Structure

Physi-Chem Properties

Molecular Weight:  228.15
Volume:  239.267
LogP:  2.019
LogD:  1.729
LogS:  -2.211
# Rotatable Bonds:  7
TPSA:  78.76
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.425
Synthetic Accessibility Score:  2.861
Fsp3:  0.727
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.313
MDCK Permeability:  2.6918292860500515e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.023
30% Bioavailability (F30%):  0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.999
Plasma Protein Binding (PPB):  68.41625213623047%
Volume Distribution (VD):  0.795
Pgp-substrate:  43.14917755126953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.204
CYP1A2-substrate:  0.053
CYP2C19-inhibitor:  0.433
CYP2C19-substrate:  0.251
CYP2C9-inhibitor:  0.398
CYP2C9-substrate:  0.945
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.098
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.17

ADMET: Excretion

Clearance (CL):  2.771
Half-life (T1/2):  0.772

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.627
Drug-inuced Liver Injury (DILI):  0.318
AMES Toxicity:  0.153
Rat Oral Acute Toxicity:  0.168
Maximum Recommended Daily Dose:  0.014
Skin Sensitization:  0.203
Carcinogencity:  0.116
Eye Corrosion:  0.004
Eye Irritation:  0.411
Respiratory Toxicity:  0.024

Download Data

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

  Natural Product: NPC471131

Natural Product ID:  NPC471131
Common Name*:   Aspergilliamide
IUPAC Name:   (2E)-2-hydroxyimino-4-methyl-N-(3-methylbutanoyl)pentanamide
Synonyms:  
Standard InCHIKey:  ZBPZAHHJROEFGA-UKTHLTGXSA-N
Standard InCHI:  InChI=1S/C11H20N2O3/c1-7(2)5-9(13-16)11(15)12-10(14)6-8(3)4/h7-8,16H,5-6H2,1-4H3,(H,12,14,15)/b13-9+
SMILES:  CC(C)CC(=NO)C(=O)NC(=O)CC(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2375800
PubChem CID:   73351894
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000331] Fatty amides
          • [CHEMONTID:0001096] N-acyl amines

*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
NPO32643 aspergillus westerdijkiae dffscs013 Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23701598]

☑ 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
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[553224]
NPT111 Cell Line K562 Homo sapiens IC50 > 10000.0 nM PMID[553224]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000.0 nM PMID[553224]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[553224]

☑ 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 NPC471131 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
0.7049 Intermediate Similarity NPC105297
0.6833 Remote Similarity NPC321468
0.6833 Remote Similarity NPC327748
0.6825 Remote Similarity NPC128559
0.6786 Remote Similarity NPC322946
0.678 Remote Similarity NPC317147
0.6721 Remote Similarity NPC327170
0.6721 Remote Similarity NPC329564
0.6557 Remote Similarity NPC317143
0.6557 Remote Similarity NPC316826
0.6545 Remote Similarity NPC87359
0.6545 Remote Similarity NPC180402
0.6515 Remote Similarity NPC306696
0.6515 Remote Similarity NPC250953
0.65 Remote Similarity NPC318260
0.6452 Remote Similarity NPC471129
0.6429 Remote Similarity NPC80350
0.6429 Remote Similarity NPC21142
0.629 Remote Similarity NPC292299
0.629 Remote Similarity NPC34838
0.6286 Remote Similarity NPC266888
0.6286 Remote Similarity NPC256312
0.6286 Remote Similarity NPC161774
0.6271 Remote Similarity NPC316889
0.6271 Remote Similarity NPC321118
0.619 Remote Similarity NPC263207
0.6102 Remote Similarity NPC137327
0.6061 Remote Similarity NPC262615
0.6056 Remote Similarity NPC209156
0.6032 Remote Similarity NPC254541
0.6 Remote Similarity NPC214532
0.6 Remote Similarity NPC76297
0.6 Remote Similarity NPC196007
0.5962 Remote Similarity NPC33721
0.5873 Remote Similarity NPC176164
0.5873 Remote Similarity NPC189301
0.5867 Remote Similarity NPC312315
0.5862 Remote Similarity NPC328378
0.5781 Remote Similarity NPC320598
0.5735 Remote Similarity NPC470108
0.5714 Remote Similarity NPC470783
0.5694 Remote Similarity NPC315897
0.5672 Remote Similarity NPC57420
0.5652 Remote Similarity NPC470109
0.5645 Remote Similarity NPC322573
0.5641 Remote Similarity NPC53858
0.5641 Remote Similarity NPC84128
0.5634 Remote Similarity NPC478256
0.5625 Remote Similarity NPC472578
0.5606 Remote Similarity NPC314510

  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 NPC471131 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
0.6786 Remote Similarity NPD9441 Phase 2
0.6429 Remote Similarity NPD9200 Approved
0.6418 Remote Similarity NPD620 Approved
0.6167 Remote Similarity NPD1830 Clinical (unspecified phase)
0.6119 Remote Similarity NPD2263 Discontinued
0.6071 Remote Similarity NPD379 Clinical (unspecified phase)
0.6061 Remote Similarity NPD6437 Approved
0.6061 Remote Similarity NPD6438 Approved
0.6034 Remote Similarity NPD325 Approved
0.6032 Remote Similarity NPD354 Approved
0.6 Remote Similarity NPD9658 Clinical (unspecified phase)
0.5965 Remote Similarity NPD362 Phase 1
0.5962 Remote Similarity NPD8576 Approved
0.5946 Remote Similarity NPD836 Clinical (unspecified phase)
0.5942 Remote Similarity NPD3724 Clinical (unspecified phase)
0.5862 Remote Similarity NPD323 Approved
0.5833 Remote Similarity NPD611 Approved
0.5833 Remote Similarity NPD609 Approved
0.5818 Remote Similarity NPD9400 Approved
0.5818 Remote Similarity NPD9399 Approved
0.5763 Remote Similarity NPD324 Approved
0.5738 Remote Similarity NPD610 Approved
0.5738 Remote Similarity NPD608 Approved
0.5714 Remote Similarity NPD9647 Approved
0.5694 Remote Similarity NPD1825 Clinical (unspecified phase)
0.5694 Remote Similarity NPD1147 Phase 2
0.566 Remote Similarity NPD9453 Phase 3
0.5641 Remote Similarity NPD2683 Discontinued
0.5625 Remote Similarity NPD9433 Approved
0.5606 Remote Similarity NPD574 Approved

  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