Natural Product: NPC469403

Natural Product ID:  NPC469403
Common Name:   Gracilin L
IUPAC Name:   [(1S,3R,3aR,4Z,7S,7aS)-3-acetyloxy-4-ethylidene-7-hydroxy-5-[(1S)-1,3,3-trimethylcyclohexyl]-3,3a,7,7a-tetrahydro-1H-2-benzofuran-1-yl] acetate
Synonyms:   Gracilin L
Molecular Formula:   C23H34O6
Standard InCHIKey:  MHDUGZBUXWJHKW-JEBUWBOWSA-N
Standard InCHI:  InChI=1S/C23H34O6/c1-7-15-16(23(6)10-8-9-22(4,5)12-23)11-17(26)19-18(15)20(27-13(2)24)29-21(19)28-14(3)25/h7,11,17-21,26H,8-10,12H2,1-6H3/b15-7+/t17-,18-,19+,20-,21+,23-/m0/s1
Canonical SMILES:  C/C=C1/[C@@H]2[C@@H](OC(=O)C)O[C@H]([C@@H]2[C@H](C=C1[C@@]1(C)CCCC(C1)(C)C)O)OC(=O)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
NPO33347 spongionella sp. Species Dictyodendrillidae Eukaryota PMID[19601607]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT927 Cell Line PBMC Homo sapiens IC50 = 3000 nM 11430012
NPT111 Cell Line K562 Homo sapiens IC50 = 2650 nM 11430012
NPT285 Individual Protein Epidermal growth factor receptor erbB1 Homo sapiens Inhibition = 75 % 18611050

  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 NPC469403 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
0.9121 High Similarity NPC98112
0.881 High Similarity NPC473685
0.8646 High Similarity NPC134270
0.8587 High Similarity NPC104925
0.8587 High Similarity NPC298973
0.8557 High Similarity NPC470321
0.8557 High Similarity NPC201880
0.8557 High Similarity NPC81567
0.8557 High Similarity NPC264867
0.8557 High Similarity NPC473207
0.8556 High Similarity NPC470734
0.8542 High Similarity NPC471363
0.8542 High Similarity NPC238397
0.8495 Intermediate Similarity NPC286612
0.8495 Intermediate Similarity NPC230347
0.8495 Intermediate Similarity NPC275310
0.8485 Intermediate Similarity NPC470024
0.8469 Intermediate Similarity NPC252296
0.8454 Intermediate Similarity NPC7644
0.8454 Intermediate Similarity NPC7613
0.8454 Intermediate Similarity NPC127933
0.8454 Intermediate Similarity NPC475889
0.8391 Intermediate Similarity NPC109938
0.8391 Intermediate Similarity NPC122945
0.8387 Intermediate Similarity NPC88507
0.8387 Intermediate Similarity NPC469697
0.8384 Intermediate Similarity NPC109376
0.8384 Intermediate Similarity NPC184512
0.8352 Intermediate Similarity NPC293044
0.83 Intermediate Similarity NPC311223
0.83 Intermediate Similarity NPC224660
0.8298 Intermediate Similarity NPC471372
0.8298 Intermediate Similarity NPC471362
0.8298 Intermediate Similarity NPC472189
0.8283 Intermediate Similarity NPC172867
0.8261 Intermediate Similarity NPC470817
0.8242 Intermediate Similarity NPC472809
0.8242 Intermediate Similarity NPC472810
0.8242 Intermediate Similarity NPC474629
0.8235 Intermediate Similarity NPC17791
0.8218 Intermediate Similarity NPC316974
0.8211 Intermediate Similarity NPC311166
0.8211 Intermediate Similarity NPC171598
0.8211 Intermediate Similarity NPC162346
0.82 Intermediate Similarity NPC88013
0.82 Intermediate Similarity NPC125423
0.8191 Intermediate Similarity NPC470255
0.8172 Intermediate Similarity NPC165904
0.8172 Intermediate Similarity NPC179517
0.8163 Intermediate Similarity NPC470571
0.8161 Intermediate Similarity NPC206062
0.8155 Intermediate Similarity NPC470025
0.8155 Intermediate Similarity NPC321272
0.8155 Intermediate Similarity NPC328074
0.8155 Intermediate Similarity NPC317460
0.8152 Intermediate Similarity NPC470819
0.8144 Intermediate Similarity NPC161527
0.8144 Intermediate Similarity NPC228251
0.8144 Intermediate Similarity NPC477972
0.8144 Intermediate Similarity NPC477968
0.8144 Intermediate Similarity NPC219285
0.8144 Intermediate Similarity NPC477971
0.8144 Intermediate Similarity NPC473204
0.8144 Intermediate Similarity NPC20113
0.8137 Intermediate Similarity NPC316708
0.8137 Intermediate Similarity NPC119550
0.8125 Intermediate Similarity NPC472188
0.8119 Intermediate Similarity NPC128795
0.8119 Intermediate Similarity NPC217921
0.8119 Intermediate Similarity NPC135015
0.8119 Intermediate Similarity NPC48548
0.8111 Intermediate Similarity NPC473251
0.8111 Intermediate Similarity NPC42586
0.8111 Intermediate Similarity NPC119001
0.81 Intermediate Similarity NPC218158
0.8085 Intermediate Similarity NPC472812
0.8077 Intermediate Similarity NPC470027
0.8065 Intermediate Similarity NPC159876
0.8058 Intermediate Similarity NPC470026
0.8046 Intermediate Similarity NPC242767
0.8046 Intermediate Similarity NPC17550
0.8043 Intermediate Similarity NPC472378
0.8043 Intermediate Similarity NPC263079
0.8041 Intermediate Similarity NPC472186
0.8041 Intermediate Similarity NPC474440
0.8041 Intermediate Similarity NPC471366
0.8041 Intermediate Similarity NPC473154
0.8041 Intermediate Similarity NPC318917
0.8041 Intermediate Similarity NPC476800
0.8039 Intermediate Similarity NPC40728
0.8022 Intermediate Similarity NPC173917
0.8022 Intermediate Similarity NPC118266
0.8 Intermediate Similarity NPC470768
0.7979 Intermediate Similarity NPC302584
0.7979 Intermediate Similarity NPC472811
0.7979 Intermediate Similarity NPC477122
0.7959 Intermediate Similarity NPC477721
0.7959 Intermediate Similarity NPC477716
0.7959 Intermediate Similarity NPC472187
0.7959 Intermediate Similarity NPC473545
0.7957 Intermediate Similarity NPC473058
0.7957 Intermediate Similarity NPC16265
0.7938 Intermediate Similarity NPC155319
0.7938 Intermediate Similarity NPC91197
0.7938 Intermediate Similarity NPC239547
0.7938 Intermediate Similarity NPC477719
0.7938 Intermediate Similarity NPC125551
0.7938 Intermediate Similarity NPC309503
0.7938 Intermediate Similarity NPC477718
0.7938 Intermediate Similarity NPC96597
0.7935 Intermediate Similarity NPC166857
0.7917 Intermediate Similarity NPC13924
0.7912 Intermediate Similarity NPC472442
0.7912 Intermediate Similarity NPC329738
0.7912 Intermediate Similarity NPC163606
0.79 Intermediate Similarity NPC120009
0.7889 Intermediate Similarity NPC472440
0.7879 Intermediate Similarity NPC21064
0.7879 Intermediate Similarity NPC477717
0.7879 Intermediate Similarity NPC121072
0.7872 Intermediate Similarity NPC48732
0.7872 Intermediate Similarity NPC220216
0.7872 Intermediate Similarity NPC78973
0.7872 Intermediate Similarity NPC471370
0.7872 Intermediate Similarity NPC471371
0.7864 Intermediate Similarity NPC206618
0.7843 Intermediate Similarity NPC475074
0.7835 Intermediate Similarity NPC94905
0.7835 Intermediate Similarity NPC8954
0.7835 Intermediate Similarity NPC112654
0.7812 Intermediate Similarity NPC474554
0.7812 Intermediate Similarity NPC211238
0.7802 Intermediate Similarity NPC126518
0.7802 Intermediate Similarity NPC470800
0.7802 Intermediate Similarity NPC102048
0.7802 Intermediate Similarity NPC319238
0.78 Intermediate Similarity NPC154452
0.78 Intermediate Similarity NPC134077
0.7789 Intermediate Similarity NPC141831
0.7789 Intermediate Similarity NPC120539
0.7789 Intermediate Similarity NPC124374
0.7778 Intermediate Similarity NPC324841
0.7778 Intermediate Similarity NPC469942
0.7778 Intermediate Similarity NPC471298
0.7778 Intermediate Similarity NPC477720
0.7778 Intermediate Similarity NPC146188
0.7778 Intermediate Similarity NPC323251
0.7778 Intermediate Similarity NPC256112
0.7767 Intermediate Similarity NPC38948
0.7766 Intermediate Similarity NPC477917
0.7766 Intermediate Similarity NPC261320
0.7755 Intermediate Similarity NPC141401
0.7745 Intermediate Similarity NPC470056
0.7745 Intermediate Similarity NPC470767
0.7745 Intermediate Similarity NPC470763
0.7745 Intermediate Similarity NPC470055
0.7736 Intermediate Similarity NPC474410
0.7736 Intermediate Similarity NPC293658
0.7732 Intermediate Similarity NPC477970
0.7732 Intermediate Similarity NPC477969
0.7732 Intermediate Similarity NPC100892
0.7732 Intermediate Similarity NPC472441
0.7732 Intermediate Similarity NPC135224
0.7723 Intermediate Similarity NPC132395
0.7723 Intermediate Similarity NPC471365
0.7723 Intermediate Similarity NPC471364
0.7723 Intermediate Similarity NPC45897
0.7717 Intermediate Similarity NPC329630
0.7717 Intermediate Similarity NPC35933
0.7717 Intermediate Similarity NPC109528
0.7708 Intermediate Similarity NPC99653
0.7708 Intermediate Similarity NPC166346
0.77 Intermediate Similarity NPC469657
0.77 Intermediate Similarity NPC470434
0.77 Intermediate Similarity NPC244456
0.77 Intermediate Similarity NPC280991
0.77 Intermediate Similarity NPC63249
0.7692 Intermediate Similarity NPC52108
0.7692 Intermediate Similarity NPC23748
0.7692 Intermediate Similarity NPC311070
0.7692 Intermediate Similarity NPC471297
0.7692 Intermediate Similarity NPC474789
0.7692 Intermediate Similarity NPC42476
0.7684 Intermediate Similarity NPC281942
0.7684 Intermediate Similarity NPC232426
0.7677 Intermediate Similarity NPC241657
0.7677 Intermediate Similarity NPC477928
0.767 Intermediate Similarity NPC472390
0.767 Intermediate Similarity NPC293512
0.7653 Intermediate Similarity NPC240673
0.7653 Intermediate Similarity NPC165632
0.7653 Intermediate Similarity NPC17578
0.7647 Intermediate Similarity NPC31430
0.7647 Intermediate Similarity NPC85593
0.764 Intermediate Similarity NPC100906
0.7634 Intermediate Similarity NPC477668
0.7634 Intermediate Similarity NPC329692
0.7634 Intermediate Similarity NPC473226
0.7634 Intermediate Similarity NPC474970
0.7629 Intermediate Similarity NPC189513

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469403 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
0.7802 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7637 Suspended
0.7419 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD6695 Phase 3
0.7264 Intermediate Similarity NPD6686 Approved
0.7172 Intermediate Similarity NPD5778 Approved
0.7172 Intermediate Similarity NPD6399 Phase 3
0.7172 Intermediate Similarity NPD5779 Approved
0.7157 Intermediate Similarity NPD4225 Approved
0.7105 Intermediate Similarity NPD7503 Approved
0.7071 Intermediate Similarity NPD6411 Approved
0.7065 Intermediate Similarity NPD6929 Approved
0.701 Intermediate Similarity NPD7524 Approved
0.701 Intermediate Similarity NPD7750 Discontinued
0.7009 Intermediate Similarity NPD6412 Phase 2
0.7 Intermediate Similarity NPD8264 Approved
0.6989 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6931 Approved
0.6989 Remote Similarity NPD6930 Phase 2
0.6923 Remote Similarity NPD7639 Approved
0.6923 Remote Similarity NPD7640 Approved
0.6889 Remote Similarity NPD6926 Approved
0.6889 Remote Similarity NPD6924 Approved
0.6869 Remote Similarity NPD6101 Approved
0.6869 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6051 Approved
0.6848 Remote Similarity NPD6925 Approved
0.6848 Remote Similarity NPD5776 Phase 2
0.6842 Remote Similarity NPD7327 Approved
0.6842 Remote Similarity NPD7328 Approved
0.6827 Remote Similarity NPD7638 Approved
0.6827 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6942 Approved
0.6813 Remote Similarity NPD7339 Approved
0.681 Remote Similarity NPD8517 Approved
0.681 Remote Similarity NPD8516 Approved
0.681 Remote Similarity NPD8033 Approved
0.681 Remote Similarity NPD8515 Approved
0.681 Remote Similarity NPD8513 Phase 3
0.6809 Remote Similarity NPD4819 Approved
0.6809 Remote Similarity NPD4822 Approved
0.6809 Remote Similarity NPD7514 Phase 3
0.6809 Remote Similarity NPD7332 Phase 2
0.6809 Remote Similarity NPD4820 Approved
0.6809 Remote Similarity NPD4821 Approved
0.6783 Remote Similarity NPD7516 Approved
0.6774 Remote Similarity NPD4271 Approved
0.6774 Remote Similarity NPD4268 Approved
0.6774 Remote Similarity NPD7145 Approved
0.6774 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6771 Remote Similarity NPD7154 Phase 3
0.6739 Remote Similarity NPD6933 Approved
0.6739 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6737 Remote Similarity NPD6902 Approved
0.6733 Remote Similarity NPD7087 Discontinued
0.6731 Remote Similarity NPD6083 Phase 2
0.6731 Remote Similarity NPD6084 Phase 2
0.6724 Remote Similarity NPD8294 Approved
0.6724 Remote Similarity NPD8377 Approved
0.6702 Remote Similarity NPD7645 Phase 2
0.6701 Remote Similarity NPD4786 Approved
0.6696 Remote Similarity NPD6882 Approved
0.6667 Remote Similarity NPD8380 Approved
0.6667 Remote Similarity NPD8335 Approved
0.6667 Remote Similarity NPD8379 Approved
0.6667 Remote Similarity NPD3667 Approved
0.6667 Remote Similarity NPD8296 Approved
0.6667 Remote Similarity NPD4251 Approved
0.6667 Remote Similarity NPD4250 Approved
0.6667 Remote Similarity NPD8378 Approved
0.6635 Remote Similarity NPD7839 Suspended
0.6634 Remote Similarity NPD7838 Discovery
0.6633 Remote Similarity NPD6893 Approved
0.6632 Remote Similarity NPD7509 Discontinued
0.6632 Remote Similarity NPD7525 Registered
0.6629 Remote Similarity NPD6922 Approved
0.6629 Remote Similarity NPD6923 Approved
0.6606 Remote Similarity NPD6675 Approved
0.6606 Remote Similarity NPD7128 Approved
0.6606 Remote Similarity NPD6402 Approved
0.6606 Remote Similarity NPD5739 Approved
0.6602 Remote Similarity NPD7748 Approved
0.6598 Remote Similarity NPD5362 Discontinued
0.6596 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6577 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7902 Approved
0.6569 Remote Similarity NPD7515 Phase 2
0.6569 Remote Similarity NPD7983 Approved
0.6566 Remote Similarity NPD6409 Approved
0.6566 Remote Similarity NPD6684 Approved
0.6566 Remote Similarity NPD5330 Approved
0.6566 Remote Similarity NPD7521 Approved
0.6566 Remote Similarity NPD7146 Approved
0.6566 Remote Similarity NPD4249 Approved
0.6566 Remote Similarity NPD7334 Approved
0.6562 Remote Similarity NPD6898 Phase 1
0.6556 Remote Similarity NPD7143 Approved
0.6556 Remote Similarity NPD7144 Approved
0.6538 Remote Similarity NPD5695 Phase 3
0.65 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6495 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6489 Remote Similarity NPD6932 Approved
0.6486 Remote Similarity NPD7320 Approved
0.6486 Remote Similarity NPD6899 Approved
0.6486 Remote Similarity NPD6881 Approved
0.6484 Remote Similarity NPD7151 Approved
0.6484 Remote Similarity NPD7152 Approved
0.6484 Remote Similarity NPD7150 Approved
0.6466 Remote Similarity NPD7115 Discovery
0.6465 Remote Similarity NPD1694 Approved
0.6465 Remote Similarity NPD6082 Clinical (unspecified phase)
0.646 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6648 Approved
0.6446 Remote Similarity NPD7507 Approved
0.6436 Remote Similarity NPD6672 Approved
0.6436 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6436 Remote Similarity NPD5737 Approved
0.6436 Remote Similarity NPD6903 Approved
0.6429 Remote Similarity NPD5332 Approved
0.6429 Remote Similarity NPD5331 Approved
0.6429 Remote Similarity NPD6372 Approved
0.6429 Remote Similarity NPD6373 Approved
0.6408 Remote Similarity NPD5284 Approved
0.6408 Remote Similarity NPD5281 Approved
0.64 Remote Similarity NPD5279 Phase 3
0.6396 Remote Similarity NPD5697 Approved
0.6396 Remote Similarity NPD5701 Approved
0.6395 Remote Similarity NPD368 Approved
0.6393 Remote Similarity NPD8293 Discontinued
0.6392 Remote Similarity NPD4790 Discontinued
0.6389 Remote Similarity NPD5344 Discontinued
0.6381 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6373 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6372 Remote Similarity NPD7102 Approved
0.6372 Remote Similarity NPD7290 Approved
0.6372 Remote Similarity NPD6883 Approved
0.6364 Remote Similarity NPD3133 Approved
0.6364 Remote Similarity NPD3666 Approved
0.6364 Remote Similarity NPD3665 Phase 1
0.6355 Remote Similarity NPD5696 Approved
0.6354 Remote Similarity NPD6683 Phase 2
0.6348 Remote Similarity NPD8133 Approved
0.6341 Remote Similarity NPD7736 Approved
0.6333 Remote Similarity NPD6370 Approved
0.633 Remote Similarity NPD7632 Discontinued
0.6327 Remote Similarity NPD4270 Approved
0.6327 Remote Similarity NPD6435 Approved
0.6327 Remote Similarity NPD4269 Approved
0.6325 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6869 Approved
0.6316 Remote Similarity NPD8130 Phase 1
0.6316 Remote Similarity NPD6847 Approved
0.6316 Remote Similarity NPD6649 Approved
0.6316 Remote Similarity NPD6617 Approved
0.6316 Remote Similarity NPD6650 Approved
0.6311 Remote Similarity NPD46 Approved
0.6311 Remote Similarity NPD6698 Approved
0.6311 Remote Similarity NPD5785 Approved
0.629 Remote Similarity NPD7319 Approved
0.6286 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6286 Remote Similarity NPD7900 Approved
0.6283 Remote Similarity NPD6013 Approved
0.6283 Remote Similarity NPD6014 Approved
0.6283 Remote Similarity NPD6012 Approved
0.6281 Remote Similarity NPD8328 Phase 3
0.6277 Remote Similarity NPD8039 Approved
0.6261 Remote Similarity NPD6053 Discontinued
0.6261 Remote Similarity NPD8297 Approved
0.626 Remote Similarity NPD8074 Phase 3
0.625 Remote Similarity NPD8035 Phase 2
0.625 Remote Similarity NPD8034 Phase 2
0.625 Remote Similarity NPD6050 Approved
0.625 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6238 Remote Similarity NPD5786 Approved
0.6238 Remote Similarity NPD3618 Phase 1
0.623 Remote Similarity NPD7492 Approved
0.6214 Remote Similarity NPD4753 Phase 2
0.6214 Remote Similarity NPD5328 Approved
0.62 Remote Similarity NPD3668 Phase 3
0.6195 Remote Similarity NPD6011 Approved
0.6182 Remote Similarity NPD5211 Phase 2
0.6179 Remote Similarity NPD6616 Approved
0.6174 Remote Similarity NPD6401 Clinical (unspecified phase)
0.617 Remote Similarity NPD4784 Approved
0.617 Remote Similarity NPD4785 Approved
0.6167 Remote Similarity NPD6054 Approved
0.6167 Remote Similarity NPD6059 Approved
0.6154 Remote Similarity NPD5207 Approved
0.6154 Remote Similarity NPD5692 Phase 3
0.6154 Remote Similarity NPD7136 Phase 2
0.6148 Remote Similarity NPD6067 Discontinued
0.6148 Remote Similarity NPD7122 Discontinued
0.6147 Remote Similarity NPD6404 Discontinued
0.614 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6139 Remote Similarity NPD5363 Approved
0.6139 Remote Similarity NPD1696 Phase 3
0.6139 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6129 Remote Similarity NPD4243 Approved
0.6129 Remote Similarity NPD7078 Approved
0.6122 Remote Similarity NPD4252 Approved

Structure

External Identifiers

PubChem CID   44254080
ChEMBL   CHEMBL1077772
ZINC  

Physicochemical Properties

Molecular Weight:  406.24
ALogP:  1.2883
MLogP:  3.33
XLogP:  5.392
# Rotatable Bonds:  12
Polar Surface Area:  82.06
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# 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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