NP-MRD: Showing NP-Card for (2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one (NP0143980)

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Record Information

Version

2.0

Created at

2022-09-01 22:51:05 UTC

Updated at

2022-09-01 22:51:05 UTC

NP-MRD ID

NP0143980

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one

Description

Cyclocitrinol belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). (2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one is found in Penicillium citrinum. (2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one was first documented in 2003 (PMID: 14602008). Based on a literature review a significant number of articles have been published on cyclocitrinol (PMID: 18656987) (PMID: 32069021) (PMID: 30827095) (PMID: 30008202) (PMID: 29617567) (PMID: 26461137).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200512D          

 29 32  0  0  1  0            999 V2000
   -5.4604    1.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6510    1.8122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3845    2.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1081    1.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    1.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7557    0.7295    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3769    0.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    1.2724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    0.1083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3962   -0.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6878   -1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667   -0.5761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2476   -0.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639   -2.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826   -1.3468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3562   -0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    0.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069    0.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    0.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9541   -0.5673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7673   -0.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479   -1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -0.0142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0773    0.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8964    0.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911    0.1824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7930    0.9029    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  1  0  0  0
  9  6  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 13  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    6.1315    2.7994    0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3066    1.6944    1.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3283    2.1076    2.0959 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7948    0.8663    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9328   -0.1334    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4158   -0.9652   -0.8590 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5480   -2.4067   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3039   -0.7577   -1.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0882   -0.5500   -1.3520 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6552   -1.4545   -2.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -1.7258   -2.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095   -0.5844   -1.4067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4898   -0.5320   -0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3237   -1.5175   -0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5037   -1.9698   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7712   -3.1943   -0.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163   -1.1796    0.6684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5240   -0.3818    1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9668    0.7071    0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5671    1.8579    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0299    2.1723    0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8608    0.8906    0.5839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1851    0.6219    1.8958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2809   -0.2582   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101    0.7371    0.0259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5364    1.0793    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    0.8560    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9645   -0.4767   -0.4148 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8235   -1.5529    0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2329    2.6643    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0448    2.8512   -0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8309    3.7928    1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095    1.0227    1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5881    1.4926    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1109    1.0455   -0.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6135   -0.3197    1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425   -3.0079   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537   -2.9443   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958   -2.5185    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0344    0.0825   -2.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2149    0.4718   -1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7158   -0.9798   -3.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2299   -2.3901   -2.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3819   -1.7687   -3.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1206   -2.7177   -1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.3471   -2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0535   -2.1601   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0994   -1.8446    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0271   -0.0252    2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6962   -1.0524    1.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    2.6651    0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2318    2.6346   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3164    2.8744    1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8364    1.1467    0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8137    1.3155    2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6624    0.1059   -1.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0660   -0.9157   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779    1.5372   -0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133    2.1859    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6685    0.6037    1.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625    0.9085    1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0085    1.6630   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4459   -2.5214    0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7030   -1.7687    1.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262   -1.2255    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
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 19 18  1  0
 19 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
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 28  9  1  0
 28 12  1  0
 25 13  1  0
 18 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  4 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  9 41  1  6
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 18 49  1  0
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 25 58  1  6
 26 59  1  0
 26 60  1  0
 27 61  1  0
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 29 63  1  0
 29 64  1  0
 29 65  1  0
M  END


  Mrv1652309022200512D          

 29 32  0  0  1  0            999 V2000
   -5.4604    1.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6510    1.8122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3845    2.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1081    1.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    1.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7557    0.7295    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3769    0.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    1.2724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    0.1083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3962   -0.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6878   -1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9069    0.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    0.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9541   -0.5673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7673   -0.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479   -1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -0.0142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0773    0.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8964    0.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911    0.1824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7930    0.9029    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  1  0  0  0
  9  6  1  6  0  0  0
  9 10  1  0  0  0  0
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 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
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 28 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0143980

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)\C=C\[C@](C)(O)[C@H]1CC[C@H]2C3=CC(=O)[C@@H]4C[C@@H](O)CC=C(C4)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O4/c1-15(26)8-11-25(3,29)23-7-6-21-20-14-22(28)17-12-16(4-5-18(27)13-17)19(20)9-10-24(21,23)2/h4,8,11,14-15,17-19,21,23,26-27,29H,5-7,9-10,12-13H2,1-3H3/b11-8+/t15-,17+,18+,19-,21+,23+,24+,25+/m1/s1

> <INCHI_KEY>
QZAMIRPHNVBTIV-HRXCHONESA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.559

> <EXACT_MASS>
400.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.121833579812815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,5S,6S,9R,13S,15S)-6-[(2S,3E,5R)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0^{2,10}.0^{5,9}]octadeca-1(17),10-dien-12-one

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.726751717333333

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.020143076108354

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.280264603070908

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6677584245036225

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
117.32399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,6S,9R,13S,15S)-6-[(2S,3E,5R)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0^{2,10}.0^{5,9}]octadeca-1(17),10-dien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.193   3.085   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.682   3.383   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -8.184   4.840   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.668   2.223   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.157   2.521   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.144   1.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.303   0.348   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.984   2.375   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.130   0.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.473  -1.299   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.151  -2.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.991  -1.075   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.462  -1.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.005  -2.753   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.499  -3.275   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.613  -4.810   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.954  -2.514   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.532  -1.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.124   0.199   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.560   0.959   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.060   0.426   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.514  -1.059   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.032  -1.318   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.569  -2.340   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.461  -0.026   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.144   1.389   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.673   1.573   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.597   0.341   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.347   1.685   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    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   19   13   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    9   12   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₄

Average Mass

400.5590 Da

Monoisotopic Mass

400.26136 Da

IUPAC Name

(2R,5S,6S,9R,13S,15S)-6-[(2S,3E,5R)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0^{2,10}.0^{5,9}]octadeca-1(17),10-dien-12-one

Traditional Name

(2R,5S,6S,9R,13S,15S)-6-[(2S,3E,5R)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0^{2,10}.0^{5,9}]octadeca-1(17),10-dien-12-one

CAS Registry Number

Not Available

SMILES

C[C@@H](O)\C=C\[C@](C)(O)[C@H]1CC[C@H]2C3=CC(=O)[C@@H]4C[C@@H](O)CC=C(C4)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C25H36O4/c1-15(26)8-11-25(3,29)23-7-6-21-20-14-22(28)17-12-16(4-5-18(27)13-17)19(20)9-10-24(21,23)2/h4,8,11,14-15,17-19,21,23,26-27,29H,5-7,9-10,12-13H2,1-3H3/b11-8+/t15-,17+,18+,19-,21+,23+,24+,25+/m1/s1

InChI Key

QZAMIRPHNVBTIV-HRXCHONESA-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
Penicillium citrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	3.11	ALOGPS
logP	2.73	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	117.32 m³·mol⁻¹	ChemAxon
Polarizability	46.12 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

C00038216

Chemspider ID

24720063

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44587547

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Amagata T, Amagata A, Tenney K, Valeriote FA, Lobkovsky E, Clardy J, Crews P: Unusual C25 steroids produced by a sponge-derived Penicillium citrinum. Org Lett. 2003 Nov 13;5(23):4393-6. doi: 10.1021/ol0356800. [PubMed:14602008 ]
Du L, Zhu T, Fang Y, Gu Q, Zhu W: Unusual C25 steroid isomers with bicyclo[4.4.1]A/B rings from a volcano ash-derived fungus Penicillium citrinum. J Nat Prod. 2008 Aug;71(8):1343-51. doi: 10.1021/np8000442. Epub 2008 Jul 26. [PubMed:18656987 ]
Min L, Liu X, Li CC: Total Synthesis of Natural Products with Bridged Bicyclo[m.n.1] Ring Systems via Type II [5 + 2] Cycloaddition. Acc Chem Res. 2020 Mar 17;53(3):703-718. doi: 10.1021/acs.accounts.9b00640. Epub 2020 Feb 18. [PubMed:32069021 ]
Wang Y, Ju W, Tian H, Sun S, Li X, Tian W, Gui J: Facile Access to Bridged Ring Systems via Point-to-Planar Chirality Transfer: Unified Synthesis of Ten Cyclocitrinols. J Am Chem Soc. 2019 Mar 27;141(12):5021-5033. doi: 10.1021/jacs.9b00925. Epub 2019 Mar 12. [PubMed:30827095 ]
Wang Y, Ju W, Tian H, Tian W, Gui J: Scalable Synthesis of Cyclocitrinol. J Am Chem Soc. 2018 Aug 1;140(30):9413-9416. doi: 10.1021/jacs.8b06444. Epub 2018 Jul 19. [PubMed:30008202 ]
Liu J, Wu J, Fan JH, Yan X, Mei G, Li CC: Asymmetric Total Synthesis of Cyclocitrinol. J Am Chem Soc. 2018 Apr 25;140(16):5365-5369. doi: 10.1021/jacs.8b02629. Epub 2018 Apr 6. [PubMed:29617567 ]
Plummer CW, Wei CS, Yozwiak CE, Soheili A, Smithback SO, Leighton JL: Correction to "Design, Development, Mechanistic Elucidation, and Rational Optimization of a Tandem Ireland Claisen/Cope Rearrangement Reaction for Rapid Access to the (Iso)Cyclocitrinol Core". J Am Chem Soc. 2015 Oct 28;137(42):13722. doi: 10.1021/jacs.5b09617. Epub 2015 Oct 13. [PubMed:26461137 ]
Mei G, Liu X, Qiao C, Chen W, Li CC: Type II intramolecular [5+2] cycloaddition: facile synthesis of highly functionalized bridged ring systems. Angew Chem Int Ed Engl. 2015 Feb 2;54(6):1754-8. doi: 10.1002/anie.201410806. Epub 2014 Dec 10. [PubMed:25504815 ]
Plummer CW, Wei CS, Yozwiak CE, Soheili A, Smithback SO, Leighton JL: Design, development, mechanistic elucidation, and rational optimization of a tandem Ireland Claisen/Cope rearrangement reaction for rapid access to the (iso)cyclocitrinol core. J Am Chem Soc. 2014 Jul 16;136(28):9878-81. doi: 10.1021/ja505131v. Epub 2014 Jun 30. [PubMed:24967720 ]
LOTUS database [Link]

Showing NP-Card for (2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one (NP0143980)

MOL for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

3D MOL for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

3D SDF for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

3D-SDF for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

PDB for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

3D PDB for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

SMILES for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

INCHI for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

Structure for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)

3D Structure for NP0143980 ((2r,5s,6s,9r,13s,15s)-6-[(2s,3e,5r)-2,5-dihydroxyhex-3-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]octadeca-1(17),10-dien-12-one)