Natural Product: NPC299090

Natural Product ID:  NPC299090
Common Name:   Cimicifugic Acid N
IUPAC Name:   (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-3-[(Z)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-2-hydroxybutanedioic acid
Synonyms:   Cimicifugic Acid N
Molecular Formula:   C22H22O11
Standard InCHIKey:  YMPYAGUNPNITIL-SAEXZTQASA-N
Standard InCHI:  InChI=1S/C22H22O11/c1-31-16-7-4-12(10-17(16)32-2)5-8-18(25)33-19(20(26)27)22(30,21(28)29)11-13-3-6-14(23)15(24)9-13/h3-10,19,23-24,30H,11H2,1-2H3,(H,26,27)(H,28,29)/b8-5-/t19-,22-/m1/s1
Canonical SMILES:  COc1cc(/C=CC(=O)O[C@@H]([C@@](C(=O)O)(Cc2ccc(c(c2)O)O)O)C(=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
NPO30451 Cimicifuga simplex NA NA NA Aerial parts PMID[20184336]
NPO33345 cimicifuga japonica Species Ranunculaceae Eukaryota Aerial parts PMID[20184336]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT42 Individual Protein Hyaluronidase-1 Homo sapiens IC50 = 120000 nM 18183025

  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 NPC299090 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
1.0 High Similarity NPC283081
1.0 High Similarity NPC143892
1.0 High Similarity NPC221383
0.9856 High Similarity NPC258671
0.9856 High Similarity NPC53884
0.9784 High Similarity NPC304956
0.9653 High Similarity NPC246566
0.9653 High Similarity NPC95498
0.9496 High Similarity NPC156709
0.9496 High Similarity NPC179505
0.9388 High Similarity NPC477299
0.9357 High Similarity NPC288452
0.9357 High Similarity NPC289690
0.9353 High Similarity NPC279676
0.9353 High Similarity NPC67349
0.9205 High Similarity NPC44507
0.92 High Similarity NPC40920
0.92 High Similarity NPC223335
0.9184 High Similarity NPC300329
0.9172 High Similarity NPC229264
0.9139 High Similarity NPC469654
0.9116 High Similarity NPC221091
0.9116 High Similarity NPC259576
0.9116 High Similarity NPC32197
0.911 High Similarity NPC1580
0.9103 High Similarity NPC98356
0.9 High Similarity NPC106406
0.898 High Similarity NPC192568
0.898 High Similarity NPC471076
0.8966 High Similarity NPC160378
0.8958 High Similarity NPC31751
0.8958 High Similarity NPC253722
0.8958 High Similarity NPC253481
0.8933 High Similarity NPC44730
0.8929 High Similarity NPC168799
0.8929 High Similarity NPC155209
0.8921 High Similarity NPC108553
0.8904 High Similarity NPC223185
0.8889 High Similarity NPC100675
0.8882 High Similarity NPC470896
0.8882 High Similarity NPC473275
0.8881 High Similarity NPC284409
0.8873 High Similarity NPC90431
0.8867 High Similarity NPC163883
0.8867 High Similarity NPC93498
0.8865 High Similarity NPC135127
0.8857 High Similarity NPC5419
0.8857 High Similarity NPC61
0.8857 High Similarity NPC25581
0.8857 High Similarity NPC18074
0.8851 High Similarity NPC472969
0.8851 High Similarity NPC98009
0.8849 High Similarity NPC32626
0.8849 High Similarity NPC217052
0.8849 High Similarity NPC237506
0.8849 High Similarity NPC329344
0.8836 High Similarity NPC183824
0.8819 High Similarity NPC147379
0.8819 High Similarity NPC322021
0.8819 High Similarity NPC474784
0.8808 High Similarity NPC146277
0.8808 High Similarity NPC19380
0.8808 High Similarity NPC327225
0.8803 High Similarity NPC113295
0.8803 High Similarity NPC470990
0.8794 High Similarity NPC475468
0.8786 High Similarity NPC198388
0.8784 High Similarity NPC322660
0.8782 High Similarity NPC173729
0.8782 High Similarity NPC134047
0.8782 High Similarity NPC223006
0.8782 High Similarity NPC272750
0.8767 High Similarity NPC285550
0.8742 High Similarity NPC476434
0.8718 High Similarity NPC144557
0.8707 High Similarity NPC474692
0.8693 High Similarity NPC145425
0.8693 High Similarity NPC38699
0.869 High Similarity NPC303683
0.869 High Similarity NPC295492
0.869 High Similarity NPC476820
0.869 High Similarity NPC205751
0.869 High Similarity NPC476819
0.869 High Similarity NPC274891
0.869 High Similarity NPC474875
0.869 High Similarity NPC26241
0.8675 High Similarity NPC243891
0.8667 High Similarity NPC478242
0.8667 High Similarity NPC125570
0.8667 High Similarity NPC98809
0.8667 High Similarity NPC476394
0.8639 High Similarity NPC258469
0.8639 High Similarity NPC319628
0.8639 High Similarity NPC43158
0.8639 High Similarity NPC472016
0.8639 High Similarity NPC277315
0.8639 High Similarity NPC284948
0.8639 High Similarity NPC37331
0.8639 High Similarity NPC220664
0.8639 High Similarity NPC303090
0.8639 High Similarity NPC192831
0.8621 High Similarity NPC302857
0.8621 High Similarity NPC152942
0.8621 High Similarity NPC219428
0.8621 High Similarity NPC37250
0.8621 High Similarity NPC142703
0.8621 High Similarity NPC278068
0.8618 High Similarity NPC75695
0.8618 High Similarity NPC267091
0.8611 High Similarity NPC471988
0.8601 High Similarity NPC5310
0.8601 High Similarity NPC4982
0.8601 High Similarity NPC68779
0.8601 High Similarity NPC176814
0.8601 High Similarity NPC471110
0.8601 High Similarity NPC300776
0.8582 High Similarity NPC275724
0.8582 High Similarity NPC215941
0.8582 High Similarity NPC137427
0.8582 High Similarity NPC244246
0.8582 High Similarity NPC172673
0.8582 High Similarity NPC123196
0.8582 High Similarity NPC319282
0.8582 High Similarity NPC311419
0.8582 High Similarity NPC65935
0.8581 High Similarity NPC473090
0.8581 High Similarity NPC469615
0.8571 High Similarity NPC297517
0.8571 High Similarity NPC471027
0.8571 High Similarity NPC13818
0.8571 High Similarity NPC206095
0.8571 High Similarity NPC224389
0.8571 High Similarity NPC110313
0.8571 High Similarity NPC131532
0.8571 High Similarity NPC35702
0.8571 High Similarity NPC477335
0.8571 High Similarity NPC476642
0.8571 High Similarity NPC67467
0.8562 High Similarity NPC473236
0.8561 High Similarity NPC120225
0.8561 High Similarity NPC213552
0.8553 High Similarity NPC178048
0.8552 High Similarity NPC281780
0.8552 High Similarity NPC126206
0.8535 High Similarity NPC112418
0.8531 High Similarity NPC327410
0.8526 High Similarity NPC76211
0.8523 High Similarity NPC469683
0.8521 High Similarity NPC469480
0.8521 High Similarity NPC318799
0.8516 High Similarity NPC163635
0.8514 High Similarity NPC477696
0.8514 High Similarity NPC273657
0.8514 High Similarity NPC470811
0.8514 High Similarity NPC106920
0.8514 High Similarity NPC477697
0.8511 High Similarity NPC241354
0.8511 High Similarity NPC83062
0.8511 High Similarity NPC304622
0.8503 High Similarity NPC9218
0.8503 High Similarity NPC477279
0.8503 High Similarity NPC326065
0.8503 High Similarity NPC470991
0.85 High Similarity NPC276466
0.85 High Similarity NPC151167
0.85 High Similarity NPC5018
0.85 High Similarity NPC123722
0.85 High Similarity NPC123228
0.8489 Intermediate Similarity NPC280767
0.8489 Intermediate Similarity NPC289459
0.8489 Intermediate Similarity NPC132921
0.8487 Intermediate Similarity NPC473091
0.8483 Intermediate Similarity NPC471664
0.8483 Intermediate Similarity NPC471665
0.8481 Intermediate Similarity NPC471745
0.8472 Intermediate Similarity NPC67247
0.8471 Intermediate Similarity NPC130955
0.8471 Intermediate Similarity NPC471744
0.8471 Intermediate Similarity NPC472962
0.8471 Intermediate Similarity NPC472961
0.8467 Intermediate Similarity NPC9370
0.8467 Intermediate Similarity NPC287495
0.8462 Intermediate Similarity NPC239302
0.8462 Intermediate Similarity NPC226759
0.8456 Intermediate Similarity NPC46161
0.8456 Intermediate Similarity NPC239608
0.8451 Intermediate Similarity NPC142985
0.8451 Intermediate Similarity NPC195292
0.8447 Intermediate Similarity NPC186100
0.8447 Intermediate Similarity NPC216403
0.8447 Intermediate Similarity NPC41494
0.8446 Intermediate Similarity NPC140502
0.8446 Intermediate Similarity NPC477277
0.8446 Intermediate Similarity NPC477278
0.8446 Intermediate Similarity NPC52664
0.8442 Intermediate Similarity NPC295646
0.8442 Intermediate Similarity NPC199773
0.8431 Intermediate Similarity NPC32079
0.8429 Intermediate Similarity NPC168653
0.8429 Intermediate Similarity NPC251407

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC299090 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
0.8639 High Similarity NPD6190 Approved
0.828 Intermediate Similarity NPD3882 Suspended
0.8217 Intermediate Similarity NPD3817 Phase 2
0.8165 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD1934 Approved
0.8085 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD6166 Phase 2
0.8024 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD6233 Phase 2
0.8 Intermediate Similarity NPD7075 Discontinued
0.8 Intermediate Similarity NPD3027 Phase 3
0.7988 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD6234 Discontinued
0.7945 Intermediate Similarity NPD6798 Discontinued
0.7939 Intermediate Similarity NPD3818 Discontinued
0.7933 Intermediate Similarity NPD2935 Discontinued
0.7925 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD2801 Approved
0.7922 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD6232 Discontinued
0.7905 Intermediate Similarity NPD6355 Discontinued
0.7881 Intermediate Similarity NPD7266 Discontinued
0.7875 Intermediate Similarity NPD5402 Approved
0.7843 Intermediate Similarity NPD4628 Phase 3
0.7812 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD6799 Approved
0.7798 Intermediate Similarity NPD6797 Phase 2
0.7798 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD447 Suspended
0.7785 Intermediate Similarity NPD230 Phase 1
0.7771 Intermediate Similarity NPD7473 Discontinued
0.777 Intermediate Similarity NPD4062 Phase 3
0.7755 Intermediate Similarity NPD7095 Approved
0.7751 Intermediate Similarity NPD7685 Pre-registration
0.7751 Intermediate Similarity NPD7251 Discontinued
0.775 Intermediate Similarity NPD6801 Discontinued
0.775 Intermediate Similarity NPD37 Approved
0.774 Intermediate Similarity NPD9494 Approved
0.7738 Intermediate Similarity NPD7074 Phase 3
0.7718 Intermediate Similarity NPD4060 Phase 1
0.7716 Intermediate Similarity NPD4966 Approved
0.7716 Intermediate Similarity NPD4967 Phase 2
0.7716 Intermediate Similarity NPD4965 Approved
0.7707 Intermediate Similarity NPD1512 Approved
0.7706 Intermediate Similarity NPD7808 Phase 3
0.7679 Intermediate Similarity NPD7054 Approved
0.7658 Intermediate Similarity NPD5403 Approved
0.7644 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD7472 Approved
0.7625 Intermediate Similarity NPD4380 Phase 2
0.7625 Intermediate Similarity NPD6599 Discontinued
0.7619 Intermediate Similarity NPD7228 Approved
0.7613 Intermediate Similarity NPD4110 Phase 3
0.7613 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD1465 Phase 2
0.7589 Intermediate Similarity NPD5536 Phase 2
0.758 Intermediate Similarity NPD1511 Approved
0.7557 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD5401 Approved
0.753 Intermediate Similarity NPD8127 Discontinued
0.7515 Intermediate Similarity NPD3751 Discontinued
0.75 Intermediate Similarity NPD1653 Approved
0.75 Intermediate Similarity NPD8166 Discontinued
0.7484 Intermediate Similarity NPD4534 Discontinued
0.7483 Intermediate Similarity NPD1613 Approved
0.7483 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD5844 Phase 1
0.7469 Intermediate Similarity NPD6385 Approved
0.7469 Intermediate Similarity NPD6386 Approved
0.7455 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD3455 Phase 2
0.7429 Intermediate Similarity NPD8434 Phase 2
0.7421 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD228 Approved
0.741 Intermediate Similarity NPD919 Approved
0.7403 Intermediate Similarity NPD2799 Discontinued
0.7403 Intermediate Similarity NPD7033 Discontinued
0.7378 Intermediate Similarity NPD7819 Suspended
0.7372 Intermediate Similarity NPD5958 Discontinued
0.7368 Intermediate Similarity NPD943 Approved
0.7368 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD5494 Approved
0.7355 Intermediate Similarity NPD2438 Suspended
0.7351 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD3764 Approved
0.7346 Intermediate Similarity NPD3226 Approved
0.7342 Intermediate Similarity NPD3887 Approved
0.7342 Intermediate Similarity NPD2354 Approved
0.7341 Intermediate Similarity NPD6559 Discontinued
0.7338 Intermediate Similarity NPD7097 Phase 1
0.7337 Intermediate Similarity NPD3926 Phase 2
0.7333 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6832 Phase 2
0.7325 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD7199 Phase 2
0.732 Intermediate Similarity NPD4340 Discontinued
0.732 Intermediate Similarity NPD1933 Approved
0.7305 Intermediate Similarity NPD5283 Phase 1
0.729 Intermediate Similarity NPD1510 Phase 2
0.7279 Intermediate Similarity NPD1608 Approved
0.7278 Intermediate Similarity NPD3787 Discontinued
0.7278 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD1549 Phase 2
0.7256 Intermediate Similarity NPD7411 Suspended
0.7255 Intermediate Similarity NPD1240 Approved
0.7248 Intermediate Similarity NPD1203 Approved
0.7248 Intermediate Similarity NPD2797 Approved
0.7244 Intermediate Similarity NPD1551 Phase 2
0.7244 Intermediate Similarity NPD6032 Approved
0.7237 Intermediate Similarity NPD2313 Discontinued
0.7235 Intermediate Similarity NPD5242 Approved
0.7219 Intermediate Similarity NPD1247 Approved
0.7211 Intermediate Similarity NPD1535 Discovery
0.7208 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3146 Approved
0.7205 Intermediate Similarity NPD2532 Approved
0.7205 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD2533 Approved
0.7205 Intermediate Similarity NPD2534 Approved
0.72 Intermediate Similarity NPD5647 Approved
0.7197 Intermediate Similarity NPD2346 Discontinued
0.7197 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD5762 Approved
0.7197 Intermediate Similarity NPD5763 Approved
0.7186 Intermediate Similarity NPD7768 Phase 2
0.7181 Intermediate Similarity NPD1283 Approved
0.7172 Intermediate Similarity NPD1894 Discontinued
0.7172 Intermediate Similarity NPD9545 Approved
0.717 Intermediate Similarity NPD3750 Approved
0.717 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD9269 Phase 2
0.7162 Intermediate Similarity NPD1481 Phase 2
0.7161 Intermediate Similarity NPD1607 Approved
0.7161 Intermediate Similarity NPD6653 Approved
0.716 Intermediate Similarity NPD5049 Phase 3
0.7159 Intermediate Similarity NPD8313 Approved
0.7159 Intermediate Similarity NPD8312 Approved
0.7151 Intermediate Similarity NPD7435 Discontinued
0.7143 Intermediate Similarity NPD7038 Approved
0.7143 Intermediate Similarity NPD7039 Approved
0.7143 Intermediate Similarity NPD2979 Phase 3
0.7143 Intermediate Similarity NPD4357 Discontinued
0.7143 Intermediate Similarity NPD7240 Approved
0.7143 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3847 Discontinued
0.7135 Intermediate Similarity NPD8150 Discontinued
0.7134 Intermediate Similarity NPD1501 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2796 Approved
0.7126 Intermediate Similarity NPD5353 Approved
0.7124 Intermediate Similarity NPD3268 Approved
0.7122 Intermediate Similarity NPD1358 Approved
0.7099 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD2353 Approved
0.7089 Intermediate Similarity NPD2344 Approved
0.7089 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD17 Approved
0.7072 Intermediate Similarity NPD7296 Approved
0.707 Intermediate Similarity NPD4308 Phase 3
0.707 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD8455 Phase 2
0.7066 Intermediate Similarity NPD7972 Discontinued
0.7055 Intermediate Similarity NPD6273 Approved
0.7047 Intermediate Similarity NPD9717 Approved
0.7044 Intermediate Similarity NPD2424 Discontinued
0.7032 Intermediate Similarity NPD826 Approved
0.7032 Intermediate Similarity NPD3620 Phase 2
0.7032 Intermediate Similarity NPD825 Approved
0.7032 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD3496 Discontinued
0.7025 Intermediate Similarity NPD9570 Approved
0.7024 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD3022 Approved
0.7021 Intermediate Similarity NPD3021 Approved
0.7021 Intermediate Similarity NPD2067 Discontinued
0.7014 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD5585 Approved
0.7 Intermediate Similarity NPD2983 Phase 2
0.7 Intermediate Similarity NPD2982 Phase 2
0.6994 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6994 Remote Similarity NPD3536 Discontinued
0.6989 Remote Similarity NPD6777 Approved
0.6989 Remote Similarity NPD6781 Approved
0.6989 Remote Similarity NPD5953 Discontinued
0.6989 Remote Similarity NPD6779 Approved
0.6989 Remote Similarity NPD6776 Approved
0.6989 Remote Similarity NPD6782 Approved
0.6989 Remote Similarity NPD6780 Approved
0.6989 Remote Similarity NPD6778 Approved
0.6988 Remote Similarity NPD7028 Phase 2
0.6981 Remote Similarity NPD2343 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   46210734
ChEMBL   CHEMBL1094303
ZINC  

Physicochemical Properties

Molecular Weight:  462.12
ALogP:  -1.8149
MLogP:  2.67
XLogP:  1.155
# Rotatable Bonds:  18
Polar Surface Area:  180.05
# H-Bond Aceptor:  7
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  33

Download Data

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