Structure

Physi-Chem Properties

Molecular Weight:  261.12
Volume:  281.917
LogP:  3.004
LogD:  3.691
LogS:  -4.196
# Rotatable Bonds:  7
TPSA:  29.1
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.614
Synthetic Accessibility Score:  2.736
Fsp3:  0.267
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.305
MDCK Permeability:  3.557606760296039e-05
Pgp-inhibitor:  0.015
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.3
20% Bioavailability (F20%):  0.11
30% Bioavailability (F30%):  0.124

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.132
Plasma Protein Binding (PPB):  92.51331329345703%
Volume Distribution (VD):  0.541
Pgp-substrate:  7.520610809326172%

ADMET: Metabolism

CYP1A2-inhibitor:  0.903
CYP1A2-substrate:  0.151
CYP2C19-inhibitor:  0.938
CYP2C19-substrate:  0.261
CYP2C9-inhibitor:  0.76
CYP2C9-substrate:  0.993
CYP2D6-inhibitor:  0.893
CYP2D6-substrate:  0.929
CYP3A4-inhibitor:  0.856
CYP3A4-substrate:  0.129

ADMET: Excretion

Clearance (CL):  2.44
Half-life (T1/2):  0.159

ADMET: Toxicity

hERG Blockers:  0.318
Human Hepatotoxicity (H-HT):  0.408
Drug-inuced Liver Injury (DILI):  0.703
AMES Toxicity:  0.051
Rat Oral Acute Toxicity:  0.013
Maximum Recommended Daily Dose:  0.027
Skin Sensitization:  0.626
Carcinogencity:  0.271
Eye Corrosion:  0.299
Eye Irritation:  0.971
Respiratory Toxicity:  0.838

Download Data

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

  Natural Product: NPC166487

Natural Product ID:  NPC166487
Common Name*:   (2E,4E,6E)-N-Isobutyl-7-(2-Thienyl)-2,4,6-Heptatrienamide
IUPAC Name:   (2E,4E,6E)-N-(2-methylpropyl)-7-thiophen-2-ylhepta-2,4,6-trienamide
Synonyms:  
Standard InCHIKey:  HGIRIKHYYMPDAG-IZMYCKBJSA-N
Standard InCHI:  InChI=1S/C15H19NOS/c1-13(2)12-16-15(17)10-6-4-3-5-8-14-9-7-11-18-14/h3-11,13H,12H2,1-2H3,(H,16,17)/b4-3+,8-5+,10-6+
SMILES:  CC(C)CN=C(/C=C/C=C/C=C/c1cccs1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2442636
PubChem CID:   73349612
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
NPO14864 Clerodendrum cyrtophyllum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[11473423]
NPO10210 Artabotrys uncinatus Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[11575948]
NPO12347 Pseudomonas syringae Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[14714872]
NPO15548 Sinularia leptoclados Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[16724859]
NPO12993 Polypodium vulgare Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10210 Artabotrys uncinatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15166 Cephalotaxus hainanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15166 Cephalotaxus hainanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7042 Myrica arborea Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8392 Iryanthera polyneura Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10210 Artabotrys uncinatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12993 Polypodium vulgare Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9734 Vincetoxicum hirundinaria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15166 Cephalotaxus hainanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12993 Polypodium vulgare Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5469 Pseudoxandra sclerocarpa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22084 Stypandra imbricata Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7042 Myrica arborea Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4518.1 Saccharothrix mutabilis subsp. capreolus Subspecies Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12993 Polypodium vulgare Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6367 Cortinarius viola Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15166 Cephalotaxus hainanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13549 Otanthus maritimus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26712 Cladrastis kentukea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12121 Streptomyces naraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO3974 Ferula gummosa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14989 Acanthothamnus aphyllus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13320 Glycosmis puberula Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11505 Nigella aristata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9338 Polygala aureocauda Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14191 Berkheya rhapontica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15066 Iridaea membranacea Species Gigartinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15548 Sinularia leptoclados Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1027 Scrophularia leucoclada Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4699 Dracaena ombet Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12347 Pseudomonas syringae Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8392 Iryanthera polyneura Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11151 Arnebia decumbens Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19872 Achillea magnifica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10210 Artabotrys uncinatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9734 Vincetoxicum hirundinaria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4503 Bryonopsis laciniosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14864 Clerodendrum cyrtophyllum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20070 Crinum stuhlmannii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12539 Lissoclinum japonicum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11683 Crotalaria mitchellii Species Fabaceae 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
NPT1167 Individual Protein Delta opioid receptor Mus musculus Ki = 25500.0 nM PMID[487560]
NPT1168 Individual Protein Mu opioid receptor Mus musculus Ki = 52000.0 nM PMID[487560]
NPT1169 Individual Protein Cannabinoid CB2 receptor Mus musculus Ki = 8250.0 nM PMID[487560]
NPT1170 Individual Protein Cannabinoid CB1 receptor Mus musculus Ki = 8800.0 nM PMID[487560]
NPT2 Others Unspecified Ratio Ki = 0.49 n.a. PMID[487560]
NPT2 Others Unspecified Ratio Ki = 1.07 n.a. PMID[487560]

☑ 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 NPC166487 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
0.9655 High Similarity NPC300455
0.8317 Intermediate Similarity NPC190955
0.7667 Intermediate Similarity NPC471376
0.7126 Intermediate Similarity NPC105991
0.6957 Remote Similarity NPC299367
0.6869 Remote Similarity NPC2751
0.6854 Remote Similarity NPC470796
0.6827 Remote Similarity NPC120203
0.6698 Remote Similarity NPC11466
0.6667 Remote Similarity NPC14326
0.6598 Remote Similarity NPC472169
0.6429 Remote Similarity NPC307163
0.6415 Remote Similarity NPC474934
0.6374 Remote Similarity NPC470795
0.6354 Remote Similarity NPC8981
0.633 Remote Similarity NPC173019
0.63 Remote Similarity NPC3210
0.6289 Remote Similarity NPC195713
0.6263 Remote Similarity NPC471895
0.6182 Remote Similarity NPC475115
0.6176 Remote Similarity NPC473031
0.6078 Remote Similarity NPC203076
0.6036 Remote Similarity NPC472171
0.6019 Remote Similarity NPC175376
0.5983 Remote Similarity NPC475013
0.5982 Remote Similarity NPC472172
0.5929 Remote Similarity NPC472170
0.5882 Remote Similarity NPC476048
0.5882 Remote Similarity NPC470794
0.5849 Remote Similarity NPC470797
0.5843 Remote Similarity NPC324077
0.5769 Remote Similarity NPC148231
0.5714 Remote Similarity NPC198747
0.5714 Remote Similarity NPC22627
0.569 Remote Similarity NPC475086
0.5664 Remote Similarity NPC469457
0.5635 Remote Similarity NPC86966
0.5635 Remote Similarity NPC324702
0.5614 Remote Similarity NPC24122

  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 NPC166487 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
0.7455 Intermediate Similarity NPD3907 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD745 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD183 Approved
0.73 Intermediate Similarity NPD532 Approved
0.7212 Intermediate Similarity NPD793 Approved
0.6731 Remote Similarity NPD1672 Phase 2
0.6723 Remote Similarity NPD5702 Clinical (unspecified phase)
0.6696 Remote Similarity NPD4991 Discontinued
0.6496 Remote Similarity NPD9356 Discontinued
0.6283 Remote Similarity NPD2242 Phase 1
0.625 Remote Similarity NPD3459 Approved
0.6207 Remote Similarity NPD1105 Clinical (unspecified phase)
0.6098 Remote Similarity NPD2389 Approved
0.6083 Remote Similarity NPD6360 Discontinued
0.6053 Remote Similarity NPD445 Discontinued
0.605 Remote Similarity NPD1944 Phase 2
0.6032 Remote Similarity NPD4099 Approved
0.6032 Remote Similarity NPD4100 Approved
0.6 Remote Similarity NPD4728 Approved
0.5948 Remote Similarity NPD5278 Discontinued
0.5942 Remote Similarity NPD1979 Approved
0.5912 Remote Similarity NPD1978 Approved
0.5909 Remote Similarity NPD2202 Clinical (unspecified phase)
0.5905 Remote Similarity NPD1629 Approved
0.5905 Remote Similarity NPD1628 Approved
0.5902 Remote Similarity NPD483 Approved
0.582 Remote Similarity NPD1713 Approved
0.5794 Remote Similarity NPD3355 Approved
0.5794 Remote Similarity NPD3356 Approved
0.5766 Remote Similarity NPD2447 Discontinued
0.575 Remote Similarity NPD1280 Clinical (unspecified phase)
0.575 Remote Similarity NPD2587 Approved
0.5727 Remote Similarity NPD3458 Approved
0.5727 Remote Similarity NPD3457 Approved
0.5727 Remote Similarity NPD3456 Approved
0.5726 Remote Similarity NPD7156 Discontinued
0.5726 Remote Similarity NPD446 Clinical (unspecified phase)
0.5714 Remote Similarity NPD1067 Discontinued
0.5714 Remote Similarity NPD804 Clinical (unspecified phase)
0.5694 Remote Similarity NPD2019 Approved
0.5694 Remote Similarity NPD2018 Approved
0.5692 Remote Similarity NPD2158 Clinical (unspecified phase)
0.5667 Remote Similarity NPD1265 Approved
0.5667 Remote Similarity NPD1267 Approved
0.5655 Remote Similarity NPD2020 Approved
0.5645 Remote Similarity NPD430 Discontinued
0.5612 Remote Similarity NPD3599 Approved
0.5612 Remote Similarity NPD4127 Clinical (unspecified phase)

  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