity NPD8214 Approved
0.52 Remote Similarity NPD9018 Phase 3

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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