Structure

Physi-Chem Properties

Molecular Weight:  181.04
Volume:  157.067
LogP:  -3.279
LogD:  -1.696
LogS:  -1.282
# Rotatable Bonds:  4
TPSA:  97.46
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  0
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.569
Synthetic Accessibility Score:  2.664
Fsp3:  0.8
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:  -6.235
MDCK Permeability:  6.437507545342669e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.332
Plasma Protein Binding (PPB):  9.584349632263184%
Volume Distribution (VD):  0.374
Pgp-substrate:  94.53285217285156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.056
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.18
CYP2D6-inhibitor:  0.016
CYP2D6-substrate:  0.138
CYP3A4-inhibitor:  0.009
CYP3A4-substrate:  0.062

ADMET: Excretion

Clearance (CL):  2.018
Half-life (T1/2):  0.715

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.082
Drug-inuced Liver Injury (DILI):  0.029
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.019
Maximum Recommended Daily Dose:  0.008
Skin Sensitization:  0.047
Carcinogencity:  0.033
Eye Corrosion:  0.003
Eye Irritation:  0.067
Respiratory Toxicity:  0.053

Download Data

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

  Natural Product: NPC102815

Natural Product ID:  NPC102815
Common Name*:   Methionine Sulfone
IUPAC Name:   (2S)-2-azaniumyl-4-methylsulfonylbutanoate
Synonyms:   L-Methionine Sulfone
Standard InCHIKey:  UCUNFLYVYCGDHP-BYPYZUCNSA-N
Standard InCHI:  InChI=1S/C5H11NO4S/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
SMILES:  CS(=O)(=O)CC[C@@H](C(=O)O)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL442720
PubChem CID:   6994316
445282
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids and derivatives
              • [CHEMONTID:0002404] Alpha amino acids
                • [CHEMONTID:0004146] L-alpha-amino acids

*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
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. PMID[18071251]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. faeces n.a. PMID[18323202]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22874 Bombyx mori Species Bombycidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22874 Bombyx mori Species Bombycidae 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 Inhibition = 33.0 % PMID[568448]
NPT2 Others Unspecified Inhibition = 67.0 % PMID[568448]

☑ 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 NPC102815 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
0.96 High Similarity NPC317815
0.9 High Similarity NPC152451
0.9 High Similarity NPC193989
0.9 High Similarity NPC170739
0.86 High Similarity NPC204364
0.84 Intermediate Similarity NPC198196
0.8113 Intermediate Similarity NPC114990
0.8077 Intermediate Similarity NPC318523
0.8039 Intermediate Similarity NPC49952
0.8039 Intermediate Similarity NPC136476
0.7895 Intermediate Similarity NPC82239
0.7885 Intermediate Similarity NPC118187
0.7778 Intermediate Similarity NPC125736
0.7692 Intermediate Similarity NPC185755
0.7692 Intermediate Similarity NPC213876
0.75 Intermediate Similarity NPC321419
0.74 Intermediate Similarity NPC168375
0.74 Intermediate Similarity NPC326992
0.74 Intermediate Similarity NPC121517
0.7368 Intermediate Similarity NPC145235
0.7358 Intermediate Similarity NPC228932
0.7255 Intermediate Similarity NPC110533
0.7255 Intermediate Similarity NPC254482
0.7255 Intermediate Similarity NPC317691
0.7255 Intermediate Similarity NPC326808
0.7115 Intermediate Similarity NPC167986
0.7115 Intermediate Similarity NPC291186
0.7 Intermediate Similarity NPC283786
0.6981 Remote Similarity NPC126925
0.6981 Remote Similarity NPC132307
0.6981 Remote Similarity NPC325097
0.6852 Remote Similarity NPC191136
0.6852 Remote Similarity NPC327698
0.6852 Remote Similarity NPC118459
0.6731 Remote Similarity NPC53449
0.6731 Remote Similarity NPC66043
0.66 Remote Similarity NPC116709
0.66 Remote Similarity NPC272614
0.66 Remote Similarity NPC21290
0.6552 Remote Similarity NPC315977
0.6552 Remote Similarity NPC319175
0.6545 Remote Similarity NPC329263
0.6545 Remote Similarity NPC208793
0.6545 Remote Similarity NPC285322
0.6429 Remote Similarity NPC306238
0.6429 Remote Similarity NPC248970
0.6379 Remote Similarity NPC43204
0.6379 Remote Similarity NPC245027
0.6379 Remote Similarity NPC226027
0.6379 Remote Similarity NPC174246
0.6379 Remote Similarity NPC84636
0.6379 Remote Similarity NPC93888
0.6379 Remote Similarity NPC162620
0.6379 Remote Similarity NPC270805
0.6379 Remote Similarity NPC62045
0.6364 Remote Similarity NPC198301
0.6364 Remote Similarity NPC289691
0.6316 Remote Similarity NPC136159
0.6271 Remote Similarity NPC137958
0.6271 Remote Similarity NPC273330
0.6269 Remote Similarity NPC174304
0.6269 Remote Similarity NPC325597
0.6207 Remote Similarity NPC140872
0.6207 Remote Similarity NPC153370
0.6207 Remote Similarity NPC93081
0.6154 Remote Similarity NPC63621
0.614 Remote Similarity NPC297220
0.614 Remote Similarity NPC309658
0.6129 Remote Similarity NPC2801
0.6111 Remote Similarity NPC326212
0.6111 Remote Similarity NPC237525
0.6102 Remote Similarity NPC316231
0.6102 Remote Similarity NPC112890
0.6102 Remote Similarity NPC328378
0.6102 Remote Similarity NPC324825
0.6038 Remote Similarity NPC18188
0.6 Remote Similarity NPC319046
0.6 Remote Similarity NPC14778
0.5968 Remote Similarity NPC321118
0.5968 Remote Similarity NPC316889
0.5968 Remote Similarity NPC183845
0.5968 Remote Similarity NPC279661
0.5962 Remote Similarity NPC9294
0.5926 Remote Similarity NPC329545
0.5915 Remote Similarity NPC126779
0.589 Remote Similarity NPC315897
0.5873 Remote Similarity NPC327831
0.5806 Remote Similarity NPC197087
0.5806 Remote Similarity NPC190184
0.5781 Remote Similarity NPC325985
0.5781 Remote Similarity NPC38463
0.5763 Remote Similarity NPC181588
0.5714 Remote Similarity NPC226265
0.5714 Remote Similarity NPC219143
0.5714 Remote Similarity NPC60672
0.5714 Remote Similarity NPC322091
0.5692 Remote Similarity NPC278209
0.5667 Remote Similarity NPC227850
0.5645 Remote Similarity NPC200550
0.5645 Remote Similarity NPC155156
0.5625 Remote Similarity NPC322573
0.5614 Remote Similarity NPC276294
0.5606 Remote Similarity NPC189301
0.5606 Remote Similarity NPC190385
0.5606 Remote Similarity NPC176164

  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 NPC102815 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
0.9 High Similarity NPD8802 Approved
0.9 High Similarity NPD9021 Approved
0.9 High Similarity NPD8803 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD8873 Approved
0.84 Intermediate Similarity NPD9020 Approved
0.8148 Intermediate Similarity NPD8849 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD9025 Approved
0.7692 Intermediate Similarity NPD8982 Approved
0.7358 Intermediate Similarity NPD8801 Approved
0.7255 Intermediate Similarity NPD8215 Approved
0.7255 Intermediate Similarity NPD8214 Approved
0.7115 Intermediate Similarity NPD8804 Approved
0.7115 Intermediate Similarity NPD8805 Approved
0.6981 Remote Similarity NPD8798 Approved
0.6885 Remote Similarity NPD8848 Approved
0.6716 Remote Similarity NPD9452 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2262 Clinical (unspecified phase)
0.66 Remote Similarity NPD8210 Phase 3
0.66 Remote Similarity NPD8211 Approved
0.6545 Remote Similarity NPD8610 Approved
0.6491 Remote Similarity NPD8577 Discontinued
0.6429 Remote Similarity NPD8870 Approved
0.6379 Remote Similarity NPD9016 Clinical (unspecified phase)
0.6379 Remote Similarity NPD9017 Approved
0.6379 Remote Similarity NPD8624 Approved
0.6379 Remote Similarity NPD9018 Approved
0.6333 Remote Similarity NPD9386 Approved
0.6324 Remote Similarity NPD886 Clinical (unspecified phase)
0.6271 Remote Similarity NPD8872 Phase 3
0.6271 Remote Similarity NPD8871 Approved
0.6271 Remote Similarity NPD329 Discontinued
0.6269 Remote Similarity NPD348 Approved
0.6216 Remote Similarity NPD9389 Approved
0.6207 Remote Similarity NPD9213 Approved
0.6207 Remote Similarity NPD8809 Approved
0.6207 Remote Similarity NPD8614 Approved
0.6207 Remote Similarity NPD8808 Approved
0.6207 Remote Similarity NPD9214 Phase 3
0.6102 Remote Similarity NPD9044 Approved
0.6066 Remote Similarity NPD8851 Phase 1
0.6038 Remote Similarity NPD8623 Phase 1
0.6 Remote Similarity NPD4241 Registered
0.6 Remote Similarity NPD8609 Approved
0.6 Remote Similarity NPD337 Discontinued
0.5915 Remote Similarity NPD4242 Approved
0.589 Remote Similarity NPD1825 Clinical (unspecified phase)
0.5846 Remote Similarity NPD9433 Approved
0.5811 Remote Similarity NPD9387 Approved
0.5811 Remote Similarity NPD9388 Approved
0.5806 Remote Similarity NPD9420 Clinical (unspecified phase)
0.5806 Remote Similarity NPD8785 Approved
0.5789 Remote Similarity NPD8869 Approved
0.5763 Remote Similarity NPD8810 Clinical (unspecified phase)
0.575 Remote Similarity NPD7643 Phase 1
0.5714 Remote Similarity NPD8216 Approved
0.5714 Remote Similarity NPD8217 Clinical (unspecified phase)
0.5672 Remote Similarity NPD902 Approved
0.5625 Remote Similarity NPD9307 Phase 1
0.5606 Remote Similarity NPD9023 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