Natural Product: NPC166250

Natural Product ID:  NPC166250
Common Name:   Distyloside A
IUPAC Name:   (2R,3S,4R,5R,6S)-2-[(1R,2R,4S)-2-hydroxy-4-(2-hydroxypropan-2-yl)-1-methylcyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   distyloside A
Molecular Formula:   C16H30O8
Standard InCHIKey:  HWSOHMCMQHZNFN-NDRUJCHXSA-N
Standard InCHI:  InChI=1S/C16H30O8/c1-15(2,22)8-4-5-16(3,10(18)6-8)24-14-13(21)12(20)11(19)9(7-17)23-14/h8-14,17-22H,4-7H2,1-3H3/t8-,9-,10+,11-,12+,13-,14+,16+/m0/s1
Canonical SMILES:  OC[C@@H]1O[C@H](O[C@]2(C)CC[C@@H](C[C@H]2O)C(O)(C)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
NPO5829 Distylium racemosum Species Hamamelidaceae Eukaryota PMID[21489793]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT3046 Individual Protein Ribonuclease HI Escherichia coli (strain K12) IC50 > 20000 nM 17958396
NPT2 Others Unspecified IC50 > 20000 nM DrugMatrix in vitro pharmacology data
NPT2 Others Unspecified IC50 > 20000 nM 15165136
NPT3046 Individual Protein Ribonuclease HI Escherichia coli (strain K12) IC50 > 20000 nM Open TG-GATES in vivo data: Hematology
NPT2 Others Unspecified IC50 > 20000 nM 25451997
NPT2 Others Unspecified IC50 > 20000 nM 18849971
NPT2 Others Unspecified IC50 > 20000 nM 19654408

  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 NPC166250 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
0.9 High Similarity NPC471879
0.8919 High Similarity NPC272841
0.8831 High Similarity NPC241959
0.8667 High Similarity NPC177343
0.863 High Similarity NPC308489
0.8571 High Similarity NPC179823
0.85 High Similarity NPC268633
0.831 Intermediate Similarity NPC477758
0.831 Intermediate Similarity NPC477761
0.831 Intermediate Similarity NPC477760
0.831 Intermediate Similarity NPC477759
0.831 Intermediate Similarity NPC477754
0.8272 Intermediate Similarity NPC107603
0.8205 Intermediate Similarity NPC186588
0.8171 Intermediate Similarity NPC43912
0.8171 Intermediate Similarity NPC140446
0.8171 Intermediate Similarity NPC472396
0.8169 Intermediate Similarity NPC477756
0.8169 Intermediate Similarity NPC477752
0.8169 Intermediate Similarity NPC477751
0.8169 Intermediate Similarity NPC477764
0.8158 Intermediate Similarity NPC279575
0.8148 Intermediate Similarity NPC290612
0.8133 Intermediate Similarity NPC31046
0.8133 Intermediate Similarity NPC209666
0.8133 Intermediate Similarity NPC200167
0.8133 Intermediate Similarity NPC53868
0.8088 Intermediate Similarity NPC185116
0.8049 Intermediate Similarity NPC471410
0.8049 Intermediate Similarity NPC471411
0.8025 Intermediate Similarity NPC474156
0.8 Intermediate Similarity NPC293609
0.7976 Intermediate Similarity NPC82955
0.7976 Intermediate Similarity NPC473472
0.7976 Intermediate Similarity NPC131466
0.7907 Intermediate Similarity NPC277774
0.7882 Intermediate Similarity NPC223143
0.7882 Intermediate Similarity NPC279329
0.7857 Intermediate Similarity NPC281004
0.7857 Intermediate Similarity NPC470872
0.7848 Intermediate Similarity NPC170595
0.7816 Intermediate Similarity NPC113500
0.7816 Intermediate Similarity NPC477224
0.7816 Intermediate Similarity NPC3538
0.7805 Intermediate Similarity NPC18953
0.7791 Intermediate Similarity NPC5632
0.7791 Intermediate Similarity NPC307167
0.7791 Intermediate Similarity NPC210759
0.7791 Intermediate Similarity NPC36372
0.7791 Intermediate Similarity NPC229801
0.7791 Intermediate Similarity NPC149966
0.7765 Intermediate Similarity NPC102725
0.7765 Intermediate Similarity NPC20822
0.7763 Intermediate Similarity NPC470660
0.7763 Intermediate Similarity NPC470659
0.7738 Intermediate Similarity NPC45833
0.7738 Intermediate Similarity NPC213658
0.7738 Intermediate Similarity NPC62202
0.7738 Intermediate Similarity NPC110365
0.7733 Intermediate Similarity NPC5209
0.7733 Intermediate Similarity NPC29005
0.7733 Intermediate Similarity NPC51956
0.7727 Intermediate Similarity NPC477494
0.7727 Intermediate Similarity NPC92196
0.7727 Intermediate Similarity NPC94582
0.7727 Intermediate Similarity NPC57964
0.7701 Intermediate Similarity NPC476669
0.7701 Intermediate Similarity NPC171741
0.7701 Intermediate Similarity NPC224003
0.7701 Intermediate Similarity NPC167644
0.7701 Intermediate Similarity NPC323231
0.7701 Intermediate Similarity NPC311246
0.7701 Intermediate Similarity NPC18724
0.7701 Intermediate Similarity NPC470623
0.7701 Intermediate Similarity NPC475307
0.7692 Intermediate Similarity NPC107963
0.7674 Intermediate Similarity NPC474249
0.7674 Intermediate Similarity NPC65550
0.7674 Intermediate Similarity NPC261990
0.7674 Intermediate Similarity NPC473542
0.7662 Intermediate Similarity NPC138273
0.7662 Intermediate Similarity NPC470151
0.7654 Intermediate Similarity NPC470156
0.764 Intermediate Similarity NPC473287
0.7614 Intermediate Similarity NPC151214
0.7614 Intermediate Similarity NPC77717
0.7614 Intermediate Similarity NPC252253
0.7614 Intermediate Similarity NPC305418
0.7614 Intermediate Similarity NPC175
0.7614 Intermediate Similarity NPC471373
0.7614 Intermediate Similarity NPC475325
0.7614 Intermediate Similarity NPC253611
0.7614 Intermediate Similarity NPC191915
0.7614 Intermediate Similarity NPC45959
0.7614 Intermediate Similarity NPC473503
0.7614 Intermediate Similarity NPC309866
0.7614 Intermediate Similarity NPC267238
0.7614 Intermediate Similarity NPC148593
0.7595 Intermediate Similarity NPC188793
0.759 Intermediate Similarity NPC166279
0.7586 Intermediate Similarity NPC473637
0.7586 Intermediate Similarity NPC473830
0.7586 Intermediate Similarity NPC204881
0.7586 Intermediate Similarity NPC476668
0.7564 Intermediate Similarity NPC472950
0.7564 Intermediate Similarity NPC472952
0.7561 Intermediate Similarity NPC477446
0.7561 Intermediate Similarity NPC470155
0.7561 Intermediate Similarity NPC477447
0.7556 Intermediate Similarity NPC477223
0.7556 Intermediate Similarity NPC477222
0.7528 Intermediate Similarity NPC205129
0.7528 Intermediate Similarity NPC473065
0.7528 Intermediate Similarity NPC471425
0.7528 Intermediate Similarity NPC189575
0.7528 Intermediate Similarity NPC473067
0.7528 Intermediate Similarity NPC469710
0.7528 Intermediate Similarity NPC473064
0.7528 Intermediate Similarity NPC471424
0.7528 Intermediate Similarity NPC471429
0.7528 Intermediate Similarity NPC106701
0.75 Intermediate Similarity NPC473726
0.75 Intermediate Similarity NPC477577
0.75 Intermediate Similarity NPC88962
0.75 Intermediate Similarity NPC43463
0.75 Intermediate Similarity NPC144790
0.75 Intermediate Similarity NPC172838
0.75 Intermediate Similarity NPC149400
0.75 Intermediate Similarity NPC235402
0.75 Intermediate Similarity NPC137004
0.7473 Intermediate Similarity NPC473638
0.747 Intermediate Similarity NPC30102
0.747 Intermediate Similarity NPC67158
0.747 Intermediate Similarity NPC128816
0.7468 Intermediate Similarity NPC136424
0.7465 Intermediate Similarity NPC477757
0.7465 Intermediate Similarity NPC477763
0.7465 Intermediate Similarity NPC472026
0.7465 Intermediate Similarity NPC477762
0.7465 Intermediate Similarity NPC477750
0.7465 Intermediate Similarity NPC477755
0.7465 Intermediate Similarity NPC477753
0.7444 Intermediate Similarity NPC203434
0.7444 Intermediate Similarity NPC142264
0.7444 Intermediate Similarity NPC304011
0.7444 Intermediate Similarity NPC139271
0.7444 Intermediate Similarity NPC252056
0.7444 Intermediate Similarity NPC90583
0.7444 Intermediate Similarity NPC121453
0.7444 Intermediate Similarity NPC238796
0.7444 Intermediate Similarity NPC472989
0.7444 Intermediate Similarity NPC476510
0.7444 Intermediate Similarity NPC237071
0.7442 Intermediate Similarity NPC128475
0.7439 Intermediate Similarity NPC211049
0.7439 Intermediate Similarity NPC470154
0.7416 Intermediate Similarity NPC475436
0.7416 Intermediate Similarity NPC30687
0.7416 Intermediate Similarity NPC178949
0.7416 Intermediate Similarity NPC179859
0.7416 Intermediate Similarity NPC291547
0.7416 Intermediate Similarity NPC131693
0.7416 Intermediate Similarity NPC473774
0.7416 Intermediate Similarity NPC312678
0.7416 Intermediate Similarity NPC174024
0.7416 Intermediate Similarity NPC294686
0.7416 Intermediate Similarity NPC96736
0.7416 Intermediate Similarity NPC24960
0.7416 Intermediate Similarity NPC253268
0.7416 Intermediate Similarity NPC473851
0.7416 Intermediate Similarity NPC222731
0.7412 Intermediate Similarity NPC471240
0.7397 Intermediate Similarity NPC94897
0.7391 Intermediate Similarity NPC51579
0.7391 Intermediate Similarity NPC148424
0.7386 Intermediate Similarity NPC289361
0.7386 Intermediate Similarity NPC59006
0.7368 Intermediate Similarity NPC470833
0.7363 Intermediate Similarity NPC470028
0.7363 Intermediate Similarity NPC233649
0.7349 Intermediate Similarity NPC216800
0.7333 Intermediate Similarity NPC474399
0.7326 Intermediate Similarity NPC210658
0.7326 Intermediate Similarity NPC161928
0.7317 Intermediate Similarity NPC186594
0.7317 Intermediate Similarity NPC472951
0.7317 Intermediate Similarity NPC472943
0.7317 Intermediate Similarity NPC471217
0.7317 Intermediate Similarity NPC100697
0.7317 Intermediate Similarity NPC471216
0.7312 Intermediate Similarity NPC477225
0.7308 Intermediate Similarity NPC248427
0.7303 Intermediate Similarity NPC297348
0.7303 Intermediate Similarity NPC48339
0.7303 Intermediate Similarity NPC234352
0.7303 Intermediate Similarity NPC325828
0.7303 Intermediate Similarity NPC249204
0.7303 Intermediate Similarity NPC477547
0.7303 Intermediate Similarity NPC477451
0.7303 Intermediate Similarity NPC177834

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC166250 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
0.8406 Intermediate Similarity NPD371 Approved
0.8219 Intermediate Similarity NPD7532 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD1810 Approved
0.8133 Intermediate Similarity NPD1811 Approved
0.7733 Intermediate Similarity NPD2687 Approved
0.7733 Intermediate Similarity NPD2254 Approved
0.7733 Intermediate Similarity NPD2686 Approved
0.747 Intermediate Similarity NPD3670 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD3669 Approved
0.7303 Intermediate Similarity NPD8171 Discontinued
0.6957 Remote Similarity NPD890 Clinical (unspecified phase)
0.6957 Remote Similarity NPD891 Phase 3
0.6957 Remote Similarity NPD888 Phase 3
0.6957 Remote Similarity NPD893 Approved
0.6957 Remote Similarity NPD892 Phase 3
0.6912 Remote Similarity NPD904 Phase 3
0.6912 Remote Similarity NPD905 Approved
0.6812 Remote Similarity NPD2269 Approved
0.6714 Remote Similarity NPD894 Approved
0.6714 Remote Similarity NPD887 Approved
0.6714 Remote Similarity NPD889 Approved
0.6714 Remote Similarity NPD895 Approved
0.6706 Remote Similarity NPD6928 Phase 2
0.6667 Remote Similarity NPD2267 Suspended
0.6634 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6628 Remote Similarity NPD1779 Approved
0.6628 Remote Similarity NPD1780 Approved
0.6566 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6533 Remote Similarity NPD6123 Approved
0.65 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6324 Remote Similarity NPD385 Approved
0.6324 Remote Similarity NPD384 Approved
0.6239 Remote Similarity NPD7516 Approved
0.6226 Remote Similarity NPD8133 Approved
0.6176 Remote Similarity NPD9000 Phase 3
0.6176 Remote Similarity NPD8997 Approved
0.6176 Remote Similarity NPD8993 Phase 1
0.6176 Remote Similarity NPD388 Approved
0.6176 Remote Similarity NPD386 Approved
0.6176 Remote Similarity NPD8999 Phase 3
0.6176 Remote Similarity NPD8998 Phase 2
0.617 Remote Similarity NPD3168 Discontinued
0.6164 Remote Similarity NPD7346 Approved
0.6147 Remote Similarity NPD7328 Approved
0.6147 Remote Similarity NPD7327 Approved
0.6055 Remote Similarity NPD8295 Clinical (unspecified phase)
0.604 Remote Similarity NPD8139 Approved
0.604 Remote Similarity NPD8083 Approved
0.604 Remote Similarity NPD8084 Approved
0.604 Remote Similarity NPD8138 Approved
0.604 Remote Similarity NPD8086 Approved
0.604 Remote Similarity NPD8082 Approved
0.604 Remote Similarity NPD8085 Approved
0.6036 Remote Similarity NPD8377 Approved
0.6036 Remote Similarity NPD8294 Approved
0.6 Remote Similarity NPD8966 Approved
0.6 Remote Similarity NPD8965 Approved
0.5982 Remote Similarity NPD8380 Approved
0.5982 Remote Similarity NPD8378 Approved
0.5982 Remote Similarity NPD8379 Approved
0.5982 Remote Similarity NPD8296 Approved
0.5982 Remote Similarity NPD8335 Approved
0.5982 Remote Similarity NPD8033 Approved
0.598 Remote Similarity NPD8275 Approved
0.598 Remote Similarity NPD8276 Approved
0.5962 Remote Similarity NPD6412 Phase 2
0.5949 Remote Similarity NPD847 Phase 1
0.5922 Remote Similarity NPD8081 Approved
0.5921 Remote Similarity NPD369 Approved
0.5905 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5905 Remote Similarity NPD6686 Approved
0.5897 Remote Similarity NPD1145 Discontinued
0.5865 Remote Similarity NPD8393 Approved
0.5841 Remote Similarity NPD7503 Approved
0.5818 Remote Similarity NPD6940 Discontinued
0.5811 Remote Similarity NPD9035 Clinical (unspecified phase)
0.5811 Remote Similarity NPD9036 Phase 3
0.581 Remote Similarity NPD8307 Discontinued
0.581 Remote Similarity NPD8140 Approved
0.5784 Remote Similarity NPD5344 Discontinued
0.5776 Remote Similarity NPD7507 Approved
0.5758 Remote Similarity NPD7991 Discontinued
0.5739 Remote Similarity NPD8328 Phase 3
0.5735 Remote Similarity NPD8788 Approved
0.573 Remote Similarity NPD6697 Approved
0.573 Remote Similarity NPD6114 Approved
0.573 Remote Similarity NPD6118 Approved
0.573 Remote Similarity NPD6115 Approved
0.5702 Remote Similarity NPD8513 Phase 3
0.5702 Remote Similarity NPD8517 Approved
0.5702 Remote Similarity NPD8515 Approved
0.5702 Remote Similarity NPD8516 Approved
0.5701 Remote Similarity NPD8306 Approved
0.5701 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5701 Remote Similarity NPD8305 Approved
0.5698 Remote Similarity NPD3181 Approved
0.5684 Remote Similarity NPD7524 Approved
0.5663 Remote Similarity NPD897 Approved
0.5663 Remote Similarity NPD898 Approved
0.5663 Remote Similarity NPD896 Approved
0.5652 Remote Similarity NPD367 Approved
0.5648 Remote Similarity NPD8087 Discontinued
0.563 Remote Similarity NPD7319 Approved
0.5619 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5619 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5618 Remote Similarity NPD6116 Phase 1
0.5607 Remote Similarity NPD8174 Phase 2

Structure

External Identifiers

PubChem CID   54584790
ChEMBL   CHEMBL1770692
ZINC  

Physicochemical Properties

Molecular Weight:  350.19
ALogP:  -1.9688
MLogP:  2.34
XLogP:  -0.561
# Rotatable Bonds:  13
Polar Surface Area:  139.84
# H-Bond Aceptor:  8
# H-Bond Donor:  6
# Rings:  2
# Heavy Atoms:  24

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Similar NPs/Drugs