Natural Product: NPC92231

Natural Product ID:  NPC92231
Common Name:   1S-Hydroperoxy-12S-Hydroxybromosphaerol-B
IUPAC Name:   (1S,3S,4S,4aS,4bS,5S,8R,8aS,10aS)-1-bromo-8a-(bromomethyl)-5-hydroperoxy-4,10a-dimethyl-8-propan-2-yl-2,3,4a,4b,5,8,9,10-octahydro-1H-phenanthrene-3,4-diol
Synonyms:  
Molecular Formula:   C20H32Br2O4
Standard InCHIKey:  SLASZMTUABGCGQ-VHXYLUBJSA-N
Standard InCHI:  InChI=1S/C20H32Br2O4/c1-11(2)12-5-6-13(26-25)16-17-18(3,7-8-20(12,16)10-21)14(22)9-15(23)19(17,4)24/h5-6,11-17,23-25H,7-10H2,1-4H3/t12-,13-,14-,15-,16-,17-,18+,19+,20-/m0/s1
Canonical SMILES:  OO[C@H]1C=C[C@H]([C@@]2([C@@H]1[C@@H]1[C@](C)(O)[C@@H](O)C[C@@H]([C@@]1(C)CC2)Br)CBr)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
NPO29354 Sphaerococcus coronopifolius Species Sphaerococcaceae Eukaryota PMID[20045651]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT114 Cell Line LoVo Homo sapiens IC50 = 28000 nM 25302529
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 = 28000 nM 10.6019/CHEMBL1201861
NPT2 Others Unspecified IC50 = 22000 nM 17548196
NPT81 Cell Line A549 Homo sapiens IC50 = 26000 nM 15787461
NPT2 Others Unspecified IC50 = 27000 nM 18973387
NPT306 Cell Line PC-3 Homo sapiens IC50 = 28000 nM 17145798

  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 NPC92231 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
1.0 High Similarity NPC34732
0.967 High Similarity NPC156912
0.9348 High Similarity NPC257510
0.9348 High Similarity NPC299714
0.9222 High Similarity NPC239453
0.9222 High Similarity NPC224552
0.8901 High Similarity NPC131453
0.8495 Intermediate Similarity NPC188896
0.837 Intermediate Similarity NPC313115
0.8191 Intermediate Similarity NPC174273
0.8111 Intermediate Similarity NPC129501
0.7917 Intermediate Similarity NPC133588
0.7885 Intermediate Similarity NPC133921
0.7826 Intermediate Similarity NPC287749
0.7742 Intermediate Similarity NPC476646
0.7732 Intermediate Similarity NPC474668
0.7717 Intermediate Similarity NPC476610
0.7692 Intermediate Similarity NPC130136
0.7677 Intermediate Similarity NPC97404
0.7677 Intermediate Similarity NPC41554
0.7653 Intermediate Similarity NPC187785
0.7653 Intermediate Similarity NPC259875
0.7634 Intermediate Similarity NPC96362
0.7576 Intermediate Similarity NPC80561
0.7576 Intermediate Similarity NPC329596
0.7576 Intermediate Similarity NPC204188
0.7576 Intermediate Similarity NPC11216
0.7576 Intermediate Similarity NPC3345
0.7576 Intermediate Similarity NPC291484
0.7553 Intermediate Similarity NPC249423
0.7553 Intermediate Similarity NPC311891
0.7526 Intermediate Similarity NPC299068
0.7526 Intermediate Similarity NPC261266
0.7526 Intermediate Similarity NPC237344
0.75 Intermediate Similarity NPC471798
0.75 Intermediate Similarity NPC275671
0.7475 Intermediate Similarity NPC470361
0.7475 Intermediate Similarity NPC97103
0.7475 Intermediate Similarity NPC109744
0.7449 Intermediate Similarity NPC189777
0.7449 Intermediate Similarity NPC233744
0.7449 Intermediate Similarity NPC474657
0.7449 Intermediate Similarity NPC470620
0.7449 Intermediate Similarity NPC186145
0.7447 Intermediate Similarity NPC113024
0.7447 Intermediate Similarity NPC471266
0.7447 Intermediate Similarity NPC95124
0.7423 Intermediate Similarity NPC470360
0.7423 Intermediate Similarity NPC318390
0.7419 Intermediate Similarity NPC83351
0.7419 Intermediate Similarity NPC167891
0.74 Intermediate Similarity NPC473956
0.74 Intermediate Similarity NPC475751
0.7396 Intermediate Similarity NPC185605
0.7396 Intermediate Similarity NPC207013
0.7396 Intermediate Similarity NPC253402
0.7396 Intermediate Similarity NPC159168
0.7391 Intermediate Similarity NPC477925
0.7391 Intermediate Similarity NPC274079
0.7391 Intermediate Similarity NPC253190
0.7379 Intermediate Similarity NPC288970
0.7374 Intermediate Similarity NPC212596
0.7374 Intermediate Similarity NPC4574
0.7374 Intermediate Similarity NPC280556
0.7374 Intermediate Similarity NPC475605
0.7374 Intermediate Similarity NPC475664
0.7368 Intermediate Similarity NPC471270
0.7363 Intermediate Similarity NPC475793
0.7363 Intermediate Similarity NPC237510
0.7353 Intermediate Similarity NPC127718
0.7353 Intermediate Similarity NPC65402
0.7347 Intermediate Similarity NPC94462
0.7347 Intermediate Similarity NPC6391
0.7347 Intermediate Similarity NPC139724
0.732 Intermediate Similarity NPC238992
0.7312 Intermediate Similarity NPC470758
0.7312 Intermediate Similarity NPC477924
0.7312 Intermediate Similarity NPC91594
0.7312 Intermediate Similarity NPC470711
0.7308 Intermediate Similarity NPC477226
0.73 Intermediate Similarity NPC138974
0.73 Intermediate Similarity NPC115607
0.73 Intermediate Similarity NPC105495
0.73 Intermediate Similarity NPC101886
0.73 Intermediate Similarity NPC329643
0.7292 Intermediate Similarity NPC47763
0.7292 Intermediate Similarity NPC30166
0.7283 Intermediate Similarity NPC66566
0.7283 Intermediate Similarity NPC291503
0.7283 Intermediate Similarity NPC476605
0.7283 Intermediate Similarity NPC477923
0.7283 Intermediate Similarity NPC32832
0.7282 Intermediate Similarity NPC8774
0.7273 Intermediate Similarity NPC476948
0.7273 Intermediate Similarity NPC304083
0.7263 Intermediate Similarity NPC236112
0.7263 Intermediate Similarity NPC236707
0.7255 Intermediate Similarity NPC119379
0.7255 Intermediate Similarity NPC310013
0.7253 Intermediate Similarity NPC182717
0.7234 Intermediate Similarity NPC11908
0.7228 Intermediate Similarity NPC191323
0.7228 Intermediate Similarity NPC470390
0.7228 Intermediate Similarity NPC192437
0.7228 Intermediate Similarity NPC245410
0.7228 Intermediate Similarity NPC270511
0.7228 Intermediate Similarity NPC295668
0.7228 Intermediate Similarity NPC14380
0.7216 Intermediate Similarity NPC474634
0.7216 Intermediate Similarity NPC141941
0.7216 Intermediate Similarity NPC134481
0.7216 Intermediate Similarity NPC317458
0.7216 Intermediate Similarity NPC193870
0.7212 Intermediate Similarity NPC98457
0.7212 Intermediate Similarity NPC72204
0.7212 Intermediate Similarity NPC103165
0.7212 Intermediate Similarity NPC210717
0.7212 Intermediate Similarity NPC227583
0.7212 Intermediate Similarity NPC12103
0.7204 Intermediate Similarity NPC106432
0.7204 Intermediate Similarity NPC470749
0.7204 Intermediate Similarity NPC265588
0.72 Intermediate Similarity NPC475817
0.7188 Intermediate Similarity NPC47761
0.7188 Intermediate Similarity NPC474531
0.7174 Intermediate Similarity NPC243342
0.7174 Intermediate Similarity NPC477138
0.7174 Intermediate Similarity NPC476366
0.7174 Intermediate Similarity NPC91858
0.7174 Intermediate Similarity NPC306727
0.7174 Intermediate Similarity NPC201048
0.7172 Intermediate Similarity NPC476217
0.7172 Intermediate Similarity NPC175145
0.7172 Intermediate Similarity NPC6605
0.7172 Intermediate Similarity NPC475069
0.7157 Intermediate Similarity NPC210268
0.7143 Intermediate Similarity NPC127606
0.7143 Intermediate Similarity NPC167706
0.7143 Intermediate Similarity NPC471271
0.7143 Intermediate Similarity NPC475798
0.7143 Intermediate Similarity NPC185568
0.7143 Intermediate Similarity NPC470077
0.7143 Intermediate Similarity NPC124172
0.7143 Intermediate Similarity NPC83702
0.7143 Intermediate Similarity NPC205845
0.7143 Intermediate Similarity NPC471268
0.7129 Intermediate Similarity NPC16265
0.7115 Intermediate Similarity NPC53565
0.7113 Intermediate Similarity NPC296701
0.7113 Intermediate Similarity NPC49964
0.7113 Intermediate Similarity NPC87489
0.7113 Intermediate Similarity NPC218616
0.7113 Intermediate Similarity NPC50964
0.7113 Intermediate Similarity NPC7988
0.7097 Intermediate Similarity NPC35397
0.7097 Intermediate Similarity NPC474946
0.7083 Intermediate Similarity NPC236237
0.7083 Intermediate Similarity NPC322313
0.7083 Intermediate Similarity NPC102253
0.7083 Intermediate Similarity NPC295131
0.7083 Intermediate Similarity NPC13554
0.7071 Intermediate Similarity NPC290731
0.7065 Intermediate Similarity NPC476609
0.7065 Intermediate Similarity NPC95165
0.7065 Intermediate Similarity NPC471799
0.7064 Intermediate Similarity NPC160843
0.7059 Intermediate Similarity NPC92885
0.7059 Intermediate Similarity NPC77796
0.7059 Intermediate Similarity NPC476226
0.7053 Intermediate Similarity NPC300499
0.7053 Intermediate Similarity NPC274750
0.7053 Intermediate Similarity NPC215307
0.7053 Intermediate Similarity NPC148977
0.7048 Intermediate Similarity NPC471903
0.7048 Intermediate Similarity NPC90583
0.7041 Intermediate Similarity NPC85095
0.7041 Intermediate Similarity NPC477818
0.7041 Intermediate Similarity NPC211135
0.7041 Intermediate Similarity NPC110778
0.7041 Intermediate Similarity NPC216420
0.7041 Intermediate Similarity NPC470558
0.7041 Intermediate Similarity NPC82623
0.703 Intermediate Similarity NPC67872
0.7021 Intermediate Similarity NPC63958
0.7021 Intermediate Similarity NPC61080
0.7021 Intermediate Similarity NPC476606
0.7019 Intermediate Similarity NPC305160
0.7019 Intermediate Similarity NPC477605
0.701 Intermediate Similarity NPC23852
0.701 Intermediate Similarity NPC264245
0.701 Intermediate Similarity NPC209620
0.701 Intermediate Similarity NPC242350
0.7 Intermediate Similarity NPC152808
0.7 Intermediate Similarity NPC166607
0.7 Intermediate Similarity NPC201273
0.7 Intermediate Similarity NPC269058
0.7 Intermediate Similarity NPC24277
0.7 Intermediate Similarity NPC71520
0.7 Intermediate Similarity NPC293287
0.6989 Remote Similarity NPC100334

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC92231 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
0.7083 Intermediate Similarity NPD7525 Registered
0.6804 Remote Similarity NPD7645 Phase 2
0.6602 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6562 Remote Similarity NPD6942 Approved
0.6562 Remote Similarity NPD7339 Approved
0.6495 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6442 Remote Similarity NPD7524 Approved
0.6429 Remote Similarity NPD7632 Discontinued
0.6392 Remote Similarity NPD8264 Approved
0.6327 Remote Similarity NPD6933 Approved
0.6311 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6306 Remote Similarity NPD7638 Approved
0.625 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD7639 Approved
0.6238 Remote Similarity NPD6931 Approved
0.6238 Remote Similarity NPD7332 Phase 2
0.6238 Remote Similarity NPD6930 Phase 2
0.6238 Remote Similarity NPD7514 Phase 3
0.6214 Remote Similarity NPD6695 Phase 3
0.6204 Remote Similarity NPD6079 Approved
0.6204 Remote Similarity NPD7515 Phase 2
0.619 Remote Similarity NPD3618 Phase 1
0.6186 Remote Similarity NPD4634 Approved
0.6168 Remote Similarity NPD5328 Approved
0.6154 Remote Similarity NPD4786 Approved
0.6147 Remote Similarity NPD4202 Approved
0.614 Remote Similarity NPD5211 Phase 2
0.6139 Remote Similarity NPD6929 Approved
0.6122 Remote Similarity NPD4784 Approved
0.6122 Remote Similarity NPD6924 Approved
0.6122 Remote Similarity NPD4785 Approved
0.6122 Remote Similarity NPD6926 Approved
0.6117 Remote Similarity NPD3667 Approved
0.6106 Remote Similarity NPD5286 Approved
0.6106 Remote Similarity NPD5285 Approved
0.6106 Remote Similarity NPD4696 Approved
0.6102 Remote Similarity NPD4061 Clinical (unspecified phase)
0.61 Remote Similarity NPD6932 Approved
0.6082 Remote Similarity NPD4243 Approved
0.6078 Remote Similarity NPD7509 Discontinued
0.6071 Remote Similarity NPD4755 Approved
0.6053 Remote Similarity NPD5344 Discontinued
0.6053 Remote Similarity NPD5223 Approved
0.6048 Remote Similarity NPD7516 Approved
0.6042 Remote Similarity NPD4267 Clinical (unspecified phase)
0.604 Remote Similarity NPD7145 Approved
0.604 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6034 Remote Similarity NPD5141 Approved
0.6033 Remote Similarity NPD4632 Approved
0.6019 Remote Similarity NPD6902 Approved
0.6017 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6 Remote Similarity NPD5226 Approved
0.6 Remote Similarity NPD4633 Approved
0.6 Remote Similarity NPD5225 Approved
0.6 Remote Similarity NPD5224 Approved
0.5982 Remote Similarity NPD5221 Approved
0.5982 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5982 Remote Similarity NPD5222 Approved
0.5981 Remote Similarity NPD7750 Discontinued
0.5978 Remote Similarity NPD368 Approved
0.5968 Remote Similarity NPD7328 Approved
0.5968 Remote Similarity NPD7327 Approved
0.5965 Remote Similarity NPD4700 Approved
0.5952 Remote Similarity NPD7503 Approved
0.5948 Remote Similarity NPD5174 Approved
0.5948 Remote Similarity NPD5175 Approved
0.5946 Remote Similarity NPD7748 Approved
0.5943 Remote Similarity NPD6893 Approved
0.5941 Remote Similarity NPD6925 Approved
0.5941 Remote Similarity NPD5776 Phase 2
0.5935 Remote Similarity NPD6274 Approved
0.5929 Remote Similarity NPD5173 Approved
0.5929 Remote Similarity NPD7902 Approved
0.5922 Remote Similarity NPD4748 Discontinued
0.5918 Remote Similarity NPD7151 Approved
0.5918 Remote Similarity NPD7150 Approved
0.5918 Remote Similarity NPD7152 Approved
0.5913 Remote Similarity NPD4159 Approved
0.5887 Remote Similarity NPD7115 Discovery
0.5882 Remote Similarity NPD6881 Approved
0.5882 Remote Similarity NPD6899 Approved
0.5877 Remote Similarity NPD4225 Approved
0.5873 Remote Similarity NPD8294 Approved
0.5873 Remote Similarity NPD8377 Approved
0.5865 Remote Similarity NPD6898 Phase 1
0.5856 Remote Similarity NPD6399 Phase 3
0.5849 Remote Similarity NPD3666 Approved
0.5849 Remote Similarity NPD3133 Approved
0.5849 Remote Similarity NPD3665 Phase 1
0.5847 Remote Similarity NPD6402 Approved
0.5847 Remote Similarity NPD7128 Approved
0.5847 Remote Similarity NPD6675 Approved
0.5847 Remote Similarity NPD5739 Approved
0.5841 Remote Similarity NPD4697 Phase 3
0.5833 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5827 Remote Similarity NPD8380 Approved
0.5827 Remote Similarity NPD8033 Approved
0.5827 Remote Similarity NPD8379 Approved
0.5827 Remote Similarity NPD8378 Approved
0.5827 Remote Similarity NPD8296 Approved
0.5827 Remote Similarity NPD8335 Approved
0.5825 Remote Similarity NPD4195 Approved
0.5825 Remote Similarity NPD6683 Phase 2
0.582 Remote Similarity NPD8297 Approved
0.5816 Remote Similarity NPD7143 Approved
0.5816 Remote Similarity NPD7144 Approved
0.5812 Remote Similarity NPD4754 Approved
0.5798 Remote Similarity NPD6412 Phase 2
0.5798 Remote Similarity NPD5697 Approved
0.5785 Remote Similarity NPD6883 Approved
0.5785 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5785 Remote Similarity NPD7290 Approved
0.5785 Remote Similarity NPD7102 Approved
0.5766 Remote Similarity NPD7087 Discontinued
0.576 Remote Similarity NPD6009 Approved
0.575 Remote Similarity NPD4729 Approved
0.575 Remote Similarity NPD6011 Approved
0.575 Remote Similarity NPD6686 Approved
0.575 Remote Similarity NPD4730 Approved
0.575 Remote Similarity NPD7320 Approved
0.5748 Remote Similarity NPD6054 Approved
0.5748 Remote Similarity NPD6319 Approved
0.5743 Remote Similarity NPD4190 Phase 3
0.5743 Remote Similarity NPD5275 Approved
0.5741 Remote Similarity NPD4519 Discontinued
0.5741 Remote Similarity NPD4623 Approved
0.5739 Remote Similarity NPD5290 Discontinued
0.5738 Remote Similarity NPD6847 Approved
0.5738 Remote Similarity NPD6650 Approved
0.5738 Remote Similarity NPD6617 Approved
0.5738 Remote Similarity NPD6649 Approved
0.5738 Remote Similarity NPD8130 Phase 1
0.5738 Remote Similarity NPD6869 Approved
0.5727 Remote Similarity NPD6051 Approved
0.5727 Remote Similarity NPD4753 Phase 2
0.5714 Remote Similarity NPD6922 Approved
0.5714 Remote Similarity NPD6923 Approved
0.5714 Remote Similarity NPD4767 Approved
0.5714 Remote Similarity NPD4768 Approved
0.5702 Remote Similarity NPD6372 Approved
0.5702 Remote Similarity NPD6013 Approved
0.5702 Remote Similarity NPD6373 Approved
0.5702 Remote Similarity NPD6012 Approved
0.5702 Remote Similarity NPD6014 Approved
0.5701 Remote Similarity NPD3668 Phase 3
0.5691 Remote Similarity NPD6882 Approved
0.569 Remote Similarity NPD6648 Approved
0.5667 Remote Similarity NPD5701 Approved
0.5664 Remote Similarity NPD7900 Approved
0.5664 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5659 Remote Similarity NPD6370 Approved
0.5656 Remote Similarity NPD5247 Approved
0.5656 Remote Similarity NPD5135 Approved
0.5656 Remote Similarity NPD5249 Phase 3
0.5656 Remote Similarity NPD5251 Approved
0.5656 Remote Similarity NPD5248 Approved
0.5656 Remote Similarity NPD5250 Approved
0.5656 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5656 Remote Similarity NPD5169 Approved
0.5649 Remote Similarity NPD7507 Approved
0.5648 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5625 Remote Similarity NPD7637 Suspended
0.5625 Remote Similarity NPD6059 Approved
0.562 Remote Similarity NPD5128 Approved
0.5615 Remote Similarity NPD7604 Phase 2
0.5614 Remote Similarity NPD4629 Approved
0.5614 Remote Similarity NPD5210 Approved
0.561 Remote Similarity NPD6401 Clinical (unspecified phase)
0.561 Remote Similarity NPD5216 Approved
0.561 Remote Similarity NPD5215 Approved
0.561 Remote Similarity NPD5217 Approved
0.561 Remote Similarity NPD5127 Approved

Structure

External Identifiers

PubChem CID   24850581
ChEMBL   CHEMBL599689
ZINC  

Physicochemical Properties

Molecular Weight:  494.07
ALogP:  1.312
MLogP:  3
XLogP:  5.314
# Rotatable Bonds:  12
Polar Surface Area:  69.92
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  26

Download Data

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