NPASS Natural Product

Natural Product: NPC329906

Natural Product ID:	NPC329906
Common Name:	1-O-[(Z)-(2S)-2-Methoxy-12-Methyloctadeca-7,17-Dien-5-Ynoyl]-Sn-Glycero-3-Phosphocholine
IUPAC Name:	[(2R)-2-hydroxy-3-[(2S,7Z)-2-methoxy-12-methyloctadeca-7,17-dien-5-ynoyl]oxypropoxy]-[2-(trimethylazaniumyl)ethyl]phosphinate
Synonyms:
Molecular Formula:	C28H50NO7P
Standard InCHIKey:	TWBNKXFGAHSGNJ-AFWIEJNYSA-N
Standard InCHI:	InChI=1S/C28H50NO7P/c1-7-8-9-15-18-25(2)19-16-13-11-10-12-14-17-20-27(34-6)28(31)35-23-26(30)24-36-37(32,33)22-21-29(3,4)5/h7,10-11,25-27,30H,1,8-9,13,15-24H2,2-6H3/b11-10-/t25?,26-,27+/m1/s1
Canonical SMILES:	C=CCCCCC(CCC/C=CC#CCC[C@@H](C(=O)OC[C@H](COP(=O)(CC[N+](C)(C)C)[O-])O)OC)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
NPO33189	Stelletta sp.	Species	Ancorinidae	Eukaryota				PMID[12762820]

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
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	13.6	ug/ml	22197393
NPT81	Cell Line	A549	Homo sapiens	ED50	=	11.8	ug/ml	22197393
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	9.1	ug/ml	22197393
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	15.1	ug/ml	22197393
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	14.5	ug/ml	22197393

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 NPC329906 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	51
0.1-0.2	450
0.2-0.3	5429
0.3-0.4	14062
0.4-0.5	8529
0.5-0.6	2296
0.6-0.7	57
0.7-0.8	14
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8023	Intermediate Similarity	NPC470899
0.7802	Intermediate Similarity	NPC196102
0.7802	Intermediate Similarity	NPC178758
0.7558	Intermediate Similarity	NPC477981
0.7558	Intermediate Similarity	NPC477983
0.7416	Intermediate Similarity	NPC330017
0.7333	Intermediate Similarity	NPC325936
0.7209	Intermediate Similarity	NPC273508
0.7209	Intermediate Similarity	NPC477980
0.7209	Intermediate Similarity	NPC209327
0.7176	Intermediate Similarity	NPC477982
0.7126	Intermediate Similarity	NPC475930
0.7126	Intermediate Similarity	NPC127145
0.7079	Intermediate Similarity	NPC305223
0.7045	Intermediate Similarity	NPC474674
0.6989	Remote Similarity	NPC474702
0.6932	Remote Similarity	NPC137620
0.6932	Remote Similarity	NPC474675
0.6737	Remote Similarity	NPC200446
0.6632	Remote Similarity	NPC209995
0.6526	Remote Similarity	NPC469495
0.6526	Remote Similarity	NPC11796
0.6526	Remote Similarity	NPC218817
0.6484	Remote Similarity	NPC170963
0.6484	Remote Similarity	NPC169976
0.6484	Remote Similarity	NPC114640
0.6484	Remote Similarity	NPC33267
0.6484	Remote Similarity	NPC324165
0.6484	Remote Similarity	NPC126366
0.6477	Remote Similarity	NPC476654
0.6477	Remote Similarity	NPC476657
0.6477	Remote Similarity	NPC476655
0.6404	Remote Similarity	NPC476659
0.6404	Remote Similarity	NPC476656
0.6395	Remote Similarity	NPC321919
0.6395	Remote Similarity	NPC81896
0.6354	Remote Similarity	NPC317263
0.6333	Remote Similarity	NPC475443
0.6333	Remote Similarity	NPC148192
0.6333	Remote Similarity	NPC127091
0.6333	Remote Similarity	NPC473829
0.6333	Remote Similarity	NPC330426
0.6333	Remote Similarity	NPC104537
0.6333	Remote Similarity	NPC22101
0.6333	Remote Similarity	NPC271921
0.6292	Remote Similarity	NPC238646
0.6264	Remote Similarity	NPC48218
0.6264	Remote Similarity	NPC473559
0.6264	Remote Similarity	NPC141481
0.6264	Remote Similarity	NPC324981
0.6237	Remote Similarity	NPC54460
0.6224	Remote Similarity	NPC103634
0.6211	Remote Similarity	NPC81052
0.6196	Remote Similarity	NPC473772
0.618	Remote Similarity	NPC476658
0.6163	Remote Similarity	NPC329819
0.6154	Remote Similarity	NPC473357
0.6154	Remote Similarity	NPC193029
0.6132	Remote Similarity	NPC478036
0.6132	Remote Similarity	NPC478037
0.6129	Remote Similarity	NPC476660
0.6129	Remote Similarity	NPC470268
0.6105	Remote Similarity	NPC160540
0.61	Remote Similarity	NPC477487
0.6078	Remote Similarity	NPC475206
0.6068	Remote Similarity	NPC261750
0.6068	Remote Similarity	NPC1111
0.6058	Remote Similarity	NPC201046
0.6022	Remote Similarity	NPC130618
0.6	Remote Similarity	NPC39290
0.6	Remote Similarity	NPC477984
0.6	Remote Similarity	NPC159369
0.598	Remote Similarity	NPC9868
0.5962	Remote Similarity	NPC179659
0.5957	Remote Similarity	NPC42526
0.5955	Remote Similarity	NPC321838
0.5943	Remote Similarity	NPC158388
0.5943	Remote Similarity	NPC478003
0.5943	Remote Similarity	NPC313670
0.5943	Remote Similarity	NPC478004
0.5938	Remote Similarity	NPC474321
0.5932	Remote Similarity	NPC60432
0.5926	Remote Similarity	NPC121825
0.5918	Remote Similarity	NPC40049
0.5914	Remote Similarity	NPC224700
0.5914	Remote Similarity	NPC320663
0.5909	Remote Similarity	NPC476344
0.5909	Remote Similarity	NPC473866
0.5893	Remote Similarity	NPC472753
0.5889	Remote Similarity	NPC54925
0.5882	Remote Similarity	NPC469597
0.5882	Remote Similarity	NPC315559
0.5877	Remote Similarity	NPC64168
0.5872	Remote Similarity	NPC150041
0.587	Remote Similarity	NPC83965
0.5868	Remote Similarity	NPC475642
0.5862	Remote Similarity	NPC323436
0.5859	Remote Similarity	NPC127526
0.5859	Remote Similarity	NPC474833
0.5856	Remote Similarity	NPC313440
0.5851	Remote Similarity	NPC101622
0.5842	Remote Similarity	NPC474894
0.5842	Remote Similarity	NPC112868
0.5841	Remote Similarity	NPC472754
0.5833	Remote Similarity	NPC469645
0.5833	Remote Similarity	NPC167145
0.5833	Remote Similarity	NPC469692
0.5826	Remote Similarity	NPC154601
0.5825	Remote Similarity	NPC474776
0.5825	Remote Similarity	NPC243618
0.5825	Remote Similarity	NPC70424
0.5824	Remote Similarity	NPC34883
0.5818	Remote Similarity	NPC255410
0.5816	Remote Similarity	NPC469514
0.5816	Remote Similarity	NPC474527
0.5816	Remote Similarity	NPC279537
0.5816	Remote Similarity	NPC471726
0.581	Remote Similarity	NPC248602
0.581	Remote Similarity	NPC45409
0.5806	Remote Similarity	NPC478100
0.5806	Remote Similarity	NPC25298
0.58	Remote Similarity	NPC321728
0.58	Remote Similarity	NPC471537
0.5798	Remote Similarity	NPC275100
0.5794	Remote Similarity	NPC471399
0.5794	Remote Similarity	NPC473448
0.5789	Remote Similarity	NPC173690
0.5789	Remote Similarity	NPC472750
0.5789	Remote Similarity	NPC6271
0.5789	Remote Similarity	NPC199831
0.5789	Remote Similarity	NPC473361
0.5789	Remote Similarity	NPC68001
0.5789	Remote Similarity	NPC472747
0.5789	Remote Similarity	NPC279833
0.5789	Remote Similarity	NPC80439
0.5789	Remote Similarity	NPC474828
0.5789	Remote Similarity	NPC318766
0.5789	Remote Similarity	NPC4299
0.5789	Remote Similarity	NPC474827
0.5789	Remote Similarity	NPC329904
0.5785	Remote Similarity	NPC30196
0.5784	Remote Similarity	NPC474252
0.5784	Remote Similarity	NPC474291
0.5784	Remote Similarity	NPC313677
0.5778	Remote Similarity	NPC66460
0.5778	Remote Similarity	NPC64971
0.5778	Remote Similarity	NPC271282
0.5778	Remote Similarity	NPC325929
0.5773	Remote Similarity	NPC330016
0.5773	Remote Similarity	NPC474551
0.5773	Remote Similarity	NPC104644
0.5773	Remote Similarity	NPC107654
0.5769	Remote Similarity	NPC477746
0.5769	Remote Similarity	NPC477747
0.5766	Remote Similarity	NPC52820
0.5766	Remote Similarity	NPC120299
0.5761	Remote Similarity	NPC176215
0.5761	Remote Similarity	NPC296436
0.5758	Remote Similarity	NPC281296
0.5755	Remote Similarity	NPC309656
0.5743	Remote Similarity	NPC233377
0.5743	Remote Similarity	NPC469920
0.5741	Remote Similarity	NPC208839
0.5741	Remote Similarity	NPC472199
0.5741	Remote Similarity	NPC184463
0.5741	Remote Similarity	NPC472197
0.5739	Remote Similarity	NPC472748
0.5739	Remote Similarity	NPC472756
0.5738	Remote Similarity	NPC6531
0.573	Remote Similarity	NPC328786
0.573	Remote Similarity	NPC329424
0.573	Remote Similarity	NPC201338
0.573	Remote Similarity	NPC474627
0.5728	Remote Similarity	NPC11620
0.5728	Remote Similarity	NPC16488
0.5728	Remote Similarity	NPC161045
0.5727	Remote Similarity	NPC54905
0.5727	Remote Similarity	NPC314009
0.5727	Remote Similarity	NPC300710
0.5714	Remote Similarity	NPC474411
0.5714	Remote Similarity	NPC29697
0.5714	Remote Similarity	NPC472009
0.5714	Remote Similarity	NPC475753
0.5714	Remote Similarity	NPC199445
0.5714	Remote Similarity	NPC475653
0.5714	Remote Similarity	NPC202394
0.5714	Remote Similarity	NPC161855
0.5714	Remote Similarity	NPC477993
0.5714	Remote Similarity	NPC21713
0.5714	Remote Similarity	NPC258824
0.5714	Remote Similarity	NPC477994
0.5714	Remote Similarity	NPC469483
0.5714	Remote Similarity	NPC474431
0.5714	Remote Similarity	NPC217725
0.5714	Remote Similarity	NPC475608
0.5702	Remote Similarity	NPC473596
0.57	Remote Similarity	NPC27949
0.57	Remote Similarity	NPC192006
0.57	Remote Similarity	NPC121200
0.57	Remote Similarity	NPC3852

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	63
0.1-0.2	636
0.2-0.3	4172
0.3-0.4	3286
0.4-0.5	812
0.5-0.6	189
0.6-0.7	3
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
0.6163	Remote Similarity	NPD6109	Phase 1
0.6022	Remote Similarity	NPD8277	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.5955	Remote Similarity	NPD6949	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6435	Approved
0.5914	Remote Similarity	NPD8278	Approved
0.59	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7983	Approved
0.5882	Remote Similarity	NPD5332	Approved
0.5882	Remote Similarity	NPD5331	Approved
0.5882	Remote Similarity	NPD7154	Phase 3
0.5833	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7641	Discontinued
0.5794	Remote Similarity	NPD46	Approved
0.5794	Remote Similarity	NPD6698	Approved
0.5769	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4821	Approved
0.5743	Remote Similarity	NPD4822	Approved
0.5743	Remote Similarity	NPD4820	Approved
0.5743	Remote Similarity	NPD4819	Approved
0.5743	Remote Similarity	NPD5368	Approved
0.57	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4271	Approved
0.57	Remote Similarity	NPD4268	Approved
0.5686	Remote Similarity	NPD5369	Approved
0.5676	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD7838	Discovery
0.563	Remote Similarity	NPD6421	Discontinued
0.5625	Remote Similarity	NPD3212	Clinical (unspecified phase)

Structure

NPC329906 OpenBabel07101718232D 37 36 0 0 1 0 0 0 0 0999 V2000 13.3660 -5.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8660 -9.4282 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 1.8660 -5.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8660 -5.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3660 -6.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3660 -6.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 -10.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3660 -10.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -9.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8660 -9.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 -8.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8660 -7.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8660 -9.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 -7.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8660 -7.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3660 -8.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 -7.6962 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 2.3660 -5.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3660 -8.5622 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.8660 -4.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3660 -6.8301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8660 -5.9641 0.0000 C 0 0 0 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 0.8660 -4.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 -5.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1340 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 2.3660 -6.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 -5.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 25 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 6 34 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 15 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 3 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 25 1 0 0 0 0 19 25 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 37 1 0 0 0 0 23 26 1 0 0 0 0 23 35 1 0 0 0 0 24 26 1 0 0 0 0 24 36 1 0 0 0 0 26 30 1 1 0 0 0 27 20 1 6 0 0 0 27 28 1 0 0 0 0 27 34 1 0 0 0 0 28 31 2 0 0 0 0 28 35 1 0 0 0 0 32 37 2 0 0 0 0 33 37 1 0 0 0 0 36 37 1 0 0 0 0 M CHG 2 29 1 33 -1 M END $$$$

External Identifiers

PubChem CID	44584542
ChEMBL	CHEMBL2304267
ZINC

Physicochemical Properties

Molecular Weight:	543.33
ALogP:	-1.8707
MLogP:	3.55
XLogP:	5.373
# Rotatable Bonds:	29
Polar Surface Area:	114.93
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	37

Download Data

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