NPASS Natural Product

Natural Product: NPC474674

Natural Product ID:	NPC474674
Common Name:	1-O-(2'-Methoxy-4'z-Hexadecenyl)-Sn-Glycero-3-Phosphocholine
IUPAC Name:	[(2S)-2-hydroxy-3-[(Z)-2-methoxyhexadec-4-enoxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
Synonyms:
Molecular Formula:	C25H52NO7P
Standard InCHIKey:	NYFGVUCTLCDUFF-VTYVONMNSA-N
Standard InCHI:	InChI=1S/C25H52NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-25(30-5)23-31-21-24(27)22-33-34(28,29)32-20-19-26(2,3)4/h16-17,24-25,27H,6-15,18-23H2,1-5H3/b17-16-/t24-,25?/m0/s1
Canonical SMILES:	CCCCCCCCCCC/C=CCC(COC[C@@H](COP(=O)(OCC[N+](C)(C)C)[O-])O)OC
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
NPO85	Spirastrella abata	Species	Spirastrellidae	Eukaryota				PMID[11325244]

Biological Activity

Activity Type	# Activity
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	5.9	ug/ml	22209564
NPT2358	Cell Line	SK-MEL3	Homo sapiens	ED50	=	3.8	ug/ml	PubChem BioAssay data set
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	4	ug/ml	9584409
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	3.7	ug/ml	22037378
NPT81	Cell Line	A549	Homo sapiens	ED50	=	6.3	ug/ml	21513293

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 NPC474674 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	39
0.1-0.2	691
0.2-0.3	13842
0.3-0.4	11837
0.4-0.5	3906
0.5-0.6	498
0.6-0.7	61
0.7-0.8	8
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC474675
0.9846	High Similarity	NPC475930
0.9846	High Similarity	NPC137620
0.9846	High Similarity	NPC127145
0.9412	High Similarity	NPC305223
0.8205	Intermediate Similarity	NPC178758
0.8205	Intermediate Similarity	NPC196102
0.7895	Intermediate Similarity	NPC325936
0.7647	Intermediate Similarity	NPC328786
0.7647	Intermediate Similarity	NPC201338
0.7647	Intermediate Similarity	NPC474627
0.7333	Intermediate Similarity	NPC324638
0.7284	Intermediate Similarity	NPC82799
0.7123	Intermediate Similarity	NPC238646
0.7045	Intermediate Similarity	NPC329906
0.6667	Remote Similarity	NPC169976
0.6667	Remote Similarity	NPC114640
0.6667	Remote Similarity	NPC33267
0.6667	Remote Similarity	NPC324165
0.6667	Remote Similarity	NPC126366
0.6667	Remote Similarity	NPC170963
0.6543	Remote Similarity	NPC3094
0.642	Remote Similarity	NPC288086
0.64	Remote Similarity	NPC55068
0.6364	Remote Similarity	NPC81384
0.6341	Remote Similarity	NPC62293
0.6341	Remote Similarity	NPC140327
0.6341	Remote Similarity	NPC264417
0.6341	Remote Similarity	NPC217095
0.6341	Remote Similarity	NPC51055
0.6341	Remote Similarity	NPC212008
0.6316	Remote Similarity	NPC476658
0.631	Remote Similarity	NPC474833
0.625	Remote Similarity	NPC97614
0.6234	Remote Similarity	NPC296436
0.6234	Remote Similarity	NPC176215
0.6234	Remote Similarity	NPC476655
0.6234	Remote Similarity	NPC476654
0.6234	Remote Similarity	NPC476657
0.6216	Remote Similarity	NPC326524
0.6216	Remote Similarity	NPC329003
0.6216	Remote Similarity	NPC325550
0.6184	Remote Similarity	NPC477106
0.6163	Remote Similarity	NPC79367
0.6154	Remote Similarity	NPC83965
0.6154	Remote Similarity	NPC476659
0.6154	Remote Similarity	NPC476656
0.6154	Remote Similarity	NPC113224
0.6133	Remote Similarity	NPC81896
0.6133	Remote Similarity	NPC321919
0.6125	Remote Similarity	NPC103712
0.6125	Remote Similarity	NPC291196
0.6118	Remote Similarity	NPC317263
0.6111	Remote Similarity	NPC242930
0.6098	Remote Similarity	NPC314678
0.6081	Remote Similarity	NPC321030
0.6076	Remote Similarity	NPC127091
0.6076	Remote Similarity	NPC330426
0.6076	Remote Similarity	NPC22101
0.6076	Remote Similarity	NPC104537
0.6076	Remote Similarity	NPC271921
0.6076	Remote Similarity	NPC475443
0.6076	Remote Similarity	NPC148192
0.6076	Remote Similarity	NPC473829
0.6047	Remote Similarity	NPC474702
0.6023	Remote Similarity	NPC474312
0.6	Remote Similarity	NPC48218
0.6	Remote Similarity	NPC23721
0.6	Remote Similarity	NPC209327
0.6	Remote Similarity	NPC473559
0.6	Remote Similarity	NPC224700
0.6	Remote Similarity	NPC324981
0.6	Remote Similarity	NPC273508
0.6	Remote Similarity	NPC141481
0.6	Remote Similarity	NPC320663
0.6	Remote Similarity	NPC29234
0.5977	Remote Similarity	NPC207657
0.5976	Remote Similarity	NPC54460
0.5957	Remote Similarity	NPC182632
0.5957	Remote Similarity	NPC282705
0.5926	Remote Similarity	NPC473772
0.5921	Remote Similarity	NPC130807
0.5914	Remote Similarity	NPC39290
0.5914	Remote Similarity	NPC159369
0.5897	Remote Similarity	NPC235311
0.5897	Remote Similarity	NPC253468
0.5897	Remote Similarity	NPC475221
0.5889	Remote Similarity	NPC477199
0.5882	Remote Similarity	NPC330017
0.5854	Remote Similarity	NPC476660
0.5851	Remote Similarity	NPC209047
0.5851	Remote Similarity	NPC74672
0.5851	Remote Similarity	NPC43074
0.5851	Remote Similarity	NPC242503
0.5851	Remote Similarity	NPC139782
0.5844	Remote Similarity	NPC321838
0.5844	Remote Similarity	NPC47333
0.5833	Remote Similarity	NPC470992
0.5833	Remote Similarity	NPC262312
0.5833	Remote Similarity	NPC23454
0.5833	Remote Similarity	NPC35269
0.5833	Remote Similarity	NPC470993
0.5833	Remote Similarity	NPC70323
0.5789	Remote Similarity	NPC263545
0.5789	Remote Similarity	NPC186840
0.5789	Remote Similarity	NPC475125
0.5789	Remote Similarity	NPC473604
0.5789	Remote Similarity	NPC473581
0.5789	Remote Similarity	NPC61894
0.5789	Remote Similarity	NPC473866
0.5789	Remote Similarity	NPC111567
0.5789	Remote Similarity	NPC15851
0.5789	Remote Similarity	NPC473950
0.5789	Remote Similarity	NPC309898
0.5789	Remote Similarity	NPC475603
0.5778	Remote Similarity	NPC228638
0.5778	Remote Similarity	NPC315559
0.5769	Remote Similarity	NPC471023
0.575	Remote Similarity	NPC315141
0.575	Remote Similarity	NPC129995
0.5733	Remote Similarity	NPC323436
0.5733	Remote Similarity	NPC121034
0.5733	Remote Similarity	NPC52012
0.5714	Remote Similarity	NPC55652
0.5714	Remote Similarity	NPC258788
0.5714	Remote Similarity	NPC45313
0.5714	Remote Similarity	NPC470435
0.5694	Remote Similarity	NPC473872
0.5679	Remote Similarity	NPC25298
0.5679	Remote Similarity	NPC473357
0.5679	Remote Similarity	NPC193029
0.5679	Remote Similarity	NPC478100
0.5676	Remote Similarity	NPC281590
0.567	Remote Similarity	NPC54961
0.567	Remote Similarity	NPC282088
0.567	Remote Similarity	NPC17290
0.567	Remote Similarity	NPC157353
0.567	Remote Similarity	NPC256570
0.567	Remote Similarity	NPC158445
0.567	Remote Similarity	NPC156782
0.567	Remote Similarity	NPC192066
0.567	Remote Similarity	NPC3568
0.5667	Remote Similarity	NPC313677
0.5663	Remote Similarity	NPC42526
0.5647	Remote Similarity	NPC470994
0.5647	Remote Similarity	NPC474321
0.5641	Remote Similarity	NPC29468
0.5625	Remote Similarity	NPC477525
0.5618	Remote Similarity	NPC209232
0.561	Remote Similarity	NPC249713
0.561	Remote Similarity	NPC474812

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	48
0.1-0.2	934
0.2-0.3	5102
0.3-0.4	2484
0.4-0.5	557
0.5-0.6	25
0.6-0.7	8
0.7-0.8	3
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
0.7941	Intermediate Similarity	NPD6949	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3212	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6950	Discontinued
0.64	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9462	Approved
0.6364	Remote Similarity	NPD9463	Phase 3
0.6184	Remote Similarity	NPD7347	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD8277	Approved
0.6029	Remote Similarity	NPD4840	Approved
0.6	Remote Similarity	NPD6948	Phase 3
0.6	Remote Similarity	NPD8278	Approved
0.5867	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD8522	Clinical (unspecified phase)

Structure

NPC474674 OpenBabel07101718312D 34 33 0 0 1 0 0 0 0 0999 V2000 15.5000 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0000 0.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0000 0.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5000 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0000 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5000 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 3.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0000 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 1.5000 -2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.1340 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 4.5000 -2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 32 1 0 0 0 0 21 24 1 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 0 0 0 0 24 27 1 1 0 0 0 25 30 1 0 0 0 0 28 34 2 0 0 0 0 29 34 1 0 0 0 0 32 34 1 0 0 0 0 33 34 1 0 0 0 0 M CHG 2 26 1 29 -1 M END $$$$

External Identifiers

PubChem CID	44584786
ChEMBL	CHEMBL479108
ZINC

Physicochemical Properties

Molecular Weight:	509.35
ALogP:	-4.3329
MLogP:	3.22
XLogP:	4.531
# Rotatable Bonds:	31
Polar Surface Area:	107.09
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	34

Download Data

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