Structure

Physi-Chem Properties

Molecular Weight:  126.1
Volume:  150.442
LogP:  2.769
LogD:  2.648
LogS:  -2.245
# Rotatable Bonds:  4
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.417
Synthetic Accessibility Score:  3.055
Fsp3:  0.625
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.24
MDCK Permeability:  2.8727366952807643e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.013
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.997
Plasma Protein Binding (PPB):  73.93610382080078%
Volume Distribution (VD):  1.002
Pgp-substrate:  30.43596649169922%

ADMET: Metabolism

CYP1A2-inhibitor:  0.84
CYP1A2-substrate:  0.923
CYP2C19-inhibitor:  0.349
CYP2C19-substrate:  0.837
CYP2C9-inhibitor:  0.079
CYP2C9-substrate:  0.894
CYP2D6-inhibitor:  0.036
CYP2D6-substrate:  0.669
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.219

ADMET: Excretion

Clearance (CL):  5.162
Half-life (T1/2):  0.768

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.304
Drug-inuced Liver Injury (DILI):  0.119
AMES Toxicity:  0.084
Rat Oral Acute Toxicity:  0.018
Maximum Recommended Daily Dose:  0.489
Skin Sensitization:  0.95
Carcinogencity:  0.719
Eye Corrosion:  0.98
Eye Irritation:  0.99
Respiratory Toxicity:  0.843

Download Data

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

  Natural Product: NPC101147

Natural Product ID:  NPC101147
Common Name*:   2-Ethylhex-2-Enal
IUPAC Name:   2-ethylhex-2-enal
Synonyms:  
Standard InCHIKey:  PYLMCYQHBRSDND-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H14O/c1-3-5-6-8(4-2)7-9/h6-7H,3-5H2,1-2H3
SMILES:  CCCC=C(C=O)CC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3181995
PubChem CID:   12582
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000124] Aldehydes
            • [CHEMONTID:0002229] Medium-chain aldehydes

*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
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. bark n.a. PMID[21875098]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[24868863]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[25089845]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[28682072]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[29883114]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9546 Cinamomum cassia n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18951 Ligusticum sinense Species Apiaceae 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
NPT2 Others Unspecified Potency n.a. 173.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19493.8 nM PubChem BioAssay data set

☑ 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 NPC101147 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
0.9189 High Similarity NPC254764
0.8974 High Similarity NPC12319
0.8974 High Similarity NPC18205
0.8421 Intermediate Similarity NPC75204
0.825 Intermediate Similarity NPC33761
0.8205 Intermediate Similarity NPC279300
0.8158 Intermediate Similarity NPC72258
0.8108 Intermediate Similarity NPC109034
0.8049 Intermediate Similarity NPC323278
0.7907 Intermediate Similarity NPC106819
0.7872 Intermediate Similarity NPC234829
0.7857 Intermediate Similarity NPC33489
0.7838 Intermediate Similarity NPC273054
0.775 Intermediate Similarity NPC8416
0.7692 Intermediate Similarity NPC269641
0.7674 Intermediate Similarity NPC298710
0.7674 Intermediate Similarity NPC208936
0.7674 Intermediate Similarity NPC67920
0.7674 Intermediate Similarity NPC287397
0.7619 Intermediate Similarity NPC111474
0.7609 Intermediate Similarity NPC324812
0.75 Intermediate Similarity NPC30433
0.75 Intermediate Similarity NPC38497
0.7447 Intermediate Similarity NPC477789
0.7436 Intermediate Similarity NPC12889
0.74 Intermediate Similarity NPC100809
0.74 Intermediate Similarity NPC209431
0.7391 Intermediate Similarity NPC276009
0.7391 Intermediate Similarity NPC22098
0.7391 Intermediate Similarity NPC195246
0.7333 Intermediate Similarity NPC477686
0.7317 Intermediate Similarity NPC185839
0.7255 Intermediate Similarity NPC188789
0.7179 Intermediate Similarity NPC266979
0.7174 Intermediate Similarity NPC191337
0.7174 Intermediate Similarity NPC166788
0.7143 Intermediate Similarity NPC180840
0.7111 Intermediate Similarity NPC301972
0.7111 Intermediate Similarity NPC216921
0.7021 Intermediate Similarity NPC471752
0.7 Intermediate Similarity NPC146507
0.6957 Remote Similarity NPC25771
0.6957 Remote Similarity NPC471753
0.6939 Remote Similarity NPC236338
0.6939 Remote Similarity NPC225974
0.6842 Remote Similarity NPC8466
0.6809 Remote Similarity NPC239754
0.675 Remote Similarity NPC144407
0.6739 Remote Similarity NPC292463
0.6735 Remote Similarity NPC145311
0.6667 Remote Similarity NPC8610
0.6667 Remote Similarity NPC163751
0.6667 Remote Similarity NPC44363
0.6667 Remote Similarity NPC100380
0.6667 Remote Similarity NPC262558
0.6667 Remote Similarity NPC110234
0.66 Remote Similarity NPC176819
0.66 Remote Similarity NPC15325
0.66 Remote Similarity NPC220191
0.66 Remote Similarity NPC58970
0.66 Remote Similarity NPC163984
0.66 Remote Similarity NPC15789
0.66 Remote Similarity NPC118788
0.6596 Remote Similarity NPC114841
0.6591 Remote Similarity NPC217923
0.6585 Remote Similarity NPC310810
0.6545 Remote Similarity NPC21946
0.6538 Remote Similarity NPC474805
0.6512 Remote Similarity NPC24833
0.6481 Remote Similarity NPC477790
0.6471 Remote Similarity NPC22329
0.6458 Remote Similarity NPC270706
0.6444 Remote Similarity NPC113082
0.6429 Remote Similarity NPC82465
0.6415 Remote Similarity NPC95581
0.6415 Remote Similarity NPC189677
0.64 Remote Similarity NPC267110
0.64 Remote Similarity NPC135698
0.6364 Remote Similarity NPC92863
0.6364 Remote Similarity NPC321568
0.6364 Remote Similarity NPC22019
0.6364 Remote Similarity NPC155880
0.6364 Remote Similarity NPC281986
0.6364 Remote Similarity NPC208749
0.6364 Remote Similarity NPC268185
0.6346 Remote Similarity NPC471751
0.6327 Remote Similarity NPC128280
0.6275 Remote Similarity NPC228776
0.6275 Remote Similarity NPC20934
0.6275 Remote Similarity NPC288381
0.6275 Remote Similarity NPC32351
0.6271 Remote Similarity NPC52449
0.6271 Remote Similarity NPC169275
0.625 Remote Similarity NPC6963
0.625 Remote Similarity NPC304079
0.625 Remote Similarity NPC12907
0.6226 Remote Similarity NPC37644
0.6226 Remote Similarity NPC296311
0.6222 Remote Similarity NPC29091
0.6222 Remote Similarity NPC103213
0.6222 Remote Similarity NPC182840
0.6222 Remote Similarity NPC255042
0.617 Remote Similarity NPC187922
0.6167 Remote Similarity NPC183422
0.6154 Remote Similarity NPC64866
0.6122 Remote Similarity NPC26600
0.6122 Remote Similarity NPC47946
0.6111 Remote Similarity NPC300121
0.6111 Remote Similarity NPC250539
0.6111 Remote Similarity NPC317796
0.6087 Remote Similarity NPC48930
0.6087 Remote Similarity NPC123357
0.6071 Remote Similarity NPC293437
0.6071 Remote Similarity NPC71755
0.6071 Remote Similarity NPC249850
0.6071 Remote Similarity NPC135863
0.6038 Remote Similarity NPC137396
0.6038 Remote Similarity NPC170167
0.6034 Remote Similarity NPC79756
0.6034 Remote Similarity NPC309408
0.6 Remote Similarity NPC197467
0.6 Remote Similarity NPC130923
0.6 Remote Similarity NPC308331
0.6 Remote Similarity NPC317899
0.6 Remote Similarity NPC87137
0.6 Remote Similarity NPC226511
0.6 Remote Similarity NPC155900
0.5968 Remote Similarity NPC4370
0.5968 Remote Similarity NPC290350
0.5965 Remote Similarity NPC254095
0.5962 Remote Similarity NPC221467
0.5957 Remote Similarity NPC221250
0.5957 Remote Similarity NPC269823
0.5932 Remote Similarity NPC260573
0.5932 Remote Similarity NPC151648
0.5926 Remote Similarity NPC268564
0.5926 Remote Similarity NPC217188
0.5926 Remote Similarity NPC23117
0.5926 Remote Similarity NPC45283
0.5918 Remote Similarity NPC145755
0.5918 Remote Similarity NPC267514
0.5882 Remote Similarity NPC91962
0.5873 Remote Similarity NPC155198
0.5862 Remote Similarity NPC473494
0.5849 Remote Similarity NPC244452
0.5849 Remote Similarity NPC43053
0.5833 Remote Similarity NPC68110
0.5833 Remote Similarity NPC57923
0.5833 Remote Similarity NPC474658
0.5833 Remote Similarity NPC213538
0.5833 Remote Similarity NPC256766
0.5818 Remote Similarity NPC474127
0.5818 Remote Similarity NPC478120
0.5818 Remote Similarity NPC129710
0.5789 Remote Similarity NPC200831
0.5789 Remote Similarity NPC294938
0.5789 Remote Similarity NPC235797
0.5789 Remote Similarity NPC129150
0.5789 Remote Similarity NPC224103
0.5789 Remote Similarity NPC299369
0.5789 Remote Similarity NPC283502
0.5781 Remote Similarity NPC261398
0.5781 Remote Similarity NPC61702
0.5781 Remote Similarity NPC162867
0.5778 Remote Similarity NPC220061
0.5769 Remote Similarity NPC234597
0.5745 Remote Similarity NPC8270
0.5741 Remote Similarity NPC229046
0.5741 Remote Similarity NPC191643
0.5741 Remote Similarity NPC22182
0.5741 Remote Similarity NPC216407
0.5741 Remote Similarity NPC46565
0.5714 Remote Similarity NPC173157
0.5714 Remote Similarity NPC116934
0.5714 Remote Similarity NPC270796
0.5714 Remote Similarity NPC275472
0.569 Remote Similarity NPC311852
0.569 Remote Similarity NPC471619
0.569 Remote Similarity NPC281195
0.569 Remote Similarity NPC223679
0.569 Remote Similarity NPC139056
0.5686 Remote Similarity NPC4079
0.5686 Remote Similarity NPC236355
0.5686 Remote Similarity NPC14917
0.5682 Remote Similarity NPC58957
0.5667 Remote Similarity NPC228574
0.5667 Remote Similarity NPC294304
0.566 Remote Similarity NPC289388
0.566 Remote Similarity NPC275316
0.566 Remote Similarity NPC474391
0.5652 Remote Similarity NPC40434
0.5652 Remote Similarity NPC34873
0.5636 Remote Similarity NPC168521
0.5636 Remote Similarity NPC474141
0.5636 Remote Similarity NPC14002
0.5625 Remote Similarity NPC270170
0.5625 Remote Similarity NPC7754
0.5614 Remote Similarity NPC150717
0.5614 Remote Similarity NPC252860
0.5614 Remote Similarity NPC473733

  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 NPC101147 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
0.6977 Remote Similarity NPD5783 Phase 3
0.625 Remote Similarity NPD6097 Approved
0.625 Remote Similarity NPD6096 Approved
0.6154 Remote Similarity NPD6927 Phase 3
0.5882 Remote Similarity NPD5343 Approved
0.5789 Remote Similarity NPD8779 Phase 3
0.5769 Remote Similarity NPD4220 Pre-registration
0.5714 Remote Similarity NPD9411 Phase 1
0.5714 Remote Similarity NPD5326 Phase 3

  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