Natural Product: NPC308178

Natural Product ID:  NPC308178
Common Name:   6'-(3,4-Dimethoxycinnamoyl)Ayugol
IUPAC Name:   [(2R,3S,4S,5R,6S)-6-[[(1R,4aS,5S,7R,7aR)-5,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
Synonyms:   6'-(3,4-Dimethoxycinnamoyl)Ayugol
Molecular Formula:   C26H34O12
Standard InCHIKey:  DPTCISVVKXAAHY-NXOJDJGZSA-N
Standard InCHI:  InChI=1S/C26H34O12/c1-26(32)11-15(27)14-8-9-35-24(20(14)26)38-25-23(31)22(30)21(29)18(37-25)12-36-19(28)7-5-13-4-6-16(33-2)17(10-13)34-3/h4-10,14-15,18,20-25,27,29-32H,11-12H2,1-3H3/b7-5+/t14-,15+,18-,20+,21-,22+,23-,24-,25+,26-/m1/s1
Canonical SMILES:  COc1cc(/C=C/C(=O)OC[C@H]2O[C@@H](O[C@H]3OC=C[C@H]4[C@@H]3[C@](C)(O)C[C@@H]4O)[C@@H]([C@H]([C@@H]2O)O)O)ccc1OC
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
NPO33377 teucrium chamaedris Species Lamiaceae Eukaryota PMID[19674906]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1 Others Radical scavenging activity IC50 > 300000 nM 22277277

  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 NPC308178 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
0.9859 High Similarity NPC147224
0.979 High Similarity NPC478249
0.979 High Similarity NPC269914
0.9521 High Similarity NPC229548
0.9521 High Similarity NPC478241
0.9521 High Similarity NPC89693
0.9366 High Similarity NPC302286
0.9366 High Similarity NPC88754
0.9366 High Similarity NPC263397
0.9366 High Similarity NPC237872
0.9366 High Similarity NPC116104
0.9329 High Similarity NPC478248
0.9301 High Similarity NPC478240
0.9272 High Similarity NPC474936
0.9272 High Similarity NPC478265
0.9172 High Similarity NPC37838
0.911 High Similarity NPC18789
0.9079 High Similarity NPC179914
0.9041 High Similarity NPC474234
0.9026 High Similarity NPC206815
0.9026 High Similarity NPC476011
0.8974 High Similarity NPC282551
0.8951 High Similarity NPC49597
0.8947 High Similarity NPC478266
0.8933 High Similarity NPC203664
0.8917 High Similarity NPC208818
0.8904 High Similarity NPC110063
0.8854 High Similarity NPC130730
0.8854 High Similarity NPC301910
0.8828 High Similarity NPC46644
0.8819 High Similarity NPC226005
0.8811 High Similarity NPC157554
0.8811 High Similarity NPC37468
0.8776 High Similarity NPC251062
0.8776 High Similarity NPC184464
0.8767 High Similarity NPC140502
0.875 High Similarity NPC470685
0.8742 High Similarity NPC475379
0.8742 High Similarity NPC21956
0.8716 High Similarity NPC34587
0.8716 High Similarity NPC100998
0.8716 High Similarity NPC252292
0.8716 High Similarity NPC34927
0.8716 High Similarity NPC476382
0.8716 High Similarity NPC216819
0.8716 High Similarity NPC287615
0.8716 High Similarity NPC262182
0.8716 High Similarity NPC83743
0.8707 High Similarity NPC478239
0.8693 High Similarity NPC478232
0.869 High Similarity NPC100389
0.8684 High Similarity NPC478268
0.8679 High Similarity NPC286809
0.8675 High Similarity NPC188393
0.8675 High Similarity NPC470934
0.8649 High Similarity NPC297342
0.8639 High Similarity NPC157816
0.8636 High Similarity NPC475484
0.863 High Similarity NPC202700
0.8627 High Similarity NPC469699
0.8611 High Similarity NPC55040
0.8609 High Similarity NPC478242
0.86 High Similarity NPC232992
0.859 High Similarity NPC469384
0.8581 High Similarity NPC186296
0.8581 High Similarity NPC475213
0.8581 High Similarity NPC152796
0.8571 High Similarity NPC186406
0.8571 High Similarity NPC154262
0.8571 High Similarity NPC159387
0.8571 High Similarity NPC7518
0.8571 High Similarity NPC137501
0.8553 High Similarity NPC117346
0.8553 High Similarity NPC240592
0.8552 High Similarity NPC186418
0.8543 High Similarity NPC215095
0.8543 High Similarity NPC261122
0.8543 High Similarity NPC28651
0.8543 High Similarity NPC300262
0.8543 High Similarity NPC3460
0.8543 High Similarity NPC96294
0.8543 High Similarity NPC210611
0.8543 High Similarity NPC201148
0.8543 High Similarity NPC199311
0.8543 High Similarity NPC80732
0.8543 High Similarity NPC192763
0.8535 High Similarity NPC138993
0.8533 High Similarity NPC476865
0.8533 High Similarity NPC199928
0.8526 High Similarity NPC286919
0.8526 High Similarity NPC475663
0.8523 High Similarity NPC232228
0.85 High Similarity NPC475621
0.8493 Intermediate Similarity NPC304152
0.8491 Intermediate Similarity NPC109990
0.8487 Intermediate Similarity NPC90896
0.8487 Intermediate Similarity NPC470933
0.8487 Intermediate Similarity NPC476386
0.8487 Intermediate Similarity NPC473427
0.8487 Intermediate Similarity NPC106138
0.8487 Intermediate Similarity NPC478234
0.8487 Intermediate Similarity NPC471062
0.8487 Intermediate Similarity NPC478236
0.8487 Intermediate Similarity NPC94871
0.8487 Intermediate Similarity NPC306890
0.8487 Intermediate Similarity NPC476398
0.8487 Intermediate Similarity NPC283839
0.8487 Intermediate Similarity NPC259347
0.8477 Intermediate Similarity NPC52740
0.8472 Intermediate Similarity NPC25821
0.8472 Intermediate Similarity NPC6836
0.8472 Intermediate Similarity NPC254398
0.8467 Intermediate Similarity NPC476868
0.8467 Intermediate Similarity NPC476866
0.8467 Intermediate Similarity NPC476864
0.8467 Intermediate Similarity NPC476869
0.8462 Intermediate Similarity NPC254819
0.8462 Intermediate Similarity NPC11411
0.8451 Intermediate Similarity NPC295970
0.8446 Intermediate Similarity NPC472711
0.8442 Intermediate Similarity NPC470264
0.8435 Intermediate Similarity NPC156376
0.8435 Intermediate Similarity NPC321184
0.8435 Intermediate Similarity NPC321638
0.8435 Intermediate Similarity NPC171134
0.8435 Intermediate Similarity NPC328273
0.8431 Intermediate Similarity NPC257970
0.8431 Intermediate Similarity NPC158635
0.8431 Intermediate Similarity NPC69367
0.8431 Intermediate Similarity NPC229882
0.8431 Intermediate Similarity NPC470927
0.8431 Intermediate Similarity NPC114740
0.8428 Intermediate Similarity NPC145847
0.8421 Intermediate Similarity NPC93924
0.8414 Intermediate Similarity NPC471883
0.8414 Intermediate Similarity NPC187194
0.8414 Intermediate Similarity NPC470881
0.8414 Intermediate Similarity NPC35731
0.8403 Intermediate Similarity NPC252833
0.8403 Intermediate Similarity NPC473924
0.8403 Intermediate Similarity NPC473285
0.84 Intermediate Similarity NPC129417
0.84 Intermediate Similarity NPC84181
0.84 Intermediate Similarity NPC202391
0.84 Intermediate Similarity NPC296659
0.84 Intermediate Similarity NPC292443
0.84 Intermediate Similarity NPC283995
0.84 Intermediate Similarity NPC470235
0.84 Intermediate Similarity NPC476867
0.8392 Intermediate Similarity NPC472024
0.8392 Intermediate Similarity NPC80600
0.8389 Intermediate Similarity NPC296643
0.8389 Intermediate Similarity NPC246947
0.838 Intermediate Similarity NPC302378
0.8378 Intermediate Similarity NPC210478
0.8377 Intermediate Similarity NPC125823
0.8377 Intermediate Similarity NPC85192
0.8377 Intermediate Similarity NPC143480
0.8377 Intermediate Similarity NPC158546
0.8377 Intermediate Similarity NPC7145
0.8377 Intermediate Similarity NPC289021
0.8377 Intermediate Similarity NPC213197
0.8367 Intermediate Similarity NPC476376
0.8366 Intermediate Similarity NPC111785
0.8366 Intermediate Similarity NPC96599
0.8357 Intermediate Similarity NPC145287
0.8356 Intermediate Similarity NPC476870
0.8355 Intermediate Similarity NPC473149
0.8355 Intermediate Similarity NPC41844
0.8354 Intermediate Similarity NPC478269
0.8344 Intermediate Similarity NPC228357
0.8333 Intermediate Similarity NPC470950
0.8333 Intermediate Similarity NPC477898
0.8333 Intermediate Similarity NPC248307
0.8333 Intermediate Similarity NPC46092
0.8333 Intermediate Similarity NPC65942
0.8333 Intermediate Similarity NPC185307
0.8333 Intermediate Similarity NPC219677
0.8333 Intermediate Similarity NPC9912
0.8323 Intermediate Similarity NPC472612
0.8323 Intermediate Similarity NPC476352
0.8323 Intermediate Similarity NPC194705
0.8323 Intermediate Similarity NPC289967
0.8323 Intermediate Similarity NPC472611
0.8323 Intermediate Similarity NPC302610
0.8323 Intermediate Similarity NPC215060
0.8322 Intermediate Similarity NPC134405
0.8322 Intermediate Similarity NPC166040
0.8322 Intermediate Similarity NPC229784
0.8322 Intermediate Similarity NPC270849
0.8322 Intermediate Similarity NPC476385
0.8322 Intermediate Similarity NPC477293
0.8322 Intermediate Similarity NPC248355
0.8322 Intermediate Similarity NPC307110
0.8322 Intermediate Similarity NPC477294
0.8322 Intermediate Similarity NPC471908
0.8322 Intermediate Similarity NPC26653
0.8312 Intermediate Similarity NPC476871
0.8311 Intermediate Similarity NPC197316
0.8311 Intermediate Similarity NPC89105

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC308178 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
0.8696 High Similarity NPD7685 Pre-registration
0.8311 Intermediate Similarity NPD7266 Discontinued
0.8247 Intermediate Similarity NPD1653 Approved
0.7697 Intermediate Similarity NPD7199 Phase 2
0.7682 Intermediate Similarity NPD6653 Approved
0.7639 Intermediate Similarity NPD3705 Approved
0.763 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6674 Discontinued
0.7597 Intermediate Similarity NPD5762 Approved
0.7597 Intermediate Similarity NPD5763 Approved
0.7593 Intermediate Similarity NPD37 Approved
0.759 Intermediate Similarity NPD8127 Discontinued
0.7574 Intermediate Similarity NPD7228 Approved
0.7561 Intermediate Similarity NPD4966 Approved
0.7561 Intermediate Similarity NPD4965 Approved
0.7561 Intermediate Similarity NPD4967 Phase 2
0.7532 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD6234 Discontinued
0.7469 Intermediate Similarity NPD7028 Phase 2
0.7431 Intermediate Similarity NPD1357 Approved
0.7427 Intermediate Similarity NPD7054 Approved
0.7399 Intermediate Similarity NPD7240 Approved
0.7397 Intermediate Similarity NPD1091 Approved
0.7384 Intermediate Similarity NPD7472 Approved
0.7368 Intermediate Similarity NPD3818 Discontinued
0.7351 Intermediate Similarity NPD3027 Phase 3
0.732 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4140 Approved
0.732 Intermediate Similarity NPD3620 Phase 2
0.7296 Intermediate Similarity NPD6190 Approved
0.7284 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7074 Phase 3
0.7257 Intermediate Similarity NPD7808 Phase 3
0.7257 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD8455 Phase 2
0.72 Intermediate Similarity NPD7251 Discontinued
0.72 Intermediate Similarity NPD6362 Approved
0.7181 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7097 Phase 1
0.717 Intermediate Similarity NPD1652 Phase 2
0.7161 Intermediate Similarity NPD5735 Approved
0.7143 Intermediate Similarity NPD6797 Phase 2
0.7125 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD4110 Phase 3
0.7105 Intermediate Similarity NPD2861 Phase 2
0.7101 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1613 Approved
0.7083 Intermediate Similarity NPD3817 Phase 2
0.7071 Intermediate Similarity NPD1358 Approved
0.7055 Intermediate Similarity NPD5536 Phase 2
0.7051 Intermediate Similarity NPD5124 Phase 1
0.7051 Intermediate Similarity NPD6355 Discontinued
0.7051 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6002 Phase 3
0.7044 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6004 Phase 3
0.7044 Intermediate Similarity NPD6005 Phase 3
0.7041 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD5058 Phase 3
0.7019 Intermediate Similarity NPD4628 Phase 3
0.7014 Intermediate Similarity NPD5283 Phase 1
0.7013 Intermediate Similarity NPD7095 Approved
0.7012 Intermediate Similarity NPD6273 Approved
0.7012 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6559 Discontinued
0.7 Intermediate Similarity NPD3134 Approved
0.6961 Remote Similarity NPD6841 Approved
0.6961 Remote Similarity NPD6843 Phase 3
0.6961 Remote Similarity NPD6842 Approved
0.6937 Remote Similarity NPD1375 Discontinued
0.6932 Remote Similarity NPD5844 Phase 1
0.6928 Remote Similarity NPD5647 Approved
0.6927 Remote Similarity NPD8312 Approved
0.6927 Remote Similarity NPD8313 Approved
0.6918 Remote Similarity NPD7157 Approved
0.6899 Remote Similarity NPD6353 Approved
0.6882 Remote Similarity NPD5353 Approved
0.6879 Remote Similarity NPD4060 Phase 1
0.6875 Remote Similarity NPD228 Approved
0.6872 Remote Similarity NPD7549 Discontinued
0.6864 Remote Similarity NPD1934 Approved
0.6863 Remote Similarity NPD3094 Phase 2
0.6848 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2983 Phase 2
0.6842 Remote Similarity NPD2982 Phase 2
0.6842 Remote Similarity NPD5327 Phase 3
0.6839 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6836 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6835 Remote Similarity NPD230 Phase 1
0.6835 Remote Similarity NPD1933 Approved
0.6835 Remote Similarity NPD4340 Discontinued
0.6835 Remote Similarity NPD3657 Discovery
0.6831 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7843 Approved
0.6826 Remote Similarity NPD3686 Approved
0.6826 Remote Similarity NPD3687 Approved
0.6818 Remote Similarity NPD4624 Approved
0.6815 Remote Similarity NPD6233 Phase 2
0.6813 Remote Similarity NPD7033 Discontinued
0.681 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6802 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6792 Remote Similarity NPD2492 Phase 1
0.679 Remote Similarity NPD2424 Discontinued
0.6776 Remote Similarity NPD2981 Phase 2
0.6774 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6774 Remote Similarity NPD5736 Approved
0.6774 Remote Similarity NPD3018 Phase 2
0.6761 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6761 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6761 Remote Similarity NPD6166 Phase 2
0.6759 Remote Similarity NPD969 Suspended
0.6755 Remote Similarity NPD3496 Discontinued
0.6754 Remote Similarity NPD7680 Approved
0.6748 Remote Similarity NPD4237 Approved
0.6748 Remote Similarity NPD4236 Phase 3
0.6748 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6747 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6746 Remote Similarity NPD4380 Phase 2
0.6733 Remote Similarity NPD5691 Approved
0.673 Remote Similarity NPD447 Suspended
0.6725 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6725 Remote Similarity NPD2977 Approved
0.6725 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6725 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6725 Remote Similarity NPD2978 Approved
0.6725 Remote Similarity NPD7819 Suspended
0.6725 Remote Similarity NPD2801 Approved
0.6724 Remote Similarity NPD5494 Approved
0.6723 Remote Similarity NPD7473 Discontinued
0.6711 Remote Similarity NPD422 Phase 1
0.6708 Remote Similarity NPD4108 Discontinued
0.6707 Remote Similarity NPD6331 Phase 2
0.6707 Remote Similarity NPD7982 Clinical (unspecified phase)
0.6707 Remote Similarity NPD8166 Discontinued
0.6706 Remote Similarity NPD6385 Approved
0.6706 Remote Similarity NPD6386 Approved
0.6705 Remote Similarity NPD7075 Discontinued
0.6703 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6689 Remote Similarity NPD4626 Approved
0.6689 Remote Similarity NPD5125 Phase 3
0.6689 Remote Similarity NPD5126 Approved
0.6688 Remote Similarity NPD8651 Approved
0.6687 Remote Similarity NPD4357 Discontinued
0.6686 Remote Similarity NPD5402 Approved
0.6686 Remote Similarity NPD7458 Discontinued
0.6685 Remote Similarity NPD3751 Discontinued
0.6685 Remote Similarity NPD7799 Discontinued
0.6667 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2684 Approved
0.6667 Remote Similarity NPD7296 Approved
0.6667 Remote Similarity NPD9494 Approved
0.6667 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6648 Remote Similarity NPD6232 Discontinued
0.6648 Remote Similarity NPD3787 Discontinued
0.6647 Remote Similarity NPD3882 Suspended
0.6646 Remote Similarity NPD6798 Discontinued
0.6646 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4538 Approved
0.6646 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6646 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4536 Approved
0.6628 Remote Similarity NPD1465 Phase 2
0.6627 Remote Similarity NPD4210 Discontinued
0.6624 Remote Similarity NPD4908 Phase 1
0.6623 Remote Similarity NPD5585 Approved
0.6606 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6605 Remote Similarity NPD5588 Approved
0.6604 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6663 Approved
0.6603 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6601 Remote Similarity NPD3092 Approved
0.6598 Remote Similarity NPD7999 Approved
0.6597 Remote Similarity NPD290 Approved
0.6585 Remote Similarity NPD970 Clinical (unspecified phase)
0.658 Remote Similarity NPD7497 Discontinued
0.6579 Remote Similarity NPD1778 Approved
0.657 Remote Similarity NPD7945 Clinical (unspecified phase)
0.657 Remote Similarity NPD6801 Discontinued
0.6568 Remote Similarity NPD5403 Approved
0.6564 Remote Similarity NPD2438 Suspended
0.6564 Remote Similarity NPD2161 Phase 2
0.6558 Remote Similarity NPD1608 Approved
0.6548 Remote Similarity NPD5401 Approved
0.6543 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6541 Remote Similarity NPD8434 Phase 2
0.6541 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6538 Remote Similarity NPD2797 Approved
0.6538 Remote Similarity NPD7039 Approved
0.6538 Remote Similarity NPD7038 Approved
0.6532 Remote Similarity NPD5760 Phase 2
0.6532 Remote Similarity NPD5772 Approved
0.6532 Remote Similarity NPD5761 Phase 2
0.6532 Remote Similarity NPD5773 Approved
0.6516 Remote Similarity NPD4749 Approved
0.6513 Remote Similarity NPD7503 Approved
0.6509 Remote Similarity NPD52 Approved

Structure

External Identifiers

PubChem CID   46227181
ChEMBL   CHEMBL606147
ZINC  

Physicochemical Properties

Molecular Weight:  538.21
ALogP:  -2.8286
MLogP:  3
XLogP:  0.578
# Rotatable Bonds:  17
Polar Surface Area:  173.6
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  38

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs