Structure

Physi-Chem Properties

Molecular Weight:  175.02
Volume:  149.926
LogP:  -1.39
LogD:  -0.418
LogS:  -0.359
# Rotatable Bonds:  2
TPSA:  117.12
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.448
Synthetic Accessibility Score:  4.536
Fsp3:  0.333
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:  -5.637
MDCK Permeability:  2.6022156816907227e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.182
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.12
30% Bioavailability (F30%):  0.411

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.096
Plasma Protein Binding (PPB):  68.76958465576172%
Volume Distribution (VD):  1.008
Pgp-substrate:  38.21217346191406%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.044
CYP2C19-inhibitor:  0.012
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.41
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.037

ADMET: Excretion

Clearance (CL):  6.663
Half-life (T1/2):  0.926

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.862
Drug-inuced Liver Injury (DILI):  0.915
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.542
Maximum Recommended Daily Dose:  0.358
Skin Sensitization:  0.527
Carcinogencity:  0.927
Eye Corrosion:  0.004
Eye Irritation:  0.217
Respiratory Toxicity:  0.238

Download Data

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

  Natural Product: NPC319423

Natural Product ID:  NPC319423
Common Name*:   Sodium Ascorbate
IUPAC Name:   sodium;(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2H-furan-3-olate
Synonyms:   Ascorbin; Cevalin; E301; Sodium Ascorbate
Standard InCHIKey:  PPASLZSBLFJQEF-RXSVEWSESA-M
Standard InCHI:  InChI=1S/C6H8O6.Na/c7-1-2(8)5-3(9)4(10)6(11)12-5;/h2,5,7-10H,1H2;/q;+1/p-1/t2-,5+;/m0./s1
SMILES:  OC[C@@H]([C@H]1OC(=O)C(=C1[O-])O)O.[Na+]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL591665
PubChem CID:   23667548
54685048
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

☑ 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
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -5.67 % PMID[512947]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -1.944 % PMID[512948]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.07 % PMID[512949]
NPT2 Others Unspecified Potency n.a. 61614.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34341.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12293.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43233.1 nM PubChem BioAssay data set

☑ 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 NPC319423 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
0.9815 High Similarity NPC187770
0.7895 Intermediate Similarity NPC327103
0.7812 Intermediate Similarity NPC276299
0.7656 Intermediate Similarity NPC470123
0.726 Intermediate Similarity NPC179933
0.7213 Intermediate Similarity NPC230296
0.7121 Intermediate Similarity NPC19769
0.7077 Intermediate Similarity NPC475073
0.6875 Remote Similarity NPC302564
0.6866 Remote Similarity NPC282760
0.6812 Remote Similarity NPC63873
0.678 Remote Similarity NPC107703
0.6765 Remote Similarity NPC475555
0.6765 Remote Similarity NPC475675
0.6765 Remote Similarity NPC201356
0.6716 Remote Similarity NPC470808
0.6712 Remote Similarity NPC478193
0.6712 Remote Similarity NPC478196
0.6712 Remote Similarity NPC478194
0.6712 Remote Similarity NPC478195
0.6712 Remote Similarity NPC478191
0.6712 Remote Similarity NPC478192
0.6667 Remote Similarity NPC318481
0.6667 Remote Similarity NPC122627
0.662 Remote Similarity NPC202011
0.6618 Remote Similarity NPC476589
0.6618 Remote Similarity NPC273600
0.6618 Remote Similarity NPC96414
0.6615 Remote Similarity NPC97570
0.6613 Remote Similarity NPC135537
0.6575 Remote Similarity NPC473489
0.6575 Remote Similarity NPC326504
0.6522 Remote Similarity NPC37382
0.6494 Remote Similarity NPC47653
0.6491 Remote Similarity NPC75134
0.6486 Remote Similarity NPC473582
0.6486 Remote Similarity NPC161038
0.6479 Remote Similarity NPC475982
0.6471 Remote Similarity NPC471611
0.6452 Remote Similarity NPC116366
0.6418 Remote Similarity NPC26810
0.64 Remote Similarity NPC470705
0.6364 Remote Similarity NPC99651
0.6351 Remote Similarity NPC107654
0.6338 Remote Similarity NPC238223
0.6324 Remote Similarity NPC473737
0.6316 Remote Similarity NPC474026
0.6316 Remote Similarity NPC275530
0.6286 Remote Similarity NPC478101
0.6286 Remote Similarity NPC146811
0.6269 Remote Similarity NPC98519
0.625 Remote Similarity NPC130618
0.6234 Remote Similarity NPC248775
0.6232 Remote Similarity NPC148233
0.6232 Remote Similarity NPC25747
0.6197 Remote Similarity NPC478100
0.6197 Remote Similarity NPC132286
0.619 Remote Similarity NPC477781
0.619 Remote Similarity NPC477780
0.6184 Remote Similarity NPC209113
0.6184 Remote Similarity NPC301207
0.6184 Remote Similarity NPC127118
0.6154 Remote Similarity NPC1180
0.6154 Remote Similarity NPC470149
0.6154 Remote Similarity NPC180725
0.6154 Remote Similarity NPC470148
0.6143 Remote Similarity NPC478098
0.6143 Remote Similarity NPC478099
0.6133 Remote Similarity NPC114727
0.6133 Remote Similarity NPC476590
0.6133 Remote Similarity NPC315843
0.6133 Remote Similarity NPC474280
0.6125 Remote Similarity NPC474959
0.6125 Remote Similarity NPC475046
0.6125 Remote Similarity NPC310450
0.6125 Remote Similarity NPC11383
0.6111 Remote Similarity NPC474823
0.6104 Remote Similarity NPC51809
0.6104 Remote Similarity NPC176329
0.6104 Remote Similarity NPC474818
0.6104 Remote Similarity NPC49302
0.6104 Remote Similarity NPC475711
0.6104 Remote Similarity NPC125365
0.6081 Remote Similarity NPC178575
0.6076 Remote Similarity NPC470147
0.6076 Remote Similarity NPC133226
0.6056 Remote Similarity NPC124586
0.6056 Remote Similarity NPC470033
0.6053 Remote Similarity NPC473948
0.6049 Remote Similarity NPC286770
0.6049 Remote Similarity NPC284472
0.6049 Remote Similarity NPC229799
0.6029 Remote Similarity NPC130953
0.6029 Remote Similarity NPC26223
0.6027 Remote Similarity NPC475004
0.6026 Remote Similarity NPC28049
0.6026 Remote Similarity NPC279214
0.6026 Remote Similarity NPC473471
0.6026 Remote Similarity NPC221095
0.6 Remote Similarity NPC284006
0.6 Remote Similarity NPC297440
0.6 Remote Similarity NPC308457
0.5976 Remote Similarity NPC163093
0.5974 Remote Similarity NPC203277
0.5972 Remote Similarity NPC25298
0.5972 Remote Similarity NPC478097
0.5968 Remote Similarity NPC275316
0.5952 Remote Similarity NPC178215
0.5952 Remote Similarity NPC45409
0.5946 Remote Similarity NPC476012
0.5946 Remote Similarity NPC476037
0.5942 Remote Similarity NPC15193
0.5942 Remote Similarity NPC55376
0.5926 Remote Similarity NPC251026
0.5915 Remote Similarity NPC476586
0.5904 Remote Similarity NPC107986
0.5904 Remote Similarity NPC473651
0.5904 Remote Similarity NPC231009
0.5904 Remote Similarity NPC110710
0.5904 Remote Similarity NPC223871
0.5904 Remote Similarity NPC477014
0.5904 Remote Similarity NPC473669
0.5904 Remote Similarity NPC103284
0.5904 Remote Similarity NPC283085
0.5904 Remote Similarity NPC66346
0.5904 Remote Similarity NPC1083
0.5904 Remote Similarity NPC473478
0.5904 Remote Similarity NPC471567
0.5904 Remote Similarity NPC286338
0.5904 Remote Similarity NPC120398
0.5904 Remote Similarity NPC132496
0.5904 Remote Similarity NPC477013
0.5904 Remote Similarity NPC82795
0.5904 Remote Similarity NPC182383
0.5897 Remote Similarity NPC474278
0.589 Remote Similarity NPC287705
0.589 Remote Similarity NPC310210
0.589 Remote Similarity NPC475760
0.5882 Remote Similarity NPC21208
0.5882 Remote Similarity NPC280621
0.5882 Remote Similarity NPC20339
0.5882 Remote Similarity NPC286189
0.5882 Remote Similarity NPC48338
0.5882 Remote Similarity NPC233551
0.5882 Remote Similarity NPC40376
0.5875 Remote Similarity NPC121374
0.5867 Remote Similarity NPC316185
0.5867 Remote Similarity NPC293114
0.5862 Remote Similarity NPC327760
0.5857 Remote Similarity NPC474774
0.5857 Remote Similarity NPC68110
0.5857 Remote Similarity NPC474729
0.5857 Remote Similarity NPC474723
0.5854 Remote Similarity NPC473315
0.5854 Remote Similarity NPC315559
0.5854 Remote Similarity NPC142111
0.5833 Remote Similarity NPC107717
0.5833 Remote Similarity NPC204686
0.5833 Remote Similarity NPC473687
0.5833 Remote Similarity NPC62118
0.5833 Remote Similarity NPC171174
0.5833 Remote Similarity NPC134865
0.5833 Remote Similarity NPC103523
0.5833 Remote Similarity NPC142117
0.5833 Remote Similarity NPC219498
0.5833 Remote Similarity NPC231096
0.5833 Remote Similarity NPC240695
0.5833 Remote Similarity NPC47937
0.5833 Remote Similarity NPC248125
0.5833 Remote Similarity NPC477015
0.5833 Remote Similarity NPC210218
0.5833 Remote Similarity NPC69082
0.5833 Remote Similarity NPC134807
0.5833 Remote Similarity NPC308412
0.5833 Remote Similarity NPC232555
0.5833 Remote Similarity NPC134885
0.5833 Remote Similarity NPC112685
0.5833 Remote Similarity NPC114694
0.5833 Remote Similarity NPC475581
0.5833 Remote Similarity NPC279267
0.5823 Remote Similarity NPC477314
0.5823 Remote Similarity NPC279532
0.5823 Remote Similarity NPC474816
0.5823 Remote Similarity NPC209135
0.5821 Remote Similarity NPC135863
0.5802 Remote Similarity NPC469469
0.5802 Remote Similarity NPC150502
0.5797 Remote Similarity NPC321919
0.5797 Remote Similarity NPC81896
0.5789 Remote Similarity NPC329890
0.5789 Remote Similarity NPC144419
0.5789 Remote Similarity NPC329914
0.5789 Remote Similarity NPC185186
0.5789 Remote Similarity NPC327383
0.5783 Remote Similarity NPC30915
0.5783 Remote Similarity NPC473308
0.5783 Remote Similarity NPC156804
0.5775 Remote Similarity NPC475221
0.5775 Remote Similarity NPC114464
0.5775 Remote Similarity NPC475618

  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 NPC319423 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
1.0 High Similarity NPD9118 Approved
0.9815 High Similarity NPD9119 Approved
0.9815 High Similarity NPD69 Approved
0.6269 Remote Similarity NPD9120 Clinical (unspecified phase)
0.597 Remote Similarity NPD585 Clinical (unspecified phase)
0.5735 Remote Similarity NPD6109 Phase 1

  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