Natural Product: NPC30502

Natural Product ID:  NPC30502
Common Name:   Volemolide
IUPAC Name:   (3aS,5aR,6R,8aR)-6-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3a-methoxy-5a-methyl-4,5,6,7,8,8a-hexahydrocyclopenta[e][1]benzofuran-2-one
Synonyms:  
Molecular Formula:   C22H34O3
Standard InCHIKey:  FCFUSYHGZLEMJM-IIVOHCRVSA-N
Standard InCHI:  InChI=1S/C22H34O3/c1-14(2)15(3)7-8-16(4)17-9-10-18-19-13-20(23)25-22(19,24-6)12-11-21(17,18)5/h7-8,13-18H,9-12H2,1-6H3/b8-7+/t15-,16+,17+,18-,21+,22-/m0/s1
Canonical SMILES:  CO[C@@]12CC[C@]3([C@H](C2=CC(=O)O1)CC[C@@H]3[C@@H](/C=C/[C@@H](C(C)C)C)C)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO33483 diaporthe sp. Species Diaporthaceae Eukaryota PMID[26186257]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota mycelium PMID[21848266]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 10 ug/ml 26186257
NPT19 Organism Escherichia coli Escherichia coli MIC > 10 ug/ml 26186257
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC > 10 ug/ml 26186257
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 10 ug/ml 26186257
NPT1228 Organism Streptococcus pyogenes Streptococcus pyogenes MIC > 10 ug/ml 26186257

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC30502 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9259 High Similarity NPC473659
0.9259 High Similarity NPC474694
0.9259 High Similarity NPC475860
0.9136 High Similarity NPC474693
0.8235 Intermediate Similarity NPC96055
0.8171 Intermediate Similarity NPC184737
0.814 Intermediate Similarity NPC472442
0.8118 Intermediate Similarity NPC472440
0.809 Intermediate Similarity NPC302280
0.8049 Intermediate Similarity NPC189206
0.8 Intermediate Similarity NPC471218
0.7976 Intermediate Similarity NPC10636
0.7976 Intermediate Similarity NPC268827
0.7931 Intermediate Similarity NPC474013
0.7826 Intermediate Similarity NPC201725
0.7816 Intermediate Similarity NPC475100
0.7802 Intermediate Similarity NPC329842
0.7789 Intermediate Similarity NPC472826
0.7778 Intermediate Similarity NPC177141
0.7778 Intermediate Similarity NPC476489
0.7778 Intermediate Similarity NPC476490
0.7701 Intermediate Similarity NPC12283
0.7701 Intermediate Similarity NPC474193
0.7692 Intermediate Similarity NPC273199
0.7667 Intermediate Similarity NPC471956
0.7667 Intermediate Similarity NPC93411
0.7667 Intermediate Similarity NPC473879
0.7647 Intermediate Similarity NPC170561
0.764 Intermediate Similarity NPC131813
0.7634 Intermediate Similarity NPC470255
0.7619 Intermediate Similarity NPC54996
0.7614 Intermediate Similarity NPC471301
0.7614 Intermediate Similarity NPC471302
0.7609 Intermediate Similarity NPC472811
0.7604 Intermediate Similarity NPC201406
0.7595 Intermediate Similarity NPC472266
0.7582 Intermediate Similarity NPC288699
0.7582 Intermediate Similarity NPC285982
0.7579 Intermediate Similarity NPC231751
0.7579 Intermediate Similarity NPC476768
0.7576 Intermediate Similarity NPC127790
0.7558 Intermediate Similarity NPC472470
0.7558 Intermediate Similarity NPC469802
0.7529 Intermediate Similarity NPC105197
0.7528 Intermediate Similarity NPC471795
0.7528 Intermediate Similarity NPC42586
0.7528 Intermediate Similarity NPC473251
0.7527 Intermediate Similarity NPC472812
0.7527 Intermediate Similarity NPC472303
0.7526 Intermediate Similarity NPC222875
0.7526 Intermediate Similarity NPC295110
0.7526 Intermediate Similarity NPC25177
0.7526 Intermediate Similarity NPC268829
0.7526 Intermediate Similarity NPC247701
0.7525 Intermediate Similarity NPC475030
0.75 Intermediate Similarity NPC78973
0.75 Intermediate Similarity NPC476317
0.75 Intermediate Similarity NPC310479
0.75 Intermediate Similarity NPC182136
0.75 Intermediate Similarity NPC477124
0.75 Intermediate Similarity NPC311070
0.75 Intermediate Similarity NPC321385
0.75 Intermediate Similarity NPC474440
0.7475 Intermediate Similarity NPC472819
0.7473 Intermediate Similarity NPC472378
0.7473 Intermediate Similarity NPC472810
0.7473 Intermediate Similarity NPC472809
0.7471 Intermediate Similarity NPC170303
0.747 Intermediate Similarity NPC475517
0.747 Intermediate Similarity NPC474524
0.7468 Intermediate Similarity NPC116013
0.7447 Intermediate Similarity NPC477722
0.7444 Intermediate Similarity NPC471219
0.7442 Intermediate Similarity NPC44083
0.7442 Intermediate Similarity NPC153987
0.7442 Intermediate Similarity NPC190211
0.7419 Intermediate Similarity NPC177641
0.7419 Intermediate Similarity NPC472953
0.7419 Intermediate Similarity NPC289479
0.7416 Intermediate Similarity NPC318515
0.7412 Intermediate Similarity NPC476439
0.7407 Intermediate Similarity NPC22301
0.7407 Intermediate Similarity NPC265574
0.74 Intermediate Similarity NPC85670
0.74 Intermediate Similarity NPC239961
0.74 Intermediate Similarity NPC472818
0.7396 Intermediate Similarity NPC110937
0.7396 Intermediate Similarity NPC476253
0.7391 Intermediate Similarity NPC470734
0.7386 Intermediate Similarity NPC256112
0.7386 Intermediate Similarity NPC200513
0.7386 Intermediate Similarity NPC471298
0.7374 Intermediate Similarity NPC97487
0.7374 Intermediate Similarity NPC120009
0.7374 Intermediate Similarity NPC112009
0.7374 Intermediate Similarity NPC160583
0.7374 Intermediate Similarity NPC187302
0.7374 Intermediate Similarity NPC189588
0.7374 Intermediate Similarity NPC196471
0.7374 Intermediate Similarity NPC180204
0.7374 Intermediate Similarity NPC10232
0.7368 Intermediate Similarity NPC472441
0.7368 Intermediate Similarity NPC474909
0.7368 Intermediate Similarity NPC471362
0.7368 Intermediate Similarity NPC33473
0.7368 Intermediate Similarity NPC471372
0.7368 Intermediate Similarity NPC472189
0.7368 Intermediate Similarity NPC281134
0.7363 Intermediate Similarity NPC476600
0.7363 Intermediate Similarity NPC471796
0.7363 Intermediate Similarity NPC471657
0.7363 Intermediate Similarity NPC45957
0.7356 Intermediate Similarity NPC233332
0.7349 Intermediate Similarity NPC222244
0.7349 Intermediate Similarity NPC16349
0.7347 Intermediate Similarity NPC198992
0.734 Intermediate Similarity NPC38232
0.734 Intermediate Similarity NPC162615
0.734 Intermediate Similarity NPC205034
0.734 Intermediate Similarity NPC53555
0.734 Intermediate Similarity NPC152778
0.734 Intermediate Similarity NPC7349
0.7333 Intermediate Similarity NPC30984
0.7333 Intermediate Similarity NPC189311
0.7327 Intermediate Similarity NPC472820
0.7326 Intermediate Similarity NPC471220
0.732 Intermediate Similarity NPC252295
0.732 Intermediate Similarity NPC473154
0.7317 Intermediate Similarity NPC64234
0.7317 Intermediate Similarity NPC37929
0.7312 Intermediate Similarity NPC280149
0.7312 Intermediate Similarity NPC221111
0.7303 Intermediate Similarity NPC476927
0.7303 Intermediate Similarity NPC139206
0.7303 Intermediate Similarity NPC472473
0.7303 Intermediate Similarity NPC471297
0.7303 Intermediate Similarity NPC193198
0.7303 Intermediate Similarity NPC474809
0.73 Intermediate Similarity NPC189616
0.7292 Intermediate Similarity NPC171598
0.7292 Intermediate Similarity NPC307164
0.7292 Intermediate Similarity NPC470801
0.7292 Intermediate Similarity NPC16967
0.7283 Intermediate Similarity NPC226863
0.7283 Intermediate Similarity NPC106332
0.7273 Intermediate Similarity NPC471993
0.7273 Intermediate Similarity NPC25554
0.7273 Intermediate Similarity NPC472471
0.7273 Intermediate Similarity NPC476769
0.7263 Intermediate Similarity NPC105490
0.7263 Intermediate Similarity NPC120351
0.7263 Intermediate Similarity NPC161998
0.7263 Intermediate Similarity NPC471994
0.7263 Intermediate Similarity NPC298973
0.7263 Intermediate Similarity NPC104925
0.7263 Intermediate Similarity NPC128488
0.7263 Intermediate Similarity NPC166143
0.7263 Intermediate Similarity NPC140277
0.7263 Intermediate Similarity NPC469697
0.7263 Intermediate Similarity NPC304968
0.7255 Intermediate Similarity NPC61411
0.7253 Intermediate Similarity NPC286153
0.7253 Intermediate Similarity NPC118266
0.725 Intermediate Similarity NPC185587
0.7245 Intermediate Similarity NPC473219
0.7245 Intermediate Similarity NPC324841
0.7245 Intermediate Similarity NPC470761
0.7245 Intermediate Similarity NPC470906
0.7241 Intermediate Similarity NPC469690
0.7241 Intermediate Similarity NPC242767
0.7234 Intermediate Similarity NPC2882
0.7234 Intermediate Similarity NPC477122
0.7234 Intermediate Similarity NPC141831
0.7234 Intermediate Similarity NPC234335
0.7229 Intermediate Similarity NPC257618
0.7228 Intermediate Similarity NPC186668
0.7228 Intermediate Similarity NPC220217
0.7228 Intermediate Similarity NPC119855
0.7222 Intermediate Similarity NPC238197
0.7222 Intermediate Similarity NPC71626
0.7222 Intermediate Similarity NPC306951
0.7222 Intermediate Similarity NPC149869
0.7222 Intermediate Similarity NPC30486
0.7216 Intermediate Similarity NPC472188
0.7216 Intermediate Similarity NPC2049
0.7215 Intermediate Similarity NPC329698
0.7209 Intermediate Similarity NPC473756
0.7204 Intermediate Similarity NPC251528
0.7204 Intermediate Similarity NPC474396
0.7204 Intermediate Similarity NPC262858
0.7204 Intermediate Similarity NPC293044
0.7204 Intermediate Similarity NPC472240
0.7204 Intermediate Similarity NPC50488
0.72 Intermediate Similarity NPC471365
0.72 Intermediate Similarity NPC297617
0.72 Intermediate Similarity NPC45897
0.72 Intermediate Similarity NPC472821
0.72 Intermediate Similarity NPC476770
0.72 Intermediate Similarity NPC471364
0.72 Intermediate Similarity NPC281378

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC30502 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7386 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD6051 Approved
0.7143 Intermediate Similarity NPD7638 Approved
0.7071 Intermediate Similarity NPD7639 Approved
0.7071 Intermediate Similarity NPD7640 Approved
0.6972 Remote Similarity NPD7328 Approved
0.6972 Remote Similarity NPD7327 Approved
0.6957 Remote Similarity NPD1694 Approved
0.6915 Remote Similarity NPD5737 Approved
0.6915 Remote Similarity NPD6903 Approved
0.6915 Remote Similarity NPD6672 Approved
0.6909 Remote Similarity NPD7516 Approved
0.6882 Remote Similarity NPD7521 Approved
0.6882 Remote Similarity NPD7146 Approved
0.6882 Remote Similarity NPD6684 Approved
0.6882 Remote Similarity NPD7334 Approved
0.6882 Remote Similarity NPD5330 Approved
0.6882 Remote Similarity NPD6409 Approved
0.6875 Remote Similarity NPD5693 Phase 1
0.6848 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6847 Remote Similarity NPD8294 Approved
0.6847 Remote Similarity NPD8377 Approved
0.6837 Remote Similarity NPD6356 Clinical (unspecified phase)
0.679 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8380 Approved
0.6786 Remote Similarity NPD8033 Approved
0.6786 Remote Similarity NPD8379 Approved
0.6786 Remote Similarity NPD8296 Approved
0.6786 Remote Similarity NPD8335 Approved
0.6786 Remote Similarity NPD8378 Approved
0.6782 Remote Similarity NPD8039 Approved
0.6771 Remote Similarity NPD5207 Approved
0.6737 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6707 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6080 Approved
0.6667 Remote Similarity NPD6904 Approved
0.6667 Remote Similarity NPD6673 Approved
0.6634 Remote Similarity NPD4225 Approved
0.6604 Remote Similarity NPD6686 Approved
0.6596 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6566 Remote Similarity NPD6001 Approved
0.6562 Remote Similarity NPD5208 Approved
0.6552 Remote Similarity NPD7507 Approved
0.6531 Remote Similarity NPD5694 Approved
0.6531 Remote Similarity NPD7637 Suspended
0.6531 Remote Similarity NPD6050 Approved
0.6526 Remote Similarity NPD6098 Approved
0.6514 Remote Similarity NPD6882 Approved
0.6491 Remote Similarity NPD7503 Approved
0.6484 Remote Similarity NPD4195 Approved
0.6465 Remote Similarity NPD6399 Phase 3
0.6458 Remote Similarity NPD3573 Approved
0.6452 Remote Similarity NPD5209 Approved
0.6442 Remote Similarity NPD7632 Discontinued
0.6429 Remote Similarity NPD7115 Discovery
0.6429 Remote Similarity NPD5785 Approved
0.6429 Remote Similarity NPD5692 Phase 3
0.6408 Remote Similarity NPD6648 Approved
0.6387 Remote Similarity NPD7319 Approved
0.6383 Remote Similarity NPD5362 Discontinued
0.6374 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6083 Phase 2
0.6373 Remote Similarity NPD6084 Phase 2
0.6364 Remote Similarity NPD6079 Approved
0.6346 Remote Similarity NPD5344 Discontinued
0.6337 Remote Similarity NPD5695 Phase 3
0.6327 Remote Similarity NPD5328 Approved
0.6296 Remote Similarity NPD7320 Approved
0.6296 Remote Similarity NPD6899 Approved
0.6296 Remote Similarity NPD6881 Approved
0.6292 Remote Similarity NPD6924 Approved
0.6292 Remote Similarity NPD6926 Approved
0.6262 Remote Similarity NPD6008 Approved
0.6262 Remote Similarity NPD5739 Approved
0.6262 Remote Similarity NPD6675 Approved
0.6262 Remote Similarity NPD7128 Approved
0.6262 Remote Similarity NPD6402 Approved
0.625 Remote Similarity NPD7151 Approved
0.625 Remote Similarity NPD7150 Approved
0.625 Remote Similarity NPD7152 Approved
0.6238 Remote Similarity NPD7900 Approved
0.6238 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6238 Remote Similarity NPD7748 Approved
0.6237 Remote Similarity NPD7525 Registered
0.6222 Remote Similarity NPD7339 Approved
0.6222 Remote Similarity NPD6942 Approved
0.6211 Remote Similarity NPD6695 Phase 3
0.6211 Remote Similarity NPD5332 Approved
0.6211 Remote Similarity NPD5331 Approved
0.6204 Remote Similarity NPD5697 Approved
0.62 Remote Similarity NPD5281 Approved
0.62 Remote Similarity NPD5284 Approved
0.6186 Remote Similarity NPD3618 Phase 1
0.6182 Remote Similarity NPD7290 Approved
0.6182 Remote Similarity NPD7102 Approved
0.6182 Remote Similarity NPD6883 Approved
0.617 Remote Similarity NPD4790 Discontinued
0.6154 Remote Similarity NPD6933 Approved
0.6154 Remote Similarity NPD5696 Approved
0.6147 Remote Similarity NPD6011 Approved
0.6146 Remote Similarity NPD4786 Approved
0.6146 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6145 Remote Similarity NPD4193 Approved
0.6145 Remote Similarity NPD4191 Approved
0.6145 Remote Similarity NPD4194 Approved
0.6145 Remote Similarity NPD4192 Approved
0.6136 Remote Similarity NPD7143 Approved
0.6136 Remote Similarity NPD7144 Approved
0.6129 Remote Similarity NPD6929 Approved
0.6126 Remote Similarity NPD6847 Approved
0.6126 Remote Similarity NPD6649 Approved
0.6126 Remote Similarity NPD6869 Approved
0.6126 Remote Similarity NPD8130 Phase 1
0.6126 Remote Similarity NPD6617 Approved
0.6126 Remote Similarity NPD6650 Approved
0.6111 Remote Similarity NPD4785 Approved
0.6111 Remote Similarity NPD4784 Approved
0.6105 Remote Similarity NPD4221 Approved
0.6105 Remote Similarity NPD4223 Phase 3
0.6091 Remote Similarity NPD6373 Approved
0.6091 Remote Similarity NPD6372 Approved
0.6091 Remote Similarity NPD6014 Approved
0.6091 Remote Similarity NPD6012 Approved
0.6091 Remote Similarity NPD6013 Approved
0.6082 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6082 Remote Similarity NPD5329 Approved
0.6075 Remote Similarity NPD6052 Approved
0.6071 Remote Similarity NPD8297 Approved
0.6067 Remote Similarity NPD4243 Approved
0.6064 Remote Similarity NPD6931 Approved
0.6064 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6064 Remote Similarity NPD6930 Phase 2
0.6064 Remote Similarity NPD7514 Phase 3
0.6058 Remote Similarity NPD7902 Approved
0.6055 Remote Similarity NPD5701 Approved
0.605 Remote Similarity NPD7492 Approved
0.604 Remote Similarity NPD8035 Phase 2
0.604 Remote Similarity NPD8034 Phase 2
0.604 Remote Similarity NPD7515 Phase 2
0.6024 Remote Similarity NPD1145 Discontinued
0.6023 Remote Similarity NPD6922 Approved
0.6023 Remote Similarity NPD6923 Approved
0.6022 Remote Similarity NPD7145 Approved
0.6022 Remote Similarity NPD7322 Clinical (unspecified phase)
0.602 Remote Similarity NPD5690 Phase 2
0.602 Remote Similarity NPD5279 Phase 3
0.6019 Remote Similarity NPD5654 Approved
0.6019 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6 Remote Similarity NPD1695 Approved
0.6 Remote Similarity NPD6009 Approved
0.6 Remote Similarity NPD6616 Approved
0.6 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6 Remote Similarity NPD6902 Approved
0.5983 Remote Similarity NPD6054 Approved
0.5982 Remote Similarity NPD6401 Clinical (unspecified phase)
0.598 Remote Similarity NPD4202 Approved
0.5979 Remote Similarity NPD3133 Approved
0.5979 Remote Similarity NPD4197 Approved
0.5979 Remote Similarity NPD3666 Approved
0.5979 Remote Similarity NPD3665 Phase 1
0.5978 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5962 Remote Similarity NPD5221 Approved
0.5962 Remote Similarity NPD5222 Approved
0.5962 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5962 Remote Similarity NPD4792 Clinical (unspecified phase)
0.596 Remote Similarity NPD7524 Approved
0.596 Remote Similarity NPD7750 Discontinued
0.5955 Remote Similarity NPD4747 Approved
0.595 Remote Similarity NPD7078 Approved
0.5943 Remote Similarity NPD6404 Discontinued
0.5941 Remote Similarity NPD7838 Discovery
0.5938 Remote Similarity NPD3667 Approved
0.5934 Remote Similarity NPD4687 Approved
0.5934 Remote Similarity NPD5733 Approved
0.5929 Remote Similarity NPD6053 Discontinued
0.5922 Remote Similarity NPD5707 Approved
0.5918 Remote Similarity NPD5363 Approved
0.5914 Remote Similarity NPD6925 Approved
0.5914 Remote Similarity NPD6932 Approved
0.5914 Remote Similarity NPD5776 Phase 2
0.5913 Remote Similarity NPD6868 Approved
0.5909 Remote Similarity NPD6614 Approved
0.5909 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5909 Remote Similarity NPD6412 Phase 2
0.5905 Remote Similarity NPD5173 Approved
0.5905 Remote Similarity NPD5959 Approved
0.5902 Remote Similarity NPD7736 Approved
0.5895 Remote Similarity NPD4822 Approved
0.5895 Remote Similarity NPD7332 Phase 2
0.5895 Remote Similarity NPD4821 Approved
0.5895 Remote Similarity NPD4820 Approved
0.5895 Remote Similarity NPD7509 Discontinued
0.5895 Remote Similarity NPD4819 Approved
0.5889 Remote Similarity NPD5276 Approved
0.5882 Remote Similarity NPD6370 Approved
0.5882 Remote Similarity NPD6411 Approved
0.5876 Remote Similarity NPD7154 Phase 3
0.587 Remote Similarity NPD8264 Approved
0.5859 Remote Similarity NPD4694 Approved
0.5859 Remote Similarity NPD4693 Phase 3

Structure

External Identifiers

PubChem CID   14584691
ChEMBL   CHEMBL3593355
ZINC  

Physicochemical Properties

Molecular Weight:  346.25
ALogP:  1.7427
MLogP:  3.55
XLogP:  7.001
# Rotatable Bonds:  11
Polar Surface Area:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  25

Download Data

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Biological Activities  
Similar NPs/Drugs