Natural Product: NPC171665

Natural Product ID:  NPC171665
Common Name:   Calamusin A
IUPAC Name:   (3aS,4R,8S,8aS)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-4,8-dimethyl-5,6,8,8a-tetrahydro-4H-azulene-1,7-dione
Synonyms:   Calamusin A
Molecular Formula:   C15H22O4
Standard InCHIKey:  WTUUXOKSFWSVCT-YGDJUROISA-N
Standard InCHI:  InChI=1S/C15H22O4/c1-8-5-6-11(16)9(2)12-13(17)10(14(3,4)18)7-15(8,12)19/h7-9,12,18-19H,5-6H2,1-4H3/t8-,9-,12-,15-/m1/s1
Canonical SMILES:  O=C1CC[C@H]([C@]2([C@H]([C@@H]1C)C(=O)C(=C2)C(O)(C)C)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
NPO25682 Acorus calamus Species Acoraceae Eukaryota Rhizomes PMID[22671987]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10000 nM 25136754
NPT179 Cell Line A2780 Homo sapiens IC50 > 10000 nM 20159656
NPT81 Cell Line A549 Homo sapiens IC50 > 10000 nM 23819871
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 10000 nM 10.6019/CHEMBL1201861
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10000 nM 22037378

  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 NPC171665 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 NPC476628
0.8333 Intermediate Similarity NPC7382
0.8272 Intermediate Similarity NPC472013
0.8272 Intermediate Similarity NPC476624
0.8228 Intermediate Similarity NPC89374
0.8125 Intermediate Similarity NPC124289
0.8125 Intermediate Similarity NPC142759
0.8125 Intermediate Similarity NPC115719
0.8125 Intermediate Similarity NPC473437
0.8125 Intermediate Similarity NPC141346
0.8125 Intermediate Similarity NPC25908
0.8025 Intermediate Similarity NPC472014
0.7976 Intermediate Similarity NPC133844
0.7955 Intermediate Similarity NPC205548
0.7927 Intermediate Similarity NPC476627
0.7901 Intermediate Similarity NPC182848
0.7625 Intermediate Similarity NPC469737
0.7625 Intermediate Similarity NPC29328
0.7619 Intermediate Similarity NPC84185
0.7619 Intermediate Similarity NPC471890
0.7619 Intermediate Similarity NPC66677
0.7586 Intermediate Similarity NPC472957
0.7586 Intermediate Similarity NPC472958
0.7582 Intermediate Similarity NPC144629
0.7582 Intermediate Similarity NPC261607
0.7582 Intermediate Similarity NPC111114
0.7582 Intermediate Similarity NPC300312
0.7558 Intermediate Similarity NPC20262
0.7558 Intermediate Similarity NPC256750
0.7556 Intermediate Similarity NPC170775
0.7531 Intermediate Similarity NPC300940
0.7529 Intermediate Similarity NPC138492
0.7529 Intermediate Similarity NPC287817
0.7529 Intermediate Similarity NPC164218
0.7529 Intermediate Similarity NPC233352
0.7529 Intermediate Similarity NPC74445
0.7529 Intermediate Similarity NPC824
0.7529 Intermediate Similarity NPC30675
0.75 Intermediate Similarity NPC135776
0.75 Intermediate Similarity NPC125290
0.7473 Intermediate Similarity NPC77337
0.7444 Intermediate Similarity NPC472677
0.7444 Intermediate Similarity NPC58532
0.7419 Intermediate Similarity NPC167219
0.7412 Intermediate Similarity NPC32758
0.7412 Intermediate Similarity NPC301769
0.7391 Intermediate Similarity NPC476705
0.7375 Intermediate Similarity NPC67608
0.7375 Intermediate Similarity NPC469914
0.7363 Intermediate Similarity NPC32922
0.7349 Intermediate Similarity NPC77501
0.7342 Intermediate Similarity NPC476626
0.734 Intermediate Similarity NPC261341
0.7326 Intermediate Similarity NPC470946
0.7326 Intermediate Similarity NPC476625
0.7326 Intermediate Similarity NPC470947
0.7326 Intermediate Similarity NPC470945
0.732 Intermediate Similarity NPC474742
0.732 Intermediate Similarity NPC206079
0.7317 Intermediate Similarity NPC275098
0.7294 Intermediate Similarity NPC19443
0.7292 Intermediate Similarity NPC244411
0.7292 Intermediate Similarity NPC470541
0.7292 Intermediate Similarity NPC141191
0.7284 Intermediate Similarity NPC280256
0.7283 Intermediate Similarity NPC106510
0.7283 Intermediate Similarity NPC230332
0.7283 Intermediate Similarity NPC2946
0.7283 Intermediate Similarity NPC71533
0.7273 Intermediate Similarity NPC65350
0.7263 Intermediate Similarity NPC185553
0.7253 Intermediate Similarity NPC474854
0.7234 Intermediate Similarity NPC323008
0.7234 Intermediate Similarity NPC470010
0.7234 Intermediate Similarity NPC262133
0.7234 Intermediate Similarity NPC477131
0.7234 Intermediate Similarity NPC470013
0.7229 Intermediate Similarity NPC206875
0.7222 Intermediate Similarity NPC476043
0.7216 Intermediate Similarity NPC280963
0.7195 Intermediate Similarity NPC106309
0.7191 Intermediate Similarity NPC230527
0.7191 Intermediate Similarity NPC7927
0.7188 Intermediate Similarity NPC169205
0.7176 Intermediate Similarity NPC34110
0.7174 Intermediate Similarity NPC52198
0.7174 Intermediate Similarity NPC117405
0.7174 Intermediate Similarity NPC232747
0.7174 Intermediate Similarity NPC123912
0.7174 Intermediate Similarity NPC41217
0.7172 Intermediate Similarity NPC475871
0.7172 Intermediate Similarity NPC475945
0.7172 Intermediate Similarity NPC270046
0.7172 Intermediate Similarity NPC110989
0.7172 Intermediate Similarity NPC475873
0.7158 Intermediate Similarity NPC304886
0.7158 Intermediate Similarity NPC48803
0.7158 Intermediate Similarity NPC90121
0.7158 Intermediate Similarity NPC275960
0.7158 Intermediate Similarity NPC193645
0.7143 Intermediate Similarity NPC237540
0.7143 Intermediate Similarity NPC474011
0.7143 Intermediate Similarity NPC62670
0.7143 Intermediate Similarity NPC251435
0.7143 Intermediate Similarity NPC116139
0.7126 Intermediate Similarity NPC45495
0.7125 Intermediate Similarity NPC278895
0.7111 Intermediate Similarity NPC474853
0.7111 Intermediate Similarity NPC179006
0.71 Intermediate Similarity NPC474741
0.71 Intermediate Similarity NPC100487
0.71 Intermediate Similarity NPC203659
0.7097 Intermediate Similarity NPC62815
0.7093 Intermediate Similarity NPC192006
0.7089 Intermediate Similarity NPC61473
0.7083 Intermediate Similarity NPC135576
0.7083 Intermediate Similarity NPC93271
0.7083 Intermediate Similarity NPC9812
0.7071 Intermediate Similarity NPC66110
0.7071 Intermediate Similarity NPC474747
0.7071 Intermediate Similarity NPC225353
0.7065 Intermediate Similarity NPC476707
0.7065 Intermediate Similarity NPC476708
0.7065 Intermediate Similarity NPC476706
0.7065 Intermediate Similarity NPC91248
0.7059 Intermediate Similarity NPC239758
0.7059 Intermediate Similarity NPC151622
0.7059 Intermediate Similarity NPC71220
0.7059 Intermediate Similarity NPC137286
0.7059 Intermediate Similarity NPC469646
0.7059 Intermediate Similarity NPC472305
0.7059 Intermediate Similarity NPC215481
0.7059 Intermediate Similarity NPC7629
0.7053 Intermediate Similarity NPC298919
0.7053 Intermediate Similarity NPC90453
0.7053 Intermediate Similarity NPC198853
0.7053 Intermediate Similarity NPC469632
0.7045 Intermediate Similarity NPC275766
0.7041 Intermediate Similarity NPC306856
0.7037 Intermediate Similarity NPC476614
0.7037 Intermediate Similarity NPC476629
0.7033 Intermediate Similarity NPC472869
0.7033 Intermediate Similarity NPC194417
0.7033 Intermediate Similarity NPC472479
0.703 Intermediate Similarity NPC314244
0.703 Intermediate Similarity NPC223450
0.703 Intermediate Similarity NPC243998
0.7021 Intermediate Similarity NPC133698
0.7021 Intermediate Similarity NPC284185
0.7021 Intermediate Similarity NPC131209
0.7011 Intermediate Similarity NPC181195
0.7011 Intermediate Similarity NPC469617
0.7011 Intermediate Similarity NPC7232
0.7011 Intermediate Similarity NPC261125
0.701 Intermediate Similarity NPC477949
0.701 Intermediate Similarity NPC108475
0.701 Intermediate Similarity NPC170143
0.701 Intermediate Similarity NPC213947
0.7 Intermediate Similarity NPC90446
0.7 Intermediate Similarity NPC197089
0.6989 Remote Similarity NPC295312
0.6989 Remote Similarity NPC268298
0.6988 Remote Similarity NPC288667
0.6977 Remote Similarity NPC471061
0.6977 Remote Similarity NPC86917
0.697 Remote Similarity NPC472924
0.697 Remote Similarity NPC195192
0.697 Remote Similarity NPC475099
0.697 Remote Similarity NPC477950
0.697 Remote Similarity NPC304738
0.6966 Remote Similarity NPC227925
0.6966 Remote Similarity NPC92226
0.6966 Remote Similarity NPC279186
0.6957 Remote Similarity NPC72513
0.6947 Remote Similarity NPC131840
0.6947 Remote Similarity NPC125180
0.6941 Remote Similarity NPC244166
0.6941 Remote Similarity NPC201263
0.6939 Remote Similarity NPC64742
0.6932 Remote Similarity NPC472948
0.6923 Remote Similarity NPC257240
0.6923 Remote Similarity NPC261380
0.6923 Remote Similarity NPC477103
0.6923 Remote Similarity NPC137033
0.6915 Remote Similarity NPC253144
0.6915 Remote Similarity NPC129419
0.6915 Remote Similarity NPC472866
0.6915 Remote Similarity NPC145666
0.6907 Remote Similarity NPC184065
0.6907 Remote Similarity NPC471463
0.6905 Remote Similarity NPC247586
0.69 Remote Similarity NPC86077
0.6897 Remote Similarity NPC62336
0.6897 Remote Similarity NPC207772
0.6897 Remote Similarity NPC169095
0.6897 Remote Similarity NPC478122
0.6889 Remote Similarity NPC39588
0.6882 Remote Similarity NPC472870
0.6882 Remote Similarity NPC87189
0.6882 Remote Similarity NPC227379

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC171665 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
0.7976 Intermediate Similarity NPD4800 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD7341 Phase 2
0.7 Intermediate Similarity NPD7331 Phase 2
0.6923 Remote Similarity NPD5363 Approved
0.6923 Remote Similarity NPD6371 Approved
0.6848 Remote Similarity NPD5786 Approved
0.6848 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6701 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD4623 Approved
0.6667 Remote Similarity NPD4519 Discontinued
0.6635 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6593 Remote Similarity NPD4269 Approved
0.6593 Remote Similarity NPD4270 Approved
0.6562 Remote Similarity NPD5785 Approved
0.6458 Remote Similarity NPD1695 Approved
0.6429 Remote Similarity NPD5779 Approved
0.6429 Remote Similarity NPD5778 Approved
0.6413 Remote Similarity NPD4221 Approved
0.6413 Remote Similarity NPD4223 Phase 3
0.6383 Remote Similarity NPD1696 Phase 3
0.6374 Remote Similarity NPD4252 Approved
0.6374 Remote Similarity NPD4695 Discontinued
0.6344 Remote Similarity NPD5362 Discontinued
0.6333 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5690 Phase 2
0.6304 Remote Similarity NPD5369 Approved
0.6277 Remote Similarity NPD4197 Approved
0.625 Remote Similarity NPD5211 Phase 2
0.6238 Remote Similarity NPD4697 Phase 3
0.622 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6211 Remote Similarity NPD5329 Approved
0.6162 Remote Similarity NPD5284 Approved
0.6162 Remote Similarity NPD7983 Approved
0.6162 Remote Similarity NPD6079 Approved
0.6162 Remote Similarity NPD5281 Approved
0.6147 Remote Similarity NPD4634 Approved
0.6146 Remote Similarity NPD4694 Approved
0.6146 Remote Similarity NPD4688 Approved
0.6146 Remote Similarity NPD4693 Phase 3
0.6146 Remote Similarity NPD5280 Approved
0.6146 Remote Similarity NPD5205 Approved
0.6146 Remote Similarity NPD4138 Approved
0.6146 Remote Similarity NPD4689 Approved
0.6146 Remote Similarity NPD4690 Approved
0.6139 Remote Similarity NPD4629 Approved
0.6139 Remote Similarity NPD5210 Approved
0.6132 Remote Similarity NPD5141 Approved
0.6122 Remote Similarity NPD4753 Phase 2
0.6122 Remote Similarity NPD5328 Approved
0.6078 Remote Similarity NPD5221 Approved
0.6078 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6078 Remote Similarity NPD5222 Approved
0.6058 Remote Similarity NPD5286 Approved
0.6058 Remote Similarity NPD5285 Approved
0.6058 Remote Similarity NPD4696 Approved
0.6042 Remote Similarity NPD1694 Approved
0.6042 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6022 Remote Similarity NPD5368 Approved
0.602 Remote Similarity NPD4518 Approved
0.6019 Remote Similarity NPD5173 Approved
0.6019 Remote Similarity NPD4755 Approved
0.6 Remote Similarity NPD5223 Approved
0.6 Remote Similarity NPD6110 Phase 1
0.6 Remote Similarity NPD7154 Phase 3
0.5979 Remote Similarity NPD3618 Phase 1
0.5979 Remote Similarity NPD5279 Phase 3
0.5978 Remote Similarity NPD3617 Approved
0.5943 Remote Similarity NPD4633 Approved
0.5943 Remote Similarity NPD5224 Approved
0.5943 Remote Similarity NPD5225 Approved
0.5943 Remote Similarity NPD5226 Approved
0.5938 Remote Similarity NPD3665 Phase 1
0.5938 Remote Similarity NPD3666 Approved
0.5938 Remote Similarity NPD3133 Approved
0.5922 Remote Similarity NPD7839 Suspended
0.5914 Remote Similarity NPD4195 Approved
0.5905 Remote Similarity NPD4700 Approved
0.59 Remote Similarity NPD4096 Approved
0.5895 Remote Similarity NPD6435 Approved
0.5895 Remote Similarity NPD5209 Approved
0.5895 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5893 Remote Similarity NPD6053 Discontinued
0.5888 Remote Similarity NPD5175 Approved
0.5888 Remote Similarity NPD5174 Approved
0.587 Remote Similarity NPD4756 Discovery
0.5851 Remote Similarity NPD4821 Approved
0.5851 Remote Similarity NPD4820 Approved
0.5851 Remote Similarity NPD4819 Approved
0.5851 Remote Similarity NPD4822 Approved
0.5833 Remote Similarity NPD5332 Approved
0.5833 Remote Similarity NPD5331 Approved
0.5826 Remote Similarity NPD7115 Discovery
0.5825 Remote Similarity NPD5695 Phase 3
0.581 Remote Similarity NPD5696 Approved
0.581 Remote Similarity NPD4225 Approved
0.5804 Remote Similarity NPD6649 Approved
0.5804 Remote Similarity NPD6650 Approved
0.58 Remote Similarity NPD5764 Clinical (unspecified phase)
0.58 Remote Similarity NPD6101 Approved
0.5794 Remote Similarity NPD5091 Approved
0.5789 Remote Similarity NPD4139 Approved
0.5789 Remote Similarity NPD857 Phase 3
0.5789 Remote Similarity NPD4790 Discontinued
0.5789 Remote Similarity NPD4692 Approved
0.5784 Remote Similarity NPD5133 Approved
0.5784 Remote Similarity NPD6399 Phase 3
0.5784 Remote Similarity NPD4202 Approved
0.5773 Remote Similarity NPD4786 Approved
0.5766 Remote Similarity NPD6373 Approved
0.5766 Remote Similarity NPD6372 Approved
0.5758 Remote Similarity NPD3573 Approved
0.5743 Remote Similarity NPD46 Approved
0.5743 Remote Similarity NPD6698 Approved
0.5741 Remote Similarity NPD4754 Approved
0.5729 Remote Similarity NPD3667 Approved
0.5727 Remote Similarity NPD5697 Approved
0.5714 Remote Similarity NPD6083 Phase 2
0.5714 Remote Similarity NPD6084 Phase 2
0.5702 Remote Similarity NPD4632 Approved
0.5686 Remote Similarity NPD5693 Phase 1
0.5686 Remote Similarity NPD7637 Suspended
0.5686 Remote Similarity NPD6411 Approved
0.5678 Remote Similarity NPD6054 Approved
0.5678 Remote Similarity NPD6319 Approved
0.5676 Remote Similarity NPD6881 Approved
0.5676 Remote Similarity NPD6899 Approved
0.5676 Remote Similarity NPD6011 Approved
0.5676 Remote Similarity NPD4730 Approved
0.5676 Remote Similarity NPD4729 Approved
0.5676 Remote Similarity NPD5128 Approved
0.567 Remote Similarity NPD4788 Approved
0.566 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5644 Remote Similarity NPD5370 Suspended
0.5644 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5644 Remote Similarity NPD6673 Approved
0.5644 Remote Similarity NPD6904 Approved
0.5644 Remote Similarity NPD6080 Approved
0.5638 Remote Similarity NPD4268 Approved
0.5638 Remote Similarity NPD4271 Approved
0.5636 Remote Similarity NPD4768 Approved
0.5636 Remote Similarity NPD4767 Approved
0.5636 Remote Similarity NPD6675 Approved
0.5636 Remote Similarity NPD5739 Approved
0.5636 Remote Similarity NPD7128 Approved
0.5636 Remote Similarity NPD6402 Approved
0.5636 Remote Similarity NPD6008 Approved
0.563 Remote Similarity NPD6015 Approved
0.563 Remote Similarity NPD6016 Approved
0.5625 Remote Similarity NPD6012 Approved
0.5625 Remote Similarity NPD6013 Approved
0.5625 Remote Similarity NPD6014 Approved
0.5619 Remote Similarity NPD7614 Phase 1
0.5607 Remote Similarity NPD7640 Approved
0.5607 Remote Similarity NPD7639 Approved
0.5607 Remote Similarity NPD6404 Discontinued

Structure

External Identifiers

PubChem CID   60156050
ChEMBL   CHEMBL2063009
ZINC  

Physicochemical Properties

Molecular Weight:  266.15
ALogP:  -0.2929
MLogP:  2.67
XLogP:  -0.03
# Rotatable Bonds:  7
Polar Surface Area:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  19

Download Data

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