Natural Product: NPC233744

Natural Product ID:  NPC233744
Common Name:   Sipholenol M
IUPAC Name:   (3S,5aS,6S,7S,9aS)-6-[2-[(3R,4aS,5S,8aR)-3-hydroperoxy-5-hydroxy-2,5,8,8-tetramethyl-3,4,4a,6,7,8a-hexahydronaphthalen-1-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
Synonyms:   Sipholenol M
Molecular Formula:   C30H52O6
Standard InCHIKey:  CXYXLYVALJRWSW-CAEUIZDWSA-N
Standard InCHI:  InChI=1S/C30H52O6/c1-18-19(25-20(17-21(18)36-34)29(7,32)16-15-26(25,2)3)9-10-22-28(6)13-11-23(31)27(4,5)35-24(28)12-14-30(22,8)33/h20-25,31-34H,9-17H2,1-8H3/t20-,21+,22-,23-,24-,25+,28-,29-,30-/m0/s1
Canonical SMILES:  OO[C@@H]1C[C@H]2[C@@H](C(=C1C)CC[C@@H]1[C@@](C)(O)CC[C@H]3[C@@]1(C)CC[C@@H](C(O3)(C)C)O)C(C)(C)CC[C@]2(C)O
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 = 0.8 8864235
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio IC50 = 140 8864235

  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 NPC233744 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
0.9286 High Similarity NPC189777
0.9167 High Similarity NPC476217
0.907 High Similarity NPC97103
0.8851 High Similarity NPC115607
0.8824 High Similarity NPC290731
0.8652 High Similarity NPC210268
0.8478 Intermediate Similarity NPC91439
0.8352 Intermediate Similarity NPC119379
0.8242 Intermediate Similarity NPC114389
0.8191 Intermediate Similarity NPC272451
0.8152 Intermediate Similarity NPC137461
0.8095 Intermediate Similarity NPC130136
0.8085 Intermediate Similarity NPC90583
0.8085 Intermediate Similarity NPC72204
0.8065 Intermediate Similarity NPC473258
0.8 Intermediate Similarity NPC476948
0.8 Intermediate Similarity NPC26307
0.7979 Intermediate Similarity NPC8774
0.7935 Intermediate Similarity NPC470832
0.7931 Intermediate Similarity NPC476646
0.7917 Intermediate Similarity NPC470066
0.7917 Intermediate Similarity NPC470067
0.7912 Intermediate Similarity NPC133588
0.7912 Intermediate Similarity NPC474668
0.7895 Intermediate Similarity NPC288970
0.7895 Intermediate Similarity NPC129569
0.7895 Intermediate Similarity NPC12103
0.7895 Intermediate Similarity NPC210717
0.7895 Intermediate Similarity NPC103165
0.7895 Intermediate Similarity NPC98457
0.7895 Intermediate Similarity NPC227583
0.7872 Intermediate Similarity NPC305160
0.7872 Intermediate Similarity NPC65402
0.7872 Intermediate Similarity NPC127718
0.7865 Intermediate Similarity NPC83702
0.7865 Intermediate Similarity NPC166279
0.7849 Intermediate Similarity NPC302584
0.7849 Intermediate Similarity NPC41554
0.7849 Intermediate Similarity NPC97404
0.7841 Intermediate Similarity NPC7988
0.7835 Intermediate Similarity NPC188968
0.7835 Intermediate Similarity NPC79303
0.7826 Intermediate Similarity NPC477917
0.7826 Intermediate Similarity NPC16265
0.7826 Intermediate Similarity NPC187785
0.7826 Intermediate Similarity NPC470361
0.7826 Intermediate Similarity NPC259875
0.7816 Intermediate Similarity NPC96362
0.7816 Intermediate Similarity NPC287749
0.7812 Intermediate Similarity NPC240372
0.7812 Intermediate Similarity NPC261807
0.7766 Intermediate Similarity NPC98193
0.7765 Intermediate Similarity NPC274079
0.7765 Intermediate Similarity NPC477925
0.7755 Intermediate Similarity NPC11974
0.7755 Intermediate Similarity NPC96784
0.7755 Intermediate Similarity NPC475617
0.7755 Intermediate Similarity NPC235920
0.7753 Intermediate Similarity NPC132635
0.7742 Intermediate Similarity NPC11216
0.7742 Intermediate Similarity NPC329596
0.7742 Intermediate Similarity NPC191323
0.7742 Intermediate Similarity NPC295668
0.7742 Intermediate Similarity NPC291484
0.7742 Intermediate Similarity NPC80561
0.7742 Intermediate Similarity NPC204188
0.7742 Intermediate Similarity NPC3345
0.7732 Intermediate Similarity NPC216260
0.7732 Intermediate Similarity NPC477876
0.7732 Intermediate Similarity NPC476895
0.7732 Intermediate Similarity NPC5358
0.7732 Intermediate Similarity NPC247233
0.7732 Intermediate Similarity NPC477875
0.7727 Intermediate Similarity NPC249423
0.7717 Intermediate Similarity NPC280556
0.7692 Intermediate Similarity NPC125399
0.7692 Intermediate Similarity NPC255143
0.7692 Intermediate Similarity NPC6391
0.7692 Intermediate Similarity NPC261266
0.7692 Intermediate Similarity NPC237344
0.7684 Intermediate Similarity NPC477927
0.7684 Intermediate Similarity NPC472360
0.7684 Intermediate Similarity NPC472416
0.7684 Intermediate Similarity NPC182826
0.7684 Intermediate Similarity NPC105490
0.7684 Intermediate Similarity NPC72817
0.7684 Intermediate Similarity NPC105375
0.7674 Intermediate Similarity NPC477924
0.7674 Intermediate Similarity NPC471798
0.7674 Intermediate Similarity NPC470711
0.7674 Intermediate Similarity NPC470758
0.7667 Intermediate Similarity NPC102048
0.766 Intermediate Similarity NPC41239
0.7653 Intermediate Similarity NPC64348
0.7653 Intermediate Similarity NPC271295
0.7647 Intermediate Similarity NPC66566
0.7647 Intermediate Similarity NPC32832
0.7647 Intermediate Similarity NPC477923
0.764 Intermediate Similarity NPC30166
0.764 Intermediate Similarity NPC471408
0.7634 Intermediate Similarity NPC246028
0.7629 Intermediate Similarity NPC476040
0.7629 Intermediate Similarity NPC210337
0.7629 Intermediate Similarity NPC476021
0.7629 Intermediate Similarity NPC474994
0.7629 Intermediate Similarity NPC476893
0.7629 Intermediate Similarity NPC473244
0.7629 Intermediate Similarity NPC475032
0.7629 Intermediate Similarity NPC475033
0.7614 Intermediate Similarity NPC22403
0.7609 Intermediate Similarity NPC471779
0.7609 Intermediate Similarity NPC245004
0.7609 Intermediate Similarity NPC470620
0.7604 Intermediate Similarity NPC476894
0.7604 Intermediate Similarity NPC477969
0.7604 Intermediate Similarity NPC292178
0.7604 Intermediate Similarity NPC135224
0.7604 Intermediate Similarity NPC86893
0.76 Intermediate Similarity NPC162354
0.76 Intermediate Similarity NPC473123
0.76 Intermediate Similarity NPC474124
0.76 Intermediate Similarity NPC473124
0.76 Intermediate Similarity NPC473523
0.7586 Intermediate Similarity NPC167891
0.7586 Intermediate Similarity NPC83351
0.7582 Intermediate Similarity NPC318390
0.7579 Intermediate Similarity NPC91654
0.7579 Intermediate Similarity NPC7349
0.7579 Intermediate Similarity NPC67398
0.7579 Intermediate Similarity NPC474792
0.7579 Intermediate Similarity NPC27918
0.7576 Intermediate Similarity NPC476896
0.7576 Intermediate Similarity NPC280991
0.7558 Intermediate Similarity NPC470766
0.7558 Intermediate Similarity NPC253190
0.7558 Intermediate Similarity NPC106432
0.7558 Intermediate Similarity NPC470749
0.7556 Intermediate Similarity NPC474634
0.7556 Intermediate Similarity NPC477978
0.7556 Intermediate Similarity NPC159168
0.7556 Intermediate Similarity NPC207013
0.7556 Intermediate Similarity NPC253402
0.7553 Intermediate Similarity NPC92885
0.7553 Intermediate Similarity NPC261990
0.7553 Intermediate Similarity NPC476226
0.7553 Intermediate Similarity NPC474249
0.7553 Intermediate Similarity NPC77796
0.7551 Intermediate Similarity NPC470068
0.7551 Intermediate Similarity NPC275865
0.7549 Intermediate Similarity NPC469318
0.7549 Intermediate Similarity NPC473173
0.7529 Intermediate Similarity NPC306727
0.7529 Intermediate Similarity NPC476366
0.7529 Intermediate Similarity NPC201048
0.7528 Intermediate Similarity NPC70927
0.7527 Intermediate Similarity NPC475605
0.7527 Intermediate Similarity NPC473436
0.7526 Intermediate Similarity NPC221801
0.7526 Intermediate Similarity NPC284194
0.7526 Intermediate Similarity NPC471765
0.7526 Intermediate Similarity NPC88009
0.7526 Intermediate Similarity NPC211810
0.7525 Intermediate Similarity NPC110656
0.7525 Intermediate Similarity NPC75608
0.7525 Intermediate Similarity NPC473543
0.7525 Intermediate Similarity NPC203354
0.7525 Intermediate Similarity NPC471435
0.7525 Intermediate Similarity NPC473127
0.7525 Intermediate Similarity NPC471434
0.75 Intermediate Similarity NPC164022
0.75 Intermediate Similarity NPC96736
0.75 Intermediate Similarity NPC178949
0.75 Intermediate Similarity NPC476367
0.75 Intermediate Similarity NPC476471
0.75 Intermediate Similarity NPC189513
0.75 Intermediate Similarity NPC167706
0.75 Intermediate Similarity NPC475344
0.75 Intermediate Similarity NPC144202
0.75 Intermediate Similarity NPC470571
0.75 Intermediate Similarity NPC94462
0.75 Intermediate Similarity NPC211238
0.75 Intermediate Similarity NPC299068
0.75 Intermediate Similarity NPC72755
0.7476 Intermediate Similarity NPC80210
0.7476 Intermediate Similarity NPC38376
0.7475 Intermediate Similarity NPC473510
0.7475 Intermediate Similarity NPC230546
0.7475 Intermediate Similarity NPC38855
0.7475 Intermediate Similarity NPC473790
0.7475 Intermediate Similarity NPC324598
0.7475 Intermediate Similarity NPC475877
0.7474 Intermediate Similarity NPC477574
0.7474 Intermediate Similarity NPC476417
0.7473 Intermediate Similarity NPC124172
0.7473 Intermediate Similarity NPC46320
0.7473 Intermediate Similarity NPC319238
0.7473 Intermediate Similarity NPC470077
0.7473 Intermediate Similarity NPC15534
0.7473 Intermediate Similarity NPC238992
0.7473 Intermediate Similarity NPC474047

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC233744 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
0.7416 Intermediate Similarity NPD7525 Registered
0.7404 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD7645 Phase 2
0.7053 Intermediate Similarity NPD7524 Approved
0.703 Intermediate Similarity NPD7638 Approved
0.7009 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7640 Approved
0.6961 Remote Similarity NPD7639 Approved
0.6916 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6915 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6893 Remote Similarity NPD4159 Approved
0.6875 Remote Similarity NPD7328 Approved
0.6875 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7327 Approved
0.6854 Remote Similarity NPD7339 Approved
0.6854 Remote Similarity NPD6942 Approved
0.6827 Remote Similarity NPD7632 Discontinued
0.6814 Remote Similarity NPD7516 Approved
0.6809 Remote Similarity NPD6695 Phase 3
0.6778 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6742 Remote Similarity NPD1811 Approved
0.6742 Remote Similarity NPD1810 Approved
0.6731 Remote Similarity NPD5344 Discontinued
0.6729 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4748 Discontinued
0.6609 Remote Similarity NPD8294 Approved
0.6609 Remote Similarity NPD8377 Approved
0.6593 Remote Similarity NPD6933 Approved
0.6574 Remote Similarity NPD6412 Phase 2
0.6552 Remote Similarity NPD8335 Approved
0.6552 Remote Similarity NPD8379 Approved
0.6552 Remote Similarity NPD7503 Approved
0.6552 Remote Similarity NPD8378 Approved
0.6552 Remote Similarity NPD8296 Approved
0.6552 Remote Similarity NPD8380 Approved
0.6552 Remote Similarity NPD8033 Approved
0.6538 Remote Similarity NPD4225 Approved
0.6531 Remote Similarity NPD7750 Discontinued
0.6518 Remote Similarity NPD4632 Approved
0.6514 Remote Similarity NPD6686 Approved
0.6491 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6489 Remote Similarity NPD6930 Phase 2
0.6489 Remote Similarity NPD6931 Approved
0.6484 Remote Similarity NPD8264 Approved
0.6471 Remote Similarity NPD371 Approved
0.6471 Remote Similarity NPD7748 Approved
0.6442 Remote Similarity NPD7902 Approved
0.6436 Remote Similarity NPD7515 Phase 2
0.6429 Remote Similarity NPD3618 Phase 1
0.6404 Remote Similarity NPD2687 Approved
0.6404 Remote Similarity NPD2254 Approved
0.6404 Remote Similarity NPD2686 Approved
0.64 Remote Similarity NPD5328 Approved
0.6392 Remote Similarity NPD4786 Approved
0.6383 Remote Similarity NPD6929 Approved
0.6374 Remote Similarity NPD6926 Approved
0.6374 Remote Similarity NPD6924 Approved
0.6373 Remote Similarity NPD6399 Phase 3
0.6373 Remote Similarity NPD4202 Approved
0.6354 Remote Similarity NPD3667 Approved
0.6348 Remote Similarity NPD7115 Discovery
0.6337 Remote Similarity NPD3168 Discontinued
0.6333 Remote Similarity NPD7507 Approved
0.6333 Remote Similarity NPD4243 Approved
0.633 Remote Similarity NPD6402 Approved
0.633 Remote Similarity NPD6675 Approved
0.633 Remote Similarity NPD5739 Approved
0.633 Remote Similarity NPD7128 Approved
0.6325 Remote Similarity NPD6059 Approved
0.6325 Remote Similarity NPD6054 Approved
0.6325 Remote Similarity NPD6319 Approved
0.6321 Remote Similarity NPD6648 Approved
0.6316 Remote Similarity NPD7509 Discontinued
0.6316 Remote Similarity NPD7332 Phase 2
0.6316 Remote Similarity NPD7514 Phase 3
0.6286 Remote Similarity NPD4755 Approved
0.6283 Remote Similarity NPD8297 Approved
0.6275 Remote Similarity NPD7087 Discontinued
0.6275 Remote Similarity NPD6079 Approved
0.625 Remote Similarity NPD4634 Approved
0.6238 Remote Similarity NPD6051 Approved
0.6235 Remote Similarity NPD368 Approved
0.6228 Remote Similarity NPD8133 Approved
0.6218 Remote Similarity NPD6370 Approved
0.6216 Remote Similarity NPD6881 Approved
0.6216 Remote Similarity NPD7320 Approved
0.6216 Remote Similarity NPD6899 Approved
0.6207 Remote Similarity NPD6009 Approved
0.6204 Remote Similarity NPD5211 Phase 2
0.6196 Remote Similarity NPD4784 Approved
0.6196 Remote Similarity NPD4785 Approved
0.6179 Remote Similarity NPD7319 Approved
0.617 Remote Similarity NPD5776 Phase 2
0.617 Remote Similarity NPD6925 Approved
0.617 Remote Similarity NPD6932 Approved
0.6168 Remote Similarity NPD5286 Approved
0.6168 Remote Similarity NPD5285 Approved
0.6168 Remote Similarity NPD4700 Approved
0.6168 Remote Similarity NPD4696 Approved
0.6167 Remote Similarity NPD7604 Phase 2
0.6167 Remote Similarity NPD8328 Phase 3
0.6162 Remote Similarity NPD6893 Approved
0.6161 Remote Similarity NPD6373 Approved
0.6161 Remote Similarity NPD6372 Approved
0.6154 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7900 Approved
0.6146 Remote Similarity NPD6928 Phase 2
0.6134 Remote Similarity NPD6015 Approved
0.6134 Remote Similarity NPD5983 Phase 2
0.6134 Remote Similarity NPD6016 Approved
0.6126 Remote Similarity NPD5697 Approved
0.6126 Remote Similarity NPD5701 Approved
0.6122 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6122 Remote Similarity NPD3669 Approved
0.6117 Remote Similarity NPD8034 Phase 2
0.6117 Remote Similarity NPD8035 Phase 2
0.6116 Remote Similarity NPD7492 Approved
0.6111 Remote Similarity NPD5223 Approved
0.6106 Remote Similarity NPD6883 Approved
0.6106 Remote Similarity NPD7102 Approved
0.6106 Remote Similarity NPD7290 Approved
0.6105 Remote Similarity NPD7145 Approved
0.6105 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6091 Remote Similarity NPD5141 Approved
0.6083 Remote Similarity NPD5988 Approved
0.6082 Remote Similarity NPD6902 Approved
0.6082 Remote Similarity NPD6898 Phase 1
0.6071 Remote Similarity NPD6011 Approved
0.6066 Remote Similarity NPD6336 Discontinued
0.6066 Remote Similarity NPD6616 Approved
0.6061 Remote Similarity NPD3666 Approved
0.6061 Remote Similarity NPD3133 Approved
0.6061 Remote Similarity NPD3665 Phase 1
0.6058 Remote Similarity NPD8171 Discontinued
0.6055 Remote Similarity NPD5224 Approved
0.6055 Remote Similarity NPD5225 Approved
0.6055 Remote Similarity NPD5226 Approved
0.6055 Remote Similarity NPD4633 Approved
0.6053 Remote Similarity NPD6649 Approved
0.6053 Remote Similarity NPD6617 Approved
0.6053 Remote Similarity NPD6869 Approved
0.6053 Remote Similarity NPD6847 Approved
0.6053 Remote Similarity NPD6650 Approved
0.6053 Remote Similarity NPD8130 Phase 1
0.6053 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6044 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6042 Remote Similarity NPD6683 Phase 2
0.6038 Remote Similarity NPD5221 Approved
0.6038 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6038 Remote Similarity NPD5222 Approved
0.6038 Remote Similarity NPD4697 Phase 3
0.6036 Remote Similarity NPD6008 Approved
0.6033 Remote Similarity NPD6067 Discontinued
0.6018 Remote Similarity NPD6014 Approved
0.6018 Remote Similarity NPD6012 Approved
0.6018 Remote Similarity NPD6013 Approved
0.6016 Remote Similarity NPD7078 Approved
0.6016 Remote Similarity NPD8293 Discontinued
0.6 Remote Similarity NPD4754 Approved
0.6 Remote Similarity NPD5175 Approved
0.6 Remote Similarity NPD6882 Approved
0.6 Remote Similarity NPD5174 Approved
0.6 Remote Similarity NPD6053 Discontinued
0.6 Remote Similarity NPD6921 Approved
0.6 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5981 Remote Similarity NPD6084 Phase 2
0.5981 Remote Similarity NPD6083 Phase 2
0.5981 Remote Similarity NPD5173 Approved
0.5978 Remote Similarity NPD7150 Approved
0.5978 Remote Similarity NPD7151 Approved
0.5978 Remote Similarity NPD7152 Approved
0.5968 Remote Similarity NPD6033 Approved
0.5968 Remote Similarity NPD7736 Approved
0.5962 Remote Similarity NPD7637 Suspended
0.5957 Remote Similarity NPD4190 Phase 3
0.5957 Remote Similarity NPD5275 Approved
0.5941 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6697 Approved
0.5938 Remote Similarity NPD6115 Approved
0.5938 Remote Similarity NPD6118 Approved
0.5938 Remote Similarity NPD6114 Approved
0.5934 Remote Similarity NPD6922 Approved
0.5934 Remote Similarity NPD6923 Approved
0.5922 Remote Similarity NPD4753 Phase 2
0.5905 Remote Similarity NPD5778 Approved
0.5905 Remote Similarity NPD5779 Approved
0.59 Remote Similarity NPD3668 Phase 3
0.5893 Remote Similarity NPD6640 Phase 3
0.5893 Remote Similarity NPD4768 Approved
0.5893 Remote Similarity NPD4767 Approved
0.5893 Remote Similarity NPD5357 Phase 1
0.5876 Remote Similarity NPD4195 Approved
0.587 Remote Similarity NPD4787 Phase 1
0.587 Remote Similarity NPD7144 Approved
0.587 Remote Similarity NPD7143 Approved
0.5865 Remote Similarity NPD46 Approved
0.5865 Remote Similarity NPD7838 Discovery
0.5865 Remote Similarity NPD6698 Approved

Structure

External Identifiers

PubChem CID   44234955
ChEMBL   CHEMBL562995
ZINC  

Physicochemical Properties

Molecular Weight:  508.38
ALogP:  1.37
MLogP:  4.1
XLogP:  4.365
# Rotatable Bonds:  16
Polar Surface Area:  99.38
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  36

Download Data

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