NPASS Natural Product

Natural Product: NPC319537

Natural Product ID:	NPC319537
Common Name:	Validoxylamine A
IUPAC Name:	(1S,2S,3R,6S)-4-(hydroxymethyl)-6-[[(1S,2S,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]amino]cyclohex-4-ene-1,2,3-triol
Synonyms:
Molecular Formula:	C14H25NO8
Standard InCHIKey:	YCJYNBLLJHFIIW-MBABXGOBSA-N
Standard InCHI:	InChI=1S/C14H25NO8/c16-3-5-1-7(11(20)13(22)9(5)18)15-8-2-6(4-17)10(19)14(23)12(8)21/h1,6-23H,2-4H2/t6-,7+,8+,9-,10-,11+,12+,13+,14+/m1/s1
Canonical SMILES:	OC[C@H]1C[C@H](N[C@H]2C=C(CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)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
NPO13391.10	Streptomyces hygroscopicus subsp. limoneus	Varieties	Streptomycetaceae	Bacteria				PMID[23028689]
NPO2746	Apis cerana	Species	Apidae	Eukaryota				PMID[16377847]

Biological Activity

Activity Type	# Activity
IC50	6
LD50	2
Others	46

Activity Type	# Activity
Individual Protein	6
Organism	46
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6043	Individual Protein	Trehalase	Bombyx mori	Inhibition	=	78	%	10.1584/jpestics.19.39
NPT6044	Individual Protein	Chitinase A1	Thanatephorus cucumeris (strain AG1-IB / isolate 7/3/14) (Lettucebottom rot fungus) (Rhizoctonia solani)	IC50	>	1000000	nM	10.1584/jpestics.19.39
NPT2	Others	Unspecified		IC50	>	1000000	nM	10.1584/jpestics.19.39
NPT1050	Individual Protein	Trehalase	Rattus norvegicus	IC50	=	4.9	nM	10.1584/jpestics.19.39
NPT6045	Individual Protein	Vacuolar acid trehalase	Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)	IC50	=	3	nM	10.1584/jpestics.19.39
NPT6043	Individual Protein	Trehalase	Bombyx mori	IC50	=	48	nM	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	LD50	=	2.42	ug	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	LD50	<	1	ug	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	5	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	58	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	25	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	15	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	0	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	30	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	40	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	20	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	10	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	13	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	85	%	10.1584/jpestics.19.39
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	60	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	0	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	100	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	80	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	60	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	27	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	40	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	13	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	10	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	7	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	20	%	10.1584/jpestics.19.39
NPT6046	Organism	Mamestra brassicae	Mamestra brassicae	Activity	=	90	%	10.1584/jpestics.19.39

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 NPC319537 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	82
0.1-0.2	539
0.2-0.3	3085
0.3-0.4	18201
0.4-0.5	8133
0.5-0.6	824
0.6-0.7	19
0.7-0.8	3
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC313272
0.875	High Similarity	NPC20035
0.835	Intermediate Similarity	NPC315170
0.7449	Intermediate Similarity	NPC314762
0.7041	Intermediate Similarity	NPC244539
0.7034	Intermediate Similarity	NPC314306
0.68	Remote Similarity	NPC478138
0.68	Remote Similarity	NPC313762
0.6557	Remote Similarity	NPC241597
0.6218	Remote Similarity	NPC473254
0.6204	Remote Similarity	NPC297058
0.619	Remote Similarity	NPC304646
0.619	Remote Similarity	NPC28280
0.6182	Remote Similarity	NPC470365
0.6136	Remote Similarity	NPC237286
0.6119	Remote Similarity	NPC471471
0.6119	Remote Similarity	NPC121601
0.6119	Remote Similarity	NPC164476
0.6048	Remote Similarity	NPC472359
0.6034	Remote Similarity	NPC25033
0.6034	Remote Similarity	NPC476261
0.6034	Remote Similarity	NPC119225
0.6034	Remote Similarity	NPC470382
0.6034	Remote Similarity	NPC471635
0.6	Remote Similarity	NPC176012
0.595	Remote Similarity	NPC55336
0.594	Remote Similarity	NPC296686
0.5935	Remote Similarity	NPC315426
0.5932	Remote Similarity	NPC140300
0.5932	Remote Similarity	NPC474164
0.5931	Remote Similarity	NPC233770
0.5931	Remote Similarity	NPC77481
0.5929	Remote Similarity	NPC316186
0.5926	Remote Similarity	NPC207657
0.5902	Remote Similarity	NPC477000
0.5902	Remote Similarity	NPC477001
0.5887	Remote Similarity	NPC159367
0.5872	Remote Similarity	NPC471270
0.5854	Remote Similarity	NPC93179
0.5842	Remote Similarity	NPC471418
0.5839	Remote Similarity	NPC478139
0.5833	Remote Similarity	NPC56298
0.5833	Remote Similarity	NPC471628
0.5806	Remote Similarity	NPC46981
0.5797	Remote Similarity	NPC15249
0.5797	Remote Similarity	NPC25455
0.5794	Remote Similarity	NPC287764
0.5789	Remote Similarity	NPC469943
0.5784	Remote Similarity	NPC268922
0.578	Remote Similarity	NPC236707
0.578	Remote Similarity	NPC95124
0.578	Remote Similarity	NPC471266
0.5772	Remote Similarity	NPC44514
0.5769	Remote Similarity	NPC474468
0.5755	Remote Similarity	NPC122819
0.5745	Remote Similarity	NPC208757
0.5741	Remote Similarity	NPC68119
0.5741	Remote Similarity	NPC13823
0.5739	Remote Similarity	NPC259875
0.5739	Remote Similarity	NPC187785
0.5739	Remote Similarity	NPC473100
0.5738	Remote Similarity	NPC247060
0.5738	Remote Similarity	NPC50815
0.5735	Remote Similarity	NPC96010
0.5735	Remote Similarity	NPC317654
0.5728	Remote Similarity	NPC473710
0.5728	Remote Similarity	NPC475694
0.5726	Remote Similarity	NPC55462
0.5725	Remote Similarity	NPC322366
0.5714	Remote Similarity	NPC85001
0.5714	Remote Similarity	NPC253645
0.5714	Remote Similarity	NPC147753
0.5714	Remote Similarity	NPC26932
0.5714	Remote Similarity	NPC150057
0.5714	Remote Similarity	NPC289140
0.5714	Remote Similarity	NPC476903
0.5714	Remote Similarity	NPC95920
0.5714	Remote Similarity	NPC147835
0.5714	Remote Similarity	NPC242692
0.5704	Remote Similarity	NPC68327
0.5703	Remote Similarity	NPC76660
0.5703	Remote Similarity	NPC276995
0.57	Remote Similarity	NPC142290
0.57	Remote Similarity	NPC471892
0.57	Remote Similarity	NPC471780
0.57	Remote Similarity	NPC198341
0.57	Remote Similarity	NPC75435
0.57	Remote Similarity	NPC223386
0.569	Remote Similarity	NPC84171
0.569	Remote Similarity	NPC473099
0.5673	Remote Similarity	NPC476695
0.5673	Remote Similarity	NPC285014
0.5673	Remote Similarity	NPC28959
0.5673	Remote Similarity	NPC299603
0.5673	Remote Similarity	NPC255535
0.5673	Remote Similarity	NPC476694
0.5673	Remote Similarity	NPC137554
0.5673	Remote Similarity	NPC476696
0.5672	Remote Similarity	NPC472458
0.5659	Remote Similarity	NPC478137
0.5656	Remote Similarity	NPC118275
0.5644	Remote Similarity	NPC116377
0.5644	Remote Similarity	NPC315980
0.5644	Remote Similarity	NPC69798
0.5644	Remote Similarity	NPC303798
0.5644	Remote Similarity	NPC473952
0.5644	Remote Similarity	NPC101746
0.5644	Remote Similarity	NPC77191
0.5644	Remote Similarity	NPC286851
0.5641	Remote Similarity	NPC97404
0.5641	Remote Similarity	NPC41554
0.5641	Remote Similarity	NPC160931
0.5641	Remote Similarity	NPC37205
0.5625	Remote Similarity	NPC29501
0.562	Remote Similarity	NPC476951
0.5615	Remote Similarity	NPC476499
0.5614	Remote Similarity	NPC255143
0.5612	Remote Similarity	NPC323775
0.5612	Remote Similarity	NPC236347
0.561	Remote Similarity	NPC471083
0.561	Remote Similarity	NPC251884
0.5607	Remote Similarity	NPC140327
0.5607	Remote Similarity	NPC212008
0.5607	Remote Similarity	NPC51055
0.5607	Remote Similarity	NPC62293
0.5606	Remote Similarity	NPC235625
0.5603	Remote Similarity	NPC470361
0.5603	Remote Similarity	NPC120420
0.56	Remote Similarity	NPC475837
0.56	Remote Similarity	NPC471259

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC319537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	86
0.1-0.2	335
0.2-0.3	2861
0.3-0.4	4286
0.4-0.5	1385
0.5-0.6	200
0.6-0.7	5
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	Drug ID	Developmental Stage
0.77	Intermediate Similarity	NPD394	Phase 3
0.7034	Intermediate Similarity	NPD6430	Approved
0.7034	Intermediate Similarity	NPD6429	Approved
0.6721	Remote Similarity	NPD4831	Approved
0.6721	Remote Similarity	NPD4832	Approved
0.6721	Remote Similarity	NPD4830	Approved
0.6557	Remote Similarity	NPD3731	Phase 3
0.6406	Remote Similarity	NPD6436	Phase 3
0.5971	Remote Similarity	NPD1136	Approved
0.5971	Remote Similarity	NPD1130	Approved
0.5971	Remote Similarity	NPD1132	Approved
0.5957	Remote Similarity	NPD817	Approved
0.5957	Remote Similarity	NPD823	Approved
0.5899	Remote Similarity	NPD597	Approved
0.5899	Remote Similarity	NPD598	Approved
0.5899	Remote Similarity	NPD601	Approved
0.5845	Remote Similarity	NPD2568	Approved
0.5839	Remote Similarity	NPD602	Approved
0.5839	Remote Similarity	NPD599	Approved
0.5833	Remote Similarity	NPD4837	Approved
0.5833	Remote Similarity	NPD4838	Approved
0.5833	Remote Similarity	NPD4836	Approved
0.5833	Remote Similarity	NPD4835	Approved
0.5816	Remote Similarity	NPD3061	Approved
0.5816	Remote Similarity	NPD3062	Approved
0.5816	Remote Similarity	NPD3059	Approved
0.5755	Remote Similarity	NPD8449	Approved
0.5738	Remote Similarity	NPD244	Clinical (unspecified phase)
0.5734	Remote Similarity	NPD5314	Approved
0.5726	Remote Similarity	NPD5357	Phase 1
0.5725	Remote Similarity	NPD859	Approved
0.5725	Remote Similarity	NPD858	Approved
0.5714	Remote Similarity	NPD8450	Suspended
0.5667	Remote Similarity	NPD4282	Approved
0.5634	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD9619	Approved
0.5612	Remote Similarity	NPD9620	Approved
0.5612	Remote Similarity	NPD9621	Approved

Structure

CID319537 OpenBabel06191716142D 23 24 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -1.7321 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 7 1 0 0 0 0 2 6 1 0 0 0 0 2 8 1 0 0 0 0 3 5 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 9 1 0 0 0 0 6 4 1 6 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 1 0 0 0 8 12 1 0 0 0 0 8 15 1 1 0 0 0 9 13 1 0 0 0 0 9 18 1 1 0 0 0 10 14 1 0 0 0 0 10 19 1 1 0 0 0 11 13 1 0 0 0 0 11 20 1 1 0 0 0 12 14 1 0 0 0 0 12 21 1 1 0 0 0 13 22 1 6 0 0 0 14 23 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	11450478
ChEMBL	CHEMBL1236649
ZINC

Physicochemical Properties

Molecular Weight:	335.16
ALogP:	-4.2611
MLogP:	2.01
XLogP:	-1.695
# Rotatable Bonds:	12
Polar Surface Area:	173.87
# H-Bond Aceptor:	9
# H-Bond Donor:	9
# Rings:	2
# Heavy Atoms:	23

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