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Compound Summary

cyclosporin A

Compound Information

cyclosporin A

Compound Name:	cyclosporin A
Compound CID:	5284373
Synonyms:	cyclosporin A cyclosporine Ciclosporin 59865-13-3 Cyclosporine A More...
Iupac Name:	(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
InChI:	InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1
InChIKey:	PMATZTZNYRCHOR-CGLBZJNRSA-N
Canonical Smiles:	CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
Isomeric Smiles:	CC[C@H]1C(=O)N(CC(=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@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
Molecular Weight:	1202.6
Molecular Formula:	C62H111N11O12

Compound Structure

2D Structure:

3D Structure:

Computed Properties

cyclosporin A

Molecular Weight:	1202.6
Molecular Formula:	C62H111N11O12
Hydrogen Bond Donor Count:	5
Hydrogen Bond Acceptor Count:	12
Rotatable Bond Count:	15
Heavy Atom Count:	85
Complexity:	2330

Synonyms

cyclosporin A

cyclosporin A	cyclosporin A
cyclosporin A	cyclosporine
Ciclosporin	59865-13-3
Cyclosporine A	Sandimmune
Sandimmun	Neoral
Cyclosporin	Ciclosporine
Gengraf	Ramihyphin A
Sandimmun Neoral	Sang-35
Ciclosporina	Ciclosporinum
Consupren	Equoral
Neoplanta	UNII-83HN0GTJ6D
Antibiotic S 7481F1	SangCyA
MFCD00274558	83HN0GTJ6D
MLS001333756	CHEBI:4031
CSA	S-Neoral
Cipol N	Sigmasporin Microoral
Cyclosporin A solution	DSSTox_CID_365
Ciclosporin (Ciclosporin A)	DSSTox_RID_75541
DSSTox_GSID_20365	SDZ-OXL 400
Ciclosporin A	OL 27-400
Abrammune	Imusporin
Optimmune	Seciera
Vekacia	Papilock Mini
Arpimune ME	Zinograf ME
Sandimmune Neoral	Ciclosporina Germed
(R-(R,R-(E)))-Cyclic(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl)	CYA
SMR000058578	Cicloral (antibiotic)
Debio088	Sang 35
Cyclosporine USAN:USP	Ciclosporine INN-French
Ciclosporinum INN-Latin	Ciclosporina INN-Spanish
Cyclospori	Sigmasporin
Cyclokat	Mitogard
Papilock	Pulminiq
Zyclorin	CicloMulsion
Ciclosporin;	CCRIS 1590
Ciclosporin DT	Consupren S
NSC290193	Modusik-A
HSDB 6881	NeuroSTAT
1cyn	2wfj
4jjm	NSC-290193
Cipol-N	NCGC00016890-01
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,2	(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone	(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19
(R-R,R-(E))-Cyclic(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl)	Cyclo(((E)-(2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl)-L-2-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl)
Cyclo(E)-(2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl	DRG-0275
Prestwick_731	Ciclosporin INN
CAS-59865-13-3	NSC 290193
CsA & IFN.alpha.	1c5f
2z6w	S 7481F1
Cyclosporine manufacturer	Prestwick2_000435
Prestwick3_000435	CHEMBL160
Sang-2000	SCHEMBL3491
SCHEMBL4442	Nova-22007
Ikervis (opthalmic solution)	BSPBio_000450
Cyclosporin A & IFN.alpha.	MLS000028376
MLS002153454	MLS002207033
Verkazia (opthalmic solution)	SDZ-OXL-400
BPBio1_000496	GTPL1024
ANTIBIOTIC S-7481F1	DTXSID0020365
CHEBI:92233	AOB2581
ATH-002	OLO-400
CB-01-09 MMX	HMS1569G12
HMS2089A09	HMS2096G12
HMS2230M14	HMS3713G12
1,11-cycloL-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(E)-(2S,3R,4R)-2-amino-3-hydroxy-N,4-dimethyloct-6-enoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucine	30-Ethyl-33-(1-hydroxy-2-methyl-hex-4-enyl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31undecaaza-cyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone
30-ethyl-33-(4E)-1-hydroxy-2-methylhex-4-en-1-yl-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone	30-ethyl-33-(4E)-1-hydroxy-2-methylhex-4-en-1-yl-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
Cyclo(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-((3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-dimethyl-L-2-aminooctanoyl)-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methylleucyl)	Cyclosporin A, Ready Made Solution
EX-A4110	HY-B0579
Tox21_110667	Tox21_301849
BDBM50022815	DE-076
ST-603	Cyclosporin A, >=98.5% (TLC)
AKOS015969287	Tox21_110667_1
CCG-208184	DB00091
EBD2126862	KS-1257
SDCCGSBI-0050230.P004	NCGC00093704-12
NCGC00164258-01	NCGC00164258-02
NCGC00164258-03	NCGC00255232-01
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone	AT-12519
BC164336	C042
Cyclo(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-((3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-dimethyl-L-2-aminooctanoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methylleucyl)	OL-27400
SBI-0050230.P003	AB0090560
OL-27-400	5946-EP0930075A1
5946-EP2289877A1	5946-EP2292601A1
5946-EP2292602A1	5946-EP2292603A1
5946-EP2292604A2	5946-EP2292618A1
5946-EP2293650A1	5946-EP2298737A1
5946-EP2298739A1	5946-EP2298740A1
5946-EP2298741A1	5946-EP2298771A2
5946-EP2301920A1	5946-EP2301940A1
5946-EP2308843A1	5946-EP2308861A1
J10181	J90049
M01532	865C133
A832514	Cyclosporin A, VETRANAL(TM), analytical standard
Q367700	SR-01000780563
Q-200913	SR-01000780563-3
BRD-K03222093-001-01-8	BRD-K13533483-001-03-0
Ciclosporin, European Pharmacopoeia (EP) Reference Standard	Cyclosporin A, from Tolypocladium inflatum, >=95% (HPLC), solid
Cyclosporine, United States Pharmacopeia (USP) Reference Standard	Ciclosporin for system suitability, European Pharmacopoeia (EP) Reference Standard
Cyclosporin A, from Tolypocladium inflatum, BioReagent, for molecular biology, >=95%	Cyclosporine, Pharmaceutical Secondary Standard; Certified Reference Material
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-((1R,2R,E)-1-hydroxy-2-methylhex-4-en-1-yl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone	(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-(E,1R,2R)-1-hydroxy-2-methyl-pent-3-enyl-3,6,9,18,24-pentaisobutyl-21-isopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32	104250-72-8
30-Ethyl-33-((E)-1-hydroxy-2-methyl-hex-4-enyl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,28-octamethyl-1,4,7,10,13,16,19,22,25,28,31undecaaza-cyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone

Experimental Data

cyclosporin A

Species	Dose	Unit	Control(Avg days)	Treatment(Avg days)	Avg/Med Lifespan Change(%)	Control(Max days)	Treatment(Max days)	Max Lifespan Change(%)	Significant	Strain	Gender	PubMed	Avg/Med Lifespan Change tab
Caenorhabditis elegans	88.000000000000000	umol/L			18.000000000000000				S	N2		24134630	Active
Caenorhabditis elegans	33.000000000000000	umol/L			18.000000000000000				S	N2		33683565	Active

Experimental Data Visualization

cyclosporin A

Statistics Data

cyclosporin A

Species	Avg/Med Lifespan Change(%)	Max Lifespan Change(%)	Count Reference	Count Data point
Caenorhabditis elegans	18.000000000000000		2	2

Statistics Data Visualization

cyclosporin A

Compound Name:

cyclosporin A

Compound CID:

5284373

Synonyms:

cyclosporin A cyclosporine Ciclosporin 59865-13-3 Cyclosporine A More...

Iupac Name:

(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone

InChI:

InChIKey:

PMATZTZNYRCHOR-CGLBZJNRSA-N

Canonical Smiles:

CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C

Isomeric Smiles:

CC[C@H]1C(=O)N(CC(=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@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C

Molecular Weight:

1202.6

Molecular Formula:

C62H111N11O12

Molecular Weight:

1202.6

Molecular Formula:

C62H111N11O12

Hydrogen Bond Donor Count:

5

Hydrogen Bond Acceptor Count:

12

Rotatable Bond Count:

15

Heavy Atom Count:

85

Complexity:

2330

cyclosporin A

cyclosporine

Ciclosporin

59865-13-3

Cyclosporine A

Sandimmune

Sandimmun

Neoral

Cyclosporin

Ciclosporine

Gengraf

Ramihyphin A

Sandimmun Neoral

Sang-35

Ciclosporina

Ciclosporinum

Consupren

Equoral

Neoplanta

UNII-83HN0GTJ6D

Antibiotic S 7481F1

SangCyA

MFCD00274558

83HN0GTJ6D

MLS001333756

CHEBI:4031

CSA

S-Neoral

Cipol N

Sigmasporin Microoral

Cyclosporin A solution

DSSTox_CID_365

Ciclosporin (Ciclosporin A)

DSSTox_RID_75541

DSSTox_GSID_20365

SDZ-OXL 400

Ciclosporin A

OL 27-400

Abrammune

Imusporin

Optimmune

Seciera

Vekacia

Papilock Mini

Arpimune ME

Zinograf ME

Sandimmune Neoral

cyclosporin A

cyclosporine

Ciclosporin

59865-13-3

Cyclosporine A

More...

(R-(R,R-(E)))-Cyclic(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl)

(R-R,R-(E))-Cyclic(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl)