NP-MRD: Showing NP-Card for 3beta-chlorodehydrocostuslactone (NP0030007)

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Record Information

Version

1.0

Created at

2021-06-19 21:28:42 UTC

Updated at

2021-06-29 23:57:43 UTC

NP-MRD ID

NP0030007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta-chlorodehydrocostuslactone

Provided By

JEOL Database JEOL Logo

Description

3Beta-Chlorodehydrocostuslactone belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 3beta-chlorodehydrocostuslactone is found in Laurus nobilis. It was first documented in 2006 (PMID: 16880666). Based on a literature review very few articles have been published on 3beta-Chlorodehydrocostuslactone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123283D          

 35 37  0  0  0  0            999 V2000
    2.2775    3.3816    1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421    2.8770    1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    3.7358    1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665    4.9508    1.2229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1862    2.9183    0.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    1.5482    0.7636 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5734    1.4628    1.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5594    0.4328    0.9554 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9588   -0.9218    0.5881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1371   -1.3804    1.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410   -2.2254    2.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549   -0.9033    1.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1211   -1.3041   -0.1013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4347   -0.5342   -0.1848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8576   -0.1937   -1.8705 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758    0.7147    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446    1.7280    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396    0.6158    1.3560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4530    4.4518    1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    2.7509    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.3776   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3863    1.2445    2.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    0.2761    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0669    0.8262    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -1.6622    0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -0.8868   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507   -2.5853    2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276   -2.5866    3.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2028   -1.3831    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.0196   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847   -2.3854   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -1.1135    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0015    1.7355    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    2.5870    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024    0.8892    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 16 18  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  3  0  0  0
 10 12  1  0  0  0  0
  2  1  2  3  0  0  0
  6  5  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  0  0  0  0
 16 17  2  3  0  0  0
  3  2  1  0  0  0  0
 14 15  1  0  0  0  0
  7  2  1  0  0  0  0
 18 35  1  1  0  0  0
 18 12  1  0  0  0  0
 12 29  1  1  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  8 23  1  0  0  0  0
  8 24  1  0  0  0  0
  7 22  1  1  0  0  0
  6 21  1  6  0  0  0
 13 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  1  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    2.2775    3.3816    1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421    2.8770    1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    3.7358    1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665    4.9508    1.2229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1862    2.9183    0.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    1.5482    0.7636 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5734    1.4628    1.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5594    0.4328    0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9588   -0.9218    0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371   -1.3804    1.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410   -2.2254    2.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549   -0.9033    1.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1211   -1.3041   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347   -0.5342   -0.1848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8576   -0.1937   -1.8705 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758    0.7147    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446    1.7280    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396    0.6158    1.3560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4530    4.4518    1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    2.7509    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.3776   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3863    1.2445    2.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    0.2761    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0669    0.8262    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -1.6622    0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -0.8868   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507   -2.5853    2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276   -2.5866    3.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2028   -1.3831    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.0196   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847   -2.3854   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -1.1135    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0015    1.7355    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    2.5870    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024    0.8892    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
  7  6  1  0
  9  8  1  0
  8  7  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 16 18  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
  2  1  2  3
  6  5  1  0
  3  4  2  0
  5  3  1  0
 16 17  2  3
  3  2  1  0
 14 15  1  0
  7  2  1  0
 18 35  1  1
 18 12  1  0
 12 29  1  1
  9 25  1  0
  9 26  1  0
  8 23  1  0
  8 24  1  0
  7 22  1  1
  6 21  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  1
 11 27  1  0
 11 28  1  0
  1 19  1  0
  1 20  1  0
 17 33  1  0
 17 34  1  0
M  END


  Mrv1652306192123283D          

 35 37  0  0  0  0            999 V2000
    2.2775    3.3816    1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421    2.8770    1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    3.7358    1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665    4.9508    1.2229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1862    2.9183    0.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    1.5482    0.7636 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5734    1.4628    1.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5594    0.4328    0.9554 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9588   -0.9218    0.5881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1371   -1.3804    1.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410   -2.2254    2.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549   -0.9033    1.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1211   -1.3041   -0.1013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4347   -0.5342   -0.1848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8576   -0.1937   -1.8705 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758    0.7147    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446    1.7280    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396    0.6158    1.3560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4530    4.4518    1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    2.7509    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.3776   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3863    1.2445    2.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    0.2761    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0669    0.8262    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -1.6622    0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -0.8868   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507   -2.5853    2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276   -2.5866    3.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2028   -1.3831    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.0196   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847   -2.3854   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -1.1135    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0015    1.7355    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    2.5870    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024    0.8892    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 16 18  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  3  0  0  0
 10 12  1  0  0  0  0
  2  1  2  3  0  0  0
  6  5  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  0  0  0  0
 16 17  2  3  0  0  0
  3  2  1  0  0  0  0
 14 15  1  0  0  0  0
  7  2  1  0  0  0  0
 18 35  1  1  0  0  0
 18 12  1  0  0  0  0
 12 29  1  1  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  8 23  1  0  0  0  0
  8 24  1  0  0  0  0
  7 22  1  1  0  0  0
  6 21  1  6  0  0  0
 13 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  1  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C(=O)O[C@@]2([H])[C@@]1([H])C([H])([H])C([H])([H])C(=C([H])[H])[C@]1([H])C([H])([H])[C@]([H])(Cl)C(=C([H])[H])[C@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H17ClO2/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14H,1-6H2/t10-,11-,12-,13-,14-/m0/s1

> <INCHI_KEY>
XVGIEOUYQLZGPH-PEDHHIEDSA-N

> <FORMULA>
C15H17ClO2

> <MOLECULAR_WEIGHT>
264.747

> <EXACT_MASS>
264.091707495

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.0795793708578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.1990360063333334

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.865905204973273

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
70.53790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    2.2775    3.3816    1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421    2.8770    1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    3.7358    1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665    4.9508    1.2229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1862    2.9183    0.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    1.5482    0.7636 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5734    1.4628    1.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5594    0.4328    0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9588   -0.9218    0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371   -1.3804    1.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410   -2.2254    2.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549   -0.9033    1.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1211   -1.3041   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347   -0.5342   -0.1848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8576   -0.1937   -1.8705 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758    0.7147    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446    1.7280    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396    0.6158    1.3560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4530    4.4518    1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    2.7509    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.3776   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3863    1.2445    2.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    0.2761    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0669    0.8262    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -1.6622    0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -0.8868   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507   -2.5853    2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276   -2.5866    3.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2028   -1.3831    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.0196   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847   -2.3854   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -1.1135    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0015    1.7355    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    2.5870    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024    0.8892    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
  7  6  1  0
  9  8  1  0
  8  7  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 16 18  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
  2  1  2  3
  6  5  1  0
  3  4  2  0
  5  3  1  0
 16 17  2  3
  3  2  1  0
 14 15  1  0
  7  2  1  0
 18 35  1  1
 18 12  1  0
 12 29  1  1
  9 25  1  0
  9 26  1  0
  8 23  1  0
  8 24  1  0
  7 22  1  1
  6 21  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  1
 11 27  1  0
 11 28  1  0
  1 19  1  0
  1 20  1  0
 17 33  1  0
 17 34  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       2.277   3.382   1.543  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.042   2.877   1.435  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.134   3.736   1.185  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.167   4.951   1.223  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.186   2.918   0.931  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.757   1.548   0.764  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.573   1.463   1.511  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.559   0.433   0.955  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.959  -0.922   0.588  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.137  -1.380   1.517  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.141  -2.225   2.525  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.555  -0.903   1.268  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.121  -1.304  -0.101  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.435  -0.534  -0.185  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -3.858  -0.194  -1.871  0.00  0.00          Cl+0
HETATM   16  C   UNK     0      -3.176   0.715   0.621  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.045   1.728   0.765  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.840   0.616   1.356  0.00  0.00           C+0
HETATM   19  H   UNK     0       2.453   4.452   1.458  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.140   2.751   1.728  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.639   1.378  -0.315  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.386   1.244   2.572  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.351   0.276   1.701  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.067   0.826   0.064  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.770  -1.662   0.563  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.594  -0.887  -0.443  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.151  -2.585   2.705  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.628  -2.587   3.203  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.203  -1.383   2.021  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.449  -1.020  -0.918  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.285  -2.385  -0.173  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.246  -1.113   0.271  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.002   1.736   0.251  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.817   2.587   1.390  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.002   0.889   2.408  0.00  0.00           H+0
CONECT    1    2   19   20                                                  
CONECT    2    1    3    7                                                  
CONECT    3    4    5    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6   18    7    5   21                                             
CONECT    7    6    8    2   22                                             
CONECT    8    9    7   23   24                                             
CONECT    9    8   10   25   26                                             
CONECT   10    9   11   12                                                  
CONECT   11   10   27   28                                                  
CONECT   12   13   10   18   29                                             
CONECT   13   12   14   30   31                                             
CONECT   14   13   16   15   32                                             
CONECT   15   14                                                            
CONECT   16   14   18   17                                                  
CONECT   17   16   33   34                                                  
CONECT   18    6   16   35   12                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    6                                                            
CONECT   22    7                                                            
CONECT   23    8                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27   11                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   17                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
    2.2775    3.3816    1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421    2.8770    1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    3.7358    1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665    4.9508    1.2229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1862    2.9183    0.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    1.5482    0.7636 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5734    1.4628    1.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5594    0.4328    0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9588   -0.9218    0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371   -1.3804    1.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410   -2.2254    2.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549   -0.9033    1.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1211   -1.3041   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347   -0.5342   -0.1848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8576   -0.1937   -1.8705 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758    0.7147    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446    1.7280    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396    0.6158    1.3560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4530    4.4518    1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    2.7509    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.3776   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3863    1.2445    2.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    0.2761    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0669    0.8262    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -1.6622    0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -0.8868   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507   -2.5853    2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276   -2.5866    3.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2028   -1.3831    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.0196   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847   -2.3854   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -1.1135    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0015    1.7355    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    2.5870    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024    0.8892    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
  7  6  1  0
  9  8  1  0
  8  7  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 16 18  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
  2  1  2  3
  6  5  1  0
  3  4  2  0
  5  3  1  0
 16 17  2  3
  3  2  1  0
 14 15  1  0
  7  2  1  0
 18 35  1  1
 18 12  1  0
 12 29  1  1
  9 25  1  0
  9 26  1  0
  8 23  1  0
  8 24  1  0
  7 22  1  1
  6 21  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  1
 11 27  1  0
 11 28  1  0
  1 19  1  0
  1 20  1  0
 17 33  1  0
 17 34  1  0
M  END

View in JSmol

Synonyms

Value	Source
3b-Chlorodehydrocostuslactone	Generator
3Β-chlorodehydrocostuslactone	Generator

Chemical Formula

C₁₅H₁₇ClO₂

Average Mass

264.7470 Da

Monoisotopic Mass

264.09171 Da

IUPAC Name

(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C(=O)O[C@@]2([H])[C@@]1([H])C([H])([H])C([H])([H])C(=C([H])[H])[C@]1([H])C([H])([H])[C@]([H])(Cl)C(=C([H])[H])[C@]21[H]

InChI Identifier

InChI=1S/C15H17ClO2/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14H,1-6H2/t10-,11-,12-,13-,14-/m0/s1

InChI Key

XVGIEOUYQLZGPH-PEDHHIEDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Laurus nobilis	KNApSAcK Database	22123792
Laurus nobilis L.	JEOL database	Dall'Acqua, S., et al, Chem. Pharm. Bull. 54, 1187 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic 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	3.14	ALOGPS
logP	3.2	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.54 m³·mol⁻¹	ChemAxon
Polarizability	28.08 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001782

KNApSAcK ID

C00029488

Chemspider ID

8834671

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10659317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dall'Acqua S, Viola G, Giorgetti M, Loi MC, Innocenti G: Two new sesquiterpene lactones from the leaves of Laurus nobilis. Chem Pharm Bull (Tokyo). 2006 Aug;54(8):1187-9. doi: 10.1248/cpb.54.1187. [PubMed:16880666 ]
Dall'Acqua, S., et al. (2006). Dall'Acqua, S., et al, Chem. Pharm. Bull. 54, 1187 (2006). Chem. Pharm. Bull..

Showing NP-Card for 3beta-chlorodehydrocostuslactone (NP0030007)

MOL for NP0030007 (3beta-chlorodehydrocostuslactone)

3D MOL for NP0030007 (3beta-chlorodehydrocostuslactone)

3D SDF for NP0030007 (3beta-chlorodehydrocostuslactone)

3D-SDF for NP0030007 (3beta-chlorodehydrocostuslactone)

PDB for NP0030007 (3beta-chlorodehydrocostuslactone)

3D PDB for NP0030007 (3beta-chlorodehydrocostuslactone)

SMILES for NP0030007 (3beta-chlorodehydrocostuslactone)

INCHI for NP0030007 (3beta-chlorodehydrocostuslactone)

Structure for NP0030007 (3beta-chlorodehydrocostuslactone)

3D Structure for NP0030007 (3beta-chlorodehydrocostuslactone)