NP-MRD: Showing NP-Card for methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate (NP0251497)

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Record Information

Version

2.0

Created at

2022-09-07 14:42:48 UTC

Updated at

2022-09-07 14:42:48 UTC

NP-MRD ID

NP0251497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

Description

Salvinorin G belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate is found in Salvia divinorum. methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate was first documented in 2005 (PMID: 16084728). Based on a literature review very few articles have been published on Salvinorin G (PMID: 19279674).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216422D          

 31 34  0  0  1  0            999 V2000
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    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
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  2  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
    2.7770    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  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
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  1  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
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9310    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025    2.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    3.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250    2.5951    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
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.8486    3.6136   -2.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3415    2.3755   -1.6116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2757    2.3011   -0.6915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252    3.3889   -0.2962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7587    1.0393   -0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061   -0.0876   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551   -1.3420   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276   -2.2780    0.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715   -1.4267   -0.2143 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9406   -2.4720    0.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978   -3.6502    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438   -4.7742    1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1731   -3.8287   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6712   -0.0770    0.1284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6524    0.8397    0.7424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3104    0.3792    2.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344    2.1850    1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    1.9474    1.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1818    1.2432    1.0162 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5165    1.0965    1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662    1.7530    2.6537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3822    0.1863    1.0547 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0682   -0.6224   -0.0541 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0184   -0.2553   -1.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011   -1.1377   -1.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4845   -0.4000   -2.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2724    0.8625   -2.5410 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4170    0.9937   -1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6415   -0.5530   -0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -0.1640    0.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9877   -1.1023    1.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6684    3.9196   -1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1023    4.4319   -2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2678    3.5739   -3.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371   -0.0406   -1.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.7570   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -5.5802    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665   -5.2021    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407   -4.4412    2.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5173    0.3985   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7434    1.3149    2.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -0.0450    2.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1979   -0.2654    1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6675    2.6023    0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7502    2.8594    1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    2.9444    2.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394    1.4428    2.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082    1.8424    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2495   -1.6802    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6407   -2.2127   -1.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1479   -0.8176   -3.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0802    1.9546   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023    0.2649   -1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -1.4800   -0.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789   -1.4792    2.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7036   -0.5844    2.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6011   -1.9980    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 30  1  0
 30 31  1  1
 30 29  1  0
 29 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  1
 23 24  1  0
 24 28  2  0
 28 27  1  0
 27 26  1  0
 26 25  2  0
 15  5  1  0
 25 24  1  0
 15 14  1  0
 19 30  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  9 36  1  6
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  6
 31 55  1  0
 31 56  1  0
 31 57  1  0
 29 53  1  0
 29 54  1  0
 23 49  1  1
 19 48  1  6
 18 46  1  0
 18 47  1  0
 17 44  1  0
 17 45  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 28 52  1  0
 26 51  1  0
 25 50  1  0
M  END


  Mrv1652309072216422D          

 31 34  0  0  1  0            999 V2000
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    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
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  2  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
    2.7770    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  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
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  1  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
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9310    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025    2.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    3.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250    2.5951    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
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0251497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(=O)[C@H](OC(C)=O)C2[C@@]3(C)C[C@H](OC(=O)[C@@H]3CC[C@@]12C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O8/c1-12(24)30-18-16(25)9-15(20(26)28-4)22(2)7-5-14-21(27)31-17(13-6-8-29-11-13)10-23(14,3)19(18)22/h6,8-9,11,14,17-19H,5,7,10H2,1-4H3/t14-,17-,18-,19?,22-,23-/m0/s1

> <INCHI_KEY>
KLIYEWBCXJFOSK-HOXPKSMJSA-N

> <FORMULA>
C23H26O8

> <MOLECULAR_WEIGHT>
430.453

> <EXACT_MASS>
430.162767797

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.207791495271906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,4aR,6aR,10R,10bR)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1H,2H,4H,4aH,5H,6H,6aH,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylate

> <JCHEM_LOGP>
2.654466584333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.898842318226404

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888530095801868

> <JCHEM_POLAR_SURFACE_AREA>
109.11000000000001

> <JCHEM_REFRACTIVITY>
106.74509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,4aR,6aR,10R,10bR)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1H,2H,4aH,5H,6H,10H,10aH-naphtho[2,1-c]pyran-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       5.184  -3.231   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.724  -3.231   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.034  -1.897   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   6.105   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.724   4.771   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.206   0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.738   3.598   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.058   5.105   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.724   5.875   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.420   4.844   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   30                                                  
CONECT   15   14    5   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   30                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   23   30                                                       
CONECT   30   29   14   19   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₈

Average Mass

430.4530 Da

Monoisotopic Mass

430.16277 Da

IUPAC Name

methyl (2S,4aR,6aR,10R,10bR)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1H,2H,4H,4aH,5H,6H,6aH,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylate

Traditional Name

methyl (2S,4aR,6aR,10R,10bR)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1H,2H,4aH,5H,6H,10H,10aH-naphtho[2,1-c]pyran-7-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(=O)[C@H](OC(C)=O)C2[C@@]3(C)C[C@H](OC(=O)[C@@H]3CC[C@@]12C)C1=COC=C1

InChI Identifier

InChI=1S/C23H26O8/c1-12(24)30-18-16(25)9-15(20(26)28-4)22(2)7-5-14-21(27)31-17(13-6-8-29-11-13)10-23(14,3)19(18)22/h6,8-9,11,14,17-19H,5,7,10H2,1-4H3/t14-,17-,18-,19?,22-,23-/m0/s1

InChI Key

KLIYEWBCXJFOSK-HOXPKSMJSA-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
Salvia divinorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Clerodane diterpenoid
Diterpenoid
Diterpene lactone
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Cyclohexenone
Alpha-acyloxy ketone
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.65	ChemAxon
pKa (Strongest Acidic)	16.9	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	109.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.75 m³·mol⁻¹	ChemAxon
Polarizability	43.21 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

C00047346

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

101385631

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma Z, Lee DY: Synthesis of deacetyl-1,10-didehydrosalvinorin G. Tetrahedron Lett. 2008 Mar 10;49(11):1782-1785. doi: 10.1016/j.tetlet.2008.01.065. [PubMed:19279674 ]
Lee DY, Ma Z, Liu-Chen LY, Wang Y, Chen Y, Carlezon WA Jr, Cohen B: New neoclerodane diterpenoids isolated from the leaves of Salvia divinorum and their binding affinities for human kappa opioid receptors. Bioorg Med Chem. 2005 Oct 1;13(19):5635-9. doi: 10.1016/j.bmc.2005.05.054. [PubMed:16084728 ]
LOTUS database [Link]

Showing NP-Card for methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate (NP0251497)

MOL for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D MOL for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D SDF for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D-SDF for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

PDB for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D PDB for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

SMILES for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

INCHI for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

Structure for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D Structure for NP0251497 (methyl (2s,4ar,6ar,10r,10br)-10-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-1h,2h,4ah,5h,6h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)