CAS 86639-52-3|SN-38|(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,2<su...

General Information

Structure

Molecular Formula

C₂₂H₂₀N₂O₅

Molecular Mass

392.4046

Exact Mass

392.13722175

Charge

InChI

InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1

InChIKey

FJHBVJOVLFPMQE-QFIPXVFZSA-N

Canonic Smiles

CC[C@@]1(O)C(=O)OCc2c1cc1-c3nc4ccc(cc4c(c3Cn1c2=O)CC)O

Isomeric Smiles

O=c1n2c(cc3c1COC(=O)[C@]3(O)CC)c1nc3c(c(c1C2)CC)cc(O)cc3

Calculated Properties

JChem

LogD (pH = 7.4)

1.87

LogD (pH = 5.5)

1.86

Log P

1.87

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.66

Polar Surface Area

99.96

Polarizability

41.69

Molar Refractivity

106.12

LOG S

-4.32

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

SN-387-Ethyl-10-hydroxy-camptothecin(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione10-Hydroxy-7-ethylcamptothecin7-Ethyl-10-hydroxycamptothecin(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)dione7-Ethyl-10-hydroxycamptothecinSN 38 Lactone10-Hydroxy-7-ethylcamptothecin7-Ethyl-10-hydroxy-20(S)-camptothecinSN 387-Ethyl-10-hydroxycamptothecinSN 38 lactoneSN-38NK 012NK-012

IUPAC name

(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

IUPAC Traditional name

7-ethyl-10-hydroxycamptothecin (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

Names and Identifiers

Registration numbers

PubChem CID

104842

Unique Ingredient Identifier

CAS Number

Chemspider ID

CHEMBL

Wikipedia Title

PubChem SID

MDL Number

MFCD00871873MFCD06762720

PDBeChem Database

RS4

ACToR Database

86639-52-3113015-38-6

MetaboLights Database

MTBLS1757MTBLS2825MTBLS379MTBLS2267MTBLS2145

BRENDA Ligand Database

BRENDA Database

Reaxys Registry

CHEBI ID

ArrayExpress (Gene Expression Altlas)

KEGG ID

BKMS React Database

Protein Data Bank

Rhea Database

SureChEMBL Database

HMDB Database

CompTox Database

Registration numbers

Properties

Physical Property

Apperance

Light-Yellow Solid

Solubility

DMSO

Melting Point

218-221°C dec.

Hydrophobicity(logP)

1.974

Safety Information

Storage Condition

-20°C Freezer

MSDS Link

Download link

Product Information

Certificate of Analysis

Download link

Purity

95%

95+%

Properties

Related Proteins

PDB Bank

6VXJ

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

SN-38

TRC

S589950

A metabolite of Irinotecan, a DNA topoisomerase inhibitor.

ChEBI

CHEBI:8988

A member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself.

Molecule Details

References

PubChem Literature

From Data Sources

• Ashley, G., et al.: J. Antibiot., 57, 224 (2000)

• Billecke, S., et al.: Drug Metab. Dispos., 28, 1335 (2000)

• Teiber, J., et al.: Biochem. Pharmacol., 66, 887 (2000)

References

Bioactivity

PubChem BioAssay

Bioactivity

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