Structure

Physi-Chem Properties

Molecular Weight:  196.15
Volume:  219.859
LogP:  4.111
LogD:  3.972
LogS:  -4.568
# Rotatable Bonds:  4
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.512
Synthetic Accessibility Score:  3.187
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.406
MDCK Permeability:  2.741668686212506e-05
Pgp-inhibitor:  0.813
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.8
30% Bioavailability (F30%):  0.757

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.965
Plasma Protein Binding (PPB):  78.01361846923828%
Volume Distribution (VD):  1.772
Pgp-substrate:  32.83385467529297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.705
CYP1A2-substrate:  0.311
CYP2C19-inhibitor:  0.519
CYP2C19-substrate:  0.86
CYP2C9-inhibitor:  0.124
CYP2C9-substrate:  0.153
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.256
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.287

ADMET: Excretion

Clearance (CL):  10.535
Half-life (T1/2):  0.065

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.35
Drug-inuced Liver Injury (DILI):  0.217
AMES Toxicity:  0.044
Rat Oral Acute Toxicity:  0.054
Maximum Recommended Daily Dose:  0.028
Skin Sensitization:  0.082
Carcinogencity:  0.024
Eye Corrosion:  0.064
Eye Irritation:  0.652
Respiratory Toxicity:  0.776

Download Data

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

  Natural Product: NPC252860

Natural Product ID:  NPC252860
Common Name*:   Chrysanthemic Acid, Ethyl Ester
IUPAC Name:   ethyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
Synonyms:  
Standard InCHIKey:  VIMXTGUGWLAOFZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H20O2/c1-6-14-11(13)10-9(7-8(2)3)12(10,4)5/h7,9-10H,6H2,1-5H3
SMILES:  CCOC(=O)C1C(C1(C)C)C=C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1596099
PubChem CID:   7334
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001563] Monocyclic monoterpenoids

*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
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. stem n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. flower n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain Asteraceae 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
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 35481.3 nM PMID[512927]
NPT2 Others Unspecified Potency = 1000.0 nM PMID[512927]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 83.17 % PMID[512928]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 89.36 % PMID[512928]

☑ 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 NPC252860 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
0.8727 High Similarity NPC67367
0.8519 High Similarity NPC170167
0.8333 Intermediate Similarity NPC244452
0.8182 Intermediate Similarity NPC216407
0.8148 Intermediate Similarity NPC289388
0.7344 Intermediate Similarity NPC34883
0.7321 Intermediate Similarity NPC135698
0.7321 Intermediate Similarity NPC62755
0.7321 Intermediate Similarity NPC234597
0.7246 Intermediate Similarity NPC470237
0.7241 Intermediate Similarity NPC151919
0.7222 Intermediate Similarity NPC253749
0.7213 Intermediate Similarity NPC165808
0.7188 Intermediate Similarity NPC474658
0.7167 Intermediate Similarity NPC46151
0.7077 Intermediate Similarity NPC469723
0.7069 Intermediate Similarity NPC48162
0.7069 Intermediate Similarity NPC148056
0.7059 Intermediate Similarity NPC473603
0.7059 Intermediate Similarity NPC476059
0.7059 Intermediate Similarity NPC144511
0.7059 Intermediate Similarity NPC296522
0.7049 Intermediate Similarity NPC141699
0.7037 Intermediate Similarity NPC106819
0.7018 Intermediate Similarity NPC163345
0.7 Intermediate Similarity NPC95581
0.6964 Remote Similarity NPC22098
0.6964 Remote Similarity NPC195246
0.6964 Remote Similarity NPC276009
0.6957 Remote Similarity NPC475310
0.6957 Remote Similarity NPC472955
0.6897 Remote Similarity NPC27264
0.6897 Remote Similarity NPC142103
0.6885 Remote Similarity NPC477984
0.6875 Remote Similarity NPC19241
0.6857 Remote Similarity NPC257618
0.6857 Remote Similarity NPC129665
0.6852 Remote Similarity NPC187922
0.6818 Remote Similarity NPC329698
0.6812 Remote Similarity NPC199557
0.6812 Remote Similarity NPC22301
0.6806 Remote Similarity NPC475861
0.6786 Remote Similarity NPC47946
0.6786 Remote Similarity NPC26600
0.6774 Remote Similarity NPC327388
0.6774 Remote Similarity NPC96663
0.6769 Remote Similarity NPC228574
0.6769 Remote Similarity NPC294304
0.6765 Remote Similarity NPC194871
0.6761 Remote Similarity NPC107783
0.6761 Remote Similarity NPC135703
0.6761 Remote Similarity NPC92909
0.6757 Remote Similarity NPC35574
0.6757 Remote Similarity NPC4827
0.6724 Remote Similarity NPC15912
0.6712 Remote Similarity NPC41017
0.6667 Remote Similarity NPC166797
0.6667 Remote Similarity NPC117746
0.6667 Remote Similarity NPC306928
0.6667 Remote Similarity NPC323498
0.6667 Remote Similarity NPC167049
0.6667 Remote Similarity NPC469690
0.6667 Remote Similarity NPC211752
0.6667 Remote Similarity NPC259599
0.6667 Remote Similarity NPC474758
0.6667 Remote Similarity NPC472966
0.6667 Remote Similarity NPC470256
0.6667 Remote Similarity NPC197467
0.6667 Remote Similarity NPC323597
0.6667 Remote Similarity NPC155849
0.6667 Remote Similarity NPC469691
0.6667 Remote Similarity NPC327674
0.6667 Remote Similarity NPC15499
0.6667 Remote Similarity NPC294434
0.662 Remote Similarity NPC163003
0.6618 Remote Similarity NPC154728
0.6618 Remote Similarity NPC304665
0.6618 Remote Similarity NPC126899
0.6618 Remote Similarity NPC477982
0.6613 Remote Similarity NPC200845
0.6613 Remote Similarity NPC223677
0.6613 Remote Similarity NPC28779
0.6613 Remote Similarity NPC128061
0.6613 Remote Similarity NPC10316
0.661 Remote Similarity NPC236338
0.6579 Remote Similarity NPC195424
0.6579 Remote Similarity NPC304795
0.6575 Remote Similarity NPC324762
0.6575 Remote Similarity NPC228978
0.6575 Remote Similarity NPC329852
0.6575 Remote Similarity NPC469678
0.6575 Remote Similarity NPC469669
0.6575 Remote Similarity NPC475771
0.6571 Remote Similarity NPC476591
0.6571 Remote Similarity NPC88877
0.6562 Remote Similarity NPC478096
0.6562 Remote Similarity NPC329819
0.6557 Remote Similarity NPC165755
0.6557 Remote Similarity NPC71761
0.6538 Remote Similarity NPC475622
0.6538 Remote Similarity NPC108045
0.6533 Remote Similarity NPC207186
0.6533 Remote Similarity NPC474341
0.6533 Remote Similarity NPC471220
0.6528 Remote Similarity NPC58956
0.6528 Remote Similarity NPC269206
0.6528 Remote Similarity NPC295633
0.6528 Remote Similarity NPC144947
0.6515 Remote Similarity NPC151648
0.6494 Remote Similarity NPC229584
0.6494 Remote Similarity NPC327002
0.6494 Remote Similarity NPC475665
0.6494 Remote Similarity NPC14203
0.6491 Remote Similarity NPC117572
0.6486 Remote Similarity NPC471726
0.6486 Remote Similarity NPC472967
0.6486 Remote Similarity NPC226242
0.6486 Remote Similarity NPC61863
0.6486 Remote Similarity NPC27205
0.6486 Remote Similarity NPC899
0.6486 Remote Similarity NPC474527
0.6486 Remote Similarity NPC472959
0.6486 Remote Similarity NPC110461
0.6486 Remote Similarity NPC12740
0.6486 Remote Similarity NPC266159
0.6481 Remote Similarity NPC123357
0.6479 Remote Similarity NPC469660
0.6479 Remote Similarity NPC472017
0.6471 Remote Similarity NPC470688
0.6462 Remote Similarity NPC478095
0.6447 Remote Similarity NPC469620
0.6447 Remote Similarity NPC325869
0.6441 Remote Similarity NPC207815
0.6438 Remote Similarity NPC140287
0.6438 Remote Similarity NPC476355
0.6438 Remote Similarity NPC474551
0.6429 Remote Similarity NPC276290
0.6429 Remote Similarity NPC209327
0.6429 Remote Similarity NPC469688
0.6429 Remote Similarity NPC273508
0.6429 Remote Similarity NPC469679
0.6418 Remote Similarity NPC217940
0.6418 Remote Similarity NPC68110
0.6418 Remote Similarity NPC322457
0.641 Remote Similarity NPC200513
0.641 Remote Similarity NPC35556
0.64 Remote Similarity NPC107668
0.64 Remote Similarity NPC473825
0.64 Remote Similarity NPC476325
0.64 Remote Similarity NPC186109
0.64 Remote Similarity NPC472300
0.64 Remote Similarity NPC474760
0.64 Remote Similarity NPC195785
0.64 Remote Similarity NPC476264
0.64 Remote Similarity NPC15975
0.64 Remote Similarity NPC57744
0.6389 Remote Similarity NPC160817
0.6389 Remote Similarity NPC40327
0.6375 Remote Similarity NPC283733
0.6364 Remote Similarity NPC79756
0.6351 Remote Similarity NPC113639
0.6351 Remote Similarity NPC472327
0.6351 Remote Similarity NPC226669
0.6351 Remote Similarity NPC138408
0.6351 Remote Similarity NPC474419
0.6351 Remote Similarity NPC193351
0.6351 Remote Similarity NPC155587
0.6338 Remote Similarity NPC269841
0.6338 Remote Similarity NPC261398
0.6338 Remote Similarity NPC477448
0.6338 Remote Similarity NPC469677
0.6338 Remote Similarity NPC329656
0.6338 Remote Similarity NPC107130
0.6338 Remote Similarity NPC477449
0.6329 Remote Similarity NPC222358
0.6329 Remote Similarity NPC22611
0.6329 Remote Similarity NPC193198
0.6329 Remote Similarity NPC470948
0.6324 Remote Similarity NPC226066
0.6324 Remote Similarity NPC234767
0.6316 Remote Similarity NPC59436
0.6316 Remote Similarity NPC474056
0.6316 Remote Similarity NPC184737
0.6316 Remote Similarity NPC469510
0.6316 Remote Similarity NPC321514
0.6316 Remote Similarity NPC474005
0.6316 Remote Similarity NPC239098
0.6316 Remote Similarity NPC128276
0.6308 Remote Similarity NPC311852
0.6301 Remote Similarity NPC472018
0.6301 Remote Similarity NPC472956
0.6301 Remote Similarity NPC474543
0.6301 Remote Similarity NPC238425
0.6301 Remote Similarity NPC276336
0.6296 Remote Similarity NPC474045
0.6296 Remote Similarity NPC261253
0.629 Remote Similarity NPC309606
0.629 Remote Similarity NPC139545
0.629 Remote Similarity NPC39633
0.6286 Remote Similarity NPC472875

  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 NPC252860 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 NPD5343 Approved
0.7069 Intermediate Similarity NPD6927 Phase 3
0.6909 Remote Similarity NPD6097 Approved
0.6909 Remote Similarity NPD6096 Approved
0.6842 Remote Similarity NPD5209 Approved
0.6575 Remote Similarity NPD8039 Approved
0.6491 Remote Similarity NPD3174 Discontinued
0.6491 Remote Similarity NPD4222 Approved
0.6471 Remote Similarity NPD2685 Clinical (unspecified phase)
0.641 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6324 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6167 Remote Similarity NPD3173 Approved
0.6104 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6098 Remote Similarity NPD5330 Approved
0.6098 Remote Similarity NPD7334 Approved
0.6098 Remote Similarity NPD7146 Approved
0.6098 Remote Similarity NPD7521 Approved
0.6098 Remote Similarity NPD6684 Approved
0.6098 Remote Similarity NPD6409 Approved
0.6061 Remote Similarity NPD6109 Phase 1
0.5976 Remote Similarity NPD1694 Approved
0.5968 Remote Similarity NPD28 Approved
0.5968 Remote Similarity NPD29 Approved
0.5952 Remote Similarity NPD6903 Approved
0.5952 Remote Similarity NPD6672 Approved
0.5952 Remote Similarity NPD5737 Approved
0.5952 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5949 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5932 Remote Similarity NPD39 Approved
0.5862 Remote Similarity NPD5326 Phase 3
0.5821 Remote Similarity NPD287 Approved
0.5802 Remote Similarity NPD6435 Approved
0.5783 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5781 Remote Similarity NPD3172 Approved
0.5747 Remote Similarity NPD6411 Approved
0.5738 Remote Similarity NPD2266 Phase 2
0.5732 Remote Similarity NPD5362 Discontinued
0.5732 Remote Similarity NPD7154 Phase 3
0.573 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5783 Phase 3
0.5714 Remote Similarity NPD6098 Approved
0.5698 Remote Similarity NPD1695 Approved
0.5696 Remote Similarity NPD4271 Approved
0.5696 Remote Similarity NPD4268 Approved
0.5692 Remote Similarity NPD4266 Approved
0.5692 Remote Similarity NPD3194 Approved
0.5692 Remote Similarity NPD3196 Approved
0.5692 Remote Similarity NPD3195 Phase 2
0.5682 Remote Similarity NPD6399 Phase 3
0.5679 Remote Similarity NPD5369 Approved
0.5679 Remote Similarity NPD857 Phase 3
0.5652 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5647 Remote Similarity NPD3573 Approved
0.5618 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5618 Remote Similarity NPD7748 Approved
0.5618 Remote Similarity NPD6001 Approved
0.5618 Remote Similarity NPD7900 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