NP-MRD: Showing NP-Card for (4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione (NP0167605)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 03:13:43 UTC

Updated at

2022-09-03 03:13:43 UTC

NP-MRD ID

NP0167605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione

Description

Dichrostachine B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione is found in Dichrostachys cinerea. Based on a literature review very few articles have been published on Dichrostachine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032205132D          

 45 50  0  0  1  0            999 V2000
    3.2029   -1.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180   -2.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700   -3.1462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0770   -2.9747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151   -3.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2081   -4.1024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9532   -4.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7702   -5.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820   -5.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1462   -5.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942   -4.4454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2128   -4.6170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491   -3.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -3.4893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1041   -2.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9110   -2.7047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3590   -2.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -2.2631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2971   -3.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3833   -3.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5099   -3.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619   -2.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070   -1.8215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3590   -1.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660   -1.3800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561    0.1893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4012    0.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2971   -0.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905   -0.1117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  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   -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
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 37 44  1  0  0  0  0
 44 45  1  0  0  0  0
 33 45  1  0  0  0  0
M  END

     RDKit          3D

 87 92  0  0  0  0  0  0  0  0999 V2000
    0.1204    2.1464   -1.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    1.1792   -1.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8282    1.3675   -2.6683 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5331    2.5943   -3.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2374    1.3594   -2.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    0.5006   -0.9580 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7059    1.0039   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567    1.0389   -1.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667    2.3581    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1445    0.0450    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361   -0.5796    1.6532 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5319   -1.7504    2.2622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688   -1.0485    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4063    0.1697    0.0141 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1932    1.1604    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190   -0.0811   -0.7746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0034   -0.6323   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2221   -1.1732   -0.6915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9363   -0.7032   -1.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122   -0.1121   -3.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2595   -0.8283   -1.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649   -1.4778   -0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3419   -2.3665   -0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9885   -3.6019   -0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462   -3.9462   -1.8057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -4.4326   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -5.7178   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189   -6.6843   -0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -3.9127    0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3885   -2.5469    1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9103   -2.2449    2.4394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1619   -1.6159    0.4609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6513   -0.4165    1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1526   -0.4902    2.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6100    0.6450    3.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777    0.6089    4.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5605    1.8377    2.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0247    2.9837    2.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5189    2.8752    4.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9697    4.1665    2.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640    4.2075    0.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142    5.4038    0.2795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0148    3.0657    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0545    1.8572    1.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343    0.7348    0.5508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016    3.0668   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4469    2.0468   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    0.5936   -3.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    3.0259   -3.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950    1.0559   -2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4965    2.4496   -1.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8471   -0.5095   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7265    0.1504   -1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8143    1.9731   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8126    0.9401   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8583    3.0409   -0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3222    2.3273    1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5653    2.8911    0.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -0.7250    0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7536    0.6398    1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7024    0.0758    2.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3680   -1.4823    2.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2933   -1.8369    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1222   -1.4472    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    0.7353    2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224    2.0009    0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376    1.9573    0.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4545   -0.8602   -1.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -1.4773    0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034    0.1331    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8478   -2.2839   -1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048    0.9642   -3.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -0.5782   -3.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9217   -0.4830   -3.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7690   -0.4281   -2.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -2.1023   -1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6783   -0.6837   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9802   -2.6301    0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4668   -7.6194   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7233   -6.3509   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556   -6.8713    0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -4.5385    1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.4350    2.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8509    3.7243    4.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3260    5.0821    2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    5.4436   -0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150    3.0782   -0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 26  1  0
 26 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 18  1  0
 18 17  1  0
 17 16  1  0
 16  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  1
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 32 33  1  1
 33 34  2  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 38 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 24 26  1  0
 45 33  1  0
 23 32  1  0
 44 37  1  0
 14 16  1  0
 14  6  1  0
 28 79  1  0
 28 80  1  0
 28 81  1  0
 29 82  1  0
 18 71  1  6
 17 69  1  0
 17 70  1  0
 16 68  1  6
  1 46  1  0
  1 47  1  0
  3 48  1  6
  4 49  1  0
  5 50  1  0
  5 51  1  0
  6 52  1  6
  8 53  1  0
  8 54  1  0
  8 55  1  0
  9 56  1  0
  9 57  1  0
  9 58  1  0
 10 59  1  0
 10 60  1  0
 11 61  1  1
 12 62  1  0
 13 63  1  0
 13 64  1  0
 15 65  1  0
 15 66  1  0
 15 67  1  0
 20 72  1  0
 20 73  1  0
 20 74  1  0
 21 75  1  0
 22 76  1  0
 22 77  1  0
 23 78  1  1
 34 83  1  0
 39 84  1  0
 40 85  1  0
 42 86  1  0
 43 87  1  0
M  END


  Mrv1652309032205132D          

 45 50  0  0  1  0            999 V2000
    3.2029   -1.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180   -2.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700   -3.1462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0770   -2.9747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151   -3.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2081   -4.1024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9532   -4.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7702   -5.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820   -5.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1462   -5.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942   -4.4454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2128   -4.6170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491   -3.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -3.4893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1041   -2.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9110   -2.7047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3590   -2.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -2.2631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2971   -3.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3833   -3.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5099   -3.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619   -2.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070   -1.8215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3590   -1.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660   -1.3800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -0.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561    0.1893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4012    0.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2971   -0.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905   -0.1117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  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   -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
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 37 44  1  0  0  0  0
 44 45  1  0  0  0  0
 33 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)[C@]2([C@H](C[C@H]3C(=C)[C@@H](O)C[C@H]4C(C)(C)C[C@H](O)C[C@]34C)C(C)=CC[C@H]2C1=O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C36H42O9/c1-17-7-8-21-33(43)28(44-6)14-30(42)36(21,31-13-26(41)32-25(40)9-19(37)10-27(32)45-31)22(17)11-23-18(2)24(39)12-29-34(3,4)15-20(38)16-35(23,29)5/h7,9-10,13-14,20-24,29,37-40H,2,8,11-12,15-16H2,1,3-6H3/t20-,21-,22+,23-,24-,29-,35+,36-/m0/s1

> <INCHI_KEY>
DYFMUBBDBHDXDV-QUUXZHRUSA-N

> <FORMULA>
C36H42O9

> <MOLECULAR_WEIGHT>
618.723

> <EXACT_MASS>
618.282882932

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
65.30068943378433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,5R,8aR)-5-{[(1R,3S,4aS,7S,8aS)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxy-6-methyl-1,4,4a,5,8,8a-hexahydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.5465356303333335

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.1913797507267

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.588591429884643

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7397973583548055

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
170.76649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,5R,8aR)-5-{[(1R,3S,4aS,7S,8aS)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5H-naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.979  -3.483   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.074  -4.729   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.104  -5.873   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.610  -5.553   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.628  -7.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.122  -7.658   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.646  -9.122   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.171  -9.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.700 -10.661   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.140  -9.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.109  -8.298   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.397  -8.618   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.585  -6.834   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.091  -6.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.061  -5.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.567  -5.049   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.537  -3.904   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.030  -4.224   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.555  -5.689   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.716  -7.221   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.952  -6.009   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.982  -4.865   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.506  -3.400   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.537  -2.256   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.043  -2.576   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.061  -0.791   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.091   0.353   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.615   1.818   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.555  -0.471   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.476  -1.615   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.102  -0.209   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    6   15   16                                             
CONECT   15   14                                                            
CONECT   16   14    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   18   33                                             
CONECT   33   32   34   45                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   44                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   37   45                                                  
CONECT   45   44   33                                                       
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₄₂O₉

Average Mass

618.7230 Da

Monoisotopic Mass

618.28288 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)[C@]2([C@H](C[C@H]3C(=C)[C@@H](O)C[C@H]4C(C)(C)C[C@H](O)C[C@]34C)C(C)=CC[C@H]2C1=O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C36H42O9/c1-17-7-8-21-33(43)28(44-6)14-30(42)36(21,31-13-26(41)32-25(40)9-19(37)10-27(32)45-31)22(17)11-23-18(2)24(39)12-29-34(3,4)15-20(38)16-35(23,29)5/h7,9-10,13-14,20-24,29,37-40H,2,8,11-12,15-16H2,1,3-6H3/t20-,21-,22+,23-,24-,29-,35+,36-/m0/s1

InChI Key

DYFMUBBDBHDXDV-QUUXZHRUSA-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
Dichrostachys cinerea	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

Labdane diterpenoid
Diterpenoid
Chromone
Benzopyran
1-benzopyran
Cyclohexenone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Cyclic alcohol
Vinylogous ester
Vinylogous acid
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
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	4.32	ALOGPS
logP	4.55	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	6.59	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

24665299

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44557089

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione (NP0167605)

MOL for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

3D MOL for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

3D SDF for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

3D-SDF for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

PDB for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

3D PDB for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

SMILES for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

INCHI for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

Structure for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)

3D Structure for NP0167605 ((4as,5r,8ar)-5-{[(1r,3s,4as,7s,8as)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4a-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxy-6-methyl-8,8a-dihydro-5h-naphthalene-1,4-dione)