NPASS Compound

Natural Product: NPC61651

Natural Product ID	NPC61651
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YHHGNIYHQAAXRC-QZZPBPMGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419287
PubChem CID	73350741
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

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 92 95 0 0 0 0 0 0 0 0999 V2000 -4.9966 -3.1514 -1.0933 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9527 -3.1985 -2.1343 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0191 -2.2748 -2.1908 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0242 -1.1475 -1.1651 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7759 -1.1550 -0.3904 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6239 -0.1323 0.7237 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7927 -0.4274 1.6525 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8328 1.2595 0.1581 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3168 2.2257 1.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6014 3.5789 0.7071 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9671 4.0362 -0.4583 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1500 5.5708 -0.5173 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2919 3.3126 -1.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6089 1.8280 -0.4746 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6819 1.5576 0.2017 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5643 2.7752 0.3378 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1081 2.9058 -1.0689 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5526 3.3858 -1.0624 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0381 3.4963 -2.4907 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7280 4.6666 -0.3067 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1549 1.5648 -1.5648 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4878 0.7026 -0.7237 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4284 -0.6133 -0.5910 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2895 -1.4182 -1.5191 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2009 -2.2300 -0.6738 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2656 -3.5468 -0.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1872 -4.3492 0.0844 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4131 -4.2273 -1.7831 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5799 -1.2048 0.4007 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5573 -2.4590 0.4962 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3060 -0.4043 1.3567 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2782 -1.1872 2.5998 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3769 -1.5859 3.1012 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8912 -1.5697 3.3436 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7612 -2.2771 4.5160 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8494 -2.6771 5.2685 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1204 -2.3643 4.8428 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2431 -1.6560 3.6684 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1476 -1.2601 2.9220 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4405 0.8877 1.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 1.3647 2.5360 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9547 -4.2977 -3.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6759 -2.2743 -1.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5776 -3.0959 -0.0647 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5973 -4.1041 -1.0981 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2318 -2.2609 -2.9317 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9503 -1.2304 -0.6146 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0884 -0.1972 -1.7777 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8685 -1.2016 -1.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7307 -2.1509 0.1495 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 -1.5075 1.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7472 -0.0273 1.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7594 0.0132 2.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5872 1.1508 -0.6284 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2011 1.8071 1.7641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5582 2.3385 2.0208 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4884 4.3979 1.4991 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5155 6.0553 0.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8716 5.8986 -1.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2296 5.7114 -0.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7689 4.0455 -2.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4793 2.8651 -2.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1354 2.6034 -1.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5898 1.5531 -1.5710 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7662 2.9560 -0.5216 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4113 2.4904 1.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0270 3.6789 0.6699 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 3.5508 -1.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2089 2.6230 -0.5780 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2091 3.5968 -3.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6998 4.3782 -2.6143 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6343 2.6149 -2.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4802 4.5831 0.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7700 5.0921 0.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1681 5.4305 -1.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9246 -0.7401 -2.1061 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6485 -2.0642 -2.1676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8381 -1.7404 0.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6923 -5.2839 0.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0887 -4.5973 -0.4986 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4949 -3.6970 0.9465 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7470 -5.2945 -1.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3631 -4.1864 -1.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5420 -3.7697 -2.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2152 -2.5708 4.9317 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7439 -3.2284 6.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9938 -2.6724 5.4238 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2347 -1.4137 3.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3835 -0.7165 2.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8567 -4.9490 -3.0065 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0063 -4.8963 -3.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9658 -3.8678 -4.1681 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 6 5 1 6 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 3 11 12 1 0 11 13 1 0 8 14 1 0 15 14 1 6 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 17 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 2 3 26 27 1 0 26 28 1 0 23 29 1 0 29 30 2 0 29 31 1 0 31 32 1 1 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 31 40 1 0 40 41 2 0 2 42 1 0 31 6 1 0 39 34 1 0 22 15 1 0 40 15 1 0 1 43 1 0 1 44 1 0 1 45 1 0 3 46 1 0 4 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 6 9 55 1 0 9 56 1 0 10 57 1 0 12 58 1 0 12 59 1 0 12 60 1 0 13 61 1 0 13 62 1 0 13 63 1 0 14 64 1 0 14 65 1 0 16 66 1 0 16 67 1 0 17 68 1 6 18 69 1 0 19 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 20 75 1 0 24 76 1 0 24 77 1 0 25 78 1 0 27 79 1 0 27 80 1 0 27 81 1 0 28 82 1 0 28 83 1 0 28 84 1 0 35 85 1 0 36 86 1 0 37 87 1 0 38 88 1 0 39 89 1 0 42 90 1 0 42 91 1 0 42 92 1 0 M END

Standard InCHIKey	YHHGNIYHQAAXRC-QZZPBPMGSA-N
Standard InCHI	InChI=1S/C38H50O4/c1-24(2)14-13-21-36(9)29(19-17-25(3)4)22-37-23-31(27(7)8)42-34(37)30(20-18-26(5)6)33(40)38(36,35(37)41)32(39)28-15-11-10-12-16-28/h10-12,14-18,27,29,31H,13,19-23H2,1-9H3/t29-,31-,36+,37-,38-/m0/s1
SMILES	CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]23C[C@@H](C(C)C)OC2=C(CC=C(C)C)C(=O)[C@@]1(C(=O)c1ccccc1)C3=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	570.37	Volume:	640.374 ? Van der Waals volume.
Dense:	0.891	LogP:	6.598 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.967 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.315 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	26.0
TPSA:	60.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.16	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.142	Fsp³:	0.553
MCE-18:	139.831 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.996	Fluc inhibitor:	0.086 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.141 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.444 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.417	Promiscuous compounds:	0.009

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.559	MDCK Permeability:	-4.724
Pgp-inhibitor:	0.489	Pgp-substrate:	0.001
PAMPA:	0.084 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.257

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956	MRP1:	0.947
Plasma Protein Binding (PPB):	95.059%	Volume Distribution (VD):	0.364
Fu:	5.272% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.103	BCRP inhibitor:	0.005
BSEP inhibitor:	0.783

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.822
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.338 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.934

Half-life (T1/2):

0.717

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.194
Human Hepatotoxicity (H-HT):	0.702	Drug-induced Liver Injury (DILI):	0.121
AMES Toxicity:	0.315	Rat Oral Acute Toxicity:	0.606
Maximum Recommended Daily Dose:	0.246	Skin Sensitization:	0.999
Carcinogencity:	0.912	Eye Corrosion:	0.01
Eye Irritation:	0.313	Respiratory Toxicity:	0.543
Drug-induced Neurotoxicity:	0.24	Ototoxicity:	0.216
Hematotoxicity:	0.131	Drug-induced Nephrotoxicity:	0.963
Genotoxicity:	0.545	RPMI-8226 Immunitoxicity:	0.029
A549 Cytotoxicity:	0.038	Hek293 Cytotoxicity:	0.092
BCF:	2.083 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.563 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.922 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	8.151 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33449	hypericum cohaerens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23957453]
NPO33449	hypericum cohaerens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Inhibition	1
IC50	5

Activity Type	# Activity
Individual protein	1
Cell line	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6226	Individual protein	Acetylcholine receptor protein epsilon chain	Homo sapiens	Inhibition	=	31.7	%	PMID[11473422]

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	>	20000.0	nM	PMID[22880631]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	20000.0	nM	PMID[19853440]
NPT81	Cell line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[17284071]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	>	20000.0	nM	PMID[20117930]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	20000.0	nM	PMID[10820113]

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 NPC61651 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	14123
0.1-0.2	34747
0.2-0.3	828
0.3-0.4	99
0.4-0.5	25
0.5-0.6	22
0.6-0.7	6
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8286	Intermediate Similarity	NPC146239
0.8286	Intermediate Similarity	NPC483095
0.7162	Intermediate Similarity	NPC47466
0.7162	Intermediate Similarity	NPC116274
0.6912	Remote Similarity	NPC38885
0.6627	Remote Similarity	NPC144257
0.6494	Remote Similarity	NPC483065
0.6447	Remote Similarity	NPC482993
0.6125	Remote Similarity	NPC483077
0.6	Remote Similarity	NPC483066
0.5921	Remote Similarity	NPC260886
0.5844	Remote Similarity	NPC328997
0.5844	Remote Similarity	NPC294050
0.5844	Remote Similarity	NPC610705
0.575	Remote Similarity	NPC482994
0.5625	Remote Similarity	NPC482995
0.5526	Remote Similarity	NPC471331
0.5526	Remote Similarity	NPC99657
0.5526	Remote Similarity	NPC203388
0.55	Remote Similarity	NPC482999
0.5488	Remote Similarity	NPC483079
0.5467	Remote Similarity	NPC483058
0.5422	Remote Similarity	NPC483098
0.5244	Remote Similarity	NPC325740
0.5244	Remote Similarity	NPC482998
0.5244	Remote Similarity	NPC482997
0.5244	Remote Similarity	NPC482996
0.519	Remote Similarity	NPC471330
0.519	Remote Similarity	NPC472687
0.5176	Remote Similarity	NPC483092
0.5176	Remote Similarity	NPC483093
0.5116	Remote Similarity	NPC483099

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC61651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3772
0.1-0.2	5356
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