Structure

Physi-Chem Properties

Molecular Weight:  237.14
Volume:  245.749
LogP:  1.239
LogD:  1.36
LogS:  -1.088
# Rotatable Bonds:  4
TPSA:  49.77
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.449
Synthetic Accessibility Score:  3.951
Fsp3:  0.615
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:  -4.48
MDCK Permeability:  6.729952292516828e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.03
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.333
30% Bioavailability (F30%):  0.851

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.613
Plasma Protein Binding (PPB):  27.3248233795166%
Volume Distribution (VD):  1.014
Pgp-substrate:  75.88371276855469%

ADMET: Metabolism

CYP1A2-inhibitor:  0.108
CYP1A2-substrate:  0.111
CYP2C19-inhibitor:  0.04
CYP2C19-substrate:  0.494
CYP2C9-inhibitor:  0.012
CYP2C9-substrate:  0.116
CYP2D6-inhibitor:  0.389
CYP2D6-substrate:  0.385
CYP3A4-inhibitor:  0.044
CYP3A4-substrate:  0.317

ADMET: Excretion

Clearance (CL):  8.715
Half-life (T1/2):  0.845

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.236
Drug-inuced Liver Injury (DILI):  0.167
AMES Toxicity:  0.125
Rat Oral Acute Toxicity:  0.968
Maximum Recommended Daily Dose:  0.753
Skin Sensitization:  0.551
Carcinogencity:  0.936
Eye Corrosion:  0.013
Eye Irritation:  0.386
Respiratory Toxicity:  0.849

Download Data

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

  Natural Product: NPC44015

Natural Product ID:  NPC44015
Common Name*:   TYGYPIIOOQNWBU-SPVDEYDNSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  TYGYPIIOOQNWBU-SPVDEYDNSA-N
Standard InCHI:  InChI=1S/C13H19NO3/c1-3-9(2)13(16)17-11-5-7-14-6-4-10(8-15)12(11)14/h3-4,11-12,15H,5-8H2,1-2H3/b9-3+/t11-,12?/m0/s1
SMILES:  C/C=C(C)/C(=O)O[C@H]1CCN2CC=C(CO)C12
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   6432671
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)89267-5]
NPO17694 Nicotiana tabacum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[11559179]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12882150]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[15666542]
NPO17694 Nicotiana tabacum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[18001808]
NPO17694 Nicotiana tabacum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[20954721]
NPO17694 Nicotiana tabacum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[23479199]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. trunk bark n.a. PMID[556731]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Tuber n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Tubers n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17694 Nicotiana tabacum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15024 Senecio rivularis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15024 Senecio rivularis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17694 Nicotiana tabacum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28746 Cynoglossum zeylanicum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17694 Nicotiana tabacum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17694 Nicotiana tabacum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15024 Senecio rivularis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28746 Cynoglossum zeylanicum Species Boraginaceae 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 NPC44015 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 NPC44015 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