Natural Product: NPC53581

Natural Product ID:  NPC53581
Common Name:   Curcumanolides B
IUPAC Name:   (5R,6S,9R)-6-methyl-3-propan-2-ylidene-9-prop-1-en-2-yl-1-oxaspiro[4.4]nonan-2-one
Synonyms:   Curcumanolides B
Molecular Formula:   C15H22O2
Standard InCHIKey:  KHOTZHZBHNDKOB-NJZAAPMLSA-N
Standard InCHI:  InChI=1S/C15H22O2/c1-9(2)12-8-15(17-14(12)16)11(5)6-7-13(15)10(3)4/h11,13H,3,6-8H2,1-2,4-5H3/t11-,13+,15+/m0/s1
Canonical SMILES:  CC(=C1C[C@@]2(OC1=O)[C@@H](C)CC[C@@H]2C(=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
NPO17780 Curcuma heyneana Species Zingiberaceae Eukaryota Rhizomes PMID[23387824]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition < 65 % 26227773

  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 NPC53581 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
1.0 High Similarity NPC103987
0.8816 High Similarity NPC222210
0.8816 High Similarity NPC63445
0.8462 Intermediate Similarity NPC182550
0.8395 Intermediate Similarity NPC156485
0.8354 Intermediate Similarity NPC74673
0.8354 Intermediate Similarity NPC69271
0.8354 Intermediate Similarity NPC276356
0.8293 Intermediate Similarity NPC235792
0.8235 Intermediate Similarity NPC301969
0.8235 Intermediate Similarity NPC37607
0.8205 Intermediate Similarity NPC122264
0.8193 Intermediate Similarity NPC67493
0.8125 Intermediate Similarity NPC47747
0.8125 Intermediate Similarity NPC302426
0.8077 Intermediate Similarity NPC235906
0.8072 Intermediate Similarity NPC78089
0.8052 Intermediate Similarity NPC469643
0.8052 Intermediate Similarity NPC143979
0.8052 Intermediate Similarity NPC320537
0.8052 Intermediate Similarity NPC469641
0.8049 Intermediate Similarity NPC245665
0.8025 Intermediate Similarity NPC59994
0.8025 Intermediate Similarity NPC78677
0.8025 Intermediate Similarity NPC10276
0.8025 Intermediate Similarity NPC35089
0.8 Intermediate Similarity NPC224652
0.7976 Intermediate Similarity NPC107787
0.7975 Intermediate Similarity NPC15975
0.7975 Intermediate Similarity NPC41780
0.7975 Intermediate Similarity NPC65603
0.7975 Intermediate Similarity NPC187568
0.7975 Intermediate Similarity NPC195785
0.7875 Intermediate Similarity NPC299235
0.7865 Intermediate Similarity NPC52044
0.7865 Intermediate Similarity NPC67584
0.7857 Intermediate Similarity NPC245434
0.7857 Intermediate Similarity NPC284534
0.7857 Intermediate Similarity NPC300082
0.7857 Intermediate Similarity NPC204105
0.7848 Intermediate Similarity NPC123360
0.7831 Intermediate Similarity NPC39588
0.7821 Intermediate Similarity NPC476355
0.7805 Intermediate Similarity NPC141810
0.7792 Intermediate Similarity NPC129665
0.7792 Intermediate Similarity NPC163003
0.7791 Intermediate Similarity NPC91248
0.7778 Intermediate Similarity NPC213078
0.7778 Intermediate Similarity NPC617
0.7765 Intermediate Similarity NPC64153
0.7763 Intermediate Similarity NPC5714
0.7763 Intermediate Similarity NPC265574
0.7753 Intermediate Similarity NPC477131
0.7753 Intermediate Similarity NPC127019
0.775 Intermediate Similarity NPC208223
0.775 Intermediate Similarity NPC476794
0.775 Intermediate Similarity NPC470240
0.7738 Intermediate Similarity NPC238197
0.7738 Intermediate Similarity NPC115786
0.7722 Intermediate Similarity NPC244166
0.7722 Intermediate Similarity NPC155587
0.7722 Intermediate Similarity NPC226669
0.7722 Intermediate Similarity NPC193351
0.7722 Intermediate Similarity NPC138408
0.7711 Intermediate Similarity NPC186276
0.7711 Intermediate Similarity NPC173609
0.7701 Intermediate Similarity NPC212664
0.7701 Intermediate Similarity NPC288699
0.7701 Intermediate Similarity NPC4986
0.7692 Intermediate Similarity NPC58956
0.7692 Intermediate Similarity NPC161493
0.7692 Intermediate Similarity NPC269206
0.7692 Intermediate Similarity NPC295633
0.7683 Intermediate Similarity NPC293418
0.7683 Intermediate Similarity NPC6823
0.7683 Intermediate Similarity NPC73052
0.7683 Intermediate Similarity NPC223904
0.7683 Intermediate Similarity NPC290508
0.7674 Intermediate Similarity NPC270270
0.7674 Intermediate Similarity NPC475703
0.7667 Intermediate Similarity NPC170120
0.7667 Intermediate Similarity NPC213698
0.7654 Intermediate Similarity NPC128276
0.7647 Intermediate Similarity NPC161957
0.7647 Intermediate Similarity NPC215364
0.7647 Intermediate Similarity NPC33570
0.7647 Intermediate Similarity NPC21471
0.764 Intermediate Similarity NPC135776
0.7625 Intermediate Similarity NPC473223
0.7619 Intermediate Similarity NPC22611
0.7619 Intermediate Similarity NPC215294
0.7609 Intermediate Similarity NPC221615
0.7595 Intermediate Similarity NPC140287
0.759 Intermediate Similarity NPC281949
0.759 Intermediate Similarity NPC39411
0.759 Intermediate Similarity NPC325031
0.759 Intermediate Similarity NPC25684
0.759 Intermediate Similarity NPC471325
0.759 Intermediate Similarity NPC255580
0.759 Intermediate Similarity NPC301477
0.7586 Intermediate Similarity NPC79549
0.7561 Intermediate Similarity NPC264227
0.7561 Intermediate Similarity NPC178277
0.7561 Intermediate Similarity NPC470239
0.7561 Intermediate Similarity NPC89128
0.7561 Intermediate Similarity NPC63649
0.7561 Intermediate Similarity NPC470244
0.7561 Intermediate Similarity NPC472965
0.7561 Intermediate Similarity NPC469620
0.7561 Intermediate Similarity NPC469690
0.7558 Intermediate Similarity NPC261253
0.7558 Intermediate Similarity NPC284902
0.7558 Intermediate Similarity NPC474045
0.7556 Intermediate Similarity NPC470010
0.7556 Intermediate Similarity NPC323008
0.7556 Intermediate Similarity NPC470013
0.7556 Intermediate Similarity NPC262133
0.7531 Intermediate Similarity NPC472014
0.7531 Intermediate Similarity NPC57744
0.7529 Intermediate Similarity NPC475100
0.7528 Intermediate Similarity NPC261607
0.7528 Intermediate Similarity NPC221282
0.7528 Intermediate Similarity NPC300312
0.7528 Intermediate Similarity NPC111114
0.7528 Intermediate Similarity NPC472953
0.7528 Intermediate Similarity NPC133698
0.7528 Intermediate Similarity NPC290651
0.7528 Intermediate Similarity NPC131209
0.75 Intermediate Similarity NPC472872
0.75 Intermediate Similarity NPC268298
0.75 Intermediate Similarity NPC89555
0.75 Intermediate Similarity NPC215556
0.75 Intermediate Similarity NPC35556
0.75 Intermediate Similarity NPC32922
0.75 Intermediate Similarity NPC246076
0.7473 Intermediate Similarity NPC224689
0.7471 Intermediate Similarity NPC160138
0.7471 Intermediate Similarity NPC201658
0.7471 Intermediate Similarity NPC237540
0.747 Intermediate Similarity NPC156658
0.747 Intermediate Similarity NPC258965
0.747 Intermediate Similarity NPC195424
0.7447 Intermediate Similarity NPC150923
0.7444 Intermediate Similarity NPC37816
0.7442 Intermediate Similarity NPC471185
0.7442 Intermediate Similarity NPC146850
0.7442 Intermediate Similarity NPC287015
0.7439 Intermediate Similarity NPC108816
0.7439 Intermediate Similarity NPC472960
0.7439 Intermediate Similarity NPC267231
0.7439 Intermediate Similarity NPC93763
0.7436 Intermediate Similarity NPC472955
0.7416 Intermediate Similarity NPC49946
0.7416 Intermediate Similarity NPC216284
0.7416 Intermediate Similarity NPC129419
0.7416 Intermediate Similarity NPC312042
0.7416 Intermediate Similarity NPC62815
0.7416 Intermediate Similarity NPC306168
0.7412 Intermediate Similarity NPC53867
0.7412 Intermediate Similarity NPC54468
0.7412 Intermediate Similarity NPC193198
0.7412 Intermediate Similarity NPC250315
0.7412 Intermediate Similarity NPC272814
0.7412 Intermediate Similarity NPC475947
0.7386 Intermediate Similarity NPC226863
0.7386 Intermediate Similarity NPC178875
0.7381 Intermediate Similarity NPC42470
0.7368 Intermediate Similarity NPC18252
0.7363 Intermediate Similarity NPC198853
0.7363 Intermediate Similarity NPC167219
0.7363 Intermediate Similarity NPC96541
0.7356 Intermediate Similarity NPC279859
0.7356 Intermediate Similarity NPC50637
0.7356 Intermediate Similarity NPC469676
0.7356 Intermediate Similarity NPC38576
0.7356 Intermediate Similarity NPC305475
0.7356 Intermediate Similarity NPC475461
0.7356 Intermediate Similarity NPC236692
0.7356 Intermediate Similarity NPC56593
0.7356 Intermediate Similarity NPC309757
0.7349 Intermediate Similarity NPC270126
0.7349 Intermediate Similarity NPC469617
0.7349 Intermediate Similarity NPC472013
0.7349 Intermediate Similarity NPC476624
0.7333 Intermediate Similarity NPC155215
0.7333 Intermediate Similarity NPC475925
0.7326 Intermediate Similarity NPC82297
0.7326 Intermediate Similarity NPC470918
0.7326 Intermediate Similarity NPC159635
0.7326 Intermediate Similarity NPC191476
0.7326 Intermediate Similarity NPC165287
0.7326 Intermediate Similarity NPC114979
0.7317 Intermediate Similarity NPC7563
0.7317 Intermediate Similarity NPC474760
0.7317 Intermediate Similarity NPC171204
0.7317 Intermediate Similarity NPC97516
0.7317 Intermediate Similarity NPC116177
0.7317 Intermediate Similarity NPC476028
0.7317 Intermediate Similarity NPC320630
0.7317 Intermediate Similarity NPC141789

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC53581 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
0.7701 Intermediate Similarity NPD1695 Approved
0.7416 Intermediate Similarity NPD5207 Approved
0.7333 Intermediate Similarity NPD5693 Phase 1
0.7241 Intermediate Similarity NPD1694 Approved
0.7209 Intermediate Similarity NPD5362 Discontinued
0.7174 Intermediate Similarity NPD6001 Approved
0.7097 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD5785 Approved
0.7 Intermediate Similarity NPD5208 Approved
0.6923 Remote Similarity NPD6673 Approved
0.6923 Remote Similarity NPD6080 Approved
0.6923 Remote Similarity NPD6904 Approved
0.6915 Remote Similarity NPD1698 Clinical (unspecified phase)
0.69 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6854 Remote Similarity NPD5363 Approved
0.6848 Remote Similarity NPD5692 Phase 3
0.6813 Remote Similarity NPD6903 Approved
0.6795 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6782 Remote Similarity NPD5369 Approved
0.6778 Remote Similarity NPD7146 Approved
0.6778 Remote Similarity NPD6684 Approved
0.6778 Remote Similarity NPD5330 Approved
0.6778 Remote Similarity NPD7521 Approved
0.6778 Remote Similarity NPD6098 Approved
0.6778 Remote Similarity NPD7334 Approved
0.6778 Remote Similarity NPD6409 Approved
0.6774 Remote Similarity NPD6050 Approved
0.6774 Remote Similarity NPD5694 Approved
0.6705 Remote Similarity NPD4269 Approved
0.6705 Remote Similarity NPD4270 Approved
0.6634 Remote Similarity NPD6008 Approved
0.663 Remote Similarity NPD7513 Clinical (unspecified phase)
0.663 Remote Similarity NPD6672 Approved
0.663 Remote Similarity NPD5737 Approved
0.6629 Remote Similarity NPD5332 Approved
0.6629 Remote Similarity NPD5331 Approved
0.66 Remote Similarity NPD6052 Approved
0.6596 Remote Similarity NPD5284 Approved
0.6596 Remote Similarity NPD5281 Approved
0.6593 Remote Similarity NPD5786 Approved
0.6591 Remote Similarity NPD4790 Discontinued
0.6571 Remote Similarity NPD6053 Discontinued
0.6562 Remote Similarity NPD5695 Phase 3
0.6531 Remote Similarity NPD5696 Approved
0.6517 Remote Similarity NPD4221 Approved
0.6517 Remote Similarity NPD4223 Phase 3
0.6517 Remote Similarity NPD5209 Approved
0.6477 Remote Similarity NPD4821 Approved
0.6477 Remote Similarity NPD4819 Approved
0.6477 Remote Similarity NPD4252 Approved
0.6477 Remote Similarity NPD4820 Approved
0.6477 Remote Similarity NPD4822 Approved
0.6477 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6471 Remote Similarity NPD8039 Approved
0.6444 Remote Similarity NPD7154 Phase 3
0.6437 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6083 Phase 2
0.6429 Remote Similarity NPD6084 Phase 2
0.6413 Remote Similarity NPD4249 Approved
0.6392 Remote Similarity NPD5654 Approved
0.6383 Remote Similarity NPD6051 Approved
0.6381 Remote Similarity NPD6371 Approved
0.6374 Remote Similarity NPD4197 Approved
0.6354 Remote Similarity NPD6399 Phase 3
0.6344 Remote Similarity NPD4251 Approved
0.6344 Remote Similarity NPD4250 Approved
0.6333 Remote Similarity NPD6435 Approved
0.6316 Remote Similarity NPD46 Approved
0.6316 Remote Similarity NPD6698 Approved
0.6304 Remote Similarity NPD5329 Approved
0.6277 Remote Similarity NPD4518 Approved
0.6263 Remote Similarity NPD5959 Approved
0.625 Remote Similarity NPD4271 Approved
0.625 Remote Similarity NPD4268 Approved
0.6237 Remote Similarity NPD4138 Approved
0.6237 Remote Similarity NPD4689 Approved
0.6237 Remote Similarity NPD4694 Approved
0.6237 Remote Similarity NPD4693 Phase 3
0.6237 Remote Similarity NPD5690 Phase 2
0.6237 Remote Similarity NPD5280 Approved
0.6237 Remote Similarity NPD4688 Approved
0.6237 Remote Similarity NPD4690 Approved
0.6237 Remote Similarity NPD5205 Approved
0.62 Remote Similarity NPD4225 Approved
0.62 Remote Similarity NPD7638 Approved
0.6182 Remote Similarity NPD7115 Discovery
0.6173 Remote Similarity NPD7341 Phase 2
0.617 Remote Similarity NPD3573 Approved
0.6154 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6139 Remote Similarity NPD7640 Approved
0.6139 Remote Similarity NPD7639 Approved
0.6122 Remote Similarity NPD5282 Discontinued
0.6111 Remote Similarity NPD5368 Approved
0.6098 Remote Similarity NPD7331 Phase 2
0.6095 Remote Similarity NPD6614 Approved
0.6064 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6042 Remote Similarity NPD4753 Phase 2
0.6038 Remote Similarity NPD7320 Approved
0.6022 Remote Similarity NPD3665 Phase 1
0.6022 Remote Similarity NPD3666 Approved
0.6022 Remote Similarity NPD3133 Approved
0.6 Remote Similarity NPD6675 Approved
0.6 Remote Similarity NPD4747 Approved
0.6 Remote Similarity NPD5739 Approved
0.6 Remote Similarity NPD7128 Approved
0.6 Remote Similarity NPD6402 Approved
0.5981 Remote Similarity NPD6372 Approved
0.5981 Remote Similarity NPD6373 Approved
0.5979 Remote Similarity NPD4096 Approved
0.5943 Remote Similarity NPD5701 Approved
0.5943 Remote Similarity NPD5697 Approved
0.593 Remote Similarity NPD5276 Approved
0.59 Remote Similarity NPD5210 Approved
0.59 Remote Similarity NPD4629 Approved
0.5895 Remote Similarity NPD4623 Approved
0.5895 Remote Similarity NPD4519 Discontinued
0.5895 Remote Similarity NPD3618 Phase 1
0.5895 Remote Similarity NPD5279 Phase 3
0.5889 Remote Similarity NPD3617 Approved
0.5888 Remote Similarity NPD6881 Approved
0.5888 Remote Similarity NPD6899 Approved
0.5888 Remote Similarity NPD6011 Approved
0.5882 Remote Similarity NPD4137 Phase 3
0.5872 Remote Similarity NPD6650 Approved
0.5872 Remote Similarity NPD6649 Approved
0.587 Remote Similarity NPD4139 Approved
0.587 Remote Similarity NPD857 Phase 3
0.587 Remote Similarity NPD4692 Approved
0.5859 Remote Similarity NPD5778 Approved
0.5859 Remote Similarity NPD5779 Approved
0.5859 Remote Similarity NPD4202 Approved
0.5851 Remote Similarity NPD4786 Approved
0.5833 Remote Similarity NPD6013 Approved
0.5833 Remote Similarity NPD6012 Approved
0.5833 Remote Similarity NPD6014 Approved
0.5825 Remote Similarity NPD6404 Discontinued
0.5824 Remote Similarity NPD4195 Approved
0.5816 Remote Similarity NPD7838 Discovery
0.5814 Remote Similarity NPD4691 Approved
0.5806 Remote Similarity NPD3667 Approved
0.58 Remote Similarity NPD7901 Clinical (unspecified phase)
0.58 Remote Similarity NPD7900 Approved
0.5795 Remote Similarity NPD5733 Approved
0.5795 Remote Similarity NPD4687 Approved
0.5794 Remote Similarity NPD5954 Clinical (unspecified phase)
0.578 Remote Similarity NPD6883 Approved
0.578 Remote Similarity NPD7102 Approved
0.578 Remote Similarity NPD7290 Approved
0.5778 Remote Similarity NPD4756 Discovery
0.5763 Remote Similarity NPD7507 Approved
0.5761 Remote Similarity NPD4695 Discontinued
0.5758 Remote Similarity NPD8035 Phase 2
0.5758 Remote Similarity NPD7637 Suspended
0.5758 Remote Similarity NPD8034 Phase 2
0.5745 Remote Similarity NPD4788 Approved
0.5741 Remote Similarity NPD6686 Approved
0.5733 Remote Similarity NPD28 Approved
0.5733 Remote Similarity NPD29 Approved
0.5728 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5727 Remote Similarity NPD6617 Approved
0.5727 Remote Similarity NPD2181 Clinical (unspecified phase)
0.5727 Remote Similarity NPD8130 Phase 1
0.5727 Remote Similarity NPD6869 Approved
0.5727 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5727 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5727 Remote Similarity NPD6847 Approved
0.5714 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7632 Discontinued
0.5714 Remote Similarity NPD6101 Approved
0.5714 Remote Similarity NPD5328 Approved
0.5714 Remote Similarity NPD9298 Approved
0.5714 Remote Similarity NPD5370 Suspended
0.57 Remote Similarity NPD5133 Approved
0.569 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5684 Remote Similarity NPD3668 Phase 3
0.5676 Remote Similarity NPD6882 Approved
0.5676 Remote Similarity NPD8297 Approved
0.5644 Remote Similarity NPD7748 Approved
0.5636 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5631 Remote Similarity NPD7902 Approved
0.5631 Remote Similarity NPD4755 Approved
0.5625 Remote Similarity NPD7520 Clinical (unspecified phase)
0.562 Remote Similarity NPD7319 Approved
0.5618 Remote Similarity NPD4058 Approved
0.5607 Remote Similarity NPD5909 Discontinued
0.56 Remote Similarity NPD7983 Approved
0.56 Remote Similarity NPD6079 Approved
0.56 Remote Similarity NPD6411 Approved
0.56 Remote Similarity NPD4810 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   14191394
ChEMBL   CHEMBL2332434
ZINC  

Physicochemical Properties

Molecular Weight:  234.16
ALogP:  3.07
MLogP:  2.89
XLogP:  3.028
# Rotatable Bonds:  5
Polar Surface Area:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  17

Download Data

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