(6R)-L-erythro-6,7-dihydrobiopterin (CHEBI:43120)

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CHEBI:43120 - (6R)-L-erythro-6,7-dihydrobiopterin

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ChEBI Name	*(6R)-L-erythro-6,7-dihydrobiopterin*

ChEBI ID	CHEBI:43120

ChEBI ASCII Name	(6R)-L-erythro-6,7-dihydrobiopterin

Definition	A 6,7-dihydrobiopterin that has R configuration at position 6 and in which the 1,2-dihydroxypropyl substituent has 1R,2S configuration.

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

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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30 31 0 0 0 0 999 V2000

-1.1420 -0.0460 -2.7920 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.0370 0.0480 -3.5360 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1890 0.0960 -4.8980 N 0 0 0 0 0 0 0 0 0 0 0 0

1.1900 0.0980 -3.0540 N 0 0 0 0 0 0 0 0 0 0 0 0

1.4380 0.0400 -1.7380 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5730 0.0920 -1.3010 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2590 -0.0880 -0.8340 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0790 -0.1040 -1.4830 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3730 -0.1760 0.4420 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.1850 -0.1740 -0.6830 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.7900 -0.3390 1.3140 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.0250 0.3210 0.6970 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4980 0.3050 2.6700 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.6260 0.1370 3.5300 O 0 0 0 0 0 0 0 0 0 0 0 0

0.7270 -0.3610 3.2980 C 0 0 2 0 0 0 0 0 0 0 0 0

1.0190 0.2830 4.6550 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8550 -0.1920 2.4380 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9850 -1.4020 1.4560 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9080 0.0650 1.2820 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8930 1.4030 0.6840 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0280 -0.5300 -1.0040 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3020 1.3680 2.5320 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7650 -0.8150 3.6260 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5310 -1.4240 3.4360 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8920 -0.1910 5.1020 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2150 1.3470 4.5160 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1580 0.1550 5.3110 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9940 0.7590 2.3420 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5900 0.1650 -5.4710 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0760 0.0620 -5.2890 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 8 2 0 0 0 0

2 3 1 0 0 0 0

2 4 2 0 0 0 0

3 29 1 0 0 0 0

3 30 1 0 0 0 0

4 5 1 0 0 0 0

5 6 2 0 0 0 0

5 7 1 0 0 0 0

7 8 1 0 0 0 0

7 9 2 0 0 0 0

8 10 1 0 0 0 0

9 11 1 0 0 0 0

10 12 1 0 0 0 0

10 21 1 0 0 0 0

11 12 1 0 0 0 0

11 13 1 0 0 0 0

11 18 1 0 0 0 0

12 19 1 0 0 0 0

12 20 1 0 0 0 0

13 14 1 0 0 0 0

13 15 1 0 0 0 0

13 22 1 0 0 0 0

14 23 1 0 0 0 0

15 16 1 0 0 0 0

15 17 1 0 0 0 0

15 24 1 0 0 0 0

16 25 1 0 0 0 0

16 26 1 0 0 0 0

16 27 1 0 0 0 0

17 28 1 0 0 0 0

M END): 32 ms

reading 30 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

30 atoms created

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

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Formula

C9H13N5O3

Net Charge

Average Mass

239.232

Monoisotopic Mass

239.10184

InChI

InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,15-16H,2H2,1H3,(H3,10,11,13,14,17)/t3-,4+,6-/m0/s1

InChIKey

ZHQJVZLJDXWFFX-RPDRRWSUSA-N

SMILES

C1=2C(=N[C@H](CN1)[C@H]([C@H](C)O)O)C(N=C(N2)N)=O

Roles Classification
Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via 6,7-dihydrobiopterin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(6R)-L-erythro-6,7-dihydrobiopterin (CHEBI:43120) is a 6,7-dihydrobiopterin (CHEBI:20680)

IUPAC Name

(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-6,7-dihydropteridin-4(1H)-one

Synonyms	Sources
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-6,7-dihydro-4(1H)-pteridinone	ChEBI
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-7,8-dihydro-6H-pteridin-4-one	ChEBI
(6R)-6-[(1R,2S)-1,2-dihydroxypropyl]-7,8-dihydro-6H-pterin	ChEBI
(6R)-L-erythro-6,7-dihydrobiopterin	UniProt
4a-carbinolamine tetrahydrobiopterin	ChemIDplus
6,7-Dihydrobiopterin	KEGG COMPOUND
q-H2BPT	ChEBI
Quinoid-dihydrobiopterin	KEGG COMPOUND
quinonoid 6,7-dihydrobiopterin	ChEBI

Manual Xrefs	Databases
C00268	KEGG COMPOUND
H2B	PDBeChem
HMDB0002215	HMDB
View more database links

Registry Numbers	Types	Sources
5569323	Reaxys Registry Number	Reaxys
79647-29-3	CAS Registry Number	ChemIDplus

Citations

Liudnikova TA, Dashina OA, Telegina TA, Kritskiĭ MS (2009)
[Study of the photochemical properties of biopterin and its reduced forms].
Prikladnaia biokhimiia i mikrobiologiia 45, 117-123 [PubMed:19235519]
[show Abstract]

Schallreuter KU, Wood JM, Pittelkow MR, Gütlich M, Lemke KR, Rödl W, Swanson NN, Hitzemann K, Ziegler I (1994)
Regulation of melanin biosynthesis in the human epidermis by tetrahydrobiopterin.
Science (New York, N.Y.) 263, 1444-1446 [PubMed:8128228]
[show Abstract]

Schmidt HH, Pollock JS, Nakane M, Förstermann U, Murad F (1992)
Ca2+/calmodulin-regulated nitric oxide synthases.
Cell calcium 13, 427-434 [PubMed:1380405]
[show Abstract]

Davis MD, Kaufman S (1989)
Evidence for the formation of the 4a-carbinolamine during the tyrosine-dependent oxidation of tetrahydrobiopterin by rat liver phenylalanine hydroxylase.
The Journal of biological chemistry 264, 8585-8596 [PubMed:2722790]
[show Abstract]

Bailey SW, Ayling JE (1983)
6,6-Dimethylpterins: stable quinoid dihydropterin substrate for dihydropteridine reductase and tetrahydropterin cofactor for phenylalanine hydroxylase.
Biochemistry 22, 1790-1798 [PubMed:6849887]
[show Abstract]

Armarego WL, Randles D, Taguchi H (1983)
Peroxidase catalysed aerobic degradation of 5,6,7,8-tetrahydrobiopterin at physiological pH.
European journal of biochemistry 135, 393-403 [PubMed:6617639]
[show Abstract]

Last Modified

07 March 2023

CHEBI:43120 - (6R)-L-erythro-6,7-dihydrobiopterin

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