Structure

Physi-Chem Properties

Molecular Weight:  247.08
Volume:  246.63
LogP:  0.828
LogD:  1.332
LogS:  -2.892
# Rotatable Bonds:  1
TPSA:  65.37
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.742
Synthetic Accessibility Score:  2.739
Fsp3:  0.308
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.765
MDCK Permeability:  2.2154275939101353e-05
Pgp-inhibitor:  0.332
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.325
Plasma Protein Binding (PPB):  82.01516723632812%
Volume Distribution (VD):  1.003
Pgp-substrate:  15.068669319152832%

ADMET: Metabolism

CYP1A2-inhibitor:  0.956
CYP1A2-substrate:  0.936
CYP2C19-inhibitor:  0.444
CYP2C19-substrate:  0.665
CYP2C9-inhibitor:  0.233
CYP2C9-substrate:  0.456
CYP2D6-inhibitor:  0.368
CYP2D6-substrate:  0.144
CYP3A4-inhibitor:  0.166
CYP3A4-substrate:  0.267

ADMET: Excretion

Clearance (CL):  3.752
Half-life (T1/2):  0.226

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.165
Drug-inuced Liver Injury (DILI):  0.225
AMES Toxicity:  0.904
Rat Oral Acute Toxicity:  0.363
Maximum Recommended Daily Dose:  0.484
Skin Sensitization:  0.098
Carcinogencity:  0.107
Eye Corrosion:  0.004
Eye Irritation:  0.654
Respiratory Toxicity:  0.185

Download Data

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

  Natural Product: NPC475614

Natural Product ID:  NPC475614
Common Name*:   Mimosamycin
IUPAC Name:   7-methoxy-1,2,6-trimethylisoquinoline-3,5,8-trione
Synonyms:   Mimosamycin
Standard InCHIKey:  ZYWCMKYDEGVQCK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H13NO4/c1-6-11(16)8-5-9(15)14(3)7(2)10(8)12(17)13(6)18-4/h5H,1-4H3
SMILES:  CC1=C(C(=O)C2=C(N(C(=O)C=C2C1=O)C)C)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL509316
PubChem CID:   44566893
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0002567] Isoquinoline quinones

*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
NPO33502 Haliclona sp. Species Chalinidae Eukaryota n.a. n.a. n.a. PMID[11575970]
NPO33502 Haliclona sp. Species Chalinidae Eukaryota n.a. n.a. n.a. PMID[17848089]
NPO33502 Haliclona sp. Species Chalinidae Eukaryota n.a. Pacific n.a. PMID[19133758]
NPO33502 Haliclona sp. Species Chalinidae Eukaryota n.a. Culasian Point, Leyte, Philippines (S 1119.00', E 12435.60') 1991-MAR PMID[22873824]
NPO33502 Haliclona sp. Species Chalinidae Eukaryota n.a. New Zealand n.a. PMID[24128145]

☑ 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
NPT377 Cell Line OVCAR-3 Homo sapiens IC50 = 10.0 ug.mL-1 PMID[524228]
NPT3973 Individual Protein Endothelial PAS domain-containing protein 1 Homo sapiens EC50 > 100000.0 nM PMID[524231]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 10.0 ug.mL-1 PMID[524228]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 17.0 mm PMID[524229]
NPT2709 Organism Bacillus subtilis subsp. subtilis str. 168 Bacillus subtilis subsp. subtilis str. 168 IZ = 22.0 mm PMID[524229]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis Activity = 15.0 % PMID[524229]
NPT985 Organism Cladosporium cucumerinum Cladosporium cucumerinum IZ = 18.0 mm PMID[524229]
NPT985 Organism Cladosporium cucumerinum Cladosporium cucumerinum IZ = 15.0 mm PMID[524229]
NPT985 Organism Cladosporium cucumerinum Cladosporium cucumerinum IZ = 18.0 mm PMID[524230]
NPT985 Organism Cladosporium cucumerinum Cladosporium cucumerinum IZ = 15.0 mm PMID[524230]

☑ 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 NPC475614 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
0.9036 High Similarity NPC2640
0.6966 Remote Similarity NPC28529
0.6835 Remote Similarity NPC139056
0.675 Remote Similarity NPC473494
0.6562 Remote Similarity NPC472136
0.6562 Remote Similarity NPC472161
0.6506 Remote Similarity NPC151728
0.6506 Remote Similarity NPC57463
0.6429 Remote Similarity NPC34622
0.6429 Remote Similarity NPC116231
0.6429 Remote Similarity NPC474400
0.6395 Remote Similarity NPC474619
0.6395 Remote Similarity NPC243272
0.6353 Remote Similarity NPC98897
0.6322 Remote Similarity NPC125578
0.6322 Remote Similarity NPC263382
0.6322 Remote Similarity NPC146376
0.6322 Remote Similarity NPC134385
0.6279 Remote Similarity NPC16119
0.625 Remote Similarity NPC94488
0.625 Remote Similarity NPC262673
0.622 Remote Similarity NPC320421
0.618 Remote Similarity NPC94743
0.618 Remote Similarity NPC291062
0.6154 Remote Similarity NPC264178
0.6122 Remote Similarity NPC296589
0.6095 Remote Similarity NPC472166
0.6095 Remote Similarity NPC472167
0.6055 Remote Similarity NPC9436
0.6042 Remote Similarity NPC312419
0.6 Remote Similarity NPC474805
0.5981 Remote Similarity NPC316730
0.5957 Remote Similarity NPC283087
0.5943 Remote Similarity NPC472162
0.593 Remote Similarity NPC143168
0.593 Remote Similarity NPC53109
0.5926 Remote Similarity NPC317796
0.5862 Remote Similarity NPC7029
0.5843 Remote Similarity NPC251429
0.5843 Remote Similarity NPC298249
0.581 Remote Similarity NPC313265
0.5789 Remote Similarity NPC473536
0.575 Remote Similarity NPC22329
0.575 Remote Similarity NPC315110
0.5748 Remote Similarity NPC179224
0.5747 Remote Similarity NPC477830
0.5743 Remote Similarity NPC476141
0.5732 Remote Similarity NPC129710
0.5728 Remote Similarity NPC81195
0.5714 Remote Similarity NPC200831
0.5714 Remote Similarity NPC299369
0.5714 Remote Similarity NPC224103
0.5702 Remote Similarity NPC21324
0.57 Remote Similarity NPC469884
0.5693 Remote Similarity NPC246412
0.5678 Remote Similarity NPC472164
0.5676 Remote Similarity NPC318544
0.5673 Remote Similarity NPC236322
0.5673 Remote Similarity NPC53240
0.5644 Remote Similarity NPC470177
0.5632 Remote Similarity NPC68044
0.5625 Remote Similarity NPC220191
0.5625 Remote Similarity NPC470073
0.5619 Remote Similarity NPC193396
0.5619 Remote Similarity NPC32944
0.5604 Remote Similarity NPC96272
0.56 Remote Similarity NPC471595
0.56 Remote Similarity NPC288281

  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 NPC475614 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
0.6279 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6129 Remote Similarity NPD4756 Discovery
0.593 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5909 Remote Similarity NPD3704 Approved
0.5882 Remote Similarity NPD7299 Clinical (unspecified phase)
0.575 Remote Similarity NPD7196 Clinical (unspecified phase)
0.5745 Remote Similarity NPD1452 Discontinued
0.5714 Remote Similarity NPD5115 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8779 Phase 3

  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