Structure

Physi-Chem Properties

Molecular Weight:  274.16
Volume:  292.744
LogP:  3.957
LogD:  3.758
LogS:  -4.367
# Rotatable Bonds:  2
TPSA:  42.6
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.901
Synthetic Accessibility Score:  4.622
Fsp3:  0.529
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.71
MDCK Permeability:  1.9317276382935233e-05
Pgp-inhibitor:  0.175
Pgp-substrate:  0.011
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.018
30% Bioavailability (F30%):  0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  97.72769927978516%
Volume Distribution (VD):  2.547
Pgp-substrate:  3.6536521911621094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.972
CYP1A2-substrate:  0.744
CYP2C19-inhibitor:  0.404
CYP2C19-substrate:  0.829
CYP2C9-inhibitor:  0.551
CYP2C9-substrate:  0.635
CYP2D6-inhibitor:  0.411
CYP2D6-substrate:  0.343
CYP3A4-inhibitor:  0.522
CYP3A4-substrate:  0.502

ADMET: Excretion

Clearance (CL):  9.073
Half-life (T1/2):  0.581

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.789
Drug-inuced Liver Injury (DILI):  0.526
AMES Toxicity:  0.101
Rat Oral Acute Toxicity:  0.195
Maximum Recommended Daily Dose:  0.572
Skin Sensitization:  0.919
Carcinogencity:  0.858
Eye Corrosion:  0.219
Eye Irritation:  0.293
Respiratory Toxicity:  0.948

Download Data

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

  Natural Product: NPC154537

Natural Product ID:  NPC154537
Common Name*:   NVLKRIFJOPPSSC-GLZQIGESSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  NVLKRIFJOPPSSC-GLZQIGESSA-N
Standard InCHI:  InChI=1S/C17H22O3/c1-5-19-15-14-11(3)16(18)20-13(14)9-12-8-6-7-10(2)17(12,15)4/h8-10,15H,5-7H2,1-4H3/t10-,15-,17+/m0/s1
SMILES:  CCO[C@H]1C2=C(C)C(=O)OC2=CC2=CCC[C@H](C)[C@@]12C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones

*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
NPO29103 Spongia matamata Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[10075761]
NPO28939 Piptanthus nepalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28939 Piptanthus nepalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28939 Piptanthus nepalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28974 Smilax ornata Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29103 Spongia matamata Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26540 Echinopsis spachiana Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29402 Launaea arborescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29194 Harziella entomophila n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO29013 Annulohypoxylon cohaerens Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25969 Aspergillus nomius Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28870 Clausena lenis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11524 Macrotomia ugamensis Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28808 Piptanthus mongolicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28939 Piptanthus nepalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29157 Reichardia gaditana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28829 Pelvetia wrightii Species Fucaceae 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 NPC154537 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 NPC154537 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