Natural Product: NPC238227

Natural Product ID:  NPC238227
Common Name:   Methylmitrekaurenate
IUPAC Name:   (1R,4S,5R)-4-[(1S,2S,3R)-2-carboxy-3-methoxycarbonyl-1,3-dimethylcyclohexyl]-7-methylidenebicyclo[3.2.1]octane-5-carboxylic acid
Synonyms:   Methylmitrekaurenate
Molecular Formula:   C21H30O6
Standard InCHIKey:  KXRIJKYODUQSSO-XAKDGQKMSA-N
Standard InCHI:  InChI=1S/C21H30O6/c1-12-10-21(17(24)25)11-13(12)6-7-14(21)19(2)8-5-9-20(3,18(26)27-4)15(19)16(22)23/h13-15H,1,5-11H2,2-4H3,(H,22,23)(H,24,25)/t13-,14+,15+,19+,20-,21+/m1/s1
Canonical SMILES:  COC(=O)[C@]1(C)CCC[C@@]([C@@H]1C(=O)O)(C)[C@@H]1CC[C@@H]2C[C@]1(CC2=C)C(=O)O
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
NPO10501 Mitrephora glabra Species Annonaceae Eukaryota Stem barks PMID[19874044]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 75 ug/ml 15189040
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 150 ug/ml 10509925
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC = 150 ug/ml 23234407
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 150 ug/ml 23234407
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000 nM 19679472
NPT91 Cell Line KB Homo sapiens IC50 > 10000 nM 19679472
NPT397 Cell Line NCI-H460 Homo sapiens IC50 > 10000 nM 21958738
NPT395 Cell Line SF-268 Homo sapiens IC50 > 10000 nM 21958738

  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 NPC238227 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
0.8904 High Similarity NPC330659
0.8904 High Similarity NPC161187
0.8904 High Similarity NPC244708
0.88 High Similarity NPC246445
0.8718 High Similarity NPC232625
0.8649 High Similarity NPC279241
0.8611 High Similarity NPC290445
0.8611 High Similarity NPC36616
0.8553 High Similarity NPC476601
0.85 High Similarity NPC471037
0.8462 Intermediate Similarity NPC118987
0.8442 Intermediate Similarity NPC471035
0.8442 Intermediate Similarity NPC212661
0.8442 Intermediate Similarity NPC66105
0.8442 Intermediate Similarity NPC68828
0.8378 Intermediate Similarity NPC91369
0.8375 Intermediate Similarity NPC133391
0.8354 Intermediate Similarity NPC170038
0.8353 Intermediate Similarity NPC160506
0.8333 Intermediate Similarity NPC321690
0.8312 Intermediate Similarity NPC20466
0.8267 Intermediate Similarity NPC72343
0.825 Intermediate Similarity NPC209318
0.825 Intermediate Similarity NPC223330
0.8228 Intermediate Similarity NPC192744
0.8228 Intermediate Similarity NPC158846
0.8214 Intermediate Similarity NPC255176
0.8214 Intermediate Similarity NPC56413
0.8193 Intermediate Similarity NPC472505
0.8171 Intermediate Similarity NPC263974
0.8158 Intermediate Similarity NPC472813
0.8158 Intermediate Similarity NPC36310
0.8148 Intermediate Similarity NPC240302
0.8148 Intermediate Similarity NPC170985
0.814 Intermediate Similarity NPC154101
0.8133 Intermediate Similarity NPC235586
0.8125 Intermediate Similarity NPC104545
0.8101 Intermediate Similarity NPC63020
0.8101 Intermediate Similarity NPC321514
0.8095 Intermediate Similarity NPC167877
0.8095 Intermediate Similarity NPC33768
0.8095 Intermediate Similarity NPC128644
0.8095 Intermediate Similarity NPC134197
0.8072 Intermediate Similarity NPC201655
0.8072 Intermediate Similarity NPC283733
0.8049 Intermediate Similarity NPC245866
0.8049 Intermediate Similarity NPC167103
0.8025 Intermediate Similarity NPC147066
0.8 Intermediate Similarity NPC327674
0.8 Intermediate Similarity NPC4309
0.8 Intermediate Similarity NPC471475
0.8 Intermediate Similarity NPC229407
0.8 Intermediate Similarity NPC474719
0.8 Intermediate Similarity NPC477371
0.8 Intermediate Similarity NPC254572
0.8 Intermediate Similarity NPC250687
0.8 Intermediate Similarity NPC294480
0.8 Intermediate Similarity NPC476438
0.8 Intermediate Similarity NPC263951
0.8 Intermediate Similarity NPC183546
0.8 Intermediate Similarity NPC192999
0.8 Intermediate Similarity NPC48824
0.7976 Intermediate Similarity NPC12774
0.7976 Intermediate Similarity NPC185638
0.7976 Intermediate Similarity NPC2783
0.7976 Intermediate Similarity NPC212843
0.7976 Intermediate Similarity NPC70661
0.7976 Intermediate Similarity NPC475007
0.7976 Intermediate Similarity NPC80590
0.7975 Intermediate Similarity NPC474433
0.7975 Intermediate Similarity NPC106078
0.7952 Intermediate Similarity NPC476038
0.7952 Intermediate Similarity NPC194937
0.7949 Intermediate Similarity NPC192540
0.7949 Intermediate Similarity NPC279666
0.7931 Intermediate Similarity NPC297265
0.7931 Intermediate Similarity NPC250753
0.7927 Intermediate Similarity NPC476292
0.7927 Intermediate Similarity NPC474605
0.7927 Intermediate Similarity NPC296367
0.7907 Intermediate Similarity NPC66344
0.7907 Intermediate Similarity NPC54689
0.7907 Intermediate Similarity NPC269267
0.7907 Intermediate Similarity NPC474570
0.7901 Intermediate Similarity NPC477057
0.7889 Intermediate Similarity NPC10864
0.7882 Intermediate Similarity NPC96496
0.7882 Intermediate Similarity NPC264005
0.7882 Intermediate Similarity NPC269360
0.7882 Intermediate Similarity NPC312215
0.7875 Intermediate Similarity NPC260385
0.7875 Intermediate Similarity NPC476810
0.7875 Intermediate Similarity NPC280654
0.7875 Intermediate Similarity NPC110094
0.7865 Intermediate Similarity NPC98639
0.7857 Intermediate Similarity NPC269638
0.7857 Intermediate Similarity NPC264317
0.7857 Intermediate Similarity NPC294438
0.7857 Intermediate Similarity NPC329738
0.7848 Intermediate Similarity NPC69143
0.7848 Intermediate Similarity NPC89294
0.7848 Intermediate Similarity NPC92489
0.7841 Intermediate Similarity NPC470376
0.7841 Intermediate Similarity NPC170220
0.7841 Intermediate Similarity NPC107674
0.7841 Intermediate Similarity NPC470375
0.7841 Intermediate Similarity NPC294263
0.7841 Intermediate Similarity NPC141497
0.7838 Intermediate Similarity NPC477931
0.7838 Intermediate Similarity NPC103734
0.7838 Intermediate Similarity NPC268736
0.7831 Intermediate Similarity NPC472740
0.7831 Intermediate Similarity NPC477373
0.7831 Intermediate Similarity NPC200752
0.7831 Intermediate Similarity NPC170862
0.7821 Intermediate Similarity NPC46610
0.7821 Intermediate Similarity NPC161923
0.7821 Intermediate Similarity NPC251970
0.7821 Intermediate Similarity NPC283908
0.7821 Intermediate Similarity NPC18819
0.7821 Intermediate Similarity NPC183503
0.7821 Intermediate Similarity NPC3753
0.7821 Intermediate Similarity NPC255168
0.7821 Intermediate Similarity NPC241854
0.7821 Intermediate Similarity NPC103958
0.7821 Intermediate Similarity NPC237591
0.7821 Intermediate Similarity NPC476046
0.7816 Intermediate Similarity NPC471896
0.7805 Intermediate Similarity NPC14203
0.7805 Intermediate Similarity NPC477372
0.7805 Intermediate Similarity NPC38350
0.7805 Intermediate Similarity NPC327002
0.7805 Intermediate Similarity NPC201912
0.7805 Intermediate Similarity NPC40228
0.7805 Intermediate Similarity NPC229584
0.7805 Intermediate Similarity NPC475951
0.7802 Intermediate Similarity NPC89099
0.7792 Intermediate Similarity NPC469940
0.7792 Intermediate Similarity NPC160817
0.7791 Intermediate Similarity NPC16377
0.7791 Intermediate Similarity NPC472870
0.7791 Intermediate Similarity NPC211162
0.7791 Intermediate Similarity NPC183374
0.7778 Intermediate Similarity NPC274996
0.7778 Intermediate Similarity NPC104568
0.7778 Intermediate Similarity NPC200054
0.7778 Intermediate Similarity NPC196827
0.7778 Intermediate Similarity NPC29410
0.7778 Intermediate Similarity NPC201459
0.7778 Intermediate Similarity NPC199595
0.7765 Intermediate Similarity NPC186975
0.7765 Intermediate Similarity NPC471042
0.7765 Intermediate Similarity NPC155011
0.7765 Intermediate Similarity NPC85698
0.7753 Intermediate Similarity NPC303863
0.7753 Intermediate Similarity NPC159410
0.775 Intermediate Similarity NPC61952
0.775 Intermediate Similarity NPC471897
0.775 Intermediate Similarity NPC469867
0.775 Intermediate Similarity NPC471899
0.775 Intermediate Similarity NPC107039
0.7738 Intermediate Similarity NPC472864
0.7738 Intermediate Similarity NPC97505
0.7738 Intermediate Similarity NPC100391
0.7738 Intermediate Similarity NPC165064
0.7738 Intermediate Similarity NPC19849
0.7738 Intermediate Similarity NPC164577
0.7733 Intermediate Similarity NPC469868
0.7727 Intermediate Similarity NPC110657
0.7727 Intermediate Similarity NPC471901
0.7727 Intermediate Similarity NPC212301
0.7727 Intermediate Similarity NPC471747
0.7727 Intermediate Similarity NPC476187
0.7727 Intermediate Similarity NPC86266
0.7727 Intermediate Similarity NPC470113
0.7727 Intermediate Similarity NPC23434
0.7722 Intermediate Similarity NPC476844
0.7722 Intermediate Similarity NPC201027
0.7722 Intermediate Similarity NPC39362
0.7717 Intermediate Similarity NPC293866
0.7711 Intermediate Similarity NPC476458
0.7711 Intermediate Similarity NPC320514
0.7711 Intermediate Similarity NPC15910
0.7711 Intermediate Similarity NPC260956
0.7711 Intermediate Similarity NPC145143
0.7711 Intermediate Similarity NPC258153
0.7701 Intermediate Similarity NPC271974
0.7701 Intermediate Similarity NPC475921
0.7701 Intermediate Similarity NPC215029
0.7701 Intermediate Similarity NPC155479
0.7701 Intermediate Similarity NPC474889
0.7701 Intermediate Similarity NPC474704
0.7701 Intermediate Similarity NPC213832
0.7701 Intermediate Similarity NPC220498
0.7701 Intermediate Similarity NPC247312
0.7701 Intermediate Similarity NPC476733
0.7701 Intermediate Similarity NPC253618
0.7701 Intermediate Similarity NPC77001
0.7701 Intermediate Similarity NPC57954
0.7701 Intermediate Similarity NPC116146

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC238227 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
0.8353 Intermediate Similarity NPD8034 Phase 2
0.8353 Intermediate Similarity NPD8035 Phase 2
0.8256 Intermediate Similarity NPD6399 Phase 3
0.7857 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD4224 Phase 2
0.7528 Intermediate Similarity NPD5281 Approved
0.7528 Intermediate Similarity NPD5284 Approved
0.7419 Intermediate Similarity NPD5696 Approved
0.7412 Intermediate Similarity NPD4788 Approved
0.7386 Intermediate Similarity NPD5737 Approved
0.7386 Intermediate Similarity NPD6672 Approved
0.7342 Intermediate Similarity NPD6081 Approved
0.7326 Intermediate Similarity NPD4786 Approved
0.7317 Intermediate Similarity NPD6116 Phase 1
0.7312 Intermediate Similarity NPD6083 Phase 2
0.7312 Intermediate Similarity NPD6084 Phase 2
0.7312 Intermediate Similarity NPD7902 Approved
0.7294 Intermediate Similarity NPD4223 Phase 3
0.7294 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD4221 Approved
0.7294 Intermediate Similarity NPD3667 Approved
0.7284 Intermediate Similarity NPD3702 Approved
0.7283 Intermediate Similarity NPD5695 Phase 3
0.7237 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6117 Approved
0.716 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD7146 Approved
0.7159 Intermediate Similarity NPD6409 Approved
0.7159 Intermediate Similarity NPD6098 Approved
0.7159 Intermediate Similarity NPD7521 Approved
0.7159 Intermediate Similarity NPD7334 Approved
0.7159 Intermediate Similarity NPD3618 Phase 1
0.7159 Intermediate Similarity NPD6684 Approved
0.7159 Intermediate Similarity NPD5330 Approved
0.7126 Intermediate Similarity NPD3666 Approved
0.7126 Intermediate Similarity NPD3133 Approved
0.7126 Intermediate Similarity NPD3665 Phase 1
0.7126 Intermediate Similarity NPD4197 Approved
0.7111 Intermediate Similarity NPD6673 Approved
0.7111 Intermediate Similarity NPD6080 Approved
0.7111 Intermediate Similarity NPD4753 Phase 2
0.7111 Intermediate Similarity NPD6904 Approved
0.71 Intermediate Similarity NPD6373 Approved
0.71 Intermediate Similarity NPD6372 Approved
0.7097 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD5329 Approved
0.7024 Intermediate Similarity NPD3617 Approved
0.7024 Intermediate Similarity NPD6118 Approved
0.7024 Intermediate Similarity NPD6115 Approved
0.7024 Intermediate Similarity NPD6114 Approved
0.7024 Intermediate Similarity NPD6697 Approved
0.7021 Intermediate Similarity NPD4697 Phase 3
0.7 Intermediate Similarity NPD6903 Approved
0.7 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5208 Approved
0.6989 Remote Similarity NPD7748 Approved
0.6989 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7900 Approved
0.697 Remote Similarity NPD6402 Approved
0.697 Remote Similarity NPD7128 Approved
0.697 Remote Similarity NPD5739 Approved
0.697 Remote Similarity NPD6675 Approved
0.6966 Remote Similarity NPD5205 Approved
0.6966 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4688 Approved
0.6966 Remote Similarity NPD4138 Approved
0.6966 Remote Similarity NPD4693 Phase 3
0.6966 Remote Similarity NPD4690 Approved
0.6966 Remote Similarity NPD4689 Approved
0.6961 Remote Similarity NPD6649 Approved
0.6961 Remote Similarity NPD6650 Approved
0.6957 Remote Similarity NPD7515 Phase 2
0.6957 Remote Similarity NPD5693 Phase 1
0.6932 Remote Similarity NPD3668 Phase 3
0.6923 Remote Similarity NPD5328 Approved
0.6915 Remote Similarity NPD4629 Approved
0.6915 Remote Similarity NPD5210 Approved
0.69 Remote Similarity NPD5697 Approved
0.69 Remote Similarity NPD5701 Approved
0.6882 Remote Similarity NPD4202 Approved
0.686 Remote Similarity NPD4695 Discontinued
0.6848 Remote Similarity NPD5207 Approved
0.6848 Remote Similarity NPD5692 Phase 3
0.6832 Remote Similarity NPD6881 Approved
0.6832 Remote Similarity NPD6899 Approved
0.6832 Remote Similarity NPD6011 Approved
0.6832 Remote Similarity NPD7320 Approved
0.6809 Remote Similarity NPD6001 Approved
0.679 Remote Similarity NPD4789 Approved
0.6782 Remote Similarity NPD4139 Approved
0.6782 Remote Similarity NPD4692 Approved
0.6778 Remote Similarity NPD5690 Phase 2
0.6778 Remote Similarity NPD5280 Approved
0.6778 Remote Similarity NPD5279 Phase 3
0.6778 Remote Similarity NPD4694 Approved
0.6774 Remote Similarity NPD6050 Approved
0.6774 Remote Similarity NPD5694 Approved
0.6774 Remote Similarity NPD6079 Approved
0.6771 Remote Similarity NPD4755 Approved
0.6765 Remote Similarity NPD6013 Approved
0.6765 Remote Similarity NPD6014 Approved
0.6765 Remote Similarity NPD6012 Approved
0.675 Remote Similarity NPD5360 Phase 3
0.675 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6739 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6707 Remote Similarity NPD5777 Approved
0.6707 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6701 Remote Similarity NPD7638 Approved
0.6699 Remote Similarity NPD6883 Approved
0.6699 Remote Similarity NPD7290 Approved
0.6699 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7525 Registered
0.6667 Remote Similarity NPD5221 Approved
0.6667 Remote Similarity NPD5222 Approved
0.6667 Remote Similarity NPD3698 Phase 2
0.6667 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6635 Remote Similarity NPD8130 Phase 1
0.6635 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6635 Remote Similarity NPD6617 Approved
0.6635 Remote Similarity NPD6869 Approved
0.6635 Remote Similarity NPD6847 Approved
0.6634 Remote Similarity NPD6008 Approved
0.6633 Remote Similarity NPD4696 Approved
0.6633 Remote Similarity NPD7639 Approved
0.6633 Remote Similarity NPD5285 Approved
0.6633 Remote Similarity NPD7640 Approved
0.6633 Remote Similarity NPD5286 Approved
0.6633 Remote Similarity NPD4700 Approved
0.6628 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5173 Approved
0.6593 Remote Similarity NPD4623 Approved
0.6593 Remote Similarity NPD4519 Discontinued
0.6585 Remote Similarity NPD4747 Approved
0.6585 Remote Similarity NPD4245 Approved
0.6585 Remote Similarity NPD4244 Approved
0.6575 Remote Similarity NPD615 Clinical (unspecified phase)
0.6571 Remote Similarity NPD8297 Approved
0.6571 Remote Similarity NPD6882 Approved
0.6566 Remote Similarity NPD5223 Approved
0.6552 Remote Similarity NPD4195 Approved
0.6522 Remote Similarity NPD3573 Approved
0.6509 Remote Similarity NPD4632 Approved
0.6509 Remote Similarity NPD8133 Approved
0.6506 Remote Similarity NPD4758 Discontinued
0.6506 Remote Similarity NPD4243 Approved
0.65 Remote Similarity NPD5225 Approved
0.65 Remote Similarity NPD5226 Approved
0.65 Remote Similarity NPD5211 Phase 2
0.65 Remote Similarity NPD5224 Approved
0.65 Remote Similarity NPD4633 Approved
0.6471 Remote Similarity NPD7339 Approved
0.6471 Remote Similarity NPD6942 Approved
0.6465 Remote Similarity NPD6404 Discontinued
0.6463 Remote Similarity NPD4137 Phase 3
0.6444 Remote Similarity NPD5362 Discontinued
0.6436 Remote Similarity NPD4754 Approved
0.6436 Remote Similarity NPD6052 Approved
0.6436 Remote Similarity NPD5174 Approved
0.6436 Remote Similarity NPD5175 Approved
0.6421 Remote Similarity NPD7637 Suspended
0.6421 Remote Similarity NPD6411 Approved
0.6408 Remote Similarity NPD6412 Phase 2
0.6404 Remote Similarity NPD5369 Approved
0.6395 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6392 Remote Similarity NPD5654 Approved
0.6389 Remote Similarity NPD6274 Approved
0.6386 Remote Similarity NPD4691 Approved
0.6383 Remote Similarity NPD6051 Approved
0.6381 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6373 Remote Similarity NPD5141 Approved
0.6364 Remote Similarity NPD4225 Approved
0.6353 Remote Similarity NPD4784 Approved
0.6353 Remote Similarity NPD6924 Approved
0.6353 Remote Similarity NPD6926 Approved
0.6353 Remote Similarity NPD4785 Approved
0.6346 Remote Similarity NPD6686 Approved
0.6341 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5091 Approved
0.6333 Remote Similarity NPD6435 Approved
0.633 Remote Similarity NPD7115 Discovery
0.633 Remote Similarity NPD6317 Approved
0.633 Remote Similarity NPD6009 Approved
0.6327 Remote Similarity NPD7614 Phase 1
0.6316 Remote Similarity NPD4096 Approved
0.6311 Remote Similarity NPD4767 Approved
0.6311 Remote Similarity NPD4768 Approved
0.6304 Remote Similarity NPD1694 Approved
0.6292 Remote Similarity NPD5368 Approved
0.6286 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6279 Remote Similarity NPD3703 Phase 2
0.6279 Remote Similarity NPD5275 Approved
0.6279 Remote Similarity NPD4190 Phase 3
0.6273 Remote Similarity NPD6335 Approved
0.6273 Remote Similarity NPD6314 Approved
0.6273 Remote Similarity NPD6313 Approved
0.6263 Remote Similarity NPD5959 Approved
0.625 Remote Similarity NPD6291 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   44606073
ChEMBL   CHEMBL1079780
ZINC  

Physicochemical Properties

Molecular Weight:  378.20
ALogP:  0.7618
MLogP:  3.11
XLogP:  3.129
# Rotatable Bonds:  10
Polar Surface Area:  100.9
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  27

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Biological Activities  
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