Natural Product: NPC190008

Natural Product ID:  NPC190008
Common Name:   Xenibecin
IUPAC Name:   (E,5E)-5-[(1S,3S,4aS,7E,11aR)-1,3-dimethoxy-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydro-1H-cyclonona[c]pyran-4-ylidene]-2-methylpent-3-en-2-ol
Synonyms:   Xenibecin
Molecular Formula:   C22H34O4
Standard InCHIKey:  FQSNNBZYQHKNDZ-AQUXDQNHSA-N
Standard InCHI:  InChI=1S/C22H34O4/c1-15-9-7-10-16(2)19-17(13-12-15)18(11-8-14-22(3,4)23)20(24-5)26-21(19)25-6/h8-9,11,14,17,19-21,23H,2,7,10,12-13H2,1,3-6H3/b14-8+,15-9+,18-11+/t17-,19+,20+,21+/m1/s1
Canonical SMILES:  CO[C@H]1O[C@H](OC)[C@@H]2[C@@H](/C/1=CC=CC(O)(C)C)CC/C(=C/CCC2=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
NPO14298 Xenia umbellata Species Xeniidae Eukaryota PMID[12502332]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT139 Cell Line HT-29 Homo sapiens ED50 = 12.5 ug/ml 25729554
NPT168 Cell Line P388 Mus musculus ED50 = 3.96 ug/ml 25729554
NPT81 Cell Line A549 Homo sapiens ED50 = 13.4 ug/ml DrugMatrix in vitro pharmacology data

  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 NPC190008 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
0.9211 High Similarity NPC4436
0.7816 Intermediate Similarity NPC313658
0.7816 Intermediate Similarity NPC316138
0.764 Intermediate Similarity NPC309310
0.7586 Intermediate Similarity NPC471494
0.75 Intermediate Similarity NPC234038
0.75 Intermediate Similarity NPC471480
0.7471 Intermediate Similarity NPC196487
0.7471 Intermediate Similarity NPC14575
0.7447 Intermediate Similarity NPC98112
0.7391 Intermediate Similarity NPC476049
0.7386 Intermediate Similarity NPC474369
0.7349 Intermediate Similarity NPC229655
0.7333 Intermediate Similarity NPC248312
0.7333 Intermediate Similarity NPC233997
0.7303 Intermediate Similarity NPC116575
0.7303 Intermediate Similarity NPC311163
0.7294 Intermediate Similarity NPC471537
0.7294 Intermediate Similarity NPC204270
0.7262 Intermediate Similarity NPC84360
0.7262 Intermediate Similarity NPC107668
0.7209 Intermediate Similarity NPC100697
0.7204 Intermediate Similarity NPC91654
0.7204 Intermediate Similarity NPC472196
0.7204 Intermediate Similarity NPC474792
0.7204 Intermediate Similarity NPC472195
0.7204 Intermediate Similarity NPC238090
0.7204 Intermediate Similarity NPC67398
0.7195 Intermediate Similarity NPC477085
0.7188 Intermediate Similarity NPC203627
0.7174 Intermediate Similarity NPC470817
0.7174 Intermediate Similarity NPC202886
0.7174 Intermediate Similarity NPC477865
0.7174 Intermediate Similarity NPC477866
0.716 Intermediate Similarity NPC4299
0.7143 Intermediate Similarity NPC473151
0.7143 Intermediate Similarity NPC256720
0.7143 Intermediate Similarity NPC236228
0.7128 Intermediate Similarity NPC88507
0.7128 Intermediate Similarity NPC159698
0.7125 Intermediate Similarity NPC470040
0.7125 Intermediate Similarity NPC305698
0.7111 Intermediate Similarity NPC198314
0.7097 Intermediate Similarity NPC302584
0.7093 Intermediate Similarity NPC321728
0.7079 Intermediate Similarity NPC471301
0.7079 Intermediate Similarity NPC471302
0.7079 Intermediate Similarity NPC474776
0.7073 Intermediate Similarity NPC477087
0.7073 Intermediate Similarity NPC477086
0.7073 Intermediate Similarity NPC477084
0.7065 Intermediate Similarity NPC212598
0.7065 Intermediate Similarity NPC470819
0.7065 Intermediate Similarity NPC115179
0.7065 Intermediate Similarity NPC106040
0.7065 Intermediate Similarity NPC477748
0.7053 Intermediate Similarity NPC272050
0.7045 Intermediate Similarity NPC324170
0.7037 Intermediate Similarity NPC74722
0.7037 Intermediate Similarity NPC101622
0.7037 Intermediate Similarity NPC304690
0.7033 Intermediate Similarity NPC471056
0.7033 Intermediate Similarity NPC199382
0.7033 Intermediate Similarity NPC471055
0.7011 Intermediate Similarity NPC475946
0.7 Intermediate Similarity NPC259299
0.7 Intermediate Similarity NPC470658
0.7 Intermediate Similarity NPC119001
0.6989 Remote Similarity NPC469403
0.6979 Remote Similarity NPC311166
0.6977 Remote Similarity NPC477089
0.6977 Remote Similarity NPC470944
0.697 Remote Similarity NPC470571
0.6962 Remote Similarity NPC308844
0.6947 Remote Similarity NPC470255
0.6941 Remote Similarity NPC12740
0.6941 Remote Similarity NPC152017
0.6941 Remote Similarity NPC110461
0.6932 Remote Similarity NPC184208
0.6932 Remote Similarity NPC246621
0.6932 Remote Similarity NPC8538
0.6932 Remote Similarity NPC315731
0.6923 Remote Similarity NPC61527
0.6923 Remote Similarity NPC472379
0.6923 Remote Similarity NPC208473
0.6915 Remote Similarity NPC472199
0.6915 Remote Similarity NPC477749
0.6915 Remote Similarity NPC472197
0.6907 Remote Similarity NPC155319
0.6907 Remote Similarity NPC91197
0.6907 Remote Similarity NPC309503
0.6907 Remote Similarity NPC125551
0.6907 Remote Similarity NPC239547
0.6907 Remote Similarity NPC96597
0.69 Remote Similarity NPC134270
0.6897 Remote Similarity NPC139712
0.6897 Remote Similarity NPC86971
0.6889 Remote Similarity NPC266718
0.6883 Remote Similarity NPC127824
0.6882 Remote Similarity NPC104129
0.6882 Remote Similarity NPC249408
0.6875 Remote Similarity NPC472189
0.6875 Remote Similarity NPC471372
0.6875 Remote Similarity NPC471362
0.6875 Remote Similarity NPC13924
0.6869 Remote Similarity NPC20673
0.6869 Remote Similarity NPC57586
0.6869 Remote Similarity NPC475655
0.6869 Remote Similarity NPC2313
0.6869 Remote Similarity NPC471637
0.6869 Remote Similarity NPC154127
0.6869 Remote Similarity NPC154132
0.6869 Remote Similarity NPC475157
0.6867 Remote Similarity NPC472254
0.686 Remote Similarity NPC476439
0.6854 Remote Similarity NPC471298
0.6854 Remote Similarity NPC477385
0.6854 Remote Similarity NPC477390
0.6854 Remote Similarity NPC20072
0.6848 Remote Similarity NPC74139
0.6842 Remote Similarity NPC320089
0.6842 Remote Similarity NPC109406
0.6842 Remote Similarity NPC280390
0.6837 Remote Similarity NPC151093
0.6837 Remote Similarity NPC312325
0.6832 Remote Similarity NPC470321
0.6832 Remote Similarity NPC473207
0.6832 Remote Similarity NPC81567
0.6832 Remote Similarity NPC264867
0.6832 Remote Similarity NPC201880
0.6829 Remote Similarity NPC239373
0.6829 Remote Similarity NPC269841
0.6829 Remote Similarity NPC329989
0.6824 Remote Similarity NPC265921
0.6824 Remote Similarity NPC215215
0.6824 Remote Similarity NPC85831
0.6818 Remote Similarity NPC186072
0.6813 Remote Similarity NPC472442
0.6809 Remote Similarity NPC327253
0.6804 Remote Similarity NPC90583
0.6804 Remote Similarity NPC173329
0.6804 Remote Similarity NPC171598
0.6804 Remote Similarity NPC288350
0.68 Remote Similarity NPC238397
0.68 Remote Similarity NPC471363
0.6796 Remote Similarity NPC470024
0.679 Remote Similarity NPC73603
0.6786 Remote Similarity NPC135703
0.6782 Remote Similarity NPC474005
0.6782 Remote Similarity NPC474341
0.6782 Remote Similarity NPC475980
0.6778 Remote Similarity NPC471297
0.6778 Remote Similarity NPC2379
0.6778 Remote Similarity NPC31019
0.6778 Remote Similarity NPC106912
0.6778 Remote Similarity NPC263087
0.6778 Remote Similarity NPC27314
0.6778 Remote Similarity NPC49208
0.6778 Remote Similarity NPC475714
0.6778 Remote Similarity NPC23748
0.6774 Remote Similarity NPC60765
0.6771 Remote Similarity NPC472198
0.6771 Remote Similarity NPC469491
0.6768 Remote Similarity NPC477716
0.6768 Remote Similarity NPC475053
0.6768 Remote Similarity NPC477721
0.6768 Remote Similarity NPC473204
0.6768 Remote Similarity NPC244878
0.6765 Remote Similarity NPC315070
0.6765 Remote Similarity NPC252296
0.6765 Remote Similarity NPC172867
0.6753 Remote Similarity NPC122239
0.6747 Remote Similarity NPC473361
0.6747 Remote Similarity NPC329904
0.6744 Remote Similarity NPC301525
0.6744 Remote Similarity NPC61863
0.6742 Remote Similarity NPC112868
0.6742 Remote Similarity NPC474894
0.6742 Remote Similarity NPC15978
0.6739 Remote Similarity NPC323209
0.6739 Remote Similarity NPC470836
0.6739 Remote Similarity NPC173917
0.6737 Remote Similarity NPC476075
0.6737 Remote Similarity NPC206679
0.6737 Remote Similarity NPC471324
0.6737 Remote Similarity NPC114172
0.6737 Remote Similarity NPC476084
0.6735 Remote Similarity NPC472188
0.6735 Remote Similarity NPC240372
0.6733 Remote Similarity NPC7644
0.6733 Remote Similarity NPC7613
0.6733 Remote Similarity NPC475889
0.6733 Remote Similarity NPC197736
0.6733 Remote Similarity NPC127933
0.6733 Remote Similarity NPC471450
0.6707 Remote Similarity NPC272961
0.6706 Remote Similarity NPC472173
0.6706 Remote Similarity NPC472174
0.6705 Remote Similarity NPC17550
0.6705 Remote Similarity NPC233295

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC190008 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
0.7188 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.66 Remote Similarity NPD6648 Approved
0.6593 Remote Similarity NPD6695 Phase 3
0.6522 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6465 Remote Similarity NPD7839 Suspended
0.6458 Remote Similarity NPD7838 Discovery
0.6444 Remote Similarity NPD7514 Phase 3
0.6444 Remote Similarity NPD7332 Phase 2
0.6437 Remote Similarity NPD8264 Approved
0.6404 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6372 Remote Similarity NPD8513 Phase 3
0.6372 Remote Similarity NPD8517 Approved
0.6372 Remote Similarity NPD8516 Approved
0.6372 Remote Similarity NPD8515 Approved
0.6327 Remote Similarity NPD5778 Approved
0.6327 Remote Similarity NPD5779 Approved
0.6316 Remote Similarity NPD7750 Discontinued
0.6316 Remote Similarity NPD7524 Approved
0.6289 Remote Similarity NPD6698 Approved
0.6289 Remote Similarity NPD46 Approved
0.6264 Remote Similarity NPD6930 Phase 2
0.6264 Remote Similarity NPD6931 Approved
0.625 Remote Similarity NPD8039 Approved
0.6224 Remote Similarity NPD7637 Suspended
0.6224 Remote Similarity NPD7983 Approved
0.6222 Remote Similarity NPD7145 Approved
0.622 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5344 Discontinued
0.6196 Remote Similarity NPD6902 Approved
0.6173 Remote Similarity NPD368 Approved
0.6168 Remote Similarity NPD6686 Approved
0.6154 Remote Similarity NPD6929 Approved
0.6147 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6145 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6136 Remote Similarity NPD6924 Approved
0.6136 Remote Similarity NPD6926 Approved
0.6111 Remote Similarity NPD6932 Approved
0.6111 Remote Similarity NPD5776 Phase 2
0.6111 Remote Similarity NPD6925 Approved
0.6087 Remote Similarity NPD4820 Approved
0.6087 Remote Similarity NPD7503 Approved
0.6087 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6087 Remote Similarity NPD4822 Approved
0.6087 Remote Similarity NPD4821 Approved
0.6087 Remote Similarity NPD4819 Approved
0.6064 Remote Similarity NPD7154 Phase 3
0.6064 Remote Similarity NPD5362 Discontinued
0.6061 Remote Similarity NPD7087 Discontinued
0.6023 Remote Similarity NPD4732 Discontinued
0.6022 Remote Similarity NPD6898 Phase 1
0.602 Remote Similarity NPD6101 Approved
0.602 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6 Remote Similarity NPD6933 Approved
0.5979 Remote Similarity NPD4251 Approved
0.5979 Remote Similarity NPD4250 Approved
0.5977 Remote Similarity NPD7143 Approved
0.5977 Remote Similarity NPD7144 Approved
0.596 Remote Similarity NPD3168 Discontinued
0.5949 Remote Similarity NPD4219 Approved
0.5938 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6893 Approved
0.5909 Remote Similarity NPD7151 Approved
0.5909 Remote Similarity NPD7152 Approved
0.5909 Remote Similarity NPD7150 Approved
0.59 Remote Similarity NPD6411 Approved
0.5895 Remote Similarity NPD5331 Approved
0.5895 Remote Similarity NPD5332 Approved
0.5876 Remote Similarity NPD4249 Approved
0.587 Remote Similarity NPD4271 Approved
0.587 Remote Similarity NPD4268 Approved
0.5862 Remote Similarity NPD6923 Approved
0.5862 Remote Similarity NPD6922 Approved
0.5854 Remote Similarity NPD1145 Discontinued
0.5851 Remote Similarity NPD4790 Discontinued
0.5833 Remote Similarity NPD8074 Phase 3
0.5826 Remote Similarity NPD7328 Approved
0.5826 Remote Similarity NPD7327 Approved
0.5823 Remote Similarity NPD342 Phase 1
0.5812 Remote Similarity NPD8033 Approved
0.5812 Remote Similarity NPD8444 Approved
0.581 Remote Similarity NPD7640 Approved
0.581 Remote Similarity NPD7639 Approved
0.5806 Remote Similarity NPD6683 Phase 2
0.58 Remote Similarity NPD8522 Clinical (unspecified phase)
0.58 Remote Similarity NPD5785 Approved
0.5789 Remote Similarity NPD5209 Approved
0.5789 Remote Similarity NPD4269 Approved
0.5789 Remote Similarity NPD4270 Approved
0.5776 Remote Similarity NPD7516 Approved
0.575 Remote Similarity NPD8451 Approved
0.5745 Remote Similarity NPD7509 Discontinued
0.5726 Remote Similarity NPD8377 Approved
0.5726 Remote Similarity NPD8294 Approved
0.5714 Remote Similarity NPD7638 Approved
0.5714 Remote Similarity NPD7829 Approved
0.5714 Remote Similarity NPD7830 Approved
0.5714 Remote Similarity NPD5786 Approved
0.5702 Remote Similarity NPD8448 Approved
0.57 Remote Similarity NPD6051 Approved
0.5699 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5688 Remote Similarity NPD6640 Phase 3
0.5684 Remote Similarity NPD5369 Approved
0.5678 Remote Similarity NPD8378 Approved
0.5678 Remote Similarity NPD8380 Approved
0.5678 Remote Similarity NPD8296 Approved
0.5678 Remote Similarity NPD8379 Approved
0.5678 Remote Similarity NPD8335 Approved
0.5673 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5667 Remote Similarity NPD8342 Approved
0.5667 Remote Similarity NPD8340 Approved
0.5667 Remote Similarity NPD8299 Approved
0.5667 Remote Similarity NPD8341 Approved
0.5644 Remote Similarity NPD7136 Phase 2
0.5636 Remote Similarity NPD6412 Phase 2
0.5631 Remote Similarity NPD5282 Discontinued
0.5625 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5612 Remote Similarity NPD5363 Approved
0.5603 Remote Similarity NPD7500 Approved

Structure

External Identifiers

PubChem CID   5323571
ChEMBL   CHEMBL516882
ZINC  

Physicochemical Properties

Molecular Weight:  362.25
ALogP:  2.6022
MLogP:  3.44
XLogP:  3.121
# Rotatable Bonds:  10
Polar Surface Area:  47.92
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  26

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Similar NPs/Drugs