Natural Product: NPC44199

Natural Product ID:  NPC44199
Common Name:   Massarinin A
IUPAC Name:   3-hydroxy-2-(7-hydroxy-2,2-dimethylchromene-8-carbonyl)-6-methoxy-5-methylbenzaldehyde
Synonyms:  
Molecular Formula:   C21H20O6
Standard InCHIKey:  MEPDGCUSJWFRRO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H20O6/c1-11-9-15(24)16(13(10-22)19(11)26-4)18(25)17-14(23)6-5-12-7-8-21(2,3)27-20(12)17/h5-10,23-24H,1-4H3
Canonical SMILES:  COc1c(C)cc(c(c1C=O)C(=O)c1c(O)ccc2c1OC(C)(C)C=C2)O
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[12542349]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 7 mm 15711537
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 17 mm 15711537

  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 NPC44199 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
0.9536 High Similarity NPC135522
0.929 High Similarity NPC186113
0.9281 High Similarity NPC280530
0.9281 High Similarity NPC178964
0.9281 High Similarity NPC169990
0.9281 High Similarity NPC210942
0.9281 High Similarity NPC95842
0.9236 High Similarity NPC473961
0.9216 High Similarity NPC40356
0.9216 High Similarity NPC154683
0.9211 High Similarity NPC227122
0.9205 High Similarity NPC5537
0.9167 High Similarity NPC477692
0.9156 High Similarity NPC329844
0.9156 High Similarity NPC477691
0.915 High Similarity NPC474417
0.915 High Similarity NPC478148
0.915 High Similarity NPC149526
0.9145 High Similarity NPC65775
0.9145 High Similarity NPC158338
0.9145 High Similarity NPC100985
0.9145 High Similarity NPC97028
0.9145 High Similarity NPC65589
0.9145 High Similarity NPC97029
0.9145 High Similarity NPC10027
0.9145 High Similarity NPC288036
0.9139 High Similarity NPC71055
0.9108 High Similarity NPC143050
0.9097 High Similarity NPC55662
0.9097 High Similarity NPC166054
0.9091 High Similarity NPC474843
0.9091 High Similarity NPC477690
0.9091 High Similarity NPC281272
0.9085 High Similarity NPC294646
0.9085 High Similarity NPC202595
0.9085 High Similarity NPC37348
0.9079 High Similarity NPC7025
0.9079 High Similarity NPC27221
0.9079 High Similarity NPC256672
0.9057 High Similarity NPC207690
0.9051 High Similarity NPC66288
0.9032 High Similarity NPC208806
0.9026 High Similarity NPC232645
0.9026 High Similarity NPC72958
0.902 High Similarity NPC266499
0.9013 High Similarity NPC123202
0.9013 High Similarity NPC7943
0.9013 High Similarity NPC22005
0.9012 High Similarity NPC241874
0.9006 High Similarity NPC76647
0.9006 High Similarity NPC225419
0.9 High Similarity NPC136641
0.8994 High Similarity NPC229632
0.8994 High Similarity NPC472402
0.8993 High Similarity NPC187843
0.8987 High Similarity NPC470810
0.8981 High Similarity NPC272196
0.8968 High Similarity NPC87708
0.8968 High Similarity NPC175978
0.8961 High Similarity NPC470568
0.8961 High Similarity NPC290954
0.8961 High Similarity NPC255641
0.8961 High Similarity NPC147735
0.8961 High Similarity NPC29777
0.8961 High Similarity NPC101957
0.8961 High Similarity NPC120105
0.8961 High Similarity NPC471115
0.8961 High Similarity NPC472633
0.8954 High Similarity NPC37135
0.8954 High Similarity NPC186397
0.8947 High Similarity NPC469758
0.8944 High Similarity NPC37870
0.8938 High Similarity NPC197168
0.8938 High Similarity NPC100849
0.8938 High Similarity NPC270837
0.8931 High Similarity NPC474187
0.891 High Similarity NPC193200
0.891 High Similarity NPC214632
0.8903 High Similarity NPC258249
0.8903 High Similarity NPC39819
0.8903 High Similarity NPC470569
0.8896 High Similarity NPC269420
0.8896 High Similarity NPC70764
0.8896 High Similarity NPC223988
0.8896 High Similarity NPC474004
0.8896 High Similarity NPC329933
0.8896 High Similarity NPC474052
0.8889 High Similarity NPC312929
0.8889 High Similarity NPC118027
0.8889 High Similarity NPC34802
0.8889 High Similarity NPC126767
0.8889 High Similarity NPC308200
0.8889 High Similarity NPC56433
0.8889 High Similarity NPC245584
0.8889 High Similarity NPC190648
0.8889 High Similarity NPC289042
0.8882 High Similarity NPC469764
0.8882 High Similarity NPC472450
0.8882 High Similarity NPC239752
0.8882 High Similarity NPC311741
0.8882 High Similarity NPC234629
0.8882 High Similarity NPC25361
0.8882 High Similarity NPC275780
0.8875 High Similarity NPC294965
0.8875 High Similarity NPC329760
0.8868 High Similarity NPC119224
0.8868 High Similarity NPC475886
0.8868 High Similarity NPC474287
0.8861 High Similarity NPC212967
0.8861 High Similarity NPC268360
0.8861 High Similarity NPC246647
0.8861 High Similarity NPC164110
0.8861 High Similarity NPC196448
0.8861 High Similarity NPC217677
0.8861 High Similarity NPC281137
0.8861 High Similarity NPC263483
0.8861 High Similarity NPC282390
0.8861 High Similarity NPC96342
0.8861 High Similarity NPC165977
0.8861 High Similarity NPC476981
0.8854 High Similarity NPC89625
0.8854 High Similarity NPC149618
0.8848 High Similarity NPC289147
0.8846 High Similarity NPC271681
0.8846 High Similarity NPC142527
0.8846 High Similarity NPC273483
0.8846 High Similarity NPC45934
0.8846 High Similarity NPC217447
0.8839 High Similarity NPC295036
0.8839 High Similarity NPC158866
0.8831 High Similarity NPC145467
0.8831 High Similarity NPC37139
0.8831 High Similarity NPC266572
0.8831 High Similarity NPC39195
0.8827 High Similarity NPC43319
0.8827 High Similarity NPC39091
0.8827 High Similarity NPC30027
0.8827 High Similarity NPC272502
0.8827 High Similarity NPC178173
0.8824 High Similarity NPC24136
0.8824 High Similarity NPC124729
0.8824 High Similarity NPC300540
0.8824 High Similarity NPC196114
0.8824 High Similarity NPC60389
0.8824 High Similarity NPC290133
0.8824 High Similarity NPC187282
0.882 High Similarity NPC23298
0.882 High Similarity NPC236132
0.882 High Similarity NPC189473
0.882 High Similarity NPC101769
0.8816 High Similarity NPC189650
0.8812 High Similarity NPC475883
0.8812 High Similarity NPC32694
0.8812 High Similarity NPC474186
0.8812 High Similarity NPC61010
0.8812 High Similarity NPC474351
0.8805 High Similarity NPC85121
0.8805 High Similarity NPC474290
0.8805 High Similarity NPC324736
0.8797 High Similarity NPC142339
0.8797 High Similarity NPC180924
0.8797 High Similarity NPC146211
0.878 High Similarity NPC20543
0.878 High Similarity NPC239440
0.8774 High Similarity NPC233267
0.8774 High Similarity NPC471114
0.8774 High Similarity NPC291049
0.8774 High Similarity NPC5173
0.8774 High Similarity NPC317492
0.8773 High Similarity NPC234331
0.8773 High Similarity NPC218226
0.8766 High Similarity NPC237635
0.8766 High Similarity NPC473077
0.8766 High Similarity NPC296998
0.8766 High Similarity NPC259632
0.8766 High Similarity NPC201731
0.8766 High Similarity NPC79469
0.8766 High Similarity NPC104406
0.8766 High Similarity NPC24673
0.8766 High Similarity NPC97716
0.8765 High Similarity NPC156432
0.8765 High Similarity NPC303174
0.8758 High Similarity NPC49282
0.8758 High Similarity NPC216538
0.8758 High Similarity NPC470694
0.8758 High Similarity NPC311144
0.8758 High Similarity NPC273538
0.8758 High Similarity NPC271288
0.8758 High Similarity NPC224714
0.875 High Similarity NPC228785
0.875 High Similarity NPC186325
0.875 High Similarity NPC471976
0.875 High Similarity NPC284495
0.875 High Similarity NPC476980
0.875 High Similarity NPC310340
0.875 High Similarity NPC84266
0.875 High Similarity NPC235018
0.875 High Similarity NPC11561
0.875 High Similarity NPC14353
0.875 High Similarity NPC80375

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC44199 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
0.8758 High Similarity NPD4378 Clinical (unspecified phase)
0.858 High Similarity NPD6959 Discontinued
0.8553 High Similarity NPD7819 Suspended
0.8553 High Similarity NPD2801 Approved
0.8553 High Similarity NPD2393 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD6232 Discontinued
0.8397 Intermediate Similarity NPD2534 Approved
0.8397 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD2532 Approved
0.8397 Intermediate Similarity NPD2533 Approved
0.8373 Intermediate Similarity NPD7473 Discontinued
0.8302 Intermediate Similarity NPD3226 Approved
0.8301 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8289 Intermediate Similarity NPD1510 Phase 2
0.8272 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD1934 Approved
0.8258 Intermediate Similarity NPD3750 Approved
0.825 Intermediate Similarity NPD4380 Phase 2
0.8247 Intermediate Similarity NPD1549 Phase 2
0.8235 Intermediate Similarity NPD2935 Discontinued
0.8235 Intermediate Similarity NPD6559 Discontinued
0.8235 Intermediate Similarity NPD1551 Phase 2
0.8235 Intermediate Similarity NPD2796 Approved
0.8217 Intermediate Similarity NPD1511 Approved
0.8182 Intermediate Similarity NPD5494 Approved
0.8182 Intermediate Similarity NPD2346 Discontinued
0.817 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8166 Intermediate Similarity NPD5844 Phase 1
0.8158 Intermediate Similarity NPD1607 Approved
0.8129 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD1512 Approved
0.811 Intermediate Similarity NPD7768 Phase 2
0.8086 Intermediate Similarity NPD7411 Suspended
0.8061 Intermediate Similarity NPD7075 Discontinued
0.8049 Intermediate Similarity NPD5402 Approved
0.8026 Intermediate Similarity NPD1240 Approved
0.8 Intermediate Similarity NPD3882 Suspended
0.7988 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD2800 Approved
0.7952 Intermediate Similarity NPD3749 Approved
0.7952 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD920 Approved
0.7947 Intermediate Similarity NPD4625 Phase 3
0.7939 Intermediate Similarity NPD3817 Phase 2
0.7935 Intermediate Similarity NPD3748 Approved
0.7927 Intermediate Similarity NPD6801 Discontinued
0.7921 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD1247 Approved
0.7914 Intermediate Similarity NPD6599 Discontinued
0.7895 Intermediate Similarity NPD3818 Discontinued
0.7885 Intermediate Similarity NPD6099 Approved
0.7885 Intermediate Similarity NPD6100 Approved
0.7882 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD6166 Phase 2
0.7875 Intermediate Similarity NPD7390 Discontinued
0.7849 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD2799 Discontinued
0.7799 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2313 Discontinued
0.7771 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD5711 Approved
0.7765 Intermediate Similarity NPD5710 Approved
0.7764 Intermediate Similarity NPD6799 Approved
0.7746 Intermediate Similarity NPD7054 Approved
0.7736 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD7074 Phase 3
0.7701 Intermediate Similarity NPD7472 Approved
0.7682 Intermediate Similarity NPD1470 Approved
0.7679 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD5953 Discontinued
0.7657 Intermediate Similarity NPD6797 Phase 2
0.7636 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD8312 Approved
0.7627 Intermediate Similarity NPD8313 Approved
0.7622 Intermediate Similarity NPD6779 Approved
0.7622 Intermediate Similarity NPD6780 Approved
0.7622 Intermediate Similarity NPD5403 Approved
0.7622 Intermediate Similarity NPD6776 Approved
0.7622 Intermediate Similarity NPD6782 Approved
0.7622 Intermediate Similarity NPD6781 Approved
0.7622 Intermediate Similarity NPD6777 Approved
0.7622 Intermediate Similarity NPD6778 Approved
0.7614 Intermediate Similarity NPD7251 Discontinued
0.7611 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD2344 Approved
0.7607 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD919 Approved
0.7571 Intermediate Similarity NPD7808 Phase 3
0.7548 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD5406 Approved
0.7547 Intermediate Similarity NPD5405 Approved
0.7547 Intermediate Similarity NPD5404 Approved
0.7547 Intermediate Similarity NPD5408 Approved
0.7543 Intermediate Similarity NPD7286 Phase 2
0.7533 Intermediate Similarity NPD1201 Approved
0.7532 Intermediate Similarity NPD4908 Phase 1
0.7516 Intermediate Similarity NPD1243 Approved
0.75 Intermediate Similarity NPD7696 Phase 3
0.75 Intermediate Similarity NPD7435 Discontinued
0.75 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5401 Approved
0.75 Intermediate Similarity NPD7698 Approved
0.75 Intermediate Similarity NPD8434 Phase 2
0.75 Intermediate Similarity NPD7697 Approved
0.7486 Intermediate Similarity NPD3751 Discontinued
0.7484 Intermediate Similarity NPD4308 Phase 3
0.7469 Intermediate Similarity NPD4628 Phase 3
0.7468 Intermediate Similarity NPD6651 Approved
0.746 Intermediate Similarity NPD7871 Phase 2
0.746 Intermediate Similarity NPD7870 Phase 2
0.7457 Intermediate Similarity NPD7229 Phase 3
0.7456 Intermediate Similarity NPD1465 Phase 2
0.7447 Intermediate Similarity NPD6823 Phase 2
0.7436 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD4749 Approved
0.7423 Intermediate Similarity NPD2309 Approved
0.7417 Intermediate Similarity NPD1610 Phase 2
0.7414 Intermediate Similarity NPD3926 Phase 2
0.7403 Intermediate Similarity NPD2798 Approved
0.7396 Intermediate Similarity NPD6844 Discontinued
0.7396 Intermediate Similarity NPD37 Approved
0.7384 Intermediate Similarity NPD6234 Discontinued
0.7383 Intermediate Similarity NPD1548 Phase 1
0.7368 Intermediate Similarity NPD4966 Approved
0.7368 Intermediate Similarity NPD4967 Phase 2
0.7368 Intermediate Similarity NPD4965 Approved
0.7362 Intermediate Similarity NPD7003 Approved
0.7356 Intermediate Similarity NPD3787 Discontinued
0.7355 Intermediate Similarity NPD2861 Phase 2
0.7353 Intermediate Similarity NPD5760 Phase 2
0.7353 Intermediate Similarity NPD5761 Phase 2
0.7351 Intermediate Similarity NPD6535 Approved
0.7351 Intermediate Similarity NPD4363 Phase 3
0.7351 Intermediate Similarity NPD4360 Phase 2
0.7351 Intermediate Similarity NPD6534 Approved
0.7344 Intermediate Similarity NPD7701 Phase 2
0.7342 Intermediate Similarity NPD943 Approved
0.734 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD1203 Approved
0.7338 Intermediate Similarity NPD2797 Approved
0.7337 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1651 Approved
0.7325 Intermediate Similarity NPD3764 Approved
0.7325 Intermediate Similarity NPD3268 Approved
0.732 Intermediate Similarity NPD7783 Phase 2
0.732 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD4288 Approved
0.7308 Intermediate Similarity NPD8150 Discontinued
0.7308 Intermediate Similarity NPD6832 Phase 2
0.7303 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD5124 Phase 1
0.7296 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD1471 Phase 3
0.7273 Intermediate Similarity NPD6696 Suspended
0.7273 Intermediate Similarity NPD1283 Approved
0.7268 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7874 Approved
0.7267 Intermediate Similarity NPD7033 Discontinued
0.7263 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6273 Approved
0.7234 Intermediate Similarity NPD7699 Phase 2
0.7234 Intermediate Similarity NPD7700 Phase 2
0.7233 Intermediate Similarity NPD4060 Phase 1
0.7233 Intermediate Similarity NPD2979 Phase 3
0.7233 Intermediate Similarity NPD1613 Approved
0.7233 Intermediate Similarity NPD4307 Phase 2
0.7233 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD7801 Approved
0.7219 Intermediate Similarity NPD4361 Phase 2
0.7219 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD8151 Discontinued
0.7215 Intermediate Similarity NPD411 Approved
0.7197 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7177 Discontinued
0.719 Intermediate Similarity NPD422 Phase 1
0.7188 Intermediate Similarity NPD447 Suspended
0.7171 Intermediate Similarity NPD4626 Approved
0.716 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9717 Approved
0.7134 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD3658 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7458 Discontinued
0.7117 Intermediate Similarity NPD4476 Approved
0.7117 Intermediate Similarity NPD4477 Approved
0.7105 Intermediate Similarity NPD5691 Approved
0.7102 Intermediate Similarity NPD7199 Phase 2
0.7095 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7228 Approved

Structure

External Identifiers

PubChem CID   10044532
ChEMBL   CHEMBL451710
ZINC  

Physicochemical Properties

Molecular Weight:  368.13
ALogP:  0.1212
MLogP:  3.11
XLogP:  3.099
# Rotatable Bonds:  10
Polar Surface Area:  93.06
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  27

Download Data

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