Natural Product: NPC224356

Natural Product ID:  NPC224356
Common Name:   3-Acetylsesterstatin 1
IUPAC Name:   [(5aS,5bR,7aR,9S,11aR,11bR,13R,13aS)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-1-oxo-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-3H-phenanthro[2,1-e][2]benzofuran-9-yl] acetate
Synonyms:   19-Acetyl Sesterstatin 3; 3-Acetylsesterstatin 1
Molecular Formula:   C27H40O5
Standard InCHIKey:  GRIVEGVPDUNMNE-JNBLGKNQSA-N
Standard InCHI:  InChI=1S/C27H40O5/c1-15(28)32-21-10-12-25(4)17(24(21,2)3)9-11-26(5)18-8-7-16-14-31-23(30)22(16)27(18,6)20(29)13-19(25)26/h17-21,29H,7-14H2,1-6H3/t17-,18-,19+,20+,21-,25-,26-,27+/m0/s1
Canonical SMILES:  CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C[C@@H](O)[C@]2([C@H]1CCC1=C2C(=O)OC1)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
NPO33333 hyrtios erecta Species Thorectidae Eukaryota Red Sea PMID[16378375]
NPO33333 hyrtios erecta Species Thorectidae Eukaryota Red Sea PMID[11809054]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis Inhibition = 13 % 24440480
NPT139 Cell Line HT-29 Homo sapiens IC50 >= 1 ug/ml 26383126
NPT168 Cell Line P388 Mus musculus IC50 >= 1 ug/ml 23398362
NPT81 Cell Line A549 Homo sapiens IC50 >= 1 ug/ml 22168134

  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 NPC224356 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 NPC132753
1.0 High Similarity NPC121402
1.0 High Similarity NPC151681
1.0 High Similarity NPC175351
0.9889 High Similarity NPC472362
0.9889 High Similarity NPC472363
0.9889 High Similarity NPC154526
0.9574 High Similarity NPC165250
0.9474 High Similarity NPC471208
0.9091 High Similarity NPC325054
0.89 High Similarity NPC275539
0.89 High Similarity NPC189075
0.89 High Similarity NPC300614
0.89 High Similarity NPC90946
0.8812 High Similarity NPC31522
0.88 High Similarity NPC110496
0.8776 High Similarity NPC476081
0.8681 High Similarity NPC250981
0.8673 High Similarity NPC471075
0.866 High Similarity NPC478056
0.8632 High Similarity NPC91010
0.8571 High Similarity NPC201406
0.8571 High Similarity NPC476299
0.8571 High Similarity NPC474012
0.8571 High Similarity NPC117685
0.8558 High Similarity NPC194951
0.8558 High Similarity NPC12046
0.8542 High Similarity NPC183012
0.8526 High Similarity NPC139692
0.8515 High Similarity NPC478052
0.85 High Similarity NPC112009
0.85 High Similarity NPC254202
0.85 High Similarity NPC120321
0.85 High Similarity NPC159533
0.8485 Intermediate Similarity NPC235142
0.8485 Intermediate Similarity NPC63249
0.8485 Intermediate Similarity NPC303559
0.8476 Intermediate Similarity NPC157441
0.8469 Intermediate Similarity NPC234617
0.8469 Intermediate Similarity NPC124703
0.8454 Intermediate Similarity NPC327179
0.8438 Intermediate Similarity NPC471720
0.8431 Intermediate Similarity NPC301666
0.8431 Intermediate Similarity NPC187435
0.8431 Intermediate Similarity NPC67321
0.8421 Intermediate Similarity NPC233345
0.8421 Intermediate Similarity NPC187722
0.8421 Intermediate Similarity NPC235704
0.8421 Intermediate Similarity NPC186363
0.84 Intermediate Similarity NPC134077
0.84 Intermediate Similarity NPC273005
0.84 Intermediate Similarity NPC295791
0.84 Intermediate Similarity NPC469606
0.84 Intermediate Similarity NPC31058
0.84 Intermediate Similarity NPC476890
0.84 Intermediate Similarity NPC136289
0.8381 Intermediate Similarity NPC476163
0.8367 Intermediate Similarity NPC253826
0.8367 Intermediate Similarity NPC38530
0.8367 Intermediate Similarity NPC84335
0.8333 Intermediate Similarity NPC474436
0.8333 Intermediate Similarity NPC472303
0.8333 Intermediate Similarity NPC214756
0.8333 Intermediate Similarity NPC272075
0.8333 Intermediate Similarity NPC158059
0.8333 Intermediate Similarity NPC34768
0.8333 Intermediate Similarity NPC295643
0.8333 Intermediate Similarity NPC49776
0.8333 Intermediate Similarity NPC63118
0.8333 Intermediate Similarity NPC202728
0.8333 Intermediate Similarity NPC469607
0.8333 Intermediate Similarity NPC229281
0.8333 Intermediate Similarity NPC118519
0.8317 Intermediate Similarity NPC180204
0.8317 Intermediate Similarity NPC478057
0.8317 Intermediate Similarity NPC476889
0.8317 Intermediate Similarity NPC95899
0.8317 Intermediate Similarity NPC324001
0.8316 Intermediate Similarity NPC227467
0.8316 Intermediate Similarity NPC78973
0.8316 Intermediate Similarity NPC210037
0.8316 Intermediate Similarity NPC280149
0.8316 Intermediate Similarity NPC477872
0.8316 Intermediate Similarity NPC221111
0.8316 Intermediate Similarity NPC474728
0.8316 Intermediate Similarity NPC273621
0.8316 Intermediate Similarity NPC18872
0.8316 Intermediate Similarity NPC7260
0.8316 Intermediate Similarity NPC120968
0.8316 Intermediate Similarity NPC290614
0.8302 Intermediate Similarity NPC25909
0.83 Intermediate Similarity NPC476888
0.83 Intermediate Similarity NPC81530
0.83 Intermediate Similarity NPC93744
0.83 Intermediate Similarity NPC471412
0.8298 Intermediate Similarity NPC277771
0.8283 Intermediate Similarity NPC471966
0.8283 Intermediate Similarity NPC164349
0.8283 Intermediate Similarity NPC194196
0.828 Intermediate Similarity NPC185638
0.828 Intermediate Similarity NPC56588
0.8265 Intermediate Similarity NPC134072
0.8265 Intermediate Similarity NPC116457
0.8265 Intermediate Similarity NPC235053
0.8265 Intermediate Similarity NPC242848
0.8265 Intermediate Similarity NPC234993
0.8265 Intermediate Similarity NPC7124
0.8261 Intermediate Similarity NPC171789
0.8247 Intermediate Similarity NPC74751
0.8247 Intermediate Similarity NPC6818
0.8247 Intermediate Similarity NPC191412
0.8247 Intermediate Similarity NPC474554
0.8247 Intermediate Similarity NPC114159
0.8235 Intermediate Similarity NPC222161
0.8229 Intermediate Similarity NPC329842
0.8229 Intermediate Similarity NPC158030
0.8229 Intermediate Similarity NPC105189
0.8229 Intermediate Similarity NPC4036
0.8229 Intermediate Similarity NPC470590
0.8229 Intermediate Similarity NPC65120
0.8229 Intermediate Similarity NPC77099
0.8229 Intermediate Similarity NPC72845
0.8229 Intermediate Similarity NPC60755
0.8229 Intermediate Similarity NPC145067
0.8229 Intermediate Similarity NPC285184
0.8229 Intermediate Similarity NPC233455
0.8229 Intermediate Similarity NPC38754
0.8229 Intermediate Similarity NPC289479
0.8218 Intermediate Similarity NPC32577
0.8218 Intermediate Similarity NPC80781
0.8218 Intermediate Similarity NPC162973
0.8218 Intermediate Similarity NPC40918
0.8218 Intermediate Similarity NPC155332
0.8218 Intermediate Similarity NPC273668
0.8218 Intermediate Similarity NPC137430
0.8218 Intermediate Similarity NPC114540
0.8211 Intermediate Similarity NPC290972
0.8211 Intermediate Similarity NPC198664
0.8211 Intermediate Similarity NPC5509
0.8211 Intermediate Similarity NPC174342
0.8211 Intermediate Similarity NPC64872
0.8211 Intermediate Similarity NPC470588
0.8211 Intermediate Similarity NPC274330
0.8211 Intermediate Similarity NPC25906
0.8211 Intermediate Similarity NPC30522
0.8211 Intermediate Similarity NPC143232
0.8208 Intermediate Similarity NPC277769
0.82 Intermediate Similarity NPC474190
0.82 Intermediate Similarity NPC307954
0.82 Intermediate Similarity NPC251680
0.82 Intermediate Similarity NPC47024
0.82 Intermediate Similarity NPC471413
0.82 Intermediate Similarity NPC476767
0.8191 Intermediate Similarity NPC312561
0.8191 Intermediate Similarity NPC305029
0.8182 Intermediate Similarity NPC89225
0.8182 Intermediate Similarity NPC51499
0.8182 Intermediate Similarity NPC259788
0.8182 Intermediate Similarity NPC170131
0.8182 Intermediate Similarity NPC474343
0.8182 Intermediate Similarity NPC255589
0.8173 Intermediate Similarity NPC306265
0.8172 Intermediate Similarity NPC474013
0.8172 Intermediate Similarity NPC197823
0.8163 Intermediate Similarity NPC96916
0.8163 Intermediate Similarity NPC290481
0.8163 Intermediate Similarity NPC276110
0.8163 Intermediate Similarity NPC139570
0.8163 Intermediate Similarity NPC53565
0.8155 Intermediate Similarity NPC478208
0.8144 Intermediate Similarity NPC86368
0.8144 Intermediate Similarity NPC271652
0.8144 Intermediate Similarity NPC169343
0.8144 Intermediate Similarity NPC477436
0.8144 Intermediate Similarity NPC53555
0.8144 Intermediate Similarity NPC477435
0.8137 Intermediate Similarity NPC8196
0.8137 Intermediate Similarity NPC99266
0.8137 Intermediate Similarity NPC36688
0.8137 Intermediate Similarity NPC476237
0.8137 Intermediate Similarity NPC90177
0.8131 Intermediate Similarity NPC122056
0.8125 Intermediate Similarity NPC470589
0.8125 Intermediate Similarity NPC8062
0.8125 Intermediate Similarity NPC130278
0.8125 Intermediate Similarity NPC111110
0.8125 Intermediate Similarity NPC198818
0.8125 Intermediate Similarity NPC161638
0.8125 Intermediate Similarity NPC126369
0.8125 Intermediate Similarity NPC193750
0.8125 Intermediate Similarity NPC120840
0.8125 Intermediate Similarity NPC472307
0.8125 Intermediate Similarity NPC113989
0.8125 Intermediate Similarity NPC281942
0.8125 Intermediate Similarity NPC291028
0.8125 Intermediate Similarity NPC232426
0.8119 Intermediate Similarity NPC54909
0.8119 Intermediate Similarity NPC473160
0.8119 Intermediate Similarity NPC472637
0.8119 Intermediate Similarity NPC233012

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC224356 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
0.8367 Intermediate Similarity NPD7902 Approved
0.8283 Intermediate Similarity NPD7638 Approved
0.8247 Intermediate Similarity NPD7748 Approved
0.8229 Intermediate Similarity NPD7515 Phase 2
0.82 Intermediate Similarity NPD7639 Approved
0.82 Intermediate Similarity NPD7640 Approved
0.8095 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD7900 Approved
0.8061 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD7632 Discontinued
0.8019 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD6399 Phase 3
0.7909 Intermediate Similarity NPD7115 Discovery
0.7857 Intermediate Similarity NPD8034 Phase 2
0.7857 Intermediate Similarity NPD8035 Phase 2
0.7745 Intermediate Similarity NPD4225 Approved
0.7736 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD3618 Phase 1
0.766 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD5739 Approved
0.7642 Intermediate Similarity NPD6675 Approved
0.7642 Intermediate Similarity NPD6402 Approved
0.7642 Intermediate Similarity NPD7128 Approved
0.7604 Intermediate Similarity NPD1694 Approved
0.7604 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD6372 Approved
0.7593 Intermediate Similarity NPD6373 Approved
0.7551 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6881 Approved
0.75 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD6899 Approved
0.75 Intermediate Similarity NPD6686 Approved
0.7475 Intermediate Similarity NPD5328 Approved
0.7455 Intermediate Similarity NPD6650 Approved
0.7455 Intermediate Similarity NPD6649 Approved
0.7407 Intermediate Similarity NPD5701 Approved
0.7407 Intermediate Similarity NPD5697 Approved
0.7373 Intermediate Similarity NPD7507 Approved
0.7364 Intermediate Similarity NPD6883 Approved
0.7364 Intermediate Similarity NPD7102 Approved
0.7364 Intermediate Similarity NPD7290 Approved
0.7347 Intermediate Similarity NPD5330 Approved
0.7347 Intermediate Similarity NPD7146 Approved
0.7347 Intermediate Similarity NPD7521 Approved
0.7347 Intermediate Similarity NPD7334 Approved
0.7347 Intermediate Similarity NPD6409 Approved
0.7347 Intermediate Similarity NPD6684 Approved
0.7339 Intermediate Similarity NPD6011 Approved
0.7327 Intermediate Similarity NPD6079 Approved
0.732 Intermediate Similarity NPD4786 Approved
0.7312 Intermediate Similarity NPD6116 Phase 1
0.7308 Intermediate Similarity NPD6084 Phase 2
0.7308 Intermediate Similarity NPD6083 Phase 2
0.73 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD8130 Phase 1
0.7297 Intermediate Similarity NPD6847 Approved
0.7297 Intermediate Similarity NPD6869 Approved
0.7297 Intermediate Similarity NPD6617 Approved
0.7292 Intermediate Similarity NPD3667 Approved
0.7273 Intermediate Similarity NPD6012 Approved
0.7273 Intermediate Similarity NPD6014 Approved
0.7273 Intermediate Similarity NPD6013 Approved
0.7273 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD4202 Approved
0.7232 Intermediate Similarity NPD6882 Approved
0.7232 Intermediate Similarity NPD8297 Approved
0.7212 Intermediate Similarity NPD4697 Phase 3
0.7204 Intermediate Similarity NPD6117 Approved
0.72 Intermediate Similarity NPD6903 Approved
0.72 Intermediate Similarity NPD6672 Approved
0.72 Intermediate Similarity NPD5737 Approved
0.719 Intermediate Similarity NPD7319 Approved
0.7156 Intermediate Similarity NPD6008 Approved
0.7143 Intermediate Similarity NPD4755 Approved
0.7143 Intermediate Similarity NPD3133 Approved
0.7143 Intermediate Similarity NPD3665 Phase 1
0.7143 Intermediate Similarity NPD3666 Approved
0.713 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD3573 Approved
0.7075 Intermediate Similarity NPD5696 Approved
0.7069 Intermediate Similarity NPD7328 Approved
0.7069 Intermediate Similarity NPD7327 Approved
0.7053 Intermediate Similarity NPD6697 Approved
0.7053 Intermediate Similarity NPD6115 Approved
0.7053 Intermediate Similarity NPD6114 Approved
0.7053 Intermediate Similarity NPD6118 Approved
0.7048 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5222 Approved
0.7048 Intermediate Similarity NPD5221 Approved
0.7037 Intermediate Similarity NPD5211 Phase 2
0.7034 Intermediate Similarity NPD8033 Approved
0.7009 Intermediate Similarity NPD5286 Approved
0.7009 Intermediate Similarity NPD4700 Approved
0.7009 Intermediate Similarity NPD4696 Approved
0.7009 Intermediate Similarity NPD5285 Approved
0.7009 Intermediate Similarity NPD7516 Approved
0.7 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.699 Remote Similarity NPD5693 Phase 1
0.699 Remote Similarity NPD6411 Approved
0.6989 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5173 Approved
0.6979 Remote Similarity NPD7645 Phase 2
0.6952 Remote Similarity NPD5695 Phase 3
0.6949 Remote Similarity NPD8294 Approved
0.6949 Remote Similarity NPD8377 Approved
0.6944 Remote Similarity NPD5223 Approved
0.6937 Remote Similarity NPD6412 Phase 2
0.693 Remote Similarity NPD6053 Discontinued
0.6923 Remote Similarity NPD6335 Approved
0.6917 Remote Similarity NPD8328 Phase 3
0.6909 Remote Similarity NPD5141 Approved
0.6907 Remote Similarity NPD7525 Registered
0.6897 Remote Similarity NPD6274 Approved
0.6897 Remote Similarity NPD6868 Approved
0.6893 Remote Similarity NPD5785 Approved
0.6891 Remote Similarity NPD8379 Approved
0.6891 Remote Similarity NPD8335 Approved
0.6891 Remote Similarity NPD8296 Approved
0.6891 Remote Similarity NPD8380 Approved
0.6891 Remote Similarity NPD8378 Approved
0.6881 Remote Similarity NPD5225 Approved
0.6881 Remote Similarity NPD5226 Approved
0.6881 Remote Similarity NPD5224 Approved
0.6881 Remote Similarity NPD4633 Approved
0.6875 Remote Similarity NPD3617 Approved
0.6875 Remote Similarity NPD5345 Clinical (unspecified phase)
0.687 Remote Similarity NPD8133 Approved
0.687 Remote Similarity NPD4632 Approved
0.6864 Remote Similarity NPD7100 Approved
0.6864 Remote Similarity NPD7101 Approved
0.6838 Remote Similarity NPD6317 Approved
0.6827 Remote Similarity NPD5281 Approved
0.6827 Remote Similarity NPD5284 Approved
0.6818 Remote Similarity NPD5175 Approved
0.6818 Remote Similarity NPD5174 Approved
0.6818 Remote Similarity NPD4754 Approved
0.68 Remote Similarity NPD6400 Clinical (unspecified phase)
0.68 Remote Similarity NPD3668 Phase 3
0.6796 Remote Similarity NPD6080 Approved
0.6796 Remote Similarity NPD6051 Approved
0.6796 Remote Similarity NPD6673 Approved
0.6796 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6796 Remote Similarity NPD6904 Approved
0.6796 Remote Similarity NPD6101 Approved
0.6796 Remote Similarity NPD4753 Phase 2
0.6792 Remote Similarity NPD1698 Clinical (unspecified phase)
0.678 Remote Similarity NPD6313 Approved
0.678 Remote Similarity NPD6314 Approved
0.6762 Remote Similarity NPD5779 Approved
0.6762 Remote Similarity NPD5778 Approved
0.675 Remote Similarity NPD6909 Approved
0.675 Remote Similarity NPD6291 Clinical (unspecified phase)
0.675 Remote Similarity NPD6908 Approved
0.6735 Remote Similarity NPD4695 Discontinued
0.6731 Remote Similarity NPD6698 Approved
0.6731 Remote Similarity NPD46 Approved
0.6729 Remote Similarity NPD7614 Phase 1
0.6698 Remote Similarity NPD6001 Approved
0.6696 Remote Similarity NPD4768 Approved
0.6696 Remote Similarity NPD4767 Approved
0.6695 Remote Similarity NPD6009 Approved
0.6694 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD4623 Approved
0.6667 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD5279 Phase 3
0.6667 Remote Similarity NPD4519 Discontinued
0.6639 Remote Similarity NPD7604 Phase 2
0.6636 Remote Similarity NPD4629 Approved
0.6636 Remote Similarity NPD5210 Approved
0.6612 Remote Similarity NPD5983 Phase 2
0.6612 Remote Similarity NPD7503 Approved
0.66 Remote Similarity NPD4221 Approved
0.66 Remote Similarity NPD4223 Phase 3
0.6596 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6596 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6585 Remote Similarity NPD7492 Approved
0.6579 Remote Similarity NPD5128 Approved
0.6579 Remote Similarity NPD4730 Approved
0.6579 Remote Similarity NPD4729 Approved
0.6574 Remote Similarity NPD7732 Phase 3
0.6569 Remote Similarity NPD5329 Approved
0.6562 Remote Similarity NPD7339 Approved
0.6562 Remote Similarity NPD6942 Approved
0.6559 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6559 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6538 Remote Similarity NPD5208 Approved
0.6535 Remote Similarity NPD4788 Approved
0.6532 Remote Similarity NPD6336 Discontinued
0.6532 Remote Similarity NPD6616 Approved
0.6529 Remote Similarity NPD6059 Approved
0.6529 Remote Similarity NPD6054 Approved
0.6509 Remote Similarity NPD6050 Approved
0.6509 Remote Similarity NPD7637 Suspended
0.6505 Remote Similarity NPD6098 Approved
0.6495 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6486 Remote Similarity NPD5344 Discontinued
0.648 Remote Similarity NPD7078 Approved
0.648 Remote Similarity NPD8293 Discontinued

Structure

External Identifiers

PubChem CID   21629517
ChEMBL   CHEMBL514733
ZINC  

Physicochemical Properties

Molecular Weight:  444.29
ALogP:  1.3589
MLogP:  3.88
XLogP:  5.252
# Rotatable Bonds:  9
Polar Surface Area:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  32

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs