NPASS Natural Product

Natural Product: NPC325900

Natural Product ID:	NPC325900
Common Name:	Nbeta-Acetylstreptothricin D
IUPAC Name:	[(2R,3R,4S,5R,6R)-6-[[(3aS,7R,7aS)-7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl]amino]-5-[[(3S)-3-acetamido-6-[[(3S)-3-amino-6-[[(3S)-3,6-diaminohexanoyl]amino]hexanoyl]amino]hexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] carbamate
Synonyms:	N-Beta-Acetylstreptothricin D
Molecular Formula:	C33H60N12O11
Standard InCHIKey:	WPMGFKKSCCXUAK-YFZUDYRPSA-N
Standard InCHI:	InChI=1S/C33H60N12O11/c1-16(47)41-19(7-4-10-39-23(50)12-18(36)6-3-9-38-22(49)11-17(35)5-2-8-34)13-24(51)42-27-28(52)29(56-32(37)54)21(15-46)55-31(27)45-33-43-25-20(48)14-40-30(53)26(25)44-33/h17-21,25-29,31,46,48,52H,2-15,34-36H2,1H3,(H2,37,54)(H,38,49)(H,39,50)(H,40,53)(H,41,47)(H,42,51)(H2,43,44,45)/t17-,18-,19-,20+,21+,25+,26-,27+,28-,29-,31+/m0/s1
Canonical SMILES:	NCCC[C@@H](CC(=NCCC[C@@H](CC(=NCCC[C@@H](CC(=N[C@H]1[C@H](NC2=N[C@H]3[C@H](N2)C(=NC[C@H]3O)O)O[C@@H]([C@@H]([C@H]1O)OC(=N)O)CO)O)N=C(O)C)O)N)O)N
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
NPO31206	Streptomyces sp. i08a 1776	Species	Streptomycetaceae	Bacteria				PMID[21510638]

Biological Activity

Activity Type	# Activity
IC50	3
MIC	9

Activity Type	# Activity
Cell Line	3
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128	ug/ml	21510638
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	128	ug/ml	21510638
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128	ug/ml	21510638
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC	>	128	ug/ml	21510638
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	128	ug/ml	21510638
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128	ug/ml	21510638
NPT3495	Organism	Morganella morganii	Morganella morganii	MIC	>	128	ug/ml	21510638
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128	ug/ml	21510638
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128	ug/ml	21510638
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	21510638
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000	nM	21510638
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000	nM	21510638

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 NPC325900 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	195
0.1-0.2	9727
0.2-0.3	16441
0.3-0.4	3585
0.4-0.5	715
0.5-0.6	192
0.6-0.7	22
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC10897
0.9897	High Similarity	NPC92874
0.9897	High Similarity	NPC62845
0.9897	High Similarity	NPC322449
0.9897	High Similarity	NPC166242
0.9897	High Similarity	NPC189854
0.9794	High Similarity	NPC314398
0.9794	High Similarity	NPC239705
0.9794	High Similarity	NPC314413
0.8624	High Similarity	NPC470621
0.8624	High Similarity	NPC222481
0.8532	High Similarity	NPC259586
0.6923	Remote Similarity	NPC57436
0.6923	Remote Similarity	NPC121479
0.6777	Remote Similarity	NPC313813
0.6636	Remote Similarity	NPC216278
0.6387	Remote Similarity	NPC59589
0.6372	Remote Similarity	NPC330590
0.6328	Remote Similarity	NPC94319
0.625	Remote Similarity	NPC316807
0.6239	Remote Similarity	NPC306838
0.6238	Remote Similarity	NPC315806
0.6154	Remote Similarity	NPC314772
0.6154	Remote Similarity	NPC314968
0.6154	Remote Similarity	NPC315036
0.6107	Remote Similarity	NPC477518
0.6038	Remote Similarity	NPC70574
0.6038	Remote Similarity	NPC318258
0.6038	Remote Similarity	NPC100204
0.6038	Remote Similarity	NPC83248
0.6036	Remote Similarity	NPC214376
0.6019	Remote Similarity	NPC165119
0.6017	Remote Similarity	NPC56298
0.6017	Remote Similarity	NPC471628
0.5965	Remote Similarity	NPC328646
0.5946	Remote Similarity	NPC313552
0.5943	Remote Similarity	NPC98750
0.5941	Remote Similarity	NPC327486
0.5941	Remote Similarity	NPC223174
0.5941	Remote Similarity	NPC327753
0.5929	Remote Similarity	NPC195969
0.5929	Remote Similarity	NPC176381
0.5926	Remote Similarity	NPC36927
0.5926	Remote Similarity	NPC271772
0.5926	Remote Similarity	NPC242077
0.5909	Remote Similarity	NPC325750
0.5905	Remote Similarity	NPC329077
0.5893	Remote Similarity	NPC328806
0.5893	Remote Similarity	NPC314408
0.5893	Remote Similarity	NPC314007
0.5893	Remote Similarity	NPC43850
0.5893	Remote Similarity	NPC123746
0.5893	Remote Similarity	NPC477060
0.587	Remote Similarity	NPC318142
0.5865	Remote Similarity	NPC474467
0.5841	Remote Similarity	NPC470284
0.5804	Remote Similarity	NPC62927
0.5804	Remote Similarity	NPC190334
0.5798	Remote Similarity	NPC328914
0.5776	Remote Similarity	NPC315334
0.5752	Remote Similarity	NPC317377
0.5752	Remote Similarity	NPC319334
0.5752	Remote Similarity	NPC321485
0.5752	Remote Similarity	NPC322372
0.5752	Remote Similarity	NPC327517
0.5752	Remote Similarity	NPC470282
0.5727	Remote Similarity	NPC263058
0.5714	Remote Similarity	NPC471262
0.5714	Remote Similarity	NPC469363
0.5714	Remote Similarity	NPC139857
0.5704	Remote Similarity	NPC315058
0.5702	Remote Similarity	NPC275715
0.5701	Remote Similarity	NPC325902
0.5693	Remote Similarity	NPC313962
0.569	Remote Similarity	NPC208537
0.569	Remote Similarity	NPC270005
0.5688	Remote Similarity	NPC471420
0.5678	Remote Similarity	NPC90240
0.5646	Remote Similarity	NPC477519
0.5644	Remote Similarity	NPC129100
0.5644	Remote Similarity	NPC322801
0.5644	Remote Similarity	NPC291650
0.5639	Remote Similarity	NPC245534
0.5636	Remote Similarity	NPC315969
0.563	Remote Similarity	NPC313821
0.563	Remote Similarity	NPC75839
0.563	Remote Similarity	NPC68327
0.563	Remote Similarity	NPC328779
0.5625	Remote Similarity	NPC476523
0.561	Remote Similarity	NPC221148
0.5606	Remote Similarity	NPC477237

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC325900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	93
0.1-0.2	1554
0.2-0.3	5340
0.3-0.4	1643
0.4-0.5	319
0.5-0.6	170
0.6-0.7	42
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
0.6991	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD35	Approved
0.6923	Remote Similarity	NPD4833	Approved
0.6881	Remote Similarity	NPD6424	Approved
0.6838	Remote Similarity	NPD284	Phase 1
0.6832	Remote Similarity	NPD9429	Discontinued
0.6699	Remote Similarity	NPD2691	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6426	Approved
0.6636	Remote Similarity	NPD6425	Approved
0.6636	Remote Similarity	NPD6423	Approved
0.6636	Remote Similarity	NPD6427	Approved
0.6606	Remote Similarity	NPD6431	Approved
0.6606	Remote Similarity	NPD6434	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6433	Approved
0.6606	Remote Similarity	NPD6432	Approved
0.6581	Remote Similarity	NPD5376	Approved
0.6372	Remote Similarity	NPD5377	Approved
0.6372	Remote Similarity	NPD5378	Approved
0.6372	Remote Similarity	NPD5381	Approved
0.6328	Remote Similarity	NPD4826	Approved
0.6328	Remote Similarity	NPD4828	Approved
0.6328	Remote Similarity	NPD4827	Approved
0.6316	Remote Similarity	NPD6428	Approved
0.629	Remote Similarity	NPD3204	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD9407	Approved
0.6238	Remote Similarity	NPD9653	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3716	Discontinued
0.6204	Remote Similarity	NPD9654	Phase 2
0.6154	Remote Similarity	NPD9434	Approved
0.6154	Remote Similarity	NPD9435	Approved
0.6121	Remote Similarity	NPD4282	Approved
0.6111	Remote Similarity	NPD869	Approved
0.6087	Remote Similarity	NPD7844	Discontinued
0.6061	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5386	Phase 2
0.6036	Remote Similarity	NPD2698	Approved
0.6018	Remote Similarity	NPD6943	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD4837	Approved
0.6017	Remote Similarity	NPD4835	Approved
0.6017	Remote Similarity	NPD4836	Approved
0.6017	Remote Similarity	NPD4838	Approved
0.6	Remote Similarity	NPD3213	Discontinued
0.598	Remote Similarity	NPD9405	Approved
0.5968	Remote Similarity	NPD1804	Phase 2
0.5968	Remote Similarity	NPD1805	Phase 2
0.5954	Remote Similarity	NPD6436	Phase 3
0.595	Remote Similarity	NPD6946	Approved
0.595	Remote Similarity	NPD2700	Approved
0.5941	Remote Similarity	NPD9445	Approved
0.5929	Remote Similarity	NPD5796	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5798	Approved
0.5929	Remote Similarity	NPD5795	Approved
0.5929	Remote Similarity	NPD5797	Approved
0.5929	Remote Similarity	NPD5794	Approved
0.5926	Remote Similarity	NPD9644	Approved
0.5926	Remote Similarity	NPD9645	Approved
0.5926	Remote Similarity	NPD9646	Approved
0.5917	Remote Similarity	NPD1061	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD1428	Phase 2
0.5893	Remote Similarity	NPD3202	Approved
0.5893	Remote Similarity	NPD3201	Approved
0.5893	Remote Similarity	NPD3203	Approved
0.5893	Remote Similarity	NPD3208	Approved
0.5893	Remote Similarity	NPD3209	Approved
0.5893	Remote Similarity	NPD3207	Approved
0.5877	Remote Similarity	NPD285	Discontinued
0.5877	Remote Similarity	NPD9585	Discontinued
0.5804	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD9603	Phase 3
0.5804	Remote Similarity	NPD9602	Phase 3
0.5804	Remote Similarity	NPD9604	Approved
0.5798	Remote Similarity	NPD1455	Phase 3
0.5798	Remote Similarity	NPD223	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD1454	Phase 3
0.5784	Remote Similarity	NPD2702	Phase 1
0.5784	Remote Similarity	NPD2704	Phase 3
0.5738	Remote Similarity	NPD4743	Phase 2
0.5727	Remote Similarity	NPD4829	Discontinued
0.57	Remote Similarity	NPD2703	Discontinued
0.5664	Remote Similarity	NPD1760	Approved
0.5645	Remote Similarity	NPD1385	Discontinued
0.5644	Remote Similarity	NPD373	Approved
0.5644	Remote Similarity	NPD374	Approved
0.5644	Remote Similarity	NPD9030	Approved
0.5644	Remote Similarity	NPD9031	Approved
0.5644	Remote Similarity	NPD9033	Approved
0.5644	Remote Similarity	NPD9032	Approved
0.5635	Remote Similarity	NPD6941	Approved
0.563	Remote Similarity	NPD591	Approved
0.563	Remote Similarity	NPD3190	Approved
0.563	Remote Similarity	NPD3189	Approved
0.563	Remote Similarity	NPD3191	Approved
0.563	Remote Similarity	NPD577	Phase 3
0.5615	Remote Similarity	NPD4830	Approved
0.5615	Remote Similarity	NPD4832	Approved
0.5615	Remote Similarity	NPD4831	Approved
0.561	Remote Similarity	NPD1449	Approved
0.561	Remote Similarity	NPD1450	Approved

Structure

CID325900 OpenBabel06191716182D 56 58 0 0 1 0 0 0 0 0999 V2000 0.9135 -6.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6127 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1486 -4.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7467 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1486 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -4.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6127 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0147 -4.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 -6.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8807 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7467 -1.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2826 -6.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 -4.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6691 -2.4752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3776 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8807 -2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5506 -6.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6456 -1.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5116 -1.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3776 -1.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2437 -2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4788 1.5933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.6127 -1.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2826 -7.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -3.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0147 -3.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6845 -5.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1691 -1.6092 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -4.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -1.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -6.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -3.3412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7467 -3.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5506 -7.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -3.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -2.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1691 0.1229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -3.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 5 1 0 0 0 0 2 8 1 0 0 0 0 3 6 1 0 0 0 0 3 9 1 0 0 0 0 4 7 1 0 0 0 0 4 10 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 8 34 1 0 0 0 0 9 38 1 0 0 0 0 10 39 1 0 0 0 0 11 17 1 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 14 40 1 0 0 0 0 15 46 1 0 0 0 0 16 41 2 3 0 0 0 16 47 1 0 0 0 0 17 35 1 1 0 0 0 18 36 1 1 0 0 0 19 7 1 1 0 0 0 19 41 1 0 0 0 0 20 25 1 0 0 0 0 20 48 1 6 0 0 0 21 15 1 6 0 0 0 21 29 1 0 0 0 0 21 55 1 0 0 0 0 22 38 2 3 0 0 0 22 49 1 0 0 0 0 23 39 2 3 0 0 0 23 50 1 0 0 0 0 24 42 2 3 0 0 0 24 51 1 0 0 0 0 25 26 1 0 0 0 0 25 43 1 6 0 0 0 26 30 1 1 0 0 0 26 44 1 0 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 27 42 1 1 0 0 0 28 29 1 0 0 0 0 28 52 1 1 0 0 0 29 56 1 6 0 0 0 30 40 2 0 0 0 0 30 53 1 0 0 0 0 31 45 1 6 0 0 0 31 55 1 0 0 0 0 32 37 2 0 0 0 0 32 54 1 0 0 0 0 32 56 1 0 0 0 0 33 43 2 0 0 0 0 33 44 1 0 0 0 0 33 45 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	163567
ChEMBL	CHEMBL1801946
ZINC

Physicochemical Properties

Molecular Weight:	800.45
ALogP:	-7.2361
MLogP:	2.56
XLogP:	-2.769
# Rotatable Bonds:	37
Polar Surface Area:	400.66
# H-Bond Aceptor:	23
# H-Bond Donor:	15
# Rings:	3
# Heavy Atoms:	56

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