Natural Product: NPC290106

Natural Product ID:  NPC290106
Common Name:   3-Epifagomine
IUPAC Name:   (2R,3R,4S)-2-(hydroxymethyl)piperidine-3,4-diol
Synonyms:   3-Epi-Fagomine; 3-Epifagomine
Molecular Formula:   C6H13NO3
Standard InCHIKey:  YZNNBIPIQWYLDM-NGJCXOISSA-N
Standard InCHI:  InChI=1S/C6H13NO3/c8-3-4-6(10)5(9)1-2-7-4/h4-10H,1-3H2/t4-,5+,6-/m1/s1
Canonical SMILES:  OC[C@H]1NCC[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
NPO10350 Erythrina speciosa Species Fabaceae Eukaryota UNPD*
NPO25832 Helichrysum drakensbergense Species Asteraceae Eukaryota UNPD*
NPO25797 Piper divaricatum Species Piperaceae Eukaryota UNPD*
NPO27030 Commiphora sphaerocarpa Species Burseraceae Eukaryota UNPD*
NPO21156 Xanthocercis zambesiaca Species Fabaceae Eukaryota PMID[9157194]
NPO21156 Xanthocercis zambesiaca Species Fabaceae Eukaryota PMID[9544568]
NPO16194 Morus bombycis Species Moraceae Eukaryota PMID[9544568]
NPO33446 aglaonema treubii Species Araceae Eukaryota PMID[9544568]
NPO12473 Castanospermum australe Species Fabaceae Eukaryota PMID[9544568]
NPO10677 Prunus prostrata Species Rosaceae Eukaryota UNPD*
NPO17806 Richteria pyrethroides Species Asteraceae Eukaryota UNPD*
NPO21156 Xanthocercis zambesiaca Species Fabaceae Eukaryota Root PMID[9544568]
NPO21156 Xanthocercis zambesiaca Species Fabaceae Eukaryota Leaves PMID[9157194]
NPO22874 Bombyx mori Species Bombycidae Eukaryota Faeces PMID[18323202]
NPO28265 Morus alba Species Moraceae Eukaryota TCM_Taiwan*
NPO28265 Morus alba Species Moraceae Eukaryota Leaves PMID[22207282]
NPO26847 Lecidea quernea Species Lecideaceae Eukaryota UNPD*
NPO23250 Plakortis angulospiculatus Species Plakinidae Eukaryota UNPD*
NPO27103 Satureja vulgaris Species Lamiaceae Eukaryota UNPD*
NPO26218 Prosopis africana Species Fabaceae Eukaryota UNPD*
NPO26151 Santolina pectinata Species Asteraceae Eukaryota UNPD*
NPO28265 Morus alba Species Moraceae Eukaryota TM-MC*
NPO16194 Morus bombycis Species Moraceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT671 Individual Protein Acidic alpha-glucosidase Rattus norvegicus IC50 = 500000 nM 7966130
NPT1055 Individual Protein Neutral alpha-glucosidase C Mus musculus IC50 = 6400 nM 7966130
NPT503 Individual Protein Alpha-L-fucosidase I Homo sapiens IC50 = 1000000 nM 7966130
NPT495 Individual Protein Beta-galactosidase Rattus norvegicus IC50 = 4000 nM 7966130
NPT509 Individual Protein Beta-galactosidase Bos taurus IC50 = 3100 nM 7966130
NPT1058 Individual Protein Beta-glucosidase A Caldicellulosiruptor saccharolyticus IC50 = 100000 nM 7966130
NPT1051 Individual Protein Lactase-glycosylceramidase Rattus norvegicus IC50 = 1900 nM 7966130
NPT509 Individual Protein Beta-galactosidase Bos taurus IC50 = 1500 nM 7966130
NPT2 Others Unspecified IC50 = 120000 nM 9157194
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 6000 nM 9157194
NPT2 Others Unspecified IC50 = 740000 nM 9157194
NPT2 Others Unspecified IC50 = 100000 nM 9157194
NPT2 Others Unspecified Inhibition < 50 % 9157194
NPT2 Others Unspecified IC50 = 4000 nM 9157194
NPT2 Others Unspecified IC50 = 3000 nM 9157194
NPT1051 Individual Protein Lactase-glycosylceramidase Rattus norvegicus IC50 = 4300 nM 21546253
NPT2 Others Unspecified Inhibition < 50 % 21546253
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus Inhibition < 50 % 21546253
NPT61 Individual Protein Beta-glucocerebrosidase Homo sapiens Inhibition < 50 % 21546253
NPT496 Individual Protein Alpha-L-fucosidase 1 Bos taurus Inhibition < 50 % 21546253
NPT2 Others Unspecified IC50 = 120000 nM 21546253
NPT2 Others Unspecified IC50 = 39000 nM 21546253
NPT3767 Individual Protein Glucosylceramidase Bos taurus IC50 = 5600 nM 21546253
NPT509 Individual Protein Beta-galactosidase Bos taurus IC50 = 3000 nM 21546253
NPT3907 Individual Protein Ceramide glucosyltransferase Mus musculus IC50 > 10000 nM 24900342
NPT2 Others Unspecified IC50 = 700000 nM 24900342
NPT513 Individual Protein Beta-glucosidase Homo sapiens IC50 > 1000000 nM 24900342

  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 NPC290106 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 NPC143809
1.0 High Similarity NPC76726
1.0 High Similarity NPC193593
0.9474 High Similarity NPC69669
0.9474 High Similarity NPC2432
0.9474 High Similarity NPC22774
0.9474 High Similarity NPC150680
0.9474 High Similarity NPC218150
0.9474 High Similarity NPC306462
0.9455 High Similarity NPC204709
0.9153 High Similarity NPC223386
0.9153 High Similarity NPC75435
0.9153 High Similarity NPC471892
0.9153 High Similarity NPC198341
0.9153 High Similarity NPC471780
0.9153 High Similarity NPC142290
0.9 High Similarity NPC315980
0.9 High Similarity NPC303798
0.9 High Similarity NPC286851
0.871 High Similarity NPC471418
0.8571 High Similarity NPC268922
0.8333 Intermediate Similarity NPC8087
0.8333 Intermediate Similarity NPC30126
0.8333 Intermediate Similarity NPC474014
0.8333 Intermediate Similarity NPC57846
0.8333 Intermediate Similarity NPC62507
0.8308 Intermediate Similarity NPC299603
0.8308 Intermediate Similarity NPC28959
0.8308 Intermediate Similarity NPC255535
0.8308 Intermediate Similarity NPC137554
0.8308 Intermediate Similarity NPC476696
0.8308 Intermediate Similarity NPC285014
0.8308 Intermediate Similarity NPC476694
0.8308 Intermediate Similarity NPC476695
0.8305 Intermediate Similarity NPC170172
0.8276 Intermediate Similarity NPC65832
0.8276 Intermediate Similarity NPC311668
0.8276 Intermediate Similarity NPC10262
0.7937 Intermediate Similarity NPC474928
0.7812 Intermediate Similarity NPC116377
0.7812 Intermediate Similarity NPC77191
0.7812 Intermediate Similarity NPC101746
0.7812 Intermediate Similarity NPC69798
0.7812 Intermediate Similarity NPC473952
0.7778 Intermediate Similarity NPC471419
0.7778 Intermediate Similarity NPC163134
0.7759 Intermediate Similarity NPC272396
0.7656 Intermediate Similarity NPC233034
0.7576 Intermediate Similarity NPC107224
0.75 Intermediate Similarity NPC98750
0.7397 Intermediate Similarity NPC70574
0.7353 Intermediate Similarity NPC475694
0.7353 Intermediate Similarity NPC473710
0.7313 Intermediate Similarity NPC34291
0.7313 Intermediate Similarity NPC126664
0.72 Intermediate Similarity NPC271772
0.72 Intermediate Similarity NPC36927
0.7143 Intermediate Similarity NPC474468
0.7143 Intermediate Similarity NPC471421
0.7143 Intermediate Similarity NPC233364
0.7097 Intermediate Similarity NPC8979
0.7067 Intermediate Similarity NPC219340
0.7049 Intermediate Similarity NPC275727
0.7 Intermediate Similarity NPC306973
0.6933 Remote Similarity NPC100204
0.6933 Remote Similarity NPC83248
0.6912 Remote Similarity NPC291650
0.6912 Remote Similarity NPC129100
0.6912 Remote Similarity NPC322801
0.6901 Remote Similarity NPC185084
0.6835 Remote Similarity NPC469363
0.6667 Remote Similarity NPC165119
0.6622 Remote Similarity NPC477002
0.6618 Remote Similarity NPC472609
0.6615 Remote Similarity NPC268927
0.6615 Remote Similarity NPC276928
0.6615 Remote Similarity NPC64250
0.6613 Remote Similarity NPC277072
0.6613 Remote Similarity NPC178263
0.6571 Remote Similarity NPC171850
0.6571 Remote Similarity NPC474469
0.6522 Remote Similarity NPC294883
0.6522 Remote Similarity NPC12514
0.6479 Remote Similarity NPC473419
0.6479 Remote Similarity NPC475715
0.6479 Remote Similarity NPC475127
0.6452 Remote Similarity NPC123814
0.6429 Remote Similarity NPC59221
0.6429 Remote Similarity NPC196359
0.6429 Remote Similarity NPC78312
0.6429 Remote Similarity NPC135539
0.6429 Remote Similarity NPC221764
0.6429 Remote Similarity NPC141156
0.6429 Remote Similarity NPC184150
0.6364 Remote Similarity NPC150557
0.6351 Remote Similarity NPC26932
0.6341 Remote Similarity NPC306838
0.6338 Remote Similarity NPC254617
0.6338 Remote Similarity NPC306763
0.6338 Remote Similarity NPC266242
0.6338 Remote Similarity NPC74555
0.6333 Remote Similarity NPC121062
0.6333 Remote Similarity NPC29222
0.6333 Remote Similarity NPC96966
0.6324 Remote Similarity NPC17455
0.6203 Remote Similarity NPC471420
0.619 Remote Similarity NPC474322
0.6164 Remote Similarity NPC163538
0.6164 Remote Similarity NPC115800
0.6061 Remote Similarity NPC293551
0.5974 Remote Similarity NPC244539
0.5949 Remote Similarity NPC475363
0.5949 Remote Similarity NPC473971
0.5949 Remote Similarity NPC473972
0.5946 Remote Similarity NPC327486
0.5946 Remote Similarity NPC223174
0.5946 Remote Similarity NPC327753
0.5921 Remote Similarity NPC208657
0.5915 Remote Similarity NPC41429
0.5897 Remote Similarity NPC313762
0.5875 Remote Similarity NPC318258
0.5873 Remote Similarity NPC224624
0.5857 Remote Similarity NPC145627
0.5844 Remote Similarity NPC78562
0.5844 Remote Similarity NPC473588
0.5811 Remote Similarity NPC223893
0.5797 Remote Similarity NPC319131
0.5797 Remote Similarity NPC68974
0.5775 Remote Similarity NPC88898
0.5775 Remote Similarity NPC106216
0.5761 Remote Similarity NPC315170
0.5741 Remote Similarity NPC328729
0.5732 Remote Similarity NPC242077
0.5732 Remote Similarity NPC315969
0.5679 Remote Similarity NPC314762
0.5663 Remote Similarity NPC263058
0.5634 Remote Similarity NPC47333
0.5625 Remote Similarity NPC314772
0.5625 Remote Similarity NPC314968
0.5606 Remote Similarity NPC270041
0.56 Remote Similarity NPC23721

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC290106 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
0.9474 High Similarity NPD9029 Phase 3
0.9474 High Similarity NPD9028 Phase 2
0.9474 High Similarity NPD9026 Phase 2
0.9474 High Similarity NPD9027 Phase 3
0.8333 Intermediate Similarity NPD9022 Phase 2
0.8333 Intermediate Similarity NPD9024 Phase 2
0.8167 Intermediate Similarity NPD9455 Approved
0.8033 Intermediate Similarity NPD393 Approved
0.7869 Intermediate Similarity NPD9239 Approved
0.7869 Intermediate Similarity NPD9240 Approved
0.7656 Intermediate Similarity NPD9440 Discontinued
0.7313 Intermediate Similarity NPD9443 Clinical (unspecified phase)
0.6923 Remote Similarity NPD9401 Discovery
0.6912 Remote Similarity NPD9031 Approved
0.6912 Remote Similarity NPD9030 Approved
0.6912 Remote Similarity NPD9032 Approved
0.6912 Remote Similarity NPD9033 Approved
0.6452 Remote Similarity NPD3215 Phase 1
0.6429 Remote Similarity NPD8868 Approved
0.642 Remote Similarity NPD394 Phase 3
0.6351 Remote Similarity NPD9034 Approved
0.6351 Remote Similarity NPD67 Phase 2
0.6338 Remote Similarity NPD9444 Discontinued
0.6167 Remote Similarity NPD400 Approved
0.6167 Remote Similarity NPD399 Approved
0.6167 Remote Similarity NPD398 Approved
0.6129 Remote Similarity NPD3214 Discontinued
0.6056 Remote Similarity NPD9442 Clinical (unspecified phase)
0.6049 Remote Similarity NPD882 Phase 2
0.6049 Remote Similarity NPD883 Phase 2
0.5946 Remote Similarity NPD9445 Approved
0.5897 Remote Similarity NPD372 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6704 Discontinued
0.5775 Remote Similarity NPD9211 Clinical (unspecified phase)
0.5741 Remote Similarity NPD8556 Phase 3
0.5732 Remote Similarity NPD9646 Approved
0.5732 Remote Similarity NPD9644 Approved
0.5732 Remote Similarity NPD9645 Approved
0.5679 Remote Similarity NPD9429 Discontinued
0.5652 Remote Similarity NPD4282 Approved
0.5625 Remote Similarity NPD9434 Approved
0.5625 Remote Similarity NPD9435 Approved

Structure

External Identifiers

PubChem CID   10290867
ChEMBL   CHEMBL456583
ZINC  

Physicochemical Properties

Molecular Weight:  147.09
ALogP:  -2.2173
MLogP:  1.68
XLogP:  -0.757
# Rotatable Bonds:  4
Polar Surface Area:  72.72
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  10

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