NPASS Compound

Natural Product: NPC134925

Natural Product ID	NPC134925
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JQVXKQDWMIXILH-ZVLUUUFJSA-N
IUPAC Name	n.a.
Synonyms	1,3,4,5 Tetra-O-Galloylquinic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL36985
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic acids and derivatives [CHEMONTID:0002513] O-galloylquinic acids and derivatives

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 85 89 0 0 0 0 0 0 0 0999 V2000 -1.1926 -1.9997 -2.4031 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5392 -2.8233 -1.7172 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5577 -4.2258 -2.0584 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1625 -5.1324 -1.3215 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1292 -6.4836 -1.6641 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8547 -7.3864 -0.9197 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6206 -6.9151 -2.7353 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3463 -6.0116 -3.4800 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3007 -4.6621 -3.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1125 -6.4433 -4.5729 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6744 -8.2688 -3.1045 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1732 -2.3077 -0.6501 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2089 -0.9340 -0.2921 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5460 -0.3303 -0.3422 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2231 0.0664 0.9116 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2986 0.6064 1.9808 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1409 0.6820 1.4998 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5285 -0.6751 0.9984 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8965 -0.9308 0.9201 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5583 -1.9051 1.6436 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8063 -2.5552 2.3944 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9632 -2.1857 1.5790 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8572 -1.5213 0.7823 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2027 -1.8418 0.7686 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1139 -1.1717 -0.0370 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6726 -2.8652 1.5814 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8059 -3.5492 2.3890 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4891 -3.2003 2.3713 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2140 -4.5811 3.2230 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0112 -3.2292 1.6080 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4081 1.7239 0.6444 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2278 2.7834 0.7936 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8628 2.8881 1.8397 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3586 3.7781 -0.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2067 4.8547 -0.0786 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3528 5.8141 -1.0559 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2061 6.8768 -0.8503 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6597 5.7446 -2.2559 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8236 4.6661 -2.4083 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6601 3.6936 -1.4464 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1150 4.5718 -3.6043 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8375 6.7279 -3.2057 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1638 1.1071 0.5673 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9924 1.7091 1.4957 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8998 1.3038 2.6813 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9387 2.7538 1.1967 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1311 3.2843 -0.0597 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0598 4.2858 -0.2533 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2642 4.8298 -1.5134 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8264 4.7939 0.7868 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6404 4.2683 2.0487 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7110 3.2740 2.2116 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3820 4.7423 3.1196 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7604 5.8022 0.5884 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0549 -1.0567 1.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4947 -2.1238 1.7678 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4263 -1.0018 1.4820 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7673 -4.8569 -0.4734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8288 -8.3823 -1.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8876 -3.9906 -3.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1573 -5.8198 -5.3863 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0883 -8.6974 -3.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4511 -0.4450 -1.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2248 -1.0624 -0.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5480 0.5509 -1.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6272 1.5837 2.3868 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3998 -0.0980 2.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 0.8494 2.4112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1270 -1.4041 1.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5102 -0.7250 0.1452 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9422 -1.6307 -0.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8020 -3.7424 3.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0985 -4.5601 4.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7233 -2.5325 1.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7534 4.9132 0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0007 7.7556 -1.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 2.8457 -1.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0174 3.7183 -4.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7363 6.5186 -4.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5355 2.8898 -0.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0417 5.8125 -1.6138 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5997 2.8859 3.2358 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6560 4.2225 3.9197 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6051 5.8896 1.1323 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0151 -1.8026 1.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 5 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 7 11 1 0 2 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 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 24 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 26 30 1 0 17 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 36 38 2 0 38 39 1 0 39 40 2 0 39 41 1 0 38 42 1 0 15 43 1 6 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 1 0 48 50 2 0 50 51 1 0 51 52 2 0 51 53 1 0 50 54 1 0 15 55 1 0 55 56 2 0 55 57 1 0 9 3 1 0 18 13 1 0 28 22 1 0 40 34 1 0 52 46 1 0 4 58 1 0 6 59 1 0 9 60 1 0 10 61 1 0 11 62 1 0 13 63 1 6 14 64 1 0 14 65 1 0 16 66 1 0 16 67 1 0 17 68 1 1 18 69 1 1 23 70 1 0 25 71 1 0 28 72 1 0 29 73 1 0 30 74 1 0 35 75 1 0 37 76 1 0 40 77 1 0 41 78 1 0 42 79 1 0 47 80 1 0 49 81 1 0 52 82 1 0 53 83 1 0 54 84 1 0 57 85 1 0 M END

Standard InCHIKey	JQVXKQDWMIXILH-ZVLUUUFJSA-N
Standard InCHI	InChI=1S/C35H28O22/c36-15-1-11(2-16(37)25(15)44)30(48)54-23-9-35(34(52)53,57-33(51)14-7-21(42)28(47)22(43)8-14)10-24(55-31(49)12-3-17(38)26(45)18(39)4-12)29(23)56-32(50)13-5-19(40)27(46)20(41)6-13/h1-8,23-24,29,36-47H,9-10H2,(H,52,53)/t23-,24-,29-,35+/m1/s1
SMILES	O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1C[C@](C[C@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)(OC(=O)c1cc(O)c(c(c1)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	800.11	Volume:	719.699 ? Van der Waals volume.
Dense:	1.112	LogP:	0.551 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.372 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.907 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	35.0
TPSA:	385.26 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	13.0	Rings:	5.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.065	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.23	Fsp³:	0.171
MCE-18:	138.293 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.978	Fluc inhibitor:	0.05 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.221 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.651 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.72	Promiscuous compounds:	0.751

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.556	MDCK Permeability:	-4.807
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	1.0 ? 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%):	0.798	30% Bioavailability (F30%):	0.507
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	72.078%	Volume Distribution (VD):	-0.236
Fu:	16.006% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.024
OATP1B3 inhibitor:	0.019	BCRP inhibitor:	0.374
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.56
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

5.209

Half-life (T1/2):

3.445

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.98
Human Hepatotoxicity (H-HT):	0.008	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.451	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.905	Skin Sensitization:	1.0
Carcinogencity:	0.042	Eye Corrosion:	0.0
Eye Irritation:	0.891	Respiratory Toxicity:	0.016
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.053
BCF:	0.172 ? 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:	3.197 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.111 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.159 ? 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
NPO32818	lepidobotrys staudtii	Species	Lepidobotryaceae	Eukaryota	n.a.	Cameroon	n.a.	PMID[11430019]

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
Phorbol displacement	1
Inhibition	7
ED50	5
EC50	2

Activity Type	# Activity
Individual protein	1
Cell line	5
Protein family	2
Organism	5
Others	4
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT316	Protein family	Protein kinase C (PKC)	Homo sapiens	IC50	=	64000.0	nM	PMID[17524651]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	800.0	nM	PMID[11430019]
NPT727	Protein family	Protein kinase C, PKC; classical/novel	Homo sapiens	Phorbol displacement	<=	50.0	uM	DOI[10.1016/S0960-894X(01)81072-6]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell line	H9	Homo sapiens	Inhibition	=	25.0	%	DrugMatrix in vitro pharmacology data
NPT672	Cell line	TE-671	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[17438054]
NPT180	Cell line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[19902967]
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	DrugMatrix in vitro pharmacology data
NPT91	Cell line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[21807523]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.43	ug ml-1	PMID[1431932]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	EC50	=	10000000.0	nM	PMID[17428663]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	66.0	%	DrugMatrix in vitro pharmacology data
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	52.0	%	PMID[19902967]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	15.0	%	PMID[23030848]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	500.0	nM	PMID[9157192]
NPT2	Others	Unspecified	n.a.	Inhibition	=	94.0	%	PMID[12617583]
NPT2	Others	Unspecified	n.a.	Inhibition	=	84.0	%	PMID[25443644]
NPT2	Others	Unspecified	n.a.	Inhibition	=	36.0	%	PMID[25443644]
NPT2	Others	Unspecified	n.a.	IC50	=	800.0	nM	PMID[24079846]

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 NPC134925 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	18713
0.1-0.2	29691
0.2-0.3	1309
0.3-0.4	114
0.4-0.5	26
0.5-0.6	4
0.6-0.7	1
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
0.68	Remote Similarity	NPC252979
0.5893	Remote Similarity	NPC608793
0.5714	Remote Similarity	NPC43123
0.5273	Remote Similarity	NPC114242
0.5094	Remote Similarity	NPC610546

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC134925 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3521
0.1-0.2	5502
0.2-0.3	124
0.3-0.4	2
0.4-0.5	1
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