Natural Product: NPC163606

Natural Product ID:  NPC163606
Common Name:   Manoalide 25-Acetate
IUPAC Name:   [(2R)-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2H-furan-2-yl] acetate
Synonyms:   Manoalide 25-Acetate
Molecular Formula:   C27H38O6
Standard InCHIKey:  IBDCHSSSHBQBDQ-RFUQPTSVSA-N
Standard InCHI:  InChI=1S/C27H38O6/c1-17(11-13-22-18(2)9-7-15-27(22,4)5)8-6-10-20-12-14-23(32-25(20)30)21-16-24(29)33-26(21)31-19(3)28/h8,12,16,23,25-26,30H,6-7,9-11,13-15H2,1-5H3/b17-8+/t23-,25-,26-/m1/s1
Canonical SMILES:  CC(=O)O[C@@H]1OC(=O)C=C1[C@H]1CC=C([C@@H](O1)O)CC/C=C(/CCC1=C(C)CCCC1(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
NPO33331 brachiaster sp. Species NA NA Thailand PMID[15497961]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 7000 nM 10.6019/CHEMBL1201861
NPT83 Cell Line MCF7 Homo sapiens IC50 = 260 nM 15104478
NPT165 Cell Line HeLa Homo sapiens IC50 = 1680 nM 15104478
NPT139 Cell Line HT-29 Homo sapiens IC50 = 760 nM 15104478
NPT91 Cell Line KB Homo sapiens IC50 = 630 nM 15104478

  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 NPC163606 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
0.9873 High Similarity NPC126518
0.962 High Similarity NPC323251
0.9136 High Similarity NPC471298
0.9114 High Similarity NPC474816
0.9114 High Similarity NPC209135
0.9024 High Similarity NPC471297
0.8987 High Similarity NPC473756
0.8987 High Similarity NPC262747
0.8941 High Similarity NPC474629
0.8902 High Similarity NPC324170
0.8864 High Similarity NPC104925
0.8864 High Similarity NPC298973
0.878 High Similarity NPC475944
0.869 High Similarity NPC471301
0.8652 High Similarity NPC469697
0.8621 High Similarity NPC470734
0.8588 High Similarity NPC474860
0.8588 High Similarity NPC471300
0.8571 High Similarity NPC474809
0.8506 High Similarity NPC472810
0.8506 High Similarity NPC472378
0.8506 High Similarity NPC472809
0.8481 Intermediate Similarity NPC476489
0.8481 Intermediate Similarity NPC16349
0.8481 Intermediate Similarity NPC476490
0.8481 Intermediate Similarity NPC222244
0.8471 Intermediate Similarity NPC31086
0.8471 Intermediate Similarity NPC471302
0.8471 Intermediate Similarity NPC474865
0.8462 Intermediate Similarity NPC162346
0.8353 Intermediate Similarity NPC42476
0.8333 Intermediate Similarity NPC472812
0.8235 Intermediate Similarity NPC471296
0.8222 Intermediate Similarity NPC472811
0.8161 Intermediate Similarity NPC42586
0.8161 Intermediate Similarity NPC473251
0.8068 Intermediate Similarity NPC211892
0.8046 Intermediate Similarity NPC470800
0.8043 Intermediate Similarity NPC470255
0.8022 Intermediate Similarity NPC141831
0.8022 Intermediate Similarity NPC477122
0.8021 Intermediate Similarity NPC201191
0.8 Intermediate Similarity NPC477716
0.8 Intermediate Similarity NPC477721
0.7979 Intermediate Similarity NPC477719
0.7979 Intermediate Similarity NPC477718
0.7955 Intermediate Similarity NPC329630
0.7955 Intermediate Similarity NPC472442
0.7931 Intermediate Similarity NPC311070
0.7931 Intermediate Similarity NPC472440
0.7931 Intermediate Similarity NPC472377
0.7917 Intermediate Similarity NPC477717
0.7912 Intermediate Similarity NPC281942
0.7912 Intermediate Similarity NPC232426
0.7912 Intermediate Similarity NPC469403
0.7912 Intermediate Similarity NPC78973
0.7895 Intermediate Similarity NPC474440
0.7882 Intermediate Similarity NPC471299
0.7849 Intermediate Similarity NPC474554
0.7789 Intermediate Similarity NPC475709
0.7789 Intermediate Similarity NPC98112
0.7766 Intermediate Similarity NPC472441
0.7742 Intermediate Similarity NPC242069
0.7717 Intermediate Similarity NPC477782
0.7717 Intermediate Similarity NPC202886
0.7708 Intermediate Similarity NPC473154
0.7684 Intermediate Similarity NPC17578
0.7684 Intermediate Similarity NPC165632
0.7684 Intermediate Similarity NPC240673
0.7667 Intermediate Similarity NPC131813
0.766 Intermediate Similarity NPC324078
0.7634 Intermediate Similarity NPC477783
0.7634 Intermediate Similarity NPC329842
0.7629 Intermediate Similarity NPC324841
0.7624 Intermediate Similarity NPC470024
0.7614 Intermediate Similarity NPC471218
0.7609 Intermediate Similarity NPC477748
0.7595 Intermediate Similarity NPC282760
0.7582 Intermediate Similarity NPC316138
0.7582 Intermediate Similarity NPC313658
0.7582 Intermediate Similarity NPC312561
0.7576 Intermediate Similarity NPC120009
0.7561 Intermediate Similarity NPC4299
0.7556 Intermediate Similarity NPC217394
0.7553 Intermediate Similarity NPC156553
0.7553 Intermediate Similarity NPC469939
0.7553 Intermediate Similarity NPC53555
0.7553 Intermediate Similarity NPC472196
0.7553 Intermediate Similarity NPC238090
0.7553 Intermediate Similarity NPC472195
0.7551 Intermediate Similarity NPC198992
0.7549 Intermediate Similarity NPC206618
0.7529 Intermediate Similarity NPC477202
0.7528 Intermediate Similarity NPC12283
0.7528 Intermediate Similarity NPC474193
0.7525 Intermediate Similarity NPC109376
0.7475 Intermediate Similarity NPC238397
0.7475 Intermediate Similarity NPC471363
0.7475 Intermediate Similarity NPC472815
0.7474 Intermediate Similarity NPC256368
0.7474 Intermediate Similarity NPC477722
0.7474 Intermediate Similarity NPC474555
0.7474 Intermediate Similarity NPC475572
0.7474 Intermediate Similarity NPC159698
0.7471 Intermediate Similarity NPC139712
0.7471 Intermediate Similarity NPC242767
0.747 Intermediate Similarity NPC257618
0.7451 Intermediate Similarity NPC38948
0.7451 Intermediate Similarity NPC224660
0.7449 Intermediate Similarity NPC477720
0.7447 Intermediate Similarity NPC477749
0.7444 Intermediate Similarity NPC186155
0.7444 Intermediate Similarity NPC78673
0.7444 Intermediate Similarity NPC160517
0.7442 Intermediate Similarity NPC477203
0.7439 Intermediate Similarity NPC101622
0.7439 Intermediate Similarity NPC151481
0.7426 Intermediate Similarity NPC172867
0.7426 Intermediate Similarity NPC153095
0.7426 Intermediate Similarity NPC82251
0.7426 Intermediate Similarity NPC239961
0.7419 Intermediate Similarity NPC251528
0.7419 Intermediate Similarity NPC293044
0.7404 Intermediate Similarity NPC17791
0.74 Intermediate Similarity NPC127933
0.74 Intermediate Similarity NPC134270
0.74 Intermediate Similarity NPC475889
0.74 Intermediate Similarity NPC45897
0.74 Intermediate Similarity NPC7613
0.74 Intermediate Similarity NPC7644
0.7396 Intermediate Similarity NPC276110
0.7396 Intermediate Similarity NPC476488
0.7396 Intermediate Similarity NPC476487
0.7391 Intermediate Similarity NPC199382
0.7374 Intermediate Similarity NPC471075
0.7368 Intermediate Similarity NPC115021
0.7368 Intermediate Similarity NPC152778
0.7368 Intermediate Similarity NPC162615
0.7368 Intermediate Similarity NPC205034
0.7363 Intermediate Similarity NPC471795
0.7363 Intermediate Similarity NPC471494
0.7363 Intermediate Similarity NPC35933
0.7356 Intermediate Similarity NPC326753
0.7349 Intermediate Similarity NPC469660
0.734 Intermediate Similarity NPC182136
0.734 Intermediate Similarity NPC470817
0.734 Intermediate Similarity NPC280149
0.734 Intermediate Similarity NPC221111
0.734 Intermediate Similarity NPC253186
0.7333 Intermediate Similarity NPC470025
0.7333 Intermediate Similarity NPC317460
0.7333 Intermediate Similarity NPC328074
0.7333 Intermediate Similarity NPC161045
0.7333 Intermediate Similarity NPC321272
0.7333 Intermediate Similarity NPC469
0.7333 Intermediate Similarity NPC44261
0.7327 Intermediate Similarity NPC470321
0.7327 Intermediate Similarity NPC201880
0.7327 Intermediate Similarity NPC264867
0.7327 Intermediate Similarity NPC473207
0.7327 Intermediate Similarity NPC81567
0.7326 Intermediate Similarity NPC27205
0.7326 Intermediate Similarity NPC469880
0.732 Intermediate Similarity NPC16967
0.732 Intermediate Similarity NPC143446
0.732 Intermediate Similarity NPC112654
0.7312 Intermediate Similarity NPC106051
0.7312 Intermediate Similarity NPC196407
0.7308 Intermediate Similarity NPC316708
0.73 Intermediate Similarity NPC121423
0.73 Intermediate Similarity NPC134077
0.7283 Intermediate Similarity NPC471219
0.7283 Intermediate Similarity NPC311163
0.7283 Intermediate Similarity NPC61527
0.7283 Intermediate Similarity NPC474062
0.7282 Intermediate Similarity NPC392
0.7282 Intermediate Similarity NPC177524
0.7282 Intermediate Similarity NPC219900
0.7273 Intermediate Similarity NPC228251
0.7273 Intermediate Similarity NPC161527
0.7273 Intermediate Similarity NPC474012
0.7273 Intermediate Similarity NPC20113
0.7273 Intermediate Similarity NPC321728
0.7273 Intermediate Similarity NPC477971
0.7273 Intermediate Similarity NPC477968
0.7273 Intermediate Similarity NPC227865
0.7273 Intermediate Similarity NPC477972
0.7273 Intermediate Similarity NPC476299
0.7273 Intermediate Similarity NPC219285
0.7273 Intermediate Similarity NPC472644
0.7273 Intermediate Similarity NPC38855
0.7264 Intermediate Similarity NPC470027
0.7263 Intermediate Similarity NPC177037
0.7263 Intermediate Similarity NPC72845
0.7263 Intermediate Similarity NPC472814
0.7263 Intermediate Similarity NPC179517
0.7263 Intermediate Similarity NPC165904
0.7262 Intermediate Similarity NPC316185
0.7262 Intermediate Similarity NPC472254
0.7255 Intermediate Similarity NPC252296

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC163606 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
0.9873 High Similarity NPD6400 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD6686 Approved
0.7 Intermediate Similarity NPD4225 Approved
0.6907 Remote Similarity NPD7637 Suspended
0.6832 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6829 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7640 Approved
0.6765 Remote Similarity NPD7639 Approved
0.6747 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7328 Approved
0.6696 Remote Similarity NPD7327 Approved
0.6667 Remote Similarity NPD8033 Approved
0.6667 Remote Similarity NPD7638 Approved
0.6667 Remote Similarity NPD7503 Approved
0.6667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7516 Approved
0.6633 Remote Similarity NPD5785 Approved
0.6633 Remote Similarity NPD46 Approved
0.6633 Remote Similarity NPD6698 Approved
0.6596 Remote Similarity NPD7154 Phase 3
0.6585 Remote Similarity NPD4191 Approved
0.6585 Remote Similarity NPD4194 Approved
0.6585 Remote Similarity NPD4192 Approved
0.6585 Remote Similarity NPD4193 Approved
0.6579 Remote Similarity NPD8294 Approved
0.6579 Remote Similarity NPD8377 Approved
0.6522 Remote Similarity NPD8378 Approved
0.6522 Remote Similarity NPD8379 Approved
0.6522 Remote Similarity NPD8335 Approved
0.6522 Remote Similarity NPD8380 Approved
0.6522 Remote Similarity NPD8296 Approved
0.65 Remote Similarity NPD5778 Approved
0.65 Remote Similarity NPD5779 Approved
0.6465 Remote Similarity NPD7838 Discovery
0.646 Remote Similarity NPD7115 Discovery
0.6452 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6452 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6444 Remote Similarity NPD8039 Approved
0.6444 Remote Similarity NPD8264 Approved
0.6421 Remote Similarity NPD6695 Phase 3
0.6413 Remote Similarity NPD5784 Clinical (unspecified phase)
0.64 Remote Similarity NPD6411 Approved
0.6389 Remote Similarity NPD6412 Phase 2
0.6381 Remote Similarity NPD5344 Discontinued
0.6364 Remote Similarity NPD6051 Approved
0.6354 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6306 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6304 Remote Similarity NPD5776 Phase 2
0.6304 Remote Similarity NPD6925 Approved
0.6303 Remote Similarity NPD7507 Approved
0.6289 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6277 Remote Similarity NPD4819 Approved
0.6277 Remote Similarity NPD4821 Approved
0.6277 Remote Similarity NPD4822 Approved
0.6277 Remote Similarity NPD4820 Approved
0.6277 Remote Similarity NPD7332 Phase 2
0.6277 Remote Similarity NPD7514 Phase 3
0.625 Remote Similarity NPD6083 Phase 2
0.625 Remote Similarity NPD6053 Discontinued
0.625 Remote Similarity NPD6084 Phase 2
0.625 Remote Similarity NPD5362 Discontinued
0.6239 Remote Similarity NPD8513 Phase 3
0.6237 Remote Similarity NPD7145 Approved
0.6237 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6237 Remote Similarity NPD4271 Approved
0.6237 Remote Similarity NPD4268 Approved
0.6214 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6211 Remote Similarity NPD6902 Approved
0.62 Remote Similarity NPD6101 Approved
0.62 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6399 Phase 3
0.617 Remote Similarity NPD6929 Approved
0.6168 Remote Similarity NPD7632 Discontinued
0.6162 Remote Similarity NPD7524 Approved
0.6162 Remote Similarity NPD7750 Discontinued
0.6154 Remote Similarity NPD7839 Suspended
0.6148 Remote Similarity NPD7319 Approved
0.6146 Remote Similarity NPD5209 Approved
0.6132 Remote Similarity NPD6648 Approved
0.6122 Remote Similarity NPD5363 Approved
0.6122 Remote Similarity NPD1694 Approved
0.6117 Remote Similarity NPD7748 Approved
0.6106 Remote Similarity NPD6882 Approved
0.6105 Remote Similarity NPD6931 Approved
0.6105 Remote Similarity NPD6930 Phase 2
0.6102 Remote Similarity NPD8515 Approved
0.6102 Remote Similarity NPD8516 Approved
0.6102 Remote Similarity NPD8517 Approved
0.6082 Remote Similarity NPD5332 Approved
0.6082 Remote Similarity NPD5331 Approved
0.6078 Remote Similarity NPD7515 Phase 2
0.6071 Remote Similarity NPD6371 Approved
0.6067 Remote Similarity NPD6922 Approved
0.6067 Remote Similarity NPD6923 Approved
0.6061 Remote Similarity NPD7146 Approved
0.6061 Remote Similarity NPD7521 Approved
0.6061 Remote Similarity NPD5330 Approved
0.6061 Remote Similarity NPD6409 Approved
0.6061 Remote Similarity NPD6684 Approved
0.6061 Remote Similarity NPD7334 Approved
0.6058 Remote Similarity NPD5695 Phase 3
0.6042 Remote Similarity NPD6898 Phase 1
0.6042 Remote Similarity NPD4790 Discontinued
0.6 Remote Similarity NPD7144 Approved
0.6 Remote Similarity NPD6675 Approved
0.6 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6 Remote Similarity NPD4250 Approved
0.6 Remote Similarity NPD7143 Approved
0.6 Remote Similarity NPD5739 Approved
0.6 Remote Similarity NPD7128 Approved
0.6 Remote Similarity NPD6402 Approved
0.6 Remote Similarity NPD4251 Approved
0.5982 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5979 Remote Similarity NPD4269 Approved
0.5979 Remote Similarity NPD4270 Approved
0.5978 Remote Similarity NPD6926 Approved
0.5978 Remote Similarity NPD6924 Approved
0.5976 Remote Similarity NPD4219 Approved
0.5957 Remote Similarity NPD6932 Approved
0.5943 Remote Similarity NPD7902 Approved
0.5941 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5941 Remote Similarity NPD6672 Approved
0.5941 Remote Similarity NPD5737 Approved
0.5941 Remote Similarity NPD6903 Approved
0.5938 Remote Similarity NPD4252 Approved
0.5934 Remote Similarity NPD7152 Approved
0.5934 Remote Similarity NPD7150 Approved
0.5934 Remote Similarity NPD7151 Approved
0.5922 Remote Similarity NPD7087 Discontinued
0.5922 Remote Similarity NPD7983 Approved
0.5914 Remote Similarity NPD7339 Approved
0.5914 Remote Similarity NPD6942 Approved
0.59 Remote Similarity NPD4249 Approved
0.59 Remote Similarity NPD5786 Approved
0.5893 Remote Similarity NPD7320 Approved
0.5893 Remote Similarity NPD6899 Approved
0.5893 Remote Similarity NPD6881 Approved
0.5888 Remote Similarity NPD5696 Approved
0.5882 Remote Similarity NPD689 Discontinued
0.5859 Remote Similarity NPD3665 Phase 1
0.5859 Remote Similarity NPD4786 Approved
0.5859 Remote Similarity NPD3666 Approved
0.5859 Remote Similarity NPD3133 Approved
0.5856 Remote Similarity NPD4211 Phase 1
0.5851 Remote Similarity NPD6933 Approved
0.5851 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5841 Remote Similarity NPD6372 Approved
0.5841 Remote Similarity NPD6373 Approved
0.5833 Remote Similarity NPD7645 Phase 2
0.5833 Remote Similarity NPD6683 Phase 2
0.5816 Remote Similarity NPD6435 Approved
0.5816 Remote Similarity NPD3667 Approved
0.5814 Remote Similarity NPD368 Approved
0.5804 Remote Similarity NPD5701 Approved
0.5804 Remote Similarity NPD5697 Approved
0.58 Remote Similarity NPD1696 Phase 3
0.58 Remote Similarity NPD6893 Approved
0.5789 Remote Similarity NPD6883 Approved
0.5789 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7290 Approved
0.5789 Remote Similarity NPD4756 Discovery
0.5789 Remote Similarity NPD7102 Approved
0.5776 Remote Similarity NPD8133 Approved
0.5769 Remote Similarity NPD5693 Phase 1
0.5763 Remote Similarity NPD7505 Discontinued
0.5743 Remote Similarity NPD3618 Phase 1
0.5743 Remote Similarity NPD5279 Phase 3
0.5739 Remote Similarity NPD6847 Approved
0.5739 Remote Similarity NPD6650 Approved
0.5739 Remote Similarity NPD6617 Approved
0.5739 Remote Similarity NPD8130 Phase 1
0.5739 Remote Similarity NPD6649 Approved
0.5739 Remote Similarity NPD6869 Approved
0.5738 Remote Similarity NPD7830 Approved
0.5738 Remote Similarity NPD7829 Approved
0.5738 Remote Similarity NPD8328 Phase 3
0.5728 Remote Similarity NPD4753 Phase 2
0.5728 Remote Similarity NPD5328 Approved
0.5726 Remote Similarity NPD8293 Discontinued
0.5714 Remote Similarity NPD6640 Phase 3
0.5714 Remote Similarity NPD5369 Approved
0.5702 Remote Similarity NPD6013 Approved
0.5702 Remote Similarity NPD6012 Approved
0.5702 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5702 Remote Similarity NPD6014 Approved
0.5699 Remote Similarity NPD4732 Discontinued
0.5698 Remote Similarity NPD4246 Clinical (unspecified phase)
0.569 Remote Similarity NPD8297 Approved
0.5686 Remote Similarity NPD4751 Clinical (unspecified phase)
0.568 Remote Similarity NPD7736 Approved
0.5673 Remote Similarity NPD7136 Phase 2
0.5664 Remote Similarity NPD7899 Clinical (unspecified phase)
0.566 Remote Similarity NPD7901 Clinical (unspecified phase)
0.566 Remote Similarity NPD7900 Approved
0.5656 Remote Similarity NPD6370 Approved
0.5619 Remote Similarity NPD6079 Approved
0.5619 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5614 Remote Similarity NPD6011 Approved
0.5612 Remote Similarity NPD5368 Approved
0.5612 Remote Similarity NPD7525 Registered

Structure

External Identifiers

PubChem CID   44575737
ChEMBL   CHEMBL490765
ZINC  

Physicochemical Properties

Molecular Weight:  458.27
ALogP:  2.9472
MLogP:  3.77
XLogP:  5.155
# Rotatable Bonds:  15
Polar Surface Area:  82.06
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  33

Download Data

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