Natural Product: NPC93498

Natural Product ID:  NPC93498
Common Name:   Methyl 5-O-Caffeoyl-3-O-Sinapoylquinate
IUPAC Name:   methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate
Synonyms:  
Molecular Formula:   C28H30O13
Standard InCHIKey:  HNVWFUAOTFONLC-WMUFCWPYSA-N
Standard InCHI:  InChI=1S/C28H30O13/c1-37-20-11-16(12-21(38-2)25(20)34)6-9-24(33)41-26-19(31)13-28(36,27(35)39-3)14-22(26)40-23(32)8-5-15-4-7-17(29)18(30)10-15/h4-12,19,22,26,29-31,34,36H,13-14H2,1-3H3/b8-5+,9-6+/t19-,22-,26-,28+/m1/s1
Canonical SMILES:  COc1cc(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](C[C@H]2OC(=O)/C=C/c2ccc(c(c2)O)O)(O)C(=O)OC)cc(c1O)OC
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
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota Seoul, Korea 2000-JUN PMID[16643034]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota TCM_Taiwan*
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1 Others Radical scavenging activity IC50 = 8.3 ug/ml 16643034
NPT2 Others Unspecified IC50 = 1.8 ug/ml 16643034
NPT2 Others Unspecified Inhibition = 56 % 16643034
NPT23 Individual Protein Integrase Human immunodeficiency virus 1 IC50 = 19.4 ug/ml 16643034

  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 NPC93498 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 NPC163883
0.9931 High Similarity NPC19380
0.9931 High Similarity NPC146277
0.9796 High Similarity NPC145425
0.9583 High Similarity NPC98356
0.9456 High Similarity NPC306343
0.9388 High Similarity NPC42464
0.9375 High Similarity NPC43158
0.9375 High Similarity NPC258469
0.9375 High Similarity NPC472016
0.9375 High Similarity NPC277315
0.9375 High Similarity NPC192831
0.9338 High Similarity NPC473275
0.9338 High Similarity NPC470896
0.932 High Similarity NPC43123
0.9306 High Similarity NPC206095
0.9306 High Similarity NPC13818
0.9306 High Similarity NPC224389
0.9306 High Similarity NPC297517
0.9306 High Similarity NPC35702
0.9306 High Similarity NPC477335
0.9306 High Similarity NPC471027
0.9241 High Similarity NPC220664
0.9241 High Similarity NPC284948
0.9241 High Similarity NPC37331
0.9241 High Similarity NPC319628
0.9241 High Similarity NPC303090
0.92 High Similarity NPC75695
0.92 High Similarity NPC95498
0.92 High Similarity NPC246566
0.9189 High Similarity NPC192568
0.9189 High Similarity NPC471076
0.9167 High Similarity NPC476820
0.9167 High Similarity NPC295492
0.9167 High Similarity NPC205751
0.9167 High Similarity NPC274891
0.9167 High Similarity NPC476819
0.9167 High Similarity NPC474875
0.9167 High Similarity NPC26241
0.9167 High Similarity NPC303683
0.9108 High Similarity NPC471823
0.9097 High Similarity NPC152942
0.9097 High Similarity NPC37250
0.9097 High Similarity NPC278068
0.9097 High Similarity NPC219428
0.9097 High Similarity NPC142703
0.9097 High Similarity NPC302857
0.9073 High Similarity NPC476434
0.9067 High Similarity NPC473091
0.9048 High Similarity NPC114242
0.9048 High Similarity NPC50221
0.9026 High Similarity NPC472860
0.9013 High Similarity NPC44730
0.9007 High Similarity NPC252979
0.8993 High Similarity NPC322660
0.8986 High Similarity NPC477333
0.8974 High Similarity NPC25389
0.8974 High Similarity NPC311803
0.8974 High Similarity NPC472859
0.8968 High Similarity NPC289811
0.8968 High Similarity NPC160780
0.8966 High Similarity NPC24295
0.8966 High Similarity NPC283560
0.8933 High Similarity NPC472969
0.8919 High Similarity NPC226738
0.8919 High Similarity NPC22176
0.8919 High Similarity NPC121573
0.8919 High Similarity NPC190587
0.8917 High Similarity NPC285108
0.8917 High Similarity NPC33298
0.891 High Similarity NPC239966
0.891 High Similarity NPC119125
0.891 High Similarity NPC53889
0.891 High Similarity NPC166277
0.891 High Similarity NPC476373
0.891 High Similarity NPC203020
0.8904 High Similarity NPC289690
0.8904 High Similarity NPC288452
0.8903 High Similarity NPC1913
0.8889 High Similarity NPC182217
0.8889 High Similarity NPC233350
0.8889 High Similarity NPC70680
0.8874 High Similarity NPC476394
0.8874 High Similarity NPC98809
0.8867 High Similarity NPC221383
0.8867 High Similarity NPC143892
0.8867 High Similarity NPC299090
0.8867 High Similarity NPC283081
0.8861 High Similarity NPC227297
0.8846 High Similarity NPC74319
0.8846 High Similarity NPC287872
0.8846 High Similarity NPC87317
0.8819 High Similarity NPC68517
0.8808 High Similarity NPC142528
0.8805 High Similarity NPC142614
0.8797 High Similarity NPC476372
0.8797 High Similarity NPC476371
0.8797 High Similarity NPC4013
0.8797 High Similarity NPC90905
0.8792 High Similarity NPC160378
0.879 High Similarity NPC24627
0.879 High Similarity NPC24164
0.879 High Similarity NPC301089
0.879 High Similarity NPC289346
0.8782 High Similarity NPC68324
0.8782 High Similarity NPC114179
0.8782 High Similarity NPC289322
0.8782 High Similarity NPC160512
0.8782 High Similarity NPC156818
0.8782 High Similarity NPC38779
0.8758 High Similarity NPC243891
0.8758 High Similarity NPC300329
0.8733 High Similarity NPC258671
0.8733 High Similarity NPC53884
0.8718 High Similarity NPC300845
0.8718 High Similarity NPC250436
0.8718 High Similarity NPC291948
0.8718 High Similarity NPC104983
0.8718 High Similarity NPC88803
0.8718 High Similarity NPC134925
0.8712 High Similarity NPC476374
0.871 High Similarity NPC191046
0.871 High Similarity NPC327032
0.871 High Similarity NPC194095
0.8701 High Similarity NPC267091
0.8696 High Similarity NPC128403
0.8693 High Similarity NPC221091
0.8693 High Similarity NPC259576
0.869 High Similarity NPC135127
0.8688 High Similarity NPC471788
0.8684 High Similarity NPC294972
0.8684 High Similarity NPC139839
0.8684 High Similarity NPC98009
0.8684 High Similarity NPC120621
0.8684 High Similarity NPC248257
0.8667 High Similarity NPC473090
0.8667 High Similarity NPC304956
0.8667 High Similarity NPC134975
0.8662 High Similarity NPC226759
0.8662 High Similarity NPC133984
0.8654 High Similarity NPC203757
0.865 High Similarity NPC5786
0.865 High Similarity NPC476370
0.865 High Similarity NPC102851
0.8649 High Similarity NPC12218
0.8649 High Similarity NPC105525
0.8649 High Similarity NPC225036
0.8649 High Similarity NPC75763
0.8645 High Similarity NPC178574
0.8645 High Similarity NPC105827
0.8645 High Similarity NPC310661
0.8645 High Similarity NPC65591
0.8642 High Similarity NPC197708
0.8642 High Similarity NPC658
0.8642 High Similarity NPC280493
0.8639 High Similarity NPC125417
0.8639 High Similarity NPC95679
0.8639 High Similarity NPC25305
0.8639 High Similarity NPC110899
0.8639 High Similarity NPC112068
0.8636 High Similarity NPC140151
0.8636 High Similarity NPC477334
0.8627 High Similarity NPC475250
0.8627 High Similarity NPC107636
0.8627 High Similarity NPC478242
0.8627 High Similarity NPC92117
0.8627 High Similarity NPC75945
0.8618 High Similarity NPC165389
0.8616 High Similarity NPC112418
0.8616 High Similarity NPC308992
0.86 High Similarity NPC477696
0.86 High Similarity NPC273657
0.86 High Similarity NPC106920
0.86 High Similarity NPC477697
0.86 High Similarity NPC470811
0.8599 High Similarity NPC471405
0.8599 High Similarity NPC318432
0.8599 High Similarity NPC165483
0.8591 High Similarity NPC326065
0.859 High Similarity NPC43872
0.859 High Similarity NPC469888
0.859 High Similarity NPC144801
0.859 High Similarity NPC477299
0.859 High Similarity NPC287504
0.859 High Similarity NPC116850
0.859 High Similarity NPC25127
0.859 High Similarity NPC291510
0.859 High Similarity NPC197188
0.859 High Similarity NPC238672
0.8581 High Similarity NPC284409
0.8581 High Similarity NPC239943
0.8581 High Similarity NPC134905
0.8581 High Similarity NPC36130
0.858 High Similarity NPC295082
0.858 High Similarity NPC116745
0.858 High Similarity NPC283041
0.8571 High Similarity NPC191930
0.8571 High Similarity NPC120426
0.8571 High Similarity NPC294522
0.8571 High Similarity NPC21184

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC93498 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
0.9241 High Similarity NPD6190 Approved
0.8718 High Similarity NPD4868 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD6166 Phase 2
0.8457 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8424 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD3817 Phase 2
0.8367 Intermediate Similarity NPD230 Phase 1
0.8365 Intermediate Similarity NPD3882 Suspended
0.8354 Intermediate Similarity NPD2801 Approved
0.8291 Intermediate Similarity NPD1934 Approved
0.8284 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD6234 Discontinued
0.8242 Intermediate Similarity NPD3818 Discontinued
0.8219 Intermediate Similarity NPD3027 Phase 3
0.8193 Intermediate Similarity NPD5844 Phase 1
0.8176 Intermediate Similarity NPD37 Approved
0.8153 Intermediate Similarity NPD1653 Approved
0.8137 Intermediate Similarity NPD4966 Approved
0.8137 Intermediate Similarity NPD4967 Phase 2
0.8137 Intermediate Similarity NPD4965 Approved
0.8125 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.811 Intermediate Similarity NPD6232 Discontinued
0.8095 Intermediate Similarity NPD6797 Phase 2
0.8089 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD7075 Discontinued
0.8084 Intermediate Similarity NPD7054 Approved
0.8075 Intermediate Similarity NPD5402 Approved
0.8047 Intermediate Similarity NPD7251 Discontinued
0.8047 Intermediate Similarity NPD7685 Pre-registration
0.8036 Intermediate Similarity NPD7074 Phase 3
0.8036 Intermediate Similarity NPD7472 Approved
0.8025 Intermediate Similarity NPD1512 Approved
0.8024 Intermediate Similarity NPD7228 Approved
0.8013 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD1465 Phase 2
0.8 Intermediate Similarity NPD7808 Phase 3
0.7964 Intermediate Similarity NPD7473 Discontinued
0.7952 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD6801 Discontinued
0.7939 Intermediate Similarity NPD7199 Phase 2
0.7937 Intermediate Similarity NPD4380 Phase 2
0.7901 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD6799 Approved
0.7898 Intermediate Similarity NPD1511 Approved
0.7867 Intermediate Similarity NPD6233 Phase 2
0.7857 Intermediate Similarity NPD7266 Discontinued
0.7821 Intermediate Similarity NPD4628 Phase 3
0.7815 Intermediate Similarity NPD1613 Approved
0.7815 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD3751 Discontinued
0.7808 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.78 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD5403 Approved
0.7718 Intermediate Similarity NPD9494 Approved
0.7679 Intermediate Similarity NPD3787 Discontinued
0.7665 Intermediate Similarity NPD5494 Approved
0.764 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD5353 Approved
0.7625 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD5401 Approved
0.7619 Intermediate Similarity NPD9269 Phase 2
0.7607 Intermediate Similarity NPD6599 Discontinued
0.7576 Intermediate Similarity NPD7819 Suspended
0.7566 Intermediate Similarity NPD6798 Discontinued
0.7561 Intermediate Similarity NPD7411 Suspended
0.7558 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7240 Approved
0.7529 Intermediate Similarity NPD5242 Approved
0.7528 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1510 Phase 2
0.7483 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD1549 Phase 2
0.7455 Intermediate Similarity NPD6386 Approved
0.7455 Intermediate Similarity NPD6385 Approved
0.7453 Intermediate Similarity NPD4357 Discontinued
0.7452 Intermediate Similarity NPD2935 Discontinued
0.7429 Intermediate Similarity NPD6559 Discontinued
0.7421 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD447 Suspended
0.7416 Intermediate Similarity NPD8434 Phase 2
0.7412 Intermediate Similarity NPD8127 Discontinued
0.7407 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD919 Approved
0.7386 Intermediate Similarity NPD7095 Approved
0.7375 Intermediate Similarity NPD3750 Approved
0.7375 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD1240 Approved
0.7355 Intermediate Similarity NPD943 Approved
0.7347 Intermediate Similarity NPD9268 Approved
0.7342 Intermediate Similarity NPD1551 Phase 2
0.7342 Intermediate Similarity NPD2796 Approved
0.7333 Intermediate Similarity NPD2983 Phase 2
0.7333 Intermediate Similarity NPD2982 Phase 2
0.7329 Intermediate Similarity NPD5536 Phase 2
0.7326 Intermediate Similarity NPD3926 Phase 2
0.7321 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD8150 Discontinued
0.731 Intermediate Similarity NPD1247 Approved
0.7308 Intermediate Similarity NPD6355 Discontinued
0.7303 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD2532 Approved
0.7301 Intermediate Similarity NPD2534 Approved
0.7301 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD2533 Approved
0.729 Intermediate Similarity NPD4062 Phase 3
0.7283 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD9545 Approved
0.7278 Intermediate Similarity NPD7033 Discontinued
0.7278 Intermediate Similarity NPD7768 Phase 2
0.7267 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD8166 Discontinued
0.7267 Intermediate Similarity NPD2981 Phase 2
0.7261 Intermediate Similarity NPD1607 Approved
0.7255 Intermediate Similarity NPD3018 Phase 2
0.7235 Intermediate Similarity NPD3749 Approved
0.7234 Intermediate Similarity NPD7435 Discontinued
0.7232 Intermediate Similarity NPD7038 Approved
0.7232 Intermediate Similarity NPD7039 Approved
0.7226 Intermediate Similarity NPD3764 Approved
0.7209 Intermediate Similarity NPD6959 Discontinued
0.7205 Intermediate Similarity NPD1652 Phase 2
0.7204 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7549 Discontinued
0.717 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD7229 Phase 3
0.7166 Intermediate Similarity NPD6776 Approved
0.7166 Intermediate Similarity NPD6780 Approved
0.7166 Intermediate Similarity NPD6777 Approved
0.7166 Intermediate Similarity NPD6782 Approved
0.7166 Intermediate Similarity NPD6779 Approved
0.7166 Intermediate Similarity NPD6778 Approved
0.7166 Intermediate Similarity NPD6781 Approved
0.716 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD4110 Phase 3
0.7152 Intermediate Similarity NPD1608 Approved
0.7143 Intermediate Similarity NPD7680 Approved
0.7143 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6971 Discontinued
0.7134 Intermediate Similarity NPD4060 Phase 1
0.7126 Intermediate Similarity NPD3455 Phase 2
0.7125 Intermediate Similarity NPD6100 Approved
0.7125 Intermediate Similarity NPD6099 Approved
0.7097 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4908 Phase 1
0.7091 Intermediate Similarity NPD3146 Approved
0.7091 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD4340 Discontinued
0.7089 Intermediate Similarity NPD1933 Approved
0.7089 Intermediate Similarity NPD5124 Phase 1
0.7086 Intermediate Similarity NPD422 Phase 1
0.7063 Intermediate Similarity NPD3748 Approved
0.7059 Intermediate Similarity NPD3225 Approved
0.7059 Intermediate Similarity NPD8455 Phase 2
0.7034 Intermediate Similarity NPD228 Approved
0.7024 Intermediate Similarity NPD3226 Approved
0.7013 Intermediate Similarity NPD2797 Approved
0.7012 Intermediate Similarity NPD2354 Approved
0.7012 Intermediate Similarity NPD3887 Approved
0.701 Intermediate Similarity NPD7874 Approved
0.701 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3268 Approved
0.7006 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7097 Phase 1
0.6983 Remote Similarity NPD5953 Discontinued
0.6974 Remote Similarity NPD1535 Discovery
0.6963 Remote Similarity NPD7697 Approved
0.6963 Remote Similarity NPD7696 Phase 3
0.6963 Remote Similarity NPD7698 Approved
0.6961 Remote Similarity NPD8312 Approved
0.6961 Remote Similarity NPD8313 Approved
0.6959 Remote Similarity NPD8151 Discontinued
0.6954 Remote Similarity NPD17 Approved
0.6946 Remote Similarity NPD6273 Approved
0.6937 Remote Similarity NPD6653 Approved
0.6933 Remote Similarity NPD1548 Phase 1
0.6933 Remote Similarity NPD4534 Discontinued
0.6928 Remote Similarity NPD1481 Phase 2
0.6927 Remote Similarity NPD7870 Phase 2
0.6927 Remote Similarity NPD7871 Phase 2
0.6923 Remote Similarity NPD7458 Discontinued
0.6923 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6918 Remote Similarity NPD3620 Phase 2
0.6918 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6914 Remote Similarity NPD2438 Suspended
0.6907 Remote Similarity NPD7701 Phase 2
0.6905 Remote Similarity NPD920 Approved
0.6903 Remote Similarity NPD1203 Approved
0.6898 Remote Similarity NPD6535 Approved
0.6898 Remote Similarity NPD6534 Approved
0.6879 Remote Similarity NPD6832 Phase 2
0.6875 Remote Similarity NPD1358 Approved
0.6875 Remote Similarity NPD1899 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   11635556
ChEMBL   CHEMBL474262
ZINC  

Physicochemical Properties

Molecular Weight:  574.17
ALogP:  -1.7788
MLogP:  3.11
XLogP:  1.052
# Rotatable Bonds:  20
Polar Surface Area:  198.51
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  41

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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