NPASS Natural Product

Natural Product: NPC97614

Natural Product ID:	NPC97614
Common Name:	Serinolamide A
IUPAC Name:	(E)-N-[(2R)-1-hydroxy-3-methoxypropan-2-yl]-N-methyloctadec-4-enamide
Synonyms:	Serinolamide A
Molecular Formula:	C23H45NO3
Standard InCHIKey:	CJAVPRNATZCNLN-NBRGKURFSA-N
Standard InCHI:	InChI=1S/C23H45NO3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)24(2)22(20-25)21-27-3/h16-17,22,25H,4-15,18-21H2,1-3H3/b17-16+/t22-/m1/s1
Canonical SMILES:	CCCCCCCCCCCCC/C=C/CCC(=O)N([C@@H](COC)CO)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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria				PMID[21999614]

Biological Activity

Activity Type	# Activity
IC50	2
Ki	1
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1300	nM	21999614
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	2300	nM	21999614
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	IC50	>	10000	nM	21999614
NPT2	Others	Unspecified		Ratio IC50	>	5		21999614
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	0	%	21999614
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	60	%	21999614

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 NPC97614 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	36
0.1-0.2	268
0.2-0.3	16193
0.3-0.4	10830
0.4-0.5	3047
0.5-0.6	449
0.6-0.7	63
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	Natural Product ID
0.7821	Intermediate Similarity	NPC477523
0.7722	Intermediate Similarity	NPC477524
0.7176	Intermediate Similarity	NPC324506
0.6962	Remote Similarity	NPC34672
0.6951	Remote Similarity	NPC209232
0.6632	Remote Similarity	NPC188785
0.6628	Remote Similarity	NPC475975
0.6623	Remote Similarity	NPC23721
0.6533	Remote Similarity	NPC206660
0.6486	Remote Similarity	NPC252684
0.6471	Remote Similarity	NPC277341
0.6471	Remote Similarity	NPC226982
0.642	Remote Similarity	NPC470993
0.642	Remote Similarity	NPC470994
0.642	Remote Similarity	NPC470992
0.64	Remote Similarity	NPC55068
0.6374	Remote Similarity	NPC53240
0.6364	Remote Similarity	NPC476328
0.6354	Remote Similarity	NPC233932
0.6353	Remote Similarity	NPC19497
0.6329	Remote Similarity	NPC475930
0.6329	Remote Similarity	NPC137620
0.6329	Remote Similarity	NPC127145
0.6329	Remote Similarity	NPC474675
0.6329	Remote Similarity	NPC280065
0.6329	Remote Similarity	NPC45060
0.6327	Remote Similarity	NPC476877
0.6277	Remote Similarity	NPC469739
0.6267	Remote Similarity	NPC29468
0.625	Remote Similarity	NPC474674
0.6238	Remote Similarity	NPC476276
0.6234	Remote Similarity	NPC477525
0.6216	Remote Similarity	NPC133923
0.6216	Remote Similarity	NPC326524
0.6216	Remote Similarity	NPC329003
0.6216	Remote Similarity	NPC325550
0.6207	Remote Similarity	NPC474312
0.6203	Remote Similarity	NPC96272
0.6203	Remote Similarity	NPC249713
0.62	Remote Similarity	NPC476876
0.6184	Remote Similarity	NPC477106
0.6154	Remote Similarity	NPC113224
0.6145	Remote Similarity	NPC3094
0.6136	Remote Similarity	NPC196102
0.6136	Remote Similarity	NPC178758
0.6133	Remote Similarity	NPC130807
0.6133	Remote Similarity	NPC42477
0.6125	Remote Similarity	NPC103712
0.6125	Remote Similarity	NPC291196
0.6118	Remote Similarity	NPC474833
0.6111	Remote Similarity	NPC242930
0.6098	Remote Similarity	NPC26932
0.6098	Remote Similarity	NPC305223
0.6081	Remote Similarity	NPC321030
0.6081	Remote Similarity	NPC385
0.6078	Remote Similarity	NPC207820
0.6064	Remote Similarity	NPC38172
0.6058	Remote Similarity	NPC476875
0.6053	Remote Similarity	NPC47333
0.6047	Remote Similarity	NPC471768
0.6022	Remote Similarity	NPC17143
0.6022	Remote Similarity	NPC47230
0.6	Remote Similarity	NPC46268
0.6	Remote Similarity	NPC325936
0.6	Remote Similarity	NPC163537
0.6	Remote Similarity	NPC474812
0.5962	Remote Similarity	NPC251122
0.5952	Remote Similarity	NPC217095
0.5952	Remote Similarity	NPC264417
0.5952	Remote Similarity	NPC281154
0.593	Remote Similarity	NPC473972
0.593	Remote Similarity	NPC475363
0.593	Remote Similarity	NPC473971
0.5914	Remote Similarity	NPC81195
0.5914	Remote Similarity	NPC39290
0.5914	Remote Similarity	NPC159369
0.5909	Remote Similarity	NPC82799
0.5888	Remote Similarity	NPC472536
0.5888	Remote Similarity	NPC103391
0.5854	Remote Similarity	NPC470662
0.5854	Remote Similarity	NPC324638
0.5849	Remote Similarity	NPC314550
0.5833	Remote Similarity	NPC78562
0.5833	Remote Similarity	NPC473588
0.5833	Remote Similarity	NPC288086
0.5824	Remote Similarity	NPC319913
0.5824	Remote Similarity	NPC264014
0.5816	Remote Similarity	NPC91036
0.5804	Remote Similarity	NPC273185
0.58	Remote Similarity	NPC77703
0.5795	Remote Similarity	NPC79367
0.5784	Remote Similarity	NPC205176
0.5769	Remote Similarity	NPC171734
0.5769	Remote Similarity	NPC316674
0.5765	Remote Similarity	NPC62293
0.5765	Remote Similarity	NPC212008
0.5765	Remote Similarity	NPC51055
0.5765	Remote Similarity	NPC140327
0.5761	Remote Similarity	NPC322672
0.5758	Remote Similarity	NPC475758
0.5743	Remote Similarity	NPC474244
0.573	Remote Similarity	NPC6902
0.573	Remote Similarity	NPC184473
0.573	Remote Similarity	NPC284456
0.5714	Remote Similarity	NPC326126
0.5714	Remote Similarity	NPC470943
0.57	Remote Similarity	NPC475791
0.57	Remote Similarity	NPC13175
0.5699	Remote Similarity	NPC473525
0.5696	Remote Similarity	NPC476658
0.5667	Remote Similarity	NPC473810
0.5658	Remote Similarity	NPC325734
0.5657	Remote Similarity	NPC52820
0.5644	Remote Similarity	NPC144714
0.5644	Remote Similarity	NPC100810
0.5641	Remote Similarity	NPC477459
0.5641	Remote Similarity	NPC201939
0.5641	Remote Similarity	NPC477461
0.5641	Remote Similarity	NPC51166
0.5638	Remote Similarity	NPC155230
0.5634	Remote Similarity	NPC59051
0.5632	Remote Similarity	NPC308050
0.5631	Remote Similarity	NPC476921
0.5625	Remote Similarity	NPC176215
0.5625	Remote Similarity	NPC476654
0.5625	Remote Similarity	NPC476655
0.5625	Remote Similarity	NPC476657
0.5625	Remote Similarity	NPC145707
0.5625	Remote Similarity	NPC296436
0.5619	Remote Similarity	NPC474099
0.5616	Remote Similarity	NPC284224

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC97614 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	55
0.1-0.2	306
0.2-0.3	4498
0.3-0.4	3303
0.4-0.5	928
0.5-0.6	69
0.6-0.7	2
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
0.64	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6949	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD1452	Discontinued
0.5854	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD9512	Approved
0.5747	Remote Similarity	NPD3732	Approved
0.5714	Remote Similarity	NPD9511	Approved
0.5676	Remote Similarity	NPD4281	Clinical (unspecified phase)

Structure

CID97614 OpenBabel06191715432D 27 26 0 0 1 0 0 0 0 0999 V2000 13.8564 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 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 -2.5981 1.5000 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 -1.7321 1.0000 0.0000 C 0 0 2 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 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 24 1 0 0 0 0 3 27 1 0 0 0 0 4 5 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 19 1 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 0 0 0 0 22 20 1 1 0 0 0 22 24 1 0 0 0 0 23 24 1 0 0 0 0 23 26 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	56597771
ChEMBL	CHEMBL1928586
ZINC

Physicochemical Properties

Molecular Weight:	383.34
ALogP:	-3.1747
MLogP:	3.55
XLogP:	7.262
# Rotatable Bonds:	24
Polar Surface Area:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	27

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