Natural Product: NPC191283

Natural Product ID:  NPC191283
Common Name:   4Beta,10Alpha-Dihydroxy-5Betah-Guai-7(11),8-Dien-12,8-Olide
IUPAC Name:   (5S,5aS,8S,8aS)-5,8-dihydroxy-1,5,8-trimethyl-6,7,8a,9-tetrahydro-5aH-azuleno[6,5-b]furan-2-one
Synonyms:  
Molecular Formula:   C15H20O4
Standard InCHIKey:  SPLDFKJIFZMZQH-LWWSYDQCSA-N
Standard InCHI:  InChI=1S/C15H20O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h7,10-11,17-18H,4-6H2,1-3H3/t10-,11-,14-,15+/m0/s1
Canonical SMILES:  O=C1OC2=C[C@@](C)(O)[C@@H]3[C@H](CC2=C1C)[C@@](C)(O)CC3
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
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota Rhizomes PMID[23755850]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 2900 nM 21624500

  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 NPC191283 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
0.9419 High Similarity NPC32862
0.9419 High Similarity NPC272293
0.9419 High Similarity NPC40821
0.9277 High Similarity NPC471185
0.9048 High Similarity NPC146850
0.9048 High Similarity NPC287015
0.8706 High Similarity NPC290052
0.8488 Intermediate Similarity NPC16887
0.8488 Intermediate Similarity NPC53011
0.8488 Intermediate Similarity NPC37005
0.8488 Intermediate Similarity NPC154893
0.7789 Intermediate Similarity NPC37408
0.7789 Intermediate Similarity NPC67584
0.7789 Intermediate Similarity NPC220221
0.7789 Intermediate Similarity NPC52044
0.7789 Intermediate Similarity NPC469873
0.7778 Intermediate Similarity NPC245434
0.7742 Intermediate Similarity NPC471184
0.7742 Intermediate Similarity NPC301969
0.7742 Intermediate Similarity NPC37607
0.7732 Intermediate Similarity NPC221615
0.7727 Intermediate Similarity NPC78677
0.7727 Intermediate Similarity NPC59994
0.7708 Intermediate Similarity NPC98165
0.7708 Intermediate Similarity NPC213078
0.77 Intermediate Similarity NPC200861
0.7629 Intermediate Similarity NPC161493
0.7629 Intermediate Similarity NPC477949
0.7609 Intermediate Similarity NPC45957
0.7609 Intermediate Similarity NPC471657
0.7604 Intermediate Similarity NPC170120
0.7576 Intermediate Similarity NPC150923
0.7576 Intermediate Similarity NPC116139
0.7576 Intermediate Similarity NPC62670
0.7551 Intermediate Similarity NPC244411
0.75 Intermediate Similarity NPC127019
0.75 Intermediate Similarity NPC323008
0.75 Intermediate Similarity NPC470013
0.75 Intermediate Similarity NPC470010
0.75 Intermediate Similarity NPC262133
0.75 Intermediate Similarity NPC66110
0.7474 Intermediate Similarity NPC2882
0.7447 Intermediate Similarity NPC212664
0.7447 Intermediate Similarity NPC225283
0.7423 Intermediate Similarity NPC213698
0.7396 Intermediate Similarity NPC472954
0.7381 Intermediate Similarity NPC315597
0.7381 Intermediate Similarity NPC316029
0.7374 Intermediate Similarity NPC181147
0.7374 Intermediate Similarity NPC64742
0.7368 Intermediate Similarity NPC3436
0.7356 Intermediate Similarity NPC476317
0.7353 Intermediate Similarity NPC472822
0.7347 Intermediate Similarity NPC9812
0.7347 Intermediate Similarity NPC473333
0.734 Intermediate Similarity NPC260343
0.732 Intermediate Similarity NPC198853
0.732 Intermediate Similarity NPC477131
0.7312 Intermediate Similarity NPC67493
0.7303 Intermediate Similarity NPC226226
0.7303 Intermediate Similarity NPC55304
0.73 Intermediate Similarity NPC280963
0.73 Intermediate Similarity NPC469864
0.73 Intermediate Similarity NPC469872
0.73 Intermediate Similarity NPC290802
0.7292 Intermediate Similarity NPC475925
0.7292 Intermediate Similarity NPC470520
0.7273 Intermediate Similarity NPC2666
0.7273 Intermediate Similarity NPC476439
0.7273 Intermediate Similarity NPC315394
0.7264 Intermediate Similarity NPC262083
0.7264 Intermediate Similarity NPC471484
0.7262 Intermediate Similarity NPC232812
0.7255 Intermediate Similarity NPC280566
0.7255 Intermediate Similarity NPC124881
0.7255 Intermediate Similarity NPC183570
0.7245 Intermediate Similarity NPC471492
0.7245 Intermediate Similarity NPC329435
0.7238 Intermediate Similarity NPC475274
0.7228 Intermediate Similarity NPC475099
0.7222 Intermediate Similarity NPC106446
0.7216 Intermediate Similarity NPC59646
0.7184 Intermediate Similarity NPC121099
0.7184 Intermediate Similarity NPC272632
0.7176 Intermediate Similarity NPC315285
0.7176 Intermediate Similarity NPC37929
0.7176 Intermediate Similarity NPC64234
0.717 Intermediate Similarity NPC238850
0.717 Intermediate Similarity NPC181298
0.7159 Intermediate Similarity NPC152017
0.7158 Intermediate Similarity NPC473658
0.7158 Intermediate Similarity NPC26078
0.7158 Intermediate Similarity NPC79549
0.7158 Intermediate Similarity NPC471956
0.7158 Intermediate Similarity NPC91248
0.7157 Intermediate Similarity NPC140591
0.7157 Intermediate Similarity NPC197835
0.7157 Intermediate Similarity NPC303653
0.7157 Intermediate Similarity NPC291500
0.7157 Intermediate Similarity NPC189609
0.7143 Intermediate Similarity NPC470521
0.7143 Intermediate Similarity NPC90453
0.7143 Intermediate Similarity NPC96541
0.7143 Intermediate Similarity NPC472467
0.7143 Intermediate Similarity NPC313444
0.7113 Intermediate Similarity NPC175842
0.7113 Intermediate Similarity NPC131209
0.7113 Intermediate Similarity NPC133698
0.7113 Intermediate Similarity NPC32494
0.7103 Intermediate Similarity NPC284162
0.7103 Intermediate Similarity NPC255401
0.71 Intermediate Similarity NPC47834
0.71 Intermediate Similarity NPC471490
0.7097 Intermediate Similarity NPC474693
0.7087 Intermediate Similarity NPC472821
0.7087 Intermediate Similarity NPC160583
0.7083 Intermediate Similarity NPC51358
0.7083 Intermediate Similarity NPC32922
0.7083 Intermediate Similarity NPC307092
0.7083 Intermediate Similarity NPC215556
0.7083 Intermediate Similarity NPC205548
0.7079 Intermediate Similarity NPC53581
0.7079 Intermediate Similarity NPC316324
0.7079 Intermediate Similarity NPC103987
0.7079 Intermediate Similarity NPC54996
0.7071 Intermediate Similarity NPC304886
0.7065 Intermediate Similarity NPC133844
0.7059 Intermediate Similarity NPC25177
0.7059 Intermediate Similarity NPC477950
0.7059 Intermediate Similarity NPC144647
0.7059 Intermediate Similarity NPC268829
0.7059 Intermediate Similarity NPC206079
0.7059 Intermediate Similarity NPC222875
0.7059 Intermediate Similarity NPC295110
0.7059 Intermediate Similarity NPC298233
0.7059 Intermediate Similarity NPC219038
0.7059 Intermediate Similarity NPC247701
0.7053 Intermediate Similarity NPC316629
0.7053 Intermediate Similarity NPC160138
0.7045 Intermediate Similarity NPC265921
0.7045 Intermediate Similarity NPC85831
0.7045 Intermediate Similarity NPC215215
0.7041 Intermediate Similarity NPC135776
0.7041 Intermediate Similarity NPC258216
0.7021 Intermediate Similarity NPC475860
0.7021 Intermediate Similarity NPC253604
0.7021 Intermediate Similarity NPC67081
0.7021 Intermediate Similarity NPC473659
0.7021 Intermediate Similarity NPC284534
0.7021 Intermediate Similarity NPC474694
0.7021 Intermediate Similarity NPC471223
0.7021 Intermediate Similarity NPC476628
0.7021 Intermediate Similarity NPC235792
0.7021 Intermediate Similarity NPC300082
0.7021 Intermediate Similarity NPC204105
0.7019 Intermediate Similarity NPC309190
0.701 Intermediate Similarity NPC473448
0.701 Intermediate Similarity NPC216284
0.7009 Intermediate Similarity NPC15551
0.7 Intermediate Similarity NPC24956
0.7 Intermediate Similarity NPC63445
0.7 Intermediate Similarity NPC222210
0.7 Intermediate Similarity NPC18019
0.699 Remote Similarity NPC86077
0.699 Remote Similarity NPC471599
0.6989 Remote Similarity NPC471340
0.6988 Remote Similarity NPC469326
0.6988 Remote Similarity NPC205618
0.6988 Remote Similarity NPC261782
0.6979 Remote Similarity NPC242448
0.6979 Remote Similarity NPC224652
0.6979 Remote Similarity NPC58532
0.6979 Remote Similarity NPC472677
0.697 Remote Similarity NPC281775
0.6961 Remote Similarity NPC70865
0.6952 Remote Similarity NPC223450
0.6952 Remote Similarity NPC220217
0.6952 Remote Similarity NPC119855
0.6952 Remote Similarity NPC243998
0.6947 Remote Similarity NPC64153
0.6947 Remote Similarity NPC122502
0.6947 Remote Similarity NPC137253
0.6947 Remote Similarity NPC477668
0.6944 Remote Similarity NPC71680
0.6939 Remote Similarity NPC472468
0.6939 Remote Similarity NPC155215
0.6939 Remote Similarity NPC290651
0.6939 Remote Similarity NPC221282
0.6932 Remote Similarity NPC470686
0.6923 Remote Similarity NPC84185
0.6923 Remote Similarity NPC97487
0.6923 Remote Similarity NPC471890
0.6923 Remote Similarity NPC196471
0.6923 Remote Similarity NPC187302
0.6923 Remote Similarity NPC189588
0.6923 Remote Similarity NPC66677
0.6923 Remote Similarity NPC10232
0.6915 Remote Similarity NPC472957
0.6915 Remote Similarity NPC472958
0.6915 Remote Similarity NPC156485

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC191283 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
0.7128 Intermediate Similarity NPD4249 Approved
0.7053 Intermediate Similarity NPD4251 Approved
0.7053 Intermediate Similarity NPD4250 Approved
0.7037 Intermediate Similarity NPD6053 Discontinued
0.7021 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.6735 Remote Similarity NPD1695 Approved
0.6729 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6697 Remote Similarity NPD6371 Approved
0.6667 Remote Similarity NPD7838 Discovery
0.6635 Remote Similarity NPD7640 Approved
0.6635 Remote Similarity NPD7639 Approved
0.6632 Remote Similarity NPD5362 Discontinued
0.6538 Remote Similarity NPD7638 Approved
0.6489 Remote Similarity NPD4820 Approved
0.6489 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6489 Remote Similarity NPD4821 Approved
0.6489 Remote Similarity NPD4819 Approved
0.6489 Remote Similarity NPD4822 Approved
0.6458 Remote Similarity NPD5332 Approved
0.6458 Remote Similarity NPD5331 Approved
0.6436 Remote Similarity NPD5284 Approved
0.6436 Remote Similarity NPD5281 Approved
0.6421 Remote Similarity NPD4790 Discontinued
0.641 Remote Similarity NPD7503 Approved
0.6381 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5785 Approved
0.6321 Remote Similarity NPD6648 Approved
0.6293 Remote Similarity NPD7328 Approved
0.6293 Remote Similarity NPD7327 Approved
0.6289 Remote Similarity NPD7154 Phase 3
0.6277 Remote Similarity NPD4268 Approved
0.6277 Remote Similarity NPD4271 Approved
0.6275 Remote Similarity NPD7637 Suspended
0.6275 Remote Similarity NPD5693 Phase 1
0.6239 Remote Similarity NPD7516 Approved
0.6224 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6204 Remote Similarity NPD7632 Discontinued
0.6186 Remote Similarity NPD8377 Approved
0.6186 Remote Similarity NPD8294 Approved
0.6176 Remote Similarity NPD6698 Approved
0.6176 Remote Similarity NPD5692 Phase 3
0.6176 Remote Similarity NPD5207 Approved
0.6176 Remote Similarity NPD46 Approved
0.6162 Remote Similarity NPD5363 Approved
0.6134 Remote Similarity NPD8033 Approved
0.6134 Remote Similarity NPD8335 Approved
0.6134 Remote Similarity NPD8296 Approved
0.6134 Remote Similarity NPD8380 Approved
0.6134 Remote Similarity NPD8379 Approved
0.6134 Remote Similarity NPD8378 Approved
0.6122 Remote Similarity NPD6695 Phase 3
0.6117 Remote Similarity NPD5694 Approved
0.6117 Remote Similarity NPD6050 Approved
0.6111 Remote Similarity NPD5344 Discontinued
0.6095 Remote Similarity NPD5695 Phase 3
0.6095 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6078 Remote Similarity NPD6051 Approved
0.6066 Remote Similarity NPD7507 Approved
0.6023 Remote Similarity NPD2685 Clinical (unspecified phase)
0.602 Remote Similarity NPD6435 Approved
0.602 Remote Similarity NPD5209 Approved
0.602 Remote Similarity NPD4270 Approved
0.602 Remote Similarity NPD4752 Clinical (unspecified phase)
0.602 Remote Similarity NPD4269 Approved
0.6 Remote Similarity NPD5282 Discontinued
0.5981 Remote Similarity NPD6083 Phase 2
0.5981 Remote Similarity NPD6084 Phase 2
0.5962 Remote Similarity NPD7983 Approved
0.5943 Remote Similarity NPD5654 Approved
0.5941 Remote Similarity NPD5280 Approved
0.5941 Remote Similarity NPD4694 Approved
0.5941 Remote Similarity NPD5786 Approved
0.5938 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5929 Remote Similarity NPD6686 Approved
0.5926 Remote Similarity NPD5696 Approved
0.5922 Remote Similarity NPD6904 Approved
0.5922 Remote Similarity NPD6080 Approved
0.5922 Remote Similarity NPD6673 Approved
0.592 Remote Similarity NPD7319 Approved
0.5918 Remote Similarity NPD5369 Approved
0.5905 Remote Similarity NPD5778 Approved
0.5905 Remote Similarity NPD5779 Approved
0.5893 Remote Similarity NPD6008 Approved
0.5882 Remote Similarity NPD7750 Discontinued
0.5882 Remote Similarity NPD7524 Approved
0.5876 Remote Similarity NPD4195 Approved
0.5859 Remote Similarity NPD4223 Phase 3
0.5859 Remote Similarity NPD4221 Approved
0.5833 Remote Similarity NPD4756 Discovery
0.5833 Remote Similarity NPD5959 Approved
0.5825 Remote Similarity NPD5208 Approved
0.5825 Remote Similarity NPD4518 Approved
0.5816 Remote Similarity NPD5368 Approved
0.5816 Remote Similarity NPD6931 Approved
0.5816 Remote Similarity NPD6930 Phase 2
0.5816 Remote Similarity NPD4252 Approved
0.5794 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7320 Approved
0.578 Remote Similarity NPD4225 Approved
0.5752 Remote Similarity NPD5739 Approved
0.5752 Remote Similarity NPD6402 Approved
0.5752 Remote Similarity NPD7128 Approved
0.5752 Remote Similarity NPD6675 Approved
0.5743 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5743 Remote Similarity NPD4197 Approved
0.5739 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5714 Remote Similarity NPD4096 Approved
0.5714 Remote Similarity NPD6929 Approved
0.5702 Remote Similarity NPD5701 Approved
0.5702 Remote Similarity NPD6685 Approved
0.5702 Remote Similarity NPD5697 Approved
0.5701 Remote Similarity NPD6001 Approved
0.569 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5686 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5686 Remote Similarity NPD5329 Approved
0.5686 Remote Similarity NPD1694 Approved
0.5678 Remote Similarity NPD4632 Approved
0.5673 Remote Similarity NPD6903 Approved
0.566 Remote Similarity NPD7087 Discontinued
0.5657 Remote Similarity NPD7514 Phase 3
0.5652 Remote Similarity NPD6899 Approved
0.5652 Remote Similarity NPD6011 Approved
0.5652 Remote Similarity NPD6881 Approved
0.5631 Remote Similarity NPD4693 Phase 3
0.5631 Remote Similarity NPD7334 Approved
0.5631 Remote Similarity NPD4138 Approved
0.5631 Remote Similarity NPD5330 Approved
0.5631 Remote Similarity NPD5690 Phase 2
0.5631 Remote Similarity NPD6098 Approved
0.5631 Remote Similarity NPD6409 Approved
0.5631 Remote Similarity NPD4688 Approved
0.5631 Remote Similarity NPD5205 Approved
0.5631 Remote Similarity NPD7521 Approved
0.5631 Remote Similarity NPD4689 Approved
0.5631 Remote Similarity NPD7146 Approved
0.5631 Remote Similarity NPD6684 Approved
0.5631 Remote Similarity NPD4690 Approved
0.5625 Remote Similarity NPD6007 Clinical (unspecified phase)
0.5619 Remote Similarity NPD4753 Phase 2
0.5607 Remote Similarity NPD6399 Phase 3
0.5607 Remote Similarity NPD5133 Approved
0.5603 Remote Similarity NPD6372 Approved
0.5603 Remote Similarity NPD6012 Approved
0.5603 Remote Similarity NPD6014 Approved
0.5603 Remote Similarity NPD6373 Approved
0.5603 Remote Similarity NPD6013 Approved

Structure

External Identifiers

PubChem CID   71725778
ChEMBL   CHEMBL2386505
ZINC  

Physicochemical Properties

Molecular Weight:  264.14
ALogP:  0.2573
MLogP:  2.67
XLogP:  0.86
# Rotatable Bonds:  5
Polar Surface Area:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  19

Download Data

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