NP-MRD: Showing NP-Card for 4alpha-acetoxycadina-2,9-diene-1,8-dione (NP0034342)

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Record Information

Version

2.0

Created at

2021-06-20 18:05:58 UTC

Updated at

2021-06-30 00:04:40 UTC

NP-MRD ID

NP0034342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4alpha-acetoxycadina-2,9-diene-1,8-dione

Provided By

JEOL Database JEOL Logo

Description

(4S)-3,8-Dimethyl-4beta-acetoxy-5alpha-isopropyl 1,4,4aalpha,5,6,7-hexahydronaphthalene-1,7-dione belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 4alpha-acetoxycadina-2,9-diene-1,8-dione is found in Curcuma parviflora. 4alpha-acetoxycadina-2,9-diene-1,8-dione was first documented in 2009 (Sadhu, S. K., et al.). Based on a literature review very few articles have been published on (4S)-3,8-Dimethyl-4beta-acetoxy-5alpha-isopropyl 1,4,4aalpha,5,6,7-hexahydronaphthalene-1,7-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120063D          

 43 44  0  0  0  0            999 V2000
   -4.8600   -3.3772   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718   -3.2141   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -3.6490   -2.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -2.5135   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379   -2.2600   -0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0146   -3.1492    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7413   -4.5799    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -2.6969    1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -1.3087    2.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453   -0.9535    3.5232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.3871    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518    0.7092    1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8357    1.0426    3.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    1.7344    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047    2.6870    0.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.6114   -0.6675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0342    0.1567   -1.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5187   -0.0212   -2.6005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0681    0.4209   -2.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    0.6936   -3.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991   -0.7450   -0.0986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3404   -2.3958   -1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1877   -3.9476   -2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1309    1.7159    3.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2398    0.2378   -3.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203   -0.1357   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4709    0.4130   -3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3423    1.7824   -3.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442    0.4146   -4.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185   -0.5604   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 21  1  0  0  0  0
 14 15  2  0  0  0  0
  9 10  2  0  0  0  0
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  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
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M  END

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -4.8600   -3.3772   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718   -3.2141   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -3.6490   -2.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -2.5135   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379   -2.2600   -0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0146   -3.1492    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7413   -4.5799    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -2.6969    1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -1.3087    2.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453   -0.9535    3.5232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.3871    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518    0.7092    1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8357    1.0426    3.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    1.7344    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047    2.6870    0.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.6114   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3404   -2.3958   -1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1877   -3.9476   -2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1469   -3.9252   -0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -2.5110   -1.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276   -5.1489    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -4.6298   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633   -5.0783    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152   -3.3333    2.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309    1.7159    3.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    0.1530    3.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8153    1.5322    3.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    1.9887   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303    2.2615   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944   -0.1373   -1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.0849   -2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4709    0.4130   -3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2185   -0.5604   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 21  1  0
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  8  6  2  0
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  7 26  1  0
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  7 28  1  0
M  END


  Mrv1652306202120063D          

 43 44  0  0  0  0            999 V2000
   -4.8600   -3.3772   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718   -3.2141   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -3.6490   -2.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -2.5135   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379   -2.2600   -0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0146   -3.1492    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7413   -4.5799    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -2.6969    1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -1.3087    2.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453   -0.9535    3.5232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.3871    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518    0.7092    1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8357    1.0426    3.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    1.7344    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047    2.6870    0.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.6114   -0.6675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0342    0.1567   -1.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5187   -0.0212   -2.6005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0681    0.4209   -2.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    0.6936   -3.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991   -0.7450   -0.0986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3404   -2.3958   -1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1442    0.4146   -4.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185   -0.5604   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14 15  2  0  0  0  0
  9 10  2  0  0  0  0
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  2  3  2  0  0  0  0
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  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
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 19 37  1  0  0  0  0
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 20 40  1  0  0  0  0
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  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]2([H])C(C1=O)=C(C(=O)C([H])([H])[C@@]2([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-8(2)12-7-13(19)10(4)15-14(20)6-9(3)17(16(12)15)21-11(5)18/h6,8,12,16-17H,7H2,1-5H3/t12-,16-,17+/m0/s1

> <INCHI_KEY>
IMPYLWTUBJWLNC-AFAVFJNCSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.359

> <EXACT_MASS>
290.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.469865996552574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,8S,8aS)-2,5-dimethyl-4,6-dioxo-8-(propan-2-yl)-1,4,6,7,8,8a-hexahydronaphthalen-1-yl acetate

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.71813637

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.616421110618717

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.400466336056994

> <JCHEM_PKA_STRONGEST_BASIC>
-6.534611426548717

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
80.28490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8S,8aS)-8-isopropyl-2,5-dimethyl-4,6-dioxo-1,7,8,8a-tetrahydronaphthalen-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -4.8600   -3.3772   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718   -3.2141   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -3.6490   -2.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -2.5135   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379   -2.2600   -0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0146   -3.1492    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7413   -4.5799    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -2.6969    1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -1.3087    2.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453   -0.9535    3.5232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.3871    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518    0.7092    1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8357    1.0426    3.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    1.7344    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047    2.6870    0.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.6114   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342    0.1567   -1.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5187   -0.0212   -2.6005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0681    0.4209   -2.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    0.6936   -3.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991   -0.7450   -0.0986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3404   -2.3958   -1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1877   -3.9476   -2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1469   -3.9252   -0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -2.5110   -1.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276   -5.1489    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -4.6298   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633   -5.0783    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152   -3.3333    2.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309    1.7159    3.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    0.1530    3.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8153    1.5322    3.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    1.9887   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303    2.2615   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944   -0.1373   -1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.0849   -2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    1.4893   -2.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2398    0.2378   -3.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203   -0.1357   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4709    0.4130   -3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3423    1.7824   -3.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442    0.4146   -4.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185   -0.5604   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 21  1  0
 14 15  2  0
  9 10  2  0
  8  6  2  0
 12 13  1  0
  8  9  1  0
 17 18  1  0
  6  5  1  0
 21 43  1  1
  5 21  1  0
  5  4  1  0
 11  9  1  0
  4  2  1  0
 11 12  2  0
  2  1  1  0
 21 17  1  0
  2  3  2  0
 17 16  1  0
 18 19  1  0
 16 14  1  0
 18 20  1  0
 14 12  1  0
  6  7  1  0
  8 29  1  0
  5 25  1  6
 17 35  1  6
 16 33  1  0
 16 34  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 18 36  1  6
  1 22  1  0
  1 23  1  0
  1 24  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.860  -3.377  -1.527  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.372  -3.214  -1.571  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.655  -3.649  -2.459  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.952  -2.514  -0.484  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.538  -2.260  -0.377  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.015  -3.149   0.725  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.741  -4.580   0.356  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.799  -2.697   1.969  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.105  -1.309   2.380  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.845  -0.954   3.523  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.662  -0.387   1.337  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.352   0.709   1.718  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.836   1.043   3.102  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.670   1.734   0.676  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.405   2.687   0.927  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.992   1.611  -0.668  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.034   0.157  -1.140  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.519  -0.021  -2.600  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.068   0.421  -2.811  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.422   0.694  -3.613  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.299  -0.745  -0.099  0.00  0.00           C+0
HETATM   22  H   UNK     0      -5.340  -2.396  -1.551  0.00  0.00           H+0
HETATM   23  H   UNK     0      -5.188  -3.948  -2.401  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.147  -3.925  -0.627  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.003  -2.511  -1.300  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.328  -5.149   1.195  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.019  -4.630  -0.466  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.663  -5.078   0.041  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.415  -3.333   2.760  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.131   1.716   3.599  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.978   0.153   3.722  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.815   1.532   3.073  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.969   1.989  -0.570  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.530   2.261  -1.364  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.094  -0.137  -1.142  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.572  -1.085  -2.856  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.064   1.489  -2.615  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.240   0.238  -3.847  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.620  -0.136  -2.169  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.471   0.413  -3.469  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.342   1.782  -3.539  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.144   0.415  -4.636  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.219  -0.560  -0.177  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6   21    4   25                                             
CONECT    6    8    5    7                                                  
CONECT    7    6   26   27   28                                             
CONECT    8    6    9   29                                                  
CONECT    9   10    8   11                                                  
CONECT   10    9                                                            
CONECT   11   21    9   12                                                  
CONECT   12   13   11   14                                                  
CONECT   13   12   30   31   32                                             
CONECT   14   15   16   12                                                  
CONECT   15   14                                                            
CONECT   16   17   14   33   34                                             
CONECT   17   18   21   16   35                                             
CONECT   18   17   19   20   36                                             
CONECT   19   18   37   38   39                                             
CONECT   20   18   40   41   42                                             
CONECT   21   11   43    5   17                                             
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30   13                                                            
CONECT   31   13                                                            
CONECT   32   13                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   19                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   20                                                            
CONECT   42   20                                                            
CONECT   43   21                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   88    0
END

RDKit          3D

43 44  0  0  0  0  0  0  0  0999 V2000
   -4.8600   -3.3772   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718   -3.2141   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546   -3.6490   -2.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -2.5135   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379   -2.2600   -0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0146   -3.1492    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7413   -4.5799    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -2.6969    1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -1.3087    2.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453   -0.9535    3.5232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.3871    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518    0.7092    1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8357    1.0426    3.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    1.7344    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047    2.6870    0.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.6114   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342    0.1567   -1.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5187   -0.0212   -2.6005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0681    0.4209   -2.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    0.6936   -3.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991   -0.7450   -0.0986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3404   -2.3958   -1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1877   -3.9476   -2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1469   -3.9252   -0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -2.5110   -1.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276   -5.1489    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -4.6298   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633   -5.0783    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152   -3.3333    2.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309    1.7159    3.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    0.1530    3.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8153    1.5322    3.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    1.9887   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303    2.2615   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944   -0.1373   -1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.0849   -2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    1.4893   -2.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2398    0.2378   -3.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203   -0.1357   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4709    0.4130   -3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3423    1.7824   -3.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442    0.4146   -4.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185   -0.5604   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 21  1  0
 14 15  2  0
  9 10  2  0
  8  6  2  0
 12 13  1  0
  8  9  1  0
 17 18  1  0
  6  5  1  0
 21 43  1  1
  5 21  1  0
  5  4  1  0
 11  9  1  0
  4  2  1  0
 11 12  2  0
  2  1  1  0
 21 17  1  0
  2  3  2  0
 17 16  1  0
 18 19  1  0
 16 14  1  0
 18 20  1  0
 14 12  1  0
  6  7  1  0
  8 29  1  0
  5 25  1  6
 17 35  1  6
 16 33  1  0
 16 34  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 18 36  1  6
  1 22  1  0
  1 23  1  0
  1 24  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4S)-3,8-Dimethyl-4b-acetoxy-5a-isopropyl 1,4,4aalpha,5,6,7-hexahydronaphthalene-1,7-dione	Generator
(4S)-3,8-Dimethyl-4β-acetoxy-5α-isopropyl 1,4,4aalpha,5,6,7-hexahydronaphthalene-1,7-dione	Generator

Chemical Formula

C₁₇H₂₂O₄

Average Mass

290.3590 Da

Monoisotopic Mass

290.15181 Da

IUPAC Name

(1S,8S,8aS)-2,5-dimethyl-4,6-dioxo-8-(propan-2-yl)-1,4,6,7,8,8a-hexahydronaphthalen-1-yl acetate

Traditional Name

(1S,8S,8aS)-8-isopropyl-2,5-dimethyl-4,6-dioxo-1,7,8,8a-tetrahydronaphthalen-1-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C1=C(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]2([H])C(C1=O)=C(C(=O)C([H])([H])[C@@]2([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C17H22O4/c1-8(2)12-7-13(19)10(4)15-14(20)6-9(3)17(16(12)15)21-11(5)18/h6,8,12,16-17H,7H2,1-5H3/t12-,16-,17+/m0/s1

InChI Key

IMPYLWTUBJWLNC-AFAVFJNCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Curcuma parviflora	JEOL database	Sadhu, S. K., et al, J. Nat. Prod. 72, 782 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cadinane sesquiterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.78	ALOGPS
logP	2.72	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	15.4	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.28 m³·mol⁻¹	ChemAxon
Polarizability	31.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28286274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42638465

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sadhu, S. K., et al. (2009). Sadhu, S. K., et al, J. Nat. Prod. 72, 782 (2009). J. Nat. Prod..

Showing NP-Card for 4alpha-acetoxycadina-2,9-diene-1,8-dione (NP0034342)

MOL for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

3D MOL for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

3D SDF for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

3D-SDF for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

PDB for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

3D PDB for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

SMILES for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

INCHI for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

Structure for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)

3D Structure for NP0034342 (4alpha-acetoxycadina-2,9-diene-1,8-dione)