NPASS Compound

Natural Product: NPC470512

Natural Product ID	NPC470512
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sorbifoliaside A
IUPAC Name	(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aR,9R,10R,12aS,14aR,14bR)-8a-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-9,10-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms	sorbifoliaside A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2058157
PubChem CID	66552717
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 189198 0 0 0 0 0 0 0 0999 V2000 -4.0551 1.2009 -3.1597 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7670 0.4507 -2.8980 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1514 0.7518 -1.5526 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6731 -0.5538 -0.9874 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6750 -0.4288 0.0991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0912 0.7018 0.4812 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9060 0.7761 1.5747 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7491 -0.4465 1.7130 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1969 -0.0803 1.5436 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1283 -1.0798 2.1994 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5648 -0.7419 2.0889 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0731 -0.3462 0.7386 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0523 0.3257 -0.1321 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6173 -0.0065 0.1223 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2748 -1.3052 -0.5550 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8157 -1.5928 -0.4229 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2581 -1.6247 0.9488 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2486 -1.6263 0.8485 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7716 -2.8267 0.1178 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2534 -2.7550 -0.0392 C 0 0 0 0 0 0 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76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 78 80 1 0 80 81 1 0 77 82 1 0 76 83 1 0 75 84 1 0 69 85 1 0 68 86 1 0 67 87 1 0 9 88 1 0 2 89 1 0 23 2 1 0 79 74 1 0 21 4 1 0 18 5 1 0 17 8 1 0 14 9 1 0 33 28 1 0 41 36 1 0 55 50 1 0 71 66 1 0 1 90 1 0 1 91 1 0 1 92 1 0 3 93 1 0 3 94 1 0 4 95 1 0 6 96 1 0 7 97 1 0 7 98 1 0 8 99 1 0 10100 1 0 10101 1 0 11102 1 0 11103 1 0 12104 1 0 14105 1 0 15106 1 0 15107 1 0 16108 1 0 16109 1 0 19110 1 0 19111 1 0 20112 1 0 20113 1 0 22114 1 0 23115 1 0 24116 1 0 25117 1 0 26118 1 0 26119 1 0 28120 1 0 29121 1 0 30122 1 0 31123 1 0 32124 1 0 34125 1 0 34126 1 0 36127 1 0 37128 1 0 38129 1 0 39130 1 0 40131 1 0 42132 1 0 42133 1 0 43134 1 0 44135 1 0 45136 1 0 46137 1 0 47138 1 0 48139 1 0 50140 1 0 51141 1 0 52142 1 0 53143 1 0 54144 1 0 56145 1 0 56146 1 0 57147 1 0 58148 1 0 59149 1 0 60150 1 0 61151 1 0 61152 1 0 61153 1 0 62154 1 0 62155 1 0 62156 1 0 63157 1 0 63158 1 0 63159 1 0 64160 1 0 64161 1 0 64162 1 0 66163 1 0 67164 1 0 68165 1 0 69166 1 0 70167 1 0 72168 1 0 72169 1 0 74170 1 0 75171 1 0 76172 1 0 77173 1 0 78174 1 0 80175 1 0 80176 1 0 81177 1 0 82178 1 0 83179 1 0 84180 1 0 85181 1 0 86182 1 0 87183 1 0 88184 1 0 88185 1 0 88186 1 0 89187 1 0 89188 1 0 89189 1 0 M END

Standard InCHIKey	KOFDPGMKUXQIII-YVDNPAFXSA-N
Standard InCHI	InChI=1S/C60H100O29/c1-55(2)16-24-23-8-9-31-57(5)12-11-32(88-52-45(76)41(72)36(67)28(86-52)20-80-50-43(74)38(69)33(64)25(17-61)83-50)56(3,4)30(57)10-13-59(31,7)58(23,6)14-15-60(24,49(79)48(55)78)22-82-54-47(89-53-46(77)40(71)35(66)27(19-63)85-53)42(73)37(68)29(87-54)21-81-51-44(75)39(70)34(65)26(18-62)84-51/h8,24-54,61-79H,9-22H2,1-7H3/t24-,25+,26+,27+,28+,29+,30-,31+,32-,33+,34+,35+,36+,37+,38-,39-,40-,41-,42-,43+,44+,45+,46+,47+,48-,49-,50+,51+,52-,53-,54+,57-,58+,59+,60-/m0/s1
SMILES	CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CCC2(C(C1O)O)COC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)(C)C)OC9C(C(C(C(O9)COC1C(C(C(C(O1)CO)O)O)O)O)O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1284.64	Volume:	1213.031 ? Van der Waals volume.
Dense:	1.059	LogP:	-2.087 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.732 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.598 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	56.0
TPSA:	476.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	29.0
H-Bond Donor:	19.0	Rings:	10.0
Heavy Atoms:	29.0

MedChem Properties

QED Drug-Likeness Score:	0.051	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.385	Fsp³:	0.967
MCE-18:	221.017 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.0	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.284 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.435	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.704	MDCK Permeability:	-4.9
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	1.0
20% Bioavailability (F20%):	0.981	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	17.278%	Volume Distribution (VD):	-0.331
Fu:	36.593% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.002	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.938	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.415	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

-0.778

Half-life (T1/2):

3.827

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.331
Human Hepatotoxicity (H-HT):	0.189	Drug-induced Liver Injury (DILI):	0.166
AMES Toxicity:	0.592	Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.058	Skin Sensitization:	0.003
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.441	Ototoxicity:	1.0
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.001
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.093
A549 Cytotoxicity:	0.023	Hek293 Cytotoxicity:	0.958
BCF:	0.896 ? 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:	4.047 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.401 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.367 ? 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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	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
IC50	10

Activity Type	# Activity
Cell line	8
Non-molecular	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
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[12502320]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	>	100000.0	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	DrugMatrix in vivo data: Biochemistry
NPT306	Cell line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PubChem BioAssay data set
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[15104485]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[24904961]
NPT453	Cell line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[26034885]
NPT1171	Cell line	HEp-2	Homo sapiens	IC50	>	100000.0	nM	PMID[14510593]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[22801644]

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 NPC470512 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	23105
0.1-0.2	22083
0.2-0.3	3205
0.3-0.4	817
0.4-0.5	456
0.5-0.6	164
0.6-0.7	8
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC173859
0.9111	High Similarity	NPC148603
0.8218	Intermediate Similarity	NPC470911
0.8182	Intermediate Similarity	NPC470915
0.8125	Intermediate Similarity	NPC470513
0.7885	Intermediate Similarity	NPC470517
0.7653	Intermediate Similarity	NPC470515
0.7576	Intermediate Similarity	NPC470514
0.6735	Remote Similarity	NPC48499
0.6698	Remote Similarity	NPC481079
0.6635	Remote Similarity	NPC63159
0.6455	Remote Similarity	NPC185466
0.633	Remote Similarity	NPC470516
0.6204	Remote Similarity	NPC471435
0.6204	Remote Similarity	NPC471434
0.6053	Remote Similarity	NPC79643
0.5982	Remote Similarity	NPC207738
0.5948	Remote Similarity	NPC135904
0.5872	Remote Similarity	NPC148417
0.5856	Remote Similarity	NPC470914
0.5818	Remote Similarity	NPC123796
0.5812	Remote Similarity	NPC123199
0.5804	Remote Similarity	NPC291903
0.5794	Remote Similarity	NPC469946
0.578	Remote Similarity	NPC480475
0.5763	Remote Similarity	NPC470218
0.5763	Remote Similarity	NPC475140
0.5755	Remote Similarity	NPC473373
0.5741	Remote Similarity	NPC112352
0.5727	Remote Similarity	NPC105800
0.5701	Remote Similarity	NPC295371
0.569	Remote Similarity	NPC60557
0.569	Remote Similarity	NPC473824
0.569	Remote Similarity	NPC67857
0.569	Remote Similarity	NPC607904
0.569	Remote Similarity	NPC610204
0.5678	Remote Similarity	NPC603137
0.5676	Remote Similarity	NPC222580
0.5676	Remote Similarity	NPC257468
0.5664	Remote Similarity	NPC606145
0.5656	Remote Similarity	NPC41061
0.5656	Remote Similarity	NPC227551
0.5625	Remote Similarity	NPC484832
0.5625	Remote Similarity	NPC119794
0.5614	Remote Similarity	NPC488564
0.561	Remote Similarity	NPC43550
0.5607	Remote Similarity	NPC127056
0.5603	Remote Similarity	NPC475119
0.56	Remote Similarity	NPC70809
0.5588	Remote Similarity	NPC128925
0.5577	Remote Similarity	NPC90856
0.5566	Remote Similarity	NPC136877
0.5565	Remote Similarity	NPC305981
0.5546	Remote Similarity	NPC219180
0.5545	Remote Similarity	NPC309714
0.5536	Remote Similarity	NPC297263
0.5528	Remote Similarity	NPC258617
0.5524	Remote Similarity	NPC164194
0.552	Remote Similarity	NPC261506
0.552	Remote Similarity	NPC4328
0.5505	Remote Similarity	NPC263756
0.5505	Remote Similarity	NPC213674
0.55	Remote Similarity	NPC475160
0.55	Remote Similarity	NPC473714
0.5495	Remote Similarity	NPC251768
0.5495	Remote Similarity	NPC164389
0.5495	Remote Similarity	NPC104400
0.5495	Remote Similarity	NPC488526
0.5495	Remote Similarity	NPC10320
0.5495	Remote Similarity	NPC232237
0.5478	Remote Similarity	NPC295823
0.5478	Remote Similarity	NPC174720
0.5478	Remote Similarity	NPC475467
0.547	Remote Similarity	NPC288205
0.547	Remote Similarity	NPC51465
0.5463	Remote Similarity	NPC173583
0.5462	Remote Similarity	NPC471384
0.5462	Remote Similarity	NPC165204
0.5455	Remote Similarity	NPC478066
0.5439	Remote Similarity	NPC37134
0.5433	Remote Similarity	NPC224381
0.5431	Remote Similarity	NPC104137
0.5431	Remote Similarity	NPC31838
0.5431	Remote Similarity	NPC26626
0.5431	Remote Similarity	NPC609281
0.5429	Remote Similarity	NPC214484
0.5413	Remote Similarity	NPC39211
0.541	Remote Similarity	NPC481080
0.5391	Remote Similarity	NPC250247
0.5385	Remote Similarity	NPC606553
0.5378	Remote Similarity	NPC151543
0.5377	Remote Similarity	NPC29069
0.537	Remote Similarity	NPC475516
0.5364	Remote Similarity	NPC76497
0.5347	Remote Similarity	NPC606107
0.5317	Remote Similarity	NPC136768
0.5317	Remote Similarity	NPC481081
0.5315	Remote Similarity	NPC192791
0.5304	Remote Similarity	NPC78034
0.5299	Remote Similarity	NPC481078
0.5294	Remote Similarity	NPC610461
0.5289	Remote Similarity	NPC166422
0.5289	Remote Similarity	NPC609305
0.5276	Remote Similarity	NPC309223
0.5273	Remote Similarity	NPC472949
0.5273	Remote Similarity	NPC488561
0.5268	Remote Similarity	NPC160415
0.5268	Remote Similarity	NPC605226
0.5259	Remote Similarity	NPC301449
0.5259	Remote Similarity	NPC601290
0.5242	Remote Similarity	NPC476068
0.5234	Remote Similarity	NPC1046
0.5234	Remote Similarity	NPC78046
0.5229	Remote Similarity	NPC235405
0.5229	Remote Similarity	NPC25605
0.5229	Remote Similarity	NPC208650
0.5225	Remote Similarity	NPC473343
0.5225	Remote Similarity	NPC161674
0.5225	Remote Similarity	NPC80843
0.5221	Remote Similarity	NPC305267
0.5221	Remote Similarity	NPC46665
0.5217	Remote Similarity	NPC488515
0.52	Remote Similarity	NPC110633
0.5197	Remote Similarity	NPC236638
0.5197	Remote Similarity	NPC294453
0.5194	Remote Similarity	NPC220160
0.5182	Remote Similarity	NPC249848
0.5182	Remote Similarity	NPC107966
0.5179	Remote Similarity	NPC488573
0.5179	Remote Similarity	NPC223301
0.5179	Remote Similarity	NPC488572
0.5179	Remote Similarity	NPC171544
0.5175	Remote Similarity	NPC139044
0.5175	Remote Similarity	NPC235438
0.5172	Remote Similarity	NPC104372
0.5169	Remote Similarity	NPC36831
0.5167	Remote Similarity	NPC475287
0.5167	Remote Similarity	NPC76972
0.5167	Remote Similarity	NPC469782
0.5167	Remote Similarity	NPC204414
0.5167	Remote Similarity	NPC268184
0.5143	Remote Similarity	NPC69737
0.514	Remote Similarity	NPC204458
0.5135	Remote Similarity	NPC220427
0.5135	Remote Similarity	NPC488516
0.5133	Remote Similarity	NPC30735
0.5133	Remote Similarity	NPC114304
0.5133	Remote Similarity	NPC117714
0.5133	Remote Similarity	NPC30289
0.5128	Remote Similarity	NPC324875
0.5128	Remote Similarity	NPC292677
0.5124	Remote Similarity	NPC123522
0.5122	Remote Similarity	NPC100639
0.512	Remote Similarity	NPC57484
0.5118	Remote Similarity	NPC65105
0.5115	Remote Similarity	NPC102505
0.5115	Remote Similarity	NPC488514
0.5113	Remote Similarity	NPC33012
0.5091	Remote Similarity	NPC59804
0.5088	Remote Similarity	NPC10607
0.5088	Remote Similarity	NPC473459
0.5086	Remote Similarity	NPC64715
0.5086	Remote Similarity	NPC302887
0.5085	Remote Similarity	NPC480473
0.5085	Remote Similarity	NPC80986
0.5085	Remote Similarity	NPC480474
0.5082	Remote Similarity	NPC284449
0.5081	Remote Similarity	NPC54636
0.5081	Remote Similarity	NPC488560
0.5079	Remote Similarity	NPC13998
0.5072	Remote Similarity	NPC484831
0.5071	Remote Similarity	NPC45606
0.5043	Remote Similarity	NPC475591
0.5043	Remote Similarity	NPC236870
0.5043	Remote Similarity	NPC118440
0.5042	Remote Similarity	NPC187290
0.504	Remote Similarity	NPC85154
0.5039	Remote Similarity	NPC298034
0.5039	Remote Similarity	NPC71065
0.5038	Remote Similarity	NPC8524

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7602
0.1-0.2	1488
0.2-0.3	53
0.3-0.4	7
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