Natural Product: NPC322526

Natural Product ID:  NPC322526
Common Name:   Militarinone C
IUPAC Name:   (3E)-5-[hydroxy-(4-hydroxyphenyl)methyl]-3-[(2E,4E,6E,8R,10R)-1-hydroxy-6,8,10-trimethyldodeca-2,4,6-trienylidene]pyrrolidine-2,4-dione
Synonyms:   Militarinone B
Molecular Formula:   C26H33NO5
Standard InCHIKey:  NKHVQSJVSMTQID-YNUTZCEOSA-N
Standard InCHI:  InChI=1S/C26H33NO5/c1-5-16(2)14-18(4)15-17(3)8-6-7-9-21(29)22-25(31)23(27-26(22)32)24(30)19-10-12-20(28)13-11-19/h6-13,15-16,18,23-24,28-30H,5,14H2,1-4H3,(H,27,32)/b8-6+,9-7+,17-15+,22-21+/t16-,18-,23?,24?/m1/s1
Canonical SMILES:  CC[C@H](C[C@H](/C=C(/C=C/C=C/C(=C/1C(=NC(C1=O)C(c1ccc(cc1)O)O)O)/O)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
NPO32803 paecilomyces militaris Species NA Eukaryota PMID[12662096]
NPO10809 Isaria farinosa Species Cordycipitaceae Eukaryota PMID[21158423]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT681 Cell Line PC-12 Rattus norvegicus Activity = 16.8 % 12662096

  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 NPC322526 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
0.9922 High Similarity NPC473055
0.9922 High Similarity NPC473052
0.9612 High Similarity NPC328070
0.9398 High Similarity NPC471201
0.8581 High Similarity NPC476194
0.8444 Intermediate Similarity NPC296712
0.8271 Intermediate Similarity NPC474862
0.8248 Intermediate Similarity NPC478147
0.8195 Intermediate Similarity NPC473050
0.8195 Intermediate Similarity NPC473051
0.8182 Intermediate Similarity NPC91953
0.8112 Intermediate Similarity NPC197921
0.8056 Intermediate Similarity NPC469360
0.8045 Intermediate Similarity NPC319950
0.7971 Intermediate Similarity NPC476353
0.7902 Intermediate Similarity NPC6570
0.7879 Intermediate Similarity NPC317254
0.7872 Intermediate Similarity NPC45191
0.7868 Intermediate Similarity NPC142577
0.7817 Intermediate Similarity NPC244866
0.7786 Intermediate Similarity NPC116057
0.7769 Intermediate Similarity NPC474149
0.7752 Intermediate Similarity NPC317305
0.7746 Intermediate Similarity NPC326966
0.7742 Intermediate Similarity NPC471203
0.7737 Intermediate Similarity NPC27581
0.773 Intermediate Similarity NPC325651
0.7721 Intermediate Similarity NPC190663
0.7669 Intermediate Similarity NPC285350
0.766 Intermediate Similarity NPC472413
0.7655 Intermediate Similarity NPC208725
0.7647 Intermediate Similarity NPC283760
0.7639 Intermediate Similarity NPC169766
0.7619 Intermediate Similarity NPC150712
0.7612 Intermediate Similarity NPC188010
0.7612 Intermediate Similarity NPC23402
0.7609 Intermediate Similarity NPC160493
0.7576 Intermediate Similarity NPC177576
0.7569 Intermediate Similarity NPC470392
0.7568 Intermediate Similarity NPC251439
0.7557 Intermediate Similarity NPC258056
0.7547 Intermediate Similarity NPC15506
0.7538 Intermediate Similarity NPC142297
0.7537 Intermediate Similarity NPC118202
0.7534 Intermediate Similarity NPC64205
0.7532 Intermediate Similarity NPC39431
0.75 Intermediate Similarity NPC307020
0.75 Intermediate Similarity NPC252544
0.75 Intermediate Similarity NPC321252
0.7484 Intermediate Similarity NPC244509
0.7483 Intermediate Similarity NPC16188
0.7468 Intermediate Similarity NPC156348
0.7466 Intermediate Similarity NPC473360
0.7464 Intermediate Similarity NPC80150
0.7462 Intermediate Similarity NPC231705
0.7451 Intermediate Similarity NPC473491
0.7438 Intermediate Similarity NPC71205
0.7426 Intermediate Similarity NPC106551
0.7426 Intermediate Similarity NPC281686
0.7426 Intermediate Similarity NPC188867
0.7417 Intermediate Similarity NPC81026
0.7417 Intermediate Similarity NPC473804
0.7415 Intermediate Similarity NPC6913
0.7394 Intermediate Similarity NPC29477
0.7372 Intermediate Similarity NPC38458
0.7372 Intermediate Similarity NPC311737
0.7368 Intermediate Similarity NPC119569
0.7362 Intermediate Similarity NPC328494
0.7357 Intermediate Similarity NPC268348
0.7355 Intermediate Similarity NPC262166
0.7351 Intermediate Similarity NPC266741
0.7346 Intermediate Similarity NPC101207
0.7343 Intermediate Similarity NPC305717
0.7342 Intermediate Similarity NPC244336
0.7338 Intermediate Similarity NPC478016
0.7338 Intermediate Similarity NPC478015
0.7338 Intermediate Similarity NPC478014
0.7324 Intermediate Similarity NPC62101
0.7324 Intermediate Similarity NPC95733
0.7324 Intermediate Similarity NPC472414
0.7319 Intermediate Similarity NPC249435
0.731 Intermediate Similarity NPC183722
0.7308 Intermediate Similarity NPC68967
0.7305 Intermediate Similarity NPC472415
0.7299 Intermediate Similarity NPC82963
0.7293 Intermediate Similarity NPC145638
0.7293 Intermediate Similarity NPC290566
0.729 Intermediate Similarity NPC233702
0.7273 Intermediate Similarity NPC132771
0.7273 Intermediate Similarity NPC476444
0.7266 Intermediate Similarity NPC239697
0.7261 Intermediate Similarity NPC476268
0.7248 Intermediate Similarity NPC313694
0.7248 Intermediate Similarity NPC242159
0.7244 Intermediate Similarity NPC202198
0.7231 Intermediate Similarity NPC178902
0.7226 Intermediate Similarity NPC213
0.7226 Intermediate Similarity NPC10286
0.7226 Intermediate Similarity NPC324081
0.7218 Intermediate Similarity NPC24101
0.7218 Intermediate Similarity NPC153690
0.7218 Intermediate Similarity NPC96224
0.7205 Intermediate Similarity NPC67080
0.7203 Intermediate Similarity NPC474803
0.7197 Intermediate Similarity NPC70843
0.7195 Intermediate Similarity NPC314693
0.7192 Intermediate Similarity NPC120251
0.7185 Intermediate Similarity NPC114682
0.7183 Intermediate Similarity NPC86900
0.7183 Intermediate Similarity NPC469927
0.7181 Intermediate Similarity NPC109580
0.7178 Intermediate Similarity NPC209463
0.7172 Intermediate Similarity NPC71271
0.717 Intermediate Similarity NPC56635
0.7169 Intermediate Similarity NPC26108
0.7169 Intermediate Similarity NPC136797
0.7164 Intermediate Similarity NPC88141
0.7163 Intermediate Similarity NPC56634
0.7162 Intermediate Similarity NPC477680
0.716 Intermediate Similarity NPC63931
0.7152 Intermediate Similarity NPC256689
0.7152 Intermediate Similarity NPC476989
0.7152 Intermediate Similarity NPC123011
0.7143 Intermediate Similarity NPC182240
0.7143 Intermediate Similarity NPC257390
0.7143 Intermediate Similarity NPC42423
0.7134 Intermediate Similarity NPC56685
0.7133 Intermediate Similarity NPC211218
0.7133 Intermediate Similarity NPC236795
0.7126 Intermediate Similarity NPC211713
0.7126 Intermediate Similarity NPC88378
0.7123 Intermediate Similarity NPC469930
0.7114 Intermediate Similarity NPC279045
0.7114 Intermediate Similarity NPC113325
0.7108 Intermediate Similarity NPC306804
0.7108 Intermediate Similarity NPC163924
0.7108 Intermediate Similarity NPC12890
0.7108 Intermediate Similarity NPC137627
0.7108 Intermediate Similarity NPC54661
0.7105 Intermediate Similarity NPC33011
0.7105 Intermediate Similarity NPC168861
0.7097 Intermediate Similarity NPC313414
0.7095 Intermediate Similarity NPC475042
0.7092 Intermediate Similarity NPC34634
0.7092 Intermediate Similarity NPC265454
0.709 Intermediate Similarity NPC31274
0.7086 Intermediate Similarity NPC471316
0.7083 Intermediate Similarity NPC171372
0.7083 Intermediate Similarity NPC4974
0.708 Intermediate Similarity NPC309808
0.7073 Intermediate Similarity NPC294516
0.7073 Intermediate Similarity NPC107938
0.7071 Intermediate Similarity NPC142638
0.7071 Intermediate Similarity NPC317784
0.7071 Intermediate Similarity NPC5932
0.7071 Intermediate Similarity NPC310467
0.7068 Intermediate Similarity NPC95178
0.7068 Intermediate Similarity NPC69332
0.7068 Intermediate Similarity NPC29989
0.7068 Intermediate Similarity NPC188677
0.7067 Intermediate Similarity NPC175870
0.7066 Intermediate Similarity NPC159767
0.7066 Intermediate Similarity NPC155506
0.7066 Intermediate Similarity NPC95412
0.7066 Intermediate Similarity NPC279871
0.7066 Intermediate Similarity NPC476227
0.7063 Intermediate Similarity NPC207675
0.7063 Intermediate Similarity NPC212699
0.7054 Intermediate Similarity NPC260000
0.7051 Intermediate Similarity NPC146097
0.7051 Intermediate Similarity NPC227905
0.7051 Intermediate Similarity NPC339338
0.705 Intermediate Similarity NPC28951
0.705 Intermediate Similarity NPC325646
0.7048 Intermediate Similarity NPC89831
0.7047 Intermediate Similarity NPC228511
0.7045 Intermediate Similarity NPC8931
0.7045 Intermediate Similarity NPC261573
0.7045 Intermediate Similarity NPC120693
0.7042 Intermediate Similarity NPC86966
0.7042 Intermediate Similarity NPC149246
0.7042 Intermediate Similarity NPC98305
0.7042 Intermediate Similarity NPC326079
0.7041 Intermediate Similarity NPC475421
0.7041 Intermediate Similarity NPC194671
0.7041 Intermediate Similarity NPC269750
0.7037 Intermediate Similarity NPC95172
0.7034 Intermediate Similarity NPC127975
0.703 Intermediate Similarity NPC280022
0.7025 Intermediate Similarity NPC5194
0.7025 Intermediate Similarity NPC261934
0.7024 Intermediate Similarity NPC477115
0.7021 Intermediate Similarity NPC473767
0.7021 Intermediate Similarity NPC43275
0.7015 Intermediate Similarity NPC228737
0.7014 Intermediate Similarity NPC472029
0.7014 Intermediate Similarity NPC236981
0.7014 Intermediate Similarity NPC65761
0.7007 Intermediate Similarity NPC17693
0.7006 Intermediate Similarity NPC476743

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC322526 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
0.8058 Intermediate Similarity NPD3136 Phase 2
0.7891 Intermediate Similarity NPD3400 Discontinued
0.7817 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD7978 Discontinued
0.75 Intermediate Similarity NPD4659 Approved
0.75 Intermediate Similarity NPD7450 Phase 2
0.7445 Intermediate Similarity NPD1759 Phase 1
0.7426 Intermediate Similarity NPD9568 Approved
0.7389 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6682 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD9570 Approved
0.7372 Intermediate Similarity NPD1758 Phase 1
0.7372 Intermediate Similarity NPD317 Approved
0.7372 Intermediate Similarity NPD318 Approved
0.7353 Intermediate Similarity NPD256 Approved
0.7353 Intermediate Similarity NPD255 Approved
0.7305 Intermediate Similarity NPD2562 Approved
0.7305 Intermediate Similarity NPD2561 Approved
0.7296 Intermediate Similarity NPD7972 Discontinued
0.7293 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6390 Discontinued
0.7285 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4103 Phase 2
0.7273 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD3552 Approved
0.7248 Intermediate Similarity NPD3555 Approved
0.7248 Intermediate Similarity NPD3553 Approved
0.7248 Intermediate Similarity NPD3554 Approved
0.7246 Intermediate Similarity NPD856 Approved
0.7246 Intermediate Similarity NPD16 Approved
0.7214 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7131 Phase 3
0.7134 Intermediate Similarity NPD7523 Phase 3
0.7133 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD7495 Discontinued
0.7103 Intermediate Similarity NPD7451 Discontinued
0.7083 Intermediate Similarity NPD6325 Discontinued
0.7076 Intermediate Similarity NPD5035 Approved
0.7063 Intermediate Similarity NPD5108 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD3123 Discovery
0.7034 Intermediate Similarity NPD1129 Approved
0.7034 Intermediate Similarity NPD1133 Approved
0.7034 Intermediate Similarity NPD1135 Approved
0.7034 Intermediate Similarity NPD1134 Approved
0.7034 Intermediate Similarity NPD1131 Approved
0.7 Intermediate Similarity NPD555 Phase 2
0.698 Remote Similarity NPD259 Phase 1
0.6957 Remote Similarity NPD2228 Approved
0.6957 Remote Similarity NPD2234 Approved
0.6957 Remote Similarity NPD2229 Approved
0.6939 Remote Similarity NPD9569 Approved
0.6933 Remote Similarity NPD825 Approved
0.6933 Remote Similarity NPD826 Approved
0.6923 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6919 Remote Similarity NPD5026 Approved
0.6919 Remote Similarity NPD5034 Approved
0.6919 Remote Similarity NPD4955 Approved
0.6919 Remote Similarity NPD36 Approved
0.6919 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6919 Remote Similarity NPD5028 Approved
0.6919 Remote Similarity NPD4954 Approved
0.6917 Remote Similarity NPD9610 Approved
0.6917 Remote Similarity NPD9608 Approved
0.6914 Remote Similarity NPD8019 Approved
0.6906 Remote Similarity NPD9618 Approved
0.6906 Remote Similarity NPD9614 Approved
0.6897 Remote Similarity NPD5157 Phase 1
0.6897 Remote Similarity NPD9622 Approved
0.6897 Remote Similarity NPD5159 Phase 2
0.6897 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6871 Remote Similarity NPD257 Approved
0.6871 Remote Similarity NPD258 Approved
0.6867 Remote Similarity NPD6405 Approved
0.6867 Remote Similarity NPD6407 Approved
0.686 Remote Similarity NPD5030 Phase 2
0.6857 Remote Similarity NPD5038 Approved
0.6857 Remote Similarity NPD5037 Approved
0.6849 Remote Similarity NPD196 Phase 1
0.6842 Remote Similarity NPD2568 Approved
0.6832 Remote Similarity NPD3455 Phase 2
0.6821 Remote Similarity NPD6346 Approved
0.6821 Remote Similarity NPD468 Phase 1
0.6818 Remote Similarity NPD2161 Phase 2
0.6806 Remote Similarity NPD3421 Phase 3
0.6802 Remote Similarity NPD3823 Discontinued
0.68 Remote Similarity NPD597 Approved
0.68 Remote Similarity NPD5036 Approved
0.68 Remote Similarity NPD601 Approved
0.68 Remote Similarity NPD598 Approved
0.6786 Remote Similarity NPD7315 Approved
0.6781 Remote Similarity NPD3685 Discontinued
0.6781 Remote Similarity NPD1755 Approved
0.6766 Remote Similarity NPD6746 Phase 2
0.6759 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6759 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6755 Remote Similarity NPD1136 Approved
0.6755 Remote Similarity NPD1132 Approved
0.6755 Remote Similarity NPD1130 Approved
0.6748 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6746 Remote Similarity NPD5137 Approved
0.6744 Remote Similarity NPD5557 Phase 1
0.6739 Remote Similarity NPD3642 Approved
0.6739 Remote Similarity NPD3643 Approved
0.6739 Remote Similarity NPD3644 Approved
0.6736 Remote Similarity NPD9381 Approved
0.6736 Remote Similarity NPD9384 Approved
0.6733 Remote Similarity NPD9536 Phase 1
0.6733 Remote Similarity NPD4738 Phase 2
0.6733 Remote Similarity NPD9537 Phase 1
0.6732 Remote Similarity NPD3052 Approved
0.6732 Remote Similarity NPD3054 Approved
0.6732 Remote Similarity NPD8173 Phase 2
0.6732 Remote Similarity NPD8172 Phase 2
0.6725 Remote Similarity NPD3909 Discontinued
0.6724 Remote Similarity NPD5032 Approved
0.6713 Remote Similarity NPD2217 Approved
0.6713 Remote Similarity NPD5303 Approved
0.6713 Remote Similarity NPD2218 Phase 2
0.6713 Remote Similarity NPD5304 Approved
0.6709 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6691 Remote Similarity NPD1444 Approved
0.6691 Remote Similarity NPD1445 Approved
0.6688 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6687 Remote Similarity NPD6502 Phase 2
0.6686 Remote Similarity NPD7608 Discontinued
0.6685 Remote Similarity NPD6836 Approved
0.6667 Remote Similarity NPD7811 Phase 3
0.6667 Remote Similarity NPD5031 Approved
0.6667 Remote Similarity NPD2613 Approved
0.6667 Remote Similarity NPD5029 Approved
0.6667 Remote Similarity NPD7810 Phase 3
0.6667 Remote Similarity NPD5027 Approved
0.6667 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6645 Remote Similarity NPD829 Discontinued
0.6644 Remote Similarity NPD9621 Approved
0.6644 Remote Similarity NPD9620 Approved
0.6644 Remote Similarity NPD9619 Approved
0.6644 Remote Similarity NPD602 Approved
0.6644 Remote Similarity NPD599 Approved
0.6643 Remote Similarity NPD9616 Approved
0.6643 Remote Similarity NPD9613 Approved
0.6643 Remote Similarity NPD9615 Approved
0.6642 Remote Similarity NPD855 Approved
0.6642 Remote Similarity NPD854 Approved
0.6627 Remote Similarity NPD7318 Phase 3
0.6627 Remote Similarity NPD3286 Discontinued
0.6625 Remote Similarity NPD4357 Discontinued
0.6623 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6623 Remote Similarity NPD823 Approved
0.6623 Remote Similarity NPD5314 Approved
0.6623 Remote Similarity NPD817 Approved
0.6621 Remote Similarity NPD3019 Approved
0.6621 Remote Similarity NPD2932 Approved
0.6611 Remote Similarity NPD5968 Phase 3
0.6607 Remote Similarity NPD8303 Discontinued
0.6603 Remote Similarity NPD2239 Approved
0.6603 Remote Similarity NPD2240 Approved
0.6601 Remote Similarity NPD3061 Approved
0.6601 Remote Similarity NPD3059 Approved
0.6601 Remote Similarity NPD3062 Approved
0.66 Remote Similarity NPD4208 Discontinued
0.6599 Remote Similarity NPD6624 Discontinued
0.6597 Remote Similarity NPD316 Approved
0.6597 Remote Similarity NPD9545 Approved
0.6584 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6584 Remote Similarity NPD3536 Discontinued
0.6582 Remote Similarity NPD2654 Approved
0.6575 Remote Similarity NPD3143 Discontinued
0.6568 Remote Similarity NPD7133 Discontinued
0.6566 Remote Similarity NPD5773 Approved
0.6566 Remote Similarity NPD5772 Approved
0.6562 Remote Similarity NPD6667 Approved
0.6562 Remote Similarity NPD3300 Phase 2
0.6562 Remote Similarity NPD6666 Approved
0.6558 Remote Similarity NPD274 Approved
0.6558 Remote Similarity NPD7113 Clinical (unspecified phase)
0.6558 Remote Similarity NPD275 Approved
0.6556 Remote Similarity NPD4207 Discontinued
0.6552 Remote Similarity NPD4956 Approved
0.6552 Remote Similarity NPD4093 Discontinued
0.6552 Remote Similarity NPD5981 Approved
0.6552 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6547 Remote Similarity NPD1792 Phase 2
0.6543 Remote Similarity NPD7526 Approved
0.6543 Remote Similarity NPD7303 Discontinued
0.6543 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6543 Remote Similarity NPD52 Approved
0.6541 Remote Similarity NPD9609 Approved
0.6541 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6541 Remote Similarity NPD9611 Approved
0.6541 Remote Similarity NPD9612 Approved
0.6541 Remote Similarity NPD2575 Approved
0.6536 Remote Similarity NPD3090 Approved
0.6536 Remote Similarity NPD3087 Approved
0.6536 Remote Similarity NPD3089 Approved
0.6536 Remote Similarity NPD3616 Approved
0.6536 Remote Similarity NPD2574 Discontinued

Structure

External Identifiers

PubChem CID   54691340
ChEMBL   CHEMBL478579
ZINC  

Physicochemical Properties

Molecular Weight:  439.24
ALogP:  0.1779
MLogP:  3.66
XLogP:  7.147
# Rotatable Bonds:  17
Polar Surface Area:  110.35
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  32

Download Data

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Biological Activities  
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