NP-MRD: Showing NP-Card for (1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde (NP0308354)

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Record Information

Version

2.0

Created at

2022-09-11 02:04:17 UTC

Updated at

2022-09-11 02:04:18 UTC

NP-MRD ID

NP0308354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde

Description

Ophiobolin K belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position. (1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde is found in Aspergillus ustus. (1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde was first documented in 2016 (PMID: 25812930). Based on a literature review a small amount of articles have been published on Ophiobolin K (PMID: 31212583) (PMID: 35163826) (PMID: 31766362) (PMID: 29375031).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112204042D          

 28 30  0  0  1  0            999 V2000
   -0.2861    0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8219    0.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    0.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -0.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823   -1.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069   -2.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -2.3121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2797   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -0.9873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8073   -0.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -0.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -0.9873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5184   -1.7495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3408   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766   -2.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.4515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1774    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    0.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860   -3.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5725   -3.8919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -1.7495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  2  0  0  0  0
 26 27  1  4  0  0  0
 28 27  1  1  0  0  0
  9 28  1  0  0  0  0
 12 28  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    6.2261   -2.0057    1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9298   -0.7072    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9837    0.3480    1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7901   -0.4763    0.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944    0.8113   -0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4924    1.0787   -0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    0.1356   -1.0431 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2303   -0.0817   -2.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    0.7910   -0.4136 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8626    2.1345   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686    2.4157   -0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796    1.0653   -0.5401 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7483    1.1250   -1.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1752    0.9056    0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4968    0.3795    0.2175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6349   -0.8612   -0.5433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9507   -1.3763   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8047   -1.9644   -0.6427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0558   -1.0492    1.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2543    0.2000    1.5432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1661    1.3465    1.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3280    0.0786    2.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6319   -1.8896   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530   -3.1546    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031   -4.1749    0.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359   -2.0195   -0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184   -1.1887   -1.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0727    0.0486   -0.3302 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3251   -2.6292    1.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0211   -2.5192    1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6801   -1.7801    2.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2884    0.6374    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4513    1.2485    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8093    0.0503    1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -1.2782    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3948    1.5939   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3788    2.0834   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5031   -0.8365   -0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047   -1.1493   -2.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1705    0.2200   -3.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351    0.4833   -3.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5410    1.0267    0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6066    2.9008   -0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7072    2.1446   -2.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0055    3.2248   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368    2.6027    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792    1.5833   -1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297    1.8706   -2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984    0.2032   -2.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509    0.2682    1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454    1.8965    1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0807    1.2000   -0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8887   -0.5917   -1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1133   -0.9085    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442   -1.8068    2.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6571    2.2376    2.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9426    1.0292    2.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650    1.6319    0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0725    0.9885    2.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1841   -3.3288    0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9550   -3.0351   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7323   -1.7670   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2235   -1.0457   -2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1658   -0.3638    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
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  6  5  2  0
  5  4  1  0
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  2  1  1  0
  2  3  1  0
  7  9  1  0
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 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  1
 16 23  1  0
 23 24  1  0
 24 25  2  0
 23 26  2  0
 26 27  1  0
 27 28  1  0
 28  9  1  0
 28 12  1  0
 20 15  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
  7 38  1  1
  6 37  1  0
  5 36  1  0
  4 35  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  9 42  1  1
 10 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  6
 16 53  1  6
 19 54  1  0
 19 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 24 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  1
M  END


  Mrv1652309112204042D          

 28 30  0  0  1  0            999 V2000
   -0.2861    0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8219    0.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    0.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -0.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823   -1.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069   -2.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -2.3121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2797   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -0.9873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8073   -0.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -0.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -0.9873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5184   -1.7495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3408   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766   -2.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.4515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1774    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    0.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860   -3.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5725   -3.8919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -1.7495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  2  0  0  0  0
 26 27  1  4  0  0  0
 28 27  1  1  0  0  0
  9 28  1  0  0  0  0
 12 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](\C=C/C=C(C)C)C1CC[C@]2(C)C[C@H]3[C@H](C(=O)C[C@@]3(C)O)C(C=O)=CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h6-9,15,17,19-21,23,28H,10-14H2,1-5H3/b8-6-,18-9?/t17-,19?,20-,21-,23+,24+,25+/m0/s1

> <INCHI_KEY>
TXEVVAPERSDMTN-HEEBETNSSA-N

> <FORMULA>
C25H36O3

> <MOLECULAR_WEIGHT>
384.56

> <EXACT_MASS>
384.266445019

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
44.980638257409794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,4R,7S,11S)-4-hydroxy-1,4-dimethyl-12-[(2S,3Z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0^{3,7}]tetradec-8-ene-8-carbaldehyde

> <JCHEM_LOGP>
4.401742575666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.948073298950991

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.616878198542476

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9894153670755346

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
116.62689999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,7S,11S)-4-hydroxy-1,4-dimethyl-12-[(2S,3Z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0^{3,7}]tetradec-8-ene-8-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.534   1.210   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.534   0.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.048   0.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.020  -1.413   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.020  -2.584   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.506  -4.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.008  -4.316   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.522  -5.768   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.008  -3.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.649  -1.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.962  -0.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.133  -1.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.374  -0.322   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.556  -1.254   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.978  -1.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.568  -3.266   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.103  -3.145   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.103  -4.316   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.462  -1.647   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.149  -0.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.798   0.554   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.290   0.435   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.978  -4.688   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.067  -5.777   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.669  -7.265   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.556  -5.278   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.133  -4.688   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.543  -3.266   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   28                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    9   12                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₃

Average Mass

384.5600 Da

Monoisotopic Mass

384.26645 Da

IUPAC Name

(1R,3S,4R,7S,11S)-4-hydroxy-1,4-dimethyl-12-[(2S,3Z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0^{3,7}]tetradec-8-ene-8-carbaldehyde

Traditional Name

(1R,3S,4R,7S,11S)-4-hydroxy-1,4-dimethyl-12-[(2S,3Z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0^{3,7}]tetradec-8-ene-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@H](\C=C/C=C(C)C)C1CC[C@]2(C)C[C@H]3[C@H](C(=O)C[C@@]3(C)O)C(C=O)=CC[C@@H]12

InChI Identifier

InChI=1S/C25H36O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h6-9,15,17,19-21,23,28H,10-14H2,1-5H3/b8-6-,18-9?/t17-,19?,20-,21-,23+,24+,25+/m0/s1

InChI Key

TXEVVAPERSDMTN-HEEBETNSSA-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
Aspergillus ustus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Ophiobolane sesterterpenoids

Alternative Parents

Substituents

Ophiobolane sesterterpenoid
Tertiary alcohol
Cyclic alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	4.4	ChemAxon
pKa (Strongest Acidic)	10.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.63 m³·mol⁻¹	ChemAxon
Polarizability	44.98 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

139588269

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Choi BK, Trinh PTH, Lee HS, Choi BW, Kang JS, Ngoc NTD, Van TTT, Shin HJ: New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells. Mar Drugs. 2019 Jun 11;17(6). pii: md17060346. doi: 10.3390/md17060346. [PubMed:31212583 ]
Yan J, Pang J, Liang J, Yu W, Liao X, Aobulikasimu A, Yi X, Yin Y, Deng Z, Hong K: The Biosynthesis and Transport of Ophiobolins in Aspergillus ustus 094102. Int J Mol Sci. 2022 Feb 8;23(3):1903. doi: 10.3390/ijms23031903. [PubMed:35163826 ]
Salo MJ, Marik T, Bencsik O, Mikkola R, Kredics L, Szekeres A, Andersson MA, Salonen H, Kurnitski J: Screening Mold Colonies by Using Two Toxicity Assays Revealed Indoor Strains of Aspergillus calidoustus Producing Ophiobolins G and K. Toxins (Basel). 2019 Nov 21;11(12):683. doi: 10.3390/toxins11120683. [PubMed:31766362 ]
Sohsomboon N, Kanzaki H, Nitoda T: Unique antimicrobial spectrum of ophiobolin K produced by Aspergillus ustus. Biosci Biotechnol Biochem. 2018 Mar;82(3):422-424. doi: 10.1080/09168451.2018.1429890. Epub 2018 Jan 29. [PubMed:29375031 ]
de Carvalho CR, Vieira Mde L, Cantrell CL, Wedge DE, Alves TM, Zani CL, Pimenta RS, Sales Junior PA, Murta SM, Romanha AJ, Rosa CA, Rosa LH: Biological activities of ophiobolin K and 6-epi-ophiobolin K produced by the endophytic fungus Aspergillus calidoustus. Nat Prod Res. 2016;30(4):478-81. doi: 10.1080/14786419.2015.1022777. Epub 2015 Mar 27. [PubMed:25812930 ]
LOTUS database [Link]

Showing NP-Card for (1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde (NP0308354)

MOL for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

3D MOL for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

3D SDF for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

3D-SDF for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

PDB for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

3D PDB for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

SMILES for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

INCHI for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

Structure for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)

3D Structure for NP0308354 ((1r,3s,4r,7s,11s)-4-hydroxy-1,4-dimethyl-12-[(2s,3z)-6-methylhepta-3,5-dien-2-yl]-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde)