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Mitomycin

ChemSpider ID: 5544
Molecular Formula: C₁₅H₁₈N₄O₅
Average mass: 334.327209 Da
Monoisotopic mass: 334.127716 Da
Systematic name

[(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
SMILES and InChIs

SMILES:

CC1=C(C(=O)C2=C(C1=O)N3C[C@H]4[C@@H]([C@@]3([C@@H]2COC(=O)N)OC)N4)N Copied

Std. 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 Copied

Std. InChIKey:

NWIBSHFKIJFRCO-WUDYKRTCSA-N Copied
Cite this record
CSID:5544, http://www.chemspider.com/Chemical-Structure.5544.html (accessed 01:35, May 26, 2012) Copied

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

Mitomycin [Wiki] [USP] [USAN]

[(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 [ACD/IUPAC Name]

[(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]methylcarbamat

[1aS-(1aa,8b,8aa,8ba)]-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

50-07-7 [RN]

azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-[(hydroxyiminomethoxy)methyl]-8a-methoxy-5-methyl-, (1aS,8S,8aR,8bS)-

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)-

carbamate de [(1aS,8S,8aR,8bS)-6-amino-8a-méthoxy-5-méthyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroaziréno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]méthyle

MitoExtra

Mito-medac

More...

Mitonco

Mitoplus

Mitostat

MMC complex

Oncomicina C

Oncotaxina

7-Amino-9&α;-methoxymitosane

Mitomycin C (JP14)

(1ar)-6-amino-8-(((aminoc arbonyl)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-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

[1aR-(1aα,8β,8aα,8bα)]-6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-α]indole-4,7-dione

1404-00-8 [RN]

144085-53-0 [RN]

200-008-6 [EINECS]

337376-15-5

3570056 [Beilstein]

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)

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)

6-amino-1,1A,2,8,8A-hexahydro-8-(hydroxymethyl)-8A-methoxy-5-methylazirino-(2',3':3,4)pyrrolo(1,2-A)indole-4,7-dione carbamate

6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl, [1aS-(1aα,8β,8aα,8bα)]-azirino[2',3':3,4]pyrrol o[1,2a]indole-4,7-dione

7481-68-7 [RN]

7-amino-9-α-methoxymitosane

7-Amino-9α-methoxymitosane

Ametycin

Ametycine

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-(1aα,8β,8aα,8bα))-

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-(1aα,8β,8aα,8bα))- (9CI)

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)-

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-(1aα,8β,8aα,8bα)]-

Mitamycin

Mit-C

Mito-C

Mitocin-C

Mitomycin (TN)

Mitomycin [USAN:BAN:INN] [INN] [USAN]

Mitomycin C [JP15]

mitomycin-C

Mitomycinum

Mitomycinum C

Mitomycyna C [Polish]

Mitozytrex

Muamycin

Muamycin (TN)

Mutamycin

Mytomycin

Mytomycin.

Mytozytrex

NSC-26980

Toxic solid, organic, n.o.s. (Mitomycin C)

丝裂霉素 [Chinese]

Less...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

AI3-26199 [DBID]

AIDS031090 [DBID]

AIDS-031090 [DBID]

Bio1_000213 [DBID]

Bio1_000702 [DBID]

Bio1_001191 [DBID]

Bio2_000464 [DBID]

Bio2_000944 [DBID]

C06681 [DBID]

CBiol_001927 [DBID]

More...

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Properties

Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

Data supplied by datasources and users.

experimental physchem properties
- Solubility:
  
  Soluble to 5 mM in water and to 100 mM in DMSO Tocris Bioscience

miscellaneous

Appearance:

dark blue grey crystalline powder Oxford University Chemical Safety Data

Stability:

Stable. Incompatible with strong acids, strong bases, strongoxidizing agents. Oxford University Chemical Safety Data

Toxicity:

ORL-RAT LD50 30 mg kg-1, IPR-RAT LD50 2 mg kg-1, IVN-RAT LD50 3 mg kg-1, IVN-DOG LD50 1 mg kg-1 Oxford University Chemical Safety Data

Safety:

Safety glasses, gloves, good ventilation. Oxford University Chemical Safety Data

Predicted data is generated using the ACD/Labs’ ACD/PhysChem Suite, for more information see their website.

ACD/LogP:	-0.298	# of Rule of 5 Violations:	1
ACD/LogD (pH 5.5):	-0.44	ACD/LogD (pH 7.4):	-0.30
ACD/BCF (pH 5.5):	1.00	ACD/BCF (pH 7.4):	1.00
ACD/KOC (pH 5.5):	11.77	ACD/KOC (pH 7.4):	16.33
#H bond acceptors:	9	#H bond donors:	5
#Freely Rotating Bonds:	5	Polar Surface Area:	146.89 Å²
Index of Refraction:	1.68	Molar Refractivity:	80.792 cm³
Molar Volume:	213.699 cm³	Polarizability:	32.028 10^-24cm³
Surface Tension:	77.2770004272461 dyne/cm	Density:	1.564 g/cm³
Flash Point:	305.65 °C	Enthalpy of Vaporization:	86.993 kJ/mol
Boiling Point:	581.78 °C at 760 mmHg	Vapour Pressure:	0 mmHg at 25°C

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™, for more information see their website.

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -1.18
    Log Kow (Exper. database match) =  -0.40
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  487.40  (Adapted Stein & Brown method)
    Melting Pt (deg C):  206.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.45E-011  (Modified Grain method)
    MP  (exp database):  >360 deg C
    BP  (exp database):  534 deg C
    Subcooled liquid VP: 3.75E-009 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  8430
       log Kow used: -0.40 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Aziridines
       Esters
       Quinone/Hydroquinone

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.14E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.322E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.40  (exp database)
  Log Kaw used:  -22.332  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.932
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2527
   Biowin2 (Non-Linear Model)     :   0.0011
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9420  (months      )
   Biowin4 (Primary Survey Model) :   3.1499  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0676
   Biowin6 (MITI Non-Linear Model):   0.0029
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3943
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  5E-007 Pa (3.75E-009 mm Hg)
  Log Koa (Koawin est  ): 21.932
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6 
       Octanol/air (Koa) model:  2.1E+009 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.995 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  71.8764 E-12 cm3/molecule-sec
      Half-Life =     0.149 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.786 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.275000 E-17 cm3/molecule-sec
      Half-Life =     0.504 Days (at 7E11 mol/cm3)
      Half-Life =     12.090 Hrs
   Fraction sorbed to airborne particulates (phi): 0.997 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  13.29
      Log Koc:  1.123 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  6.602E-005  L/mol-sec
  Kb Half-Life at pH 8:     332.653  years  
  Kb Half-Life at pH 7:    3326.534  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.40 (expkow database)

 Volatilization from Water:
    Henry LC:  1.14E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.391E+020  hours   (3.913E+019 days)
    Half-Life from Model Lake : 1.024E+022  hours   (4.268E+020 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       4.28e-015       2.76         1000       
   Water     49.2            1.44e+003    1000       
   Soil      50.7            2.88e+003    1000       
   Sediment  0.096           1.3e+004     0          
     Persistence Time: 1.18e+003 hr

Click to predict properties on the Chemicalize site

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Category	Target	PDB Code	LASSO Score
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.95
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.16
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.04
Other Enzymes	NA, neuraminidase	1a4g	0.04
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.02
Kinases	TK, thymidine kinase	1kim	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Serine Proteases	Thrombin	1ba8	0.00

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Mitomycin

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