Natural Product: NPC116922

Natural Product ID:  NPC116922
Common Name:   Triphyllin A
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[[(2S,4R)-4-hydroxy-6-(hydroxymethyl)-2-(4-methoxyphenyl)-8-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Molecular Formula:   C30H40O16
Standard InCHIKey:  KIOGDCNEFKPDDB-HSKOKGOGSA-N
Standard InCHI:  InChI=1S/C30H40O16/c1-11-26(45-29-24(39)22(37)20(35)17(9-32)43-29)14(8-31)28(46-30-25(40)23(38)21(36)18(10-33)44-30)19-15(34)7-16(42-27(11)19)12-3-5-13(41-2)6-4-12/h3-6,15-18,20-25,29-40H,7-10H2,1-2H3/t15-,16+,17-,18-,20-,21-,22+,23+,24-,25-,29+,30+/m1/s1
Canonical SMILES:  COc1ccc(cc1)[C@@H]1C[C@@H](O)c2c(O1)c(C)c(c(c2O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)CO)O[C@@H]1O[C@H](CO)[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
NPO16914 Abacopteris penangiana NA NA NA Aerial parts Jiangxi Province, China 2004-JUN PMID[17922550]
NPO16914 Abacopteris penangiana NA NA NA Rhizomes PMID[16499328]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens IC50 = 5.7 ug/ml 25646964

  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 NPC116922 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
0.9926 High Similarity NPC225445
0.9781 High Similarity NPC177597
0.9493 High Similarity NPC5253
0.9493 High Similarity NPC128337
0.9493 High Similarity NPC49542
0.9493 High Similarity NPC139976
0.9493 High Similarity NPC230718
0.9493 High Similarity NPC84207
0.9485 High Similarity NPC87777
0.9485 High Similarity NPC262328
0.9231 High Similarity NPC280945
0.9225 High Similarity NPC107120
0.9225 High Similarity NPC74320
0.9172 High Similarity NPC259707
0.9172 High Similarity NPC473621
0.9161 High Similarity NPC15538
0.9161 High Similarity NPC473480
0.9143 High Similarity NPC257095
0.9143 High Similarity NPC89686
0.9143 High Similarity NPC108674
0.9143 High Similarity NPC273932
0.9091 High Similarity NPC155564
0.9091 High Similarity NPC102280
0.9091 High Similarity NPC248053
0.9078 High Similarity NPC472353
0.9007 High Similarity NPC210192
0.8993 High Similarity NPC165482
0.8993 High Similarity NPC40664
0.8993 High Similarity NPC469383
0.8993 High Similarity NPC3293
0.8993 High Similarity NPC197723
0.8993 High Similarity NPC138350
0.8958 High Similarity NPC125755
0.8951 High Similarity NPC138227
0.8951 High Similarity NPC469313
0.8951 High Similarity NPC168579
0.8951 High Similarity NPC76176
0.8921 High Similarity NPC79957
0.8921 High Similarity NPC238243
0.8912 High Similarity NPC471403
0.8905 High Similarity NPC103799
0.8889 High Similarity NPC226722
0.8889 High Similarity NPC277867
0.8889 High Similarity NPC475096
0.8889 High Similarity NPC161700
0.8881 High Similarity NPC37793
0.8874 High Similarity NPC185231
0.8851 High Similarity NPC59692
0.8849 High Similarity NPC130496
0.8849 High Similarity NPC188555
0.8836 High Similarity NPC270751
0.8794 High Similarity NPC134260
0.8777 High Similarity NPC215037
0.8777 High Similarity NPC294166
0.8777 High Similarity NPC115022
0.8768 High Similarity NPC475067
0.8767 High Similarity NPC227902
0.8767 High Similarity NPC87950
0.8767 High Similarity NPC471764
0.8741 High Similarity NPC5155
0.8741 High Similarity NPC277331
0.8741 High Similarity NPC100482
0.8732 High Similarity NPC475836
0.8725 High Similarity NPC226108
0.8725 High Similarity NPC46283
0.8725 High Similarity NPC44192
0.8725 High Similarity NPC469944
0.8725 High Similarity NPC134911
0.8725 High Similarity NPC272552
0.8725 High Similarity NPC322899
0.8716 High Similarity NPC472710
0.8716 High Similarity NPC472709
0.8716 High Similarity NPC107197
0.8705 High Similarity NPC165686
0.8705 High Similarity NPC85799
0.8705 High Similarity NPC26080
0.8705 High Similarity NPC303422
0.8701 High Similarity NPC190450
0.8699 High Similarity NPC190714
0.8699 High Similarity NPC99515
0.869 High Similarity NPC475492
0.8686 High Similarity NPC222572
0.8686 High Similarity NPC274717
0.8686 High Similarity NPC87224
0.8684 High Similarity NPC73517
0.8684 High Similarity NPC147743
0.8684 High Similarity NPC4809
0.8681 High Similarity NPC469559
0.8681 High Similarity NPC475084
0.8681 High Similarity NPC189115
0.8676 High Similarity NPC276212
0.8643 High Similarity NPC92805
0.8633 High Similarity NPC121376
0.863 High Similarity NPC85624
0.863 High Similarity NPC43508
0.863 High Similarity NPC476301
0.8627 High Similarity NPC159526
0.8627 High Similarity NPC106601
0.8627 High Similarity NPC471404
0.8627 High Similarity NPC205613
0.8627 High Similarity NPC212614
0.8627 High Similarity NPC151474
0.8627 High Similarity NPC86630
0.8621 High Similarity NPC473044
0.8611 High Similarity NPC469661
0.8603 High Similarity NPC278552
0.8603 High Similarity NPC103420
0.8603 High Similarity NPC285040
0.8603 High Similarity NPC102540
0.8603 High Similarity NPC167571
0.8603 High Similarity NPC17809
0.8603 High Similarity NPC188022
0.8603 High Similarity NPC207179
0.86 High Similarity NPC21902
0.86 High Similarity NPC233467
0.86 High Similarity NPC302610
0.8592 High Similarity NPC262585
0.8592 High Similarity NPC20829
0.8592 High Similarity NPC18189
0.8592 High Similarity NPC164857
0.8582 High Similarity NPC117048
0.8582 High Similarity NPC124085
0.8581 High Similarity NPC169510
0.8581 High Similarity NPC175976
0.8571 High Similarity NPC142860
0.8571 High Similarity NPC271270
0.8571 High Similarity NPC246469
0.8571 High Similarity NPC97285
0.8562 High Similarity NPC79429
0.8562 High Similarity NPC471667
0.8562 High Similarity NPC217635
0.8562 High Similarity NPC473045
0.8562 High Similarity NPC25292
0.8561 High Similarity NPC474491
0.8561 High Similarity NPC262606
0.8543 High Similarity NPC306267
0.8543 High Similarity NPC20050
0.8542 High Similarity NPC106944
0.8531 High Similarity NPC124149
0.8529 High Similarity NPC134195
0.8529 High Similarity NPC246648
0.8529 High Similarity NPC197351
0.8529 High Similarity NPC106914
0.8529 High Similarity NPC86502
0.8526 High Similarity NPC124155
0.8526 High Similarity NPC257566
0.8523 High Similarity NPC295573
0.8523 High Similarity NPC55715
0.8523 High Similarity NPC470208
0.8523 High Similarity NPC95392
0.8523 High Similarity NPC35877
0.8521 High Similarity NPC470236
0.8519 High Similarity NPC476142
0.8514 High Similarity NPC39657
0.8514 High Similarity NPC193473
0.8514 High Similarity NPC213074
0.8514 High Similarity NPC31325
0.8514 High Similarity NPC275284
0.8514 High Similarity NPC15956
0.8514 High Similarity NPC114505
0.8514 High Similarity NPC224674
0.8514 High Similarity NPC296377
0.8511 High Similarity NPC85435
0.8493 Intermediate Similarity NPC252169
0.8489 Intermediate Similarity NPC93962
0.8489 Intermediate Similarity NPC218003
0.8478 Intermediate Similarity NPC149796
0.8477 Intermediate Similarity NPC476352
0.8477 Intermediate Similarity NPC215060
0.8477 Intermediate Similarity NPC53587
0.8477 Intermediate Similarity NPC176186
0.8477 Intermediate Similarity NPC279406
0.8477 Intermediate Similarity NPC169404
0.8477 Intermediate Similarity NPC226809
0.8472 Intermediate Similarity NPC98777
0.8472 Intermediate Similarity NPC212770
0.8467 Intermediate Similarity NPC260781
0.8467 Intermediate Similarity NPC9933
0.8467 Intermediate Similarity NPC182368
0.8467 Intermediate Similarity NPC145979
0.8467 Intermediate Similarity NPC469706
0.8467 Intermediate Similarity NPC238140
0.8467 Intermediate Similarity NPC185955
0.8467 Intermediate Similarity NPC218041
0.8467 Intermediate Similarity NPC469707
0.8467 Intermediate Similarity NPC214326
0.8467 Intermediate Similarity NPC225815
0.8462 Intermediate Similarity NPC242028
0.8462 Intermediate Similarity NPC475382
0.8462 Intermediate Similarity NPC3049
0.8462 Intermediate Similarity NPC44947
0.8462 Intermediate Similarity NPC470802
0.8462 Intermediate Similarity NPC166180
0.8462 Intermediate Similarity NPC203230
0.8456 Intermediate Similarity NPC38761
0.8456 Intermediate Similarity NPC76465
0.8456 Intermediate Similarity NPC472339
0.8452 Intermediate Similarity NPC100936
0.8452 Intermediate Similarity NPC1253
0.8451 Intermediate Similarity NPC13745

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC116922 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
0.8444 Intermediate Similarity NPD1091 Approved
0.8366 Intermediate Similarity NPD8455 Phase 2
0.8313 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8298 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1613 Approved
0.8182 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8156 Intermediate Similarity NPD4908 Phase 1
0.8148 Intermediate Similarity NPD7074 Phase 3
0.8089 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD7472 Approved
0.7987 Intermediate Similarity NPD6674 Discontinued
0.7975 Intermediate Similarity NPD7054 Approved
0.7939 Intermediate Similarity NPD7251 Discontinued
0.7914 Intermediate Similarity NPD1610 Phase 2
0.7902 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD7808 Phase 3
0.7883 Intermediate Similarity NPD1548 Phase 1
0.7879 Intermediate Similarity NPD6797 Phase 2
0.7877 Intermediate Similarity NPD5124 Phase 1
0.7877 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD3027 Phase 3
0.7832 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD5058 Phase 3
0.7806 Intermediate Similarity NPD1653 Approved
0.7805 Intermediate Similarity NPD7228 Approved
0.777 Intermediate Similarity NPD7097 Phase 1
0.7733 Intermediate Similarity NPD7266 Discontinued
0.7725 Intermediate Similarity NPD6559 Discontinued
0.7707 Intermediate Similarity NPD4380 Phase 2
0.7671 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD4536 Approved
0.7651 Intermediate Similarity NPD4538 Approved
0.7651 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD7075 Discontinued
0.7632 Intermediate Similarity NPD1652 Phase 2
0.7632 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD8651 Approved
0.7619 Intermediate Similarity NPD7240 Approved
0.7603 Intermediate Similarity NPD4625 Phase 3
0.7574 Intermediate Similarity NPD7843 Approved
0.7562 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD7213 Phase 3
0.7548 Intermediate Similarity NPD7212 Phase 2
0.7547 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7447 Phase 1
0.75 Intermediate Similarity NPD6801 Discontinued
0.75 Intermediate Similarity NPD37 Approved
0.7485 Intermediate Similarity NPD3818 Discontinued
0.7483 Intermediate Similarity NPD5960 Phase 3
0.7483 Intermediate Similarity NPD5588 Approved
0.747 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD6166 Phase 2
0.747 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD4965 Approved
0.7469 Intermediate Similarity NPD4967 Phase 2
0.7469 Intermediate Similarity NPD4966 Approved
0.7466 Intermediate Similarity NPD2861 Phase 2
0.7453 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD7411 Suspended
0.7427 Intermediate Similarity NPD8312 Approved
0.7427 Intermediate Similarity NPD8313 Approved
0.741 Intermediate Similarity NPD7157 Approved
0.7407 Intermediate Similarity NPD2684 Approved
0.7407 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7199 Phase 2
0.7378 Intermediate Similarity NPD6234 Discontinued
0.7368 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4060 Phase 1
0.7333 Intermediate Similarity NPD290 Approved
0.7315 Intermediate Similarity NPD6798 Discontinued
0.731 Intermediate Similarity NPD4749 Approved
0.7296 Intermediate Similarity NPD5403 Approved
0.7292 Intermediate Similarity NPD422 Phase 1
0.7284 Intermediate Similarity NPD1934 Approved
0.7278 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5125 Phase 3
0.7273 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5126 Approved
0.7273 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD3787 Discontinued
0.7239 Intermediate Similarity NPD7819 Suspended
0.7235 Intermediate Similarity NPD5844 Phase 1
0.7226 Intermediate Similarity NPD1549 Phase 2
0.7226 Intermediate Similarity NPD2424 Discontinued
0.7202 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD6959 Discontinued
0.7171 Intermediate Similarity NPD6355 Discontinued
0.717 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD5401 Approved
0.7162 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD5846 Approved
0.7153 Intermediate Similarity NPD6516 Phase 2
0.7152 Intermediate Similarity NPD6233 Phase 2
0.7152 Intermediate Similarity NPD7768 Phase 2
0.7143 Intermediate Similarity NPD7033 Discontinued
0.7135 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD4535 Phase 3
0.7114 Intermediate Similarity NPD3018 Phase 2
0.7108 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD6799 Approved
0.7099 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD5402 Approved
0.7078 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD3751 Discontinued
0.707 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD5763 Approved
0.7051 Intermediate Similarity NPD5762 Approved
0.7042 Intermediate Similarity NPD6671 Approved
0.7032 Intermediate Similarity NPD4108 Discontinued
0.7025 Intermediate Similarity NPD4628 Phase 3
0.7025 Intermediate Similarity NPD7466 Approved
0.7025 Intermediate Similarity NPD3750 Approved
0.7024 Intermediate Similarity NPD5494 Approved
0.7012 Intermediate Similarity NPD6072 Discontinued
0.7005 Intermediate Similarity NPD7584 Approved
0.7005 Intermediate Similarity NPD7583 Approved
0.6995 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7458 Discontinued
0.6988 Remote Similarity NPD3817 Phase 2
0.6987 Remote Similarity NPD2796 Approved
0.6968 Remote Similarity NPD7585 Approved
0.6959 Remote Similarity NPD3685 Discontinued
0.6959 Remote Similarity NPD2982 Phase 2
0.6959 Remote Similarity NPD2983 Phase 2
0.6957 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6951 Remote Similarity NPD6599 Discontinued
0.695 Remote Similarity NPD5535 Approved
0.6948 Remote Similarity NPD4340 Discontinued
0.6948 Remote Similarity NPD5735 Approved
0.6947 Remote Similarity NPD7783 Phase 2
0.6947 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6939 Remote Similarity NPD3705 Approved
0.6937 Remote Similarity NPD6667 Approved
0.6937 Remote Similarity NPD6666 Approved
0.6935 Remote Similarity NPD7680 Approved
0.6931 Remote Similarity NPD8151 Discontinued
0.6928 Remote Similarity NPD2801 Approved
0.6918 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6913 Remote Similarity NPD3225 Approved
0.6908 Remote Similarity NPD7095 Approved
0.6892 Remote Similarity NPD2981 Phase 2
0.6884 Remote Similarity NPD968 Approved
0.6879 Remote Similarity NPD6100 Approved
0.6879 Remote Similarity NPD6099 Approved
0.6872 Remote Similarity NPD6842 Approved
0.6872 Remote Similarity NPD6841 Approved
0.6872 Remote Similarity NPD6843 Phase 3
0.6867 Remote Similarity NPD4433 Discontinued
0.6867 Remote Similarity NPD2797 Approved
0.6855 Remote Similarity NPD5062 Approved
0.6855 Remote Similarity NPD5061 Approved
0.6849 Remote Similarity NPD1357 Approved
0.6846 Remote Similarity NPD6582 Phase 2
0.6846 Remote Similarity NPD6583 Phase 3
0.6846 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7229 Phase 3
0.6838 Remote Similarity NPD846 Approved
0.6838 Remote Similarity NPD940 Approved
0.6835 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6004 Phase 3
0.6835 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6005 Phase 3
0.6835 Remote Similarity NPD6002 Phase 3
0.6826 Remote Similarity NPD1465 Phase 2
0.6821 Remote Similarity NPD3690 Phase 2
0.6821 Remote Similarity NPD3691 Phase 2
0.6818 Remote Similarity NPD4062 Phase 3
0.6815 Remote Similarity NPD3748 Approved
0.6815 Remote Similarity NPD1510 Phase 2
0.6813 Remote Similarity NPD3892 Phase 2
0.6806 Remote Similarity NPD6387 Discontinued
0.6791 Remote Similarity NPD6823 Phase 2
0.679 Remote Similarity NPD1511 Approved
0.679 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6374 Clinical (unspecified phase)
0.678 Remote Similarity NPD7549 Discontinued
0.6774 Remote Similarity NPD6782 Approved
0.6774 Remote Similarity NPD6779 Approved
0.6774 Remote Similarity NPD6776 Approved
0.6774 Remote Similarity NPD6777 Approved
0.6774 Remote Similarity NPD1240 Approved
0.6774 Remote Similarity NPD6778 Approved
0.6774 Remote Similarity NPD6781 Approved
0.6774 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6780 Approved
0.677 Remote Similarity NPD2677 Approved
0.6768 Remote Similarity NPD6980 Clinical (unspecified phase)
0.676 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6755 Remote Similarity NPD7435 Discontinued
0.6755 Remote Similarity NPD7697 Approved
0.6755 Remote Similarity NPD7698 Approved
0.6755 Remote Similarity NPD7696 Phase 3
0.6753 Remote Similarity NPD3268 Approved
0.6752 Remote Similarity NPD7119 Phase 2
0.6752 Remote Similarity NPD2200 Suspended
0.6746 Remote Similarity NPD3882 Suspended

Structure

External Identifiers

PubChem CID   44445356
ChEMBL   CHEMBL427819
ZINC  

Physicochemical Properties

Molecular Weight:  656.23
ALogP:  -5.2761
MLogP:  3
XLogP:  -1.665
# Rotatable Bonds:  21
Polar Surface Area:  257.68
# H-Bond Aceptor:  12
# H-Bond Donor:  10
# Rings:  5
# Heavy Atoms:  46

Download Data

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