NPASS Compound

Natural Product: NPC485504

Natural Product ID	NPC485504
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BYZKFKFGPLUFIH-QHWVUYPCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	45484581
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 68 71 0 0 0 0 0 0 0 0999 V2000 5.8369 1.6612 -1.6900 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6381 1.2026 -0.9137 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5361 1.3754 0.3961 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6668 2.0503 1.0863 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3542 0.9149 1.1117 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2537 1.0771 2.3539 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3491 0.3012 0.4177 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1588 -0.1852 1.0062 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0039 0.4961 0.4251 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3510 1.7790 0.1065 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5608 2.6296 -0.4979 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8364 2.1827 -0.7878 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2348 0.8994 -0.4895 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3025 0.0911 0.1149 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0440 -1.1436 0.3554 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7484 -2.4964 0.1072 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5297 -3.1721 -0.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6346 -2.1734 -0.4551 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7463 -2.8903 -1.1936 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1133 -1.6861 0.8441 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5045 -2.2221 1.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2863 -2.1817 1.8546 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7068 -3.4059 0.3958 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9272 -3.0087 0.9159 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1859 -1.6501 1.1546 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2344 -0.7044 0.8751 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3577 0.6502 1.0851 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4555 -1.5087 1.6688 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0944 -2.7643 1.5926 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0667 -3.7058 1.2940 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4702 0.3714 -0.7629 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7880 -0.2946 -1.9748 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7943 2.9914 -1.3946 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6191 3.7432 -0.5038 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1861 3.9102 -0.8029 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0838 4.4532 -0.5493 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6554 2.7010 -2.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8986 1.0177 -2.5880 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7536 1.5956 -1.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8063 0.7054 -1.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8669 3.0395 0.6376 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5616 1.4152 1.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4370 2.1524 2.1836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2122 0.0356 2.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3605 2.1097 0.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6843 -3.6657 -1.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2396 -3.9165 0.3910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2762 -1.3620 -1.1238 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4667 -2.1978 -1.6533 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2072 -3.6827 -0.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2397 -3.4317 -2.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4368 -3.2848 1.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9606 -1.6703 1.9567 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1864 -2.0965 0.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7636 -2.1789 2.7331 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4965 -4.4726 0.2082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9480 1.1435 1.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5262 -2.9882 2.5778 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8881 -2.7848 0.7956 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8390 -0.1146 -2.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1063 0.1553 -2.7547 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5424 -1.3525 -1.9328 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0237 4.1000 0.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0158 4.6499 -1.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4420 3.1164 -0.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1709 5.5043 -0.8665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3043 4.3012 0.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8132 3.8702 -1.1821 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 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 1 16 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 13 31 1 0 31 32 1 0 12 33 1 0 33 34 1 0 11 35 1 0 35 36 1 0 20 8 1 0 30 24 1 0 14 9 1 0 26 15 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 4 41 1 0 4 42 1 0 4 43 1 0 8 44 1 1 10 45 1 0 17 46 1 0 17 47 1 0 18 48 1 6 19 49 1 0 19 50 1 0 19 51 1 0 21 52 1 0 21 53 1 0 21 54 1 0 22 55 1 0 23 56 1 0 27 57 1 0 29 58 1 0 29 59 1 0 32 60 1 0 32 61 1 0 32 62 1 0 34 63 1 0 34 64 1 0 34 65 1 0 36 66 1 0 36 67 1 0 36 68 1 0 M END

Standard InCHIKey	BYZKFKFGPLUFIH-QHWVUYPCSA-N
Standard InCHI	InChI=1S/C27H32O9/c1-8-13(2)26(29)36-25-16-11-17(31-5)23(32-6)24(33-7)20(16)19-15(9-14(3)27(25,4)30)10-18-22(21(19)28)35-12-34-18/h8,10-11,14,25,28,30H,9,12H2,1-7H3/b13-8+/t14-,25-,27-/m0/s1
SMILES	C/C=C(C)/C(=O)O[C@H]1c2cc(c(c(c2-c2c(C[C@H](C)[C@]1(C)O)cc1c(c2O)OCO1)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	500.2	Volume:	499.343 ? Van der Waals volume.
Dense:	1.002	LogP:	3.243 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.005 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.904 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	112.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.458	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.193	Fsp³:	0.444
MCE-18:	94.436 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.23	Fluc inhibitor:	0.094 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.366 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.547 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.119	Promiscuous compounds:	0.33

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.221	MDCK Permeability:	-4.927
Pgp-inhibitor:	0.003	Pgp-substrate:	0.014
PAMPA:	0.871 ? 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):	0.005
20% Bioavailability (F20%):	0.495	30% Bioavailability (F30%):	0.023
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019	MRP1:	0.999
Plasma Protein Binding (PPB):	93.367%	Volume Distribution (VD):	0.211
Fu:	6.853% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.959
OATP1B3 inhibitor:	0.951	BCRP inhibitor:	0.008
BSEP inhibitor:	0.964

ADMET: Metabolism

CYP1A2-inhibitor:	0.994	CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.321
CYP2C9-inhibitor:	0.983	CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.73	CYP2D6-substrate:	0.982
CYP3A4-inhibitor:	0.991	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.004	CYP2C8-inhibitor:	0.043
HLM stability:	0.407 ? 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):

3.588

Half-life (T1/2):

1.302

ADMET: Toxicity

hERG Blockers:	0.122	hERG Blockers (10um):	0.517
Human Hepatotoxicity (H-HT):	0.761	Drug-induced Liver Injury (DILI):	0.914
AMES Toxicity:	0.696	Rat Oral Acute Toxicity:	0.633
Maximum Recommended Daily Dose:	0.917	Skin Sensitization:	0.969
Carcinogencity:	0.965	Eye Corrosion:	0.001
Eye Irritation:	0.315	Respiratory Toxicity:	0.795
Drug-induced Neurotoxicity:	0.805	Ototoxicity:	0.505
Hematotoxicity:	0.574	Drug-induced Nephrotoxicity:	0.899
Genotoxicity:	0.877	RPMI-8226 Immunitoxicity:	0.418
A549 Cytotoxicity:	0.785	Hek293 Cytotoxicity:	0.794
BCF:	1.291 ? 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:	3.896 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.589 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.785 ? 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
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	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	7
Activity	21
GI	2
Inhibition	5

Activity Type	# Activity
Cell line	28
Organism	4
Others	3

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
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	33500.0	nM	PMID[18063366]
NPT1086	Cell line	SK-HEP1	Homo sapiens	IC50	=	19900.0	nM	PMID[18063366]
NPT2548	Cell line	SNU-638	Homo sapiens	IC50	=	15300.0	nM	PMID[18063366]
NPT396	Cell line	T47D	Homo sapiens	IC50	=	26100.0	nM	PMID[18063366]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	5600.0	nM	PMID[18063366]
NPT111	Cell line	K562	Homo sapiens	IC50	=	11300.0	nM	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	IC50	=	5600.0	nM	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	50.1	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	31.8	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	18.1	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	0.6	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	50.4	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	31.6	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	18.0	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	1.5	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	57.9	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	26.0	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	16.2	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	65.3	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	75.0	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	18.8	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	8.2	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	15.9	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	10.8	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	1.1	%	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	Activity	=	2.5	%	PMID[18063366]
NPT71	Cell line	HEK293	Homo sapiens	Inhibition	=	-9.3	%	PMID[24018191]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	59.7	%	PMID[19640714]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	22.1	%	PMID[19640714]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	34.7	%	PMID[19640714]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	16.9	%	PMID[19640714]
NPT27	Others	Unspecified	n.a.	GI	>=	25.0	%	PMID[19640714]
NPT2	Others	Unspecified	n.a.	Activity	=	201.0	%	PMID[25302569]

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 NPC485504 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	7067
0.1-0.2	39142
0.2-0.3	3418
0.3-0.4	138
0.4-0.5	56
0.5-0.6	19
0.6-0.7	5
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	Natural Product ID
0.7606	Intermediate Similarity	NPC126405
0.7606	Intermediate Similarity	NPC53669
0.7606	Intermediate Similarity	NPC77237
0.7606	Intermediate Similarity	NPC297271
0.7606	Intermediate Similarity	NPC16791
0.7606	Intermediate Similarity	NPC217708
0.7324	Intermediate Similarity	NPC198461
0.7101	Intermediate Similarity	NPC295297
0.7089	Intermediate Similarity	NPC88557
0.6986	Remote Similarity	NPC470916
0.641	Remote Similarity	NPC476065
0.641	Remote Similarity	NPC475592
0.6234	Remote Similarity	NPC224472
0.6053	Remote Similarity	NPC308739
0.5875	Remote Similarity	NPC475756
0.5854	Remote Similarity	NPC29727
0.5789	Remote Similarity	NPC252286
0.5775	Remote Similarity	NPC184684
0.5775	Remote Similarity	NPC184641
0.5542	Remote Similarity	NPC474606
0.5529	Remote Similarity	NPC238834
0.5513	Remote Similarity	NPC121661
0.5357	Remote Similarity	NPC483406
0.5325	Remote Similarity	NPC474393
0.5325	Remote Similarity	NPC474347
0.5256	Remote Similarity	NPC73467
0.5238	Remote Similarity	NPC469512
0.5238	Remote Similarity	NPC83049
0.5238	Remote Similarity	NPC320471
0.5238	Remote Similarity	NPC118162
0.5135	Remote Similarity	NPC180602
0.5125	Remote Similarity	NPC154971
0.5063	Remote Similarity	NPC85141

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC485504 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3166
0.1-0.2	5878
0.2-0.3	105
0.3-0.4	1
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