Natural Product: NPC76116

Natural Product ID:  NPC76116
Common Name:   Tylophoridicine F
IUPAC Name:   (13aS,14R)-3,6,7-trimethoxy-10-oxido-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-10-ium-14-ol
Synonyms:   Tylophoridicine F
Molecular Formula:   C23H25NO5
Standard InCHIKey:  SHQULSXBVKOENG-OSAZCDQKSA-N
Standard InCHI:  InChI=1S/C23H25NO5/c1-27-13-6-7-14-15(9-13)16-10-20(28-2)21(29-3)11-17(16)18-12-24(26)8-4-5-19(24)23(25)22(14)18/h6-7,9-11,19,23,25H,4-5,8,12H2,1-3H3/t19-,23-,24?/m0/s1
Canonical SMILES:  COc1ccc2c(c1)c1cc(OC)c(cc1c1c2[C@@H](O)[C@H]2N(=O)(C1)CCC2)OC
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
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens GI50 = 71 nM 17531481
NPT461 Cell Line PANC-1 Homo sapiens GI50 = 63 nM 17531481
NPT2 Others Unspecified IC50 = 367 nM 17531481
NPT2 Others Unspecified IC50 > 1000 nM 17531481
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens IC50 > 3000 nM 17531481

  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 NPC76116 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
0.9806 High Similarity NPC160570
0.9806 High Similarity NPC164429
0.9618 High Similarity NPC329911
0.9211 High Similarity NPC44869
0.8981 High Similarity NPC477133
0.8981 High Similarity NPC477132
0.8938 High Similarity NPC233650
0.8882 High Similarity NPC134858
0.8773 High Similarity NPC150879
0.8773 High Similarity NPC210140
0.8588 High Similarity NPC233718
0.8457 Intermediate Similarity NPC475326
0.8438 Intermediate Similarity NPC470924
0.8438 Intermediate Similarity NPC37272
0.8355 Intermediate Similarity NPC475828
0.8323 Intermediate Similarity NPC26601
0.8313 Intermediate Similarity NPC169743
0.8312 Intermediate Similarity NPC210086
0.8282 Intermediate Similarity NPC147091
0.8282 Intermediate Similarity NPC186063
0.825 Intermediate Similarity NPC219162
0.8242 Intermediate Similarity NPC205167
0.8199 Intermediate Similarity NPC274026
0.8187 Intermediate Similarity NPC130941
0.8182 Intermediate Similarity NPC59028
0.8182 Intermediate Similarity NPC92191
0.8133 Intermediate Similarity NPC249274
0.8125 Intermediate Similarity NPC90844
0.8125 Intermediate Similarity NPC253883
0.8125 Intermediate Similarity NPC95075
0.807 Intermediate Similarity NPC477640
0.807 Intermediate Similarity NPC470739
0.807 Intermediate Similarity NPC225597
0.8059 Intermediate Similarity NPC266176
0.8059 Intermediate Similarity NPC290759
0.8059 Intermediate Similarity NPC475686
0.8059 Intermediate Similarity NPC158148
0.8059 Intermediate Similarity NPC82533
0.8059 Intermediate Similarity NPC58766
0.8057 Intermediate Similarity NPC248642
0.8046 Intermediate Similarity NPC126284
0.8024 Intermediate Similarity NPC215829
0.8024 Intermediate Similarity NPC97072
0.8012 Intermediate Similarity NPC474475
0.8011 Intermediate Similarity NPC156576
0.8 Intermediate Similarity NPC244112
0.8 Intermediate Similarity NPC185838
0.7989 Intermediate Similarity NPC477560
0.7988 Intermediate Similarity NPC82285
0.7988 Intermediate Similarity NPC133011
0.7963 Intermediate Similarity NPC476571
0.7963 Intermediate Similarity NPC135538
0.7963 Intermediate Similarity NPC24233
0.7963 Intermediate Similarity NPC147390
0.7963 Intermediate Similarity NPC428
0.7963 Intermediate Similarity NPC246587
0.7919 Intermediate Similarity NPC2314
0.7917 Intermediate Similarity NPC27410
0.7917 Intermediate Similarity NPC166014
0.7914 Intermediate Similarity NPC92541
0.7901 Intermediate Similarity NPC476151
0.7901 Intermediate Similarity NPC191376
0.7901 Intermediate Similarity NPC179825
0.7901 Intermediate Similarity NPC321505
0.7898 Intermediate Similarity NPC193528
0.7895 Intermediate Similarity NPC298979
0.7895 Intermediate Similarity NPC100566
0.7895 Intermediate Similarity NPC181653
0.7895 Intermediate Similarity NPC190332
0.7888 Intermediate Similarity NPC130926
0.7885 Intermediate Similarity NPC11147
0.787 Intermediate Similarity NPC60186
0.7866 Intermediate Similarity NPC88249
0.7866 Intermediate Similarity NPC97221
0.7866 Intermediate Similarity NPC192768
0.7866 Intermediate Similarity NPC151895
0.7866 Intermediate Similarity NPC220858
0.7862 Intermediate Similarity NPC213206
0.7862 Intermediate Similarity NPC188163
0.7862 Intermediate Similarity NPC474915
0.7862 Intermediate Similarity NPC328750
0.7829 Intermediate Similarity NPC474470
0.7824 Intermediate Similarity NPC320104
0.7824 Intermediate Similarity NPC324144
0.7821 Intermediate Similarity NPC214116
0.7818 Intermediate Similarity NPC81733
0.7818 Intermediate Similarity NPC326316
0.7811 Intermediate Similarity NPC4304
0.7805 Intermediate Similarity NPC477565
0.7805 Intermediate Similarity NPC103379
0.7799 Intermediate Similarity NPC314682
0.7798 Intermediate Similarity NPC40389
0.7798 Intermediate Similarity NPC78359
0.7798 Intermediate Similarity NPC148014
0.7798 Intermediate Similarity NPC315707
0.7798 Intermediate Similarity NPC65490
0.7791 Intermediate Similarity NPC306555
0.7791 Intermediate Similarity NPC158376
0.7791 Intermediate Similarity NPC145832
0.7791 Intermediate Similarity NPC117188
0.7791 Intermediate Similarity NPC144863
0.7791 Intermediate Similarity NPC205421
0.7791 Intermediate Similarity NPC474931
0.7791 Intermediate Similarity NPC81218
0.7791 Intermediate Similarity NPC12053
0.7784 Intermediate Similarity NPC249797
0.7784 Intermediate Similarity NPC110416
0.7784 Intermediate Similarity NPC469817
0.7784 Intermediate Similarity NPC207757
0.7784 Intermediate Similarity NPC295691
0.7784 Intermediate Similarity NPC193949
0.7784 Intermediate Similarity NPC39701
0.7784 Intermediate Similarity NPC278799
0.7784 Intermediate Similarity NPC204828
0.7784 Intermediate Similarity NPC78733
0.7784 Intermediate Similarity NPC127674
0.7784 Intermediate Similarity NPC76079
0.7784 Intermediate Similarity NPC276588
0.7784 Intermediate Similarity NPC54379
0.7784 Intermediate Similarity NPC172765
0.7784 Intermediate Similarity NPC189266
0.7784 Intermediate Similarity NPC5238
0.7784 Intermediate Similarity NPC2413
0.7784 Intermediate Similarity NPC184026
0.7778 Intermediate Similarity NPC253043
0.7778 Intermediate Similarity NPC212794
0.7778 Intermediate Similarity NPC136508
0.7778 Intermediate Similarity NPC477563
0.7778 Intermediate Similarity NPC306843
0.7778 Intermediate Similarity NPC78222
0.7778 Intermediate Similarity NPC196447
0.7778 Intermediate Similarity NPC13504
0.7778 Intermediate Similarity NPC96603
0.7764 Intermediate Similarity NPC128019
0.7764 Intermediate Similarity NPC136860
0.7764 Intermediate Similarity NPC476567
0.7759 Intermediate Similarity NPC57272
0.7751 Intermediate Similarity NPC111485
0.7751 Intermediate Similarity NPC477080
0.7744 Intermediate Similarity NPC475959
0.774 Intermediate Similarity NPC244554
0.7738 Intermediate Similarity NPC37205
0.7738 Intermediate Similarity NPC160931
0.7733 Intermediate Similarity NPC476002
0.7727 Intermediate Similarity NPC237044
0.7706 Intermediate Similarity NPC306902
0.7706 Intermediate Similarity NPC232924
0.7706 Intermediate Similarity NPC160298
0.7706 Intermediate Similarity NPC477559
0.7706 Intermediate Similarity NPC18402
0.7706 Intermediate Similarity NPC266753
0.7697 Intermediate Similarity NPC207824
0.7697 Intermediate Similarity NPC60538
0.7692 Intermediate Similarity NPC118419
0.7692 Intermediate Similarity NPC476572
0.7688 Intermediate Similarity NPC252960
0.7688 Intermediate Similarity NPC301189
0.7688 Intermediate Similarity NPC298186
0.7684 Intermediate Similarity NPC114364
0.7684 Intermediate Similarity NPC320223
0.7684 Intermediate Similarity NPC474325
0.7684 Intermediate Similarity NPC294790
0.7684 Intermediate Similarity NPC148693
0.7684 Intermediate Similarity NPC118633
0.7683 Intermediate Similarity NPC51957
0.7683 Intermediate Similarity NPC16107
0.7683 Intermediate Similarity NPC210437
0.7683 Intermediate Similarity NPC476144
0.7683 Intermediate Similarity NPC106295
0.7679 Intermediate Similarity NPC325871
0.7679 Intermediate Similarity NPC99659
0.7674 Intermediate Similarity NPC238530
0.7674 Intermediate Similarity NPC276944
0.7674 Intermediate Similarity NPC232514
0.7674 Intermediate Similarity NPC247972
0.767 Intermediate Similarity NPC128560
0.767 Intermediate Similarity NPC229166
0.767 Intermediate Similarity NPC304675
0.767 Intermediate Similarity NPC199465
0.7665 Intermediate Similarity NPC148898
0.7657 Intermediate Similarity NPC476331
0.7654 Intermediate Similarity NPC476575
0.764 Intermediate Similarity NPC474745
0.7636 Intermediate Similarity NPC7467
0.763 Intermediate Similarity NPC35627
0.763 Intermediate Similarity NPC81247
0.763 Intermediate Similarity NPC124657
0.763 Intermediate Similarity NPC476573
0.763 Intermediate Similarity NPC476432
0.763 Intermediate Similarity NPC24264
0.7627 Intermediate Similarity NPC241704
0.7616 Intermediate Similarity NPC1229
0.7616 Intermediate Similarity NPC218614
0.761 Intermediate Similarity NPC131204
0.761 Intermediate Similarity NPC301050
0.7605 Intermediate Similarity NPC476568
0.7605 Intermediate Similarity NPC76213
0.7605 Intermediate Similarity NPC277669
0.7588 Intermediate Similarity NPC129603
0.7586 Intermediate Similarity NPC247389

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC76116 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
0.7937 Intermediate Similarity NPD5241 Discontinued
0.7862 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD2563 Approved
0.7798 Intermediate Similarity NPD2560 Approved
0.7738 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD4773 Phase 2
0.7725 Intermediate Similarity NPD4772 Phase 2
0.7719 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD7831 Phase 2
0.7706 Intermediate Similarity NPD7833 Phase 2
0.7706 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD2969 Approved
0.7688 Intermediate Similarity NPD2970 Approved
0.7683 Intermediate Similarity NPD4584 Approved
0.7644 Intermediate Similarity NPD27 Approved
0.7644 Intermediate Similarity NPD2489 Approved
0.763 Intermediate Similarity NPD6071 Discontinued
0.7593 Intermediate Similarity NPD4236 Phase 3
0.7593 Intermediate Similarity NPD4237 Approved
0.7544 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD2898 Approved
0.7529 Intermediate Similarity NPD3051 Approved
0.7403 Intermediate Similarity NPD7313 Approved
0.7403 Intermediate Similarity NPD7310 Approved
0.7403 Intermediate Similarity NPD7312 Approved
0.7403 Intermediate Similarity NPD7311 Approved
0.7378 Intermediate Similarity NPD3060 Approved
0.7363 Intermediate Similarity NPD7309 Approved
0.7342 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7906 Approved
0.7294 Intermediate Similarity NPD4017 Approved
0.7283 Intermediate Similarity NPD4663 Approved
0.7278 Intermediate Similarity NPD6031 Approved
0.7278 Intermediate Similarity NPD3639 Approved
0.7278 Intermediate Similarity NPD3641 Approved
0.7278 Intermediate Similarity NPD3640 Phase 3
0.7278 Intermediate Similarity NPD6030 Approved
0.7267 Intermediate Similarity NPD7298 Approved
0.7262 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD7400 Phase 3
0.7247 Intermediate Similarity NPD4481 Phase 3
0.7246 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD4010 Discontinued
0.7229 Intermediate Similarity NPD6331 Phase 2
0.7225 Intermediate Similarity NPD5772 Approved
0.7225 Intermediate Similarity NPD2977 Approved
0.7225 Intermediate Similarity NPD2978 Approved
0.7225 Intermediate Similarity NPD5773 Approved
0.7219 Intermediate Similarity NPD6090 Discontinued
0.7213 Intermediate Similarity NPD4577 Approved
0.7213 Intermediate Similarity NPD4578 Approved
0.7212 Intermediate Similarity NPD7037 Approved
0.7202 Intermediate Similarity NPD2421 Approved
0.7202 Intermediate Similarity NPD2420 Approved
0.7186 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD6107 Approved
0.7169 Intermediate Similarity NPD4162 Approved
0.7093 Intermediate Similarity NPD4005 Discontinued
0.7083 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD5177 Phase 3
0.7063 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5709 Phase 3
0.7049 Intermediate Similarity NPD6297 Approved
0.7041 Intermediate Similarity NPD3845 Phase 1
0.7039 Intermediate Similarity NPD4166 Phase 2
0.7037 Intermediate Similarity NPD2674 Phase 3
0.7035 Intermediate Similarity NPD4210 Discontinued
0.703 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD4666 Phase 3
0.7017 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6688 Approved
0.7 Intermediate Similarity NPD6687 Approved
0.6989 Remote Similarity NPD8053 Approved
0.6989 Remote Similarity NPD6853 Approved
0.6989 Remote Similarity NPD8054 Approved
0.6989 Remote Similarity NPD6851 Approved
0.6975 Remote Similarity NPD5718 Phase 2
0.6974 Remote Similarity NPD3533 Approved
0.6974 Remote Similarity NPD2491 Approved
0.6974 Remote Similarity NPD2972 Approved
0.6974 Remote Similarity NPD3448 Approved
0.6973 Remote Similarity NPD7132 Clinical (unspecified phase)
0.697 Remote Similarity NPD6896 Approved
0.697 Remote Similarity NPD6895 Approved
0.6959 Remote Similarity NPD4123 Phase 3
0.695 Remote Similarity NPD5676 Approved
0.694 Remote Similarity NPD8156 Discontinued
0.6928 Remote Similarity NPD1753 Discontinued
0.6927 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6927 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6909 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6901 Remote Similarity NPD3124 Discontinued
0.6895 Remote Similarity NPD2490 Approved
0.6895 Remote Similarity NPD2488 Approved
0.6895 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6891 Remote Similarity NPD2973 Approved
0.6891 Remote Similarity NPD2975 Approved
0.6891 Remote Similarity NPD2974 Approved
0.689 Remote Similarity NPD3110 Approved
0.689 Remote Similarity NPD3109 Approved
0.689 Remote Similarity NPD2238 Phase 2
0.6889 Remote Similarity NPD7802 Discontinued
0.6888 Remote Similarity NPD3057 Approved
0.6886 Remote Similarity NPD2161 Phase 2
0.6885 Remote Similarity NPD8252 Approved
0.6885 Remote Similarity NPD8251 Approved
0.6885 Remote Similarity NPD8099 Discontinued
0.6882 Remote Similarity NPD3692 Discontinued
0.6879 Remote Similarity NPD5976 Discontinued
0.6878 Remote Similarity NPD3398 Discontinued
0.6871 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6871 Remote Similarity NPD3145 Approved
0.6871 Remote Similarity NPD3144 Approved
0.6854 Remote Similarity NPD6788 Approved
0.6848 Remote Similarity NPD5313 Approved
0.6848 Remote Similarity NPD5312 Approved
0.6845 Remote Similarity NPD7281 Phase 3
0.6845 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7280 Phase 3
0.6839 Remote Similarity NPD3687 Approved
0.6839 Remote Similarity NPD3686 Approved
0.6839 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6837 Remote Similarity NPD3450 Approved
0.6837 Remote Similarity NPD3452 Approved
0.6837 Remote Similarity NPD2494 Approved
0.6837 Remote Similarity NPD2493 Approved
0.6829 Remote Similarity NPD4474 Approved
0.6829 Remote Similarity NPD4475 Approved
0.6821 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6813 Remote Similarity NPD2388 Discontinued
0.6805 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6805 Remote Similarity NPD7153 Discontinued
0.68 Remote Similarity NPD7261 Clinical (unspecified phase)
0.68 Remote Similarity NPD4859 Phase 1
0.68 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6789 Remote Similarity NPD7291 Discontinued
0.6789 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4580 Approved
0.6784 Remote Similarity NPD5160 Discontinued
0.6782 Remote Similarity NPD1914 Approved
0.6774 Remote Similarity NPD6996 Clinical (unspecified phase)
0.6768 Remote Similarity NPD1039 Discontinued
0.6763 Remote Similarity NPD2874 Phase 2
0.6763 Remote Similarity NPD3645 Discontinued
0.6761 Remote Similarity NPD4678 Approved
0.6761 Remote Similarity NPD4675 Approved
0.6757 Remote Similarity NPD6042 Phase 2
0.6757 Remote Similarity NPD42 Phase 2
0.6755 Remote Similarity NPD2968 Approved
0.6755 Remote Similarity NPD5917 Clinical (unspecified phase)
0.6755 Remote Similarity NPD2971 Approved
0.6753 Remote Similarity NPD5582 Discontinued
0.675 Remote Similarity NPD1669 Approved
0.6744 Remote Similarity NPD2422 Clinical (unspecified phase)
0.674 Remote Similarity NPD2904 Discontinued
0.6734 Remote Similarity NPD4583 Approved
0.6734 Remote Similarity NPD4582 Approved
0.6727 Remote Similarity NPD554 Clinical (unspecified phase)
0.6726 Remote Similarity NPD2156 Approved
0.6726 Remote Similarity NPD2154 Approved
0.6726 Remote Similarity NPD2155 Approved
0.6724 Remote Similarity NPD7526 Approved
0.6724 Remote Similarity NPD52 Approved
0.6724 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6723 Remote Similarity NPD7438 Suspended
0.6722 Remote Similarity NPD4055 Discovery
0.6721 Remote Similarity NPD4083 Discontinued
0.6709 Remote Similarity NPD2667 Approved
0.6709 Remote Similarity NPD2668 Approved
0.6704 Remote Similarity NPD5977 Approved
0.6704 Remote Similarity NPD5978 Approved
0.6702 Remote Similarity NPD8453 Clinical (unspecified phase)
0.6687 Remote Similarity NPD2232 Approved
0.6687 Remote Similarity NPD2233 Approved
0.6687 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6687 Remote Similarity NPD2230 Approved
0.6687 Remote Similarity NPD3620 Phase 2
0.6686 Remote Similarity NPD2677 Approved
0.6685 Remote Similarity NPD5720 Discontinued
0.6685 Remote Similarity NPD4227 Discontinued
0.6684 Remote Similarity NPD4420 Approved
0.6683 Remote Similarity NPD4004 Approved
0.6683 Remote Similarity NPD4002 Approved
0.6667 Remote Similarity NPD7019 Approved
0.6667 Remote Similarity NPD6747 Phase 1
0.6667 Remote Similarity NPD597 Approved
0.6667 Remote Similarity NPD7020 Approved
0.6667 Remote Similarity NPD601 Approved
0.6667 Remote Similarity NPD4482 Phase 3
0.6667 Remote Similarity NPD598 Approved
0.6667 Remote Similarity NPD3638 Discontinued
0.6649 Remote Similarity NPD7038 Approved
0.6649 Remote Similarity NPD7039 Approved
0.6649 Remote Similarity NPD4951 Discontinued
0.6647 Remote Similarity NPD6666 Approved
0.6647 Remote Similarity NPD6667 Approved
0.6647 Remote Similarity NPD1375 Discontinued
0.6647 Remote Similarity NPD7124 Phase 2

Structure

External Identifiers

PubChem CID   44443383
ChEMBL   CHEMBL401479
ZINC  

Physicochemical Properties

Molecular Weight:  395.17
ALogP:  
MLogP:  3.33
XLogP:  
# Rotatable Bonds:  7
Polar Surface Area:  64.99
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  29

Download Data

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