Natural Product: NPC60556

Natural Product ID:  NPC60556
Common Name:   Caryophyllene
IUPAC Name:   (1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Synonyms:   Caryophyllene; Gamma-Caryophyllene
Molecular Formula:   C15H24
Standard InCHIKey:  NPNUFJAVOOONJE-FLFDDASRSA-N
Standard InCHI:  InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m1/s1
Canonical SMILES:  C/C/1=C/CCC(=C)[C@@H]2[C@@H](CC1)C(C2)(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
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota TM-MC*
NPO27171 Euphorbia sessiliflora Species Euphorbiaceae Eukaryota UNPD*
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota TM-MC*
NPO8314 Euodia ruticarpa Species Rutaceae Eukaryota TM-MC*
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota TM-MC*
NPO17229 Catha cassinoides Species Celastraceae Eukaryota UNPD*
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota TM-MC*
NPO19935 Tetradium ruticarpum Species Rutaceae Eukaryota TM-MC*
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota TM-MC*
NPO27462 Webera corymbosa NA NA NA UNPD*
NPO25825 Saussurea costus Species Asteraceae Eukaryota TM-MC*
NPO3083 Ferula assafoetida Species Apiaceae Eukaryota TM-MC*
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota TM-MC*
NPO1797 Homo sapiens Species Hominidae Eukaryota saliva PMID[24421258]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota TM-MC*
NPO3780 Ferula fukanensis Species Apiaceae Eukaryota TM-MC*
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota TM-MC*
NPO3412 Ferula sinkiangensis Species Apiaceae Eukaryota TM-MC*
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota TM-MC*
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota HerDing*
NPO9546 Cinamomum cassia NA NA NA TM-MC*
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota TM-MC*
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota TM-MC*
NPO30339 Nardostachys chinensis Species Caprifoliaceae Eukaryota HerDing*
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota TM-MC*
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota TM-MC*
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota TM-MC*
NPO29641 Rhododendri daurici folium NA NA NA TCMSP*
NPO7317 Citrus aurantium Species Rutaceae Eukaryota TM-MC*
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota TM-MC*
NPO14602 Vitex negundo Species Lamiaceae Eukaryota TM-MC*
NPO646 Moslae herba NA NA NA TCMSP*
NPO15730 Citrus medica Species Rutaceae Eukaryota TM-MC*
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota TM-MC*
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota TM-MC*
NPO29564 Farfarae flos NA NA NA TCMSP*
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota TM-MC*
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota TM-MC*
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota TM-MC*
NPO29575 Ardisiae japonicae herba NA NA NA TCMSP*
NPO25443 Citrus reticulata Species Rutaceae Eukaryota TM-MC*
NPO13274 Illicium verum Species Schisandraceae Eukaryota TM-MC*
NPO6884 Ailanthi cortex NA NA NA TCMSP*
NPO17728 Fritillariaeussuriensis bulbus NA NA NA TCMSP*
NPO19787 Citrus sinensis Species Rutaceae Eukaryota TM-MC*
NPO28807 Laggera pterodonta Species Asteraceae Eukaryota TM-MC*
NPO13736 Cnidii fructus NA NA NA TCMSP*
NPO10082 Citrus unshiu Species Rutaceae Eukaryota TM-MC*
NPO23548 Leonurus japonicus Species Lamiaceae Eukaryota TM-MC*
NPO29687 Houttuyniae herba NA NA NA TCMSP*
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota TM-MC*
NPO29110 Litsea cubeba Species Lauraceae Eukaryota TM-MC*
NPO17399 Kadsurae coccineae radix et caulis NA NA NA TCMSP*
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota TM-MC*
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota TM-MC*
NPO29374 Anisi stellati fructus NA NA NA TCMSP*
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota TM-MC*
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota TM-MC*
NPO29610 Aristolochiae fructus NA NA NA TCMSP*
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota TM-MC*
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota TM-MC*
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota TM-MC*
NPO29642 Centipedae herba NA NA NA TCMSP*
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota TM-MC*
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota TM-MC*
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota TM-MC*
NPO29630 Panacis quinquefolii radix NA NA NA TCMSP*
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota TM-MC*
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota TM-MC*
NPO29559 Cinnamomi ramulus NA NA NA TCMSP*
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota TM-MC*
NPO5986 Ziziphus jujuba Species Rhamnaceae Eukaryota TM-MC*
NPO29556 Piperis longi fructus NA NA NA TCMSP*
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota TM-MC*
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota TCMID*
NPO26351 Agastache rugosa Species Lamiaceae Eukaryota TM-MC*
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota TM-MC*
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota TCMID*
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota TM-MC*
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota TM-MC*
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota TCMID*
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota TM-MC*
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota TM-MC*
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota TM-MC*
NPO4460 Vincetoxicum glaucescens Species Apocynaceae Eukaryota TM-MC*
NPO12182 Murraya exotica Species Rutaceae Eukaryota TM-MC*
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota TM-MC*
NPO2761 Cynanchum stauntoni Species Apocynaceae Eukaryota TM-MC*
NPO2715 Murraya paniculata Species Rutaceae Eukaryota TM-MC*
NPO26589 Artemisia annua Species Asteraceae Eukaryota TM-MC*
NPO10366 Vincetoxicum stauntonii Species Apocynaceae Eukaryota TM-MC*
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota TM-MC*
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota TM-MC*
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota TM-MC*
NPO29141 Panax ginseng Species Araliaceae Eukaryota TM-MC*
NPO28276 Artemisia argyi Species Asteraceae Eukaryota TM-MC*
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota TM-MC*
NPO21891 Panax notoginseng Species Araliaceae Eukaryota TM-MC*
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota TM-MC*
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota TM-MC*
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota TM-MC*
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota TM-MC*
NPO10492 Artemisia montana Species Asteraceae Eukaryota TM-MC*
NPO16845 Euodia bodinieri Species Rutaceae Eukaryota TM-MC*
NPO11169 Piper cubeba Species Piperaceae Eukaryota TM-MC*
NPO25094 Artemisia princeps Species Asteraceae Eukaryota TM-MC*
NPO4877 Euodia officinalis Species Rutaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1 Others Radical scavenging activity EC50 = 3.7 ug/ml 8594153
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 800 ug/ml 1517735
NPT878 Organism Streptococcus mutans Streptococcus mutans MIC > 800 ug/ml 1517735
NPT19 Organism Escherichia coli Escherichia coli MIC > 800 ug/ml 1517735
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 800 ug/ml 1517735
NPT720 Organism Enterobacter aerogenes Enterobacter aerogenes MIC > 800 ug/ml 1517735
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC > 800 ug/ml 1517735
NPT767 Organism Pichia jadinii Cyberlindnera jadinii MIC > 800 ug/ml 1517735
NPT523 Organism Malassezia furfur Malassezia furfur MIC > 800 ug/ml 1517735
NPT2242 Organism Penicillium chrysogenum Penicillium chrysogenum MIC > 800 ug/ml 1517735
NPT2539 Organism Corynebacterium ammoniagenes Corynebacterium ammoniagenes MIC = 100 ug/ml 1517735
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 50 ug/ml 1517735
NPT167 Organism Propionibacterium acnes Propionibacterium acnes MIC = 6.25 ug/ml 1517735
NPT563 Organism Escherichia coli O157:H7 Escherichia coli O157:H7 GI = 12.8 % 14969531
NPT16 Organism Staphylococcus aureus Staphylococcus aureus GI = 54.7 % 14969531
NPT564 Organism Listeria monocytogenes Listeria monocytogenes GI = 7.2 % 14969531
NPT565 Organism Vibrio parahaemolyticus Vibrio parahaemolyticus GI = 26.5 % 14969531
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium GI = 10.2 % 14969531
NPT314 Organism Bacillus cereus Bacillus cereus GI = 32.1 % 14969531

  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 NPC60556 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
1.0 High Similarity NPC109813
0.8222 Intermediate Similarity NPC13991
0.8222 Intermediate Similarity NPC241784
0.8222 Intermediate Similarity NPC114239
0.8182 Intermediate Similarity NPC86538
0.8 Intermediate Similarity NPC248411
0.7907 Intermediate Similarity NPC62086
0.7907 Intermediate Similarity NPC227632
0.7907 Intermediate Similarity NPC78551
0.7826 Intermediate Similarity NPC49088
0.7826 Intermediate Similarity NPC296337
0.7826 Intermediate Similarity NPC86683
0.766 Intermediate Similarity NPC323445
0.7556 Intermediate Similarity NPC473912
0.7556 Intermediate Similarity NPC177470
0.75 Intermediate Similarity NPC124851
0.7442 Intermediate Similarity NPC229262
0.7442 Intermediate Similarity NPC297643
0.7442 Intermediate Similarity NPC139717
0.7391 Intermediate Similarity NPC474118
0.7391 Intermediate Similarity NPC51762
0.7381 Intermediate Similarity NPC92224
0.7347 Intermediate Similarity NPC17518
0.7347 Intermediate Similarity NPC22765
0.7333 Intermediate Similarity NPC144023
0.7333 Intermediate Similarity NPC218918
0.7333 Intermediate Similarity NPC120926
0.7273 Intermediate Similarity NPC285594
0.7273 Intermediate Similarity NPC96551
0.7234 Intermediate Similarity NPC202189
0.7209 Intermediate Similarity NPC76145
0.7209 Intermediate Similarity NPC190810
0.7209 Intermediate Similarity NPC34764
0.7174 Intermediate Similarity NPC105246
0.7174 Intermediate Similarity NPC190232
0.7143 Intermediate Similarity NPC178644
0.7111 Intermediate Similarity NPC183670
0.7111 Intermediate Similarity NPC246165
0.7045 Intermediate Similarity NPC239039
0.7045 Intermediate Similarity NPC266298
0.7021 Intermediate Similarity NPC192529
0.6977 Remote Similarity NPC282119
0.6957 Remote Similarity NPC473614
0.6957 Remote Similarity NPC103290
0.6897 Remote Similarity NPC473759
0.6897 Remote Similarity NPC474155
0.6863 Remote Similarity NPC200129
0.6829 Remote Similarity NPC206088
0.6829 Remote Similarity NPC66577
0.6809 Remote Similarity NPC193180
0.6731 Remote Similarity NPC471681
0.6667 Remote Similarity NPC141777
0.6667 Remote Similarity NPC48638
0.6667 Remote Similarity NPC90506
0.6667 Remote Similarity NPC23145
0.6667 Remote Similarity NPC227670
0.6667 Remote Similarity NPC90803
0.6667 Remote Similarity NPC166362
0.6667 Remote Similarity NPC45727
0.6667 Remote Similarity NPC17810
0.6667 Remote Similarity NPC213749
0.6545 Remote Similarity NPC470893
0.6545 Remote Similarity NPC469770
0.6481 Remote Similarity NPC476679
0.6429 Remote Similarity NPC3649
0.6429 Remote Similarity NPC100879
0.6429 Remote Similarity NPC471327
0.6415 Remote Similarity NPC27438
0.64 Remote Similarity NPC229403
0.6364 Remote Similarity NPC286752
0.6346 Remote Similarity NPC106990
0.6316 Remote Similarity NPC474528
0.6316 Remote Similarity NPC474415
0.6316 Remote Similarity NPC55004
0.6316 Remote Similarity NPC49575
0.6316 Remote Similarity NPC11130
0.6316 Remote Similarity NPC267626
0.6316 Remote Similarity NPC475696
0.6316 Remote Similarity NPC474457
0.6316 Remote Similarity NPC230823
0.6296 Remote Similarity NPC473728
0.6296 Remote Similarity NPC179169
0.6296 Remote Similarity NPC306195
0.6296 Remote Similarity NPC181255
0.6296 Remote Similarity NPC35519
0.6296 Remote Similarity NPC157781
0.625 Remote Similarity NPC123194
0.625 Remote Similarity NPC10183
0.623 Remote Similarity NPC475124
0.623 Remote Similarity NPC6697
0.6226 Remote Similarity NPC182102
0.6226 Remote Similarity NPC26960
0.6226 Remote Similarity NPC329773
0.6207 Remote Similarity NPC30215
0.6207 Remote Similarity NPC472830
0.6207 Remote Similarity NPC170799
0.6207 Remote Similarity NPC94991
0.6207 Remote Similarity NPC469769
0.6207 Remote Similarity NPC308108
0.6207 Remote Similarity NPC266295
0.6207 Remote Similarity NPC60772
0.6182 Remote Similarity NPC23117
0.6182 Remote Similarity NPC14002
0.6182 Remote Similarity NPC165755
0.6111 Remote Similarity NPC26906
0.6111 Remote Similarity NPC214584
0.6102 Remote Similarity NPC5698
0.6102 Remote Similarity NPC474420
0.6102 Remote Similarity NPC475716
0.6102 Remote Similarity NPC474455
0.6102 Remote Similarity NPC474454
0.6102 Remote Similarity NPC259261
0.6102 Remote Similarity NPC309825
0.6071 Remote Similarity NPC63396
0.6071 Remote Similarity NPC202850
0.6071 Remote Similarity NPC5626
0.6047 Remote Similarity NPC151719
0.6038 Remote Similarity NPC62755
0.6034 Remote Similarity NPC65786
0.6034 Remote Similarity NPC115385
0.6034 Remote Similarity NPC27853
0.6034 Remote Similarity NPC101285
0.6034 Remote Similarity NPC7491
0.6034 Remote Similarity NPC13789
0.6 Remote Similarity NPC323153
0.6 Remote Similarity NPC177112
0.6 Remote Similarity NPC234264
0.6 Remote Similarity NPC252809
0.6 Remote Similarity NPC25853
0.6 Remote Similarity NPC127582
0.6 Remote Similarity NPC71506
0.6 Remote Similarity NPC176621
0.6 Remote Similarity NPC135648
0.6 Remote Similarity NPC68014
0.6 Remote Similarity NPC47840
0.6 Remote Similarity NPC311809
0.5968 Remote Similarity NPC107540
0.5952 Remote Similarity NPC123965
0.5952 Remote Similarity NPC138113
0.5952 Remote Similarity NPC115959
0.5938 Remote Similarity NPC171225
0.5932 Remote Similarity NPC10017
0.5926 Remote Similarity NPC476681
0.5918 Remote Similarity NPC188596
0.5902 Remote Similarity NPC213152
0.5902 Remote Similarity NPC469728
0.5902 Remote Similarity NPC210346
0.5902 Remote Similarity NPC219621
0.5902 Remote Similarity NPC60565
0.5902 Remote Similarity NPC475795
0.5893 Remote Similarity NPC268564
0.5893 Remote Similarity NPC295777
0.5893 Remote Similarity NPC69898
0.5893 Remote Similarity NPC296311
0.5862 Remote Similarity NPC249645
0.5862 Remote Similarity NPC55412
0.5818 Remote Similarity NPC236623
0.5818 Remote Similarity NPC244038
0.5814 Remote Similarity NPC60288
0.5806 Remote Similarity NPC124112
0.5806 Remote Similarity NPC165695
0.5806 Remote Similarity NPC474086
0.5806 Remote Similarity NPC211291
0.5806 Remote Similarity NPC197238
0.5806 Remote Similarity NPC202118
0.5806 Remote Similarity NPC283247
0.5806 Remote Similarity NPC133368
0.5806 Remote Similarity NPC474480
0.5789 Remote Similarity NPC95581
0.5769 Remote Similarity NPC24824
0.5769 Remote Similarity NPC165651
0.5769 Remote Similarity NPC210560
0.5763 Remote Similarity NPC22019
0.5763 Remote Similarity NPC278550
0.5763 Remote Similarity NPC321568
0.5763 Remote Similarity NPC470370
0.5763 Remote Similarity NPC208749
0.5763 Remote Similarity NPC470369
0.5763 Remote Similarity NPC193695
0.5763 Remote Similarity NPC281986
0.5758 Remote Similarity NPC474248
0.5738 Remote Similarity NPC471081
0.5735 Remote Similarity NPC329763
0.5714 Remote Similarity NPC52449
0.5714 Remote Similarity NPC287744
0.5714 Remote Similarity NPC475704
0.5714 Remote Similarity NPC140233
0.5714 Remote Similarity NPC285371
0.5714 Remote Similarity NPC225415
0.5714 Remote Similarity NPC294358
0.5714 Remote Similarity NPC212210
0.5714 Remote Similarity NPC329698
0.5714 Remote Similarity NPC40417
0.5714 Remote Similarity NPC309300
0.5714 Remote Similarity NPC469662
0.5714 Remote Similarity NPC290367
0.5714 Remote Similarity NPC169275
0.5714 Remote Similarity NPC473902
0.569 Remote Similarity NPC200258
0.569 Remote Similarity NPC275472

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC60556 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
0.7209 Intermediate Similarity NPD319 Phase 1
0.7174 Intermediate Similarity NPD1799 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8262 Approved
0.6207 Remote Similarity NPD287 Approved
0.5862 Remote Similarity NPD4219 Approved

Structure

External Identifiers

PubChem CID   5281522
ChEMBL   CHEMBL448700
ZINC  

Physicochemical Properties

Molecular Weight:  204.19
ALogP:  3.2289
MLogP:  3.11
XLogP:  6.044
# Rotatable Bonds:  3
Polar Surface Area:  0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  15

Download Data

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