Natural Product: NPC161827

Natural Product ID:  NPC161827
Common Name:   Macrophyllionium
IUPAC Name:   (1R,4R,6R,7S,8aR)-7-[(Z)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-6-ethyl-4-methylspiro[3,5,6,7,8,8a-hexahydro-2H-indolizin-4-ium-1,3'-indole]-2'-olate
Synonyms:   Macrophyllionium
Molecular Formula:   C23H30N2O4
Standard InCHIKey:  QVNYBASBMONTJV-VSDFPOAWSA-N
Standard InCHI:  InChI=1S/C23H30N2O4/c1-5-15-13-25(2)11-10-23(18-8-6-7-9-19(18)24-22(23)27)20(25)12-16(15)17(14-28-3)21(26)29-4/h6-9,14-16,20H,5,10-13H2,1-4H3/b17-14-/t15-,16-,20+,23+,25+/m0/s1
Canonical SMILES:  CO/C=C(/[C@H]1C[C@H]2[N@+](C[C@@H]1CC)(C)CC[C@@]12C(=Nc2c1cccc2)[O-])C(=O)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
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota PMID[21070010]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT660 Cell Line SW480 Homo sapiens IC50 > 40000 nM 19743809
NPT177 Tissue Aorta Rattus norvegicus IC50 > 30 ug/ml 15270577
NPT116 Cell Line HL-60 Homo sapiens IC50 > 40000 nM 10617079

  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 NPC161827 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
0.9795 High Similarity NPC310403
0.9795 High Similarity NPC97380
0.9795 High Similarity NPC243673
0.9795 High Similarity NPC148468
0.9795 High Similarity NPC63210
0.9795 High Similarity NPC263709
0.9592 High Similarity NPC153694
0.9592 High Similarity NPC211525
0.9533 High Similarity NPC470069
0.9533 High Similarity NPC52059
0.9226 High Similarity NPC298851
0.9226 High Similarity NPC276993
0.9226 High Similarity NPC21752
0.9226 High Similarity NPC181138
0.9226 High Similarity NPC293255
0.9226 High Similarity NPC210415
0.8654 High Similarity NPC472121
0.7987 Intermediate Similarity NPC473297
0.7927 Intermediate Similarity NPC278887
0.7901 Intermediate Similarity NPC474058
0.7885 Intermediate Similarity NPC472100
0.784 Intermediate Similarity NPC193410
0.7829 Intermediate Similarity NPC28510
0.7812 Intermediate Similarity NPC478076
0.7798 Intermediate Similarity NPC13367
0.7791 Intermediate Similarity NPC248117
0.7778 Intermediate Similarity NPC61013
0.7756 Intermediate Similarity NPC472103
0.7738 Intermediate Similarity NPC476425
0.7684 Intermediate Similarity NPC204970
0.7683 Intermediate Similarity NPC143457
0.7683 Intermediate Similarity NPC225319
0.7674 Intermediate Similarity NPC475962
0.7647 Intermediate Similarity NPC203202
0.7647 Intermediate Similarity NPC264482
0.7605 Intermediate Similarity NPC279527
0.7605 Intermediate Similarity NPC214960
0.7571 Intermediate Similarity NPC174629
0.7561 Intermediate Similarity NPC123241
0.756 Intermediate Similarity NPC224970
0.756 Intermediate Similarity NPC167724
0.756 Intermediate Similarity NPC469462
0.756 Intermediate Similarity NPC223595
0.7558 Intermediate Similarity NPC6974
0.7544 Intermediate Similarity NPC476441
0.7543 Intermediate Similarity NPC472209
0.7543 Intermediate Similarity NPC469460
0.7542 Intermediate Similarity NPC203972
0.753 Intermediate Similarity NPC282339
0.753 Intermediate Similarity NPC99632
0.7515 Intermediate Similarity NPC469461
0.75 Intermediate Similarity NPC243162
0.75 Intermediate Similarity NPC29285
0.75 Intermediate Similarity NPC186669
0.7457 Intermediate Similarity NPC99043
0.7457 Intermediate Similarity NPC218594
0.7455 Intermediate Similarity NPC113946
0.7429 Intermediate Similarity NPC159963
0.7425 Intermediate Similarity NPC293458
0.7416 Intermediate Similarity NPC102338
0.7416 Intermediate Similarity NPC63199
0.7416 Intermediate Similarity NPC196251
0.7416 Intermediate Similarity NPC111602
0.741 Intermediate Similarity NPC36495
0.7401 Intermediate Similarity NPC282092
0.7399 Intermediate Similarity NPC476326
0.7396 Intermediate Similarity NPC472115
0.7396 Intermediate Similarity NPC472114
0.7383 Intermediate Similarity NPC317758
0.736 Intermediate Similarity NPC14994
0.736 Intermediate Similarity NPC21425
0.7333 Intermediate Similarity NPC25401
0.7312 Intermediate Similarity NPC474077
0.7288 Intermediate Similarity NPC472119
0.7288 Intermediate Similarity NPC97584
0.7283 Intermediate Similarity NPC469726
0.7283 Intermediate Similarity NPC329338
0.7273 Intermediate Similarity NPC476428
0.7257 Intermediate Similarity NPC321211
0.7247 Intermediate Similarity NPC322621
0.7237 Intermediate Similarity NPC478079
0.7225 Intermediate Similarity NPC214626
0.7225 Intermediate Similarity NPC251212
0.7225 Intermediate Similarity NPC139085
0.7219 Intermediate Similarity NPC176983
0.7219 Intermediate Similarity NPC286871
0.7216 Intermediate Similarity NPC39822
0.7198 Intermediate Similarity NPC55493
0.7191 Intermediate Similarity NPC258480
0.7191 Intermediate Similarity NPC245741
0.7189 Intermediate Similarity NPC100863
0.7174 Intermediate Similarity NPC245916
0.716 Intermediate Similarity NPC201424
0.716 Intermediate Similarity NPC116519
0.7152 Intermediate Similarity NPC281104
0.7151 Intermediate Similarity NPC473007
0.7143 Intermediate Similarity NPC22476
0.7126 Intermediate Similarity NPC96901
0.7118 Intermediate Similarity NPC472101
0.7118 Intermediate Similarity NPC472117
0.7118 Intermediate Similarity NPC472120
0.7112 Intermediate Similarity NPC254240
0.7112 Intermediate Similarity NPC294909
0.7112 Intermediate Similarity NPC128265
0.7112 Intermediate Similarity NPC312870
0.7112 Intermediate Similarity NPC199851
0.7111 Intermediate Similarity NPC291759
0.7088 Intermediate Similarity NPC473008
0.7088 Intermediate Similarity NPC473298
0.7088 Intermediate Similarity NPC5630
0.7072 Intermediate Similarity NPC181928
0.7059 Intermediate Similarity NPC309531
0.7059 Intermediate Similarity NPC472102
0.7056 Intermediate Similarity NPC133591
0.7049 Intermediate Similarity NPC203628
0.7043 Intermediate Similarity NPC302548
0.7043 Intermediate Similarity NPC475559
0.7035 Intermediate Similarity NPC472106
0.7029 Intermediate Similarity NPC285622
0.7027 Intermediate Similarity NPC474121
0.7027 Intermediate Similarity NPC19692
0.7027 Intermediate Similarity NPC220151
0.7021 Intermediate Similarity NPC214428
0.7017 Intermediate Similarity NPC66210
0.7017 Intermediate Similarity NPC207033
0.7017 Intermediate Similarity NPC38823
0.7016 Intermediate Similarity NPC277350
0.7011 Intermediate Similarity NPC473004
0.7006 Intermediate Similarity NPC260075
0.7006 Intermediate Similarity NPC234987
0.7 Intermediate Similarity NPC319645
0.6995 Remote Similarity NPC22689
0.6995 Remote Similarity NPC472112
0.6995 Remote Similarity NPC329858
0.6995 Remote Similarity NPC314333
0.6995 Remote Similarity NPC105055
0.6988 Remote Similarity NPC473329
0.6982 Remote Similarity NPC477157
0.6982 Remote Similarity NPC477156
0.698 Remote Similarity NPC264580
0.6978 Remote Similarity NPC472323
0.6977 Remote Similarity NPC313757
0.6974 Remote Similarity NPC472098
0.6963 Remote Similarity NPC14339
0.6954 Remote Similarity NPC148183
0.6954 Remote Similarity NPC152768
0.6947 Remote Similarity NPC1464
0.6947 Remote Similarity NPC162730
0.6946 Remote Similarity NPC243756
0.6944 Remote Similarity NPC98197
0.6935 Remote Similarity NPC34717
0.6931 Remote Similarity NPC138830
0.6927 Remote Similarity NPC246140
0.6927 Remote Similarity NPC195787
0.6919 Remote Similarity NPC476231
0.6915 Remote Similarity NPC218733
0.6915 Remote Similarity NPC138615
0.6915 Remote Similarity NPC132874
0.6915 Remote Similarity NPC265642
0.6898 Remote Similarity NPC303214
0.6895 Remote Similarity NPC232600
0.6894 Remote Similarity NPC469560
0.689 Remote Similarity NPC190945
0.6878 Remote Similarity NPC241024
0.6875 Remote Similarity NPC475147
0.6875 Remote Similarity NPC87714
0.6868 Remote Similarity NPC52262
0.6862 Remote Similarity NPC90967
0.6859 Remote Similarity NPC474116
0.6851 Remote Similarity NPC143533
0.6848 Remote Similarity NPC217294
0.6845 Remote Similarity NPC243626
0.6845 Remote Similarity NPC230313
0.6842 Remote Similarity NPC67904
0.6839 Remote Similarity NPC238457
0.6833 Remote Similarity NPC15840
0.6828 Remote Similarity NPC472113
0.6826 Remote Similarity NPC242000
0.6825 Remote Similarity NPC52557
0.6818 Remote Similarity NPC469915
0.6818 Remote Similarity NPC472118
0.6816 Remote Similarity NPC472099
0.6811 Remote Similarity NPC474059
0.6811 Remote Similarity NPC473569
0.6806 Remote Similarity NPC469732
0.6802 Remote Similarity NPC471122
0.6796 Remote Similarity NPC113626
0.6788 Remote Similarity NPC475847
0.6788 Remote Similarity NPC185742
0.6776 Remote Similarity NPC79062
0.6776 Remote Similarity NPC472107
0.6774 Remote Similarity NPC472097
0.6774 Remote Similarity NPC325013
0.6771 Remote Similarity NPC473005
0.677 Remote Similarity NPC471123
0.6763 Remote Similarity NPC315368
0.676 Remote Similarity NPC84347
0.6758 Remote Similarity NPC477159
0.6758 Remote Similarity NPC159125
0.6757 Remote Similarity NPC175474

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC161827 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
0.7403 Intermediate Similarity NPD5185 Approved
0.7403 Intermediate Similarity NPD5182 Approved
0.7403 Intermediate Similarity NPD5184 Approved
0.7325 Intermediate Similarity NPD3170 Approved
0.7211 Intermediate Similarity NPD2994 Approved
0.7152 Intermediate Similarity NPD2569 Approved
0.7152 Intermediate Similarity NPD2670 Approved
0.7152 Intermediate Similarity NPD2567 Approved
0.7143 Intermediate Similarity NPD2115 Approved
0.7143 Intermediate Similarity NPD2117 Pre-registration
0.7143 Intermediate Similarity NPD2116 Approved
0.7112 Intermediate Similarity NPD4501 Approved
0.7112 Intermediate Similarity NPD4500 Approved
0.7067 Intermediate Similarity NPD2946 Phase 2
0.7047 Intermediate Similarity NPD3030 Approved
0.7047 Intermediate Similarity NPD3032 Approved
0.7047 Intermediate Similarity NPD3031 Approved
0.7 Intermediate Similarity NPD1110 Approved
0.7 Intermediate Similarity NPD7599 Phase 2
0.7 Intermediate Similarity NPD1109 Approved
0.6995 Remote Similarity NPD4499 Approved
0.6978 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7600 Phase 2
0.6936 Remote Similarity NPD7591 Clinical (unspecified phase)
0.6909 Remote Similarity NPD4041 Approved
0.689 Remote Similarity NPD2435 Approved
0.6867 Remote Similarity NPD1801 Approved
0.6867 Remote Similarity NPD1802 Approved
0.6864 Remote Similarity NPD4120 Approved
0.6864 Remote Similarity NPD4121 Phase 3
0.6857 Remote Similarity NPD2844 Phase 3
0.6848 Remote Similarity NPD5595 Clinical (unspecified phase)
0.6826 Remote Similarity NPD7528 Approved
0.6825 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5743 Approved
0.6824 Remote Similarity NPD5742 Approved
0.6824 Remote Similarity NPD5741 Approved
0.6821 Remote Similarity NPD2210 Approved
0.6821 Remote Similarity NPD2212 Approved
0.6805 Remote Similarity NPD2948 Discontinued
0.6803 Remote Similarity NPD2607 Approved
0.6802 Remote Similarity NPD7114 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6414 Clinical (unspecified phase)
0.6744 Remote Similarity NPD5715 Clinical (unspecified phase)
0.6738 Remote Similarity NPD7569 Approved
0.6738 Remote Similarity NPD7570 Approved
0.6727 Remote Similarity NPD2820 Phase 3
0.6726 Remote Similarity NPD4682 Phase 2
0.6712 Remote Similarity NPD1752 Approved
0.6712 Remote Similarity NPD1756 Approved
0.6707 Remote Similarity NPD6416 Phase 2
0.6706 Remote Similarity NPD3399 Approved
0.6705 Remote Similarity NPD8002 Clinical (unspecified phase)
0.6705 Remote Similarity NPD8003 Clinical (unspecified phase)
0.6688 Remote Similarity NPD2611 Approved
0.6688 Remote Similarity NPD4216 Approved
0.6688 Remote Similarity NPD4217 Approved
0.6688 Remote Similarity NPD4218 Approved
0.6688 Remote Similarity NPD4215 Approved
0.6688 Remote Similarity NPD2608 Approved
0.6688 Remote Similarity NPD2612 Approved
0.6688 Remote Similarity NPD2610 Approved
0.6688 Remote Similarity NPD2609 Approved
0.6688 Remote Similarity NPD3132 Approved
0.6688 Remote Similarity NPD3131 Approved
0.6667 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7252 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5811 Approved
0.6667 Remote Similarity NPD4602 Approved
0.6667 Remote Similarity NPD2365 Approved
0.6648 Remote Similarity NPD6878 Phase 2
0.6648 Remote Similarity NPD6879 Phase 2
0.663 Remote Similarity NPD8006 Clinical (unspecified phase)
0.6629 Remote Similarity NPD7795 Phase 2
0.6628 Remote Similarity NPD7463 Clinical (unspecified phase)
0.6624 Remote Similarity NPD552 Approved
0.6624 Remote Similarity NPD9567 Approved
0.6624 Remote Similarity NPD553 Approved
0.6615 Remote Similarity NPD6874 Approved
0.6615 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6612 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6359 Clinical (unspecified phase)
0.6592 Remote Similarity NPD7687 Clinical (unspecified phase)
0.6573 Remote Similarity NPD3983 Phase 3
0.6573 Remote Similarity NPD6457 Approved
0.6573 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7244 Discontinued
0.6554 Remote Similarity NPD7036 Phase 3
0.6554 Remote Similarity NPD4796 Discontinued
0.6554 Remote Similarity NPD7035 Approved
0.6552 Remote Similarity NPD3812 Clinical (unspecified phase)
0.6538 Remote Similarity NPD5600 Discontinued
0.6538 Remote Similarity NPD3965 Phase 1
0.6536 Remote Similarity NPD5186 Approved
0.6536 Remote Similarity NPD5183 Approved
0.6534 Remote Similarity NPD19 Approved
0.6534 Remote Similarity NPD1742 Approved
0.6534 Remote Similarity NPD1743 Approved
0.6533 Remote Similarity NPD1373 Approved
0.6533 Remote Similarity NPD1370 Approved
0.6533 Remote Similarity NPD1371 Approved
0.6533 Remote Similarity NPD1374 Approved
0.6528 Remote Similarity NPD6999 Discontinued
0.6528 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6522 Remote Similarity NPD3435 Discontinued
0.6515 Remote Similarity NPD2509 Approved
0.6515 Remote Similarity NPD2510 Approved
0.6513 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6508 Remote Similarity NPD5076 Approved
0.6508 Remote Similarity NPD5077 Approved
0.65 Remote Similarity NPD2613 Approved
0.6497 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6495 Remote Similarity NPD4601 Approved
0.6495 Remote Similarity NPD4600 Approved
0.6494 Remote Similarity NPD6570 Approved
0.6494 Remote Similarity NPD6571 Approved
0.6491 Remote Similarity NPD2737 Clinical (unspecified phase)
0.649 Remote Similarity NPD4766 Approved
0.6488 Remote Similarity NPD7487 Discontinued
0.6485 Remote Similarity NPD6655 Clinical (unspecified phase)
0.6484 Remote Similarity NPD8022 Clinical (unspecified phase)
0.648 Remote Similarity NPD2680 Approved
0.648 Remote Similarity NPD6176 Phase 1
0.648 Remote Similarity NPD2681 Approved
0.648 Remote Similarity NPD4986 Clinical (unspecified phase)
0.6477 Remote Similarity NPD4397 Phase 1
0.6474 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6467 Remote Similarity NPD2923 Approved
0.6467 Remote Similarity NPD181 Approved
0.6464 Remote Similarity NPD5997 Discontinued
0.6462 Remote Similarity NPD6238 Discontinued
0.6457 Remote Similarity NPD3589 Clinical (unspecified phase)
0.6456 Remote Similarity NPD5577 Clinical (unspecified phase)
0.6456 Remote Similarity NPD5578 Approved
0.6456 Remote Similarity NPD1036 Approved
0.6453 Remote Similarity NPD3329 Clinical (unspecified phase)
0.6453 Remote Similarity NPD7606 Phase 3
0.6452 Remote Similarity NPD3436 Approved
0.645 Remote Similarity NPD4900 Clinical (unspecified phase)
0.645 Remote Similarity NPD6017 Discontinued
0.6448 Remote Similarity NPD3050 Clinical (unspecified phase)
0.6447 Remote Similarity NPD8283 Approved
0.6447 Remote Similarity NPD56 Approved
0.6447 Remote Similarity NPD8282 Approved
0.6447 Remote Similarity NPD2622 Approved
0.6442 Remote Similarity NPD8416 Discontinued
0.6437 Remote Similarity NPD1093 Approved
0.6437 Remote Similarity NPD1092 Approved
0.6433 Remote Similarity NPD2584 Suspended
0.6433 Remote Similarity NPD3623 Clinical (unspecified phase)
0.6433 Remote Similarity NPD3622 Clinical (unspecified phase)
0.6433 Remote Similarity NPD5942 Approved
0.6433 Remote Similarity NPD5941 Approved
0.6432 Remote Similarity NPD8399 Phase 1
0.6432 Remote Similarity NPD8423 Phase 2
0.6429 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5919 Clinical (unspecified phase)
0.6425 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6424 Remote Similarity NPD2659 Approved
0.6424 Remote Similarity NPD3150 Approved
0.6424 Remote Similarity NPD3149 Approved
0.6424 Remote Similarity NPD3147 Approved
0.6424 Remote Similarity NPD3148 Approved
0.6424 Remote Similarity NPD2658 Approved
0.6418 Remote Similarity NPD7470 Discontinued
0.6414 Remote Similarity NPD7001 Phase 3
0.6414 Remote Similarity NPD6732 Clinical (unspecified phase)
0.641 Remote Similarity NPD6805 Discontinued
0.6407 Remote Similarity NPD3625 Discontinued
0.6405 Remote Similarity NPD4574 Approved
0.6405 Remote Similarity NPD4576 Approved
0.6404 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6402 Remote Similarity NPD8643 Discontinued
0.64 Remote Similarity NPD4506 Discontinued
0.64 Remote Similarity NPD1663 Discontinued
0.6396 Remote Similarity NPD7205 Discontinued
0.6396 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6393 Remote Similarity NPD5104 Approved
0.6391 Remote Similarity NPD2387 Approved
0.6386 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6382 Remote Similarity NPD5631 Phase 3
0.638 Remote Similarity NPD3089 Approved
0.638 Remote Similarity NPD3614 Approved
0.638 Remote Similarity NPD2571 Approved
0.638 Remote Similarity NPD3087 Approved
0.638 Remote Similarity NPD2573 Approved
0.638 Remote Similarity NPD4746 Phase 3
0.638 Remote Similarity NPD3090 Approved
0.638 Remote Similarity NPD3088 Approved
0.638 Remote Similarity NPD2570 Approved
0.638 Remote Similarity NPD2566 Approved
0.638 Remote Similarity NPD3615 Approved
0.638 Remote Similarity NPD4745 Approved
0.638 Remote Similarity NPD3616 Approved
0.638 Remote Similarity NPD7634 Clinical (unspecified phase)
0.638 Remote Similarity NPD2574 Discontinued
0.638 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6374 Remote Similarity NPD2248 Approved
0.6374 Remote Similarity NPD7478 Approved
0.6374 Remote Similarity NPD2246 Approved

Structure

External Identifiers

PubChem CID   53322220
ChEMBL   CHEMBL1668784
ZINC  

Physicochemical Properties

Molecular Weight:  398.22
ALogP:  -2.8533
MLogP:  3.33
XLogP:  3.204
# Rotatable Bonds:  10
Polar Surface Area:  70.95
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  29

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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