NP-MRD: Showing NP-Card for (3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde (NP0290412)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...

Record Information

Version

2.0

Created at

2022-09-09 21:05:10 UTC

Updated at

2022-09-09 21:05:10 UTC

NP-MRD ID

NP0290412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde

Description

Erinacine A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde is found in Hericium erinaceus. (3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde was first documented in 2019 (PMID: 31680958). Based on a literature review a significant number of articles have been published on Erinacine A (PMID: 32485283) (PMID: 35882273) (PMID: 35054997) (PMID: 34865649) (PMID: 34684662) (PMID: 34361662).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309092223052D          

 31 34  0  0  1  0            999 V2000
    0.0904    0.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6702   -0.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519   -1.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672   -1.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908   -2.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -1.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377   -1.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911   -1.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3284   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0176   -1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6047   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -2.9146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1649   -3.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -4.2868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7772   -4.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1818   -4.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -5.4288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7831   -5.9998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708   -5.6589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3675   -6.4601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7662   -5.0879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5585   -5.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -2.7442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4749   -3.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075   -3.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -3.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5138   -2.6480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0093   -3.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2818   -2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -1.6055    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 13 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 31  1  0  0  0  0
M  END

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
   -5.3854    1.1142   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565    0.8994   -0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    0.4870   -2.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3476   -0.2399   -0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2641   -0.3414    0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2554    0.5810    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    1.7716    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601    2.9341    1.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715    3.2252    1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    4.4270    1.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    5.1290    2.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246    2.4450    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1874    1.0384    0.5110 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6454    0.3505   -0.6371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029    0.0661   -0.5948 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5638    0.8931   -1.6003 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9277    0.7169   -1.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1548   -0.6305   -2.3376 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5260   -0.9216   -2.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4126   -1.7434   -1.6835 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9626   -2.5856   -2.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2479   -1.3711   -0.8397 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4083   -2.0182    0.4116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    0.2199    1.1880 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4191    0.5257    2.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461   -1.2527    1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9064   -1.9043    1.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -1.8300    0.8190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4549   -2.4780   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3595   -2.2686    1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0756   -1.5790   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4569    0.7474    0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234    0.5424   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6047    2.2041   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3615    1.8105   -1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899    1.2637   -2.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610   -0.5139   -2.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0788    0.3876   -2.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8967    1.7958    1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5300    3.5683    2.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356    4.7097    1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610    2.5274   -0.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290    2.9667    0.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1255    1.0668    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4768    0.3762    0.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3156    1.4759   -2.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4486    0.7188   -0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231   -0.5497   -3.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9423   -0.4939   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1257   -2.4126   -1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441   -2.0544   -3.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3322   -1.8300   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8532   -1.3827    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791    0.4477    3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1559   -0.1877    3.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7406    1.5767    2.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1748   -1.5424    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812   -1.6629    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6031   -2.9704    1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.4851    2.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879   -3.0326   -0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778   -3.2242   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788   -1.7427   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8058   -1.9338    1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5127   -3.3589    0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0845   -1.3298    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0229   -2.1377   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 13 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
  9 10  1  0
 10 11  2  0
 31  4  1  0
 28  5  1  0
 24  6  1  0
 22 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  7 39  1  0
  8 40  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  1
 15 45  1  1
 17 46  1  0
 17 47  1  0
 18 48  1  6
 19 49  1  0
 20 50  1  1
 21 51  1  0
 22 52  1  6
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
 10 41  1  0
M  END

  Mrv1652309092223052D          

 31 34  0  0  1  0            999 V2000
    0.0904    0.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6702   -0.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519   -1.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672   -1.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908   -2.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -1.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377   -1.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911   -1.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3284   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0176   -1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6047   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -2.9146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1649   -3.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -4.2868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7772   -4.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1818   -4.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -5.4288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7831   -5.9998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708   -5.6589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3675   -6.4601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7662   -5.0879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5585   -5.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -2.7442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4749   -3.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075   -3.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -3.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5138   -2.6480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0093   -3.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2818   -2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -1.6055    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 13 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2C3=CC=C(C[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@]3(C)CC[C@@]2(C)CC1)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O6/c1-14(2)16-7-8-24(3)9-10-25(4)17(20(16)24)6-5-15(12-26)11-19(25)31-23-22(29)21(28)18(27)13-30-23/h5-6,12,14,18-19,21-23,27-29H,7-11,13H2,1-4H3/t18-,19+,21+,22-,23+,24-,25-/m1/s1

> <INCHI_KEY>
LPPCHLAEVDUIIW-NLLUTMDRSA-N

> <FORMULA>
C25H36O6

> <MOLECULAR_WEIGHT>
432.557

> <EXACT_MASS>
432.251188879

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.86744636906536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,5aR,6S)-3a,5a-dimethyl-1-(propan-2-yl)-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H,3H,3aH,4H,5H,5aH,6H,7H-cyclohepta[e]indene-8-carbaldehyde

> <JCHEM_LOGP>
1.9733997313333345

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.403212287166475

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.246231746121753

> <JCHEM_PKA_STRONGEST_BASIC>
-3.52658062854581

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
118.83849999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,5aR,6S)-1-isopropyl-3a,5a-dimethyl-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H,3H,4H,5H,6H,7H-cyclohepta[e]indene-8-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.169   0.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.251  -0.969   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.741  -0.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.844  -2.454   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.806  -3.656   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.343  -3.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.988  -2.348   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.484  -1.981   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.703  -2.921   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.080  -2.230   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.366  -3.077   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.729  -4.461   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.541  -5.441   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.908  -6.936   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.796  -8.002   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.318  -7.572   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.206  -8.638   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.573 -10.134   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.462 -11.200   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.052 -10.563   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.419 -12.059   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.164  -9.498   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.642  -9.927   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.034  -5.123   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.620  -6.547   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.187  -6.409   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.650  -6.319   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.959  -4.943   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.017  -6.134   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.526  -4.535   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.597  -2.997   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22                                                            
CONECT   24   13    6   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    5   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30    4                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₆

Average Mass

432.5570 Da

Monoisotopic Mass

432.25119 Da

IUPAC Name

(3aR,5aR,6S)-3a,5a-dimethyl-1-(propan-2-yl)-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H,3H,3aH,4H,5H,5aH,6H,7H-cyclohepta[e]indene-8-carbaldehyde

Traditional Name

(3aR,5aR,6S)-1-isopropyl-3a,5a-dimethyl-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H,3H,4H,5H,6H,7H-cyclohepta[e]indene-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2C3=CC=C(C[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@]3(C)CC[C@@]2(C)CC1)C=O

InChI Identifier

InChI=1S/C25H36O6/c1-14(2)16-7-8-24(3)9-10-25(4)17(20(16)24)6-5-15(12-26)11-19(25)31-23-22(29)21(28)18(27)13-30-23/h5-6,12,14,18-19,21-23,27-29H,7-11,13H2,1-4H3/t18-,19+,21+,22-,23+,24-,25-/m1/s1

InChI Key

LPPCHLAEVDUIIW-NLLUTMDRSA-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
Hericium erinaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aldehyde
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	1.97	ChemAxon
pKa (Strongest Acidic)	12.25	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.84 m³·mol⁻¹	ChemAxon
Polarizability	46.87 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

8586005

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10410568

PDB ID

Not Available

ChEBI ID

175499

Good Scents ID

Not Available

References

General References

Bailly C, Gao JM: Erinacine A and related cyathane diterpenoids: Molecular diversity and mechanisms underlying their neuroprotection and anticancer activities. Pharmacol Res. 2020 Sep;159:104953. doi: 10.1016/j.phrs.2020.104953. Epub 2020 May 30. [PubMed:32485283 ]
Hsu PC, Lan YJ, Chen CC, Lee LY, Chen WP, Wang YC, Lee YH: Erinacine A attenuates glutamate transporter 1 downregulation and protects against ischemic brain injury. Life Sci. 2022 Oct 1;306:120833. doi: 10.1016/j.lfs.2022.120833. Epub 2022 Jul 23. [PubMed:35882273 ]
Lee SL, Hsu JY, Chen TC, Huang CC, Wu TY, Chin TY: Erinacine A Prevents Lipopolysaccharide-Mediated Glial Cell Activation to Protect Dopaminergic Neurons against Inflammatory Factor-Induced Cell Death In Vitro and In Vivo. Int J Mol Sci. 2022 Jan 12;23(2):810. doi: 10.3390/ijms23020810. [PubMed:35054997 ]
Li TJ, Lee TY, Lo Y, Lee LY, Li IC, Chen CC, Chang FC: Hericium erinaceus mycelium ameliorate anxiety induced by continuous sleep disturbance in vivo. BMC Complement Med Ther. 2021 Dec 5;21(1):295. doi: 10.1186/s12906-021-03463-3. [PubMed:34865649 ]
Lee LY, Chou W, Chen WP, Wang MF, Chen YJ, Chen CC, Tung KC: Erinacine A-Enriched Hericium erinaceus Mycelium Delays Progression of Age-Related Cognitive Decline in Senescence Accelerated Mouse Prone 8 (SAMP8) Mice. Nutrients. 2021 Oct 19;13(10):3659. doi: 10.3390/nu13103659. [PubMed:34684662 ]
Tsai PC, Wu YK, Hu JH, Li IC, Lin TW, Chen CC, Kuo CF: Preclinical Bioavailability, Tissue Distribution, and Protein Binding Studies of Erinacine A, a Bioactive Compound from Hericium erinaceus Mycelia Using Validated LC-MS/MS Method. Molecules. 2021 Jul 27;26(15):4510. doi: 10.3390/molecules26154510. [PubMed:34361662 ]
Roda E, Priori EC, Ratto D, De Luca F, Di Iorio C, Angelone P, Locatelli CA, Desiderio A, Goppa L, Savino E, Bottone MG, Rossi P: Neuroprotective Metabolites of Hericium erinaceus Promote Neuro-Healthy Aging. Int J Mol Sci. 2021 Jun 15;22(12):6379. doi: 10.3390/ijms22126379. [PubMed:34203691 ]
Huang HT, Ho CH, Sung HY, Lee LY, Chen WP, Chen YW, Chen CC, Yang CS, Tzeng SF: Hericium erinaceus mycelium and its small bioactive compounds promote oligodendrocyte maturation with an increase in myelin basic protein. Sci Rep. 2021 Mar 22;11(1):6551. doi: 10.1038/s41598-021-85972-2. [PubMed:33753806 ]
Kuo HC, Lu CC, Shen CH, Tung SY, Hsieh MC, Lee KC, Lee LY, Chen CC, Teng CC, Huang WS, Chen TC, Lee KF: Retraction Note to: Hericium erinaceus mycelium and its isolated erinacine A protection from MPTP-induced neurotoxicity through the ER stress, triggering an apoptosis cascade. J Transl Med. 2021 Feb 15;19(1):67. doi: 10.1186/s12967-021-02748-y. [PubMed:33588874 ]
Kawagishi H: Chemical studies on bioactive compounds related to higher fungi. Biosci Biotechnol Biochem. 2021 Jan 7;85(1):1-7. doi: 10.1093/bbb/zbaa072. [PubMed:33577664 ]
Valu MV, Soare LC, Sutan NA, Ducu C, Moga S, Hritcu L, Boiangiu RS, Carradori S: Optimization of Ultrasonic Extraction to Obtain Erinacine A and Polyphenols with Antioxidant Activity from the Fungal Biomass of Hericium erinaceus. Foods. 2020 Dec 18;9(12):1889. doi: 10.3390/foods9121889. [PubMed:33352839 ]
Li IC, Chang HH, Lin CH, Chen WP, Lu TH, Lee LY, Chen YW, Chen YP, Chen CC, Lin DP: Prevention of Early Alzheimer's Disease by Erinacine A-Enriched Hericium erinaceus Mycelia Pilot Double-Blind Placebo-Controlled Study. Front Aging Neurosci. 2020 Jun 3;12:155. doi: 10.3389/fnagi.2020.00155. eCollection 2020. [PubMed:32581767 ]
Lee KF, Tung SY, Teng CC, Shen CH, Hsieh MC, Huang CY, Lee KC, Lee LY, Chen WP, Chen CC, Huang WS, Kuo HC: Post-Treatment with Erinacine A, a Derived Diterpenoid of H. erinaceus, Attenuates Neurotoxicity in MPTP Model of Parkinson's Disease. Antioxidants (Basel). 2020 Feb 4;9(2):137. doi: 10.3390/antiox9020137. [PubMed:32033220 ]
Lee KC, Lee KF, Tung SY, Huang WS, Lee LY, Chen WP, Chen CC, Teng CC, Shen CH, Hsieh MC, Kuo HC: Induction Apoptosis of Erinacine A in Human Colorectal Cancer Cells Involving the Expression of TNFR, Fas, and Fas Ligand via the JNK/p300/p50 Signaling Pathway With Histone Acetylation. Front Pharmacol. 2019 Oct 15;10:1174. doi: 10.3389/fphar.2019.01174. eCollection 2019. [PubMed:31680958 ]
LOTUS database [Link]

Showing NP-Card for (3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde (NP0290412)

MOL for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

3D MOL for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

3D SDF for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

3D-SDF for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

PDB for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

3D PDB for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

SMILES for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

INCHI for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

Structure for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)

3D Structure for NP0290412 ((3ar,5ar,6s)-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,7h-cyclohepta[e]indene-8-carbaldehyde)