Structure

Physi-Chem Properties

Molecular Weight:  257.18
Volume:  298.0
LogP:  5.007
LogD:  3.111
LogS:  -4.504
# Rotatable Bonds:  5
TPSA:  29.1
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.595
Synthetic Accessibility Score:  3.25
Fsp3:  0.588
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.108
MDCK Permeability:  2.695691910048481e-05
Pgp-inhibitor:  0.084
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.035
30% Bioavailability (F30%):  0.555

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  99.06548309326172%
Volume Distribution (VD):  1.684
Pgp-substrate:  0.6412710547447205%

ADMET: Metabolism

CYP1A2-inhibitor:  0.912
CYP1A2-substrate:  0.416
CYP2C19-inhibitor:  0.904
CYP2C19-substrate:  0.528
CYP2C9-inhibitor:  0.733
CYP2C9-substrate:  0.98
CYP2D6-inhibitor:  0.757
CYP2D6-substrate:  0.677
CYP3A4-inhibitor:  0.796
CYP3A4-substrate:  0.107

ADMET: Excretion

Clearance (CL):  3.288
Half-life (T1/2):  0.25

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.746
Drug-inuced Liver Injury (DILI):  0.953
AMES Toxicity:  0.524
Rat Oral Acute Toxicity:  0.046
Maximum Recommended Daily Dose:  0.606
Skin Sensitization:  0.972
Carcinogencity:  0.482
Eye Corrosion:  0.755
Eye Irritation:  0.869
Respiratory Toxicity:  0.935

Download Data

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

  Natural Product: NPC309877

Natural Product ID:  NPC309877
Common Name*:   Montiporyine E
IUPAC Name:   5-undeca-1,3-diynyl-1,2,3,4-tetrahydroazepin-7-one
Synonyms:   montiporyine E
Standard InCHIKey:  OBLFKWWWBVRLNJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H23NO/c1-2-3-4-5-6-7-8-9-10-12-16-13-11-14-18-17(19)15-16/h15H,2-7,11,13-14H2,1H3,(H,18,19)
SMILES:  CCCCCCCC#CC#CC1=CC(=NCCC1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL506860
PubChem CID:   10729862
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000069] Azepines

*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
NPO33414 montipora sp. Species Acroporidae Eukaryota n.a. n.a. n.a. PMID[11087594]
NPO33414 montipora sp. Species Acroporidae Eukaryota n.a. n.a. n.a. PMID[11520227]

☑ 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
NPT81 Cell Line A549 Homo sapiens ED50 > 50.0 ug ml-1 PMID[500139]
NPT146 Cell Line SK-OV-3 Homo sapiens ED50 > 50.0 ug ml-1 PMID[500139]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 > 50.0 ug ml-1 PMID[500139]
NPT574 Cell Line XF498 Homo sapiens ED50 > 50.0 ug ml-1 PMID[500139]
NPT148 Cell Line HCT-15 Homo sapiens ED50 > 50.0 ug ml-1 PMID[500139]

☑ 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 NPC309877 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
0.7966 Intermediate Similarity NPC13011
0.7966 Intermediate Similarity NPC124382
0.7833 Intermediate Similarity NPC273023
0.7833 Intermediate Similarity NPC471991
0.7705 Intermediate Similarity NPC261158
0.7705 Intermediate Similarity NPC24216
0.7705 Intermediate Similarity NPC477049
0.7705 Intermediate Similarity NPC306420
0.7705 Intermediate Similarity NPC104138
0.7667 Intermediate Similarity NPC163912
0.7667 Intermediate Similarity NPC305288
0.7667 Intermediate Similarity NPC167759
0.7667 Intermediate Similarity NPC56028
0.7541 Intermediate Similarity NPC297020
0.75 Intermediate Similarity NPC303672
0.75 Intermediate Similarity NPC119655
0.7377 Intermediate Similarity NPC123669
0.7344 Intermediate Similarity NPC312826
0.7333 Intermediate Similarity NPC195986
0.7258 Intermediate Similarity NPC471992
0.7231 Intermediate Similarity NPC130807
0.7167 Intermediate Similarity NPC54542
0.7167 Intermediate Similarity NPC304223
0.7167 Intermediate Similarity NPC145032
0.7167 Intermediate Similarity NPC243539
0.7167 Intermediate Similarity NPC267340
0.7121 Intermediate Similarity NPC29468
0.7 Intermediate Similarity NPC267692
0.7 Intermediate Similarity NPC307435
0.6825 Remote Similarity NPC184014
0.6825 Remote Similarity NPC132669
0.6825 Remote Similarity NPC14234
0.6825 Remote Similarity NPC246519
0.6825 Remote Similarity NPC44193
0.6825 Remote Similarity NPC269800
0.6812 Remote Similarity NPC477525
0.6716 Remote Similarity NPC6795
0.6714 Remote Similarity NPC187315
0.6709 Remote Similarity NPC39966
0.6615 Remote Similarity NPC4881
0.6528 Remote Similarity NPC249713
0.6522 Remote Similarity NPC182758
0.6438 Remote Similarity NPC45060
0.6438 Remote Similarity NPC280065
0.6418 Remote Similarity NPC210999
0.6333 Remote Similarity NPC269074
0.6324 Remote Similarity NPC150505
0.6324 Remote Similarity NPC74617
0.6286 Remote Similarity NPC471023
0.6271 Remote Similarity NPC470439
0.625 Remote Similarity NPC129995
0.625 Remote Similarity NPC315141
0.6143 Remote Similarity NPC324077
0.6098 Remote Similarity NPC224072
0.6087 Remote Similarity NPC329003
0.6087 Remote Similarity NPC326524
0.6087 Remote Similarity NPC325550
0.6032 Remote Similarity NPC31194
0.6032 Remote Similarity NPC248884
0.6032 Remote Similarity NPC85079
0.6029 Remote Similarity NPC245650
0.6026 Remote Similarity NPC476923
0.6 Remote Similarity NPC86121
0.6 Remote Similarity NPC103712
0.6 Remote Similarity NPC291196
0.5974 Remote Similarity NPC314678
0.5972 Remote Similarity NPC235311
0.5972 Remote Similarity NPC253468
0.597 Remote Similarity NPC242930
0.5968 Remote Similarity NPC19834
0.5968 Remote Similarity NPC55063
0.5968 Remote Similarity NPC180575
0.5942 Remote Similarity NPC321030
0.5938 Remote Similarity NPC72699
0.5938 Remote Similarity NPC474642
0.5938 Remote Similarity NPC249670
0.5938 Remote Similarity NPC473913
0.5915 Remote Similarity NPC273614
0.5873 Remote Similarity NPC91044
0.5846 Remote Similarity NPC151782
0.5846 Remote Similarity NPC261571
0.5833 Remote Similarity NPC228638
0.5833 Remote Similarity NPC316674
0.5833 Remote Similarity NPC77891
0.5833 Remote Similarity NPC304151
0.5823 Remote Similarity NPC476924
0.5789 Remote Similarity NPC471022
0.5781 Remote Similarity NPC125122
0.5781 Remote Similarity NPC471280
0.5781 Remote Similarity NPC153538
0.5781 Remote Similarity NPC471275
0.5781 Remote Similarity NPC471276
0.5758 Remote Similarity NPC188341
0.5758 Remote Similarity NPC49494
0.5747 Remote Similarity NPC473031
0.5735 Remote Similarity NPC474644
0.5714 Remote Similarity NPC14326
0.5714 Remote Similarity NPC35141
0.5714 Remote Similarity NPC124183
0.5714 Remote Similarity NPC325734
0.5698 Remote Similarity NPC152684
0.5696 Remote Similarity NPC288086
0.5692 Remote Similarity NPC182102
0.5692 Remote Similarity NPC26960
0.5692 Remote Similarity NPC471281
0.5692 Remote Similarity NPC199286
0.5692 Remote Similarity NPC477727
0.5667 Remote Similarity NPC269823
0.5652 Remote Similarity NPC474643
0.5652 Remote Similarity NPC473865
0.5645 Remote Similarity NPC108195
0.5645 Remote Similarity NPC101616
0.5641 Remote Similarity NPC469836
0.5632 Remote Similarity NPC166458
0.5632 Remote Similarity NPC203076
0.5616 Remote Similarity NPC477106
0.5606 Remote Similarity NPC471959
0.5606 Remote Similarity NPC89824
0.5606 Remote Similarity NPC477723
0.5606 Remote Similarity NPC55383
0.5606 Remote Similarity NPC256656
0.5606 Remote Similarity NPC197272
0.5606 Remote Similarity NPC76198
0.5606 Remote Similarity NPC165447
0.5606 Remote Similarity NPC473672
0.5606 Remote Similarity NPC475477
0.5606 Remote Similarity NPC93639
0.5606 Remote Similarity NPC129263
0.5606 Remote Similarity NPC224148
0.5606 Remote Similarity NPC170776
0.5606 Remote Similarity NPC474495
0.5606 Remote Similarity NPC329608
0.5606 Remote Similarity NPC9273
0.5606 Remote Similarity NPC294278

  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 NPC309877 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
NPD

  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