NPASS Compound

Natural Product: NPC473520

Natural Product ID	NPC473520
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S)-4-[7-[(2R,5S)-5-[(4S,7R)-7-[(2R,5R)-5-[(1R)-1-Hydroxytridecyl]Oxolan-2-Yl]-1,3-Dioxepan-4-Yl]Oxolan-2-Yl]Heptyl]-2-Methyl-2H-Furan-5-One
IUPAC Name	(2S)-4-[7-[(2R,5S)-5-[(4S,7R)-7-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-1,3-dioxepan-4-yl]oxolan-2-yl]heptyl]-2-methyl-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444465
PubChem CID	10627838
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 111114 0 0 0 0 0 0 0 0999 V2000 15.0281 -1.1914 0.8420 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9935 0.2651 0.5119 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6722 0.5698 -0.2026 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5589 -0.2312 -1.4676 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2768 0.1112 -2.1678 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1081 -0.2300 -1.2498 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8621 0.1265 -1.9941 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6478 -0.2430 -1.1184 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6604 0.4584 0.1777 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5399 0.2161 1.0891 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1960 0.7256 0.7766 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5206 0.3634 -0.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1395 0.8688 -0.6984 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0396 0.4831 0.2218 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1319 0.8880 1.6414 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6758 1.2648 2.0005 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 1.7886 0.6798 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9004 1.1228 -0.2832 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2711 1.7336 0.4613 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9681 2.3890 1.4476 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3153 2.0842 1.3503 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8605 2.1422 0.1160 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0435 0.9920 -0.5914 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7256 0.3266 -0.8932 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 0.3464 0.2905 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0326 0.0775 0.0729 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4451 -1.0785 -0.7718 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2780 -0.3975 -1.8341 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7704 0.8240 -1.0957 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2472 0.7654 0.1816 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2773 0.7475 -1.0055 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9678 0.7310 -2.3265 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4714 0.6611 -2.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9019 -0.6116 -1.5623 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4097 -0.7113 -1.4791 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0443 0.3707 -0.7094 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7088 0.5639 0.7129 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0193 -0.5041 1.6599 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8795 -0.3360 2.6902 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9955 -1.5797 3.4767 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.1331 -2.5130 2.8867 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5490 -1.8723 1.7857 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7232 -2.4442 1.0268 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.5925 -1.3597 4.9336 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6947 0.4343 -1.9989 O 0 0 0 0 0 0 0 0 0 0 0 0 15.7188 -1.7649 0.1650 H 0 0 0 0 0 0 0 0 0 0 0 0 15.3994 -1.4114 1.8749 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0353 -1.6861 0.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8449 0.6079 -0.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0397 0.9188 1.4270 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6529 1.6350 -0.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8888 0.2152 0.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4232 -0.0732 -2.1477 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5737 -1.3307 -1.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1487 -0.4035 -3.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2593 1.2209 -2.2801 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1335 -1.2789 -0.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1644 0.5044 -0.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7776 -0.4299 -2.9519 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8136 1.2279 -2.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7430 -1.3721 -0.8919 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8008 -0.1722 -1.7741 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6100 0.1119 0.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7584 1.5778 0.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4220 -0.9248 1.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7992 0.5253 2.1528 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4979 0.3615 1.6172 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1571 1.8524 0.9606 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1105 0.9681 -1.2955 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6772 -0.6755 -0.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1923 1.9891 -0.8313 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8774 -0.6344 0.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4198 0.0433 2.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6940 1.8233 1.8472 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1638 0.3204 2.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6673 2.0035 2.8181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5849 2.8646 0.6399 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4434 2.3395 -0.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5002 1.1660 1.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8287 2.8915 1.9621 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4817 1.2710 -1.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2085 0.8777 -1.7037 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8227 -0.7124 -1.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1566 -0.1512 1.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0969 -0.2931 -0.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7466 -0.2405 1.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6427 -1.6981 -1.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -1.7135 -0.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5998 -0.0608 -2.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0894 -1.0522 -2.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4601 1.7645 -1.6114 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6968 1.5546 -0.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5197 -0.1988 -0.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6051 -0.0523 -3.0228 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6750 1.6994 -2.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9120 1.5670 -1.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8457 0.6541 -3.2978 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5496 -1.4607 -2.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4357 -0.7139 -0.5641 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6997 -1.7347 -1.2943 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7380 -0.5401 -2.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1676 0.1622 -0.7382 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9902 1.3451 -1.2875 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2279 1.5225 1.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6262 0.8211 0.8809 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4083 0.5736 2.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0630 -1.8998 3.4260 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2797 -1.8352 5.6367 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5833 -1.8108 5.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5711 -0.2690 5.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0956 -0.4423 -2.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 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 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 40 44 1 0 13 45 1 0 18 14 1 0 25 19 1 0 30 26 1 0 42 38 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 0 8 62 1 0 9 63 1 0 9 64 1 0 10 65 1 0 10 66 1 0 11 67 1 0 11 68 1 0 12 69 1 0 12 70 1 0 13 71 1 6 14 72 1 1 15 73 1 0 15 74 1 0 16 75 1 0 16 76 1 0 17 77 1 1 19 78 1 6 21 79 1 0 21 80 1 0 23 81 1 6 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 26 86 1 1 27 87 1 0 27 88 1 0 28 89 1 0 28 90 1 0 29 91 1 6 31 92 1 0 31 93 1 0 32 94 1 0 32 95 1 0 33 96 1 0 33 97 1 0 34 98 1 0 34 99 1 0 35100 1 0 35101 1 0 36102 1 0 36103 1 0 37104 1 0 37105 1 0 39106 1 0 40107 1 1 44108 1 0 44109 1 0 44110 1 0 45111 1 0 M END

Standard InCHIKey	FJNAHVKQVREHDF-VUODRKSTSA-N
Standard InCHI	InChI=1S/C38H66O7/c1-3-4-5-6-7-8-9-10-14-17-20-32(39)33-23-26-37(45-33)35-25-24-34(41-28-42-35)36-22-21-31(44-36)19-16-13-11-12-15-18-30-27-29(2)43-38(30)40/h27,29,31-37,39H,3-26,28H2,1-2H3/t29-,31+,32+,33+,34-,35+,36-,37+/m0/s1
SMILES	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H]1OCO[C@@H](CC1)[C@@H]1CC[C@H](O1)CCCCCCCC1=C[C@@H](OC1=O)C)O

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
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	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
ED50	6

Activity Type	# Activity
Cell line	6

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	3.82	10'-2 ug/ml	PMID[16872140]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	4.95	10'-1 ug/ml	PMID[19928902]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.83	10'-1 ug/ml	PMID[19928902]
NPT376	Cell line	A498	Homo sapiens	ED50	=	1.62	10'-1 ug/ml	PMID[18663020]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	1.32	10'-1 ug/ml	PMID[22921081]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	2.17	10'-1 ug/ml	PMID[23501116]

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 NPC473520 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	15915
0.1-0.2	31312
0.2-0.3	2329
0.3-0.4	76
0.4-0.5	42
0.5-0.6	63
0.6-0.7	72
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC473995
0.7843	Intermediate Similarity	NPC25764
0.7843	Intermediate Similarity	NPC235809
0.7843	Intermediate Similarity	NPC39279
0.7843	Intermediate Similarity	NPC39167
0.7843	Intermediate Similarity	NPC292809
0.7843	Intermediate Similarity	NPC202055
0.7843	Intermediate Similarity	NPC606804
0.7843	Intermediate Similarity	NPC607425
0.7843	Intermediate Similarity	NPC608574
0.7627	Intermediate Similarity	NPC473663
0.7627	Intermediate Similarity	NPC473723
0.7627	Intermediate Similarity	NPC475173
0.7593	Intermediate Similarity	NPC241360
0.7593	Intermediate Similarity	NPC293136
0.7455	Intermediate Similarity	NPC65930
0.7407	Intermediate Similarity	NPC473156
0.7407	Intermediate Similarity	NPC282815
0.7407	Intermediate Similarity	NPC600956
0.7368	Intermediate Similarity	NPC169511
0.7368	Intermediate Similarity	NPC287164
0.7368	Intermediate Similarity	NPC234077
0.7273	Intermediate Similarity	NPC473671
0.7273	Intermediate Similarity	NPC219652
0.7273	Intermediate Similarity	NPC475268
0.7273	Intermediate Similarity	NPC473840
0.7273	Intermediate Similarity	NPC470400
0.7273	Intermediate Similarity	NPC77871
0.7273	Intermediate Similarity	NPC9678
0.7273	Intermediate Similarity	NPC319036
0.7273	Intermediate Similarity	NPC605867
0.7143	Intermediate Similarity	NPC132940
0.7091	Intermediate Similarity	NPC610454
0.7069	Intermediate Similarity	NPC258068
0.7069	Intermediate Similarity	NPC476583
0.7018	Intermediate Similarity	NPC329615
0.7018	Intermediate Similarity	NPC20533
0.7018	Intermediate Similarity	NPC485250
0.7018	Intermediate Similarity	NPC605396
0.7	Intermediate Similarity	NPC91067
0.6964	Remote Similarity	NPC25703
0.6923	Remote Similarity	NPC73310
0.6923	Remote Similarity	NPC473529
0.6923	Remote Similarity	NPC180363
0.6923	Remote Similarity	NPC94875
0.6923	Remote Similarity	NPC11332
0.6923	Remote Similarity	NPC145914
0.6923	Remote Similarity	NPC601174
0.6923	Remote Similarity	NPC601403
0.6923	Remote Similarity	NPC603568
0.6923	Remote Similarity	NPC604330
0.6923	Remote Similarity	NPC608300
0.6923	Remote Similarity	NPC611200
0.6923	Remote Similarity	NPC611571
0.6786	Remote Similarity	NPC473649
0.6786	Remote Similarity	NPC154097
0.6786	Remote Similarity	NPC159750
0.6786	Remote Similarity	NPC73248
0.6786	Remote Similarity	NPC470401
0.6786	Remote Similarity	NPC600524
0.6786	Remote Similarity	NPC608355
0.678	Remote Similarity	NPC120398
0.678	Remote Similarity	NPC471567
0.6667	Remote Similarity	NPC480082
0.6667	Remote Similarity	NPC604764
0.6613	Remote Similarity	NPC253801
0.6545	Remote Similarity	NPC329829
0.6545	Remote Similarity	NPC475159
0.6545	Remote Similarity	NPC131002
0.6545	Remote Similarity	NPC473780
0.6545	Remote Similarity	NPC604521
0.6452	Remote Similarity	NPC473791
0.6393	Remote Similarity	NPC320458
0.6393	Remote Similarity	NPC477014
0.6393	Remote Similarity	NPC477013
0.6349	Remote Similarity	NPC473905
0.6316	Remote Similarity	NPC81045
0.6316	Remote Similarity	NPC39754
0.6316	Remote Similarity	NPC171135
0.6316	Remote Similarity	NPC61257
0.6316	Remote Similarity	NPC320569
0.6316	Remote Similarity	NPC133730
0.6316	Remote Similarity	NPC191929
0.6316	Remote Similarity	NPC100454
0.6316	Remote Similarity	NPC242364
0.6316	Remote Similarity	NPC172821
0.6316	Remote Similarity	NPC156804
0.6316	Remote Similarity	NPC274446
0.6316	Remote Similarity	NPC485251
0.6316	Remote Similarity	NPC151403
0.6316	Remote Similarity	NPC261952
0.6316	Remote Similarity	NPC605171
0.6207	Remote Similarity	NPC93794
0.6207	Remote Similarity	NPC473504
0.6207	Remote Similarity	NPC163093
0.6207	Remote Similarity	NPC144415
0.6207	Remote Similarity	NPC81778
0.6207	Remote Similarity	NPC40066
0.6207	Remote Similarity	NPC607439
0.6207	Remote Similarity	NPC608157
0.619	Remote Similarity	NPC322529
0.6167	Remote Similarity	NPC20621
0.6167	Remote Similarity	NPC318963
0.6167	Remote Similarity	NPC602738
0.6167	Remote Similarity	NPC605101
0.6129	Remote Similarity	NPC89001
0.6094	Remote Similarity	NPC477015
0.6066	Remote Similarity	NPC473707
0.6066	Remote Similarity	NPC473478
0.6066	Remote Similarity	NPC473651
0.6066	Remote Similarity	NPC66346
0.6	Remote Similarity	NPC42598
0.5968	Remote Similarity	NPC283085
0.5968	Remote Similarity	NPC132496
0.5965	Remote Similarity	NPC100921
0.5965	Remote Similarity	NPC477018
0.5902	Remote Similarity	NPC329838
0.5714	Remote Similarity	NPC231096
0.5714	Remote Similarity	NPC475581
0.5714	Remote Similarity	NPC62118
0.5714	Remote Similarity	NPC107717
0.5714	Remote Similarity	NPC488252
0.5556	Remote Similarity	NPC609415
0.5538	Remote Similarity	NPC239517
0.5517	Remote Similarity	NPC606043
0.5469	Remote Similarity	NPC606740
0.5469	Remote Similarity	NPC608614
0.5455	Remote Similarity	NPC480081
0.5424	Remote Similarity	NPC107986
0.5424	Remote Similarity	NPC223871
0.5424	Remote Similarity	NPC231009
0.5424	Remote Similarity	NPC103284
0.5424	Remote Similarity	NPC110710
0.5424	Remote Similarity	NPC1083
0.5424	Remote Similarity	NPC82795
0.5424	Remote Similarity	NPC286338
0.5424	Remote Similarity	NPC603931
0.5424	Remote Similarity	NPC604237
0.5397	Remote Similarity	NPC309211
0.5397	Remote Similarity	NPC477010
0.5362	Remote Similarity	NPC477017
0.5362	Remote Similarity	NPC477016
0.5333	Remote Similarity	NPC488253
0.5333	Remote Similarity	NPC473669
0.5333	Remote Similarity	NPC488251
0.5312	Remote Similarity	NPC477012
0.5246	Remote Similarity	NPC232555
0.5246	Remote Similarity	NPC171174
0.5246	Remote Similarity	NPC182383
0.5246	Remote Similarity	NPC114694
0.5246	Remote Similarity	NPC485248
0.5246	Remote Similarity	NPC142117
0.5246	Remote Similarity	NPC480249
0.5246	Remote Similarity	NPC485249
0.5246	Remote Similarity	NPC240695
0.5224	Remote Similarity	NPC488630
0.5224	Remote Similarity	NPC488625
0.5224	Remote Similarity	NPC488626
0.5224	Remote Similarity	NPC280612
0.5161	Remote Similarity	NPC488632
0.5161	Remote Similarity	NPC480078
0.5161	Remote Similarity	NPC480071
0.5161	Remote Similarity	NPC134865
0.5161	Remote Similarity	NPC103523
0.5161	Remote Similarity	NPC488627
0.5161	Remote Similarity	NPC488631
0.5161	Remote Similarity	NPC477011
0.5152	Remote Similarity	NPC488623
0.5152	Remote Similarity	NPC488624
0.5152	Remote Similarity	NPC488629
0.5143	Remote Similarity	NPC482766
0.5143	Remote Similarity	NPC279267
0.5079	Remote Similarity	NPC280621
0.5079	Remote Similarity	NPC48338
0.5079	Remote Similarity	NPC488628

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6637
0.1-0.2	2465
0.2-0.3	48
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