NP-MRD: Showing NP-Card for 10'-Hydroxy-1'betaH-lycoserone (NP0065462)

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Record Information

Version

2.0

Created at

2022-04-28 09:40:59 UTC

Updated at

2022-04-28 09:40:59 UTC

NP-MRD ID

NP0065462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10'-Hydroxy-1'betaH-lycoserone

Description

3-[(1R,4aS,7S,7aR)-3-[(2R)-2-hydroxy-3-methylbutanoyl]-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]-4-hydroxy-5-methyl-2H-chromen-2-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 10'-Hydroxy-1'betaH-lycoserone is found in Aphyllocladus denticulatus and Gypothamnium pinifolium. Based on a literature review very few articles have been published on 3-[(1R,4aS,7S,7aR)-3-[(2R)-2-hydroxy-3-methylbutanoyl]-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]-4-hydroxy-5-methyl-2H-chromen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282211412D          

 31 34  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -3.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -2.6326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7540   -1.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  6  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  1  0  0  0
 12 22  1  0  0  0  0
 11 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  6  0  0  0
  2 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  1 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
    3.2907   -1.5476   -2.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9678   -1.1094   -1.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686   -0.4877   -0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9897   -0.1881    0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350   -0.5500   -0.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681    0.5240    1.5477 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5575    0.8872    1.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180    1.7819    1.4841 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6401    2.5943    2.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1838    1.4104    1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6210   -0.0600   -0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5717   -0.8039   -0.4534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6599    0.1928   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2363    0.4951    0.8692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310   -0.1327    2.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2228    1.4406    0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375    1.7741    2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4272    1.0927    3.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8241    2.7247    2.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2114    3.3453    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6145    3.0301   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6044    2.0576   -0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0538    1.7617   -1.3852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0971    0.8551   -1.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6692    0.7002   -2.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5183   -1.4625   -1.7693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6108   -3.0197   -1.5385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9642   -3.3586   -1.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -3.4719   -2.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8316   -2.6666   -3.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -1.3591   -2.5627 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2401   -2.0649   -3.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7049   -2.2898   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0269   -0.7171   -2.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440   -0.1571    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4799    1.8431    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060    2.4413    0.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5315    2.3650    3.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6968    3.6949    2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7328    2.4063    3.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3140    1.4239    0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4475    0.4353    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8083    2.1859    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6614   -1.5935    0.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1216   -0.8312    2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1045    1.5169    4.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756    0.0166    3.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232    1.3634    3.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3067    2.9862    3.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0017    4.1038    0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9114    3.5080   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025   -1.3271   -2.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2279   -3.3571   -0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179   -2.9894   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1335   -2.8205   -0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0421   -4.4590   -0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900   -3.1672   -3.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248   -4.5642   -3.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6850   -3.2985   -3.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8262   -2.5357   -4.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6270   -0.5684   -3.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
  8  6  1  0
  6  7  1  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 31  1  0
 31 30  1  0
 30 29  1  0
 29 27  1  0
 27 28  1  0
 27 26  1  0
 26 12  1  0
 12 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 11  3  1  0
 24 13  1  0
 26 31  1  0
 22 16  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
  8 37  1  6
 10 41  1  0
 10 42  1  0
 10 43  1  0
  6 35  1  1
  7 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 31 61  1  6
 30 59  1  0
 30 60  1  0
 29 57  1  0
 29 58  1  0
 27 53  1  1
 28 54  1  0
 28 55  1  0
 28 56  1  0
 26 52  1  6
 12 44  1  1
 15 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
M  END


  Mrv1652304282211412D          

 31 34  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -3.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -2.6326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7540   -1.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  6  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  1  0  0  0
 12 22  1  0  0  0  0
 11 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  6  0  0  0
  2 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  1 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065462

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](O)C(=O)C1=C(C)[C@H]2CC[C@H](C)[C@H]2[C@@H](O1)C1=C(O)C2=C(C)C=CC=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O6/c1-11(2)20(26)22(28)23-14(5)15-10-9-13(4)17(15)24(31-23)19-21(27)18-12(3)7-6-8-16(18)30-25(19)29/h6-8,11,13,15,17,20,24,26-27H,9-10H2,1-5H3/t13-,15+,17+,20+,24+/m0/s1

> <INCHI_KEY>
DGKDRSQFWYQETD-HDGCVAHASA-N

> <FORMULA>
C25H30O6

> <MOLECULAR_WEIGHT>
426.509

> <EXACT_MASS>
426.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.265615921162016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1R,4aS,7S,7aR)-3-[(2R)-2-hydroxy-3-methylbutanoyl]-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]-4-hydroxy-5-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
3.8529973476666672

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.089591026995251

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.6654732683726206

> <JCHEM_PKA_STRONGEST_BASIC>
-3.634542439302276

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
117.96809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1R,4aS,7S,7aR)-3-[(2R)-2-hydroxy-3-methylbutanoyl]-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]-4-hydroxy-5-methylchromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.798  -7.406   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.703  -6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.798  -4.914   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.274  -3.449   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    7   30                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   14                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   12                                                            
CONECT   23   11   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   10   26                                                  
CONECT   26   25                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    1   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₆

Average Mass

426.5090 Da

Monoisotopic Mass

426.20424 Da

IUPAC Name

3-[(1R,4aS,7S,7aR)-3-[(2R)-2-hydroxy-3-methylbutanoyl]-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]-4-hydroxy-5-methyl-2H-chromen-2-one

Traditional Name

3-[(1R,4aS,7S,7aR)-3-[(2R)-2-hydroxy-3-methylbutanoyl]-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]-4-hydroxy-5-methylchromen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](O)C(=O)C1=C(C)[C@H]2CC[C@H](C)[C@H]2[C@@H](O1)C1=C(O)C2=C(C)C=CC=C2OC1=O

InChI Identifier

InChI=1S/C25H30O6/c1-11(2)20(26)22(28)23-14(5)15-10-9-13(4)17(15)24(31-23)19-21(27)18-12(3)7-6-8-16(18)30-25(19)29/h6-8,11,13,15,17,20,24,26-27H,9-10H2,1-5H3/t13-,15+,17+,20+,24+/m0/s1

InChI Key

DGKDRSQFWYQETD-HDGCVAHASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aphyllocladus denticulatus	Plant	KNApSAcK
Gypothamnium pinifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
4-hydroxycoumarin
Hydroxycoumarin
Coumarin
Iridoid-skeleton
Benzopyran
1-benzopyran
Pyranone
Acyloin
Pyran
Benzenoid
Heteroaromatic compound
Alpha-hydroxy ketone
Vinylogous acid
Lactone
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.22	ALOGPS
logP	3.85	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.67	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.97 m³·mol⁻¹	ChemAxon
Polarizability	46.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

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

162943902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 10'-Hydroxy-1'betaH-lycoserone (NP0065462)

MOL for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

3D MOL for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

3D SDF for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

3D-SDF for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

PDB for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

3D PDB for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

SMILES for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

INCHI for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

Structure for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)

3D Structure for NP0065462 (10'-Hydroxy-1'betaH-lycoserone)