Natural Product: NPC258824

Natural Product ID:  NPC258824
Common Name:   Myriocin
IUPAC Name:   (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Synonyms:   Myriocin
Molecular Formula:   C21H39NO6
Standard InCHIKey:  ZZIKIHCNFWXKDY-GNTQXERDSA-N
Standard InCHI:  InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
Canonical SMILES:  CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@](C(=O)O)(CO)N)O)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
NPO33185 cordyceps heteropoda Species Cordycipitaceae Eukaryota PMID[15679316]
NPO1825 Isaria sinclairii Species Cordycipitaceae Eukaryota PMID[8893839]
NPO1825 Isaria sinclairii Species Cordycipitaceae Eukaryota PMID[21456524]
NPO29751 Myriococcum albomyces Species Atheliaceae Eukaryota PMID[21456524]
NPO27451 Ophiocordyceps sinensis Species Ophiocordycipitaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT32 Organism Mus musculus Mus musculus IC50 = 3 nM 10.1016/0960-894X(95)00126-E
NPT2 Others Unspecified IC50 = 3 nM 8893839
NPT32 Organism Mus musculus Mus musculus IC50 = 8 nM 10.1016/0960-894X(95)00304-C
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana IZ = 28 mm 15679316
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae IZ = 14 mm 15679316
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides IZ = 8 mm 15679316
NPT637 Organism Fusarium oxysporum Fusarium oxysporum IZ = 17 mm 15679316
NPT2 Others Unspecified Activity = 10.5 ms 18641634
NPT2 Others Unspecified Activity = 0.8 um2/s 18641634
NPT2 Others Unspecified Activity = 0.9 ms 18641634
NPT2 Others Unspecified Activity = 22.6 ms 18641634
NPT2 Others Unspecified Activity = 12.3 ms 18641634
NPT2 Others Unspecified Activity = 0.7 um2/s 18641634
NPT2 Others Unspecified Activity = 19.3 ms 18641634
NPT2 Others Unspecified Activity = 5.7 ms 18641634
NPT2 Others Unspecified Activity = 1 um2/s 18641634
NPT2 Others Unspecified Activity = 98 % 18641634
NPT2 Others Unspecified Activity = 24 % 18641634
NPT4221 Individual Protein Squalene synthetase Homo sapiens Activity = 97 % 18641634
NPT2 Others Unspecified Activity = 28 % 18641634
NPT2 Others Unspecified Activity = 92 % 18641634
NPT4901 Individual Protein RAC-alpha serine/threonine-protein kinase Mus musculus Inhibition = 50.8 % 18641634
NPT4901 Individual Protein RAC-alpha serine/threonine-protein kinase Mus musculus Inhibition = 51.2 % 18641634
NPT728 Individual Protein Serine/threonine-protein kinase AKT Homo sapiens Inhibition = 46.1 % 18641634
NPT728 Individual Protein Serine/threonine-protein kinase AKT Homo sapiens Inhibition = 48.8 % 18641634
NPT2 Others Unspecified Activity = 30 % 18641634
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 15811.4 nM PubChem BioAssay data set
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 1 mg/kg 21456524
NPT2 Others Unspecified IC50 = 3 nM 21456524
NPT445 Individual Protein Peripheral myelin protein 22 Rattus norvegicus Potency 2.3 nM PubChem BioAssay data set
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = -8.15 % 23062825
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 1.5 % 23062825
NPT2 Others Unspecified Potency 26.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 59.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 84.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 5353.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 8197.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 35481.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 11.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 21.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 10.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 23.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 13.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 13333.2 nM PubChem BioAssay data set
NPT2 Others Unspecified AC50 316.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 316.2 nM PubChem BioAssay data set

  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 NPC258824 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
0.7262 Intermediate Similarity NPC42526
0.7111 Intermediate Similarity NPC207657
0.7079 Intermediate Similarity NPC218817
0.7079 Intermediate Similarity NPC11796
0.6932 Remote Similarity NPC51055
0.6932 Remote Similarity NPC212008
0.6932 Remote Similarity NPC62293
0.6932 Remote Similarity NPC140327
0.6931 Remote Similarity NPC234542
0.6923 Remote Similarity NPC115418
0.6914 Remote Similarity NPC321838
0.6905 Remote Similarity NPC26500
0.6905 Remote Similarity NPC104537
0.6905 Remote Similarity NPC127091
0.6905 Remote Similarity NPC330426
0.6905 Remote Similarity NPC99619
0.6905 Remote Similarity NPC271921
0.6905 Remote Similarity NPC148192
0.6905 Remote Similarity NPC22101
0.6863 Remote Similarity NPC473224
0.6857 Remote Similarity NPC472615
0.6854 Remote Similarity NPC469514
0.6824 Remote Similarity NPC209327
0.6824 Remote Similarity NPC141481
0.6824 Remote Similarity NPC473559
0.6824 Remote Similarity NPC273508
0.6824 Remote Similarity NPC324981
0.6824 Remote Similarity NPC48218
0.6813 Remote Similarity NPC164308
0.6804 Remote Similarity NPC159369
0.6804 Remote Similarity NPC39290
0.6796 Remote Similarity NPC316250
0.679 Remote Similarity NPC243532
0.6778 Remote Similarity NPC281296
0.6774 Remote Similarity NPC477487
0.6774 Remote Similarity NPC7414
0.6762 Remote Similarity NPC472616
0.6707 Remote Similarity NPC201939
0.6706 Remote Similarity NPC473829
0.6706 Remote Similarity NPC475443
0.6705 Remote Similarity NPC470435
0.6703 Remote Similarity NPC121200
0.6702 Remote Similarity NPC477786
0.6702 Remote Similarity NPC477785
0.6702 Remote Similarity NPC477784
0.6667 Remote Similarity NPC47031
0.6667 Remote Similarity NPC49392
0.6667 Remote Similarity NPC190400
0.6667 Remote Similarity NPC476660
0.6636 Remote Similarity NPC261750
0.6636 Remote Similarity NPC1111
0.6634 Remote Similarity NPC314009
0.6634 Remote Similarity NPC54905
0.663 Remote Similarity NPC308545
0.663 Remote Similarity NPC201225
0.663 Remote Similarity NPC113363
0.663 Remote Similarity NPC82488
0.6629 Remote Similarity NPC474321
0.6625 Remote Similarity NPC323436
0.6604 Remote Similarity NPC14537
0.6579 Remote Similarity NPC477515
0.6579 Remote Similarity NPC314268
0.6579 Remote Similarity NPC67917
0.6579 Remote Similarity NPC313802
0.6556 Remote Similarity NPC60718
0.6552 Remote Similarity NPC473772
0.6542 Remote Similarity NPC473252
0.6535 Remote Similarity NPC5418
0.6531 Remote Similarity NPC201046
0.6517 Remote Similarity NPC167145
0.6514 Remote Similarity NPC133729
0.6495 Remote Similarity NPC469910
0.6489 Remote Similarity NPC88735
0.6486 Remote Similarity NPC60432
0.6484 Remote Similarity NPC279537
0.6481 Remote Similarity NPC315531
0.6477 Remote Similarity NPC318766
0.6471 Remote Similarity NPC476657
0.6471 Remote Similarity NPC476654
0.6471 Remote Similarity NPC476655
0.6444 Remote Similarity NPC330016
0.6429 Remote Similarity NPC472007
0.6421 Remote Similarity NPC474252
0.6421 Remote Similarity NPC474312
0.6408 Remote Similarity NPC180722
0.6408 Remote Similarity NPC165332
0.6408 Remote Similarity NPC195645
0.6404 Remote Similarity NPC126061
0.64 Remote Similarity NPC471399
0.64 Remote Similarity NPC316228
0.64 Remote Similarity NPC313670
0.64 Remote Similarity NPC319021
0.6395 Remote Similarity NPC476659
0.6395 Remote Similarity NPC113224
0.6395 Remote Similarity NPC476656
0.6392 Remote Similarity NPC475206
0.6389 Remote Similarity NPC154601
0.6389 Remote Similarity NPC271269
0.6386 Remote Similarity NPC321919
0.6386 Remote Similarity NPC81896
0.6383 Remote Similarity NPC469920
0.6383 Remote Similarity NPC200446
0.6374 Remote Similarity NPC3094
0.6374 Remote Similarity NPC199445
0.6374 Remote Similarity NPC473948
0.6364 Remote Similarity NPC470436
0.6364 Remote Similarity NPC476803
0.6356 Remote Similarity NPC315783
0.6354 Remote Similarity NPC196102
0.6354 Remote Similarity NPC178758
0.6354 Remote Similarity NPC69469
0.6353 Remote Similarity NPC68343
0.6353 Remote Similarity NPC328089
0.6346 Remote Similarity NPC475438
0.6344 Remote Similarity NPC27949
0.6344 Remote Similarity NPC127526
0.6344 Remote Similarity NPC474833
0.6344 Remote Similarity NPC192006
0.6344 Remote Similarity NPC260814
0.6344 Remote Similarity NPC39547
0.6344 Remote Similarity NPC323249
0.6344 Remote Similarity NPC182292
0.6333 Remote Similarity NPC325627
0.6333 Remote Similarity NPC326024
0.633 Remote Similarity NPC251330
0.6327 Remote Similarity NPC469483
0.6327 Remote Similarity NPC476982
0.6327 Remote Similarity NPC472009
0.6316 Remote Similarity NPC117960
0.6316 Remote Similarity NPC14044
0.6316 Remote Similarity NPC474980
0.6316 Remote Similarity NPC172309
0.6316 Remote Similarity NPC30196
0.6306 Remote Similarity NPC477997
0.6304 Remote Similarity NPC266119
0.6304 Remote Similarity NPC239127
0.6304 Remote Similarity NPC470899
0.6304 Remote Similarity NPC474447
0.63 Remote Similarity NPC14901
0.63 Remote Similarity NPC130359
0.6296 Remote Similarity NPC74035
0.6296 Remote Similarity NPC477201
0.6289 Remote Similarity NPC158756
0.6289 Remote Similarity NPC477199
0.6279 Remote Similarity NPC296436
0.6279 Remote Similarity NPC136164
0.6279 Remote Similarity NPC245947
0.6279 Remote Similarity NPC318420
0.6279 Remote Similarity NPC176215
0.6279 Remote Similarity NPC255863
0.6279 Remote Similarity NPC326268
0.6277 Remote Similarity NPC209995
0.6277 Remote Similarity NPC469747
0.6277 Remote Similarity NPC263574
0.6275 Remote Similarity NPC469692
0.6275 Remote Similarity NPC478037
0.6275 Remote Similarity NPC478036
0.6275 Remote Similarity NPC469645
0.6265 Remote Similarity NPC278202
0.6264 Remote Similarity NPC227396
0.6263 Remote Similarity NPC477926
0.6263 Remote Similarity NPC86005
0.6263 Remote Similarity NPC471738
0.6263 Remote Similarity NPC179659
0.6263 Remote Similarity NPC477959
0.6261 Remote Similarity NPC6531
0.625 Remote Similarity NPC473291
0.6238 Remote Similarity NPC478003
0.6238 Remote Similarity NPC474232
0.6238 Remote Similarity NPC478004
0.6238 Remote Similarity NPC158388
0.6237 Remote Similarity NPC476325
0.6237 Remote Similarity NPC122847
0.6237 Remote Similarity NPC476264
0.6235 Remote Similarity NPC54925
0.6228 Remote Similarity NPC50694
0.6224 Remote Similarity NPC470755
0.6222 Remote Similarity NPC320119
0.6218 Remote Similarity NPC314629
0.6214 Remote Similarity NPC121825
0.6211 Remote Similarity NPC472948
0.6211 Remote Similarity NPC47653
0.6211 Remote Similarity NPC103634
0.6207 Remote Similarity NPC314221
0.6207 Remote Similarity NPC83965
0.6207 Remote Similarity NPC60424
0.62 Remote Similarity NPC476706
0.62 Remote Similarity NPC476707
0.62 Remote Similarity NPC472008
0.6196 Remote Similarity NPC255060
0.6196 Remote Similarity NPC264417
0.6196 Remote Similarity NPC217095
0.6196 Remote Similarity NPC217725
0.6196 Remote Similarity NPC260396
0.619 Remote Similarity NPC40812
0.6186 Remote Similarity NPC52609
0.6186 Remote Similarity NPC1761
0.6186 Remote Similarity NPC284472
0.6186 Remote Similarity NPC229799
0.6186 Remote Similarity NPC16488

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC258824 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
0.8537 High Similarity NPD3732 Approved
0.6923 Remote Similarity NPD4252 Approved
0.6848 Remote Similarity NPD5369 Approved
0.6774 Remote Similarity NPD4270 Approved
0.6774 Remote Similarity NPD4269 Approved
0.6747 Remote Similarity NPD3197 Phase 1
0.6609 Remote Similarity NPD8444 Approved
0.6562 Remote Similarity NPD5363 Approved
0.6559 Remote Similarity NPD5368 Approved
0.65 Remote Similarity NPD7983 Approved
0.6495 Remote Similarity NPD5786 Approved
0.6421 Remote Similarity NPD6435 Approved
0.6408 Remote Similarity NPD7839 Suspended
0.6356 Remote Similarity NPD7830 Approved
0.6356 Remote Similarity NPD7829 Approved
0.6344 Remote Similarity NPD4268 Approved
0.6344 Remote Similarity NPD4271 Approved
0.6344 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6238 Remote Similarity NPD5785 Approved
0.6211 Remote Similarity NPD4821 Approved
0.6211 Remote Similarity NPD4819 Approved
0.6211 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6211 Remote Similarity NPD4822 Approved
0.6211 Remote Similarity NPD4820 Approved
0.6207 Remote Similarity NPD7641 Discontinued
0.6186 Remote Similarity NPD7154 Phase 3
0.6161 Remote Similarity NPD6421 Discontinued
0.6139 Remote Similarity NPD6101 Approved
0.6139 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6139 Remote Similarity NPD5370 Suspended
0.6106 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6106 Remote Similarity NPD1719 Phase 1
0.6083 Remote Similarity NPD7642 Approved
0.6078 Remote Similarity NPD6698 Approved
0.6078 Remote Similarity NPD46 Approved
0.6049 Remote Similarity NPD4266 Approved
0.6049 Remote Similarity NPD3194 Approved
0.6049 Remote Similarity NPD3195 Phase 2
0.6049 Remote Similarity NPD3196 Approved
0.6033 Remote Similarity NPD8341 Approved
0.6033 Remote Similarity NPD8299 Approved
0.6033 Remote Similarity NPD8342 Approved
0.6033 Remote Similarity NPD8340 Approved
0.602 Remote Similarity NPD5362 Discontinued
0.6019 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6411 Approved
0.6 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5984 Remote Similarity NPD8451 Approved
0.5983 Remote Similarity NPD7500 Approved
0.5962 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5962 Remote Similarity NPD5779 Approved
0.5962 Remote Similarity NPD5778 Approved
0.5957 Remote Similarity NPD819 Approved
0.5957 Remote Similarity NPD818 Approved
0.5955 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5943 Remote Similarity NPD4228 Discovery
0.5935 Remote Similarity NPD8448 Approved
0.5926 Remote Similarity NPD3172 Approved
0.5862 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5826 Remote Similarity NPD2204 Approved
0.5794 Remote Similarity NPD8392 Approved
0.5794 Remote Similarity NPD8391 Approved
0.5794 Remote Similarity NPD8390 Approved
0.5784 Remote Similarity NPD4251 Approved
0.5784 Remote Similarity NPD4250 Approved
0.5739 Remote Similarity NPD6371 Approved
0.5739 Remote Similarity NPD6420 Discontinued
0.5738 Remote Similarity NPD7623 Phase 3
0.5738 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5736 Remote Similarity NPD8415 Approved
0.5726 Remote Similarity NPD8273 Phase 1
0.5714 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6935 Phase 3
0.5714 Remote Similarity NPD6936 Clinical (unspecified phase)
0.5702 Remote Similarity NPD2217 Approved
0.5702 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5702 Remote Similarity NPD2218 Phase 2
0.57 Remote Similarity NPD5331 Approved
0.57 Remote Similarity NPD5332 Approved
0.5686 Remote Similarity NPD4249 Approved
0.5679 Remote Similarity NPD29 Approved
0.5679 Remote Similarity NPD28 Approved
0.566 Remote Similarity NPD6399 Phase 3
0.5657 Remote Similarity NPD857 Phase 3
0.5657 Remote Similarity NPD4790 Discontinued
0.5656 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5652 Remote Similarity NPD6413 Approved
0.5625 Remote Similarity NPD3173 Approved
0.5619 Remote Similarity NPD7838 Discovery
0.5614 Remote Similarity NPD7899 Clinical (unspecified phase)
0.561 Remote Similarity NPD8080 Discontinued
0.5607 Remote Similarity NPD8394 Approved
0.5607 Remote Similarity NPD5282 Discontinued

Structure

External Identifiers

PubChem CID   6438394
ChEMBL   CHEMBL55076
ZINC  

Physicochemical Properties

Molecular Weight:  401.28
ALogP:  -4.2126
MLogP:  3
XLogP:  0.124
# Rotatable Bonds:  24
Polar Surface Area:  141.08
# H-Bond Aceptor:  7
# H-Bond Donor:  5
# Rings:  0
# Heavy Atoms:  28

Download Data

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