Natural Product: NPC471335

Natural Product ID:  NPC471335
Common Name:   19-Hydroxypsammaplysine X
IUPAC Name:   (4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[2-[[(Z)-(3-chloro-2,5-dioxocyclopentylidene)methyl]amino]-1-hydroxyethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:  
Molecular Formula:   C27H26Br4ClN3O9
Standard InCHIKey:  FGYQWPOMHRREQY-ILXFYYIXSA-N
Standard InCHI:  InChI=1S/C27H26Br4ClN3O9/c1-41-23-16(30)8-27(43-11-17(23)31)25(39)21(35-44-27)26(40)34-3-2-4-42-24-14(28)5-12(6-15(24)29)20(37)10-33-9-13-19(36)7-18(32)22(13)38/h5-6,9,11,18,20,25,33,37,39H,2-4,7-8,10H2,1H3,(H,34,40)/b13-9-/t18?,20?,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)C(CN/C=C1/C(=O)CC(C1=O)Cl)O
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
NPT2477 Cell Line NUGC-3 Homo sapiens GI50 = 4000 nM 8423591
NPT369 Cell Line ACHN Homo sapiens GI50 = 2500 nM 21074429
NPT370 Cell Line NCI-H23 Homo sapiens GI50 = 3500 nM 9392875
NPT148 Cell Line HCT-15 Homo sapiens GI50 = 3500 nM 15568791
NPT306 Cell Line PC-3 Homo sapiens GI50 = 2100 nM DrugMatrix in vitro pharmacology data
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 = 800 nM Open TG-GATES in vivo data: Hematology

  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 NPC471335 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 NPC471339
0.933 High Similarity NPC471336
0.933 High Similarity NPC470746
0.9005 High Similarity NPC475843
0.8969 High Similarity NPC123140
0.8953 High Similarity NPC471338
0.8953 High Similarity NPC474678
0.8776 High Similarity NPC471337
0.8639 High Similarity NPC121571
0.8639 High Similarity NPC8093
0.8063 Intermediate Similarity NPC477255
0.798 Intermediate Similarity NPC77435
0.798 Intermediate Similarity NPC259071
0.7882 Intermediate Similarity NPC202866
0.7879 Intermediate Similarity NPC477254
0.7833 Intermediate Similarity NPC227953
0.7586 Intermediate Similarity NPC174607
0.7549 Intermediate Similarity NPC147847
0.7202 Intermediate Similarity NPC469711
0.7005 Intermediate Similarity NPC156311
0.6814 Remote Similarity NPC326027
0.68 Remote Similarity NPC326333
0.6754 Remote Similarity NPC474673
0.675 Remote Similarity NPC233926
0.6717 Remote Similarity NPC258222
0.6699 Remote Similarity NPC143450
0.6683 Remote Similarity NPC47672
0.6667 Remote Similarity NPC248822
0.6636 Remote Similarity NPC323662
0.6632 Remote Similarity NPC128877
0.6615 Remote Similarity NPC308571
0.6583 Remote Similarity NPC76412
0.6577 Remote Similarity NPC473450
0.655 Remote Similarity NPC109968
0.653 Remote Similarity NPC328763
0.6528 Remote Similarity NPC475658
0.6528 Remote Similarity NPC473892
0.6522 Remote Similarity NPC209463
0.6498 Remote Similarity NPC82741
0.6498 Remote Similarity NPC246591
0.6498 Remote Similarity NPC473409
0.6498 Remote Similarity NPC141405
0.6482 Remote Similarity NPC71629
0.6452 Remote Similarity NPC471591
0.6435 Remote Similarity NPC92235
0.6425 Remote Similarity NPC80514
0.6414 Remote Similarity NPC78530
0.6409 Remote Similarity NPC102245
0.6406 Remote Similarity NPC49172
0.64 Remote Similarity NPC296085
0.6381 Remote Similarity NPC471568
0.6381 Remote Similarity NPC473693
0.6368 Remote Similarity NPC469731
0.6351 Remote Similarity NPC469721
0.6335 Remote Similarity NPC64066
0.6332 Remote Similarity NPC135349
0.6327 Remote Similarity NPC214368
0.6316 Remote Similarity NPC469479
0.6313 Remote Similarity NPC474128
0.6308 Remote Similarity NPC470471
0.6306 Remote Similarity NPC65714
0.6303 Remote Similarity NPC196091
0.6301 Remote Similarity NPC96275
0.6284 Remote Similarity NPC299806
0.6256 Remote Similarity NPC186617
0.625 Remote Similarity NPC470472
0.6245 Remote Similarity NPC81845
0.6244 Remote Similarity NPC235033
0.6244 Remote Similarity NPC470470
0.6244 Remote Similarity NPC471235
0.6244 Remote Similarity NPC283207
0.6244 Remote Similarity NPC73132
0.6237 Remote Similarity NPC247018
0.6237 Remote Similarity NPC307123
0.6237 Remote Similarity NPC97870
0.6222 Remote Similarity NPC471592
0.6221 Remote Similarity NPC475396
0.6193 Remote Similarity NPC74618
0.6193 Remote Similarity NPC301941
0.6193 Remote Similarity NPC214188
0.618 Remote Similarity NPC295795
0.6179 Remote Similarity NPC469505
0.6171 Remote Similarity NPC230539
0.6157 Remote Similarity NPC469979
0.6157 Remote Similarity NPC226001
0.6154 Remote Similarity NPC80337
0.6129 Remote Similarity NPC298981
0.6129 Remote Similarity NPC207819
0.6129 Remote Similarity NPC110454
0.6129 Remote Similarity NPC473462
0.6129 Remote Similarity NPC126128
0.6127 Remote Similarity NPC324081
0.6126 Remote Similarity NPC272463
0.6123 Remote Similarity NPC477550
0.6123 Remote Similarity NPC477552
0.6101 Remote Similarity NPC290534
0.6096 Remote Similarity NPC123859
0.6094 Remote Similarity NPC110131
0.6081 Remote Similarity NPC144823
0.607 Remote Similarity NPC242728
0.607 Remote Similarity NPC204546
0.607 Remote Similarity NPC477551
0.6063 Remote Similarity NPC315542
0.6055 Remote Similarity NPC475421
0.6045 Remote Similarity NPC167763
0.6045 Remote Similarity NPC470903
0.6045 Remote Similarity NPC470112
0.6038 Remote Similarity NPC158900
0.6037 Remote Similarity NPC225130
0.6036 Remote Similarity NPC276120
0.6009 Remote Similarity NPC144314
0.6009 Remote Similarity NPC254700
0.6 Remote Similarity NPC213471
0.5991 Remote Similarity NPC471165
0.5983 Remote Similarity NPC50548
0.5983 Remote Similarity NPC219350
0.5983 Remote Similarity NPC194699
0.5971 Remote Similarity NPC20755
0.597 Remote Similarity NPC40321
0.5965 Remote Similarity NPC149962
0.5962 Remote Similarity NPC472923
0.5956 Remote Similarity NPC223384
0.5952 Remote Similarity NPC56635
0.5948 Remote Similarity NPC311357
0.5933 Remote Similarity NPC123011
0.5933 Remote Similarity NPC256689
0.5933 Remote Similarity NPC470710
0.5931 Remote Similarity NPC476661
0.5929 Remote Similarity NPC477526
0.5928 Remote Similarity NPC320242
0.5921 Remote Similarity NPC59827
0.5921 Remote Similarity NPC184933
0.5919 Remote Similarity NPC138083
0.5917 Remote Similarity NPC67658
0.5909 Remote Similarity NPC474753
0.5907 Remote Similarity NPC197125
0.5905 Remote Similarity NPC476662
0.5905 Remote Similarity NPC156055
0.5899 Remote Similarity NPC328494
0.5899 Remote Similarity NPC89831
0.5897 Remote Similarity NPC14339
0.5896 Remote Similarity NPC476194
0.5896 Remote Similarity NPC471203
0.5888 Remote Similarity NPC63931
0.5882 Remote Similarity NPC277306
0.5882 Remote Similarity NPC469442
0.5872 Remote Similarity NPC248670
0.587 Remote Similarity NPC281629
0.5865 Remote Similarity NPC293347
0.5865 Remote Similarity NPC477160
0.5862 Remote Similarity NPC470709
0.5859 Remote Similarity NPC475735
0.5859 Remote Similarity NPC473724
0.585 Remote Similarity NPC303993
0.585 Remote Similarity NPC470441
0.5847 Remote Similarity NPC79130
0.5844 Remote Similarity NPC477527
0.5841 Remote Similarity NPC471395
0.5841 Remote Similarity NPC124626
0.5837 Remote Similarity NPC175150
0.5837 Remote Similarity NPC243633
0.5837 Remote Similarity NPC475615
0.5833 Remote Similarity NPC25539
0.5833 Remote Similarity NPC473502
0.5829 Remote Similarity NPC470392
0.5826 Remote Similarity NPC308709
0.5818 Remote Similarity NPC477115
0.5815 Remote Similarity NPC29531
0.5811 Remote Similarity NPC32064
0.581 Remote Similarity NPC39431
0.5808 Remote Similarity NPC474091
0.5808 Remote Similarity NPC474087
0.5802 Remote Similarity NPC185172
0.58 Remote Similarity NPC169766
0.58 Remote Similarity NPC132308
0.5799 Remote Similarity NPC273755
0.5797 Remote Similarity NPC313414
0.5796 Remote Similarity NPC94862
0.5796 Remote Similarity NPC34780
0.5794 Remote Similarity NPC471031
0.5794 Remote Similarity NPC469689
0.5792 Remote Similarity NPC473052
0.5792 Remote Similarity NPC477665
0.5792 Remote Similarity NPC473055
0.5789 Remote Similarity NPC473378
0.5789 Remote Similarity NPC473407
0.5787 Remote Similarity NPC71205
0.5783 Remote Similarity NPC322424
0.5782 Remote Similarity NPC476268
0.5782 Remote Similarity NPC244509
0.578 Remote Similarity NPC46009
0.5778 Remote Similarity NPC235194
0.5778 Remote Similarity NPC128683
0.5778 Remote Similarity NPC206061
0.5775 Remote Similarity NPC287757
0.5775 Remote Similarity NPC319320
0.5774 Remote Similarity NPC14390
0.5773 Remote Similarity NPC164608
0.5773 Remote Similarity NPC26108
0.5771 Remote Similarity NPC470951

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471335 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
0.6372 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6294 Remote Similarity NPD2239 Approved
0.6294 Remote Similarity NPD2240 Approved
0.6261 Remote Similarity NPD5165 Clinical (unspecified phase)
0.6256 Remote Similarity NPD3153 Approved
0.6256 Remote Similarity NPD3154 Approved
0.6237 Remote Similarity NPD1423 Approved
0.6207 Remote Similarity NPD3536 Discontinued
0.6202 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4018 Clinical (unspecified phase)
0.615 Remote Similarity NPD7608 Discontinued
0.6134 Remote Similarity NPD3180 Approved
0.6134 Remote Similarity NPD3179 Approved
0.6132 Remote Similarity NPD8059 Phase 3
0.6132 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6119 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6108 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6106 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6093 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6863 Phase 2
0.6081 Remote Similarity NPD3857 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6049 Remote Similarity NPD4661 Approved
0.6049 Remote Similarity NPD4662 Approved
0.6039 Remote Similarity NPD3686 Approved
0.6039 Remote Similarity NPD3687 Approved
0.6038 Remote Similarity NPD8031 Discontinued
0.6037 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6019 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6018 Remote Similarity NPD4466 Phase 1
0.6009 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6 Remote Similarity NPD7039 Approved
0.6 Remote Similarity NPD7038 Approved
0.5991 Remote Similarity NPD3366 Approved
0.599 Remote Similarity NPD7131 Phase 3
0.598 Remote Similarity NPD3054 Approved
0.598 Remote Similarity NPD3052 Approved
0.5973 Remote Similarity NPD3936 Clinical (unspecified phase)
0.5972 Remote Similarity NPD7972 Discontinued
0.597 Remote Similarity NPD3175 Clinical (unspecified phase)
0.5957 Remote Similarity NPD7811 Phase 3
0.5957 Remote Similarity NPD7810 Phase 3
0.5953 Remote Similarity NPD7485 Phase 3
0.5953 Remote Similarity NPD7484 Phase 3
0.5943 Remote Similarity NPD7318 Phase 3
0.5935 Remote Similarity NPD6315 Phase 2
0.5933 Remote Similarity NPD2649 Approved
0.5933 Remote Similarity NPD2651 Approved
0.5928 Remote Similarity NPD1817 Approved
0.5928 Remote Similarity NPD1820 Approved
0.5928 Remote Similarity NPD1819 Approved
0.5928 Remote Similarity NPD1298 Discontinued
0.5928 Remote Similarity NPD1818 Approved
0.5921 Remote Similarity NPD7256 Discontinued
0.5898 Remote Similarity NPD8398 Clinical (unspecified phase)
0.5894 Remote Similarity NPD3985 Discontinued
0.5888 Remote Similarity NPD9718 Approved
0.5888 Remote Similarity NPD3165 Approved
0.5888 Remote Similarity NPD3164 Approved
0.5888 Remote Similarity NPD3167 Approved
0.5888 Remote Similarity NPD3166 Approved
0.5885 Remote Similarity NPD4258 Approved
0.5885 Remote Similarity NPD4259 Approved
0.5877 Remote Similarity NPD6677 Suspended
0.5877 Remote Similarity NPD6072 Discontinued
0.5857 Remote Similarity NPD3769 Discontinued
0.5849 Remote Similarity NPD7317 Phase 3
0.5847 Remote Similarity NPD7584 Approved
0.5837 Remote Similarity NPD7476 Discontinued
0.5833 Remote Similarity NPD4666 Phase 3
0.5829 Remote Similarity NPD3163 Approved
0.5829 Remote Similarity NPD3162 Approved
0.5826 Remote Similarity NPD2215 Approved
0.5826 Remote Similarity NPD2216 Approved
0.5825 Remote Similarity NPD2677 Approved
0.5822 Remote Similarity NPD5772 Approved
0.5822 Remote Similarity NPD5773 Approved
0.5819 Remote Similarity NPD7565 Approved
0.5818 Remote Similarity NPD2163 Approved
0.5818 Remote Similarity NPD6620 Discovery
0.5817 Remote Similarity NPD3158 Phase 1
0.5817 Remote Similarity NPD5348 Clinical (unspecified phase)
0.5817 Remote Similarity NPD3157 Approved
0.5815 Remote Similarity NPD6377 Clinical (unspecified phase)
0.5813 Remote Similarity NPD1725 Approved
0.5805 Remote Similarity NPD4162 Approved
0.5802 Remote Similarity NPD7118 Clinical (unspecified phase)
0.5792 Remote Similarity NPD3933 Discontinued
0.5792 Remote Similarity NPD5095 Phase 3
0.5792 Remote Similarity NPD5096 Phase 3
0.5789 Remote Similarity NPD1975 Clinical (unspecified phase)
0.5787 Remote Similarity NPD5709 Phase 3
0.5779 Remote Similarity NPD3056 Clinical (unspecified phase)
0.5766 Remote Similarity NPD5557 Phase 1
0.5765 Remote Similarity NPD1794 Approved
0.5765 Remote Similarity NPD1770 Clinical (unspecified phase)
0.576 Remote Similarity NPD2041 Clinical (unspecified phase)
0.576 Remote Similarity NPD2042 Clinical (unspecified phase)
0.5758 Remote Similarity NPD7880 Clinical (unspecified phase)
0.5753 Remote Similarity NPD2388 Discontinued
0.5748 Remote Similarity NPD2977 Approved
0.5748 Remote Similarity NPD2978 Approved
0.5742 Remote Similarity NPD6419 Discontinued
0.5735 Remote Similarity NPD4210 Discontinued
0.5728 Remote Similarity NPD2459 Approved
0.5728 Remote Similarity NPD3060 Approved
0.5728 Remote Similarity NPD2458 Approved
0.5728 Remote Similarity NPD2460 Phase 3
0.5726 Remote Similarity NPD6519 Phase 2
0.5726 Remote Similarity NPD7827 Phase 1
0.5721 Remote Similarity NPD2296 Approved
0.5721 Remote Similarity NPD3808 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7583 Approved
0.5714 Remote Similarity NPD2183 Approved
0.5714 Remote Similarity NPD3473 Clinical (unspecified phase)
0.5714 Remote Similarity NPD2184 Approved
0.5714 Remote Similarity NPD2186 Approved
0.5702 Remote Similarity NPD4157 Discontinued
0.5701 Remote Similarity NPD5356 Approved
0.5701 Remote Similarity NPD5355 Approved
0.5696 Remote Similarity NPD7296 Approved
0.5694 Remote Similarity NPD1774 Approved
0.569 Remote Similarity NPD4362 Clinical (unspecified phase)
0.569 Remote Similarity NPD4361 Phase 2
0.569 Remote Similarity NPD7585 Approved
0.5688 Remote Similarity NPD2904 Discontinued
0.5687 Remote Similarity NPD5586 Clinical (unspecified phase)
0.5682 Remote Similarity NPD5137 Approved
0.5678 Remote Similarity NPD6823 Phase 2
0.5677 Remote Similarity NPD5910 Clinical (unspecified phase)
0.5676 Remote Similarity NPD3909 Discontinued
0.5674 Remote Similarity NPD6668 Clinical (unspecified phase)
0.5672 Remote Similarity NPD5745 Approved
0.5667 Remote Similarity NPD2874 Phase 2
0.566 Remote Similarity NPD4124 Clinical (unspecified phase)
0.5659 Remote Similarity NPD2161 Phase 2
0.5658 Remote Similarity NPD6793 Clinical (unspecified phase)
0.565 Remote Similarity NPD42 Phase 2
0.565 Remote Similarity NPD5163 Phase 2
0.565 Remote Similarity NPD6042 Phase 2
0.5649 Remote Similarity NPD6973 Clinical (unspecified phase)
0.5647 Remote Similarity NPD4413 Clinical (unspecified phase)
0.5644 Remote Similarity NPD3597 Clinical (unspecified phase)
0.564 Remote Similarity NPD52 Approved
0.564 Remote Similarity NPD7526 Approved
0.564 Remote Similarity NPD7527 Clinical (unspecified phase)
0.5639 Remote Similarity NPD6851 Approved
0.5639 Remote Similarity NPD6853 Approved
0.5631 Remote Similarity NPD5605 Phase 2
0.5631 Remote Similarity NPD7978 Discontinued
0.563 Remote Similarity NPD7891 Discontinued
0.5628 Remote Similarity NPD3819 Phase 2
0.5628 Remote Similarity NPD3269 Clinical (unspecified phase)
0.5628 Remote Similarity NPD2250 Discontinued
0.5625 Remote Similarity NPD2325 Approved
0.5622 Remote Similarity NPD7547 Clinical (unspecified phase)
0.562 Remote Similarity NPD7801 Approved
0.5619 Remote Similarity NPD4419 Clinical (unspecified phase)
0.5618 Remote Similarity NPD8469 Approved
0.5612 Remote Similarity NPD4971 Clinical (unspecified phase)
0.5611 Remote Similarity NPD644 Clinical (unspecified phase)
0.5605 Remote Similarity NPD5940 Clinical (unspecified phase)
0.5604 Remote Similarity NPD6681 Discovery
0.5604 Remote Similarity NPD7153 Discontinued
0.5604 Remote Similarity NPD7596 Clinical (unspecified phase)
0.56 Remote Similarity NPD7959 Clinical (unspecified phase)
0.56 Remote Similarity NPD6297 Approved

Structure

External Identifiers

PubChem CID   73346123
ChEMBL   CHEMBL2419314
ZINC  

Physicochemical Properties

Molecular Weight:  886.81
ALogP:  -0.2842
MLogP:  2.56
XLogP:  5.063
# Rotatable Bonds:  20
Polar Surface Area:  165.01
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  44

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs