Natural Product: NPC189777

Natural Product ID:  NPC189777
Common Name:   Sipholenol L
IUPAC Name:   (3S,5aS,6S,7S,9aS)-6-[2-[(1S,4aS,5S,8aR)-5-hydroxy-2,5,8,8-tetramethyl-1,4,4a,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 L
Molecular Formula:   C30H52O4
Standard InCHIKey:  KNWLCYSMHRPQLC-ZWULGDALSA-N
Standard InCHI:  InChI=1S/C30H52O4/c1-19-9-11-21-25(26(2,3)17-18-29(21,7)32)20(19)10-12-22-28(6)15-13-23(31)27(4,5)34-24(28)14-16-30(22,8)33/h9,20-25,31-33H,10-18H2,1-8H3/t20-,21+,22+,23+,24+,25-,28+,29+,30+/m1/s1
Canonical SMILES:  CC1=CC[C@H]2[C@@H]([C@@H]1CC[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 = 0.9 8864235
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio IC50 = 27 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 NPC189777 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
0.9512 High Similarity NPC290731
0.9302 High Similarity NPC210268
0.9286 High Similarity NPC233744
0.9167 High Similarity NPC476217
0.907 High Similarity NPC115607
0.907 High Similarity NPC97103
0.8791 High Similarity NPC272451
0.8765 High Similarity NPC130136
0.8764 High Similarity NPC119379
0.8539 High Similarity NPC470832
0.8478 Intermediate Similarity NPC91439
0.8462 Intermediate Similarity NPC305160
0.8452 Intermediate Similarity NPC287749
0.8415 Intermediate Similarity NPC477925
0.8415 Intermediate Similarity NPC274079
0.8352 Intermediate Similarity NPC98193
0.8313 Intermediate Similarity NPC477924
0.8313 Intermediate Similarity NPC471798
0.8298 Intermediate Similarity NPC470067
0.8298 Intermediate Similarity NPC216260
0.8298 Intermediate Similarity NPC477875
0.8298 Intermediate Similarity NPC5358
0.8298 Intermediate Similarity NPC470066
0.8298 Intermediate Similarity NPC477876
0.8295 Intermediate Similarity NPC237344
0.8295 Intermediate Similarity NPC125399
0.8293 Intermediate Similarity NPC66566
0.8293 Intermediate Similarity NPC477923
0.828 Intermediate Similarity NPC90583
0.8261 Intermediate Similarity NPC473258
0.8261 Intermediate Similarity NPC477927
0.8261 Intermediate Similarity NPC72817
0.8256 Intermediate Similarity NPC30166
0.8202 Intermediate Similarity NPC476948
0.8191 Intermediate Similarity NPC26307
0.8191 Intermediate Similarity NPC475033
0.8191 Intermediate Similarity NPC474994
0.8191 Intermediate Similarity NPC476040
0.8191 Intermediate Similarity NPC475032
0.8191 Intermediate Similarity NPC476021
0.8172 Intermediate Similarity NPC8774
0.8161 Intermediate Similarity NPC159168
0.8161 Intermediate Similarity NPC207013
0.8161 Intermediate Similarity NPC253402
0.8148 Intermediate Similarity NPC164022
0.8148 Intermediate Similarity NPC167706
0.814 Intermediate Similarity NPC70927
0.814 Intermediate Similarity NPC476646
0.8111 Intermediate Similarity NPC474668
0.8111 Intermediate Similarity NPC133588
0.8095 Intermediate Similarity NPC90979
0.8095 Intermediate Similarity NPC472805
0.809 Intermediate Similarity NPC94462
0.8085 Intermediate Similarity NPC12103
0.8085 Intermediate Similarity NPC103165
0.8085 Intermediate Similarity NPC227583
0.8085 Intermediate Similarity NPC210717
0.8085 Intermediate Similarity NPC288970
0.8085 Intermediate Similarity NPC72204
0.8085 Intermediate Similarity NPC98457
0.8072 Intermediate Similarity NPC291503
0.8068 Intermediate Similarity NPC83702
0.8068 Intermediate Similarity NPC319238
0.8068 Intermediate Similarity NPC238992
0.8068 Intermediate Similarity NPC124172
0.8065 Intermediate Similarity NPC65402
0.8065 Intermediate Similarity NPC127718
0.8065 Intermediate Similarity NPC178949
0.8065 Intermediate Similarity NPC211238
0.8065 Intermediate Similarity NPC96736
0.8061 Intermediate Similarity NPC471434
0.8061 Intermediate Similarity NPC471435
0.8049 Intermediate Similarity NPC182717
0.8046 Intermediate Similarity NPC47763
0.8043 Intermediate Similarity NPC41554
0.8043 Intermediate Similarity NPC97404
0.8043 Intermediate Similarity NPC302584
0.8023 Intermediate Similarity NPC96362
0.8023 Intermediate Similarity NPC102253
0.8023 Intermediate Similarity NPC13554
0.8023 Intermediate Similarity NPC322313
0.8023 Intermediate Similarity NPC236237
0.8023 Intermediate Similarity NPC236112
0.8022 Intermediate Similarity NPC477917
0.8022 Intermediate Similarity NPC473058
0.8022 Intermediate Similarity NPC470361
0.8022 Intermediate Similarity NPC105495
0.8022 Intermediate Similarity NPC259875
0.8022 Intermediate Similarity NPC187785
0.8021 Intermediate Similarity NPC473790
0.8021 Intermediate Similarity NPC324598
0.8 Intermediate Similarity NPC240372
0.8 Intermediate Similarity NPC300499
0.8 Intermediate Similarity NPC261807
0.8 Intermediate Similarity NPC316604
0.7976 Intermediate Similarity NPC470766
0.7976 Intermediate Similarity NPC106432
0.7959 Intermediate Similarity NPC475701
0.7957 Intermediate Similarity NPC474792
0.7957 Intermediate Similarity NPC91654
0.7957 Intermediate Similarity NPC67398
0.7955 Intermediate Similarity NPC110778
0.7952 Intermediate Similarity NPC91858
0.7952 Intermediate Similarity NPC477138
0.7952 Intermediate Similarity NPC100334
0.7952 Intermediate Similarity NPC243342
0.7938 Intermediate Similarity NPC155974
0.7938 Intermediate Similarity NPC309425
0.7938 Intermediate Similarity NPC472023
0.7938 Intermediate Similarity NPC11974
0.7938 Intermediate Similarity NPC4831
0.7938 Intermediate Similarity NPC263756
0.7938 Intermediate Similarity NPC117714
0.7938 Intermediate Similarity NPC129372
0.7938 Intermediate Similarity NPC96784
0.7938 Intermediate Similarity NPC475617
0.7938 Intermediate Similarity NPC160734
0.7938 Intermediate Similarity NPC47566
0.7938 Intermediate Similarity NPC235920
0.7938 Intermediate Similarity NPC88000
0.7938 Intermediate Similarity NPC476132
0.7935 Intermediate Similarity NPC11216
0.7935 Intermediate Similarity NPC3345
0.7935 Intermediate Similarity NPC191323
0.7935 Intermediate Similarity NPC329596
0.7935 Intermediate Similarity NPC159876
0.7935 Intermediate Similarity NPC204188
0.7935 Intermediate Similarity NPC295668
0.7935 Intermediate Similarity NPC291484
0.7935 Intermediate Similarity NPC80561
0.7931 Intermediate Similarity NPC474531
0.7931 Intermediate Similarity NPC249423
0.7931 Intermediate Similarity NPC242350
0.7917 Intermediate Similarity NPC280825
0.7917 Intermediate Similarity NPC247233
0.7917 Intermediate Similarity NPC477928
0.7917 Intermediate Similarity NPC476895
0.7917 Intermediate Similarity NPC234287
0.7917 Intermediate Similarity NPC470068
0.7912 Intermediate Similarity NPC473436
0.7907 Intermediate Similarity NPC273410
0.7907 Intermediate Similarity NPC80530
0.7907 Intermediate Similarity NPC291379
0.7907 Intermediate Similarity NPC328714
0.7907 Intermediate Similarity NPC472463
0.7889 Intermediate Similarity NPC6391
0.7889 Intermediate Similarity NPC24277
0.7889 Intermediate Similarity NPC470836
0.7889 Intermediate Similarity NPC261266
0.7889 Intermediate Similarity NPC201273
0.7889 Intermediate Similarity NPC255143
0.7882 Intermediate Similarity NPC470711
0.7882 Intermediate Similarity NPC157996
0.7882 Intermediate Similarity NPC101475
0.7882 Intermediate Similarity NPC40394
0.7882 Intermediate Similarity NPC34177
0.7882 Intermediate Similarity NPC470758
0.7879 Intermediate Similarity NPC474464
0.7879 Intermediate Similarity NPC85593
0.7879 Intermediate Similarity NPC31430
0.7879 Intermediate Similarity NPC470885
0.7879 Intermediate Similarity NPC187400
0.7879 Intermediate Similarity NPC221562
0.7872 Intermediate Similarity NPC215700
0.7872 Intermediate Similarity NPC105490
0.7865 Intermediate Similarity NPC102048
0.7865 Intermediate Similarity NPC166279
0.7857 Intermediate Similarity NPC213674
0.7857 Intermediate Similarity NPC136816
0.7857 Intermediate Similarity NPC256133
0.7857 Intermediate Similarity NPC32832
0.7857 Intermediate Similarity NPC76497
0.7857 Intermediate Similarity NPC30289
0.7849 Intermediate Similarity NPC114389
0.7841 Intermediate Similarity NPC470614
0.7841 Intermediate Similarity NPC248886
0.7841 Intermediate Similarity NPC1272
0.7841 Intermediate Similarity NPC7988
0.7835 Intermediate Similarity NPC476195
0.7835 Intermediate Similarity NPC473200
0.7835 Intermediate Similarity NPC474571
0.7835 Intermediate Similarity NPC254567
0.7835 Intermediate Similarity NPC7341
0.7835 Intermediate Similarity NPC64348
0.7835 Intermediate Similarity NPC208358
0.7831 Intermediate Similarity NPC471799
0.7831 Intermediate Similarity NPC95165
0.7826 Intermediate Similarity NPC109744
0.7826 Intermediate Similarity NPC16265
0.7826 Intermediate Similarity NPC246028
0.7812 Intermediate Similarity NPC210337
0.7812 Intermediate Similarity NPC243728
0.7812 Intermediate Similarity NPC476893
0.7812 Intermediate Similarity NPC473890
0.7805 Intermediate Similarity NPC92801
0.7802 Intermediate Similarity NPC474657
0.7802 Intermediate Similarity NPC470620
0.7802 Intermediate Similarity NPC186145
0.78 Intermediate Similarity NPC477877
0.78 Intermediate Similarity NPC474015

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC189777 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
0.8023 Intermediate Similarity NPD7525 Registered
0.7907 Intermediate Similarity NPD7645 Phase 2
0.7442 Intermediate Similarity NPD7339 Approved
0.7442 Intermediate Similarity NPD6942 Approved
0.7419 Intermediate Similarity NPD7524 Approved
0.7356 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7638 Approved
0.7174 Intermediate Similarity NPD6695 Phase 3
0.7159 Intermediate Similarity NPD6933 Approved
0.7129 Intermediate Similarity NPD7640 Approved
0.7129 Intermediate Similarity NPD7639 Approved
0.7075 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6412 Phase 2
0.7027 Intermediate Similarity NPD7327 Approved
0.7027 Intermediate Similarity NPD7328 Approved
0.6972 Remote Similarity NPD4632 Approved
0.697 Remote Similarity NPD7748 Approved
0.6964 Remote Similarity NPD7516 Approved
0.6947 Remote Similarity NPD3618 Phase 1
0.6939 Remote Similarity NPD7515 Phase 2
0.6932 Remote Similarity NPD6926 Approved
0.6932 Remote Similarity NPD6924 Approved
0.6931 Remote Similarity NPD7902 Approved
0.6916 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6915 Remote Similarity NPD4786 Approved
0.6907 Remote Similarity NPD5328 Approved
0.6897 Remote Similarity NPD4243 Approved
0.6893 Remote Similarity NPD5344 Discontinued
0.6882 Remote Similarity NPD3667 Approved
0.6875 Remote Similarity NPD7750 Discontinued
0.6869 Remote Similarity NPD4202 Approved
0.6869 Remote Similarity NPD6399 Phase 3
0.6848 Remote Similarity NPD6930 Phase 2
0.6848 Remote Similarity NPD6931 Approved
0.6848 Remote Similarity NPD7509 Discontinued
0.6837 Remote Similarity NPD3168 Discontinued
0.6822 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6792 Remote Similarity NPD6402 Approved
0.6792 Remote Similarity NPD5739 Approved
0.6792 Remote Similarity NPD6675 Approved
0.6792 Remote Similarity NPD7128 Approved
0.6768 Remote Similarity NPD6079 Approved
0.6765 Remote Similarity NPD4755 Approved
0.6754 Remote Similarity NPD6059 Approved
0.6754 Remote Similarity NPD8377 Approved
0.6754 Remote Similarity NPD6054 Approved
0.6754 Remote Similarity NPD8294 Approved
0.6754 Remote Similarity NPD6319 Approved
0.6742 Remote Similarity NPD4784 Approved
0.6742 Remote Similarity NPD4785 Approved
0.6739 Remote Similarity NPD6929 Approved
0.6727 Remote Similarity NPD8297 Approved
0.6703 Remote Similarity NPD6932 Approved
0.6699 Remote Similarity NPD4225 Approved
0.6697 Remote Similarity NPD4634 Approved
0.6697 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7503 Approved
0.6696 Remote Similarity NPD8380 Approved
0.6696 Remote Similarity NPD8296 Approved
0.6696 Remote Similarity NPD8379 Approved
0.6696 Remote Similarity NPD8335 Approved
0.6696 Remote Similarity NPD8033 Approved
0.6696 Remote Similarity NPD8378 Approved
0.6667 Remote Similarity NPD4748 Discontinued
0.6667 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7320 Approved
0.6667 Remote Similarity NPD8264 Approved
0.6667 Remote Similarity NPD6899 Approved
0.6667 Remote Similarity NPD6686 Approved
0.6667 Remote Similarity NPD6881 Approved
0.6638 Remote Similarity NPD6370 Approved
0.6637 Remote Similarity NPD6009 Approved
0.6635 Remote Similarity NPD4696 Approved
0.6635 Remote Similarity NPD4700 Approved
0.6635 Remote Similarity NPD5286 Approved
0.6635 Remote Similarity NPD5285 Approved
0.6634 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6634 Remote Similarity NPD7900 Approved
0.6606 Remote Similarity NPD6372 Approved
0.6606 Remote Similarity NPD6373 Approved
0.66 Remote Similarity NPD7087 Discontinued
0.6581 Remote Similarity NPD8328 Phase 3
0.6581 Remote Similarity NPD7604 Phase 2
0.6574 Remote Similarity NPD5697 Approved
0.6574 Remote Similarity NPD5701 Approved
0.6571 Remote Similarity NPD5223 Approved
0.6571 Remote Similarity NPD4159 Approved
0.6562 Remote Similarity NPD3133 Approved
0.6562 Remote Similarity NPD3665 Phase 1
0.6562 Remote Similarity NPD3666 Approved
0.6559 Remote Similarity NPD6683 Phase 2
0.6556 Remote Similarity NPD1810 Approved
0.6556 Remote Similarity NPD1811 Approved
0.6552 Remote Similarity NPD5983 Phase 2
0.6552 Remote Similarity NPD6016 Approved
0.6552 Remote Similarity NPD6015 Approved
0.6545 Remote Similarity NPD6883 Approved
0.6545 Remote Similarity NPD7102 Approved
0.6545 Remote Similarity NPD7290 Approved
0.6525 Remote Similarity NPD7492 Approved
0.6522 Remote Similarity NPD6925 Approved
0.6522 Remote Similarity NPD5776 Phase 2
0.6517 Remote Similarity NPD7151 Approved
0.6517 Remote Similarity NPD7150 Approved
0.6517 Remote Similarity NPD7152 Approved
0.6514 Remote Similarity NPD6011 Approved
0.6509 Remote Similarity NPD7632 Discontinued
0.6509 Remote Similarity NPD5224 Approved
0.6509 Remote Similarity NPD5225 Approved
0.6509 Remote Similarity NPD5226 Approved
0.6509 Remote Similarity NPD4633 Approved
0.6509 Remote Similarity NPD5211 Phase 2
0.6505 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6505 Remote Similarity NPD5222 Approved
0.6505 Remote Similarity NPD5221 Approved
0.6505 Remote Similarity NPD4697 Phase 3
0.6496 Remote Similarity NPD5988 Approved
0.6495 Remote Similarity NPD6893 Approved
0.6491 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6491 Remote Similarity NPD7115 Discovery
0.6489 Remote Similarity NPD7514 Phase 3
0.6489 Remote Similarity NPD7332 Phase 2
0.6486 Remote Similarity NPD8130 Phase 1
0.6486 Remote Similarity NPD6617 Approved
0.6486 Remote Similarity NPD6649 Approved
0.6486 Remote Similarity NPD6847 Approved
0.6486 Remote Similarity NPD6869 Approved
0.6486 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6486 Remote Similarity NPD6650 Approved
0.6484 Remote Similarity NPD5275 Approved
0.6484 Remote Similarity NPD4190 Phase 3
0.6481 Remote Similarity NPD6008 Approved
0.6477 Remote Similarity NPD6922 Approved
0.6477 Remote Similarity NPD6923 Approved
0.6476 Remote Similarity NPD6648 Approved
0.6471 Remote Similarity NPD6336 Discontinued
0.6471 Remote Similarity NPD7507 Approved
0.6471 Remote Similarity NPD371 Approved
0.6471 Remote Similarity NPD6616 Approved
0.6455 Remote Similarity NPD6013 Approved
0.6455 Remote Similarity NPD6012 Approved
0.6455 Remote Similarity NPD6014 Approved
0.6452 Remote Similarity NPD7145 Approved
0.6449 Remote Similarity NPD5174 Approved
0.6449 Remote Similarity NPD4754 Approved
0.6449 Remote Similarity NPD5175 Approved
0.6442 Remote Similarity NPD6084 Phase 2
0.6442 Remote Similarity NPD5173 Approved
0.6442 Remote Similarity NPD6083 Phase 2
0.6441 Remote Similarity NPD6067 Discontinued
0.6436 Remote Similarity NPD8035 Phase 2
0.6436 Remote Similarity NPD8034 Phase 2
0.6429 Remote Similarity NPD6882 Approved
0.6429 Remote Similarity NPD368 Approved
0.6422 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6421 Remote Similarity NPD6898 Phase 1
0.6417 Remote Similarity NPD7078 Approved
0.6417 Remote Similarity NPD8293 Discontinued
0.6404 Remote Similarity NPD7143 Approved
0.6404 Remote Similarity NPD7144 Approved
0.64 Remote Similarity NPD6051 Approved
0.64 Remote Similarity NPD4753 Phase 2
0.6392 Remote Similarity NPD3668 Phase 3
0.6389 Remote Similarity NPD5141 Approved
0.6383 Remote Similarity NPD4195 Approved
0.6372 Remote Similarity NPD8133 Approved
0.6364 Remote Similarity NPD7736 Approved
0.6364 Remote Similarity NPD6033 Approved
0.633 Remote Similarity NPD4767 Approved
0.633 Remote Similarity NPD5357 Phase 1
0.633 Remote Similarity NPD4768 Approved
0.6327 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7319 Approved
0.6277 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6275 Remote Similarity NPD6411 Approved
0.6263 Remote Similarity NPD7334 Approved
0.6263 Remote Similarity NPD7146 Approved
0.6263 Remote Similarity NPD5330 Approved
0.6263 Remote Similarity NPD7521 Approved
0.6263 Remote Similarity NPD6684 Approved
0.6263 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6263 Remote Similarity NPD6409 Approved
0.625 Remote Similarity NPD6902 Approved
0.6226 Remote Similarity NPD5290 Discontinued
0.6222 Remote Similarity NPD2254 Approved
0.6222 Remote Similarity NPD2687 Approved
0.6222 Remote Similarity NPD2686 Approved
0.6216 Remote Similarity NPD4730 Approved
0.6216 Remote Similarity NPD5128 Approved
0.6216 Remote Similarity NPD4729 Approved
0.6204 Remote Similarity NPD3653 Clinical (unspecified phase)
0.62 Remote Similarity NPD3573 Approved
0.6186 Remote Similarity NPD4221 Approved
0.6186 Remote Similarity NPD4223 Phase 3
0.6162 Remote Similarity NPD5329 Approved
0.6154 Remote Similarity NPD6335 Approved
0.6146 Remote Similarity NPD6928 Phase 2
0.6146 Remote Similarity NPD4695 Discontinued

Structure

External Identifiers

PubChem CID   44234954
ChEMBL   CHEMBL562568
ZINC  

Physicochemical Properties

Molecular Weight:  476.39
ALogP:  1.4961
MLogP:  4.32
XLogP:  6.474
# Rotatable Bonds:  14
Polar Surface Area:  69.92
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  34

Download Data

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