Natural Product: NPC163598

Natural Product ID:  NPC163598
Common Name:   Repenin C
IUPAC Name:   [(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-5-methoxy-9-oxo-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:   Repenin C
Molecular Formula:   C29H24O11
Standard InCHIKey:  SBHOYULRLAYYGT-BWSLMISRSA-N
Standard InCHI:  InChI=1S/C29H24O11/c1-35-21-12-16(5-8-19(21)31)26-23(14-37-24(33)9-4-15-3-7-18(30)20(32)11-15)38-29-27-17(6-10-25(34)39-27)13-22(36-2)28(29)40-26/h3-13,23,26,30-32H,14H2,1-2H3/b9-4+/t23-,26-/m1/s1
Canonical SMILES:  COc1cc(ccc1O)[C@H]1Oc2c(OC)cc3c(c2O[C@@H]1COC(=O)/C=C/c1ccc(c(c1)O)O)oc(=O)cc3
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
NPO32501 Duranta erecta Species Verbenaceae Eukaryota PMID[19464173]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1 Others Radical scavenging activity IC50 = 450000 nM 21071520

  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 NPC163598 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 NPC264875
1.0 High Similarity NPC120774
0.9792 High Similarity NPC30688
0.9792 High Similarity NPC176903
0.9724 High Similarity NPC205727
0.9724 High Similarity NPC21184
0.9724 High Similarity NPC120426
0.9724 High Similarity NPC294522
0.9586 High Similarity NPC187398
0.9586 High Similarity NPC476348
0.9517 High Similarity NPC476347
0.9517 High Similarity NPC15577
0.9463 High Similarity NPC8712
0.9448 High Similarity NPC268515
0.9448 High Similarity NPC40222
0.929 High Similarity NPC142614
0.9241 High Similarity NPC256555
0.9241 High Similarity NPC110067
0.9241 High Similarity NPC91492
0.9241 High Similarity NPC34245
0.9241 High Similarity NPC7439
0.9205 High Similarity NPC268484
0.9139 High Similarity NPC150442
0.9139 High Similarity NPC223720
0.9133 High Similarity NPC213197
0.9128 High Similarity NPC475250
0.9122 High Similarity NPC231149
0.9097 High Similarity NPC13067
0.9073 High Similarity NPC53587
0.9073 High Similarity NPC476352
0.9073 High Similarity NPC176186
0.9073 High Similarity NPC169404
0.9073 High Similarity NPC215060
0.906 High Similarity NPC139839
0.906 High Similarity NPC48366
0.9028 High Similarity NPC148835
0.9028 High Similarity NPC139548
0.9028 High Similarity NPC76336
0.9028 High Similarity NPC95162
0.9028 High Similarity NPC20511
0.9028 High Similarity NPC52086
0.9 High Similarity NPC212670
0.9 High Similarity NPC313334
0.9 High Similarity NPC206264
0.8993 High Similarity NPC275125
0.8993 High Similarity NPC178129
0.8993 High Similarity NPC97937
0.8993 High Similarity NPC170239
0.8973 High Similarity NPC300611
0.8966 High Similarity NPC43500
0.8966 High Similarity NPC164148
0.8961 High Similarity NPC284810
0.8958 High Similarity NPC126682
0.8958 High Similarity NPC82271
0.8954 High Similarity NPC62903
0.8954 High Similarity NPC7178
0.894 High Similarity NPC114740
0.8933 High Similarity NPC281549
0.8933 High Similarity NPC96294
0.8933 High Similarity NPC93924
0.8933 High Similarity NPC478237
0.8926 High Similarity NPC205361
0.8919 High Similarity NPC185127
0.8912 High Similarity NPC278469
0.8912 High Similarity NPC193722
0.891 High Similarity NPC53889
0.8903 High Similarity NPC125495
0.8897 High Similarity NPC474886
0.8897 High Similarity NPC326797
0.8897 High Similarity NPC102904
0.8897 High Similarity NPC107551
0.8897 High Similarity NPC176051
0.8897 High Similarity NPC103976
0.8897 High Similarity NPC126206
0.8897 High Similarity NPC474282
0.8897 High Similarity NPC38874
0.8896 High Similarity NPC142479
0.8896 High Similarity NPC155015
0.8889 High Similarity NPC474656
0.8874 High Similarity NPC106138
0.8874 High Similarity NPC113790
0.8867 High Similarity NPC41844
0.8859 High Similarity NPC473909
0.8859 High Similarity NPC143120
0.8859 High Similarity NPC125617
0.8859 High Similarity NPC274960
0.8851 High Similarity NPC138212
0.8846 High Similarity NPC87317
0.8844 High Similarity NPC224876
0.8844 High Similarity NPC83375
0.8828 High Similarity NPC471664
0.8828 High Similarity NPC286843
0.8828 High Similarity NPC471665
0.8819 High Similarity NPC474600
0.8819 High Similarity NPC111635
0.8819 High Similarity NPC309953
0.8819 High Similarity NPC92830
0.8808 High Similarity NPC252402
0.8808 High Similarity NPC102934
0.88 High Similarity NPC199928
0.8792 High Similarity NPC171932
0.8792 High Similarity NPC471763
0.8792 High Similarity NPC28440
0.879 High Similarity NPC24164
0.879 High Similarity NPC301089
0.8784 High Similarity NPC469564
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
0.8776 High Similarity NPC267291
0.8776 High Similarity NPC262189
0.8776 High Similarity NPC22317
0.8767 High Similarity NPC211549
0.8767 High Similarity NPC276490
0.8766 High Similarity NPC476154
0.8766 High Similarity NPC475141
0.8759 High Similarity NPC470356
0.8759 High Similarity NPC94750
0.8759 High Similarity NPC224941
0.8759 High Similarity NPC112246
0.8759 High Similarity NPC474206
0.8759 High Similarity NPC112939
0.8759 High Similarity NPC472337
0.8759 High Similarity NPC121812
0.8759 High Similarity NPC234865
0.8759 High Similarity NPC311430
0.8758 High Similarity NPC476279
0.875 High Similarity NPC26673
0.875 High Similarity NPC277021
0.875 High Similarity NPC241341
0.875 High Similarity NPC229442
0.875 High Similarity NPC233018
0.875 High Similarity NPC36437
0.875 High Similarity NPC168059
0.8742 High Similarity NPC52740
0.8734 High Similarity NPC124747
0.8734 High Similarity NPC155754
0.8734 High Similarity NPC109061
0.8725 High Similarity NPC230157
0.8725 High Similarity NPC6568
0.8725 High Similarity NPC236419
0.8718 High Similarity NPC300845
0.8718 High Similarity NPC104983
0.8718 High Similarity NPC318432
0.8718 High Similarity NPC250436
0.8718 High Similarity NPC291948
0.8718 High Similarity NPC88803
0.8716 High Similarity NPC178054
0.8716 High Similarity NPC471389
0.871 High Similarity NPC473736
0.8707 High Similarity NPC25966
0.8707 High Similarity NPC245207
0.8707 High Similarity NPC127218
0.8707 High Similarity NPC319647
0.8699 High Similarity NPC306441
0.8699 High Similarity NPC472336
0.8699 High Similarity NPC471719
0.8699 High Similarity NPC230734
0.8699 High Similarity NPC16435
0.8699 High Similarity NPC227503
0.8699 High Similarity NPC472334
0.8699 High Similarity NPC474639
0.8696 High Similarity NPC243877
0.8696 High Similarity NPC473818
0.869 High Similarity NPC135127
0.869 High Similarity NPC310854
0.869 High Similarity NPC170694
0.869 High Similarity NPC106215
0.8681 High Similarity NPC319969
0.8681 High Similarity NPC137669
0.8681 High Similarity NPC137949
0.8681 High Similarity NPC245120
0.8679 High Similarity NPC476372
0.8679 High Similarity NPC55121
0.8679 High Similarity NPC12326
0.8679 High Similarity NPC174311
0.8679 High Similarity NPC476371
0.8667 High Similarity NPC471824
0.8667 High Similarity NPC292443
0.8667 High Similarity NPC232228
0.8658 High Similarity NPC107161
0.8658 High Similarity NPC67467
0.8654 High Similarity NPC125709
0.8654 High Similarity NPC292385
0.8645 High Similarity NPC470769
0.8645 High Similarity NPC78809
0.8645 High Similarity NPC149735
0.8645 High Similarity NPC115203
0.8642 High Similarity NPC280493
0.8636 High Similarity NPC300329
0.8634 High Similarity NPC471823
0.863 High Similarity NPC151224
0.863 High Similarity NPC260898
0.863 High Similarity NPC47398
0.863 High Similarity NPC195022
0.863 High Similarity NPC61946
0.863 High Similarity NPC234333

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC163598 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
0.9 High Similarity NPD1653 Approved
0.8718 High Similarity NPD4868 Clinical (unspecified phase)
0.8425 Intermediate Similarity NPD1613 Approved
0.8425 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD5844 Phase 1
0.8344 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD6166 Phase 2
0.8323 Intermediate Similarity NPD7549 Discontinued
0.8276 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD2801 Approved
0.8219 Intermediate Similarity NPD3027 Phase 3
0.8214 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8207 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD7054 Approved
0.8176 Intermediate Similarity NPD1934 Approved
0.8144 Intermediate Similarity NPD7472 Approved
0.8092 Intermediate Similarity NPD7266 Discontinued
0.8075 Intermediate Similarity NPD3817 Phase 2
0.8036 Intermediate Similarity NPD7074 Phase 3
0.8027 Intermediate Similarity NPD4908 Phase 1
0.8012 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD1465 Phase 2
0.7988 Intermediate Similarity NPD6797 Phase 2
0.7987 Intermediate Similarity NPD1652 Phase 2
0.7963 Intermediate Similarity NPD5402 Approved
0.7941 Intermediate Similarity NPD7251 Discontinued
0.7919 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD422 Phase 1
0.7917 Intermediate Similarity NPD3818 Discontinued
0.7895 Intermediate Similarity NPD7808 Phase 3
0.7881 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD5124 Phase 1
0.7818 Intermediate Similarity NPD6234 Discontinued
0.7811 Intermediate Similarity NPD7228 Approved
0.7805 Intermediate Similarity NPD3882 Suspended
0.7785 Intermediate Similarity NPD1511 Approved
0.7771 Intermediate Similarity NPD6190 Approved
0.7758 Intermediate Similarity NPD7075 Discontinued
0.7758 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD7199 Phase 2
0.7716 Intermediate Similarity NPD4380 Phase 2
0.7688 Intermediate Similarity NPD1512 Approved
0.7679 Intermediate Similarity NPD6232 Discontinued
0.7669 Intermediate Similarity NPD7411 Suspended
0.7665 Intermediate Similarity NPD5494 Approved
0.764 Intermediate Similarity NPD5403 Approved
0.7639 Intermediate Similarity NPD1548 Phase 1
0.7633 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD6233 Phase 2
0.7627 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD37 Approved
0.76 Intermediate Similarity NPD2861 Phase 2
0.7595 Intermediate Similarity NPD3750 Approved
0.759 Intermediate Similarity NPD4967 Phase 2
0.759 Intermediate Similarity NPD4966 Approved
0.759 Intermediate Similarity NPD4965 Approved
0.7578 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD1610 Phase 2
0.7544 Intermediate Similarity NPD7473 Discontinued
0.7531 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6559 Discontinued
0.7516 Intermediate Similarity NPD5401 Approved
0.7515 Intermediate Similarity NPD6801 Discontinued
0.7485 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7768 Phase 2
0.7483 Intermediate Similarity NPD3018 Phase 2
0.7483 Intermediate Similarity NPD3496 Discontinued
0.747 Intermediate Similarity NPD7819 Suspended
0.7468 Intermediate Similarity NPD4060 Phase 1
0.7457 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD7213 Phase 3
0.7453 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6799 Approved
0.7453 Intermediate Similarity NPD7212 Phase 2
0.7451 Intermediate Similarity NPD6798 Discontinued
0.7425 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD230 Phase 1
0.7412 Intermediate Similarity NPD6959 Discontinued
0.7412 Intermediate Similarity NPD8127 Discontinued
0.7407 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD7447 Phase 1
0.74 Intermediate Similarity NPD3225 Approved
0.7399 Intermediate Similarity NPD3751 Discontinued
0.7375 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD8455 Phase 2
0.7358 Intermediate Similarity NPD1549 Phase 2
0.7342 Intermediate Similarity NPD2935 Discontinued
0.7333 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2982 Phase 2
0.7333 Intermediate Similarity NPD2983 Phase 2
0.733 Intermediate Similarity NPD7240 Approved
0.733 Intermediate Similarity NPD7685 Pre-registration
0.7325 Intermediate Similarity NPD7097 Phase 1
0.7312 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD6674 Discontinued
0.7308 Intermediate Similarity NPD447 Suspended
0.7308 Intermediate Similarity NPD4340 Discontinued
0.7301 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD3748 Approved
0.7273 Intermediate Similarity NPD4625 Phase 3
0.7267 Intermediate Similarity NPD3787 Discontinued
0.7267 Intermediate Similarity NPD2981 Phase 2
0.7267 Intermediate Similarity NPD4628 Phase 3
0.7237 Intermediate Similarity NPD2797 Approved
0.7235 Intermediate Similarity NPD3749 Approved
0.7233 Intermediate Similarity NPD1551 Phase 2
0.7233 Intermediate Similarity NPD2796 Approved
0.7219 Intermediate Similarity NPD4749 Approved
0.72 Intermediate Similarity NPD1091 Approved
0.7193 Intermediate Similarity NPD919 Approved
0.7186 Intermediate Similarity NPD6599 Discontinued
0.717 Intermediate Similarity NPD1510 Phase 2
0.7161 Intermediate Similarity NPD7095 Approved
0.7158 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD228 Approved
0.7152 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD8312 Approved
0.7151 Intermediate Similarity NPD8313 Approved
0.7143 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7038 Approved
0.7135 Intermediate Similarity NPD7039 Approved
0.7134 Intermediate Similarity NPD4357 Discontinued
0.7126 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD3268 Approved
0.7115 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD8054 Approved
0.7111 Intermediate Similarity NPD8053 Approved
0.7103 Intermediate Similarity NPD5535 Approved
0.7099 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD5536 Phase 2
0.7089 Intermediate Similarity NPD6355 Discontinued
0.7089 Intermediate Similarity NPD1933 Approved
0.7075 Intermediate Similarity NPD6671 Approved
0.7066 Intermediate Similarity NPD3687 Approved
0.7066 Intermediate Similarity NPD3686 Approved
0.7063 Intermediate Similarity NPD7033 Discontinued
0.7055 Intermediate Similarity NPD8166 Discontinued
0.7053 Intermediate Similarity NPD7680 Approved
0.7052 Intermediate Similarity NPD5677 Discontinued
0.7035 Intermediate Similarity NPD6971 Discontinued
0.7025 Intermediate Similarity NPD1558 Phase 1
0.7021 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD1247 Approved
0.7005 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.6987 Remote Similarity NPD6832 Phase 2
0.6982 Remote Similarity NPD4675 Approved
0.6982 Remote Similarity NPD4678 Approved
0.6975 Remote Similarity NPD5762 Approved
0.6975 Remote Similarity NPD5763 Approved
0.6975 Remote Similarity NPD3540 Phase 1
0.6971 Remote Similarity NPD7229 Phase 3
0.6957 Remote Similarity NPD4308 Phase 3
0.6951 Remote Similarity NPD4110 Phase 3
0.6951 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6951 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6939 Remote Similarity NPD5283 Phase 1
0.6936 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6933 Remote Similarity NPD2424 Discontinued
0.6932 Remote Similarity NPD3926 Phase 2
0.6923 Remote Similarity NPD3226 Approved
0.6919 Remote Similarity NPD5353 Approved
0.6918 Remote Similarity NPD4140 Approved
0.6918 Remote Similarity NPD3620 Phase 2
0.6918 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1240 Approved
0.6915 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6032 Approved
0.6914 Remote Similarity NPD6100 Approved
0.6914 Remote Similarity NPD3539 Phase 1
0.6914 Remote Similarity NPD6099 Approved
0.6903 Remote Similarity NPD1203 Approved
0.6902 Remote Similarity NPD6842 Approved
0.6902 Remote Similarity NPD6843 Phase 3
0.6902 Remote Similarity NPD6841 Approved
0.6902 Remote Similarity NPD7906 Approved
0.6899 Remote Similarity NPD1296 Phase 2
0.6894 Remote Similarity NPD4536 Approved
0.6894 Remote Similarity NPD4538 Approved
0.6894 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6888 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6888 Remote Similarity NPD7783 Phase 2
0.6886 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1358 Approved
0.6875 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6871 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6863 Remote Similarity NPD1535 Discovery
0.6863 Remote Similarity NPD3705 Approved
0.6863 Remote Similarity NPD1611 Approved
0.6859 Remote Similarity NPD6584 Phase 3

Structure

External Identifiers

PubChem CID   44583434
ChEMBL   CHEMBL525988
ZINC  

Physicochemical Properties

Molecular Weight:  548.13
ALogP:  -1.3419
MLogP:  3.44
XLogP:  3.147
# Rotatable Bonds:  13
Polar Surface Area:  150.21
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  40

Download Data

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