Natural Product: NPC147168

Natural Product ID:  NPC147168
Common Name:   Dictamnusine
IUPAC Name:   (1R,5S,6S,8aR)-1-(furan-3-yl)-4-hydroxy-5,8a-dimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,8-tetrahydro-1H-isochromen-3-one
Synonyms:   Dictamnusine
Molecular Formula:   C21H28O10
Standard InCHIKey:  XAOOOVFRRCYNSK-GHYKFGOFSA-N
Standard InCHI:  InChI=1S/C21H28O10/c1-9-11(29-20-17(26)16(25)14(23)12(7-22)30-20)3-5-21(2)13(9)15(24)19(27)31-18(21)10-4-6-28-8-10/h4,6,8-9,11-12,14,16-18,20,22-26H,3,5,7H2,1-2H3/t9-,11+,12-,14-,16+,17-,18+,20-,21-/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C(=C(O)C(=O)O[C@H]3c3cocc3)[C@@H]2C)C)[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
NPO10830 Dictamnus dasycarpus Species Rutaceae Eukaryota Root barks PMID[18198838]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified EC50 = 42 nM 23999046

  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 NPC147168 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
0.92 High Similarity NPC476940
0.92 High Similarity NPC476939
0.9189 High Similarity NPC7388
0.9156 High Similarity NPC211777
0.9097 High Similarity NPC198047
0.9051 High Similarity NPC82602
0.9032 High Similarity NPC207978
0.9026 High Similarity NPC262872
0.8994 High Similarity NPC169299
0.8994 High Similarity NPC160818
0.8993 High Similarity NPC476938
0.8993 High Similarity NPC476937
0.8981 High Similarity NPC97574
0.8981 High Similarity NPC93172
0.8933 High Similarity NPC476942
0.8933 High Similarity NPC476941
0.8924 High Similarity NPC100333
0.8917 High Similarity NPC146991
0.8903 High Similarity NPC307383
0.8839 High Similarity NPC45101
0.8831 High Similarity NPC214541
0.8831 High Similarity NPC44675
0.8827 High Similarity NPC262386
0.8792 High Similarity NPC137295
0.879 High Similarity NPC69028
0.8782 High Similarity NPC475967
0.8734 High Similarity NPC477405
0.8726 High Similarity NPC477402
0.8718 High Similarity NPC261597
0.8718 High Similarity NPC472777
0.8718 High Similarity NPC36655
0.8718 High Similarity NPC472776
0.8718 High Similarity NPC472778
0.8679 High Similarity NPC276551
0.8679 High Similarity NPC271657
0.8671 High Similarity NPC329938
0.8654 High Similarity NPC469485
0.8625 High Similarity NPC470875
0.8616 High Similarity NPC39986
0.8616 High Similarity NPC292389
0.8616 High Similarity NPC302369
0.8616 High Similarity NPC134254
0.8616 High Similarity NPC469338
0.8608 High Similarity NPC472653
0.8608 High Similarity NPC335761
0.8599 High Similarity NPC187149
0.8599 High Similarity NPC173544
0.859 High Similarity NPC35000
0.8581 High Similarity NPC44577
0.8581 High Similarity NPC469503
0.8571 High Similarity NPC476936
0.8571 High Similarity NPC472282
0.8571 High Similarity NPC472651
0.8571 High Similarity NPC472774
0.8571 High Similarity NPC472775
0.8562 High Similarity NPC470940
0.8562 High Similarity NPC469849
0.8562 High Similarity NPC470182
0.8562 High Similarity NPC476858
0.8562 High Similarity NPC476857
0.8562 High Similarity NPC476856
0.8553 High Similarity NPC82851
0.8553 High Similarity NPC5079
0.8553 High Similarity NPC263432
0.8553 High Similarity NPC200782
0.8553 High Similarity NPC18347
0.8553 High Similarity NPC149896
0.8544 High Similarity NPC477403
0.8526 High Similarity NPC30222
0.8519 High Similarity NPC471397
0.8519 High Similarity NPC271235
0.8519 High Similarity NPC472652
0.8509 High Similarity NPC23387
0.8509 High Similarity NPC472141
0.85 High Similarity NPC51568
0.85 High Similarity NPC234660
0.85 High Similarity NPC472773
0.8497 Intermediate Similarity NPC250228
0.8491 Intermediate Similarity NPC25255
0.8481 Intermediate Similarity NPC299038
0.8481 Intermediate Similarity NPC249021
0.8471 Intermediate Similarity NPC469336
0.8471 Intermediate Similarity NPC281258
0.8471 Intermediate Similarity NPC264943
0.8457 Intermediate Similarity NPC476853
0.8457 Intermediate Similarity NPC476850
0.8457 Intermediate Similarity NPC476861
0.8457 Intermediate Similarity NPC173516
0.8447 Intermediate Similarity NPC123088
0.8447 Intermediate Similarity NPC476860
0.8443 Intermediate Similarity NPC470938
0.8438 Intermediate Similarity NPC117986
0.8438 Intermediate Similarity NPC472771
0.8438 Intermediate Similarity NPC193798
0.8421 Intermediate Similarity NPC476944
0.8418 Intermediate Similarity NPC126723
0.8408 Intermediate Similarity NPC178932
0.8408 Intermediate Similarity NPC57998
0.8408 Intermediate Similarity NPC282445
0.8405 Intermediate Similarity NPC160651
0.8387 Intermediate Similarity NPC195325
0.8385 Intermediate Similarity NPC472139
0.8375 Intermediate Similarity NPC470789
0.8365 Intermediate Similarity NPC286722
0.8365 Intermediate Similarity NPC472283
0.8365 Intermediate Similarity NPC472772
0.8344 Intermediate Similarity NPC476201
0.8323 Intermediate Similarity NPC290400
0.8323 Intermediate Similarity NPC96443
0.8322 Intermediate Similarity NPC186626
0.8313 Intermediate Similarity NPC475295
0.8313 Intermediate Similarity NPC473473
0.8303 Intermediate Similarity NPC159232
0.8302 Intermediate Similarity NPC107646
0.8302 Intermediate Similarity NPC209364
0.8301 Intermediate Similarity NPC86935
0.8291 Intermediate Similarity NPC253201
0.8291 Intermediate Similarity NPC302054
0.8282 Intermediate Similarity NPC475779
0.8282 Intermediate Similarity NPC472670
0.8282 Intermediate Similarity NPC214600
0.8282 Intermediate Similarity NPC307781
0.8274 Intermediate Similarity NPC325176
0.8272 Intermediate Similarity NPC419
0.8269 Intermediate Similarity NPC472654
0.8269 Intermediate Similarity NPC125182
0.8269 Intermediate Similarity NPC69647
0.8261 Intermediate Similarity NPC475381
0.8258 Intermediate Similarity NPC10088
0.8258 Intermediate Similarity NPC470941
0.8239 Intermediate Similarity NPC476262
0.8235 Intermediate Similarity NPC476946
0.8228 Intermediate Similarity NPC472672
0.8217 Intermediate Similarity NPC476122
0.8217 Intermediate Similarity NPC159927
0.8217 Intermediate Similarity NPC469335
0.8212 Intermediate Similarity NPC90953
0.821 Intermediate Similarity NPC470939
0.821 Intermediate Similarity NPC188649
0.8204 Intermediate Similarity NPC94763
0.8204 Intermediate Similarity NPC471437
0.8204 Intermediate Similarity NPC236004
0.82 Intermediate Similarity NPC310830
0.8199 Intermediate Similarity NPC475226
0.8199 Intermediate Similarity NPC237155
0.8199 Intermediate Similarity NPC472779
0.8194 Intermediate Similarity NPC262198
0.8194 Intermediate Similarity NPC276676
0.8194 Intermediate Similarity NPC346
0.8187 Intermediate Similarity NPC60973
0.8187 Intermediate Similarity NPC263265
0.8182 Intermediate Similarity NPC472766
0.8182 Intermediate Similarity NPC472673
0.8182 Intermediate Similarity NPC472765
0.8176 Intermediate Similarity NPC474425
0.8176 Intermediate Similarity NPC98206
0.8176 Intermediate Similarity NPC474407
0.8176 Intermediate Similarity NPC474426
0.8176 Intermediate Similarity NPC237259
0.8176 Intermediate Similarity NPC34421
0.8171 Intermediate Similarity NPC121995
0.8171 Intermediate Similarity NPC478178
0.8165 Intermediate Similarity NPC18135
0.816 Intermediate Similarity NPC469846
0.816 Intermediate Similarity NPC288602
0.816 Intermediate Similarity NPC88841
0.8148 Intermediate Similarity NPC305016
0.8146 Intermediate Similarity NPC476943
0.8141 Intermediate Similarity NPC221809
0.8141 Intermediate Similarity NPC255414
0.8137 Intermediate Similarity NPC167142
0.8133 Intermediate Similarity NPC470995
0.8129 Intermediate Similarity NPC41182
0.8121 Intermediate Similarity NPC472764
0.8121 Intermediate Similarity NPC478179
0.8117 Intermediate Similarity NPC223415
0.8117 Intermediate Similarity NPC243577
0.8117 Intermediate Similarity NPC242756
0.8113 Intermediate Similarity NPC268905
0.8113 Intermediate Similarity NPC75906
0.8107 Intermediate Similarity NPC478177
0.8101 Intermediate Similarity NPC104172
0.8101 Intermediate Similarity NPC477404
0.8101 Intermediate Similarity NPC88886
0.8101 Intermediate Similarity NPC196864
0.8101 Intermediate Similarity NPC46551
0.8098 Intermediate Similarity NPC18986
0.8098 Intermediate Similarity NPC472767
0.8098 Intermediate Similarity NPC470792
0.8095 Intermediate Similarity NPC469576
0.8086 Intermediate Similarity NPC474611
0.8081 Intermediate Similarity NPC242068
0.8081 Intermediate Similarity NPC105395
0.8081 Intermediate Similarity NPC247563
0.8065 Intermediate Similarity NPC251865
0.8063 Intermediate Similarity NPC183536
0.8063 Intermediate Similarity NPC34965
0.8061 Intermediate Similarity NPC149945
0.8052 Intermediate Similarity NPC121158
0.805 Intermediate Similarity NPC473966

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC147168 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
0.8047 Intermediate Similarity NPD6559 Discontinued
0.7901 Intermediate Similarity NPD5760 Phase 2
0.7901 Intermediate Similarity NPD5761 Phase 2
0.7816 Intermediate Similarity NPD8434 Phase 2
0.7758 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD3818 Discontinued
0.7576 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7075 Discontinued
0.7515 Intermediate Similarity NPD6801 Discontinued
0.7486 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD5402 Approved
0.7423 Intermediate Similarity NPD5403 Approved
0.7407 Intermediate Similarity NPD5401 Approved
0.7375 Intermediate Similarity NPD4628 Phase 3
0.7371 Intermediate Similarity NPD6797 Phase 2
0.7345 Intermediate Similarity NPD8313 Approved
0.7345 Intermediate Similarity NPD8312 Approved
0.733 Intermediate Similarity NPD7251 Discontinued
0.7317 Intermediate Similarity NPD920 Approved
0.7289 Intermediate Similarity NPD4380 Phase 2
0.7289 Intermediate Similarity NPD6599 Discontinued
0.7288 Intermediate Similarity NPD7808 Phase 3
0.7262 Intermediate Similarity NPD8455 Phase 2
0.7257 Intermediate Similarity NPD7054 Approved
0.7253 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD6799 Approved
0.7232 Intermediate Similarity NPD6764 Approved
0.7232 Intermediate Similarity NPD6765 Approved
0.7219 Intermediate Similarity NPD3817 Phase 2
0.7216 Intermediate Similarity NPD7472 Approved
0.7216 Intermediate Similarity NPD7074 Phase 3
0.7195 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD919 Approved
0.7188 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD1049 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD37 Approved
0.7091 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD4967 Phase 2
0.7076 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD4965 Approved
0.7076 Intermediate Similarity NPD4966 Approved
0.7073 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD6784 Approved
0.7072 Intermediate Similarity NPD6785 Approved
0.7059 Intermediate Similarity NPD7819 Suspended
0.7041 Intermediate Similarity NPD7411 Suspended
0.7039 Intermediate Similarity NPD7685 Pre-registration
0.7011 Intermediate Similarity NPD1247 Approved
0.7006 Intermediate Similarity NPD7228 Approved
0.7006 Intermediate Similarity NPD2313 Discontinued
0.6994 Remote Similarity NPD6234 Discontinued
0.6989 Remote Similarity NPD6166 Phase 2
0.6989 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6355 Discontinued
0.6981 Remote Similarity NPD1933 Approved
0.6978 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6977 Remote Similarity NPD3882 Suspended
0.697 Remote Similarity NPD8404 Phase 2
0.6964 Remote Similarity NPD1653 Approved
0.6959 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6957 Remote Similarity NPD2799 Discontinued
0.6954 Remote Similarity NPD5494 Approved
0.6932 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7458 Discontinued
0.6918 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1551 Phase 2
0.6914 Remote Similarity NPD2796 Approved
0.6914 Remote Similarity NPD7199 Phase 2
0.691 Remote Similarity NPD7799 Discontinued
0.6905 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6901 Remote Similarity NPD1934 Approved
0.6899 Remote Similarity NPD6798 Discontinued
0.6894 Remote Similarity NPD7097 Phase 1
0.689 Remote Similarity NPD7421 Clinical (unspecified phase)
0.689 Remote Similarity NPD1243 Approved
0.6889 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6832 Phase 2
0.6875 Remote Similarity NPD7435 Discontinued
0.6863 Remote Similarity NPD1091 Approved
0.6855 Remote Similarity NPD6233 Phase 2
0.6852 Remote Similarity NPD7033 Discontinued
0.6851 Remote Similarity NPD7240 Approved
0.6848 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6847 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6273 Approved
0.6839 Remote Similarity NPD3749 Approved
0.6829 Remote Similarity NPD1549 Phase 2
0.6826 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6821 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6818 Remote Similarity NPD8127 Discontinued
0.6816 Remote Similarity NPD3751 Discontinued
0.681 Remote Similarity NPD2935 Discontinued
0.6806 Remote Similarity NPD6776 Approved
0.6806 Remote Similarity NPD6779 Approved
0.6806 Remote Similarity NPD6782 Approved
0.6806 Remote Similarity NPD6781 Approved
0.6806 Remote Similarity NPD6780 Approved
0.6806 Remote Similarity NPD6778 Approved
0.6806 Remote Similarity NPD6777 Approved
0.6782 Remote Similarity NPD7768 Phase 2
0.678 Remote Similarity NPD3787 Discontinued
0.6778 Remote Similarity NPD5844 Phase 1
0.677 Remote Similarity NPD447 Suspended
0.6768 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6005 Phase 3
0.6768 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6002 Phase 3
0.6768 Remote Similarity NPD6004 Phase 3
0.6768 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6768 Remote Similarity NPD2346 Discontinued
0.6768 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6763 Remote Similarity NPD2801 Approved
0.6752 Remote Similarity NPD2798 Approved
0.6747 Remote Similarity NPD3750 Approved
0.6727 Remote Similarity NPD2424 Discontinued
0.6725 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6725 Remote Similarity NPD3226 Approved
0.671 Remote Similarity NPD9717 Approved
0.6704 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6688 Remote Similarity NPD2797 Approved
0.6687 Remote Similarity NPD2800 Approved
0.6687 Remote Similarity NPD1652 Phase 2
0.6686 Remote Similarity NPD2534 Approved
0.6686 Remote Similarity NPD2532 Approved
0.6686 Remote Similarity NPD2533 Approved
0.6686 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6685 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7266 Discontinued
0.6667 Remote Similarity NPD7874 Approved
0.6667 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5124 Phase 1
0.6649 Remote Similarity NPD8407 Phase 2
0.6648 Remote Similarity NPD3926 Phase 2
0.6647 Remote Similarity NPD1512 Approved
0.6646 Remote Similarity NPD4308 Phase 3
0.6646 Remote Similarity NPD1510 Phase 2
0.6646 Remote Similarity NPD3748 Approved
0.6646 Remote Similarity NPD5647 Approved
0.6627 Remote Similarity NPD970 Clinical (unspecified phase)
0.6625 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6615 Remote Similarity NPD7696 Phase 3
0.6615 Remote Similarity NPD7698 Approved
0.6615 Remote Similarity NPD7697 Approved
0.6599 Remote Similarity NPD7583 Approved
0.6599 Remote Similarity NPD7584 Approved
0.6596 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6592 Remote Similarity NPD6232 Discontinued
0.6584 Remote Similarity NPD3268 Approved
0.6584 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6582 Remote Similarity NPD7871 Phase 2
0.6582 Remote Similarity NPD7870 Phase 2
0.6582 Remote Similarity NPD8319 Approved
0.6582 Remote Similarity NPD1203 Approved
0.6582 Remote Similarity NPD8320 Phase 1
0.6578 Remote Similarity NPD8150 Discontinued
0.6576 Remote Similarity NPD8368 Discontinued
0.6575 Remote Similarity NPD7473 Discontinued
0.6568 Remote Similarity NPD5058 Phase 3
0.6566 Remote Similarity NPD1471 Phase 3
0.6566 Remote Similarity NPD5762 Approved
0.6566 Remote Similarity NPD2344 Approved
0.6566 Remote Similarity NPD7585 Approved
0.6566 Remote Similarity NPD5763 Approved
0.6566 Remote Similarity NPD7701 Phase 2
0.6564 Remote Similarity NPD6823 Phase 2
0.6564 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6562 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7615 Clinical (unspecified phase)
0.655 Remote Similarity NPD7783 Phase 2
0.655 Remote Similarity NPD7801 Approved
0.655 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6535 Approved
0.6545 Remote Similarity NPD6534 Approved
0.6543 Remote Similarity NPD4062 Phase 3
0.6541 Remote Similarity NPD1019 Discontinued
0.6538 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6529 Remote Similarity NPD1511 Approved
0.6527 Remote Similarity NPD4534 Discontinued
0.6522 Remote Similarity NPD7095 Approved
0.6519 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6509 Remote Similarity NPD6190 Approved
0.6503 Remote Similarity NPD4307 Phase 2
0.6481 Remote Similarity NPD3764 Approved
0.6477 Remote Similarity NPD1465 Phase 2
0.6453 Remote Similarity NPD7930 Approved
0.6453 Remote Similarity NPD5049 Phase 3
0.645 Remote Similarity NPD8151 Discontinued
0.645 Remote Similarity NPD4110 Phase 3
0.645 Remote Similarity NPD7003 Approved
0.645 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6448 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6444 Remote Similarity NPD6959 Discontinued
0.6443 Remote Similarity NPD7699 Phase 2
0.6443 Remote Similarity NPD7700 Phase 2

Structure

External Identifiers

PubChem CID   24799851
ChEMBL   CHEMBL402945
ZINC  

Physicochemical Properties

Molecular Weight:  440.17
ALogP:  -2.6641
MLogP:  2.67
XLogP:  0.119
# Rotatable Bonds:  11
Polar Surface Area:  159.05
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  31

Download Data

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