Structure

Physi-Chem Properties

Molecular Weight:  956.5
Volume:  929.417
LogP:  1.714
LogD:  1.007
LogS:  -3.725
# Rotatable Bonds:  9
TPSA:  312.05
# H-Bond Aceptor:  19
# H-Bond Donor:  11
# Rings:  8
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.106
Synthetic Accessibility Score:  6.548
Fsp3:  0.917
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.054
MDCK Permeability:  9.34875279199332e-05
Pgp-inhibitor:  0.964
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.976
20% Bioavailability (F20%):  0.097
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.199
Plasma Protein Binding (PPB):  45.980194091796875%
Volume Distribution (VD):  0.27
Pgp-substrate:  21.584339141845703%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.37
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.394
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.018
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.054
CYP3A4-inhibitor:  0.096
CYP3A4-substrate:  0.019

ADMET: Excretion

Clearance (CL):  0.436
Half-life (T1/2):  0.638

ADMET: Toxicity

hERG Blockers:  0.116
Human Hepatotoxicity (H-HT):  0.197
Drug-inuced Liver Injury (DILI):  0.028
AMES Toxicity:  0.111
Rat Oral Acute Toxicity:  0.345
Maximum Recommended Daily Dose:  0.918
Skin Sensitization:  0.037
Carcinogencity:  0.149
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC38269

Natural Product ID:  NPC38269
Common Name*:   KEXOKWCAAZNETD-BXGBBSSXSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  KEXOKWCAAZNETD-BXGBBSSXSA-N
Standard InCHI:  InChI=1S/C13H19NO3/c1-8-12(15)13(16)11(14(8)2)9-5-4-6-10(7-9)17-3/h4-8,11-13,15-16H,1-3H3/t8-,11+,12+,13+/m0/s1
SMILES:  C[C@H]1[C@H]([C@@H]([C@@H](c2cccc(c2)OC)N1C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000218] Pyrrolidines
        • [CHEMONTID:0002336] Phenylpyrrolidines

*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
NPO17780 Curcuma heyneana Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23387824]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[26110519]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11837 Codonopsis clematidea Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20907 Costus afer Species Costaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15465 Mikania microptera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17780 Curcuma heyneana Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10359 Chaiturus marrubiastrum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15038 Withania adpressa Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15789 Leucas cephalotes Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1547 Symphytum uplandicum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11837 Codonopsis clematidea Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3719 Potamophylax latipennis Species Limnephilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20907 Costus afer Species Costaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17627 Senecio rufus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16940 Phebalium ralstonii Species Rutaceae 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 NPC38269 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 NPC38269 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