NPASS Natural Product

Natural Product: NPC233273

Natural Product ID:	NPC233273
Common Name:	Palmerolide A
IUPAC Name:	[(2R,4E,6E,10S,11S,12E,14S,18E)-11,14-dihydroxy-4-methyl-2-[(2R,3E,5E)-4-methyl-6-(3-methylbut-2-enoylamino)hexa-3,5-dien-2-yl]-20-oxo-1-oxacycloicosa-4,6,12,18-tetraen-10-yl] carbamate
Synonyms:
Molecular Formula:	C33H48N2O7
Standard InCHIKey:	HEOKDDVDVGNHMR-DAUCKHFQSA-N
Standard InCHI:	InChI=1S/C33H48N2O7/c1-23(2)20-31(38)35-19-18-25(4)21-26(5)30-22-24(3)12-8-6-10-14-29(42-33(34)40)28(37)17-16-27(36)13-9-7-11-15-32(39)41-30/h6,8,11-12,15-21,26-30,36-37H,7,9-10,13-14,22H2,1-5H3,(H2,34,40)(H,35,38)/b8-6+,15-11+,17-16+,19-18+,24-12+,25-21+/t26-,27+,28+,29+,30-/m1/s1
Canonical SMILES:	O[C@H]1CCC/C=C/C(=O)O[C@H](C/C(=C/C=C/CC[C@@H]([C@H](/C=C/1)O)OC(=N)O)/C)[C@@H](/C=C(/C=C/N=C(C=C(C)C)O)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
NPO17267	Synoicum adareanum	Species	Polyclinidae	Eukaryota				PMID[21737286]

Biological Activity

Activity Type	# Activity
IC50	2
Others	3

Activity Type	# Activity
Cell Line	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	2	nM	18298075
NPT2	Others	Unspecified		Ratio IC50	=	0.083		18298075
NPT398	Cell Line	UACC-62	Homo sapiens	LC50	=	18	nM	22934671
NPT2	Others	Unspecified		LC50	=	18	nM	19653666
NPT398	Cell Line	UACC-62	Homo sapiens	IC50	=	24	nM	6481359

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 NPC233273 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	49
0.1-0.2	281
0.2-0.3	2622
0.3-0.4	15927
0.4-0.5	9264
0.5-0.6	2435
0.6-0.7	301
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC205546
1.0	High Similarity	NPC50902
0.9775	High Similarity	NPC189764
0.8242	Intermediate Similarity	NPC161670
0.7528	Intermediate Similarity	NPC315843
0.7528	Intermediate Similarity	NPC107654
0.7525	Intermediate Similarity	NPC175614
0.7303	Intermediate Similarity	NPC316185
0.7	Intermediate Similarity	NPC473361
0.7	Intermediate Similarity	NPC329904
0.6964	Remote Similarity	NPC29501
0.6957	Remote Similarity	NPC27413
0.6957	Remote Similarity	NPC271621
0.6957	Remote Similarity	NPC59751
0.69	Remote Similarity	NPC45409
0.686	Remote Similarity	NPC473249
0.6848	Remote Similarity	NPC314678
0.6742	Remote Similarity	NPC146811
0.6703	Remote Similarity	NPC471022
0.67	Remote Similarity	NPC471494
0.6696	Remote Similarity	NPC5485
0.6667	Remote Similarity	NPC279532
0.6667	Remote Similarity	NPC475642
0.6667	Remote Similarity	NPC316325
0.6639	Remote Similarity	NPC473808
0.6638	Remote Similarity	NPC471645
0.6637	Remote Similarity	NPC133625
0.6637	Remote Similarity	NPC298484
0.6636	Remote Similarity	NPC52820
0.6634	Remote Similarity	NPC311163
0.6633	Remote Similarity	NPC315731
0.6629	Remote Similarity	NPC19769
0.6606	Remote Similarity	NPC175531
0.6606	Remote Similarity	NPC313234
0.66	Remote Similarity	NPC266718
0.66	Remote Similarity	NPC475706
0.6598	Remote Similarity	NPC314854
0.6598	Remote Similarity	NPC313911
0.6583	Remote Similarity	NPC315915
0.6581	Remote Similarity	NPC7905
0.6581	Remote Similarity	NPC315652
0.6579	Remote Similarity	NPC113012
0.6579	Remote Similarity	NPC122926
0.6569	Remote Similarity	NPC313658
0.6569	Remote Similarity	NPC316138
0.6556	Remote Similarity	NPC201356
0.6556	Remote Similarity	NPC315141
0.6556	Remote Similarity	NPC129995
0.6538	Remote Similarity	NPC475995
0.6538	Remote Similarity	NPC475879
0.6538	Remote Similarity	NPC474098
0.6535	Remote Similarity	NPC474424
0.6522	Remote Similarity	NPC151481
0.6518	Remote Similarity	NPC154601
0.6518	Remote Similarity	NPC271269
0.6518	Remote Similarity	NPC472433
0.65	Remote Similarity	NPC142111
0.65	Remote Similarity	NPC315559
0.65	Remote Similarity	NPC473315
0.65	Remote Similarity	NPC161045
0.6496	Remote Similarity	NPC103391
0.6496	Remote Similarity	NPC472536
0.6486	Remote Similarity	NPC55336
0.6486	Remote Similarity	NPC199831
0.6486	Remote Similarity	NPC68001
0.6486	Remote Similarity	NPC474828
0.6486	Remote Similarity	NPC474827
0.6471	Remote Similarity	NPC316426
0.6471	Remote Similarity	NPC315395
0.6465	Remote Similarity	NPC184208
0.6465	Remote Similarity	NPC8538
0.646	Remote Similarity	NPC251330
0.6458	Remote Similarity	NPC203277
0.6452	Remote Similarity	NPC476037
0.6452	Remote Similarity	NPC59558
0.6446	Remote Similarity	NPC475383
0.6446	Remote Similarity	NPC156379
0.6444	Remote Similarity	NPC96414
0.6436	Remote Similarity	NPC473308
0.6436	Remote Similarity	NPC475035
0.6429	Remote Similarity	NPC471537
0.6429	Remote Similarity	NPC1180
0.6422	Remote Similarity	NPC203627
0.6421	Remote Similarity	NPC470686
0.6415	Remote Similarity	NPC472195
0.6415	Remote Similarity	NPC238090
0.6415	Remote Similarity	NPC472196
0.6413	Remote Similarity	NPC63873
0.6408	Remote Similarity	NPC475186
0.6408	Remote Similarity	NPC118077
0.64	Remote Similarity	NPC474439
0.64	Remote Similarity	NPC251026
0.64	Remote Similarity	NPC313677
0.64	Remote Similarity	NPC474028
0.6396	Remote Similarity	NPC474244
0.6389	Remote Similarity	NPC45313
0.6389	Remote Similarity	NPC288350
0.6389	Remote Similarity	NPC173329
0.6383	Remote Similarity	NPC293114
0.6379	Remote Similarity	NPC21713
0.6379	Remote Similarity	NPC170375
0.6379	Remote Similarity	NPC323007
0.6379	Remote Similarity	NPC475608
0.6373	Remote Similarity	NPC475034
0.6373	Remote Similarity	NPC11804
0.6372	Remote Similarity	NPC472615
0.6355	Remote Similarity	NPC159698
0.6354	Remote Similarity	NPC315552
0.6348	Remote Similarity	NPC182549
0.6348	Remote Similarity	NPC114741
0.6346	Remote Similarity	NPC475739
0.6346	Remote Similarity	NPC470137
0.6344	Remote Similarity	NPC475982
0.6337	Remote Similarity	NPC16488
0.6337	Remote Similarity	NPC286770
0.6337	Remote Similarity	NPC284472
0.6337	Remote Similarity	NPC44261
0.6337	Remote Similarity	NPC229799
0.6337	Remote Similarity	NPC475714
0.6333	Remote Similarity	NPC253468
0.6333	Remote Similarity	NPC235311
0.6333	Remote Similarity	NPC296361
0.6325	Remote Similarity	NPC279383
0.6325	Remote Similarity	NPC295444
0.6325	Remote Similarity	NPC273215
0.6325	Remote Similarity	NPC268327
0.6316	Remote Similarity	NPC284006
0.6316	Remote Similarity	NPC316851
0.6316	Remote Similarity	NPC329890
0.6316	Remote Similarity	NPC315426
0.6311	Remote Similarity	NPC61527
0.6311	Remote Similarity	NPC208473
0.63	Remote Similarity	NPC474894
0.6292	Remote Similarity	NPC26810
0.6281	Remote Similarity	NPC241050
0.6277	Remote Similarity	NPC476012
0.6277	Remote Similarity	NPC4299
0.6273	Remote Similarity	NPC475653
0.6264	Remote Similarity	NPC282760
0.6264	Remote Similarity	NPC273600
0.6263	Remote Similarity	NPC99651
0.6263	Remote Similarity	NPC470149
0.6263	Remote Similarity	NPC470148
0.6262	Remote Similarity	NPC320552
0.6261	Remote Similarity	NPC474099
0.625	Remote Similarity	NPC472614
0.625	Remote Similarity	NPC475037
0.625	Remote Similarity	NPC199382
0.6239	Remote Similarity	NPC165332
0.6239	Remote Similarity	NPC180722
0.6239	Remote Similarity	NPC255410
0.6239	Remote Similarity	NPC195645
0.6239	Remote Similarity	NPC197294
0.6239	Remote Similarity	NPC8098
0.6239	Remote Similarity	NPC475503
0.6239	Remote Similarity	NPC183449
0.6238	Remote Similarity	NPC474959
0.6238	Remote Similarity	NPC324170
0.6238	Remote Similarity	NPC475046
0.6238	Remote Similarity	NPC11383
0.6238	Remote Similarity	NPC310450
0.6237	Remote Similarity	NPC249713
0.6228	Remote Similarity	NPC201128
0.6226	Remote Similarity	NPC3952
0.6226	Remote Similarity	NPC477866
0.6226	Remote Similarity	NPC477865
0.6226	Remote Similarity	NPC327253
0.6222	Remote Similarity	NPC471023
0.6222	Remote Similarity	NPC77891
0.6211	Remote Similarity	NPC477087
0.6211	Remote Similarity	NPC477086
0.6207	Remote Similarity	NPC133729
0.6207	Remote Similarity	NPC24389
0.6204	Remote Similarity	NPC262312
0.6204	Remote Similarity	NPC70323
0.6204	Remote Similarity	NPC23454
0.6204	Remote Similarity	NPC35269
0.6204	Remote Similarity	NPC256368
0.6204	Remote Similarity	NPC5418
0.6202	Remote Similarity	NPC314361
0.62	Remote Similarity	NPC470147
0.62	Remote Similarity	NPC133226
0.6196	Remote Similarity	NPC276299
0.619	Remote Similarity	NPC262845
0.619	Remote Similarity	NPC68293
0.6186	Remote Similarity	NPC478191
0.6186	Remote Similarity	NPC478194
0.6186	Remote Similarity	NPC478196
0.6186	Remote Similarity	NPC161038
0.6186	Remote Similarity	NPC260396
0.6186	Remote Similarity	NPC478193
0.6186	Remote Similarity	NPC478192
0.6186	Remote Similarity	NPC478195
0.6182	Remote Similarity	NPC120299
0.6182	Remote Similarity	NPC475332
0.617	Remote Similarity	NPC101622
0.6162	Remote Similarity	NPC279214
0.6162	Remote Similarity	NPC221095
0.6162	Remote Similarity	NPC248775
0.6162	Remote Similarity	NPC473471

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC233273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	66
0.1-0.2	190
0.2-0.3	2581
0.3-0.4	4884
0.4-0.5	1292
0.5-0.6	128
0.6-0.7	19
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7273	Intermediate Similarity	NPD7116	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7623	Phase 3
0.6949	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7747	Phase 1
0.686	Remote Similarity	NPD7746	Phase 1
0.681	Remote Similarity	NPD7505	Discontinued
0.6667	Remote Similarity	NPD7500	Approved
0.6538	Remote Similarity	NPD7838	Discovery
0.6422	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6094	Approved
0.6381	Remote Similarity	NPD6095	Approved
0.6379	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7839	Suspended
0.623	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4228	Discovery
0.608	Remote Similarity	NPD7829	Approved
0.608	Remote Similarity	NPD7830	Approved
0.6068	Remote Similarity	NPD6413	Approved
0.6017	Remote Similarity	NPD6421	Discontinued
0.5962	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6640	Phase 3
0.5926	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7983	Approved
0.5865	Remote Similarity	NPD205	Approved
0.5812	Remote Similarity	NPD4211	Phase 1
0.5794	Remote Similarity	NPD8444	Approved
0.578	Remote Similarity	NPD6698	Approved
0.578	Remote Similarity	NPD46	Approved
0.5776	Remote Similarity	NPD2259	Approved
0.5776	Remote Similarity	NPD2258	Approved
0.5776	Remote Similarity	NPD1407	Approved
0.5739	Remote Similarity	NPD5344	Discontinued
0.5692	Remote Similarity	NPD8074	Phase 3
0.568	Remote Similarity	NPD7641	Discontinued
0.5676	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD2251	Approved
0.5676	Remote Similarity	NPD2252	Approved
0.5652	Remote Similarity	NPD6648	Approved
0.5615	Remote Similarity	NPD8273	Phase 1

Structure

NPC233273 OpenBabel07101719512D 42 42 0 0 1 0 0 0 0 0999 V2000 -5.2734 0.8279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7260 -0.1155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9165 -1.8845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5530 -3.2608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8997 -2.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1079 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 3.7111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5201 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.5201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4169 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8968 2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7111 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 5.1079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4169 2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8968 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7601 5.4169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7111 5.1079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0962 -2.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6409 -1.6358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1828 -0.9018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6436 -1.5311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7274 -0.0631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7601 -0.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0976 -2.4221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3550 -1.4788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7601 5.4169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5201 4.5201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1079 3.7111 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1841 -0.8495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8376 3.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7853 2.6219 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6395 -1.6881 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6036 6.4046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2273 5.2273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7301 0.0415 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4788 0.3550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7286 4.0745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9989 4.1651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 24 2 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 32 1 0 0 0 0 16 17 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 35 1 0 0 0 0 20 23 2 0 0 0 0 20 31 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 26 5 1 6 0 0 0 27 36 1 6 0 0 0 28 29 1 0 0 0 0 28 37 1 6 0 0 0 29 42 1 1 0 0 0 30 26 1 6 0 0 0 30 41 1 0 0 0 0 31 35 2 3 0 0 0 31 38 1 0 0 0 0 32 39 2 0 0 0 0 32 41 1 0 0 0 0 33 34 2 0 0 0 0 33 40 1 0 0 0 0 33 42 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	17756325
ChEMBL	CHEMBL573783
ZINC

Physicochemical Properties

Molecular Weight:	584.35
ALogP:	2.9836
MLogP:	4.1
XLogP:	5.305
# Rotatable Bonds:	16
Polar Surface Area:	152.66
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	42

Download Data

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