Structure

Physi-Chem Properties

Molecular Weight:  342.11
Volume:  343.16
LogP:  3.236
LogD:  2.975
LogS:  -4.289
# Rotatable Bonds:  5
TPSA:  67.13
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.707
Synthetic Accessibility Score:  2.336
Fsp3:  0.211
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:  -4.546
MDCK Permeability:  2.8716076485579833e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.087
Plasma Protein Binding (PPB):  78.45267486572266%
Volume Distribution (VD):  0.891
Pgp-substrate:  15.994708061218262%

ADMET: Metabolism

CYP1A2-inhibitor:  0.562
CYP1A2-substrate:  0.98
CYP2C19-inhibitor:  0.872
CYP2C19-substrate:  0.824
CYP2C9-inhibitor:  0.812
CYP2C9-substrate:  0.897
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.82
CYP3A4-inhibitor:  0.532
CYP3A4-substrate:  0.729

ADMET: Excretion

Clearance (CL):  3.184
Half-life (T1/2):  0.288

ADMET: Toxicity

hERG Blockers:  0.264
Human Hepatotoxicity (H-HT):  0.107
Drug-inuced Liver Injury (DILI):  0.953
AMES Toxicity:  0.499
Rat Oral Acute Toxicity:  0.398
Maximum Recommended Daily Dose:  0.028
Skin Sensitization:  0.436
Carcinogencity:  0.184
Eye Corrosion:  0.003
Eye Irritation:  0.18
Respiratory Toxicity:  0.039

Download Data

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

  Natural Product: NPC241317

Natural Product ID:  NPC241317
Common Name*:   HLBQIAYRCJIRCQ-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HLBQIAYRCJIRCQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H18O6/c1-21-15-14-12(20)10-13(11-8-6-5-7-9-11)25-16(14)18(23-3)19(24-4)17(15)22-2/h5-10H,1-4H3
SMILES:  COc1c2c(=O)cc(c3ccccc3)oc2c(c(c1OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   122876
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002593] 8-O-methylated flavonoids

*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
NPO20278 Scutellaria indica Species Lamiaceae Eukaryota whole plant n.a. n.a. PMID[25637363]
NPO9585 Oenothera biennis Species Onagraceae Eukaryota Seeds Yichun, Heilongjiang Province, China 2018-Sep PMID[31292343]
NPO9585 Oenothera biennis Species Onagraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO9585 Oenothera biennis Species Onagraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO20278 Scutellaria indica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20278 Scutellaria indica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20278 Scutellaria indica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7411 Pandanus odoratissimus Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25029 Trifolium incarnatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7022 0tholaena neglecta Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1670 Salvia beckeri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8784 Podocytisus caramanicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1285 Helenium linifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20278 Scutellaria indica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13622 Lespedeza thunbergii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8929 Adenium boehmianum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO141 Scutellaria alpina Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9859 Argyrolobium uniflorum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26168 Isatis quadrialata Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9585 Oenothera biennis Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5309 Eucalyptus jensenii Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3526 Moronobea pulchra Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2007 Hygrophorus persoonii Species Hygrophoraceae 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 NPC241317 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 NPC241317 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