Structure

Physi-Chem Properties

Molecular Weight:  328.09
Volume:  319.945
LogP:  2.792
LogD:  3.053
LogS:  -6.021
# Rotatable Bonds:  3
TPSA:  63.22
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.862
Synthetic Accessibility Score:  2.828
Fsp3:  0.278
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:  -4.692
MDCK Permeability:  7.900950004113838e-05
Pgp-inhibitor:  0.632
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.315
Plasma Protein Binding (PPB):  85.8241195678711%
Volume Distribution (VD):  1.086
Pgp-substrate:  8.802327156066895%

ADMET: Metabolism

CYP1A2-inhibitor:  0.887
CYP1A2-substrate:  0.91
CYP2C19-inhibitor:  0.979
CYP2C19-substrate:  0.717
CYP2C9-inhibitor:  0.899
CYP2C9-substrate:  0.909
CYP2D6-inhibitor:  0.934
CYP2D6-substrate:  0.922
CYP3A4-inhibitor:  0.965
CYP3A4-substrate:  0.476

ADMET: Excretion

Clearance (CL):  14.038
Half-life (T1/2):  0.164

ADMET: Toxicity

hERG Blockers:  0.064
Human Hepatotoxicity (H-HT):  0.429
Drug-inuced Liver Injury (DILI):  0.934
AMES Toxicity:  0.308
Rat Oral Acute Toxicity:  0.391
Maximum Recommended Daily Dose:  0.706
Skin Sensitization:  0.099
Carcinogencity:  0.904
Eye Corrosion:  0.004
Eye Irritation:  0.272
Respiratory Toxicity:  0.949

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

  Natural Product: NPC80142

Natural Product ID:  NPC80142
Common Name*:   BJDCWCLMFKKGEE-HVDUHBCDSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BJDCWCLMFKKGEE-HVDUHBCDSA-N
Standard InCHI:  InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12?,13-,14-,15-/m1/s1
SMILES:  C[C@@H]1CC[C@H]2[C@@H](C)C(O)O[C@H]3[C@]42[C@H]1CC[C@](C)(O3)OO4
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   6918483
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002440] Artemisinins

*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]
NPO40450 Aspergillus sclerotiorum PSU-RSPG178 Strain Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[27228159]
NPO40089 Corymbia torelliana Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[29969262]
NPO40380 Tomophagus sp. Species Polyporaceae Eukaryota n.a. n.a. n.a. PMID[30983350]
NPO40293 Plasmodium falciparum Species Plasmodiidae Eukaryota n.a. n.a. n.a. PMID[31403291]
NPO40512 Favolaschia sp. BCC 18686 Strain Favolaschiaceae Eukaryota n.a. n.a. n.a. PMID[32193929]
NPO40511 Favolaschia calocera BCC 36684 Strain Favolaschiaceae Eukaryota n.a. n.a. n.a. PMID[32193929]
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
NPT71 Cell Line HEK293 Homo sapiens Activity = 83.0 % PMID[29969262]
NPT82 Cell Line MDA-MB-231 Homo sapiens EC50 = 10690.0 nM PMID[30429957]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 8240.0 nM PMID[30429957]
NPT2245 Cell Line SiHa Homo sapiens EC50 = 29800.0 nM PMID[30429957]
NPT165 Cell Line HeLa Homo sapiens EC50 = 10460.0 nM PMID[30429957]
NPT396 Cell Line T47D Homo sapiens EC50 = 4600.0 nM PMID[30429957]
NPT2473 Cell Line MDA-MB-361 Homo sapiens EC50 = 1710.0 nM PMID[30429957]
NPT2277 Cell Line C-33-A Homo sapiens EC50 = 1710.0 nM PMID[30429957]
NPT404 Cell Line CCRF-CEM Homo sapiens IC50 = 870.0 nM PMID[30837097]
NPT2251 Cell Line ADR5000 cell line IC50 = 1840.0 nM PMID[30837097]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 34290.0 nM PMID[30837097]
NPT81 Cell Line A549 Homo sapiens IC50 = 45330.0 nM PMID[30837097]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 31710.0 nM PMID[30837097]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 58690.0 nM PMID[30837097]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 100.0 nM PMID[30852384]
NPT1161 Cell Line CHO Cricetulus griseus IC50 > 100000.0 nM PMID[32987134]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 61400.0 nM PMID[33691167]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 73600.0 nM PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens IC50 = 87200.0 nM PMID[33691167]
NPT81 Cell Line A549 Homo sapiens IC50 = 27800.0 nM PMID[33691167]
NPT1505 Cell Line J82 Homo sapiens IC50 = 146200.0 nM PMID[33691167]
NPT737 Cell Line HUVEC Homo sapiens IC50 = 180100.0 nM PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens Activity = 3.61 % PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens Activity = 1.97 % PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens Activity = 0.062 % PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens Activity = 94.4 % PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens Activity = 95.7 % PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens Activity = 0.01 % PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens Activity = 1.56 % PMID[33691167]
NPT377 Cell Line OVCAR-3 Homo sapiens Activity = 2.74 % PMID[33691167]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2.3 nM PMID[27228159]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.4 nM PMID[29969262]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.43 nM PMID[29969262]
NPT2262 Organism Human herpesvirus 5 strain AD169 Human herpesvirus 5 strain AD169 EC50 > 10000.0 nM PMID[30429957]
NPT21742 CELL-LINE L02 Homo sapiens IC50 = 40210.0 nM PMID[30837097]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2.8 nM PMID[30983350]
NPT21742 CELL-LINE L02 Homo sapiens IC50 = 360.0 nM PMID[30852384]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 4100.0 nM PMID[30878827]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3.1 nM PMID[32193929]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2.2 nM PMID[32987134]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 1.2 nM PMID[32987134]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 26970.0 nM PMID[32987134]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 31230.0 nM PMID[32987134]
NPT841 Organism Leishmania major Leishmania major IC50 = 42600.0 nM PMID[32987134]
NPT2 Others Unspecified Ratio IC50 = 4.0 n.a. PMID[32987134]
NPT2 Others Unspecified Ratio IC50 = 3.0 n.a. PMID[32987134]
NPT2 Others Unspecified Ratio IC50 = 2.0 n.a. PMID[32987134]
NPT2 Others Unspecified IC50 = 4030.0 nM PMID[32631539]
NPT2 Others Unspecified IC50 = 5530.0 nM PMID[32631539]

☑ 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 NPC80142 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

  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 NPC80142 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

  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