Natural Product: NPC59682

Natural Product ID:  NPC59682
Common Name:   6 Alpha-Malonyloxymanoyl Oxide
IUPAC Name:   3-[[(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-6-yl]oxy]-3-oxopropanoic acid
Synonyms:   6 Alpha-Malonyloxymanoyl Oxide
Molecular Formula:   C23H36O5
Standard InCHIKey:  JZRGFUZJIZSKTF-ALFLKXBZSA-N
Standard InCHI:  InChI=1S/C23H36O5/c1-7-21(4)12-9-16-22(5)11-8-10-20(2,3)19(22)15(14-23(16,6)28-21)27-18(26)13-17(24)25/h7,15-16,19H,1,8-14H2,2-6H3,(H,24,25)/t15-,16+,19-,21-,22+,23+/m0/s1
Canonical SMILES:  C=C[C@@]1(C)CC[C@H]2[C@@](O1)(C)C[C@@H]([C@@H]1[C@]2(C)CCCC1(C)C)OC(=O)CC(=O)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
NPO29102 Stemodia foliosa Species Plantaginaceae Eukaryota PMID[18582112]
NPO29102 Stemodia foliosa Species Plantaginaceae Eukaryota Aerial parts PMID[18582112]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 15 ug/ml 18582112
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 15 ug/ml 18582112
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 15 ug/ml 18582112
NPT1550 Organism Bacillus anthracis Bacillus anthracis MIC = 20 ug/ml 18582112
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 17 ug/ml 18582112
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 7 ug/ml 18582112
NPT1177 Organism Mycobacterium phlei Mycobacterium phlei MIC = 9 ug/ml 18582112

  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 NPC59682 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
0.8587 High Similarity NPC217329
0.8202 Intermediate Similarity NPC164424
0.82 Intermediate Similarity NPC208461
0.82 Intermediate Similarity NPC289702
0.8161 Intermediate Similarity NPC48673
0.8161 Intermediate Similarity NPC20096
0.8118 Intermediate Similarity NPC169994
0.8065 Intermediate Similarity NPC130840
0.8065 Intermediate Similarity NPC477574
0.7979 Intermediate Similarity NPC199543
0.7978 Intermediate Similarity NPC473592
0.7959 Intermediate Similarity NPC111292
0.7957 Intermediate Similarity NPC474249
0.7957 Intermediate Similarity NPC261990
0.7938 Intermediate Similarity NPC477653
0.7895 Intermediate Similarity NPC3359
0.7889 Intermediate Similarity NPC299963
0.7879 Intermediate Similarity NPC164551
0.7865 Intermediate Similarity NPC474979
0.7857 Intermediate Similarity NPC477656
0.7835 Intermediate Similarity NPC51499
0.7812 Intermediate Similarity NPC276110
0.7789 Intermediate Similarity NPC7349
0.7789 Intermediate Similarity NPC474835
0.7778 Intermediate Similarity NPC242666
0.7778 Intermediate Similarity NPC11974
0.7766 Intermediate Similarity NPC123252
0.7766 Intermediate Similarity NPC219937
0.7766 Intermediate Similarity NPC194485
0.7766 Intermediate Similarity NPC10274
0.7766 Intermediate Similarity NPC53890
0.7765 Intermediate Similarity NPC71152
0.7755 Intermediate Similarity NPC325229
0.7755 Intermediate Similarity NPC275086
0.7753 Intermediate Similarity NPC476101
0.7745 Intermediate Similarity NPC263729
0.7732 Intermediate Similarity NPC473964
0.7708 Intermediate Similarity NPC105490
0.7708 Intermediate Similarity NPC469982
0.7684 Intermediate Similarity NPC289361
0.7684 Intermediate Similarity NPC219516
0.7677 Intermediate Similarity NPC477655
0.7667 Intermediate Similarity NPC472504
0.766 Intermediate Similarity NPC16265
0.7653 Intermediate Similarity NPC287668
0.7653 Intermediate Similarity NPC253586
0.7653 Intermediate Similarity NPC274793
0.7653 Intermediate Similarity NPC473963
0.7647 Intermediate Similarity NPC295366
0.764 Intermediate Similarity NPC474978
0.764 Intermediate Similarity NPC469802
0.7634 Intermediate Similarity NPC166857
0.7629 Intermediate Similarity NPC37603
0.7629 Intermediate Similarity NPC111273
0.7629 Intermediate Similarity NPC259042
0.7629 Intermediate Similarity NPC157686
0.7629 Intermediate Similarity NPC471786
0.7624 Intermediate Similarity NPC222153
0.7624 Intermediate Similarity NPC45897
0.7624 Intermediate Similarity NPC189588
0.7624 Intermediate Similarity NPC187302
0.7624 Intermediate Similarity NPC97487
0.7624 Intermediate Similarity NPC196471
0.7624 Intermediate Similarity NPC471938
0.7624 Intermediate Similarity NPC99510
0.7624 Intermediate Similarity NPC10232
0.7624 Intermediate Similarity NPC23584
0.7614 Intermediate Similarity NPC137587
0.7609 Intermediate Similarity NPC477205
0.7604 Intermediate Similarity NPC26046
0.76 Intermediate Similarity NPC49532
0.76 Intermediate Similarity NPC236585
0.76 Intermediate Similarity NPC308824
0.7582 Intermediate Similarity NPC477978
0.7576 Intermediate Similarity NPC119036
0.7576 Intermediate Similarity NPC474724
0.7576 Intermediate Similarity NPC469986
0.7576 Intermediate Similarity NPC474793
0.7576 Intermediate Similarity NPC472028
0.7576 Intermediate Similarity NPC278673
0.7573 Intermediate Similarity NPC475570
0.7553 Intermediate Similarity NPC106332
0.7553 Intermediate Similarity NPC160304
0.7551 Intermediate Similarity NPC93245
0.7551 Intermediate Similarity NPC194132
0.7551 Intermediate Similarity NPC471903
0.7551 Intermediate Similarity NPC284518
0.7551 Intermediate Similarity NPC165528
0.7551 Intermediate Similarity NPC317573
0.7551 Intermediate Similarity NPC228766
0.7549 Intermediate Similarity NPC471937
0.7549 Intermediate Similarity NPC239162
0.7547 Intermediate Similarity NPC4573
0.7547 Intermediate Similarity NPC277769
0.7547 Intermediate Similarity NPC476964
0.7547 Intermediate Similarity NPC90952
0.7526 Intermediate Similarity NPC225474
0.7526 Intermediate Similarity NPC471446
0.7526 Intermediate Similarity NPC47853
0.7526 Intermediate Similarity NPC473434
0.7526 Intermediate Similarity NPC148000
0.7526 Intermediate Similarity NPC469596
0.7526 Intermediate Similarity NPC474841
0.7525 Intermediate Similarity NPC170615
0.7525 Intermediate Similarity NPC11956
0.7525 Intermediate Similarity NPC475038
0.7525 Intermediate Similarity NPC471914
0.7525 Intermediate Similarity NPC472552
0.7525 Intermediate Similarity NPC476081
0.7525 Intermediate Similarity NPC109195
0.7525 Intermediate Similarity NPC475091
0.75 Intermediate Similarity NPC124374
0.75 Intermediate Similarity NPC37047
0.75 Intermediate Similarity NPC41239
0.75 Intermediate Similarity NPC251680
0.75 Intermediate Similarity NPC94906
0.75 Intermediate Similarity NPC180733
0.75 Intermediate Similarity NPC476934
0.75 Intermediate Similarity NPC38855
0.75 Intermediate Similarity NPC198054
0.75 Intermediate Similarity NPC41971
0.75 Intermediate Similarity NPC471413
0.75 Intermediate Similarity NPC47024
0.75 Intermediate Similarity NPC32223
0.75 Intermediate Similarity NPC473483
0.75 Intermediate Similarity NPC475156
0.75 Intermediate Similarity NPC234335
0.75 Intermediate Similarity NPC163216
0.75 Intermediate Similarity NPC473576
0.75 Intermediate Similarity NPC16601
0.75 Intermediate Similarity NPC102048
0.75 Intermediate Similarity NPC108371
0.7476 Intermediate Similarity NPC51719
0.7476 Intermediate Similarity NPC471206
0.7475 Intermediate Similarity NPC309503
0.7475 Intermediate Similarity NPC476879
0.7475 Intermediate Similarity NPC474395
0.7475 Intermediate Similarity NPC473244
0.7475 Intermediate Similarity NPC91197
0.7475 Intermediate Similarity NPC96597
0.7475 Intermediate Similarity NPC476878
0.7475 Intermediate Similarity NPC239547
0.7475 Intermediate Similarity NPC155319
0.7475 Intermediate Similarity NPC125551
0.7474 Intermediate Similarity NPC261320
0.7474 Intermediate Similarity NPC170633
0.7474 Intermediate Similarity NPC82876
0.7474 Intermediate Similarity NPC246028
0.7473 Intermediate Similarity NPC474605
0.7473 Intermediate Similarity NPC476292
0.7453 Intermediate Similarity NPC270586
0.7451 Intermediate Similarity NPC120009
0.7451 Intermediate Similarity NPC120321
0.7451 Intermediate Similarity NPC72842
0.7451 Intermediate Similarity NPC473523
0.7451 Intermediate Similarity NPC156681
0.7449 Intermediate Similarity NPC470229
0.7449 Intermediate Similarity NPC241047
0.7447 Intermediate Similarity NPC131329
0.7447 Intermediate Similarity NPC471779
0.7444 Intermediate Similarity NPC206735
0.7429 Intermediate Similarity NPC257082
0.7429 Intermediate Similarity NPC5475
0.7429 Intermediate Similarity NPC285298
0.7429 Intermediate Similarity NPC173905
0.7429 Intermediate Similarity NPC471250
0.7429 Intermediate Similarity NPC284828
0.7429 Intermediate Similarity NPC475030
0.7429 Intermediate Similarity NPC472216
0.7426 Intermediate Similarity NPC295110
0.7426 Intermediate Similarity NPC477053
0.7426 Intermediate Similarity NPC477052
0.7426 Intermediate Similarity NPC25177
0.7426 Intermediate Similarity NPC471412
0.7426 Intermediate Similarity NPC75941
0.7426 Intermediate Similarity NPC46848
0.7426 Intermediate Similarity NPC280991
0.7426 Intermediate Similarity NPC477051
0.7426 Intermediate Similarity NPC235142
0.7426 Intermediate Similarity NPC222875
0.7426 Intermediate Similarity NPC268829
0.7426 Intermediate Similarity NPC472554
0.7426 Intermediate Similarity NPC475617
0.7426 Intermediate Similarity NPC247701
0.7423 Intermediate Similarity NPC99653
0.7423 Intermediate Similarity NPC472640
0.7423 Intermediate Similarity NPC27531
0.7423 Intermediate Similarity NPC472641
0.7423 Intermediate Similarity NPC110022
0.7419 Intermediate Similarity NPC224345
0.7407 Intermediate Similarity NPC470953
0.7404 Intermediate Similarity NPC302788
0.7404 Intermediate Similarity NPC475781
0.7404 Intermediate Similarity NPC122816
0.7404 Intermediate Similarity NPC471205
0.74 Intermediate Similarity NPC78427
0.74 Intermediate Similarity NPC218107
0.74 Intermediate Similarity NPC477875
0.74 Intermediate Similarity NPC16911
0.74 Intermediate Similarity NPC470068

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC59682 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
0.82 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7638 Approved
0.75 Intermediate Similarity NPD7640 Approved
0.75 Intermediate Similarity NPD7639 Approved
0.7321 Intermediate Similarity NPD6921 Approved
0.7059 Intermediate Similarity NPD4225 Approved
0.7019 Intermediate Similarity NPD7632 Discontinued
0.697 Remote Similarity NPD7637 Suspended
0.6944 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7327 Approved
0.6903 Remote Similarity NPD7328 Approved
0.6881 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6847 Remote Similarity NPD8133 Approved
0.6842 Remote Similarity NPD7516 Approved
0.6832 Remote Similarity NPD7748 Approved
0.6814 Remote Similarity NPD7115 Discovery
0.68 Remote Similarity NPD8034 Phase 2
0.68 Remote Similarity NPD6411 Approved
0.68 Remote Similarity NPD8035 Phase 2
0.6762 Remote Similarity NPD5344 Discontinued
0.675 Remote Similarity NPD7319 Approved
0.6724 Remote Similarity NPD8379 Approved
0.6724 Remote Similarity NPD8378 Approved
0.6724 Remote Similarity NPD8335 Approved
0.6724 Remote Similarity NPD8296 Approved
0.6724 Remote Similarity NPD8380 Approved
0.6701 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6697 Remote Similarity NPD6686 Approved
0.6667 Remote Similarity NPD6648 Approved
0.6667 Remote Similarity NPD6118 Approved
0.6667 Remote Similarity NPD6114 Approved
0.6667 Remote Similarity NPD6115 Approved
0.6667 Remote Similarity NPD6697 Approved
0.6638 Remote Similarity NPD8377 Approved
0.6638 Remote Similarity NPD8294 Approved
0.6635 Remote Similarity NPD7902 Approved
0.6634 Remote Similarity NPD7515 Phase 2
0.6606 Remote Similarity NPD5954 Clinical (unspecified phase)
0.66 Remote Similarity NPD6051 Approved
0.66 Remote Similarity NPD5764 Clinical (unspecified phase)
0.66 Remote Similarity NPD6101 Approved
0.6596 Remote Similarity NPD7645 Phase 2
0.6581 Remote Similarity NPD7503 Approved
0.6581 Remote Similarity NPD8033 Approved
0.6569 Remote Similarity NPD5779 Approved
0.6569 Remote Similarity NPD5778 Approved
0.6569 Remote Similarity NPD6399 Phase 3
0.6545 Remote Similarity NPD6899 Approved
0.6545 Remote Similarity NPD6881 Approved
0.6526 Remote Similarity NPD7525 Registered
0.6514 Remote Similarity NPD5739 Approved
0.6514 Remote Similarity NPD6675 Approved
0.6514 Remote Similarity NPD6402 Approved
0.6514 Remote Similarity NPD7128 Approved
0.65 Remote Similarity NPD7507 Approved
0.6496 Remote Similarity NPD6319 Approved
0.6495 Remote Similarity NPD6695 Phase 3
0.6486 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6455 Remote Similarity NPD5697 Approved
0.6452 Remote Similarity NPD6117 Approved
0.6429 Remote Similarity NPD6883 Approved
0.6429 Remote Similarity NPD7290 Approved
0.6429 Remote Similarity NPD7102 Approved
0.6429 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6417 Remote Similarity NPD7492 Approved
0.64 Remote Similarity NPD3573 Approved
0.6396 Remote Similarity NPD7320 Approved
0.6383 Remote Similarity NPD6116 Phase 1
0.6379 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6372 Remote Similarity NPD6649 Approved
0.6372 Remote Similarity NPD6869 Approved
0.6372 Remote Similarity NPD6617 Approved
0.6372 Remote Similarity NPD6650 Approved
0.6372 Remote Similarity NPD8130 Phase 1
0.6372 Remote Similarity NPD6847 Approved
0.6364 Remote Similarity NPD6616 Approved
0.6356 Remote Similarity NPD6054 Approved
0.6346 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6346 Remote Similarity NPD7900 Approved
0.6339 Remote Similarity NPD6014 Approved
0.6339 Remote Similarity NPD6012 Approved
0.6339 Remote Similarity NPD6373 Approved
0.6339 Remote Similarity NPD6013 Approved
0.6339 Remote Similarity NPD6372 Approved
0.6333 Remote Similarity NPD8328 Phase 3
0.6321 Remote Similarity NPD6084 Phase 2
0.6321 Remote Similarity NPD6083 Phase 2
0.6316 Remote Similarity NPD6882 Approved
0.6316 Remote Similarity NPD8297 Approved
0.6311 Remote Similarity NPD7078 Approved
0.6306 Remote Similarity NPD5701 Approved
0.6261 Remote Similarity NPD4632 Approved
0.626 Remote Similarity NPD7736 Approved
0.625 Remote Similarity NPD6011 Approved
0.625 Remote Similarity NPD6370 Approved
0.6238 Remote Similarity NPD7750 Discontinued
0.6238 Remote Similarity NPD7524 Approved
0.6237 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6224 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6218 Remote Similarity NPD6059 Approved
0.6216 Remote Similarity NPD6008 Approved
0.62 Remote Similarity NPD1694 Approved
0.6186 Remote Similarity NPD6930 Phase 2
0.6186 Remote Similarity NPD6931 Approved
0.6179 Remote Similarity NPD8293 Discontinued
0.617 Remote Similarity NPD3702 Approved
0.6167 Remote Similarity NPD6015 Approved
0.6167 Remote Similarity NPD8516 Approved
0.6167 Remote Similarity NPD8513 Phase 3
0.6167 Remote Similarity NPD6016 Approved
0.6167 Remote Similarity NPD8517 Approved
0.6167 Remote Similarity NPD8515 Approved
0.6162 Remote Similarity NPD3669 Approved
0.6162 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6161 Remote Similarity NPD6412 Phase 2
0.6154 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6079 Approved
0.614 Remote Similarity NPD4634 Approved
0.6139 Remote Similarity NPD7521 Approved
0.6139 Remote Similarity NPD5330 Approved
0.6139 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6139 Remote Similarity NPD6409 Approved
0.6139 Remote Similarity NPD6684 Approved
0.6139 Remote Similarity NPD7334 Approved
0.6139 Remote Similarity NPD7146 Approved
0.6139 Remote Similarity NPD3618 Phase 1
0.6132 Remote Similarity NPD5695 Phase 3
0.6117 Remote Similarity NPD5328 Approved
0.6116 Remote Similarity NPD5988 Approved
0.6111 Remote Similarity NPD5696 Approved
0.6102 Remote Similarity NPD6009 Approved
0.61 Remote Similarity NPD4786 Approved
0.6091 Remote Similarity NPD5211 Phase 2
0.6087 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6082 Remote Similarity NPD6929 Approved
0.6066 Remote Similarity NPD7604 Phase 2
0.6061 Remote Similarity NPD3667 Approved
0.6058 Remote Similarity NPD6698 Approved
0.6058 Remote Similarity NPD7838 Discovery
0.6058 Remote Similarity NPD46 Approved
0.6055 Remote Similarity NPD5286 Approved
0.6055 Remote Similarity NPD5285 Approved
0.6055 Remote Similarity NPD4696 Approved
0.6042 Remote Similarity NPD6932 Approved
0.6038 Remote Similarity NPD5282 Discontinued
0.6034 Remote Similarity NPD6053 Discontinued
0.6033 Remote Similarity NPD5983 Phase 2
0.602 Remote Similarity NPD6928 Phase 2
0.602 Remote Similarity NPD7514 Phase 3
0.602 Remote Similarity NPD7332 Phase 2
0.6019 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6903 Approved
0.6019 Remote Similarity NPD4755 Approved
0.6019 Remote Similarity NPD5737 Approved
0.6019 Remote Similarity NPD6672 Approved
0.6 Remote Similarity NPD7100 Approved
0.6 Remote Similarity NPD3703 Phase 2
0.6 Remote Similarity NPD7101 Approved
0.6 Remote Similarity NPD6942 Approved
0.6 Remote Similarity NPD7087 Discontinued
0.6 Remote Similarity NPD7339 Approved
0.6 Remote Similarity NPD5693 Phase 1
0.5982 Remote Similarity NPD5141 Approved
0.5981 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5979 Remote Similarity NPD7145 Approved
0.5968 Remote Similarity NPD6336 Discontinued
0.5963 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5955 Remote Similarity NPD371 Approved
0.5946 Remote Similarity NPD4633 Approved
0.5946 Remote Similarity NPD5225 Approved
0.5946 Remote Similarity NPD5226 Approved
0.5946 Remote Similarity NPD5224 Approved
0.5943 Remote Similarity NPD4202 Approved
0.5938 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5926 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5926 Remote Similarity NPD5222 Approved
0.5926 Remote Similarity NPD5221 Approved
0.5922 Remote Similarity NPD4751 Clinical (unspecified phase)
0.592 Remote Similarity NPD8074 Phase 3
0.5917 Remote Similarity NPD6335 Approved
0.5909 Remote Similarity NPD4700 Approved
0.5905 Remote Similarity NPD5785 Approved
0.5893 Remote Similarity NPD5174 Approved
0.5893 Remote Similarity NPD5175 Approved
0.5882 Remote Similarity NPD6274 Approved
0.5882 Remote Similarity NPD6868 Approved
0.5882 Remote Similarity NPD6893 Approved
0.5876 Remote Similarity NPD5776 Phase 2
0.5876 Remote Similarity NPD6925 Approved
0.5872 Remote Similarity NPD5173 Approved
0.5862 Remote Similarity NPD6371 Approved
0.5856 Remote Similarity NPD4159 Approved
0.5856 Remote Similarity NPD5223 Approved
0.5856 Remote Similarity NPD1700 Approved
0.5851 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5851 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5851 Remote Similarity NPD5777 Approved
0.5849 Remote Similarity NPD7983 Approved
0.5842 Remote Similarity NPD4788 Approved
0.5833 Remote Similarity NPD1698 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   24970705
ChEMBL   CHEMBL480513
ZINC  

Physicochemical Properties

Molecular Weight:  392.26
ALogP:  2.1409
MLogP:  3.44
XLogP:  6.076
# Rotatable Bonds:  11
Polar Surface Area:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  28

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