NP-MRD: Showing NP-Card for (-)-alpha-Cedrene (NP0030845)

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Record Information

Version

2.0

Created at

2021-06-19 22:05:37 UTC

Updated at

2021-08-20 00:00:20 UTC

NP-MRD ID

NP0030845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-alpha-Cedrene

Provided By

JEOL Database JEOL Logo

Description

Alpha-Cedrene, also known as a-cedrene, belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Thus, alpha-cedrene is considered to be an isoprenoid. Alpha-Cedrene is a sweet, cedar, and fresh tasting compound. Alpha-Cedrene is found, on average, in the highest concentration within safflowers (Carthamus tinctorius). Alpha-Cedrene has also been detected, but not quantified in, several different foods, such as common sages (Salvia officinalis), wild celeries (Apium graveolens), rabbiteye blueberries (Vaccinium virgatum), tarragons (Artemisia dracunculus), and sweet basils (Ocimum basilicum). This could make alpha-cedrene a potential biomarker for the consumption of these foods. Alpha-Cedrene is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (-)-alpha-Cedrene is found in Acorus calamus, Eupatorium adenophorum , Artemisia annua, Artemisia herba-alba, Asarum simile, Cupressus funebris Endl., Curcuma wenyujin , Juniperus horizontalis, Juniperus procera, Juniperus thurifera, Osyris quadripartita, Persicaria minor, Sideritis athoa, Tagetes filifolia, Thuja occidentalis , Thymus citriodorus, Tordylium apulum, Trachyspermum anethifolium and Vitis vinifera. (-)-alpha-Cedrene was first documented in 1993 (PMID: 16348930). Based on a literature review very few articles have been published on alpha-Cedrene.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100053D          

 39 41  0  0  0  0            999 V2000
   -2.2110   -0.2924   -4.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6848    0.0924   -3.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    0.3983   -3.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193    0.8197   -1.7192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9695    0.7300   -0.6151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2726    1.2996   -1.2024 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6875    0.1492   -2.1433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6050   -1.0882   -1.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4376   -2.4339   -1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.1959   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.7698   -0.3338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4139   -0.8788    1.1887 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3430    0.1006    1.6488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5927    1.3269    0.7632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5782    2.2982    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -0.3122   -5.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.2860   -4.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    0.4267   -4.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3312    0.3712   -3.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    1.8523   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856    0.2035   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0313    1.4772   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    2.2503   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6997    0.3184   -2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -2.6193   -2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -2.4824   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027   -3.2616   -1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8642   -2.0314    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7652   -1.3750   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.2889    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009   -1.4066   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -0.5594    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -1.8975    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.3360    2.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -0.3166    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    1.8571    1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    2.6612    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808    3.1687    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093    1.8286    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 13 12  1  0  0  0  0
  8  7  1  0  0  0  0
  3  2  2  0  0  0  0
  7  2  1  0  0  0  0
 11  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
 12 11  1  0  0  0  0
  8  9  1  6  0  0  0
  5  4  1  6  0  0  0
 14 15  1  0  0  0  0
  5 14  1  0  0  0  0
 11 31  1  6  0  0  0
 11  8  1  0  0  0  0
  8 10  1  0  0  0  0
 14 13  1  0  0  0  0
  2  1  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 14 36  1  1  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  3 19  1  0  0  0  0
  7 24  1  6  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.2110   -0.2924   -4.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6848    0.0924   -3.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    0.3983   -3.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193    0.8197   -1.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9695    0.7300   -0.6151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2726    1.2996   -1.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6875    0.1492   -2.1433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6050   -1.0882   -1.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4376   -2.4339   -1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.1959   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.7698   -0.3338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4139   -0.8788    1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    0.1006    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    1.3269    0.7632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5782    2.2982    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -0.3122   -5.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.2860   -4.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    0.4267   -4.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3312    0.3712   -3.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    1.8523   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856    0.2035   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0313    1.4772   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    2.2503   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6997    0.3184   -2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -2.6193   -2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -2.4824   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027   -3.2616   -1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8642   -2.0314    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7652   -1.3750   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.2889    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009   -1.4066   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -0.5594    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -1.8975    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.3360    2.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -0.3166    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    1.8571    1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    2.6612    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808    3.1687    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093    1.8286    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 13 12  1  0
  8  7  1  0
  3  2  2  0
  7  2  1  0
 11  5  1  0
  5  6  1  0
  7  6  1  0
 12 11  1  0
  8  9  1  6
  5  4  1  6
 14 15  1  0
  5 14  1  0
 11 31  1  6
 11  8  1  0
  8 10  1  0
 14 13  1  0
  2  1  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  0
 12 33  1  0
 14 36  1  1
  4 20  1  0
  4 21  1  0
  3 19  1  0
  7 24  1  6
  6 22  1  0
  6 23  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
M  END


  Mrv1652306202100053D          

 39 41  0  0  0  0            999 V2000
   -2.2110   -0.2924   -4.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6848    0.0924   -3.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    0.3983   -3.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193    0.8197   -1.7192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9695    0.7300   -0.6151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2726    1.2996   -1.2024 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6875    0.1492   -2.1433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6050   -1.0882   -1.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4376   -2.4339   -1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.1959   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.7698   -0.3338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4139   -0.8788    1.1887 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3430    0.1006    1.6488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5927    1.3269    0.7632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5782    2.2982    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -0.3122   -5.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.2860   -4.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    0.4267   -4.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3312    0.3712   -3.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    1.8523   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856    0.2035   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0313    1.4772   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    2.2503   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6997    0.3184   -2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -2.6193   -2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -2.4824   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027   -3.2616   -1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8642   -2.0314    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7652   -1.3750   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.2889    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009   -1.4066   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -0.5594    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -1.8975    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.3360    2.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -0.3166    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    1.8571    1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    2.6612    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808    3.1687    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093    1.8286    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 13 12  1  0  0  0  0
  8  7  1  0  0  0  0
  3  2  2  0  0  0  0
  7  2  1  0  0  0  0
 11  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
 12 11  1  0  0  0  0
  8  9  1  6  0  0  0
  5  4  1  6  0  0  0
 14 15  1  0  0  0  0
  5 14  1  0  0  0  0
 11 31  1  6  0  0  0
 11  8  1  0  0  0  0
  8 10  1  0  0  0  0
 14 13  1  0  0  0  0
  2  1  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 14 36  1  1  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  3 19  1  0  0  0  0
  7 24  1  6  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C([H])([H])[H])[C@]2([H])C([H])([H])[C@@]3(C1([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]3([H])C2(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1

> <INCHI_KEY>
IRAQOCYXUMOFCW-OSFYFWSMSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.628158060679286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
4.101158186333333

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.6944

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.2110   -0.2924   -4.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6848    0.0924   -3.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    0.3983   -3.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193    0.8197   -1.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9695    0.7300   -0.6151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2726    1.2996   -1.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6875    0.1492   -2.1433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6050   -1.0882   -1.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4376   -2.4339   -1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.1959   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.7698   -0.3338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4139   -0.8788    1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    0.1006    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    1.3269    0.7632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5782    2.2982    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -0.3122   -5.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.2860   -4.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    0.4267   -4.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3312    0.3712   -3.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    1.8523   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856    0.2035   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0313    1.4772   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    2.2503   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6997    0.3184   -2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -2.6193   -2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -2.4824   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027   -3.2616   -1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8642   -2.0314    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7652   -1.3750   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.2889    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009   -1.4066   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -0.5594    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -1.8975    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.3360    2.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -0.3166    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    1.8571    1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    2.6612    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808    3.1687    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093    1.8286    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 13 12  1  0
  8  7  1  0
  3  2  2  0
  7  2  1  0
 11  5  1  0
  5  6  1  0
  7  6  1  0
 12 11  1  0
  8  9  1  6
  5  4  1  6
 14 15  1  0
  5 14  1  0
 11 31  1  6
 11  8  1  0
  8 10  1  0
 14 13  1  0
  2  1  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  0
 12 33  1  0
 14 36  1  1
  4 20  1  0
  4 21  1  0
  3 19  1  0
  7 24  1  6
  6 22  1  0
  6 23  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
  1 16  1  0
  1 17  1  0
  1 18  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      -2.211  -0.292  -4.643  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.685   0.092  -3.293  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.390   0.398  -3.078  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.119   0.820  -1.719  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.970   0.730  -0.615  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.273   1.300  -1.202  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.688   0.149  -2.143  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.605  -1.088  -1.186  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.438  -2.434  -1.916  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.909  -1.196  -0.366  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.337  -0.770  -0.334  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.414  -0.879   1.189  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.343   0.101   1.649  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.593   1.327   0.763  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.578   2.298   0.799  0.00  0.00           C+0
HETATM   16  H   UNK     0      -1.419  -0.312  -5.400  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.667  -1.286  -4.614  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.968   0.427  -4.972  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.331   0.371  -3.890  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.472   1.852  -1.822  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.986   0.204  -1.452  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.031   1.477  -0.433  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.119   2.250  -1.727  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.700   0.318  -2.527  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.275  -2.619  -2.597  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.512  -2.482  -2.498  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.403  -3.262  -1.198  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.864  -2.031   0.342  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.765  -1.375  -1.027  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.131  -0.289   0.203  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.501  -1.407  -0.657  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.379  -0.559   1.592  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.219  -1.898   1.537  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.436   0.336   2.714  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.656  -0.317   1.476  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.464   1.857   1.173  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.741   2.661   1.819  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.381   3.169   0.165  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.509   1.829   0.466  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    3    7    1                                                  
CONECT    3    4    2   19                                                  
CONECT    4    3    5   20   21                                             
CONECT    5   11    6    4   14                                             
CONECT    6    5    7   22   23                                             
CONECT    7    8    2    6   24                                             
CONECT    8    7    9   11   10                                             
CONECT    9    8   25   26   27                                             
CONECT   10    8   28   29   30                                             
CONECT   11    5   12   31    8                                             
CONECT   12   13   11   32   33                                             
CONECT   13   12   14   34   35                                             
CONECT   14   15    5   13   36                                             
CONECT   15   14   37   38   39                                             
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    4                                                            
CONECT   21    4                                                            
CONECT   22    6                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
   -2.2110   -0.2924   -4.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6848    0.0924   -3.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    0.3983   -3.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193    0.8197   -1.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9695    0.7300   -0.6151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2726    1.2996   -1.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6875    0.1492   -2.1433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6050   -1.0882   -1.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4376   -2.4339   -1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.1959   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.7698   -0.3338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4139   -0.8788    1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    0.1006    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    1.3269    0.7632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5782    2.2982    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -0.3122   -5.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.2860   -4.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    0.4267   -4.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3312    0.3712   -3.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    1.8523   -1.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856    0.2035   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0313    1.4772   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    2.2503   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6997    0.3184   -2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -2.6193   -2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -2.4824   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027   -3.2616   -1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8642   -2.0314    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7652   -1.3750   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.2889    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009   -1.4066   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -0.5594    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -1.8975    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.3360    2.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -0.3166    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    1.8571    1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    2.6612    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808    3.1687    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093    1.8286    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 13 12  1  0
  8  7  1  0
  3  2  2  0
  7  2  1  0
 11  5  1  0
  5  6  1  0
  7  6  1  0
 12 11  1  0
  8  9  1  6
  5  4  1  6
 14 15  1  0
  5 14  1  0
 11 31  1  6
 11  8  1  0
  8 10  1  0
 14 13  1  0
  2  1  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  0
 12 33  1  0
 14 36  1  1
  4 20  1  0
  4 21  1  0
  3 19  1  0
  7 24  1  6
  6 22  1  0
  6 23  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-alpha-Cedrene	ChEBI
(1S,2R,5S,7S)-2,6,6,8-Tetramethyltricyclo[5.3.1.0(1,5)]undec-8-ene	ChEBI
[3R-(3alpha,3Abeta,7beta,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene	ChEBI
(-)-a-Cedrene	Generator
(-)-Α-cedrene	Generator
[3R-(3a,3Abeta,7b,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene	Generator
[3R-(3Α,3abeta,7β,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene	Generator
a-Cedrene	Generator
Α-cedrene	Generator
beta-Cedrene	HMDB
Cedrone	HMDB
Cedrene	HMDB
alpha-Cedrene	ChEBI

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene

Traditional Name

(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene

CAS Registry Number

Not Available

SMILES

[H]C1=C(C([H])([H])[H])[C@]2([H])C([H])([H])[C@@]3(C1([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]3([H])C2(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1

InChI Key

IRAQOCYXUMOFCW-OSFYFWSMSA-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
Acorus calamus	LOTUS Database	35616633
Acorus calanus L.	KNApSAcK Database	22123792
Ageratina adenophora	Plant	KNApSAcK
Artemisia annua	JEOL database	Brown, G. D., et al, Phytochemistry 64, 303 (2003)
Artemisia herba-alba	LOTUS Database	35616633
Asarum simile	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Cupressus funebris Endl.	Plant	KNApSAcK
Curcuma kwangsiensis	KNApSAcK Database	22123792
Curcuma longa	KNApSAcK Database	22123792
Curcuma phaeocaulis	KNApSAcK Database	22123792
Curcuma wenyujin	Plant	KNApSAcK
Dysoxylum malabaricum	KNApSAcK Database	22123792
Juniperus horizontalis	LOTUS Database	35616633
Juniperus procera	LOTUS Database	35616633
Juniperus thurifera	LOTUS Database	35616633
Juniperus virginiana	KNApSAcK Database	22123792
Murraya exotica	KNApSAcK Database	22123792
Nicotiana langsdorffii	KNApSAcK Database	22123792
Osyris quadripartita	LOTUS Database	35616633
Osyris tenuifolia	KNApSAcK Database	22123792
Persicaria minor	LOTUS Database	35616633
Petasites albus	KNApSAcK Database	22123792
Petasites hybridus	KNApSAcK Database	22123792
Polygonum minus	KNApSAcK Database	22123792
Psidium guajava	KNApSAcK Database	22123792
Rhaponticum carthamoides	KNApSAcK Database	22123792
Rhynchosia minima	KNApSAcK Database	22123792
Sideritis athoa	LOTUS Database	35616633
Tagetes filifolia	LOTUS Database	35616633
Thuja occidentalis	Plant	KNApSAcK
Thymus citriodorus	LOTUS Database	35616633
Tordylium apulum	LOTUS Database	35616633
Trachyspermum anethifolium	LOTUS Database	35616633
Trocholejeunea sandvicensis	KNApSAcK Database	22123792
Vitis vinifera	LOTUS Database	35616633
Zingiber officinale ROSC.	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Cedrane and isocedrane sesquiterpenoids

Alternative Parents

Not Available

Substituents

Not Available

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	261.00 to 262.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.15 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.308 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	5.18	ALOGPS
logP	4.1	ChemAxon
logS	-5.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.69 m³·mol⁻¹	ChemAxon
Polarizability	25.63 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

HMDB0059695

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6431015

PDB ID

Not Available

ChEBI ID

10216

Good Scents ID

rw1032351

References

General References

Takigawa H, Kubota H, Sonohara H, Okuda M, Tanaka S, Fujikura Y, Ito S: Novel Allylic Oxidation of alpha-Cedrene to sec-Cedrenol by a Rhodococcus Strain. Appl Environ Microbiol. 1993 May;59(5):1336-41. doi: 10.1128/aem.59.5.1336-1341.1993. [PubMed:16348930 ]
Brown, G. D., et al. (2003). Brown, G. D., et al, Phytochemistry 64, 303 (2003). Phytochem..

Showing NP-Card for (-)-alpha-Cedrene (NP0030845)

MOL for NP0030845 ((-)-alpha-Cedrene)

3D MOL for NP0030845 ((-)-alpha-Cedrene)

3D SDF for NP0030845 ((-)-alpha-Cedrene)

3D-SDF for NP0030845 ((-)-alpha-Cedrene)

PDB for NP0030845 ((-)-alpha-Cedrene)

3D PDB for NP0030845 ((-)-alpha-Cedrene)

SMILES for NP0030845 ((-)-alpha-Cedrene)

INCHI for NP0030845 ((-)-alpha-Cedrene)

Structure for NP0030845 ((-)-alpha-Cedrene)

3D Structure for NP0030845 ((-)-alpha-Cedrene)