Structure

Physi-Chem Properties

Molecular Weight:  268.07
Volume:  273.692
LogP:  3.735
LogD:  3.028
LogS:  -5.753
# Rotatable Bonds:  1
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.736
Synthetic Accessibility Score:  2.098
Fsp3:  0.125
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.832
MDCK Permeability:  1.9454670109553263e-05
Pgp-inhibitor:  0.072
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.249
Plasma Protein Binding (PPB):  98.13282775878906%
Volume Distribution (VD):  0.434
Pgp-substrate:  1.1450245380401611%

ADMET: Metabolism

CYP1A2-inhibitor:  0.952
CYP1A2-substrate:  0.864
CYP2C19-inhibitor:  0.508
CYP2C19-substrate:  0.112
CYP2C9-inhibitor:  0.682
CYP2C9-substrate:  0.702
CYP2D6-inhibitor:  0.429
CYP2D6-substrate:  0.403
CYP3A4-inhibitor:  0.727
CYP3A4-substrate:  0.211

ADMET: Excretion

Clearance (CL):  8.103
Half-life (T1/2):  0.124

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.055
Drug-inuced Liver Injury (DILI):  0.929
AMES Toxicity:  0.883
Rat Oral Acute Toxicity:  0.306
Maximum Recommended Daily Dose:  0.885
Skin Sensitization:  0.192
Carcinogencity:  0.92
Eye Corrosion:  0.005
Eye Irritation:  0.975
Respiratory Toxicity:  0.1

Download Data

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

  Natural Product: NPC311120

Natural Product ID:  NPC311120
Common Name*:   HOGWLZYYLVDAOW-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HOGWLZYYLVDAOW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H12O4/c1-8-6-10-13(11(17)7-8)16(19)14-9(15(10)18)4-3-5-12(14)20-2/h3-7,17H,1-2H3
SMILES:  Cc1cc2c(c(c1)O)C(=O)c1c(cccc1OC)C2=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   11300144
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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
NPO7198 Scilla socialis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. PMID[17536859]
NPO11174 Hemsleya graciliflora Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11174 Hemsleya graciliflora Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO921 Helichrysum subulifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8780 Melicope triphylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2762 Senna lindheimeriana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10120 Nuxia floribunda Species Stilbaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5544 Endiandra xanthocarpa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3524 Endothia longirostris Species Cryphonectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5070 Mycocepurus goeldii Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7834 Tricholoma portentosum Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5575 Parmelia alpicola Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2417 Xylaria longiana Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4111 Schistostephium artemisiifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2779 Syzygium australe Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11174 Hemsleya graciliflora Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9987 Tricholomopsis rutilans Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8156.1 Taraxacum platycarpum subsp. hondoense Subspecies Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25664 Halorhodospira halochloris Species Ectothiorhodospiraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6497 Patiria miniata Species Asterinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7644 Dysoxylum muelleri Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4620 Marasmius prasiosmus Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7198 Scilla socialis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9 Camarops microspora Species Boliniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9082 Phialophora asteris Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4511 Canarium bengalense Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2603 Lactuca plumieri Species Asteraceae 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 NPC311120 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 NPC311120 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