NP-MRD: Showing NP-Card for ({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid (NP0319336)

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Record Information

Version

1.0

Created at

2022-09-11 20:18:34 UTC

Updated at

2022-09-11 20:18:34 UTC

NP-MRD ID

NP0319336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid

Description

2-({5-[(1,2,4A-trimethyl-5-methylidene-decahydronaphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. ({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid is found in Dactylospongia elegans. 2-({5-[(1,2,4A-trimethyl-5-methylidene-decahydronaphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161505552D          

 29 31  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    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
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617    0.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116    2.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360    2.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9242    2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0997    2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    3.5846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496    4.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    5.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995    5.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0622    5.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619    2.1853    0.0000 O   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  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  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
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -4.9272   -0.9679   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2985    0.1600   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9974    1.2372    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9470    2.0987    0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7887    1.1623    1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0107    0.9173   -0.0259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9636    0.4773   -1.0777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2211    1.6427   -2.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4931   -0.6380   -1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087   -1.6893   -1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340   -1.0331   -0.6574 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2245   -2.2025   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7747    0.1026    0.2431 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8700   -0.5482    1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676    1.0673    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846    0.6761    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    0.9698    1.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244    1.6306    2.8275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559    0.6004    2.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    0.8749    3.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3098   -0.0726    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804   -0.3591    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931   -1.0096   -0.5650 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2799   -0.6390   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0491   -1.4435   -1.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4743   -2.3485   -2.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3851   -1.2330   -1.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289    0.0152   -0.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4060   -0.2936   -1.3717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4824   -1.7820   -1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9317   -1.0971   -0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6992    1.8130   -0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5516    0.7409    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3121    2.6187    1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5424    2.8914    0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    0.2211    1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283    1.7927    1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968    1.9746   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    1.3510   -3.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2011    2.0939   -1.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603    2.4567   -1.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3172   -1.0094   -2.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -0.3111   -2.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5972   -2.5694   -1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368   -1.9251   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323   -0.7532   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978   -2.5643   -0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4211   -3.1201    0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9002   -2.0298    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1658   -0.7492    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -1.4942    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3096    0.0928    2.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0501    1.9652    0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3989    1.5804   -0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0614    2.6412    2.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2996   -0.3396    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5472   -1.7760   -1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4240    0.4339   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7727   -0.7720    0.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0442   -1.5292   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  6 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 27  1  0
 25 26  2  0
 22 28  1  0
 28 29  2  0
 13 11  1  0
 28 16  1  0
  2  7  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 11 46  1  6
 10 44  1  0
 10 45  1  0
  9 42  1  0
  9 43  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
  6 38  1  6
  5 36  1  0
  5 37  1  0
  4 34  1  0
  4 35  1  0
  3 32  1  0
  3 33  1  0
  1 30  1  0
  1 31  1  0
 14 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 18 55  1  0
 21 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 27 60  1  0
M  END


  Mrv1533004161505552D          

 29 31  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    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
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617    0.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116    2.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360    2.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9242    2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0997    2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    3.5846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496    4.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    5.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995    5.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0622    5.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619    2.1853    0.0000 O   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  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  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
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0319336

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)C(CCCC2=C)C1(C)CC1=C(O)C(=O)C=C(NCC(O)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H31NO5/c1-13-6-5-7-18-22(13,3)9-8-14(2)23(18,4)11-15-20(28)16(24-12-19(26)27)10-17(25)21(15)29/h10,14,18,24,29H,1,5-9,11-12H2,2-4H3,(H,26,27)

> <INCHI_KEY>
NNDNTSLKXNJKMJ-UHFFFAOYSA-N

> <FORMULA>
C23H31NO5

> <MOLECULAR_WEIGHT>
401.503

> <EXACT_MASS>
401.220223102

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.745752616766325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-({5-[(1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.5278044893333345

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.1030128321499495

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.710545918282408

> <JCHEM_PKA_STRONGEST_BASIC>
-5.092202376659469

> <JCHEM_POLAR_SURFACE_AREA>
103.70000000000002

> <JCHEM_REFRACTIVITY>
111.91069999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.723   1.360   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.093   2.666   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.632   2.612   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.355   1.252   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.448   3.918   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.987   3.864   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.725   5.278   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.186   5.331   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.537   6.691   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.279   7.997   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.444   9.357   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.372  10.663   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.983   9.411   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.630   4.025   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.169   4.079   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13    7    2   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   16   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
2-({5-[(1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetate	Generator

Chemical Formula

C₂₃H₃₁NO₅

Average Mass

401.5030 Da

Monoisotopic Mass

401.22022 Da

IUPAC Name

2-({5-[(1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid

Traditional Name

({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)C(CCCC2=C)C1(C)CC1=C(O)C(=O)C=C(NCC(O)=O)C1=O

InChI Identifier

InChI=1S/C23H31NO5/c1-13-6-5-7-18-22(13,3)9-8-14(2)23(18,4)11-15-20(28)16(24-12-19(26)27)10-17(25)21(15)29/h10,14,18,24,29H,1,5-9,11-12H2,2-4H3,(H,26,27)

InChI Key

NNDNTSLKXNJKMJ-UHFFFAOYSA-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
Dactylospongia elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

Prenylbenzoquinone
Alpha-amino acid
Alpha-amino acid or derivatives
P-benzoquinone
Quinone
Vinylogous amide
Vinylogous acid
Amino acid or derivatives
Ketone
Amino acid
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Enamine
Enol
Monocarboxylic acid or derivatives
Secondary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.53	ALOGPS
logP	3.53	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.91 m³·mol⁻¹	ChemAxon
Polarizability	42.75 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	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid (NP0319336)

MOL for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

3D MOL for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

3D SDF for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

3D-SDF for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

PDB for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

3D PDB for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

SMILES for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

INCHI for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

Structure for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)

3D Structure for NP0319336 (({5-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl}amino)acetic acid)