Structure

Physi-Chem Properties

Molecular Weight:  356.11
Volume:  334.109
LogP:  -0.396
LogD:  0.549
LogS:  -1.233
# Rotatable Bonds:  6
TPSA:  145.91
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.323
Synthetic Accessibility Score:  3.612
Fsp3:  0.438
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.017
MDCK Permeability:  0.00018519657896831632
Pgp-inhibitor:  0.001
Pgp-substrate:  0.727
Human Intestinal Absorption (HIA):  0.917
20% Bioavailability (F20%):  0.645
30% Bioavailability (F30%):  0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.743
Plasma Protein Binding (PPB):  68.09693145751953%
Volume Distribution (VD):  0.414
Pgp-substrate:  34.84524917602539%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.061
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.308
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.736
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.3
CYP3A4-inhibitor:  0.01
CYP3A4-substrate:  0.038

ADMET: Excretion

Clearance (CL):  3.816
Half-life (T1/2):  0.821

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.07
Drug-inuced Liver Injury (DILI):  0.066
AMES Toxicity:  0.331
Rat Oral Acute Toxicity:  0.243
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.12
Carcinogencity:  0.213
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.042

Download Data

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

  Natural Product: NPC490242

Natural Product ID:  NPC490242
Common Name*:   Feruloyl glucose
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  JWRQVQWBNRGGPK-HWKANZROSA-N
Standard InCHI:  InChI=1S/C16H20O9/c1-23-10-6-8(2-4-9(10)18)3-5-12(19)25-16-15(22)14(21)13(20)11(7-17)24-16/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+
SMILES:  COC1=C(O)C=CC(C=CC(=O)OC2OC(CO)C(O)C(O)C2O)=C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0003002] Hydroxycinnamic acid esters
            • [CHEMONTID:0003003] Hydroxycinnamic acid glycosides

*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
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. DOI[10.1021/jf970571j]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Roots (runner plant) Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruits Suwon, Korea 2012-Nov DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Leaves Suwon, Korea DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Runners Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Leaves (runner plant) Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Roots (mother plant) Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Leaves (mother plant) Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[12932131]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[1453178]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruits n.a. n.a. PMID[15568772]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. fruit n.a. PMID[16417304]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[20460582]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. fruit n.a. PMID[240326]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[25172746]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[8910532]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Pollen Or Spore n.a. n.a. Database[FooDB]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Seed n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO27436 Ribes uva-crispa Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Bulb n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruits n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit n.a. n.a. Database[FooDB]
NPO27436 Ribes uva-crispa Species n.a. n.a. Fruits n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO42025 Ribes nidigrolaria Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO16230 Malus pumila Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO27436 Ribes uva-crispa Species n.a. n.a. Fruit n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit Juice n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Leaf n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16230 Malus pumila Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27436 Ribes uva-crispa Species n.a. n.a. 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
NPO1751 NPC490242 Raw n.a. 1.299999992 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO42025 NPC490242 Raw n.a. 3.200000048 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO27436 NPC490242 Raw n.a. 0.300000012 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO16501 NPC490242 Raw n.a. 0.325000008 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO10339 NPC490242 Raw n.a. 0.100000001 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO16501 NPC490242 Raw n.a. 0.36499999 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO16230 NPC490242 n.a. n.a. 0.1562 n.a. n.a. mg/100g Database [PHENOL EXPLORER]

☑ 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 NPC490242 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 NPC490242 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