Structure

Physi-Chem Properties

Molecular Weight:  279.11
Volume:  275.353
LogP:  0.953
LogD:  0.494
LogS:  -2.93
# Rotatable Bonds:  3
TPSA:  83.91
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.596
Synthetic Accessibility Score:  5.07
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.767
MDCK Permeability:  1.2963944755028933e-05
Pgp-inhibitor:  0.023
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.343
20% Bioavailability (F20%):  0.178
30% Bioavailability (F30%):  0.882

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.997
Plasma Protein Binding (PPB):  64.66732025146484%
Volume Distribution (VD):  0.809
Pgp-substrate:  44.08860778808594%

ADMET: Metabolism

CYP1A2-inhibitor:  0.071
CYP1A2-substrate:  0.788
CYP2C19-inhibitor:  0.069
CYP2C19-substrate:  0.864
CYP2C9-inhibitor:  0.059
CYP2C9-substrate:  0.118
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.11
CYP3A4-inhibitor:  0.036
CYP3A4-substrate:  0.583

ADMET: Excretion

Clearance (CL):  7.194
Half-life (T1/2):  0.245

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.158
Drug-inuced Liver Injury (DILI):  0.126
AMES Toxicity:  0.781
Rat Oral Acute Toxicity:  0.811
Maximum Recommended Daily Dose:  0.893
Skin Sensitization:  0.55
Carcinogencity:  0.939
Eye Corrosion:  0.005
Eye Irritation:  0.021
Respiratory Toxicity:  0.934

Download Data

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

  Natural Product: NPC126719

Natural Product ID:  NPC126719
Common Name*:   UEEZHRJFRYRGNC-VXJKQWIASA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UEEZHRJFRYRGNC-VXJKQWIASA-N
Standard InCHI:  InChI=1S/C14H17NO5/c1-4-5-9-6-7-10(16)12(18)14(9)11(17)8(2)15(20-3)13(14)19/h5-7,11-12,17-18H,2,4H2,1,3H3/b9-5-/t11-,12+,14-/m0/s1
SMILES:  CC/C=C1/C=CC(=O)[C@H]([C@]21[C@H](C(=C)N(C2=O)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   10333817
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003487] Cyclic ketones
              • [CHEMONTID:0004325] Cyclohexenones

*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
NPO40488 Cochliobolus lunatus SCSIO41401 Strain Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[29786436]
NPO40488 Cochliobolus lunatus SCSIO41401 Strain Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[30516983]

☑ 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
NPT369 Cell Line ACHN Homo sapiens IC50 > 50000.0 nM PMID[30516983]
NPT401 Cell Line 786-0 Homo sapiens IC50 > 50000.0 nM PMID[30516983]
NPT1997 Cell Line OS-RC-2 Homo sapiens IC50 > 50000.0 nM PMID[30516983]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 50000.0 nM PMID[30516983]
NPT515 Cell Line SGC-7901 Homo sapiens IC50 > 50000.0 nM PMID[30516983]
NPT19 Organism Escherichia coli Escherichia coli MIC > 100.0 ug.mL-1 PMID[30516983]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 100.0 ug.mL-1 PMID[30516983]
NPT6472 Organism Erysipelothrix rhusiopathiae Erysipelothrix rhusiopathiae MIC > 100.0 ug.mL-1 PMID[30516983]
NPT2 Others Unspecified MIC > 100.0 ug.mL-1 PMID[30516983]
NPT742 Organism Influenza A virus Influenza A virus IC50 = 21000.0 nM PMID[30516983]

☑ 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 NPC126719 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 NPC126719 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