Natural Product: NPC137163

Natural Product ID:  NPC137163
Common Name:   Capilloquinone
IUPAC Name:   2-[(2E,6E,10E,14S)-14,15-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10-trienyl]-5-methylcyclohexa-2,5-diene-1,4-dione
Synonyms:   Capilloquinone
Molecular Formula:   C27H40O4
Standard InCHIKey:  BIWLGTXOHXWEFP-WJJHDEEPSA-N
Standard InCHI:  InChI=1S/C27H40O4/c1-19(10-8-12-21(3)14-16-26(30)27(5,6)31)9-7-11-20(2)13-15-23-18-24(28)22(4)17-25(23)29/h9,12-13,17-18,26,30-31H,7-8,10-11,14-16H2,1-6H3/b19-9+,20-13+,21-12+/t26-/m0/s1
Canonical SMILES:  C/C(=CCC/C(=C/CC1=CC(=O)C(=CC1=O)C)/C)/CC/C=C(/CC[C@@H](C(O)(C)C)O)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
NPO22108 Sinularia capillosa Species Alcyoniidae Eukaryota PMID[20155971]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 39.6 % 22071302
NPT168 Cell Line P388 Mus musculus ED50 = 9.8 nM 19223647

  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 NPC137163 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
0.9016 High Similarity NPC278202
0.873 High Similarity NPC64971
0.8696 High Similarity NPC160540
0.8361 Intermediate Similarity NPC281590
0.8095 Intermediate Similarity NPC52012
0.7812 Intermediate Similarity NPC268185
0.7692 Intermediate Similarity NPC477784
0.7692 Intermediate Similarity NPC477786
0.7692 Intermediate Similarity NPC477785
0.7681 Intermediate Similarity NPC83965
0.7612 Intermediate Similarity NPC260573
0.7606 Intermediate Similarity NPC469914
0.76 Intermediate Similarity NPC325946
0.7571 Intermediate Similarity NPC193029
0.7571 Intermediate Similarity NPC96962
0.7571 Intermediate Similarity NPC106613
0.7571 Intermediate Similarity NPC473357
0.7568 Intermediate Similarity NPC114236
0.7541 Intermediate Similarity NPC20934
0.7541 Intermediate Similarity NPC288381
0.7541 Intermediate Similarity NPC225974
0.7532 Intermediate Similarity NPC472948
0.75 Intermediate Similarity NPC318766
0.75 Intermediate Similarity NPC227135
0.75 Intermediate Similarity NPC478122
0.75 Intermediate Similarity NPC231739
0.746 Intermediate Similarity NPC217188
0.7429 Intermediate Similarity NPC472072
0.7368 Intermediate Similarity NPC471061
0.7353 Intermediate Similarity NPC475251
0.7286 Intermediate Similarity NPC474304
0.7286 Intermediate Similarity NPC176215
0.7286 Intermediate Similarity NPC296436
0.7286 Intermediate Similarity NPC474329
0.7284 Intermediate Similarity NPC187529
0.7273 Intermediate Similarity NPC475994
0.725 Intermediate Similarity NPC161045
0.7237 Intermediate Similarity NPC250621
0.7222 Intermediate Similarity NPC273508
0.7222 Intermediate Similarity NPC117804
0.7222 Intermediate Similarity NPC209327
0.7215 Intermediate Similarity NPC474980
0.7179 Intermediate Similarity NPC291260
0.7162 Intermediate Similarity NPC95863
0.7162 Intermediate Similarity NPC67076
0.7162 Intermediate Similarity NPC319163
0.716 Intermediate Similarity NPC9868
0.7143 Intermediate Similarity NPC40049
0.7143 Intermediate Similarity NPC203403
0.7143 Intermediate Similarity NPC7029
0.7125 Intermediate Similarity NPC212083
0.7123 Intermediate Similarity NPC10758
0.7123 Intermediate Similarity NPC250928
0.7108 Intermediate Similarity NPC300779
0.7105 Intermediate Similarity NPC474885
0.7101 Intermediate Similarity NPC269737
0.7101 Intermediate Similarity NPC321838
0.7089 Intermediate Similarity NPC470947
0.7089 Intermediate Similarity NPC470945
0.7089 Intermediate Similarity NPC103634
0.7089 Intermediate Similarity NPC74086
0.7089 Intermediate Similarity NPC470946
0.7083 Intermediate Similarity NPC269985
0.7073 Intermediate Similarity NPC79573
0.7073 Intermediate Similarity NPC11804
0.7067 Intermediate Similarity NPC29542
0.7067 Intermediate Similarity NPC323437
0.7067 Intermediate Similarity NPC201562
0.7067 Intermediate Similarity NPC186042
0.7059 Intermediate Similarity NPC166554
0.7059 Intermediate Similarity NPC265856
0.7059 Intermediate Similarity NPC475931
0.7051 Intermediate Similarity NPC192006
0.7051 Intermediate Similarity NPC326753
0.7042 Intermediate Similarity NPC471200
0.7042 Intermediate Similarity NPC61473
0.7037 Intermediate Similarity NPC11620
0.7027 Intermediate Similarity NPC291062
0.7027 Intermediate Similarity NPC203819
0.7027 Intermediate Similarity NPC94743
0.7027 Intermediate Similarity NPC107848
0.7024 Intermediate Similarity NPC476707
0.7024 Intermediate Similarity NPC476706
0.7024 Intermediate Similarity NPC476708
0.7015 Intermediate Similarity NPC323436
0.7015 Intermediate Similarity NPC283502
0.7013 Intermediate Similarity NPC477708
0.7013 Intermediate Similarity NPC1973
0.7013 Intermediate Similarity NPC470525
0.7013 Intermediate Similarity NPC167873
0.7011 Intermediate Similarity NPC472977
0.7011 Intermediate Similarity NPC472976
0.7 Intermediate Similarity NPC6663
0.7 Intermediate Similarity NPC143168
0.7 Intermediate Similarity NPC116797
0.7 Intermediate Similarity NPC477830
0.7 Intermediate Similarity NPC53109
0.7 Intermediate Similarity NPC67254
0.7 Intermediate Similarity NPC477707
0.7 Intermediate Similarity NPC470298
0.6988 Remote Similarity NPC472009
0.6988 Remote Similarity NPC164393
0.6986 Remote Similarity NPC125578
0.6986 Remote Similarity NPC146376
0.6986 Remote Similarity NPC263382
0.6986 Remote Similarity NPC310210
0.6984 Remote Similarity NPC228776
0.6977 Remote Similarity NPC146852
0.6974 Remote Similarity NPC147438
0.6974 Remote Similarity NPC474321
0.6974 Remote Similarity NPC227814
0.6974 Remote Similarity NPC144995
0.6974 Remote Similarity NPC470299
0.6974 Remote Similarity NPC78527
0.6951 Remote Similarity NPC70424
0.6951 Remote Similarity NPC472265
0.6951 Remote Similarity NPC243618
0.6951 Remote Similarity NPC476412
0.6944 Remote Similarity NPC267027
0.6933 Remote Similarity NPC474884
0.6923 Remote Similarity NPC82666
0.6923 Remote Similarity NPC97173
0.6923 Remote Similarity NPC197659
0.6923 Remote Similarity NPC476007
0.6914 Remote Similarity NPC103486
0.6914 Remote Similarity NPC279186
0.6914 Remote Similarity NPC474291
0.6912 Remote Similarity NPC320421
0.6905 Remote Similarity NPC90652
0.6905 Remote Similarity NPC472007
0.6897 Remote Similarity NPC61275
0.6892 Remote Similarity NPC472947
0.6892 Remote Similarity NPC16964
0.6892 Remote Similarity NPC236208
0.6892 Remote Similarity NPC94488
0.6892 Remote Similarity NPC262673
0.6885 Remote Similarity NPC191337
0.6883 Remote Similarity NPC474011
0.6883 Remote Similarity NPC329852
0.6883 Remote Similarity NPC199445
0.6883 Remote Similarity NPC472256
0.6875 Remote Similarity NPC2482
0.6875 Remote Similarity NPC233377
0.6875 Remote Similarity NPC471514
0.6867 Remote Similarity NPC137033
0.6867 Remote Similarity NPC32037
0.6867 Remote Similarity NPC77971
0.6867 Remote Similarity NPC477747
0.6867 Remote Similarity NPC477746
0.686 Remote Similarity NPC471399
0.686 Remote Similarity NPC469464
0.686 Remote Similarity NPC477684
0.6857 Remote Similarity NPC207007
0.6857 Remote Similarity NPC68679
0.6857 Remote Similarity NPC228574
0.6857 Remote Similarity NPC321867
0.6857 Remote Similarity NPC294304
0.6849 Remote Similarity NPC82337
0.6849 Remote Similarity NPC243272
0.6849 Remote Similarity NPC251429
0.6842 Remote Similarity NPC275098
0.6835 Remote Similarity NPC279532
0.6835 Remote Similarity NPC62336
0.6829 Remote Similarity NPC62214
0.6829 Remote Similarity NPC251475
0.6829 Remote Similarity NPC16488
0.6829 Remote Similarity NPC169941
0.6829 Remote Similarity NPC44261
0.6824 Remote Similarity NPC476704
0.6824 Remote Similarity NPC470417
0.6824 Remote Similarity NPC106051
0.6824 Remote Similarity NPC472008
0.6824 Remote Similarity NPC158778
0.6818 Remote Similarity NPC189677
0.6818 Remote Similarity NPC473172
0.6812 Remote Similarity NPC122239
0.68 Remote Similarity NPC173321
0.68 Remote Similarity NPC280256
0.68 Remote Similarity NPC286154
0.6795 Remote Similarity NPC263582
0.6795 Remote Similarity NPC469646
0.6795 Remote Similarity NPC26504
0.679 Remote Similarity NPC136150
0.679 Remote Similarity NPC275766
0.679 Remote Similarity NPC112868
0.6786 Remote Similarity NPC196381
0.6786 Remote Similarity NPC472974
0.6786 Remote Similarity NPC473168
0.6786 Remote Similarity NPC179591
0.6786 Remote Similarity NPC183736
0.6782 Remote Similarity NPC472978
0.6782 Remote Similarity NPC476705
0.6782 Remote Similarity NPC472010
0.6782 Remote Similarity NPC477749
0.6782 Remote Similarity NPC142838
0.6774 Remote Similarity NPC8610
0.6774 Remote Similarity NPC262558
0.6769 Remote Similarity NPC137396
0.6765 Remote Similarity NPC192843
0.6765 Remote Similarity NPC71755

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC137163 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
0.7681 Intermediate Similarity NPD7331 Phase 2
0.7089 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD7341 Phase 2
0.7037 Intermediate Similarity NPD6110 Phase 1
0.7 Intermediate Similarity NPD2664 Clinical (unspecified phase)
0.6857 Remote Similarity NPD368 Approved
0.6712 Remote Similarity NPD3704 Approved
0.6667 Remote Similarity NPD3197 Phase 1
0.6548 Remote Similarity NPD3666 Approved
0.6548 Remote Similarity NPD3665 Phase 1
0.6548 Remote Similarity NPD3133 Approved
0.6522 Remote Similarity NPD8779 Phase 3
0.6486 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6479 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6477 Remote Similarity NPD6698 Approved
0.6477 Remote Similarity NPD46 Approved
0.6471 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5363 Approved
0.6463 Remote Similarity NPD4695 Discontinued
0.642 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6404 Remote Similarity NPD7515 Phase 2
0.6404 Remote Similarity NPD6079 Approved
0.6395 Remote Similarity NPD5279 Phase 3
0.6395 Remote Similarity NPD3618 Phase 1
0.6386 Remote Similarity NPD5369 Approved
0.6375 Remote Similarity NPD6933 Approved
0.6364 Remote Similarity NPD4753 Phase 2
0.6364 Remote Similarity NPD5328 Approved
0.6353 Remote Similarity NPD4786 Approved
0.6351 Remote Similarity NPD2685 Clinical (unspecified phase)
0.631 Remote Similarity NPD3667 Approved
0.6296 Remote Similarity NPD4756 Discovery
0.6292 Remote Similarity NPD7838 Discovery
0.6279 Remote Similarity NPD1696 Phase 3
0.6265 Remote Similarity NPD4821 Approved
0.6265 Remote Similarity NPD4819 Approved
0.6265 Remote Similarity NPD5368 Approved
0.6265 Remote Similarity NPD4822 Approved
0.6265 Remote Similarity NPD4820 Approved
0.6232 Remote Similarity NPD342 Phase 1
0.6197 Remote Similarity NPD6109 Phase 1
0.6196 Remote Similarity NPD5210 Approved
0.6196 Remote Similarity NPD4629 Approved
0.617 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6163 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4202 Approved
0.6145 Remote Similarity NPD4195 Approved
0.6129 Remote Similarity NPD5221 Approved
0.6129 Remote Similarity NPD5222 Approved
0.6129 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6125 Remote Similarity NPD6924 Approved
0.6125 Remote Similarity NPD6926 Approved
0.6118 Remote Similarity NPD4221 Approved
0.6118 Remote Similarity NPD6435 Approved
0.6118 Remote Similarity NPD4269 Approved
0.6118 Remote Similarity NPD4223 Phase 3
0.6118 Remote Similarity NPD4270 Approved
0.6111 Remote Similarity NPD5785 Approved
0.6105 Remote Similarity NPD5285 Approved
0.6105 Remote Similarity NPD5286 Approved
0.6105 Remote Similarity NPD4696 Approved
0.6094 Remote Similarity NPD4265 Approved
0.6092 Remote Similarity NPD5329 Approved
0.6087 Remote Similarity NPD7748 Approved
0.6071 Remote Similarity NPD4252 Approved
0.6064 Remote Similarity NPD6084 Phase 2
0.6064 Remote Similarity NPD6083 Phase 2
0.6064 Remote Similarity NPD4755 Approved
0.6064 Remote Similarity NPD5173 Approved
0.6049 Remote Similarity NPD8264 Approved
0.6047 Remote Similarity NPD5332 Approved
0.6047 Remote Similarity NPD7154 Phase 3
0.6047 Remote Similarity NPD5362 Discontinued
0.6047 Remote Similarity NPD5331 Approved
0.6042 Remote Similarity NPD5223 Approved
0.6026 Remote Similarity NPD6922 Approved
0.6026 Remote Similarity NPD6923 Approved
0.6024 Remote Similarity NPD4268 Approved
0.6024 Remote Similarity NPD4271 Approved
0.6023 Remote Similarity NPD5690 Phase 2
0.6023 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6 Remote Similarity NPD4790 Discontinued
0.6 Remote Similarity NPD4225 Approved
0.6 Remote Similarity NPD6101 Approved
0.5979 Remote Similarity NPD5225 Approved
0.5979 Remote Similarity NPD4633 Approved
0.5979 Remote Similarity NPD5226 Approved
0.5979 Remote Similarity NPD5224 Approved
0.5979 Remote Similarity NPD5211 Phase 2
0.5977 Remote Similarity NPD4197 Approved
0.5974 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5957 Remote Similarity NPD4697 Phase 3
0.5949 Remote Similarity NPD7144 Approved
0.5949 Remote Similarity NPD7143 Approved
0.5938 Remote Similarity NPD4700 Approved
0.593 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5918 Remote Similarity NPD5174 Approved
0.5918 Remote Similarity NPD5175 Approved
0.5914 Remote Similarity NPD5282 Discontinued
0.5909 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5904 Remote Similarity NPD6932 Approved
0.5902 Remote Similarity NPD5783 Phase 3
0.59 Remote Similarity NPD6412 Phase 2
0.5895 Remote Similarity NPD7902 Approved
0.5882 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5882 Remote Similarity NPD7525 Registered
0.5882 Remote Similarity NPD4634 Approved
0.5876 Remote Similarity NPD5344 Discontinued
0.5875 Remote Similarity NPD7150 Approved
0.5875 Remote Similarity NPD7151 Approved
0.5875 Remote Similarity NPD7152 Approved
0.587 Remote Similarity NPD6411 Approved
0.587 Remote Similarity NPD7983 Approved
0.5862 Remote Similarity NPD4788 Approved
0.5859 Remote Similarity NPD5141 Approved
0.5857 Remote Similarity NPD4266 Approved
0.5857 Remote Similarity NPD3195 Phase 2
0.5857 Remote Similarity NPD3194 Approved
0.5857 Remote Similarity NPD3196 Approved
0.5854 Remote Similarity NPD7339 Approved
0.5854 Remote Similarity NPD6942 Approved
0.5851 Remote Similarity NPD5695 Phase 3
0.5846 Remote Similarity NPD39 Approved
0.5843 Remote Similarity NPD7334 Approved
0.5843 Remote Similarity NPD5280 Approved
0.5843 Remote Similarity NPD4690 Approved
0.5843 Remote Similarity NPD4623 Approved
0.5843 Remote Similarity NPD4689 Approved
0.5843 Remote Similarity NPD7146 Approved
0.5843 Remote Similarity NPD4693 Phase 3
0.5843 Remote Similarity NPD6684 Approved
0.5843 Remote Similarity NPD5786 Approved
0.5843 Remote Similarity NPD4694 Approved
0.5843 Remote Similarity NPD6409 Approved
0.5843 Remote Similarity NPD4519 Discontinued
0.5843 Remote Similarity NPD4688 Approved
0.5843 Remote Similarity NPD7521 Approved
0.5843 Remote Similarity NPD4138 Approved
0.5843 Remote Similarity NPD5205 Approved
0.5843 Remote Similarity NPD5330 Approved
0.5842 Remote Similarity NPD6899 Approved
0.5842 Remote Similarity NPD6881 Approved
0.5833 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5825 Remote Similarity NPD4141 Clinical (unspecified phase)
0.5825 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5821 Remote Similarity NPD3173 Approved
0.5806 Remote Similarity NPD5779 Approved
0.5806 Remote Similarity NPD6399 Phase 3
0.5806 Remote Similarity NPD5778 Approved
0.5802 Remote Similarity NPD4732 Discontinued
0.58 Remote Similarity NPD7128 Approved
0.58 Remote Similarity NPD5739 Approved
0.58 Remote Similarity NPD6402 Approved
0.58 Remote Similarity NPD6675 Approved
0.5795 Remote Similarity NPD3668 Phase 3
0.5783 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5778 Remote Similarity NPD7524 Approved
0.5769 Remote Similarity NPD8297 Approved
0.5765 Remote Similarity NPD6683 Phase 2
0.5765 Remote Similarity NPD7645 Phase 2
0.5758 Remote Similarity NPD4754 Approved
0.5753 Remote Similarity NPD287 Approved
0.575 Remote Similarity NPD4691 Approved
0.5747 Remote Similarity NPD5209 Approved
0.5743 Remote Similarity NPD5697 Approved
0.5733 Remote Similarity NPD4192 Approved
0.5733 Remote Similarity NPD4191 Approved
0.5733 Remote Similarity NPD4194 Approved
0.5733 Remote Similarity NPD4193 Approved
0.5728 Remote Similarity NPD7102 Approved
0.5728 Remote Similarity NPD6371 Approved
0.5728 Remote Similarity NPD7290 Approved
0.5728 Remote Similarity NPD6883 Approved
0.5714 Remote Similarity NPD5737 Approved
0.5714 Remote Similarity NPD5776 Phase 2
0.5714 Remote Similarity NPD3172 Approved
0.5714 Remote Similarity NPD6925 Approved
0.5714 Remote Similarity NPD4632 Approved
0.5714 Remote Similarity NPD6672 Approved
0.5714 Remote Similarity NPD6903 Approved
0.5714 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5714 Remote Similarity NPD4518 Approved
0.5701 Remote Similarity NPD7115 Discovery
0.5699 Remote Similarity NPD5284 Approved
0.5699 Remote Similarity NPD7637 Suspended
0.5699 Remote Similarity NPD5281 Approved
0.5698 Remote Similarity NPD7332 Phase 2
0.5698 Remote Similarity NPD7509 Discontinued
0.5698 Remote Similarity NPD6931 Approved
0.5698 Remote Similarity NPD7514 Phase 3
0.5698 Remote Similarity NPD6930 Phase 2
0.5694 Remote Similarity NPD4219 Approved
0.5686 Remote Similarity NPD5128 Approved
0.5686 Remote Similarity NPD4730 Approved
0.5686 Remote Similarity NPD7320 Approved
0.5686 Remote Similarity NPD6686 Approved
0.5686 Remote Similarity NPD6011 Approved
0.5686 Remote Similarity NPD4729 Approved
0.5684 Remote Similarity NPD1698 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   46210742
ChEMBL   CHEMBL1095580
ZINC  

Physicochemical Properties

Molecular Weight:  428.29
ALogP:  3.5427
MLogP:  3.99
XLogP:  4.693
# Rotatable Bonds:  20
Polar Surface Area:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  31

Download Data

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