Natural Product: NPC474085

Natural Product ID:  NPC474085
Common Name:   21-Dehydroxybolinaquinone
IUPAC Name:   2-[[(1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl]-6-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:   21-Dehydroxybolinaquinone
Molecular Formula:   C22H30O3
Standard InCHIKey:  XTCHHUSMSVQHIH-ZOIWCPRRSA-N
Standard InCHI:  InChI=1S/C22H30O3/c1-14-7-6-8-18-15(2)21(3,9-10-22(14,18)4)13-16-11-17(23)12-19(25-5)20(16)24/h7,11-12,15,18H,6,8-10,13H2,1-5H3/t15-,18+,21-,22-/m1/s1
Canonical SMILES:  COC1=CC(=O)C=C(C1=O)C[C@@]1(C)CC[C@]2([C@H]([C@H]1C)CCC=C2C)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
NPO26203 Dysidea villosa Species Dysideidae Eukaryota Hainan Province, China PMID[19091557]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens IC50 = 19450 nM 10425143
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 39500 nM 24063567

  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 NPC474085 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
0.9494 High Similarity NPC263997
0.9494 High Similarity NPC8518
0.9494 High Similarity NPC132228
0.9494 High Similarity NPC133652
0.925 High Similarity NPC241512
0.925 High Similarity NPC6185
0.9103 High Similarity NPC108955
0.8987 High Similarity NPC55869
0.875 High Similarity NPC99308
0.8706 High Similarity NPC223093
0.8642 High Similarity NPC103486
0.8608 High Similarity NPC23778
0.859 High Similarity NPC92080
0.8554 High Similarity NPC474680
0.8519 High Similarity NPC225515
0.8519 High Similarity NPC475833
0.85 High Similarity NPC476177
0.85 High Similarity NPC27817
0.8488 Intermediate Similarity NPC474209
0.8488 Intermediate Similarity NPC475823
0.8481 Intermediate Similarity NPC472300
0.8481 Intermediate Similarity NPC283087
0.8375 Intermediate Similarity NPC478247
0.8375 Intermediate Similarity NPC478246
0.8375 Intermediate Similarity NPC469996
0.8375 Intermediate Similarity NPC30321
0.8375 Intermediate Similarity NPC189485
0.8354 Intermediate Similarity NPC1254
0.8354 Intermediate Similarity NPC26504
0.8313 Intermediate Similarity NPC105803
0.8313 Intermediate Similarity NPC53733
0.8312 Intermediate Similarity NPC474539
0.8293 Intermediate Similarity NPC149237
0.8171 Intermediate Similarity NPC2482
0.8158 Intermediate Similarity NPC188292
0.8158 Intermediate Similarity NPC260474
0.8125 Intermediate Similarity NPC110725
0.8125 Intermediate Similarity NPC470525
0.8118 Intermediate Similarity NPC33663
0.8101 Intermediate Similarity NPC147438
0.8095 Intermediate Similarity NPC8091
0.809 Intermediate Similarity NPC263780
0.8072 Intermediate Similarity NPC116797
0.8072 Intermediate Similarity NPC121984
0.8046 Intermediate Similarity NPC478260
0.8046 Intermediate Similarity NPC478259
0.8046 Intermediate Similarity NPC478261
0.8046 Intermediate Similarity NPC53454
0.8023 Intermediate Similarity NPC94666
0.8 Intermediate Similarity NPC237712
0.8 Intermediate Similarity NPC23170
0.7978 Intermediate Similarity NPC26865
0.7978 Intermediate Similarity NPC470036
0.7978 Intermediate Similarity NPC174167
0.7976 Intermediate Similarity NPC327969
0.7976 Intermediate Similarity NPC321289
0.7955 Intermediate Similarity NPC280833
0.7952 Intermediate Similarity NPC476809
0.7927 Intermediate Similarity NPC74410
0.7927 Intermediate Similarity NPC476808
0.7922 Intermediate Similarity NPC310992
0.7922 Intermediate Similarity NPC87141
0.7907 Intermediate Similarity NPC469993
0.7907 Intermediate Similarity NPC32037
0.7901 Intermediate Similarity NPC899
0.7867 Intermediate Similarity NPC34622
0.7867 Intermediate Similarity NPC474400
0.7857 Intermediate Similarity NPC278459
0.7841 Intermediate Similarity NPC307298
0.7831 Intermediate Similarity NPC472490
0.7831 Intermediate Similarity NPC192329
0.7831 Intermediate Similarity NPC475681
0.7816 Intermediate Similarity NPC472974
0.7816 Intermediate Similarity NPC327115
0.7805 Intermediate Similarity NPC165711
0.7791 Intermediate Similarity NPC144258
0.7791 Intermediate Similarity NPC473246
0.7791 Intermediate Similarity NPC320801
0.7791 Intermediate Similarity NPC469569
0.7778 Intermediate Similarity NPC175079
0.7778 Intermediate Similarity NPC99380
0.7766 Intermediate Similarity NPC104861
0.7765 Intermediate Similarity NPC100297
0.7765 Intermediate Similarity NPC470813
0.7763 Intermediate Similarity NPC98897
0.7763 Intermediate Similarity NPC251118
0.7753 Intermediate Similarity NPC305039
0.7753 Intermediate Similarity NPC65615
0.7753 Intermediate Similarity NPC112454
0.7753 Intermediate Similarity NPC68148
0.7738 Intermediate Similarity NPC267517
0.7738 Intermediate Similarity NPC18955
0.7738 Intermediate Similarity NPC472478
0.7733 Intermediate Similarity NPC57463
0.7733 Intermediate Similarity NPC151728
0.7727 Intermediate Similarity NPC220930
0.7727 Intermediate Similarity NPC272039
0.7727 Intermediate Similarity NPC230016
0.7727 Intermediate Similarity NPC470523
0.7727 Intermediate Similarity NPC38885
0.7722 Intermediate Similarity NPC251929
0.7722 Intermediate Similarity NPC265782
0.7722 Intermediate Similarity NPC2634
0.7717 Intermediate Similarity NPC147232
0.7717 Intermediate Similarity NPC777
0.7711 Intermediate Similarity NPC471409
0.7711 Intermediate Similarity NPC62336
0.7711 Intermediate Similarity NPC275494
0.7711 Intermediate Similarity NPC4827
0.7708 Intermediate Similarity NPC179208
0.7701 Intermediate Similarity NPC469948
0.7701 Intermediate Similarity NPC90287
0.7701 Intermediate Similarity NPC189311
0.7701 Intermediate Similarity NPC2709
0.7701 Intermediate Similarity NPC478245
0.7701 Intermediate Similarity NPC474537
0.7701 Intermediate Similarity NPC323765
0.7692 Intermediate Similarity NPC155198
0.7692 Intermediate Similarity NPC211230
0.7683 Intermediate Similarity NPC180886
0.7683 Intermediate Similarity NPC263582
0.7683 Intermediate Similarity NPC40353
0.7674 Intermediate Similarity NPC49019
0.7674 Intermediate Similarity NPC288281
0.7667 Intermediate Similarity NPC113393
0.7667 Intermediate Similarity NPC129913
0.7667 Intermediate Similarity NPC38952
0.7662 Intermediate Similarity NPC16119
0.7654 Intermediate Similarity NPC166797
0.7654 Intermediate Similarity NPC306928
0.7647 Intermediate Similarity NPC473217
0.7647 Intermediate Similarity NPC471898
0.7647 Intermediate Similarity NPC474353
0.7647 Intermediate Similarity NPC44963
0.7647 Intermediate Similarity NPC472684
0.764 Intermediate Similarity NPC472302
0.764 Intermediate Similarity NPC58271
0.764 Intermediate Similarity NPC470524
0.764 Intermediate Similarity NPC471722
0.7625 Intermediate Similarity NPC54123
0.7614 Intermediate Similarity NPC195640
0.7614 Intermediate Similarity NPC20688
0.7614 Intermediate Similarity NPC31564
0.7614 Intermediate Similarity NPC474733
0.7614 Intermediate Similarity NPC475022
0.7614 Intermediate Similarity NPC222613
0.7614 Intermediate Similarity NPC51014
0.7614 Intermediate Similarity NPC474778
0.7614 Intermediate Similarity NPC118648
0.7614 Intermediate Similarity NPC203795
0.7614 Intermediate Similarity NPC474732
0.7614 Intermediate Similarity NPC145879
0.7609 Intermediate Similarity NPC474328
0.7609 Intermediate Similarity NPC474882
0.7595 Intermediate Similarity NPC139397
0.7595 Intermediate Similarity NPC256846
0.759 Intermediate Similarity NPC197659
0.759 Intermediate Similarity NPC257666
0.759 Intermediate Similarity NPC476811
0.759 Intermediate Similarity NPC97377
0.759 Intermediate Similarity NPC266193
0.7586 Intermediate Similarity NPC227064
0.7586 Intermediate Similarity NPC312660
0.7586 Intermediate Similarity NPC321187
0.7586 Intermediate Similarity NPC476412
0.7586 Intermediate Similarity NPC214043
0.7586 Intermediate Similarity NPC329043
0.7586 Intermediate Similarity NPC85774
0.7586 Intermediate Similarity NPC53385
0.7586 Intermediate Similarity NPC58841
0.7586 Intermediate Similarity NPC161423
0.7564 Intermediate Similarity NPC474619
0.7558 Intermediate Similarity NPC328351
0.7558 Intermediate Similarity NPC260956
0.7558 Intermediate Similarity NPC302661
0.7558 Intermediate Similarity NPC142683
0.7558 Intermediate Similarity NPC238991
0.7558 Intermediate Similarity NPC193347
0.7558 Intermediate Similarity NPC151519
0.7558 Intermediate Similarity NPC48362
0.7558 Intermediate Similarity NPC310989
0.7558 Intermediate Similarity NPC163236
0.7556 Intermediate Similarity NPC474918
0.7556 Intermediate Similarity NPC477973
0.7556 Intermediate Similarity NPC326627
0.7556 Intermediate Similarity NPC469546
0.7556 Intermediate Similarity NPC310010
0.7556 Intermediate Similarity NPC119416
0.7531 Intermediate Similarity NPC470045
0.7531 Intermediate Similarity NPC470044
0.7531 Intermediate Similarity NPC303613
0.7531 Intermediate Similarity NPC474228
0.7529 Intermediate Similarity NPC474956
0.7529 Intermediate Similarity NPC26139
0.7529 Intermediate Similarity NPC304795
0.7529 Intermediate Similarity NPC287063
0.7529 Intermediate Similarity NPC469637
0.7528 Intermediate Similarity NPC181327
0.7528 Intermediate Similarity NPC471728
0.7528 Intermediate Similarity NPC30421

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474085 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
0.8625 High Similarity NPD4695 Discontinued
0.8046 Intermediate Similarity NPD5737 Approved
0.8046 Intermediate Similarity NPD6672 Approved
0.8023 Intermediate Similarity NPD5690 Phase 2
0.7927 Intermediate Similarity NPD3617 Approved
0.7865 Intermediate Similarity NPD5692 Phase 3
0.7816 Intermediate Similarity NPD5279 Phase 3
0.7816 Intermediate Similarity NPD5280 Approved
0.7816 Intermediate Similarity NPD4694 Approved
0.7791 Intermediate Similarity NPD4197 Approved
0.7778 Intermediate Similarity NPD5694 Approved
0.7778 Intermediate Similarity NPD6050 Approved
0.7753 Intermediate Similarity NPD6904 Approved
0.7753 Intermediate Similarity NPD6080 Approved
0.7753 Intermediate Similarity NPD6673 Approved
0.7753 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD4691 Approved
0.7717 Intermediate Similarity NPD5695 Phase 3
0.7701 Intermediate Similarity NPD5329 Approved
0.7662 Intermediate Similarity NPD6108 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD7146 Approved
0.7614 Intermediate Similarity NPD6409 Approved
0.7614 Intermediate Similarity NPD5330 Approved
0.7614 Intermediate Similarity NPD6098 Approved
0.7614 Intermediate Similarity NPD6684 Approved
0.7614 Intermediate Similarity NPD7334 Approved
0.7614 Intermediate Similarity NPD7521 Approved
0.7595 Intermediate Similarity NPD4137 Phase 3
0.7586 Intermediate Similarity NPD3665 Phase 1
0.7586 Intermediate Similarity NPD3133 Approved
0.7586 Intermediate Similarity NPD3666 Approved
0.7582 Intermediate Similarity NPD5693 Phase 1
0.7558 Intermediate Similarity NPD4223 Phase 3
0.7558 Intermediate Similarity NPD4221 Approved
0.7558 Intermediate Similarity NPD3667 Approved
0.7556 Intermediate Similarity NPD4753 Phase 2
0.7528 Intermediate Similarity NPD3573 Approved
0.75 Intermediate Similarity NPD4747 Approved
0.7444 Intermediate Similarity NPD6903 Approved
0.7444 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD5733 Approved
0.7439 Intermediate Similarity NPD4687 Approved
0.7439 Intermediate Similarity NPD4058 Approved
0.7416 Intermediate Similarity NPD3618 Phase 1
0.7407 Intermediate Similarity NPD5276 Approved
0.7386 Intermediate Similarity NPD4786 Approved
0.7386 Intermediate Similarity NPD3668 Phase 3
0.7368 Intermediate Similarity NPD6084 Phase 2
0.7368 Intermediate Similarity NPD6083 Phase 2
0.734 Intermediate Similarity NPD5210 Approved
0.734 Intermediate Similarity NPD5654 Approved
0.734 Intermediate Similarity NPD4629 Approved
0.7292 Intermediate Similarity NPD5696 Approved
0.7283 Intermediate Similarity NPD5207 Approved
0.7263 Intermediate Similarity NPD5222 Approved
0.7263 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5221 Approved
0.7253 Intermediate Similarity NPD5208 Approved
0.7222 Intermediate Similarity NPD4690 Approved
0.7222 Intermediate Similarity NPD4519 Discontinued
0.7222 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4689 Approved
0.7222 Intermediate Similarity NPD4623 Approved
0.7222 Intermediate Similarity NPD4693 Phase 3
0.7222 Intermediate Similarity NPD5205 Approved
0.7222 Intermediate Similarity NPD4138 Approved
0.7222 Intermediate Similarity NPD4688 Approved
0.7204 Intermediate Similarity NPD6079 Approved
0.7188 Intermediate Similarity NPD5959 Approved
0.7188 Intermediate Similarity NPD5173 Approved
0.7174 Intermediate Similarity NPD5328 Approved
0.7159 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD5133 Approved
0.7083 Intermediate Similarity NPD4697 Phase 3
0.7083 Intermediate Similarity NPD7732 Phase 3
0.7053 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD7748 Approved
0.7053 Intermediate Similarity NPD7900 Approved
0.7041 Intermediate Similarity NPD5285 Approved
0.7041 Intermediate Similarity NPD5286 Approved
0.7041 Intermediate Similarity NPD4696 Approved
0.7037 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD5281 Approved
0.7021 Intermediate Similarity NPD7515 Phase 2
0.7021 Intermediate Similarity NPD5284 Approved
0.7011 Intermediate Similarity NPD4195 Approved
0.701 Intermediate Similarity NPD4755 Approved
0.6979 Remote Similarity NPD6356 Clinical (unspecified phase)
0.697 Remote Similarity NPD5223 Approved
0.6961 Remote Similarity NPD5697 Approved
0.6947 Remote Similarity NPD6399 Phase 3
0.6947 Remote Similarity NPD4202 Approved
0.6923 Remote Similarity NPD1694 Approved
0.6915 Remote Similarity NPD4096 Approved
0.69 Remote Similarity NPD5225 Approved
0.69 Remote Similarity NPD5226 Approved
0.69 Remote Similarity NPD4633 Approved
0.69 Remote Similarity NPD5224 Approved
0.69 Remote Similarity NPD5211 Phase 2
0.6893 Remote Similarity NPD6899 Approved
0.6893 Remote Similarity NPD6881 Approved
0.6893 Remote Similarity NPD6011 Approved
0.6889 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6889 Remote Similarity NPD4788 Approved
0.6882 Remote Similarity NPD4518 Approved
0.6875 Remote Similarity NPD6001 Approved
0.6869 Remote Similarity NPD4700 Approved
0.6863 Remote Similarity NPD7128 Approved
0.6863 Remote Similarity NPD5739 Approved
0.6863 Remote Similarity NPD6402 Approved
0.6863 Remote Similarity NPD6675 Approved
0.6854 Remote Similarity NPD4692 Approved
0.6854 Remote Similarity NPD8028 Phase 2
0.6854 Remote Similarity NPD4139 Approved
0.6837 Remote Similarity NPD7902 Approved
0.6835 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5174 Approved
0.6832 Remote Similarity NPD5175 Approved
0.6827 Remote Similarity NPD6012 Approved
0.6827 Remote Similarity NPD6013 Approved
0.6827 Remote Similarity NPD6014 Approved
0.6796 Remote Similarity NPD6614 Approved
0.6796 Remote Similarity NPD5701 Approved
0.679 Remote Similarity NPD3704 Approved
0.6782 Remote Similarity NPD4756 Discovery
0.6765 Remote Similarity NPD5141 Approved
0.6762 Remote Similarity NPD7290 Approved
0.6762 Remote Similarity NPD7102 Approved
0.6762 Remote Similarity NPD6883 Approved
0.6753 Remote Similarity NPD287 Approved
0.6742 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6735 Remote Similarity NPD7614 Phase 1
0.6733 Remote Similarity NPD5091 Approved
0.6731 Remote Similarity NPD7320 Approved
0.6701 Remote Similarity NPD5282 Discontinued
0.6698 Remote Similarity NPD6847 Approved
0.6698 Remote Similarity NPD6649 Approved
0.6698 Remote Similarity NPD6869 Approved
0.6698 Remote Similarity NPD6617 Approved
0.6698 Remote Similarity NPD6650 Approved
0.6698 Remote Similarity NPD8130 Phase 1
0.6667 Remote Similarity NPD6372 Approved
0.6667 Remote Similarity NPD4754 Approved
0.6667 Remote Similarity NPD6373 Approved
0.6636 Remote Similarity NPD6882 Approved
0.6636 Remote Similarity NPD8297 Approved
0.6585 Remote Similarity NPD7331 Phase 2
0.6571 Remote Similarity NPD4730 Approved
0.6571 Remote Similarity NPD5168 Approved
0.6571 Remote Similarity NPD5128 Approved
0.6571 Remote Similarity NPD4729 Approved
0.6559 Remote Similarity NPD1696 Phase 3
0.6542 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6008 Approved
0.6538 Remote Similarity NPD4767 Approved
0.6538 Remote Similarity NPD4768 Approved
0.6495 Remote Similarity NPD6411 Approved
0.6477 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6463 Remote Similarity NPD7341 Phase 2
0.6455 Remote Similarity NPD6274 Approved
0.6455 Remote Similarity NPD6868 Approved
0.6449 Remote Similarity NPD5135 Approved
0.6449 Remote Similarity NPD5251 Approved
0.6449 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6449 Remote Similarity NPD5249 Phase 3
0.6449 Remote Similarity NPD4634 Approved
0.6449 Remote Similarity NPD5250 Approved
0.6449 Remote Similarity NPD5247 Approved
0.6449 Remote Similarity NPD5169 Approved
0.6449 Remote Similarity NPD5248 Approved
0.6422 Remote Similarity NPD4632 Approved
0.641 Remote Similarity NPD8779 Phase 3
0.6396 Remote Similarity NPD6009 Approved
0.6396 Remote Similarity NPD6317 Approved
0.6389 Remote Similarity NPD5217 Approved
0.6389 Remote Similarity NPD5215 Approved
0.6389 Remote Similarity NPD5127 Approved
0.6389 Remote Similarity NPD5216 Approved
0.6373 Remote Similarity NPD6404 Discontinued
0.6364 Remote Similarity NPD7339 Approved
0.6364 Remote Similarity NPD6942 Approved
0.6346 Remote Similarity NPD6052 Approved
0.6339 Remote Similarity NPD6313 Approved
0.6339 Remote Similarity NPD6335 Approved
0.6339 Remote Similarity NPD6314 Approved
0.6321 Remote Similarity NPD6412 Phase 2
0.6289 Remote Similarity NPD6101 Approved
0.6289 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6283 Remote Similarity NPD7101 Approved
0.6283 Remote Similarity NPD7100 Approved
0.6264 Remote Similarity NPD7645 Phase 2
0.625 Remote Similarity NPD4784 Approved
0.625 Remote Similarity NPD4785 Approved
0.6228 Remote Similarity NPD6319 Approved
0.6228 Remote Similarity NPD6054 Approved
0.6216 Remote Similarity NPD5167 Approved
0.6207 Remote Similarity NPD4243 Approved
0.618 Remote Similarity NPD8039 Approved
0.6174 Remote Similarity NPD6016 Approved
0.6174 Remote Similarity NPD6015 Approved

Structure

External Identifiers

PubChem CID   25211684
ChEMBL   CHEMBL460643
ZINC  

Physicochemical Properties

Molecular Weight:  342.22
ALogP:  2.1503
MLogP:  3.55
XLogP:  5.983
# Rotatable Bonds:  8
Polar Surface Area:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  25

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Biological Activities  
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