Structure

Physi-Chem Properties

Molecular Weight:  344.24
Volume:  385.144
LogP:  5.636
LogD:  4.436
LogS:  -4.869
# Rotatable Bonds:  7
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.386
Synthetic Accessibility Score:  5.269
Fsp3:  0.636
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.607
MDCK Permeability:  3.787078458117321e-05
Pgp-inhibitor:  0.194
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.581
20% Bioavailability (F20%):  0.73
30% Bioavailability (F30%):  0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.388
Plasma Protein Binding (PPB):  94.33922576904297%
Volume Distribution (VD):  2.358
Pgp-substrate:  4.939002990722656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.863
CYP1A2-substrate:  0.096
CYP2C19-inhibitor:  0.365
CYP2C19-substrate:  0.528
CYP2C9-inhibitor:  0.242
CYP2C9-substrate:  0.21
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.091
CYP3A4-inhibitor:  0.548
CYP3A4-substrate:  0.292

ADMET: Excretion

Clearance (CL):  4.342
Half-life (T1/2):  0.239

ADMET: Toxicity

hERG Blockers:  0.309
Human Hepatotoxicity (H-HT):  0.963
Drug-inuced Liver Injury (DILI):  0.437
AMES Toxicity:  0.041
Rat Oral Acute Toxicity:  0.148
Maximum Recommended Daily Dose:  0.763
Skin Sensitization:  0.947
Carcinogencity:  0.802
Eye Corrosion:  0.727
Eye Irritation:  0.413
Respiratory Toxicity:  0.971

Download Data

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

  Natural Product: NPC290369

Natural Product ID:  NPC290369
Common Name*:   SBNUGTOVRAJHEA-MPRQEMDOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SBNUGTOVRAJHEA-MPRQEMDOSA-N
Standard InCHI:  InChI=1S/C22H32O3/c1-14(2)7-6-8-15(3)19-11-9-16(4)20-12-10-18(13-23)21(19)22(20)25-17(5)24/h7,10,13,15,19-22H,4,6,8-9,11-12H2,1-3,5H3/t15-,19+,20+,21-,22-/m1/s1
SMILES:  CC(=CCC[C@@H](C)[C@@H]1CCC(=C)[C@@H]2CC=C(C=O)[C@H]1[C@@H]2OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001093] Carboxylic acid derivatives
          • [CHEMONTID:0001238] Carboxylic acid esters

*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
NPO6812 Bulbine frutescens Species Xanthorrhoeaceae Eukaryota n.a. root n.a. PMID[12193014]
NPO8948 Streptomyces pristinaespiralis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25708513]
NPO8796 Cnemidocarpa bicornuta Species Styelidae Eukaryota n.a. New Zealand n.a. PMID[9644087]
NPO604 Erysimum crepidifolium Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO604 Erysimum crepidifolium Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9742 Entada scandens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO604 Erysimum crepidifolium Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26935 Coprinopsis lagopus Species Psathyrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1481 Balfourodendron riedelianum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16389 Anodonta cygnea Species Unionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12335 Aristolochia reticulata Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8796 Cnemidocarpa bicornuta Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8948 Streptomyces pristinaespiralis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8033 Sordaria macrospora Species Sordariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6812 Bulbine frutescens Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7039 Espeletia uribei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5863 Amyris plumieri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12648 Uragoga ipecacuanha n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2958 Euphorbia glareosa Species Euphorbiaceae 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

☑ 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 NPC290369 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 NPC290369 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