NPASS Natural Product

Natural Product: NPC55068

Natural Product ID:	NPC55068
Common Name:	Sphingosine
IUPAC Name:	(E,2S,3R)-2-aminooctadec-4-ene-1,3-diol
Synonyms:	D-Sphingosine
Molecular Formula:	C18H37NO2
Standard InCHIKey:	WWUZIQQURGPMPG-KRWOKUGFSA-N
Standard InCHI:	InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
Canonical SMILES:	CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota		PMID[24731183]
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	blood	PMID[17085324]
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	urine	PMID[11339295]
NPO20338	Mus musculus	Species	Muridae	Eukaryota		PMID[19425150]
NPO25096	Cucurbitae moschatae semen	NA	NA	NA		TCMSP*
NPO29672	Benincasae semen	NA	NA	NA		TCMSP*
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota		TM-MC*

Biological Activity

Activity Type	# Activity
EC50	4
ED50	2
IC50	22
MIC	6
Others	9
Potency	47

Activity Type	# Activity
Cell Line	8
Individual Protein	43
Organism	14
Others	17
Protein Family	6
Protein-Protein Interaction	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1284	Protein Family	Protein kinase C (PKC)	Rattus norvegicus	IC50	=	23400	nM	10.1016/0960-894X(95)00428-V
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	IC50	=	4200	nM	10.1016/0960-894X(95)00428-V
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.31	mg ear-1	10.1016/0960-894X(95)00428-V
NPT3191	Cell Line	Leukemia 60 cell line		TC50	=	2.42	nM	10636242
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	30	ug/ml	12127527
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	100000	nM	12127527
NPT1284	Protein Family	Protein kinase C (PKC)	Rattus norvegicus	IC50	=	40000	nM	8289196
NPT1284	Protein Family	Protein kinase C (PKC)	Rattus norvegicus	IC50	=	23000	nM	8289196
NPT1284	Protein Family	Protein kinase C (PKC)	Rattus norvegicus	IC50	=	6700	nM	10.1016/0960-894X(95)00427-U
NPT1284	Protein Family	Protein kinase C (PKC)	Rattus norvegicus	IC50	=	23400	nM	10.1016/0960-894X(95)00427-U
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.31	mg ear-1	10.1016/0960-894X(95)00427-U
NPT910	Individual Protein	Cholesteryl ester transfer protein	Homo sapiens	IC50	=	11500	nM	10.1016/S0960-894X(97)00248-5
NPT3030	Protein Family	Protein kinase C, PKC; classical	Rattus norvegicus	IC50	=	57000	nM	1895309
NPT3192	Individual Protein	cAMP-dependent protein kinase alpha-catalytic subunit	Rattus norvegicus	IC50	=	98	nM	1895309
NPT3193	Individual Protein	Sphingosine kinase 1	Homo sapiens	Activity	=	100	%	17070046
NPT3194	Individual Protein	Sphingosine kinase 2	Homo sapiens	Activity	=	100	%	17070046
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	2010	nM	17400555
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	3480	nM	17400555
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	2880	nM	17400555
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	3380	nM	17400555
NPT15	Cell Line	Jurkat	Homo sapiens	Ratio IC50	=	1.7		17400555
NPT15	Cell Line	Jurkat	Homo sapiens	Ratio IC50	=	1.4		17400555
NPT3195	Organism	Ulva	Ulva	Activity	=	15	%	9644076
NPT3195	Organism	Ulva	Ulva	Activity	=	0	%	9644076
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	6	ug/ml	18778047
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2	ug/ml	18778047
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4	ug/ml	18778047
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	42	ug/ml	18778047
NPT3193	Individual Protein	Sphingosine kinase 1	Homo sapiens	IC50	=	3860	nM	19467599
NPT3194	Individual Protein	Sphingosine kinase 2	Homo sapiens	IC50	=	1560	nM	19467599
NPT554	Organism	Candida glabrata	Candida glabrata	Activity	=	30	ug/ml	20171099
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	8099	nM	PubChem BioAssay data set
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	5011.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	17782.8	nM	PubChem BioAssay data set
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	1519	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	15848.9	nM	PubChem BioAssay data set
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	631	nM	PubChem BioAssay data set
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT794	Individual Protein	Endonuclease 4	Escherichia coli K-12	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	79432.8	nM	PubChem BioAssay data set
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	19952.6	nM	PubChem BioAssay data set
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	>	150000	nM	PubChem BioAssay data set
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	22387.2	nM	PubChem BioAssay data set
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	44668.4	nM	PubChem BioAssay data set
NPT501	Individual Protein	Alpha-galactosidase A	Homo sapiens	Potency	=	4466.8	nM	PubChem BioAssay data set
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	2560	nM	PubChem BioAssay data set
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	>	150000	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	11.2	nM	PubChem BioAssay data set
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency		12589.3	nM	PubChem BioAssay data set
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency		25118.9	nM	PubChem BioAssay data set
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency		2818.4	nM	PubChem BioAssay data set
NPT2800	Individual Protein	Bcl-2-related protein A1	Mus musculus	IC50	>	20000	nM	PubChem BioAssay data set
NPT2801	Individual Protein	Ubiquitin-conjugating enzyme E2 N	Homo sapiens	IC50	=	6425	nM	PubChem BioAssay data set
NPT2801	Individual Protein	Ubiquitin-conjugating enzyme E2 N	Homo sapiens	IC50	=	6200	nM	PubChem BioAssay data set
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency		14125.4	nM	PubChem BioAssay data set
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency		39810.7	nM	PubChem BioAssay data set
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency		56234.1	nM	PubChem BioAssay data set
NPT1109	Individual Protein	Apelin receptor	Homo sapiens	IC50	>	66600	nM	PubChem BioAssay data set
NPT1110	Individual Protein	C-C chemokine receptor type 6	Homo sapiens	IC50	=	20900	nM	PubChem BioAssay data set
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency		89125.1	nM	PubChem BioAssay data set
NPT98	Individual Protein	HERG	Homo sapiens	Potency		35481.3	nM	PubChem BioAssay data set
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency		35481.3	nM	PubChem BioAssay data set
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency		33807.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1000	nM	PubChem BioAssay data set
NPT1111	Individual Protein	C-X-C chemokine receptor type 5	Homo sapiens	IC50	=	32494	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		29092.9	nM	PubChem BioAssay data set
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency		70794.6	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		580.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		11582.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1636	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		9200	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		16360.1	nM	PubChem BioAssay data set
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency		29092.9	nM	PubChem BioAssay data set
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency		44668.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		11220.2	nM	PubChem BioAssay data set

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 NPC55068 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	33
0.1-0.2	357
0.2-0.3	13970
0.3-0.4	11212
0.4-0.5	4323
0.5-0.6	770
0.6-0.7	202
0.7-0.8	19
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8923	High Similarity	NPC324638
0.8308	Intermediate Similarity	NPC113224
0.8254	Intermediate Similarity	NPC47333
0.7941	Intermediate Similarity	NPC103712
0.7941	Intermediate Similarity	NPC291196
0.7639	Intermediate Similarity	NPC140327
0.7639	Intermediate Similarity	NPC51055
0.7639	Intermediate Similarity	NPC3094
0.7639	Intermediate Similarity	NPC212008
0.7639	Intermediate Similarity	NPC62293
0.7619	Intermediate Similarity	NPC168308
0.7619	Intermediate Similarity	NPC302569
0.75	Intermediate Similarity	NPC288086
0.7424	Intermediate Similarity	NPC29468
0.7353	Intermediate Similarity	NPC477525
0.7273	Intermediate Similarity	NPC130807
0.7213	Intermediate Similarity	NPC474495
0.7213	Intermediate Similarity	NPC473672
0.7213	Intermediate Similarity	NPC151782
0.7143	Intermediate Similarity	NPC79367
0.7143	Intermediate Similarity	NPC207657
0.7049	Intermediate Similarity	NPC72699
0.6984	Remote Similarity	NPC474496
0.6935	Remote Similarity	NPC59408
0.6935	Remote Similarity	NPC71053
0.6892	Remote Similarity	NPC314678
0.6892	Remote Similarity	NPC26932
0.6885	Remote Similarity	NPC85079
0.6885	Remote Similarity	NPC248884
0.6885	Remote Similarity	NPC31194
0.6885	Remote Similarity	NPC153538
0.6883	Remote Similarity	NPC475363
0.6883	Remote Similarity	NPC473971
0.6883	Remote Similarity	NPC473972
0.6875	Remote Similarity	NPC473532
0.6875	Remote Similarity	NPC256209
0.6875	Remote Similarity	NPC49059
0.6866	Remote Similarity	NPC326524
0.6866	Remote Similarity	NPC325550
0.6866	Remote Similarity	NPC329003
0.6835	Remote Similarity	NPC82799
0.6825	Remote Similarity	NPC123814
0.6812	Remote Similarity	NPC471023
0.68	Remote Similarity	NPC473588
0.68	Remote Similarity	NPC78562
0.6774	Remote Similarity	NPC473913
0.6774	Remote Similarity	NPC199286
0.6774	Remote Similarity	NPC477727
0.6774	Remote Similarity	NPC474642
0.6774	Remote Similarity	NPC471281
0.6774	Remote Similarity	NPC249670
0.6769	Remote Similarity	NPC473896
0.6769	Remote Similarity	NPC473735
0.6769	Remote Similarity	NPC473725
0.6769	Remote Similarity	NPC473721
0.6769	Remote Similarity	NPC475353
0.6769	Remote Similarity	NPC473910
0.6769	Remote Similarity	NPC477726
0.6769	Remote Similarity	NPC477725
0.6769	Remote Similarity	NPC242930
0.6761	Remote Similarity	NPC129995
0.6761	Remote Similarity	NPC315141
0.6716	Remote Similarity	NPC321030
0.6716	Remote Similarity	NPC181872
0.6711	Remote Similarity	NPC217095
0.6711	Remote Similarity	NPC264417
0.6667	Remote Similarity	NPC475477
0.6667	Remote Similarity	NPC170776
0.6667	Remote Similarity	NPC475384
0.6667	Remote Similarity	NPC470968
0.6667	Remote Similarity	NPC471959
0.6667	Remote Similarity	NPC55383
0.6667	Remote Similarity	NPC470967
0.6667	Remote Similarity	NPC89824
0.6667	Remote Similarity	NPC477723
0.6667	Remote Similarity	NPC471960
0.6667	Remote Similarity	NPC477661
0.6667	Remote Similarity	NPC9273
0.6667	Remote Similarity	NPC470969
0.6667	Remote Similarity	NPC470966
0.6667	Remote Similarity	NPC165447
0.6667	Remote Similarity	NPC76198
0.6667	Remote Similarity	NPC294278
0.6667	Remote Similarity	NPC197272
0.6667	Remote Similarity	NPC256656
0.6667	Remote Similarity	NPC329608
0.6667	Remote Similarity	NPC473847
0.6667	Remote Similarity	NPC224148
0.6667	Remote Similarity	NPC161838
0.6667	Remote Similarity	NPC93639
0.6618	Remote Similarity	NPC312826
0.6615	Remote Similarity	NPC110732
0.6613	Remote Similarity	NPC125122
0.6613	Remote Similarity	NPC471275
0.6613	Remote Similarity	NPC471276
0.6613	Remote Similarity	NPC471280
0.6567	Remote Similarity	NPC470970
0.6562	Remote Similarity	NPC474322
0.6557	Remote Similarity	NPC124183
0.6557	Remote Similarity	NPC55063
0.6557	Remote Similarity	NPC35141
0.6557	Remote Similarity	NPC19834
0.6508	Remote Similarity	NPC291437
0.6508	Remote Similarity	NPC328784
0.6508	Remote Similarity	NPC474460
0.6486	Remote Similarity	NPC127145
0.6486	Remote Similarity	NPC475930
0.6486	Remote Similarity	NPC280065
0.6486	Remote Similarity	NPC45060
0.6438	Remote Similarity	NPC470663
0.6429	Remote Similarity	NPC51166
0.6418	Remote Similarity	NPC8979
0.6406	Remote Similarity	NPC129263
0.6406	Remote Similarity	NPC261571
0.64	Remote Similarity	NPC97614
0.64	Remote Similarity	NPC315199
0.64	Remote Similarity	NPC474674
0.6393	Remote Similarity	NPC76976
0.6393	Remote Similarity	NPC160628
0.6393	Remote Similarity	NPC140501
0.6393	Remote Similarity	NPC269074
0.6377	Remote Similarity	NPC122239
0.6377	Remote Similarity	NPC475931
0.6375	Remote Similarity	NPC314762
0.6364	Remote Similarity	NPC48058
0.6351	Remote Similarity	NPC249713
0.6351	Remote Similarity	NPC23721
0.6349	Remote Similarity	NPC302310
0.6338	Remote Similarity	NPC477106
0.6333	Remote Similarity	NPC116934
0.6324	Remote Similarity	NPC193975
0.6308	Remote Similarity	NPC188341
0.6308	Remote Similarity	NPC35756
0.6308	Remote Similarity	NPC49494
0.6308	Remote Similarity	NPC142092
0.6286	Remote Similarity	NPC327112
0.6269	Remote Similarity	NPC146551
0.6269	Remote Similarity	NPC474513
0.6269	Remote Similarity	NPC317899
0.6269	Remote Similarity	NPC329686
0.6269	Remote Similarity	NPC470963
0.6269	Remote Similarity	NPC474644
0.6267	Remote Similarity	NPC137620
0.6267	Remote Similarity	NPC474675
0.6267	Remote Similarity	NPC471022
0.625	Remote Similarity	NPC235311
0.625	Remote Similarity	NPC253468
0.6234	Remote Similarity	NPC305223
0.6232	Remote Similarity	NPC226848
0.623	Remote Similarity	NPC108195
0.623	Remote Similarity	NPC101616
0.6212	Remote Similarity	NPC26102
0.6212	Remote Similarity	NPC217188
0.6212	Remote Similarity	NPC477724
0.6212	Remote Similarity	NPC34577
0.6212	Remote Similarity	NPC187361
0.6207	Remote Similarity	NPC15934
0.6197	Remote Similarity	NPC475984
0.619	Remote Similarity	NPC121062
0.619	Remote Similarity	NPC29222
0.619	Remote Similarity	NPC96966
0.6176	Remote Similarity	NPC104138
0.6176	Remote Similarity	NPC311648
0.6176	Remote Similarity	NPC261158
0.6176	Remote Similarity	NPC470964
0.6176	Remote Similarity	NPC24216
0.6176	Remote Similarity	NPC306420
0.6176	Remote Similarity	NPC473865
0.6176	Remote Similarity	NPC474643
0.6167	Remote Similarity	NPC249801
0.6167	Remote Similarity	NPC46248
0.6164	Remote Similarity	NPC245947
0.6164	Remote Similarity	NPC255863
0.6164	Remote Similarity	NPC136164
0.6164	Remote Similarity	NPC308844
0.6154	Remote Similarity	NPC470993
0.6154	Remote Similarity	NPC470992
0.6145	Remote Similarity	NPC474312
0.6143	Remote Similarity	NPC319131
0.6143	Remote Similarity	NPC74617
0.6143	Remote Similarity	NPC150505
0.6136	Remote Similarity	NPC74672
0.6136	Remote Similarity	NPC43074
0.6136	Remote Similarity	NPC242503
0.6136	Remote Similarity	NPC209047
0.6136	Remote Similarity	NPC139782
0.6111	Remote Similarity	NPC29697
0.6111	Remote Similarity	NPC470965
0.6087	Remote Similarity	NPC44542
0.6087	Remote Similarity	NPC48968
0.6087	Remote Similarity	NPC594
0.6071	Remote Similarity	NPC228638
0.6067	Remote Similarity	NPC263545
0.6067	Remote Similarity	NPC186840
0.6067	Remote Similarity	NPC15851
0.6067	Remote Similarity	NPC182632
0.6067	Remote Similarity	NPC473604
0.6067	Remote Similarity	NPC473950
0.6067	Remote Similarity	NPC282705
0.6067	Remote Similarity	NPC475125

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC55068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	51
0.1-0.2	629
0.2-0.3	4973
0.3-0.4	2876
0.4-0.5	545
0.5-0.6	79
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3210	Clinical (unspecified phase)
0.8923	High Similarity	NPD3212	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3215	Phase 1
0.6508	Remote Similarity	NPD3214	Discontinued
0.6393	Remote Similarity	NPD4265	Approved
0.6286	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD3732	Approved
0.5972	Remote Similarity	NPD6949	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD585	Clinical (unspecified phase)
0.56	Remote Similarity	NPD3197	Phase 1

Structure

External Identifiers

PubChem CID	5280335
ChEMBL	CHEMBL67166
ZINC

Physicochemical Properties

Molecular Weight:	299.28
ALogP:	-4.153
MLogP:	3.11
XLogP:	6.018
# Rotatable Bonds:	19
Polar Surface Area:	66.48
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	21

Download Data

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General Info & Identifiers & Properties
Structure MOL file
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Biological Activities
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