Natural Product: NPC474349

Natural Product ID:  NPC474349
Common Name:   17Alpha-Hydroxy-22,23-Epoxycholest-5-En-3Beta-Ol
IUPAC Name:   (3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-[(1R)-1-[3-(2-methylpropyl)oxiran-2-yl]ethyl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol
Synonyms:  
Molecular Formula:   C27H44O3
Standard InCHIKey:  OTLGIMRBKLQCNY-GRFKYTCVSA-N
Standard InCHI:  InChI=1S/C27H44O3/c1-16(2)14-23-24(30-23)17(3)27(29)13-10-22-20-7-6-18-15-19(28)8-11-25(18,4)21(20)9-12-26(22,27)5/h6,16-17,19-24,28-29H,7-15H2,1-5H3/t17-,19+,20-,21+,22+,23?,24?,25+,26+,27+/m1/s1
Canonical SMILES:  CC(CC1OC1[C@H]([C@@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)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
NPO32762 axinella cf. bidderi Species Axinellidae Eukaryota Indian Ocean PMID[15043442]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT461 Cell Line PANC-1 Homo sapiens GI50 = 2.17 ug/ml 11325244
NPT2 Others Unspecified GI50 = 2 ug/ml 11325244
NPT114 Cell Line LoVo Homo sapiens GI50 = 6.23 ug/ml 3655795
NPT2 Others Unspecified GI50 = 1.24 ug/ml 10.6019/CHEMBL1201861
NPT858 Cell Line LNCaP Homo sapiens GI50 = 3.09 ug/ml 10.6019/CHEMBL1201861

  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 NPC474349 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 NPC474189
0.9114 High Similarity NPC477522
0.9024 High Similarity NPC475789
0.8987 High Similarity NPC155986
0.8987 High Similarity NPC198968
0.8987 High Similarity NPC318495
0.8929 High Similarity NPC125399
0.8916 High Similarity NPC474047
0.8902 High Similarity NPC470614
0.8902 High Similarity NPC1272
0.8889 High Similarity NPC26117
0.8861 High Similarity NPC321016
0.8861 High Similarity NPC96319
0.8861 High Similarity NPC321381
0.8861 High Similarity NPC107059
0.8765 High Similarity NPC1319
0.8765 High Similarity NPC328714
0.875 High Similarity NPC34019
0.8734 High Similarity NPC28657
0.8734 High Similarity NPC304309
0.8734 High Similarity NPC162742
0.8734 High Similarity NPC134847
0.8734 High Similarity NPC288035
0.8734 High Similarity NPC136188
0.8734 High Similarity NPC230301
0.8734 High Similarity NPC285893
0.8734 High Similarity NPC22105
0.8706 High Similarity NPC293287
0.8706 High Similarity NPC152808
0.869 High Similarity NPC124172
0.8675 High Similarity NPC5985
0.8659 High Similarity NPC241290
0.8659 High Similarity NPC164840
0.8659 High Similarity NPC209944
0.8642 High Similarity NPC87604
0.8642 High Similarity NPC473943
0.8642 High Similarity NPC477514
0.8642 High Similarity NPC474216
0.8625 High Similarity NPC240604
0.8625 High Similarity NPC300324
0.8625 High Similarity NPC113733
0.8554 High Similarity NPC474759
0.8554 High Similarity NPC82986
0.8554 High Similarity NPC47761
0.8554 High Similarity NPC474683
0.8554 High Similarity NPC474731
0.8554 High Similarity NPC470383
0.8554 High Similarity NPC264245
0.8554 High Similarity NPC474752
0.8554 High Similarity NPC7505
0.8539 High Similarity NPC98193
0.8537 High Similarity NPC143182
0.8537 High Similarity NPC28862
0.8537 High Similarity NPC80530
0.8537 High Similarity NPC47982
0.8537 High Similarity NPC81306
0.8537 High Similarity NPC109546
0.8537 High Similarity NPC84694
0.8537 High Similarity NPC273410
0.8506 High Similarity NPC471952
0.85 High Similarity NPC257347
0.85 High Similarity NPC141071
0.85 High Similarity NPC471723
0.8488 Intermediate Similarity NPC201273
0.8488 Intermediate Similarity NPC24277
0.8481 Intermediate Similarity NPC474140
0.8471 Intermediate Similarity NPC209802
0.8471 Intermediate Similarity NPC205845
0.8452 Intermediate Similarity NPC30166
0.8452 Intermediate Similarity NPC101462
0.8452 Intermediate Similarity NPC201852
0.8452 Intermediate Similarity NPC49964
0.8434 Intermediate Similarity NPC322313
0.8434 Intermediate Similarity NPC236237
0.8434 Intermediate Similarity NPC234193
0.8434 Intermediate Similarity NPC102253
0.8415 Intermediate Similarity NPC18603
0.8415 Intermediate Similarity NPC285761
0.8415 Intermediate Similarity NPC244385
0.8415 Intermediate Similarity NPC6978
0.8415 Intermediate Similarity NPC275910
0.8415 Intermediate Similarity NPC138621
0.8415 Intermediate Similarity NPC307965
0.8415 Intermediate Similarity NPC76931
0.8415 Intermediate Similarity NPC167037
0.8395 Intermediate Similarity NPC129165
0.8395 Intermediate Similarity NPC134330
0.8395 Intermediate Similarity NPC189883
0.8391 Intermediate Similarity NPC149224
0.8375 Intermediate Similarity NPC471797
0.8372 Intermediate Similarity NPC157257
0.8372 Intermediate Similarity NPC318390
0.8372 Intermediate Similarity NPC266511
0.8372 Intermediate Similarity NPC274448
0.8353 Intermediate Similarity NPC110778
0.8353 Intermediate Similarity NPC474634
0.8353 Intermediate Similarity NPC477818
0.8333 Intermediate Similarity NPC242419
0.8333 Intermediate Similarity NPC209620
0.8333 Intermediate Similarity NPC474531
0.8333 Intermediate Similarity NPC23852
0.8333 Intermediate Similarity NPC235126
0.8313 Intermediate Similarity NPC30986
0.8313 Intermediate Similarity NPC209430
0.8295 Intermediate Similarity NPC470542
0.8295 Intermediate Similarity NPC2158
0.8293 Intermediate Similarity NPC214570
0.828 Intermediate Similarity NPC309493
0.8276 Intermediate Similarity NPC6605
0.8276 Intermediate Similarity NPC94462
0.8276 Intermediate Similarity NPC6391
0.8276 Intermediate Similarity NPC474970
0.8272 Intermediate Similarity NPC328104
0.8272 Intermediate Similarity NPC319090
0.8256 Intermediate Similarity NPC470077
0.8256 Intermediate Similarity NPC475798
0.8256 Intermediate Similarity NPC185568
0.8256 Intermediate Similarity NPC86238
0.8256 Intermediate Similarity NPC127606
0.825 Intermediate Similarity NPC471799
0.8242 Intermediate Similarity NPC174051
0.8242 Intermediate Similarity NPC67831
0.8235 Intermediate Similarity NPC470049
0.8235 Intermediate Similarity NPC189972
0.8235 Intermediate Similarity NPC20853
0.8235 Intermediate Similarity NPC50964
0.8222 Intermediate Similarity NPC210268
0.8222 Intermediate Similarity NPC262870
0.8214 Intermediate Similarity NPC236112
0.8214 Intermediate Similarity NPC13554
0.8202 Intermediate Similarity NPC473647
0.8202 Intermediate Similarity NPC105495
0.8202 Intermediate Similarity NPC76879
0.8202 Intermediate Similarity NPC470361
0.8193 Intermediate Similarity NPC476314
0.8193 Intermediate Similarity NPC85346
0.8193 Intermediate Similarity NPC65897
0.8193 Intermediate Similarity NPC302041
0.8182 Intermediate Similarity NPC271967
0.8172 Intermediate Similarity NPC261807
0.8172 Intermediate Similarity NPC177818
0.8171 Intermediate Similarity NPC46160
0.8171 Intermediate Similarity NPC202642
0.8171 Intermediate Similarity NPC247325
0.8171 Intermediate Similarity NPC470362
0.8171 Intermediate Similarity NPC237460
0.8171 Intermediate Similarity NPC73875
0.8171 Intermediate Similarity NPC244488
0.8152 Intermediate Similarity NPC8774
0.8148 Intermediate Similarity NPC27395
0.8148 Intermediate Similarity NPC329090
0.814 Intermediate Similarity NPC141941
0.814 Intermediate Similarity NPC113978
0.814 Intermediate Similarity NPC193870
0.814 Intermediate Similarity NPC317458
0.814 Intermediate Similarity NPC207013
0.814 Intermediate Similarity NPC232023
0.8118 Intermediate Similarity NPC116202
0.8118 Intermediate Similarity NPC70927
0.8111 Intermediate Similarity NPC291484
0.8111 Intermediate Similarity NPC80561
0.8111 Intermediate Similarity NPC329596
0.8111 Intermediate Similarity NPC171441
0.8111 Intermediate Similarity NPC204188
0.8111 Intermediate Similarity NPC475751
0.8111 Intermediate Similarity NPC473956
0.8111 Intermediate Similarity NPC3345
0.8111 Intermediate Similarity NPC11216
0.8105 Intermediate Similarity NPC474022
0.8095 Intermediate Similarity NPC153987
0.8095 Intermediate Similarity NPC44083
0.809 Intermediate Similarity NPC67872
0.809 Intermediate Similarity NPC328313
0.809 Intermediate Similarity NPC474668
0.809 Intermediate Similarity NPC475664
0.8068 Intermediate Similarity NPC261266
0.8068 Intermediate Similarity NPC299068
0.8065 Intermediate Similarity NPC72204
0.8065 Intermediate Similarity NPC12103
0.8065 Intermediate Similarity NPC210717
0.8065 Intermediate Similarity NPC103165
0.8065 Intermediate Similarity NPC304899
0.8065 Intermediate Similarity NPC227583
0.8065 Intermediate Similarity NPC253115
0.8065 Intermediate Similarity NPC98457
0.8049 Intermediate Similarity NPC118508
0.8049 Intermediate Similarity NPC291503
0.8049 Intermediate Similarity NPC3403
0.8049 Intermediate Similarity NPC121744
0.8049 Intermediate Similarity NPC322353
0.8046 Intermediate Similarity NPC472265
0.8046 Intermediate Similarity NPC238485
0.8046 Intermediate Similarity NPC33913
0.8046 Intermediate Similarity NPC59453
0.8046 Intermediate Similarity NPC221758
0.8046 Intermediate Similarity NPC82902
0.8046 Intermediate Similarity NPC478102
0.8043 Intermediate Similarity NPC65402
0.8043 Intermediate Similarity NPC127718
0.8023 Intermediate Similarity NPC218616

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474349 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
0.8861 High Similarity NPD3701 Clinical (unspecified phase)
0.8734 High Similarity NPD7339 Approved
0.8734 High Similarity NPD6942 Approved
0.8434 Intermediate Similarity NPD7525 Registered
0.8375 Intermediate Similarity NPD4784 Approved
0.8375 Intermediate Similarity NPD4785 Approved
0.8354 Intermediate Similarity NPD4243 Approved
0.8182 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD6924 Approved
0.8148 Intermediate Similarity NPD6926 Approved
0.8046 Intermediate Similarity NPD4786 Approved
0.8046 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD4748 Discontinued
0.7952 Intermediate Similarity NPD6933 Approved
0.7931 Intermediate Similarity NPD6695 Phase 3
0.7882 Intermediate Similarity NPD7645 Phase 2
0.7831 Intermediate Similarity NPD5275 Approved
0.7831 Intermediate Similarity NPD4190 Phase 3
0.7816 Intermediate Similarity NPD3667 Approved
0.7791 Intermediate Similarity NPD6930 Phase 2
0.7791 Intermediate Similarity NPD6931 Approved
0.7742 Intermediate Similarity NPD4202 Approved
0.7742 Intermediate Similarity NPD6399 Phase 3
0.7683 Intermediate Similarity NPD7151 Approved
0.7683 Intermediate Similarity NPD7152 Approved
0.7683 Intermediate Similarity NPD7150 Approved
0.7674 Intermediate Similarity NPD6929 Approved
0.7674 Intermediate Similarity NPD4195 Approved
0.7654 Intermediate Similarity NPD6922 Approved
0.7654 Intermediate Similarity NPD6923 Approved
0.7647 Intermediate Similarity NPD6932 Approved
0.764 Intermediate Similarity NPD3133 Approved
0.764 Intermediate Similarity NPD3665 Phase 1
0.764 Intermediate Similarity NPD3666 Approved
0.7609 Intermediate Similarity NPD4753 Phase 2
0.7604 Intermediate Similarity NPD6083 Phase 2
0.7604 Intermediate Similarity NPD4755 Approved
0.7604 Intermediate Similarity NPD6084 Phase 2
0.76 Intermediate Similarity NPD5739 Approved
0.76 Intermediate Similarity NPD7128 Approved
0.76 Intermediate Similarity NPD6675 Approved
0.76 Intermediate Similarity NPD6402 Approved
0.7586 Intermediate Similarity NPD7509 Discontinued
0.7582 Intermediate Similarity NPD7750 Discontinued
0.7582 Intermediate Similarity NPD7524 Approved
0.7561 Intermediate Similarity NPD7143 Approved
0.7561 Intermediate Similarity NPD7144 Approved
0.7471 Intermediate Similarity NPD6683 Phase 2
0.7451 Intermediate Similarity NPD7320 Approved
0.7451 Intermediate Similarity NPD6899 Approved
0.7451 Intermediate Similarity NPD6881 Approved
0.7449 Intermediate Similarity NPD5286 Approved
0.7449 Intermediate Similarity NPD4700 Approved
0.7449 Intermediate Similarity NPD4696 Approved
0.7449 Intermediate Similarity NPD5285 Approved
0.7442 Intermediate Similarity NPD5776 Phase 2
0.7442 Intermediate Similarity NPD6925 Approved
0.7419 Intermediate Similarity NPD5328 Approved
0.7419 Intermediate Similarity NPD6051 Approved
0.7416 Intermediate Similarity NPD4223 Phase 3
0.7416 Intermediate Similarity NPD4221 Approved
0.7386 Intermediate Similarity NPD7514 Phase 3
0.7379 Intermediate Similarity NPD6373 Approved
0.7379 Intermediate Similarity NPD6372 Approved
0.7374 Intermediate Similarity NPD4159 Approved
0.7363 Intermediate Similarity NPD6893 Approved
0.7363 Intermediate Similarity NPD5329 Approved
0.7356 Intermediate Similarity NPD7145 Approved
0.7353 Intermediate Similarity NPD5697 Approved
0.7353 Intermediate Similarity NPD5701 Approved
0.7308 Intermediate Similarity NPD7102 Approved
0.7308 Intermediate Similarity NPD7290 Approved
0.7308 Intermediate Similarity NPD6883 Approved
0.7303 Intermediate Similarity NPD6902 Approved
0.73 Intermediate Similarity NPD5225 Approved
0.73 Intermediate Similarity NPD5211 Phase 2
0.73 Intermediate Similarity NPD4633 Approved
0.73 Intermediate Similarity NPD5226 Approved
0.73 Intermediate Similarity NPD5224 Approved
0.7283 Intermediate Similarity NPD7146 Approved
0.7283 Intermediate Similarity NPD3618 Phase 1
0.7283 Intermediate Similarity NPD7521 Approved
0.7283 Intermediate Similarity NPD6409 Approved
0.7283 Intermediate Similarity NPD5330 Approved
0.7283 Intermediate Similarity NPD7334 Approved
0.7283 Intermediate Similarity NPD6684 Approved
0.7263 Intermediate Similarity NPD6079 Approved
0.7263 Intermediate Similarity NPD7087 Discontinued
0.7253 Intermediate Similarity NPD4197 Approved
0.7238 Intermediate Similarity NPD6617 Approved
0.7238 Intermediate Similarity NPD6869 Approved
0.7238 Intermediate Similarity NPD6650 Approved
0.7238 Intermediate Similarity NPD6847 Approved
0.7238 Intermediate Similarity NPD6649 Approved
0.7238 Intermediate Similarity NPD8130 Phase 1
0.7228 Intermediate Similarity NPD5175 Approved
0.7228 Intermediate Similarity NPD5174 Approved
0.7216 Intermediate Similarity NPD5695 Phase 3
0.7216 Intermediate Similarity NPD4629 Approved
0.7216 Intermediate Similarity NPD5210 Approved
0.7212 Intermediate Similarity NPD6012 Approved
0.7212 Intermediate Similarity NPD6013 Approved
0.7212 Intermediate Similarity NPD6014 Approved
0.72 Intermediate Similarity NPD5223 Approved
0.7191 Intermediate Similarity NPD7332 Phase 2
0.7172 Intermediate Similarity NPD5696 Approved
0.717 Intermediate Similarity NPD8297 Approved
0.717 Intermediate Similarity NPD6882 Approved
0.7159 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD5141 Approved
0.7143 Intermediate Similarity NPD4788 Approved
0.7128 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD6903 Approved
0.7115 Intermediate Similarity NPD6011 Approved
0.7111 Intermediate Similarity NPD6898 Phase 1
0.7097 Intermediate Similarity NPD5205 Approved
0.7097 Intermediate Similarity NPD4693 Phase 3
0.7097 Intermediate Similarity NPD6098 Approved
0.7097 Intermediate Similarity NPD4690 Approved
0.7097 Intermediate Similarity NPD4688 Approved
0.7097 Intermediate Similarity NPD4689 Approved
0.7097 Intermediate Similarity NPD4138 Approved
0.7087 Intermediate Similarity NPD6008 Approved
0.7087 Intermediate Similarity NPD4767 Approved
0.7087 Intermediate Similarity NPD4768 Approved
0.7075 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD3668 Phase 3
0.7059 Intermediate Similarity NPD4754 Approved
0.7019 Intermediate Similarity NPD6412 Phase 2
0.7 Intermediate Similarity NPD7638 Approved
0.6952 Remote Similarity NPD5128 Approved
0.6952 Remote Similarity NPD4730 Approved
0.6952 Remote Similarity NPD4729 Approved
0.6947 Remote Similarity NPD4723 Approved
0.6947 Remote Similarity NPD4722 Approved
0.6941 Remote Similarity NPD4787 Phase 1
0.6931 Remote Similarity NPD7640 Approved
0.6931 Remote Similarity NPD7639 Approved
0.6915 Remote Similarity NPD5280 Approved
0.6915 Remote Similarity NPD5279 Phase 3
0.6915 Remote Similarity NPD4694 Approved
0.6915 Remote Similarity NPD5690 Phase 2
0.6909 Remote Similarity NPD7115 Discovery
0.6875 Remote Similarity NPD6904 Approved
0.6875 Remote Similarity NPD6673 Approved
0.6875 Remote Similarity NPD6080 Approved
0.6869 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6824 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6822 Remote Similarity NPD5251 Approved
0.6822 Remote Similarity NPD4634 Approved
0.6822 Remote Similarity NPD5250 Approved
0.6822 Remote Similarity NPD5249 Phase 3
0.6822 Remote Similarity NPD5248 Approved
0.6822 Remote Similarity NPD5247 Approved
0.6818 Remote Similarity NPD8264 Approved
0.6818 Remote Similarity NPD6274 Approved
0.6809 Remote Similarity NPD7520 Clinical (unspecified phase)
0.68 Remote Similarity NPD5221 Approved
0.68 Remote Similarity NPD5222 Approved
0.68 Remote Similarity NPD5220 Clinical (unspecified phase)
0.68 Remote Similarity NPD4697 Phase 3
0.6786 Remote Similarity NPD7100 Approved
0.6786 Remote Similarity NPD7101 Approved
0.6771 Remote Similarity NPD5208 Approved
0.6771 Remote Similarity NPD6672 Approved
0.6771 Remote Similarity NPD5737 Approved
0.6759 Remote Similarity NPD5217 Approved
0.6759 Remote Similarity NPD5216 Approved
0.6759 Remote Similarity NPD5215 Approved
0.6739 Remote Similarity NPD4692 Approved
0.6739 Remote Similarity NPD4139 Approved
0.6735 Remote Similarity NPD8034 Phase 2
0.6735 Remote Similarity NPD8035 Phase 2
0.6735 Remote Similarity NPD7637 Suspended
0.6735 Remote Similarity NPD5281 Approved
0.6735 Remote Similarity NPD5284 Approved
0.6733 Remote Similarity NPD5173 Approved
0.6726 Remote Similarity NPD6054 Approved
0.6726 Remote Similarity NPD6059 Approved
0.6696 Remote Similarity NPD6335 Approved
0.6696 Remote Similarity NPD7327 Approved
0.6696 Remote Similarity NPD7328 Approved
0.6667 Remote Similarity NPD5169 Approved
0.6667 Remote Similarity NPD6908 Approved
0.6667 Remote Similarity NPD5135 Approved
0.6667 Remote Similarity NPD8033 Approved
0.6667 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6909 Approved
0.6637 Remote Similarity NPD7516 Approved
0.6636 Remote Similarity NPD4632 Approved
0.663 Remote Similarity NPD6928 Phase 2
0.6609 Remote Similarity NPD6370 Approved
0.6607 Remote Similarity NPD6317 Approved
0.6606 Remote Similarity NPD5127 Approved
0.66 Remote Similarity NPD6001 Approved
0.66 Remote Similarity NPD7748 Approved
0.66 Remote Similarity NPD5707 Approved
0.6579 Remote Similarity NPD6319 Approved
0.6579 Remote Similarity NPD8294 Approved
0.6579 Remote Similarity NPD8377 Approved

Structure

External Identifiers

PubChem CID   21577172
ChEMBL   CHEMBL465543
ZINC  

Physicochemical Properties

Molecular Weight:  416.33
ALogP:  0.6214
MLogP:  4.1
XLogP:  5.823
# Rotatable Bonds:  11
Polar Surface Area:  52.99
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  30

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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