Structure

Physi-Chem Properties

Molecular Weight:  133.04
Volume:  118.625
LogP:  -3.721
LogD:  -0.79
LogS:  -1.137
# Rotatable Bonds:  3
TPSA:  100.62
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  0
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.452
Synthetic Accessibility Score:  2.412
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:  -6.173
MDCK Permeability:  0.0075979228131473064
Pgp-inhibitor:  0.0
Pgp-substrate:  0.056
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.358
Plasma Protein Binding (PPB):  9.952251434326172%
Volume Distribution (VD):  0.289
Pgp-substrate:  84.22208404541016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.023
CYP2C19-inhibitor:  0.039
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.511
CYP2D6-inhibitor:  0.037
CYP2D6-substrate:  0.134
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.006

ADMET: Excretion

Clearance (CL):  9.451
Half-life (T1/2):  0.667

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.085
Drug-inuced Liver Injury (DILI):  0.015
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.031
Maximum Recommended Daily Dose:  0.006
Skin Sensitization:  0.158
Carcinogencity:  0.044
Eye Corrosion:  0.026
Eye Irritation:  0.205
Respiratory Toxicity:  0.086

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  Natural Product: NPC193154

Natural Product ID:  NPC193154
Common Name*:   GROIBJFMWIHJHX-WNQIDUERSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  GROIBJFMWIHJHX-WNQIDUERSA-N
Standard InCHI:  InChI=1S/C5H11NO2.C4H7NO4/c1-6(2,3)4-5(7)8;5-2(4(8)9)1-3(6)7/h4H2,1-3H3;2H,1,5H2,(H,6,7)(H,8,9)/t;2-/m.0/s1
SMILES:  C[N+](C)(C)CC(=O)[O-].C([C@@H](C(=O)O)N)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   104358
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:0004317] Aspartic acid 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
NPO24846 Astragalus membranaceus Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1021/np50075a009]
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[12467621]
NPO12068 Firmiana simplex Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[16124753]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. root n.a. PMID[16212233]
NPO24846 Astragalus membranaceus Species Fabaceae Eukaryota n.a. root n.a. PMID[17253088]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. whole plant n.a. PMID[17473466]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[18270436]
NPO28146 Liriope spicata Species Asparagaceae Eukaryota Tuberous root n.a. n.a. PMID[19874043]
NPO17823 Lycium chinense Species Solanaceae Eukaryota root bark n.a. n.a. PMID[23282106]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. PMID[23357036]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[23793896]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. PMID[24634069]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. seed n.a. PMID[24967651]
NPO24846 Astragalus membranaceus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25068786]
NPO17823 Lycium chinense Species Solanaceae Eukaryota Root Bark n.a. n.a. PMID[26982999]
NPO24846 Astragalus membranaceus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[30758201]
NPO8159 Digenea simplex Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[31117523]
NPO25583 Beta vulgaris Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[33118348]
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[9090870]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO25583 Beta vulgaris Species Chenopodiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae 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]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25583 Beta vulgaris Species Chenopodiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25583 Beta vulgaris Species Chenopodiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO12299 Dens draconis n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO11411 Gossypium herbaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8159 Digenea simplex Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28146 Liriope spicata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25583 Beta vulgaris Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12068 Firmiana simplex Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31531 Adhatoda vasica n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4363 Amaranthus caudatus Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24846 Astragalus membranaceus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31566 Massa fermentata n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO11411 Gossypium herbaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4363 Amaranthus caudatus Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28146 Liriope spicata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25583 Beta vulgaris Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12299 Dens draconis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24846 Astragalus membranaceus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8159 Digenea simplex Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12068 Firmiana simplex Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12068 Firmiana simplex Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4363 Amaranthus caudatus Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31531 Adhatoda vasica n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24846 Astragalus membranaceus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25583 Beta vulgaris Species Chenopodiaceae 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]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28146 Liriope spicata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24846 Astragalus membranaceus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25583 Beta vulgaris Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11411 Gossypium herbaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4363 Amaranthus caudatus Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8159 Digenea simplex Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12068 Firmiana simplex Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28146 Liriope spicata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24846 Astragalus membranaceus Species Fabaceae 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

☑ 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 NPC193154 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

  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 NPC193154 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

  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