Natural Product: NPC311668

Natural Product ID:  NPC311668
Common Name:   (2R,3R,4R)-2-(Hydroxymethyl)Pyrrolidine-3,4-Diol
IUPAC Name:   (2R,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol
Synonyms:   Imino-D-Arabinitol
Molecular Formula:   C5H11NO3
Standard InCHIKey:  OQEBIHBLFRADNM-UOWFLXDJSA-N
Standard InCHI:  InChI=1S/C5H11NO3/c7-2-3-5(9)4(8)1-6-3/h3-9H,1-2H2/t3-,4-,5-/m1/s1
Canonical SMILES:  OC[C@H]1NC[C@H]([C@@H]1O)O
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO7826 Agrobacterium aurantiacum Species Rhizobiaceae Bacteria UNPD*
NPO25301 Angylocalyx pynaertii Species Fabaceae Eukaryota Seeds PMID[8229017]
NPO25301 Angylocalyx pynaertii Species Fabaceae Eukaryota pods PMID[11858756]
NPO6450 Desmodium canum Species Fabaceae Eukaryota UNPD*
NPO28265 Morus alba Species Moraceae Eukaryota TCM_Taiwan*
NPO1605 Cleidion spiciflorum Species Euphorbiaceae Eukaryota UNPD*
NPO407 Chlorurus gibbus Species Labridae Eukaryota UNPD*
NPO28265 Morus alba Species Moraceae Eukaryota TM-MC*
NPO16194 Morus bombycis Species Moraceae Eukaryota TM-MC*
NPO11597 Stellaria dichotoma Species Caryophyllaceae Eukaryota UNPD*
NPO28265 Morus alba Species Moraceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1667 Individual Protein Liver glycogen phosphorylase Homo sapiens Ki = 400 nM 15214781
NPT497 Individual Protein Maltase-glucoamylase Homo sapiens IC50 = 55000 nM 7608901
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 16000 nM 7608901
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 5800 nM 7608901
NPT1050 Individual Protein Trehalase Rattus norvegicus IC50 = 25000 nM 7608901
NPT1051 Individual Protein Lactase-glycosylceramidase Rattus norvegicus IC50 = 260000 nM 7608901
NPT2 Others Unspecified IC50 < 50000 nM 7608901
NPT2 Others Unspecified IC50 = 20000 nM 7608901
NPT2 Others Unspecified IC50 = 130000 nM 7608901
NPT1052 Individual Protein Mannosidase 2 alpha 1 Rattus norvegicus IC50 = 46000 nM 7608901
NPT1053 Individual Protein Alpha-mannosidase 2C1 Rattus norvegicus IC50 < 50000 nM 7608901
NPT1054 Individual Protein Mannosidase 2, alpha B1 Rattus norvegicus IC50 = 110000 nM 7608901
NPT2 Others Unspecified Ki = 9700 nM 7608901
NPT1052 Individual Protein Mannosidase 2 alpha 1 Rattus norvegicus Ki = 35000 nM 7608901
NPT25 Cell Line MT4 Homo sapiens EC50 > 100000 ug/ml 7608901
NPT25 Cell Line MT4 Homo sapiens CC50 > 100000 ug/ml 7608901
NPT112 Cell Line MOLT-4 Homo sapiens EC50 > 100000 ug/ml 7608901
NPT112 Cell Line MOLT-4 Homo sapiens CC50 > 100000 ug/ml 7608901
NPT1053 Individual Protein Alpha-mannosidase 2C1 Rattus norvegicus IC50 = 100000 nM 2504921
NPT2 Others Unspecified IC50 = 0.16 ug/ml 17378534
NPT5874 Individual Protein Glucoamylase, intracellular sporulation-specific Saccharomyces cerevisiae S288c IC50 = 150 nM 17434740
NPT2 Others Unspecified IC50 = 500000 nM 17434740
NPT2 Others Unspecified IC50 = 200000 nM 17434740
NPT2 Others Unspecified IC50 = 430 nM 18258441
NPT514 Individual Protein Glycogen debranching enzyme Homo sapiens IC50 = 8400 nM 18258441
NPT2 Others Unspecified IC50 = 250000 nM 18258441
NPT2 Others Unspecified IC50 = 180 nM 18258441
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 55000 nM 18258441
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 5800 nM 18258441
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 16000 nM 18258441
NPT2 Others Unspecified IC50 = 900000 nM 18258441
NPT1135 Cell Line Hepatocyte Rattus norvegicus IC50 = 1000 nM 18258441
NPT513 Individual Protein Beta-glucosidase Homo sapiens IC50 = 120000 nM 18258441
NPT526 Individual Protein Alpha-glucosidase MAL62 Saccharomyces cerevisiae IC50 = 840 nM 11858756
NPT2 Others Unspecified IC50 = 110 nM 11858756
NPT2 Others Unspecified IC50 = 120000 nM 11858756
NPT1131 Individual Protein Alpha-galactosidase Coffea arabica Inhibition < 50 % 11858756
NPT509 Individual Protein Beta-galactosidase Bos taurus Inhibition < 50 % 11858756
NPT496 Individual Protein Alpha-L-fucosidase 1 Bos taurus Inhibition < 50 % 11858756
NPT2 Others Unspecified IC50 = 1200 nM 11858756
NPT671 Individual Protein Acidic alpha-glucosidase Rattus norvegicus IC50 = 55000 nM 11858756
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 16000 nM 11858756
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 5800 nM 11858756
NPT2 Others Unspecified IC50 = 150000 nM 11858756
NPT506 Individual Protein Beta-mannosidase Rattus norvegicus IC50 = 290000 nM 11858756
NPT2 Others Unspecified IC50 = 400000 nM 11858756
NPT2 Others Unspecified IC50 = 2500 nM 11858756
NPT1135 Cell Line Hepatocyte Rattus norvegicus IC50 = 9000 nM 18595718
NPT1135 Cell Line Hepatocyte Rattus norvegicus IC50 = 1000 nM 18595718
NPT514 Individual Protein Glycogen debranching enzyme Homo sapiens IC50 = 8400 nM 18595718
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Potency = 6513.1 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency 65.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 562.3 nM PubChem BioAssay data set
NPT71 Cell Line HEK293 Homo sapiens Potency 5802.4 nM PubChem BioAssay data set
NPT10 Individual Protein Geminin Homo sapiens Potency 1258.9 nM PubChem BioAssay data set
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency 35481.3 nM PubChem BioAssay data set
NPT3784 Individual Protein Liver glycogen phosphorylase Rattus norvegicus IC50 = 1000 nM 23378626
NPT3784 Individual Protein Liver glycogen phosphorylase Rattus norvegicus IC50 = 1100 nM 23378626
NPT32 Organism Mus musculus Mus musculus Ki = 392 nM 23378626
NPT2681 Individual Protein Glycogen phosphorylase, muscle form Oryctolagus cuniculus Ki = 400 nM 26708111

  Similar Natural Products 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 NPC311668 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 NPC10262
1.0 High Similarity NPC65832
0.9423 High Similarity NPC272396
0.9286 High Similarity NPC57846
0.9286 High Similarity NPC8087
0.9286 High Similarity NPC474014
0.9286 High Similarity NPC30126
0.9286 High Similarity NPC62507
0.8814 High Similarity NPC474928
0.8667 High Similarity NPC69798
0.8667 High Similarity NPC116377
0.8667 High Similarity NPC101746
0.8667 High Similarity NPC77191
0.8667 High Similarity NPC473952
0.8545 High Similarity NPC275727
0.8276 Intermediate Similarity NPC143809
0.8276 Intermediate Similarity NPC290106
0.8276 Intermediate Similarity NPC76726
0.8276 Intermediate Similarity NPC193593
0.8125 Intermediate Similarity NPC473710
0.8125 Intermediate Similarity NPC475694
0.8103 Intermediate Similarity NPC204709
0.8 Intermediate Similarity NPC255535
0.8 Intermediate Similarity NPC137554
0.8 Intermediate Similarity NPC299603
0.8 Intermediate Similarity NPC285014
0.8 Intermediate Similarity NPC28959
0.7879 Intermediate Similarity NPC474468
0.7869 Intermediate Similarity NPC22774
0.7869 Intermediate Similarity NPC69669
0.7869 Intermediate Similarity NPC150680
0.7869 Intermediate Similarity NPC306462
0.7869 Intermediate Similarity NPC218150
0.7869 Intermediate Similarity NPC2432
0.7778 Intermediate Similarity NPC315980
0.7656 Intermediate Similarity NPC196359
0.7656 Intermediate Similarity NPC135539
0.7656 Intermediate Similarity NPC221764
0.7656 Intermediate Similarity NPC78312
0.7619 Intermediate Similarity NPC223386
0.7619 Intermediate Similarity NPC142290
0.7619 Intermediate Similarity NPC471892
0.7619 Intermediate Similarity NPC75435
0.7619 Intermediate Similarity NPC471780
0.7619 Intermediate Similarity NPC198341
0.75 Intermediate Similarity NPC286851
0.75 Intermediate Similarity NPC303798
0.7344 Intermediate Similarity NPC233034
0.7273 Intermediate Similarity NPC471418
0.7231 Intermediate Similarity NPC294883
0.7231 Intermediate Similarity NPC12514
0.7164 Intermediate Similarity NPC268922
0.7123 Intermediate Similarity NPC100204
0.7123 Intermediate Similarity NPC83248
0.7121 Intermediate Similarity NPC184150
0.7121 Intermediate Similarity NPC141156
0.7121 Intermediate Similarity NPC59221
0.7015 Intermediate Similarity NPC266242
0.7015 Intermediate Similarity NPC254617
0.7015 Intermediate Similarity NPC34291
0.7015 Intermediate Similarity NPC74555
0.7015 Intermediate Similarity NPC126664
0.7015 Intermediate Similarity NPC306763
0.7015 Intermediate Similarity NPC474469
0.6957 Remote Similarity NPC476695
0.6957 Remote Similarity NPC476694
0.6957 Remote Similarity NPC476696
0.6912 Remote Similarity NPC473419
0.6912 Remote Similarity NPC475127
0.6912 Remote Similarity NPC475715
0.6842 Remote Similarity NPC165119
0.6825 Remote Similarity NPC170172
0.6812 Remote Similarity NPC163538
0.6812 Remote Similarity NPC115800
0.6774 Remote Similarity NPC8979
0.6667 Remote Similarity NPC11433
0.6667 Remote Similarity NPC302003
0.6667 Remote Similarity NPC245346
0.6567 Remote Similarity NPC160661
0.6522 Remote Similarity NPC171850
0.6522 Remote Similarity NPC107224
0.6515 Remote Similarity NPC17455
0.6508 Remote Similarity NPC293551
0.65 Remote Similarity NPC306838
0.6418 Remote Similarity NPC471419
0.6418 Remote Similarity NPC163134
0.6375 Remote Similarity NPC469363
0.6364 Remote Similarity NPC314510
0.6316 Remote Similarity NPC98750
0.629 Remote Similarity NPC277072
0.629 Remote Similarity NPC178263
0.6234 Remote Similarity NPC70574
0.6197 Remote Similarity NPC223893
0.6143 Remote Similarity NPC129100
0.6143 Remote Similarity NPC291650
0.6143 Remote Similarity NPC322801
0.6129 Remote Similarity NPC123814
0.6087 Remote Similarity NPC41429
0.6076 Remote Similarity NPC36927
0.6076 Remote Similarity NPC271772
0.6 Remote Similarity NPC121062
0.6 Remote Similarity NPC29222
0.6 Remote Similarity NPC96966
0.5962 Remote Similarity NPC328729
0.5949 Remote Similarity NPC219340
0.5946 Remote Similarity NPC185084
0.5938 Remote Similarity NPC471423
0.5938 Remote Similarity NPC471442
0.5873 Remote Similarity NPC474322
0.5867 Remote Similarity NPC315806
0.5867 Remote Similarity NPC126186
0.5821 Remote Similarity NPC233364
0.5821 Remote Similarity NPC471421
0.5811 Remote Similarity NPC306973
0.5806 Remote Similarity NPC224624
0.5765 Remote Similarity NPC275715
0.5758 Remote Similarity NPC471443
0.5758 Remote Similarity NPC471605
0.5753 Remote Similarity NPC15864
0.5714 Remote Similarity NPC470782
0.5714 Remote Similarity NPC88898
0.5714 Remote Similarity NPC106216
0.5672 Remote Similarity NPC190385
0.5641 Remote Similarity NPC329077
0.5634 Remote Similarity NPC472609

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC311668 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
0.7869 Intermediate Similarity NPD9029 Phase 3
0.7869 Intermediate Similarity NPD9027 Phase 3
0.7869 Intermediate Similarity NPD9028 Phase 2
0.7869 Intermediate Similarity NPD9026 Phase 2
0.7705 Intermediate Similarity NPD9024 Phase 2
0.7705 Intermediate Similarity NPD9022 Phase 2
0.7656 Intermediate Similarity NPD8868 Approved
0.7541 Intermediate Similarity NPD9239 Approved
0.7541 Intermediate Similarity NPD9240 Approved
0.7344 Intermediate Similarity NPD9440 Discontinued
0.7015 Intermediate Similarity NPD9443 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD9444 Discontinued
0.6719 Remote Similarity NPD9455 Approved
0.6667 Remote Similarity NPD8865 Approved
0.6615 Remote Similarity NPD393 Approved
0.6456 Remote Similarity NPD9401 Discovery
0.6379 Remote Similarity NPD399 Approved
0.6379 Remote Similarity NPD400 Approved
0.6379 Remote Similarity NPD398 Approved
0.6143 Remote Similarity NPD9030 Approved
0.6143 Remote Similarity NPD9031 Approved
0.6143 Remote Similarity NPD9032 Approved
0.6143 Remote Similarity NPD9033 Approved
0.6129 Remote Similarity NPD3215 Phase 1
0.6026 Remote Similarity NPD9429 Discontinued
0.5976 Remote Similarity NPD394 Phase 3
0.5962 Remote Similarity NPD8556 Phase 3
0.5921 Remote Similarity NPD9407 Approved
0.5867 Remote Similarity NPD9653 Clinical (unspecified phase)
0.5854 Remote Similarity NPD9640 Clinical (unspecified phase)
0.5806 Remote Similarity NPD3214 Discontinued
0.5802 Remote Similarity NPD883 Phase 2
0.5802 Remote Similarity NPD882 Phase 2
0.5672 Remote Similarity NPD9023 Clinical (unspecified phase)
0.5658 Remote Similarity NPD67 Phase 2
0.5658 Remote Similarity NPD9034 Approved
0.5652 Remote Similarity NPD3193 Approved
0.5652 Remote Similarity NPD3192 Approved
0.5647 Remote Similarity NPD3177 Phase 3

Structure

External Identifiers

PubChem CID   451991
ChEMBL   CHEMBL80254
ZINC  

Physicochemical Properties

Molecular Weight:  133.07
ALogP:  -1.9293
MLogP:  1.57
XLogP:  -0.686
# Rotatable Bonds:  4
Polar Surface Area:  72.72
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  9

Download Data

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Similar NPs/Drugs