Natural Product: NPC243746

Natural Product ID:  NPC243746
Common Name:   Yardenone
IUPAC Name:   (5'S,5aR,6S,7S,9aS)-5'-[(5aS,6S,8aS)-2,2,5a,6-tetramethyl-3-oxo-5,7,8,8a-tetrahydro-4H-cyclopenta[b]oxepin-6-yl]-2,2,5a,7-tetramethylspiro[4,5,7,8,9,9a-hexahydrobenzo[b]oxepine-6,2'-oxolane]-3-one
Synonyms:   Yardenone
Molecular Formula:   C30H48O5
Standard InCHIKey:  QITDIIMEVNRCKY-YDAHQQQXSA-N
Standard InCHI:  InChI=1S/C30H48O5/c1-19-9-10-22-29(8,16-12-21(32)25(2,3)33-22)30(19)18-14-24(35-30)28(7)17-13-23-27(28,6)15-11-20(31)26(4,5)34-23/h19,22-24H,9-18H2,1-8H3/t19-,22-,23-,24-,27+,28+,29+,30-/m0/s1
Canonical SMILES:  O=C1CC[C@@]2([C@@H](OC1(C)C)CC[C@]2(C)[C@@H]1CC[C@]2(O1)[C@@H](C)CC[C@H]1[C@@]2(C)CCC(=O)C(O1)(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
NPO32762 axinella cf. bidderi Species Axinellidae Eukaryota Indian Ocean PMID[12542339]
NPO32663 Axinella Genus Axinellidae Eukaryota South African PMID[17190448]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 30000 nM 9358635
NPT2 Others Unspecified IC50 > 30000 nM 19640616
NPT90 Cell Line DU-145 Homo sapiens IC50 > 30000 nM 22194678
NPT306 Cell Line PC-3 Homo sapiens IC50 > 30000 nM 18077425
NPT396 Cell Line T47D Homo sapiens IC50 > 30000 nM 15026054

  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 NPC243746 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
0.9195 High Similarity NPC76136
0.9195 High Similarity NPC329713
0.9195 High Similarity NPC217567
0.7778 Intermediate Similarity NPC477441
0.7609 Intermediate Similarity NPC191221
0.7604 Intermediate Similarity NPC476728
0.7579 Intermediate Similarity NPC470424
0.7553 Intermediate Similarity NPC216137
0.7527 Intermediate Similarity NPC61688
0.75 Intermediate Similarity NPC305808
0.7447 Intermediate Similarity NPC477433
0.7447 Intermediate Similarity NPC477442
0.7447 Intermediate Similarity NPC477444
0.7444 Intermediate Similarity NPC476721
0.7444 Intermediate Similarity NPC327451
0.7423 Intermediate Similarity NPC260223
0.7419 Intermediate Similarity NPC226491
0.7419 Intermediate Similarity NPC477614
0.7396 Intermediate Similarity NPC477495
0.7391 Intermediate Similarity NPC476726
0.7391 Intermediate Similarity NPC476727
0.7368 Intermediate Similarity NPC52756
0.7347 Intermediate Similarity NPC470834
0.734 Intermediate Similarity NPC477440
0.734 Intermediate Similarity NPC477443
0.7303 Intermediate Similarity NPC134227
0.7292 Intermediate Similarity NPC474379
0.7283 Intermediate Similarity NPC477445
0.7273 Intermediate Similarity NPC476294
0.7273 Intermediate Similarity NPC253995
0.7273 Intermediate Similarity NPC211087
0.7273 Intermediate Similarity NPC17183
0.7255 Intermediate Similarity NPC88469
0.7255 Intermediate Similarity NPC327093
0.7222 Intermediate Similarity NPC254123
0.7204 Intermediate Similarity NPC80700
0.7204 Intermediate Similarity NPC476717
0.7188 Intermediate Similarity NPC474065
0.7174 Intermediate Similarity NPC50438
0.7174 Intermediate Similarity NPC477434
0.7174 Intermediate Similarity NPC475689
0.7143 Intermediate Similarity NPC287354
0.7143 Intermediate Similarity NPC62407
0.7113 Intermediate Similarity NPC476189
0.7113 Intermediate Similarity NPC161035
0.7111 Intermediate Similarity NPC125366
0.7097 Intermediate Similarity NPC473350
0.7097 Intermediate Similarity NPC476715
0.7087 Intermediate Similarity NPC469629
0.7083 Intermediate Similarity NPC476296
0.7071 Intermediate Similarity NPC116683
0.7059 Intermediate Similarity NPC470840
0.7053 Intermediate Similarity NPC476435
0.7048 Intermediate Similarity NPC316930
0.7033 Intermediate Similarity NPC328639
0.7033 Intermediate Similarity NPC329490
0.7011 Intermediate Similarity NPC55508
0.699 Remote Similarity NPC470839
0.6989 Remote Similarity NPC291310
0.6989 Remote Similarity NPC105895
0.6989 Remote Similarity NPC65133
0.6981 Remote Similarity NPC320475
0.6981 Remote Similarity NPC321661
0.697 Remote Similarity NPC17336
0.6966 Remote Similarity NPC143250
0.6961 Remote Similarity NPC178853
0.6957 Remote Similarity NPC24556
0.6947 Remote Similarity NPC263802
0.6947 Remote Similarity NPC239938
0.6923 Remote Similarity NPC474714
0.6923 Remote Similarity NPC473526
0.6923 Remote Similarity NPC473701
0.6909 Remote Similarity NPC475490
0.6907 Remote Similarity NPC77756
0.6893 Remote Similarity NPC213528
0.6893 Remote Similarity NPC244969
0.6882 Remote Similarity NPC15091
0.6881 Remote Similarity NPC97002
0.6857 Remote Similarity NPC50535
0.6852 Remote Similarity NPC473062
0.6848 Remote Similarity NPC469745
0.6848 Remote Similarity NPC473257
0.6842 Remote Similarity NPC474448
0.6842 Remote Similarity NPC472272
0.6842 Remote Similarity NPC472745
0.6832 Remote Similarity NPC190080
0.6832 Remote Similarity NPC111187
0.6818 Remote Similarity NPC470116
0.6818 Remote Similarity NPC470115
0.6818 Remote Similarity NPC96759
0.6813 Remote Similarity NPC275243
0.6809 Remote Similarity NPC474996
0.6804 Remote Similarity NPC200580
0.68 Remote Similarity NPC470031
0.6796 Remote Similarity NPC304624
0.6796 Remote Similarity NPC259654
0.6796 Remote Similarity NPC298266
0.6796 Remote Similarity NPC474053
0.6792 Remote Similarity NPC86852
0.6792 Remote Similarity NPC251824
0.6782 Remote Similarity NPC470243
0.6778 Remote Similarity NPC471151
0.6774 Remote Similarity NPC148740
0.6774 Remote Similarity NPC477284
0.6774 Remote Similarity NPC328007
0.6774 Remote Similarity NPC102156
0.6774 Remote Similarity NPC13494
0.6774 Remote Similarity NPC317066
0.6768 Remote Similarity NPC228700
0.6762 Remote Similarity NPC47281
0.6762 Remote Similarity NPC100078
0.6742 Remote Similarity NPC159789
0.6737 Remote Similarity NPC477205
0.6733 Remote Similarity NPC193785
0.6733 Remote Similarity NPC477264
0.6706 Remote Similarity NPC328304
0.6706 Remote Similarity NPC329466
0.6705 Remote Similarity NPC123122
0.6705 Remote Similarity NPC109510
0.6705 Remote Similarity NPC476718
0.6702 Remote Similarity NPC29342
0.6702 Remote Similarity NPC2572
0.6702 Remote Similarity NPC69953
0.6702 Remote Similarity NPC227170
0.6701 Remote Similarity NPC471221
0.6701 Remote Similarity NPC221993
0.6701 Remote Similarity NPC236459
0.67 Remote Similarity NPC476722
0.6699 Remote Similarity NPC108371
0.6698 Remote Similarity NPC306776
0.6698 Remote Similarity NPC168890
0.6698 Remote Similarity NPC28791
0.6698 Remote Similarity NPC475571
0.6698 Remote Similarity NPC166079
0.6667 Remote Similarity NPC469985
0.6667 Remote Similarity NPC471046
0.6667 Remote Similarity NPC469810
0.6667 Remote Similarity NPC131365
0.6667 Remote Similarity NPC475878
0.6667 Remote Similarity NPC475743
0.6667 Remote Similarity NPC83242
0.6667 Remote Similarity NPC217041
0.6667 Remote Similarity NPC475729
0.6667 Remote Similarity NPC474215
0.6667 Remote Similarity NPC266417
0.6667 Remote Similarity NPC469350
0.6637 Remote Similarity NPC324253
0.6636 Remote Similarity NPC176756
0.6635 Remote Similarity NPC253886
0.6635 Remote Similarity NPC162024
0.6635 Remote Similarity NPC121218
0.6633 Remote Similarity NPC471459
0.6633 Remote Similarity NPC67653
0.6633 Remote Similarity NPC472233
0.6633 Remote Similarity NPC472234
0.6632 Remote Similarity NPC473336
0.6632 Remote Similarity NPC473299
0.6632 Remote Similarity NPC471044
0.663 Remote Similarity NPC476176
0.663 Remote Similarity NPC477287
0.663 Remote Similarity NPC245029
0.663 Remote Similarity NPC31302
0.6629 Remote Similarity NPC475458
0.6629 Remote Similarity NPC215030
0.6606 Remote Similarity NPC182185
0.6604 Remote Similarity NPC29705
0.6602 Remote Similarity NPC472144
0.6602 Remote Similarity NPC474724
0.6598 Remote Similarity NPC5943
0.6598 Remote Similarity NPC202937
0.6596 Remote Similarity NPC271163
0.6596 Remote Similarity NPC268040
0.6591 Remote Similarity NPC311102
0.6574 Remote Similarity NPC220773
0.6574 Remote Similarity NPC167044
0.6574 Remote Similarity NPC278693
0.6571 Remote Similarity NPC470172
0.6571 Remote Similarity NPC170615
0.6569 Remote Similarity NPC163685
0.6569 Remote Similarity NPC235109
0.6566 Remote Similarity NPC470114
0.6566 Remote Similarity NPC46758
0.6562 Remote Similarity NPC266651
0.6559 Remote Similarity NPC66766
0.6559 Remote Similarity NPC470609
0.6559 Remote Similarity NPC117137
0.6559 Remote Similarity NPC1882
0.6556 Remote Similarity NPC35871
0.6556 Remote Similarity NPC72444
0.6556 Remote Similarity NPC155441
0.6556 Remote Similarity NPC68565
0.6549 Remote Similarity NPC179429
0.6542 Remote Similarity NPC215408
0.6535 Remote Similarity NPC293086
0.6535 Remote Similarity NPC206878
0.6535 Remote Similarity NPC212812
0.6535 Remote Similarity NPC476716
0.6535 Remote Similarity NPC470423
0.6531 Remote Similarity NPC90676
0.6526 Remote Similarity NPC217559

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC243746 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
0.73 Intermediate Similarity NPD1700 Approved
0.6742 Remote Similarity NPD3703 Phase 2
0.6604 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6591 Remote Similarity NPD5777 Approved
0.6574 Remote Similarity NPD7320 Approved
0.6542 Remote Similarity NPD7128 Approved
0.6542 Remote Similarity NPD6402 Approved
0.6542 Remote Similarity NPD5739 Approved
0.6542 Remote Similarity NPD6675 Approved
0.6542 Remote Similarity NPD6008 Approved
0.6522 Remote Similarity NPD6054 Approved
0.6522 Remote Similarity NPD6059 Approved
0.6422 Remote Similarity NPD6899 Approved
0.6422 Remote Similarity NPD6881 Approved
0.641 Remote Similarity NPD6370 Approved
0.6364 Remote Similarity NPD6373 Approved
0.6364 Remote Similarity NPD6372 Approved
0.6346 Remote Similarity NPD4755 Approved
0.6344 Remote Similarity NPD6114 Approved
0.6344 Remote Similarity NPD6697 Approved
0.6344 Remote Similarity NPD6115 Approved
0.6344 Remote Similarity NPD6118 Approved
0.633 Remote Similarity NPD5697 Approved
0.633 Remote Similarity NPD5701 Approved
0.6325 Remote Similarity NPD6015 Approved
0.6325 Remote Similarity NPD6016 Approved
0.6306 Remote Similarity NPD7102 Approved
0.6306 Remote Similarity NPD6883 Approved
0.6306 Remote Similarity NPD7290 Approved
0.6303 Remote Similarity NPD7492 Approved
0.6292 Remote Similarity NPD4244 Approved
0.6292 Remote Similarity NPD4245 Approved
0.6271 Remote Similarity NPD5988 Approved
0.625 Remote Similarity NPD8130 Phase 1
0.625 Remote Similarity NPD6847 Approved
0.625 Remote Similarity NPD6617 Approved
0.625 Remote Similarity NPD6649 Approved
0.625 Remote Similarity NPD6869 Approved
0.625 Remote Similarity NPD6650 Approved
0.625 Remote Similarity NPD6616 Approved
0.6237 Remote Similarity NPD6116 Phase 1
0.6226 Remote Similarity NPD5286 Approved
0.6226 Remote Similarity NPD4700 Approved
0.6226 Remote Similarity NPD5285 Approved
0.6226 Remote Similarity NPD4696 Approved
0.6222 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6222 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6216 Remote Similarity NPD6013 Approved
0.6216 Remote Similarity NPD6014 Approved
0.6216 Remote Similarity NPD6012 Approved
0.6198 Remote Similarity NPD7078 Approved
0.6198 Remote Similarity NPD8293 Discontinued
0.6196 Remote Similarity NPD3702 Approved
0.6195 Remote Similarity NPD8297 Approved
0.6195 Remote Similarity NPD6882 Approved
0.618 Remote Similarity NPD3699 Clinical (unspecified phase)
0.618 Remote Similarity NPD3700 Clinical (unspecified phase)
0.618 Remote Similarity NPD3698 Phase 2
0.6148 Remote Similarity NPD7736 Approved
0.6129 Remote Similarity NPD6117 Approved
0.6126 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6126 Remote Similarity NPD6011 Approved
0.6111 Remote Similarity NPD5224 Approved
0.6111 Remote Similarity NPD4789 Approved
0.6111 Remote Similarity NPD5211 Phase 2
0.6111 Remote Similarity NPD5225 Approved
0.6111 Remote Similarity NPD5226 Approved
0.6111 Remote Similarity NPD4633 Approved
0.6106 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6102 Remote Similarity NPD6319 Approved
0.6067 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6067 Remote Similarity NPD5360 Phase 3
0.6055 Remote Similarity NPD5175 Approved
0.6055 Remote Similarity NPD5174 Approved
0.6042 Remote Similarity NPD6928 Phase 2
0.6019 Remote Similarity NPD5223 Approved
0.6018 Remote Similarity NPD4634 Approved
0.6016 Remote Similarity NPD6033 Approved
0.6 Remote Similarity NPD4632 Approved
0.6 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6 Remote Similarity NPD5141 Approved
0.5983 Remote Similarity NPD6009 Approved
0.5979 Remote Similarity NPD1780 Approved
0.5979 Remote Similarity NPD1779 Approved
0.595 Remote Similarity NPD7604 Phase 2
0.5946 Remote Similarity NPD4768 Approved
0.5946 Remote Similarity NPD4767 Approved
0.5917 Remote Similarity NPD5983 Phase 2
0.5914 Remote Similarity NPD6113 Clinical (unspecified phase)
0.5909 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5909 Remote Similarity NPD4754 Approved
0.5897 Remote Similarity NPD6274 Approved
0.5889 Remote Similarity NPD229 Approved
0.5888 Remote Similarity NPD6084 Phase 2
0.5888 Remote Similarity NPD6083 Phase 2
0.5882 Remote Similarity NPD7101 Approved
0.5882 Remote Similarity NPD7100 Approved
0.5854 Remote Similarity NPD6336 Discontinued
0.5849 Remote Similarity NPD5695 Phase 3
0.5849 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5842 Remote Similarity NPD6098 Approved
0.5841 Remote Similarity NPD4729 Approved
0.5841 Remote Similarity NPD5128 Approved
0.5841 Remote Similarity NPD4730 Approved
0.5833 Remote Similarity NPD4802 Phase 2
0.5833 Remote Similarity NPD4238 Approved
0.5825 Remote Similarity NPD6080 Approved
0.5825 Remote Similarity NPD6904 Approved
0.5825 Remote Similarity NPD6673 Approved
0.5798 Remote Similarity NPD6335 Approved
0.5785 Remote Similarity NPD6908 Approved
0.5785 Remote Similarity NPD6909 Approved
0.5755 Remote Similarity NPD5282 Discontinued
0.5739 Remote Similarity NPD5248 Approved
0.5739 Remote Similarity NPD5250 Approved
0.5739 Remote Similarity NPD5251 Approved
0.5739 Remote Similarity NPD5247 Approved
0.5739 Remote Similarity NPD5249 Phase 3
0.5728 Remote Similarity NPD5737 Approved
0.5728 Remote Similarity NPD6903 Approved
0.5728 Remote Similarity NPD6672 Approved
0.5714 Remote Similarity NPD8034 Phase 2
0.5714 Remote Similarity NPD6050 Approved
0.5714 Remote Similarity NPD8035 Phase 2
0.5714 Remote Similarity NPD6317 Approved
0.5699 Remote Similarity NPD4758 Discontinued
0.569 Remote Similarity NPD5217 Approved
0.569 Remote Similarity NPD5216 Approved
0.569 Remote Similarity NPD5215 Approved
0.5688 Remote Similarity NPD5696 Approved
0.5686 Remote Similarity NPD5330 Approved
0.5686 Remote Similarity NPD6684 Approved
0.5686 Remote Similarity NPD7146 Approved
0.5686 Remote Similarity NPD7521 Approved
0.5686 Remote Similarity NPD6409 Approved
0.5686 Remote Similarity NPD7334 Approved
0.5673 Remote Similarity NPD4753 Phase 2
0.5673 Remote Similarity NPD5328 Approved
0.567 Remote Similarity NPD3671 Phase 1
0.567 Remote Similarity NPD5364 Discontinued
0.5667 Remote Similarity NPD6313 Approved
0.5667 Remote Similarity NPD6314 Approved
0.566 Remote Similarity NPD8171 Discontinued
0.566 Remote Similarity NPD4202 Approved
0.5656 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5652 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5648 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5648 Remote Similarity NPD4697 Phase 3
0.5648 Remote Similarity NPD5221 Approved
0.5648 Remote Similarity NPD5222 Approved
0.5641 Remote Similarity NPD6053 Discontinued
0.5619 Remote Similarity NPD5692 Phase 3
0.5614 Remote Similarity NPD6412 Phase 2
0.5603 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5603 Remote Similarity NPD5135 Approved
0.5603 Remote Similarity NPD5169 Approved
0.56 Remote Similarity NPD7507 Approved
0.56 Remote Similarity NPD6435 Approved

Structure

External Identifiers

PubChem CID   15378863
ChEMBL   CHEMBL457936
ZINC  

Physicochemical Properties

Molecular Weight:  488.35
ALogP:  0.6162
MLogP:  4.21
XLogP:  4.358
# Rotatable Bonds:  9
Polar Surface Area:  61.83
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  35

Download Data

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