Natural Product: NPC478073

Natural Product ID:  NPC478073
Common Name:   Trichirubine B
IUPAC Name:  
Synonyms:   Trichirubine B
Molecular Formula:   C33H34O8
Standard InCHIKey:  PFMJYSWUJIOQAK-NUHWSDSJSA-N
Standard InCHI:  InChI=1S/C33H34O8/c1-29-13-12-21(34)32(4)25(29)24(38-16-29)26(40-27(36)17-8-6-5-7-9-17)31(3)20-11-10-19(18-14-23(35)39-28(18)37)30(20,2)15-22-33(31,32)41-22/h5-9,11-14,19,22-26,35H,10,15-16H2,1-4H3/t19-,22-,23?,24+,25-,26+,29-,30-,31+,32-,33-/m0/s1
Canonical SMILES:  OC1OC(=O)C(=C1)[C@@H]1CC=C2[C@@]1(C)C[C@@H]1O[C@@]31[C@@]2(C)[C@H](OC(=O)c1ccccc1)[C@H]1[C@@H]2[C@]3(C)C(=O)C=C[C@]2(CO1)C
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
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota leaves Kibale National Park, Uganda 2000-2001 PMID[19299148]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.2 ug/ml 19299148

  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 NPC478073 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
0.8875 High Similarity NPC322420
0.8765 High Similarity NPC324769
0.8765 High Similarity NPC325732
0.8696 High Similarity NPC477190
0.8696 High Similarity NPC477188
0.8696 High Similarity NPC43304
0.8671 High Similarity NPC471176
0.8671 High Similarity NPC5115
0.865 High Similarity NPC61891
0.865 High Similarity NPC477491
0.8625 High Similarity NPC469399
0.8608 High Similarity NPC133430
0.8608 High Similarity NPC469477
0.8589 High Similarity NPC471134
0.8589 High Similarity NPC471493
0.8562 High Similarity NPC469417
0.8553 High Similarity NPC251139
0.8545 High Similarity NPC40138
0.8544 High Similarity NPC472548
0.8528 High Similarity NPC66193
0.8526 High Similarity NPC132652
0.8509 High Similarity NPC49297
0.8506 High Similarity NPC477894
0.85 High Similarity NPC11410
0.85 High Similarity NPC106895
0.8494 Intermediate Similarity NPC477488
0.8491 Intermediate Similarity NPC472657
0.8491 Intermediate Similarity NPC472658
0.8481 Intermediate Similarity NPC472398
0.8481 Intermediate Similarity NPC51602
0.8481 Intermediate Similarity NPC197037
0.8481 Intermediate Similarity NPC471103
0.8466 Intermediate Similarity NPC275477
0.8452 Intermediate Similarity NPC469421
0.8447 Intermediate Similarity NPC181924
0.8438 Intermediate Similarity NPC473670
0.8438 Intermediate Similarity NPC472549
0.8438 Intermediate Similarity NPC282239
0.8438 Intermediate Similarity NPC21410
0.8434 Intermediate Similarity NPC102465
0.8431 Intermediate Similarity NPC183270
0.8431 Intermediate Similarity NPC477904
0.8428 Intermediate Similarity NPC477905
0.8428 Intermediate Similarity NPC22571
0.8428 Intermediate Similarity NPC469648
0.8428 Intermediate Similarity NPC138641
0.8428 Intermediate Similarity NPC469647
0.8428 Intermediate Similarity NPC283875
0.8418 Intermediate Similarity NPC91730
0.8418 Intermediate Similarity NPC7095
0.8418 Intermediate Similarity NPC254558
0.8397 Intermediate Similarity NPC471100
0.8397 Intermediate Similarity NPC471107
0.8387 Intermediate Similarity NPC95449
0.8375 Intermediate Similarity NPC229545
0.8375 Intermediate Similarity NPC134685
0.8375 Intermediate Similarity NPC248265
0.8375 Intermediate Similarity NPC11588
0.8365 Intermediate Similarity NPC470153
0.8354 Intermediate Similarity NPC60509
0.8354 Intermediate Similarity NPC250046
0.8354 Intermediate Similarity NPC81698
0.8344 Intermediate Similarity NPC240115
0.8344 Intermediate Similarity NPC469513
0.8333 Intermediate Similarity NPC472393
0.8323 Intermediate Similarity NPC473611
0.8323 Intermediate Similarity NPC473632
0.8323 Intermediate Similarity NPC469730
0.8323 Intermediate Similarity NPC469420
0.8323 Intermediate Similarity NPC114357
0.8323 Intermediate Similarity NPC469422
0.8323 Intermediate Similarity NPC155329
0.8323 Intermediate Similarity NPC132599
0.8323 Intermediate Similarity NPC228204
0.8323 Intermediate Similarity NPC26033
0.8323 Intermediate Similarity NPC34066
0.8323 Intermediate Similarity NPC259144
0.8313 Intermediate Similarity NPC145649
0.8313 Intermediate Similarity NPC233581
0.8312 Intermediate Similarity NPC90614
0.8312 Intermediate Similarity NPC472547
0.8303 Intermediate Similarity NPC329960
0.8303 Intermediate Similarity NPC295408
0.8303 Intermediate Similarity NPC150893
0.8302 Intermediate Similarity NPC475417
0.8302 Intermediate Similarity NPC165260
0.8302 Intermediate Similarity NPC475561
0.8302 Intermediate Similarity NPC112216
0.8302 Intermediate Similarity NPC161239
0.8302 Intermediate Similarity NPC198455
0.8291 Intermediate Similarity NPC217918
0.8282 Intermediate Similarity NPC471102
0.828 Intermediate Similarity NPC471104
0.828 Intermediate Similarity NPC174982
0.828 Intermediate Similarity NPC476973
0.828 Intermediate Similarity NPC472572
0.828 Intermediate Similarity NPC177940
0.828 Intermediate Similarity NPC472571
0.828 Intermediate Similarity NPC472556
0.828 Intermediate Similarity NPC200471
0.828 Intermediate Similarity NPC127857
0.828 Intermediate Similarity NPC472568
0.828 Intermediate Similarity NPC171525
0.828 Intermediate Similarity NPC158663
0.828 Intermediate Similarity NPC70403
0.828 Intermediate Similarity NPC470159
0.828 Intermediate Similarity NPC473088
0.828 Intermediate Similarity NPC472575
0.828 Intermediate Similarity NPC96903
0.828 Intermediate Similarity NPC29704
0.828 Intermediate Similarity NPC184817
0.828 Intermediate Similarity NPC469349
0.828 Intermediate Similarity NPC470157
0.8272 Intermediate Similarity NPC290683
0.8272 Intermediate Similarity NPC217091
0.8272 Intermediate Similarity NPC475638
0.8272 Intermediate Similarity NPC475548
0.8269 Intermediate Similarity NPC163087
0.8269 Intermediate Similarity NPC91703
0.8261 Intermediate Similarity NPC265395
0.8261 Intermediate Similarity NPC249471
0.8261 Intermediate Similarity NPC256142
0.8261 Intermediate Similarity NPC473414
0.8261 Intermediate Similarity NPC242262
0.8261 Intermediate Similarity NPC304876
0.8261 Intermediate Similarity NPC257213
0.8261 Intermediate Similarity NPC146310
0.8261 Intermediate Similarity NPC472022
0.8261 Intermediate Similarity NPC158333
0.8261 Intermediate Similarity NPC472005
0.8261 Intermediate Similarity NPC237549
0.8261 Intermediate Similarity NPC219419
0.8261 Intermediate Similarity NPC1173
0.8261 Intermediate Similarity NPC472030
0.8258 Intermediate Similarity NPC27377
0.8258 Intermediate Similarity NPC41481
0.8258 Intermediate Similarity NPC472576
0.8258 Intermediate Similarity NPC16912
0.8258 Intermediate Similarity NPC97947
0.8258 Intermediate Similarity NPC118080
0.8258 Intermediate Similarity NPC87448
0.8258 Intermediate Similarity NPC291599
0.825 Intermediate Similarity NPC101043
0.825 Intermediate Similarity NPC306799
0.825 Intermediate Similarity NPC469415
0.8232 Intermediate Similarity NPC471138
0.8232 Intermediate Similarity NPC326328
0.8232 Intermediate Similarity NPC309991
0.8232 Intermediate Similarity NPC323356
0.8232 Intermediate Similarity NPC477623
0.8228 Intermediate Similarity NPC474935
0.8228 Intermediate Similarity NPC473602
0.8221 Intermediate Similarity NPC477735
0.8217 Intermediate Similarity NPC475122
0.8217 Intermediate Similarity NPC472569
0.8217 Intermediate Similarity NPC11685
0.8217 Intermediate Similarity NPC95810
0.8217 Intermediate Similarity NPC95265
0.8217 Intermediate Similarity NPC57628
0.8217 Intermediate Similarity NPC476974
0.8217 Intermediate Similarity NPC34943
0.8217 Intermediate Similarity NPC470152
0.8217 Intermediate Similarity NPC163719
0.8217 Intermediate Similarity NPC25768
0.8217 Intermediate Similarity NPC125106
0.8217 Intermediate Similarity NPC472573
0.8217 Intermediate Similarity NPC70716
0.8217 Intermediate Similarity NPC188865
0.8217 Intermediate Similarity NPC472570
0.8217 Intermediate Similarity NPC475759
0.8217 Intermediate Similarity NPC241951
0.821 Intermediate Similarity NPC469398
0.821 Intermediate Similarity NPC469456
0.821 Intermediate Similarity NPC114410
0.821 Intermediate Similarity NPC112523
0.8205 Intermediate Similarity NPC140021
0.8205 Intermediate Similarity NPC34012
0.8194 Intermediate Similarity NPC100913
0.8194 Intermediate Similarity NPC97667
0.8194 Intermediate Similarity NPC476094
0.8194 Intermediate Similarity NPC4341
0.8194 Intermediate Similarity NPC275592
0.8194 Intermediate Similarity NPC48017
0.8194 Intermediate Similarity NPC200592
0.8194 Intermediate Similarity NPC43241
0.8194 Intermediate Similarity NPC473613
0.8194 Intermediate Similarity NPC147880
0.8194 Intermediate Similarity NPC211137
0.8194 Intermediate Similarity NPC473081
0.8194 Intermediate Similarity NPC473109
0.8194 Intermediate Similarity NPC171207
0.8194 Intermediate Similarity NPC473085
0.8194 Intermediate Similarity NPC473060
0.8194 Intermediate Similarity NPC184747
0.8194 Intermediate Similarity NPC473758
0.8194 Intermediate Similarity NPC473112
0.8187 Intermediate Similarity NPC470245
0.8187 Intermediate Similarity NPC473214
0.8187 Intermediate Similarity NPC222102
0.8187 Intermediate Similarity NPC469448

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC478073 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
0.8333 Intermediate Similarity NPD7799 Discontinued
0.7797 Intermediate Similarity NPD8407 Phase 2
0.7727 Intermediate Similarity NPD8368 Discontinued
0.7716 Intermediate Similarity NPD7236 Approved
0.7624 Intermediate Similarity NPD8360 Approved
0.7624 Intermediate Similarity NPD8361 Approved
0.7611 Intermediate Similarity NPD8434 Phase 2
0.759 Intermediate Similarity NPD7239 Suspended
0.7557 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD8435 Approved
0.7459 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7685 Pre-registration
0.7228 Intermediate Similarity NPD8150 Discontinued
0.7196 Intermediate Similarity NPD8485 Approved
0.7184 Intermediate Similarity NPD7058 Phase 2
0.7184 Intermediate Similarity NPD7057 Phase 3
0.717 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.6973 Remote Similarity NPD8312 Approved
0.6973 Remote Similarity NPD8313 Approved
0.6971 Remote Similarity NPD5760 Phase 2
0.6971 Remote Similarity NPD5761 Phase 2
0.6968 Remote Similarity NPD8397 Clinical (unspecified phase)
0.695 Remote Similarity NPD8462 Phase 1
0.6923 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3818 Discontinued
0.691 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6893 Remote Similarity NPD4967 Phase 2
0.6893 Remote Similarity NPD4965 Approved
0.6893 Remote Similarity NPD4966 Approved
0.6891 Remote Similarity NPD7699 Phase 2
0.6891 Remote Similarity NPD7700 Phase 2
0.6875 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6854 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6853 Remote Similarity NPD8320 Phase 1
0.6853 Remote Similarity NPD8319 Approved
0.6839 Remote Similarity NPD7458 Discontinued
0.6833 Remote Similarity NPD8127 Discontinued
0.6831 Remote Similarity NPD7228 Approved
0.6823 Remote Similarity NPD6534 Approved
0.6823 Remote Similarity NPD6535 Approved
0.6818 Remote Similarity NPD37 Approved
0.6814 Remote Similarity NPD8404 Phase 2
0.6802 Remote Similarity NPD7435 Discontinued
0.6793 Remote Similarity NPD7804 Clinical (unspecified phase)
0.678 Remote Similarity NPD7819 Suspended
0.6778 Remote Similarity NPD5494 Approved
0.6776 Remote Similarity NPD7473 Discontinued
0.6774 Remote Similarity NPD6559 Discontinued
0.6774 Remote Similarity NPD6765 Approved
0.6774 Remote Similarity NPD6764 Approved
0.6768 Remote Similarity NPD7961 Discontinued
0.6765 Remote Similarity NPD4628 Phase 3
0.6757 Remote Similarity NPD7074 Phase 3
0.6752 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6739 Remote Similarity NPD3751 Discontinued
0.6738 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6731 Remote Similarity NPD7741 Discontinued
0.6722 Remote Similarity NPD6234 Discontinued
0.6717 Remote Similarity NPD7698 Approved
0.6717 Remote Similarity NPD7696 Phase 3
0.6717 Remote Similarity NPD7697 Approved
0.6708 Remote Similarity NPD7319 Approved
0.6705 Remote Similarity NPD7028 Phase 2
0.6705 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6705 Remote Similarity NPD4380 Phase 2
0.6703 Remote Similarity NPD7054 Approved
0.6703 Remote Similarity NPD5844 Phase 1
0.6683 Remote Similarity NPD7874 Approved
0.6683 Remote Similarity NPD7871 Phase 2
0.6683 Remote Similarity NPD7870 Phase 2
0.6683 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7472 Approved
0.6667 Remote Similarity NPD8166 Discontinued
0.6667 Remote Similarity NPD7075 Discontinued
0.665 Remote Similarity NPD6778 Approved
0.665 Remote Similarity NPD6777 Approved
0.665 Remote Similarity NPD6782 Approved
0.665 Remote Similarity NPD6779 Approved
0.665 Remote Similarity NPD6780 Approved
0.665 Remote Similarity NPD6776 Approved
0.665 Remote Similarity NPD6781 Approved
0.6649 Remote Similarity NPD7808 Phase 3
0.6648 Remote Similarity NPD5402 Approved
0.6648 Remote Similarity NPD7199 Phase 2
0.6647 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6646 Remote Similarity NPD7736 Approved
0.6645 Remote Similarity NPD7115 Discovery
0.6634 Remote Similarity NPD7930 Approved
0.6632 Remote Similarity NPD6785 Approved
0.6632 Remote Similarity NPD6784 Approved
0.6629 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6629 Remote Similarity NPD6801 Discontinued
0.6628 Remote Similarity NPD6190 Approved
0.6612 Remote Similarity NPD6232 Discontinued
0.661 Remote Similarity NPD6599 Discontinued
0.6609 Remote Similarity NPD2532 Approved
0.6609 Remote Similarity NPD2533 Approved
0.6609 Remote Similarity NPD2534 Approved
0.6596 Remote Similarity NPD7251 Discontinued
0.6596 Remote Similarity NPD7240 Approved
0.6592 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6584 Remote Similarity NPD7701 Phase 2
0.6569 Remote Similarity NPD7801 Approved
0.6567 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6556 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6552 Remote Similarity NPD8151 Discontinued
0.655 Remote Similarity NPD7497 Discontinued
0.6545 Remote Similarity NPD7008 Discontinued
0.6543 Remote Similarity NPD6797 Phase 2
0.6536 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6522 Remote Similarity NPD3787 Discontinued
0.6522 Remote Similarity NPD7507 Approved
0.6519 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6513 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6513 Remote Similarity NPD6213 Phase 3
0.6513 Remote Similarity NPD6212 Phase 3
0.6506 Remote Similarity NPD3764 Approved
0.65 Remote Similarity NPD6823 Phase 2
0.6491 Remote Similarity NPD7266 Discontinued
0.6486 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6485 Remote Similarity NPD7999 Approved
0.648 Remote Similarity NPD7411 Suspended
0.6478 Remote Similarity NPD8513 Phase 3
0.6478 Remote Similarity NPD8516 Approved
0.6478 Remote Similarity NPD8517 Approved
0.6478 Remote Similarity NPD8515 Approved
0.6477 Remote Similarity NPD6273 Approved
0.6474 Remote Similarity NPD2629 Approved
0.6464 Remote Similarity NPD3817 Phase 2
0.6461 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6461 Remote Similarity NPD3226 Approved
0.6441 Remote Similarity NPD5403 Approved
0.6438 Remote Similarity NPD5126 Approved
0.6438 Remote Similarity NPD6370 Approved
0.6438 Remote Similarity NPD5125 Phase 3
0.642 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6409 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6409 Remote Similarity NPD8455 Phase 2
0.6408 Remote Similarity NPD7783 Phase 2
0.6408 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6393 Remote Similarity NPD3749 Approved
0.6385 Remote Similarity NPD5619 Clinical (unspecified phase)
0.638 Remote Similarity NPD7078 Approved
0.638 Remote Similarity NPD8293 Discontinued
0.6379 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6374 Remote Similarity NPD7305 Phase 1
0.6368 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6368 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6166 Phase 2
0.6364 Remote Similarity NPD6799 Approved
0.6358 Remote Similarity NPD7492 Approved
0.6354 Remote Similarity NPD1934 Approved
0.6352 Remote Similarity NPD7516 Approved
0.6346 Remote Similarity NPD6858 Approved
0.6346 Remote Similarity NPD7094 Approved
0.6343 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6339 Remote Similarity NPD7768 Phase 2
0.6339 Remote Similarity NPD3882 Suspended
0.6328 Remote Similarity NPD5401 Approved
0.6328 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6322 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6322 Remote Similarity NPD2800 Approved
0.6319 Remote Similarity NPD2801 Approved
0.6319 Remote Similarity NPD6616 Approved
0.6312 Remote Similarity NPD6054 Approved
0.6305 Remote Similarity NPD7680 Approved
0.6301 Remote Similarity NPD2346 Discontinued
0.6301 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6299 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6299 Remote Similarity NPD2182 Approved
0.6294 Remote Similarity NPD230 Phase 1
0.629 Remote Similarity NPD6959 Discontinued
0.6289 Remote Similarity NPD7327 Approved
0.6289 Remote Similarity NPD7328 Approved
0.6286 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6286 Remote Similarity NPD3750 Approved
0.6282 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6272 Remote Similarity NPD6663 Approved
0.6269 Remote Similarity NPD8285 Discontinued
0.6266 Remote Similarity NPD5951 Approved
0.6266 Remote Similarity NPD690 Clinical (unspecified phase)
0.6265 Remote Similarity NPD6085 Phase 2
0.6265 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6264 Remote Similarity NPD970 Clinical (unspecified phase)
0.6258 Remote Similarity NPD5955 Clinical (unspecified phase)
0.625 Remote Similarity NPD7610 Discontinued
0.6243 Remote Similarity NPD2796 Approved
0.6243 Remote Similarity NPD2935 Discontinued
0.6236 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6235 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6226 Remote Similarity NPD4198 Discontinued
0.6221 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6221 Remote Similarity NPD8059 Phase 3

Structure

External Identifiers

PubChem CID   10392982
ChEMBL   CHEMBL1172172
ZINC  

Physicochemical Properties

Molecular Weight:  558.23
ALogP:  1.5583
MLogP:  4.21
XLogP:  1.656
# Rotatable Bonds:  9
Polar Surface Area:  111.66
# H-Bond Aceptor:  8
# H-Bond Donor:  1
# Rings:  8
# Heavy Atoms:  41

Download Data

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Structure MOL file  
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Biological Activities  
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