Structure

Physi-Chem Properties

Molecular Weight:  244.14
Volume:  248.057
LogP:  1.854
LogD:  1.413
LogS:  -2.207
# Rotatable Bonds:  7
TPSA:  101.98
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  0
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.314
Synthetic Accessibility Score:  3.444
Fsp3:  0.727
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.551
MDCK Permeability:  5.8513269323157147e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.026
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.261

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.995
Plasma Protein Binding (PPB):  60.76875305175781%
Volume Distribution (VD):  0.666
Pgp-substrate:  58.2254753112793%

ADMET: Metabolism

CYP1A2-inhibitor:  0.052
CYP1A2-substrate:  0.061
CYP2C19-inhibitor:  0.069
CYP2C19-substrate:  0.073
CYP2C9-inhibitor:  0.085
CYP2C9-substrate:  0.462
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.106
CYP3A4-inhibitor:  0.034
CYP3A4-substrate:  0.233

ADMET: Excretion

Clearance (CL):  3.283
Half-life (T1/2):  0.151

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.305
Drug-inuced Liver Injury (DILI):  0.811
AMES Toxicity:  0.104
Rat Oral Acute Toxicity:  0.059
Maximum Recommended Daily Dose:  0.013
Skin Sensitization:  0.122
Carcinogencity:  0.473
Eye Corrosion:  0.016
Eye Irritation:  0.318
Respiratory Toxicity:  0.219

Download Data

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

  Natural Product: NPC471129

Natural Product ID:  NPC471129
Common Name*:   Aspergilliamide B
IUPAC Name:   [(2Z)-1-amino-2-hydroxyimino-4-methyl-1-oxopentan-3-yl] 3-methylbutanoate
Synonyms:  
Standard InCHIKey:  CYFXYPOYWBHJDO-LCYFTJDESA-N
Standard InCHI:  InChI=1S/C11H20N2O4/c1-6(2)5-8(14)17-10(7(3)4)9(13-16)11(12)15/h6-7,10,16H,5H2,1-4H3,(H2,12,15)/b13-9-
SMILES:  O/N=C(/C(C(C)C)OC(=O)CC(C)C)C(=N)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2375797
PubChem CID:   71712816
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000324] Fatty acid esters

*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[485130]
NPT111 Cell Line K562 Homo sapiens IC50 > 10000.0 nM PMID[485130]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000.0 nM PMID[485130]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[485130]

☑ 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 NPC471129 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
0.7 Intermediate Similarity NPC478256
0.7 Intermediate Similarity NPC476285
0.6944 Remote Similarity NPC476248
0.6761 Remote Similarity NPC476291
0.6712 Remote Similarity NPC138435
0.6622 Remote Similarity NPC472595
0.6575 Remote Similarity NPC141325
0.6533 Remote Similarity NPC476324
0.6533 Remote Similarity NPC476130
0.6515 Remote Similarity NPC321468
0.6515 Remote Similarity NPC327748
0.6486 Remote Similarity NPC43219
0.6462 Remote Similarity NPC317147
0.6452 Remote Similarity NPC471131
0.6447 Remote Similarity NPC472594
0.6418 Remote Similarity NPC329564
0.6418 Remote Similarity NPC327170
0.64 Remote Similarity NPC86064
0.6389 Remote Similarity NPC314273
0.6389 Remote Similarity NPC193280
0.6269 Remote Similarity NPC317143
0.6269 Remote Similarity NPC316826
0.625 Remote Similarity NPC321118
0.625 Remote Similarity NPC316889
0.6212 Remote Similarity NPC318260
0.6207 Remote Similarity NPC325102
0.6197 Remote Similarity NPC470108
0.6164 Remote Similarity NPC472579
0.6125 Remote Similarity NPC314466
0.6119 Remote Similarity NPC328447
0.6111 Remote Similarity NPC118524
0.6111 Remote Similarity NPC470109
0.6056 Remote Similarity NPC128559
0.6029 Remote Similarity NPC473599
0.6027 Remote Similarity NPC470110
0.5949 Remote Similarity NPC316242
0.5946 Remote Similarity NPC474298
0.5946 Remote Similarity NPC475808
0.5946 Remote Similarity NPC473985
0.5946 Remote Similarity NPC474299
0.5946 Remote Similarity NPC28348
0.5938 Remote Similarity NPC322946
0.5921 Remote Similarity NPC474403
0.5904 Remote Similarity NPC95478
0.5904 Remote Similarity NPC155670
0.5904 Remote Similarity NPC145748
0.5875 Remote Similarity NPC315535
0.5875 Remote Similarity NPC315131
0.5875 Remote Similarity NPC473984
0.5875 Remote Similarity NPC478017
0.5873 Remote Similarity NPC328378
0.5862 Remote Similarity NPC477729
0.5833 Remote Similarity NPC227051
0.5775 Remote Similarity NPC105297
0.575 Remote Similarity NPC37681
0.5714 Remote Similarity NPC470363
0.5694 Remote Similarity NPC145658
0.5672 Remote Similarity NPC322573
0.5652 Remote Similarity NPC190385
0.5634 Remote Similarity NPC477644
0.5625 Remote Similarity NPC162620
0.5625 Remote Similarity NPC245027
0.5625 Remote Similarity NPC62045
0.5616 Remote Similarity NPC41429
0.5614 Remote Similarity NPC14608
0.5606 Remote Similarity NPC137327

  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 NPC471129 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
0.6812 Remote Similarity NPD2263 Discontinued
0.6667 Remote Similarity NPD2689 Clinical (unspecified phase)
0.662 Remote Similarity NPD3724 Clinical (unspecified phase)
0.6533 Remote Similarity NPD1453 Phase 1
0.6119 Remote Similarity NPD9661 Approved
0.6056 Remote Similarity NPD1831 Phase 3
0.5938 Remote Similarity NPD9441 Phase 2
0.5932 Remote Similarity NPD9664 Approved
0.5902 Remote Similarity NPD380 Approved
0.5875 Remote Similarity NPD7917 Clinical (unspecified phase)
0.5875 Remote Similarity NPD7918 Clinical (unspecified phase)
0.5781 Remote Similarity NPD903 Approved
0.5775 Remote Similarity NPD1146 Phase 2
0.5714 Remote Similarity NPD2266 Phase 2
0.569 Remote Similarity NPD9453 Phase 3
0.5676 Remote Similarity NPD8842 Clinical (unspecified phase)
0.5652 Remote Similarity NPD9433 Approved
0.5652 Remote Similarity NPD9023 Clinical (unspecified phase)
0.5625 Remote Similarity NPD9018 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