Mitomycin C

Details

• Internal ID: e00922f4-7270-4dcc-bbeb-94add2aab6fd
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolequinones > Mitomycins, mitosane and mitosene derivatives > Mitomycins
• IUPAC Name: [(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
• InChI: InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1
• InChI Key: NWIBSHFKIJFRCO-WUDYKRTCSA-N
• Popularity: 34,767 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈N₄O₅
• Molecular Weight: 334.33 g/mol
• Exact Mass: 334.12771969 g/mol
• Topological Polar Surface Area (TPSA): 147.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.65
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• Mitomycin
• 50-07-7
• Ametycine
• Mutamycin
• Mitomycin-C
• Mitocin-C
• Ametycin
• Mytozytrex
• Mitomycinum
• Mytomycin
• Mitomycinum C
• Mitamycin
• Mitozytrex
• Mitosol
• Muamycin
• Mitomycyna C
• 7-Amino-9alpha-methoxymitosane
• MMC
• Mito-C
• NSC-26980
• Mit-C
• RCRA waste number U010
• NCI-C04706
• CCRIS 414
• HSDB 3239
• NSC26980
• EINECS 200-008-6
• UNII-50SG953SK6
• JELMYTO
• DTXSID2020898
• CHEBI:27504
• AI3-26199
• Mitocin C
• 50SG953SK6
• DTXCID00898
• 6-Amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methylazirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione carbamate (ester)
• Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1aS-(1aalpha,8beta,8aalpha,8balpha))-
• UGN-101
• UGN-102
• Mitomycin [USAN:USP:INN:BAN]
• Mitomycyna C [Polish]
• [(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methyl carbamate
• MITOMYCIN (MART.)
• MITOMYCIN [MART.]
• MITOMYCIN (USP-RS)
• MITOMYCIN [USP-RS]
• MITOMYCIN C (IARC)
• MITOMYCIN C [IARC]
• Mitomycin (TN)
• Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-, carbamate (ester)
• Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1aS,8S,8aR,8bS)-
• C15H18N4O5
• MITOMYCIN (EP MONOGRAPH)
• MITOMYCIN [EP MONOGRAPH]
• MITOMYCIN (USP MONOGRAPH)
• MITOMYCIN [USP MONOGRAPH]
• Mitomycin (USAN:USP:INN:BAN)
• CAS-50-07-7
• Muamycin (TN)
• NSC 26980
• ((1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate
• [(1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate
• Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-, (1aS,8S,8aR,8bS)-
• Mitomycin (USP/INN)
• MLS002702984
• (amino-methoxy-methyl-dioxo-[?]yl)methyl carbamate
• RCRA waste no. U010
• 7-Amino-9.alpha.-methoxymitosane
• Mutamycine
• Mitocin
• Mitolem
• Mitomycine C
• Mito-Medac
• Mitomycin-X
• NCGC00095258-01
• ((1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino(2',3':3,4)pyrrolo(1,2-a)indol-8-yl)methyl carbamate
• [(1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate
• Mitomycin; [(1aS,8S,8aR,8bS)-6-Amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2'',3'':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate; Mitomycin C
• Jelmyto (TN)
• MFCD00078109
• MITO
• Mitomycin C- Bio-X
• Mitomycin C from Streptomyces caespitosus
• MITOMYCIN [INN]
• Mitomycin C (JP17)
• MITOMYCIN [HSDB]
• MITOMYCIN [USAN]
• MITOMYCIN [VANDF]
• MITOMYCIN C [MI]
• CHEMBL105
• MITOMYCIN C [JAN]
• MITOMYCIN [WHO-DD]
• SCHEMBL3760
• CBiol_001927
• BSPBio_001267
• KBioGR_000607
• KBioSS_000607
• Mitomycin C (4% in NaCl)
• MLS001332654
• Mitozytrex (TN) (Supergene)
• 50-07-7 (non-salt)
• AMETYCIN pound notmitomycin C
• GTPL7089
• MITOMYCIN [ORANGE BOOK]
• KBio2_000607
• KBio2_003175
• KBio2_005743
• KBio3_001073
• KBio3_001074
• DTXSID00858942
• EX-A501
• L01DC03
• NWIBSHFKIJFRCO-WUDYKRTCSA-N
• BCPP000410
• Bio1_000213
• Bio1_000702
• Bio1_001191
• Bio2_000464
• Bio2_000944
• HMS1362O09
• HMS1792O09
• HMS1990O09
• HMS2089F16
• HMS3403O09
• Mutamycin(mitomycin for injection)
• (1as,8s,8ar,8bs)-6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione
• AMY10316
• AZIRINO(2',3':3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE, 6-AMINO-8-(((AMINOCARBONYL)OXY)METHYL)-1,1A,2,8,8A,8B-HEXAHYDRO-8A-METHOXY-5-METHYL-, (1AS-(1A.ALPHA.,8.BETA.,8A.ALPHA.,8B.ALPHA.))-
• Tox21_111493
• AC-918
• BDBM50428658
• GR-311
• HB4458
• s8146
• AKOS015895703
• Tox21_111493_1
• BCP9000285
• CCG-208564
• CS-0564
• DB00305
• KS-5148
• 7-AMINO-9-ALPHA-METHOXYMITOSANE
• IDI1_002219
• SMP1_000307
• Mitomycin 100 microg/mL in Acetonitrile
• NCGC00163468-02
• NCGC00163468-03
• NCGC00163468-05
• NCGC00163468-06
• [1aS-(1aalpha,8beta,8aalpha,8balpha)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
• 1404-00-8
• BM164668
• HY-13316
• SMR000058401
• BCP0726000181
• M2320
• C06681
• D00208
• D91590
• AB00918689-03
• AB00918689-04
• EN300-7405455
• Mitomycin C, Antibiotic for Culture Media Use Only
• Q-201410
• BRD-K59670716-001-02-6
• BRD-K59670716-001-06-7
• Q19856779
• WLN: T D3 B556 BN EM JV MVTTT&J GO1 H1OVZ KZ L1
• Mitomycin C from Streptomyces caespitosus, >=970 mug/mg (USP XXIV)
• Mitomycin C from Streptomyces caespitosus, powder, BioReagent, suitable for cell culture
• Mitomycin C from Streptomyces caespitosus, powder, contains NaCl as solubilizer
• (1AR)-6-AMINO-8-(((AMINOCARBONYL)OXY)METHYL)-1,1A,2,8,8A,8B-HEXAHYDRO-8A-METHOXY-5-METHYLAZIRINO(2',3':3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE
• (1aS,8S,8aR,8bS)-6-Amino-4,7-dioxo-8a-methoxy-5-methyl-1,1a,2,8,8a,8b-hexahydroazirino(2',3':3,4)pyrrolo(1,2-a)indol-8-ylmethyl carbamate
• (1aS-(1a alpha,8beta,8a alpha,8b alpha))-6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione
• [1aS-(1a?,8?,8a?,8b?)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
• 6-AMINO-1,1A,2,8,8A,8B-HEXAHYDRO-8-(HYDROXYMETHYL)-8A-METHOXY-5-METHYLAZIRINO-(2',3':3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE, CARBAMATE (ESTER)
• AZIRINO(2',3':3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE, 6-AMINO-8-(((AMINOCARBONYL)OXY)METHYL)-1,1A,2,8,8A,8B-HEXAHYDRO-8A-METHOXY-5-METHYL-, (1AS-(1AALPHA,8BETA,8AALPHA,8B.ALPHA)).-
• AZIRINO(2',3':3,4)PYRROLO(1,2-A)INDOLE-4,7-DIONE, 6-AMINO-8-(((AMINOCARBONYL)OXY)METHYL)-1,1A,2,8,8A,8B-HEXAHYDRO-8A-METHOXY-5-METHYL-,(1AR-(1AALPHA,8BETA,8AALPHA,8BALPHA))-
• Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione,6-amino-8-(((aminocarbonyl)oxy) methyl)-1,1a,2,8,8a,8b-hexahydro-8-a-methoxy-5-methyl-, (1aS-(1aalpha,8beta, 8aalpha,8balpha))-
• Azirino[2',4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a- methoxy-5-methyl-, carbamate (ester)
• Azirino[2',4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b- hexahydro-8a-methoxy-5-methyl-, [1aR-(1a.alpha.,8.beta.,8a.alpha.,8b.alpha.)]-
• Mitomycin C from Streptomyces caespitosus, >=98% (HPLC), potency: >=970 mug per mg (USP XXIV), gamma-irradiated, suitable for cell culture

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9074	90.74%
Caco-2	-	0.6402	64.02%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4831	48.31%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9470	94.70%
OATP1B3 inhibitior	+	0.9355	93.55%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7670	76.70%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.9298	92.98%
CYP3A4 substrate	+	0.5998	59.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8496	84.96%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.7642	76.42%
CYP2C19 inhibition	-	0.6115	61.15%
CYP2D6 inhibition	-	0.7464	74.64%
CYP1A2 inhibition	-	0.5813	58.13%
CYP2C8 inhibition	-	0.8371	83.71%
CYP inhibitory promiscuity	+	0.5204	52.04%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Danger	0.7522	75.22%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9694	96.94%
Skin irritation	-	0.7611	76.11%
Skin corrosion	-	0.9228	92.28%
Ames mutagenesis	+	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4008	40.08%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	+	0.6425	64.25%
skin sensitisation	-	0.8477	84.77%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	I	0.7789	77.89%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5411	54.11%
Glucocorticoid receptor binding	+	0.7165	71.65%
Aromatase binding	-	0.5145	51.45%
PPAR gamma	+	0.8707	87.07%
Honey bee toxicity	-	0.8290	82.90%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.8586	85.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.89%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.12%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.34%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	92.78%	83.82%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.44%	92.94%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.37%	96.95%
CHEMBL230	P35354	Cyclooxygenase-2	85.43%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.82%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.84%	97.25%
CHEMBL2581	P07339	Cathepsin D	83.54%	98.95%
CHEMBL255	P29275	Adenosine A2b receptor	82.78%	98.59%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.62%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.88%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.78%	94.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.63%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	80.00%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5746
• LOTUS: LTS0176580
• wikiData: Q19856779