Structure

Physi-Chem Properties

Molecular Weight:  274.12
Volume:  287.521
LogP:  4.549
LogD:  3.481
LogS:  -3.239
# Rotatable Bonds:  4
TPSA:  73.83
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.582
Synthetic Accessibility Score:  2.937
Fsp3:  0.25
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.719
MDCK Permeability:  1.7166494217235595e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.351
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.966
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.029
Plasma Protein Binding (PPB):  99.21300506591797%
Volume Distribution (VD):  1.592
Pgp-substrate:  2.4897232055664062%

ADMET: Metabolism

CYP1A2-inhibitor:  0.914
CYP1A2-substrate:  0.159
CYP2C19-inhibitor:  0.37
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.631
CYP2C9-substrate:  0.912
CYP2D6-inhibitor:  0.844
CYP2D6-substrate:  0.793
CYP3A4-inhibitor:  0.63
CYP3A4-substrate:  0.145

ADMET: Excretion

Clearance (CL):  12.589
Half-life (T1/2):  0.669

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.388
Drug-inuced Liver Injury (DILI):  0.168
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.19
Maximum Recommended Daily Dose:  0.111
Skin Sensitization:  0.756
Carcinogencity:  0.33
Eye Corrosion:  0.005
Eye Irritation:  0.839
Respiratory Toxicity:  0.155

Download Data

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

  Natural Product: NPC171104

Natural Product ID:  NPC171104
Common Name*:   MUFBROGJHZSIKT-HNNXBMFYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MUFBROGJHZSIKT-HNNXBMFYSA-N
Standard InCHI:  InChI=1S/C16H18O4/c1-10(2)4-3-5-11-8-15(20-16(11)19)13-9-12(17)6-7-14(13)18/h4,6-9,15,17-18H,3,5H2,1-2H3/t15-/m0/s1
SMILES:  CC(=CCCC1=C[C@@H](c2cc(ccc2O)O)OC1=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   122662599
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0001286] Benzenediols
          • [CHEMONTID:0000136] Hydroquinones

*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
NPO26499 Dorstenia kameruniana Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24129 Bifurcaria bifurcata Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17880 Phlomis spinidens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26499 Dorstenia kameruniana Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26441 Sideritis angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22023 Scutellaria tenax Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24129 Bifurcaria bifurcata Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23515 Chrysanthemum yoshinaganthum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17880 Phlomis spinidens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26499 Dorstenia kameruniana Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28723 Ia io Species Vespertilionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23310 Flourensia resinosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26067 Acacia sutherlandii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24345 Amoora stellato-squamosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26837 Laurencia grevilleana Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22255 Dendrodochium toxicum Species Bionectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6443 Amesia atrobrunnea Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24680 Evernia illyrica Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25315 Tragopogon dasyrhynchus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25750 Irvingia gabonensis Species Irvingiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25882 Salix americana Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10307 Leccinum extremiorientale Species Boletaceae 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 NPC171104 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 NPC171104 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