NPASS Natural Product

Natural Product: NPC167380

Natural Product ID:	NPC167380
Common Name:	Hippolide A
IUPAC Name:	(3S)-3-[(2R,6S)-6-hydroxy-5-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,6-dihydro-2H-pyran-2-yl]pyrrolidine-2,5-dione
Synonyms:	Hippolide A
Molecular Formula:	C25H37NO4
Standard InCHIKey:	DHMXAXCAWHUFET-HVFQXGRFSA-N
Standard InCHI:	InChI=1S/C25H37NO4/c1-17(2)8-5-9-18(3)10-6-11-19(4)12-7-13-20-14-15-22(30-25(20)29)21-16-23(27)26-24(21)28/h8,10,12,14,21-22,25,29H,5-7,9,11,13,15-16H2,1-4H3,(H,26,27,28)/b18-10+,19-12+/t21-,22+,25-/m0/s1
Canonical SMILES:	C/C(=CCCC1=CC[C@@H](O[C@@H]1O)[C@@H]1CC(=NC1=O)O)/CC/C=C(/CCC=C(C)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
NPO15322	Hippospongia lachne	Species	Spongiidae	Eukaryota				PMID[21548579]

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	3
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	52.2	nM	21548579
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	48	nM	21548579
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	9780	nM	21548579
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	23810	nM	21548579
NPT880	Individual Protein	Protein kinase C gamma	Homo sapiens	IC50	=	61970	nM	21548579

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 NPC167380 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	57
0.1-0.2	354
0.2-0.3	2606
0.3-0.4	15537
0.4-0.5	8681
0.5-0.6	3408
0.6-0.7	239
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.967	High Similarity	NPC121857
0.7156	Intermediate Similarity	NPC271269
0.7117	Intermediate Similarity	NPC24389
0.7103	Intermediate Similarity	NPC175531
0.7103	Intermediate Similarity	NPC313234
0.7091	Intermediate Similarity	NPC251330
0.7	Intermediate Similarity	NPC154601
0.699	Remote Similarity	NPC472264
0.6726	Remote Similarity	NPC475150
0.6667	Remote Similarity	NPC9447
0.6633	Remote Similarity	NPC321728
0.6602	Remote Similarity	NPC241054
0.6571	Remote Similarity	NPC475879
0.6538	Remote Similarity	NPC472011
0.6538	Remote Similarity	NPC106051
0.6538	Remote Similarity	NPC137368
0.6509	Remote Similarity	NPC314500
0.6496	Remote Similarity	NPC469865
0.6481	Remote Similarity	NPC150041
0.6476	Remote Similarity	NPC471054
0.6471	Remote Similarity	NPC158756
0.6466	Remote Similarity	NPC122926
0.6466	Remote Similarity	NPC113012
0.646	Remote Similarity	NPC472616
0.646	Remote Similarity	NPC14537
0.6455	Remote Similarity	NPC234542
0.6442	Remote Similarity	NPC45409
0.6435	Remote Similarity	NPC140251
0.6435	Remote Similarity	NPC307903
0.6429	Remote Similarity	NPC128501
0.6422	Remote Similarity	NPC475503
0.6417	Remote Similarity	NPC316325
0.6412	Remote Similarity	NPC230889
0.6408	Remote Similarity	NPC470755
0.6404	Remote Similarity	NPC473252
0.6404	Remote Similarity	NPC472615
0.6396	Remote Similarity	NPC473224
0.6372	Remote Similarity	NPC474563
0.6364	Remote Similarity	NPC476344
0.6364	Remote Similarity	NPC150967
0.6364	Remote Similarity	NPC296361
0.6364	Remote Similarity	NPC265662
0.6364	Remote Similarity	NPC127526
0.6364	Remote Similarity	NPC4834
0.6356	Remote Similarity	NPC7797
0.6355	Remote Similarity	NPC472199
0.6355	Remote Similarity	NPC472010
0.6355	Remote Similarity	NPC471059
0.6346	Remote Similarity	NPC469910
0.6341	Remote Similarity	NPC469515
0.632	Remote Similarity	NPC469494
0.6316	Remote Similarity	NPC64168
0.6311	Remote Similarity	NPC126518
0.6299	Remote Similarity	NPC477793
0.6299	Remote Similarity	NPC329919
0.6286	Remote Similarity	NPC142583
0.6283	Remote Similarity	NPC469598
0.6275	Remote Similarity	NPC471298
0.6275	Remote Similarity	NPC323251
0.6275	Remote Similarity	NPC471296
0.6271	Remote Similarity	NPC170375
0.6271	Remote Similarity	NPC29501
0.6269	Remote Similarity	NPC315848
0.6269	Remote Similarity	NPC315210
0.6263	Remote Similarity	NPC7563
0.6263	Remote Similarity	NPC116177
0.6263	Remote Similarity	NPC320630
0.625	Remote Similarity	NPC474860
0.625	Remote Similarity	NPC471300
0.625	Remote Similarity	NPC163606
0.6239	Remote Similarity	NPC475927
0.6239	Remote Similarity	NPC475832
0.6239	Remote Similarity	NPC473578
0.6239	Remote Similarity	NPC472198
0.6239	Remote Similarity	NPC298484
0.6228	Remote Similarity	NPC80439
0.6228	Remote Similarity	NPC279833
0.6228	Remote Similarity	NPC6271
0.6228	Remote Similarity	NPC173690
0.6226	Remote Similarity	NPC476805
0.6226	Remote Similarity	NPC476803
0.6226	Remote Similarity	NPC475819
0.6216	Remote Similarity	NPC475709
0.6216	Remote Similarity	NPC475646
0.6214	Remote Similarity	NPC131669
0.6214	Remote Similarity	NPC229799
0.6214	Remote Similarity	NPC40746
0.6214	Remote Similarity	NPC473390
0.6214	Remote Similarity	NPC286770
0.6214	Remote Similarity	NPC169575
0.6214	Remote Similarity	NPC16488
0.6214	Remote Similarity	NPC471297
0.6214	Remote Similarity	NPC284472
0.621	Remote Similarity	NPC315915
0.6204	Remote Similarity	NPC472197
0.62	Remote Similarity	NPC108816
0.62	Remote Similarity	NPC93763
0.6198	Remote Similarity	NPC7905
0.6198	Remote Similarity	NPC315652
0.6195	Remote Similarity	NPC28304
0.6195	Remote Similarity	NPC298255
0.619	Remote Similarity	NPC315395
0.619	Remote Similarity	NPC204639
0.619	Remote Similarity	NPC316426
0.619	Remote Similarity	NPC469483
0.6186	Remote Similarity	NPC92829
0.6182	Remote Similarity	NPC476487
0.6182	Remote Similarity	NPC189764
0.6182	Remote Similarity	NPC476488
0.6182	Remote Similarity	NPC314009
0.6182	Remote Similarity	NPC54905
0.6176	Remote Similarity	NPC52861
0.6176	Remote Similarity	NPC24417
0.6174	Remote Similarity	NPC259476
0.6167	Remote Similarity	NPC5485
0.6162	Remote Similarity	NPC68819
0.6161	Remote Similarity	NPC313440
0.6154	Remote Similarity	NPC476804
0.6154	Remote Similarity	NPC168733
0.6148	Remote Similarity	NPC216335
0.6146	Remote Similarity	NPC4299
0.6139	Remote Similarity	NPC99651
0.6134	Remote Similarity	NPC316984
0.6134	Remote Similarity	NPC30911
0.6129	Remote Similarity	NPC477140
0.6129	Remote Similarity	NPC473808
0.6129	Remote Similarity	NPC477143
0.6126	Remote Similarity	NPC180722
0.6126	Remote Similarity	NPC165332
0.6126	Remote Similarity	NPC175614
0.6126	Remote Similarity	NPC306041
0.6126	Remote Similarity	NPC195645
0.6126	Remote Similarity	NPC54731
0.6122	Remote Similarity	NPC476590
0.6122	Remote Similarity	NPC114727
0.6121	Remote Similarity	NPC472433
0.6121	Remote Similarity	NPC201128
0.6121	Remote Similarity	NPC475918
0.6117	Remote Similarity	NPC469838
0.6117	Remote Similarity	NPC11383
0.6117	Remote Similarity	NPC469833
0.6117	Remote Similarity	NPC475046
0.6117	Remote Similarity	NPC229825
0.6117	Remote Similarity	NPC310450
0.6117	Remote Similarity	NPC474959
0.6111	Remote Similarity	NPC477866
0.6111	Remote Similarity	NPC477865
0.6111	Remote Similarity	NPC232426
0.6111	Remote Similarity	NPC474232
0.6111	Remote Similarity	NPC66855
0.6111	Remote Similarity	NPC281942
0.6107	Remote Similarity	NPC314361
0.6106	Remote Similarity	NPC255677
0.6106	Remote Similarity	NPC469872
0.6106	Remote Similarity	NPC306344
0.6106	Remote Similarity	NPC22149
0.6106	Remote Similarity	NPC469864
0.6102	Remote Similarity	NPC474725
0.6102	Remote Similarity	NPC474891
0.6102	Remote Similarity	NPC329305
0.6102	Remote Similarity	NPC133729
0.6095	Remote Similarity	NPC255307
0.6095	Remote Similarity	NPC475034
0.6091	Remote Similarity	NPC104925
0.6091	Remote Similarity	NPC298973
0.6091	Remote Similarity	NPC469697
0.609	Remote Similarity	NPC472430
0.6087	Remote Similarity	NPC118761
0.6087	Remote Similarity	NPC284929
0.6087	Remote Similarity	NPC234304
0.6087	Remote Similarity	NPC55336
0.6087	Remote Similarity	NPC197541
0.6087	Remote Similarity	NPC267869
0.6083	Remote Similarity	NPC268327
0.6083	Remote Similarity	NPC273215
0.6083	Remote Similarity	NPC295444
0.6082	Remote Similarity	NPC477086
0.6082	Remote Similarity	NPC477087
0.6075	Remote Similarity	NPC474629
0.6071	Remote Similarity	NPC471462
0.6068	Remote Similarity	NPC475800
0.6068	Remote Similarity	NPC315426
0.6068	Remote Similarity	NPC474285
0.6068	Remote Similarity	NPC254538
0.6061	Remote Similarity	NPC78189
0.6061	Remote Similarity	NPC315552
0.6058	Remote Similarity	NPC188717
0.6058	Remote Similarity	NPC211455
0.6058	Remote Similarity	NPC116543
0.6058	Remote Similarity	NPC52923
0.6058	Remote Similarity	NPC69469
0.6055	Remote Similarity	NPC141831
0.6053	Remote Similarity	NPC98859
0.6053	Remote Similarity	NPC188785
0.6053	Remote Similarity	NPC4637
0.6053	Remote Similarity	NPC20673
0.605	Remote Similarity	NPC127578
0.6042	Remote Similarity	NPC101622
0.604	Remote Similarity	NPC196653
0.604	Remote Similarity	NPC471465

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC167380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	420
0.2-0.3	3072
0.3-0.4	4303
0.4-0.5	1126
0.5-0.6	151
0.6-0.7	11
0.7-0.8	0
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
0.6466	Remote Similarity	NPD6420	Discontinued
0.6422	Remote Similarity	NPD4228	Discovery
0.6417	Remote Similarity	NPD7500	Approved
0.6311	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6421	Discontinued
0.6134	Remote Similarity	NPD2204	Approved
0.6126	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD1719	Phase 1
0.5969	Remote Similarity	NPD8074	Phase 3
0.5966	Remote Similarity	NPD6413	Approved
0.5954	Remote Similarity	NPD6914	Discontinued
0.5922	Remote Similarity	NPD4252	Approved
0.5922	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7505	Discontinued
0.5847	Remote Similarity	NPD4211	Phase 1
0.5818	Remote Similarity	NPD5785	Approved
0.581	Remote Similarity	NPD4269	Approved
0.581	Remote Similarity	NPD4270	Approved
0.5794	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD7623	Phase 3
0.5781	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD1376	Discontinued
0.5769	Remote Similarity	NPD8451	Approved
0.5755	Remote Similarity	NPD7154	Phase 3
0.5741	Remote Similarity	NPD5786	Approved
0.5739	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD7642	Approved
0.5728	Remote Similarity	NPD4268	Approved
0.5728	Remote Similarity	NPD4271	Approved
0.5725	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD8390	Approved
0.5714	Remote Similarity	NPD8391	Approved
0.5714	Remote Similarity	NPD8392	Approved
0.5703	Remote Similarity	NPD8513	Phase 3
0.5703	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD8444	Approved
0.5692	Remote Similarity	NPD8341	Approved
0.5692	Remote Similarity	NPD8299	Approved
0.5692	Remote Similarity	NPD8340	Approved
0.5692	Remote Similarity	NPD8342	Approved
0.5678	Remote Similarity	NPD1407	Approved
0.5676	Remote Similarity	NPD46	Approved
0.5676	Remote Similarity	NPD6698	Approved
0.5676	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5363	Approved
0.5625	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7637	Suspended
0.5625	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7983	Approved
0.562	Remote Similarity	NPD6686	Approved
0.5619	Remote Similarity	NPD4819	Approved
0.5619	Remote Similarity	NPD4822	Approved
0.5619	Remote Similarity	NPD4820	Approved
0.5619	Remote Similarity	NPD4821	Approved
0.5615	Remote Similarity	NPD7829	Approved
0.5615	Remote Similarity	NPD7830	Approved
0.561	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5362	Discontinued
0.5606	Remote Similarity	NPD7747	Phase 1
0.5606	Remote Similarity	NPD7746	Phase 1
0.5603	Remote Similarity	NPD4225	Approved

Structure

CID167380 OpenBabel06191715542D 30 31 0 0 1 0 0 0 0 0999 V2000 2.5981 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4487 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4432 -1.7319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2274 -3.1637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 16 23 1 0 0 0 0 20 25 1 0 0 0 0 21 16 1 1 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 15 1 6 0 0 0 22 30 1 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 24 26 1 0 0 0 0 24 28 2 0 0 0 0 25 29 1 6 0 0 0 25 30 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	53262772
ChEMBL	CHEMBL1782082
ZINC

Physicochemical Properties

Molecular Weight:	415.27
ALogP:	3.3726
MLogP:	3.66
XLogP:	4.801
# Rotatable Bonds:	16
Polar Surface Area:	79.12
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	30

Download Data

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General Info & Identifiers & Properties
Structure MOL file
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