Natural Product: NPC471267

Natural Product ID:  NPC471267
Common Name:   Wilsonol C
IUPAC Name:   (E)-4-[(1R,4S,5S,6R)-1,4,5-trihydroxy-2,2,6-trimethylcyclohexyl]but-3-en-2-one
Synonyms:  
Molecular Formula:   C13H22O4
Standard InCHIKey:  OJRIULXCUMIXBT-VZTUNGRISA-N
Standard InCHI:  InChI=1S/C13H22O4/c1-8(14)5-6-13(17)9(2)11(16)10(15)7-12(13,3)4/h5-6,9-11,15-17H,7H2,1-4H3/b6-5+/t9-,10+,11+,13-/m1/s1
Canonical SMILES:  CC(=O)/C=C/[C@@]1(O)[C@H](C)[C@H](O)[C@H](CC1(C)C)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
NPO32875 cinnamomum wilsonii Species Lauraceae Eukaryota Leaves PMID[23822611]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000 nM 8277308
NPT81 Cell Line A549 Homo sapiens IC50 > 10000 nM 10.6019/CHEMBL1201861
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000 nM 19581457
NPT660 Cell Line SW480 Homo sapiens IC50 > 10000 nM 18024584
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 10000 nM 10.1021/np50041a029

  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 NPC471267 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
0.95 High Similarity NPC471987
0.9125 High Similarity NPC95124
0.9125 High Similarity NPC471266
0.9012 High Similarity NPC471270
0.8987 High Similarity NPC85105
0.8987 High Similarity NPC149550
0.8889 High Similarity NPC236707
0.8404 Intermediate Similarity NPC214277
0.8353 Intermediate Similarity NPC185605
0.8202 Intermediate Similarity NPC473100
0.8172 Intermediate Similarity NPC120446
0.8125 Intermediate Similarity NPC471268
0.8125 Intermediate Similarity NPC471272
0.8125 Intermediate Similarity NPC471271
0.8111 Intermediate Similarity NPC473099
0.8021 Intermediate Similarity NPC150463
0.7957 Intermediate Similarity NPC476245
0.7931 Intermediate Similarity NPC79945
0.7865 Intermediate Similarity NPC475069
0.7865 Intermediate Similarity NPC175145
0.7857 Intermediate Similarity NPC194941
0.7849 Intermediate Similarity NPC196227
0.7826 Intermediate Similarity NPC116726
0.7816 Intermediate Similarity NPC259858
0.7802 Intermediate Similarity NPC314727
0.775 Intermediate Similarity NPC471238
0.7742 Intermediate Similarity NPC110022
0.7727 Intermediate Similarity NPC251475
0.7727 Intermediate Similarity NPC169941
0.7723 Intermediate Similarity NPC163004
0.7717 Intermediate Similarity NPC134321
0.7701 Intermediate Similarity NPC249423
0.7677 Intermediate Similarity NPC473068
0.766 Intermediate Similarity NPC103527
0.7634 Intermediate Similarity NPC473675
0.7634 Intermediate Similarity NPC97404
0.7634 Intermediate Similarity NPC275671
0.7634 Intermediate Similarity NPC41554
0.7629 Intermediate Similarity NPC38855
0.7609 Intermediate Similarity NPC187785
0.7609 Intermediate Similarity NPC82876
0.7609 Intermediate Similarity NPC259875
0.7609 Intermediate Similarity NPC115607
0.7576 Intermediate Similarity NPC473070
0.7551 Intermediate Similarity NPC470184
0.7529 Intermediate Similarity NPC1973
0.7529 Intermediate Similarity NPC167873
0.7527 Intermediate Similarity NPC128672
0.7527 Intermediate Similarity NPC204188
0.7527 Intermediate Similarity NPC11216
0.7527 Intermediate Similarity NPC291484
0.7527 Intermediate Similarity NPC329596
0.7527 Intermediate Similarity NPC3345
0.7527 Intermediate Similarity NPC80561
0.7527 Intermediate Similarity NPC19771
0.75 Intermediate Similarity NPC472995
0.75 Intermediate Similarity NPC133588
0.7474 Intermediate Similarity NPC469491
0.7474 Intermediate Similarity NPC472976
0.7474 Intermediate Similarity NPC478089
0.7474 Intermediate Similarity NPC472977
0.7473 Intermediate Similarity NPC472986
0.7473 Intermediate Similarity NPC472985
0.7473 Intermediate Similarity NPC299068
0.7473 Intermediate Similarity NPC179591
0.7451 Intermediate Similarity NPC473069
0.7451 Intermediate Similarity NPC181994
0.7451 Intermediate Similarity NPC65941
0.7447 Intermediate Similarity NPC472978
0.7444 Intermediate Similarity NPC83702
0.7444 Intermediate Similarity NPC40687
0.7442 Intermediate Similarity NPC203403
0.7423 Intermediate Similarity NPC477226
0.7423 Intermediate Similarity NPC474938
0.7423 Intermediate Similarity NPC474785
0.7423 Intermediate Similarity NPC287668
0.7419 Intermediate Similarity NPC257485
0.7419 Intermediate Similarity NPC97103
0.7419 Intermediate Similarity NPC472983
0.7419 Intermediate Similarity NPC470361
0.7419 Intermediate Similarity NPC109744
0.7416 Intermediate Similarity NPC92226
0.7416 Intermediate Similarity NPC2524
0.74 Intermediate Similarity NPC474822
0.74 Intermediate Similarity NPC474575
0.7396 Intermediate Similarity NPC276110
0.7396 Intermediate Similarity NPC272617
0.7396 Intermediate Similarity NPC180950
0.7391 Intermediate Similarity NPC472324
0.7386 Intermediate Similarity NPC281880
0.7386 Intermediate Similarity NPC287749
0.7386 Intermediate Similarity NPC96362
0.7379 Intermediate Similarity NPC475586
0.7375 Intermediate Similarity NPC86856
0.7374 Intermediate Similarity NPC472554
0.7374 Intermediate Similarity NPC11974
0.7368 Intermediate Similarity NPC119379
0.7368 Intermediate Similarity NPC310013
0.7363 Intermediate Similarity NPC470360
0.7363 Intermediate Similarity NPC109528
0.7358 Intermediate Similarity NPC472400
0.7356 Intermediate Similarity NPC476949
0.7353 Intermediate Similarity NPC471205
0.7353 Intermediate Similarity NPC477916
0.7353 Intermediate Similarity NPC122816
0.7353 Intermediate Similarity NPC83744
0.734 Intermediate Similarity NPC475751
0.734 Intermediate Similarity NPC472642
0.734 Intermediate Similarity NPC473956
0.734 Intermediate Similarity NPC191323
0.734 Intermediate Similarity NPC230332
0.7333 Intermediate Similarity NPC472002
0.7333 Intermediate Similarity NPC477978
0.7326 Intermediate Similarity NPC253190
0.732 Intermediate Similarity NPC471903
0.732 Intermediate Similarity NPC210717
0.732 Intermediate Similarity NPC165632
0.732 Intermediate Similarity NPC473153
0.732 Intermediate Similarity NPC473158
0.732 Intermediate Similarity NPC202833
0.732 Intermediate Similarity NPC103165
0.732 Intermediate Similarity NPC288970
0.7317 Intermediate Similarity NPC117804
0.7312 Intermediate Similarity NPC158778
0.7312 Intermediate Similarity NPC104560
0.7312 Intermediate Similarity NPC471793
0.7312 Intermediate Similarity NPC475605
0.7312 Intermediate Similarity NPC471791
0.7312 Intermediate Similarity NPC280556
0.7312 Intermediate Similarity NPC474668
0.7312 Intermediate Similarity NPC291665
0.7303 Intermediate Similarity NPC159148
0.7303 Intermediate Similarity NPC476646
0.73 Intermediate Similarity NPC11956
0.73 Intermediate Similarity NPC475038
0.73 Intermediate Similarity NPC109195
0.73 Intermediate Similarity NPC472552
0.7294 Intermediate Similarity NPC22134
0.7294 Intermediate Similarity NPC306727
0.7292 Intermediate Similarity NPC258674
0.7292 Intermediate Similarity NPC119562
0.7292 Intermediate Similarity NPC299100
0.7292 Intermediate Similarity NPC279410
0.7292 Intermediate Similarity NPC105490
0.7283 Intermediate Similarity NPC472974
0.7283 Intermediate Similarity NPC255143
0.7282 Intermediate Similarity NPC329417
0.7282 Intermediate Similarity NPC217201
0.7273 Intermediate Similarity NPC470429
0.7273 Intermediate Similarity NPC16601
0.7273 Intermediate Similarity NPC475877
0.7273 Intermediate Similarity NPC308038
0.7264 Intermediate Similarity NPC108721
0.7264 Intermediate Similarity NPC73300
0.7264 Intermediate Similarity NPC472757
0.7263 Intermediate Similarity NPC73457
0.7263 Intermediate Similarity NPC230623
0.7263 Intermediate Similarity NPC78594
0.7263 Intermediate Similarity NPC252433
0.7262 Intermediate Similarity NPC164022
0.7262 Intermediate Similarity NPC477792
0.7262 Intermediate Similarity NPC23954
0.7255 Intermediate Similarity NPC296945
0.7255 Intermediate Similarity NPC171137
0.7255 Intermediate Similarity NPC150531
0.7255 Intermediate Similarity NPC214264
0.7255 Intermediate Similarity NPC260268
0.7255 Intermediate Similarity NPC97202
0.7255 Intermediate Similarity NPC476027
0.7255 Intermediate Similarity NPC302607
0.7255 Intermediate Similarity NPC49958
0.7255 Intermediate Similarity NPC152695
0.7255 Intermediate Similarity NPC202167
0.7255 Intermediate Similarity NPC50692
0.7255 Intermediate Similarity NPC85829
0.7255 Intermediate Similarity NPC319077
0.7255 Intermediate Similarity NPC48733
0.7253 Intermediate Similarity NPC102048
0.7253 Intermediate Similarity NPC302360
0.7245 Intermediate Similarity NPC205143
0.7245 Intermediate Similarity NPC99726
0.7241 Intermediate Similarity NPC470428
0.7234 Intermediate Similarity NPC472973
0.7234 Intermediate Similarity NPC16265
0.7228 Intermediate Similarity NPC23584
0.7228 Intermediate Similarity NPC471938
0.7228 Intermediate Similarity NPC247957
0.7228 Intermediate Similarity NPC249187
0.7222 Intermediate Similarity NPC477116
0.7222 Intermediate Similarity NPC93590
0.7222 Intermediate Similarity NPC27999
0.7222 Intermediate Similarity NPC224455
0.7222 Intermediate Similarity NPC156252
0.7216 Intermediate Similarity NPC86893
0.7216 Intermediate Similarity NPC292178
0.7216 Intermediate Similarity NPC471915
0.7216 Intermediate Similarity NPC472824
0.7216 Intermediate Similarity NPC266899
0.7216 Intermediate Similarity NPC111273
0.7212 Intermediate Similarity NPC11710

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471267 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
0.7732 Intermediate Similarity NPD5344 Discontinued
0.7273 Intermediate Similarity NPD6648 Approved
0.7 Intermediate Similarity NPD4225 Approved
0.6961 Remote Similarity NPD5211 Phase 2
0.6887 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7524 Approved
0.6827 Remote Similarity NPD5141 Approved
0.6822 Remote Similarity NPD4634 Approved
0.6765 Remote Similarity NPD5285 Approved
0.6765 Remote Similarity NPD5286 Approved
0.6765 Remote Similarity NPD4696 Approved
0.6702 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7516 Approved
0.6636 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6635 Remote Similarity NPD5226 Approved
0.6635 Remote Similarity NPD5225 Approved
0.6635 Remote Similarity NPD4633 Approved
0.6635 Remote Similarity NPD5224 Approved
0.6632 Remote Similarity NPD1696 Phase 3
0.663 Remote Similarity NPD7514 Phase 3
0.663 Remote Similarity NPD6930 Phase 2
0.663 Remote Similarity NPD7525 Registered
0.663 Remote Similarity NPD7332 Phase 2
0.663 Remote Similarity NPD6931 Approved
0.6602 Remote Similarity NPD7640 Approved
0.6602 Remote Similarity NPD7639 Approved
0.6596 Remote Similarity NPD6695 Phase 3
0.6571 Remote Similarity NPD5175 Approved
0.6571 Remote Similarity NPD5174 Approved
0.6569 Remote Similarity NPD4755 Approved
0.6566 Remote Similarity NPD6079 Approved
0.6562 Remote Similarity NPD3618 Phase 1
0.6549 Remote Similarity NPD7328 Approved
0.6549 Remote Similarity NPD7327 Approved
0.6538 Remote Similarity NPD5223 Approved
0.6522 Remote Similarity NPD6929 Approved
0.6514 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6505 Remote Similarity NPD7638 Approved
0.65 Remote Similarity NPD4202 Approved
0.6486 Remote Similarity NPD4632 Approved
0.6471 Remote Similarity NPD5222 Approved
0.6471 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5221 Approved
0.646 Remote Similarity NPD7115 Discovery
0.6444 Remote Similarity NPD8264 Approved
0.6442 Remote Similarity NPD4700 Approved
0.6413 Remote Similarity NPD7145 Approved
0.6408 Remote Similarity NPD5173 Approved
0.64 Remote Similarity NPD7515 Phase 2
0.6389 Remote Similarity NPD5697 Approved
0.6386 Remote Similarity NPD368 Approved
0.6383 Remote Similarity NPD6902 Approved
0.6364 Remote Similarity NPD5328 Approved
0.6344 Remote Similarity NPD4195 Approved
0.6344 Remote Similarity NPD7645 Phase 2
0.633 Remote Similarity NPD6686 Approved
0.633 Remote Similarity NPD6881 Approved
0.633 Remote Similarity NPD6899 Approved
0.633 Remote Similarity NPD4730 Approved
0.633 Remote Similarity NPD4729 Approved
0.6327 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6327 Remote Similarity NPD7750 Discontinued
0.6304 Remote Similarity NPD5776 Phase 2
0.6304 Remote Similarity NPD6925 Approved
0.6304 Remote Similarity NPD6932 Approved
0.63 Remote Similarity NPD3168 Discontinued
0.63 Remote Similarity NPD7838 Discovery
0.6293 Remote Similarity NPD6319 Approved
0.6289 Remote Similarity NPD6893 Approved
0.6273 Remote Similarity NPD6013 Approved
0.6273 Remote Similarity NPD6012 Approved
0.6273 Remote Similarity NPD6014 Approved
0.625 Remote Similarity NPD8297 Approved
0.6239 Remote Similarity NPD8335 Approved
0.6239 Remote Similarity NPD7503 Approved
0.6239 Remote Similarity NPD8296 Approved
0.6239 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6239 Remote Similarity NPD8378 Approved
0.6239 Remote Similarity NPD8380 Approved
0.6239 Remote Similarity NPD8379 Approved
0.6238 Remote Similarity NPD7637 Suspended
0.6235 Remote Similarity NPD371 Approved
0.6224 Remote Similarity NPD4623 Approved
0.6224 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6224 Remote Similarity NPD4519 Discontinued
0.6222 Remote Similarity NPD4732 Discontinued
0.6216 Remote Similarity NPD5248 Approved
0.6216 Remote Similarity NPD7290 Approved
0.6216 Remote Similarity NPD5250 Approved
0.6216 Remote Similarity NPD5247 Approved
0.6216 Remote Similarity NPD5249 Phase 3
0.6216 Remote Similarity NPD5251 Approved
0.6216 Remote Similarity NPD7102 Approved
0.6216 Remote Similarity NPD6883 Approved
0.6214 Remote Similarity NPD5210 Approved
0.6214 Remote Similarity NPD4629 Approved
0.6211 Remote Similarity NPD6898 Phase 1
0.62 Remote Similarity NPD4753 Phase 2
0.6196 Remote Similarity NPD6933 Approved
0.619 Remote Similarity NPD5290 Discontinued
0.6186 Remote Similarity NPD3133 Approved
0.6186 Remote Similarity NPD3666 Approved
0.6186 Remote Similarity NPD3665 Phase 1
0.6182 Remote Similarity NPD6011 Approved
0.6182 Remote Similarity NPD5128 Approved
0.6174 Remote Similarity NPD6009 Approved
0.6168 Remote Similarity NPD7632 Discontinued
0.6161 Remote Similarity NPD5215 Approved
0.6161 Remote Similarity NPD5217 Approved
0.6161 Remote Similarity NPD6650 Approved
0.6161 Remote Similarity NPD6617 Approved
0.6161 Remote Similarity NPD6649 Approved
0.6161 Remote Similarity NPD6869 Approved
0.6161 Remote Similarity NPD6847 Approved
0.6161 Remote Similarity NPD5216 Approved
0.6161 Remote Similarity NPD8130 Phase 1
0.6154 Remote Similarity NPD8294 Approved
0.6154 Remote Similarity NPD4697 Phase 3
0.6154 Remote Similarity NPD8377 Approved
0.6154 Remote Similarity NPD6054 Approved
0.6147 Remote Similarity NPD6402 Approved
0.6147 Remote Similarity NPD6675 Approved
0.6147 Remote Similarity NPD5739 Approved
0.6147 Remote Similarity NPD7128 Approved
0.6147 Remote Similarity NPD4768 Approved
0.6147 Remote Similarity NPD4767 Approved
0.6146 Remote Similarity NPD3667 Approved
0.6122 Remote Similarity NPD1694 Approved
0.6117 Remote Similarity NPD5282 Discontinued
0.6117 Remote Similarity NPD7748 Approved
0.6111 Remote Similarity NPD4754 Approved
0.6106 Remote Similarity NPD6882 Approved
0.6105 Remote Similarity NPD4819 Approved
0.6105 Remote Similarity NPD4822 Approved
0.6105 Remote Similarity NPD4821 Approved
0.6105 Remote Similarity NPD4695 Discontinued
0.6105 Remote Similarity NPD4820 Approved
0.6102 Remote Similarity NPD8033 Approved
0.6102 Remote Similarity NPD6016 Approved
0.6102 Remote Similarity NPD6015 Approved
0.6095 Remote Similarity NPD7902 Approved
0.6091 Remote Similarity NPD5701 Approved
0.6091 Remote Similarity NPD6412 Phase 2
0.6082 Remote Similarity NPD6110 Phase 1
0.6078 Remote Similarity NPD7087 Discontinued
0.6071 Remote Similarity NPD5135 Approved
0.6071 Remote Similarity NPD5169 Approved
0.6071 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6071 Remote Similarity NPD6371 Approved
0.6064 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6064 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6061 Remote Similarity NPD5279 Phase 3
0.605 Remote Similarity NPD6370 Approved
0.605 Remote Similarity NPD5988 Approved
0.6036 Remote Similarity NPD7320 Approved
0.6022 Remote Similarity NPD3701 Clinical (unspecified phase)
0.602 Remote Similarity NPD4786 Approved
0.6019 Remote Similarity NPD5779 Approved
0.6019 Remote Similarity NPD5778 Approved
0.6018 Remote Similarity NPD5127 Approved
0.6 Remote Similarity NPD6683 Phase 2
0.5982 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5982 Remote Similarity NPD6372 Approved
0.5982 Remote Similarity NPD6373 Approved
0.598 Remote Similarity NPD6698 Approved
0.598 Remote Similarity NPD5785 Approved
0.598 Remote Similarity NPD46 Approved
0.5978 Remote Similarity NPD6926 Approved
0.5978 Remote Similarity NPD6924 Approved
0.5966 Remote Similarity NPD5983 Phase 2
0.5966 Remote Similarity NPD6921 Approved
0.596 Remote Similarity NPD5363 Approved
0.595 Remote Similarity NPD7492 Approved
0.5938 Remote Similarity NPD7509 Discontinued
0.5938 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5932 Remote Similarity NPD4522 Approved
0.5926 Remote Similarity NPD4159 Approved
0.5914 Remote Similarity NPD7339 Approved
0.5914 Remote Similarity NPD6942 Approved
0.5905 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5902 Remote Similarity NPD6616 Approved
0.5902 Remote Similarity NPD7507 Approved
0.59 Remote Similarity NPD5690 Phase 2
0.5895 Remote Similarity NPD4271 Approved
0.5895 Remote Similarity NPD4268 Approved
0.5893 Remote Similarity NPD5168 Approved
0.5889 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5888 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5887 Remote Similarity NPD7319 Approved
0.5882 Remote Similarity NPD6059 Approved
0.5872 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5868 Remote Similarity NPD7604 Phase 2
0.5862 Remote Similarity NPD5167 Approved
0.5854 Remote Similarity NPD7078 Approved
0.5842 Remote Similarity NPD3573 Approved
0.5825 Remote Similarity NPD7136 Phase 2
0.5824 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5816 Remote Similarity NPD4223 Phase 3
0.5816 Remote Similarity NPD4221 Approved
0.5816 Remote Similarity NPD4752 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   71746439
ChEMBL   CHEMBL2407694
ZINC  

Physicochemical Properties

Molecular Weight:  242.15
ALogP:  -0.5494
MLogP:  2.45
XLogP:  0.478
# Rotatable Bonds:  9
Polar Surface Area:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  1
# 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