Natural Product: NPC471738

Natural Product ID:  NPC471738
Common Name:   Chandonanone D
IUPAC Name:   [(1R,6R,9R,10E,14S)-9-hydroxy-6,10,14-trimethyl-2-oxo-3-propan-2-ylidene-15-oxabicyclo[12.1.0]pentadec-10-en-6-yl] acetate
Synonyms:  
Molecular Formula:   C22H34O5
Standard InCHIKey:  YDCIWGCXNIKFHT-ATAUPYBZSA-N
Standard InCHI:  InChI=1S/C22H34O5/c1-14(2)17-9-12-21(5,26-16(4)23)13-10-18(24)15(3)8-7-11-22(6)20(27-22)19(17)25/h8,18,20,24H,7,9-13H2,1-6H3/b15-8+/t18-,20+,21-,22+/m1/s1
Canonical SMILES:  CC(=O)O[C@]1(C)CCC(=C(C)C)C(=O)[C@@H]2O[C@@]2(C)CC/C=C(/[C@@H](CC1)O)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
NPO11601 Chandonanthus hirtellus Species Anastrophyllaceae Eukaryota China PMID[24491225]
NPO32786 chandonanthus birmensis Species Anastrophyllaceae Eukaryota China PMID[24491225]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2410 Cell Line NCI-H1299 Homo sapiens IC50 = 20900 nM 19161316
NPT2452 Cell Line NCI-H292 IC50 > 50000 nM 10.6019/CHEMBL3301361
NPT306 Cell Line PC-3 Homo sapiens IC50 > 50000 nM 10.6019/CHEMBL1201861
NPT90 Cell Line DU-145 Homo sapiens IC50 > 50000 nM 17685651
NPT2 Others Unspecified IC50 = 30200 nM 23347584
NPT81 Cell Line A549 Homo sapiens IC50 = 21500 nM 18824363
NPT2 Others Unspecified IC50 > 50000 nM Open TG-GATES in vivo data: Biochemistry

  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 NPC471738 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
0.9012 High Similarity NPC471740
0.8795 High Similarity NPC286229
0.8409 Intermediate Similarity NPC197333
0.8409 Intermediate Similarity NPC471739
0.8333 Intermediate Similarity NPC276647
0.8333 Intermediate Similarity NPC622
0.8315 Intermediate Similarity NPC475902
0.8315 Intermediate Similarity NPC472008
0.8261 Intermediate Similarity NPC469632
0.8202 Intermediate Similarity NPC179659
0.8144 Intermediate Similarity NPC472755
0.814 Intermediate Similarity NPC112868
0.8125 Intermediate Similarity NPC128733
0.8125 Intermediate Similarity NPC110443
0.8125 Intermediate Similarity NPC133907
0.8125 Intermediate Similarity NPC46998
0.8125 Intermediate Similarity NPC185141
0.8125 Intermediate Similarity NPC472753
0.809 Intermediate Similarity NPC261721
0.809 Intermediate Similarity NPC472009
0.8085 Intermediate Similarity NPC473291
0.8043 Intermediate Similarity NPC20713
0.8041 Intermediate Similarity NPC39996
0.8041 Intermediate Similarity NPC118405
0.8041 Intermediate Similarity NPC472754
0.8 Intermediate Similarity NPC472007
0.8 Intermediate Similarity NPC72513
0.7978 Intermediate Similarity NPC261380
0.7938 Intermediate Similarity NPC201718
0.7935 Intermediate Similarity NPC477684
0.7935 Intermediate Similarity NPC316228
0.7935 Intermediate Similarity NPC471399
0.7917 Intermediate Similarity NPC161855
0.7895 Intermediate Similarity NPC184065
0.7889 Intermediate Similarity NPC122502
0.7872 Intermediate Similarity NPC121825
0.7849 Intermediate Similarity NPC219874
0.7841 Intermediate Similarity NPC85772
0.7835 Intermediate Similarity NPC288876
0.7826 Intermediate Similarity NPC83423
0.7822 Intermediate Similarity NPC322903
0.7812 Intermediate Similarity NPC87090
0.7812 Intermediate Similarity NPC20066
0.7802 Intermediate Similarity NPC86005
0.7802 Intermediate Similarity NPC477959
0.7791 Intermediate Similarity NPC478122
0.7766 Intermediate Similarity NPC475302
0.7766 Intermediate Similarity NPC469645
0.7766 Intermediate Similarity NPC469692
0.7765 Intermediate Similarity NPC271070
0.7755 Intermediate Similarity NPC477356
0.7755 Intermediate Similarity NPC474339
0.7755 Intermediate Similarity NPC476270
0.7755 Intermediate Similarity NPC164598
0.7753 Intermediate Similarity NPC477785
0.7753 Intermediate Similarity NPC52609
0.7753 Intermediate Similarity NPC477784
0.7753 Intermediate Similarity NPC477786
0.7753 Intermediate Similarity NPC1761
0.7742 Intermediate Similarity NPC265856
0.7742 Intermediate Similarity NPC166554
0.7732 Intermediate Similarity NPC300584
0.7727 Intermediate Similarity NPC79277
0.7727 Intermediate Similarity NPC475481
0.7723 Intermediate Similarity NPC477513
0.7717 Intermediate Similarity NPC469653
0.7717 Intermediate Similarity NPC469631
0.7717 Intermediate Similarity NPC471047
0.7717 Intermediate Similarity NPC469628
0.7717 Intermediate Similarity NPC475906
0.7717 Intermediate Similarity NPC201046
0.7708 Intermediate Similarity NPC476315
0.7708 Intermediate Similarity NPC476275
0.7708 Intermediate Similarity NPC473859
0.7708 Intermediate Similarity NPC230800
0.7701 Intermediate Similarity NPC136033
0.77 Intermediate Similarity NPC472756
0.77 Intermediate Similarity NPC474741
0.7692 Intermediate Similarity NPC316426
0.7692 Intermediate Similarity NPC202394
0.7692 Intermediate Similarity NPC315395
0.7684 Intermediate Similarity NPC474035
0.7684 Intermediate Similarity NPC81386
0.7674 Intermediate Similarity NPC473536
0.7667 Intermediate Similarity NPC243618
0.7667 Intermediate Similarity NPC70424
0.766 Intermediate Similarity NPC476705
0.766 Intermediate Similarity NPC300312
0.766 Intermediate Similarity NPC111114
0.766 Intermediate Similarity NPC261607
0.7653 Intermediate Similarity NPC475949
0.7653 Intermediate Similarity NPC469551
0.7647 Intermediate Similarity NPC60718
0.764 Intermediate Similarity NPC47450
0.7629 Intermediate Similarity NPC471916
0.7624 Intermediate Similarity NPC472751
0.7624 Intermediate Similarity NPC472749
0.7614 Intermediate Similarity NPC470947
0.7614 Intermediate Similarity NPC470945
0.7614 Intermediate Similarity NPC470946
0.7609 Intermediate Similarity NPC237540
0.7609 Intermediate Similarity NPC474765
0.7604 Intermediate Similarity NPC475659
0.7604 Intermediate Similarity NPC474947
0.7604 Intermediate Similarity NPC214694
0.7604 Intermediate Similarity NPC270013
0.7604 Intermediate Similarity NPC14961
0.76 Intermediate Similarity NPC118902
0.76 Intermediate Similarity NPC469980
0.76 Intermediate Similarity NPC104161
0.76 Intermediate Similarity NPC472750
0.76 Intermediate Similarity NPC475945
0.76 Intermediate Similarity NPC475871
0.76 Intermediate Similarity NPC472747
0.7596 Intermediate Similarity NPC317107
0.7586 Intermediate Similarity NPC121200
0.7586 Intermediate Similarity NPC192006
0.7586 Intermediate Similarity NPC231739
0.7582 Intermediate Similarity NPC11804
0.7582 Intermediate Similarity NPC125290
0.7582 Intermediate Similarity NPC470755
0.7582 Intermediate Similarity NPC137033
0.7579 Intermediate Similarity NPC228451
0.7579 Intermediate Similarity NPC165383
0.7579 Intermediate Similarity NPC475838
0.7579 Intermediate Similarity NPC125674
0.7576 Intermediate Similarity NPC469851
0.7556 Intermediate Similarity NPC69469
0.7556 Intermediate Similarity NPC161045
0.7556 Intermediate Similarity NPC475989
0.7556 Intermediate Similarity NPC16488
0.7556 Intermediate Similarity NPC170377
0.7553 Intermediate Similarity NPC77337
0.7553 Intermediate Similarity NPC313670
0.7553 Intermediate Similarity NPC469718
0.7553 Intermediate Similarity NPC71533
0.7553 Intermediate Similarity NPC329857
0.7553 Intermediate Similarity NPC474761
0.7553 Intermediate Similarity NPC106510
0.7553 Intermediate Similarity NPC476004
0.7551 Intermediate Similarity NPC141191
0.7551 Intermediate Similarity NPC477355
0.7527 Intermediate Similarity NPC474471
0.7527 Intermediate Similarity NPC476805
0.7527 Intermediate Similarity NPC227379
0.7525 Intermediate Similarity NPC472748
0.7524 Intermediate Similarity NPC317687
0.75 Intermediate Similarity NPC164393
0.75 Intermediate Similarity NPC279859
0.75 Intermediate Similarity NPC474247
0.75 Intermediate Similarity NPC474747
0.75 Intermediate Similarity NPC149371
0.75 Intermediate Similarity NPC196381
0.75 Intermediate Similarity NPC57405
0.75 Intermediate Similarity NPC38576
0.75 Intermediate Similarity NPC469483
0.75 Intermediate Similarity NPC471148
0.75 Intermediate Similarity NPC475461
0.75 Intermediate Similarity NPC303942
0.75 Intermediate Similarity NPC305475
0.7475 Intermediate Similarity NPC174314
0.7474 Intermediate Similarity NPC30515
0.7474 Intermediate Similarity NPC475441
0.7473 Intermediate Similarity NPC96259
0.7473 Intermediate Similarity NPC32565
0.7473 Intermediate Similarity NPC72464
0.7473 Intermediate Similarity NPC82297
0.7473 Intermediate Similarity NPC9868
0.7473 Intermediate Similarity NPC31086
0.7473 Intermediate Similarity NPC120726
0.7473 Intermediate Similarity NPC158756
0.7473 Intermediate Similarity NPC474776
0.7473 Intermediate Similarity NPC141193
0.7471 Intermediate Similarity NPC281296
0.7471 Intermediate Similarity NPC84360
0.747 Intermediate Similarity NPC477448
0.747 Intermediate Similarity NPC477449
0.7451 Intermediate Similarity NPC314244
0.7451 Intermediate Similarity NPC469852
0.7449 Intermediate Similarity NPC169205
0.7449 Intermediate Similarity NPC40812
0.7449 Intermediate Similarity NPC69385
0.7447 Intermediate Similarity NPC268298
0.7447 Intermediate Similarity NPC212598
0.7447 Intermediate Similarity NPC106040
0.7447 Intermediate Similarity NPC115179
0.7447 Intermediate Similarity NPC295312
0.7444 Intermediate Similarity NPC7414
0.7442 Intermediate Similarity NPC199445
0.7431 Intermediate Similarity NPC477092
0.7426 Intermediate Similarity NPC131366
0.7423 Intermediate Similarity NPC474490
0.7423 Intermediate Similarity NPC134067
0.7423 Intermediate Similarity NPC36954
0.7423 Intermediate Similarity NPC91408
0.7419 Intermediate Similarity NPC266957
0.7416 Intermediate Similarity NPC103634
0.7416 Intermediate Similarity NPC472948
0.7407 Intermediate Similarity NPC471146
0.7407 Intermediate Similarity NPC475305

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471738 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
0.7692 Intermediate Similarity NPD5786 Approved
0.766 Intermediate Similarity NPD7983 Approved
0.7582 Intermediate Similarity NPD5363 Approved
0.7553 Intermediate Similarity NPD46 Approved
0.7553 Intermediate Similarity NPD6698 Approved
0.7444 Intermediate Similarity NPD4269 Approved
0.7444 Intermediate Similarity NPD4270 Approved
0.7396 Intermediate Similarity NPD5779 Approved
0.7396 Intermediate Similarity NPD5778 Approved
0.7368 Intermediate Similarity NPD5785 Approved
0.7363 Intermediate Similarity NPD7154 Phase 3
0.7333 Intermediate Similarity NPD5369 Approved
0.7273 Intermediate Similarity NPD4756 Discovery
0.7253 Intermediate Similarity NPD6435 Approved
0.7245 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4252 Approved
0.7174 Intermediate Similarity NPD5362 Discontinued
0.7172 Intermediate Similarity NPD7839 Suspended
0.7108 Intermediate Similarity NPD7331 Phase 2
0.7083 Intermediate Similarity NPD6101 Approved
0.7083 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD5368 Approved
0.7033 Intermediate Similarity NPD4820 Approved
0.7033 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD4819 Approved
0.7033 Intermediate Similarity NPD4821 Approved
0.7033 Intermediate Similarity NPD4822 Approved
0.7009 Intermediate Similarity NPD6371 Approved
0.7 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.6988 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6952 Remote Similarity NPD5739 Approved
0.6952 Remote Similarity NPD6675 Approved
0.6952 Remote Similarity NPD7128 Approved
0.6952 Remote Similarity NPD6402 Approved
0.6939 Remote Similarity NPD6411 Approved
0.6887 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7838 Discovery
0.6822 Remote Similarity NPD6899 Approved
0.6822 Remote Similarity NPD6881 Approved
0.6822 Remote Similarity NPD7320 Approved
0.6813 Remote Similarity NPD4268 Approved
0.6813 Remote Similarity NPD4271 Approved
0.68 Remote Similarity NPD5282 Discontinued
0.6765 Remote Similarity NPD6084 Phase 2
0.6765 Remote Similarity NPD6083 Phase 2
0.6759 Remote Similarity NPD6372 Approved
0.6759 Remote Similarity NPD6373 Approved
0.6735 Remote Similarity NPD5370 Suspended
0.6729 Remote Similarity NPD5697 Approved
0.6729 Remote Similarity NPD5701 Approved
0.6706 Remote Similarity NPD3704 Approved
0.6702 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6697 Remote Similarity NPD6883 Approved
0.6697 Remote Similarity NPD7290 Approved
0.6697 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD3197 Phase 1
0.6637 Remote Similarity NPD7115 Discovery
0.6636 Remote Similarity NPD6617 Approved
0.6636 Remote Similarity NPD6869 Approved
0.6636 Remote Similarity NPD8130 Phase 1
0.6636 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6636 Remote Similarity NPD6649 Approved
0.6636 Remote Similarity NPD6650 Approved
0.6636 Remote Similarity NPD6847 Approved
0.6632 Remote Similarity NPD5332 Approved
0.6632 Remote Similarity NPD5331 Approved
0.6632 Remote Similarity NPD6110 Phase 1
0.6628 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6014 Approved
0.6606 Remote Similarity NPD6013 Approved
0.6606 Remote Similarity NPD6012 Approved
0.66 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6596 Remote Similarity NPD4790 Discontinued
0.6588 Remote Similarity NPD7341 Phase 2
0.6577 Remote Similarity NPD8297 Approved
0.6577 Remote Similarity NPD6882 Approved
0.6569 Remote Similarity NPD5695 Phase 3
0.6538 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6531 Remote Similarity NPD4250 Approved
0.6531 Remote Similarity NPD4251 Approved
0.6526 Remote Similarity NPD5209 Approved
0.6495 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6495 Remote Similarity NPD1696 Phase 3
0.6489 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6465 Remote Similarity NPD6672 Approved
0.6465 Remote Similarity NPD5737 Approved
0.6436 Remote Similarity NPD7637 Suspended
0.6429 Remote Similarity NPD6053 Discontinued
0.6429 Remote Similarity NPD6422 Discontinued
0.6429 Remote Similarity NPD4249 Approved
0.6415 Remote Similarity NPD5344 Discontinued
0.6392 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6381 Remote Similarity NPD5696 Approved
0.6381 Remote Similarity NPD4225 Approved
0.6373 Remote Similarity NPD6399 Phase 3
0.6355 Remote Similarity NPD5211 Phase 2
0.6353 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6339 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6325 Remote Similarity NPD6319 Approved
0.6322 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7748 Approved
0.631 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6304 Remote Similarity NPD8039 Approved
0.6303 Remote Similarity NPD7642 Approved
0.6293 Remote Similarity NPD6335 Approved
0.6286 Remote Similarity NPD4755 Approved
0.6286 Remote Similarity NPD7902 Approved
0.6275 Remote Similarity NPD7515 Phase 2
0.6261 Remote Similarity NPD6274 Approved
0.625 Remote Similarity NPD7492 Approved
0.6239 Remote Similarity NPD7101 Approved
0.6239 Remote Similarity NPD5141 Approved
0.6239 Remote Similarity NPD7100 Approved
0.6238 Remote Similarity NPD6080 Approved
0.6238 Remote Similarity NPD6904 Approved
0.6238 Remote Similarity NPD1695 Approved
0.6238 Remote Similarity NPD6673 Approved
0.6207 Remote Similarity NPD6317 Approved
0.6198 Remote Similarity NPD6616 Approved
0.6186 Remote Similarity NPD6054 Approved
0.6186 Remote Similarity NPD6059 Approved
0.6186 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6182 Remote Similarity NPD6008 Approved
0.6168 Remote Similarity NPD5286 Approved
0.6168 Remote Similarity NPD5285 Approved
0.6168 Remote Similarity NPD7639 Approved
0.6168 Remote Similarity NPD7640 Approved
0.6168 Remote Similarity NPD4696 Approved
0.6168 Remote Similarity NPD6648 Approved
0.6168 Remote Similarity NPD4700 Approved
0.6167 Remote Similarity NPD7829 Approved
0.6167 Remote Similarity NPD7830 Approved
0.6167 Remote Similarity NPD7604 Phase 2
0.6167 Remote Similarity NPD8328 Phase 3
0.6154 Remote Similarity NPD6313 Approved
0.6154 Remote Similarity NPD6314 Approved
0.6148 Remote Similarity NPD7078 Approved
0.6148 Remote Similarity NPD8293 Discontinued
0.6146 Remote Similarity NPD4695 Discontinued
0.6134 Remote Similarity NPD8517 Approved
0.6134 Remote Similarity NPD8515 Approved
0.6134 Remote Similarity NPD8516 Approved
0.6134 Remote Similarity NPD6909 Approved
0.6134 Remote Similarity NPD6908 Approved
0.6134 Remote Similarity NPD8513 Phase 3
0.6121 Remote Similarity NPD6868 Approved
0.6117 Remote Similarity NPD6050 Approved
0.6117 Remote Similarity NPD5693 Phase 1
0.6111 Remote Similarity NPD5223 Approved
0.6105 Remote Similarity NPD3732 Approved
0.61 Remote Similarity NPD7146 Approved
0.61 Remote Similarity NPD6409 Approved
0.61 Remote Similarity NPD7334 Approved
0.61 Remote Similarity NPD5279 Phase 3
0.61 Remote Similarity NPD7521 Approved
0.61 Remote Similarity NPD5330 Approved
0.61 Remote Similarity NPD6684 Approved
0.6098 Remote Similarity NPD7736 Approved
0.6087 Remote Similarity NPD4632 Approved
0.6083 Remote Similarity NPD8080 Discontinued
0.6083 Remote Similarity NPD6370 Approved
0.6078 Remote Similarity NPD4753 Phase 2
0.6078 Remote Similarity NPD5328 Approved
0.6078 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6075 Remote Similarity NPD7638 Approved
0.6071 Remote Similarity NPD6686 Approved
0.6071 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6068 Remote Similarity NPD6009 Approved
0.6055 Remote Similarity NPD5226 Approved
0.6055 Remote Similarity NPD5225 Approved
0.6055 Remote Similarity NPD4633 Approved
0.6055 Remote Similarity NPD5224 Approved
0.6038 Remote Similarity NPD5221 Approved
0.6038 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6038 Remote Similarity NPD5222 Approved
0.6038 Remote Similarity NPD4697 Phase 3
0.6019 Remote Similarity NPD5692 Phase 3
0.6 Remote Similarity NPD6015 Approved
0.6 Remote Similarity NPD6016 Approved
0.6 Remote Similarity NPD6647 Phase 2
0.6 Remote Similarity NPD1694 Approved
0.6 Remote Similarity NPD4754 Approved
0.6 Remote Similarity NPD5174 Approved
0.6 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6 Remote Similarity NPD7900 Approved
0.6 Remote Similarity NPD5175 Approved
0.6 Remote Similarity NPD5983 Phase 2
0.5981 Remote Similarity NPD5173 Approved
0.598 Remote Similarity NPD6903 Approved
0.598 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5976 Remote Similarity NPD3195 Phase 2
0.5976 Remote Similarity NPD4266 Approved
0.5976 Remote Similarity NPD3196 Approved
0.5976 Remote Similarity NPD3194 Approved
0.5965 Remote Similarity NPD4634 Approved
0.5962 Remote Similarity NPD5694 Approved
0.5962 Remote Similarity NPD6079 Approved
0.595 Remote Similarity NPD5988 Approved

Structure

External Identifiers

PubChem CID   76332079
ChEMBL   CHEMBL3109416
ZINC  

Physicochemical Properties

Molecular Weight:  378.24
ALogP:  2.2139
MLogP:  3.33
XLogP:  2.61
# Rotatable Bonds:  9
Polar Surface Area:  76.13
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  27

Download Data

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