Natural Product: NPC471339

Natural Product ID:  NPC471339
Common Name:   Psammaplysine X
IUPAC Name:   (4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[2-[[(Z)-(3-chloro-2,5-dioxocyclopentylidene)methyl]amino]ethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:  
Molecular Formula:   C27H26Br4ClN3O8
Standard InCHIKey:  YNMCLVMISHJRBL-YJGHPRERSA-N
Standard InCHI:  InChI=1S/C27H26Br4ClN3O8/c1-40-23-17(30)10-27(42-12-18(23)31)25(38)21(35-43-27)26(39)34-4-2-6-41-24-15(28)7-13(8-16(24)29)3-5-33-11-14-20(36)9-19(32)22(14)37/h7-8,11-12,19,25,33,38H,2-6,9-10H2,1H3,(H,34,39)/b14-11-/t19?,25-,27-/m0/s1
Canonical SMILES:  COC1=C(Br)C[C@]2(OC=C1Br)ON=C([C@@H]2O)C(=O)NCCCOc1c(Br)cc(cc1Br)CCN/C=C1/C(=O)CC(C1=O)Cl
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
NPO32567 suberea sp. Species Aplysinellidae Eukaryota PMID[23964644]

  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 GI50 = 1200 nM 19453174
NPT2477 Cell Line NUGC-3 Homo sapiens GI50 = 3500 nM 25953722
NPT369 Cell Line ACHN Homo sapiens GI50 = 3300 nM 21074429
NPT370 Cell Line NCI-H23 Homo sapiens GI50 = 6400 nM 9917297
NPT148 Cell Line HCT-15 Homo sapiens GI50 = 3300 nM 15568791
NPT306 Cell Line PC-3 Homo sapiens GI50 = 2300 nM DrugMatrix in vitro pharmacology data

  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 NPC471339 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
0.9634 High Similarity NPC471335
0.9305 High Similarity NPC123140
0.8969 High Similarity NPC471336
0.8969 High Similarity NPC470746
0.8967 High Similarity NPC8093
0.8967 High Similarity NPC121571
0.8684 High Similarity NPC474678
0.8684 High Similarity NPC471338
0.8639 High Similarity NPC475843
0.8513 High Similarity NPC471337
0.837 Intermediate Similarity NPC477255
0.8177 Intermediate Similarity NPC259071
0.8177 Intermediate Similarity NPC77435
0.8168 Intermediate Similarity NPC477254
0.8071 Intermediate Similarity NPC202866
0.7929 Intermediate Similarity NPC227953
0.7766 Intermediate Similarity NPC174607
0.7727 Intermediate Similarity NPC147847
0.7173 Intermediate Similarity NPC156311
0.6927 Remote Similarity NPC469711
0.6882 Remote Similarity NPC128877
0.6875 Remote Similarity NPC258222
0.6862 Remote Similarity NPC308571
0.6847 Remote Similarity NPC143450
0.6753 Remote Similarity NPC47672
0.6736 Remote Similarity NPC76412
0.6735 Remote Similarity NPC233926
0.6719 Remote Similarity NPC71629
0.6701 Remote Similarity NPC109968
0.6651 Remote Similarity NPC248822
0.6632 Remote Similarity NPC296085
0.6562 Remote Similarity NPC78530
0.6504 Remote Similarity NPC326027
0.6489 Remote Similarity NPC326333
0.6484 Remote Similarity NPC473450
0.6477 Remote Similarity NPC135349
0.6474 Remote Similarity NPC474673
0.6455 Remote Similarity NPC470471
0.6422 Remote Similarity NPC209463
0.6402 Remote Similarity NPC246591
0.6392 Remote Similarity NPC470472
0.6387 Remote Similarity NPC470470
0.6373 Remote Similarity NPC474128
0.6359 Remote Similarity NPC473693
0.6359 Remote Similarity NPC272463
0.6359 Remote Similarity NPC471568
0.6351 Remote Similarity NPC475396
0.633 Remote Similarity NPC80514
0.6324 Remote Similarity NPC110131
0.6318 Remote Similarity NPC323662
0.6313 Remote Similarity NPC102245
0.628 Remote Similarity NPC196091
0.6279 Remote Similarity NPC471591
0.6279 Remote Similarity NPC475658
0.6279 Remote Similarity NPC473892
0.6262 Remote Similarity NPC299806
0.625 Remote Similarity NPC82741
0.625 Remote Similarity NPC141405
0.625 Remote Similarity NPC473409
0.6244 Remote Similarity NPC301941
0.6244 Remote Similarity NPC214188
0.6244 Remote Similarity NPC74618
0.6239 Remote Similarity NPC64066
0.6232 Remote Similarity NPC186617
0.6211 Remote Similarity NPC247018
0.6211 Remote Similarity NPC307123
0.6211 Remote Similarity NPC97870
0.621 Remote Similarity NPC65714
0.621 Remote Similarity NPC328763
0.6209 Remote Similarity NPC469979
0.6209 Remote Similarity NPC226001
0.6204 Remote Similarity NPC96275
0.6199 Remote Similarity NPC469731
0.6179 Remote Similarity NPC207819
0.6179 Remote Similarity NPC298981
0.6179 Remote Similarity NPC473462
0.6179 Remote Similarity NPC126128
0.6179 Remote Similarity NPC110454
0.6157 Remote Similarity NPC49172
0.615 Remote Similarity NPC81845
0.615 Remote Similarity NPC290534
0.6135 Remote Similarity NPC469479
0.6134 Remote Similarity NPC213471
0.613 Remote Similarity NPC92235
0.6129 Remote Similarity NPC144823
0.6126 Remote Similarity NPC471592
0.6109 Remote Similarity NPC469721
0.61 Remote Similarity NPC324081
0.6094 Remote Similarity NPC67658
0.6087 Remote Similarity NPC295795
0.6085 Remote Similarity NPC225130
0.6073 Remote Similarity NPC230539
0.6073 Remote Similarity NPC283207
0.6059 Remote Similarity NPC235033
0.6059 Remote Similarity NPC471235
0.6059 Remote Similarity NPC73132
0.6055 Remote Similarity NPC80337
0.6041 Remote Similarity NPC204546
0.6028 Remote Similarity NPC475421
0.602 Remote Similarity NPC20755
0.6019 Remote Similarity NPC167763
0.6019 Remote Similarity NPC470112
0.6019 Remote Similarity NPC470903
0.6018 Remote Similarity NPC214368
0.601 Remote Similarity NPC132308
0.6009 Remote Similarity NPC14339
0.6008 Remote Similarity NPC243633
0.6008 Remote Similarity NPC175150
0.6 Remote Similarity NPC469505
0.5981 Remote Similarity NPC254700
0.598 Remote Similarity NPC470710
0.5979 Remote Similarity NPC470441
0.5979 Remote Similarity NPC303993
0.5963 Remote Similarity NPC315542
0.5959 Remote Similarity NPC474753
0.5957 Remote Similarity NPC219350
0.5957 Remote Similarity NPC194699
0.5953 Remote Similarity NPC475615
0.5949 Remote Similarity NPC196708
0.5939 Remote Similarity NPC40321
0.5938 Remote Similarity NPC474087
0.5936 Remote Similarity NPC276120
0.5933 Remote Similarity NPC158900
0.5933 Remote Similarity NPC472923
0.5928 Remote Similarity NPC169766
0.5922 Remote Similarity NPC56635
0.5907 Remote Similarity NPC473724
0.5907 Remote Similarity NPC475735
0.5902 Remote Similarity NPC256689
0.5902 Remote Similarity NPC123011
0.5895 Remote Similarity NPC320242
0.5885 Remote Similarity NPC67080
0.5882 Remote Similarity NPC124626
0.5876 Remote Similarity NPC470392
0.5859 Remote Similarity NPC123859
0.5855 Remote Similarity NPC277306
0.5855 Remote Similarity NPC469442
0.5855 Remote Similarity NPC474091
0.5847 Remote Similarity NPC50562
0.5833 Remote Similarity NPC242728
0.5829 Remote Similarity NPC71205
0.5829 Remote Similarity NPC470709
0.582 Remote Similarity NPC116562
0.5818 Remote Similarity NPC138083
0.5815 Remote Similarity NPC477550
0.5815 Remote Similarity NPC477552
0.5811 Remote Similarity NPC470951
0.5808 Remote Similarity NPC197045
0.5805 Remote Similarity NPC25539
0.5802 Remote Similarity NPC473502
0.5794 Remote Similarity NPC89831
0.5792 Remote Similarity NPC119569
0.5785 Remote Similarity NPC223384
0.5782 Remote Similarity NPC63931
0.5782 Remote Similarity NPC293164
0.5782 Remote Similarity NPC471394
0.5773 Remote Similarity NPC99280
0.5767 Remote Similarity NPC248670
0.5765 Remote Similarity NPC163810
0.5764 Remote Similarity NPC477551
0.5758 Remote Similarity NPC106606
0.5758 Remote Similarity NPC307682
0.5753 Remote Similarity NPC28368
0.575 Remote Similarity NPC81137
0.5747 Remote Similarity NPC128683
0.5744 Remote Similarity NPC11449
0.5743 Remote Similarity NPC147137
0.5743 Remote Similarity NPC473804
0.5742 Remote Similarity NPC319320
0.5742 Remote Similarity NPC287757
0.5741 Remote Similarity NPC164608
0.5741 Remote Similarity NPC471165
0.574 Remote Similarity NPC471650
0.5739 Remote Similarity NPC156055
0.5735 Remote Similarity NPC132771
0.5729 Remote Similarity NPC141739
0.5729 Remote Similarity NPC471237
0.5729 Remote Similarity NPC177967
0.5729 Remote Similarity NPC136112
0.5727 Remote Similarity NPC475283
0.5727 Remote Similarity NPC152205
0.5727 Remote Similarity NPC149962
0.5714 Remote Similarity NPC471203
0.5708 Remote Similarity NPC32064
0.5707 Remote Similarity NPC235633
0.5702 Remote Similarity NPC144314
0.5702 Remote Similarity NPC293347
0.5702 Remote Similarity NPC281629
0.57 Remote Similarity NPC39431
0.5695 Remote Similarity NPC4910
0.5695 Remote Similarity NPC94862
0.5694 Remote Similarity NPC90245
0.5689 Remote Similarity NPC473378
0.5689 Remote Similarity NPC473407
0.5686 Remote Similarity NPC272868
0.5686 Remote Similarity NPC270848
0.5686 Remote Similarity NPC122599
0.5685 Remote Similarity NPC168209
0.5684 Remote Similarity NPC79130
0.5678 Remote Similarity NPC470249

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471339 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
0.6313 Remote Similarity NPD5165 Clinical (unspecified phase)
0.6274 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6269 Remote Similarity NPD2240 Approved
0.6269 Remote Similarity NPD2239 Approved
0.6238 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6233 Remote Similarity NPD3154 Approved
0.6233 Remote Similarity NPD3153 Approved
0.6211 Remote Similarity NPD1423 Approved
0.6202 Remote Similarity NPD7608 Discontinued
0.6193 Remote Similarity NPD5525 Clinical (unspecified phase)
0.619 Remote Similarity NPD3366 Approved
0.6162 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6098 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6049 Remote Similarity NPD4018 Clinical (unspecified phase)
0.602 Remote Similarity NPD3175 Clinical (unspecified phase)
0.602 Remote Similarity NPD4662 Approved
0.602 Remote Similarity NPD4661 Approved
0.601 Remote Similarity NPD8031 Discontinued
0.601 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6 Remote Similarity NPD2541 Clinical (unspecified phase)
0.5991 Remote Similarity NPD6863 Phase 2
0.5982 Remote Similarity NPD3863 Clinical (unspecified phase)
0.5982 Remote Similarity NPD3857 Clinical (unspecified phase)
0.5942 Remote Similarity NPD7972 Discontinued
0.5941 Remote Similarity NPD3536 Discontinued
0.5924 Remote Similarity NPD7484 Phase 3
0.5924 Remote Similarity NPD7485 Phase 3
0.5913 Remote Similarity NPD7318 Phase 3
0.5909 Remote Similarity NPD8059 Phase 3
0.5909 Remote Similarity NPD8058 Clinical (unspecified phase)
0.5905 Remote Similarity NPD6315 Phase 2
0.5902 Remote Similarity NPD2651 Approved
0.5902 Remote Similarity NPD2649 Approved
0.5895 Remote Similarity NPD1819 Approved
0.5895 Remote Similarity NPD1818 Approved
0.5895 Remote Similarity NPD1817 Approved
0.5895 Remote Similarity NPD1770 Clinical (unspecified phase)
0.5895 Remote Similarity NPD1820 Approved
0.5882 Remote Similarity NPD7131 Phase 3
0.5872 Remote Similarity NPD3936 Clinical (unspecified phase)
0.5862 Remote Similarity NPD5348 Clinical (unspecified phase)
0.5859 Remote Similarity NPD1725 Approved
0.5856 Remote Similarity NPD4259 Approved
0.5856 Remote Similarity NPD4258 Approved
0.5855 Remote Similarity NPD3164 Approved
0.5855 Remote Similarity NPD3180 Approved
0.5855 Remote Similarity NPD3165 Approved
0.5855 Remote Similarity NPD3166 Approved
0.5855 Remote Similarity NPD3179 Approved
0.5855 Remote Similarity NPD9718 Approved
0.5855 Remote Similarity NPD3167 Approved
0.5848 Remote Similarity NPD4466 Phase 1
0.5845 Remote Similarity NPD6677 Suspended
0.5826 Remote Similarity NPD1298 Discontinued
0.5817 Remote Similarity NPD7317 Phase 3
0.5806 Remote Similarity NPD2325 Approved
0.5805 Remote Similarity NPD5586 Clinical (unspecified phase)
0.5795 Remote Similarity NPD3162 Approved
0.5795 Remote Similarity NPD3163 Approved
0.5787 Remote Similarity NPD6620 Discovery
0.5785 Remote Similarity NPD6377 Clinical (unspecified phase)
0.5784 Remote Similarity NPD3985 Discontinued
0.5779 Remote Similarity NPD2161 Phase 2
0.5773 Remote Similarity NPD5163 Phase 2
0.5771 Remote Similarity NPD4162 Approved
0.5767 Remote Similarity NPD4575 Clinical (unspecified phase)
0.5767 Remote Similarity NPD3451 Clinical (unspecified phase)
0.5762 Remote Similarity NPD2296 Approved
0.5756 Remote Similarity NPD1975 Clinical (unspecified phase)
0.5752 Remote Similarity NPD4413 Clinical (unspecified phase)
0.5752 Remote Similarity NPD7256 Discontinued
0.575 Remote Similarity NPD3656 Approved
0.5749 Remote Similarity NPD3769 Discontinued
0.5742 Remote Similarity NPD5355 Approved
0.5742 Remote Similarity NPD5356 Approved
0.5741 Remote Similarity NPD5605 Phase 2
0.5729 Remote Similarity NPD1794 Approved
0.5728 Remote Similarity NPD2042 Clinical (unspecified phase)
0.5728 Remote Similarity NPD2041 Clinical (unspecified phase)
0.5727 Remote Similarity NPD7880 Clinical (unspecified phase)
0.5721 Remote Similarity NPD2388 Discontinued
0.5721 Remote Similarity NPD7596 Clinical (unspecified phase)
0.5721 Remote Similarity NPD7565 Approved
0.5714 Remote Similarity NPD1726 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5910 Clinical (unspecified phase)
0.5708 Remote Similarity NPD1309 Phase 2
0.5708 Remote Similarity NPD1307 Phase 2
0.5707 Remote Similarity NPD6419 Discontinued
0.5707 Remote Similarity NPD3054 Approved
0.5707 Remote Similarity NPD3052 Approved
0.57 Remote Similarity NPD3687 Approved
0.57 Remote Similarity NPD5712 Approved
0.57 Remote Similarity NPD3686 Approved
0.57 Remote Similarity NPD4124 Clinical (unspecified phase)
0.5694 Remote Similarity NPD7118 Clinical (unspecified phase)
0.5693 Remote Similarity NPD2460 Phase 3
0.5693 Remote Similarity NPD2458 Approved
0.5693 Remote Similarity NPD2459 Approved
0.5688 Remote Similarity NPD5095 Phase 3
0.5688 Remote Similarity NPD5096 Phase 3
0.5688 Remote Similarity NPD3933 Discontinued
0.5684 Remote Similarity NPD7584 Approved
0.5682 Remote Similarity NPD7038 Approved
0.5682 Remote Similarity NPD7039 Approved
0.5681 Remote Similarity NPD6862 Phase 2
0.568 Remote Similarity NPD7527 Clinical (unspecified phase)
0.568 Remote Similarity NPD52 Approved
0.568 Remote Similarity NPD7526 Approved
0.568 Remote Similarity NPD4186 Clinical (unspecified phase)
0.567 Remote Similarity NPD2250 Discontinued
0.5664 Remote Similarity NPD3269 Clinical (unspecified phase)
0.5663 Remote Similarity NPD3056 Clinical (unspecified phase)
0.5662 Remote Similarity NPD5557 Phase 1
0.5654 Remote Similarity NPD2904 Discontinued
0.5652 Remote Similarity NPD7810 Phase 3
0.5652 Remote Similarity NPD7811 Phase 3
0.5644 Remote Similarity NPD7153 Discontinued
0.5635 Remote Similarity NPD5745 Approved
0.5635 Remote Similarity NPD2245 Discovery
0.5631 Remote Similarity NPD2874 Phase 2
0.5628 Remote Similarity NPD6519 Phase 2
0.5625 Remote Similarity NPD6793 Clinical (unspecified phase)
0.5625 Remote Similarity NPD8398 Clinical (unspecified phase)
0.5616 Remote Similarity NPD1416 Approved
0.561 Remote Similarity NPD5295 Discontinued
0.5606 Remote Similarity NPD3597 Clinical (unspecified phase)
0.5605 Remote Similarity NPD6853 Approved
0.5605 Remote Similarity NPD6851 Approved
0.5604 Remote Similarity NPD2186 Approved
0.5604 Remote Similarity NPD6390 Discontinued
0.5603 Remote Similarity NPD7476 Discontinued
0.56 Remote Similarity NPD7693 Approved
0.56 Remote Similarity NPD3490 Discontinued

Structure

External Identifiers

PubChem CID   73349161
ChEMBL   CHEMBL2419320
ZINC  

Physicochemical Properties

Molecular Weight:  870.81
ALogP:  0.4821
MLogP:  2.67
XLogP:  6.093
# Rotatable Bonds:  19
Polar Surface Area:  144.78
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  43

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs