Natural Product: NPC268185

Natural Product ID:  NPC268185
Common Name:   Chabrolobenzoquinone E
IUPAC Name:   2-[(2E,6E,10Z)-11-(hydroxymethyl)-3,7,15-trimethylhexadeca-2,6,10,14-tetraenyl]-5-methylcyclohexa-2,5-diene-1,4-dione
Synonyms:   Chabrolobenzoquinone E
Molecular Formula:   C27H38O3
Standard InCHIKey:  AYWHRUOIEOXDRX-TZDKVAQASA-N
Standard InCHI:  InChI=1S/C27H38O3/c1-20(2)9-6-13-24(19-28)14-8-12-21(3)10-7-11-22(4)15-16-25-18-26(29)23(5)17-27(25)30/h9-10,14-15,17-18,28H,6-8,11-13,16,19H2,1-5H3/b21-10+,22-15+,24-14-
Canonical SMILES:  OC/C(=CCC/C(=C/CC/C(=C/CC1=CC(=O)C(=CC1=O)C)/C)/C)/CCC=C(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
NPO16934 Nephthea chabrolii Species Nephtheidae Eukaryota PMID[16309317]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens IC50 > 48800 nM 15711537
NPT81 Cell Line A549 Homo sapiens IC50 > 48800 nM 15711537
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 48800 nM 15711537

  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 NPC268185 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
0.8491 Intermediate Similarity NPC267110
0.8333 Intermediate Similarity NPC225974
0.8276 Intermediate Similarity NPC283502
0.8254 Intermediate Similarity NPC106613
0.8214 Intermediate Similarity NPC217188
0.807 Intermediate Similarity NPC189677
0.7966 Intermediate Similarity NPC71755
0.7925 Intermediate Similarity NPC140501
0.7869 Intermediate Similarity NPC79756
0.7812 Intermediate Similarity NPC137163
0.7742 Intermediate Similarity NPC269737
0.7736 Intermediate Similarity NPC477686
0.7679 Intermediate Similarity NPC288381
0.7679 Intermediate Similarity NPC20934
0.7593 Intermediate Similarity NPC191337
0.7547 Intermediate Similarity NPC116934
0.7544 Intermediate Similarity NPC473672
0.7544 Intermediate Similarity NPC474495
0.7538 Intermediate Similarity NPC472072
0.7465 Intermediate Similarity NPC471061
0.7458 Intermediate Similarity NPC300121
0.7424 Intermediate Similarity NPC269985
0.7414 Intermediate Similarity NPC137396
0.7377 Intermediate Similarity NPC293437
0.7377 Intermediate Similarity NPC135863
0.7377 Intermediate Similarity NPC249850
0.7368 Intermediate Similarity NPC474460
0.7344 Intermediate Similarity NPC68110
0.7333 Intermediate Similarity NPC317899
0.7313 Intermediate Similarity NPC117804
0.7288 Intermediate Similarity NPC474496
0.7273 Intermediate Similarity NPC160628
0.7258 Intermediate Similarity NPC254095
0.7258 Intermediate Similarity NPC223679
0.7246 Intermediate Similarity NPC95863
0.7213 Intermediate Similarity NPC324224
0.7213 Intermediate Similarity NPC472808
0.7206 Intermediate Similarity NPC236208
0.717 Intermediate Similarity NPC269823
0.7167 Intermediate Similarity NPC474127
0.7164 Intermediate Similarity NPC203335
0.7143 Intermediate Similarity NPC323437
0.7143 Intermediate Similarity NPC201562
0.7143 Intermediate Similarity NPC29542
0.7143 Intermediate Similarity NPC186042
0.7143 Intermediate Similarity NPC308331
0.7143 Intermediate Similarity NPC322002
0.7143 Intermediate Similarity NPC278202
0.7123 Intermediate Similarity NPC475994
0.7123 Intermediate Similarity NPC231739
0.7121 Intermediate Similarity NPC282760
0.7101 Intermediate Similarity NPC203819
0.7097 Intermediate Similarity NPC224103
0.7097 Intermediate Similarity NPC200831
0.7097 Intermediate Similarity NPC299369
0.7097 Intermediate Similarity NPC129150
0.7083 Intermediate Similarity NPC16279
0.7083 Intermediate Similarity NPC205615
0.7083 Intermediate Similarity NPC256640
0.7077 Intermediate Similarity NPC477707
0.7077 Intermediate Similarity NPC477830
0.7069 Intermediate Similarity NPC15325
0.7069 Intermediate Similarity NPC118788
0.7067 Intermediate Similarity NPC474980
0.7042 Intermediate Similarity NPC227396
0.7042 Intermediate Similarity NPC215050
0.7037 Intermediate Similarity NPC256766
0.7037 Intermediate Similarity NPC213538
0.7031 Intermediate Similarity NPC327112
0.7 Intermediate Similarity NPC319163
0.7 Intermediate Similarity NPC61177
0.7 Intermediate Similarity NPC474884
0.7 Intermediate Similarity NPC474805
0.7 Intermediate Similarity NPC67076
0.6986 Remote Similarity NPC203403
0.6986 Remote Similarity NPC473536
0.6984 Remote Similarity NPC21946
0.6981 Remote Similarity NPC111474
0.697 Remote Similarity NPC7029
0.6964 Remote Similarity NPC166788
0.6957 Remote Similarity NPC136473
0.6957 Remote Similarity NPC143396
0.6935 Remote Similarity NPC40148
0.6923 Remote Similarity NPC151648
0.6923 Remote Similarity NPC260573
0.6923 Remote Similarity NPC26810
0.6923 Remote Similarity NPC64971
0.6923 Remote Similarity NPC263732
0.6923 Remote Similarity NPC64985
0.6923 Remote Similarity NPC168407
0.6901 Remote Similarity NPC153660
0.6892 Remote Similarity NPC478122
0.6885 Remote Similarity NPC317796
0.6885 Remote Similarity NPC322461
0.6875 Remote Similarity NPC86789
0.6875 Remote Similarity NPC322186
0.6875 Remote Similarity NPC82465
0.6866 Remote Similarity NPC7940
0.6857 Remote Similarity NPC286154
0.6857 Remote Similarity NPC291062
0.6857 Remote Similarity NPC202011
0.6857 Remote Similarity NPC94743
0.6857 Remote Similarity NPC107848
0.6842 Remote Similarity NPC6663
0.6825 Remote Similarity NPC192843
0.6825 Remote Similarity NPC294938
0.6825 Remote Similarity NPC281230
0.6818 Remote Similarity NPC190049
0.6818 Remote Similarity NPC2328
0.6818 Remote Similarity NPC53109
0.6818 Remote Similarity NPC143168
0.6812 Remote Similarity NPC263382
0.6812 Remote Similarity NPC125578
0.6812 Remote Similarity NPC146376
0.6806 Remote Similarity NPC114727
0.6806 Remote Similarity NPC476590
0.6806 Remote Similarity NPC160540
0.68 Remote Similarity NPC19900
0.6795 Remote Similarity NPC476412
0.6792 Remote Similarity NPC29091
0.6792 Remote Similarity NPC182840
0.6792 Remote Similarity NPC103213
0.6792 Remote Similarity NPC255042
0.6786 Remote Similarity NPC6963
0.6786 Remote Similarity NPC138935
0.6786 Remote Similarity NPC304079
0.6774 Remote Similarity NPC232247
0.6774 Remote Similarity NPC251666
0.6774 Remote Similarity NPC471239
0.6765 Remote Similarity NPC83965
0.6765 Remote Similarity NPC146811
0.6761 Remote Similarity NPC316185
0.6757 Remote Similarity NPC82666
0.6757 Remote Similarity NPC97173
0.6721 Remote Similarity NPC284224
0.6719 Remote Similarity NPC320421
0.6719 Remote Similarity NPC471619
0.6719 Remote Similarity NPC226848
0.6716 Remote Similarity NPC150162
0.6714 Remote Similarity NPC469914
0.6714 Remote Similarity NPC94488
0.6714 Remote Similarity NPC262673
0.6714 Remote Similarity NPC475982
0.6712 Remote Similarity NPC260396
0.6712 Remote Similarity NPC315552
0.6712 Remote Similarity NPC474885
0.6711 Remote Similarity NPC91332
0.6711 Remote Similarity NPC162741
0.6711 Remote Similarity NPC471514
0.6709 Remote Similarity NPC77971
0.6667 Remote Similarity NPC122627
0.6667 Remote Similarity NPC275098
0.6667 Remote Similarity NPC325977
0.6667 Remote Similarity NPC477786
0.6667 Remote Similarity NPC477784
0.6667 Remote Similarity NPC251429
0.6667 Remote Similarity NPC215745
0.6667 Remote Similarity NPC192006
0.6667 Remote Similarity NPC284006
0.6667 Remote Similarity NPC96962
0.6667 Remote Similarity NPC48891
0.6667 Remote Similarity NPC238948
0.6667 Remote Similarity NPC316851
0.6667 Remote Similarity NPC62336
0.6667 Remote Similarity NPC12815
0.6667 Remote Similarity NPC43053
0.6667 Remote Similarity NPC243272
0.6667 Remote Similarity NPC477785
0.6622 Remote Similarity NPC477708
0.6622 Remote Similarity NPC203277
0.6622 Remote Similarity NPC263582
0.662 Remote Similarity NPC318766
0.6618 Remote Similarity NPC101670
0.6618 Remote Similarity NPC255863
0.6618 Remote Similarity NPC96414
0.6618 Remote Similarity NPC471566
0.6618 Remote Similarity NPC273600
0.6618 Remote Similarity NPC296436
0.6618 Remote Similarity NPC317881
0.6618 Remote Similarity NPC176215
0.6618 Remote Similarity NPC98897
0.6618 Remote Similarity NPC471565
0.6618 Remote Similarity NPC245947
0.6618 Remote Similarity NPC471556
0.6618 Remote Similarity NPC323045
0.6618 Remote Similarity NPC136164
0.6615 Remote Similarity NPC329249
0.6615 Remote Similarity NPC318306
0.6615 Remote Similarity NPC274927
0.6615 Remote Similarity NPC122239
0.6615 Remote Similarity NPC106851
0.6615 Remote Similarity NPC475931
0.6604 Remote Similarity NPC180840
0.6582 Remote Similarity NPC219966
0.6582 Remote Similarity NPC474865
0.6582 Remote Similarity NPC31086
0.6579 Remote Similarity NPC291260
0.6579 Remote Similarity NPC308038
0.6575 Remote Similarity NPC315843
0.6575 Remote Similarity NPC144995

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC268185 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
0.7925 Intermediate Similarity NPD4265 Approved
0.7097 Intermediate Similarity NPD8779 Phase 3
0.7031 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.6818 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6792 Remote Similarity NPD5783 Phase 3
0.6774 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7331 Phase 2
0.6757 Remote Similarity NPD4756 Discovery
0.6667 Remote Similarity NPD6927 Phase 3
0.6667 Remote Similarity NPD6110 Phase 1
0.661 Remote Similarity NPD4220 Pre-registration
0.6522 Remote Similarity NPD3704 Approved
0.6522 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6508 Remote Similarity NPD342 Phase 1
0.6429 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6418 Remote Similarity NPD368 Approved
0.6379 Remote Similarity NPD39 Approved
0.6379 Remote Similarity NPD4222 Approved
0.6316 Remote Similarity NPD5326 Phase 3
0.6316 Remote Similarity NPD9411 Phase 1
0.6282 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6212 Remote Similarity NPD6109 Phase 1
0.6167 Remote Similarity NPD5343 Approved
0.6143 Remote Similarity NPD7341 Phase 2
0.6098 Remote Similarity NPD1696 Phase 3
0.6098 Remote Similarity NPD5363 Approved
0.6066 Remote Similarity NPD3173 Approved
0.6026 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6 Remote Similarity NPD3197 Phase 1
0.5976 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5942 Remote Similarity NPD4192 Approved
0.5942 Remote Similarity NPD4191 Approved
0.5942 Remote Similarity NPD4194 Approved
0.5942 Remote Similarity NPD4193 Approved
0.5932 Remote Similarity NPD6096 Approved
0.5932 Remote Similarity NPD6097 Approved
0.5909 Remote Similarity NPD4219 Approved
0.5875 Remote Similarity NPD4252 Approved
0.5846 Remote Similarity NPD3195 Phase 2
0.5846 Remote Similarity NPD3196 Approved
0.5846 Remote Similarity NPD3194 Approved
0.5846 Remote Similarity NPD4266 Approved
0.5844 Remote Similarity NPD8264 Approved
0.5823 Remote Similarity NPD4268 Approved
0.5823 Remote Similarity NPD4271 Approved
0.5783 Remote Similarity NPD3666 Approved
0.5783 Remote Similarity NPD3665 Phase 1
0.5783 Remote Similarity NPD3133 Approved
0.5747 Remote Similarity NPD5785 Approved
0.5732 Remote Similarity NPD4269 Approved
0.5732 Remote Similarity NPD4270 Approved
0.5694 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5692 Remote Similarity NPD3172 Approved
0.5682 Remote Similarity NPD6079 Approved
0.5679 Remote Similarity NPD4819 Approved
0.5679 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5679 Remote Similarity NPD4695 Discontinued
0.5679 Remote Similarity NPD4821 Approved
0.5679 Remote Similarity NPD4820 Approved
0.5679 Remote Similarity NPD4822 Approved
0.5663 Remote Similarity NPD5331 Approved
0.5663 Remote Similarity NPD5332 Approved
0.5663 Remote Similarity NPD5362 Discontinued
0.5663 Remote Similarity NPD7154 Phase 3
0.5647 Remote Similarity NPD4623 Approved
0.5647 Remote Similarity NPD5279 Phase 3
0.5647 Remote Similarity NPD3618 Phase 1
0.5647 Remote Similarity NPD4519 Discontinued
0.5634 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5632 Remote Similarity NPD5328 Approved
0.561 Remote Similarity NPD4790 Discontinued

Structure

External Identifiers

PubChem CID   5326350
ChEMBL   CHEMBL464735
ZINC  

Physicochemical Properties

Molecular Weight:  410.28
ALogP:  4.9287
MLogP:  4.1
XLogP:  5.161
# Rotatable Bonds:  18
Polar Surface Area:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  30

Download Data

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