(S)-NADHX (CHEBI:44236)

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CHEBI:44236 - (S)-NADHX

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ChEBI Name	(S)-NADHX

ChEBI ID	CHEBI:44236

ChEBI ASCII Name	(S)-NADHX

Definition	A tetrahydronicotinamide adenine dinucleotide obtained by formal stereo- and regioselective hydration across the 5,6-double bond in the nicotinyl ring of NADH, with the hydroxy group located at position 6, having (S)-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ZINC000095615753

Download	Molfile XML SDF

more structures >>

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76 80 0 0 0 0 999 V2000

0.7780 1.0330 -1.0880 P 0 0 2 0 0 0 0 0 0 0 0 0

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2.1840 1.5610 -0.5090 O 0 0 0 0 0 0 0 0 0 0 0 0

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1.7390 0.8340 -3.3240 C 0 0 0 0 0 0 0 0 0 0 0 0

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4.0440 0.2180 -5.9080 O 0 0 0 0 0 0 0 0 0 0 0 0

1.8430 0.7170 -6.8610 C 0 0 1 0 0 0 0 0 0 0 0 0

2.6090 0.5460 -8.0550 O 0 0 0 0 0 0 0 0 0 0 0 0

0.9960 -0.5450 -6.5600 C 0 0 2 0 0 0 0 0 0 0 0 0

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-1.9020 -0.7440 -8.7650 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4540 -1.2000 -9.9740 C 0 0 0 0 0 0 0 0 0 0 0 0

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-1.6810 -1.8980 -10.8000 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.4230 -2.1610 -10.5000 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1360 -1.7540 -9.3800 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.5560 -1.0450 -8.4950 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0040 0.2220 0.0610 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.2370 1.2490 1.2790 P 0 0 2 0 0 0 0 0 0 0 0 0

-1.0400 2.3990 0.8070 O 0 0 0 0 0 0 0 0 0 0 0 0

1.1860 1.7740 1.8180 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.0190 0.5000 2.4700 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.1950 1.4590 3.5150 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9360 0.8080 4.6850 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.1660 -0.2910 5.2180 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.0700 1.8020 5.8600 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.3600 2.4160 5.8510 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.8960 0.9210 7.1200 C 0 0 1 0 0 0 0 0 0 0 0 0

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-1.6740 -0.4980 6.5540 C 0 0 2 0 0 0 0 0 0 0 0 0

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0.5680 -0.7270 7.5340 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3940 -1.2040 8.4760 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6830 -0.6350 8.6030 C 0 0 0 0 0 0 0 0 0 0 0 0

3.0240 0.2700 7.8650 O 0 0 0 0 0 0 0 0 0 0 0 0

3.5340 -1.0960 9.5420 N 0 0 0 0 0 0 0 0 0 0 0 0

1.0050 -2.3250 9.3990 C 0 0 0 0 0 0 0 0 0 0 0 0

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2.6800 1.1930 -2.9050 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6310 -0.8940 -4.2610 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8810 1.8250 -5.2880 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4300 0.7430 -6.6220 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2100 1.6020 -6.9300 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1100 1.3620 -8.1850 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5450 -1.4480 -6.8280 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5210 0.6500 -5.9000 H 0 0 0 0 0 0 0 0 0 0 0 0

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-2.6170 -1.0450 6.5210 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9090 0.0710 6.8910 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4170 -0.7060 9.6290 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 2 2 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

1 23 1 0 0 0 0

3 46 1 0 0 0 0

4 5 1 0 0 0 0

5 6 1 0 0 0 0

5 47 1 0 0 0 0

5 48 1 0 0 0 0

6 7 1 0 0 0 0

6 8 1 0 0 0 0

6 49 1 0 0 0 0

7 12 1 0 0 0 0

8 9 1 0 0 0 0

8 10 1 0 0 0 0

8 50 1 0 0 0 0

9 51 1 0 0 0 0

10 11 1 0 0 0 0

10 12 1 0 0 0 0

10 52 1 0 0 0 0

11 53 1 0 0 0 0

12 13 1 0 0 0 0

12 54 1 0 0 0 0

13 14 4 0 0 0 0

13 22 4 0 0 0 0

14 15 4 0 0 0 0

14 55 1 0 0 0 0

15 16 4 0 0 0 0

16 17 4 0 0 0 0

16 22 4 0 0 0 0

17 18 1 0 0 0 0

17 19 4 0 0 0 0

18 56 1 0 0 0 0

18 57 1 0 0 0 0

19 20 4 0 0 0 0

20 21 4 0 0 0 0

20 58 1 0 0 0 0

21 22 4 0 0 0 0

23 24 1 0 0 0 0

24 25 2 0 0 0 0

24 26 1 0 0 0 0

24 27 1 0 0 0 0

26 59 1 0 0 0 0

27 28 1 0 0 0 0

28 29 1 0 0 0 0

28 60 1 0 0 0 0

28 61 1 0 0 0 0

29 30 1 0 0 0 0

29 31 1 0 0 0 0

29 62 1 0 0 0 0

30 35 1 0 0 0 0

31 32 1 0 0 0 0

31 33 1 0 0 0 0

31 63 1 0 0 0 0

32 64 1 0 0 0 0

33 34 1 0 0 0 0

33 35 1 0 0 0 0

33 65 1 0 0 0 0

34 66 1 0 0 0 0

35 36 1 0 0 0 0

35 67 1 0 0 0 0

36 37 1 0 0 0 0

36 44 1 0 0 0 0

37 38 2 0 0 0 0

37 68 1 0 0 0 0

38 39 1 0 0 0 0

38 42 1 0 0 0 0

39 40 2 0 0 0 0

39 41 1 0 0 0 0

41 69 1 0 0 0 0

41 70 1 0 0 0 0

42 43 1 0 0 0 0

42 71 1 0 0 0 0

42 72 1 0 0 0 0

43 44 1 0 0 0 0

43 73 1 0 0 0 0

43 74 1 0 0 0 0

44 45 1 0 0 0 0

44 75 1 0 0 0 0

45 76 1 0 0 0 0

M END): 21 ms

reading 76 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

76 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C21H31N7O15P2

Net Charge

Average Mass

683.45630

Monoisotopic Mass

683.13534

InChI

InChI=1S/C21H31N7O15P2/c22-17-12-19(25-6-24-17)28(7-26-12)21-16(33)14(31)10(42-21)5-40-45(37,38)43-44(35,36)39-4-9-13(30)15(32)20(41-9)27-3-8(18(23)34)1-2-11(27)29/h3,6-7,9-11,13-16,20-21,29-33H,1-2,4-5H2,(H2,23,34)(H,35,36)(H,37,38)(H2,22,24,25)/t9-,10-,11+,13-,14-,15-,16-,20-,21-/m1/s1

InChIKey

IDBZKGQRLBFUFQ-VPHRTNKSSA-N

SMILES

NC(=O)C1=CN([C@@H](O)CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	fundamental metabolite Any metabolite produced by all living cells. (via NAD ) coenzyme A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons. (via NAD(P) )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(S)-NADHX (CHEBI:44236) has functional parent NADH (CHEBI:16908) (S)-NADHX (CHEBI:44236) is a hemiaminal (CHEBI:73080) (S)-NADHX (CHEBI:44236) is a tetrahydronicotinamide adenine dinucleotide (CHEBI:26916) (S)-NADHX (CHEBI:44236) is conjugate acid of (S)-NADHX(1−) (CHEBI:57458) (S)-NADHX (CHEBI:44236) is conjugate base of (S)-NADHX(1+) (CHEBI:15644)

Incoming	(S)-NADHX(1+) (CHEBI:15644) is conjugate acid of (S)-NADHX (CHEBI:44236) (S)-NADHX(1−) (CHEBI:57458) is conjugate base of (S)-NADHX (CHEBI:44236)

IUPAC Name

adenosine 5'-(3-{5-[(2S)-5-carbamoyl-2-hydroxy-3,4-dihydropyridin-1-yl]-5-deoxy-β-D-ribofuranosyl} dihydrogen diphosphate)

Synonyms	Sources
(6S)-6β-hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotide	ChEBI
6beta-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	KEGG COMPOUND
BETA-6-HYDROXY-1,4,5,6-TETRHYDRONICOTINAMIDE ADENINE DINUCLEOTIDE	PDBeChem

Manual Xrefs	Databases
C04856	KEGG COMPOUND
CPD-653	MetaCyc
HMDB0059644	HMDB
NAX	PDBeChem
View more database links

Citation	Type	Source
21994945	PubMed citation	Europe PMC

Last Modified

13 December 2016

CHEBI:44236 - (S)-NADHX

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