Structure

Physi-Chem Properties

Molecular Weight:  501.6
Volume:  212.502
LogP:  3.014
LogD:  1.822
LogS:  -4.785
# Rotatable Bonds:  1
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.555
Synthetic Accessibility Score:  4.822
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.558
MDCK Permeability:  3.1596435292158276e-05
Pgp-inhibitor:  0.988
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.623
20% Bioavailability (F20%):  0.929
30% Bioavailability (F30%):  0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.872
Plasma Protein Binding (PPB):  94.03789520263672%
Volume Distribution (VD):  1.926
Pgp-substrate:  9.74608325958252%

ADMET: Metabolism

CYP1A2-inhibitor:  0.922
CYP1A2-substrate:  0.637
CYP2C19-inhibitor:  0.687
CYP2C19-substrate:  0.82
CYP2C9-inhibitor:  0.947
CYP2C9-substrate:  0.317
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.246
CYP3A4-inhibitor:  0.288
CYP3A4-substrate:  0.859

ADMET: Excretion

Clearance (CL):  1.144
Half-life (T1/2):  0.183

ADMET: Toxicity

hERG Blockers:  0.039
Human Hepatotoxicity (H-HT):  0.665
Drug-inuced Liver Injury (DILI):  0.913
AMES Toxicity:  0.821
Rat Oral Acute Toxicity:  0.145
Maximum Recommended Daily Dose:  0.02
Skin Sensitization:  0.942
Carcinogencity:  0.901
Eye Corrosion:  0.957
Eye Irritation:  0.906
Respiratory Toxicity:  0.982

Download Data

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

  Natural Product: NPC487937

Natural Product ID:  NPC487937
Common Name*:   YUPZHKUNWOZQRP-XINAWCOVSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  YUPZHKUNWOZQRP-XINAWCOVSA-N
Standard InCHI:  InChI=1S/C6H3Br5O2/c7-1-2(12)4(9)6(13,3(1)8)5(10)11/h4-5,13H/t4-,6+/m1/s1
SMILES:  C1(=C([C@]([C@@H](C1=O)Br)(C(Br)Br)O)Br)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   86765313
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001670] Tertiary alcohols

*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
NPO16478 Asparagopsis taxiformis Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. PMID[24746270]
NPO16478 Asparagopsis taxiformis Species Bonnemaisoniaceae 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
NPT6040 Organism Vibrio fischeri Aliivibrio fischeri EC50 = 0.08 ug.mL-1 PMID[24746270]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii MIC80 = 16.0 ug.mL-1 PMID[24746270]
NPT19 Organism Escherichia coli Escherichia coli MIC80 > 32.0 ug.mL-1 PMID[24746270]
NPT19 Organism Escherichia coli Escherichia coli MIC80 = 32.0 ug.mL-1 PMID[24746270]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC80 > 10.0 ug.mL-1 PMID[24746270]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC80 = 16.0 ug.mL-1 PMID[24746270]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC80 > 32.0 ug.mL-1 PMID[24746270]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC80 > 32.0 ug.mL-1 PMID[24746270]
NPT20 Organism Candida albicans Candida albicans MIC80 > 32.0 ug.mL-1 PMID[24746270]

☑ 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 NPC487937 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 NPC487937 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