NP-MRD: Showing NP-Card for 3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid (NP0153357)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 10:00:15 UTC

Updated at

2022-09-02 10:00:15 UTC

NP-MRD ID

NP0153357

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid

Description

3-{[(3S)-5-[(6aR,7R,8S,9R,10aS)-9-hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid is found in Olearia teretifolia. Based on a literature review very few articles have been published on 3-{[(3S)-5-[(6aR,7R,8S,9R,10aS)-9-hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022212002D          

 30 32  0  0  1  0            999 V2000
   12.6138    2.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6138    1.3991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8993    0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1848    1.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4704    0.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7559    1.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7559    2.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0414    0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269    1.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125    0.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269    2.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3282    0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0427    1.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7572    0.9866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2269    0.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0393    1.7619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5090    2.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8518    1.9052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1340    2.6804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2835    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0999    0.4979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5371    1.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3376    0.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3952    0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0948   -0.2622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6302   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3481   -0.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5356   -1.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0053   -0.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2875    0.3547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
 21 30  1  0  0  0  0
 14 30  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    2.0657    0.9233    2.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827    0.0207    1.3484 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5092    0.2475    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6987   -0.0151    1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    0.2152    0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2560   -0.4781   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251   -1.3972   -0.7786 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5218   -0.1567   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6759   -1.0629   -2.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6996   -2.3214   -2.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -0.5156   -3.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841    0.2932    0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612    0.0667    0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224    0.2985   -0.0043 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3507    1.7263   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -0.6823   -1.1516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0162   -0.0605   -2.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080   -1.6595   -1.2884 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2808   -2.1884   -2.5997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -1.1211   -1.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825    0.0131   -0.1578 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2608    1.2203   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5073    0.7448   -1.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320    0.0469   -0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3100   -0.4141   -0.4166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1615   -0.0859    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925   -0.2019    1.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9767   -0.2501    2.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8072    0.4255    2.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6993   -0.0664    0.6746 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8932    0.6502    3.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234    0.7042    3.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    1.9902    2.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750   -1.0224    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    1.3438    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5725   -0.2892   -0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7461   -1.0603    1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7390    0.7231    2.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3736   -0.3748   -0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5197    0.8841   -1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0727    0.1601   -3.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3215   -0.3421   -0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2662    1.3428    0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317   -0.9096    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    0.9148    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4942    2.3007   -0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824    1.8658   -1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383    2.3093   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769   -1.3574   -0.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851    0.5445   -2.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946    0.4250   -2.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788   -0.9309   -3.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -2.5703   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442   -2.6538   -2.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4532   -1.9227   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2024   -0.8472   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6541    1.4981   -1.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019    2.0870   -0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1461   -0.2722    2.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7677   -1.2529    3.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093    0.3934    3.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142    0.0821    2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555    1.5208    2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590   -1.2060    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  2 12  1  0
 12 13  1  0
 14 13  1  1
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 21 20  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 14  1  0
 26 21  1  0
 30 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  1
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  0
  8 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  1
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  1
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 27 59  1  0
 28 60  1  0
 28 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  1
M  END


  Mrv1652309022212002D          

 30 32  0  0  1  0            999 V2000
   12.6138    2.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6138    1.3991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8993    0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1848    1.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4704    0.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7559    1.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7559    2.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0414    0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269    1.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125    0.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269    2.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3282    0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0427    1.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7572    0.9866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2269    0.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0393    1.7619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5090    2.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8518    1.9052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1340    2.6804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2835    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0999    0.4979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5371    1.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3376    0.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3952    0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0948   -0.2622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6302   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3481   -0.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5356   -1.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0053   -0.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2875    0.3547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
 21 30  1  0  0  0  0
 14 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCOC(=O)CC(O)=O)CC[C@@]1(C)[C@H](C)[C@H](O)C[C@@]23COC(=O)C2=CCC[C@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O7/c1-14(8-10-29-20(27)11-19(25)26)7-9-22(3)15(2)17(24)12-23-13-30-21(28)16(23)5-4-6-18(22)23/h5,14-15,17-18,24H,4,6-13H2,1-3H3,(H,25,26)/t14-,15+,17+,18+,22-,23+/m0/s1

> <INCHI_KEY>
CCAVMGBTZLRHDV-GWPPXWQZSA-N

> <FORMULA>
C23H34O7

> <MOLECULAR_WEIGHT>
422.518

> <EXACT_MASS>
422.230453435

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
45.341011464326705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(3S)-5-[(6aR,7R,8S,9R,10aS)-9-hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
3.184363756999999

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.907680826550191

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.218156193105928

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8391804064708284

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
109.51809999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(3S)-5-[(6aR,7R,8S,9R,10aS)-9-hydroxy-7,8-dimethyl-3-oxo-1H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      23.546   4.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.546   2.612   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.212   1.842   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.878   2.612   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      19.545   1.842   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      18.211   2.612   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      18.211   4.152   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      16.877   1.842   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.544   2.612   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.210   1.842   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      15.544   4.152   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      24.879   1.842   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.213   2.612   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.547   1.842   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.557   0.662   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.073   3.289   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.084   4.469   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.590   3.556   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      30.117   5.003   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      30.396   2.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.053   0.929   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.869   2.235   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      32.364   1.863   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      32.471   0.327   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      33.777  -0.489   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      31.043  -0.250   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.516  -1.697   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.000  -1.965   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.010  -0.785   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      28.537   0.662   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26   30                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   21   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   21   14                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
3-{[(3S)-5-[(6ar,7R,8S,9R,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6ah,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoate	Generator

Chemical Formula

C₂₃H₃₄O₇

Average Mass

422.5180 Da

Monoisotopic Mass

422.23045 Da

IUPAC Name

3-{[(3S)-5-[(6aR,7R,8S,9R,10aS)-9-hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[(3S)-5-[(6aR,7R,8S,9R,10aS)-9-hydroxy-7,8-dimethyl-3-oxo-1H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCOC(=O)CC(O)=O)CC[C@@]1(C)[C@H](C)[C@H](O)C[C@@]23COC(=O)C2=CCC[C@H]13

InChI Identifier

InChI=1S/C23H34O7/c1-14(8-10-29-20(27)11-19(25)26)7-9-22(3)15(2)17(24)12-23-13-30-21(28)16(23)5-4-6-18(22)23/h5,14-15,17-18,24H,4,6-13H2,1-3H3,(H,25,26)/t14-,15+,17+,18+,22-,23+/m0/s1

InChI Key

CCAVMGBTZLRHDV-GWPPXWQZSA-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
Olearia teretifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Naphthofuran
Tricarboxylic acid or derivatives
Gamma butyrolactone
1,3-dicarbonyl compound
Cyclic alcohol
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	3.39	ALOGPS
logP	3.18	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	109.52 m³·mol⁻¹	ChemAxon
Polarizability	45.34 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162865524

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid (NP0153357)

MOL for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

3D MOL for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

3D SDF for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

3D-SDF for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

PDB for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

3D PDB for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

SMILES for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

INCHI for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

Structure for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)

3D Structure for NP0153357 (3-{[(3s)-5-[(6ar,7r,8s,9r,10as)-9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl]-3-methylpentyl]oxy}-3-oxopropanoic acid)