Structure

Physi-Chem Properties

Molecular Weight:  339.26
Volume:  393.219
LogP:  6.141
LogD:  4.363
LogS:  -3.077
# Rotatable Bonds:  11
TPSA:  22.0
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.354
Synthetic Accessibility Score:  2.372
Fsp3:  0.522
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.748
MDCK Permeability:  1.623845128051471e-05
Pgp-inhibitor:  0.091
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.859
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.888
Plasma Protein Binding (PPB):  98.4388198852539%
Volume Distribution (VD):  2.04
Pgp-substrate:  0.6133973598480225%

ADMET: Metabolism

CYP1A2-inhibitor:  0.349
CYP1A2-substrate:  0.497
CYP2C19-inhibitor:  0.554
CYP2C19-substrate:  0.411
CYP2C9-inhibitor:  0.265
CYP2C9-substrate:  0.947
CYP2D6-inhibitor:  0.491
CYP2D6-substrate:  0.923
CYP3A4-inhibitor:  0.583
CYP3A4-substrate:  0.134

ADMET: Excretion

Clearance (CL):  4.526
Half-life (T1/2):  0.462

ADMET: Toxicity

hERG Blockers:  0.383
Human Hepatotoxicity (H-HT):  0.132
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.68
Rat Oral Acute Toxicity:  0.125
Maximum Recommended Daily Dose:  0.551
Skin Sensitization:  0.961
Carcinogencity:  0.173
Eye Corrosion:  0.005
Eye Irritation:  0.95
Respiratory Toxicity:  0.666

Download Data

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

  Natural Product: NPC289145

Natural Product ID:  NPC289145
Common Name*:   HWFYWIVOYBPLQU-SREVYHEPSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HWFYWIVOYBPLQU-SREVYHEPSA-N
Standard InCHI:  InChI=1S/C23H33NO/c1-3-4-5-6-7-8-9-10-11-12-13-16-20-19-23(25)21-17-14-15-18-22(21)24(20)2/h6-7,14-15,17-19H,3-5,8-13,16H2,1-2H3/b7-6-
SMILES:  CCCC/C=CCCCCCCCc1cc(=O)c2ccccc2n1C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   5317303
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0000056] Quinolones and derivatives
          • [CHEMONTID:0001716] Hydroquinolones

*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
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8201313]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8699182]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22281 Warburgia salutaris Species Canellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14163.1 Hesperocyparis goveniana var. abramsiana Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22281 Warburgia salutaris Species Canellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4877 Euodia officinalis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8314 Euodia ruticarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16845 Euodia bodinieri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21954 Streptomyces levoris Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17513 Lagochilus hirsutissimus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14163.1 Hesperocyparis goveniana var. abramsiana Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22281 Warburgia salutaris Species Canellaceae 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 NPC289145 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 NPC289145 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