Natural Product: NPC477277

Natural Product ID:  NPC477277
Common Name:   Brevipolide C
IUPAC Name:   [1-[(1S,2S)-2-[(S)-hydroxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:   Brevipolide C
Molecular Formula:   C21H22O8
Standard InCHIKey:  PMVFYHVSZOZDAN-WJWNCLPLSA-N
Standard InCHI:  InChI=1S/C21H22O8/c1-11(28-19(25)8-6-12-5-7-15(22)16(23)9-12)20(26)13-10-14(13)21(27)17-3-2-4-18(24)29-17/h2,4-9,11,13-14,17,21-23,27H,3,10H2,1H3/b8-6+/t11?,13-,14-,17+,21-/m0/s1
Canonical SMILES:  O=C(OC(C(=O)[C@H]1C[C@@H]1[C@@H]([C@H]1CC=CC(=O)O1)O)C)/C=C/c1ccc(c(c1)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
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota Whole Plant Tawangmangu village, Karanganyar, Central Java, Indonesia 2003-FEB PMID[19422206]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens ED50 > 10 nM 19422206
NPT2 Others Unspecified ED50 = 38 nM 19422206
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens ED50 > 50 nM 19422206
NPT139 Cell Line HT-29 Homo sapiens ED50 = 8.5 nM 19422206

  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 NPC477277 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 NPC477278
0.9925 High Similarity NPC477279
0.9571 High Similarity NPC98009
0.9403 High Similarity NPC19719
0.9403 High Similarity NPC477280
0.9403 High Similarity NPC477281
0.9328 High Similarity NPC323379
0.9328 High Similarity NPC327204
0.9118 High Similarity NPC168799
0.9118 High Similarity NPC155209
0.9044 High Similarity NPC25581
0.9044 High Similarity NPC18074
0.9044 High Similarity NPC5419
0.9044 High Similarity NPC61
0.9 High Similarity NPC295492
0.9 High Similarity NPC476819
0.9 High Similarity NPC474875
0.9 High Similarity NPC476820
0.9 High Similarity NPC303683
0.9 High Similarity NPC274891
0.9 High Similarity NPC205751
0.9 High Similarity NPC26241
0.8971 High Similarity NPC198388
0.8929 High Similarity NPC219428
0.8929 High Similarity NPC142703
0.8929 High Similarity NPC278068
0.8929 High Similarity NPC152942
0.8929 High Similarity NPC302857
0.8929 High Similarity NPC37250
0.8921 High Similarity NPC71638
0.8921 High Similarity NPC64230
0.8811 High Similarity NPC303090
0.8811 High Similarity NPC319628
0.8811 High Similarity NPC37331
0.8811 High Similarity NPC258469
0.8811 High Similarity NPC472016
0.8811 High Similarity NPC284948
0.8811 High Similarity NPC220664
0.8811 High Similarity NPC43158
0.8811 High Similarity NPC277315
0.8811 High Similarity NPC192831
0.8767 High Similarity NPC192568
0.8767 High Similarity NPC471076
0.8741 High Similarity NPC35702
0.8741 High Similarity NPC471027
0.8741 High Similarity NPC297517
0.8741 High Similarity NPC206095
0.8741 High Similarity NPC13818
0.8741 High Similarity NPC224389
0.8741 High Similarity NPC477335
0.8732 High Similarity NPC322021
0.8732 High Similarity NPC156709
0.8732 High Similarity NPC179505
0.8732 High Similarity NPC289690
0.8732 High Similarity NPC288452
0.8714 High Similarity NPC182217
0.8714 High Similarity NPC70680
0.8714 High Similarity NPC233350
0.8705 High Similarity NPC471749
0.8699 High Similarity NPC229264
0.8643 High Similarity NPC474895
0.8643 High Similarity NPC68517
0.863 High Similarity NPC98356
0.8592 High Similarity NPC279676
0.8592 High Similarity NPC67349
0.8552 High Similarity NPC285550
0.8542 High Similarity NPC38473
0.8531 High Similarity NPC284409
0.8531 High Similarity NPC283560
0.8531 High Similarity NPC24295
0.8523 High Similarity NPC32197
0.8511 High Similarity NPC106406
0.8493 Intermediate Similarity NPC183824
0.8493 Intermediate Similarity NPC474692
0.8477 Intermediate Similarity NPC44730
0.8477 Intermediate Similarity NPC327225
0.8446 Intermediate Similarity NPC221383
0.8446 Intermediate Similarity NPC143892
0.8446 Intermediate Similarity NPC299090
0.8446 Intermediate Similarity NPC283081
0.8446 Intermediate Similarity NPC322660
0.8435 Intermediate Similarity NPC477333
0.8435 Intermediate Similarity NPC469683
0.8429 Intermediate Similarity NPC318799
0.8417 Intermediate Similarity NPC226855
0.8414 Intermediate Similarity NPC9218
0.84 Intermediate Similarity NPC306343
0.8392 Intermediate Similarity NPC475111
0.8389 Intermediate Similarity NPC1580
0.8389 Intermediate Similarity NPC472969
0.8367 Intermediate Similarity NPC50221
0.8367 Intermediate Similarity NPC160378
0.8367 Intermediate Similarity NPC114242
0.8367 Intermediate Similarity NPC469615
0.8366 Intermediate Similarity NPC475484
0.8356 Intermediate Similarity NPC296643
0.8345 Intermediate Similarity NPC105525
0.8345 Intermediate Similarity NPC225036
0.8345 Intermediate Similarity NPC12218
0.8345 Intermediate Similarity NPC75763
0.8333 Intermediate Similarity NPC42464
0.8322 Intermediate Similarity NPC139519
0.8321 Intermediate Similarity NPC85565
0.8312 Intermediate Similarity NPC473275
0.8312 Intermediate Similarity NPC470896
0.8311 Intermediate Similarity NPC258671
0.8311 Intermediate Similarity NPC53884
0.831 Intermediate Similarity NPC129889
0.831 Intermediate Similarity NPC307006
0.8301 Intermediate Similarity NPC125487
0.8301 Intermediate Similarity NPC477299
0.8301 Intermediate Similarity NPC281703
0.8289 Intermediate Similarity NPC95498
0.8289 Intermediate Similarity NPC163883
0.8289 Intermediate Similarity NPC246566
0.8289 Intermediate Similarity NPC93498
0.8276 Intermediate Similarity NPC325625
0.8276 Intermediate Similarity NPC239943
0.8273 Intermediate Similarity NPC158654
0.8267 Intermediate Similarity NPC43123
0.8264 Intermediate Similarity NPC156892
0.8264 Intermediate Similarity NPC90431
0.8255 Intermediate Similarity NPC473867
0.8252 Intermediate Similarity NPC471110
0.8243 Intermediate Similarity NPC473090
0.8243 Intermediate Similarity NPC46161
0.8243 Intermediate Similarity NPC22176
0.8243 Intermediate Similarity NPC304956
0.8243 Intermediate Similarity NPC121573
0.8243 Intermediate Similarity NPC190587
0.8243 Intermediate Similarity NPC239608
0.8243 Intermediate Similarity NPC226738
0.8239 Intermediate Similarity NPC239302
0.8235 Intermediate Similarity NPC322332
0.8235 Intermediate Similarity NPC266084
0.8235 Intermediate Similarity NPC475162
0.8235 Intermediate Similarity NPC83663
0.8235 Intermediate Similarity NPC475216
0.8235 Intermediate Similarity NPC475595
0.8235 Intermediate Similarity NPC472271
0.8235 Intermediate Similarity NPC475145
0.8235 Intermediate Similarity NPC473544
0.8235 Intermediate Similarity NPC146277
0.8235 Intermediate Similarity NPC19380
0.8235 Intermediate Similarity NPC147654
0.8231 Intermediate Similarity NPC253481
0.8231 Intermediate Similarity NPC253722
0.8231 Intermediate Similarity NPC31751
0.8227 Intermediate Similarity NPC217052
0.8227 Intermediate Similarity NPC285361
0.8227 Intermediate Similarity NPC32626
0.8227 Intermediate Similarity NPC329344
0.8227 Intermediate Similarity NPC237506
0.8227 Intermediate Similarity NPC172673
0.8224 Intermediate Similarity NPC477334
0.8224 Intermediate Similarity NPC243891
0.8219 Intermediate Similarity NPC191280
0.8219 Intermediate Similarity NPC147379
0.8219 Intermediate Similarity NPC474784
0.8212 Intermediate Similarity NPC476394
0.8212 Intermediate Similarity NPC98809
0.8209 Intermediate Similarity NPC63126
0.8209 Intermediate Similarity NPC309434
0.8205 Intermediate Similarity NPC471750
0.8201 Intermediate Similarity NPC475695
0.8201 Intermediate Similarity NPC147192
0.8201 Intermediate Similarity NPC251407
0.8201 Intermediate Similarity NPC168653
0.8194 Intermediate Similarity NPC18646
0.8182 Intermediate Similarity NPC239855
0.8182 Intermediate Similarity NPC475468
0.817 Intermediate Similarity NPC267091
0.817 Intermediate Similarity NPC75695
0.8169 Intermediate Similarity NPC108553
0.8163 Intermediate Similarity NPC100675
0.8162 Intermediate Similarity NPC470849
0.8162 Intermediate Similarity NPC470848
0.8156 Intermediate Similarity NPC64111
0.8156 Intermediate Similarity NPC94810
0.8151 Intermediate Similarity NPC220942
0.8151 Intermediate Similarity NPC257173
0.8129 Intermediate Similarity NPC132921
0.8129 Intermediate Similarity NPC203757
0.8129 Intermediate Similarity NPC197832
0.8129 Intermediate Similarity NPC145425
0.8125 Intermediate Similarity NPC204582
0.8125 Intermediate Similarity NPC135127
0.8125 Intermediate Similarity NPC248150
0.8121 Intermediate Similarity NPC229036
0.8121 Intermediate Similarity NPC470130
0.8117 Intermediate Similarity NPC161159
0.8113 Intermediate Similarity NPC272750
0.8113 Intermediate Similarity NPC173729
0.8113 Intermediate Similarity NPC223006
0.8113 Intermediate Similarity NPC134047
0.8108 Intermediate Similarity NPC476842
0.8108 Intermediate Similarity NPC476840
0.8105 Intermediate Similarity NPC140151
0.8105 Intermediate Similarity NPC300329
0.8105 Intermediate Similarity NPC56204

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477277 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
0.8811 High Similarity NPD6190 Approved
0.8056 Intermediate Similarity NPD230 Phase 1
0.7905 Intermediate Similarity NPD7266 Discontinued
0.7867 Intermediate Similarity NPD8166 Discontinued
0.7748 Intermediate Similarity NPD4628 Phase 3
0.7736 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD3882 Suspended
0.7681 Intermediate Similarity NPD9545 Approved
0.7673 Intermediate Similarity NPD3817 Phase 2
0.7619 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD7075 Discontinued
0.756 Intermediate Similarity NPD7685 Pre-registration
0.7547 Intermediate Similarity NPD6801 Discontinued
0.753 Intermediate Similarity NPD3818 Discontinued
0.7517 Intermediate Similarity NPD9494 Approved
0.7515 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6166 Phase 2
0.75 Intermediate Similarity NPD6797 Phase 2
0.7483 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD7251 Discontinued
0.745 Intermediate Similarity NPD6355 Discontinued
0.7438 Intermediate Similarity NPD1934 Approved
0.7413 Intermediate Similarity NPD9269 Phase 2
0.7391 Intermediate Similarity NPD2801 Approved
0.7391 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD943 Approved
0.7372 Intermediate Similarity NPD6799 Approved
0.7365 Intermediate Similarity NPD6798 Discontinued
0.7358 Intermediate Similarity NPD3455 Phase 2
0.7346 Intermediate Similarity NPD5402 Approved
0.7317 Intermediate Similarity NPD6234 Discontinued
0.7312 Intermediate Similarity NPD4380 Phase 2
0.731 Intermediate Similarity NPD7808 Phase 3
0.7297 Intermediate Similarity NPD3027 Phase 3
0.7278 Intermediate Similarity NPD7054 Approved
0.7278 Intermediate Similarity NPD1512 Approved
0.7267 Intermediate Similarity NPD826 Approved
0.7267 Intermediate Similarity NPD825 Approved
0.7267 Intermediate Similarity NPD4060 Phase 1
0.7267 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD2629 Approved
0.7248 Intermediate Similarity NPD3764 Approved
0.7246 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7472 Approved
0.7235 Intermediate Similarity NPD7074 Phase 3
0.7233 Intermediate Similarity NPD5403 Approved
0.7233 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD37 Approved
0.7205 Intermediate Similarity NPD6599 Discontinued
0.72 Intermediate Similarity NPD6233 Phase 2
0.72 Intermediate Similarity NPD4062 Phase 3
0.7195 Intermediate Similarity NPD4966 Approved
0.7195 Intermediate Similarity NPD4965 Approved
0.7195 Intermediate Similarity NPD4967 Phase 2
0.719 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD1653 Approved
0.7179 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD4110 Phase 3
0.7172 Intermediate Similarity NPD1608 Approved
0.7161 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7473 Discontinued
0.7153 Intermediate Similarity NPD3022 Approved
0.7153 Intermediate Similarity NPD3021 Approved
0.7152 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1511 Approved
0.7143 Intermediate Similarity NPD8150 Discontinued
0.7133 Intermediate Similarity NPD9268 Approved
0.7126 Intermediate Similarity NPD7199 Phase 2
0.7126 Intermediate Similarity NPD8127 Discontinued
0.7118 Intermediate Similarity NPD7228 Approved
0.7108 Intermediate Similarity NPD919 Approved
0.7107 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5401 Approved
0.7107 Intermediate Similarity NPD3146 Approved
0.7083 Intermediate Similarity NPD6232 Discontinued
0.7076 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD5844 Phase 1
0.7073 Intermediate Similarity NPD1465 Phase 2
0.7067 Intermediate Similarity NPD7095 Approved
0.7062 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD6385 Approved
0.7055 Intermediate Similarity NPD6386 Approved
0.7029 Intermediate Similarity NPD2067 Discontinued
0.7025 Intermediate Similarity NPD2354 Approved
0.7025 Intermediate Similarity NPD3887 Approved
0.7021 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD3751 Discontinued
0.7007 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.6993 Remote Similarity NPD4340 Discontinued
0.6993 Remote Similarity NPD555 Phase 2
0.6993 Remote Similarity NPD5536 Phase 2
0.6987 Remote Similarity NPD5762 Approved
0.6987 Remote Similarity NPD5763 Approved
0.6983 Remote Similarity NPD7879 Clinical (unspecified phase)
0.698 Remote Similarity NPD258 Approved
0.698 Remote Similarity NPD257 Approved
0.698 Remote Similarity NPD5647 Approved
0.6974 Remote Similarity NPD6663 Approved
0.697 Remote Similarity NPD7819 Suspended
0.6968 Remote Similarity NPD1510 Phase 2
0.6968 Remote Similarity NPD7033 Discontinued
0.6966 Remote Similarity NPD17 Approved
0.6962 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6949 Remote Similarity NPD8434 Phase 2
0.6943 Remote Similarity NPD4534 Discontinued
0.6943 Remote Similarity NPD5958 Discontinued
0.6933 Remote Similarity NPD5736 Approved
0.6929 Remote Similarity NPD228 Approved
0.6928 Remote Similarity NPD1613 Approved
0.6928 Remote Similarity NPD5353 Approved
0.6928 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6923 Remote Similarity NPD9570 Approved
0.6923 Remote Similarity NPD2935 Discontinued
0.6908 Remote Similarity NPD3268 Approved
0.6894 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6894 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6883 Remote Similarity NPD447 Suspended
0.6882 Remote Similarity NPD3787 Discontinued
0.6864 Remote Similarity NPD5494 Approved
0.6863 Remote Similarity NPD259 Phase 1
0.6859 Remote Similarity NPD2799 Discontinued
0.6855 Remote Similarity NPD3750 Approved
0.6855 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7411 Suspended
0.6839 Remote Similarity NPD6653 Approved
0.6835 Remote Similarity NPD1549 Phase 2
0.6829 Remote Similarity NPD7458 Discontinued
0.6824 Remote Similarity NPD1247 Approved
0.6818 Remote Similarity NPD1240 Approved
0.6815 Remote Similarity NPD2438 Suspended
0.6815 Remote Similarity NPD2796 Approved
0.68 Remote Similarity NPD2797 Approved
0.68 Remote Similarity NPD987 Approved
0.679 Remote Similarity NPD2532 Approved
0.679 Remote Similarity NPD2534 Approved
0.679 Remote Similarity NPD2533 Approved
0.6772 Remote Similarity NPD2353 Approved
0.6772 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6772 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6772 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6763 Remote Similarity NPD1358 Approved
0.6761 Remote Similarity NPD6559 Discontinued
0.6748 Remote Similarity NPD6273 Approved
0.6744 Remote Similarity NPD5242 Approved
0.6744 Remote Similarity NPD3926 Phase 2
0.6736 Remote Similarity NPD4198 Discontinued
0.6735 Remote Similarity NPD2932 Approved
0.6735 Remote Similarity NPD3019 Approved
0.6735 Remote Similarity NPD1778 Approved
0.6733 Remote Similarity NPD1283 Approved
0.6731 Remote Similarity NPD1607 Approved
0.6727 Remote Similarity NPD3226 Approved
0.6726 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6724 Remote Similarity NPD2163 Approved
0.6713 Remote Similarity NPD1241 Discontinued
0.6713 Remote Similarity NPD5283 Phase 1
0.6711 Remote Similarity NPD9569 Approved
0.671 Remote Similarity NPD3619 Clinical (unspecified phase)
0.671 Remote Similarity NPD3620 Phase 2
0.6691 Remote Similarity NPD3134 Approved
0.669 Remote Similarity NPD9493 Approved
0.6688 Remote Similarity NPD7097 Phase 1
0.6687 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6685 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6685 Remote Similarity NPD8312 Approved
0.6685 Remote Similarity NPD8313 Approved
0.6667 Remote Similarity NPD6652 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5585 Approved
0.6667 Remote Similarity NPD7038 Approved
0.6667 Remote Similarity NPD8319 Approved
0.6667 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6002 Phase 3
0.6667 Remote Similarity NPD7039 Approved
0.6667 Remote Similarity NPD8320 Phase 1
0.6667 Remote Similarity NPD7240 Approved
0.6667 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7236 Approved
0.6667 Remote Similarity NPD6004 Phase 3
0.6667 Remote Similarity NPD275 Approved
0.6667 Remote Similarity NPD9495 Approved
0.6667 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6005 Phase 3
0.6667 Remote Similarity NPD3687 Approved
0.6667 Remote Similarity NPD3686 Approved
0.6667 Remote Similarity NPD5124 Phase 1
0.6667 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6667 Remote Similarity NPD274 Approved
0.6649 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6647 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6646 Remote Similarity NPD5049 Phase 3
0.6645 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6644 Remote Similarity NPD422 Phase 1

Structure

External Identifiers

PubChem CID   44178667
ChEMBL   CHEMBL1086650
ZINC  

Physicochemical Properties

Molecular Weight:  402.13
ALogP:  -1.4441
MLogP:  2.89
XLogP:  1.336
# Rotatable Bonds:  12
Polar Surface Area:  130.36
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  29

Download Data

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Biological Activities  
Similar NPs/Drugs