Serelaxin

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Also known as: 99489-94-8, Human relaxin 2, Human relaxin ii, Relexan 2, H2 relaxin, human, Relaxin h2, human

Molecular Formula

C₂₅₆H₄₀₈N₇₄O₇₄S₈

Molecular Weight

5963 g/mol

InChI Key

DTLOVISJEFBXLX-REAFJZEQSA-N

Recombinant human relaxin is a hormone produced during pregnancy that facilitates the birth process by causing a softening and lengthening of the cervix and the pubic symphysis (the place where the pubic bones come together).It is a heterodimer protein secreted by the corpus luteum and placenta during pregnancy.

1 2D Structure

Serelaxin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,6R,12S,15S,18S,21S,24S,27S,30S,33S,36S,39S,42R,47R,50S,53S,56S,59S,62S,65S,68S,71S,74R,80S,83S,88R)-6-[[(2S)-2-[[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-methylbutanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]-88-[[(2S)-6-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-3-hydroxy-2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-4-methyl-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]-68-(4-aminobutyl)-30-(3-amino-3-oxopropyl)-50-benzyl-33,39-bis[(2S)-butan-2-yl]-12,24,53,65-tetrakis(3-carbamimidamidopropyl)-15-(2-carboxyethyl)-42-[[2-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-2-oxoethyl]carbamoyl]-71-[(1R)-1-hydroxyethyl]-62-(hydroxymethyl)-83-(1H-imidazol-5-ylmethyl)-27,36,56-trimethyl-18,59-bis(2-methylpropyl)-7,10,13,16,19,22,25,28,31,34,37,40,49,52,55,58,61,64,67,70,73,76,79,82,85,87-hexacosaoxo-21,80-di(propan-2-yl)-3,4,44,45,90,91-hexathia-8,11,14,17,20,23,26,29,32,35,38,41,48,51,54,57,60,63,66,69,72,75,78,81,84,86-hexacosazabicyclo[72.11.7]dononacontane-47-carboxylic acid

2.1.2 InChI

InChI=1S/C256H408N74O74S8/c1-32-128(20)198-246(396)286-135(27)207(357)326-199(129(21)33-2)248(398)321-180(210(360)279-106-189(343)289-161(79-88-405-30)221(371)315-177(111-334)239(389)329-202(137(29)337)250(400)312-171(232(382)317-178(112-335)251(401)402)98-141-103-277-148-57-41-39-55-145(141)148)114-408-412-118-184(252(403)404)322-230(380)168(95-138-52-36-35-37-53-138)308-215(365)154(63-50-86-274-255(267)268)291-203(353)132(24)283-226(376)164(91-121(6)7)307-238(388)176(110-333)314-216(366)155(64-51-87-275-256(269)270)293-213(363)151(59-43-46-82-258)301-249(399)201(136(28)336)330-242(392)181-115-409-411-117-183(319-217(367)150(58-42-45-81-257)294-233(383)173(101-186(262)340)303-206(356)133(25)284-225(375)163(90-120(4)5)302-205(355)134(26)285-236(386)174(108-331)316-229(379)169(96-139-65-67-143(338)68-66-139)309-227(377)165(92-122(8)9)305-218(368)156-70-75-187(341)287-156)241(391)320-182(240(390)311-172(99-142-104-271-119-281-142)235(385)323-195(125(14)15)243(393)280-107-190(344)290-181)116-410-407-113-179(209(359)278-105-188(342)288-149(61-48-84-272-253(263)264)212(362)295-159(72-77-192(347)348)220(370)306-167(94-124(12)13)234(384)325-196(126(16)17)244(394)299-153(62-49-85-273-254(265)266)211(361)282-131(23)204(354)292-157(224(374)327-198)69-74-185(261)339)318-228(378)166(93-123(10)11)304-214(364)152(60-44-47-83-259)300-247(397)200(130(22)34-3)328-245(395)197(127(18)19)324-223(373)160(73-78-193(349)350)297-219(369)158(71-76-191(345)346)296-222(372)162(80-89-406-31)298-231(381)170(97-140-102-276-147-56-40-38-54-144(140)147)310-237(387)175(109-332)313-208(358)146(260)100-194(351)352/h35-41,52-57,65-68,102-104,119-137,146,149-184,195-202,276-277,331-338H,32-34,42-51,58-64,69-101,105-118,257-260H2,1-31H3,(H2,261,339)(H2,262,340)(H,271,281)(H,278,359)(H,279,360)(H,280,393)(H,282,361)(H,283,376)(H,284,375)(H,285,386)(H,286,396)(H,287,341)(H,288,342)(H,289,343)(H,290,344)(H,291,353)(H,292,354)(H,293,363)(H,294,383)(H,295,362)(H,296,372)(H,297,369)(H,298,381)(H,299,394)(H,300,397)(H,301,399)(H,302,355)(H,303,356)(H,304,364)(H,305,368)(H,306,370)(H,307,388)(H,308,365)(H,309,377)(H,310,387)(H,311,390)(H,312,400)(H,313,358)(H,314,366)(H,315,371)(H,316,379)(H,317,382)(H,318,378)(H,319,367)(H,320,391)(H,321,398)(H,322,380)(H,323,385)(H,324,373)(H,325,384)(H,326,357)(H,327,374)(H,328,395)(H,329,389)(H,330,392)(H,345,346)(H,347,348)(H,349,350)(H,351,352)(H,401,402)(H,403,404)(H4,263,264,272)(H4,265,266,273)(H4,267,268,274)(H4,269,270,275)/t128-,129-,130-,131-,132-,133-,134-,135-,136+,137+,146-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,195-,196-,197-,198-,199-,200-,201-,202-/m0/s1

2.1.3 InChI Key

DTLOVISJEFBXLX-REAFJZEQSA-N

2.1.4 Canonical SMILES

CCC(C)C1C(=O)NC(CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C2CSSCC(C(=O)NC(CSSCC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C)C(C)CC)CCC(=O)N)C)CCCNC(=N)N)C(C)C)CC(C)C)CCC(=O)O)CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)C(C(C)CC)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCSC)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CO)NC(=O)C(CC(=O)O)N)C(=O)NC(C(=O)NC(C(=O)NCC(=O)N2)C(C)C)CC5=CN=CN5)NC(=O)C(CCCCN)NC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CO)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CC(C)C)NC(=O)C7CCC(=O)N7)C(C)O)CCCCN)CCCNC(=N)N)CO)CC(C)C)C)CCCNC(=N)N)CC8=CC=CC=C8)C(=O)O)C(=O)NCC(=O)NC(CCSC)C(=O)NC(CO)C(=O)NC(C(C)O)C(=O)NC(CC9=CNC1=CC=CC=C19)C(=O)NC(CO)C(=O)O

2.1.5 Isomeric SMILES

CC[C@H](C)[C@H]1C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C)[C@@H](C)CC)CCC(=O)N)C)CCCNC(=N)N)C(C)C)CC(C)C)CCC(=O)O)CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)O)N)C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N2)C(C)C)CC5=CN=CN5)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]7CCC(=O)N7)[C@@H](C)O)CCCCN)CCCNC(=N)N)CO)CC(C)C)C)CCCNC(=N)N)CC8=CC=CC=C8)C(=O)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC9=CNC1=CC=CC=C19)C(=O)N[C@@H](CO)C(=O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. H2 Relaxin, Human

2. Relaxin 2 Protein, Human

3. Relaxin H2, Human

4. Relaxin-2 Protein, Human

5. Rln2 Protein, Human

6. Rlx2 Protein, Human

2.2.2 Depositor-Supplied Synonyms

1. 99489-94-8

2. Human Relaxin 2

3. Human Relaxin Ii

4. Relexan 2

5. H2 Relaxin, Human

6. Relaxin H2, Human

7. Relaxin Ii (human)

8. Serelaxin [usan:inn]

9. Relaxin-2 Protein, Human

10. Rlx030

11. Human Relaxin 2 (relaxin H2)

12. Unii-w0122b976y

13. Dtxsid40244082

14. Rlx 030

15. W0122b976y

2.3 Create Date

2013-04-19

3 Chemical and Physical Properties

Molecular Formula	C₂₅₆H₄₀₈N₇₄O₇₄S₈
Molecular Weight	5963 g/mol
XLogP3	-19.3
Hydrogen Bond Donor Count	87
Hydrogen Bond Acceptor Count	91
Rotatable Bond Count	194
Exact Mass	5960.8270502 g/mol
Monoisotopic Mass	5958.8203405 g/mol
Topological Polar Surface Area	2600 Å²
Heavy Atom Count	412
Formal Charge	0
Complexity	14800
Isotope Atom Count	0
Defined Atom Stereocenter Count	55
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in cardiovascular disorders, congestive heart failure, infertility, peripheral vascular disease, and scleroderma.

Treatment of acute heart failure

5 Pharmacology and Biochemistry

5.1 ATC Code

C01DX21

C - Cardiovascular system

C01 - Cardiac therapy

C01D - Vasodilators used in cardiac diseases

C01DX - Other vasodilators used in cardiac diseases

C01DX21 - Serelaxin

5.2 Mechanism of Action

Recombinant human relaxin inhibits contractions of the uterus and may play a role in timing of delivery. Relaxin works by simultaneously cutting collagen production and increasing collagen breakdown.