Natural Product: NPC97103

Natural Product ID:  NPC97103
Common Name:   Siphonellinol C-23-Hydroperoxide
IUPAC Name:   (3S,5aS,6S,7R,9aS)-6-[2-[(5R,6S)-6-[(E)-4-hydroperoxy-4-methylpent-2-enyl]-5-hydroxy-2,6-dimethylcyclohexen-1-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
Synonyms:   Siphonellinol C-23-Hydroperoxide
Molecular Formula:   C30H52O6
Standard InCHIKey:  KKUBOUCKYPCBMT-CDMQMTAESA-N
Standard InCHI:  InChI=1S/C30H52O6/c1-20-10-13-24(32)28(6,17-9-16-26(2,3)36-34)21(20)11-12-22-29(7)18-14-23(31)27(4,5)35-25(29)15-19-30(22,8)33/h9,16,22-25,31-34H,10-15,17-19H2,1-8H3/b16-9+/t22-,23-,24+,25-,28-,29-,30+/m0/s1
Canonical SMILES:  OOC(/C=C/C[C@]1(C)[C@H](O)CCC(=C1CC[C@@H]1[C@](C)(O)CC[C@H]2[C@@]1(C)CC[C@@H](C(O2)(C)C)O)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
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota PMID[19534474]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio IC50 = 0.7 15267229
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 50000 nM 15646539
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 50000 nM PubChem BioAssay data set
NPT83 Cell Line MCF7 Homo sapiens IC50 = 27400 nM 24941130
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 53951.06 nM PubChem BioAssay data set
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio IC50 = 270 25725376

  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 NPC97103 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
0.9762 High Similarity NPC115607
0.9639 High Similarity NPC476217
0.9518 High Similarity NPC290731
0.907 High Similarity NPC233744
0.907 High Similarity NPC189777
0.8478 Intermediate Similarity NPC473258
0.8462 Intermediate Similarity NPC210268
0.837 Intermediate Similarity NPC119379
0.8352 Intermediate Similarity NPC470832
0.8298 Intermediate Similarity NPC210717
0.8298 Intermediate Similarity NPC103165
0.8295 Intermediate Similarity NPC83702
0.8256 Intermediate Similarity NPC287749
0.8256 Intermediate Similarity NPC96362
0.8211 Intermediate Similarity NPC261807
0.8211 Intermediate Similarity NPC26307
0.8191 Intermediate Similarity NPC8774
0.8161 Intermediate Similarity NPC471270
0.8161 Intermediate Similarity NPC476646
0.8152 Intermediate Similarity NPC191323
0.8111 Intermediate Similarity NPC255143
0.8105 Intermediate Similarity NPC12103
0.8105 Intermediate Similarity NPC288970
0.8105 Intermediate Similarity NPC98457
0.8105 Intermediate Similarity NPC227583
0.8085 Intermediate Similarity NPC65402
0.8085 Intermediate Similarity NPC127718
0.8068 Intermediate Similarity NPC471408
0.8065 Intermediate Similarity NPC41554
0.8065 Intermediate Similarity NPC97404
0.8046 Intermediate Similarity NPC474592
0.8046 Intermediate Similarity NPC95124
0.8046 Intermediate Similarity NPC236707
0.8046 Intermediate Similarity NPC471266
0.8043 Intermediate Similarity NPC246028
0.8043 Intermediate Similarity NPC477917
0.8022 Intermediate Similarity NPC476948
0.8022 Intermediate Similarity NPC245004
0.8021 Intermediate Similarity NPC240372
0.8021 Intermediate Similarity NPC272451
0.8 Intermediate Similarity NPC477925
0.8 Intermediate Similarity NPC274079
0.8 Intermediate Similarity NPC265588
0.7957 Intermediate Similarity NPC329596
0.7957 Intermediate Similarity NPC204188
0.7957 Intermediate Similarity NPC80561
0.7957 Intermediate Similarity NPC295668
0.7957 Intermediate Similarity NPC291484
0.7957 Intermediate Similarity NPC3345
0.7957 Intermediate Similarity NPC11216
0.7955 Intermediate Similarity NPC249423
0.7938 Intermediate Similarity NPC312325
0.7935 Intermediate Similarity NPC474668
0.7935 Intermediate Similarity NPC133588
0.7931 Intermediate Similarity NPC233295
0.7917 Intermediate Similarity NPC72204
0.7917 Intermediate Similarity NPC90583
0.7912 Intermediate Similarity NPC261266
0.7907 Intermediate Similarity NPC130136
0.7907 Intermediate Similarity NPC471798
0.7907 Intermediate Similarity NPC477924
0.7895 Intermediate Similarity NPC72817
0.7895 Intermediate Similarity NPC305160
0.7895 Intermediate Similarity NPC477927
0.7895 Intermediate Similarity NPC472360
0.7895 Intermediate Similarity NPC472416
0.7889 Intermediate Similarity NPC102048
0.7889 Intermediate Similarity NPC46320
0.7882 Intermediate Similarity NPC291503
0.7882 Intermediate Similarity NPC477923
0.7882 Intermediate Similarity NPC66566
0.7872 Intermediate Similarity NPC302584
0.7872 Intermediate Similarity NPC114389
0.7857 Intermediate Similarity NPC64348
0.7849 Intermediate Similarity NPC49783
0.7849 Intermediate Similarity NPC128066
0.7849 Intermediate Similarity NPC20946
0.7849 Intermediate Similarity NPC470361
0.7835 Intermediate Similarity NPC473244
0.7816 Intermediate Similarity NPC167891
0.7816 Intermediate Similarity NPC83351
0.7791 Intermediate Similarity NPC253190
0.7789 Intermediate Similarity NPC474792
0.7789 Intermediate Similarity NPC67398
0.7789 Intermediate Similarity NPC137461
0.7789 Intermediate Similarity NPC310013
0.7789 Intermediate Similarity NPC91654
0.7778 Intermediate Similarity NPC472554
0.7778 Intermediate Similarity NPC475617
0.7766 Intermediate Similarity NPC470390
0.7766 Intermediate Similarity NPC245410
0.7766 Intermediate Similarity NPC192437
0.7766 Intermediate Similarity NPC270511
0.7766 Intermediate Similarity NPC14380
0.7765 Intermediate Similarity NPC306727
0.7765 Intermediate Similarity NPC243342
0.7765 Intermediate Similarity NPC477138
0.7755 Intermediate Similarity NPC470067
0.7755 Intermediate Similarity NPC247233
0.7755 Intermediate Similarity NPC476895
0.7755 Intermediate Similarity NPC470066
0.7738 Intermediate Similarity NPC164022
0.7738 Intermediate Similarity NPC471272
0.7732 Intermediate Similarity NPC221801
0.7732 Intermediate Similarity NPC211810
0.7732 Intermediate Similarity NPC91439
0.7732 Intermediate Similarity NPC284194
0.7732 Intermediate Similarity NPC471765
0.7732 Intermediate Similarity NPC129569
0.7727 Intermediate Similarity NPC72755
0.7727 Intermediate Similarity NPC476367
0.7717 Intermediate Similarity NPC6391
0.7717 Intermediate Similarity NPC237344
0.7708 Intermediate Similarity NPC469491
0.7708 Intermediate Similarity NPC105490
0.7701 Intermediate Similarity NPC91594
0.77 Intermediate Similarity NPC11956
0.77 Intermediate Similarity NPC472552
0.7692 Intermediate Similarity NPC319238
0.7684 Intermediate Similarity NPC477574
0.7677 Intermediate Similarity NPC188968
0.7677 Intermediate Similarity NPC38855
0.7677 Intermediate Similarity NPC79303
0.7674 Intermediate Similarity NPC32832
0.7667 Intermediate Similarity NPC259858
0.766 Intermediate Similarity NPC259875
0.766 Intermediate Similarity NPC187785
0.766 Intermediate Similarity NPC261320
0.766 Intermediate Similarity NPC470819
0.766 Intermediate Similarity NPC16265
0.7653 Intermediate Similarity NPC120446
0.7653 Intermediate Similarity NPC476893
0.7653 Intermediate Similarity NPC475032
0.7653 Intermediate Similarity NPC475033
0.7653 Intermediate Similarity NPC476040
0.7653 Intermediate Similarity NPC476021
0.7653 Intermediate Similarity NPC474994
0.7647 Intermediate Similarity NPC470767
0.7647 Intermediate Similarity NPC470763
0.7634 Intermediate Similarity NPC131329
0.7629 Intermediate Similarity NPC477969
0.7629 Intermediate Similarity NPC292178
0.7629 Intermediate Similarity NPC476894
0.7629 Intermediate Similarity NPC135224
0.7629 Intermediate Similarity NPC86893
0.7629 Intermediate Similarity NPC476720
0.7624 Intermediate Similarity NPC194323
0.7624 Intermediate Similarity NPC474124
0.7624 Intermediate Similarity NPC23584
0.7619 Intermediate Similarity NPC92801
0.7614 Intermediate Similarity NPC476314
0.7614 Intermediate Similarity NPC68119
0.7614 Intermediate Similarity NPC13823
0.7609 Intermediate Similarity NPC318390
0.7609 Intermediate Similarity NPC35933
0.7604 Intermediate Similarity NPC98193
0.7604 Intermediate Similarity NPC7349
0.7604 Intermediate Similarity NPC53555
0.76 Intermediate Similarity NPC11974
0.76 Intermediate Similarity NPC280991
0.76 Intermediate Similarity NPC235920
0.76 Intermediate Similarity NPC96784
0.76 Intermediate Similarity NPC476896
0.7582 Intermediate Similarity NPC477978
0.7582 Intermediate Similarity NPC49208
0.7582 Intermediate Similarity NPC474634
0.7582 Intermediate Similarity NPC23748
0.7582 Intermediate Similarity NPC185605
0.7579 Intermediate Similarity NPC92885
0.7579 Intermediate Similarity NPC48732
0.7579 Intermediate Similarity NPC476226
0.7579 Intermediate Similarity NPC470817
0.7579 Intermediate Similarity NPC220216
0.7579 Intermediate Similarity NPC77796
0.7579 Intermediate Similarity NPC159876
0.7576 Intermediate Similarity NPC477928
0.7576 Intermediate Similarity NPC477875
0.7576 Intermediate Similarity NPC216260
0.7576 Intermediate Similarity NPC477876
0.7576 Intermediate Similarity NPC5358
0.7573 Intermediate Similarity NPC33053
0.7558 Intermediate Similarity NPC476366
0.7558 Intermediate Similarity NPC91858
0.7558 Intermediate Similarity NPC201048
0.7556 Intermediate Similarity NPC47761
0.7556 Intermediate Similarity NPC142163
0.7553 Intermediate Similarity NPC280556
0.7551 Intermediate Similarity NPC57664
0.7549 Intermediate Similarity NPC470768
0.7549 Intermediate Similarity NPC75608
0.7549 Intermediate Similarity NPC473543
0.7529 Intermediate Similarity NPC471271
0.7529 Intermediate Similarity NPC242001
0.7529 Intermediate Similarity NPC242992
0.7529 Intermediate Similarity NPC23954
0.7529 Intermediate Similarity NPC167706
0.7529 Intermediate Similarity NPC471268
0.7529 Intermediate Similarity NPC477792
0.7527 Intermediate Similarity NPC125399
0.7527 Intermediate Similarity NPC299068

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC97103 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
0.7447 Intermediate Similarity NPD7524 Approved
0.7426 Intermediate Similarity NPD5344 Discontinued
0.7312 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD8264 Approved
0.7253 Intermediate Similarity NPD7525 Registered
0.7204 Intermediate Similarity NPD6695 Phase 3
0.7143 Intermediate Similarity NPD7645 Phase 2
0.7 Intermediate Similarity NPD6933 Approved
0.699 Remote Similarity NPD6648 Approved
0.6907 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6907 Remote Similarity NPD7750 Discontinued
0.6893 Remote Similarity NPD4225 Approved
0.6893 Remote Similarity NPD7638 Approved
0.6889 Remote Similarity NPD6942 Approved
0.6889 Remote Similarity NPD7339 Approved
0.6882 Remote Similarity NPD7332 Phase 2
0.6882 Remote Similarity NPD6930 Phase 2
0.6882 Remote Similarity NPD6931 Approved
0.6882 Remote Similarity NPD7514 Phase 3
0.6869 Remote Similarity NPD3168 Discontinued
0.6827 Remote Similarity NPD7640 Approved
0.6827 Remote Similarity NPD7639 Approved
0.6813 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6789 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6778 Remote Similarity NPD6926 Approved
0.6778 Remote Similarity NPD6924 Approved
0.6774 Remote Similarity NPD6929 Approved
0.6754 Remote Similarity NPD7328 Approved
0.6754 Remote Similarity NPD7327 Approved
0.6739 Remote Similarity NPD6932 Approved
0.6702 Remote Similarity NPD7509 Discontinued
0.6696 Remote Similarity NPD7516 Approved
0.6667 Remote Similarity NPD7145 Approved
0.6667 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6634 Remote Similarity NPD7087 Discontinued
0.6632 Remote Similarity NPD6902 Approved
0.6581 Remote Similarity NPD8033 Approved
0.6581 Remote Similarity NPD7503 Approved
0.6569 Remote Similarity NPD5779 Approved
0.6569 Remote Similarity NPD5778 Approved
0.6559 Remote Similarity NPD6925 Approved
0.6559 Remote Similarity NPD5776 Phase 2
0.6556 Remote Similarity NPD7151 Approved
0.6556 Remote Similarity NPD7150 Approved
0.6556 Remote Similarity NPD7152 Approved
0.6549 Remote Similarity NPD4632 Approved
0.6545 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6686 Approved
0.6535 Remote Similarity NPD7838 Discovery
0.6531 Remote Similarity NPD6893 Approved
0.6522 Remote Similarity NPD7115 Discovery
0.6496 Remote Similarity NPD8294 Approved
0.6496 Remote Similarity NPD8377 Approved
0.6471 Remote Similarity NPD368 Approved
0.6471 Remote Similarity NPD7637 Suspended
0.6458 Remote Similarity NPD6898 Phase 1
0.6455 Remote Similarity NPD6412 Phase 2
0.6449 Remote Similarity NPD4159 Approved
0.6444 Remote Similarity NPD7143 Approved
0.6444 Remote Similarity NPD7144 Approved
0.6441 Remote Similarity NPD8378 Approved
0.6441 Remote Similarity NPD8379 Approved
0.6441 Remote Similarity NPD8296 Approved
0.6441 Remote Similarity NPD8335 Approved
0.6441 Remote Similarity NPD8380 Approved
0.6429 Remote Similarity NPD4786 Approved
0.6429 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6421 Remote Similarity NPD6683 Phase 2
0.6413 Remote Similarity NPD4785 Approved
0.6413 Remote Similarity NPD4784 Approved
0.6408 Remote Similarity NPD6399 Phase 3
0.6392 Remote Similarity NPD3667 Approved
0.6373 Remote Similarity NPD6698 Approved
0.6373 Remote Similarity NPD46 Approved
0.6364 Remote Similarity NPD5357 Phase 1
0.6356 Remote Similarity NPD6319 Approved
0.6356 Remote Similarity NPD6054 Approved
0.6354 Remote Similarity NPD4748 Discontinued
0.6346 Remote Similarity NPD7748 Approved
0.6339 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6333 Remote Similarity NPD6923 Approved
0.6333 Remote Similarity NPD6922 Approved
0.6321 Remote Similarity NPD7902 Approved
0.6316 Remote Similarity NPD8297 Approved
0.6311 Remote Similarity NPD7983 Approved
0.6311 Remote Similarity NPD6411 Approved
0.6311 Remote Similarity NPD7515 Phase 2
0.6311 Remote Similarity NPD6079 Approved
0.63 Remote Similarity NPD3618 Phase 1
0.6283 Remote Similarity NPD4634 Approved
0.6275 Remote Similarity NPD5328 Approved
0.6262 Remote Similarity NPD8029 Clinical (unspecified phase)
0.625 Remote Similarity NPD6881 Approved
0.625 Remote Similarity NPD6899 Approved
0.625 Remote Similarity NPD6370 Approved
0.625 Remote Similarity NPD4202 Approved
0.6239 Remote Similarity NPD6009 Approved
0.6239 Remote Similarity NPD5211 Phase 2
0.6239 Remote Similarity NPD3653 Clinical (unspecified phase)
0.6239 Remote Similarity NPD7632 Discontinued
0.6237 Remote Similarity NPD1811 Approved
0.6237 Remote Similarity NPD1810 Approved
0.623 Remote Similarity NPD7507 Approved
0.6218 Remote Similarity NPD6059 Approved
0.6216 Remote Similarity NPD6675 Approved
0.6216 Remote Similarity NPD7128 Approved
0.6216 Remote Similarity NPD5739 Approved
0.6216 Remote Similarity NPD6640 Phase 3
0.6216 Remote Similarity NPD6402 Approved
0.6204 Remote Similarity NPD4696 Approved
0.6204 Remote Similarity NPD5286 Approved
0.6204 Remote Similarity NPD5285 Approved
0.6198 Remote Similarity NPD7604 Phase 2
0.6196 Remote Similarity NPD4243 Approved
0.6174 Remote Similarity NPD6053 Discontinued
0.6168 Remote Similarity NPD4755 Approved
0.6167 Remote Similarity NPD6015 Approved
0.6167 Remote Similarity NPD6016 Approved
0.6167 Remote Similarity NPD5983 Phase 2
0.6161 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6161 Remote Similarity NPD5697 Approved
0.6148 Remote Similarity NPD7492 Approved
0.6147 Remote Similarity NPD5223 Approved
0.614 Remote Similarity NPD6883 Approved
0.614 Remote Similarity NPD7290 Approved
0.614 Remote Similarity NPD6371 Approved
0.614 Remote Similarity NPD7102 Approved
0.6136 Remote Similarity NPD371 Approved
0.6129 Remote Similarity NPD4732 Discontinued
0.6126 Remote Similarity NPD5141 Approved
0.6117 Remote Similarity NPD6101 Approved
0.6117 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6117 Remote Similarity NPD6051 Approved
0.6116 Remote Similarity NPD5988 Approved
0.6106 Remote Similarity NPD6011 Approved
0.6106 Remote Similarity NPD7320 Approved
0.6102 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6098 Remote Similarity NPD6616 Approved
0.6098 Remote Similarity NPD6336 Discontinued
0.6091 Remote Similarity NPD5226 Approved
0.6091 Remote Similarity NPD5225 Approved
0.6091 Remote Similarity NPD4633 Approved
0.6091 Remote Similarity NPD5224 Approved
0.6087 Remote Similarity NPD8130 Phase 1
0.6087 Remote Similarity NPD6649 Approved
0.6087 Remote Similarity NPD6847 Approved
0.6087 Remote Similarity NPD6869 Approved
0.6087 Remote Similarity NPD6617 Approved
0.6087 Remote Similarity NPD6650 Approved
0.608 Remote Similarity NPD7319 Approved
0.6075 Remote Similarity NPD5221 Approved
0.6075 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6075 Remote Similarity NPD5222 Approved
0.6071 Remote Similarity NPD6008 Approved
0.6066 Remote Similarity NPD8328 Phase 3
0.6058 Remote Similarity NPD7136 Phase 2
0.6055 Remote Similarity NPD4700 Approved
0.6053 Remote Similarity NPD6013 Approved
0.6053 Remote Similarity NPD6373 Approved
0.6053 Remote Similarity NPD6372 Approved
0.6053 Remote Similarity NPD6014 Approved
0.6053 Remote Similarity NPD6012 Approved
0.6048 Remote Similarity NPD7078 Approved
0.6038 Remote Similarity NPD5282 Discontinued
0.6038 Remote Similarity NPD7900 Approved
0.6038 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6036 Remote Similarity NPD5175 Approved
0.6036 Remote Similarity NPD5174 Approved
0.6034 Remote Similarity NPD6882 Approved
0.6033 Remote Similarity NPD8517 Approved
0.6033 Remote Similarity NPD8516 Approved
0.6033 Remote Similarity NPD8515 Approved
0.6033 Remote Similarity NPD8513 Phase 3
0.602 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6019 Remote Similarity NPD5173 Approved
0.6018 Remote Similarity NPD5701 Approved
0.6 Remote Similarity NPD6110 Phase 1
0.6 Remote Similarity NPD7736 Approved
0.5983 Remote Similarity NPD8133 Approved
0.5978 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5948 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5948 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5941 Remote Similarity NPD3665 Phase 1
0.5941 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5941 Remote Similarity NPD3133 Approved
0.5941 Remote Similarity NPD3668 Phase 3
0.5941 Remote Similarity NPD3666 Approved
0.5935 Remote Similarity NPD6067 Discontinued
0.5926 Remote Similarity NPD4697 Phase 3
0.5922 Remote Similarity NPD4250 Approved
0.5922 Remote Similarity NPD4251 Approved
0.592 Remote Similarity NPD8293 Discontinued
0.5918 Remote Similarity NPD4195 Approved
0.5914 Remote Similarity NPD2687 Approved
0.5914 Remote Similarity NPD2254 Approved
0.5914 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5914 Remote Similarity NPD2686 Approved
0.5902 Remote Similarity NPD6921 Approved
0.5893 Remote Similarity NPD4754 Approved
0.5877 Remote Similarity NPD7899 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   44234958
ChEMBL   CHEMBL558129
ZINC  

Physicochemical Properties

Molecular Weight:  508.38
ALogP:  1.4649
MLogP:  4.1
XLogP:  3.599
# Rotatable Bonds:  19
Polar Surface Area:  99.38
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  36

Download Data

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Biological Activities  
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