Details of the Drug

General Information of Drug (ID: DMD4BFY)

Drug Name
SPERMINE
Synonyms
spermine; 71-44-3; neuridine; musculamine; gerontine; Spermin; 4,9-Diaza-1,12-dodecanediamine; Diaminopropyltetramethylenediamine; N,N'-Bis(3-aminopropyl)-1,4-butanediamine; Spermine, puriss; N,N'-Bis(3-aminopropyl)butane-1,4-diamine; 1,4-Butanediamine, N,N'-bis(3-aminopropyl)-; 1,4-Bis(aminopropyl)butanediamine; 4,9-Diazadodecamethylenediamine; 4,9-Diazadodecane-1,12-diamine; N1,N1'-(Butane-1,4-diyl)bis(propane-1,3-diamine); UNII-2FZ7Y3VOQX; 1,4-Bis(aminopropyl) butanediamine; Spermine Derivative; 1,4-Diaminobutane, N,N'-bis
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 202.34
Logarithm of the Partition Coefficient (xlogp) -1.1
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C10H26N4
IUPAC Name
N,N'-bis(3-aminopropyl)butane-1,4-diamine
Canonical SMILES
C(CCNCCCN)CNCCCN
InChI
InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChIKey
PFNFFQXMRSDOHW-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1103
ChEBI ID
CHEBI:15746
CAS Number
71-44-3
DrugBank ID
DB00127
TTD ID
D0LD9S
VARIDT ID
DR01249
INTEDE ID
DR1505

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Carbonic anhydrase (CA) TTUNARX NOUNIPROTAC Inhibitor [1]
Carbonic anhydrase IV (CA-IV) TTZHA0O CAH4_HUMAN Inhibitor [1]
Carbonic anhydrase IX (CA-IX) TT2LVK8 CAH9_HUMAN Inhibitor [1]
Carbonic anhydrase VI (CA-VI) TTCFSPE CAH6_HUMAN Inhibitor [1]
Carbonic anhydrase XIV (CA-XIV) TTEYTKG CAH14_HUMAN Inhibitor [1]
Glutamate receptor ionotropic NMDA 1 (NMDAR1) TTLD29N NMDZ1_HUMAN Inhibitor [2]
Glutamate receptor ionotropic NMDA 2A (NMDAR2A) TTKJEMQ NMDE1_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
MFS-type transporter SLC18B1 (SLC18B1) DTOFXP5 S18B1_HUMAN Substrate [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Putrescine acetyltransferase (SSAT1) DEMWO83 SAT1_HUMAN Substrate [4]
Spermine oxidase (SMOX) DEOH5V3 SMOX_HUMAN Substrate [5]
Polyamine oxidase (PAOX) DEW7V0G PAOX_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [7]
Beta-1 adrenergic receptor (ADRB1) OTQBWN4U ADRB1_HUMAN Protein Interaction/Cellular Processes [8]
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Protein Interaction/Cellular Processes [8]
Diablo IAP-binding mitochondrial protein (DIABLO) OTHJ9MCZ DBLOH_HUMAN Protein Interaction/Cellular Processes [7]
Mitogen-activated protein kinase 8 (MAPK8) OTEREYS5 MK08_HUMAN Gene/Protein Processing [9]
Nitric oxide synthase, inducible (NOS2) OTKKIOJ1 NOS2_HUMAN Gene/Protein Processing [9]
Spermine oxidase (SMOX) OT11E62Y SMOX_HUMAN Biotransformations [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Carbonic anhydrase IV (CA-IV) DTT CA4 1.58E-77 -2.02 -1.77
Carbonic anhydrase XIV (CA-XIV) DTT CA14 5.79E-07 -0.09 -0.16
Carbonic anhydrase VI (CA-VI) DTT CA6 3.64E-10 -0.17 -0.37
Carbonic anhydrase IX (CA-IX) DTT CA9 1.12E-10 -0.03 -0.09
MFS-type transporter SLC18B1 (SLC18B1) DTP SLC18B1 1.24E-09 -1.85E-01 -2.85E-01
Polyamine oxidase (PAOX) DME PAOX 1.25E-41 3.26E-01 1.01E+00
Spermine oxidase (SMOX) DME SMOX 1.04E-02 -6.80E-02 -2.31E-01
Putrescine acetyltransferase (SSAT1) DME SAT1 1.55E-45 6.17E-01 1.19E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem. 2010 Aug 12;53(15):5511-22.
2 Bivalent beta-carbolines as potential multitarget anti-Alzheimer agents. J Med Chem. 2010 May 13;53(9):3611-7.
3 Identification of a mammalian vesicular polyamine transporter. Sci Rep. 2014 Oct 30;4:6836.
4 Mechanistic and structural analysis of human spermidine/spermine N1-acetyltransferase. Biochemistry. 2007 Jun 19;46(24):7187-95.
5 Distinct immunomodulatory effects of spermine oxidase in colitis induced by epithelial injury or infection. Front Immunol. 2018 Jun 5;9:1242.
6 Polyamine catabolism and disease. Biochem J. 2009 Jul 15;421(3):323-38.
7 Induction of apoptosis by spermine-metabolites in primary human blood cells and various tumor cell lines. Apoptosis. 2005 Oct;10(5):1151-62. doi: 10.1007/s10495-005-1188-5.
8 Functional effects of polyamines via activation of human 1- and 2-adrenoceptors stably expressed in CHO cells. Pharmacol Rep. 2010 Jul-Aug;62(4):696-706. doi: 10.1016/s1734-1140(10)70327-3.
9 Inhibition of apoptotic signalling in spermine-treated vascular smooth muscle cells by a novel glutathione precursor. Cell Biol Int. 2010 Apr 1;34(5):503-11.
10 Acetaldehyde-induced cytotoxicity involves induction of spermine oxidase at the transcriptional level. Toxicology. 2013 Aug 9;310:1-7. doi: 10.1016/j.tox.2013.05.008. Epub 2013 May 23.