Natural Product: NPC472536

Natural Product ID:  NPC472536
Common Name:   Aurilide C
IUPAC Name:   (3S,6S,12S,15S,18R,21E,24S,25S,26S)-12-[(2R)-butan-2-yl]-24-hydroxy-3,4,10,13,21,25-hexamethyl-26-[(E)-pent-2-en-2-yl]-6,15,18-tri(propan-2-yl)-1,19-dioxa-4,7,10,13,16-pentazacyclohexacos-21-ene-2,5,8,11,14,17,20-heptone
Synonyms:   Aurilide C
Molecular Formula:   C43H73N5O10
Standard InCHIKey:  BCIDYWRVGQFMIS-NOZRKBPESA-N
Standard InCHI:  InChI=1S/C43H73N5O10/c1-17-19-27(10)37-29(12)31(49)21-20-28(11)42(55)57-36(25(7)8)38(51)45-34(24(5)6)40(53)48(16)35(26(9)18-2)41(54)46(14)22-32(50)44-33(23(3)4)39(52)47(15)30(13)43(56)58-37/h19-20,23-26,29-31,33-37,49H,17-18,21-22H2,1-16H3,(H,44,50)(H,45,51)/b27-19+,28-20+/t26-,29+,30+,31+,33+,34+,35+,36-,37-/m1/s1
Canonical SMILES:  CC/C=C(/[C@H]1OC(=O)[C@H](C)N(C)C(=O)[C@@H](N=C(O)CN(C)C(=O)[C@H]([C@@H](CC)C)N(C(=O)[C@@H](N=C([C@H](OC(=O)/C(=C/C[C@@H]([C@@H]1C)O)/C)C(C)C)O)C(C)C)C)C(C)C)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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria Papua New Guinea PMID[16643028]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT397 Cell Line NCI-H460 Homo sapiens LC50 = 130 nM PubChem BioAssay data set
NPT2 Others Unspecified LC50 = 50 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 NPC472536 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 NPC103391
0.7895 Intermediate Similarity NPC201244
0.7895 Intermediate Similarity NPC477217
0.7788 Intermediate Similarity NPC205176
0.7778 Intermediate Similarity NPC135121
0.7642 Intermediate Similarity NPC273185
0.7586 Intermediate Similarity NPC171734
0.7436 Intermediate Similarity NPC474099
0.7387 Intermediate Similarity NPC469739
0.7304 Intermediate Similarity NPC474244
0.725 Intermediate Similarity NPC476875
0.7176 Intermediate Similarity NPC120335
0.7167 Intermediate Similarity NPC251122
0.7155 Intermediate Similarity NPC475149
0.7155 Intermediate Similarity NPC471097
0.7143 Intermediate Similarity NPC207820
0.7143 Intermediate Similarity NPC315188
0.7094 Intermediate Similarity NPC68001
0.7094 Intermediate Similarity NPC474827
0.7094 Intermediate Similarity NPC199831
0.7094 Intermediate Similarity NPC474828
0.7069 Intermediate Similarity NPC188785
0.7059 Intermediate Similarity NPC127741
0.7054 Intermediate Similarity NPC309525
0.7 Intermediate Similarity NPC473249
0.6983 Remote Similarity NPC13175
0.6983 Remote Similarity NPC475791
0.6975 Remote Similarity NPC154601
0.6957 Remote Similarity NPC52820
0.6957 Remote Similarity NPC307357
0.6957 Remote Similarity NPC46098
0.6957 Remote Similarity NPC268841
0.6949 Remote Similarity NPC476877
0.6934 Remote Similarity NPC68865
0.6897 Remote Similarity NPC475758
0.6897 Remote Similarity NPC220234
0.6885 Remote Similarity NPC469603
0.6838 Remote Similarity NPC26597
0.6833 Remote Similarity NPC476876
0.6833 Remote Similarity NPC271269
0.6777 Remote Similarity NPC251330
0.6763 Remote Similarity NPC315848
0.6763 Remote Similarity NPC315210
0.6754 Remote Similarity NPC38172
0.675 Remote Similarity NPC469604
0.675 Remote Similarity NPC74035
0.6724 Remote Similarity NPC175614
0.6723 Remote Similarity NPC5864
0.6723 Remote Similarity NPC124554
0.6723 Remote Similarity NPC301148
0.672 Remote Similarity NPC469597
0.6691 Remote Similarity NPC120420
0.6667 Remote Similarity NPC168113
0.6667 Remote Similarity NPC470652
0.6667 Remote Similarity NPC246005
0.6642 Remote Similarity NPC246079
0.6642 Remote Similarity NPC99864
0.6641 Remote Similarity NPC201889
0.6641 Remote Similarity NPC106791
0.6641 Remote Similarity NPC235625
0.6638 Remote Similarity NPC189764
0.662 Remote Similarity NPC176226
0.662 Remote Similarity NPC197682
0.6612 Remote Similarity NPC64168
0.6612 Remote Similarity NPC124549
0.6596 Remote Similarity NPC239762
0.6596 Remote Similarity NPC163392
0.6591 Remote Similarity NPC470654
0.6591 Remote Similarity NPC470653
0.6591 Remote Similarity NPC470650
0.6589 Remote Similarity NPC477237
0.6587 Remote Similarity NPC130124
0.6587 Remote Similarity NPC193471
0.6585 Remote Similarity NPC67009
0.6573 Remote Similarity NPC52748
0.6567 Remote Similarity NPC477793
0.6567 Remote Similarity NPC329919
0.656 Remote Similarity NPC474411
0.656 Remote Similarity NPC474431
0.6549 Remote Similarity NPC155230
0.6529 Remote Similarity NPC198344
0.6529 Remote Similarity NPC80439
0.6529 Remote Similarity NPC6271
0.6529 Remote Similarity NPC173690
0.6529 Remote Similarity NPC279833
0.6522 Remote Similarity NPC62263
0.6522 Remote Similarity NPC173763
0.6522 Remote Similarity NPC471098
0.6507 Remote Similarity NPC471820
0.6507 Remote Similarity NPC471821
0.6496 Remote Similarity NPC233273
0.6496 Remote Similarity NPC205546
0.6496 Remote Similarity NPC50902
0.6489 Remote Similarity NPC477238
0.6484 Remote Similarity NPC296043
0.6483 Remote Similarity NPC262077
0.648 Remote Similarity NPC122926
0.648 Remote Similarity NPC113012
0.6479 Remote Similarity NPC476259
0.6463 Remote Similarity NPC2501
0.6457 Remote Similarity NPC63191
0.6457 Remote Similarity NPC471202
0.6438 Remote Similarity NPC145113
0.6435 Remote Similarity NPC474576
0.6435 Remote Similarity NPC17143
0.6435 Remote Similarity NPC47230
0.6434 Remote Similarity NPC329216
0.6433 Remote Similarity NPC196091
0.6429 Remote Similarity NPC29501
0.6429 Remote Similarity NPC471053
0.6429 Remote Similarity NPC47857
0.6429 Remote Similarity NPC181510
0.6429 Remote Similarity NPC471052
0.6429 Remote Similarity NPC471051
0.6429 Remote Similarity NPC168758
0.6429 Remote Similarity NPC316984
0.6429 Remote Similarity NPC30911
0.6423 Remote Similarity NPC201128
0.6417 Remote Similarity NPC233932
0.6406 Remote Similarity NPC471645
0.6385 Remote Similarity NPC239357
0.6385 Remote Similarity NPC284656
0.6382 Remote Similarity NPC297145
0.6382 Remote Similarity NPC197743
0.6378 Remote Similarity NPC478024
0.6376 Remote Similarity NPC162104
0.6364 Remote Similarity NPC160688
0.6364 Remote Similarity NPC53858
0.6364 Remote Similarity NPC84128
0.6356 Remote Similarity NPC150041
0.6348 Remote Similarity NPC474593
0.6348 Remote Similarity NPC475801
0.6345 Remote Similarity NPC476978
0.6343 Remote Similarity NPC36254
0.6341 Remote Similarity NPC323720
0.6336 Remote Similarity NPC471261
0.6333 Remote Similarity NPC473341
0.6333 Remote Similarity NPC122590
0.6327 Remote Similarity NPC329761
0.6327 Remote Similarity NPC225648
0.6324 Remote Similarity NPC470651
0.6324 Remote Similarity NPC470655
0.6308 Remote Similarity NPC475642
0.6306 Remote Similarity NPC474312
0.6301 Remote Similarity NPC5620
0.6299 Remote Similarity NPC471527
0.6294 Remote Similarity NPC98424
0.6294 Remote Similarity NPC476133
0.6294 Remote Similarity NPC178662
0.6294 Remote Similarity NPC92784
0.6294 Remote Similarity NPC470884
0.629 Remote Similarity NPC475918
0.6286 Remote Similarity NPC471256
0.6281 Remote Similarity NPC474985
0.6276 Remote Similarity NPC139326
0.6276 Remote Similarity NPC161069
0.627 Remote Similarity NPC298484
0.6266 Remote Similarity NPC186617
0.6262 Remote Similarity NPC476324
0.6262 Remote Similarity NPC476130
0.6259 Remote Similarity NPC314358
0.625 Remote Similarity NPC476241
0.625 Remote Similarity NPC476260
0.625 Remote Similarity NPC476344
0.625 Remote Similarity NPC150967
0.625 Remote Similarity NPC275100
0.624 Remote Similarity NPC271562
0.6239 Remote Similarity NPC472264
0.6234 Remote Similarity NPC1390
0.6234 Remote Similarity NPC62104
0.6232 Remote Similarity NPC319766
0.6231 Remote Similarity NPC315652
0.6231 Remote Similarity NPC7905
0.6226 Remote Similarity NPC471568
0.6226 Remote Similarity NPC473693
0.6226 Remote Similarity NPC138435
0.6224 Remote Similarity NPC471264
0.6224 Remote Similarity NPC471265
0.6216 Remote Similarity NPC284456
0.6216 Remote Similarity NPC6902
0.6216 Remote Similarity NPC184473
0.6211 Remote Similarity NPC26108
0.6211 Remote Similarity NPC473354
0.6207 Remote Similarity NPC469426
0.6207 Remote Similarity NPC39290
0.6207 Remote Similarity NPC469427
0.6207 Remote Similarity NPC269398
0.6207 Remote Similarity NPC263493
0.6207 Remote Similarity NPC159369
0.6204 Remote Similarity NPC476179
0.6204 Remote Similarity NPC476125
0.6202 Remote Similarity NPC5485
0.6202 Remote Similarity NPC273814
0.62 Remote Similarity NPC475168
0.62 Remote Similarity NPC7817
0.6198 Remote Similarity NPC475440
0.619 Remote Similarity NPC316008
0.619 Remote Similarity NPC313867
0.6187 Remote Similarity NPC316401
0.6184 Remote Similarity NPC475342

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC472536 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
0.7 Intermediate Similarity NPD7746 Phase 1
0.7 Intermediate Similarity NPD7747 Phase 1
0.6885 Remote Similarity NPD6421 Discontinued
0.6794 Remote Similarity NPD8273 Phase 1
0.6642 Remote Similarity NPD8415 Approved
0.6594 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6565 Remote Similarity NPD7624 Clinical (unspecified phase)
0.6565 Remote Similarity NPD7623 Phase 3
0.6429 Remote Similarity NPD2204 Approved
0.6364 Remote Similarity NPD7739 Clinical (unspecified phase)
0.6303 Remote Similarity NPD4228 Discovery
0.6299 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6288 Remote Similarity NPD7299 Clinical (unspecified phase)
0.625 Remote Similarity NPD8384 Approved
0.6202 Remote Similarity NPD1376 Discontinued
0.6154 Remote Similarity NPD6095 Approved
0.6154 Remote Similarity NPD6094 Approved
0.6148 Remote Similarity NPD7642 Approved
0.6136 Remote Similarity NPD7641 Discontinued
0.6129 Remote Similarity NPD2259 Approved
0.6129 Remote Similarity NPD2258 Approved
0.6111 Remote Similarity NPD1452 Discontinued
0.6058 Remote Similarity NPD4816 Clinical (unspecified phase)
0.6058 Remote Similarity NPD8451 Approved
0.6039 Remote Similarity NPD8414 Discontinued
0.6016 Remote Similarity NPD6413 Approved
0.6014 Remote Similarity NPD6681 Discovery
0.6014 Remote Similarity NPD8448 Approved
0.6 Remote Similarity NPD8391 Approved
0.6 Remote Similarity NPD8392 Approved
0.6 Remote Similarity NPD8390 Approved
0.594 Remote Similarity NPD7505 Discontinued
0.5917 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5896 Remote Similarity NPD2099 Approved
0.5896 Remote Similarity NPD1773 Discontinued
0.589 Remote Similarity NPD8172 Phase 2
0.589 Remote Similarity NPD8173 Phase 2
0.5882 Remote Similarity NPD46 Approved
0.5882 Remote Similarity NPD7838 Discovery
0.5882 Remote Similarity NPD6698 Approved
0.5874 Remote Similarity NPD6919 Clinical (unspecified phase)
0.587 Remote Similarity NPD8341 Approved
0.587 Remote Similarity NPD8342 Approved
0.587 Remote Similarity NPD8299 Approved
0.587 Remote Similarity NPD8340 Approved
0.5862 Remote Similarity NPD7760 Phase 2
0.5862 Remote Similarity NPD7759 Phase 2
0.5854 Remote Similarity NPD8038 Phase 2
0.5827 Remote Similarity NPD2584 Suspended
0.5822 Remote Similarity NPD5767 Discontinued
0.5821 Remote Similarity NPD7500 Approved
0.5821 Remote Similarity NPD961 Discontinued
0.582 Remote Similarity NPD7841 Clinical (unspecified phase)
0.5809 Remote Similarity NPD2645 Approved
0.5802 Remote Similarity NPD7601 Clinical (unspecified phase)
0.5797 Remote Similarity NPD7830 Approved
0.5797 Remote Similarity NPD7829 Approved
0.5796 Remote Similarity NPD8417 Discontinued
0.5789 Remote Similarity NPD8323 Discontinued
0.5758 Remote Similarity NPD2090 Approved
0.575 Remote Similarity NPD4261 Phase 1
0.5746 Remote Similarity NPD869 Approved
0.5736 Remote Similarity NPD2147 Approved
0.5735 Remote Similarity NPD2495 Phase 3
0.5735 Remote Similarity NPD3159 Discontinued
0.5734 Remote Similarity NPD3626 Phase 3
0.5726 Remote Similarity NPD3723 Clinical (unspecified phase)
0.5725 Remote Similarity NPD1806 Approved
0.5725 Remote Similarity NPD1748 Approved
0.5705 Remote Similarity NPD6077 Discontinued
0.5704 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5672 Remote Similarity NPD2100 Approved
0.5659 Remote Similarity NPD4211 Phase 1
0.5646 Remote Similarity NPD8416 Discontinued
0.5625 Remote Similarity NPD1407 Approved
0.5625 Remote Similarity NPD6122 Discontinued
0.562 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5612 Remote Similarity NPD8080 Discontinued
0.5606 Remote Similarity NPD6420 Discontinued
0.5603 Remote Similarity NPD2148 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   11585931
ChEMBL   CHEMBL354961
ZINC  

Physicochemical Properties

Molecular Weight:  819.54
ALogP:  0.1561
MLogP:  4.54
XLogP:  4.355
# Rotatable Bonds:  26
Polar Surface Area:  198.94
# H-Bond Aceptor:  15
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  58

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs