Natural Product: NPC476642

Natural Product ID:  NPC476642
Common Name:   Terphenolide
IUPAC Name:   2-[3-[2-hydroxy-4-(4-hydroxyphenyl)-3,6-dimethoxyphenyl]-5-oxo-2H-furan-2-yl]acetic acid
Synonyms:   Terphenolide
Molecular Formula:   C20H18O8
Standard InCHIKey:  LZDLOICWXKFSMI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H18O8/c1-26-15-7-12(10-3-5-11(21)6-4-10)20(27-2)19(25)18(15)13-8-17(24)28-14(13)9-16(22)23/h3-8,14,21,25H,9H2,1-2H3,(H,22,23)
Canonical SMILES:  COc1cc(c2ccc(cc2)O)c(c(c1C1=CC(=O)OC1CC(=O)O)O)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
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota healthy leaf of Ginkgo biloba campus of Nanjing University, Nanjing, China 2008-OCT PMID[22196792]
NPO33649 Aspergillus sp. YXf3 Species Aspergillaceae Eukaryota isolated from a healthy leaf of Ginkgo biloba the campus of Nanjing University, Nanjing, China 2008-OCT PMID[22196792]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 5790 nM 22196792

  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 NPC476642 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
0.915 High Similarity NPC7178
0.915 High Similarity NPC62903
0.9108 High Similarity NPC55121
0.9108 High Similarity NPC174311
0.9091 High Similarity NPC142479
0.9091 High Similarity NPC155015
0.9062 High Similarity NPC476279
0.8961 High Similarity NPC476154
0.8947 High Similarity NPC125570
0.894 High Similarity NPC208507
0.894 High Similarity NPC472333
0.8896 High Similarity NPC95498
0.8896 High Similarity NPC246566
0.8896 High Similarity NPC476434
0.8868 High Similarity NPC476200
0.8868 High Similarity NPC192258
0.8846 High Similarity NPC125709
0.8846 High Similarity NPC292385
0.8839 High Similarity NPC199773
0.8839 High Similarity NPC473236
0.8839 High Similarity NPC289968
0.8831 High Similarity NPC225129
0.8824 High Similarity NPC113790
0.88 High Similarity NPC477696
0.88 High Similarity NPC273657
0.88 High Similarity NPC106920
0.88 High Similarity NPC477697
0.88 High Similarity NPC470811
0.879 High Similarity NPC227062
0.8758 High Similarity NPC139839
0.8742 High Similarity NPC16353
0.8733 High Similarity NPC472335
0.8733 High Similarity NPC472332
0.8718 High Similarity NPC178574
0.8718 High Similarity NPC65591
0.871 High Similarity NPC164527
0.871 High Similarity NPC213382
0.8701 High Similarity NPC55327
0.8701 High Similarity NPC474393
0.8701 High Similarity NPC474347
0.8693 High Similarity NPC275125
0.8693 High Similarity NPC170239
0.8693 High Similarity NPC97937
0.8684 High Similarity NPC223185
0.8679 High Similarity NPC45846
0.8671 High Similarity NPC150227
0.8667 High Similarity NPC19158
0.8667 High Similarity NPC470991
0.8662 High Similarity NPC298802
0.8662 High Similarity NPC136757
0.8654 High Similarity NPC477699
0.8645 High Similarity NPC285527
0.8645 High Similarity NPC106334
0.8645 High Similarity NPC470916
0.8634 High Similarity NPC42797
0.8634 High Similarity NPC473445
0.8627 High Similarity NPC474799
0.8625 High Similarity NPC130955
0.8625 High Similarity NPC301089
0.8625 High Similarity NPC292415
0.8618 High Similarity NPC87883
0.8618 High Similarity NPC27159
0.8616 High Similarity NPC162869
0.8616 High Similarity NPC143328
0.8616 High Similarity NPC36077
0.8616 High Similarity NPC474836
0.8616 High Similarity NPC475267
0.8616 High Similarity NPC77679
0.8616 High Similarity NPC156057
0.8616 High Similarity NPC190020
0.8616 High Similarity NPC474208
0.8616 High Similarity NPC84935
0.8616 High Similarity NPC48208
0.8609 High Similarity NPC469564
0.8608 High Similarity NPC238834
0.8608 High Similarity NPC16082
0.8608 High Similarity NPC286052
0.8608 High Similarity NPC79998
0.8608 High Similarity NPC199926
0.8608 High Similarity NPC82592
0.8599 High Similarity NPC295646
0.8589 High Similarity NPC472452
0.8589 High Similarity NPC20216
0.8581 High Similarity NPC30688
0.8581 High Similarity NPC176903
0.858 High Similarity NPC156082
0.858 High Similarity NPC477689
0.858 High Similarity NPC291977
0.8571 High Similarity NPC473106
0.8571 High Similarity NPC283081
0.8571 High Similarity NPC178129
0.8571 High Similarity NPC221383
0.8571 High Similarity NPC143892
0.8571 High Similarity NPC112418
0.8571 High Similarity NPC349525
0.8571 High Similarity NPC299090
0.8571 High Similarity NPC103201
0.8563 High Similarity NPC196771
0.8562 High Similarity NPC238381
0.8562 High Similarity NPC83763
0.8562 High Similarity NPC36354
0.8562 High Similarity NPC168616
0.8562 High Similarity NPC125617
0.8562 High Similarity NPC474982
0.8553 High Similarity NPC7439
0.8553 High Similarity NPC469474
0.8553 High Similarity NPC34245
0.8553 High Similarity NPC110067
0.8553 High Similarity NPC54928
0.8553 High Similarity NPC256555
0.8553 High Similarity NPC477616
0.8553 High Similarity NPC91492
0.8553 High Similarity NPC255106
0.8553 High Similarity NPC235165
0.8545 High Similarity NPC124470
0.8545 High Similarity NPC109827
0.8545 High Similarity NPC17219
0.8544 High Similarity NPC124714
0.8544 High Similarity NPC477299
0.8544 High Similarity NPC281477
0.8544 High Similarity NPC25127
0.8544 High Similarity NPC250557
0.8544 High Similarity NPC287504
0.8544 High Similarity NPC18727
0.8543 High Similarity NPC100675
0.8537 High Similarity NPC311912
0.8535 High Similarity NPC204350
0.8535 High Similarity NPC93498
0.8535 High Similarity NPC56184
0.8535 High Similarity NPC75695
0.8535 High Similarity NPC163883
0.8528 High Similarity NPC112981
0.8526 High Similarity NPC21184
0.8526 High Similarity NPC102003
0.8526 High Similarity NPC92722
0.8526 High Similarity NPC205727
0.8526 High Similarity NPC120426
0.8526 High Similarity NPC294522
0.8519 High Similarity NPC84515
0.8519 High Similarity NPC312056
0.8519 High Similarity NPC471745
0.8516 High Similarity NPC1580
0.8516 High Similarity NPC102934
0.8516 High Similarity NPC252402
0.8514 High Similarity NPC106406
0.8512 High Similarity NPC297807
0.8509 High Similarity NPC24627
0.8509 High Similarity NPC53889
0.8509 High Similarity NPC471744
0.8506 High Similarity NPC474054
0.8503 High Similarity NPC139350
0.85 High Similarity NPC99597
0.85 High Similarity NPC469584
0.85 High Similarity NPC472910
0.85 High Similarity NPC35598
0.85 High Similarity NPC472913
0.85 High Similarity NPC245758
0.85 High Similarity NPC222814
0.85 High Similarity NPC96167
0.85 High Similarity NPC472911
0.85 High Similarity NPC223787
0.85 High Similarity NPC210084
0.85 High Similarity NPC108456
0.85 High Similarity NPC470402
0.85 High Similarity NPC222689
0.85 High Similarity NPC472914
0.8494 Intermediate Similarity NPC247964
0.8494 Intermediate Similarity NPC158226
0.8491 Intermediate Similarity NPC280339
0.8491 Intermediate Similarity NPC213622
0.8491 Intermediate Similarity NPC183597
0.8491 Intermediate Similarity NPC167815
0.8491 Intermediate Similarity NPC196439
0.8491 Intermediate Similarity NPC138360
0.8491 Intermediate Similarity NPC4455
0.8491 Intermediate Similarity NPC201136
0.8491 Intermediate Similarity NPC163780
0.8491 Intermediate Similarity NPC37392
0.8491 Intermediate Similarity NPC50715
0.8491 Intermediate Similarity NPC146165
0.8491 Intermediate Similarity NPC92659
0.8491 Intermediate Similarity NPC227325
0.8491 Intermediate Similarity NPC128863
0.8491 Intermediate Similarity NPC2476
0.8491 Intermediate Similarity NPC476065
0.8485 Intermediate Similarity NPC117911
0.8485 Intermediate Similarity NPC88557
0.8481 Intermediate Similarity NPC146277
0.8481 Intermediate Similarity NPC291802
0.8481 Intermediate Similarity NPC75069
0.8481 Intermediate Similarity NPC181209
0.8481 Intermediate Similarity NPC131266
0.8481 Intermediate Similarity NPC149735
0.8481 Intermediate Similarity NPC19380
0.8481 Intermediate Similarity NPC216769
0.8481 Intermediate Similarity NPC245382
0.8481 Intermediate Similarity NPC474656
0.8481 Intermediate Similarity NPC475141
0.8481 Intermediate Similarity NPC121522
0.8481 Intermediate Similarity NPC35763

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476642 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
0.8519 High Similarity NPD6232 Discontinued
0.8481 Intermediate Similarity NPD1934 Approved
0.8447 Intermediate Similarity NPD6234 Discontinued
0.8428 Intermediate Similarity NPD2801 Approved
0.8373 Intermediate Similarity NPD5844 Phase 1
0.8364 Intermediate Similarity NPD7473 Discontinued
0.8323 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD3817 Phase 2
0.825 Intermediate Similarity NPD37 Approved
0.821 Intermediate Similarity NPD4967 Phase 2
0.821 Intermediate Similarity NPD4966 Approved
0.821 Intermediate Similarity NPD3882 Suspended
0.821 Intermediate Similarity NPD4965 Approved
0.8204 Intermediate Similarity NPD3818 Discontinued
0.8193 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD6166 Phase 2
0.8193 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD3027 Phase 3
0.8107 Intermediate Similarity NPD7074 Phase 3
0.8095 Intermediate Similarity NPD7228 Approved
0.8047 Intermediate Similarity NPD7054 Approved
0.8012 Intermediate Similarity NPD6559 Discontinued
0.8 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7472 Approved
0.8 Intermediate Similarity NPD1653 Approved
0.7987 Intermediate Similarity NPD2935 Discontinued
0.7975 Intermediate Similarity NPD1465 Phase 2
0.7975 Intermediate Similarity NPD1511 Approved
0.7952 Intermediate Similarity NPD5494 Approved
0.7939 Intermediate Similarity NPD7075 Discontinued
0.7927 Intermediate Similarity NPD5402 Approved
0.7925 Intermediate Similarity NPD2533 Approved
0.7925 Intermediate Similarity NPD2532 Approved
0.7925 Intermediate Similarity NPD2534 Approved
0.7904 Intermediate Similarity NPD7199 Phase 2
0.7901 Intermediate Similarity NPD4380 Phase 2
0.7901 Intermediate Similarity NPD6599 Discontinued
0.7895 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD1613 Approved
0.7875 Intermediate Similarity NPD1512 Approved
0.7862 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD6797 Phase 2
0.7848 Intermediate Similarity NPD6190 Approved
0.7829 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD7251 Discontinued
0.7785 Intermediate Similarity NPD4628 Phase 3
0.7771 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD7808 Phase 3
0.7758 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD7819 Suspended
0.7756 Intermediate Similarity NPD1551 Phase 2
0.775 Intermediate Similarity NPD6799 Approved
0.7748 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD230 Phase 1
0.7725 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD6801 Discontinued
0.7692 Intermediate Similarity NPD6959 Discontinued
0.7682 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD1607 Approved
0.7673 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD7768 Phase 2
0.7613 Intermediate Similarity NPD6355 Discontinued
0.7607 Intermediate Similarity NPD5403 Approved
0.76 Intermediate Similarity NPD7240 Approved
0.7595 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD1510 Phase 2
0.7574 Intermediate Similarity NPD919 Approved
0.7562 Intermediate Similarity NPD3750 Approved
0.7562 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD4110 Phase 3
0.7548 Intermediate Similarity NPD1240 Approved
0.7547 Intermediate Similarity NPD1549 Phase 2
0.7533 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD7411 Suspended
0.7514 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD447 Suspended
0.75 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3926 Phase 2
0.7485 Intermediate Similarity NPD1247 Approved
0.7485 Intermediate Similarity NPD5401 Approved
0.7485 Intermediate Similarity NPD8127 Discontinued
0.7484 Intermediate Similarity NPD7266 Discontinued
0.7484 Intermediate Similarity NPD6233 Phase 2
0.7457 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD943 Approved
0.7429 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD2438 Suspended
0.7421 Intermediate Similarity NPD2796 Approved
0.7419 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6798 Discontinued
0.7401 Intermediate Similarity NPD7685 Pre-registration
0.7374 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD3751 Discontinued
0.7358 Intermediate Similarity NPD7033 Discontinued
0.7346 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD3787 Discontinued
0.7341 Intermediate Similarity NPD5710 Approved
0.7341 Intermediate Similarity NPD5711 Approved
0.7338 Intermediate Similarity NPD2861 Phase 2
0.7338 Intermediate Similarity NPD3018 Phase 2
0.7333 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD6746 Phase 2
0.7325 Intermediate Similarity NPD4060 Phase 1
0.732 Intermediate Similarity NPD2797 Approved
0.7317 Intermediate Similarity NPD4357 Discontinued
0.7312 Intermediate Similarity NPD6100 Approved
0.7312 Intermediate Similarity NPD6099 Approved
0.731 Intermediate Similarity NPD3749 Approved
0.7305 Intermediate Similarity NPD3226 Approved
0.7299 Intermediate Similarity NPD5242 Approved
0.729 Intermediate Similarity NPD4908 Phase 1
0.7285 Intermediate Similarity NPD422 Phase 1
0.7273 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7549 Discontinued
0.7255 Intermediate Similarity NPD1283 Approved
0.725 Intermediate Similarity NPD3748 Approved
0.7244 Intermediate Similarity NPD4625 Phase 3
0.7241 Intermediate Similarity NPD7229 Phase 3
0.7239 Intermediate Similarity NPD8166 Discontinued
0.7235 Intermediate Similarity NPD8455 Phase 2
0.7222 Intermediate Similarity NPD8312 Approved
0.7222 Intermediate Similarity NPD8313 Approved
0.7219 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD2979 Phase 3
0.7211 Intermediate Similarity NPD7680 Approved
0.7202 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD8434 Phase 2
0.7197 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD3268 Approved
0.719 Intermediate Similarity NPD2983 Phase 2
0.719 Intermediate Similarity NPD2982 Phase 2
0.7186 Intermediate Similarity NPD920 Approved
0.7179 Intermediate Similarity NPD6832 Phase 2
0.7178 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1652 Phase 2
0.7171 Intermediate Similarity NPD1610 Phase 2
0.717 Intermediate Similarity NPD1933 Approved
0.716 Intermediate Similarity NPD2346 Discontinued
0.7152 Intermediate Similarity NPD4626 Approved
0.7143 Intermediate Similarity NPD2799 Discontinued
0.7124 Intermediate Similarity NPD2981 Phase 2
0.7124 Intermediate Similarity NPD1608 Approved
0.712 Intermediate Similarity NPD7435 Discontinued
0.7115 Intermediate Similarity NPD9494 Approved
0.7113 Intermediate Similarity NPD8151 Discontinued
0.7108 Intermediate Similarity NPD7390 Discontinued
0.7105 Intermediate Similarity NPD3496 Discontinued
0.7104 Intermediate Similarity NPD8150 Discontinued
0.7099 Intermediate Similarity NPD5405 Approved
0.7099 Intermediate Similarity NPD5404 Approved
0.7099 Intermediate Similarity NPD5408 Approved
0.7099 Intermediate Similarity NPD5406 Approved
0.7097 Intermediate Similarity NPD1203 Approved
0.7093 Intermediate Similarity NPD5353 Approved
0.7086 Intermediate Similarity NPD5691 Approved
0.7078 Intermediate Similarity NPD4749 Approved
0.7073 Intermediate Similarity NPD1243 Approved
0.7073 Intermediate Similarity NPD2800 Approved
0.7067 Intermediate Similarity NPD5536 Phase 2
0.7066 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD5124 Phase 1
0.7063 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1535 Discovery
0.7059 Intermediate Similarity NPD1281 Approved
0.7056 Intermediate Similarity NPD5953 Discontinued
0.7055 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD6002 Phase 3
0.7055 Intermediate Similarity NPD5762 Approved
0.7055 Intermediate Similarity NPD5763 Approved
0.7055 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD6005 Phase 3
0.7055 Intermediate Similarity NPD6004 Phase 3
0.7053 Intermediate Similarity NPD6778 Approved
0.7053 Intermediate Similarity NPD6776 Approved
0.7053 Intermediate Similarity NPD6780 Approved
0.7053 Intermediate Similarity NPD6781 Approved
0.7053 Intermediate Similarity NPD6782 Approved
0.7053 Intermediate Similarity NPD6779 Approved
0.7053 Intermediate Similarity NPD6777 Approved
0.7048 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD4062 Phase 3
0.7041 Intermediate Similarity NPD7783 Phase 2
0.7041 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD1778 Approved
0.7037 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4308 Phase 3
0.703 Intermediate Similarity NPD7003 Approved
0.7027 Intermediate Similarity NPD5283 Phase 1

Structure

External Identifiers

PubChem CID   45782753
ChEMBL   CHEMBL1951869
ZINC  

Physicochemical Properties

Molecular Weight:  386.10
ALogP:  -1.2052
MLogP:  2.78
XLogP:  1.065
# Rotatable Bonds:  11
Polar Surface Area:  122.52
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  28

Download Data

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Biological Activities  
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