Natural Product: NPC122212

Natural Product ID:  NPC122212
Common Name:   (Z)-Prop-1-Ene-1,2,3-Tricarboxylic Acid
IUPAC Name:   (Z)-prop-1-ene-1,2,3-tricarboxylic acid
Synonyms:   Cis-Aconitate
Molecular Formula:   C6H6O6
Standard InCHIKey:  GTZCVFVGUGFEME-IWQZZHSRSA-N
Standard InCHI:  InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1-
Canonical SMILES:  OC(=O)C/C(=C/C(=O)O)/C(=O)O
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
NPO29118 Euonymus alatus Species Celastraceae Eukaryota UNPD*
NPO29050 Lemnalia nitida Species Nephtheidae Eukaryota UNPD*
NPO236 Sojae semen nigrum NA NA NA TCMSP*
NPO17871 Aconitum kusnezoffii reichb Species Ranunculaceae Eukaryota TCMSP*
NPO16501 Capsicum annuum Species Solanaceae Eukaryota TM-MC*
NPO2413 Saccharum officinarum Species Poaceae Eukaryota TCMID*
NPO29443 Equisetum palustre Species Equisetaceae Eukaryota TCMID*
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota TCMID*
NPO29212 Tanaecium jaroba Species Bignoniaceae Eukaryota UNPD*
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota TCMID*
NPO29323 Glaucium leiocarpum Species Papaveraceae Eukaryota UNPD*
NPO7635 Glycine max Species Fabaceae Eukaryota TCMID*
NPO29105 Meconopsis punicea Species Papaveraceae Eukaryota UNPD*
NPO23177 Achillea alpina Species Asteraceae Eukaryota TCMID*
NPO28876 Narcissus cyclamineus Species Amaryllidaceae Eukaryota UNPD*
NPO2052 Hedyotis acutangula Species Rubiaceae Eukaryota TCMID*
NPO29303 Salvia multicaulis Species Lamiaceae Eukaryota UNPD*
NPO3353 Saccharum sinensis Species Poaceae Eukaryota TCMID*
NPO24627 Chondromyces robustus Species Polyangiaceae Bacteria UNPD*
NPO29391 Papaver bracteatum Species Papaveraceae Eukaryota UNPD*
NPO1797 Homo sapiens Species Hominidae Eukaryota cerebrospinal fluid PMID[8412012]
NPO1797 Homo sapiens Species Hominidae Eukaryota saliva PMID[23857558]
NPO1797 Homo sapiens Species Hominidae Eukaryota breast milk PMID[24027187]
NPO1797 Homo sapiens Species Hominidae Eukaryota urine PMID[22932811]
NPO2052 Hedyotis acutangula Species Rubiaceae Eukaryota HerDing*
NPO23177 Achillea alpina Species Asteraceae Eukaryota TCM_Taiwan*
NPO23177 Achillea alpina Species Asteraceae Eukaryota HerDing*
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota TCM_Taiwan*
NPO23662 Arthraxon hispidus Species Poaceae Eukaryota TCM_Taiwan*
NPO2413 Saccharum officinarum Species Poaceae Eukaryota TCM_Taiwan*
NPO2413 Saccharum officinarum Species Poaceae Eukaryota HerDing*
NPO29443 Equisetum palustre Species Equisetaceae Eukaryota TCM_Taiwan*
NPO29443 Equisetum palustre Species Equisetaceae Eukaryota HerDing*
NPO3353 Saccharum sinensis Species Poaceae Eukaryota TCM_Taiwan*
NPO3353 Saccharum sinensis Species Poaceae Eukaryota HerDing*
NPO7635 Glycine max Species Fabaceae Eukaryota TCM_Taiwan*
NPO7635 Glycine max Species Fabaceae Eukaryota HerDing*
NPO29515 Laurus nobilis Species Lauraceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT945 Individual Protein ATP-citrate synthase Rattus norvegicus Ki > 1000000 nM 7853346
NPT367 Cell Line MDA-N Homo sapiens GI50 22080.05 nM PubChem BioAssay data set
NPT368 Cell Line SN12C Homo sapiens GI50 19408.86 nM PubChem BioAssay data set
NPT370 Cell Line NCI-H23 Homo sapiens GI50 23173.95 nM PubChem BioAssay data set
NPT369 Cell Line ACHN Homo sapiens GI50 18113.4 nM PubChem BioAssay data set
NPT371 Cell Line UO-31 Homo sapiens GI50 17179.08 nM PubChem BioAssay data set
NPT116 Cell Line HL-60 Homo sapiens GI50 21037.78 nM PubChem BioAssay data set
NPT374 Cell Line SF-539 Homo sapiens GI50 12302.69 nM PubChem BioAssay data set
NPT90 Cell Line DU-145 Homo sapiens GI50 19906.73 nM PubChem BioAssay data set
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 21037.78 nM PubChem BioAssay data set
NPT375 Cell Line Malme-3M Homo sapiens GI50 18706.82 nM PubChem BioAssay data set
NPT376 Cell Line A498 Homo sapiens GI50 16330.52 nM PubChem BioAssay data set
NPT111 Cell Line K562 Homo sapiens GI50 19186.69 nM PubChem BioAssay data set
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 15739.83 nM PubChem BioAssay data set
NPT112 Cell Line MOLT-4 Homo sapiens GI50 19098.53 nM PubChem BioAssay data set
NPT379 Cell Line HOP-62 Homo sapiens GI50 16749.43 nM PubChem BioAssay data set
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 20989.4 nM PubChem BioAssay data set
NPT380 Cell Line U-251 Homo sapiens GI50 19364.22 nM PubChem BioAssay data set
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 21627.19 nM PubChem BioAssay data set
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 38370.72 nM PubChem BioAssay data set
NPT383 Cell Line SNB-19 Homo sapiens GI50 22181.96 nM PubChem BioAssay data set
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 21330.45 nM PubChem BioAssay data set
NPT384 Cell Line TK-10 Homo sapiens GI50 23173.95 nM PubChem BioAssay data set
NPT323 Cell Line SW-620 Homo sapiens GI50 19010.78 nM PubChem BioAssay data set
NPT455 Cell Line NCI-H522 Homo sapiens GI50 17864.88 nM PubChem BioAssay data set
NPT386 Cell Line KM12 Homo sapiens GI50 23768.4 nM PubChem BioAssay data set
NPT387 Cell Line M14 Homo sapiens GI50 18749.95 nM PubChem BioAssay data set
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 14859.36 nM PubChem BioAssay data set
NPT388 Cell Line NCI-H322M Homo sapiens GI50 25703.96 nM PubChem BioAssay data set
NPT390 Cell Line LOX IMVI Homo sapiens GI50 22698.65 nM PubChem BioAssay data set
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 25763.21 nM PubChem BioAssay data set
NPT457 Cell Line BT-549 Homo sapiens GI50 21086.28 nM PubChem BioAssay data set
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 19543.39 nM PubChem BioAssay data set
NPT81 Cell Line A549 Homo sapiens GI50 18620.87 nM PubChem BioAssay data set
NPT392 Cell Line SNB-75 Homo sapiens GI50 14060.48 nM PubChem BioAssay data set
NPT391 Cell Line HCC 2998 Homo sapiens GI50 30831.88 nM PubChem BioAssay data set
NPT393 Cell Line HCT-116 Homo sapiens GI50 18155.16 nM PubChem BioAssay data set
NPT148 Cell Line HCT-15 Homo sapiens GI50 22698.65 nM PubChem BioAssay data set
NPT395 Cell Line SF-268 Homo sapiens GI50 19010.78 nM PubChem BioAssay data set
NPT394 Cell Line EKVX Homo sapiens GI50 19319.68 nM PubChem BioAssay data set
NPT83 Cell Line MCF7 Homo sapiens GI50 19319.68 nM PubChem BioAssay data set
NPT306 Cell Line PC-3 Homo sapiens GI50 19588.45 nM PubChem BioAssay data set
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 21478.3 nM PubChem BioAssay data set
NPT396 Cell Line T47D Homo sapiens GI50 20230.19 nM PubChem BioAssay data set
NPT397 Cell Line NCI-H460 Homo sapiens GI50 35156.04 nM PubChem BioAssay data set
NPT398 Cell Line UACC-62 Homo sapiens GI50 18155.16 nM PubChem BioAssay data set
NPT308 Cell Line CAKI-1 Homo sapiens GI50 20558.91 nM PubChem BioAssay data set
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 18323.14 nM PubChem BioAssay data set
NPT458 Cell Line IGROV-1 Homo sapiens GI50 20941.12 nM PubChem BioAssay data set
NPT399 Cell Line SF-295 Homo sapiens GI50 18113.4 nM PubChem BioAssay data set
NPT402 Cell Line Hs-578T Homo sapiens GI50 19860.95 nM PubChem BioAssay data set
NPT401 Cell Line 786-0 Homo sapiens GI50 17498.47 nM PubChem BioAssay data set
NPT403 Cell Line UACC-257 Homo sapiens GI50 33113.11 nM PubChem BioAssay data set
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 13614.45 nM PubChem BioAssay data set
NPT405 Cell Line NCI-H226 Homo sapiens GI50 21577.44 nM PubChem BioAssay data set
NPT139 Cell Line HT-29 Homo sapiens GI50 21827.3 nM PubChem BioAssay data set
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 21183.61 nM PubChem BioAssay data set
NPT407 Cell Line COLO 205 Homo sapiens GI50 17579.24 nM PubChem BioAssay data set
NPT406 Cell Line RXF 393 Homo sapiens GI50 15995.58 nM PubChem BioAssay data set
NPT1510 Individual Protein Alpha-ketoglutarate-dependent dioxygenase FTO Homo sapiens IC50 > 1000000 nM 23547775

  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 NPC122212 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 NPC137419
0.8723 High Similarity NPC87137
0.8667 High Similarity NPC169098
0.8333 Intermediate Similarity NPC471619
0.7358 Intermediate Similarity NPC43053
0.717 Intermediate Similarity NPC221467
0.7083 Intermediate Similarity NPC8270
0.7018 Intermediate Similarity NPC51846
0.6964 Remote Similarity NPC474127
0.6939 Remote Similarity NPC221250
0.6897 Remote Similarity NPC283502
0.6863 Remote Similarity NPC304079
0.6863 Remote Similarity NPC6963
0.6727 Remote Similarity NPC15129
0.6667 Remote Similarity NPC202011
0.6613 Remote Similarity NPC68110
0.661 Remote Similarity NPC135863
0.661 Remote Similarity NPC249850
0.661 Remote Similarity NPC293437
0.6604 Remote Similarity NPC308331
0.6596 Remote Similarity NPC308418
0.6522 Remote Similarity NPC122471
0.6522 Remote Similarity NPC217161
0.6522 Remote Similarity NPC224651
0.6522 Remote Similarity NPC98098
0.65 Remote Similarity NPC189700
0.65 Remote Similarity NPC34416
0.65 Remote Similarity NPC254095
0.6471 Remote Similarity NPC190649
0.6458 Remote Similarity NPC107877
0.6393 Remote Similarity NPC86789
0.6383 Remote Similarity NPC297363
0.6383 Remote Similarity NPC60675
0.6379 Remote Similarity NPC154626
0.6377 Remote Similarity NPC114727
0.6377 Remote Similarity NPC476590
0.629 Remote Similarity NPC472328
0.629 Remote Similarity NPC98519
0.6286 Remote Similarity NPC478191
0.6286 Remote Similarity NPC478196
0.6286 Remote Similarity NPC478192
0.6286 Remote Similarity NPC478195
0.6286 Remote Similarity NPC478193
0.6286 Remote Similarity NPC478194
0.625 Remote Similarity NPC15789
0.6232 Remote Similarity NPC284006
0.623 Remote Similarity NPC21946
0.623 Remote Similarity NPC223679
0.6197 Remote Similarity NPC470705
0.619 Remote Similarity NPC263732
0.6154 Remote Similarity NPC273600
0.6154 Remote Similarity NPC470123
0.6129 Remote Similarity NPC82465
0.6111 Remote Similarity NPC47844
0.6111 Remote Similarity NPC141195
0.6102 Remote Similarity NPC218486
0.6102 Remote Similarity NPC135537
0.6094 Remote Similarity NPC473737
0.6094 Remote Similarity NPC2328
0.6094 Remote Similarity NPC475073
0.6071 Remote Similarity NPC313553
0.6066 Remote Similarity NPC268185
0.6066 Remote Similarity NPC71755
0.6066 Remote Similarity NPC294938
0.6066 Remote Similarity NPC129150
0.6061 Remote Similarity NPC322035
0.6061 Remote Similarity NPC100719
0.6061 Remote Similarity NPC308294
0.6061 Remote Similarity NPC166791
0.6061 Remote Similarity NPC142423
0.6056 Remote Similarity NPC161038
0.6038 Remote Similarity NPC40805
0.6038 Remote Similarity NPC270796
0.6034 Remote Similarity NPC137396
0.6032 Remote Similarity NPC305973
0.6032 Remote Similarity NPC130953
0.6032 Remote Similarity NPC309408
0.6029 Remote Similarity NPC475982
0.6027 Remote Similarity NPC28049
0.6 Remote Similarity NPC49028
0.6 Remote Similarity NPC12815
0.6 Remote Similarity NPC173157
0.6 Remote Similarity NPC215745
0.6 Remote Similarity NPC63598
0.6 Remote Similarity NPC238948
0.6 Remote Similarity NPC470325
0.6 Remote Similarity NPC53642
0.5972 Remote Similarity NPC68819
0.5972 Remote Similarity NPC256640
0.5972 Remote Similarity NPC205615
0.5972 Remote Similarity NPC16279
0.597 Remote Similarity NPC7392
0.597 Remote Similarity NPC122627
0.597 Remote Similarity NPC98329
0.5965 Remote Similarity NPC236338
0.5938 Remote Similarity NPC26810
0.5909 Remote Similarity NPC19769
0.5909 Remote Similarity NPC471556
0.5909 Remote Similarity NPC471566
0.5909 Remote Similarity NPC282760
0.5909 Remote Similarity NPC471565
0.5902 Remote Similarity NPC324224
0.5902 Remote Similarity NPC472808
0.589 Remote Similarity NPC275530
0.5882 Remote Similarity NPC298413
0.5873 Remote Similarity NPC322002
0.5873 Remote Similarity NPC322186
0.5873 Remote Similarity NPC97570
0.5862 Remote Similarity NPC178586
0.5833 Remote Similarity NPC322461
0.5833 Remote Similarity NPC189677
0.5833 Remote Similarity NPC478120
0.5821 Remote Similarity NPC475555
0.5821 Remote Similarity NPC248125
0.5821 Remote Similarity NPC475675
0.5821 Remote Similarity NPC472072
0.5818 Remote Similarity NPC117572
0.5818 Remote Similarity NPC270706
0.5811 Remote Similarity NPC93763
0.5811 Remote Similarity NPC108816
0.5797 Remote Similarity NPC236208
0.5797 Remote Similarity NPC476591
0.5797 Remote Similarity NPC88877
0.5789 Remote Similarity NPC135698
0.5789 Remote Similarity NPC474980
0.5789 Remote Similarity NPC267110
0.5781 Remote Similarity NPC79756
0.5778 Remote Similarity NPC236709
0.5769 Remote Similarity NPC44546
0.5763 Remote Similarity NPC191643
0.5758 Remote Similarity NPC4668
0.5758 Remote Similarity NPC471611
0.5758 Remote Similarity NPC133758
0.5753 Remote Similarity NPC4492
0.5753 Remote Similarity NPC209113
0.5753 Remote Similarity NPC301207
0.5753 Remote Similarity NPC51391
0.5753 Remote Similarity NPC127118
0.5714 Remote Similarity NPC133700
0.5714 Remote Similarity NPC475046
0.5714 Remote Similarity NPC11383
0.5714 Remote Similarity NPC269641
0.5714 Remote Similarity NPC42304
0.5714 Remote Similarity NPC474084
0.5714 Remote Similarity NPC474959
0.5714 Remote Similarity NPC67183
0.5714 Remote Similarity NPC310450
0.5714 Remote Similarity NPC128280
0.5692 Remote Similarity NPC151648
0.5692 Remote Similarity NPC269737
0.5692 Remote Similarity NPC273614
0.5692 Remote Similarity NPC64985
0.569 Remote Similarity NPC225974
0.5676 Remote Similarity NPC125365
0.5676 Remote Similarity NPC474818
0.5676 Remote Similarity NPC51809
0.5676 Remote Similarity NPC49302
0.5676 Remote Similarity NPC176329
0.5672 Remote Similarity NPC96414
0.5667 Remote Similarity NPC116366
0.5652 Remote Similarity NPC323552
0.5652 Remote Similarity NPC63873
0.5652 Remote Similarity NPC287705
0.5645 Remote Similarity NPC325977
0.5645 Remote Similarity NPC150717
0.5645 Remote Similarity NPC230296
0.5641 Remote Similarity NPC40746
0.5641 Remote Similarity NPC229799
0.5641 Remote Similarity NPC286770
0.5641 Remote Similarity NPC169575
0.5641 Remote Similarity NPC284472
0.5641 Remote Similarity NPC116543
0.5634 Remote Similarity NPC319163
0.5634 Remote Similarity NPC316185
0.5634 Remote Similarity NPC67076
0.5625 Remote Similarity NPC302564
0.5625 Remote Similarity NPC329249
0.5625 Remote Similarity NPC318306
0.5616 Remote Similarity NPC166018
0.5616 Remote Similarity NPC472327
0.5616 Remote Similarity NPC169056
0.5616 Remote Similarity NPC225665
0.5614 Remote Similarity NPC91495
0.5614 Remote Similarity NPC207292
0.5606 Remote Similarity NPC322457
0.5606 Remote Similarity NPC474658
0.5606 Remote Similarity NPC190049
0.56 Remote Similarity NPC221095
0.56 Remote Similarity NPC473471
0.56 Remote Similarity NPC182292
0.56 Remote Similarity NPC279214

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC122212 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
0.7708 Intermediate Similarity NPD9411 Phase 1
0.6522 Remote Similarity NPD8573 Approved
0.6364 Remote Similarity NPD4220 Pre-registration
0.6038 Remote Similarity NPD5326 Phase 3
0.597 Remote Similarity NPD9137 Approved
0.587 Remote Similarity NPD9114 Clinical (unspecified phase)
0.5818 Remote Similarity NPD39 Approved
0.5818 Remote Similarity NPD4222 Approved
0.5778 Remote Similarity NPD8593 Approved
0.5778 Remote Similarity NPD8594 Approved
0.5676 Remote Similarity NPD4756 Discovery

Structure

External Identifiers

PubChem CID   643757
ChEMBL   CHEMBL347285
ZINC  

Physicochemical Properties

Molecular Weight:  174.02
ALogP:  -0.5191
MLogP:  1.46
XLogP:  -1.034
# Rotatable Bonds:  7
Polar Surface Area:  111.9
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  0
# Heavy Atoms:  12

Download Data

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