NP-MRD: Showing NP-Card for (+)-preisocalamenediol (NP0043121)

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Record Information

Version

1.0

Created at

2021-06-21 00:36:42 UTC

Updated at

2021-06-30 00:18:37 UTC

NP-MRD ID

NP0043121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-preisocalamenediol

Provided By

JEOL Database JEOL Logo

Description

Preisocalamendiol belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. (+)-preisocalamenediol is found in Acorus calamus , Acorus calanus L., Baccharis latifolia and Rhododendron capitatum. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on Preisocalamendiol (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454) (PMID: 26389451) (PMID: 26389436).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102363D          

 40 40  0  0  0  0            999 V2000
    1.4464    1.6717    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    1.2497    0.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501    0.7163    2.2222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4032   -0.7770    2.3134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6740   -1.6765    1.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -2.5633    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826   -3.3727    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -2.8505   -0.0310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7025   -2.2720   -1.4572 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4111   -0.7584   -1.5498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3651   -0.2052   -2.9997 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8887   -0.6825   -3.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099   -0.5331   -3.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    0.0517   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.3126   -0.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9520    1.3767   -0.1194 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2877    1.6101    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.0863   -0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8692    1.2985    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198    0.9056    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.0323    3.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -0.9493    1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359   -1.5674    2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -4.4429    0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6593   -3.1626    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540   -3.1510   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -3.9396   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -2.5146    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272   -2.8211   -2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -2.4953   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5786   -0.5927   -1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990    0.8892   -2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676   -0.1922   -4.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8739   -1.7630   -3.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.4385   -3.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -0.0273   -4.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -1.6063   -4.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.1970   -3.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    2.0545   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    1.8285    0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0  0  0  0
 16 14  1  0  0  0  0
 14 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
 14 15  2  0  0  0  0
  4  3  1  0  0  0  0
 10 11  1  0  0  0  0
  4  5  1  0  0  0  0
 11 12  1  0  0  0  0
  3  2  1  0  0  0  0
 11 13  1  0  0  0  0
  2 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  2  3  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  5 23  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 10 31  1  1  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
 11 32  1  1  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 13 38  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
    1.4464    1.6717    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    1.2497    0.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501    0.7163    2.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.7770    2.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -1.6765    1.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -2.5633    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826   -3.3727    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -2.8505   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -2.2720   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -0.7584   -1.5498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3651   -0.2052   -2.9997 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8887   -0.6825   -3.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099   -0.5331   -3.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    0.0517   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.3126   -0.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9520    1.3767   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877    1.6101    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.0863   -0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8692    1.2985    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198    0.9056    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.0323    3.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -0.9493    1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359   -1.5674    2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -4.4429    0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6593   -3.1626    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540   -3.1510   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -3.9396   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -2.5146    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272   -2.8211   -2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -2.4953   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5786   -0.5927   -1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990    0.8892   -2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676   -0.1922   -4.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8739   -1.7630   -3.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.4385   -3.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -0.0273   -4.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -1.6063   -4.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.1970   -3.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    2.0545   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    1.8285    0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0
 16 14  1  0
 14 10  1  0
 10  9  1  0
  9  8  1  0
 14 15  2  0
  4  3  1  0
 10 11  1  0
  4  5  1  0
 11 12  1  0
  3  2  1  0
 11 13  1  0
  2 16  1  0
  6  7  1  0
  6  5  2  0
  2  1  2  3
  4 21  1  0
  4 22  1  0
  3 19  1  0
  3 20  1  0
  5 23  1  0
 16 39  1  0
 16 40  1  0
 10 31  1  1
  9 29  1  0
  9 30  1  0
  8 27  1  0
  8 28  1  0
 11 32  1  1
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  1 17  1  0
  1 18  1  0
M  END


  Mrv1652306212102363D          

 40 40  0  0  0  0            999 V2000
    1.4464    1.6717    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    1.2497    0.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501    0.7163    2.2222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4032   -0.7770    2.3134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6740   -1.6765    1.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -2.5633    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826   -3.3727    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -2.8505   -0.0310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7025   -2.2720   -1.4572 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4111   -0.7584   -1.5498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3651   -0.2052   -2.9997 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8887   -0.6825   -3.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099   -0.5331   -3.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    0.0517   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.3126   -0.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9520    1.3767   -0.1194 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2877    1.6101    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.0863   -0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8692    1.2985    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198    0.9056    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.0323    3.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -0.9493    1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359   -1.5674    2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -4.4429    0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6593   -3.1626    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540   -3.1510   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -3.9396   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -2.5146    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272   -2.8211   -2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -2.4953   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5786   -0.5927   -1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990    0.8892   -2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676   -0.1922   -4.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8739   -1.7630   -3.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.4385   -3.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -0.0273   -4.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -1.6063   -4.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.1970   -3.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    2.0545   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    1.8285    0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0  0  0  0
 16 14  1  0  0  0  0
 14 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
 14 15  2  0  0  0  0
  4  3  1  0  0  0  0
 10 11  1  0  0  0  0
  4  5  1  0  0  0  0
 11 12  1  0  0  0  0
  3  2  1  0  0  0  0
 11 13  1  0  0  0  0
  2 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  2  3  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  5 23  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 10 31  1  1  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
 11 32  1  1  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 13 38  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043121

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C([H])([H])C(=O)[C@@]([H])(C([H])([H])C([H])([H])\C(=C([H])/C([H])([H])C1([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h6,11,14H,4-5,7-10H2,1-3H3/b12-6-/t14-/m0/s1

> <INCHI_KEY>
QTFJNWQFKJITEE-ZDWRTJATSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.4626458957186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5Z)-5-methyl-9-methylidene-2-(propan-2-yl)cyclodec-5-en-1-one

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
4.361855864666667

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.599532323632186

> <JCHEM_PKA_STRONGEST_BASIC>
-7.498029846767091

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
70.10019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5Z)-2-isopropyl-5-methyl-9-methylidenecyclodec-5-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
    1.4464    1.6717    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    1.2497    0.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501    0.7163    2.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.7770    2.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -1.6765    1.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -2.5633    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826   -3.3727    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -2.8505   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -2.2720   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -0.7584   -1.5498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3651   -0.2052   -2.9997 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8887   -0.6825   -3.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099   -0.5331   -3.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    0.0517   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.3126   -0.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9520    1.3767   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877    1.6101    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.0863   -0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8692    1.2985    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198    0.9056    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.0323    3.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -0.9493    1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359   -1.5674    2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -4.4429    0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6593   -3.1626    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540   -3.1510   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -3.9396   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -2.5146    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272   -2.8211   -2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -2.4953   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5786   -0.5927   -1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990    0.8892   -2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676   -0.1922   -4.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8739   -1.7630   -3.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.4385   -3.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -0.0273   -4.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -1.6063   -4.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.1970   -3.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    2.0545   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    1.8285    0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0
 16 14  1  0
 14 10  1  0
 10  9  1  0
  9  8  1  0
 14 15  2  0
  4  3  1  0
 10 11  1  0
  4  5  1  0
 11 12  1  0
  3  2  1  0
 11 13  1  0
  2 16  1  0
  6  7  1  0
  6  5  2  0
  2  1  2  3
  4 21  1  0
  4 22  1  0
  3 19  1  0
  3 20  1  0
  5 23  1  0
 16 39  1  0
 16 40  1  0
 10 31  1  1
  9 29  1  0
  9 30  1  0
  8 27  1  0
  8 28  1  0
 11 32  1  1
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  1 17  1  0
  1 18  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.446   1.672   0.474  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.219   1.250   0.827  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.050   0.716   2.222  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.403  -0.777   2.313  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.674  -1.677   1.763  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.580  -2.563   0.751  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.783  -3.373   0.336  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.684  -2.850  -0.031  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.703  -2.272  -1.457  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.411  -0.758  -1.550  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.365  -0.205  -3.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.889  -0.683  -3.740  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.610  -0.533  -3.829  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.415   0.052  -0.720  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.588  -0.313  -0.589  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.952   1.377  -0.119  0.00  0.00           C+0
HETATM   17  H   UNK     0       2.288   1.610   1.158  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.649   2.086  -0.510  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.869   1.299   2.664  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.820   0.906   2.866  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.538  -1.032   3.372  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.375  -0.949   1.847  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.636  -1.567   2.265  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.568  -4.443   0.420  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.659  -3.163   0.958  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.054  -3.151  -0.701  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.809  -3.940  -0.099  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.574  -2.515   0.509  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.027  -2.821  -2.063  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.687  -2.495  -1.886  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.579  -0.593  -1.112  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.299   0.889  -2.944  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.968  -0.192  -4.717  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.874  -1.763  -3.913  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.794  -0.439  -3.174  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.564  -0.027  -4.800  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.698  -1.606  -4.025  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.523  -0.197  -3.329  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.723   2.054  -0.950  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.798   1.829   0.414  0.00  0.00           H+0
CONECT    1    2   17   18                                                  
CONECT    2    3   16    1                                                  
CONECT    3    4    2   19   20                                             
CONECT    4    3    5   21   22                                             
CONECT    5    4    6   23                                                  
CONECT    6    8    7    5                                                  
CONECT    7    6   24   25   26                                             
CONECT    8    6    9   27   28                                             
CONECT    9   10    8   29   30                                             
CONECT   10   14    9   11   31                                             
CONECT   11   10   12   13   32                                             
CONECT   12   11   33   34   35                                             
CONECT   13   11   36   37   38                                             
CONECT   14   16   10   15                                                  
CONECT   15   14                                                            
CONECT   16   14    2   39   40                                             
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
CONECT   21    4                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    7                                                            
CONECT   25    7                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   13                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   80    0
END

RDKit          3D

40 40  0  0  0  0  0  0  0  0999 V2000
    1.4464    1.6717    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    1.2497    0.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501    0.7163    2.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.7770    2.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -1.6765    1.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -2.5633    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826   -3.3727    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -2.8505   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -2.2720   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -0.7584   -1.5498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3651   -0.2052   -2.9997 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8887   -0.6825   -3.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099   -0.5331   -3.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    0.0517   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.3126   -0.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9520    1.3767   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877    1.6101    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.0863   -0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8692    1.2985    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198    0.9056    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.0323    3.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -0.9493    1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359   -1.5674    2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -4.4429    0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6593   -3.1626    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540   -3.1510   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087   -3.9396   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -2.5146    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272   -2.8211   -2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -2.4953   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5786   -0.5927   -1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990    0.8892   -2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676   -0.1922   -4.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8739   -1.7630   -3.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.4385   -3.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -0.0273   -4.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -1.6063   -4.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.1970   -3.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    2.0545   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    1.8285    0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  1  0
 16 14  1  0
 14 10  1  0
 10  9  1  0
  9  8  1  0
 14 15  2  0
  4  3  1  0
 10 11  1  0
  4  5  1  0
 11 12  1  0
  3  2  1  0
 11 13  1  0
  2 16  1  0
  6  7  1  0
  6  5  2  0
  2  1  2  3
  4 21  1  0
  4 22  1  0
  3 19  1  0
  3 20  1  0
  5 23  1  0
 16 39  1  0
 16 40  1  0
 10 31  1  1
  9 29  1  0
  9 30  1  0
  8 27  1  0
  8 28  1  0
 11 32  1  1
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  1 17  1  0
  1 18  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3560 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

(2S,5Z)-5-methyl-9-methylidene-2-(propan-2-yl)cyclodec-5-en-1-one

Traditional Name

(2S,5Z)-2-isopropyl-5-methyl-9-methylidenecyclodec-5-en-1-one

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C([H])([H])C(=O)[C@@]([H])(C([H])([H])C([H])([H])\C(=C([H])/C([H])([H])C1([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H24O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h6,11,14H,4-5,7-10H2,1-3H3/b12-6-/t14-/m0/s1

InChI Key

QTFJNWQFKJITEE-ZDWRTJATSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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	Plant	KNApSAcK
Acorus calanus L.	Plant	KNApSAcK
Baccharis latifolia	Plant	KNApSAcK
Rhododendron capitatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	4.38	ALOGPS
logP	4.36	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	16.6	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.1 m³·mol⁻¹	ChemAxon
Polarizability	26.46 Å³	ChemAxon
Number of Rings	1	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

Not Available

KNApSAcK ID

C00011714

Chemspider ID

28426483

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12305705

PDB ID

Not Available

ChEBI ID

168606

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
Authors unspecified: Cancer Prevention Overview (PDQ(R)): Health Professional Version. 2002. [PubMed:26389451 ]
Authors unspecified: Spirituality in Cancer Care (PDQ(R)): Health Professional Version. 2002. [PubMed:26389436 ]
Authors unspecified: Oral Cavity, Oropharyngeal, Hypopharyngeal, and Laryngeal Cancer Prevention (PDQ(R)): Health Professional Version. 2002. [PubMed:26389416 ]
Authors unspecified: Adjustment to Cancer: Anxiety and Distress (PDQ(R)): Health Professional Version. 2002. [PubMed:26389397 ]
Authors unspecified: Cancer Pain (PDQ(R)): Health Professional Version. 2002. [PubMed:26389387 ]
Authors unspecified: Ovarian, Fallopian Tube, and Primary Peritoneal Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:26389336 ]
Authors unspecified: Informal Caregivers in Cancer: Roles, Burden, and Support (PDQ(R)): Health Professional Version. 2002. [PubMed:26389284 ]
Authors unspecified: Neuroblastoma Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389278 ]
Authors unspecified: Late Effects of Treatment for Childhood Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389273 ]
St-Gelais A, Mathieu M, Levasseur V, Ovando JF, Escamilla R, Marceau H: Preisocalamendiol, Shyobunol and Related Oxygenated Sesquiterpenes from Bolivian Schinus molle Essential Oil. Nat Prod Commun. 2016 Apr;11(4):547-50. [PubMed:27396215 ]
Delvalle, D. M., et al. (1987). Delvalle, D. M., et al, Planta Med. 87, 230 (1987). Planta Med..

Showing NP-Card for (+)-preisocalamenediol (NP0043121)

MOL for NP0043121 ((+)-preisocalamenediol)

3D MOL for NP0043121 ((+)-preisocalamenediol)

3D SDF for NP0043121 ((+)-preisocalamenediol)

3D-SDF for NP0043121 ((+)-preisocalamenediol)

PDB for NP0043121 ((+)-preisocalamenediol)

3D PDB for NP0043121 ((+)-preisocalamenediol)

SMILES for NP0043121 ((+)-preisocalamenediol)

INCHI for NP0043121 ((+)-preisocalamenediol)

Structure for NP0043121 ((+)-preisocalamenediol)

3D Structure for NP0043121 ((+)-preisocalamenediol)