Natural Product: NPC110072

Natural Product ID:  NPC110072
Common Name:   Crocin
IUPAC Name:   bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
Synonyms:   Crocetin Di(Beta-Gentiobiosyl)Ester; Crocin; Crocin 1
Molecular Formula:   C44H64O24
Standard InCHIKey:  SEBIKDIMAPSUBY-RTJKDTQDSA-N
Standard InCHI:  InChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@H]([C@@H]([C@H]4O)O)O)[C@H]([C@@H]([C@H]3O)O)O)C)C)/C)/C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)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
NPO15308 Stigma croci NA NA NA HerDing*
NPO9445 Crocus sativus Species Iridaceae Eukaryota DOI[10.1002/hlca.19270100148]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruits PMID[23305920]
NPO29645 Gardeniae fructus NA NA NA TCMSP*
NPO9445 Crocus sativus Species Iridaceae Eukaryota TM-MC*
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota TM-MC*
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota TCMID*
NPO15308 Stigma croci NA NA NA TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 = 140000 nM 12398542
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency 17782.8 nM PubChem BioAssay data set
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency 21192.3 nM PubChem BioAssay data set
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency 100000 nM PubChem BioAssay data set
NPT445 Individual Protein Peripheral myelin protein 22 Rattus norvegicus Potency 4.1 nM PubChem BioAssay data set
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 100000 nM 23305920
NPT3041 Organism Human enterovirus 71 Human enterovirus 71 Survival >= 80 % 23353754
NPT2 Others Unspecified Potency 33491.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 26806.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 13448.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 26603.2 nM PubChem BioAssay data set
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 170000 nM 24904963
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 = 128000 nM 24904963

  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 NPC110072 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
0.9765 High Similarity NPC285588
0.9302 High Similarity NPC475186
0.9302 High Similarity NPC118077
0.8737 High Similarity NPC2313
0.8737 High Similarity NPC57586
0.8737 High Similarity NPC475655
0.8737 High Similarity NPC154132
0.8737 High Similarity NPC475157
0.8737 High Similarity NPC471637
0.8506 High Similarity NPC251026
0.8495 Intermediate Similarity NPC294293
0.8488 Intermediate Similarity NPC127295
0.8488 Intermediate Similarity NPC163362
0.8478 Intermediate Similarity NPC477349
0.8409 Intermediate Similarity NPC473315
0.8409 Intermediate Similarity NPC142111
0.8384 Intermediate Similarity NPC315070
0.8367 Intermediate Similarity NPC197736
0.8352 Intermediate Similarity NPC470137
0.8315 Intermediate Similarity NPC473308
0.8298 Intermediate Similarity NPC477345
0.8298 Intermediate Similarity NPC477348
0.8298 Intermediate Similarity NPC163409
0.8298 Intermediate Similarity NPC44682
0.8298 Intermediate Similarity NPC238264
0.8242 Intermediate Similarity NPC125142
0.8222 Intermediate Similarity NPC470124
0.8182 Intermediate Similarity NPC469469
0.8132 Intermediate Similarity NPC208473
0.8125 Intermediate Similarity NPC475375
0.8125 Intermediate Similarity NPC475525
0.8125 Intermediate Similarity NPC475540
0.8125 Intermediate Similarity NPC475241
0.8125 Intermediate Similarity NPC473605
0.8125 Intermediate Similarity NPC476066
0.8125 Intermediate Similarity NPC475593
0.8125 Intermediate Similarity NPC473765
0.8125 Intermediate Similarity NPC475164
0.8111 Intermediate Similarity NPC266718
0.8111 Intermediate Similarity NPC475035
0.8043 Intermediate Similarity NPC475037
0.8021 Intermediate Similarity NPC469543
0.8 Intermediate Similarity NPC320552
0.7979 Intermediate Similarity NPC473311
0.7979 Intermediate Similarity NPC327253
0.7917 Intermediate Similarity NPC159698
0.7857 Intermediate Similarity NPC475332
0.7835 Intermediate Similarity NPC170204
0.7826 Intermediate Similarity NPC475034
0.7812 Intermediate Similarity NPC472196
0.7812 Intermediate Similarity NPC238090
0.7812 Intermediate Similarity NPC472195
0.7708 Intermediate Similarity NPC477749
0.7708 Intermediate Similarity NPC476075
0.7708 Intermediate Similarity NPC476084
0.7692 Intermediate Similarity NPC193765
0.764 Intermediate Similarity NPC477314
0.7629 Intermediate Similarity NPC159092
0.7614 Intermediate Similarity NPC326661
0.7604 Intermediate Similarity NPC118078
0.7604 Intermediate Similarity NPC303451
0.7604 Intermediate Similarity NPC6414
0.7528 Intermediate Similarity NPC110813
0.7526 Intermediate Similarity NPC114172
0.7526 Intermediate Similarity NPC471324
0.7526 Intermediate Similarity NPC206679
0.75 Intermediate Similarity NPC477748
0.7453 Intermediate Similarity NPC133625
0.7449 Intermediate Similarity NPC109406
0.7449 Intermediate Similarity NPC61201
0.7449 Intermediate Similarity NPC320089
0.7444 Intermediate Similarity NPC133377
0.7426 Intermediate Similarity NPC198422
0.7426 Intermediate Similarity NPC40182
0.7423 Intermediate Similarity NPC202886
0.7419 Intermediate Similarity NPC38295
0.7419 Intermediate Similarity NPC470313
0.7419 Intermediate Similarity NPC156089
0.7419 Intermediate Similarity NPC473500
0.74 Intermediate Similarity NPC255410
0.7387 Intermediate Similarity NPC470515
0.7386 Intermediate Similarity NPC472173
0.7379 Intermediate Similarity NPC222062
0.7379 Intermediate Similarity NPC201191
0.7347 Intermediate Similarity NPC472124
0.7347 Intermediate Similarity NPC472125
0.7347 Intermediate Similarity NPC469410
0.7347 Intermediate Similarity NPC472126
0.734 Intermediate Similarity NPC288471
0.7333 Intermediate Similarity NPC476740
0.7333 Intermediate Similarity NPC82251
0.7333 Intermediate Similarity NPC476738
0.7327 Intermediate Similarity NPC120299
0.7321 Intermediate Similarity NPC470915
0.7321 Intermediate Similarity NPC470517
0.7321 Intermediate Similarity NPC470911
0.7308 Intermediate Similarity NPC474581
0.7308 Intermediate Similarity NPC473816
0.7308 Intermediate Similarity NPC118761
0.7308 Intermediate Similarity NPC197541
0.7308 Intermediate Similarity NPC284929
0.7308 Intermediate Similarity NPC475367
0.7308 Intermediate Similarity NPC309398
0.7308 Intermediate Similarity NPC234304
0.7308 Intermediate Similarity NPC267869
0.73 Intermediate Similarity NPC300710
0.7292 Intermediate Similarity NPC316138
0.7292 Intermediate Similarity NPC313658
0.7283 Intermediate Similarity NPC133226
0.7283 Intermediate Similarity NPC470147
0.7265 Intermediate Similarity NPC162925
0.7265 Intermediate Similarity NPC87153
0.7257 Intermediate Similarity NPC135369
0.7255 Intermediate Similarity NPC475653
0.7255 Intermediate Similarity NPC203627
0.7245 Intermediate Similarity NPC307699
0.7241 Intermediate Similarity NPC474078
0.7228 Intermediate Similarity NPC143446
0.7228 Intermediate Similarity NPC173329
0.7228 Intermediate Similarity NPC288350
0.7222 Intermediate Similarity NPC229655
0.7204 Intermediate Similarity NPC236649
0.7204 Intermediate Similarity NPC21693
0.7203 Intermediate Similarity NPC77651
0.7203 Intermediate Similarity NPC28069
0.72 Intermediate Similarity NPC256368
0.7196 Intermediate Similarity NPC473807
0.7191 Intermediate Similarity NPC477309
0.7191 Intermediate Similarity NPC477316
0.7191 Intermediate Similarity NPC477308
0.7191 Intermediate Similarity NPC477315
0.7191 Intermediate Similarity NPC477304
0.7191 Intermediate Similarity NPC477312
0.7191 Intermediate Similarity NPC477305
0.7191 Intermediate Similarity NPC477313
0.7182 Intermediate Similarity NPC473159
0.7174 Intermediate Similarity NPC180725
0.7174 Intermediate Similarity NPC470149
0.7174 Intermediate Similarity NPC470148
0.7155 Intermediate Similarity NPC471090
0.7143 Intermediate Similarity NPC198918
0.7143 Intermediate Similarity NPC290276
0.7143 Intermediate Similarity NPC124878
0.7143 Intermediate Similarity NPC10883
0.7143 Intermediate Similarity NPC475711
0.7143 Intermediate Similarity NPC204214
0.7143 Intermediate Similarity NPC92283
0.7143 Intermediate Similarity NPC63404
0.7143 Intermediate Similarity NPC35338
0.7143 Intermediate Similarity NPC10121
0.7143 Intermediate Similarity NPC147032
0.7143 Intermediate Similarity NPC231888
0.7143 Intermediate Similarity NPC474026
0.7115 Intermediate Similarity NPC198992
0.7115 Intermediate Similarity NPC476611
0.7113 Intermediate Similarity NPC199382
0.7111 Intermediate Similarity NPC477306
0.7094 Intermediate Similarity NPC297950
0.7094 Intermediate Similarity NPC179261
0.7091 Intermediate Similarity NPC470825
0.7083 Intermediate Similarity NPC471025
0.7079 Intermediate Similarity NPC477311
0.7079 Intermediate Similarity NPC132938
0.7079 Intermediate Similarity NPC477303
0.7079 Intermediate Similarity NPC55652
0.7071 Intermediate Similarity NPC470573
0.7071 Intermediate Similarity NPC120021
0.7071 Intermediate Similarity NPC270908
0.7071 Intermediate Similarity NPC231710
0.7071 Intermediate Similarity NPC65665
0.7071 Intermediate Similarity NPC216826
0.7071 Intermediate Similarity NPC117596
0.7065 Intermediate Similarity NPC248775
0.7059 Intermediate Similarity NPC306041
0.7048 Intermediate Similarity NPC195510
0.7048 Intermediate Similarity NPC473596
0.7048 Intermediate Similarity NPC13171
0.7045 Intermediate Similarity NPC476012
0.7045 Intermediate Similarity NPC52268
0.7045 Intermediate Similarity NPC53760
0.7043 Intermediate Similarity NPC183353
0.7043 Intermediate Similarity NPC469812
0.7041 Intermediate Similarity NPC248312
0.7037 Intermediate Similarity NPC219900
0.7037 Intermediate Similarity NPC392
0.7037 Intermediate Similarity NPC177524
0.703 Intermediate Similarity NPC2003
0.703 Intermediate Similarity NPC25701
0.703 Intermediate Similarity NPC472198
0.7025 Intermediate Similarity NPC471024
0.7021 Intermediate Similarity NPC280367
0.7019 Intermediate Similarity NPC22149
0.7019 Intermediate Similarity NPC255677
0.7019 Intermediate Similarity NPC306344
0.7018 Intermediate Similarity NPC470914
0.701 Intermediate Similarity NPC47937
0.7009 Intermediate Similarity NPC239961
0.7 Intermediate Similarity NPC126897
0.7 Intermediate Similarity NPC472197
0.7 Intermediate Similarity NPC107654

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC110072 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
0.76 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD7838 Discovery
0.7043 Intermediate Similarity NPD8517 Approved
0.7043 Intermediate Similarity NPD8516 Approved
0.7043 Intermediate Similarity NPD8515 Approved
0.7037 Intermediate Similarity NPD6686 Approved
0.7 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.6897 Remote Similarity NPD8513 Phase 3
0.6752 Remote Similarity NPD7503 Approved
0.6733 Remote Similarity NPD6698 Approved
0.6733 Remote Similarity NPD46 Approved
0.6667 Remote Similarity NPD8377 Approved
0.6667 Remote Similarity NPD8294 Approved
0.6639 Remote Similarity NPD7830 Approved
0.6639 Remote Similarity NPD7829 Approved
0.661 Remote Similarity NPD8296 Approved
0.661 Remote Similarity NPD8335 Approved
0.661 Remote Similarity NPD8379 Approved
0.661 Remote Similarity NPD8380 Approved
0.661 Remote Similarity NPD8378 Approved
0.6588 Remote Similarity NPD6123 Approved
0.6471 Remote Similarity NPD8033 Approved
0.6458 Remote Similarity NPD7329 Approved
0.6356 Remote Similarity NPD7328 Approved
0.6356 Remote Similarity NPD7327 Approved
0.6346 Remote Similarity NPD7983 Approved
0.6303 Remote Similarity NPD7516 Approved
0.6293 Remote Similarity NPD8133 Approved
0.621 Remote Similarity NPD8448 Approved
0.6198 Remote Similarity NPD8444 Approved
0.619 Remote Similarity NPD8392 Approved
0.619 Remote Similarity NPD8391 Approved
0.619 Remote Similarity NPD8390 Approved
0.6139 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6129 Remote Similarity NPD8451 Approved
0.6129 Remote Similarity NPD7507 Approved
0.6098 Remote Similarity NPD8328 Phase 3
0.6095 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6083 Remote Similarity NPD7641 Discontinued
0.608 Remote Similarity NPD8074 Phase 3
0.6053 Remote Similarity NPD6412 Phase 2
0.6036 Remote Similarity NPD5344 Discontinued
0.5984 Remote Similarity NPD7319 Approved
0.5963 Remote Similarity NPD7839 Suspended
0.5946 Remote Similarity NPD6648 Approved
0.5932 Remote Similarity NPD6429 Approved
0.5932 Remote Similarity NPD6430 Approved
0.592 Remote Similarity NPD8340 Approved
0.592 Remote Similarity NPD8341 Approved
0.592 Remote Similarity NPD8299 Approved
0.592 Remote Similarity NPD8342 Approved
0.5882 Remote Similarity NPD7266 Discontinued
0.5882 Remote Similarity NPD7346 Approved
0.584 Remote Similarity NPD7642 Approved
0.5812 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5806 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5789 Remote Similarity NPD1407 Approved
0.5789 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5776 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5765 Remote Similarity NPD892 Phase 3
0.5765 Remote Similarity NPD893 Approved
0.5765 Remote Similarity NPD888 Phase 3
0.5765 Remote Similarity NPD890 Clinical (unspecified phase)
0.5765 Remote Similarity NPD891 Phase 3
0.567 Remote Similarity NPD3181 Approved
0.5667 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5647 Remote Similarity NPD2269 Approved
0.561 Remote Similarity NPD8295 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   5281233
ChEMBL   CHEMBL446785
ZINC  

Physicochemical Properties

Molecular Weight:  976.38
ALogP:  -2.722
MLogP:  3.66
XLogP:  -1.214
# Rotatable Bonds:  38
Polar Surface Area:  391.2
# H-Bond Aceptor:  24
# H-Bond Donor:  14
# Rings:  4
# Heavy Atoms:  68

Download Data

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Similar NPs/Drugs