NP-MRD: Showing NP-Card for (5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate (NP0298596)

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Record Information

Version

2.0

Created at

2022-09-10 09:56:33 UTC

Updated at

2022-09-10 09:56:34 UTC

NP-MRD ID

NP0298596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate

Description

1-Deoxyforskolin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate was first documented in 2009 (PMID: 20034210). Based on a literature review a small amount of articles have been published on 1-Deoxyforskolin (PMID: 26870691) (PMID: 19831022).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102211562D          

 28 30  0  0  1  0            999 V2000
    5.4217    0.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4532    1.2330    0.0000 C   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  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  3 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    4.6869   -1.5119   -1.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865   -0.5497   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1734   -0.2983    0.0809 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2928   -0.0498    1.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -1.5943    0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -1.8434   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3244   -2.9536   -0.9128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -0.6938   -0.8513 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7459   -0.6679   -2.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -1.1164   -0.5494 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2284   -2.0530   -1.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9007   -1.8895    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545   -2.5435    0.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -1.8392    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1501   -0.3786   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7051    0.3539    1.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1656   -0.0026   -1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7723    0.0307   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2928    1.1063    0.4852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8118    2.3270   -0.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    1.2247    0.7033 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5026    2.6173    0.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1434    3.2291    1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4422    4.6774    1.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    2.5333    2.7684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0475    0.6154   -0.3592 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0205    1.6525   -1.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120    0.7185    0.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1400   -1.7013   -2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9813   -2.1270   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5153    0.0340   -2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9695    0.6994    0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8891    0.3338    2.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8038   -1.0060    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668   -1.4544    1.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822   -2.3503    0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604   -0.1558   -2.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795   -3.0727   -1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3733   -2.2661   -2.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988   -1.6017   -2.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455   -2.6764    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7995   -1.1539    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -2.6263    1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484   -3.6112    0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776   -1.9575    0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6973   -2.3402   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8069    0.0811    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6833    1.4343    1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3355   -0.0738    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2257   -0.8174   -1.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734    0.9662   -1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1824    0.0213   -0.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177    0.4672   -1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464    1.0374    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7142    3.0204    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5255    0.8318    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7614    5.1249    2.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5010    5.1761    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    4.8610    0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260    2.5320   -1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4719    1.2418   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0069    2.0285   -1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 25  2  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  1  0
 19 18  1  0
 18 15  1  0
 15 16  1  0
 15 17  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  6
 10  8  1  0
  8  9  1  6
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3 28  1  0
 28 26  1  0
 26 27  1  6
  3  2  1  6
  2  1  2  3
 26 21  1  0
 10 18  1  0
 26  8  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 21 56  1  1
 19 54  1  1
 20 55  1  0
 18 53  1  6
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 14 45  1  0
 14 46  1  0
 13 43  1  0
 13 44  1  0
 12 41  1  0
 12 42  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
  9 37  1  0
  5 35  1  0
  5 36  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
  2 31  1  0
  1 29  1  0
  1 30  1  0
M  END


  Mrv1652309102211562D          

 28 30  0  0  1  0            999 V2000
    5.4217    0.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4532    1.2330    0.0000 C   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  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  3 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0298596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@@H](O)C2C(C)(C)CCC[C@]2(C)[C@]2(O)C(=O)CC(C)(OC12C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O6/c1-8-19(5)12-14(24)22(26)20(6)11-9-10-18(3,4)16(20)15(25)17(27-13(2)23)21(22,7)28-19/h8,15-17,25-26H,1,9-12H2,2-7H3/t15-,16?,17-,19?,20-,21?,22+/m0/s1

> <INCHI_KEY>
PXYAFNGUEZPJBI-QFAIONKOSA-N

> <FORMULA>
C22H34O6

> <MOLECULAR_WEIGHT>
394.508

> <EXACT_MASS>
394.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.35436217844255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6S,10aS,10bR)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate

> <JCHEM_LOGP>
2.586926671333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.809226360640167

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.643891784246396

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3264705404906794

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
102.9526

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S,10aS,10bR)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2H-naphtho[2,1-b]pyran-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      10.121   1.233   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.644   2.104   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -5.898   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.874  -4.565   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.713   2.302   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   12                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   27                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10    3                                                       
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   27                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   20    8   28                                             
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₆

Average Mass

394.5080 Da

Monoisotopic Mass

394.23554 Da

IUPAC Name

(5S,6S,10aS,10bR)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate

Traditional Name

(5S,6S,10aS,10bR)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2H-naphtho[2,1-b]pyran-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H](O)C2C(C)(C)CCC[C@]2(C)[C@]2(O)C(=O)CC(C)(OC12C)C=C

InChI Identifier

InChI=1S/C22H34O6/c1-8-19(5)12-14(24)22(26)20(6)11-9-10-18(3,4)16(20)15(25)17(27-13(2)23)21(22,7)28-19/h8,15-17,25-26H,1,9-12H2,2-7H3/t15-,16?,17-,19?,20-,21?,22+/m0/s1

InChI Key

PXYAFNGUEZPJBI-QFAIONKOSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Polycyclic triterpenoid
Triterpenoid
Naphthopyran
Naphthalene
Pyran
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.59	ChemAxon
pKa (Strongest Acidic)	11.64	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.95 m³·mol⁻¹	ChemAxon
Polarizability	42.35 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

134688089

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang YQ, Ma JP, Pan SL, Hou AJ, Huang JM: [Studies on the chemical constituents of Coleus forskohlii]. Zhong Yao Cai. 2009 Sep;32(9):1381-5. [PubMed:20034210 ]
Hebbani Nagarajappa S, Pandit S, Divanji M, Mariyanna B, Kumar P, Godavarthi A: Effect of Coleus forskohlii and its major constituents on cytochrome P450 induction. J Tradit Complement Med. 2015 Jan 29;6(1):130-3. doi: 10.1016/j.jtcme.2014.11.027. eCollection 2016 Jan. [PubMed:26870691 ]
Bodiwala HS, Sabde S, Mitra D, Bhutani KK, Singh IP: Anti-HIV diterpenes from Coleus forskohlii. Nat Prod Commun. 2009 Sep;4(9):1173-5. [PubMed:19831022 ]
LOTUS database [Link]

Showing NP-Card for (5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate (NP0298596)

MOL for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

3D MOL for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

3D SDF for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

3D-SDF for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

PDB for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

3D PDB for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

SMILES for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

INCHI for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

Structure for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)

3D Structure for NP0298596 ((5s,6s,10as,10br)-3-ethenyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-5-yl acetate)