NP-MRD: Showing NP-Card for (3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one (NP0246693)

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Record Information

Version

2.0

Created at

2022-09-07 08:14:52 UTC

Updated at

2022-09-07 08:14:53 UTC

NP-MRD ID

NP0246693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one

Description

Tricycloalternarene D belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one is found in Alternaria alternata. (3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one was first documented in 2018 (PMID: 29642523). Based on a literature review a small amount of articles have been published on Tricycloalternarene D (PMID: 29313358).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210142D          

 28 30  0  0  1  0            999 V2000
   -7.6405   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9260   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9260   -4.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2116   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4971   -3.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7826   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7826   -2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0681   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6392   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247   -2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1240   -4.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3170   -4.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0955   -3.6327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5804   -4.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9024   -3.4612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1574   -2.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -2.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -3.0196    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8603   -1.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3082   -0.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6672   -1.1074    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9222   -0.3227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2193   -1.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643   -2.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 13  1  1  0  0  0
 16 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    8.5232   -1.7391   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4368   -0.7322   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3078   -0.0500   -1.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449   -0.5870    0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5682    0.3882    0.6821 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7189    0.1433   -0.3936 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7726    1.3014   -1.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362   -0.0618    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3046   -0.3151   -0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9072   -0.5451   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026    0.6464    0.4066 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3560    1.9188   -0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    0.4123    1.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662    0.2926    2.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    0.0684    2.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724    0.5079    1.7514 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5567    1.9689    1.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154   -0.3107    1.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223   -0.7639    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0067   -0.9905   -0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352   -0.9110   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383    0.3117    0.5787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5555   -1.3060   -1.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791   -2.0368   -2.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8636   -0.7782   -2.1521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5379   -1.6644   -3.0029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7518   -0.4417   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2695   -1.0271    0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2604   -1.5781   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0216   -1.6367    0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0983   -2.7698   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0001   -1.5363    1.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1794   -0.3203    1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0270   -0.7857   -0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5698    2.0560   -1.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9864    0.9862   -2.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    1.8976   -1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4168   -0.9930    0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636    0.7598    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551    0.5168   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612   -1.2293   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2956   -0.8310   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9390   -1.3914    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2260    0.8739    1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3728    2.3623   -0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    1.7210   -1.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2470    2.6543    0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706    0.3616    3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389   -0.9761    3.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    0.7723    3.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526    2.6074    2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037    2.0464    2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8263    2.2772    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0015   -0.8636   -1.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2302   -1.8262    0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3827    1.1821   -0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6927    0.1555   -2.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9530   -1.1845   -3.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8268    0.6681   -0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7757   -0.8157   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4661   -2.1206    0.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8601   -0.5784    1.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 22 13  1  0
 22 16  1  0
 28 19  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  6 34  1  6
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  0
 12 46  1  0
 12 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  6
 25 57  1  6
 26 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
  4 32  1  0
  4 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652309072210142D          

 28 30  0  0  1  0            999 V2000
   -7.6405   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9260   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9260   -4.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2116   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4971   -3.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7826   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7826   -2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0681   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6392   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247   -2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1240   -4.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3170   -4.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0955   -3.6327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5804   -4.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9024   -3.4612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1574   -2.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -2.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -3.0196    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8603   -1.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3082   -0.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6672   -1.1074    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9222   -0.3227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2193   -1.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643   -2.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 13  1  1  0  0  0
 16 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCCC(C)C1=CC[C@]2(C)OC3=C(C[C@H]12)C(=O)[C@@H](O)CC3)OCC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O5/c1-14(6-5-7-16(3)27-13-15(2)24)17-10-11-23(4)19(17)12-18-21(28-23)9-8-20(25)22(18)26/h10,14,16,19-20,25H,5-9,11-13H2,1-4H3/t14?,16?,19-,20+,23+/m1/s1

> <INCHI_KEY>
JJJIYVRGEHVHMY-FSFYIAILSA-N

> <FORMULA>
C23H34O5

> <MOLECULAR_WEIGHT>
390.52

> <EXACT_MASS>
390.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.1657550646298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,7R,11S)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0^{3,7}]trideca-1(9),5-dien-10-one

> <JCHEM_LOGP>
2.765897260999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.335057862653095

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.371735198586912

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5109802514661466

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
110.19289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,7R,11S)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0^{3,7}]trideca-1(9),5-dien-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -14.262  -5.493   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.929  -6.263   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -12.929  -7.803   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0     -11.595  -5.493   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -10.261  -6.263   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -8.928  -5.493   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.928  -3.953   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.594  -6.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.260  -5.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.926  -6.263   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.593  -5.493   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.593  -3.953   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.259  -6.263   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.098  -7.795   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.592  -8.115   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.178  -6.781   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.083  -8.027   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.685  -6.461   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.160  -4.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.130  -3.852   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.376  -4.172   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.852  -5.637   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.606  -2.387   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.575  -1.243   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.112  -2.067   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.588  -0.602   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.143  -3.212   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.667  -4.676   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   13   16                                                  
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   19                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₄O₅

Average Mass

390.5200 Da

Monoisotopic Mass

390.24062 Da

IUPAC Name

(3S,7R,11S)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0^{3,7}]trideca-1(9),5-dien-10-one

Traditional Name

(3S,7R,11S)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0^{3,7}]trideca-1(9),5-dien-10-one

CAS Registry Number

Not Available

SMILES

CC(CCCC(C)C1=CC[C@]2(C)OC3=C(C[C@H]12)C(=O)[C@@H](O)CC3)OCC(C)=O

InChI Identifier

InChI=1S/C23H34O5/c1-14(6-5-7-16(3)27-13-15(2)24)17-10-11-23(4)19(17)12-18-21(28-23)9-8-20(25)22(18)26/h10,14,16,19-20,25H,5-9,11-13H2,1-4H3/t14?,16?,19-,20+,23+/m1/s1

InChI Key

JJJIYVRGEHVHMY-FSFYIAILSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alternaria alternata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Vinylogous ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

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	2.77	ChemAxon
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	110.19 m³·mol⁻¹	ChemAxon
Polarizability	44.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78440700

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang H, Zhao Z, Chen J, Bai X, Wang H: Tricycloalternarene Analogs from a Symbiotic Fungus Aspergillus sp. D and Their Antimicrobial and Cytotoxic Effects. Molecules. 2018 Apr 9;23(4). pii: molecules23040855. doi: 10.3390/molecules23040855. [PubMed:29642523 ]
Shi ZZ, Fang ST, Miao FP, Ji NY: Two new tricycloalternarene esters from an alga-epiphytic isolate of Alternaria alternata. Nat Prod Res. 2018 Nov;32(21):2523-2528. doi: 10.1080/14786419.2017.1423312. Epub 2018 Jan 9. [PubMed:29313358 ]
LOTUS database [Link]

Showing NP-Card for (3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one (NP0246693)

MOL for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

3D MOL for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

3D SDF for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

3D-SDF for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

PDB for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

3D PDB for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

SMILES for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

INCHI for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

Structure for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)

3D Structure for NP0246693 ((3s,7r,11s)-11-hydroxy-3-methyl-6-[6-(2-oxopropoxy)heptan-2-yl]-2-oxatricyclo[7.4.0.0³,⁷]trideca-1(9),5-dien-10-one)