NPASS Natural Product

Natural Product: NPC474675

Natural Product ID:	NPC474675
Common Name:	1-O-(3'z-Hexadecenyl)-Sn-Glycero-3-Phosphocholine
IUPAC Name:	[(2S)-3-[(Z)-hexadec-3-enoxy]-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
Synonyms:
Molecular Formula:	C24H50NO6P
Standard InCHIKey:	NNYXALRCDUGKCV-WIJSZAOYSA-N
Standard InCHI:	InChI=1S/C24H50NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h16-17,24,26H,5-15,18-23H2,1-4H3/b17-16-/t24-/m0/s1
Canonical SMILES:	CCCCCCCCCCCC/C=CCCOC[C@@H](COP(=O)(OCC[N+](C)(C)C)[O-])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
NPO85	Spirastrella abata	Species	Spirastrellidae	Eukaryota				PMID[11325244]

Biological Activity

Activity Type	# Activity
ED50	5
IC50	1

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30	ug/ml	22209564
NPT2358	Cell Line	SK-MEL3	Homo sapiens	ED50	>	30	ug/ml	19015352
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30	ug/ml	17904365
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30	ug/ml	9584409
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30	ug/ml	22037378
NPT2	Others	Unspecified		IC50	=	102	ug/ml	22037378

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 NPC474675 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	38
0.1-0.2	811
0.2-0.3	14840
0.3-0.4	11480
0.4-0.5	3229
0.5-0.6	436
0.6-0.7	42
0.7-0.8	6
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
1.0	High Similarity	NPC137620
0.9846	High Similarity	NPC474674
0.9692	High Similarity	NPC475930
0.9692	High Similarity	NPC127145
0.9265	High Similarity	NPC305223
0.8077	Intermediate Similarity	NPC196102
0.8077	Intermediate Similarity	NPC178758
0.7763	Intermediate Similarity	NPC325936
0.75	Intermediate Similarity	NPC328786
0.75	Intermediate Similarity	NPC474627
0.75	Intermediate Similarity	NPC201338
0.72	Intermediate Similarity	NPC324638
0.716	Intermediate Similarity	NPC82799
0.6986	Remote Similarity	NPC238646
0.6932	Remote Similarity	NPC329906
0.6538	Remote Similarity	NPC126366
0.6538	Remote Similarity	NPC170963
0.6538	Remote Similarity	NPC33267
0.6538	Remote Similarity	NPC324165
0.6538	Remote Similarity	NPC114640
0.6538	Remote Similarity	NPC169976
0.6462	Remote Similarity	NPC81384
0.642	Remote Similarity	NPC3094
0.6329	Remote Similarity	NPC97614
0.6296	Remote Similarity	NPC288086
0.6267	Remote Similarity	NPC55068
0.622	Remote Similarity	NPC140327
0.622	Remote Similarity	NPC212008
0.622	Remote Similarity	NPC62293
0.622	Remote Similarity	NPC51055
0.622	Remote Similarity	NPC217095
0.622	Remote Similarity	NPC264417
0.619	Remote Similarity	NPC474833
0.6184	Remote Similarity	NPC476658
0.6104	Remote Similarity	NPC176215
0.6104	Remote Similarity	NPC476657
0.6104	Remote Similarity	NPC476654
0.6104	Remote Similarity	NPC476655
0.6104	Remote Similarity	NPC296436
0.6087	Remote Similarity	NPC29234
0.6081	Remote Similarity	NPC329003
0.6081	Remote Similarity	NPC326524
0.6081	Remote Similarity	NPC325550
0.6053	Remote Similarity	NPC477106
0.6047	Remote Similarity	NPC79367
0.6026	Remote Similarity	NPC476659
0.6026	Remote Similarity	NPC476656
0.6026	Remote Similarity	NPC113224
0.6026	Remote Similarity	NPC83965
0.6	Remote Similarity	NPC321919
0.6	Remote Similarity	NPC103712
0.6	Remote Similarity	NPC317263
0.6	Remote Similarity	NPC81896
0.6	Remote Similarity	NPC291196
0.6	Remote Similarity	NPC130807
0.5976	Remote Similarity	NPC314678
0.5974	Remote Similarity	NPC235311
0.5974	Remote Similarity	NPC253468
0.5972	Remote Similarity	NPC242930
0.5949	Remote Similarity	NPC475443
0.5949	Remote Similarity	NPC330426
0.5949	Remote Similarity	NPC22101
0.5949	Remote Similarity	NPC127091
0.5949	Remote Similarity	NPC271921
0.5949	Remote Similarity	NPC148192
0.5949	Remote Similarity	NPC104537
0.5949	Remote Similarity	NPC473829
0.5946	Remote Similarity	NPC321030
0.593	Remote Similarity	NPC474702
0.5909	Remote Similarity	NPC474312
0.5875	Remote Similarity	NPC141481
0.5875	Remote Similarity	NPC273508
0.5875	Remote Similarity	NPC23721
0.5875	Remote Similarity	NPC473559
0.5875	Remote Similarity	NPC224700
0.5875	Remote Similarity	NPC324981
0.5875	Remote Similarity	NPC48218
0.5875	Remote Similarity	NPC320663
0.5875	Remote Similarity	NPC209327
0.5867	Remote Similarity	NPC473866
0.5862	Remote Similarity	NPC207657
0.5854	Remote Similarity	NPC54460
0.5851	Remote Similarity	NPC282705
0.5851	Remote Similarity	NPC182632
0.5823	Remote Similarity	NPC315141
0.5823	Remote Similarity	NPC129995
0.5811	Remote Similarity	NPC121034
0.5806	Remote Similarity	NPC39290
0.5806	Remote Similarity	NPC159369
0.5802	Remote Similarity	NPC473772
0.5778	Remote Similarity	NPC477199
0.5769	Remote Similarity	NPC475221
0.5765	Remote Similarity	NPC330017
0.5745	Remote Similarity	NPC242503
0.5745	Remote Similarity	NPC74672
0.5745	Remote Similarity	NPC139782
0.5745	Remote Similarity	NPC43074
0.5745	Remote Similarity	NPC209047
0.5732	Remote Similarity	NPC476660
0.5729	Remote Similarity	NPC262312
0.5729	Remote Similarity	NPC23454
0.5729	Remote Similarity	NPC70323
0.5729	Remote Similarity	NPC35269
0.5714	Remote Similarity	NPC29468
0.5714	Remote Similarity	NPC470993
0.5714	Remote Similarity	NPC470992
0.5714	Remote Similarity	NPC47333
0.5714	Remote Similarity	NPC321838
0.5696	Remote Similarity	NPC477525
0.5684	Remote Similarity	NPC61894
0.5684	Remote Similarity	NPC475125
0.5684	Remote Similarity	NPC111567
0.5684	Remote Similarity	NPC473604
0.5684	Remote Similarity	NPC473581
0.5684	Remote Similarity	NPC473950
0.5684	Remote Similarity	NPC475603
0.5684	Remote Similarity	NPC309898
0.5684	Remote Similarity	NPC186840
0.5684	Remote Similarity	NPC263545
0.5684	Remote Similarity	NPC15851
0.5679	Remote Similarity	NPC249713
0.5667	Remote Similarity	NPC315559
0.5667	Remote Similarity	NPC228638
0.5658	Remote Similarity	NPC312826
0.5652	Remote Similarity	NPC318549
0.5641	Remote Similarity	NPC471023
0.5634	Remote Similarity	NPC55383
0.5634	Remote Similarity	NPC93639
0.5612	Remote Similarity	NPC45313
0.56	Remote Similarity	NPC323436
0.56	Remote Similarity	NPC52012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	47
0.1-0.2	1027
0.2-0.3	5177
0.3-0.4	2406
0.4-0.5	473
0.5-0.6	23
0.6-0.7	6
0.7-0.8	2
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
0.7794	Intermediate Similarity	NPD6949	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3212	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6950	Discontinued
0.6462	Remote Similarity	NPD9463	Phase 3
0.6462	Remote Similarity	NPD9462	Approved
0.6267	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7347	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8277	Approved
0.5895	Remote Similarity	NPD6948	Phase 3
0.5882	Remote Similarity	NPD4840	Approved
0.5875	Remote Similarity	NPD8278	Approved
0.5745	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD585	Clinical (unspecified phase)

Structure

NPC474675 OpenBabel07101718312D 32 31 0 0 1 0 0 0 0 0999 V2000 15.1244 5.0000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1244 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2583 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3923 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5263 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6603 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7942 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9282 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0622 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7321 5.0000 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 3.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 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 3.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.0000 0.0000 C 0 0 1 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 2.1340 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 -0.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 3.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 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 20 1 0 0 0 0 19 21 1 0 0 0 0 19 25 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 31 1 0 0 0 0 24 26 1 1 0 0 0 27 32 2 0 0 0 0 28 32 1 0 0 0 0 30 32 1 0 0 0 0 31 32 1 0 0 0 0 M CHG 2 25 1 28 -1 M END $$$$

External Identifiers

PubChem CID	10480267
ChEMBL	CHEMBL479109
ZINC

Physicochemical Properties

Molecular Weight:	479.34
ALogP:	-5.0623
MLogP:	3.22
XLogP:	5.253
# Rotatable Bonds:	29
Polar Surface Area:	97.86
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	32

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