Natural Product: NPC17165

Natural Product ID:  NPC17165
Common Name:   Macrocalin B
IUPAC Name:  
Synonyms:  
Molecular Formula:   C20H26O6
Standard InCHIKey:  GSRZMSWBSLHHAD-IFKNWNSRSA-N
Standard InCHI:  InChI=1S/C20H26O6/c1-8-9-7-10(21)11-18-6-4-5-17(2,3)12(18)14(23)20(24)19(11,13(8)22)15(9)25-16(18)26-20/h9-12,14-16,21,23-24H,1,4-7H2,2-3H3/t9-,10-,11-,12+,14-,15+,16-,18+,19-,20-/m0/s1
Canonical SMILES:  C=C1[C@@H]2C[C@@H]([C@@H]3[C@]4(C1=O)[C@@H]2O[C@@H]1[C@@]23CCCC([C@H]2[C@@H]([C@]4(O)O1)O)(C)C)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
NPO18055 Isodon adenolomus Species Lamiaceae Eukaryota Aerial parts Shangrila, Yunnan Province, China 2008-AUG PMID[21534539]
NPO14230 Isodon macrocalyx Species Lamiaceae Eukaryota HerDing*
NPO8404 Isodon xerophilus Species Lamiaceae Eukaryota PMID[17665952]
NPO14230 Isodon macrocalyx Species Lamiaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT111 Cell Line K562 Homo sapiens IC50 > 10000 nM 17665952
NPT1097 Cell Line MKN-45 Homo sapiens IC50 > 10000 nM 17665952
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10000 nM 17665952
NPT111 Cell Line K562 Homo sapiens IC50 = 8.07 ug/ml 10843567
NPT116 Cell Line HL-60 Homo sapiens IC50 = 2.05 ug/ml 10843567
NPT1179 Cell Line MKN-28 Homo sapiens IC50 = 1.68 ug/ml 10843567
NPT116 Cell Line HL-60 Homo sapiens IC50 = 12400 nM 21534539
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 9100 nM 21534539
NPT81 Cell Line A549 Homo sapiens IC50 = 31900 nM 21534539
NPT83 Cell Line MCF7 Homo sapiens IC50 = 26900 nM 21534539
NPT660 Cell Line SW480 Homo sapiens IC50 = 10900 nM 21534539

  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 NPC17165 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
0.9905 High Similarity NPC94141
0.9813 High Similarity NPC78836
0.981 High Similarity NPC157929
0.972 High Similarity NPC229752
0.9714 High Similarity NPC63244
0.9623 High Similarity NPC145625
0.9623 High Similarity NPC471244
0.9623 High Similarity NPC473303
0.9619 High Similarity NPC471476
0.9533 High Similarity NPC471248
0.9528 High Similarity NPC122339
0.9524 High Similarity NPC252679
0.9524 High Similarity NPC118721
0.9439 High Similarity NPC471245
0.9434 High Similarity NPC473324
0.9429 High Similarity NPC189663
0.9429 High Similarity NPC89860
0.9358 High Similarity NPC88945
0.9352 High Similarity NPC132668
0.934 High Similarity NPC469744
0.9333 High Similarity NPC469746
0.9273 High Similarity NPC473304
0.9259 High Similarity NPC473397
0.9245 High Similarity NPC55973
0.9245 High Similarity NPC469733
0.9245 High Similarity NPC469729
0.9238 High Similarity NPC307660
0.9238 High Similarity NPC130511
0.9167 High Similarity NPC29505
0.9167 High Similarity NPC213320
0.9159 High Similarity NPC102741
0.9151 High Similarity NPC471461
0.9151 High Similarity NPC67745
0.9083 High Similarity NPC474927
0.9083 High Similarity NPC473352
0.9074 High Similarity NPC471093
0.9065 High Similarity NPC471094
0.9065 High Similarity NPC469984
0.9065 High Similarity NPC473410
0.9057 High Similarity NPC12823
0.9 High Similarity NPC471252
0.8991 High Similarity NPC329953
0.8972 High Similarity NPC471474
0.8899 High Similarity NPC85391
0.8899 High Similarity NPC137104
0.8899 High Similarity NPC320383
0.8899 High Similarity NPC474786
0.8889 High Similarity NPC63841
0.8879 High Similarity NPC56656
0.8857 High Similarity NPC14634
0.8818 High Similarity NPC471243
0.8807 High Similarity NPC131903
0.8807 High Similarity NPC274827
0.8796 High Similarity NPC186054
0.8785 High Similarity NPC202793
0.8774 High Similarity NPC309388
0.8774 High Similarity NPC475803
0.875 High Similarity NPC243354
0.8739 High Similarity NPC207845
0.8739 High Similarity NPC472719
0.8716 High Similarity NPC232133
0.8704 High Similarity NPC4115
0.8673 High Similarity NPC472718
0.8661 High Similarity NPC194273
0.8649 High Similarity NPC274833
0.8649 High Similarity NPC56025
0.8636 High Similarity NPC469983
0.8611 High Similarity NPC13149
0.8545 High Similarity NPC112895
0.8545 High Similarity NPC218123
0.8545 High Similarity NPC231278
0.8519 High Similarity NPC107385
0.8519 High Similarity NPC139347
0.8468 Intermediate Similarity NPC8431
0.8455 Intermediate Similarity NPC96333
0.8455 Intermediate Similarity NPC88833
0.844 Intermediate Similarity NPC474558
0.844 Intermediate Similarity NPC470167
0.8435 Intermediate Similarity NPC218970
0.8411 Intermediate Similarity NPC127408
0.8411 Intermediate Similarity NPC291785
0.8393 Intermediate Similarity NPC98069
0.8393 Intermediate Similarity NPC49730
0.8378 Intermediate Similarity NPC273155
0.8364 Intermediate Similarity NPC164600
0.8364 Intermediate Similarity NPC103172
0.8349 Intermediate Similarity NPC277074
0.8349 Intermediate Similarity NPC209298
0.8349 Intermediate Similarity NPC87927
0.8333 Intermediate Similarity NPC73986
0.8333 Intermediate Similarity NPC146563
0.8333 Intermediate Similarity NPC273962
0.8333 Intermediate Similarity NPC320118
0.8333 Intermediate Similarity NPC471790
0.8319 Intermediate Similarity NPC11035
0.8305 Intermediate Similarity NPC470478
0.8291 Intermediate Similarity NPC161738
0.8288 Intermediate Similarity NPC61071
0.8288 Intermediate Similarity NPC166993
0.8276 Intermediate Similarity NPC156651
0.8273 Intermediate Similarity NPC101842
0.8261 Intermediate Similarity NPC54395
0.825 Intermediate Similarity NPC248202
0.8246 Intermediate Similarity NPC205534
0.8246 Intermediate Similarity NPC470543
0.8241 Intermediate Similarity NPC470388
0.822 Intermediate Similarity NPC108072
0.822 Intermediate Similarity NPC475187
0.8208 Intermediate Similarity NPC231060
0.8208 Intermediate Similarity NPC84018
0.8208 Intermediate Similarity NPC138245
0.8205 Intermediate Similarity NPC475632
0.8205 Intermediate Similarity NPC86020
0.8198 Intermediate Similarity NPC138908
0.8198 Intermediate Similarity NPC200957
0.819 Intermediate Similarity NPC469823
0.819 Intermediate Similarity NPC137414
0.819 Intermediate Similarity NPC469820
0.8182 Intermediate Similarity NPC122811
0.8182 Intermediate Similarity NPC174367
0.8182 Intermediate Similarity NPC47113
0.8165 Intermediate Similarity NPC289148
0.8165 Intermediate Similarity NPC52899
0.8165 Intermediate Similarity NPC163963
0.8158 Intermediate Similarity NPC275668
0.8158 Intermediate Similarity NPC204392
0.8158 Intermediate Similarity NPC1876
0.8158 Intermediate Similarity NPC240734
0.8158 Intermediate Similarity NPC91838
0.8151 Intermediate Similarity NPC182900
0.8151 Intermediate Similarity NPC475182
0.8151 Intermediate Similarity NPC249553
0.8148 Intermediate Similarity NPC474793
0.8145 Intermediate Similarity NPC473805
0.8145 Intermediate Similarity NPC473519
0.8142 Intermediate Similarity NPC91583
0.8142 Intermediate Similarity NPC240125
0.8142 Intermediate Similarity NPC473844
0.8142 Intermediate Similarity NPC51947
0.8136 Intermediate Similarity NPC190939
0.8136 Intermediate Similarity NPC197003
0.8125 Intermediate Similarity NPC470166
0.812 Intermediate Similarity NPC477252
0.812 Intermediate Similarity NPC309433
0.812 Intermediate Similarity NPC470171
0.8113 Intermediate Similarity NPC191094
0.8113 Intermediate Similarity NPC302008
0.8108 Intermediate Similarity NPC301787
0.8103 Intermediate Similarity NPC165439
0.8103 Intermediate Similarity NPC102088
0.8099 Intermediate Similarity NPC469841
0.8099 Intermediate Similarity NPC469842
0.8099 Intermediate Similarity NPC473505
0.8099 Intermediate Similarity NPC130229
0.8091 Intermediate Similarity NPC76866
0.8091 Intermediate Similarity NPC148628
0.8091 Intermediate Similarity NPC304832
0.8091 Intermediate Similarity NPC88203
0.8091 Intermediate Similarity NPC286519
0.8091 Intermediate Similarity NPC246736
0.8091 Intermediate Similarity NPC214946
0.8087 Intermediate Similarity NPC474265
0.8087 Intermediate Similarity NPC243572
0.8087 Intermediate Similarity NPC210420
0.8083 Intermediate Similarity NPC305771
0.8083 Intermediate Similarity NPC94072
0.8083 Intermediate Similarity NPC156789
0.8083 Intermediate Similarity NPC15918
0.8083 Intermediate Similarity NPC169816
0.8083 Intermediate Similarity NPC475431
0.8083 Intermediate Similarity NPC28532
0.808 Intermediate Similarity NPC102015
0.8073 Intermediate Similarity NPC287676
0.807 Intermediate Similarity NPC98633
0.807 Intermediate Similarity NPC130302
0.8067 Intermediate Similarity NPC308459
0.8067 Intermediate Similarity NPC129393
0.8053 Intermediate Similarity NPC88744
0.8051 Intermediate Similarity NPC469822
0.8051 Intermediate Similarity NPC470513
0.8051 Intermediate Similarity NPC470514
0.8037 Intermediate Similarity NPC41070
0.8036 Intermediate Similarity NPC285927
0.8036 Intermediate Similarity NPC222833
0.8034 Intermediate Similarity NPC279638
0.8033 Intermediate Similarity NPC476673
0.8019 Intermediate Similarity NPC59170
0.8019 Intermediate Similarity NPC144739
0.8019 Intermediate Similarity NPC181594
0.8018 Intermediate Similarity NPC473406
0.8018 Intermediate Similarity NPC471253
0.8018 Intermediate Similarity NPC96217
0.8018 Intermediate Similarity NPC216114
0.8017 Intermediate Similarity NPC102619
0.8017 Intermediate Similarity NPC293038
0.8017 Intermediate Similarity NPC260665
0.8017 Intermediate Similarity NPC62696
0.8017 Intermediate Similarity NPC160084
0.8 Intermediate Similarity NPC236585
0.8 Intermediate Similarity NPC46848

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC17165 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
0.7869 Intermediate Similarity NPD8328 Phase 3
0.7863 Intermediate Similarity NPD8133 Approved
0.7815 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7807 Intermediate Similarity NPD6412 Phase 2
0.7788 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7787 Intermediate Similarity NPD6370 Approved
0.7672 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7623 Intermediate Similarity NPD6054 Approved
0.7619 Intermediate Similarity NPD7736 Approved
0.7561 Intermediate Similarity NPD6016 Approved
0.7561 Intermediate Similarity NPD6015 Approved
0.7559 Intermediate Similarity NPD7319 Approved
0.75 Intermediate Similarity NPD5988 Approved
0.748 Intermediate Similarity NPD6059 Approved
0.746 Intermediate Similarity NPD7507 Approved
0.7436 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD8293 Discontinued
0.7381 Intermediate Similarity NPD7492 Approved
0.7339 Intermediate Similarity NPD6319 Approved
0.7323 Intermediate Similarity NPD6616 Approved
0.7266 Intermediate Similarity NPD7078 Approved
0.7236 Intermediate Similarity NPD6009 Approved
0.72 Intermediate Similarity NPD8294 Approved
0.72 Intermediate Similarity NPD8377 Approved
0.7167 Intermediate Similarity NPD4634 Approved
0.7143 Intermediate Similarity NPD8335 Approved
0.7143 Intermediate Similarity NPD8516 Approved
0.7143 Intermediate Similarity NPD8515 Approved
0.7143 Intermediate Similarity NPD8379 Approved
0.7143 Intermediate Similarity NPD8380 Approved
0.7143 Intermediate Similarity NPD6686 Approved
0.7143 Intermediate Similarity NPD8513 Phase 3
0.7143 Intermediate Similarity NPD8033 Approved
0.7143 Intermediate Similarity NPD8378 Approved
0.7143 Intermediate Similarity NPD8517 Approved
0.7143 Intermediate Similarity NPD8296 Approved
0.7131 Intermediate Similarity NPD4632 Approved
0.712 Intermediate Similarity NPD7516 Approved
0.7049 Intermediate Similarity NPD6882 Approved
0.704 Intermediate Similarity NPD7327 Approved
0.704 Intermediate Similarity NPD7328 Approved
0.696 Remote Similarity NPD7115 Discovery
0.6947 Remote Similarity NPD6033 Approved
0.6917 Remote Similarity NPD5697 Approved
0.6911 Remote Similarity NPD8297 Approved
0.6903 Remote Similarity NPD8171 Discontinued
0.6875 Remote Similarity NPD7503 Approved
0.686 Remote Similarity NPD6899 Approved
0.686 Remote Similarity NPD6881 Approved
0.6838 Remote Similarity NPD4696 Approved
0.6838 Remote Similarity NPD5286 Approved
0.6838 Remote Similarity NPD5285 Approved
0.6833 Remote Similarity NPD6675 Approved
0.6833 Remote Similarity NPD6402 Approved
0.6833 Remote Similarity NPD7128 Approved
0.6833 Remote Similarity NPD6008 Approved
0.6833 Remote Similarity NPD5739 Approved
0.6829 Remote Similarity NPD6650 Approved
0.6829 Remote Similarity NPD6649 Approved
0.6814 Remote Similarity NPD8034 Phase 2
0.6814 Remote Similarity NPD8035 Phase 2
0.681 Remote Similarity NPD4755 Approved
0.6803 Remote Similarity NPD6013 Approved
0.6803 Remote Similarity NPD6012 Approved
0.6803 Remote Similarity NPD6014 Approved
0.6803 Remote Similarity NPD6372 Approved
0.6803 Remote Similarity NPD6373 Approved
0.6777 Remote Similarity NPD5701 Approved
0.6769 Remote Similarity NPD6067 Discontinued
0.6748 Remote Similarity NPD6883 Approved
0.6748 Remote Similarity NPD7102 Approved
0.6748 Remote Similarity NPD7290 Approved
0.6744 Remote Similarity NPD6921 Approved
0.6744 Remote Similarity NPD5983 Phase 2
0.6723 Remote Similarity NPD4633 Approved
0.6723 Remote Similarity NPD5225 Approved
0.6723 Remote Similarity NPD5224 Approved
0.6723 Remote Similarity NPD5226 Approved
0.6723 Remote Similarity NPD5211 Phase 2
0.6721 Remote Similarity NPD6011 Approved
0.6721 Remote Similarity NPD7320 Approved
0.6695 Remote Similarity NPD4700 Approved
0.6694 Remote Similarity NPD6847 Approved
0.6694 Remote Similarity NPD6869 Approved
0.6694 Remote Similarity NPD6617 Approved
0.6694 Remote Similarity NPD8130 Phase 1
0.6667 Remote Similarity NPD5175 Approved
0.6667 Remote Similarity NPD5174 Approved
0.6667 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6079 Approved
0.6641 Remote Similarity NPD7604 Phase 2
0.6639 Remote Similarity NPD5223 Approved
0.6637 Remote Similarity NPD5328 Approved
0.6612 Remote Similarity NPD5141 Approved
0.661 Remote Similarity NPD4225 Approved
0.6609 Remote Similarity NPD6399 Phase 3
0.6581 Remote Similarity NPD5221 Approved
0.6581 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6581 Remote Similarity NPD5222 Approved
0.6581 Remote Similarity NPD4697 Phase 3
0.6577 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6541 Remote Similarity NPD6336 Discontinued
0.6525 Remote Similarity NPD5173 Approved
0.6525 Remote Similarity NPD7902 Approved
0.6518 Remote Similarity NPD3618 Phase 1
0.6484 Remote Similarity NPD6274 Approved
0.648 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5956 Approved
0.6466 Remote Similarity NPD4202 Approved
0.6452 Remote Similarity NPD4729 Approved
0.6452 Remote Similarity NPD4730 Approved
0.6452 Remote Similarity NPD5128 Approved
0.6429 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6423 Remote Similarity NPD4768 Approved
0.6423 Remote Similarity NPD4767 Approved
0.641 Remote Similarity NPD7748 Approved
0.6396 Remote Similarity NPD4788 Approved
0.6393 Remote Similarity NPD4754 Approved
0.6379 Remote Similarity NPD7515 Phase 2
0.6372 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1700 Approved
0.6349 Remote Similarity NPD5249 Phase 3
0.6349 Remote Similarity NPD5248 Approved
0.6349 Remote Similarity NPD5247 Approved
0.6349 Remote Similarity NPD5250 Approved
0.6349 Remote Similarity NPD5251 Approved
0.6339 Remote Similarity NPD4786 Approved
0.6336 Remote Similarity NPD7100 Approved
0.6336 Remote Similarity NPD7101 Approved
0.6333 Remote Similarity NPD7638 Approved
0.6308 Remote Similarity NPD6317 Approved
0.6306 Remote Similarity NPD3667 Approved
0.6299 Remote Similarity NPD5217 Approved
0.6299 Remote Similarity NPD5215 Approved
0.6299 Remote Similarity NPD5216 Approved
0.6299 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6281 Remote Similarity NPD7639 Approved
0.6281 Remote Similarity NPD7640 Approved
0.6271 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6271 Remote Similarity NPD7900 Approved
0.6262 Remote Similarity NPD3703 Phase 2
0.626 Remote Similarity NPD6335 Approved
0.626 Remote Similarity NPD6313 Approved
0.626 Remote Similarity NPD6314 Approved
0.625 Remote Similarity NPD6083 Phase 2
0.625 Remote Similarity NPD8074 Phase 3
0.625 Remote Similarity NPD6084 Phase 2
0.6241 Remote Similarity NPD6291 Clinical (unspecified phase)
0.624 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6411 Approved
0.6231 Remote Similarity NPD6940 Discontinued
0.622 Remote Similarity NPD5169 Approved
0.622 Remote Similarity NPD6371 Approved
0.622 Remote Similarity NPD5135 Approved
0.622 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6218 Remote Similarity NPD5210 Approved
0.6218 Remote Similarity NPD4629 Approved
0.6216 Remote Similarity NPD1780 Approved
0.6216 Remote Similarity NPD1779 Approved
0.6207 Remote Similarity NPD4753 Phase 2
0.6198 Remote Similarity NPD5696 Approved
0.6195 Remote Similarity NPD3665 Phase 1
0.6195 Remote Similarity NPD3133 Approved
0.6195 Remote Similarity NPD3666 Approved
0.6174 Remote Similarity NPD3573 Approved
0.6172 Remote Similarity NPD5127 Approved
0.6143 Remote Similarity NPD8338 Approved
0.6143 Remote Similarity NPD8449 Approved
0.6134 Remote Similarity NPD5282 Discontinued
0.6126 Remote Similarity NPD6928 Phase 2
0.6119 Remote Similarity NPD6909 Approved
0.6119 Remote Similarity NPD6908 Approved
0.6119 Remote Similarity NPD8268 Approved
0.6119 Remote Similarity NPD8269 Approved
0.6119 Remote Similarity NPD8266 Approved
0.6119 Remote Similarity NPD8267 Approved
0.6107 Remote Similarity NPD6868 Approved
0.6106 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6106 Remote Similarity NPD3669 Approved
0.6099 Remote Similarity NPD8450 Suspended
0.6091 Remote Similarity NPD6115 Approved
0.6091 Remote Similarity NPD6118 Approved
0.6091 Remote Similarity NPD6114 Approved
0.6091 Remote Similarity NPD6697 Approved
0.609 Remote Similarity NPD4522 Approved
0.6087 Remote Similarity NPD8337 Approved
0.6087 Remote Similarity NPD8336 Approved
0.6083 Remote Similarity NPD5695 Phase 3
0.6068 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6068 Remote Similarity NPD6101 Approved
0.6063 Remote Similarity NPD5168 Approved
0.6042 Remote Similarity NPD6334 Approved
0.6042 Remote Similarity NPD6333 Approved
0.6031 Remote Similarity NPD5167 Approved
0.6 Remote Similarity NPD6116 Phase 1
0.6 Remote Similarity NPD6053 Discontinued
0.5983 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5956 Remote Similarity NPD8080 Discontinued
0.5952 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5952 Remote Similarity NPD4057 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   44445771
ChEMBL   CHEMBL401208
ZINC  

Physicochemical Properties

Molecular Weight:  362.17
ALogP:  -1.7409
MLogP:  3
XLogP:  0.942
# Rotatable Bonds:  5
Polar Surface Area:  96.22
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  26

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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