Natural Product: NPC10572

Natural Product ID:  NPC10572
Common Name:   Caucanolide A
IUPAC Name:   2-[2-[(2S)-2-[(1R)-1-[(2R)-2-methoxy-4-methyl-5-oxofuran-2-yl]-2-methylprop-2-enyl]-5-oxo-2H-furan-4-yl]ethyl]-3-methylbut-2-enal
Synonyms:  
Molecular Formula:   C21H26O6
Standard InCHIKey:  IYTPQKWQKYLEMT-WAOWUJCRSA-N
Standard InCHI:  InChI=1S/C21H26O6/c1-12(2)16(11-22)8-7-15-9-17(26-20(15)24)18(13(3)4)21(25-6)10-14(5)19(23)27-21/h9-11,17-18H,3,7-8H2,1-2,4-6H3/t17-,18+,21+/m0/s1
Canonical SMILES:  O=CC(=C(C)C)CCC1=C[C@H](OC1=O)[C@H]([C@]1(OC)OC(=O)C(=C1)C)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
NPO24654 Curculigo crassifolia Species Hypoxidaceae Eukaryota UNPD*
NPO3843 Rhododendron metternichii Species Ericaceae Eukaryota UNPD*
NPO24562 Saussurea petrovii Species Asteraceae Eukaryota UNPD*
NPO25930 Cystoseira balearica Species Sargassaceae Eukaryota UNPD*
NPO26421 Urtica laetevirens Species Urticaceae Eukaryota UNPD*
NPO25544 Encyclia michuacana Species Orchidaceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 17 ug/ml 16252918
NPT396 Cell Line T47D Homo sapiens IC50 = 25.8 ug/ml 16252918
NPT404 Cell Line CCRF-CEM Homo sapiens IC50 = 25.5 ug/ml 16252918
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 12.5 ug/ml 16252918
NPT83 Cell Line MCF7 Homo sapiens IC50 = 7.6 ug/ml 16252918
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis Activity = 21 % 16252918

  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 NPC10572 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
0.8442 Intermediate Similarity NPC68156
0.8312 Intermediate Similarity NPC123360
0.8125 Intermediate Similarity NPC281132
0.8082 Intermediate Similarity NPC248125
0.8052 Intermediate Similarity NPC474758
0.8052 Intermediate Similarity NPC476355
0.8026 Intermediate Similarity NPC84038
0.8 Intermediate Similarity NPC476591
0.8 Intermediate Similarity NPC88877
0.8 Intermediate Similarity NPC178277
0.7973 Intermediate Similarity NPC194871
0.7922 Intermediate Similarity NPC474705
0.7867 Intermediate Similarity NPC470256
0.7821 Intermediate Similarity NPC259599
0.7821 Intermediate Similarity NPC117746
0.7821 Intermediate Similarity NPC15499
0.7821 Intermediate Similarity NPC294434
0.7821 Intermediate Similarity NPC140287
0.7805 Intermediate Similarity NPC471325
0.7792 Intermediate Similarity NPC163003
0.7778 Intermediate Similarity NPC270126
0.7778 Intermediate Similarity NPC151648
0.775 Intermediate Similarity NPC476028
0.775 Intermediate Similarity NPC57744
0.775 Intermediate Similarity NPC141789
0.775 Intermediate Similarity NPC171204
0.775 Intermediate Similarity NPC97516
0.7733 Intermediate Similarity NPC203335
0.7722 Intermediate Similarity NPC329852
0.7711 Intermediate Similarity NPC173609
0.7654 Intermediate Similarity NPC108816
0.7654 Intermediate Similarity NPC93763
0.7654 Intermediate Similarity NPC128276
0.7632 Intermediate Similarity NPC218477
0.7619 Intermediate Similarity NPC59097
0.7619 Intermediate Similarity NPC475947
0.7614 Intermediate Similarity NPC475995
0.7614 Intermediate Similarity NPC474098
0.7614 Intermediate Similarity NPC80875
0.7586 Intermediate Similarity NPC471057
0.7586 Intermediate Similarity NPC471058
0.75 Intermediate Similarity NPC150967
0.7468 Intermediate Similarity NPC58956
0.7468 Intermediate Similarity NPC269206
0.7468 Intermediate Similarity NPC295633
0.7442 Intermediate Similarity NPC471060
0.7442 Intermediate Similarity NPC215364
0.7439 Intermediate Similarity NPC299235
0.7436 Intermediate Similarity NPC475113
0.7436 Intermediate Similarity NPC299932
0.7436 Intermediate Similarity NPC67183
0.7432 Intermediate Similarity NPC474658
0.7412 Intermediate Similarity NPC40746
0.7412 Intermediate Similarity NPC169575
0.7381 Intermediate Similarity NPC325031
0.7381 Intermediate Similarity NPC141810
0.7381 Intermediate Similarity NPC301477
0.7381 Intermediate Similarity NPC42470
0.7381 Intermediate Similarity NPC281949
0.7381 Intermediate Similarity NPC25684
0.7375 Intermediate Similarity NPC114727
0.7375 Intermediate Similarity NPC476590
0.7356 Intermediate Similarity NPC284902
0.7356 Intermediate Similarity NPC150755
0.7356 Intermediate Similarity NPC107787
0.7349 Intermediate Similarity NPC471299
0.7342 Intermediate Similarity NPC186531
0.7326 Intermediate Similarity NPC115786
0.7326 Intermediate Similarity NPC41856
0.7326 Intermediate Similarity NPC474865
0.7317 Intermediate Similarity NPC470240
0.7317 Intermediate Similarity NPC7563
0.7317 Intermediate Similarity NPC187568
0.7317 Intermediate Similarity NPC320630
0.7317 Intermediate Similarity NPC41780
0.7317 Intermediate Similarity NPC476794
0.7317 Intermediate Similarity NPC116177
0.7303 Intermediate Similarity NPC64913
0.7303 Intermediate Similarity NPC242877
0.7294 Intermediate Similarity NPC35556
0.7284 Intermediate Similarity NPC469414
0.7284 Intermediate Similarity NPC329826
0.7273 Intermediate Similarity NPC472266
0.7273 Intermediate Similarity NPC160138
0.7273 Intermediate Similarity NPC475703
0.7241 Intermediate Similarity NPC78089
0.7241 Intermediate Similarity NPC470755
0.7237 Intermediate Similarity NPC470688
0.7229 Intermediate Similarity NPC267231
0.7229 Intermediate Similarity NPC472960
0.7215 Intermediate Similarity NPC469660
0.7209 Intermediate Similarity NPC131669
0.7209 Intermediate Similarity NPC473390
0.7209 Intermediate Similarity NPC116543
0.72 Intermediate Similarity NPC68110
0.7195 Intermediate Similarity NPC68819
0.7195 Intermediate Similarity NPC235906
0.7191 Intermediate Similarity NPC469628
0.7191 Intermediate Similarity NPC475739
0.7191 Intermediate Similarity NPC471047
0.7191 Intermediate Similarity NPC475902
0.7191 Intermediate Similarity NPC475906
0.7191 Intermediate Similarity NPC469653
0.7191 Intermediate Similarity NPC469631
0.7179 Intermediate Similarity NPC276290
0.7176 Intermediate Similarity NPC24417
0.7174 Intermediate Similarity NPC474338
0.716 Intermediate Similarity NPC188354
0.7159 Intermediate Similarity NPC469483
0.7159 Intermediate Similarity NPC305475
0.7159 Intermediate Similarity NPC475461
0.7159 Intermediate Similarity NPC261721
0.7143 Intermediate Similarity NPC99651
0.7143 Intermediate Similarity NPC167881
0.7143 Intermediate Similarity NPC98557
0.7143 Intermediate Similarity NPC617
0.7143 Intermediate Similarity NPC141831
0.7128 Intermediate Similarity NPC471462
0.7126 Intermediate Similarity NPC476804
0.7126 Intermediate Similarity NPC158756
0.7125 Intermediate Similarity NPC269103
0.7125 Intermediate Similarity NPC124072
0.7111 Intermediate Similarity NPC295312
0.7108 Intermediate Similarity NPC65603
0.7093 Intermediate Similarity NPC229825
0.7093 Intermediate Similarity NPC475046
0.7093 Intermediate Similarity NPC474959
0.7093 Intermediate Similarity NPC310450
0.7093 Intermediate Similarity NPC11383
0.7089 Intermediate Similarity NPC265574
0.7083 Intermediate Similarity NPC245002
0.7073 Intermediate Similarity NPC226669
0.7073 Intermediate Similarity NPC138408
0.7073 Intermediate Similarity NPC155587
0.7073 Intermediate Similarity NPC193351
0.7059 Intermediate Similarity NPC223904
0.7059 Intermediate Similarity NPC302426
0.7053 Intermediate Similarity NPC279561
0.7045 Intermediate Similarity NPC474424
0.7045 Intermediate Similarity NPC130030
0.7045 Intermediate Similarity NPC255307
0.7037 Intermediate Similarity NPC222244
0.7037 Intermediate Similarity NPC287878
0.7037 Intermediate Similarity NPC16349
0.7033 Intermediate Similarity NPC232426
0.7033 Intermediate Similarity NPC281942
0.7027 Intermediate Similarity NPC286189
0.7024 Intermediate Similarity NPC471465
0.7024 Intermediate Similarity NPC471220
0.7024 Intermediate Similarity NPC196653
0.7013 Intermediate Similarity NPC282760
0.7013 Intermediate Similarity NPC131174
0.7011 Intermediate Similarity NPC229799
0.7011 Intermediate Similarity NPC193198
0.7011 Intermediate Similarity NPC286770
0.7011 Intermediate Similarity NPC53867
0.7011 Intermediate Similarity NPC318468
0.7011 Intermediate Similarity NPC474703
0.7011 Intermediate Similarity NPC475714
0.7011 Intermediate Similarity NPC284472
0.7 Intermediate Similarity NPC475819
0.7 Intermediate Similarity NPC226863
0.7 Intermediate Similarity NPC476805
0.6989 Remote Similarity NPC473316
0.6989 Remote Similarity NPC475832
0.6989 Remote Similarity NPC473330
0.6989 Remote Similarity NPC475927
0.6989 Remote Similarity NPC470521
0.6989 Remote Similarity NPC140543
0.6988 Remote Similarity NPC27205
0.6979 Remote Similarity NPC469402
0.6979 Remote Similarity NPC473219
0.6979 Remote Similarity NPC470761
0.6977 Remote Similarity NPC275507
0.6974 Remote Similarity NPC179087
0.6974 Remote Similarity NPC44343
0.6974 Remote Similarity NPC210303
0.6966 Remote Similarity NPC469910
0.6966 Remote Similarity NPC50637
0.6957 Remote Similarity NPC175842
0.6957 Remote Similarity NPC32494
0.6957 Remote Similarity NPC473707
0.6957 Remote Similarity NPC471059
0.6941 Remote Similarity NPC182550
0.6941 Remote Similarity NPC472965
0.6941 Remote Similarity NPC264227
0.6941 Remote Similarity NPC63649
0.6941 Remote Similarity NPC473981
0.6941 Remote Similarity NPC473980
0.6933 Remote Similarity NPC79756
0.6932 Remote Similarity NPC149869
0.6932 Remote Similarity NPC475100
0.6932 Remote Similarity NPC163093
0.6932 Remote Similarity NPC159635
0.6932 Remote Similarity NPC191476
0.6932 Remote Similarity NPC114979
0.6932 Remote Similarity NPC82297
0.6932 Remote Similarity NPC141193
0.6932 Remote Similarity NPC96259
0.6932 Remote Similarity NPC31086

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC10572 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
0.6897 Remote Similarity NPD5209 Approved
0.6897 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6795 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6556 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6489 Remote Similarity NPD46 Approved
0.6489 Remote Similarity NPD6698 Approved
0.6484 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6444 Remote Similarity NPD7154 Phase 3
0.6392 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6389 Remote Similarity NPD6927 Phase 3
0.6383 Remote Similarity NPD1695 Approved
0.6346 Remote Similarity NPD6686 Approved
0.6316 Remote Similarity NPD5785 Approved
0.6304 Remote Similarity NPD1694 Approved
0.6292 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6264 Remote Similarity NPD5362 Discontinued
0.62 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6146 Remote Similarity NPD7838 Discovery
0.6129 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6129 Remote Similarity NPD5363 Approved
0.6095 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6092 Remote Similarity NPD8039 Approved
0.6067 Remote Similarity NPD4271 Approved
0.6067 Remote Similarity NPD4268 Approved
0.6064 Remote Similarity NPD4249 Approved
0.604 Remote Similarity NPD4225 Approved
0.6 Remote Similarity NPD4250 Approved
0.6 Remote Similarity NPD4251 Approved
0.5955 Remote Similarity NPD4756 Discovery
0.5934 Remote Similarity NPD4819 Approved
0.5934 Remote Similarity NPD4820 Approved
0.5934 Remote Similarity NPD4252 Approved
0.5934 Remote Similarity NPD4821 Approved
0.5934 Remote Similarity NPD4822 Approved
0.5914 Remote Similarity NPD5332 Approved
0.5914 Remote Similarity NPD5331 Approved
0.5889 Remote Similarity NPD5784 Clinical (unspecified phase)
0.587 Remote Similarity NPD4790 Discontinued
0.5842 Remote Similarity NPD7839 Suspended
0.5833 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5806 Remote Similarity NPD4270 Approved
0.5806 Remote Similarity NPD6435 Approved
0.5806 Remote Similarity NPD4269 Approved
0.578 Remote Similarity NPD6371 Approved
0.5773 Remote Similarity NPD6903 Approved
0.5763 Remote Similarity NPD7507 Approved
0.5758 Remote Similarity NPD7983 Approved
0.5753 Remote Similarity NPD5343 Approved
0.5729 Remote Similarity NPD7334 Approved
0.5729 Remote Similarity NPD6684 Approved
0.5729 Remote Similarity NPD5330 Approved
0.5729 Remote Similarity NPD6409 Approved
0.5729 Remote Similarity NPD5786 Approved
0.5729 Remote Similarity NPD7146 Approved
0.5729 Remote Similarity NPD7521 Approved
0.5728 Remote Similarity NPD7638 Approved
0.5727 Remote Similarity NPD8413 Clinical (unspecified phase)
0.57 Remote Similarity NPD5779 Approved
0.57 Remote Similarity NPD5778 Approved
0.5699 Remote Similarity NPD5369 Approved
0.5694 Remote Similarity NPD3174 Discontinued
0.5679 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5676 Remote Similarity NPD6053 Discontinued
0.5673 Remote Similarity NPD7639 Approved
0.5673 Remote Similarity NPD7640 Approved
0.562 Remote Similarity NPD7319 Approved
0.5612 Remote Similarity NPD5737 Approved
0.5612 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5612 Remote Similarity NPD6672 Approved
0.56 Remote Similarity NPD5693 Phase 1
0.56 Remote Similarity NPD7637 Suspended

Structure

External Identifiers

PubChem CID   11624964
ChEMBL   CHEMBL463760
ZINC  

Physicochemical Properties

Molecular Weight:  374.17
ALogP:  3.0628
MLogP:  3.11
XLogP:  2.034
# Rotatable Bonds:  13
Polar Surface Area:  78.9
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  27

Download Data

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Similar NPs/Drugs