Natural Product: NPC16321

Natural Product ID:  NPC16321
Common Name:   Zerumin
IUPAC Name:   4-[(E)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-3-hydroxy-2H-furan-5-one
Synonyms:   Zerumin
Molecular Formula:   C20H28O3
Standard InCHIKey:  OEKNHOLIWSBXIC-NEMSWOBWSA-N
Standard InCHI:  InChI=1S/C20H28O3/c1-13-6-9-17-19(2,3)10-5-11-20(17,4)15(13)8-7-14-16(21)12-23-18(14)22/h7-8,15,17,21H,1,5-6,9-12H2,2-4H3/b8-7+/t15-,17-,20+/m0/s1
Canonical SMILES:  C=C1CC[C@@H]2[C@]([C@H]1/C=C/C1=C(O)COC1=O)(C)CCCC2(C)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
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota Aerial parts PMID[20196571]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT111 Cell Line K562 Homo sapiens FC = 1 20674349
NPT111 Cell Line K562 Homo sapiens Activity = 87.5 % 20674349

  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 NPC16321 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
0.8961 High Similarity NPC4509
0.8537 High Similarity NPC94200
0.8313 Intermediate Similarity NPC268122
0.8235 Intermediate Similarity NPC329630
0.8214 Intermediate Similarity NPC118423
0.8182 Intermediate Similarity NPC182136
0.8182 Intermediate Similarity NPC310479
0.8132 Intermediate Similarity NPC473153
0.8118 Intermediate Similarity NPC470800
0.8068 Intermediate Similarity NPC79027
0.8 Intermediate Similarity NPC205034
0.8 Intermediate Similarity NPC162615
0.8 Intermediate Similarity NPC42476
0.8 Intermediate Similarity NPC152778
0.7978 Intermediate Similarity NPC280149
0.7978 Intermediate Similarity NPC221111
0.7975 Intermediate Similarity NPC181587
0.7935 Intermediate Similarity NPC16967
0.7931 Intermediate Similarity NPC168248
0.7912 Intermediate Similarity NPC191521
0.7857 Intermediate Similarity NPC268827
0.7841 Intermediate Similarity NPC473891
0.7826 Intermediate Similarity NPC209355
0.7826 Intermediate Similarity NPC295347
0.7802 Intermediate Similarity NPC53555
0.7802 Intermediate Similarity NPC469939
0.7802 Intermediate Similarity NPC242069
0.7792 Intermediate Similarity NPC185587
0.7791 Intermediate Similarity NPC311070
0.7753 Intermediate Similarity NPC196407
0.7717 Intermediate Similarity NPC470255
0.7711 Intermediate Similarity NPC54996
0.7692 Intermediate Similarity NPC303697
0.7667 Intermediate Similarity NPC474844
0.7667 Intermediate Similarity NPC471654
0.766 Intermediate Similarity NPC208094
0.7629 Intermediate Similarity NPC23584
0.7619 Intermediate Similarity NPC184737
0.7614 Intermediate Similarity NPC30984
0.7614 Intermediate Similarity NPC86316
0.7614 Intermediate Similarity NPC106416
0.7614 Intermediate Similarity NPC65661
0.7614 Intermediate Similarity NPC217394
0.7614 Intermediate Similarity NPC471795
0.7586 Intermediate Similarity NPC474976
0.7586 Intermediate Similarity NPC49208
0.7586 Intermediate Similarity NPC474790
0.7579 Intermediate Similarity NPC474440
0.7579 Intermediate Similarity NPC181147
0.7561 Intermediate Similarity NPC20025
0.7561 Intermediate Similarity NPC104644
0.7556 Intermediate Similarity NPC472302
0.7556 Intermediate Similarity NPC474629
0.7532 Intermediate Similarity NPC329698
0.7529 Intermediate Similarity NPC190211
0.7528 Intermediate Similarity NPC131813
0.7528 Intermediate Similarity NPC471219
0.7526 Intermediate Similarity NPC11956
0.75 Intermediate Similarity NPC473825
0.75 Intermediate Similarity NPC189206
0.75 Intermediate Similarity NPC96055
0.7473 Intermediate Similarity NPC82876
0.7473 Intermediate Similarity NPC50488
0.7473 Intermediate Similarity NPC474396
0.7471 Intermediate Similarity NPC200513
0.7471 Intermediate Similarity NPC471218
0.7444 Intermediate Similarity NPC125925
0.7444 Intermediate Similarity NPC75315
0.7444 Intermediate Similarity NPC163016
0.7442 Intermediate Similarity NPC233332
0.7436 Intermediate Similarity NPC107258
0.7423 Intermediate Similarity NPC303559
0.7412 Intermediate Similarity NPC105197
0.7396 Intermediate Similarity NPC159763
0.7396 Intermediate Similarity NPC278386
0.7396 Intermediate Similarity NPC124512
0.7391 Intermediate Similarity NPC78973
0.7391 Intermediate Similarity NPC51486
0.7386 Intermediate Similarity NPC469
0.7386 Intermediate Similarity NPC23748
0.7363 Intermediate Similarity NPC472810
0.7363 Intermediate Similarity NPC472809
0.734 Intermediate Similarity NPC469491
0.7333 Intermediate Similarity NPC329692
0.7327 Intermediate Similarity NPC473482
0.7327 Intermediate Similarity NPC475418
0.7327 Intermediate Similarity NPC318363
0.732 Intermediate Similarity NPC477720
0.732 Intermediate Similarity NPC38855
0.7317 Intermediate Similarity NPC133253
0.7312 Intermediate Similarity NPC472811
0.7312 Intermediate Similarity NPC72845
0.7312 Intermediate Similarity NPC177037
0.7312 Intermediate Similarity NPC472814
0.7308 Intermediate Similarity NPC226066
0.7303 Intermediate Similarity NPC318515
0.73 Intermediate Similarity NPC477125
0.7294 Intermediate Similarity NPC262747
0.7292 Intermediate Similarity NPC205143
0.7292 Intermediate Similarity NPC73911
0.7283 Intermediate Similarity NPC177141
0.7283 Intermediate Similarity NPC174342
0.7283 Intermediate Similarity NPC284561
0.7283 Intermediate Similarity NPC251528
0.7283 Intermediate Similarity NPC5509
0.7273 Intermediate Similarity NPC469804
0.7273 Intermediate Similarity NPC469806
0.7273 Intermediate Similarity NPC324170
0.7273 Intermediate Similarity NPC469805
0.7273 Intermediate Similarity NPC469799
0.7262 Intermediate Similarity NPC65650
0.7255 Intermediate Similarity NPC475065
0.7253 Intermediate Similarity NPC312561
0.7253 Intermediate Similarity NPC471796
0.7253 Intermediate Similarity NPC476600
0.7241 Intermediate Similarity NPC469797
0.7241 Intermediate Similarity NPC10636
0.7241 Intermediate Similarity NPC469798
0.7234 Intermediate Similarity NPC139692
0.7234 Intermediate Similarity NPC156553
0.7234 Intermediate Similarity NPC472812
0.7229 Intermediate Similarity NPC276336
0.7229 Intermediate Similarity NPC16349
0.7229 Intermediate Similarity NPC222244
0.7228 Intermediate Similarity NPC329048
0.7228 Intermediate Similarity NPC330011
0.7222 Intermediate Similarity NPC35933
0.7222 Intermediate Similarity NPC42586
0.7222 Intermediate Similarity NPC189311
0.7222 Intermediate Similarity NPC473251
0.7222 Intermediate Similarity NPC474013
0.7216 Intermediate Similarity NPC278673
0.7209 Intermediate Similarity NPC474816
0.7209 Intermediate Similarity NPC209135
0.7204 Intermediate Similarity NPC212679
0.7204 Intermediate Similarity NPC273199
0.7204 Intermediate Similarity NPC477782
0.7204 Intermediate Similarity NPC469595
0.7204 Intermediate Similarity NPC220454
0.72 Intermediate Similarity NPC200861
0.72 Intermediate Similarity NPC472822
0.7191 Intermediate Similarity NPC477124
0.7191 Intermediate Similarity NPC472377
0.7191 Intermediate Similarity NPC193198
0.7191 Intermediate Similarity NPC3856
0.7191 Intermediate Similarity NPC279639
0.7191 Intermediate Similarity NPC474193
0.7191 Intermediate Similarity NPC12283
0.7188 Intermediate Similarity NPC260796
0.7179 Intermediate Similarity NPC44343
0.7179 Intermediate Similarity NPC179087
0.7179 Intermediate Similarity NPC210303
0.7176 Intermediate Similarity NPC474463
0.7174 Intermediate Similarity NPC473879
0.7172 Intermediate Similarity NPC472552
0.7172 Intermediate Similarity NPC114540
0.7172 Intermediate Similarity NPC32577
0.7172 Intermediate Similarity NPC155332
0.7159 Intermediate Similarity NPC170303
0.7159 Intermediate Similarity NPC40228
0.7159 Intermediate Similarity NPC14203
0.7159 Intermediate Similarity NPC229584
0.7159 Intermediate Similarity NPC25554
0.7158 Intermediate Similarity NPC57117
0.7158 Intermediate Similarity NPC477129
0.7158 Intermediate Similarity NPC477130
0.7158 Intermediate Similarity NPC469697
0.7157 Intermediate Similarity NPC50124
0.7143 Intermediate Similarity NPC75485
0.7143 Intermediate Similarity NPC470686
0.7143 Intermediate Similarity NPC168975
0.7143 Intermediate Similarity NPC211892
0.7129 Intermediate Similarity NPC82251
0.7129 Intermediate Similarity NPC471206
0.7128 Intermediate Similarity NPC329842
0.7128 Intermediate Similarity NPC477783
0.7126 Intermediate Similarity NPC233295
0.7126 Intermediate Similarity NPC242767
0.7125 Intermediate Similarity NPC191233
0.7125 Intermediate Similarity NPC259156
0.7125 Intermediate Similarity NPC242945
0.7125 Intermediate Similarity NPC255781
0.7113 Intermediate Similarity NPC110937
0.7113 Intermediate Similarity NPC202705
0.7113 Intermediate Similarity NPC231751
0.7111 Intermediate Similarity NPC32223
0.7111 Intermediate Similarity NPC475100
0.7111 Intermediate Similarity NPC149869
0.7108 Intermediate Similarity NPC21944
0.7108 Intermediate Similarity NPC257618
0.7097 Intermediate Similarity NPC210216
0.7097 Intermediate Similarity NPC470734
0.7083 Intermediate Similarity NPC276110
0.7079 Intermediate Similarity NPC474028
0.7079 Intermediate Similarity NPC474439
0.7073 Intermediate Similarity NPC232812
0.7071 Intermediate Similarity NPC472554
0.7071 Intermediate Similarity NPC198992
0.7059 Intermediate Similarity NPC67321
0.7059 Intermediate Similarity NPC187435

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC16321 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
0.7471 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD4225 Approved
0.7308 Intermediate Similarity NPD5325 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4191 Approved
0.7051 Intermediate Similarity NPD4192 Approved
0.7051 Intermediate Similarity NPD4194 Approved
0.7051 Intermediate Similarity NPD4193 Approved
0.6947 Remote Similarity NPD7637 Suspended
0.6923 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6827 Remote Similarity NPD6686 Approved
0.6703 Remote Similarity NPD5209 Approved
0.67 Remote Similarity NPD7638 Approved
0.6667 Remote Similarity NPD8039 Approved
0.6667 Remote Similarity NPD7838 Discovery
0.6634 Remote Similarity NPD7640 Approved
0.6634 Remote Similarity NPD7639 Approved
0.6552 Remote Similarity NPD4058 Approved
0.6489 Remote Similarity NPD1694 Approved
0.6486 Remote Similarity NPD7115 Discovery
0.6471 Remote Similarity NPD6648 Approved
0.6444 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6421 Remote Similarity NPD7334 Approved
0.6421 Remote Similarity NPD6409 Approved
0.6421 Remote Similarity NPD6684 Approved
0.6421 Remote Similarity NPD7521 Approved
0.6421 Remote Similarity NPD7146 Approved
0.6421 Remote Similarity NPD5330 Approved
0.6404 Remote Similarity NPD7503 Approved
0.6404 Remote Similarity NPD6933 Approved
0.6395 Remote Similarity NPD7143 Approved
0.6395 Remote Similarity NPD7144 Approved
0.6392 Remote Similarity NPD6051 Approved
0.6386 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6373 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4687 Approved
0.6354 Remote Similarity NPD7524 Approved
0.6327 Remote Similarity NPD6698 Approved
0.6327 Remote Similarity NPD46 Approved
0.6322 Remote Similarity NPD7152 Approved
0.6322 Remote Similarity NPD7151 Approved
0.6322 Remote Similarity NPD5276 Approved
0.6322 Remote Similarity NPD7150 Approved
0.6304 Remote Similarity NPD7332 Phase 2
0.6304 Remote Similarity NPD7514 Phase 3
0.6296 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6292 Remote Similarity NPD8264 Approved
0.6289 Remote Similarity NPD6903 Approved
0.6289 Remote Similarity NPD6672 Approved
0.6289 Remote Similarity NPD5737 Approved
0.6289 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6279 Remote Similarity NPD4137 Phase 3
0.6279 Remote Similarity NPD6923 Approved
0.6279 Remote Similarity NPD6922 Approved
0.6264 Remote Similarity NPD7145 Approved
0.6263 Remote Similarity NPD5693 Phase 1
0.625 Remote Similarity NPD5344 Discontinued
0.6237 Remote Similarity NPD6902 Approved
0.6224 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6207 Remote Similarity NPD4691 Approved
0.6207 Remote Similarity NPD4747 Approved
0.6203 Remote Similarity NPD4219 Approved
0.62 Remote Similarity NPD6399 Phase 3
0.618 Remote Similarity NPD5733 Approved
0.618 Remote Similarity NPD6926 Approved
0.618 Remote Similarity NPD6924 Approved
0.6162 Remote Similarity NPD5785 Approved
0.6162 Remote Similarity NPD5207 Approved
0.6154 Remote Similarity NPD5776 Phase 2
0.6154 Remote Similarity NPD6932 Approved
0.6154 Remote Similarity NPD6925 Approved
0.614 Remote Similarity NPD7328 Approved
0.614 Remote Similarity NPD7327 Approved
0.6139 Remote Similarity NPD7748 Approved
0.6129 Remote Similarity NPD4695 Discontinued
0.6121 Remote Similarity NPD8033 Approved
0.6117 Remote Similarity NPD6083 Phase 2
0.6117 Remote Similarity NPD6084 Phase 2
0.6105 Remote Similarity NPD6695 Phase 3
0.61 Remote Similarity NPD5281 Approved
0.61 Remote Similarity NPD6411 Approved
0.61 Remote Similarity NPD5284 Approved
0.61 Remote Similarity NPD5694 Approved
0.6091 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6087 Remote Similarity NPD7516 Approved
0.6082 Remote Similarity NPD4519 Discontinued
0.6082 Remote Similarity NPD4623 Approved
0.6082 Remote Similarity NPD5279 Phase 3
0.6078 Remote Similarity NPD5695 Phase 3
0.6058 Remote Similarity NPD5696 Approved
0.6042 Remote Similarity NPD3133 Approved
0.6042 Remote Similarity NPD3665 Phase 1
0.6042 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6042 Remote Similarity NPD3666 Approved
0.604 Remote Similarity NPD5778 Approved
0.604 Remote Similarity NPD5779 Approved
0.6038 Remote Similarity NPD7632 Discontinued
0.6034 Remote Similarity NPD8377 Approved
0.6034 Remote Similarity NPD8294 Approved
0.6022 Remote Similarity NPD6929 Approved
0.6022 Remote Similarity NPD4195 Approved
0.602 Remote Similarity NPD3573 Approved
0.6019 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6 Remote Similarity NPD5692 Phase 3
0.6 Remote Similarity NPD3667 Approved
0.5983 Remote Similarity NPD8380 Approved
0.5983 Remote Similarity NPD8378 Approved
0.5983 Remote Similarity NPD8296 Approved
0.5983 Remote Similarity NPD8379 Approved
0.5983 Remote Similarity NPD8335 Approved
0.5963 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5962 Remote Similarity NPD7902 Approved
0.596 Remote Similarity NPD5208 Approved
0.5957 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5957 Remote Similarity NPD6931 Approved
0.5957 Remote Similarity NPD6930 Phase 2
0.5941 Remote Similarity NPD6050 Approved
0.5941 Remote Similarity NPD7515 Phase 2
0.5941 Remote Similarity NPD7983 Approved
0.5938 Remote Similarity NPD7154 Phase 3
0.5926 Remote Similarity NPD5909 Discontinued
0.5922 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5922 Remote Similarity NPD6049 Phase 2
0.5922 Remote Similarity NPD6048 Clinical (unspecified phase)
0.5918 Remote Similarity NPD3618 Phase 1
0.5917 Remote Similarity NPD7507 Approved
0.5914 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5913 Remote Similarity NPD4198 Discontinued
0.59 Remote Similarity NPD6080 Approved
0.59 Remote Similarity NPD5764 Clinical (unspecified phase)
0.59 Remote Similarity NPD6673 Approved
0.59 Remote Similarity NPD6904 Approved
0.59 Remote Similarity NPD6101 Approved
0.5895 Remote Similarity NPD6898 Phase 1
0.5876 Remote Similarity NPD4786 Approved
0.5872 Remote Similarity NPD6640 Phase 3
0.587 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5859 Remote Similarity NPD7750 Discontinued
0.5851 Remote Similarity NPD6683 Phase 2
0.5841 Remote Similarity NPD8297 Approved
0.5833 Remote Similarity NPD4221 Approved
0.5833 Remote Similarity NPD4223 Phase 3
0.5826 Remote Similarity NPD2629 Approved
0.5825 Remote Similarity NPD7900 Approved
0.5825 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5818 Remote Similarity NPD6412 Phase 2
0.5818 Remote Similarity NPD5697 Approved
0.5816 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5816 Remote Similarity NPD5734 Clinical (unspecified phase)
0.5816 Remote Similarity NPD1696 Phase 3
0.5806 Remote Similarity NPD7260 Phase 2
0.5804 Remote Similarity NPD6371 Approved
0.5804 Remote Similarity NPD2067 Discontinued
0.5795 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5789 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4632 Approved
0.5789 Remote Similarity NPD7509 Discontinued
0.5784 Remote Similarity NPD6079 Approved
0.5773 Remote Similarity NPD3971 Phase 1
0.5773 Remote Similarity NPD5362 Discontinued
0.5773 Remote Similarity NPD3527 Clinical (unspecified phase)
0.5772 Remote Similarity NPD7319 Approved
0.5769 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5766 Remote Similarity NPD6899 Approved
0.5766 Remote Similarity NPD6881 Approved
0.5766 Remote Similarity NPD6011 Approved
0.5761 Remote Similarity NPD6942 Approved
0.5761 Remote Similarity NPD7339 Approved
0.5758 Remote Similarity NPD6098 Approved
0.5758 Remote Similarity NPD4694 Approved
0.5758 Remote Similarity NPD5280 Approved
0.5755 Remote Similarity NPD5926 Approved
0.5745 Remote Similarity NPD3617 Approved
0.5743 Remote Similarity NPD4753 Phase 2
0.5743 Remote Similarity NPD5328 Approved
0.5727 Remote Similarity NPD6675 Approved
0.5727 Remote Similarity NPD5739 Approved
0.5727 Remote Similarity NPD6402 Approved
0.5727 Remote Similarity NPD7128 Approved
0.5714 Remote Similarity NPD5952 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3668 Phase 3
0.5714 Remote Similarity NPD4220 Pre-registration
0.5714 Remote Similarity NPD4197 Approved
0.5714 Remote Similarity NPD6013 Approved
0.5714 Remote Similarity NPD6014 Approved
0.5714 Remote Similarity NPD6012 Approved
0.5702 Remote Similarity NPD6053 Discontinued
0.5701 Remote Similarity NPD6404 Discontinued
0.57 Remote Similarity NPD1282 Approved
0.5676 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5676 Remote Similarity NPD5701 Approved
0.5673 Remote Similarity NPD6001 Approved
0.5664 Remote Similarity NPD7290 Approved
0.5664 Remote Similarity NPD7102 Approved
0.5664 Remote Similarity NPD6883 Approved
0.5657 Remote Similarity NPD5363 Approved
0.5657 Remote Similarity NPD6893 Approved
0.5657 Remote Similarity NPD5329 Approved
0.5657 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5652 Remote Similarity NPD4785 Approved
0.5652 Remote Similarity NPD4784 Approved

Structure

External Identifiers

PubChem CID   54734314
ChEMBL   CHEMBL1098958
ZINC  

Physicochemical Properties

Molecular Weight:  316.20
ALogP:  1.8181
MLogP:  3.33
XLogP:  6.632
# Rotatable Bonds:  6
Polar Surface Area:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  23

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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