Natural Product: NPC45579

Natural Product ID:  NPC45579
Common Name:   Bharangin
IUPAC Name:   (11aS)-10-hydroxy-4,4,11a-trimethyl-8-propan-2-yl-3,11-dihydrobenzo[3,4]cyclohepta[3,5-b]pyran-2,9-dione
Synonyms:   Bharangin
Molecular Formula:   C20H24O4
Standard InCHIKey:  HMJSIJZITOCLAD-FQEVSTJZSA-N
Standard InCHI:  InChI=1S/C20H24O4/c1-11(2)13-8-12-6-7-15-19(3,4)10-16(21)24-20(15,5)9-14(12)18(23)17(13)22/h6-8,11,23H,9-10H2,1-5H3/t20-/m0/s1
Canonical SMILES:  O=C1CC(C)(C)C2=CC=C3C(=C(O)C(=O)C(=C3)C(C)C)C[C@@]2(O1)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
NPO33238 pygmacopremna herbacea Species NA NA roots PMID[21708464]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens IC50 = 0.006 ug/ml 17844994
NPT81 Cell Line A549 Homo sapiens IC50 = 2.03 ug/ml 17844994
NPT306 Cell Line PC-3 Homo sapiens IC50 = 2.95 ug/ml 19053514
NPT65 Cell Line HepG2 Homo sapiens IC50 = 14.3 ug/ml 19053514
NPT165 Cell Line HeLa Homo sapiens IC50 = 14.1 ug/ml 10.6019/CHEMBL1201861

  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 NPC45579 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
0.8851 High Similarity NPC470177
0.8211 Intermediate Similarity NPC295347
0.8163 Intermediate Similarity NPC206079
0.8144 Intermediate Similarity NPC64742
0.8125 Intermediate Similarity NPC9812
0.8041 Intermediate Similarity NPC208094
0.7959 Intermediate Similarity NPC244411
0.7955 Intermediate Similarity NPC469617
0.7935 Intermediate Similarity NPC234038
0.7931 Intermediate Similarity NPC180290
0.7895 Intermediate Similarity NPC219874
0.7889 Intermediate Similarity NPC221231
0.7889 Intermediate Similarity NPC471326
0.7872 Intermediate Similarity NPC212598
0.7849 Intermediate Similarity NPC476079
0.7849 Intermediate Similarity NPC103743
0.7849 Intermediate Similarity NPC113370
0.7826 Intermediate Similarity NPC307112
0.78 Intermediate Similarity NPC62670
0.78 Intermediate Similarity NPC116139
0.78 Intermediate Similarity NPC469851
0.7789 Intermediate Similarity NPC476369
0.7789 Intermediate Similarity NPC476437
0.7789 Intermediate Similarity NPC77337
0.7778 Intermediate Similarity NPC222011
0.7745 Intermediate Similarity NPC309190
0.7745 Intermediate Similarity NPC325769
0.7732 Intermediate Similarity NPC476415
0.7727 Intermediate Similarity NPC316324
0.7723 Intermediate Similarity NPC66110
0.7717 Intermediate Similarity NPC196487
0.7717 Intermediate Similarity NPC14575
0.7708 Intermediate Similarity NPC472705
0.7684 Intermediate Similarity NPC106040
0.7684 Intermediate Similarity NPC118011
0.7684 Intermediate Similarity NPC284561
0.7684 Intermediate Similarity NPC5509
0.7684 Intermediate Similarity NPC115179
0.7684 Intermediate Similarity NPC36668
0.7677 Intermediate Similarity NPC69385
0.7677 Intermediate Similarity NPC202705
0.7667 Intermediate Similarity NPC47747
0.766 Intermediate Similarity NPC231599
0.7653 Intermediate Similarity NPC209355
0.7653 Intermediate Similarity NPC171395
0.7634 Intermediate Similarity NPC474680
0.7629 Intermediate Similarity NPC476049
0.7624 Intermediate Similarity NPC472643
0.7619 Intermediate Similarity NPC137911
0.7619 Intermediate Similarity NPC228477
0.7609 Intermediate Similarity NPC105803
0.7609 Intermediate Similarity NPC475083
0.7609 Intermediate Similarity NPC258985
0.7596 Intermediate Similarity NPC475294
0.7579 Intermediate Similarity NPC72397
0.7553 Intermediate Similarity NPC198314
0.7553 Intermediate Similarity NPC261721
0.7553 Intermediate Similarity NPC220478
0.7553 Intermediate Similarity NPC122502
0.7553 Intermediate Similarity NPC116575
0.7551 Intermediate Similarity NPC477241
0.7549 Intermediate Similarity NPC473596
0.7527 Intermediate Similarity NPC72464
0.7527 Intermediate Similarity NPC70424
0.7527 Intermediate Similarity NPC9868
0.7527 Intermediate Similarity NPC243618
0.7526 Intermediate Similarity NPC166110
0.7525 Intermediate Similarity NPC174314
0.7525 Intermediate Similarity NPC280963
0.7525 Intermediate Similarity NPC472644
0.75 Intermediate Similarity NPC477125
0.75 Intermediate Similarity NPC170131
0.75 Intermediate Similarity NPC280833
0.75 Intermediate Similarity NPC469852
0.75 Intermediate Similarity NPC474343
0.75 Intermediate Similarity NPC239895
0.75 Intermediate Similarity NPC210216
0.75 Intermediate Similarity NPC47834
0.7477 Intermediate Similarity NPC179798
0.7477 Intermediate Similarity NPC304180
0.7476 Intermediate Similarity NPC179208
0.7476 Intermediate Similarity NPC472747
0.7476 Intermediate Similarity NPC472750
0.7475 Intermediate Similarity NPC272050
0.7474 Intermediate Similarity NPC478145
0.7474 Intermediate Similarity NPC476409
0.7474 Intermediate Similarity NPC181327
0.7473 Intermediate Similarity NPC233377
0.7449 Intermediate Similarity NPC263780
0.7449 Intermediate Similarity NPC271652
0.7449 Intermediate Similarity NPC476416
0.7449 Intermediate Similarity NPC248193
0.7447 Intermediate Similarity NPC474369
0.7447 Intermediate Similarity NPC189311
0.7447 Intermediate Similarity NPC65661
0.7444 Intermediate Similarity NPC471220
0.7444 Intermediate Similarity NPC74410
0.7423 Intermediate Similarity NPC145666
0.7423 Intermediate Similarity NPC51486
0.7423 Intermediate Similarity NPC265856
0.7419 Intermediate Similarity NPC102197
0.7419 Intermediate Similarity NPC53867
0.7419 Intermediate Similarity NPC49019
0.7419 Intermediate Similarity NPC288281
0.7416 Intermediate Similarity NPC110725
0.7416 Intermediate Similarity NPC40353
0.7407 Intermediate Similarity NPC221144
0.7404 Intermediate Similarity NPC118911
0.7404 Intermediate Similarity NPC472748
0.7396 Intermediate Similarity NPC473658
0.7396 Intermediate Similarity NPC472008
0.7396 Intermediate Similarity NPC60765
0.7396 Intermediate Similarity NPC472302
0.7391 Intermediate Similarity NPC55869
0.7391 Intermediate Similarity NPC225515
0.7391 Intermediate Similarity NPC40228
0.7391 Intermediate Similarity NPC275766
0.7383 Intermediate Similarity NPC206595
0.7374 Intermediate Similarity NPC469632
0.7374 Intermediate Similarity NPC38830
0.7374 Intermediate Similarity NPC65829
0.7368 Intermediate Similarity NPC239685
0.7368 Intermediate Similarity NPC472863
0.7368 Intermediate Similarity NPC164393
0.7356 Intermediate Similarity NPC288667
0.7353 Intermediate Similarity NPC472972
0.7347 Intermediate Similarity NPC470036
0.7347 Intermediate Similarity NPC32944
0.7347 Intermediate Similarity NPC475972
0.7347 Intermediate Similarity NPC303697
0.7347 Intermediate Similarity NPC470373
0.7347 Intermediate Similarity NPC193396
0.7347 Intermediate Similarity NPC174167
0.7347 Intermediate Similarity NPC470379
0.734 Intermediate Similarity NPC474359
0.7339 Intermediate Similarity NPC469463
0.7339 Intermediate Similarity NPC469454
0.7339 Intermediate Similarity NPC469496
0.7339 Intermediate Similarity NPC56448
0.7333 Intermediate Similarity NPC97377
0.7333 Intermediate Similarity NPC472751
0.7333 Intermediate Similarity NPC1679
0.7333 Intermediate Similarity NPC472645
0.7333 Intermediate Similarity NPC472749
0.7327 Intermediate Similarity NPC20066
0.7327 Intermediate Similarity NPC254496
0.7327 Intermediate Similarity NPC285513
0.7327 Intermediate Similarity NPC120299
0.7326 Intermediate Similarity NPC469914
0.732 Intermediate Similarity NPC474918
0.732 Intermediate Similarity NPC268298
0.732 Intermediate Similarity NPC95364
0.732 Intermediate Similarity NPC168131
0.732 Intermediate Similarity NPC307092
0.732 Intermediate Similarity NPC142159
0.732 Intermediate Similarity NPC112454
0.7312 Intermediate Similarity NPC474291
0.7308 Intermediate Similarity NPC472755
0.73 Intermediate Similarity NPC474490
0.73 Intermediate Similarity NPC300710
0.7292 Intermediate Similarity NPC478144
0.7292 Intermediate Similarity NPC477228
0.7292 Intermediate Similarity NPC312561
0.7283 Intermediate Similarity NPC108955
0.7282 Intermediate Similarity NPC474742
0.7282 Intermediate Similarity NPC472637
0.7282 Intermediate Similarity NPC323441
0.7282 Intermediate Similarity NPC472753
0.7282 Intermediate Similarity NPC146822
0.7273 Intermediate Similarity NPC109414
0.7264 Intermediate Similarity NPC469853
0.7263 Intermediate Similarity NPC110405
0.7263 Intermediate Similarity NPC86316
0.7263 Intermediate Similarity NPC8518
0.7263 Intermediate Similarity NPC32037
0.7263 Intermediate Similarity NPC106416
0.7263 Intermediate Similarity NPC197903
0.7263 Intermediate Similarity NPC132228
0.7263 Intermediate Similarity NPC6185
0.7263 Intermediate Similarity NPC261380
0.7263 Intermediate Similarity NPC241512
0.7263 Intermediate Similarity NPC99395
0.7263 Intermediate Similarity NPC165162
0.7263 Intermediate Similarity NPC263997
0.7255 Intermediate Similarity NPC141191
0.7255 Intermediate Similarity NPC23364
0.7255 Intermediate Similarity NPC475653
0.7255 Intermediate Similarity NPC316598
0.7253 Intermediate Similarity NPC315765
0.7253 Intermediate Similarity NPC198240
0.7253 Intermediate Similarity NPC169095
0.7248 Intermediate Similarity NPC100267
0.7248 Intermediate Similarity NPC475524
0.7245 Intermediate Similarity NPC213636
0.7245 Intermediate Similarity NPC281942
0.7245 Intermediate Similarity NPC469595
0.7245 Intermediate Similarity NPC472866
0.7245 Intermediate Similarity NPC469372
0.7245 Intermediate Similarity NPC232426
0.7245 Intermediate Similarity NPC129419

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC45579 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
0.7528 Intermediate Similarity NPD4756 Discovery
0.7473 Intermediate Similarity NPD4695 Discontinued
0.732 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD6411 Approved
0.7172 Intermediate Similarity NPD5693 Phase 1
0.7129 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD3573 Approved
0.7071 Intermediate Similarity NPD5692 Phase 3
0.7 Intermediate Similarity NPD5694 Approved
0.7 Intermediate Similarity NPD6050 Approved
0.6977 Remote Similarity NPD7331 Phase 2
0.697 Remote Similarity NPD5764 Clinical (unspecified phase)
0.697 Remote Similarity NPD6101 Approved
0.6961 Remote Similarity NPD5695 Phase 3
0.6931 Remote Similarity NPD5779 Approved
0.6931 Remote Similarity NPD5778 Approved
0.6923 Remote Similarity NPD8039 Approved
0.6907 Remote Similarity NPD1694 Approved
0.686 Remote Similarity NPD7341 Phase 2
0.6837 Remote Similarity NPD4694 Approved
0.6837 Remote Similarity NPD5280 Approved
0.6832 Remote Similarity NPD5281 Approved
0.6832 Remote Similarity NPD5284 Approved
0.6827 Remote Similarity NPD6084 Phase 2
0.6827 Remote Similarity NPD6083 Phase 2
0.6824 Remote Similarity NPD2664 Clinical (unspecified phase)
0.68 Remote Similarity NPD6904 Approved
0.68 Remote Similarity NPD6080 Approved
0.68 Remote Similarity NPD6673 Approved
0.6789 Remote Similarity NPD5697 Approved
0.6762 Remote Similarity NPD5696 Approved
0.6733 Remote Similarity NPD5785 Approved
0.6733 Remote Similarity NPD46 Approved
0.6733 Remote Similarity NPD6698 Approved
0.6727 Remote Similarity NPD6881 Approved
0.6727 Remote Similarity NPD6011 Approved
0.6727 Remote Similarity NPD6899 Approved
0.67 Remote Similarity NPD5737 Approved
0.67 Remote Similarity NPD6672 Approved
0.6699 Remote Similarity NPD5282 Discontinued
0.6697 Remote Similarity NPD6675 Approved
0.6697 Remote Similarity NPD7128 Approved
0.6697 Remote Similarity NPD6402 Approved
0.6697 Remote Similarity NPD5739 Approved
0.6667 Remote Similarity NPD5279 Phase 3
0.6667 Remote Similarity NPD5690 Phase 2
0.6667 Remote Similarity NPD6014 Approved
0.6667 Remote Similarity NPD6013 Approved
0.6667 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD7260 Phase 2
0.6637 Remote Similarity NPD6053 Discontinued
0.6636 Remote Similarity NPD5701 Approved
0.6635 Remote Similarity NPD5654 Approved
0.6633 Remote Similarity NPD4197 Approved
0.6607 Remote Similarity NPD6371 Approved
0.6607 Remote Similarity NPD7290 Approved
0.6607 Remote Similarity NPD6883 Approved
0.6607 Remote Similarity NPD7102 Approved
0.6604 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5209 Approved
0.6577 Remote Similarity NPD7320 Approved
0.6569 Remote Similarity NPD5207 Approved
0.6566 Remote Similarity NPD1696 Phase 3
0.6566 Remote Similarity NPD5329 Approved
0.6562 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6650 Approved
0.6549 Remote Similarity NPD8130 Phase 1
0.6549 Remote Similarity NPD6617 Approved
0.6549 Remote Similarity NPD6649 Approved
0.6549 Remote Similarity NPD6869 Approved
0.6549 Remote Similarity NPD6847 Approved
0.6538 Remote Similarity NPD7748 Approved
0.6535 Remote Similarity NPD4518 Approved
0.6526 Remote Similarity NPD3617 Approved
0.6518 Remote Similarity NPD6372 Approved
0.6518 Remote Similarity NPD6373 Approved
0.6509 Remote Similarity NPD5959 Approved
0.65 Remote Similarity NPD4519 Discontinued
0.65 Remote Similarity NPD6098 Approved
0.65 Remote Similarity NPD4623 Approved
0.6491 Remote Similarity NPD6882 Approved
0.6491 Remote Similarity NPD8297 Approved
0.6486 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4753 Phase 2
0.6449 Remote Similarity NPD4225 Approved
0.6442 Remote Similarity NPD6399 Phase 3
0.6429 Remote Similarity NPD4223 Phase 3
0.6429 Remote Similarity NPD4221 Approved
0.6429 Remote Similarity NPD6686 Approved
0.6429 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6422 Remote Similarity NPD5211 Phase 2
0.6415 Remote Similarity NPD5222 Approved
0.6415 Remote Similarity NPD7839 Suspended
0.6415 Remote Similarity NPD5221 Approved
0.6415 Remote Similarity NPD5220 Clinical (unspecified phase)
0.641 Remote Similarity NPD7115 Discovery
0.6408 Remote Similarity NPD7838 Discovery
0.6404 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6389 Remote Similarity NPD5285 Approved
0.6389 Remote Similarity NPD5286 Approved
0.6389 Remote Similarity NPD4696 Approved
0.6373 Remote Similarity NPD5208 Approved
0.6364 Remote Similarity NPD7154 Phase 3
0.6355 Remote Similarity NPD5173 Approved
0.6355 Remote Similarity NPD4755 Approved
0.6355 Remote Similarity NPD7902 Approved
0.6349 Remote Similarity NPD6845 Suspended
0.6346 Remote Similarity NPD7983 Approved
0.6346 Remote Similarity NPD7515 Phase 2
0.6337 Remote Similarity NPD6684 Approved
0.6337 Remote Similarity NPD5330 Approved
0.6337 Remote Similarity NPD7334 Approved
0.6337 Remote Similarity NPD7146 Approved
0.6337 Remote Similarity NPD6409 Approved
0.6337 Remote Similarity NPD7521 Approved
0.6337 Remote Similarity NPD3574 Clinical (unspecified phase)
0.633 Remote Similarity NPD5223 Approved
0.6325 Remote Similarity NPD6274 Approved
0.6321 Remote Similarity NPD5210 Approved
0.6321 Remote Similarity NPD4629 Approved
0.6306 Remote Similarity NPD5141 Approved
0.63 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6296 Remote Similarity NPD7638 Approved
0.6293 Remote Similarity NPD4632 Approved
0.6286 Remote Similarity NPD5133 Approved
0.6273 Remote Similarity NPD5225 Approved
0.6273 Remote Similarity NPD4633 Approved
0.6273 Remote Similarity NPD5224 Approved
0.6273 Remote Similarity NPD5226 Approved
0.6271 Remote Similarity NPD6317 Approved
0.6262 Remote Similarity NPD4697 Phase 3
0.6262 Remote Similarity NPD7614 Phase 1
0.625 Remote Similarity NPD4096 Approved
0.6239 Remote Similarity NPD6404 Discontinued
0.6239 Remote Similarity NPD7640 Approved
0.6239 Remote Similarity NPD4700 Approved
0.6239 Remote Similarity NPD7639 Approved
0.6238 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6238 Remote Similarity NPD5363 Approved
0.6222 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6222 Remote Similarity NPD3704 Approved
0.6218 Remote Similarity NPD6314 Approved
0.6218 Remote Similarity NPD6313 Approved
0.6218 Remote Similarity NPD6335 Approved
0.6216 Remote Similarity NPD5175 Approved
0.6216 Remote Similarity NPD5174 Approved
0.6214 Remote Similarity NPD6903 Approved
0.6214 Remote Similarity NPD7513 Clinical (unspecified phase)
0.619 Remote Similarity NPD6079 Approved
0.6186 Remote Similarity NPD6868 Approved
0.6186 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6176 Remote Similarity NPD5786 Approved
0.6176 Remote Similarity NPD4690 Approved
0.6176 Remote Similarity NPD4688 Approved
0.6176 Remote Similarity NPD5205 Approved
0.6176 Remote Similarity NPD4689 Approved
0.6176 Remote Similarity NPD4693 Phase 3
0.6176 Remote Similarity NPD4138 Approved
0.6176 Remote Similarity NPD6422 Discontinued
0.6168 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6167 Remote Similarity NPD7101 Approved
0.6167 Remote Similarity NPD7100 Approved
0.6154 Remote Similarity NPD5328 Approved
0.6139 Remote Similarity NPD3665 Phase 1
0.6139 Remote Similarity NPD3133 Approved
0.6139 Remote Similarity NPD3666 Approved
0.6136 Remote Similarity NPD4192 Approved
0.6136 Remote Similarity NPD4191 Approved
0.6136 Remote Similarity NPD4194 Approved
0.6136 Remote Similarity NPD4193 Approved
0.6134 Remote Similarity NPD6009 Approved
0.6121 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6116 Remote Similarity NPD6319 Approved
0.6111 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6106 Remote Similarity NPD6008 Approved
0.61 Remote Similarity NPD6435 Approved
0.61 Remote Similarity NPD3667 Approved
0.6075 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6075 Remote Similarity NPD6001 Approved
0.6075 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6075 Remote Similarity NPD7900 Approved
0.6071 Remote Similarity NPD4754 Approved
0.6066 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6066 Remote Similarity NPD5983 Phase 2
0.6053 Remote Similarity NPD6614 Approved
0.604 Remote Similarity NPD5362 Discontinued
0.6038 Remote Similarity NPD7637 Suspended
0.6019 Remote Similarity NPD3618 Phase 1
0.6018 Remote Similarity NPD5909 Discontinued
0.6 Remote Similarity NPD5128 Approved
0.6 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6 Remote Similarity NPD4729 Approved
0.6 Remote Similarity NPD1695 Approved
0.6 Remote Similarity NPD4730 Approved
0.6 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6 Remote Similarity NPD5369 Approved
0.5982 Remote Similarity NPD5091 Approved
0.598 Remote Similarity NPD4786 Approved
0.5968 Remote Similarity NPD7604 Phase 2

Structure

External Identifiers

PubChem CID   194464
ChEMBL   CHEMBL1807756
ZINC  

Physicochemical Properties

Molecular Weight:  328.17
ALogP:  2.1685
MLogP:  3.22
XLogP:  2.818
# Rotatable Bonds:  7
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  24

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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