Natural Product: NPC22149

Natural Product ID:  NPC22149
Common Name:   Methyl (1S)-7-(Hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-1,4A,5,7A-Tetrahydrocyclopenta[C]Pyran-4-Carboxylate
IUPAC Name:   methyl (1S)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:  
Molecular Formula:   C17H24O10
Standard InCHIKey:  IBFYXTRXDNAPMM-QZTNVZDFSA-N
Standard InCHI:  InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8?,10-,11?,12-,13+,14-,16+,17+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C(C3C2C(=CC3)CO)C(=O)OC)[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
NPO12588 Cornus officinalis Species Cornaceae Eukaryota TM-MC*
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota TM-MC*
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota TM-MC*
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota TM-MC*
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota TM-MC*
NPO10008 Tinospora capillipes Species Menispermaceae Eukaryota TM-MC*
NPO25734 Paratinospora sagittata Species Menispermaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency 23099.9 nM PubChem BioAssay data set
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency 89125.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 6513.1 nM PubChem BioAssay data set
NPT10 Individual Protein Geminin Homo sapiens Potency 73.1 nM PubChem BioAssay data set

  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 NPC22149 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
1.0 High Similarity NPC306344
1.0 High Similarity NPC255677
0.9892 High Similarity NPC298255
0.9892 High Similarity NPC28304
0.9684 High Similarity NPC267869
0.9684 High Similarity NPC234304
0.9684 High Similarity NPC197541
0.9684 High Similarity NPC284929
0.9684 High Similarity NPC118761
0.9674 High Similarity NPC241911
0.9583 High Similarity NPC86095
0.9579 High Similarity NPC261117
0.9579 High Similarity NPC222062
0.9579 High Similarity NPC250545
0.9579 High Similarity NPC310804
0.9375 High Similarity NPC13171
0.9375 High Similarity NPC195510
0.914 High Similarity NPC61201
0.8925 High Similarity NPC303451
0.8925 High Similarity NPC6414
0.8812 High Similarity NPC254538
0.8812 High Similarity NPC474285
0.8723 High Similarity NPC117596
0.8632 High Similarity NPC472125
0.8632 High Similarity NPC472124
0.8632 High Similarity NPC472126
0.8602 High Similarity NPC142583
0.8557 High Similarity NPC469543
0.8557 High Similarity NPC170204
0.8526 High Similarity NPC65665
0.8526 High Similarity NPC307699
0.8526 High Similarity NPC216826
0.8526 High Similarity NPC120021
0.8526 High Similarity NPC231710
0.8526 High Similarity NPC270908
0.8526 High Similarity NPC470573
0.85 High Similarity NPC20673
0.8416 Intermediate Similarity NPC471599
0.84 Intermediate Similarity NPC244878
0.837 Intermediate Similarity NPC188717
0.837 Intermediate Similarity NPC211455
0.8367 Intermediate Similarity NPC101051
0.8333 Intermediate Similarity NPC475928
0.8317 Intermediate Similarity NPC219038
0.83 Intermediate Similarity NPC151093
0.8283 Intermediate Similarity NPC306041
0.8283 Intermediate Similarity NPC161293
0.828 Intermediate Similarity NPC136699
0.828 Intermediate Similarity NPC220167
0.8235 Intermediate Similarity NPC177013
0.8235 Intermediate Similarity NPC35185
0.8235 Intermediate Similarity NPC4899
0.8235 Intermediate Similarity NPC474730
0.8235 Intermediate Similarity NPC106668
0.8173 Intermediate Similarity NPC170432
0.8163 Intermediate Similarity NPC280390
0.8155 Intermediate Similarity NPC27687
0.8155 Intermediate Similarity NPC37240
0.8137 Intermediate Similarity NPC98859
0.8137 Intermediate Similarity NPC4637
0.8137 Intermediate Similarity NPC287539
0.8137 Intermediate Similarity NPC3488
0.8119 Intermediate Similarity NPC472015
0.8095 Intermediate Similarity NPC80338
0.8095 Intermediate Similarity NPC148270
0.8095 Intermediate Similarity NPC197813
0.8061 Intermediate Similarity NPC9447
0.802 Intermediate Similarity NPC472290
0.8019 Intermediate Similarity NPC110701
0.8 Intermediate Similarity NPC470124
0.8 Intermediate Similarity NPC127235
0.798 Intermediate Similarity NPC320552
0.798 Intermediate Similarity NPC472196
0.798 Intermediate Similarity NPC238090
0.798 Intermediate Similarity NPC472195
0.7959 Intermediate Similarity NPC327253
0.7941 Intermediate Similarity NPC473307
0.7938 Intermediate Similarity NPC137368
0.7921 Intermediate Similarity NPC54731
0.79 Intermediate Similarity NPC159698
0.79 Intermediate Similarity NPC63897
0.7895 Intermediate Similarity NPC266718
0.7895 Intermediate Similarity NPC475035
0.7879 Intermediate Similarity NPC472197
0.7879 Intermediate Similarity NPC477749
0.787 Intermediate Similarity NPC193741
0.7864 Intermediate Similarity NPC473146
0.7843 Intermediate Similarity NPC153559
0.7835 Intermediate Similarity NPC475037
0.7822 Intermediate Similarity NPC291709
0.7822 Intermediate Similarity NPC241407
0.7812 Intermediate Similarity NPC470658
0.7767 Intermediate Similarity NPC124181
0.7727 Intermediate Similarity NPC475924
0.7727 Intermediate Similarity NPC475851
0.7723 Intermediate Similarity NPC2003
0.7723 Intermediate Similarity NPC475927
0.7723 Intermediate Similarity NPC25701
0.7723 Intermediate Similarity NPC475832
0.7714 Intermediate Similarity NPC304163
0.7714 Intermediate Similarity NPC201191
0.77 Intermediate Similarity NPC472199
0.7685 Intermediate Similarity NPC392
0.7685 Intermediate Similarity NPC177524
0.7685 Intermediate Similarity NPC219900
0.7677 Intermediate Similarity NPC477748
0.7677 Intermediate Similarity NPC249408
0.7677 Intermediate Similarity NPC104129
0.7652 Intermediate Similarity NPC470829
0.7652 Intermediate Similarity NPC473228
0.7629 Intermediate Similarity NPC475034
0.7624 Intermediate Similarity NPC320089
0.76 Intermediate Similarity NPC202886
0.7596 Intermediate Similarity NPC307517
0.7596 Intermediate Similarity NPC40182
0.7596 Intermediate Similarity NPC169468
0.7596 Intermediate Similarity NPC81483
0.7596 Intermediate Similarity NPC90819
0.7596 Intermediate Similarity NPC61630
0.7596 Intermediate Similarity NPC198422
0.7573 Intermediate Similarity NPC256230
0.7549 Intermediate Similarity NPC71589
0.7549 Intermediate Similarity NPC472198
0.7549 Intermediate Similarity NPC256368
0.7549 Intermediate Similarity NPC294293
0.7547 Intermediate Similarity NPC80144
0.7544 Intermediate Similarity NPC475309
0.7544 Intermediate Similarity NPC13710
0.7525 Intermediate Similarity NPC274274
0.7525 Intermediate Similarity NPC473150
0.7525 Intermediate Similarity NPC294643
0.7525 Intermediate Similarity NPC473321
0.7523 Intermediate Similarity NPC475960
0.75 Intermediate Similarity NPC476613
0.75 Intermediate Similarity NPC474194
0.75 Intermediate Similarity NPC93190
0.75 Intermediate Similarity NPC476612
0.75 Intermediate Similarity NPC41681
0.75 Intermediate Similarity NPC50464
0.7477 Intermediate Similarity NPC197736
0.7476 Intermediate Similarity NPC36954
0.7476 Intermediate Similarity NPC93869
0.7476 Intermediate Similarity NPC6765
0.7475 Intermediate Similarity NPC74139
0.7475 Intermediate Similarity NPC118077
0.7475 Intermediate Similarity NPC475186
0.7474 Intermediate Similarity NPC127295
0.7474 Intermediate Similarity NPC163362
0.7458 Intermediate Similarity NPC318135
0.7453 Intermediate Similarity NPC67296
0.7453 Intermediate Similarity NPC198992
0.7453 Intermediate Similarity NPC476611
0.7451 Intermediate Similarity NPC475912
0.7449 Intermediate Similarity NPC21469
0.7449 Intermediate Similarity NPC477746
0.7449 Intermediate Similarity NPC477747
0.7434 Intermediate Similarity NPC472274
0.7429 Intermediate Similarity NPC37866
0.7429 Intermediate Similarity NPC249171
0.7429 Intermediate Similarity NPC49833
0.7426 Intermediate Similarity NPC474232
0.7426 Intermediate Similarity NPC473619
0.7426 Intermediate Similarity NPC118078
0.7423 Intermediate Similarity NPC142111
0.7423 Intermediate Similarity NPC473315
0.7407 Intermediate Similarity NPC474917
0.74 Intermediate Similarity NPC473151
0.74 Intermediate Similarity NPC473715
0.74 Intermediate Similarity NPC470137
0.7387 Intermediate Similarity NPC83005
0.7383 Intermediate Similarity NPC86077
0.7379 Intermediate Similarity NPC274588
0.7368 Intermediate Similarity NPC277583
0.7368 Intermediate Similarity NPC323472
0.7368 Intermediate Similarity NPC321728
0.7364 Intermediate Similarity NPC473807
0.7358 Intermediate Similarity NPC469402
0.7353 Intermediate Similarity NPC470373
0.7353 Intermediate Similarity NPC470379
0.735 Intermediate Similarity NPC202051
0.7347 Intermediate Similarity NPC212363
0.7347 Intermediate Similarity NPC473308
0.7345 Intermediate Similarity NPC293658
0.7345 Intermediate Similarity NPC264153
0.7345 Intermediate Similarity NPC474410
0.7339 Intermediate Similarity NPC153095
0.7339 Intermediate Similarity NPC243998
0.7339 Intermediate Similarity NPC223450
0.7339 Intermediate Similarity NPC85670
0.7333 Intermediate Similarity NPC236580
0.7333 Intermediate Similarity NPC304445
0.7328 Intermediate Similarity NPC219656
0.732 Intermediate Similarity NPC251026
0.7315 Intermediate Similarity NPC151516
0.7315 Intermediate Similarity NPC473148
0.7308 Intermediate Similarity NPC14961
0.7308 Intermediate Similarity NPC471142
0.7308 Intermediate Similarity NPC270013
0.7297 Intermediate Similarity NPC257853
0.7297 Intermediate Similarity NPC118225

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC22149 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
0.7685 Intermediate Similarity NPD6686 Approved
0.7426 Intermediate Similarity NPD46 Approved
0.7426 Intermediate Similarity NPD6698 Approved
0.7264 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD8513 Phase 3
0.7168 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7503 Approved
0.7059 Intermediate Similarity NPD8516 Approved
0.7059 Intermediate Similarity NPD8517 Approved
0.7059 Intermediate Similarity NPD8515 Approved
0.6967 Remote Similarity NPD7507 Approved
0.6863 Remote Similarity NPD4249 Approved
0.6857 Remote Similarity NPD7983 Approved
0.6814 Remote Similarity NPD7899 Clinical (unspecified phase)
0.681 Remote Similarity NPD6053 Discontinued
0.68 Remote Similarity NPD7319 Approved
0.6796 Remote Similarity NPD4250 Approved
0.6796 Remote Similarity NPD4251 Approved
0.6783 Remote Similarity NPD6371 Approved
0.6762 Remote Similarity NPD7838 Discovery
0.6733 Remote Similarity NPD7154 Phase 3
0.6733 Remote Similarity NPD6110 Phase 1
0.6667 Remote Similarity NPD7830 Approved
0.6667 Remote Similarity NPD7328 Approved
0.6667 Remote Similarity NPD7829 Approved
0.6667 Remote Similarity NPD7327 Approved
0.6667 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6412 Phase 2
0.6639 Remote Similarity NPD8033 Approved
0.6612 Remote Similarity NPD7516 Approved
0.6557 Remote Similarity NPD8294 Approved
0.6557 Remote Similarity NPD8377 Approved
0.6508 Remote Similarity NPD8074 Phase 3
0.6504 Remote Similarity NPD8380 Approved
0.6504 Remote Similarity NPD8379 Approved
0.6504 Remote Similarity NPD8296 Approved
0.6504 Remote Similarity NPD8378 Approved
0.6504 Remote Similarity NPD8335 Approved
0.6486 Remote Similarity NPD4225 Approved
0.6471 Remote Similarity NPD8133 Approved
0.6455 Remote Similarity NPD7839 Suspended
0.6436 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6408 Remote Similarity NPD5362 Discontinued
0.64 Remote Similarity NPD7642 Approved
0.6393 Remote Similarity NPD7641 Discontinued
0.6389 Remote Similarity NPD7637 Suspended
0.6372 Remote Similarity NPD5344 Discontinued
0.6371 Remote Similarity NPD8444 Approved
0.6355 Remote Similarity NPD1695 Approved
0.633 Remote Similarity NPD5778 Approved
0.633 Remote Similarity NPD5779 Approved
0.6311 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7115 Discovery
0.6299 Remote Similarity NPD8451 Approved
0.6286 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6283 Remote Similarity NPD7639 Approved
0.6283 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD8448 Approved
0.6238 Remote Similarity NPD4271 Approved
0.6238 Remote Similarity NPD4268 Approved
0.622 Remote Similarity NPD8299 Approved
0.622 Remote Similarity NPD8342 Approved
0.622 Remote Similarity NPD8341 Approved
0.622 Remote Similarity NPD8340 Approved
0.6216 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6195 Remote Similarity NPD7638 Approved
0.619 Remote Similarity NPD8080 Discontinued
0.6147 Remote Similarity NPD5785 Approved
0.6142 Remote Similarity NPD8328 Phase 3
0.6134 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6132 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6126 Remote Similarity NPD5282 Discontinued
0.6121 Remote Similarity NPD1407 Approved
0.6117 Remote Similarity NPD4820 Approved
0.6117 Remote Similarity NPD4819 Approved
0.6117 Remote Similarity NPD4822 Approved
0.6117 Remote Similarity NPD4821 Approved
0.6111 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6107 Remote Similarity NPD8392 Approved
0.6107 Remote Similarity NPD8390 Approved
0.6107 Remote Similarity NPD8391 Approved
0.6078 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6077 Remote Similarity NPD7736 Approved
0.6074 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6063 Remote Similarity NPD6370 Approved
0.6048 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6048 Remote Similarity NPD6009 Approved
0.6032 Remote Similarity NPD6319 Approved
0.6 Remote Similarity NPD8293 Discontinued
0.6 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6 Remote Similarity NPD6648 Approved
0.6 Remote Similarity NPD6435 Approved
0.5984 Remote Similarity NPD6882 Approved
0.5981 Remote Similarity NPD5363 Approved
0.5969 Remote Similarity NPD7492 Approved
0.5962 Remote Similarity NPD4252 Approved
0.5954 Remote Similarity NPD8336 Approved
0.5954 Remote Similarity NPD8337 Approved
0.5943 Remote Similarity NPD5331 Approved
0.5943 Remote Similarity NPD5332 Approved
0.594 Remote Similarity NPD7260 Phase 2
0.5935 Remote Similarity NPD4632 Approved
0.5926 Remote Similarity NPD5786 Approved
0.5923 Remote Similarity NPD6616 Approved
0.5909 Remote Similarity NPD6101 Approved
0.5909 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5906 Remote Similarity NPD6054 Approved
0.5905 Remote Similarity NPD4790 Discontinued
0.5878 Remote Similarity NPD7078 Approved
0.5876 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5872 Remote Similarity NPD7524 Approved
0.5859 Remote Similarity NPD6015 Approved
0.5859 Remote Similarity NPD6016 Approved
0.5854 Remote Similarity NPD8297 Approved
0.5849 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5849 Remote Similarity NPD4270 Approved
0.5849 Remote Similarity NPD4269 Approved
0.5849 Remote Similarity NPD5209 Approved
0.582 Remote Similarity NPD5955 Clinical (unspecified phase)
0.582 Remote Similarity NPD6421 Discontinued
0.5814 Remote Similarity NPD5988 Approved
0.581 Remote Similarity NPD5368 Approved
0.5804 Remote Similarity NPD6411 Approved
0.5781 Remote Similarity NPD6059 Approved
0.5778 Remote Similarity NPD8338 Approved
0.5772 Remote Similarity NPD2204 Approved
0.5763 Remote Similarity NPD7632 Discontinued
0.5752 Remote Similarity NPD6399 Phase 3
0.5741 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5739 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5714 Remote Similarity NPD897 Approved
0.5714 Remote Similarity NPD898 Approved
0.5714 Remote Similarity NPD896 Approved
0.5702 Remote Similarity NPD5697 Approved
0.5682 Remote Similarity NPD8273 Phase 1
0.5673 Remote Similarity NPD4756 Discovery
0.5669 Remote Similarity NPD7500 Approved
0.5662 Remote Similarity NPD6845 Suspended
0.566 Remote Similarity NPD7332 Phase 2
0.5656 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5656 Remote Similarity NPD6899 Approved
0.5656 Remote Similarity NPD6881 Approved
0.5652 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5648 Remote Similarity NPD6695 Phase 3
0.5645 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5645 Remote Similarity NPD6649 Approved
0.5645 Remote Similarity NPD6650 Approved
0.562 Remote Similarity NPD6640 Phase 3
0.562 Remote Similarity NPD6402 Approved
0.562 Remote Similarity NPD7128 Approved
0.562 Remote Similarity NPD5739 Approved
0.562 Remote Similarity NPD6675 Approved
0.5617 Remote Similarity NPD7685 Pre-registration
0.5615 Remote Similarity NPD5983 Phase 2
0.561 Remote Similarity NPD6014 Approved
0.561 Remote Similarity NPD6372 Approved
0.561 Remote Similarity NPD6013 Approved
0.561 Remote Similarity NPD6373 Approved
0.561 Remote Similarity NPD6012 Approved
0.5607 Remote Similarity NPD5369 Approved

Structure

External Identifiers

PubChem CID   16760120
ChEMBL   CHEMBL1718933
ZINC  

Physicochemical Properties

Molecular Weight:  388.14
ALogP:  -2.9212
MLogP:  2.23
XLogP:  -1.854
# Rotatable Bonds:  12
Polar Surface Area:  155.14
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  27

Download Data

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