Structure

Physi-Chem Properties

Molecular Weight:  264.14
Volume:  281.418
LogP:  1.43
LogD:  1.08
LogS:  -2.084
# Rotatable Bonds:  5
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.468
Synthetic Accessibility Score:  4.341
Fsp3:  0.467
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.59
MDCK Permeability:  2.9370654374361038e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.042
20% Bioavailability (F20%):  0.115
30% Bioavailability (F30%):  0.174

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.252
Plasma Protein Binding (PPB):  66.6807632446289%
Volume Distribution (VD):  1.037
Pgp-substrate:  35.7474250793457%

ADMET: Metabolism

CYP1A2-inhibitor:  0.345
CYP1A2-substrate:  0.273
CYP2C19-inhibitor:  0.328
CYP2C19-substrate:  0.763
CYP2C9-inhibitor:  0.25
CYP2C9-substrate:  0.231
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.114
CYP3A4-inhibitor:  0.03
CYP3A4-substrate:  0.258

ADMET: Excretion

Clearance (CL):  8.25
Half-life (T1/2):  0.848

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.094
Drug-inuced Liver Injury (DILI):  0.757
AMES Toxicity:  0.252
Rat Oral Acute Toxicity:  0.943
Maximum Recommended Daily Dose:  0.553
Skin Sensitization:  0.92
Carcinogencity:  0.675
Eye Corrosion:  0.408
Eye Irritation:  0.927
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC476589

Natural Product ID:  NPC476589
Common Name*:   Lavjuismiztlgi-uhfffaoysa-
IUPAC Name:   7-ethyl-4-methoxy-7H-furo[3,4-b]pyran-2,5-dione
Synonyms:   Annularin F
Standard InCHIKey:  LAVJUISMIZTLGI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H10O5/c1-3-5-9-8(10(12)14-5)6(13-2)4-7(11)15-9/h4-5H,3H2,1-2H3
SMILES:  CCC1C2=C(C(=CC(=O)O2)OC)C(=O)O1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   11492190
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000086] Pyrans
        • [CHEMONTID:0000481] Pyranones and derivatives

*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
NPO33584 Annulatascus triseptatus Species Annulatascaceae Eukaryota n.a. Shaker Pond, Alfred, Maine n.a. PMID[14575427]

☑ 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
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 8 mm PMID[14575427]

☑ 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 NPC476589 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
0.8281 Intermediate Similarity NPC15193
0.8088 Intermediate Similarity NPC477117
0.8 Intermediate Similarity NPC133098
0.7846 Intermediate Similarity NPC309408
0.7808 Intermediate Similarity NPC470705
0.7692 Intermediate Similarity NPC133600
0.7571 Intermediate Similarity NPC238223
0.7536 Intermediate Similarity NPC470033
0.75 Intermediate Similarity NPC221763
0.75 Intermediate Similarity NPC271632
0.75 Intermediate Similarity NPC150717
0.7429 Intermediate Similarity NPC132286
0.7419 Intermediate Similarity NPC191643
0.7391 Intermediate Similarity NPC182794
0.7353 Intermediate Similarity NPC475073
0.7353 Intermediate Similarity NPC2328
0.7353 Intermediate Similarity NPC473737
0.7344 Intermediate Similarity NPC173157
0.7324 Intermediate Similarity NPC280374
0.7313 Intermediate Similarity NPC98519
0.7313 Intermediate Similarity NPC130953
0.7273 Intermediate Similarity NPC189700
0.726 Intermediate Similarity NPC112983
0.726 Intermediate Similarity NPC178575
0.726 Intermediate Similarity NPC162571
0.7222 Intermediate Similarity NPC494
0.7213 Intermediate Similarity NPC234084
0.72 Intermediate Similarity NPC478194
0.72 Intermediate Similarity NPC478192
0.72 Intermediate Similarity NPC478191
0.72 Intermediate Similarity NPC478196
0.72 Intermediate Similarity NPC161038
0.72 Intermediate Similarity NPC478193
0.72 Intermediate Similarity NPC478195
0.7188 Intermediate Similarity NPC218486
0.7164 Intermediate Similarity NPC286189
0.7162 Intermediate Similarity NPC146583
0.7143 Intermediate Similarity NPC131174
0.7143 Intermediate Similarity NPC273600
0.7143 Intermediate Similarity NPC470123
0.7123 Intermediate Similarity NPC59558
0.7101 Intermediate Similarity NPC210303
0.7101 Intermediate Similarity NPC474729
0.7101 Intermediate Similarity NPC179087
0.7101 Intermediate Similarity NPC474723
0.7101 Intermediate Similarity NPC44343
0.7059 Intermediate Similarity NPC26223
0.7042 Intermediate Similarity NPC475675
0.7042 Intermediate Similarity NPC37382
0.7042 Intermediate Similarity NPC475555
0.7013 Intermediate Similarity NPC275530
0.7 Intermediate Similarity NPC308457
0.7 Intermediate Similarity NPC471611
0.7 Intermediate Similarity NPC148233
0.7 Intermediate Similarity NPC25747
0.6974 Remote Similarity NPC206507
0.6974 Remote Similarity NPC210258
0.6974 Remote Similarity NPC329826
0.6974 Remote Similarity NPC147621
0.6974 Remote Similarity NPC469414
0.6957 Remote Similarity NPC151648
0.6944 Remote Similarity NPC203335
0.6901 Remote Similarity NPC471565
0.6901 Remote Similarity NPC282760
0.6901 Remote Similarity NPC476586
0.6901 Remote Similarity NPC471566
0.6901 Remote Similarity NPC471556
0.6892 Remote Similarity NPC202011
0.6883 Remote Similarity NPC301207
0.686 Remote Similarity NPC327760
0.6857 Remote Similarity NPC132243
0.6849 Remote Similarity NPC287705
0.6849 Remote Similarity NPC470032
0.6849 Remote Similarity NPC474823
0.6835 Remote Similarity NPC99651
0.6825 Remote Similarity NPC275316
0.6818 Remote Similarity NPC25038
0.6818 Remote Similarity NPC478117
0.6806 Remote Similarity NPC248125
0.6806 Remote Similarity NPC276299
0.6806 Remote Similarity NPC124586
0.6795 Remote Similarity NPC51809
0.6795 Remote Similarity NPC49302
0.6795 Remote Similarity NPC68156
0.6795 Remote Similarity NPC176329
0.6795 Remote Similarity NPC125365
0.6795 Remote Similarity NPC471225
0.6795 Remote Similarity NPC474818
0.679 Remote Similarity NPC8161
0.6782 Remote Similarity NPC282644
0.6782 Remote Similarity NPC29798
0.6769 Remote Similarity NPC327103
0.6765 Remote Similarity NPC187770
0.6757 Remote Similarity NPC475004
0.675 Remote Similarity NPC121374
0.6747 Remote Similarity NPC130030
0.6747 Remote Similarity NPC281172
0.6716 Remote Similarity NPC86948
0.6716 Remote Similarity NPC51846
0.6714 Remote Similarity NPC68044
0.6712 Remote Similarity NPC225272
0.6709 Remote Similarity NPC279214
0.6709 Remote Similarity NPC221095
0.6709 Remote Similarity NPC473471
0.6709 Remote Similarity NPC475699
0.6667 Remote Similarity NPC303230
0.6667 Remote Similarity NPC238554
0.6667 Remote Similarity NPC6099
0.6667 Remote Similarity NPC478120
0.6667 Remote Similarity NPC114345
0.6667 Remote Similarity NPC302564
0.6667 Remote Similarity NPC127118
0.6667 Remote Similarity NPC315285
0.6667 Remote Similarity NPC133904
0.6667 Remote Similarity NPC209113
0.6667 Remote Similarity NPC225022
0.6667 Remote Similarity NPC96414
0.6667 Remote Similarity NPC220766
0.6667 Remote Similarity NPC291712
0.6625 Remote Similarity NPC473980
0.6625 Remote Similarity NPC473981
0.6623 Remote Similarity NPC107654
0.6623 Remote Similarity NPC177030
0.6623 Remote Similarity NPC470686
0.6622 Remote Similarity NPC475760
0.662 Remote Similarity NPC476584
0.6618 Remote Similarity NPC319423
0.6582 Remote Similarity NPC228902
0.6582 Remote Similarity NPC315394
0.6582 Remote Similarity NPC473825
0.6582 Remote Similarity NPC24827
0.6579 Remote Similarity NPC293114
0.6575 Remote Similarity NPC469446
0.6575 Remote Similarity NPC201356
0.6575 Remote Similarity NPC315115
0.6575 Remote Similarity NPC191233
0.6571 Remote Similarity NPC429928
0.6571 Remote Similarity NPC476585
0.6571 Remote Similarity NPC79756
0.6562 Remote Similarity NPC15789
0.6562 Remote Similarity NPC236338
0.6552 Remote Similarity NPC274075
0.6543 Remote Similarity NPC47653
0.6533 Remote Similarity NPC476591
0.6533 Remote Similarity NPC473277
0.6533 Remote Similarity NPC470693
0.6533 Remote Similarity NPC88877
0.6528 Remote Similarity NPC475618
0.6528 Remote Similarity NPC470808
0.6512 Remote Similarity NPC260343
0.6494 Remote Similarity NPC287878
0.6494 Remote Similarity NPC222244
0.6494 Remote Similarity NPC16349
0.6486 Remote Similarity NPC470442
0.6479 Remote Similarity NPC263732
0.6471 Remote Similarity NPC230296
0.6463 Remote Similarity NPC297440
0.6456 Remote Similarity NPC203277
0.6447 Remote Similarity NPC299932
0.6447 Remote Similarity NPC315597
0.6447 Remote Similarity NPC475113
0.6444 Remote Similarity NPC471492
0.6438 Remote Similarity NPC7940
0.6437 Remote Similarity NPC225283
0.6437 Remote Similarity NPC95364
0.6437 Remote Similarity NPC64913
0.6437 Remote Similarity NPC242877
0.6437 Remote Similarity NPC142159
0.6429 Remote Similarity NPC159650
0.6429 Remote Similarity NPC22897
0.642 Remote Similarity NPC286816
0.642 Remote Similarity NPC199134
0.6418 Remote Similarity NPC129710
0.641 Remote Similarity NPC315843
0.6406 Remote Similarity NPC126184
0.6406 Remote Similarity NPC135698
0.64 Remote Similarity NPC313444
0.64 Remote Similarity NPC63873
0.6389 Remote Similarity NPC68110
0.6386 Remote Similarity NPC11383
0.6386 Remote Similarity NPC474439
0.6386 Remote Similarity NPC474028
0.6386 Remote Similarity NPC474959
0.6386 Remote Similarity NPC310450
0.6386 Remote Similarity NPC475690
0.6386 Remote Similarity NPC475046
0.6377 Remote Similarity NPC474825
0.6375 Remote Similarity NPC475711
0.6374 Remote Similarity NPC473333
0.6364 Remote Similarity NPC269103
0.6364 Remote Similarity NPC316185
0.6364 Remote Similarity NPC3436
0.6364 Remote Similarity NPC124072
0.6364 Remote Similarity NPC475762
0.6353 Remote Similarity NPC470124
0.6351 Remote Similarity NPC146811
0.6324 Remote Similarity NPC474913
0.6322 Remote Similarity NPC471956
0.6316 Remote Similarity NPC232812
0.6316 Remote Similarity NPC151481

  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 NPC476589 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
0.6765 Remote Similarity NPD69 Approved
0.6765 Remote Similarity NPD9119 Approved
0.6618 Remote Similarity NPD9118 Approved
0.6212 Remote Similarity NPD6927 Phase 3
0.6 Remote Similarity NPD5209 Approved
0.5862 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5843 Remote Similarity NPD1282 Approved
0.5789 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5652 Remote Similarity NPD7838 Discovery

  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