Structure

Physi-Chem Properties

Molecular Weight:  84.02
Volume:  81.491
LogP:  0.678
LogD:  0.971
LogS:  -0.098
# Rotatable Bonds:  0
TPSA:  33.37
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.508
Synthetic Accessibility Score:  3.044
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.446
MDCK Permeability:  2.2316944523481652e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.022
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.219
Plasma Protein Binding (PPB):  79.2189712524414%
Volume Distribution (VD):  2.455
Pgp-substrate:  38.78162384033203%

ADMET: Metabolism

CYP1A2-inhibitor:  0.205
CYP1A2-substrate:  0.147
CYP2C19-inhibitor:  0.048
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.014
CYP2C9-substrate:  0.399
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.597
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.178

ADMET: Excretion

Clearance (CL):  14.22
Half-life (T1/2):  0.894

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.13
Drug-inuced Liver Injury (DILI):  0.126
AMES Toxicity:  0.071
Rat Oral Acute Toxicity:  0.877
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.293
Carcinogencity:  0.908
Eye Corrosion:  0.985
Eye Irritation:  0.996
Respiratory Toxicity:  0.903

Download Data

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

  Natural Product: NPC147824

Natural Product ID:  NPC147824
Common Name*:   Furan-2(5H)-One
IUPAC Name:   2H-furan-5-one
Synonyms:   Furan-2(5H)-one
Standard InCHIKey:  VIHAEDVKXSOUAT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
SMILES:  C1OC(=O)C=C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL166223
PubChem CID:   10341
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans
        • [CHEMONTID:0001982] Furanones
          • [CHEMONTID:0002223] Butenolides

*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
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/hlca.19270100148]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Petals n.a. n.a. PMID[15043425]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24338885]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9445 Crocus sativus Species Iridaceae 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
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki > 100000.0 nM PMID[489509]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki = 13600.0 nM PMID[489509]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens Ki = 4420.0 nM PMID[489509]
NPT849 Organism Plutella xylostella Plutella xylostella mortality = 32.5 % PMID[489510]
NPT849 Organism Plutella xylostella Plutella xylostella mortality = 27.5 % PMID[489510]
NPT25998 ORGANISM Diaphania hyalinata Diaphania hyalinata mortality = 24.3 % PMID[489510]
NPT25998 ORGANISM Diaphania hyalinata Diaphania hyalinata mortality = 18.9 % PMID[489510]
NPT25999 ORGANISM Ascia monuste Ascia monuste mortality = 25.0 % PMID[489510]
NPT25999 ORGANISM Ascia monuste Ascia monuste mortality = 22.5 % PMID[489510]
NPT25999 ORGANISM Ascia monuste Ascia monuste mortality = 12.5 % PMID[489510]

☑ 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 NPC147824 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
0.8889 High Similarity NPC122676
0.825 Intermediate Similarity NPC281043
0.7857 Intermediate Similarity NPC41409
0.7805 Intermediate Similarity NPC297608
0.7692 Intermediate Similarity NPC65353
0.7632 Intermediate Similarity NPC63354
0.7561 Intermediate Similarity NPC298413
0.7391 Intermediate Similarity NPC90490
0.7381 Intermediate Similarity NPC250954
0.725 Intermediate Similarity NPC9290
0.7234 Intermediate Similarity NPC82446
0.7083 Intermediate Similarity NPC15789
0.7083 Intermediate Similarity NPC275316
0.7045 Intermediate Similarity NPC57923
0.7027 Intermediate Similarity NPC323552
0.7 Intermediate Similarity NPC60675
0.7 Intermediate Similarity NPC297363
0.6977 Remote Similarity NPC203382
0.6863 Remote Similarity NPC159535
0.6863 Remote Similarity NPC151761
0.675 Remote Similarity NPC98098
0.675 Remote Similarity NPC224651
0.6735 Remote Similarity NPC236338
0.6667 Remote Similarity NPC107877
0.6604 Remote Similarity NPC245002
0.6604 Remote Similarity NPC230296
0.6522 Remote Similarity NPC40805
0.6522 Remote Similarity NPC103560
0.6512 Remote Similarity NPC63598
0.6444 Remote Similarity NPC159773
0.6429 Remote Similarity NPC130953
0.6429 Remote Similarity NPC98519
0.6327 Remote Similarity NPC128520
0.625 Remote Similarity NPC47946
0.625 Remote Similarity NPC26600
0.625 Remote Similarity NPC270706
0.6222 Remote Similarity NPC8270
0.6207 Remote Similarity NPC179087
0.6207 Remote Similarity NPC473737
0.6207 Remote Similarity NPC210303
0.6207 Remote Similarity NPC44343
0.6182 Remote Similarity NPC129150
0.6182 Remote Similarity NPC294938
0.6154 Remote Similarity NPC8466
0.6136 Remote Similarity NPC226511
0.6122 Remote Similarity NPC128280
0.6122 Remote Similarity NPC197467
0.6111 Remote Similarity NPC478117
0.6087 Remote Similarity NPC221250
0.6071 Remote Similarity NPC189700
0.6071 Remote Similarity NPC223679
0.6071 Remote Similarity NPC474084
0.6071 Remote Similarity NPC254095
0.6047 Remote Similarity NPC308418
0.6042 Remote Similarity NPC312547
0.6042 Remote Similarity NPC51329
0.6034 Remote Similarity NPC151648
0.6 Remote Similarity NPC150717
0.6 Remote Similarity NPC51846
0.5965 Remote Similarity NPC97570
0.5965 Remote Similarity NPC159650
0.5965 Remote Similarity NPC286189
0.5965 Remote Similarity NPC302564
0.5965 Remote Similarity NPC22897
0.5965 Remote Similarity NPC82465
0.5957 Remote Similarity NPC102879
0.5957 Remote Similarity NPC190649
0.5952 Remote Similarity NPC310810
0.5932 Remote Similarity NPC68110
0.5918 Remote Similarity NPC172042
0.5902 Remote Similarity NPC276299
0.5897 Remote Similarity NPC20903
0.5893 Remote Similarity NPC135863
0.5893 Remote Similarity NPC249850
0.5893 Remote Similarity NPC293437
0.5882 Remote Similarity NPC234084
0.5882 Remote Similarity NPC135698
0.5882 Remote Similarity NPC126184
0.587 Remote Similarity NPC123357
0.5862 Remote Similarity NPC26223
0.5862 Remote Similarity NPC309408
0.5849 Remote Similarity NPC106531
0.5849 Remote Similarity NPC191643
0.5806 Remote Similarity NPC225272
0.5789 Remote Similarity NPC21946
0.5763 Remote Similarity NPC26810
0.5741 Remote Similarity NPC327103
0.5741 Remote Similarity NPC477781
0.5741 Remote Similarity NPC477780
0.5738 Remote Similarity NPC182794
0.5738 Remote Similarity NPC133904
0.5714 Remote Similarity NPC221763
0.5714 Remote Similarity NPC144407
0.5714 Remote Similarity NPC218477
0.5714 Remote Similarity NPC86948
0.569 Remote Similarity NPC133600
0.5686 Remote Similarity NPC68577
0.5652 Remote Similarity NPC200147
0.5645 Remote Similarity NPC37382
0.5645 Remote Similarity NPC248125
0.5636 Remote Similarity NPC269615
0.5636 Remote Similarity NPC478120
0.5625 Remote Similarity NPC187922

  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 NPC147824 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
0.7949 Intermediate Similarity NPD9115 Approved
0.675 Remote Similarity NPD8573 Approved
0.5897 Remote Similarity NPD8187 Phase 3
0.566 Remote Similarity NPD6927 Phase 3
0.561 Remote Similarity NPD9114 Clinical (unspecified phase)
0.56 Remote Similarity NPD9378 Approved

  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