Natural Product: NPC274522

Natural Product ID:  NPC274522
Common Name:   Sigmosceptrellin B Methyl Ester
IUPAC Name:   methyl (2S)-2-[(3R,6S)-6-[2-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-6-methyldioxan-3-yl]propanoate
Synonyms:  
Molecular Formula:   C25H42O4
Standard InCHIKey:  XZMSFDWECPXXRJ-KYABTRMWSA-N
Standard InCHI:  InChI=1S/C25H42O4/c1-17-9-8-10-21-24(17,5)14-11-18(2)25(21,6)16-15-23(4)13-12-20(28-29-23)19(3)22(26)27-7/h18-21H,1,8-16H2,2-7H3/t18-,19+,20-,21+,23-,24+,25+/m1/s1
Canonical SMILES:  COC(=O)[C@H]([C@H]1CC[C@](OO1)(C)CC[C@@]1(C)[C@H](C)CC[C@@]2([C@@H]1CCCC2=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
NPO5207 Diacarnus erythraeanus Species Podospongiidae Eukaryota Red Sea PMID[23977995]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT306 Cell Line PC-3 Homo sapiens IC50 = 44000 nM 23206866
NPT380 Cell Line U-251 Homo sapiens IC50 = 54000 nM 23711769
NPT2 Others Unspecified IC50 = 53000 nM 23711769
NPT83 Cell Line MCF7 Homo sapiens IC50 = 36000 nM 20028821
NPT81 Cell Line A549 Homo sapiens IC50 = 24000 nM 20086162
NPT2 Others Unspecified IC50 = 35000 nM PubChem BioAssay data set
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 = 44000 nM 10924166

  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 NPC274522 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 NPC476265
0.9481 High Similarity NPC474605
0.9481 High Similarity NPC476292
0.9459 High Similarity NPC476985
0.9459 High Similarity NPC474316
0.9459 High Similarity NPC475744
0.8961 High Similarity NPC470905
0.8961 High Similarity NPC476986
0.8861 High Similarity NPC476988
0.878 High Similarity NPC262085
0.8765 High Similarity NPC475193
0.8765 High Similarity NPC120158
0.875 High Similarity NPC476984
0.875 High Similarity NPC475395
0.8642 High Similarity NPC476100
0.859 High Similarity NPC469867
0.8462 Intermediate Similarity NPC476987
0.8462 Intermediate Similarity NPC59602
0.8462 Intermediate Similarity NPC152754
0.8395 Intermediate Similarity NPC475951
0.8354 Intermediate Similarity NPC476264
0.8354 Intermediate Similarity NPC476325
0.8333 Intermediate Similarity NPC476104
0.8333 Intermediate Similarity NPC475181
0.8256 Intermediate Similarity NPC471342
0.8256 Intermediate Similarity NPC469866
0.8235 Intermediate Similarity NPC134197
0.8214 Intermediate Similarity NPC471344
0.8171 Intermediate Similarity NPC172309
0.8171 Intermediate Similarity NPC14044
0.8171 Intermediate Similarity NPC117960
0.8148 Intermediate Similarity NPC268502
0.8148 Intermediate Similarity NPC254996
0.814 Intermediate Similarity NPC255176
0.8077 Intermediate Similarity NPC279241
0.8068 Intermediate Similarity NPC476934
0.8049 Intermediate Similarity NPC170038
0.7976 Intermediate Similarity NPC471037
0.7976 Intermediate Similarity NPC476983
0.7976 Intermediate Similarity NPC170862
0.7975 Intermediate Similarity NPC330016
0.7931 Intermediate Similarity NPC183374
0.7931 Intermediate Similarity NPC56413
0.7931 Intermediate Similarity NPC211162
0.7927 Intermediate Similarity NPC118987
0.7927 Intermediate Similarity NPC82488
0.7927 Intermediate Similarity NPC308545
0.7927 Intermediate Similarity NPC471475
0.7907 Intermediate Similarity NPC73038
0.7901 Intermediate Similarity NPC474433
0.7901 Intermediate Similarity NPC122847
0.7865 Intermediate Similarity NPC471901
0.7857 Intermediate Similarity NPC476935
0.7848 Intermediate Similarity NPC167145
0.7841 Intermediate Similarity NPC253618
0.7841 Intermediate Similarity NPC57954
0.7841 Intermediate Similarity NPC471043
0.7841 Intermediate Similarity NPC77001
0.7841 Intermediate Similarity NPC213832
0.7826 Intermediate Similarity NPC253586
0.7821 Intermediate Similarity NPC91369
0.7805 Intermediate Similarity NPC321514
0.7805 Intermediate Similarity NPC63020
0.7802 Intermediate Similarity NPC205173
0.7802 Intermediate Similarity NPC217329
0.7792 Intermediate Similarity NPC36616
0.7792 Intermediate Similarity NPC290445
0.7791 Intermediate Similarity NPC98270
0.7791 Intermediate Similarity NPC201655
0.7791 Intermediate Similarity NPC76333
0.7778 Intermediate Similarity NPC473690
0.7778 Intermediate Similarity NPC474447
0.7778 Intermediate Similarity NPC92489
0.7778 Intermediate Similarity NPC471902
0.7778 Intermediate Similarity NPC287118
0.7778 Intermediate Similarity NPC199543
0.775 Intermediate Similarity NPC166797
0.7742 Intermediate Similarity NPC474793
0.7738 Intermediate Similarity NPC476101
0.7738 Intermediate Similarity NPC327002
0.7727 Intermediate Similarity NPC146937
0.7727 Intermediate Similarity NPC471900
0.7722 Intermediate Similarity NPC72343
0.7717 Intermediate Similarity NPC132824
0.7711 Intermediate Similarity NPC28319
0.7701 Intermediate Similarity NPC322159
0.7701 Intermediate Similarity NPC472505
0.7701 Intermediate Similarity NPC476982
0.7701 Intermediate Similarity NPC80590
0.7701 Intermediate Similarity NPC471042
0.7701 Intermediate Similarity NPC324063
0.7692 Intermediate Similarity NPC23621
0.7692 Intermediate Similarity NPC184006
0.7692 Intermediate Similarity NPC78580
0.7692 Intermediate Similarity NPC469982
0.7683 Intermediate Similarity NPC472300
0.7683 Intermediate Similarity NPC66105
0.7683 Intermediate Similarity NPC238227
0.7674 Intermediate Similarity NPC263974
0.7674 Intermediate Similarity NPC471343
0.7674 Intermediate Similarity NPC475509
0.7674 Intermediate Similarity NPC469407
0.7667 Intermediate Similarity NPC470230
0.7667 Intermediate Similarity NPC155120
0.7667 Intermediate Similarity NPC324341
0.7667 Intermediate Similarity NPC475416
0.7667 Intermediate Similarity NPC966
0.7667 Intermediate Similarity NPC282616
0.7667 Intermediate Similarity NPC6255
0.7667 Intermediate Similarity NPC471588
0.7667 Intermediate Similarity NPC288833
0.7667 Intermediate Similarity NPC228784
0.766 Intermediate Similarity NPC108371
0.764 Intermediate Similarity NPC474700
0.764 Intermediate Similarity NPC116146
0.764 Intermediate Similarity NPC474570
0.764 Intermediate Similarity NPC24772
0.7632 Intermediate Similarity NPC215987
0.7632 Intermediate Similarity NPC306805
0.7625 Intermediate Similarity NPC36310
0.7619 Intermediate Similarity NPC267517
0.7619 Intermediate Similarity NPC104545
0.7619 Intermediate Similarity NPC37038
0.7614 Intermediate Similarity NPC46912
0.7614 Intermediate Similarity NPC264005
0.7614 Intermediate Similarity NPC158141
0.7614 Intermediate Similarity NPC173089
0.7614 Intermediate Similarity NPC269360
0.7614 Intermediate Similarity NPC96496
0.7614 Intermediate Similarity NPC162107
0.7614 Intermediate Similarity NPC33768
0.7609 Intermediate Similarity NPC23241
0.7609 Intermediate Similarity NPC210214
0.7609 Intermediate Similarity NPC195715
0.759 Intermediate Similarity NPC476810
0.759 Intermediate Similarity NPC4827
0.7586 Intermediate Similarity NPC329738
0.7582 Intermediate Similarity NPC118490
0.7579 Intermediate Similarity NPC236585
0.7568 Intermediate Similarity NPC472021
0.7561 Intermediate Similarity NPC469514
0.7561 Intermediate Similarity NPC899
0.7561 Intermediate Similarity NPC476601
0.7561 Intermediate Similarity NPC246445
0.7561 Intermediate Similarity NPC239127
0.7558 Intermediate Similarity NPC245866
0.7558 Intermediate Similarity NPC243347
0.7556 Intermediate Similarity NPC172361
0.7556 Intermediate Similarity NPC263977
0.7556 Intermediate Similarity NPC169933
0.7556 Intermediate Similarity NPC130278
0.7556 Intermediate Similarity NPC86372
0.7553 Intermediate Similarity NPC164349
0.7553 Intermediate Similarity NPC469986
0.7553 Intermediate Similarity NPC174663
0.7531 Intermediate Similarity NPC18819
0.7531 Intermediate Similarity NPC46610
0.7529 Intermediate Similarity NPC223330
0.7529 Intermediate Similarity NPC232625
0.7529 Intermediate Similarity NPC209318
0.7529 Intermediate Similarity NPC474955
0.7528 Intermediate Similarity NPC254572
0.7528 Intermediate Similarity NPC229407
0.7528 Intermediate Similarity NPC1753
0.7528 Intermediate Similarity NPC4309
0.7528 Intermediate Similarity NPC250687
0.7528 Intermediate Similarity NPC48824
0.7528 Intermediate Similarity NPC474511
0.7528 Intermediate Similarity NPC80335
0.7527 Intermediate Similarity NPC223169
0.7527 Intermediate Similarity NPC327788
0.7527 Intermediate Similarity NPC98874
0.7527 Intermediate Similarity NPC201657
0.75 Intermediate Similarity NPC187545
0.75 Intermediate Similarity NPC41649
0.75 Intermediate Similarity NPC325594
0.75 Intermediate Similarity NPC12774
0.75 Intermediate Similarity NPC329943
0.75 Intermediate Similarity NPC47853
0.75 Intermediate Similarity NPC222047
0.75 Intermediate Similarity NPC2783
0.75 Intermediate Similarity NPC195640
0.75 Intermediate Similarity NPC263951
0.75 Intermediate Similarity NPC169751
0.75 Intermediate Similarity NPC191412
0.75 Intermediate Similarity NPC114159
0.75 Intermediate Similarity NPC148964
0.75 Intermediate Similarity NPC6818
0.75 Intermediate Similarity NPC185638
0.75 Intermediate Similarity NPC272635
0.75 Intermediate Similarity NPC231431
0.75 Intermediate Similarity NPC473431
0.75 Intermediate Similarity NPC91525
0.75 Intermediate Similarity NPC70661
0.75 Intermediate Similarity NPC327674
0.75 Intermediate Similarity NPC475007
0.75 Intermediate Similarity NPC473280
0.75 Intermediate Similarity NPC192999
0.75 Intermediate Similarity NPC264127
0.75 Intermediate Similarity NPC10005

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC274522 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
0.75 Intermediate Similarity NPD6409 Approved
0.75 Intermediate Similarity NPD7334 Approved
0.75 Intermediate Similarity NPD7146 Approved
0.75 Intermediate Similarity NPD6684 Approved
0.75 Intermediate Similarity NPD7521 Approved
0.75 Intermediate Similarity NPD5330 Approved
0.7473 Intermediate Similarity NPD8035 Phase 2
0.7473 Intermediate Similarity NPD8034 Phase 2
0.7391 Intermediate Similarity NPD6399 Phase 3
0.7386 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6903 Approved
0.7333 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6672 Approved
0.7333 Intermediate Similarity NPD5737 Approved
0.7312 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD7900 Approved
0.7283 Intermediate Similarity NPD6411 Approved
0.7128 Intermediate Similarity NPD7748 Approved
0.7111 Intermediate Similarity NPD6098 Approved
0.7097 Intermediate Similarity NPD7515 Phase 2
0.7083 Intermediate Similarity NPD7902 Approved
0.7083 Intermediate Similarity NPD6083 Phase 2
0.7083 Intermediate Similarity NPD6084 Phase 2
0.7073 Intermediate Similarity NPD5777 Approved
0.7065 Intermediate Similarity NPD6101 Approved
0.7065 Intermediate Similarity NPD6673 Approved
0.7065 Intermediate Similarity NPD6080 Approved
0.7065 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD6904 Approved
0.7045 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD3573 Approved
0.6966 Remote Similarity NPD4788 Approved
0.6961 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6675 Approved
0.6931 Remote Similarity NPD6402 Approved
0.6931 Remote Similarity NPD7128 Approved
0.6931 Remote Similarity NPD5739 Approved
0.6889 Remote Similarity NPD3668 Phase 3
0.6889 Remote Similarity NPD4786 Approved
0.6875 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5695 Phase 3
0.686 Remote Similarity NPD6116 Phase 1
0.6854 Remote Similarity NPD3667 Approved
0.6837 Remote Similarity NPD5696 Approved
0.6824 Remote Similarity NPD3702 Approved
0.6796 Remote Similarity NPD6881 Approved
0.6796 Remote Similarity NPD6899 Approved
0.6796 Remote Similarity NPD7320 Approved
0.6774 Remote Similarity NPD5208 Approved
0.6744 Remote Similarity NPD6117 Approved
0.6737 Remote Similarity NPD5693 Phase 1
0.6737 Remote Similarity NPD6050 Approved
0.6731 Remote Similarity NPD6372 Approved
0.6731 Remote Similarity NPD6373 Approved
0.6706 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6703 Remote Similarity NPD3665 Phase 1
0.6703 Remote Similarity NPD3133 Approved
0.6703 Remote Similarity NPD3666 Approved
0.6702 Remote Similarity NPD4753 Phase 2
0.6702 Remote Similarity NPD6051 Approved
0.6699 Remote Similarity NPD5697 Approved
0.6699 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD6883 Approved
0.6667 Remote Similarity NPD7290 Approved
0.6667 Remote Similarity NPD7102 Approved
0.6636 Remote Similarity NPD8133 Approved
0.6635 Remote Similarity NPD6686 Approved
0.6632 Remote Similarity NPD5692 Phase 3
0.6604 Remote Similarity NPD6847 Approved
0.6604 Remote Similarity NPD6617 Approved
0.6604 Remote Similarity NPD6650 Approved
0.6604 Remote Similarity NPD6869 Approved
0.6604 Remote Similarity NPD8130 Phase 1
0.6604 Remote Similarity NPD6649 Approved
0.6602 Remote Similarity NPD6008 Approved
0.6591 Remote Similarity NPD6118 Approved
0.6591 Remote Similarity NPD6114 Approved
0.6591 Remote Similarity NPD6697 Approved
0.6591 Remote Similarity NPD6115 Approved
0.6571 Remote Similarity NPD6013 Approved
0.6571 Remote Similarity NPD6012 Approved
0.6571 Remote Similarity NPD6014 Approved
0.6566 Remote Similarity NPD4755 Approved
0.6562 Remote Similarity NPD5284 Approved
0.6562 Remote Similarity NPD5281 Approved
0.6562 Remote Similarity NPD5694 Approved
0.6559 Remote Similarity NPD3618 Phase 1
0.6559 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6542 Remote Similarity NPD6882 Approved
0.6542 Remote Similarity NPD8297 Approved
0.6538 Remote Similarity NPD6412 Phase 2
0.6526 Remote Similarity NPD5328 Approved
0.6526 Remote Similarity NPD7285 Clinical (unspecified phase)
0.65 Remote Similarity NPD7638 Approved
0.6495 Remote Similarity NPD4202 Approved
0.6495 Remote Similarity NPD5778 Approved
0.6495 Remote Similarity NPD5779 Approved
0.6484 Remote Similarity NPD4223 Phase 3
0.6484 Remote Similarity NPD4221 Approved
0.6476 Remote Similarity NPD6011 Approved
0.6471 Remote Similarity NPD6081 Approved
0.6465 Remote Similarity NPD7732 Phase 3
0.6465 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6463 Remote Similarity NPD4224 Phase 2
0.6458 Remote Similarity NPD5207 Approved
0.6455 Remote Similarity NPD7115 Discovery
0.6452 Remote Similarity NPD5329 Approved
0.6449 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6444 Remote Similarity NPD4695 Discontinued
0.6444 Remote Similarity NPD7525 Registered
0.6436 Remote Similarity NPD7639 Approved
0.6436 Remote Similarity NPD4696 Approved
0.6436 Remote Similarity NPD5286 Approved
0.6436 Remote Similarity NPD7640 Approved
0.6436 Remote Similarity NPD5285 Approved
0.6436 Remote Similarity NPD4700 Approved
0.6429 Remote Similarity NPD6001 Approved
0.6415 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6392 Remote Similarity NPD6079 Approved
0.6392 Remote Similarity NPD7637 Suspended
0.6381 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6374 Remote Similarity NPD5369 Approved
0.6364 Remote Similarity NPD5210 Approved
0.6364 Remote Similarity NPD4629 Approved
0.6353 Remote Similarity NPD4244 Approved
0.6353 Remote Similarity NPD4245 Approved
0.6344 Remote Similarity NPD4197 Approved
0.6337 Remote Similarity NPD4225 Approved
0.6333 Remote Similarity NPD7645 Phase 2
0.6311 Remote Similarity NPD5211 Phase 2
0.6311 Remote Similarity NPD5226 Approved
0.6311 Remote Similarity NPD5225 Approved
0.6311 Remote Similarity NPD5224 Approved
0.6311 Remote Similarity NPD4633 Approved
0.6306 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6319 Approved
0.6279 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6279 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6277 Remote Similarity NPD1694 Approved
0.6263 Remote Similarity NPD5282 Discontinued
0.6262 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6261 Remote Similarity NPD8328 Phase 3
0.625 Remote Similarity NPD6052 Approved
0.625 Remote Similarity NPD8039 Approved
0.625 Remote Similarity NPD5174 Approved
0.625 Remote Similarity NPD5175 Approved
0.6235 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6235 Remote Similarity NPD4137 Phase 3
0.6235 Remote Similarity NPD3698 Phase 2
0.6235 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6228 Remote Similarity NPD6921 Approved
0.6222 Remote Similarity NPD3617 Approved
0.6216 Remote Similarity NPD6274 Approved
0.6214 Remote Similarity NPD5223 Approved
0.6211 Remote Similarity NPD4689 Approved
0.6211 Remote Similarity NPD4623 Approved
0.6211 Remote Similarity NPD5205 Approved
0.6211 Remote Similarity NPD4138 Approved
0.6211 Remote Similarity NPD4688 Approved
0.6211 Remote Similarity NPD4519 Discontinued
0.6211 Remote Similarity NPD5279 Phase 3
0.6211 Remote Similarity NPD4693 Phase 3
0.6211 Remote Similarity NPD4690 Approved
0.6207 Remote Similarity NPD7492 Approved
0.6204 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6204 Remote Similarity NPD4634 Approved
0.62 Remote Similarity NPD5654 Approved
0.6196 Remote Similarity NPD1779 Approved
0.6196 Remote Similarity NPD1780 Approved
0.6195 Remote Similarity NPD7100 Approved
0.6195 Remote Similarity NPD7101 Approved
0.619 Remote Similarity NPD5141 Approved
0.6182 Remote Similarity NPD4632 Approved
0.6163 Remote Similarity NPD4691 Approved
0.6163 Remote Similarity NPD4747 Approved
0.6163 Remote Similarity NPD4789 Approved
0.6154 Remote Similarity NPD6616 Approved
0.6145 Remote Similarity NPD3171 Clinical (unspecified phase)
0.614 Remote Similarity NPD6059 Approved
0.614 Remote Similarity NPD6054 Approved
0.6139 Remote Similarity NPD5222 Approved
0.6139 Remote Similarity NPD7614 Phase 1
0.6139 Remote Similarity NPD5221 Approved
0.6139 Remote Similarity NPD4697 Phase 3
0.6139 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6134 Remote Similarity NPD7319 Approved
0.6132 Remote Similarity NPD4768 Approved
0.6132 Remote Similarity NPD4767 Approved
0.6129 Remote Similarity NPD6435 Approved
0.6118 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6118 Remote Similarity NPD229 Approved
0.6118 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6118 Remote Similarity NPD5360 Phase 3
0.6106 Remote Similarity NPD6335 Approved
0.6102 Remote Similarity NPD8293 Discontinued
0.6102 Remote Similarity NPD7078 Approved
0.6095 Remote Similarity NPD4754 Approved
0.6087 Remote Similarity NPD6909 Approved
0.6087 Remote Similarity NPD5368 Approved
0.6087 Remote Similarity NPD6908 Approved

Structure

External Identifiers

PubChem CID   73349171
ChEMBL   CHEMBL2419355
ZINC  

Physicochemical Properties

Molecular Weight:  406.31
ALogP:  2.9356
MLogP:  3.77
XLogP:  8.018
# Rotatable Bonds:  12
Polar Surface Area:  44.76
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  29

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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