Natural Product: NPC175870

Natural Product ID:  NPC175870
Common Name:   Cytochalasin Z11
IUPAC Name:   (3S,3aS,4S,6S,7S,7aS)-3-benzyl-6,7a-dihydroxy-7-[(E,4S,6S)-6-hydroxy-4-methyl-5-oxohept-1-enyl]-4-methyl-5-methylidene-2,3,3a,4,6,7-hexahydroisoindol-1-one
Synonyms:   Cytochalasin Z11
Molecular Formula:   C25H33NO5
Standard InCHIKey:  XKLGDBFKKUIZTH-UPQYTXQESA-N
Standard InCHI:  InChI=1S/C25H33NO5/c1-14(22(28)17(4)27)9-8-12-19-23(29)16(3)15(2)21-20(26-24(30)25(19,21)31)13-18-10-6-5-7-11-18/h5-8,10-12,14-15,17,19-21,23,27,29,31H,3,9,13H2,1-2,4H3,(H,26,30)/b12-8+/t14-,15+,17-,19-,20-,21-,23+,25+/m0/s1
Canonical SMILES:  O=C([C@H](C/C=C/[C@H]1[C@H](O)C(=C)[C@H]([C@@H]2[C@@]1(O)C(=N[C@H]2Cc1ccccc1)O)C)C)[C@@H](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
NPO33507 spicaria elegans Species NA NA PMID[18507474]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 100000 nM PubChem BioAssay data set
NPT116 Cell Line HL-60 Homo sapiens IC50 = 45000 nM 15270579
NPT168 Cell Line P388 Mus musculus IC50 = 69000 nM 10.6019/CHEMBL1201861
NPT81 Cell Line A549 Homo sapiens IC50 = 4300 nM 18443127

  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 NPC175870 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
0.9535 High Similarity NPC228511
0.9462 High Similarity NPC113325
0.9462 High Similarity NPC279045
0.9449 High Similarity NPC295478
0.9231 High Similarity NPC42423
0.8992 High Similarity NPC278097
0.8936 High Similarity NPC4108
0.8913 High Similarity NPC49565
0.8855 High Similarity NPC71271
0.8759 High Similarity NPC239770
0.8714 High Similarity NPC237240
0.8714 High Similarity NPC31171
0.8643 High Similarity NPC262216
0.8626 High Similarity NPC472414
0.8531 High Similarity NPC201692
0.8473 Intermediate Similarity NPC472415
0.8429 Intermediate Similarity NPC111586
0.8429 Intermediate Similarity NPC261709
0.8429 Intermediate Similarity NPC108852
0.8394 Intermediate Similarity NPC64897
0.8394 Intermediate Similarity NPC90693
0.8392 Intermediate Similarity NPC173934
0.8309 Intermediate Similarity NPC183722
0.8105 Intermediate Similarity NPC15506
0.8089 Intermediate Similarity NPC477115
0.8026 Intermediate Similarity NPC156348
0.8014 Intermediate Similarity NPC208725
0.777 Intermediate Similarity NPC472413
0.7643 Intermediate Similarity NPC116057
0.7333 Intermediate Similarity NPC188010
0.726 Intermediate Similarity NPC477680
0.7152 Intermediate Similarity NPC217801
0.7067 Intermediate Similarity NPC322526
0.7063 Intermediate Similarity NPC477249
0.7063 Intermediate Similarity NPC477248
0.705 Intermediate Similarity NPC314992
0.7042 Intermediate Similarity NPC35996
0.7029 Intermediate Similarity NPC2265
0.7023 Intermediate Similarity NPC194390
0.7023 Intermediate Similarity NPC113326
0.7023 Intermediate Similarity NPC224610
0.7023 Intermediate Similarity NPC88267
0.7 Intermediate Similarity NPC473055
0.7 Intermediate Similarity NPC473052
0.6962 Remote Similarity NPC275839
0.6957 Remote Similarity NPC235460
0.6954 Remote Similarity NPC471201
0.695 Remote Similarity NPC190663
0.6944 Remote Similarity NPC47667
0.6933 Remote Similarity NPC64205
0.6923 Remote Similarity NPC339338
0.6923 Remote Similarity NPC227905
0.6923 Remote Similarity NPC203005
0.6923 Remote Similarity NPC146097
0.6923 Remote Similarity NPC94602
0.6923 Remote Similarity NPC108286
0.6912 Remote Similarity NPC111108
0.6853 Remote Similarity NPC160493
0.6846 Remote Similarity NPC328070
0.6842 Remote Similarity NPC475345
0.6835 Remote Similarity NPC185404
0.6831 Remote Similarity NPC478014
0.6831 Remote Similarity NPC478016
0.6831 Remote Similarity NPC478015
0.6824 Remote Similarity NPC49272
0.6818 Remote Similarity NPC453583
0.6818 Remote Similarity NPC471754
0.6818 Remote Similarity NPC473300
0.6818 Remote Similarity NPC475336
0.6818 Remote Similarity NPC317882
0.6812 Remote Similarity NPC474544
0.6812 Remote Similarity NPC1986
0.6809 Remote Similarity NPC237420
0.6806 Remote Similarity NPC473871
0.6806 Remote Similarity NPC473870
0.6802 Remote Similarity NPC475649
0.68 Remote Similarity NPC132847
0.68 Remote Similarity NPC327699
0.6795 Remote Similarity NPC260194
0.6795 Remote Similarity NPC328824
0.678 Remote Similarity NPC67246
0.678 Remote Similarity NPC33372
0.6755 Remote Similarity NPC474811
0.6755 Remote Similarity NPC293377
0.6755 Remote Similarity NPC79465
0.6755 Remote Similarity NPC76785
0.6755 Remote Similarity NPC151706
0.6755 Remote Similarity NPC475598
0.6755 Remote Similarity NPC118099
0.6755 Remote Similarity NPC474855
0.6755 Remote Similarity NPC475318
0.6755 Remote Similarity NPC49577
0.6755 Remote Similarity NPC273907
0.6755 Remote Similarity NPC9687
0.6755 Remote Similarity NPC474787
0.6755 Remote Similarity NPC90194
0.6755 Remote Similarity NPC260045
0.6755 Remote Similarity NPC476102
0.6748 Remote Similarity NPC476194
0.6746 Remote Similarity NPC120667
0.6746 Remote Similarity NPC278272
0.6743 Remote Similarity NPC295531
0.6736 Remote Similarity NPC473889
0.6733 Remote Similarity NPC476976
0.673 Remote Similarity NPC470274
0.6725 Remote Similarity NPC476113
0.6723 Remote Similarity NPC206211
0.6723 Remote Similarity NPC306001
0.6723 Remote Similarity NPC471629
0.6723 Remote Similarity NPC473400
0.6723 Remote Similarity NPC275170
0.6723 Remote Similarity NPC324251
0.6716 Remote Similarity NPC474307
0.6713 Remote Similarity NPC80150
0.6713 Remote Similarity NPC477061
0.6713 Remote Similarity NPC45777
0.6709 Remote Similarity NPC476757
0.6706 Remote Similarity NPC211713
0.6706 Remote Similarity NPC88378
0.669 Remote Similarity NPC310467
0.6688 Remote Similarity NPC44649
0.6667 Remote Similarity NPC475933
0.6667 Remote Similarity NPC191193
0.6667 Remote Similarity NPC58674
0.6667 Remote Similarity NPC470158
0.6667 Remote Similarity NPC321072
0.6667 Remote Similarity NPC215892
0.6667 Remote Similarity NPC476977
0.6667 Remote Similarity NPC472862
0.6667 Remote Similarity NPC266343
0.6667 Remote Similarity NPC471189
0.6667 Remote Similarity NPC242662
0.6644 Remote Similarity NPC77691
0.663 Remote Similarity NPC181964
0.663 Remote Similarity NPC208553
0.663 Remote Similarity NPC471606
0.6626 Remote Similarity NPC477157
0.6626 Remote Similarity NPC477156
0.6623 Remote Similarity NPC80599
0.6623 Remote Similarity NPC3202
0.6622 Remote Similarity NPC476971
0.6622 Remote Similarity NPC476972
0.662 Remote Similarity NPC169328
0.661 Remote Similarity NPC471395
0.6609 Remote Similarity NPC469973
0.6603 Remote Similarity NPC475128
0.6593 Remote Similarity NPC211551
0.6593 Remote Similarity NPC473558
0.6584 Remote Similarity NPC472761
0.6582 Remote Similarity NPC475578
0.6581 Remote Similarity NPC150712
0.6581 Remote Similarity NPC197921
0.6577 Remote Similarity NPC58061
0.6575 Remote Similarity NPC273336
0.6575 Remote Similarity NPC182333
0.6573 Remote Similarity NPC471623
0.6556 Remote Similarity NPC246913
0.6554 Remote Similarity NPC476970
0.6554 Remote Similarity NPC45821
0.6552 Remote Similarity NPC476184
0.6552 Remote Similarity NPC476281
0.6541 Remote Similarity NPC301946
0.6541 Remote Similarity NPC313414
0.6541 Remote Similarity NPC469457
0.6541 Remote Similarity NPC473541
0.6541 Remote Similarity NPC277053
0.6538 Remote Similarity NPC472547
0.6538 Remote Similarity NPC469360
0.6538 Remote Similarity NPC91953
0.6533 Remote Similarity NPC93632
0.6533 Remote Similarity NPC69496
0.6525 Remote Similarity NPC473869
0.6524 Remote Similarity NPC207675
0.6524 Remote Similarity NPC212699
0.6522 Remote Similarity NPC472392
0.6522 Remote Similarity NPC476744
0.6522 Remote Similarity NPC472375
0.6516 Remote Similarity NPC39549
0.651 Remote Similarity NPC5486
0.6507 Remote Similarity NPC293831
0.6507 Remote Similarity NPC252878
0.6507 Remote Similarity NPC369
0.6507 Remote Similarity NPC474862
0.6503 Remote Similarity NPC473490
0.6503 Remote Similarity NPC476268
0.65 Remote Similarity NPC477246
0.65 Remote Similarity NPC477245
0.6494 Remote Similarity NPC6570
0.6494 Remote Similarity NPC68865
0.6489 Remote Similarity NPC25565
0.6486 Remote Similarity NPC472391
0.6486 Remote Similarity NPC471758
0.6486 Remote Similarity NPC474847
0.6484 Remote Similarity NPC316108
0.6483 Remote Similarity NPC476183
0.6481 Remote Similarity NPC122590
0.6478 Remote Similarity NPC471912
0.6478 Remote Similarity NPC80895
0.6477 Remote Similarity NPC474607
0.6467 Remote Similarity NPC259098

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC175870 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
0.8714 High Similarity NPD7274 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6325 Discontinued
0.705 Intermediate Similarity NPD2218 Phase 2
0.705 Intermediate Similarity NPD2217 Approved
0.6879 Remote Similarity NPD5981 Approved
0.6866 Remote Similarity NPD6406 Approved
0.686 Remote Similarity NPD5035 Approved
0.6857 Remote Similarity NPD7522 Discontinued
0.6838 Remote Similarity NPD3644 Approved
0.6838 Remote Similarity NPD3643 Approved
0.6838 Remote Similarity NPD3642 Approved
0.6824 Remote Similarity NPD4738 Phase 2
0.68 Remote Similarity NPD8265 Approved
0.6782 Remote Similarity NPD5036 Approved
0.6743 Remote Similarity NPD5037 Approved
0.6743 Remote Similarity NPD5038 Approved
0.6731 Remote Similarity NPD6676 Phase 2
0.6689 Remote Similarity NPD2238 Phase 2
0.6667 Remote Similarity NPD8361 Approved
0.6667 Remote Similarity NPD8360 Approved
0.6667 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4760 Clinical (unspecified phase)
0.6647 Remote Similarity NPD5030 Phase 2
0.663 Remote Similarity NPD8485 Approved
0.6629 Remote Similarity NPD8407 Phase 2
0.6624 Remote Similarity NPD2575 Approved
0.6624 Remote Similarity NPD3400 Discontinued
0.6621 Remote Similarity NPD5618 Discontinued
0.6609 Remote Similarity NPD5028 Approved
0.6609 Remote Similarity NPD5032 Approved
0.6609 Remote Similarity NPD4955 Approved
0.6609 Remote Similarity NPD5034 Approved
0.6609 Remote Similarity NPD4954 Approved
0.6609 Remote Similarity NPD5026 Approved
0.6609 Remote Similarity NPD36 Approved
0.6573 Remote Similarity NPD4479 Discontinued
0.6573 Remote Similarity NPD8435 Approved
0.6564 Remote Similarity NPD8417 Discontinued
0.6554 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6552 Remote Similarity NPD2956 Clinical (unspecified phase)
0.6552 Remote Similarity NPD8368 Discontinued
0.6552 Remote Similarity NPD5039 Approved
0.6538 Remote Similarity NPD4814 Discontinued
0.6533 Remote Similarity NPD2613 Approved
0.6532 Remote Similarity NPD4956 Approved
0.6522 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6493 Remote Similarity NPD4719 Phase 2
0.648 Remote Similarity NPD6836 Approved
0.6458 Remote Similarity NPD2227 Clinical (unspecified phase)
0.6457 Remote Similarity NPD5027 Approved
0.6457 Remote Similarity NPD5031 Approved
0.6457 Remote Similarity NPD5029 Approved
0.6447 Remote Similarity NPD4619 Approved
0.6447 Remote Similarity NPD4621 Approved
0.6443 Remote Similarity NPD2625 Approved
0.6443 Remote Similarity NPD2160 Approved
0.6443 Remote Similarity NPD2628 Approved
0.6443 Remote Similarity NPD2627 Approved
0.6443 Remote Similarity NPD2159 Approved
0.6443 Remote Similarity NPD2626 Approved
0.6434 Remote Similarity NPD3123 Discovery
0.6429 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6415 Remote Similarity NPD7488 Clinical (unspecified phase)
0.6408 Remote Similarity NPD1711 Phase 2
0.6405 Remote Similarity NPD2571 Approved
0.6405 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6405 Remote Similarity NPD3089 Approved
0.6405 Remote Similarity NPD2570 Approved
0.6405 Remote Similarity NPD3087 Approved
0.6405 Remote Similarity NPD4745 Approved
0.6405 Remote Similarity NPD7714 Approved
0.6405 Remote Similarity NPD2574 Discontinued
0.6405 Remote Similarity NPD2573 Approved
0.6405 Remote Similarity NPD2566 Approved
0.6405 Remote Similarity NPD7715 Approved
0.6405 Remote Similarity NPD3088 Approved
0.6405 Remote Similarity NPD3614 Approved
0.6405 Remote Similarity NPD3090 Approved
0.6405 Remote Similarity NPD3615 Approved
0.6405 Remote Similarity NPD3616 Approved
0.6405 Remote Similarity NPD4746 Phase 3
0.6395 Remote Similarity NPD3529 Phase 2
0.6395 Remote Similarity NPD4218 Approved
0.6395 Remote Similarity NPD4807 Approved
0.6395 Remote Similarity NPD4217 Approved
0.6395 Remote Similarity NPD4216 Approved
0.6395 Remote Similarity NPD3131 Approved
0.6395 Remote Similarity NPD4215 Approved
0.6395 Remote Similarity NPD2610 Approved
0.6395 Remote Similarity NPD2609 Approved
0.6395 Remote Similarity NPD2608 Approved
0.6395 Remote Similarity NPD3132 Approved
0.6395 Remote Similarity NPD4806 Approved
0.6395 Remote Similarity NPD2612 Approved
0.6395 Remote Similarity NPD2611 Approved
0.6387 Remote Similarity NPD8172 Phase 2
0.6387 Remote Similarity NPD8173 Phase 2
0.6382 Remote Similarity NPD3136 Phase 2
0.6375 Remote Similarity NPD8323 Discontinued
0.637 Remote Similarity NPD4818 Approved
0.637 Remote Similarity NPD7725 Approved
0.637 Remote Similarity NPD4817 Approved
0.637 Remote Similarity NPD5305 Approved
0.637 Remote Similarity NPD5306 Approved
0.6369 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6309 Approved
0.6364 Remote Similarity NPD6310 Approved
0.6364 Remote Similarity NPD6311 Approved
0.6358 Remote Similarity NPD5204 Approved
0.6357 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6351 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6333 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6333 Remote Similarity NPD4103 Phase 2
0.6329 Remote Similarity NPD7978 Discontinued
0.6329 Remote Similarity NPD2174 Clinical (unspecified phase)
0.6325 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6324 Remote Similarity NPD5765 Approved
0.6323 Remote Similarity NPD4686 Approved
0.6323 Remote Similarity NPD4685 Phase 3
0.6323 Remote Similarity NPD4684 Phase 3
0.6319 Remote Similarity NPD7613 Discontinued
0.6316 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4620 Approved
0.6316 Remote Similarity NPD5201 Approved
0.6316 Remote Similarity NPD5203 Approved
0.6316 Remote Similarity NPD4617 Approved
0.6309 Remote Similarity NPD5157 Phase 1
0.6309 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6309 Remote Similarity NPD5159 Phase 2
0.6304 Remote Similarity NPD6685 Approved
0.6301 Remote Similarity NPD1710 Approved
0.6299 Remote Similarity NPD5729 Clinical (unspecified phase)
0.6294 Remote Similarity NPD2629 Approved
0.6284 Remote Similarity NPD2173 Clinical (unspecified phase)
0.6282 Remote Similarity NPD2568 Approved
0.6277 Remote Similarity NPD179 Clinical (unspecified phase)
0.6264 Remote Similarity NPD5033 Approved
0.626 Remote Similarity NPD6690 Approved
0.6259 Remote Similarity NPD4095 Clinical (unspecified phase)
0.6259 Remote Similarity NPD6038 Clinical (unspecified phase)
0.6258 Remote Similarity NPD5119 Approved
0.6258 Remote Similarity NPD5121 Approved
0.6258 Remote Similarity NPD5120 Approved
0.625 Remote Similarity NPD3661 Approved
0.625 Remote Similarity NPD3662 Phase 3
0.625 Remote Similarity NPD7972 Discontinued
0.625 Remote Similarity NPD3663 Approved
0.625 Remote Similarity NPD7084 Phase 3
0.625 Remote Similarity NPD3626 Phase 3
0.625 Remote Similarity NPD7508 Discontinued
0.625 Remote Similarity NPD3664 Approved
0.6242 Remote Similarity NPD3554 Approved
0.6242 Remote Similarity NPD3555 Approved
0.6242 Remote Similarity NPD3553 Approved
0.6242 Remote Similarity NPD6852 Discontinued
0.6242 Remote Similarity NPD3552 Approved
0.6234 Remote Similarity NPD7908 Discontinued
0.6233 Remote Similarity NPD7741 Discontinued
0.6232 Remote Similarity NPD999 Phase 2
0.6232 Remote Similarity NPD5717 Approved
0.623 Remote Similarity NPD5968 Phase 3
0.6228 Remote Similarity NPD6072 Discontinued
0.6224 Remote Similarity NPD2234 Approved
0.6224 Remote Similarity NPD2228 Approved
0.6224 Remote Similarity NPD2229 Approved
0.622 Remote Similarity NPD52 Approved
0.622 Remote Similarity NPD7527 Clinical (unspecified phase)
0.622 Remote Similarity NPD7526 Approved
0.6218 Remote Similarity NPD7113 Clinical (unspecified phase)
0.6216 Remote Similarity NPD4135 Approved
0.6216 Remote Similarity NPD4106 Approved
0.6216 Remote Similarity NPD4136 Approved
0.6207 Remote Similarity NPD6775 Clinical (unspecified phase)
0.6205 Remote Similarity NPD4005 Discontinued
0.6204 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6204 Remote Similarity NPD3680 Approved
0.6204 Remote Similarity NPD3682 Approved
0.62 Remote Similarity NPD9622 Approved
0.62 Remote Similarity NPD4659 Approved
0.6194 Remote Similarity NPD2487 Clinical (unspecified phase)
0.619 Remote Similarity NPD4209 Clinical (unspecified phase)
0.6187 Remote Similarity NPD5704 Approved
0.6187 Remote Similarity NPD5705 Approved
0.6187 Remote Similarity NPD5706 Approved
0.6185 Remote Similarity NPD7315 Approved
0.6183 Remote Similarity NPD7282 Approved
0.6174 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6174 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6173 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6164 Remote Similarity NPD9570 Approved
0.6164 Remote Similarity NPD6360 Discontinued
0.6164 Remote Similarity NPD2161 Phase 2
0.6163 Remote Similarity NPD4666 Phase 3
0.6163 Remote Similarity NPD6746 Phase 2
0.6159 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6158 Remote Similarity NPD5190 Phase 2
0.6154 Remote Similarity NPD5772 Approved
0.6154 Remote Similarity NPD5773 Approved
0.6149 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6138 Remote Similarity NPD2493 Approved

Structure

External Identifiers

PubChem CID   24970396
ChEMBL   CHEMBL472313
ZINC  

Physicochemical Properties

Molecular Weight:  427.24
ALogP:  -1.4094
MLogP:  3.55
XLogP:  3.691
# Rotatable Bonds:  14
Polar Surface Area:  110.35
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  31

Download Data

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