Natural Product: NPC144629

Natural Product ID:  NPC144629
Common Name:   Alpha-Tocospiro A
IUPAC Name:   (2S,5R,9S)-9-acetyl-9-hydroxy-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-1-oxaspiro[4.4]non-7-en-6-one
Synonyms:   Alpha-Tocospiro A
Molecular Formula:   C29H50O4
Standard InCHIKey:  NFNYYDIZCJKCQK-FKODAYNLSA-N
Standard InCHI:  InChI=1S/C29H50O4/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-17-27(8)18-19-28(33-27)26(31)23(5)24(6)29(28,32)25(7)30/h20-22,32H,9-19H2,1-8H3/t21-,22-,27+,28+,29-/m1/s1
Canonical SMILES:  C[C@@H](CCC[C@@]1(C)CC[C@]2(O1)C(=O)C(=C([C@@]2(O)C(=O)C)C)C)CCC[C@@H](CCCC(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
NPO22674 Caulerpa racemosa Species Caulerpaceae Eukaryota PMID[25497963]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 67400 nM 12617583
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 30 ug/ml 8326318
NPT81 Cell Line A549 Homo sapiens IC50 > 100000 nM 11908959

  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 NPC144629 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
0.8526 High Similarity NPC470541
0.8352 Intermediate Similarity NPC269677
0.7619 Intermediate Similarity NPC101018
0.7582 Intermediate Similarity NPC171665
0.7556 Intermediate Similarity NPC301769
0.7556 Intermediate Similarity NPC32758
0.7551 Intermediate Similarity NPC298919
0.7549 Intermediate Similarity NPC25639
0.7549 Intermediate Similarity NPC70369
0.7524 Intermediate Similarity NPC117604
0.7523 Intermediate Similarity NPC54739
0.7476 Intermediate Similarity NPC472755
0.7453 Intermediate Similarity NPC471400
0.7451 Intermediate Similarity NPC472753
0.7451 Intermediate Similarity NPC110443
0.7451 Intermediate Similarity NPC133907
0.7451 Intermediate Similarity NPC185141
0.7451 Intermediate Similarity NPC46998
0.7451 Intermediate Similarity NPC128733
0.7447 Intermediate Similarity NPC476628
0.7429 Intermediate Similarity NPC26617
0.7429 Intermediate Similarity NPC204884
0.7416 Intermediate Similarity NPC473437
0.7416 Intermediate Similarity NPC25908
0.7416 Intermediate Similarity NPC141346
0.7416 Intermediate Similarity NPC124289
0.7416 Intermediate Similarity NPC115719
0.7416 Intermediate Similarity NPC142759
0.7404 Intermediate Similarity NPC100487
0.7396 Intermediate Similarity NPC476708
0.7383 Intermediate Similarity NPC99760
0.7379 Intermediate Similarity NPC472754
0.7347 Intermediate Similarity NPC476705
0.7333 Intermediate Similarity NPC314244
0.7312 Intermediate Similarity NPC256750
0.7312 Intermediate Similarity NPC20262
0.7303 Intermediate Similarity NPC89374
0.7292 Intermediate Similarity NPC179659
0.7283 Intermediate Similarity NPC472948
0.7282 Intermediate Similarity NPC471401
0.7282 Intermediate Similarity NPC474742
0.7228 Intermediate Similarity NPC93271
0.7228 Intermediate Similarity NPC135576
0.7216 Intermediate Similarity NPC472677
0.7216 Intermediate Similarity NPC58532
0.72 Intermediate Similarity NPC121825
0.72 Intermediate Similarity NPC469632
0.7196 Intermediate Similarity NPC29827
0.7191 Intermediate Similarity NPC7382
0.717 Intermediate Similarity NPC223450
0.717 Intermediate Similarity NPC243998
0.7168 Intermediate Similarity NPC477092
0.7143 Intermediate Similarity NPC32922
0.7143 Intermediate Similarity NPC475871
0.7143 Intermediate Similarity NPC471145
0.7143 Intermediate Similarity NPC205548
0.7143 Intermediate Similarity NPC97032
0.7143 Intermediate Similarity NPC471146
0.7143 Intermediate Similarity NPC475945
0.7143 Intermediate Similarity NPC475873
0.7129 Intermediate Similarity NPC91408
0.7128 Intermediate Similarity NPC133844
0.7115 Intermediate Similarity NPC270155
0.7115 Intermediate Similarity NPC475867
0.7115 Intermediate Similarity NPC304738
0.7115 Intermediate Similarity NPC195192
0.7113 Intermediate Similarity NPC197333
0.7103 Intermediate Similarity NPC473165
0.71 Intermediate Similarity NPC469645
0.71 Intermediate Similarity NPC469692
0.7097 Intermediate Similarity NPC74445
0.7097 Intermediate Similarity NPC287817
0.7097 Intermediate Similarity NPC30675
0.7087 Intermediate Similarity NPC109556
0.708 Intermediate Similarity NPC475401
0.7075 Intermediate Similarity NPC474741
0.7075 Intermediate Similarity NPC472756
0.7075 Intermediate Similarity NPC13385
0.7071 Intermediate Similarity NPC71533
0.7071 Intermediate Similarity NPC106510
0.7071 Intermediate Similarity NPC474761
0.7071 Intermediate Similarity NPC476004
0.7048 Intermediate Similarity NPC118405
0.7048 Intermediate Similarity NPC474747
0.7048 Intermediate Similarity NPC149371
0.7041 Intermediate Similarity NPC476707
0.7041 Intermediate Similarity NPC476706
0.7041 Intermediate Similarity NPC53158
0.7033 Intermediate Similarity NPC182848
0.703 Intermediate Similarity NPC90453
0.7009 Intermediate Similarity NPC472749
0.7009 Intermediate Similarity NPC472751
0.7 Intermediate Similarity NPC111114
0.7 Intermediate Similarity NPC261607
0.7 Intermediate Similarity NPC300312
0.6991 Remote Similarity NPC475305
0.6989 Remote Similarity NPC472013
0.6989 Remote Similarity NPC476624
0.6981 Remote Similarity NPC474207
0.6981 Remote Similarity NPC472750
0.6981 Remote Similarity NPC474330
0.6981 Remote Similarity NPC472747
0.6979 Remote Similarity NPC90446
0.6972 Remote Similarity NPC38154
0.6961 Remote Similarity NPC472469
0.6961 Remote Similarity NPC469873
0.6961 Remote Similarity NPC475900
0.6952 Remote Similarity NPC47880
0.6952 Remote Similarity NPC164598
0.6952 Remote Similarity NPC474339
0.6952 Remote Similarity NPC475099
0.6939 Remote Similarity NPC471738
0.6937 Remote Similarity NPC207251
0.6931 Remote Similarity NPC37816
0.6931 Remote Similarity NPC135776
0.6931 Remote Similarity NPC475788
0.6923 Remote Similarity NPC212465
0.6923 Remote Similarity NPC177232
0.6916 Remote Similarity NPC472748
0.6916 Remote Similarity NPC203659
0.6909 Remote Similarity NPC257240
0.6909 Remote Similarity NPC477103
0.6907 Remote Similarity NPC125290
0.69 Remote Similarity NPC477711
0.69 Remote Similarity NPC2946
0.69 Remote Similarity NPC51004
0.6887 Remote Similarity NPC105725
0.6887 Remote Similarity NPC86077
0.6882 Remote Similarity NPC476627
0.6881 Remote Similarity NPC71220
0.6881 Remote Similarity NPC137286
0.6881 Remote Similarity NPC469508
0.6869 Remote Similarity NPC469631
0.6869 Remote Similarity NPC469628
0.6869 Remote Similarity NPC476704
0.6869 Remote Similarity NPC475906
0.6869 Remote Similarity NPC469653
0.6869 Remote Similarity NPC471047
0.6869 Remote Similarity NPC472008
0.6863 Remote Similarity NPC114162
0.6863 Remote Similarity NPC469819
0.6852 Remote Similarity NPC190867
0.6847 Remote Similarity NPC287311
0.6847 Remote Similarity NPC475495
0.6842 Remote Similarity NPC275766
0.6842 Remote Similarity NPC474353
0.6833 Remote Similarity NPC172823
0.6832 Remote Similarity NPC469627
0.6832 Remote Similarity NPC30515
0.6827 Remote Similarity NPC477949
0.6827 Remote Similarity NPC27105
0.6827 Remote Similarity NPC474313
0.6822 Remote Similarity NPC110989
0.6818 Remote Similarity NPC477102
0.6818 Remote Similarity NPC470257
0.6814 Remote Similarity NPC326542
0.6809 Remote Similarity NPC84185
0.6809 Remote Similarity NPC622
0.6809 Remote Similarity NPC66677
0.6809 Remote Similarity NPC471890
0.6809 Remote Similarity NPC276647
0.6804 Remote Similarity NPC120726
0.6804 Remote Similarity NPC32565
0.68 Remote Similarity NPC170775
0.68 Remote Similarity NPC474951
0.68 Remote Similarity NPC41217
0.68 Remote Similarity NPC307411
0.6796 Remote Similarity NPC163228
0.6796 Remote Similarity NPC36954
0.6796 Remote Similarity NPC474490
0.6796 Remote Similarity NPC261341
0.6792 Remote Similarity NPC150923
0.6792 Remote Similarity NPC206079
0.6792 Remote Similarity NPC476270
0.6792 Remote Similarity NPC201718
0.6792 Remote Similarity NPC15993
0.6789 Remote Similarity NPC473169
0.6789 Remote Similarity NPC477513
0.6786 Remote Similarity NPC35069
0.6786 Remote Similarity NPC189338
0.6786 Remote Similarity NPC471933
0.6786 Remote Similarity NPC138757
0.6786 Remote Similarity NPC95290
0.6786 Remote Similarity NPC477093
0.6786 Remote Similarity NPC473522
0.6786 Remote Similarity NPC258711
0.6786 Remote Similarity NPC475277
0.678 Remote Similarity NPC186339
0.6778 Remote Similarity NPC469737
0.6777 Remote Similarity NPC13071
0.6768 Remote Similarity NPC237540
0.6765 Remote Similarity NPC475912
0.6765 Remote Similarity NPC125180
0.6765 Remote Similarity NPC475488
0.6765 Remote Similarity NPC81419
0.6765 Remote Similarity NPC61275
0.6765 Remote Similarity NPC476300
0.6765 Remote Similarity NPC179746
0.6762 Remote Similarity NPC472687
0.6762 Remote Similarity NPC471331

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC144629 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
0.809 Intermediate Similarity NPD4800 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.6909 Remote Similarity NPD6371 Approved
0.6863 Remote Similarity NPD5282 Discontinued
0.6837 Remote Similarity NPD5786 Approved
0.6701 Remote Similarity NPD5362 Discontinued
0.6667 Remote Similarity NPD7341 Phase 2
0.6667 Remote Similarity NPD6059 Approved
0.6667 Remote Similarity NPD6054 Approved
0.6566 Remote Similarity NPD5363 Approved
0.6555 Remote Similarity NPD6370 Approved
0.6505 Remote Similarity NPD7983 Approved
0.6471 Remote Similarity NPD6015 Approved
0.6471 Remote Similarity NPD6016 Approved
0.6446 Remote Similarity NPD7492 Approved
0.6429 Remote Similarity NPD4270 Approved
0.6429 Remote Similarity NPD4269 Approved
0.6417 Remote Similarity NPD5988 Approved
0.6408 Remote Similarity NPD5785 Approved
0.64 Remote Similarity NPD5329 Approved
0.6393 Remote Similarity NPD6616 Approved
0.6387 Remote Similarity NPD6319 Approved
0.6364 Remote Similarity NPD6110 Phase 1
0.6355 Remote Similarity NPD6084 Phase 2
0.6355 Remote Similarity NPD6083 Phase 2
0.6341 Remote Similarity NPD8293 Discontinued
0.6341 Remote Similarity NPD7078 Approved
0.6327 Remote Similarity NPD5369 Approved
0.6321 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6321 Remote Similarity NPD5695 Phase 3
0.6316 Remote Similarity NPD4634 Approved
0.6311 Remote Similarity NPD6904 Approved
0.6311 Remote Similarity NPD6673 Approved
0.6311 Remote Similarity NPD6080 Approved
0.63 Remote Similarity NPD4197 Approved
0.629 Remote Similarity NPD6033 Approved
0.629 Remote Similarity NPD7736 Approved
0.6286 Remote Similarity NPD5779 Approved
0.6286 Remote Similarity NPD5778 Approved
0.6283 Remote Similarity NPD7320 Approved
0.625 Remote Similarity NPD6402 Approved
0.625 Remote Similarity NPD6675 Approved
0.625 Remote Similarity NPD5739 Approved
0.625 Remote Similarity NPD7128 Approved
0.6228 Remote Similarity NPD6372 Approved
0.6228 Remote Similarity NPD6373 Approved
0.6224 Remote Similarity NPD4252 Approved
0.6222 Remote Similarity NPD7331 Phase 2
0.6207 Remote Similarity NPD6053 Discontinued
0.6207 Remote Similarity NPD8297 Approved
0.62 Remote Similarity NPD7154 Phase 3
0.619 Remote Similarity NPD5693 Phase 1
0.619 Remote Similarity NPD6050 Approved
0.6176 Remote Similarity NPD5280 Approved
0.6176 Remote Similarity NPD4694 Approved
0.6176 Remote Similarity NPD5690 Phase 2
0.6154 Remote Similarity NPD4632 Approved
0.6154 Remote Similarity NPD4753 Phase 2
0.6147 Remote Similarity NPD5696 Approved
0.614 Remote Similarity NPD6899 Approved
0.614 Remote Similarity NPD6881 Approved
0.6126 Remote Similarity NPD5211 Phase 2
0.6121 Remote Similarity NPD6649 Approved
0.6121 Remote Similarity NPD6650 Approved
0.6117 Remote Similarity NPD4251 Approved
0.6117 Remote Similarity NPD4250 Approved
0.61 Remote Similarity NPD6435 Approved
0.61 Remote Similarity NPD4221 Approved
0.61 Remote Similarity NPD4223 Phase 3
0.6095 Remote Similarity NPD46 Approved
0.6095 Remote Similarity NPD5692 Phase 3
0.6095 Remote Similarity NPD6698 Approved
0.6055 Remote Similarity NPD4755 Approved
0.6053 Remote Similarity NPD5697 Approved
0.6053 Remote Similarity NPD5701 Approved
0.604 Remote Similarity NPD5332 Approved
0.604 Remote Similarity NPD5331 Approved
0.6038 Remote Similarity NPD5694 Approved
0.6034 Remote Similarity NPD7102 Approved
0.6034 Remote Similarity NPD6883 Approved
0.6034 Remote Similarity NPD7290 Approved
0.602 Remote Similarity NPD3617 Approved
0.6019 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6019 Remote Similarity NPD4249 Approved
0.6019 Remote Similarity NPD6098 Approved
0.6018 Remote Similarity NPD5141 Approved
0.6 Remote Similarity NPD6011 Approved
0.6 Remote Similarity NPD7115 Discovery
0.6 Remote Similarity NPD6009 Approved
0.6 Remote Similarity NPD1695 Approved
0.6 Remote Similarity NPD4790 Discontinued
0.5984 Remote Similarity NPD7319 Approved
0.5983 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5983 Remote Similarity NPD6617 Approved
0.5983 Remote Similarity NPD6847 Approved
0.5983 Remote Similarity NPD8130 Phase 1
0.5983 Remote Similarity NPD6869 Approved
0.5968 Remote Similarity NPD7604 Phase 2
0.5965 Remote Similarity NPD6008 Approved
0.5948 Remote Similarity NPD6012 Approved
0.5948 Remote Similarity NPD6013 Approved
0.5948 Remote Similarity NPD6014 Approved
0.5946 Remote Similarity NPD5285 Approved
0.5946 Remote Similarity NPD4700 Approved
0.5946 Remote Similarity NPD5286 Approved
0.5946 Remote Similarity NPD4696 Approved
0.5935 Remote Similarity NPD5983 Phase 2
0.5932 Remote Similarity NPD6882 Approved
0.5913 Remote Similarity NPD6412 Phase 2
0.5905 Remote Similarity NPD4518 Approved
0.5905 Remote Similarity NPD6672 Approved
0.5905 Remote Similarity NPD5737 Approved
0.59 Remote Similarity NPD4820 Approved
0.59 Remote Similarity NPD5368 Approved
0.59 Remote Similarity NPD5790 Clinical (unspecified phase)
0.59 Remote Similarity NPD4819 Approved
0.59 Remote Similarity NPD4695 Discontinued
0.59 Remote Similarity NPD4821 Approved
0.59 Remote Similarity NPD4822 Approved
0.5893 Remote Similarity NPD5223 Approved
0.5887 Remote Similarity NPD8080 Discontinued
0.5873 Remote Similarity NPD6336 Discontinued
0.5873 Remote Similarity NPD7507 Approved
0.5872 Remote Similarity NPD4629 Approved
0.5872 Remote Similarity NPD5210 Approved
0.5872 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5872 Remote Similarity NPD5654 Approved
0.587 Remote Similarity NPD3704 Approved
0.5865 Remote Similarity NPD4689 Approved
0.5865 Remote Similarity NPD4519 Discontinued
0.5865 Remote Similarity NPD4623 Approved
0.5865 Remote Similarity NPD5205 Approved
0.5865 Remote Similarity NPD4693 Phase 3
0.5865 Remote Similarity NPD4138 Approved
0.5865 Remote Similarity NPD4690 Approved
0.5865 Remote Similarity NPD4688 Approved
0.5859 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5856 Remote Similarity NPD4225 Approved
0.5847 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5842 Remote Similarity NPD4692 Approved
0.5842 Remote Similarity NPD4139 Approved
0.5841 Remote Similarity NPD4633 Approved
0.5841 Remote Similarity NPD5226 Approved
0.5841 Remote Similarity NPD5225 Approved
0.5841 Remote Similarity NPD5224 Approved
0.5833 Remote Similarity NPD5133 Approved
0.5818 Remote Similarity NPD4697 Phase 3
0.5818 Remote Similarity NPD7839 Suspended
0.5814 Remote Similarity NPD5956 Approved
0.581 Remote Similarity NPD7524 Approved
0.5794 Remote Similarity NPD5207 Approved
0.5789 Remote Similarity NPD4754 Approved
0.5789 Remote Similarity NPD5174 Approved
0.5789 Remote Similarity NPD5175 Approved
0.5769 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5769 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5769 Remote Similarity NPD1696 Phase 3
0.5766 Remote Similarity NPD5959 Approved
0.5758 Remote Similarity NPD4756 Discovery
0.5741 Remote Similarity NPD5284 Approved
0.5741 Remote Similarity NPD7637 Suspended
0.5741 Remote Similarity NPD5281 Approved
0.5739 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5739 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5714 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5279 Phase 3
0.5701 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5701 Remote Similarity NPD6101 Approved
0.5701 Remote Similarity NPD5328 Approved
0.57 Remote Similarity NPD4271 Approved
0.57 Remote Similarity NPD4268 Approved
0.5691 Remote Similarity NPD6335 Approved
0.569 Remote Similarity NPD4768 Approved
0.569 Remote Similarity NPD4767 Approved
0.5688 Remote Similarity NPD6399 Phase 3
0.568 Remote Similarity NPD8515 Approved
0.568 Remote Similarity NPD8516 Approved
0.568 Remote Similarity NPD8517 Approved
0.568 Remote Similarity NPD8274 Clinical (unspecified phase)
0.568 Remote Similarity NPD8513 Phase 3
0.5676 Remote Similarity NPD5221 Approved
0.5676 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5676 Remote Similarity NPD5222 Approved
0.5673 Remote Similarity NPD3133 Approved
0.5673 Remote Similarity NPD3666 Approved
0.5673 Remote Similarity NPD3665 Phase 1
0.5672 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5664 Remote Similarity NPD7640 Approved
0.5664 Remote Similarity NPD7639 Approved
0.5656 Remote Similarity NPD6274 Approved
0.5648 Remote Similarity NPD4096 Approved
0.5648 Remote Similarity NPD7838 Discovery
0.5645 Remote Similarity NPD7101 Approved
0.5645 Remote Similarity NPD4522 Approved
0.5645 Remote Similarity NPD7100 Approved
0.5636 Remote Similarity NPD6001 Approved
0.5625 Remote Similarity NPD5173 Approved
0.5614 Remote Similarity NPD1700 Approved
0.561 Remote Similarity NPD6317 Approved
0.561 Remote Similarity NPD8295 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   21674156
ChEMBL   CHEMBL2204408
ZINC  

Physicochemical Properties

Molecular Weight:  462.37
ALogP:  1.8338
MLogP:  4.21
XLogP:  7.971
# Rotatable Bonds:  22
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  33

Download Data

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Structure MOL file  
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Biological Activities  
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