Structure

Physi-Chem Properties

Molecular Weight:  305.11
Volume:  310.674
LogP:  4.557
LogD:  3.149
LogS:  -6.976
# Rotatable Bonds:  1
TPSA:  38.77
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.595
Synthetic Accessibility Score:  2.604
Fsp3:  0.211
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:  -4.97
MDCK Permeability:  2.1559901142609306e-05
Pgp-inhibitor:  0.958
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.744
Plasma Protein Binding (PPB):  94.96212005615234%
Volume Distribution (VD):  0.976
Pgp-substrate:  1.6393029689788818%

ADMET: Metabolism

CYP1A2-inhibitor:  0.982
CYP1A2-substrate:  0.491
CYP2C19-inhibitor:  0.965
CYP2C19-substrate:  0.424
CYP2C9-inhibitor:  0.759
CYP2C9-substrate:  0.909
CYP2D6-inhibitor:  0.926
CYP2D6-substrate:  0.764
CYP3A4-inhibitor:  0.866
CYP3A4-substrate:  0.435

ADMET: Excretion

Clearance (CL):  5.262
Half-life (T1/2):  0.234

ADMET: Toxicity

hERG Blockers:  0.024
Human Hepatotoxicity (H-HT):  0.769
Drug-inuced Liver Injury (DILI):  0.847
AMES Toxicity:  0.754
Rat Oral Acute Toxicity:  0.042
Maximum Recommended Daily Dose:  0.77
Skin Sensitization:  0.868
Carcinogencity:  0.946
Eye Corrosion:  0.005
Eye Irritation:  0.186
Respiratory Toxicity:  0.405

Download Data

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

  Natural Product: NPC49555

Natural Product ID:  NPC49555
Common Name*:   FNUSCCFSHRMQQM-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  FNUSCCFSHRMQQM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H15NO3/c1-11(21)20-7-6-13-9-16-19(23-10-22-16)18-14-5-3-2-4-12(14)8-15(20)17(13)18/h2-5,8-9H,6-7,10H2,1H3
SMILES:  CC(=O)N1CCc2cc3c(c4c5ccccc5cc1c24)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   5315739
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1016/0031-9422(90)85209-X]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. Caribbean n.a. PMID[10021943]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. Taiwan n.a. PMID[11277748]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[15921424]
NPO26203 Dysidea villosa Species Dysideidae Eukaryota n.a. Hainan, China n.a. PMID[19091557]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[23806071]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. China n.a. PMID[25115700]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[26666037]
NPO25406 Celastrus monospermus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[28006915]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7798955]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13313 Talipariti tiliaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26789 Tephrosia bidwilli Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26203 Dysidea villosa Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3963 Hortonia floribunda Species Monimiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1267 Acronychia laurifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25802 Agave deserti Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13313 Talipariti tiliaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25714 Solanum spirale Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3005 Passiflora morifolia Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9324 0techis scutatus Species Elapidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28636 Vernonia lilacina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26160 Thielavia terricola Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25358 Senecio gilliesi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26849 Parmelia zollingeri Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22264 Inula salsoloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25833 Asclepias subulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25406 Celastrus monospermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25259 Schrebera swietenoides Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24918 Jacobaea cannabifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22890 Eutrochium purpureum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25201 Aglaia pyramidata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24547 Xanthoria parietina Species Teloschistaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26690 Lactarius subpiperatus Species Lactariidae 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 NPC49555 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 NPC49555 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