Natural Product: NPC46192

Natural Product ID:  NPC46192
Common Name:   Pinillidine
IUPAC Name:   6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3-[1-[6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-yl]ethyl]-4-hydroxypyran-2-one
Synonyms:  
Molecular Formula:   C28H22O10
Standard InCHIKey:  AVRSGNZNZIKDCF-YPCIICBESA-N
Standard InCHI:  InChI=1S/C28H22O10/c1-14(25-23(33)12-17(37-27(25)35)6-2-15-4-8-19(29)21(31)10-15)26-24(34)13-18(38-28(26)36)7-3-16-5-9-20(30)22(32)11-16/h2-14,29-34H,1H3/b6-2+,7-3+
Canonical SMILES:  Oc1cc(/C=C/c2ccc(c(c2)O)O)oc(=O)c1C(c1c(O)cc(oc1=O)/C=C/c1ccc(c(c1)O)O)C
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
NPO19202 Phaeolus schweinitzii Species Hymenochaetaceae Eukaryota fruits Tibetan Plateau, China PMID[23869482]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT625 Tissue Liver Mus musculus IC50 > 200000 nM 11325222
NPT1 Others Radical scavenging activity IC50 > 200000 nM 15568791

  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 NPC46192 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
0.9918 High Similarity NPC208536
0.9918 High Similarity NPC64111
0.9837 High Similarity NPC285361
0.9836 High Similarity NPC167463
0.912 High Similarity NPC197832
0.9113 High Similarity NPC306100
0.8968 High Similarity NPC67951
0.896 High Similarity NPC285345
0.8898 High Similarity NPC118584
0.8881 High Similarity NPC191280
0.8837 High Similarity NPC477300
0.8686 High Similarity NPC285550
0.8676 High Similarity NPC9218
0.8623 High Similarity NPC183824
0.8613 High Similarity NPC91546
0.8595 High Similarity NPC131530
0.854 High Similarity NPC290664
0.8516 High Similarity NPC212541
0.8504 High Similarity NPC147654
0.8489 Intermediate Similarity NPC470130
0.8444 Intermediate Similarity NPC311742
0.8444 Intermediate Similarity NPC477301
0.8433 Intermediate Similarity NPC168799
0.8433 Intermediate Similarity NPC155209
0.8425 Intermediate Similarity NPC470848
0.8425 Intermediate Similarity NPC470849
0.8413 Intermediate Similarity NPC141791
0.8413 Intermediate Similarity NPC263386
0.8413 Intermediate Similarity NPC241634
0.8387 Intermediate Similarity NPC474967
0.838 Intermediate Similarity NPC17042
0.838 Intermediate Similarity NPC155910
0.838 Intermediate Similarity NPC1580
0.837 Intermediate Similarity NPC106406
0.8359 Intermediate Similarity NPC472271
0.8358 Intermediate Similarity NPC18074
0.8358 Intermediate Similarity NPC25581
0.8358 Intermediate Similarity NPC5419
0.8358 Intermediate Similarity NPC61
0.8345 Intermediate Similarity NPC296643
0.8333 Intermediate Similarity NPC275519
0.832 Intermediate Similarity NPC281277
0.8309 Intermediate Similarity NPC476870
0.8308 Intermediate Similarity NPC246704
0.8308 Intermediate Similarity NPC85565
0.8308 Intermediate Similarity NPC288945
0.8306 Intermediate Similarity NPC261453
0.8306 Intermediate Similarity NPC33749
0.8306 Intermediate Similarity NPC328593
0.8284 Intermediate Similarity NPC198388
0.8271 Intermediate Similarity NPC94810
0.8252 Intermediate Similarity NPC23677
0.8248 Intermediate Similarity NPC156307
0.8244 Intermediate Similarity NPC289459
0.824 Intermediate Similarity NPC233669
0.8226 Intermediate Similarity NPC95381
0.8211 Intermediate Similarity NPC226250
0.8203 Intermediate Similarity NPC2058
0.8201 Intermediate Similarity NPC289690
0.8201 Intermediate Similarity NPC288452
0.8189 Intermediate Similarity NPC203124
0.8189 Intermediate Similarity NPC309434
0.8182 Intermediate Similarity NPC213552
0.8182 Intermediate Similarity NPC120225
0.8182 Intermediate Similarity NPC276014
0.8156 Intermediate Similarity NPC192831
0.8156 Intermediate Similarity NPC258469
0.8156 Intermediate Similarity NPC277315
0.8156 Intermediate Similarity NPC472016
0.8156 Intermediate Similarity NPC43158
0.8151 Intermediate Similarity NPC270268
0.8148 Intermediate Similarity NPC318799
0.8145 Intermediate Similarity NPC51698
0.8143 Intermediate Similarity NPC477279
0.8134 Intermediate Similarity NPC83062
0.8125 Intermediate Similarity NPC70084
0.8116 Intermediate Similarity NPC471283
0.8116 Intermediate Similarity NPC90431
0.811 Intermediate Similarity NPC145023
0.811 Intermediate Similarity NPC175799
0.811 Intermediate Similarity NPC200988
0.811 Intermediate Similarity NPC610
0.8102 Intermediate Similarity NPC248150
0.8102 Intermediate Similarity NPC135127
0.8092 Intermediate Similarity NPC229084
0.8092 Intermediate Similarity NPC160900
0.8092 Intermediate Similarity NPC18984
0.8092 Intermediate Similarity NPC106659
0.8085 Intermediate Similarity NPC13818
0.8085 Intermediate Similarity NPC477278
0.8085 Intermediate Similarity NPC206095
0.8085 Intermediate Similarity NPC477335
0.8085 Intermediate Similarity NPC35702
0.8085 Intermediate Similarity NPC477277
0.8085 Intermediate Similarity NPC471027
0.8085 Intermediate Similarity NPC224389
0.8085 Intermediate Similarity NPC297517
0.8077 Intermediate Similarity NPC70752
0.8074 Intermediate Similarity NPC237506
0.8074 Intermediate Similarity NPC32626
0.8074 Intermediate Similarity NPC329344
0.8074 Intermediate Similarity NPC217052
0.8071 Intermediate Similarity NPC205751
0.8071 Intermediate Similarity NPC303683
0.8071 Intermediate Similarity NPC476820
0.8071 Intermediate Similarity NPC26241
0.8071 Intermediate Similarity NPC274891
0.8071 Intermediate Similarity NPC295492
0.8071 Intermediate Similarity NPC476819
0.8071 Intermediate Similarity NPC474875
0.806 Intermediate Similarity NPC110313
0.8058 Intermediate Similarity NPC471152
0.8047 Intermediate Similarity NPC86198
0.8045 Intermediate Similarity NPC84076
0.8045 Intermediate Similarity NPC90128
0.8045 Intermediate Similarity NPC303680
0.8042 Intermediate Similarity NPC477333
0.8031 Intermediate Similarity NPC299252
0.8031 Intermediate Similarity NPC277394
0.8031 Intermediate Similarity NPC61062
0.8029 Intermediate Similarity NPC471749
0.8028 Intermediate Similarity NPC319628
0.8028 Intermediate Similarity NPC37331
0.8028 Intermediate Similarity NPC220664
0.8028 Intermediate Similarity NPC303090
0.8028 Intermediate Similarity NPC284948
0.8016 Intermediate Similarity NPC217472
0.8014 Intermediate Similarity NPC38473
0.8014 Intermediate Similarity NPC326065
0.8014 Intermediate Similarity NPC69367
0.8 Intermediate Similarity NPC189844
0.8 Intermediate Similarity NPC142703
0.8 Intermediate Similarity NPC152942
0.8 Intermediate Similarity NPC204466
0.8 Intermediate Similarity NPC68092
0.8 Intermediate Similarity NPC219428
0.8 Intermediate Similarity NPC472350
0.8 Intermediate Similarity NPC278068
0.8 Intermediate Similarity NPC269843
0.8 Intermediate Similarity NPC197316
0.8 Intermediate Similarity NPC89105
0.8 Intermediate Similarity NPC109083
0.8 Intermediate Similarity NPC60962
0.8 Intermediate Similarity NPC14007
0.8 Intermediate Similarity NPC158949
0.8 Intermediate Similarity NPC476383
0.8 Intermediate Similarity NPC224814
0.8 Intermediate Similarity NPC284409
0.8 Intermediate Similarity NPC37250
0.8 Intermediate Similarity NPC64141
0.8 Intermediate Similarity NPC302857
0.8 Intermediate Similarity NPC81515
0.8 Intermediate Similarity NPC226855
0.8 Intermediate Similarity NPC241354
0.7986 Intermediate Similarity NPC120852
0.7985 Intermediate Similarity NPC123722
0.7985 Intermediate Similarity NPC158654
0.7985 Intermediate Similarity NPC276466
0.7985 Intermediate Similarity NPC151167
0.7985 Intermediate Similarity NPC123228
0.7985 Intermediate Similarity NPC5018
0.7984 Intermediate Similarity NPC109371
0.7984 Intermediate Similarity NPC470214
0.7984 Intermediate Similarity NPC470215
0.7972 Intermediate Similarity NPC160378
0.7971 Intermediate Similarity NPC68779
0.7971 Intermediate Similarity NPC300776
0.7971 Intermediate Similarity NPC5310
0.7971 Intermediate Similarity NPC4982
0.7971 Intermediate Similarity NPC886
0.7971 Intermediate Similarity NPC111635
0.7971 Intermediate Similarity NPC34293
0.7971 Intermediate Similarity NPC176814
0.7971 Intermediate Similarity NPC287597
0.797 Intermediate Similarity NPC280767
0.7969 Intermediate Similarity NPC65791
0.7959 Intermediate Similarity NPC243891
0.7958 Intermediate Similarity NPC67467
0.7956 Intermediate Similarity NPC473285
0.7951 Intermediate Similarity NPC1075
0.7951 Intermediate Similarity NPC294902
0.7951 Intermediate Similarity NPC1786
0.7943 Intermediate Similarity NPC134969
0.7943 Intermediate Similarity NPC475530
0.7943 Intermediate Similarity NPC471875
0.7943 Intermediate Similarity NPC106055
0.7943 Intermediate Similarity NPC473799
0.7943 Intermediate Similarity NPC110699
0.7937 Intermediate Similarity NPC264558
0.7937 Intermediate Similarity NPC148969
0.7931 Intermediate Similarity NPC322660
0.7929 Intermediate Similarity NPC126206
0.7929 Intermediate Similarity NPC260425
0.7929 Intermediate Similarity NPC78363
0.7929 Intermediate Similarity NPC474886
0.7929 Intermediate Similarity NPC281780
0.7926 Intermediate Similarity NPC478215
0.7923 Intermediate Similarity NPC202474
0.792 Intermediate Similarity NPC297657
0.7917 Intermediate Similarity NPC53520

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC46192 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
0.8092 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8028 Intermediate Similarity NPD6190 Approved
0.8 Intermediate Similarity NPD7266 Discontinued
0.7895 Intermediate Similarity NPD3225 Approved
0.7832 Intermediate Similarity NPD8166 Discontinued
0.776 Intermediate Similarity NPD3022 Approved
0.776 Intermediate Similarity NPD3021 Approved
0.7671 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD230 Phase 1
0.7557 Intermediate Similarity NPD5536 Phase 2
0.7468 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD1511 Approved
0.7429 Intermediate Similarity NPD3268 Approved
0.7368 Intermediate Similarity NPD9545 Approved
0.7357 Intermediate Similarity NPD7095 Approved
0.7353 Intermediate Similarity NPD1608 Approved
0.7338 Intermediate Similarity NPD9494 Approved
0.7338 Intermediate Similarity NPD2801 Approved
0.7333 Intermediate Similarity NPD1512 Approved
0.7319 Intermediate Similarity NPD2797 Approved
0.7305 Intermediate Similarity NPD3764 Approved
0.7301 Intermediate Similarity NPD7685 Pre-registration
0.729 Intermediate Similarity NPD3817 Phase 2
0.7234 Intermediate Similarity NPD3027 Phase 3
0.7231 Intermediate Similarity NPD228 Approved
0.723 Intermediate Similarity NPD4628 Phase 3
0.7226 Intermediate Similarity NPD9269 Phase 2
0.7226 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD4060 Phase 1
0.719 Intermediate Similarity NPD3455 Phase 2
0.7163 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD1934 Approved
0.7152 Intermediate Similarity NPD6234 Discontinued
0.7132 Intermediate Similarity NPD17 Approved
0.7132 Intermediate Similarity NPD1778 Approved
0.7124 Intermediate Similarity NPD1653 Approved
0.7121 Intermediate Similarity NPD5283 Phase 1
0.7117 Intermediate Similarity NPD7054 Approved
0.7115 Intermediate Similarity NPD1465 Phase 2
0.7114 Intermediate Similarity NPD3750 Approved
0.7109 Intermediate Similarity NPD3134 Approved
0.7095 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD5736 Approved
0.7087 Intermediate Similarity NPD5909 Discontinued
0.7083 Intermediate Similarity NPD943 Approved
0.7083 Intermediate Similarity NPD826 Approved
0.7083 Intermediate Similarity NPD825 Approved
0.708 Intermediate Similarity NPD3847 Discontinued
0.7075 Intermediate Similarity NPD2935 Discontinued
0.7073 Intermediate Similarity NPD7472 Approved
0.7071 Intermediate Similarity NPD3266 Approved
0.7071 Intermediate Similarity NPD3267 Approved
0.7063 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6798 Discontinued
0.7059 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD5585 Approved
0.7054 Intermediate Similarity NPD1358 Approved
0.7048 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD5535 Approved
0.704 Intermediate Similarity NPD3020 Approved
0.7037 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6166 Phase 2
0.7034 Intermediate Similarity NPD6355 Discontinued
0.7034 Intermediate Similarity NPD4340 Discontinued
0.703 Intermediate Similarity NPD6797 Phase 2
0.7029 Intermediate Similarity NPD422 Phase 1
0.7029 Intermediate Similarity NPD1535 Discovery
0.7025 Intermediate Similarity NPD3882 Suspended
0.7024 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD257 Approved
0.7021 Intermediate Similarity NPD258 Approved
0.7019 Intermediate Similarity NPD6232 Discontinued
0.7014 Intermediate Similarity NPD6233 Phase 2
0.7 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4110 Phase 3
0.7 Intermediate Similarity NPD1283 Approved
0.6994 Remote Similarity NPD7473 Discontinued
0.6992 Remote Similarity NPD2934 Approved
0.6992 Remote Similarity NPD2933 Approved
0.6988 Remote Similarity NPD7251 Discontinued
0.6978 Remote Similarity NPD1481 Phase 2
0.697 Remote Similarity NPD7074 Phase 3
0.6966 Remote Similarity NPD1613 Approved
0.6966 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7199 Phase 2
0.6951 Remote Similarity NPD3818 Discontinued
0.6951 Remote Similarity NPD7228 Approved
0.6943 Remote Similarity NPD37 Approved
0.6935 Remote Similarity NPD2859 Approved
0.6935 Remote Similarity NPD2860 Approved
0.6934 Remote Similarity NPD9268 Approved
0.6929 Remote Similarity NPD2983 Phase 2
0.6929 Remote Similarity NPD2982 Phase 2
0.6928 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6928 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6923 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4380 Phase 2
0.6918 Remote Similarity NPD555 Phase 2
0.6918 Remote Similarity NPD447 Suspended
0.6918 Remote Similarity NPD4965 Approved
0.6918 Remote Similarity NPD4966 Approved
0.6918 Remote Similarity NPD4967 Phase 2
0.6897 Remote Similarity NPD259 Phase 1
0.6897 Remote Similarity NPD4062 Phase 3
0.6897 Remote Similarity NPD6663 Approved
0.6892 Remote Similarity NPD2799 Discontinued
0.6892 Remote Similarity NPD7033 Discontinued
0.6887 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6884 Remote Similarity NPD3019 Approved
0.6884 Remote Similarity NPD2932 Approved
0.6884 Remote Similarity NPD4626 Approved
0.6879 Remote Similarity NPD7411 Suspended
0.6875 Remote Similarity NPD7075 Discontinued
0.6871 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6863 Remote Similarity NPD4357 Discontinued
0.6861 Remote Similarity NPD1894 Discontinued
0.6859 Remote Similarity NPD3226 Approved
0.6857 Remote Similarity NPD2981 Phase 2
0.6855 Remote Similarity NPD5402 Approved
0.6853 Remote Similarity NPD9569 Approved
0.6852 Remote Similarity NPD8127 Discontinued
0.685 Remote Similarity NPD1242 Phase 1
0.6849 Remote Similarity NPD1558 Phase 1
0.6845 Remote Similarity NPD7808 Phase 3
0.6839 Remote Similarity NPD5403 Approved
0.6835 Remote Similarity NPD3496 Discontinued
0.6831 Remote Similarity NPD1203 Approved
0.6824 Remote Similarity NPD7097 Phase 1
0.6818 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6809 Remote Similarity NPD4359 Approved
0.6807 Remote Similarity NPD5844 Phase 1
0.6806 Remote Similarity NPD2614 Approved
0.6806 Remote Similarity NPD4908 Phase 1
0.6803 Remote Similarity NPD5124 Phase 1
0.6803 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6802 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6792 Remote Similarity NPD7819 Suspended
0.6786 Remote Similarity NPD1281 Approved
0.6783 Remote Similarity NPD2798 Approved
0.6779 Remote Similarity NPD4308 Phase 3
0.6779 Remote Similarity NPD1510 Phase 2
0.6779 Remote Similarity NPD3748 Approved
0.6776 Remote Similarity NPD7003 Approved
0.6774 Remote Similarity NPD6273 Approved
0.6772 Remote Similarity NPD6386 Approved
0.6772 Remote Similarity NPD6385 Approved
0.677 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6757 Remote Similarity NPD6653 Approved
0.6753 Remote Similarity NPD6799 Approved
0.6752 Remote Similarity NPD7458 Discontinued
0.675 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6736 Remote Similarity NPD3018 Phase 2
0.6736 Remote Similarity NPD2861 Phase 2
0.6735 Remote Similarity NPD2979 Phase 3
0.6735 Remote Similarity NPD3620 Phase 2
0.6735 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5405 Approved
0.6733 Remote Similarity NPD2438 Suspended
0.6733 Remote Similarity NPD5406 Approved
0.6733 Remote Similarity NPD5408 Approved
0.6733 Remote Similarity NPD5404 Approved
0.673 Remote Similarity NPD6801 Discontinued
0.6715 Remote Similarity NPD9493 Approved
0.6712 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6712 Remote Similarity NPD2313 Discontinued
0.671 Remote Similarity NPD5401 Approved
0.6709 Remote Similarity NPD7028 Phase 2
0.6691 Remote Similarity NPD1357 Approved
0.6691 Remote Similarity NPD5691 Approved
0.669 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6689 Remote Similarity NPD274 Approved
0.6689 Remote Similarity NPD275 Approved
0.6689 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6689 Remote Similarity NPD1933 Approved
0.6687 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8032 Phase 2
0.6644 Remote Similarity NPD9536 Phase 1
0.6644 Remote Similarity NPD9537 Phase 1
0.6642 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6627 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6623 Remote Similarity NPD6099 Approved
0.6623 Remote Similarity NPD2354 Approved
0.6623 Remote Similarity NPD6100 Approved
0.6623 Remote Similarity NPD1551 Phase 2
0.6622 Remote Similarity NPD1240 Approved
0.6622 Remote Similarity NPD4140 Approved
0.662 Remote Similarity NPD9717 Approved
0.6619 Remote Similarity NPD1548 Phase 1
0.6605 Remote Similarity NPD7768 Phase 2
0.66 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6599 Remote Similarity NPD3145 Approved
0.6599 Remote Similarity NPD3144 Approved
0.6597 Remote Similarity NPD3053 Approved
0.6597 Remote Similarity NPD3055 Approved
0.6582 Remote Similarity NPD2370 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   54683773
ChEMBL   CHEMBL2408938
ZINC  

Physicochemical Properties

Molecular Weight:  518.12
ALogP:  -1.2224
MLogP:  3.44
XLogP:  3.656
# Rotatable Bonds:  13
Polar Surface Area:  173.98
# H-Bond Aceptor:  6
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  38

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Biological Activities  
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