Structure

Physi-Chem Properties

Molecular Weight:  248.14
Volume:  272.628
LogP:  3.449
LogD:  3.073
LogS:  -2.911
# Rotatable Bonds:  5
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.62
Synthetic Accessibility Score:  3.392
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.729
MDCK Permeability:  2.4695113097550347e-05
Pgp-inhibitor:  0.064
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.984
30% Bioavailability (F30%):  0.615

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.04
Plasma Protein Binding (PPB):  69.09435272216797%
Volume Distribution (VD):  0.984
Pgp-substrate:  18.110517501831055%

ADMET: Metabolism

CYP1A2-inhibitor:  0.799
CYP1A2-substrate:  0.928
CYP2C19-inhibitor:  0.155
CYP2C19-substrate:  0.21
CYP2C9-inhibitor:  0.106
CYP2C9-substrate:  0.862
CYP2D6-inhibitor:  0.849
CYP2D6-substrate:  0.894
CYP3A4-inhibitor:  0.272
CYP3A4-substrate:  0.222

ADMET: Excretion

Clearance (CL):  15.851
Half-life (T1/2):  0.837

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.266
Drug-inuced Liver Injury (DILI):  0.039
AMES Toxicity:  0.046
Rat Oral Acute Toxicity:  0.053
Maximum Recommended Daily Dose:  0.834
Skin Sensitization:  0.965
Carcinogencity:  0.21
Eye Corrosion:  0.873
Eye Irritation:  0.965
Respiratory Toxicity:  0.596

Download Data

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

  Natural Product: NPC96117

Natural Product ID:  NPC96117
Common Name*:   UZLYFZDXWGWUGA-BJMVGYQFSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UZLYFZDXWGWUGA-BJMVGYQFSA-N
Standard InCHI:  InChI=1S/C15H20O3/c1-10(9-16)5-4-6-11(2)13-8-14(17)12(3)7-15(13)18/h5,7-9,11,15,18H,4,6H2,1-3H3/b10-5+
SMILES:  C/C(=CCCC(C)C1=CC(=O)C(=CC1O)C)/C=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   5317654
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. small food enterprises (Zvijezda d.d., Zagreb, Croatia) n.a. DOI[10.1002/EJLT.200900231]
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[16660462]
NPO454 Helianthus annuus Species Asteraceae Eukaryota flower petals n.a. n.a. PMID[17480100]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[6361218]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Pollen Or Spore n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Flower Essent. Oil n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23019 Glycyrrhiza kansuensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23019 Glycyrrhiza kansuensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO454 Helianthus annuus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23019 Glycyrrhiza kansuensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO454 Helianthus annuus 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 NPC96117 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 NPC96117 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