NPASS Compound

Natural Product: NPC245760

Natural Product ID	NPC245760
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Xanthochymol
IUPAC Name	n.a.
Synonyms	(+)-Xanthochymol; Xanthochymol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510949
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 94 96 0 0 0 0 0 0 0 0999 V2000 6.5594 -1.9721 1.0944 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0233 -0.8560 1.5330 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6144 -0.1557 2.7237 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8156 -0.2157 0.8916 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4406 -1.0718 -0.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2258 -0.5423 -1.0596 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0893 -0.4690 -0.1808 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7242 -0.0455 -0.5357 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0324 -0.9196 -1.5476 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0473 -1.7784 -0.8430 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3465 -3.0062 -1.5981 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8493 -2.8330 -2.9763 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9750 -3.3922 -3.3512 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4113 -3.1597 -4.7757 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8566 -4.2412 -2.5347 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1341 -0.8934 -0.3986 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3164 -1.6394 0.0991 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6323 -0.0568 -1.5954 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5580 0.1142 0.5719 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1617 0.1521 1.9243 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0522 -1.0645 2.7438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5797 -1.0113 3.9926 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1700 0.2962 4.5438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4397 -2.2025 4.8730 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5997 1.5053 0.0339 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7032 2.0856 -0.1696 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3229 2.1735 -0.2566 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6439 1.4185 -0.8324 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5003 2.1044 -1.6703 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1359 3.5892 -0.0424 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9604 4.0550 -0.5621 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9439 4.5443 0.6360 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9583 4.2637 1.5087 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7607 5.2627 2.0645 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5518 6.5820 1.7491 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5345 6.8769 0.8760 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7464 5.8980 0.3284 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3412 8.2266 0.5722 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3395 7.6040 2.2895 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0891 -0.2163 0.7452 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3975 -0.5767 1.7741 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2234 -1.2142 -2.3570 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9567 -2.3462 -2.5426 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5635 -0.7380 -3.6053 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4365 -2.3871 1.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1570 -2.4904 0.2522 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6893 -0.4493 2.8272 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0722 -0.4743 3.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5021 0.9273 2.5318 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0120 -0.1858 1.6859 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0190 0.8010 0.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1737 -2.0743 0.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3006 -1.1754 -0.9899 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6229 0.5595 -1.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3910 0.1807 0.7100 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9688 -1.4824 0.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3746 -0.3810 -2.3904 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7157 -1.7205 -1.9331 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4851 -2.1112 0.0972 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9786 -3.6922 -1.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3739 -3.5844 -1.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2608 -2.2236 -3.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5569 -2.9092 -5.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1139 -2.3032 -4.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9039 -4.0724 -5.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4591 -5.2977 -2.5818 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8853 -4.1989 -2.9514 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9270 -3.9766 -1.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0772 -1.7068 -0.7396 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8831 -1.1267 0.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1139 -2.7036 0.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6549 0.3144 -1.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9605 0.7490 -1.8665 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8105 -0.6581 -2.4867 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2082 0.5663 1.9251 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5958 0.9692 2.4743 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3294 -2.0717 2.4258 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9551 0.2379 5.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3031 0.6920 4.0253 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0732 0.9693 4.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3371 -2.2315 5.5313 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4547 -3.0965 4.2263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5304 -2.1822 5.4945 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2139 2.2996 -2.6405 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 3.2601 1.8709 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5636 5.0227 2.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0343 6.2240 -0.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8055 8.6338 -0.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0736 7.9877 1.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9833 -2.8758 -3.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5494 -2.7994 -1.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9420 0.1304 -3.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8969 -1.5474 -3.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3251 -0.4695 -4.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 8 7 1 1 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 3 13 14 1 0 13 15 1 0 10 16 1 0 16 17 1 0 16 18 1 0 16 19 1 0 19 20 1 1 20 21 1 0 21 22 2 3 22 23 1 0 22 24 1 0 19 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 27 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 35 39 1 0 19 40 1 0 40 41 2 0 6 42 1 0 42 43 2 0 42 44 1 0 28 8 1 0 37 32 1 0 40 8 1 0 1 45 1 0 1 46 1 0 3 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 6 7 55 1 0 7 56 1 0 9 57 1 0 9 58 1 0 10 59 1 1 11 60 1 0 11 61 1 0 12 62 1 0 14 63 1 0 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 15 68 1 0 17 69 1 0 17 70 1 0 17 71 1 0 18 72 1 0 18 73 1 0 18 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 23 78 1 0 23 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 24 83 1 0 29 84 1 0 33 85 1 0 34 86 1 0 37 87 1 0 38 88 1 0 39 89 1 0 43 90 1 0 43 91 1 0 44 92 1 0 44 93 1 0 44 94 1 0 M END

Standard InCHIKey	ZLMZRAYSIVLUPA-AKAMJVKKSA-N
Standard InCHI	InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h12,14,16-17,19,27-28,39-40,42H,1,7,11,13,15,18,20-21H2,2-6,8-10H3/t27-,28+,37+,38-/m1/s1
SMILES	C=C(C)CC[C@H](C[C@]12C[C@H](CC=C(C)C)C(C)(C)[C@](CC=C(C)C)(C(=O)C(=C1O)C(=O)c1ccc(c(c1)O)O)C2=O)C(=C)C

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
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4020(01)89039-6]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14600386]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568764]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[15787435]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	pericarp	n.a.	n.a.	PMID[16038565]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[16562837]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18166016]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20232858]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	seeds and rinds	n.a.	n.a.	PMID[21028890]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21028890]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	Database[Article]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	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	8
GI	2
ED50	1
EC50	2

Activity Type	# Activity
Cell line	9
Others	2
Organism	2

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
NPT660	Cell line	SW480	Homo sapiens	IC50	=	8300.0	nM	PMID[15787435]
NPT858	Cell line	LNCaP	Homo sapiens	GI	=	44.0	%	PMID[19161316]
NPT858	Cell line	LNCaP	Homo sapiens	ED50	=	8.0	uM	PMID[19161316]
NPT858	Cell line	LNCaP	Homo sapiens	GI	=	65.0	%	PMID[19161316]
NPT81	Cell line	A549	Homo sapiens	IC50	=	4.0	ug.mL-1	PMID[20232858]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	4.0	ug.mL-1	PMID[20232858]
NPT91	Cell line	KB	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[20232858]
NPT91	Cell line	KB	Homo sapiens	IC50	=	4.6	ug.mL-1	PMID[20232858]
NPT380	Cell line	U-251	Homo sapiens	IC50	=	2300.0	nM	PMID[28729053]
NPT20	Organism	Candida albicans	Candida albicans	EC50	=	30000.0	nM	PMID[28051303]
NPT20	Organism	Candida albicans	Candida albicans	EC50	=	13.0	ug.mL-1	PMID[28051303]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	53000.0	nM	PMID[15787435]
NPT2	Others	Unspecified	n.a.	IC50	=	2000.0	nM	PMID[10978200]

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 NPC245760 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	7813
0.1-0.2	40498
0.2-0.3	1423
0.3-0.4	42
0.4-0.5	19
0.5-0.6	20
0.6-0.7	16
0.7-0.8	0
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469857
0.8939	High Similarity	NPC46242
0.8939	High Similarity	NPC91887
0.8939	High Similarity	NPC93556
0.8571	High Similarity	NPC603871
0.831	Intermediate Similarity	NPC471971
0.831	Intermediate Similarity	NPC471972
0.831	Intermediate Similarity	NPC469855
0.8261	Intermediate Similarity	NPC297797
0.8182	Intermediate Similarity	NPC149773
0.7703	Intermediate Similarity	NPC469856
0.7671	Intermediate Similarity	NPC294330
0.76	Intermediate Similarity	NPC471970
0.7568	Intermediate Similarity	NPC469854
0.7534	Intermediate Similarity	NPC165191
0.7534	Intermediate Similarity	NPC177501
0.7397	Intermediate Similarity	NPC114333
0.7397	Intermediate Similarity	NPC28592
0.7397	Intermediate Similarity	NPC51531
0.7297	Intermediate Similarity	NPC473479
0.7297	Intermediate Similarity	NPC50615
0.7297	Intermediate Similarity	NPC30846
0.7297	Intermediate Similarity	NPC141650
0.7013	Intermediate Similarity	NPC237441
0.6757	Remote Similarity	NPC289358
0.6757	Remote Similarity	NPC4289
0.6757	Remote Similarity	NPC42384
0.6753	Remote Similarity	NPC479151
0.6456	Remote Similarity	NPC5014
0.641	Remote Similarity	NPC479148
0.6338	Remote Similarity	NPC259400
0.6338	Remote Similarity	NPC130591
0.6338	Remote Similarity	NPC234637
0.6329	Remote Similarity	NPC23667
0.6329	Remote Similarity	NPC157284
0.6296	Remote Similarity	NPC479146
0.6164	Remote Similarity	NPC611064
0.6133	Remote Similarity	NPC473779
0.6071	Remote Similarity	NPC482617
0.6071	Remote Similarity	NPC482616
0.5949	Remote Similarity	NPC473527
0.5926	Remote Similarity	NPC482621
0.5765	Remote Similarity	NPC482618
0.575	Remote Similarity	NPC198803
0.5595	Remote Similarity	NPC7464
0.5529	Remote Similarity	NPC294679
0.5529	Remote Similarity	NPC145301
0.5529	Remote Similarity	NPC302044
0.5529	Remote Similarity	NPC600911
0.5412	Remote Similarity	NPC25736
0.5244	Remote Similarity	NPC479147
0.5233	Remote Similarity	NPC264229
0.5233	Remote Similarity	NPC46549
0.5233	Remote Similarity	NPC606601
0.519	Remote Similarity	NPC474715
0.5181	Remote Similarity	NPC48949
0.5059	Remote Similarity	NPC8493
0.5059	Remote Similarity	NPC469375
0.5059	Remote Similarity	NPC110855
0.5059	Remote Similarity	NPC144247

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC245760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3751
0.1-0.2	5353
0.2-0.3	46
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