Structure

Physi-Chem Properties

Molecular Weight:  279.95
Volume:  208.62
LogP:  2.408
LogD:  1.267
LogS:  -3.073
# Rotatable Bonds:  3
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.808
Synthetic Accessibility Score:  4.017
Fsp3:  0.444
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:  -4.386
MDCK Permeability:  2.1564683265751228e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.546
30% Bioavailability (F30%):  0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.658
Plasma Protein Binding (PPB):  93.07733154296875%
Volume Distribution (VD):  0.606
Pgp-substrate:  15.225818634033203%

ADMET: Metabolism

CYP1A2-inhibitor:  0.971
CYP1A2-substrate:  0.495
CYP2C19-inhibitor:  0.823
CYP2C19-substrate:  0.145
CYP2C9-inhibitor:  0.706
CYP2C9-substrate:  0.695
CYP2D6-inhibitor:  0.49
CYP2D6-substrate:  0.086
CYP3A4-inhibitor:  0.199
CYP3A4-substrate:  0.176

ADMET: Excretion

Clearance (CL):  2.292
Half-life (T1/2):  0.62

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.428
Drug-inuced Liver Injury (DILI):  0.881
AMES Toxicity:  0.973
Rat Oral Acute Toxicity:  0.836
Maximum Recommended Daily Dose:  0.972
Skin Sensitization:  0.943
Carcinogencity:  0.909
Eye Corrosion:  0.981
Eye Irritation:  0.978
Respiratory Toxicity:  0.98

Download Data

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

  Natural Product: NPC286816

Natural Product ID:  NPC286816
Common Name*:   (R,E)-4-Bromo-5-(Chloromethylene)-3-(1-Hydroxybutyl)Furan-2(5H)-One
IUPAC Name:   (5E)-4-bromo-5-(chloromethylidene)-3-[(1R)-1-hydroxybutyl]furan-2-one
Synonyms:  
Standard InCHIKey:  VXUYDUOMEUFAII-YWSOBTQUSA-N
Standard InCHI:  InChI=1S/C9H10BrClO3/c1-2-3-5(12)7-8(10)6(4-11)14-9(7)13/h4-5,12H,2-3H2,1H3/b6-4+/t5-/m1/s1
SMILES:  CCC[C@H](C1=C(/C(=CCl)/OC1=O)Br)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504905
PubChem CID:   44583902
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
NPO14524 Delisea pulchra Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. PMID[16933872]
NPO14524 Delisea pulchra Species Bonnemaisoniaceae 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
NPT2 Others Unspecified Activity = 1.6 % PMID[497058]

☑ 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 NPC286816 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
1.0 High Similarity NPC199134
0.9067 High Similarity NPC225022
0.9067 High Similarity NPC238554
0.9054 High Similarity NPC177030
0.8947 High Similarity NPC24827
0.8947 High Similarity NPC228902
0.8289 Intermediate Similarity NPC162571
0.8289 Intermediate Similarity NPC112983
0.8267 Intermediate Similarity NPC494
0.8182 Intermediate Similarity NPC146583
0.7901 Intermediate Similarity NPC102065
0.7901 Intermediate Similarity NPC85743
0.76 Intermediate Similarity NPC173409
0.76 Intermediate Similarity NPC53136
0.7568 Intermediate Similarity NPC217537
0.7468 Intermediate Similarity NPC475113
0.7468 Intermediate Similarity NPC299932
0.7375 Intermediate Similarity NPC124072
0.7375 Intermediate Similarity NPC269103
0.7284 Intermediate Similarity NPC144419
0.7195 Intermediate Similarity NPC188354
0.7108 Intermediate Similarity NPC329826
0.7108 Intermediate Similarity NPC469414
0.7093 Intermediate Similarity NPC121374
0.7 Intermediate Similarity NPC287705
0.7 Intermediate Similarity NPC238223
0.7 Intermediate Similarity NPC474823
0.6962 Remote Similarity NPC37382
0.6914 Remote Similarity NPC475004
0.6905 Remote Similarity NPC478193
0.6905 Remote Similarity NPC478192
0.6905 Remote Similarity NPC478195
0.6905 Remote Similarity NPC161038
0.6905 Remote Similarity NPC478194
0.6905 Remote Similarity NPC478191
0.6905 Remote Similarity NPC478196
0.6875 Remote Similarity NPC132286
0.6835 Remote Similarity NPC475110
0.6809 Remote Similarity NPC303230
0.6809 Remote Similarity NPC6099
0.6809 Remote Similarity NPC114345
0.6795 Remote Similarity NPC473737
0.6747 Remote Similarity NPC133098
0.6744 Remote Similarity NPC275530
0.6742 Remote Similarity NPC8161
0.6706 Remote Similarity NPC260396
0.6705 Remote Similarity NPC47653
0.6667 Remote Similarity NPC28049
0.6632 Remote Similarity NPC327760
0.6628 Remote Similarity NPC301207
0.6625 Remote Similarity NPC282760
0.6625 Remote Similarity NPC470123
0.6582 Remote Similarity NPC68110
0.6552 Remote Similarity NPC474818
0.6552 Remote Similarity NPC49302
0.6552 Remote Similarity NPC68156
0.6552 Remote Similarity NPC125365
0.6552 Remote Similarity NPC51809
0.6552 Remote Similarity NPC176329
0.6548 Remote Similarity NPC293114
0.6526 Remote Similarity NPC475879
0.6522 Remote Similarity NPC470755
0.6512 Remote Similarity NPC329852
0.6506 Remote Similarity NPC236208
0.6506 Remote Similarity NPC473277
0.6477 Remote Similarity NPC473471
0.6477 Remote Similarity NPC221095
0.6477 Remote Similarity NPC279214
0.6444 Remote Similarity NPC150502
0.6437 Remote Similarity NPC256640
0.6437 Remote Similarity NPC16279
0.6437 Remote Similarity NPC205615
0.6437 Remote Similarity NPC209113
0.6437 Remote Similarity NPC127118
0.6421 Remote Similarity NPC225283
0.642 Remote Similarity NPC476589
0.642 Remote Similarity NPC131174
0.6413 Remote Similarity NPC158756
0.641 Remote Similarity NPC318306
0.6404 Remote Similarity NPC99651
0.6404 Remote Similarity NPC265980
0.6404 Remote Similarity NPC63326
0.6395 Remote Similarity NPC114727
0.6395 Remote Similarity NPC227396
0.6395 Remote Similarity NPC476590
0.6395 Remote Similarity NPC470686
0.6386 Remote Similarity NPC218477
0.6375 Remote Similarity NPC2328
0.6374 Remote Similarity NPC310450
0.6374 Remote Similarity NPC474959
0.6374 Remote Similarity NPC475046
0.6374 Remote Similarity NPC11383
0.6364 Remote Similarity NPC116177
0.6364 Remote Similarity NPC315394
0.6364 Remote Similarity NPC7563
0.6364 Remote Similarity NPC320630
0.6354 Remote Similarity NPC3436
0.6353 Remote Similarity NPC316185
0.6353 Remote Similarity NPC320119
0.6341 Remote Similarity NPC248125
0.6341 Remote Similarity NPC146811
0.6329 Remote Similarity NPC130953
0.6316 Remote Similarity NPC260343
0.6316 Remote Similarity NPC476805
0.6316 Remote Similarity NPC475819
0.6304 Remote Similarity NPC284472
0.6304 Remote Similarity NPC169575
0.6304 Remote Similarity NPC286770
0.6304 Remote Similarity NPC40746
0.6304 Remote Similarity NPC229799
0.6304 Remote Similarity NPC16488
0.6292 Remote Similarity NPC315765
0.6292 Remote Similarity NPC471465
0.6292 Remote Similarity NPC264391
0.6292 Remote Similarity NPC182292
0.6292 Remote Similarity NPC108816
0.6292 Remote Similarity NPC127526
0.6292 Remote Similarity NPC196653
0.6292 Remote Similarity NPC93763
0.6289 Remote Similarity NPC472814
0.6289 Remote Similarity NPC177037
0.6289 Remote Similarity NPC470520
0.6279 Remote Similarity NPC284006
0.6277 Remote Similarity NPC261721
0.6277 Remote Similarity NPC469483
0.6277 Remote Similarity NPC316426
0.6277 Remote Similarity NPC315395
0.6277 Remote Similarity NPC469910
0.6264 Remote Similarity NPC24417
0.6264 Remote Similarity NPC325031
0.6264 Remote Similarity NPC297440
0.625 Remote Similarity NPC68819
0.625 Remote Similarity NPC151648
0.625 Remote Similarity NPC470705
0.625 Remote Similarity NPC113293
0.6237 Remote Similarity NPC163093
0.6237 Remote Similarity NPC31086
0.6235 Remote Similarity NPC202011
0.6235 Remote Similarity NPC476037
0.6234 Remote Similarity NPC40148
0.6224 Remote Similarity NPC115021
0.6224 Remote Similarity NPC59646
0.6222 Remote Similarity NPC98557
0.6222 Remote Similarity NPC167881
0.622 Remote Similarity NPC182794
0.622 Remote Similarity NPC133904
0.622 Remote Similarity NPC471556
0.6211 Remote Similarity NPC45409
0.6207 Remote Similarity NPC315843
0.6196 Remote Similarity NPC473780
0.6196 Remote Similarity NPC180363
0.6196 Remote Similarity NPC329829
0.6196 Remote Similarity NPC131002
0.6196 Remote Similarity NPC473529
0.6196 Remote Similarity NPC65930
0.6196 Remote Similarity NPC11332
0.6196 Remote Similarity NPC145914
0.6196 Remote Similarity NPC473712
0.6196 Remote Similarity NPC73310
0.6196 Remote Similarity NPC94875
0.6196 Remote Similarity NPC475159
0.6196 Remote Similarity NPC229825
0.619 Remote Similarity NPC63873
0.6186 Remote Similarity NPC274075
0.6176 Remote Similarity NPC469872
0.6176 Remote Similarity NPC469864
0.617 Remote Similarity NPC477014
0.617 Remote Similarity NPC471567
0.617 Remote Similarity NPC68303
0.617 Remote Similarity NPC307126
0.617 Remote Similarity NPC120398
0.617 Remote Similarity NPC261380
0.617 Remote Similarity NPC477013
0.6163 Remote Similarity NPC84038
0.6163 Remote Similarity NPC186531
0.6162 Remote Similarity NPC475927
0.6162 Remote Similarity NPC470521
0.6162 Remote Similarity NPC469632
0.6162 Remote Similarity NPC475832
0.6146 Remote Similarity NPC475739
0.6146 Remote Similarity NPC476803
0.6145 Remote Similarity NPC315115
0.6145 Remote Similarity NPC276299
0.6139 Remote Similarity NPC53844
0.6136 Remote Similarity NPC473948
0.6132 Remote Similarity NPC232969
0.6132 Remote Similarity NPC199107
0.6129 Remote Similarity NPC59097
0.6129 Remote Similarity NPC473390
0.6129 Remote Similarity NPC144415
0.6129 Remote Similarity NPC116543
0.6129 Remote Similarity NPC131669
0.6129 Remote Similarity NPC253801
0.6125 Remote Similarity NPC327112
0.6125 Remote Similarity NPC98519
0.6122 Remote Similarity NPC2882
0.6122 Remote Similarity NPC32552
0.6118 Remote Similarity NPC316572
0.6118 Remote Similarity NPC143396
0.6118 Remote Similarity NPC475982

  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 NPC286816 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
0.6125 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5851 Remote Similarity NPD5209 Approved
0.5824 Remote Similarity NPD4756 Discovery
0.5789 Remote Similarity NPD7154 Phase 3
0.57 Remote Similarity NPD5785 Approved
0.5644 Remote Similarity NPD7983 Approved
0.5631 Remote Similarity NPD1698 Clinical (unspecified phase)

  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