Natural Product: NPC140277

Natural Product ID:  NPC140277
Common Name:   Ajugapantin A
IUPAC Name:   [(1R,4R,4aR,5S,7R,8S,8aR)-1,5-diacetyloxy-8-[(2S)-2-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
Synonyms:   Ajugapantin A
Molecular Formula:   C28H38O11
Standard InCHIKey:  KBIJVGBQDPMKKO-BAOLRMIKSA-N
Standard InCHI:  InChI=1S/C28H38O11/c1-15-9-23(39-19(5)32)28(14-35-16(2)29)25(21(37-17(3)30)7-8-27(28)13-36-27)26(15,6)11-22(38-18(4)31)20-10-24(33)34-12-20/h10,15,21-23,25H,7-9,11-14H2,1-6H3/t15-,21-,22+,23+,25-,26+,27+,28-/m1/s1
Canonical SMILES:  CC(=O)OC[C@@]12[C@@H](OC(=O)C)C[C@H]([C@]([C@H]1[C@@H](CC[C@@]12CO1)OC(=O)C)(C)C[C@@H](C1=CC(=O)OC1)OC(=O)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
NPO9680 Ajuga ciliata Species Lamiaceae Eukaryota whole plants Zhejiang Province, China 2008-AUG PMID[21682262]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota flowering whole plant PMID[10425119]
NPO9680 Ajuga ciliata Species Lamiaceae Eukaryota Whole Plants PMID[21682262]
NPO7849 Ajuga taiwanensis Species Lamiaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Activity = 100 % 10425119
NPT2 Others Unspecified Activity = 54.7 % 10425119
NPT2 Others Unspecified Activity = 79.2 % 10425119
NPT2 Others Unspecified Activity = 10.6 % 10425119
NPT80 Cell Line Raji Homo sapiens Activity = 70 % 10425119
NPT80 Cell Line Raji Homo sapiens Activity > 80 % 10425119

  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 NPC140277 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
0.9775 High Similarity NPC209297
0.9775 High Similarity NPC475380
0.9775 High Similarity NPC194132
0.9667 High Similarity NPC311241
0.9667 High Similarity NPC475446
0.9667 High Similarity NPC100912
0.956 High Similarity NPC72647
0.956 High Similarity NPC107806
0.9425 High Similarity NPC93411
0.9255 High Similarity NPC475038
0.9255 High Similarity NPC109195
0.9222 High Similarity NPC7349
0.9121 High Similarity NPC161998
0.9121 High Similarity NPC105490
0.8947 High Similarity NPC11974
0.8842 High Similarity NPC16601
0.8817 High Similarity NPC276110
0.8778 High Similarity NPC106332
0.8652 High Similarity NPC474013
0.8646 High Similarity NPC324841
0.8586 High Similarity NPC51719
0.8557 High Similarity NPC472554
0.8542 High Similarity NPC278673
0.8506 High Similarity NPC469802
0.85 High Similarity NPC319438
0.85 High Similarity NPC471205
0.85 High Similarity NPC216636
0.8469 Intermediate Similarity NPC162973
0.8469 Intermediate Similarity NPC472552
0.8454 Intermediate Similarity NPC38855
0.8438 Intermediate Similarity NPC51499
0.8416 Intermediate Similarity NPC181994
0.84 Intermediate Similarity NPC471206
0.8387 Intermediate Similarity NPC78973
0.8384 Intermediate Similarity NPC120009
0.8384 Intermediate Similarity NPC471938
0.8384 Intermediate Similarity NPC160583
0.8352 Intermediate Similarity NPC131813
0.8352 Intermediate Similarity NPC102996
0.8351 Intermediate Similarity NPC275086
0.8351 Intermediate Similarity NPC325229
0.8333 Intermediate Similarity NPC260796
0.8333 Intermediate Similarity NPC306951
0.8333 Intermediate Similarity NPC322912
0.8333 Intermediate Similarity NPC96055
0.8317 Intermediate Similarity NPC122816
0.8315 Intermediate Similarity NPC471218
0.83 Intermediate Similarity NPC471937
0.8283 Intermediate Similarity NPC476081
0.8283 Intermediate Similarity NPC471914
0.828 Intermediate Similarity NPC170633
0.8265 Intermediate Similarity NPC471413
0.8261 Intermediate Similarity NPC166857
0.8261 Intermediate Similarity NPC102640
0.8229 Intermediate Similarity NPC111273
0.8229 Intermediate Similarity NPC472441
0.8229 Intermediate Similarity NPC476519
0.8229 Intermediate Similarity NPC471915
0.8218 Intermediate Similarity NPC220217
0.8218 Intermediate Similarity NPC119855
0.82 Intermediate Similarity NPC97487
0.82 Intermediate Similarity NPC165608
0.82 Intermediate Similarity NPC281378
0.82 Intermediate Similarity NPC189588
0.82 Intermediate Similarity NPC10232
0.82 Intermediate Similarity NPC187302
0.82 Intermediate Similarity NPC45897
0.82 Intermediate Similarity NPC196471
0.8182 Intermediate Similarity NPC247701
0.8182 Intermediate Similarity NPC25177
0.8182 Intermediate Similarity NPC471412
0.8182 Intermediate Similarity NPC295110
0.8182 Intermediate Similarity NPC268829
0.8182 Intermediate Similarity NPC222875
0.8172 Intermediate Similarity NPC69713
0.8152 Intermediate Similarity NPC471219
0.8144 Intermediate Similarity NPC171598
0.8137 Intermediate Similarity NPC475074
0.8132 Intermediate Similarity NPC32223
0.8125 Intermediate Similarity NPC477722
0.8105 Intermediate Similarity NPC329842
0.8105 Intermediate Similarity NPC78594
0.81 Intermediate Similarity NPC11956
0.8077 Intermediate Similarity NPC177047
0.8065 Intermediate Similarity NPC264546
0.8065 Intermediate Similarity NPC475087
0.8058 Intermediate Similarity NPC50124
0.8058 Intermediate Similarity NPC38948
0.8041 Intermediate Similarity NPC472189
0.8041 Intermediate Similarity NPC471372
0.8041 Intermediate Similarity NPC471362
0.8039 Intermediate Similarity NPC218158
0.8039 Intermediate Similarity NPC477090
0.8039 Intermediate Similarity NPC34768
0.8022 Intermediate Similarity NPC476927
0.8021 Intermediate Similarity NPC110022
0.8021 Intermediate Similarity NPC472641
0.8021 Intermediate Similarity NPC53555
0.8021 Intermediate Similarity NPC472640
0.802 Intermediate Similarity NPC120321
0.802 Intermediate Similarity NPC473523
0.802 Intermediate Similarity NPC23584
0.802 Intermediate Similarity NPC474822
0.802 Intermediate Similarity NPC472821
0.8 Intermediate Similarity NPC170303
0.8 Intermediate Similarity NPC302280
0.7981 Intermediate Similarity NPC206618
0.798 Intermediate Similarity NPC472186
0.798 Intermediate Similarity NPC476800
0.798 Intermediate Similarity NPC471366
0.798 Intermediate Similarity NPC318917
0.7961 Intermediate Similarity NPC180744
0.7961 Intermediate Similarity NPC67321
0.7961 Intermediate Similarity NPC302788
0.7961 Intermediate Similarity NPC187435
0.7959 Intermediate Similarity NPC134072
0.7959 Intermediate Similarity NPC94905
0.7959 Intermediate Similarity NPC234993
0.7959 Intermediate Similarity NPC165632
0.7959 Intermediate Similarity NPC8954
0.7959 Intermediate Similarity NPC29952
0.7955 Intermediate Similarity NPC189206
0.7941 Intermediate Similarity NPC473543
0.7935 Intermediate Similarity NPC102048
0.7921 Intermediate Similarity NPC475344
0.7921 Intermediate Similarity NPC476471
0.7921 Intermediate Similarity NPC470972
0.7921 Intermediate Similarity NPC472815
0.7917 Intermediate Similarity NPC473944
0.7912 Intermediate Similarity NPC256112
0.7905 Intermediate Similarity NPC253906
0.79 Intermediate Similarity NPC473545
0.79 Intermediate Similarity NPC251680
0.79 Intermediate Similarity NPC271295
0.79 Intermediate Similarity NPC473204
0.79 Intermediate Similarity NPC472187
0.79 Intermediate Similarity NPC79303
0.7895 Intermediate Similarity NPC246028
0.7895 Intermediate Similarity NPC261320
0.7879 Intermediate Similarity NPC472188
0.7879 Intermediate Similarity NPC474921
0.7879 Intermediate Similarity NPC205143
0.7879 Intermediate Similarity NPC473244
0.7879 Intermediate Similarity NPC199099
0.7872 Intermediate Similarity NPC471796
0.7872 Intermediate Similarity NPC476600
0.787 Intermediate Similarity NPC470793
0.7864 Intermediate Similarity NPC186668
0.7864 Intermediate Similarity NPC81630
0.785 Intermediate Similarity NPC171126
0.7849 Intermediate Similarity NPC472442
0.7843 Intermediate Similarity NPC474124
0.7843 Intermediate Similarity NPC254202
0.7835 Intermediate Similarity NPC205034
0.7835 Intermediate Similarity NPC139692
0.7835 Intermediate Similarity NPC472812
0.7835 Intermediate Similarity NPC162615
0.7835 Intermediate Similarity NPC152778
0.783 Intermediate Similarity NPC470076
0.7826 Intermediate Similarity NPC12283
0.7826 Intermediate Similarity NPC311070
0.7826 Intermediate Similarity NPC474193
0.7822 Intermediate Similarity NPC477717
0.7822 Intermediate Similarity NPC475617
0.7812 Intermediate Similarity NPC220216
0.7812 Intermediate Similarity NPC472642
0.781 Intermediate Similarity NPC475586
0.781 Intermediate Similarity NPC299590
0.781 Intermediate Similarity NPC469370
0.781 Intermediate Similarity NPC475030
0.7802 Intermediate Similarity NPC25554
0.78 Intermediate Similarity NPC218107
0.78 Intermediate Similarity NPC264378
0.7798 Intermediate Similarity NPC290693
0.7789 Intermediate Similarity NPC473879
0.7789 Intermediate Similarity NPC291665
0.7788 Intermediate Similarity NPC475781
0.7788 Intermediate Similarity NPC109376
0.7788 Intermediate Similarity NPC473586
0.7788 Intermediate Similarity NPC179380
0.7778 Intermediate Similarity NPC16967
0.7778 Intermediate Similarity NPC221801
0.7778 Intermediate Similarity NPC211810
0.7778 Intermediate Similarity NPC471765
0.7778 Intermediate Similarity NPC284194
0.7767 Intermediate Similarity NPC477127
0.7766 Intermediate Similarity NPC137253
0.7766 Intermediate Similarity NPC286153
0.7755 Intermediate Similarity NPC57117
0.7755 Intermediate Similarity NPC472416
0.7755 Intermediate Similarity NPC38830
0.7755 Intermediate Similarity NPC472360
0.7745 Intermediate Similarity NPC121423
0.7745 Intermediate Similarity NPC165250
0.7742 Intermediate Similarity NPC318515
0.7736 Intermediate Similarity NPC103491
0.7732 Intermediate Similarity NPC234335
0.7732 Intermediate Similarity NPC124374
0.7732 Intermediate Similarity NPC72845
0.7732 Intermediate Similarity NPC49420

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC140277 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
0.8137 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.798 Intermediate Similarity NPD7638 Approved
0.7905 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.79 Intermediate Similarity NPD7640 Approved
0.79 Intermediate Similarity NPD7639 Approved
0.781 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7328 Approved
0.7727 Intermediate Similarity NPD7327 Approved
0.7723 Intermediate Similarity NPD6648 Approved
0.7658 Intermediate Similarity NPD7516 Approved
0.7647 Intermediate Similarity NPD5344 Discontinued
0.7527 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD8377 Approved
0.7434 Intermediate Similarity NPD8294 Approved
0.7383 Intermediate Similarity NPD6686 Approved
0.7368 Intermediate Similarity NPD8380 Approved
0.7368 Intermediate Similarity NPD8033 Approved
0.7368 Intermediate Similarity NPD8296 Approved
0.7368 Intermediate Similarity NPD8335 Approved
0.7368 Intermediate Similarity NPD8379 Approved
0.7368 Intermediate Similarity NPD8378 Approved
0.7358 Intermediate Similarity NPD6008 Approved
0.7347 Intermediate Similarity NPD6051 Approved
0.7282 Intermediate Similarity NPD4225 Approved
0.7238 Intermediate Similarity NPD7632 Discontinued
0.7119 Intermediate Similarity NPD7507 Approved
0.7069 Intermediate Similarity NPD7503 Approved
0.7059 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7900 Approved
0.7018 Intermediate Similarity NPD7115 Discovery
0.6942 Remote Similarity NPD7319 Approved
0.6939 Remote Similarity NPD1694 Approved
0.6931 Remote Similarity NPD6698 Approved
0.6931 Remote Similarity NPD7838 Discovery
0.6931 Remote Similarity NPD46 Approved
0.6897 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6893 Remote Similarity NPD7748 Approved
0.6881 Remote Similarity NPD6402 Approved
0.6881 Remote Similarity NPD5739 Approved
0.6881 Remote Similarity NPD6675 Approved
0.6881 Remote Similarity NPD7128 Approved
0.6869 Remote Similarity NPD5330 Approved
0.6869 Remote Similarity NPD7521 Approved
0.6869 Remote Similarity NPD6684 Approved
0.6869 Remote Similarity NPD6409 Approved
0.6869 Remote Similarity NPD7146 Approved
0.6869 Remote Similarity NPD7334 Approved
0.6857 Remote Similarity NPD7902 Approved
0.6847 Remote Similarity NPD6373 Approved
0.6847 Remote Similarity NPD6372 Approved
0.6827 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6771 Remote Similarity NPD7525 Registered
0.6757 Remote Similarity NPD7320 Approved
0.6757 Remote Similarity NPD6881 Approved
0.6757 Remote Similarity NPD6899 Approved
0.6733 Remote Similarity NPD5737 Approved
0.6733 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6733 Remote Similarity NPD6672 Approved
0.6733 Remote Similarity NPD6903 Approved
0.6726 Remote Similarity NPD6649 Approved
0.6726 Remote Similarity NPD6650 Approved
0.6699 Remote Similarity NPD5693 Phase 1
0.6699 Remote Similarity NPD7515 Phase 2
0.6667 Remote Similarity NPD5697 Approved
0.6667 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD8297 Approved
0.6667 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6882 Approved
0.6637 Remote Similarity NPD7102 Approved
0.6637 Remote Similarity NPD6883 Approved
0.6637 Remote Similarity NPD7290 Approved
0.6635 Remote Similarity NPD6399 Phase 3
0.6634 Remote Similarity NPD3573 Approved
0.6607 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6579 Remote Similarity NPD8130 Phase 1
0.6579 Remote Similarity NPD6847 Approved
0.6579 Remote Similarity NPD6869 Approved
0.6579 Remote Similarity NPD6617 Approved
0.6566 Remote Similarity NPD6695 Phase 3
0.6555 Remote Similarity NPD6319 Approved
0.6549 Remote Similarity NPD6012 Approved
0.6549 Remote Similarity NPD6013 Approved
0.6549 Remote Similarity NPD6014 Approved
0.6542 Remote Similarity NPD6083 Phase 2
0.6542 Remote Similarity NPD6084 Phase 2
0.6538 Remote Similarity NPD7637 Suspended
0.6522 Remote Similarity NPD6053 Discontinued
0.6505 Remote Similarity NPD6673 Approved
0.6505 Remote Similarity NPD6080 Approved
0.6505 Remote Similarity NPD1695 Approved
0.6505 Remote Similarity NPD6904 Approved
0.6495 Remote Similarity NPD7645 Phase 2
0.6466 Remote Similarity NPD4632 Approved
0.6466 Remote Similarity NPD8133 Approved
0.646 Remote Similarity NPD6011 Approved
0.6442 Remote Similarity NPD3168 Discontinued
0.6435 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6415 Remote Similarity NPD6001 Approved
0.6393 Remote Similarity NPD7604 Phase 2
0.6389 Remote Similarity NPD4755 Approved
0.6381 Remote Similarity NPD8034 Phase 2
0.6381 Remote Similarity NPD8035 Phase 2
0.6373 Remote Similarity NPD3618 Phase 1
0.6372 Remote Similarity NPD6412 Phase 2
0.6355 Remote Similarity NPD5695 Phase 3
0.6348 Remote Similarity NPD6371 Approved
0.6346 Remote Similarity NPD5328 Approved
0.6341 Remote Similarity NPD7492 Approved
0.633 Remote Similarity NPD8029 Clinical (unspecified phase)
0.633 Remote Similarity NPD5696 Approved
0.6321 Remote Similarity NPD4202 Approved
0.6311 Remote Similarity NPD7750 Discontinued
0.6311 Remote Similarity NPD7524 Approved
0.6306 Remote Similarity NPD5211 Phase 2
0.6303 Remote Similarity NPD6009 Approved
0.63 Remote Similarity NPD5209 Approved
0.629 Remote Similarity NPD6616 Approved
0.6281 Remote Similarity NPD6054 Approved
0.6281 Remote Similarity NPD6059 Approved
0.6275 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5285 Approved
0.6273 Remote Similarity NPD5286 Approved
0.6273 Remote Similarity NPD4700 Approved
0.6273 Remote Similarity NPD4696 Approved
0.6263 Remote Similarity NPD6930 Phase 2
0.6263 Remote Similarity NPD6931 Approved
0.6261 Remote Similarity NPD8132 Clinical (unspecified phase)
0.626 Remote Similarity NPD8328 Phase 3
0.625 Remote Similarity NPD5208 Approved
0.624 Remote Similarity NPD7078 Approved
0.624 Remote Similarity NPD8293 Discontinued
0.623 Remote Similarity NPD5983 Phase 2
0.6228 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6226 Remote Similarity NPD6050 Approved
0.6226 Remote Similarity NPD6079 Approved
0.6218 Remote Similarity NPD6274 Approved
0.6214 Remote Similarity NPD6098 Approved
0.6198 Remote Similarity NPD7101 Approved
0.6198 Remote Similarity NPD7100 Approved
0.6195 Remote Similarity NPD5141 Approved
0.619 Remote Similarity NPD7736 Approved
0.6179 Remote Similarity NPD6370 Approved
0.6168 Remote Similarity NPD5779 Approved
0.6168 Remote Similarity NPD5778 Approved
0.6162 Remote Similarity NPD6929 Approved
0.6161 Remote Similarity NPD5226 Approved
0.6161 Remote Similarity NPD4633 Approved
0.6161 Remote Similarity NPD5225 Approved
0.6161 Remote Similarity NPD3653 Clinical (unspecified phase)
0.6161 Remote Similarity NPD5224 Approved
0.616 Remote Similarity NPD6336 Discontinued
0.6154 Remote Similarity NPD4751 Clinical (unspecified phase)
0.614 Remote Similarity NPD4767 Approved
0.614 Remote Similarity NPD4768 Approved
0.6132 Remote Similarity NPD5692 Phase 3
0.6117 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6116 Remote Similarity NPD6335 Approved
0.6106 Remote Similarity NPD5174 Approved
0.6106 Remote Similarity NPD5175 Approved
0.61 Remote Similarity NPD7514 Phase 3
0.61 Remote Similarity NPD7332 Phase 2
0.6098 Remote Similarity NPD6909 Approved
0.6098 Remote Similarity NPD6015 Approved
0.6098 Remote Similarity NPD6016 Approved
0.6098 Remote Similarity NPD6921 Approved
0.6098 Remote Similarity NPD6908 Approved
0.6082 Remote Similarity NPD7339 Approved
0.6082 Remote Similarity NPD6942 Approved
0.6082 Remote Similarity NPD8039 Approved
0.6075 Remote Similarity NPD7087 Discontinued
0.6075 Remote Similarity NPD5694 Approved
0.6071 Remote Similarity NPD5223 Approved
0.6071 Remote Similarity NPD4159 Approved
0.6068 Remote Similarity NPD4634 Approved
0.6048 Remote Similarity NPD5988 Approved
0.6044 Remote Similarity NPD5325 Clinical (unspecified phase)
0.604 Remote Similarity NPD6902 Approved
0.6038 Remote Similarity NPD4753 Phase 2
0.6034 Remote Similarity NPD4729 Approved
0.6034 Remote Similarity NPD4730 Approved
0.6033 Remote Similarity NPD6317 Approved
0.602 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6019 Remote Similarity NPD3133 Approved
0.6019 Remote Similarity NPD3666 Approved
0.6019 Remote Similarity NPD3668 Phase 3
0.6019 Remote Similarity NPD4786 Approved
0.6019 Remote Similarity NPD3665 Phase 1
0.6014 Remote Similarity NPD7625 Phase 1
0.6 Remote Similarity NPD5222 Approved
0.6 Remote Similarity NPD4697 Phase 3
0.6 Remote Similarity NPD4195 Approved
0.6 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6 Remote Similarity NPD5221 Approved
0.5984 Remote Similarity NPD6314 Approved
0.5984 Remote Similarity NPD6313 Approved
0.5981 Remote Similarity NPD5207 Approved
0.598 Remote Similarity NPD3667 Approved
0.5979 Remote Similarity NPD6926 Approved
0.5979 Remote Similarity NPD6924 Approved

Structure

External Identifiers

PubChem CID   12136681
ChEMBL   CHEMBL522544
ZINC  

Physicochemical Properties

Molecular Weight:  550.24
ALogP:  -0.6153
MLogP:  3.33
XLogP:  2.915
# Rotatable Bonds:  18
Polar Surface Area:  144.03
# H-Bond Aceptor:  11
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  39

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs