Natural Product: NPC223335

Natural Product ID:  NPC223335
Common Name:   Shomaside C
IUPAC Name:   (2R,3S)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]-3-[(E)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxybutanedioic acid
Synonyms:   Shomaside C
Molecular Formula:   C27H30O15
Standard InCHIKey:  UEFRIVIHMWFPPY-NKQMXYLVSA-N
Standard InCHI:  InChI=1S/C27H30O15/c1-39-17-10-13(4-8-16(17)40-25-22(33)21(32)20(31)18(12-28)41-25)5-9-19(30)42-23(24(34)35)27(38,26(36)37)11-14-2-6-15(29)7-3-14/h2-10,18,20-23,25,28-29,31-33,38H,11-12H2,1H3,(H,34,35)(H,36,37)/b9-5+/t18-,20-,21+,22-,23-,25-,27-/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](Oc2ccc(cc2OC)/C=C/C(=O)O[C@@H]([C@@](C(=O)O)(Cc2ccc(cc2)O)O)C(=O)O)[C@@H]([C@H]([C@@H]1O)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
NPO30530 Cimicifuga dahurica Species Ranunculaceae Eukaryota PMID[20192237]
NPO32999 cimicifuga heracleifolia Species Ranunculaceae Eukaryota PMID[20192237]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 663000 nM 20041704

  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 NPC223335 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 NPC40920
0.9933 High Similarity NPC469654
0.9868 High Similarity NPC44507
0.92 High Similarity NPC221383
0.92 High Similarity NPC283081
0.92 High Similarity NPC143892
0.92 High Similarity NPC299090
0.9161 High Similarity NPC163635
0.9128 High Similarity NPC304956
0.9097 High Similarity NPC38699
0.9097 High Similarity NPC10205
0.9091 High Similarity NPC44730
0.9085 High Similarity NPC300329
0.9079 High Similarity NPC111785
0.9079 High Similarity NPC478242
0.9067 High Similarity NPC53884
0.9067 High Similarity NPC258671
0.9038 High Similarity NPC478055
0.9038 High Similarity NPC471405
0.9032 High Similarity NPC194095
0.9032 High Similarity NPC191046
0.9032 High Similarity NPC327032
0.9026 High Similarity NPC246566
0.9026 High Similarity NPC134905
0.9026 High Similarity NPC95498
0.9026 High Similarity NPC36130
0.902 High Similarity NPC259576
0.902 High Similarity NPC221091
0.8974 High Similarity NPC131532
0.8968 High Similarity NPC115466
0.8968 High Similarity NPC245615
0.8968 High Similarity NPC137813
0.8968 High Similarity NPC61604
0.8968 High Similarity NPC299706
0.8933 High Similarity NPC478239
0.891 High Similarity NPC477299
0.8896 High Similarity NPC229882
0.8896 High Similarity NPC158635
0.8889 High Similarity NPC128403
0.8868 High Similarity NPC203020
0.8868 High Similarity NPC239966
0.8867 High Similarity NPC157816
0.8867 High Similarity NPC140502
0.8861 High Similarity NPC133984
0.8861 High Similarity NPC226759
0.8854 High Similarity NPC186316
0.8846 High Similarity NPC157898
0.882 High Similarity NPC227297
0.8812 High Similarity NPC71780
0.8805 High Similarity NPC289811
0.8805 High Similarity NPC160780
0.88 High Similarity NPC186406
0.8795 High Similarity NPC472382
0.8795 High Similarity NPC472384
0.8795 High Similarity NPC472380
0.879 High Similarity NPC160882
0.8788 High Similarity NPC4390
0.8773 High Similarity NPC116745
0.8766 High Similarity NPC116229
0.8758 High Similarity NPC199928
0.8758 High Similarity NPC56735
0.8758 High Similarity NPC61594
0.875 High Similarity NPC232228
0.875 High Similarity NPC160378
0.8742 High Similarity NPC286919
0.8742 High Similarity NPC475663
0.8742 High Similarity NPC1913
0.8742 High Similarity NPC472860
0.8735 High Similarity NPC473630
0.8735 High Similarity NPC264735
0.8733 High Similarity NPC156709
0.8733 High Similarity NPC179505
0.8733 High Similarity NPC289690
0.8733 High Similarity NPC288452
0.8727 High Similarity NPC190003
0.8727 High Similarity NPC153755
0.8727 High Similarity NPC175107
0.871 High Similarity NPC106138
0.871 High Similarity NPC476394
0.871 High Similarity NPC98809
0.8704 High Similarity NPC147596
0.8696 High Similarity NPC472859
0.8696 High Similarity NPC25389
0.8696 High Similarity NPC311803
0.8693 High Similarity NPC100998
0.8693 High Similarity NPC476382
0.8693 High Similarity NPC34927
0.8693 High Similarity NPC34587
0.8693 High Similarity NPC252292
0.8688 High Similarity NPC469384
0.8688 High Similarity NPC57072
0.8688 High Similarity NPC231475
0.8683 High Similarity NPC198324
0.8683 High Similarity NPC268533
0.8683 High Similarity NPC472385
0.8679 High Similarity NPC228357
0.8667 High Similarity NPC72249
0.8667 High Similarity NPC212748
0.8667 High Similarity NPC244776
0.8667 High Similarity NPC155763
0.8667 High Similarity NPC116864
0.8667 High Similarity NPC235260
0.8667 High Similarity NPC20505
0.8667 High Similarity NPC100389
0.8667 High Similarity NPC206123
0.8659 High Similarity NPC298847
0.8658 High Similarity NPC37468
0.8655 High Similarity NPC475360
0.8654 High Similarity NPC32197
0.8654 High Similarity NPC205054
0.8654 High Similarity NPC471214
0.865 High Similarity NPC88243
0.865 High Similarity NPC165720
0.8645 High Similarity NPC472969
0.8645 High Similarity NPC1580
0.8645 High Similarity NPC192568
0.8645 High Similarity NPC471076
0.8642 High Similarity NPC22324
0.8642 High Similarity NPC33298
0.8642 High Similarity NPC148273
0.8642 High Similarity NPC285108
0.8636 High Similarity NPC98356
0.8636 High Similarity NPC476865
0.8634 High Similarity NPC166277
0.8634 High Similarity NPC119125
0.8631 High Similarity NPC217520
0.8631 High Similarity NPC35167
0.8631 High Similarity NPC477895
0.8631 High Similarity NPC139571
0.8627 High Similarity NPC110063
0.8627 High Similarity NPC292443
0.8623 High Similarity NPC49344
0.8623 High Similarity NPC43211
0.8623 High Similarity NPC135277
0.8623 High Similarity NPC115760
0.8623 High Similarity NPC101191
0.8623 High Similarity NPC210094
0.8623 High Similarity NPC477848
0.8623 High Similarity NPC237435
0.8614 High Similarity NPC472386
0.8609 High Similarity NPC202700
0.8608 High Similarity NPC87403
0.8606 High Similarity NPC203050
0.8606 High Similarity NPC120099
0.8606 High Similarity NPC223747
0.8606 High Similarity NPC270578
0.8606 High Similarity NPC138927
0.8606 High Similarity NPC225434
0.8606 High Similarity NPC52382
0.8606 High Similarity NPC229687
0.8606 High Similarity NPC219904
0.8605 High Similarity NPC205721
0.86 High Similarity NPC67349
0.86 High Similarity NPC126206
0.86 High Similarity NPC279676
0.8589 High Similarity NPC173729
0.8589 High Similarity NPC272750
0.8589 High Similarity NPC88043
0.8589 High Similarity NPC134047
0.8589 High Similarity NPC223006
0.8588 High Similarity NPC36138
0.8581 High Similarity NPC232992
0.8581 High Similarity NPC229264
0.858 High Similarity NPC217950
0.8571 High Similarity NPC211532
0.8571 High Similarity NPC61904
0.8571 High Similarity NPC233994
0.8571 High Similarity NPC76211
0.8571 High Similarity NPC476864
0.8571 High Similarity NPC476866
0.8571 High Similarity NPC476868
0.8571 High Similarity NPC287872
0.8571 High Similarity NPC74319
0.8571 High Similarity NPC144097
0.8571 High Similarity NPC476869
0.8563 High Similarity NPC169977
0.8563 High Similarity NPC199357
0.8563 High Similarity NPC175230
0.8563 High Similarity NPC42773
0.8563 High Similarity NPC172033
0.8563 High Similarity NPC88560
0.8563 High Similarity NPC45522
0.8563 High Similarity NPC21666
0.8563 High Similarity NPC24043
0.8563 High Similarity NPC101026
0.8562 High Similarity NPC470896
0.8562 High Similarity NPC473275
0.8554 High Similarity NPC44558
0.8554 High Similarity NPC149011
0.8554 High Similarity NPC204937
0.8554 High Similarity NPC105511
0.8553 High Similarity NPC185103
0.8545 High Similarity NPC317489
0.8545 High Similarity NPC149244
0.8545 High Similarity NPC84362
0.8545 High Similarity NPC325555
0.8545 High Similarity NPC173637
0.8545 High Similarity NPC223424
0.8545 High Similarity NPC52550
0.8545 High Similarity NPC265530

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC223335 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
0.8623 High Similarity NPD4338 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD3818 Discontinued
0.8402 Intermediate Similarity NPD7808 Phase 3
0.8393 Intermediate Similarity NPD6797 Phase 2
0.8343 Intermediate Similarity NPD7251 Discontinued
0.8333 Intermediate Similarity NPD7074 Phase 3
0.8323 Intermediate Similarity NPD6190 Approved
0.8301 Intermediate Similarity NPD7266 Discontinued
0.8274 Intermediate Similarity NPD7054 Approved
0.8225 Intermediate Similarity NPD7472 Approved
0.8171 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD3817 Phase 2
0.8129 Intermediate Similarity NPD7685 Pre-registration
0.8125 Intermediate Similarity NPD1653 Approved
0.811 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD6166 Phase 2
0.8061 Intermediate Similarity NPD7075 Discontinued
0.8059 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8046 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD1934 Approved
0.8037 Intermediate Similarity NPD37 Approved
0.8023 Intermediate Similarity NPD6559 Discontinued
0.8023 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD6234 Discontinued
0.8 Intermediate Similarity NPD4967 Phase 2
0.8 Intermediate Similarity NPD3751 Discontinued
0.8 Intermediate Similarity NPD4966 Approved
0.8 Intermediate Similarity NPD7228 Approved
0.8 Intermediate Similarity NPD4965 Approved
0.8 Intermediate Similarity NPD3882 Suspended
0.7939 Intermediate Similarity NPD5402 Approved
0.7929 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD6233 Phase 2
0.7829 Intermediate Similarity NPD8312 Approved
0.7829 Intermediate Similarity NPD8313 Approved
0.7818 Intermediate Similarity NPD6801 Discontinued
0.7811 Intermediate Similarity NPD7199 Phase 2
0.7799 Intermediate Similarity NPD4628 Phase 3
0.7778 Intermediate Similarity NPD6798 Discontinued
0.7771 Intermediate Similarity NPD8455 Phase 2
0.7771 Intermediate Similarity NPD2801 Approved
0.7765 Intermediate Similarity NPD3787 Discontinued
0.773 Intermediate Similarity NPD5403 Approved
0.773 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD6232 Discontinued
0.7654 Intermediate Similarity NPD6799 Approved
0.7644 Intermediate Similarity NPD5844 Phase 1
0.7628 Intermediate Similarity NPD6355 Discontinued
0.7628 Intermediate Similarity NPD1933 Approved
0.7614 Intermediate Similarity NPD7240 Approved
0.7611 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD5401 Approved
0.7597 Intermediate Similarity NPD7095 Approved
0.7597 Intermediate Similarity NPD3027 Phase 3
0.7594 Intermediate Similarity NPD7435 Discontinued
0.759 Intermediate Similarity NPD4380 Phase 2
0.7564 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD1613 Approved
0.7561 Intermediate Similarity NPD1512 Approved
0.756 Intermediate Similarity NPD1465 Phase 2
0.7532 Intermediate Similarity NPD7097 Phase 1
0.7529 Intermediate Similarity NPD7473 Discontinued
0.7516 Intermediate Similarity NPD447 Suspended
0.75 Intermediate Similarity NPD8127 Discontinued
0.75 Intermediate Similarity NPD4062 Phase 3
0.75 Intermediate Similarity NPD8434 Phase 2
0.7485 Intermediate Similarity NPD6599 Discontinued
0.7484 Intermediate Similarity NPD7033 Discontinued
0.7456 Intermediate Similarity NPD7819 Suspended
0.7452 Intermediate Similarity NPD4060 Phase 1
0.7442 Intermediate Similarity NPD5494 Approved
0.7439 Intermediate Similarity NPD1511 Approved
0.7438 Intermediate Similarity NPD2935 Discontinued
0.7434 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7433 Intermediate Similarity NPD6779 Approved
0.7433 Intermediate Similarity NPD6780 Approved
0.7433 Intermediate Similarity NPD6781 Approved
0.7433 Intermediate Similarity NPD6782 Approved
0.7433 Intermediate Similarity NPD6776 Approved
0.7433 Intermediate Similarity NPD6777 Approved
0.7433 Intermediate Similarity NPD6778 Approved
0.7407 Intermediate Similarity NPD6674 Discontinued
0.7394 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4110 Phase 3
0.7362 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD7874 Approved
0.7346 Intermediate Similarity NPD1549 Phase 2
0.7342 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7411 Suspended
0.7321 Intermediate Similarity NPD3226 Approved
0.7308 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD1091 Approved
0.7301 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD4340 Discontinued
0.7296 Intermediate Similarity NPD230 Phase 1
0.7284 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD919 Approved
0.7256 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD4534 Discontinued
0.7225 Intermediate Similarity NPD7697 Approved
0.7225 Intermediate Similarity NPD7698 Approved
0.7225 Intermediate Similarity NPD7696 Phase 3
0.7222 Intermediate Similarity NPD7038 Approved
0.7222 Intermediate Similarity NPD7039 Approved
0.7216 Intermediate Similarity NPD3926 Phase 2
0.7215 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD7871 Phase 2
0.7188 Intermediate Similarity NPD8319 Approved
0.7188 Intermediate Similarity NPD7870 Phase 2
0.7188 Intermediate Similarity NPD8320 Phase 1
0.7186 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD2346 Discontinued
0.7169 Intermediate Similarity NPD5058 Phase 3
0.7168 Intermediate Similarity NPD7768 Phase 2
0.7166 Intermediate Similarity NPD6534 Approved
0.7166 Intermediate Similarity NPD6535 Approved
0.7165 Intermediate Similarity NPD7701 Phase 2
0.716 Intermediate Similarity NPD2799 Discontinued
0.7152 Intermediate Similarity NPD3750 Approved
0.7151 Intermediate Similarity NPD7296 Approved
0.7143 Intermediate Similarity NPD7783 Phase 2
0.7143 Intermediate Similarity NPD1608 Approved
0.7143 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6386 Approved
0.7135 Intermediate Similarity NPD7680 Approved
0.7135 Intermediate Similarity NPD6385 Approved
0.7134 Intermediate Similarity NPD5958 Discontinued
0.7134 Intermediate Similarity NPD9494 Approved
0.7128 Intermediate Similarity NPD8151 Discontinued
0.712 Intermediate Similarity NPD8150 Discontinued
0.7117 Intermediate Similarity NPD2796 Approved
0.7117 Intermediate Similarity NPD1551 Phase 2
0.7115 Intermediate Similarity NPD2797 Approved
0.711 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD3887 Approved
0.7108 Intermediate Similarity NPD2354 Approved
0.7107 Intermediate Similarity NPD2313 Discontinued
0.7107 Intermediate Similarity NPD3764 Approved
0.7104 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD1247 Approved
0.7089 Intermediate Similarity NPD6832 Phase 2
0.7086 Intermediate Similarity NPD5536 Phase 2
0.7083 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6823 Phase 2
0.7083 Intermediate Similarity NPD3146 Approved
0.7079 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD3705 Approved
0.7076 Intermediate Similarity NPD7028 Phase 2
0.7073 Intermediate Similarity NPD5763 Approved
0.7073 Intermediate Similarity NPD5762 Approved
0.707 Intermediate Similarity NPD5647 Approved
0.7056 Intermediate Similarity NPD7801 Approved
0.7055 Intermediate Similarity NPD1510 Phase 2
0.7053 Intermediate Similarity NPD7700 Phase 2
0.7053 Intermediate Similarity NPD7699 Phase 2
0.7048 Intermediate Similarity NPD8166 Discontinued
0.7041 Intermediate Similarity NPD6273 Approved
0.7037 Intermediate Similarity NPD6653 Approved
0.7035 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD2424 Discontinued
0.7029 Intermediate Similarity NPD3749 Approved
0.7025 Intermediate Similarity NPD2861 Phase 2
0.7018 Intermediate Similarity NPD7458 Discontinued
0.7018 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD6032 Approved
0.701 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD1203 Approved
0.7006 Intermediate Similarity NPD6959 Discontinued
0.7 Intermediate Similarity NPD3268 Approved
0.6995 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6993 Remote Similarity NPD1357 Approved
0.6988 Remote Similarity NPD1652 Phase 2
0.6975 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6975 Remote Similarity NPD5124 Phase 1
0.6975 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1535 Discovery
0.6959 Remote Similarity NPD3687 Approved
0.6959 Remote Similarity NPD3686 Approved
0.6951 Remote Similarity NPD4308 Phase 3
0.6948 Remote Similarity NPD17 Approved
0.6941 Remote Similarity NPD5049 Phase 3
0.6939 Remote Similarity NPD7584 Approved
0.6928 Remote Similarity NPD970 Clinical (unspecified phase)
0.6928 Remote Similarity NPD1894 Discontinued
0.6927 Remote Similarity NPD5242 Approved
0.6923 Remote Similarity NPD1481 Phase 2
0.6919 Remote Similarity NPD3455 Phase 2
0.6914 Remote Similarity NPD5353 Approved

Structure

External Identifiers

PubChem CID   46209907
ChEMBL   CHEMBL1096591
ZINC  

Physicochemical Properties

Molecular Weight:  594.16
ALogP:  -3.51
MLogP:  2.78
XLogP:  0.062
# Rotatable Bonds:  22
Polar Surface Area:  249.97
# H-Bond Aceptor:  12
# H-Bond Donor:  8
# Rings:  3
# Heavy Atoms:  42

Download Data

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