Natural Product: NPC175585

Natural Product ID:  NPC175585
Common Name:   2,3-Dehydrosarsalignone
IUPAC Name:   (E)-N-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-[(1S)-1-(methylamino)ethyl]-4-oxo-1,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]-2-methylbut-2-enamide
Synonyms:   2,3-Dehydrosarsalignone
Molecular Formula:   C27H40N2O2
Standard InCHIKey:  LRFXJBOQCHWLNK-QKEASFQJSA-N
Standard InCHI:  InChI=1S/C27H40N2O2/c1-7-16(2)25(31)29-23-13-15-27(5)21-12-14-26(4)19(17(3)28-6)10-11-20(26)18(21)8-9-22(27)24(23)30/h7,9,13,17-21,28H,8,10-12,14-15H2,1-6H3,(H,29,31)/b16-7+/t17-,18-,19+,20-,21-,26+,27+/m0/s1
Canonical SMILES:  CN[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC=C(C2=O)N=C(/C(=C/C)/C)O)C
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
NPO11838 Euphorbia regis-jubae Species Euphorbiaceae Eukaryota UNPD*
NPO2332 Plantago serraria Species Plantaginaceae Eukaryota UNPD*
NPO12900 Sarcococca hookeriana Species Buxaceae Eukaryota PMID[18681480]
NPO7351 Uncaria pteropoda Species Rubiaceae Eukaryota UNPD*
NPO6711 Streptomyces mirabilis Species Streptomycetaceae Bacteria UNPD*
NPO13128 Crotalaria rosenii Species Fabaceae Eukaryota UNPD*
NPO4160 Cephalosporium polyaleurum Species NA Eukaryota UNPD*
NPO12450 Cneorum pulverulentum Species Rutaceae Eukaryota UNPD*
NPO18213 Strychnos variabilis Species Loganiaceae Eukaryota UNPD*
NPO5033 Alpinia galanga Species Zingiberaceae Eukaryota UNPD*
NPO10911 Euphorbia peplis Species Euphorbiaceae Eukaryota UNPD*
NPO9527 Dendrodoa grossularia Species Styelidae Eukaryota UNPD*
NPO12328 Ampelopsis japonica Species Vitaceae Eukaryota UNPD*
NPO12560 Cassia leptophylla Species Fabaceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT841 Organism Leishmania major Leishmania major IC50 = 21300 nM 18681480
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 20 mm 18681480
NPT2921 Organism Pseudomonas Pseudomonas IZ = 16.5 mm 18681480
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 35600 nM 18681480
NPT2921 Organism Pseudomonas Pseudomonas MIC = 35600 nM 18681480
NPT729 Organism Micrococcus luteus Micrococcus luteus IZ = 12.5 mm 18681480
NPT175 Organism Enterococcus faecalis Enterococcus faecalis IZ = 10 mm 18681480
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 142600 nM 18681480

  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 NPC175585 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
0.9216 High Similarity NPC469958
0.9126 High Similarity NPC230677
0.8835 High Similarity NPC152718
0.8654 High Similarity NPC226509
0.8095 Intermediate Similarity NPC184033
0.8037 Intermediate Similarity NPC34193
0.75 Intermediate Similarity NPC247220
0.7478 Intermediate Similarity NPC72688
0.7477 Intermediate Similarity NPC476754
0.7456 Intermediate Similarity NPC24596
0.7383 Intermediate Similarity NPC476752
0.7383 Intermediate Similarity NPC476753
0.7364 Intermediate Similarity NPC140685
0.7353 Intermediate Similarity NPC21667
0.7308 Intermediate Similarity NPC166458
0.7281 Intermediate Similarity NPC185929
0.7273 Intermediate Similarity NPC167419
0.7264 Intermediate Similarity NPC249312
0.7232 Intermediate Similarity NPC474001
0.7227 Intermediate Similarity NPC176336
0.7168 Intermediate Similarity NPC58200
0.7087 Intermediate Similarity NPC3511
0.7087 Intermediate Similarity NPC142253
0.7048 Intermediate Similarity NPC311769
0.7048 Intermediate Similarity NPC182106
0.6963 Remote Similarity NPC153007
0.6957 Remote Similarity NPC474563
0.6952 Remote Similarity NPC87552
0.6923 Remote Similarity NPC472239
0.6887 Remote Similarity NPC8571
0.6887 Remote Similarity NPC152684
0.6875 Remote Similarity NPC317654
0.6875 Remote Similarity NPC96010
0.687 Remote Similarity NPC50815
0.687 Remote Similarity NPC471083
0.6857 Remote Similarity NPC41539
0.6855 Remote Similarity NPC35037
0.6852 Remote Similarity NPC259252
0.681 Remote Similarity NPC98765
0.6774 Remote Similarity NPC474006
0.6762 Remote Similarity NPC472867
0.675 Remote Similarity NPC328052
0.6729 Remote Similarity NPC24733
0.6729 Remote Similarity NPC472931
0.6729 Remote Similarity NPC472940
0.6724 Remote Similarity NPC247060
0.6723 Remote Similarity NPC140251
0.6723 Remote Similarity NPC307903
0.6695 Remote Similarity NPC195841
0.6695 Remote Similarity NPC233256
0.6667 Remote Similarity NPC90538
0.6667 Remote Similarity NPC4166
0.6639 Remote Similarity NPC124358
0.6636 Remote Similarity NPC178025
0.6636 Remote Similarity NPC181743
0.6636 Remote Similarity NPC16287
0.6604 Remote Similarity NPC311092
0.6574 Remote Similarity NPC60350
0.6557 Remote Similarity NPC66862
0.6535 Remote Similarity NPC470044
0.6535 Remote Similarity NPC470045
0.6535 Remote Similarity NPC303613
0.6535 Remote Similarity NPC474228
0.6515 Remote Similarity NPC119326
0.6509 Remote Similarity NPC257962
0.65 Remote Similarity NPC476756
0.65 Remote Similarity NPC244982
0.6489 Remote Similarity NPC473249
0.6471 Remote Similarity NPC119329
0.6455 Remote Similarity NPC476293
0.6449 Remote Similarity NPC224072
0.6449 Remote Similarity NPC283277
0.6442 Remote Similarity NPC91665
0.6441 Remote Similarity NPC469598
0.6439 Remote Similarity NPC471586
0.6439 Remote Similarity NPC478136
0.6422 Remote Similarity NPC474083
0.6415 Remote Similarity NPC12035
0.6412 Remote Similarity NPC237286
0.6389 Remote Similarity NPC279639
0.6389 Remote Similarity NPC3856
0.6379 Remote Similarity NPC474164
0.6373 Remote Similarity NPC251705
0.6372 Remote Similarity NPC204341
0.6364 Remote Similarity NPC475610
0.6364 Remote Similarity NPC169375
0.6356 Remote Similarity NPC77703
0.6355 Remote Similarity NPC152039
0.6355 Remote Similarity NPC118329
0.6355 Remote Similarity NPC329782
0.6355 Remote Similarity NPC474122
0.6346 Remote Similarity NPC69408
0.6341 Remote Similarity NPC476290
0.6341 Remote Similarity NPC72753
0.6339 Remote Similarity NPC473999
0.6339 Remote Similarity NPC262043
0.6339 Remote Similarity NPC309603
0.6337 Remote Similarity NPC282593
0.6337 Remote Similarity NPC251929
0.6337 Remote Similarity NPC35734
0.6337 Remote Similarity NPC265782
0.6337 Remote Similarity NPC2634
0.6337 Remote Similarity NPC307176
0.6337 Remote Similarity NPC159577
0.633 Remote Similarity NPC164577
0.633 Remote Similarity NPC473246
0.6321 Remote Similarity NPC170793
0.6321 Remote Similarity NPC90965
0.6316 Remote Similarity NPC69454
0.6316 Remote Similarity NPC472930
0.6316 Remote Similarity NPC247316
0.6316 Remote Similarity NPC474736
0.6311 Remote Similarity NPC309852
0.6311 Remote Similarity NPC255021
0.6306 Remote Similarity NPC472614
0.6306 Remote Similarity NPC136948
0.6303 Remote Similarity NPC176012
0.6296 Remote Similarity NPC469799
0.6296 Remote Similarity NPC469804
0.6296 Remote Similarity NPC469805
0.6296 Remote Similarity NPC469806
0.6296 Remote Similarity NPC472312
0.6296 Remote Similarity NPC320514
0.6296 Remote Similarity NPC39966
0.6296 Remote Similarity NPC215474
0.6293 Remote Similarity NPC456
0.6293 Remote Similarity NPC472941
0.6283 Remote Similarity NPC48010
0.6281 Remote Similarity NPC55462
0.6281 Remote Similarity NPC476328
0.6275 Remote Similarity NPC54123
0.6275 Remote Similarity NPC234707
0.6275 Remote Similarity NPC305501
0.6275 Remote Similarity NPC115023
0.6273 Remote Similarity NPC11711
0.6273 Remote Similarity NPC29447
0.6273 Remote Similarity NPC471224
0.6271 Remote Similarity NPC239768
0.6271 Remote Similarity NPC135799
0.6271 Remote Similarity NPC128698
0.6271 Remote Similarity NPC275686
0.627 Remote Similarity NPC476813
0.627 Remote Similarity NPC476814
0.625 Remote Similarity NPC476346
0.625 Remote Similarity NPC293803
0.624 Remote Similarity NPC476269
0.6239 Remote Similarity NPC168188
0.6239 Remote Similarity NPC97913
0.6239 Remote Similarity NPC470015
0.6238 Remote Similarity NPC139397
0.6228 Remote Similarity NPC475806
0.6228 Remote Similarity NPC233116
0.6228 Remote Similarity NPC23217
0.6228 Remote Similarity NPC473998
0.6228 Remote Similarity NPC63748
0.6226 Remote Similarity NPC82635
0.6222 Remote Similarity NPC478139
0.6218 Remote Similarity NPC118275
0.6216 Remote Similarity NPC475022
0.6216 Remote Similarity NPC118648
0.6216 Remote Similarity NPC222613
0.6216 Remote Similarity NPC476141
0.6214 Remote Similarity NPC130016
0.6214 Remote Similarity NPC180015
0.6214 Remote Similarity NPC56747
0.6214 Remote Similarity NPC109576
0.621 Remote Similarity NPC472359
0.6207 Remote Similarity NPC472932
0.6207 Remote Similarity NPC259286
0.6204 Remote Similarity NPC38350
0.6204 Remote Similarity NPC201912
0.6204 Remote Similarity NPC477372
0.6198 Remote Similarity NPC472616
0.6198 Remote Similarity NPC475239
0.6195 Remote Similarity NPC123912
0.619 Remote Similarity NPC5485
0.619 Remote Similarity NPC1254
0.6186 Remote Similarity NPC235464
0.6186 Remote Similarity NPC166745
0.6186 Remote Similarity NPC197386
0.6182 Remote Similarity NPC214043
0.6182 Remote Similarity NPC472865
0.6182 Remote Similarity NPC85774
0.6179 Remote Similarity NPC476276
0.6176 Remote Similarity NPC260040
0.6168 Remote Similarity NPC472490
0.6168 Remote Similarity NPC211322
0.6161 Remote Similarity NPC93778
0.6154 Remote Similarity NPC249954
0.6147 Remote Similarity NPC260956
0.6147 Remote Similarity NPC477583
0.6147 Remote Similarity NPC193347
0.6147 Remote Similarity NPC477581
0.614 Remote Similarity NPC191684
0.614 Remote Similarity NPC473056
0.614 Remote Similarity NPC236322
0.614 Remote Similarity NPC84171
0.614 Remote Similarity NPC69622
0.6139 Remote Similarity NPC260474
0.6139 Remote Similarity NPC20610

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC175585 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
0.7315 Intermediate Similarity NPD5769 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD3527 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6404 Discontinued
0.688 Remote Similarity NPD7739 Clinical (unspecified phase)
0.6693 Remote Similarity NPD7623 Phase 3
0.6693 Remote Similarity NPD7624 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6914 Discontinued
0.6489 Remote Similarity NPD7747 Phase 1
0.6489 Remote Similarity NPD7746 Phase 1
0.6471 Remote Similarity NPD7812 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5733 Approved
0.6404 Remote Similarity NPD5771 Approved
0.6337 Remote Similarity NPD4747 Approved
0.6337 Remote Similarity NPD4691 Approved
0.6311 Remote Similarity NPD4687 Approved
0.629 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6275 Remote Similarity NPD5276 Approved
0.6238 Remote Similarity NPD4137 Phase 3
0.6216 Remote Similarity NPD5690 Phase 2
0.6194 Remote Similarity NPD6330 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4058 Approved
0.6147 Remote Similarity NPD4221 Approved
0.6147 Remote Similarity NPD4223 Phase 3
0.614 Remote Similarity NPD4096 Approved
0.6126 Remote Similarity NPD5329 Approved
0.6071 Remote Similarity NPD5280 Approved
0.6071 Remote Similarity NPD4694 Approved
0.6047 Remote Similarity NPD7500 Approved
0.6036 Remote Similarity NPD4197 Approved
0.6016 Remote Similarity NPD7333 Discontinued
0.5948 Remote Similarity NPD6079 Approved
0.5929 Remote Similarity NPD4689 Approved
0.5929 Remote Similarity NPD5205 Approved
0.5929 Remote Similarity NPD4688 Approved
0.5929 Remote Similarity NPD4690 Approved
0.5929 Remote Similarity NPD5279 Phase 3
0.5929 Remote Similarity NPD4693 Phase 3
0.5929 Remote Similarity NPD4138 Approved
0.5929 Remote Similarity NPD4623 Approved
0.5929 Remote Similarity NPD4519 Discontinued
0.5926 Remote Similarity NPD1402 Approved
0.5913 Remote Similarity NPD5328 Approved
0.5909 Remote Similarity NPD8028 Phase 2
0.5893 Remote Similarity NPD3666 Approved
0.5893 Remote Similarity NPD4786 Approved
0.5893 Remote Similarity NPD3133 Approved
0.5893 Remote Similarity NPD3665 Phase 1
0.5825 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5812 Remote Similarity NPD5281 Approved
0.5812 Remote Similarity NPD5284 Approved
0.5789 Remote Similarity NPD3618 Phase 1
0.5789 Remote Similarity NPD3574 Clinical (unspecified phase)
0.578 Remote Similarity NPD3617 Approved
0.578 Remote Similarity NPD4776 Phase 2
0.578 Remote Similarity NPD4777 Suspended
0.5776 Remote Similarity NPD4753 Phase 2
0.5727 Remote Similarity NPD4195 Approved
0.5714 Remote Similarity NPD6939 Phase 2
0.5714 Remote Similarity NPD6938 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3667 Approved
0.5703 Remote Similarity NPD6420 Discontinued
0.5676 Remote Similarity NPD4695 Discontinued
0.5667 Remote Similarity NPD5695 Phase 3
0.5667 Remote Similarity NPD4629 Approved
0.5667 Remote Similarity NPD5210 Approved
0.5645 Remote Similarity NPD5211 Phase 2
0.563 Remote Similarity NPD6909 Approved
0.563 Remote Similarity NPD4202 Approved
0.563 Remote Similarity NPD6908 Approved
0.563 Remote Similarity NPD2251 Approved
0.563 Remote Similarity NPD2252 Approved
0.563 Remote Similarity NPD5133 Approved
0.5625 Remote Similarity NPD4692 Approved
0.5625 Remote Similarity NPD4139 Approved
0.562 Remote Similarity NPD5220 Clinical (unspecified phase)
0.562 Remote Similarity NPD7614 Phase 1
0.562 Remote Similarity NPD5221 Approved
0.562 Remote Similarity NPD5222 Approved

Structure

External Identifiers

PubChem CID   44587283
ChEMBL   CHEMBL525190
ZINC  

Physicochemical Properties

Molecular Weight:  424.31
ALogP:  2.0607
MLogP:  3.99
XLogP:  6.092
# Rotatable Bonds:  11
Polar Surface Area:  61.69
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  31

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