Structure

Physi-Chem Properties

Molecular Weight:  219.09
Volume:  223.181
LogP:  1.371
LogD:  1.664
LogS:  -2.273
# Rotatable Bonds:  2
TPSA:  40.46
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.769
Synthetic Accessibility Score:  1.986
Fsp3:  0.25
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:  -4.53
MDCK Permeability:  3.0355096896528266e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.776
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.521

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.991
Plasma Protein Binding (PPB):  63.233306884765625%
Volume Distribution (VD):  1.357
Pgp-substrate:  26.419130325317383%

ADMET: Metabolism

CYP1A2-inhibitor:  0.866
CYP1A2-substrate:  0.971
CYP2C19-inhibitor:  0.448
CYP2C19-substrate:  0.89
CYP2C9-inhibitor:  0.055
CYP2C9-substrate:  0.837
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.885
CYP3A4-inhibitor:  0.054
CYP3A4-substrate:  0.467

ADMET: Excretion

Clearance (CL):  8.914
Half-life (T1/2):  0.677

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.648
Drug-inuced Liver Injury (DILI):  0.693
AMES Toxicity:  0.729
Rat Oral Acute Toxicity:  0.452
Maximum Recommended Daily Dose:  0.104
Skin Sensitization:  0.236
Carcinogencity:  0.303
Eye Corrosion:  0.023
Eye Irritation:  0.457
Respiratory Toxicity:  0.738

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

  Natural Product: NPC279533

Natural Product ID:  NPC279533
Common Name*:   HCHLTWGUUUDWFP-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HCHLTWGUUUDWFP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H13NO3/c1-13-5-4-8-6-10(15-2)11(16-3)7-9(8)12(13)14/h4-7H,1-3H3
SMILES:  Cn1ccc2cc(c(cc2c1=O)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   11367984
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0002054] Isoquinolones 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
NPO22181 Leibnitzia anandria Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24699147]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota Buds n.a. n.a. PMID[25927817]
NPO7002 Ardisia hortorum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26469 Thalictrum delavayi Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22181 Leibnitzia anandria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7002 Ardisia hortorum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19668.1 Euphorbia characias subsp. wulfenii Subspecies Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22181 Leibnitzia anandria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18333 Sphaerophysa salsula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20581 Sargassum fulvellum Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21780 Strychnos gossweileri Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19888 Doronicum grandiflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26469 Thalictrum delavayi Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22942 Moesziomyces antarcticus Species Ustilaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22629 Spongia vaginalis Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20704 Conus gladiator Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7002 Ardisia hortorum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21410 Populus balsamifera Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20965 Oxytropis lanata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22436 Lora quadra n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20325 Dictyodendrilla cavernosa Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22498 Lithocarpus haipinii Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21468 Dilophus guineensis Species Dictyotaceae 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 NPC279533 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 NPC279533 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