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5508-58-7 molecular structure
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(4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one

ChemBase ID: 69911
Molecular Formular: C20H30O5
Molecular Mass: 350.4492
Monoisotopic Mass: 350.20932406
SMILES and InChIs

SMILES:
O1C(=O)/C(=C/C[C@@H]2C(=C)CC[C@@H]3[C@]([C@@H](CC[C@@]23C)O)(C)CO)/[C@@H](C1)O
Canonical SMILES:
OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C/C=C/1\[C@H](O)COC1=O)C
InChI:
InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
InChIKey:
BOJKULTULYSRAS-OTESTREVSA-N

Cite this record

CBID:69911 http://www.chembase.cn/molecule-69911.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
IUPAC Traditional name
(4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
Synonyms
Andrographolide
Andrographolide
穿心莲内酯
CAS Number
5508-58-7
EC Number
226-852-5
MDL Number
MFCD07778082
Beilstein Number
42762
PubChem SID
24862550
162035636
PubChem CID
5318517

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.477876  H Acceptors
H Donor LogD (pH = 5.5) 1.6623217 
LogD (pH = 7.4) 1.6623213  Log P 1.6623217 
Molar Refractivity 94.9305 cm3 Polarizability 37.537582 Å3
Polar Surface Area 86.99 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Apperance
Powder expand Show data source
Melting Point
229-232 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -126°, c = 1.5 in acetic acid expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
LU3490750 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
false expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
95+% expand Show data source
98% expand Show data source
98.0 expand Show data source
Empirical Formula (Hill Notation)
C20H30O5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 365645 external link
Biochem/physiol Actions
Diterpenoid lactone with anti-inflammatory properties. It blocks T-cell proliferation to allogenic stimuli and the chemotactic migration of macrophages induced by complement. Blocks the proliferation of several cancer cell lines in vitro.
Packaging
100, 500 mg in glass bottle

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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