NPASS Compound

Natural Product: NPC164241

Natural Product ID	NPC164241
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BZYXGNOWZQQMDJ-JGJIUCFZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	53359228
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 103110 0 0 0 0 0 0 0 0999 V2000 6.7262 1.8732 -1.0226 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1117 2.3509 -2.3550 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2235 2.3323 -3.3121 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8557 1.8637 -3.1472 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0389 1.8699 -4.1085 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3704 1.3849 -1.9314 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0174 0.9259 -1.7807 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8847 0.5048 -0.3371 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8882 -0.6398 -0.1220 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5424 -0.6838 1.2085 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2895 -1.4213 1.0872 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9310 -0.8318 1.3183 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0531 0.0976 2.4738 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6353 -0.2074 0.0017 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3946 0.6642 0.1017 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4307 0.0735 1.2084 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0202 0.5852 2.2256 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0814 2.0043 2.6562 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2968 2.6150 2.7615 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2094 3.0478 1.8602 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9686 2.9225 0.6491 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4985 3.6778 2.2739 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7355 4.8597 1.3530 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9860 5.5608 1.6886 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7313 5.1239 2.6117 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3841 6.7001 1.0224 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5670 7.3902 1.3221 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5544 -0.4979 3.0905 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1917 -0.2422 4.1640 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2288 -1.6455 2.5175 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5312 -1.4300 1.2407 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8646 -1.9199 1.5666 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2362 -3.2060 1.0553 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0755 -4.0700 0.7544 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0313 -3.6067 0.4567 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4060 -2.1422 0.3565 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7086 -2.0237 -1.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 -1.0560 -1.6255 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8949 0.1194 -0.8866 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6486 -1.0431 -3.0591 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3759 -1.9311 -3.8926 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3152 0.0687 -3.6362 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6195 0.1139 -5.0251 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3312 -3.1933 -1.9006 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6818 -2.9787 -2.9330 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7195 -4.5946 -1.5396 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9752 -4.6377 -0.0042 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3995 -4.3929 0.3232 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4140 -5.9193 0.4884 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8552 -6.0860 1.8768 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0014 -5.5996 0.7549 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9181 -4.9200 -2.1334 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1629 1.5993 0.4619 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4991 2.8400 -2.5542 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7387 3.2696 -3.8613 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5849 1.9316 -0.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4263 0.7994 -1.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9604 2.5421 -0.6024 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5270 2.6885 -4.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9423 -0.0009 -2.3988 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3007 1.6862 -2.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1511 -1.2772 -0.9625 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4931 -1.2956 1.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7005 0.2847 1.6851 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3643 -2.5088 1.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0991 0.1422 2.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7982 1.1449 2.2967 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4706 -0.2298 3.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4856 -0.9835 -0.7574 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7019 1.6885 0.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1376 0.5507 -0.8349 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5809 2.0921 3.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3973 2.5821 1.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3404 2.9414 2.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5050 3.9764 3.3261 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8743 5.5618 1.5533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7289 4.4920 0.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5302 8.4589 1.0429 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6998 7.3235 2.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4851 6.8845 0.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9509 -2.0063 2.7292 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9041 -3.8188 1.7275 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8230 -3.2061 0.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4984 -2.2303 0.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3859 1.0498 -1.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0321 0.0086 0.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9490 0.2611 -1.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9780 0.7908 -5.6019 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5647 -0.9426 -5.4041 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6778 0.4173 -5.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9188 -5.2697 -1.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4372 -3.9734 1.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9506 -3.7873 -0.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9288 -5.3653 0.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6020 -6.8576 -0.0971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6619 -7.1504 2.1702 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1488 -5.3909 2.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 -6.1453 0.3578 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4679 -5.5378 -1.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6358 2.2672 -0.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2365 2.0126 -2.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7400 3.6269 -1.8265 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8544 4.2533 -3.9320 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 17 28 1 0 28 29 2 0 28 30 1 0 31 30 1 1 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 38 40 1 0 40 41 2 0 40 42 1 0 42 43 1 0 37 44 1 0 44 45 2 0 44 46 1 0 46 47 1 0 47 48 1 6 47 49 1 0 49 50 1 0 50 51 1 0 46 52 1 0 8 53 1 1 2 54 1 0 54 55 1 0 14 8 1 0 31 16 1 0 51 34 1 0 11 9 1 0 32 12 1 0 47 35 1 0 51 49 1 0 36 31 1 0 1 56 1 0 1 57 1 0 1 58 1 0 3 59 1 0 7 60 1 0 7 61 1 0 9 62 1 6 10 63 1 0 10 64 1 0 11 65 1 6 13 66 1 0 13 67 1 0 13 68 1 0 14 69 1 6 15 70 1 0 15 71 1 0 18 72 1 0 18 73 1 0 22 74 1 0 22 75 1 0 23 76 1 0 23 77 1 0 27 78 1 0 27 79 1 0 27 80 1 0 32 81 1 1 33 82 1 0 33 83 1 0 36 84 1 1 39 85 1 0 39 86 1 0 39 87 1 0 43 88 1 0 43 89 1 0 43 90 1 0 46 91 1 1 48 92 1 0 48 93 1 0 48 94 1 0 49 95 1 6 50 96 1 0 50 97 1 0 51 98 1 6 52 99 1 0 53100 1 0 54101 1 0 54102 1 0 55103 1 0 M END

Standard InCHIKey	BZYXGNOWZQQMDJ-JGJIUCFZSA-N
Standard InCHI	InChI=1S/C41H48O14/c1-17(14-42)9-30(45)54-16-40(50)25-12-24(25)38(3)26(40)13-23-21(15-53-29(44)8-7-28(43)51-5)37(49)55-41(23)27(38)11-20-19-10-22(19)39(4)32(20)33(41)31(34(46)35(39)47)18(2)36(48)52-6/h9,19,22,24-27,33,35,42,47,50H,7-8,10-16H2,1-6H3/b17-9+,31-18-/t19-,22-,24-,25+,26-,27+,33+,35+,38+,39+,40+,41+/m1/s1
SMILES	C/C(=CC(=O)OC[C@@]1([C@H]2C[C@H]2[C@@]2(C)[C@H]1CC1=C(COC(=O)CCC(=O)OC)C(=O)O[C@@]31[C@H]2CC1=C2[C@@H]3/C(=C(C)/C(=O)OC)/C(=O)[C@@H]([C@@]2(C)[C@@H]2C[C@H]12)O)O)/CO

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1016/j.phytol.2016.01.005]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18451544]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	whole plants	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	Whole plant	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21650224]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21650224]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22372956]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588583]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27997206]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724564]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Ratio IC50	1
Activity	1

Activity Type	# Activity
Cell line	3
Organism	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell line	WI-38	Homo sapiens	IC50	=	5390.0	nM	PMID[27997206]
NPT113	Cell line	RAW264.7	Mus musculus	Activity	=	71.5	%	PMID[30724564]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	23100.0	nM	PMID[30724564]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.1	nM	PMID[27997206]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	4900.0	n.a.	PMID[27997206]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC164241 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	21591
0.1-0.2	27825
0.2-0.3	387
0.3-0.4	8
0.4-0.5	14
0.5-0.6	10
0.6-0.7	4
0.7-0.8	0
0.8-0.85	3
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC486797
0.8876	High Similarity	NPC241935
0.8876	High Similarity	NPC486803
0.8523	High Similarity	NPC299570
0.8523	High Similarity	NPC59488
0.8427	Intermediate Similarity	NPC19772
0.8387	Intermediate Similarity	NPC486798
0.8	Intermediate Similarity	NPC486799
0.7979	Intermediate Similarity	NPC34963
0.7979	Intermediate Similarity	NPC186637
0.7835	Intermediate Similarity	NPC279478
0.7717	Intermediate Similarity	NPC35109
0.7551	Intermediate Similarity	NPC486810
0.7363	Intermediate Similarity	NPC275236
0.7263	Intermediate Similarity	NPC196921
0.7234	Intermediate Similarity	NPC486811
0.7234	Intermediate Similarity	NPC220757
0.7129	Intermediate Similarity	NPC290020
0.7097	Intermediate Similarity	NPC15095
0.6857	Remote Similarity	NPC58029
0.6346	Remote Similarity	NPC469673
0.6277	Remote Similarity	NPC486809
0.6204	Remote Similarity	NPC486801
0.56	Remote Similarity	NPC17938
0.5586	Remote Similarity	NPC486804
0.5455	Remote Similarity	NPC263046
0.5446	Remote Similarity	NPC100347
0.5259	Remote Similarity	NPC486805
0.5253	Remote Similarity	NPC486812
0.5217	Remote Similarity	NPC486800
0.5208	Remote Similarity	NPC309497
0.5208	Remote Similarity	NPC611150
0.5044	Remote Similarity	NPC213697

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC164241 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7284
0.1-0.2	1844
0.2-0.3	22
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data