Structure

Physi-Chem Properties

Molecular Weight:  233.14
Volume:  245.699
LogP:  1.903
LogD:  1.937
LogS:  -1.941
# Rotatable Bonds:  2
TPSA:  21.7
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.783
Synthetic Accessibility Score:  2.453
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.495
MDCK Permeability:  2.294107798661571e-05
Pgp-inhibitor:  0.063
Pgp-substrate:  0.986
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.045
30% Bioavailability (F30%):  0.112

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.99
Plasma Protein Binding (PPB):  49.487178802490234%
Volume Distribution (VD):  2.383
Pgp-substrate:  43.5438346862793%

ADMET: Metabolism

CYP1A2-inhibitor:  0.145
CYP1A2-substrate:  0.946
CYP2C19-inhibitor:  0.038
CYP2C19-substrate:  0.939
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.201
CYP2D6-inhibitor:  0.854
CYP2D6-substrate:  0.917
CYP3A4-inhibitor:  0.007
CYP3A4-substrate:  0.84

ADMET: Excretion

Clearance (CL):  8.958
Half-life (T1/2):  0.797

ADMET: Toxicity

hERG Blockers:  0.082
Human Hepatotoxicity (H-HT):  0.23
Drug-inuced Liver Injury (DILI):  0.347
AMES Toxicity:  0.103
Rat Oral Acute Toxicity:  0.274
Maximum Recommended Daily Dose:  0.909
Skin Sensitization:  0.283
Carcinogencity:  0.155
Eye Corrosion:  0.004
Eye Irritation:  0.038
Respiratory Toxicity:  0.955

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

  Natural Product: NPC265171

Natural Product ID:  NPC265171
Common Name*:   MVIOZTSBCZNBFR-GFCCVEGCSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MVIOZTSBCZNBFR-GFCCVEGCSA-N
Standard InCHI:  InChI=1S/C14H19NO2/c1-16-13-8-10-5-7-15-6-3-4-12(15)11(10)9-14(13)17-2/h8-9,12H,3-7H2,1-2H3/t12-/m1/s1
SMILES:  COc1cc2CCN3CCC[C@@H]3c2cc1OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   11673094
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002955] Tetrahydroisoquinolines

*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
NPO874 Narthecium asiaticum Species Nartheciaceae Eukaryota n.a. n.a. n.a. PMID[14980692]
NPO244 Stachyurus himalaicus Species Stachyuraceae Eukaryota n.a. n.a. n.a. PMID[17851408]
NPO2348 Tripterygium regelii Species Celastraceae Eukaryota n.a. bark n.a. PMID[20167482]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. PMID[21608987]
NPO2348 Tripterygium regelii Species Celastraceae Eukaryota n.a. stem n.a. PMID[27113553]
NPO2348 Tripterygium regelii Species Celastraceae Eukaryota n.a. root n.a. PMID[2801129]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. Database[FooDB]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1384 Cucumis myriocarpus Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2348 Tripterygium regelii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7026 Vismia orientalis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4129 Veronica persica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO7026 Vismia orientalis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2348 Tripterygium regelii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1384 Cucumis myriocarpus Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4129 Veronica persica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2348 Tripterygium regelii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO244 Stachyurus himalaicus Species Stachyuraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1384 Cucumis myriocarpus Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10856 Passiflora edulis Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7098 Phebalium ambiens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO874 Narthecium asiaticum Species Nartheciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7026 Vismia orientalis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2213 Chavica betle n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5599 Chrysocoma peduncularis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1249 Euphorbia sieboldiana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO591 Penicillium meleagrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7379 Clostridium butyricum Species Clostridiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO244 Stachyurus himalaicus Species Stachyuraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2277 Angylocalyx braunii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2348 Tripterygium regelii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7235 Brachychiton populneum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO962 Vernonanthura pinguis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5154 Tsuga diversifolia Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4000 Archidendron lucidum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4786 Chrysotila lamellosa Species Isochrysidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7897 Passiflora foetida Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23104 Wedelia scaberrima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4129 Veronica persica Species Plantaginaceae 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
NPT410 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Homo sapiens IC50 > 100000.0 nM PMID[465910]
NPT410 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Homo sapiens EC50 > 100000.0 nM PMID[465910]
NPT418 Protein Complex Neuronal acetylcholine receptor; alpha4/beta4 Rattus norvegicus Ki = 100000.0 nM PMID[465910]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 2500.0 nM PMID[465910]
NPT417 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Rattus norvegicus Ki = 100000.0 nM PMID[465910]
NPT964 Protein Complex Nicotinic acetylcholine receptor alpha-4/beta-2 Mus musculus IC50 = 16000.0 nM PMID[465910]
NPT417 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Rattus norvegicus IC50 > 100000.0 nM PMID[465910]

☑ 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 NPC265171 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 NPC265171 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