Natural Product: NPC244454

Natural Product ID:  NPC244454
Common Name:   Jacaglabroside B
IUPAC Name:   [(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetyl]oxy-6-[[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetyl]oxymethyl]oxan-3-yl] 2-phenylacetate
Synonyms:   jacaglabroside B
Molecular Formula:   C30H30O13
Standard InCHIKey:  AIFVFVGRWAMEBM-GSQIWVKLSA-N
Standard InCHI:  InChI=1S/C30H30O13/c31-19-6-10-29(38,11-7-19)15-23(34)40-17-21-25(36)26(37)27(42-22(33)14-18-4-2-1-3-5-18)28(41-21)43-24(35)16-30(39)12-8-20(32)9-13-30/h1-13,21,25-28,36-39H,14-17H2/t21-,25-,26+,27-,28+/m1/s1
Canonical SMILES:  O=C1C=CC(C=C1)(O)CC(=O)OC[C@H]1O[C@@H](OC(=O)CC2(O)C=CC(=O)C=C2)[C@@H]([C@H]([C@@H]1O)O)OC(=O)Cc1ccccc1
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
NPO12408 Jacaranda glabra Species Bignoniaceae Eukaryota PMID[20307077]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.56 ug/ml 12662094
NPT839 Cell Line L6 Rattus norvegicus IC50 > 90 ug/ml 12662094

  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 NPC244454 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
0.959 High Similarity NPC11025
0.8731 High Similarity NPC148080
0.8731 High Similarity NPC469623
0.8655 High Similarity NPC474641
0.8583 High Similarity NPC114096
0.856 High Similarity NPC141970
0.856 High Similarity NPC140561
0.8516 High Similarity NPC148026
0.8462 Intermediate Similarity NPC319995
0.8462 Intermediate Similarity NPC289415
0.845 Intermediate Similarity NPC301857
0.8425 Intermediate Similarity NPC87153
0.8425 Intermediate Similarity NPC162925
0.8359 Intermediate Similarity NPC28069
0.8359 Intermediate Similarity NPC77651
0.8321 Intermediate Similarity NPC17567
0.8295 Intermediate Similarity NPC231888
0.8295 Intermediate Similarity NPC63404
0.8295 Intermediate Similarity NPC147032
0.8295 Intermediate Similarity NPC204214
0.8295 Intermediate Similarity NPC198918
0.8295 Intermediate Similarity NPC124878
0.8295 Intermediate Similarity NPC92283
0.8295 Intermediate Similarity NPC10121
0.8295 Intermediate Similarity NPC35338
0.8295 Intermediate Similarity NPC290276
0.8295 Intermediate Similarity NPC10883
0.8281 Intermediate Similarity NPC57607
0.8279 Intermediate Similarity NPC29607
0.8235 Intermediate Similarity NPC184633
0.8231 Intermediate Similarity NPC471025
0.8231 Intermediate Similarity NPC231627
0.8182 Intermediate Similarity NPC470825
0.8168 Intermediate Similarity NPC226101
0.8168 Intermediate Similarity NPC471024
0.8168 Intermediate Similarity NPC237182
0.8154 Intermediate Similarity NPC471026
0.814 Intermediate Similarity NPC317163
0.811 Intermediate Similarity NPC229600
0.8106 Intermediate Similarity NPC27712
0.8099 Intermediate Similarity NPC43584
0.8095 Intermediate Similarity NPC476096
0.8088 Intermediate Similarity NPC471345
0.8045 Intermediate Similarity NPC17968
0.8045 Intermediate Similarity NPC470122
0.8045 Intermediate Similarity NPC469705
0.803 Intermediate Similarity NPC158673
0.8015 Intermediate Similarity NPC252114
0.8 Intermediate Similarity NPC470143
0.8 Intermediate Similarity NPC164172
0.8 Intermediate Similarity NPC322503
0.797 Intermediate Similarity NPC469549
0.7956 Intermediate Similarity NPC472132
0.7939 Intermediate Similarity NPC123704
0.7931 Intermediate Similarity NPC131874
0.7926 Intermediate Similarity NPC471066
0.7926 Intermediate Similarity NPC471095
0.7923 Intermediate Similarity NPC138798
0.7917 Intermediate Similarity NPC22137
0.791 Intermediate Similarity NPC305162
0.7899 Intermediate Similarity NPC47286
0.7899 Intermediate Similarity NPC475195
0.7887 Intermediate Similarity NPC475528
0.7872 Intermediate Similarity NPC478250
0.7868 Intermediate Similarity NPC136608
0.7868 Intermediate Similarity NPC38420
0.7852 Intermediate Similarity NPC476407
0.7852 Intermediate Similarity NPC281798
0.7832 Intermediate Similarity NPC475539
0.7832 Intermediate Similarity NPC212808
0.7832 Intermediate Similarity NPC119773
0.7832 Intermediate Similarity NPC474268
0.7832 Intermediate Similarity NPC143246
0.782 Intermediate Similarity NPC288416
0.7808 Intermediate Similarity NPC474620
0.7803 Intermediate Similarity NPC79608
0.7786 Intermediate Similarity NPC473881
0.7786 Intermediate Similarity NPC77493
0.7778 Intermediate Similarity NPC262826
0.777 Intermediate Similarity NPC156393
0.777 Intermediate Similarity NPC469696
0.7762 Intermediate Similarity NPC477737
0.776 Intermediate Similarity NPC87069
0.7754 Intermediate Similarity NPC123988
0.7744 Intermediate Similarity NPC267733
0.7744 Intermediate Similarity NPC276047
0.7737 Intermediate Similarity NPC114116
0.7727 Intermediate Similarity NPC145287
0.7724 Intermediate Similarity NPC473138
0.7724 Intermediate Similarity NPC276061
0.7724 Intermediate Similarity NPC474148
0.7724 Intermediate Similarity NPC28776
0.7721 Intermediate Similarity NPC235294
0.7721 Intermediate Similarity NPC46137
0.7721 Intermediate Similarity NPC478255
0.771 Intermediate Similarity NPC52097
0.7705 Intermediate Similarity NPC20485
0.7703 Intermediate Similarity NPC87403
0.7687 Intermediate Similarity NPC106677
0.7681 Intermediate Similarity NPC169398
0.7676 Intermediate Similarity NPC65833
0.7676 Intermediate Similarity NPC245219
0.7676 Intermediate Similarity NPC284957
0.7676 Intermediate Similarity NPC31081
0.7669 Intermediate Similarity NPC83218
0.7669 Intermediate Similarity NPC126991
0.7669 Intermediate Similarity NPC476033
0.7667 Intermediate Similarity NPC469527
0.7661 Intermediate Similarity NPC264784
0.7661 Intermediate Similarity NPC30563
0.7655 Intermediate Similarity NPC470330
0.7651 Intermediate Similarity NPC469417
0.7651 Intermediate Similarity NPC477735
0.7643 Intermediate Similarity NPC100558
0.7643 Intermediate Similarity NPC101686
0.7643 Intermediate Similarity NPC310252
0.7643 Intermediate Similarity NPC469364
0.7643 Intermediate Similarity NPC84789
0.7643 Intermediate Similarity NPC302583
0.7643 Intermediate Similarity NPC65262
0.7635 Intermediate Similarity NPC5115
0.7635 Intermediate Similarity NPC106818
0.7634 Intermediate Similarity NPC11724
0.7626 Intermediate Similarity NPC158325
0.7626 Intermediate Similarity NPC103398
0.7626 Intermediate Similarity NPC180171
0.7619 Intermediate Similarity NPC474363
0.7619 Intermediate Similarity NPC172525
0.7616 Intermediate Similarity NPC476026
0.7616 Intermediate Similarity NPC474398
0.7616 Intermediate Similarity NPC474441
0.7616 Intermediate Similarity NPC474401
0.7612 Intermediate Similarity NPC471157
0.7606 Intermediate Similarity NPC80098
0.7603 Intermediate Similarity NPC469448
0.76 Intermediate Similarity NPC3449
0.76 Intermediate Similarity NPC477736
0.7591 Intermediate Similarity NPC209851
0.7591 Intermediate Similarity NPC246869
0.7591 Intermediate Similarity NPC225384
0.7591 Intermediate Similarity NPC138777
0.7589 Intermediate Similarity NPC476643
0.7589 Intermediate Similarity NPC474250
0.7586 Intermediate Similarity NPC291153
0.7582 Intermediate Similarity NPC471493
0.7574 Intermediate Similarity NPC253595
0.7569 Intermediate Similarity NPC77922
0.7569 Intermediate Similarity NPC471028
0.7569 Intermediate Similarity NPC202391
0.7569 Intermediate Similarity NPC296659
0.7569 Intermediate Similarity NPC473281
0.7569 Intermediate Similarity NPC63304
0.7568 Intermediate Similarity NPC133430
0.7568 Intermediate Similarity NPC473966
0.7568 Intermediate Similarity NPC469477
0.7566 Intermediate Similarity NPC57072
0.7566 Intermediate Similarity NPC231475
0.7557 Intermediate Similarity NPC476872
0.7556 Intermediate Similarity NPC175333
0.7541 Intermediate Similarity NPC37714
0.7541 Intermediate Similarity NPC152384
0.7535 Intermediate Similarity NPC213567
0.7533 Intermediate Similarity NPC205172
0.7533 Intermediate Similarity NPC209393
0.75 Intermediate Similarity NPC225307
0.75 Intermediate Similarity NPC210531
0.75 Intermediate Similarity NPC111466
0.75 Intermediate Similarity NPC208651
0.75 Intermediate Similarity NPC242756
0.75 Intermediate Similarity NPC206641
0.75 Intermediate Similarity NPC263829
0.75 Intermediate Similarity NPC320259
0.7483 Intermediate Similarity NPC303429
0.7483 Intermediate Similarity NPC222102
0.7483 Intermediate Similarity NPC79908
0.7483 Intermediate Similarity NPC469399
0.7483 Intermediate Similarity NPC302989
0.7468 Intermediate Similarity NPC71780
0.7466 Intermediate Similarity NPC473867
0.7465 Intermediate Similarity NPC220942
0.7465 Intermediate Similarity NPC31745
0.7465 Intermediate Similarity NPC220936
0.7465 Intermediate Similarity NPC62800
0.7465 Intermediate Similarity NPC324262
0.7464 Intermediate Similarity NPC80599
0.746 Intermediate Similarity NPC234376
0.746 Intermediate Similarity NPC158282
0.745 Intermediate Similarity NPC289021
0.745 Intermediate Similarity NPC158546
0.7448 Intermediate Similarity NPC194938
0.7448 Intermediate Similarity NPC264270
0.7448 Intermediate Similarity NPC40085
0.7447 Intermediate Similarity NPC470572
0.7445 Intermediate Similarity NPC472388
0.7445 Intermediate Similarity NPC473443
0.7444 Intermediate Similarity NPC223351
0.7444 Intermediate Similarity NPC108286
0.7434 Intermediate Similarity NPC283480
0.7434 Intermediate Similarity NPC148323
0.7432 Intermediate Similarity NPC478236

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC244454 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
0.7794 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD5048 Discontinued
0.7347 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD7266 Discontinued
0.7273 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD6647 Phase 2
0.7226 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD9495 Approved
0.7154 Intermediate Similarity NPD2629 Approved
0.7054 Intermediate Similarity NPD969 Suspended
0.702 Intermediate Similarity NPD5403 Approved
0.7019 Intermediate Similarity NPD7799 Discontinued
0.6959 Remote Similarity NPD2575 Approved
0.695 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6913 Remote Similarity NPD6190 Approved
0.6905 Remote Similarity NPD1237 Approved
0.6899 Remote Similarity NPD2067 Discontinued
0.6894 Remote Similarity NPD690 Clinical (unspecified phase)
0.6887 Remote Similarity NPD5401 Approved
0.6883 Remote Similarity NPD4380 Phase 2
0.6871 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6867 Remote Similarity NPD8313 Approved
0.6867 Remote Similarity NPD8312 Approved
0.686 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6859 Remote Similarity NPD8455 Phase 2
0.6855 Remote Similarity NPD2066 Phase 3
0.6855 Remote Similarity NPD7798 Approved
0.6846 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6838 Remote Similarity NPD5125 Phase 3
0.6838 Remote Similarity NPD5126 Approved
0.6825 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6822 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6010 Discontinued
0.6815 Remote Similarity NPD5402 Approved
0.6807 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7054 Approved
0.6761 Remote Similarity NPD2613 Approved
0.6747 Remote Similarity NPD6559 Discontinued
0.6739 Remote Similarity NPD1091 Approved
0.6733 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6727 Remote Similarity NPD7472 Approved
0.6727 Remote Similarity NPD7074 Phase 3
0.6715 Remote Similarity NPD5306 Approved
0.6715 Remote Similarity NPD5305 Approved
0.6707 Remote Similarity NPD3818 Discontinued
0.6692 Remote Similarity NPD2182 Approved
0.6687 Remote Similarity NPD6797 Phase 2
0.6686 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2626 Approved
0.6667 Remote Similarity NPD2625 Approved
0.6667 Remote Similarity NPD4136 Approved
0.6667 Remote Similarity NPD4106 Approved
0.6667 Remote Similarity NPD2160 Approved
0.6667 Remote Similarity NPD2628 Approved
0.6667 Remote Similarity NPD2627 Approved
0.6667 Remote Similarity NPD2159 Approved
0.6667 Remote Similarity NPD4135 Approved
0.6667 Remote Similarity NPD6685 Approved
0.6647 Remote Similarity NPD7685 Pre-registration
0.6647 Remote Similarity NPD7251 Discontinued
0.6647 Remote Similarity NPD8368 Discontinued
0.6643 Remote Similarity NPD4620 Approved
0.6643 Remote Similarity NPD5201 Approved
0.6643 Remote Similarity NPD5203 Approved
0.6643 Remote Similarity NPD4617 Approved
0.6641 Remote Similarity NPD5909 Discontinued
0.6625 Remote Similarity NPD7075 Discontinued
0.6623 Remote Similarity NPD4628 Phase 3
0.6621 Remote Similarity NPD3090 Approved
0.6621 Remote Similarity NPD4745 Approved
0.6621 Remote Similarity NPD2570 Approved
0.6621 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6621 Remote Similarity NPD3089 Approved
0.6621 Remote Similarity NPD2571 Approved
0.6621 Remote Similarity NPD2573 Approved
0.6621 Remote Similarity NPD2574 Discontinued
0.6621 Remote Similarity NPD3615 Approved
0.6621 Remote Similarity NPD4746 Phase 3
0.6621 Remote Similarity NPD3088 Approved
0.6621 Remote Similarity NPD3087 Approved
0.6621 Remote Similarity NPD3616 Approved
0.6621 Remote Similarity NPD3614 Approved
0.6621 Remote Similarity NPD2566 Approved
0.6619 Remote Similarity NPD4807 Approved
0.6619 Remote Similarity NPD4806 Approved
0.6612 Remote Similarity NPD9258 Approved
0.6612 Remote Similarity NPD9256 Approved
0.6607 Remote Similarity NPD7808 Phase 3
0.6606 Remote Similarity NPD3751 Discontinued
0.6591 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6587 Remote Similarity NPD1238 Approved
0.6582 Remote Similarity NPD6801 Discontinued
0.6581 Remote Similarity NPD9491 Approved
0.6575 Remote Similarity NPD5121 Approved
0.6575 Remote Similarity NPD5120 Approved
0.6575 Remote Similarity NPD5119 Approved
0.6569 Remote Similarity NPD9545 Approved
0.6567 Remote Similarity NPD2650 Approved
0.6567 Remote Similarity NPD2652 Approved
0.6562 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6562 Remote Similarity NPD1930 Approved
0.6562 Remote Similarity NPD5765 Approved
0.6562 Remote Similarity NPD1929 Approved
0.6554 Remote Similarity NPD4978 Clinical (unspecified phase)
0.655 Remote Similarity NPD8150 Discontinued
0.6541 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6541 Remote Similarity NPD6912 Phase 3
0.6538 Remote Similarity NPD1653 Approved
0.6536 Remote Similarity NPD7236 Approved
0.6531 Remote Similarity NPD4684 Phase 3
0.6531 Remote Similarity NPD4686 Approved
0.6531 Remote Similarity NPD4685 Phase 3
0.6529 Remote Similarity NPD689 Discontinued
0.6529 Remote Similarity NPD8407 Phase 2
0.6528 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6522 Remote Similarity NPD8513 Phase 3
0.6522 Remote Similarity NPD4105 Approved
0.6522 Remote Similarity NPD8517 Approved
0.6522 Remote Similarity NPD8515 Approved
0.6522 Remote Similarity NPD4102 Approved
0.6522 Remote Similarity NPD8516 Approved
0.6519 Remote Similarity NPD7411 Suspended
0.651 Remote Similarity NPD7033 Discontinued
0.65 Remote Similarity NPD4218 Approved
0.65 Remote Similarity NPD2608 Approved
0.65 Remote Similarity NPD2610 Approved
0.65 Remote Similarity NPD4217 Approved
0.65 Remote Similarity NPD2612 Approved
0.65 Remote Similarity NPD2609 Approved
0.65 Remote Similarity NPD3132 Approved
0.65 Remote Similarity NPD4216 Approved
0.65 Remote Similarity NPD3131 Approved
0.65 Remote Similarity NPD4215 Approved
0.65 Remote Similarity NPD2611 Approved
0.6494 Remote Similarity NPD6799 Approved
0.6494 Remote Similarity NPD6143 Clinical (unspecified phase)
0.648 Remote Similarity NPD1989 Approved
0.6474 Remote Similarity NPD8361 Approved
0.6474 Remote Similarity NPD8360 Approved
0.6471 Remote Similarity NPD4198 Discontinued
0.6463 Remote Similarity NPD6310 Approved
0.6463 Remote Similarity NPD6309 Approved
0.6463 Remote Similarity NPD6311 Approved
0.646 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6458 Remote Similarity NPD5204 Approved
0.6452 Remote Similarity NPD1202 Approved
0.6438 Remote Similarity NPD3764 Approved
0.6433 Remote Similarity NPD7239 Suspended
0.6423 Remote Similarity NPD694 Clinical (unspecified phase)
0.6423 Remote Similarity NPD9493 Approved
0.642 Remote Similarity NPD6534 Approved
0.642 Remote Similarity NPD6535 Approved
0.6419 Remote Similarity NPD1933 Approved
0.6408 Remote Similarity NPD5157 Phase 1
0.6408 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6408 Remote Similarity NPD5159 Phase 2
0.64 Remote Similarity NPD1693 Approved
0.6397 Remote Similarity NPD5951 Approved
0.6395 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6395 Remote Similarity NPD6233 Phase 2
0.6393 Remote Similarity NPD800 Approved
0.6389 Remote Similarity NPD5647 Approved
0.6385 Remote Similarity NPD164 Approved
0.6382 Remote Similarity NPD1549 Phase 2
0.6379 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6379 Remote Similarity NPD8435 Approved
0.6378 Remote Similarity NPD8029 Clinical (unspecified phase)
0.637 Remote Similarity NPD6858 Approved
0.637 Remote Similarity NPD7008 Discontinued
0.637 Remote Similarity NPD7094 Approved
0.6364 Remote Similarity NPD9263 Approved
0.6364 Remote Similarity NPD9264 Approved
0.6364 Remote Similarity NPD3787 Discontinued
0.6364 Remote Similarity NPD6686 Approved
0.6364 Remote Similarity NPD9267 Approved
0.6357 Remote Similarity NPD1932 Approved
0.6357 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6345 Remote Similarity NPD3662 Phase 3
0.6345 Remote Similarity NPD3661 Approved
0.6345 Remote Similarity NPD3663 Approved
0.6345 Remote Similarity NPD3664 Approved
0.6341 Remote Similarity NPD1086 Approved
0.6341 Remote Similarity NPD1090 Approved
0.6341 Remote Similarity NPD1089 Approved
0.634 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7097 Phase 1
0.6327 Remote Similarity NPD2313 Discontinued
0.6319 Remote Similarity NPD7435 Discontinued
0.6316 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6316 Remote Similarity NPD74 Approved
0.6316 Remote Similarity NPD9266 Approved
0.6316 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6313 Remote Similarity NPD7700 Phase 2
0.6313 Remote Similarity NPD7699 Phase 2
0.631 Remote Similarity NPD7228 Approved
0.6309 Remote Similarity NPD230 Phase 1
0.6301 Remote Similarity NPD6832 Phase 2
0.6299 Remote Similarity NPD3750 Approved

Structure

External Identifiers

PubChem CID   45360280
ChEMBL   CHEMBL1094580
ZINC  

Physicochemical Properties

Molecular Weight:  598.17
ALogP:  -1.875
MLogP:  3.33
XLogP:  1.96
# Rotatable Bonds:  17
Polar Surface Area:  203.19
# H-Bond Aceptor:  13
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  43

Download Data

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