Structure

Physi-Chem Properties

Molecular Weight:  290.19
Volume:  318.596
LogP:  5.955
LogD:  4.259
LogS:  -5.994
# Rotatable Bonds:  8
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.695
Synthetic Accessibility Score:  2.72
Fsp3:  0.611
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:  -4.664
MDCK Permeability:  2.829991171893198e-05
Pgp-inhibitor:  0.333
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.992
30% Bioavailability (F30%):  0.633

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.629
Plasma Protein Binding (PPB):  98.07701873779297%
Volume Distribution (VD):  0.766
Pgp-substrate:  1.640333652496338%

ADMET: Metabolism

CYP1A2-inhibitor:  0.913
CYP1A2-substrate:  0.265
CYP2C19-inhibitor:  0.904
CYP2C19-substrate:  0.077
CYP2C9-inhibitor:  0.543
CYP2C9-substrate:  0.957
CYP2D6-inhibitor:  0.882
CYP2D6-substrate:  0.357
CYP3A4-inhibitor:  0.643
CYP3A4-substrate:  0.127

ADMET: Excretion

Clearance (CL):  4.34
Half-life (T1/2):  0.173

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.174
Drug-inuced Liver Injury (DILI):  0.856
AMES Toxicity:  0.58
Rat Oral Acute Toxicity:  0.111
Maximum Recommended Daily Dose:  0.884
Skin Sensitization:  0.926
Carcinogencity:  0.432
Eye Corrosion:  0.131
Eye Irritation:  0.977
Respiratory Toxicity:  0.89

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

  Natural Product: NPC303782

Natural Product ID:  NPC303782
Common Name*:   FQQQPUQXIXHMRM-CQSZACIVSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  FQQQPUQXIXHMRM-CQSZACIVSA-N
Standard InCHI:  InChI=1S/C18H26O3/c1-2-3-4-5-6-7-8-10-14-13-16(20)18-15(19)11-9-12-17(18)21-14/h9,11-12,14,19H,2-8,10,13H2,1H3/t14-/m1/s1
SMILES:  CCCCCCCCC[C@@H]1CC(=O)c2c(cccc2O1)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:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0000144] Chromones

*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
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[18270436]
NPO24632 Salvia hydrangea Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[21967089]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[23793896]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. seed n.a. PMID[24967651]
NPO24632 Salvia hydrangea Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30565934]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28731 Trifolium fragiferum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22591 Lonchocarpus xuul Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24632 Salvia hydrangea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28731 Trifolium fragiferum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25434 Asparagus adscendens Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25405 Haemophilus influenzae Species Pasteurellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22591 Lonchocarpus xuul Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24469 Myeloconis erumpens Species Myeloconidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24632 Salvia hydrangea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24819 Inezia integrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25616 Polygala macra Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22929 Cichorium pumilum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28731 Trifolium fragiferum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14647 Tylopilus felleus Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25434 Asparagus adscendens Species Asparagaceae 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 NPC303782 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 NPC303782 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