NP-MRD: Showing NP-Card for (1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate (NP0285374)

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Record Information

Version

2.0

Created at

2022-09-09 13:31:37 UTC

Updated at

2022-09-09 13:31:38 UTC

NP-MRD ID

NP0285374

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate

Description

Glaucocalyxin B belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate is found in Isodon japonicus and Isodon pharicus. (1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate was first documented in 2017 (PMID: 29241205). Based on a literature review a significant number of articles have been published on Glaucocalyxin B (PMID: 32744957) (PMID: 30409115) (PMID: 35251480) (PMID: 35100137) (PMID: 34580236) (PMID: 30304556).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092215312D          

 27 30  0  0  1  0            999 V2000
    0.0095   -0.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565   -0.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    0.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2888    0.0848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8893   -0.5679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6457   -1.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -0.9157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8145   -0.4489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0975   -1.1937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231   -2.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -2.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790   -2.5123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -0.3707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6881   -1.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3184   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1567    0.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7603    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165    1.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742    1.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551    0.4164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4015    1.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5925    0.8721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3053    1.6768    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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9  2  1  1  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 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
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    3.1620   -0.8148   -2.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102   -0.4946   -1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9004    0.6842   -1.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8595    1.7815   -1.9133 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1453    0.1894   -0.1517 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2560   -0.9109   -0.6305 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6609   -2.1900    0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814   -2.5049   -0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9168   -1.2468   -0.4483 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3567   -0.3241    0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2154    0.7087    0.9728 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414    0.9632    2.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6502    2.0954    2.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385    0.1976    3.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058   -0.6783   -0.6667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8876   -1.9337   -0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7558   -0.5848   -2.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9887    0.2300   -2.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8364    0.2309   -0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0110   -0.0963   -0.9827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1248    0.6677    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4551    2.1679    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    0.0251    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6728    0.5755    0.0055 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8140    0.8262    1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5329    1.2631    0.6262 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2486    1.8531    1.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431   -1.7040   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561   -0.2021   -3.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5367   -1.1967   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706   -3.0756   -0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475   -2.1386    1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528   -3.1717    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231   -2.9947   -1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9599   -1.5292   -0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325   -0.9184    1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6959    1.7147    2.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5171    2.9318    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316    2.4243    3.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4563   -2.2645    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -2.6992   -0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618   -1.8276    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9616   -0.0890   -2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8662   -1.6020   -2.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6295   -0.2060   -3.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    1.2712   -2.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375    2.7663   -0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5453    2.2894    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589    2.4177    1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375   -0.5752    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575    0.7705    2.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5436   -0.5925    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    1.4118   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -0.0620    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063    1.6759    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    2.0907   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6310    2.4040    2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 26  1  0
 26 27  1  0
 26 25  1  0
 25 24  1  0
 24 21  1  0
 21 22  1  0
 21 23  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  1
  5  3  1  6
  3  4  2  0
  3  2  1  0
  2  1  2  3
  5 10  1  0
 15 24  1  0
  2  9  1  0
 15  6  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 10 36  1  1
  9 35  1  1
  8 33  1  0
  8 34  1  0
  7 31  1  0
  7 32  1  0
  6 30  1  6
 26 56  1  6
 27 57  1  0
 25 54  1  0
 25 55  1  0
 24 53  1  6
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 18 45  1  0
 18 46  1  0
 17 43  1  0
 17 44  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1652309092215312D          

 27 30  0  0  1  0            999 V2000
    0.0095   -0.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565   -0.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    0.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2888    0.0848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8893   -0.5679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6457   -1.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -0.9157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8145   -0.4489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0975   -1.1937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231   -2.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -2.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790   -2.5123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -0.3707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6881   -1.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3184   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1567    0.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7603    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165    1.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742    1.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551    0.4164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4015    1.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5925    0.8721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3053    1.6768    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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9  2  1  1  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 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
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0285374

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@H]2CC[C@@H]3[C@]1([C@H](O)C[C@@H]1C(C)(C)C(=O)CC[C@@]31C)C(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-11-13-6-7-14-21(5)9-8-16(24)20(3,4)15(21)10-17(25)22(14,18(11)26)19(13)27-12(2)23/h13-15,17,19,25H,1,6-10H2,2-5H3/t13-,14-,15+,17+,19+,21-,22-/m0/s1

> <INCHI_KEY>
LSUXOKVMORWDLT-KEXKRWMXSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.4195871972041

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,9R,10S,13S,16R)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-16-yl acetate

> <JCHEM_LOGP>
2.8509628129999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.95691517896202

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.42048067395562

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0522811945615516

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
99.19009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,9R,10S,13S,16R)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-16-yl acetate

> <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       0.018  -0.131   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599  -0.265   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.759   0.870   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.770   2.127   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.273   0.158   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.393  -1.060   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.939  -2.638   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.361  -2.938   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.313  -1.709   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.387  -0.838   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.915  -2.228   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.776  -4.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.047  -4.895   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.387  -4.690   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.922  -0.692   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.884  -2.404   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.963  -1.826   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.466  -1.491   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.928  -0.022   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.492   0.206   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.886   1.113   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.111   2.156   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.352   2.605   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.383   0.777   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.349   1.943   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.839   1.628   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.303   3.130   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10   26                                             
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2   10                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    6   16   17   24                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   15   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    5   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(1R,2R,4S,9R,10S,13S,16R)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-16-yl acetate

Traditional Name

(1R,2R,4S,9R,10S,13S,16R)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-16-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@H]2CC[C@@H]3[C@]1([C@H](O)C[C@@H]1C(C)(C)C(=O)CC[C@@]31C)C(=O)C2=C

InChI Identifier

InChI=1S/C22H30O5/c1-11-13-6-7-14-21(5)9-8-16(24)20(3,4)15(21)10-17(25)22(14,18(11)26)19(13)27-12(2)23/h13-15,17,19,25H,1,6-10H2,2-5H3/t13-,14-,15+,17+,19+,21-,22-/m0/s1

InChI Key

LSUXOKVMORWDLT-KEXKRWMXSA-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
Isodon japonicus	LOTUS Database	35616633
Isodon pharicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.85	ChemAxon
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.19 m³·mol⁻¹	ChemAxon
Polarizability	40.42 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

24627850

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14193399

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mir RH, Shah AJ, Mohi-Ud-Din R, Pottoo FH, Dar MA, Jachak SM, Masoodi MH: Natural Anti-inflammatory Compounds as Drug Candidates in Alzheimer's Disease. Curr Med Chem. 2021;28(23):4799-4825. doi: 10.2174/0929867327666200730213215. [PubMed:32744957 ]
Zhao F, Sun M, Zhang W, Jiang C, Teng J, Sheng W, Li M, Zhang A, Duan Y, Xue J: Comparative transcriptome analysis of roots, stems and leaves of Isodon amethystoides reveals candidate genes involved in Wangzaozins biosynthesis. BMC Plant Biol. 2018 Nov 8;18(1):272. doi: 10.1186/s12870-018-1505-0. [PubMed:30409115 ]
Zhang T, Xu C, Zheng P, Zhang X, Qiu C, Wu F, Chen J, Xiao Z, Zhu J, Zhang J, Zou P, Ni D: Glaucocalyxin B Attenuates Ovarian Cancer Cell Growth and Cisplatin Resistance In Vitro via Activating Oxidative Stress. Oxid Med Cell Longev. 2022 Feb 25;2022:6324292. doi: 10.1155/2022/6324292. eCollection 2022. [PubMed:35251480 ]
Han C, Yang Y, Sheng Y, Wang J, Zhou X, Li W, Guo L, Zhang C, Ye Q: Correction for: Glaucocalyxin B inhibits cartilage inflammatory injury in rheumatoid arthritis by regulating M1 polarization of synovial macrophages through NF-kappaB pathway. Aging (Albany NY). 2022 Jan 31;14(2):1065-1066. doi: 10.18632/aging.203864. [PubMed:35100137 ]
Han C, Yang Y, Sheng Y, Wang J, Zhou X, Li W, Guo L, Zhang C, Ye Q: Glaucocalyxin B inhibits cartilage inflammatory injury in rheumatoid arthritis by regulating M1 polarization of synovial macrophages through NF-kappaB pathway. Aging (Albany NY). 2021 Sep 27;13(18):22544-22555. doi: 10.18632/aging.203567. Epub 2021 Sep 27. [PubMed:34580236 ]
Liu Y, Wu X, An J, Lv W, Geng Y, Lou T, Zhang Y: Glaucocalyxin B protects against oxygen-glucose-deprivation/reperfusion-induced neuronal injury in PC-12 cells. J Cell Biochem. 2019 Apr;120(4):6137-6144. doi: 10.1002/jcb.27901. Epub 2018 Oct 10. [PubMed:30304556 ]
Xu W, Zheng D, Liu Y, Li J, Yang L, Shang X: Glaucocalyxin B Alleviates Lipopolysaccharide-Induced Parkinson's Disease by Inhibiting TLR/NF-kappaB and Activating Nrf2/HO-1 Pathway. Cell Physiol Biochem. 2017;44(6):2091-2104. doi: 10.1159/000485947. Epub 2017 Dec 12. [PubMed:29241205 ]
Seo EJ, Fischer N, Efferth T: Phytochemicals as inhibitors of NF-kappaB for treatment of Alzheimer's disease. Pharmacol Res. 2018 Mar;129:262-273. doi: 10.1016/j.phrs.2017.11.030. Epub 2017 Nov 24. [PubMed:29179999 ]
Huang W, Guan X, Lv Y: Simultaneous determination of glaucocalyxin A and glaucocalyxin B in rat plasma by LC-MS/MS and its application to a pharmacokinetic study after oral administration of Rabdosia japonica extract. Biomed Chromatogr. 2018 Feb;32(2). doi: 10.1002/bmc.4089. Epub 2017 Sep 26. [PubMed:28873500 ]
Ur Rahman MS, Zhang L, Wu L, Xie Y, Li C, Cao J: Sensitization of gastric cancer cells to alkylating agents by glaucocalyxin B via cell cycle arrest and enhanced cell death. Drug Des Devel Ther. 2017 Aug 22;11:2431-2441. doi: 10.2147/DDDT.S145719. eCollection 2017. [PubMed:28860714 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate (NP0285374)

MOL for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

3D MOL for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

3D SDF for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

3D-SDF for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

PDB for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

3D PDB for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

SMILES for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

INCHI for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

Structure for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)

3D Structure for NP0285374 ((1r,2r,4s,9r,10s,13s,16r)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-16-yl acetate)