Natural Product: NPC156553

Natural Product ID:  NPC156553
Common Name:   Massarinolin A
IUPAC Name:  
Synonyms:  
Molecular Formula:   C15H18O4
Standard InCHIKey:  WSCZAOPWNOYKPC-RCZQDCHWSA-N
Standard InCHI:  InChI=1S/C15H18O4/c1-8-3-4-10-5-11(8)14(10)7-18-15(13(14)17)6-9(2)12(16)19-15/h6,10-11,13,17H,1,3-5,7H2,2H3/t10-,11-,13-,14+,15-/m0/s1
Canonical SMILES:  C=C1CC[C@H]2C[C@@H]1[C@]12CO[C@]2([C@H]1O)OC(=O)C(=C2)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
NPO32853 massarina tunicata Species Massarinaceae Eukaryota PMID[10096869]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 10 mm DrugMatrix in vitro pharmacology data
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 17 mm 17665951

  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 NPC156553 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
0.8119 Intermediate Similarity NPC239961
0.8081 Intermediate Similarity NPC198992
0.8065 Intermediate Similarity NPC472378
0.7957 Intermediate Similarity NPC473891
0.7917 Intermediate Similarity NPC53555
0.7885 Intermediate Similarity NPC206618
0.7879 Intermediate Similarity NPC159763
0.7879 Intermediate Similarity NPC278386
0.7879 Intermediate Similarity NPC473154
0.7879 Intermediate Similarity NPC124512
0.7879 Intermediate Similarity NPC474440
0.7872 Intermediate Similarity NPC472809
0.7872 Intermediate Similarity NPC472810
0.7857 Intermediate Similarity NPC165632
0.7835 Intermediate Similarity NPC256368
0.7822 Intermediate Similarity NPC472815
0.7822 Intermediate Similarity NPC121423
0.7812 Intermediate Similarity NPC141831
0.7812 Intermediate Similarity NPC72845
0.7789 Intermediate Similarity NPC79027
0.7789 Intermediate Similarity NPC470734
0.7788 Intermediate Similarity NPC219900
0.7788 Intermediate Similarity NPC38948
0.7788 Intermediate Similarity NPC392
0.7788 Intermediate Similarity NPC177524
0.7778 Intermediate Similarity NPC205143
0.7778 Intermediate Similarity NPC73911
0.7767 Intermediate Similarity NPC85670
0.7767 Intermediate Similarity NPC82251
0.7742 Intermediate Similarity NPC471795
0.7732 Intermediate Similarity NPC472196
0.7732 Intermediate Similarity NPC472195
0.7732 Intermediate Similarity NPC472812
0.7732 Intermediate Similarity NPC162615
0.7732 Intermediate Similarity NPC152778
0.7732 Intermediate Similarity NPC205034
0.7732 Intermediate Similarity NPC238090
0.7717 Intermediate Similarity NPC472377
0.7717 Intermediate Similarity NPC311070
0.7714 Intermediate Similarity NPC257853
0.7708 Intermediate Similarity NPC281942
0.7708 Intermediate Similarity NPC232426
0.7692 Intermediate Similarity NPC475944
0.7684 Intermediate Similarity NPC474629
0.7677 Intermediate Similarity NPC473153
0.766 Intermediate Similarity NPC131813
0.7653 Intermediate Similarity NPC470521
0.7653 Intermediate Similarity NPC469697
0.7653 Intermediate Similarity NPC104925
0.7653 Intermediate Similarity NPC298973
0.7653 Intermediate Similarity NPC159698
0.7647 Intermediate Similarity NPC201191
0.7634 Intermediate Similarity NPC471302
0.7629 Intermediate Similarity NPC472811
0.7629 Intermediate Similarity NPC473675
0.7624 Intermediate Similarity NPC38855
0.7619 Intermediate Similarity NPC181994
0.7609 Intermediate Similarity NPC471298
0.7609 Intermediate Similarity NPC323251
0.7604 Intermediate Similarity NPC474396
0.7604 Intermediate Similarity NPC133450
0.7604 Intermediate Similarity NPC50488
0.76 Intermediate Similarity NPC475709
0.7593 Intermediate Similarity NPC264153
0.7579 Intermediate Similarity NPC476600
0.7573 Intermediate Similarity NPC281378
0.7573 Intermediate Similarity NPC120009
0.7556 Intermediate Similarity NPC184737
0.7556 Intermediate Similarity NPC474816
0.7556 Intermediate Similarity NPC209135
0.7553 Intermediate Similarity NPC217394
0.7553 Intermediate Similarity NPC163606
0.7551 Intermediate Similarity NPC475098
0.7551 Intermediate Similarity NPC139692
0.7551 Intermediate Similarity NPC59646
0.7551 Intermediate Similarity NPC166346
0.7551 Intermediate Similarity NPC471483
0.7551 Intermediate Similarity NPC189651
0.7527 Intermediate Similarity NPC471297
0.7527 Intermediate Similarity NPC49208
0.7527 Intermediate Similarity NPC23748
0.7527 Intermediate Similarity NPC474809
0.7527 Intermediate Similarity NPC42476
0.7526 Intermediate Similarity NPC177668
0.7526 Intermediate Similarity NPC182136
0.7526 Intermediate Similarity NPC472642
0.7526 Intermediate Similarity NPC78973
0.7526 Intermediate Similarity NPC310479
0.7525 Intermediate Similarity NPC187268
0.7525 Intermediate Similarity NPC241657
0.7525 Intermediate Similarity NPC222303
0.7525 Intermediate Similarity NPC471610
0.75 Intermediate Similarity NPC471937
0.75 Intermediate Similarity NPC328074
0.75 Intermediate Similarity NPC296950
0.75 Intermediate Similarity NPC321272
0.75 Intermediate Similarity NPC162346
0.75 Intermediate Similarity NPC16967
0.75 Intermediate Similarity NPC317460
0.75 Intermediate Similarity NPC470025
0.75 Intermediate Similarity NPC161775
0.7477 Intermediate Similarity NPC316708
0.7477 Intermediate Similarity NPC177047
0.7477 Intermediate Similarity NPC235014
0.7476 Intermediate Similarity NPC472552
0.7476 Intermediate Similarity NPC58329
0.7475 Intermediate Similarity NPC470255
0.7475 Intermediate Similarity NPC57117
0.7475 Intermediate Similarity NPC191521
0.7474 Intermediate Similarity NPC311163
0.7453 Intermediate Similarity NPC128795
0.7453 Intermediate Similarity NPC135015
0.7453 Intermediate Similarity NPC48548
0.7453 Intermediate Similarity NPC217921
0.7451 Intermediate Similarity NPC472644
0.7449 Intermediate Similarity NPC303697
0.7449 Intermediate Similarity NPC472814
0.7449 Intermediate Similarity NPC177037
0.7449 Intermediate Similarity NPC470520
0.7449 Intermediate Similarity NPC175842
0.7449 Intermediate Similarity NPC477749
0.7449 Intermediate Similarity NPC32494
0.7449 Intermediate Similarity NPC477783
0.7447 Intermediate Similarity NPC126518
0.7447 Intermediate Similarity NPC474865
0.7444 Intermediate Similarity NPC262747
0.7431 Intermediate Similarity NPC470027
0.7429 Intermediate Similarity NPC477125
0.7429 Intermediate Similarity NPC218158
0.7426 Intermediate Similarity NPC471490
0.7423 Intermediate Similarity NPC168131
0.7423 Intermediate Similarity NPC225283
0.7423 Intermediate Similarity NPC174342
0.7423 Intermediate Similarity NPC5509
0.7419 Intermediate Similarity NPC11383
0.7419 Intermediate Similarity NPC474959
0.7419 Intermediate Similarity NPC475046
0.7419 Intermediate Similarity NPC310450
0.7407 Intermediate Similarity NPC470026
0.7407 Intermediate Similarity NPC17791
0.7404 Intermediate Similarity NPC472750
0.7404 Intermediate Similarity NPC471938
0.7404 Intermediate Similarity NPC472747
0.74 Intermediate Similarity NPC286612
0.74 Intermediate Similarity NPC220221
0.74 Intermediate Similarity NPC183012
0.74 Intermediate Similarity NPC275310
0.74 Intermediate Similarity NPC13924
0.74 Intermediate Similarity NPC230347
0.74 Intermediate Similarity NPC276110
0.7396 Intermediate Similarity NPC312561
0.7396 Intermediate Similarity NPC471796
0.7391 Intermediate Similarity NPC10636
0.7383 Intermediate Similarity NPC316974
0.7383 Intermediate Similarity NPC40728
0.7379 Intermediate Similarity NPC303559
0.7379 Intermediate Similarity NPC472554
0.7374 Intermediate Similarity NPC472954
0.7374 Intermediate Similarity NPC472640
0.7374 Intermediate Similarity NPC472641
0.7374 Intermediate Similarity NPC110022
0.7374 Intermediate Similarity NPC115021
0.7368 Intermediate Similarity NPC86316
0.7368 Intermediate Similarity NPC473251
0.7368 Intermediate Similarity NPC106416
0.7368 Intermediate Similarity NPC471494
0.7368 Intermediate Similarity NPC11804
0.7368 Intermediate Similarity NPC65661
0.7368 Intermediate Similarity NPC30984
0.7368 Intermediate Similarity NPC42586
0.7358 Intermediate Similarity NPC88013
0.7358 Intermediate Similarity NPC125423
0.7358 Intermediate Similarity NPC187435
0.7358 Intermediate Similarity NPC472820
0.7358 Intermediate Similarity NPC67321
0.7358 Intermediate Similarity NPC109376
0.7353 Intermediate Similarity NPC203627
0.7353 Intermediate Similarity NPC473326
0.7353 Intermediate Similarity NPC475068
0.7347 Intermediate Similarity NPC280149
0.7347 Intermediate Similarity NPC3436
0.7347 Intermediate Similarity NPC202886
0.7347 Intermediate Similarity NPC469368
0.7347 Intermediate Similarity NPC473448
0.7347 Intermediate Similarity NPC221111
0.7347 Intermediate Similarity NPC469403
0.7347 Intermediate Similarity NPC51486
0.7347 Intermediate Similarity NPC118078
0.7347 Intermediate Similarity NPC477782
0.734 Intermediate Similarity NPC161045
0.734 Intermediate Similarity NPC44261
0.734 Intermediate Similarity NPC321385
0.734 Intermediate Similarity NPC229799
0.734 Intermediate Similarity NPC474193
0.734 Intermediate Similarity NPC284472
0.734 Intermediate Similarity NPC286770
0.734 Intermediate Similarity NPC12283
0.7333 Intermediate Similarity NPC472748
0.7333 Intermediate Similarity NPC146731
0.7333 Intermediate Similarity NPC203659

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC156553 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
0.7879 Intermediate Similarity NPD4225 Approved
0.7788 Intermediate Similarity NPD6686 Approved
0.7447 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD46 Approved
0.7172 Intermediate Similarity NPD7838 Discovery
0.7172 Intermediate Similarity NPD6698 Approved
0.7053 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5344 Discontinued
0.7019 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD7328 Approved
0.7018 Intermediate Similarity NPD7327 Approved
0.6983 Remote Similarity NPD8033 Approved
0.6957 Remote Similarity NPD7516 Approved
0.6897 Remote Similarity NPD8377 Approved
0.6897 Remote Similarity NPD8294 Approved
0.6838 Remote Similarity NPD8296 Approved
0.6838 Remote Similarity NPD8335 Approved
0.6838 Remote Similarity NPD8378 Approved
0.6838 Remote Similarity NPD8380 Approved
0.6838 Remote Similarity NPD8379 Approved
0.675 Remote Similarity NPD7507 Approved
0.6727 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6698 Remote Similarity NPD7638 Approved
0.6696 Remote Similarity NPD6371 Approved
0.6695 Remote Similarity NPD7503 Approved
0.6667 Remote Similarity NPD1694 Approved
0.6667 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5785 Approved
0.6638 Remote Similarity NPD7115 Discovery
0.6636 Remote Similarity NPD7640 Approved
0.6636 Remote Similarity NPD6648 Approved
0.6636 Remote Similarity NPD7639 Approved
0.6607 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6602 Remote Similarity NPD7637 Suspended
0.6585 Remote Similarity NPD7319 Approved
0.6577 Remote Similarity NPD6412 Phase 2
0.6495 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6491 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6436 Remote Similarity NPD4249 Approved
0.6373 Remote Similarity NPD4250 Approved
0.6373 Remote Similarity NPD4251 Approved
0.6373 Remote Similarity NPD7524 Approved
0.6364 Remote Similarity NPD5209 Approved
0.6355 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6337 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6327 Remote Similarity NPD4820 Approved
0.6327 Remote Similarity NPD4819 Approved
0.6327 Remote Similarity NPD4821 Approved
0.6327 Remote Similarity NPD4822 Approved
0.63 Remote Similarity NPD5362 Discontinued
0.63 Remote Similarity NPD7154 Phase 3
0.6293 Remote Similarity NPD6882 Approved
0.6289 Remote Similarity NPD4271 Approved
0.6289 Remote Similarity NPD4268 Approved
0.6286 Remote Similarity NPD7983 Approved
0.6261 Remote Similarity NPD5955 Clinical (unspecified phase)
0.626 Remote Similarity NPD7492 Approved
0.625 Remote Similarity NPD1695 Approved
0.6238 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6226 Remote Similarity NPD6399 Phase 3
0.6222 Remote Similarity NPD2685 Clinical (unspecified phase)
0.621 Remote Similarity NPD6616 Approved
0.6198 Remote Similarity NPD6054 Approved
0.6176 Remote Similarity NPD5363 Approved
0.6168 Remote Similarity NPD5282 Discontinued
0.616 Remote Similarity NPD7078 Approved
0.6154 Remote Similarity NPD8297 Approved
0.6154 Remote Similarity NPD6053 Discontinued
0.6154 Remote Similarity NPD969 Suspended
0.6148 Remote Similarity NPD8517 Approved
0.6148 Remote Similarity NPD6016 Approved
0.6148 Remote Similarity NPD6015 Approved
0.6148 Remote Similarity NPD8515 Approved
0.6148 Remote Similarity NPD8513 Phase 3
0.6148 Remote Similarity NPD8516 Approved
0.6147 Remote Similarity NPD6084 Phase 2
0.6147 Remote Similarity NPD6083 Phase 2
0.614 Remote Similarity NPD5697 Approved
0.6139 Remote Similarity NPD6695 Phase 3
0.6139 Remote Similarity NPD5331 Approved
0.6139 Remote Similarity NPD5332 Approved
0.6132 Remote Similarity NPD6411 Approved
0.6122 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6111 Remote Similarity NPD7736 Approved
0.6111 Remote Similarity NPD5695 Phase 3
0.6102 Remote Similarity NPD8133 Approved
0.61 Remote Similarity NPD4790 Discontinued
0.6098 Remote Similarity NPD5988 Approved
0.6098 Remote Similarity NPD6370 Approved
0.6095 Remote Similarity NPD6051 Approved
0.6087 Remote Similarity NPD6881 Approved
0.6087 Remote Similarity NPD7320 Approved
0.6087 Remote Similarity NPD6899 Approved
0.6083 Remote Similarity NPD6009 Approved
0.6083 Remote Similarity NPD7505 Discontinued
0.6082 Remote Similarity NPD6933 Approved
0.6075 Remote Similarity NPD5779 Approved
0.6075 Remote Similarity NPD5778 Approved
0.6071 Remote Similarity NPD7632 Discontinued
0.6066 Remote Similarity NPD6059 Approved
0.6053 Remote Similarity NPD6675 Approved
0.6053 Remote Similarity NPD6402 Approved
0.6053 Remote Similarity NPD5739 Approved
0.6053 Remote Similarity NPD7128 Approved
0.604 Remote Similarity NPD6435 Approved
0.6034 Remote Similarity NPD6012 Approved
0.6034 Remote Similarity NPD6014 Approved
0.6034 Remote Similarity NPD6013 Approved
0.6032 Remote Similarity NPD8293 Discontinued
0.6019 Remote Similarity NPD7748 Approved
0.6 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6 Remote Similarity NPD7902 Approved
0.6 Remote Similarity NPD6903 Approved
0.6 Remote Similarity NPD5701 Approved
0.5983 Remote Similarity NPD7290 Approved
0.5983 Remote Similarity NPD6883 Approved
0.5983 Remote Similarity NPD7102 Approved
0.5981 Remote Similarity NPD7515 Phase 2
0.5979 Remote Similarity NPD8039 Approved
0.5966 Remote Similarity NPD4632 Approved
0.5962 Remote Similarity NPD6684 Approved
0.5962 Remote Similarity NPD7334 Approved
0.5962 Remote Similarity NPD7521 Approved
0.5962 Remote Similarity NPD6409 Approved
0.5962 Remote Similarity NPD5330 Approved
0.5962 Remote Similarity NPD7146 Approved
0.5948 Remote Similarity NPD6011 Approved
0.5946 Remote Similarity NPD5696 Approved
0.5943 Remote Similarity NPD6101 Approved
0.5943 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5935 Remote Similarity NPD6319 Approved
0.5932 Remote Similarity NPD8130 Phase 1
0.5932 Remote Similarity NPD6847 Approved
0.5932 Remote Similarity NPD6649 Approved
0.5932 Remote Similarity NPD6869 Approved
0.5932 Remote Similarity NPD6650 Approved
0.5932 Remote Similarity NPD6617 Approved
0.5922 Remote Similarity NPD3666 Approved
0.5922 Remote Similarity NPD3665 Phase 1
0.5922 Remote Similarity NPD3133 Approved
0.592 Remote Similarity NPD7830 Approved
0.592 Remote Similarity NPD7829 Approved
0.592 Remote Similarity NPD8328 Phase 3
0.5913 Remote Similarity NPD6640 Phase 3
0.5909 Remote Similarity NPD7839 Suspended
0.5906 Remote Similarity NPD8074 Phase 3
0.5905 Remote Similarity NPD7750 Discontinued
0.59 Remote Similarity NPD6929 Approved
0.5897 Remote Similarity NPD6373 Approved
0.5897 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5897 Remote Similarity NPD6372 Approved
0.5882 Remote Similarity NPD4269 Approved
0.5882 Remote Similarity NPD3667 Approved
0.5882 Remote Similarity NPD4270 Approved
0.5876 Remote Similarity NPD6926 Approved
0.5876 Remote Similarity NPD6924 Approved
0.5865 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5865 Remote Similarity NPD1696 Phase 3
0.5859 Remote Similarity NPD6925 Approved
0.5859 Remote Similarity NPD5776 Phase 2
0.5849 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5849 Remote Similarity NPD5737 Approved
0.5849 Remote Similarity NPD6672 Approved
0.5842 Remote Similarity NPD6930 Phase 2
0.5842 Remote Similarity NPD6931 Approved
0.5842 Remote Similarity NPD7514 Phase 3
0.5842 Remote Similarity NPD7332 Phase 2
0.5842 Remote Similarity NPD4695 Discontinued
0.5842 Remote Similarity NPD5368 Approved
0.5833 Remote Similarity NPD5693 Phase 1
0.581 Remote Similarity NPD3618 Phase 1
0.581 Remote Similarity NPD5786 Approved
0.581 Remote Similarity NPD5279 Phase 3
0.58 Remote Similarity NPD7322 Clinical (unspecified phase)
0.58 Remote Similarity NPD7145 Approved
0.5798 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5794 Remote Similarity NPD6067 Discontinued
0.5794 Remote Similarity NPD4753 Phase 2
0.5794 Remote Similarity NPD7642 Approved
0.5789 Remote Similarity NPD5211 Phase 2
0.5789 Remote Similarity NPD6922 Approved
0.5789 Remote Similarity NPD6923 Approved
0.5784 Remote Similarity NPD6902 Approved
0.5784 Remote Similarity NPD5369 Approved
0.5778 Remote Similarity NPD1145 Discontinued
0.5776 Remote Similarity NPD4211 Phase 1
0.5776 Remote Similarity NPD6008 Approved
0.5772 Remote Similarity NPD7641 Discontinued
0.5769 Remote Similarity NPD4786 Approved
0.5769 Remote Similarity NPD5956 Approved
0.5761 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5758 Remote Similarity NPD5952 Clinical (unspecified phase)
0.5758 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5752 Remote Similarity NPD5286 Approved
0.5752 Remote Similarity NPD4696 Approved
0.5752 Remote Similarity NPD5285 Approved
0.5741 Remote Similarity NPD3168 Discontinued
0.5739 Remote Similarity NPD6647 Phase 2
0.5738 Remote Similarity NPD6274 Approved

Structure

External Identifiers

PubChem CID   10635208
ChEMBL   CHEMBL508946
ZINC  

Physicochemical Properties

Molecular Weight:  262.12
ALogP:  0.2754
MLogP:  2.67
XLogP:  1.455
# Rotatable Bonds:  2
Polar Surface Area:  55.76
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  19

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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