Natural Product: NPC235051

Natural Product ID:  NPC235051
Common Name:   Patrinioside
IUPAC Name:   [(1S,2S,3R,4S)-2-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-methyl-3-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]cyclopentyl] 3-methylbutanoate
Synonyms:   Patrinioside
Molecular Formula:   C21H36O10
Standard InCHIKey:  HRAKXIGVAPGHEW-XHHYMNQSSA-N
Standard InCHI:  InChI=1S/C21H36O10/c1-10(2)5-16(24)31-15-6-12(11(3)7-22)13(21(15,4)28)9-29-20-19(27)18(26)17(25)14(8-23)30-20/h10,12-15,17-20,22-23,25-28H,3,5-9H2,1-2,4H3/t12-,13+,14-,15+,17-,18+,19-,20-,21+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](OC[C@H]2[C@H](C[C@@H]([C@@]2(C)O)OC(=O)CC(C)C)C(=C)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
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota Roots PMID[23002924]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens IC50 > 50000 nM 22194678
NPT2 Others Unspecified IC50 = 23800 nM 20439609

  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 NPC235051 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
0.9222 High Similarity NPC93869
0.9222 High Similarity NPC6765
0.9111 High Similarity NPC274588
0.8936 High Similarity NPC216911
0.8913 High Similarity NPC170527
0.883 High Similarity NPC476211
0.883 High Similarity NPC476320
0.8817 High Similarity NPC86843
0.875 High Similarity NPC329834
0.8737 High Similarity NPC27474
0.8737 High Similarity NPC476230
0.871 High Similarity NPC284063
0.8617 High Similarity NPC263674
0.8617 High Similarity NPC58267
0.8617 High Similarity NPC261372
0.8557 High Similarity NPC329704
0.8542 High Similarity NPC3488
0.8542 High Similarity NPC287539
0.8542 High Similarity NPC476228
0.8511 High Similarity NPC474297
0.8478 Intermediate Similarity NPC66504
0.8384 Intermediate Similarity NPC127235
0.8367 Intermediate Similarity NPC37240
0.828 Intermediate Similarity NPC294643
0.828 Intermediate Similarity NPC274274
0.828 Intermediate Similarity NPC473150
0.8265 Intermediate Similarity NPC474730
0.8265 Intermediate Similarity NPC177013
0.8265 Intermediate Similarity NPC35185
0.8265 Intermediate Similarity NPC4899
0.8261 Intermediate Similarity NPC93190
0.8229 Intermediate Similarity NPC236580
0.8229 Intermediate Similarity NPC304445
0.8218 Intermediate Similarity NPC110701
0.82 Intermediate Similarity NPC170432
0.8182 Intermediate Similarity NPC475928
0.8163 Intermediate Similarity NPC67296
0.8137 Intermediate Similarity NPC208307
0.8119 Intermediate Similarity NPC80338
0.8119 Intermediate Similarity NPC197813
0.8119 Intermediate Similarity NPC148270
0.8081 Intermediate Similarity NPC304163
0.8065 Intermediate Similarity NPC50464
0.8058 Intermediate Similarity NPC193741
0.8043 Intermediate Similarity NPC31349
0.8 Intermediate Similarity NPC473148
0.8 Intermediate Similarity NPC470187
0.798 Intermediate Similarity NPC20673
0.7959 Intermediate Similarity NPC249171
0.7959 Intermediate Similarity NPC49833
0.7959 Intermediate Similarity NPC469919
0.7959 Intermediate Similarity NPC223700
0.7959 Intermediate Similarity NPC469918
0.7959 Intermediate Similarity NPC117066
0.7959 Intermediate Similarity NPC96399
0.7938 Intermediate Similarity NPC161293
0.7935 Intermediate Similarity NPC470657
0.7917 Intermediate Similarity NPC472198
0.7905 Intermediate Similarity NPC475851
0.7905 Intermediate Similarity NPC475924
0.79 Intermediate Similarity NPC80144
0.79 Intermediate Similarity NPC94919
0.79 Intermediate Similarity NPC106668
0.7895 Intermediate Similarity NPC472199
0.7895 Intermediate Similarity NPC472197
0.7885 Intermediate Similarity NPC106760
0.7879 Intermediate Similarity NPC244878
0.7857 Intermediate Similarity NPC472290
0.7826 Intermediate Similarity NPC477746
0.7826 Intermediate Similarity NPC477747
0.7822 Intermediate Similarity NPC27687
0.7816 Intermediate Similarity NPC279575
0.7802 Intermediate Similarity NPC474266
0.7789 Intermediate Similarity NPC246173
0.7778 Intermediate Similarity NPC37866
0.7778 Intermediate Similarity NPC151093
0.7767 Intermediate Similarity NPC470170
0.7767 Intermediate Similarity NPC470169
0.7742 Intermediate Similarity NPC149018
0.7742 Intermediate Similarity NPC171484
0.7732 Intermediate Similarity NPC63897
0.7723 Intermediate Similarity NPC214714
0.7723 Intermediate Similarity NPC200672
0.7714 Intermediate Similarity NPC114961
0.7714 Intermediate Similarity NPC27551
0.77 Intermediate Similarity NPC130792
0.77 Intermediate Similarity NPC91497
0.77 Intermediate Similarity NPC473146
0.7692 Intermediate Similarity NPC224414
0.7692 Intermediate Similarity NPC475849
0.7684 Intermediate Similarity NPC22918
0.7677 Intermediate Similarity NPC474182
0.767 Intermediate Similarity NPC165405
0.7664 Intermediate Similarity NPC102619
0.7653 Intermediate Similarity NPC167893
0.7629 Intermediate Similarity NPC474835
0.7629 Intermediate Similarity NPC238090
0.7629 Intermediate Similarity NPC320089
0.7629 Intermediate Similarity NPC472195
0.7629 Intermediate Similarity NPC472196
0.7624 Intermediate Similarity NPC219038
0.7624 Intermediate Similarity NPC98859
0.7624 Intermediate Similarity NPC4637
0.7624 Intermediate Similarity NPC26557
0.7609 Intermediate Similarity NPC239308
0.7604 Intermediate Similarity NPC312471
0.7604 Intermediate Similarity NPC471378
0.76 Intermediate Similarity NPC157739
0.76 Intermediate Similarity NPC472015
0.76 Intermediate Similarity NPC469725
0.7596 Intermediate Similarity NPC287269
0.7582 Intermediate Similarity NPC216941
0.7579 Intermediate Similarity NPC148534
0.7579 Intermediate Similarity NPC470009
0.7576 Intermediate Similarity NPC54731
0.7573 Intermediate Similarity NPC475335
0.7573 Intermediate Similarity NPC80809
0.7573 Intermediate Similarity NPC201144
0.7573 Intermediate Similarity NPC475331
0.7573 Intermediate Similarity NPC288502
0.7573 Intermediate Similarity NPC121518
0.7573 Intermediate Similarity NPC181104
0.7573 Intermediate Similarity NPC103298
0.757 Intermediate Similarity NPC243572
0.7556 Intermediate Similarity NPC170595
0.7551 Intermediate Similarity NPC159698
0.7549 Intermediate Similarity NPC252242
0.7549 Intermediate Similarity NPC475956
0.7549 Intermediate Similarity NPC471599
0.7527 Intermediate Similarity NPC475963
0.7527 Intermediate Similarity NPC259296
0.7527 Intermediate Similarity NPC151176
0.7527 Intermediate Similarity NPC98276
0.7527 Intermediate Similarity NPC3464
0.7526 Intermediate Similarity NPC276298
0.7524 Intermediate Similarity NPC88744
0.7524 Intermediate Similarity NPC295980
0.75 Intermediate Similarity NPC200944
0.75 Intermediate Similarity NPC473555
0.75 Intermediate Similarity NPC470684
0.75 Intermediate Similarity NPC60315
0.75 Intermediate Similarity NPC470980
0.75 Intermediate Similarity NPC278939
0.75 Intermediate Similarity NPC471770
0.75 Intermediate Similarity NPC85670
0.75 Intermediate Similarity NPC473199
0.75 Intermediate Similarity NPC73455
0.75 Intermediate Similarity NPC470683
0.75 Intermediate Similarity NPC76486
0.7477 Intermediate Similarity NPC272242
0.7477 Intermediate Similarity NPC470748
0.7476 Intermediate Similarity NPC473694
0.7476 Intermediate Similarity NPC474783
0.7476 Intermediate Similarity NPC475334
0.7476 Intermediate Similarity NPC232515
0.7476 Intermediate Similarity NPC471467
0.7476 Intermediate Similarity NPC260809
0.7476 Intermediate Similarity NPC475623
0.7475 Intermediate Similarity NPC215570
0.7475 Intermediate Similarity NPC472873
0.7474 Intermediate Similarity NPC258501
0.7471 Intermediate Similarity NPC470659
0.7471 Intermediate Similarity NPC470660
0.7453 Intermediate Similarity NPC91583
0.7453 Intermediate Similarity NPC473844
0.7453 Intermediate Similarity NPC118225
0.7453 Intermediate Similarity NPC51947
0.7453 Intermediate Similarity NPC240125
0.7453 Intermediate Similarity NPC473570
0.7451 Intermediate Similarity NPC144486
0.7449 Intermediate Similarity NPC475788
0.7447 Intermediate Similarity NPC196911
0.7447 Intermediate Similarity NPC471379
0.7431 Intermediate Similarity NPC220293
0.7431 Intermediate Similarity NPC469821
0.7429 Intermediate Similarity NPC470166
0.7426 Intermediate Similarity NPC79449
0.7426 Intermediate Similarity NPC474957
0.7426 Intermediate Similarity NPC274458
0.7423 Intermediate Similarity NPC202886
0.7404 Intermediate Similarity NPC223741
0.74 Intermediate Similarity NPC111834
0.74 Intermediate Similarity NPC472989
0.74 Intermediate Similarity NPC306797
0.74 Intermediate Similarity NPC169270
0.74 Intermediate Similarity NPC292718
0.7396 Intermediate Similarity NPC92370
0.7391 Intermediate Similarity NPC118116
0.7391 Intermediate Similarity NPC77003
0.7387 Intermediate Similarity NPC13710
0.7383 Intermediate Similarity NPC129340
0.7379 Intermediate Similarity NPC31085
0.7379 Intermediate Similarity NPC475986
0.7379 Intermediate Similarity NPC154452
0.7374 Intermediate Similarity NPC39453
0.7374 Intermediate Similarity NPC96736
0.7374 Intermediate Similarity NPC178949
0.7368 Intermediate Similarity NPC322922
0.7368 Intermediate Similarity NPC321812
0.7364 Intermediate Similarity NPC277583

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC235051 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
0.75 Intermediate Similarity NPD8133 Approved
0.7264 Intermediate Similarity NPD6412 Phase 2
0.7232 Intermediate Similarity NPD7327 Approved
0.7232 Intermediate Similarity NPD7328 Approved
0.7196 Intermediate Similarity NPD6686 Approved
0.7168 Intermediate Similarity NPD7516 Approved
0.7105 Intermediate Similarity NPD8377 Approved
0.7105 Intermediate Similarity NPD8294 Approved
0.7094 Intermediate Similarity NPD7507 Approved
0.7043 Intermediate Similarity NPD7503 Approved
0.7043 Intermediate Similarity NPD8335 Approved
0.7043 Intermediate Similarity NPD8033 Approved
0.7043 Intermediate Similarity NPD8296 Approved
0.7043 Intermediate Similarity NPD8380 Approved
0.7043 Intermediate Similarity NPD8378 Approved
0.7043 Intermediate Similarity NPD8379 Approved
0.6939 Remote Similarity NPD4251 Approved
0.6939 Remote Similarity NPD4250 Approved
0.6923 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6917 Remote Similarity NPD7319 Approved
0.6915 Remote Similarity NPD4820 Approved
0.6915 Remote Similarity NPD4822 Approved
0.6915 Remote Similarity NPD4819 Approved
0.6915 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6915 Remote Similarity NPD4821 Approved
0.69 Remote Similarity NPD6698 Approved
0.69 Remote Similarity NPD46 Approved
0.6847 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6837 Remote Similarity NPD4249 Approved
0.6735 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6702 Remote Similarity NPD4268 Approved
0.6702 Remote Similarity NPD4271 Approved
0.6701 Remote Similarity NPD5362 Discontinued
0.6667 Remote Similarity NPD7983 Approved
0.6636 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6612 Remote Similarity NPD8293 Discontinued
0.661 Remote Similarity NPD8517 Approved
0.661 Remote Similarity NPD8516 Approved
0.661 Remote Similarity NPD8513 Phase 3
0.661 Remote Similarity NPD8515 Approved
0.6607 Remote Similarity NPD6371 Approved
0.6606 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6606 Remote Similarity NPD4057 Clinical (unspecified phase)
0.66 Remote Similarity NPD7524 Approved
0.6598 Remote Similarity NPD6435 Approved
0.6569 Remote Similarity NPD7838 Discovery
0.6557 Remote Similarity NPD7736 Approved
0.6555 Remote Similarity NPD6370 Approved
0.6531 Remote Similarity NPD5331 Approved
0.6531 Remote Similarity NPD5332 Approved
0.6518 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6505 Remote Similarity NPD7637 Suspended
0.6495 Remote Similarity NPD4790 Discontinued
0.6465 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6455 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6446 Remote Similarity NPD7492 Approved
0.6442 Remote Similarity NPD8171 Discontinued
0.6393 Remote Similarity NPD6616 Approved
0.6392 Remote Similarity NPD5368 Approved
0.6389 Remote Similarity NPD7639 Approved
0.6389 Remote Similarity NPD7640 Approved
0.6387 Remote Similarity NPD6054 Approved
0.6387 Remote Similarity NPD6059 Approved
0.6387 Remote Similarity NPD6319 Approved
0.6364 Remote Similarity NPD6695 Phase 3
0.6364 Remote Similarity NPD3669 Approved
0.6364 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7154 Phase 3
0.6354 Remote Similarity NPD4802 Phase 2
0.6354 Remote Similarity NPD4238 Approved
0.6348 Remote Similarity NPD6882 Approved
0.6348 Remote Similarity NPD6053 Discontinued
0.6341 Remote Similarity NPD7078 Approved
0.633 Remote Similarity NPD5344 Discontinued
0.6327 Remote Similarity NPD5369 Approved
0.6304 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6296 Remote Similarity NPD7638 Approved
0.6271 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6271 Remote Similarity NPD6009 Approved
0.6263 Remote Similarity NPD4270 Approved
0.6263 Remote Similarity NPD4269 Approved
0.6262 Remote Similarity NPD7839 Suspended
0.6207 Remote Similarity NPD8297 Approved
0.6204 Remote Similarity NPD6083 Phase 2
0.6204 Remote Similarity NPD6084 Phase 2
0.6198 Remote Similarity NPD6015 Approved
0.6198 Remote Similarity NPD6016 Approved
0.6186 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6179 Remote Similarity NPD8340 Approved
0.6179 Remote Similarity NPD8341 Approved
0.6179 Remote Similarity NPD8299 Approved
0.6179 Remote Similarity NPD8342 Approved
0.6176 Remote Similarity NPD5786 Approved
0.6154 Remote Similarity NPD4632 Approved
0.6148 Remote Similarity NPD5988 Approved
0.6134 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6132 Remote Similarity NPD5779 Approved
0.6132 Remote Similarity NPD5778 Approved
0.6117 Remote Similarity NPD7750 Discontinued
0.6106 Remote Similarity NPD6675 Approved
0.6106 Remote Similarity NPD5739 Approved
0.6106 Remote Similarity NPD6402 Approved
0.6106 Remote Similarity NPD7128 Approved
0.6098 Remote Similarity NPD6067 Discontinued
0.6098 Remote Similarity NPD8328 Phase 3
0.6087 Remote Similarity NPD6373 Approved
0.6087 Remote Similarity NPD6372 Approved
0.6083 Remote Similarity NPD7641 Discontinued
0.608 Remote Similarity NPD8074 Phase 3
0.6078 Remote Similarity NPD5363 Approved
0.6066 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6061 Remote Similarity NPD6930 Phase 2
0.6061 Remote Similarity NPD6931 Approved
0.6061 Remote Similarity NPD4252 Approved
0.6053 Remote Similarity NPD6685 Approved
0.6038 Remote Similarity NPD8035 Phase 2
0.6038 Remote Similarity NPD8034 Phase 2
0.6019 Remote Similarity NPD5695 Phase 3
0.6016 Remote Similarity NPD8080 Discontinued
0.6 Remote Similarity NPD1695 Approved
0.6 Remote Similarity NPD8451 Approved
0.6 Remote Similarity NPD6881 Approved
0.6 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6 Remote Similarity NPD7320 Approved
0.6 Remote Similarity NPD4225 Approved
0.6 Remote Similarity NPD6899 Approved
0.5983 Remote Similarity NPD6650 Approved
0.5983 Remote Similarity NPD6649 Approved
0.5982 Remote Similarity NPD8083 Approved
0.5982 Remote Similarity NPD8086 Approved
0.5982 Remote Similarity NPD8084 Approved
0.5982 Remote Similarity NPD8082 Approved
0.5982 Remote Similarity NPD8138 Approved
0.5982 Remote Similarity NPD8085 Approved
0.5982 Remote Similarity NPD7632 Discontinued
0.5982 Remote Similarity NPD8139 Approved
0.5981 Remote Similarity NPD6399 Phase 3
0.598 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5963 Remote Similarity NPD4792 Clinical (unspecified phase)
0.596 Remote Similarity NPD6929 Approved
0.5952 Remote Similarity NPD8448 Approved
0.5946 Remote Similarity NPD6648 Approved
0.5943 Remote Similarity NPD5785 Approved
0.5935 Remote Similarity NPD8444 Approved
0.5929 Remote Similarity NPD8276 Approved
0.5929 Remote Similarity NPD8275 Approved
0.5922 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5913 Remote Similarity NPD5697 Approved
0.5913 Remote Similarity NPD5701 Approved
0.5909 Remote Similarity NPD3198 Approved
0.5906 Remote Similarity NPD8336 Approved
0.5906 Remote Similarity NPD6033 Approved
0.5906 Remote Similarity NPD8337 Approved
0.59 Remote Similarity NPD6928 Phase 2
0.5897 Remote Similarity NPD7102 Approved
0.5897 Remote Similarity NPD6883 Approved
0.5897 Remote Similarity NPD7290 Approved
0.5888 Remote Similarity NPD7087 Discontinued
0.5882 Remote Similarity NPD4788 Approved
0.5877 Remote Similarity NPD8081 Approved
0.5868 Remote Similarity NPD7115 Discovery
0.5856 Remote Similarity NPD5696 Approved
0.5849 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5849 Remote Similarity NPD6051 Approved
0.5849 Remote Similarity NPD6101 Approved
0.5847 Remote Similarity NPD6617 Approved
0.5847 Remote Similarity NPD6869 Approved
0.5847 Remote Similarity NPD6847 Approved
0.5847 Remote Similarity NPD8130 Phase 1
0.5843 Remote Similarity NPD1145 Discontinued
0.584 Remote Similarity NPD7642 Approved
0.584 Remote Similarity NPD7604 Phase 2
0.584 Remote Similarity NPD7829 Approved
0.584 Remote Similarity NPD7830 Approved
0.5826 Remote Similarity NPD8393 Approved
0.5816 Remote Similarity NPD6933 Approved
0.5814 Remote Similarity NPD5956 Approved
0.5814 Remote Similarity NPD8392 Approved
0.5814 Remote Similarity NPD8390 Approved
0.5814 Remote Similarity NPD8391 Approved
0.5812 Remote Similarity NPD6013 Approved
0.5812 Remote Similarity NPD6012 Approved
0.5812 Remote Similarity NPD6014 Approved
0.5812 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5806 Remote Similarity NPD5983 Phase 2
0.5798 Remote Similarity NPD6912 Phase 3
0.5794 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5789 Remote Similarity NPD5765 Approved
0.5785 Remote Similarity NPD6940 Discontinued
0.578 Remote Similarity NPD5282 Discontinued
0.5776 Remote Similarity NPD8140 Approved
0.5776 Remote Similarity NPD8307 Discontinued
0.5773 Remote Similarity NPD1810 Approved
0.5773 Remote Similarity NPD1811 Approved
0.5769 Remote Similarity NPD6893 Approved
0.5763 Remote Similarity NPD4634 Approved
0.5758 Remote Similarity NPD6925 Approved
0.5758 Remote Similarity NPD5776 Phase 2
0.5755 Remote Similarity NPD7625 Phase 1
0.5748 Remote Similarity NPD6336 Discontinued

Structure

External Identifiers

PubChem CID   71461980
ChEMBL   CHEMBL2152449
ZINC  

Physicochemical Properties

Molecular Weight:  448.23
ALogP:  -2.0567
MLogP:  2.67
XLogP:  -0.627
# Rotatable Bonds:  19
Polar Surface Area:  166.14
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  2
# Heavy Atoms:  31

Download Data

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