NPASS Compound

Natural Product: NPC470513

Natural Product ID	NPC470513
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sorbifoliaside B
IUPAC Name	(3R,4R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-4a-[[(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]-3,4-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-3,4,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picen-5-one
Synonyms	sorbifoliaside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2058158
PubChem CID	70692680
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 188197 0 0 0 0 0 0 0 0999 V2000 -8.6267 -5.6297 -3.4316 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3291 -4.2960 -3.1845 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6256 -3.9027 -1.7564 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2970 -2.5549 -1.6149 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6926 -2.0662 -0.3648 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1984 -0.7732 -0.2615 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2706 -0.6428 0.7644 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9607 -0.0836 0.2916 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9049 -0.8336 0.7872 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1048 -1.3308 -0.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9515 -2.1748 0.3312 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2003 -2.6363 -0.8621 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3649 -3.7148 -1.3515 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1996 -1.6904 -1.4582 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1508 -1.5405 -0.3746 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7833 -1.0626 0.8791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1115 -0.2272 1.6602 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2539 0.2942 1.3926 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8904 -0.4812 0.2679 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9042 -0.5236 -0.8505 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1421 0.7760 -1.0463 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4127 -0.9662 -2.1676 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7587 -0.2845 -2.4558 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6643 -0.7068 -1.3445 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2780 -0.0370 -0.0771 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4728 1.4361 -0.0400 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1910 -0.6186 1.0128 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6359 -0.4693 0.7122 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0506 -0.9804 -0.6358 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1021 -0.6135 -1.7412 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3065 -1.6285 -2.8601 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4814 0.7347 -2.3211 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2834 -0.4012 -0.9291 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2858 -1.3259 -1.1071 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1988 -1.1612 -0.0457 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3268 -0.4353 -0.4246 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9593 0.1069 0.8306 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1093 0.8555 0.5954 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6717 1.3243 1.7749 C 0 0 2 0 0 0 0 0 0 0 0 0 12.7081 2.6786 1.9171 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7277 3.3599 1.3239 C 0 0 2 0 0 0 0 0 0 0 0 0 13.4522 3.6441 -0.1489 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5270 4.3563 -0.7107 O 0 0 0 0 0 0 0 0 0 0 0 0 15.1019 2.8007 1.5311 C 0 0 2 0 0 0 0 0 0 0 0 0 15.1449 1.3002 1.3198 C 0 0 1 0 0 0 0 0 0 0 0 0 14.0043 0.6692 2.0462 C 0 0 1 0 0 0 0 0 0 0 0 0 14.2591 0.7432 3.4155 O 0 0 0 0 0 0 0 0 0 0 0 0 15.1508 0.9914 -0.0330 O 0 0 0 0 0 0 0 0 0 0 0 0 15.6344 3.1792 2.7601 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9779 0.7133 -1.3276 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6084 0.1247 -2.6756 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9599 -1.2210 -2.4508 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8613 -2.2692 -2.6078 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7850 0.9882 -3.3865 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0458 1.5596 -1.4840 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1552 -1.4329 1.3285 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2094 -1.9925 2.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1555 -3.4701 2.8432 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5874 -4.2273 1.6037 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6396 -3.3918 0.9190 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2628 -4.1140 -0.0848 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79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 80 83 1 0 79 84 1 0 5 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 86 89 1 0 85 90 1 0 87 3 1 0 69 7 1 0 81 74 1 0 60 11 1 0 56 11 1 0 20 15 1 0 30 24 1 0 52 34 1 0 25 19 1 0 46 39 1 0 1 91 1 0 2 92 1 0 2 93 1 0 3 94 1 1 5 95 1 1 7 96 1 1 8 97 1 6 10 98 1 0 10 99 1 0 14100 1 0 14101 1 0 17102 1 0 18103 1 0 18104 1 0 19105 1 1 21106 1 0 21107 1 0 21108 1 0 22109 1 0 22110 1 0 23111 1 0 23112 1 0 24113 1 1 26114 1 0 26115 1 0 26116 1 0 27117 1 0 27118 1 0 28119 1 0 28120 1 0 29121 1 1 31122 1 0 31123 1 0 31124 1 0 32125 1 0 32126 1 0 32127 1 0 34128 1 1 36129 1 6 37130 1 0 37131 1 0 39132 1 1 41133 1 1 42134 1 0 42135 1 0 43136 1 0 44137 1 6 45138 1 1 46139 1 6 47140 1 0 48141 1 0 49142 1 0 50143 1 1 51144 1 6 52145 1 6 53146 1 0 54147 1 0 55148 1 0 56149 1 1 57150 1 0 57151 1 0 59152 1 6 60153 1 1 61154 1 0 62155 1 0 63156 1 0 63157 1 0 63158 1 0 64159 1 0 64160 1 0 64161 1 0 65162 1 0 65163 1 0 65164 1 0 67165 1 6 68166 1 1 69167 1 1 70168 1 0 71169 1 0 72170 1 0 72171 1 0 74172 1 1 76173 1 1 77174 1 0 77175 1 0 78176 1 0 79177 1 6 80178 1 1 81179 1 6 82180 1 0 83181 1 0 84182 1 0 85183 1 1 86184 1 1 87185 1 6 88186 1 0 89187 1 0 90188 1 0 M END

Standard InCHIKey	MFDCBYLTQPABTR-SUJHCHJWSA-N
Standard InCHI	InChI=1S/C60H98O30/c1-55(2)14-23-22-8-9-30-57(5)12-11-32(89-52-45(77)41(73)36(68)27(87-52)19-81-50-43(75)38(70)33(65)24(16-61)84-50)56(3,4)29(57)10-13-58(30,6)59(22,7)15-31(64)60(23,49(80)48(55)79)21-83-54-47(90-53-46(78)40(72)35(67)26(18-63)86-53)42(74)37(69)28(88-54)20-82-51-44(76)39(71)34(66)25(17-62)85-51/h8,23-30,32-54,61-63,65-80H,9-21H2,1-7H3/t23-,24+,25+,26+,27+,28+,29-,30+,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	OC[C@H]1O[C@@H](O[C@H]2[C@H](OC[C@]34C(=O)C[C@@]5(C(=CC[C@H]6[C@@]5(C)CC[C@@H]5[C@]6(C)CC[C@@H](C5(C)C)O[C@@H]5O[C@H](CO[C@@H]6O[C@H](CO)[C@H]([C@@H]([C@H]6O)O)O)[C@H]([C@@H]([C@H]5O)O)O)[C@@H]4CC([C@H]([C@@H]3O)O)(C)C)C)O[C@@H]([C@H]([C@@H]2O)O)CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1298.61	Volume:	1219.185 ? Van der Waals volume.
Dense:	1.065	LogP:	-1.102 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.061 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.969 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	57.0
TPSA:	493.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	30.0
H-Bond Donor:	19.0	Rings:	10.0
Heavy Atoms:	30.0

MedChem Properties

QED Drug-Likeness Score:	0.05	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.487	Fsp³:	0.95
MCE-18:	222.923 ? 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:	0.667	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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.356	Promiscuous compounds:	0.242

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.357	MDCK Permeability:	-4.893
Pgp-inhibitor:	0.0	Pgp-substrate:	0.852
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%):	0.302	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	56.958%	Volume Distribution (VD):	-0.258
Fu:	21.685% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.01
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):

-0.984

Half-life (T1/2):

4.5

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.584	Drug-induced Liver Injury (DILI):	0.938
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.003	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.704	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.411	RPMI-8226 Immunitoxicity:	0.485
A549 Cytotoxicity:	0.962	Hek293 Cytotoxicity:	0.416
BCF:	0.887 ? 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:	3.294 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.642 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.638 ? 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[15104487]
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[22119124]
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 NPC470513 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	20711
0.1-0.2	24006
0.2-0.3	3753
0.3-0.4	794
0.4-0.5	487
0.5-0.6	88
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC470514
0.8125	Intermediate Similarity	NPC470512
0.7864	Intermediate Similarity	NPC470516
0.78	Intermediate Similarity	NPC173859
0.7451	Intermediate Similarity	NPC148603
0.6964	Remote Similarity	NPC470911
0.6909	Remote Similarity	NPC470915
0.6696	Remote Similarity	NPC470517
0.6422	Remote Similarity	NPC470515
0.6261	Remote Similarity	NPC185466
0.6195	Remote Similarity	NPC481079
0.619	Remote Similarity	NPC48499
0.6126	Remote Similarity	NPC63159
0.5948	Remote Similarity	NPC207738
0.5702	Remote Similarity	NPC105800
0.569	Remote Similarity	NPC470914
0.562	Remote Similarity	NPC79643
0.5537	Remote Similarity	NPC607904
0.5537	Remote Similarity	NPC610204
0.5528	Remote Similarity	NPC135904
0.5528	Remote Similarity	NPC603137
0.5517	Remote Similarity	NPC123796
0.5508	Remote Similarity	NPC291903
0.5484	Remote Similarity	NPC475140
0.5478	Remote Similarity	NPC232237
0.547	Remote Similarity	NPC471435
0.547	Remote Similarity	NPC471434
0.5446	Remote Similarity	NPC473373
0.5431	Remote Similarity	NPC148417
0.541	Remote Similarity	NPC473824
0.5403	Remote Similarity	NPC123199
0.5385	Remote Similarity	NPC222580
0.5378	Remote Similarity	NPC606145
0.536	Remote Similarity	NPC470218
0.5351	Remote Similarity	NPC469946
0.5345	Remote Similarity	NPC164389
0.5345	Remote Similarity	NPC488526
0.5345	Remote Similarity	NPC480475
0.5339	Remote Similarity	NPC484832
0.5328	Remote Similarity	NPC475119
0.5304	Remote Similarity	NPC112352
0.5304	Remote Similarity	NPC478066
0.5289	Remote Similarity	NPC104137
0.5289	Remote Similarity	NPC26626
0.5289	Remote Similarity	NPC609281
0.5285	Remote Similarity	NPC60557
0.5285	Remote Similarity	NPC67857
0.5271	Remote Similarity	NPC41061
0.5271	Remote Similarity	NPC227551
0.5263	Remote Similarity	NPC295371
0.5259	Remote Similarity	NPC480947
0.5259	Remote Similarity	NPC309714
0.5254	Remote Similarity	NPC257468
0.5254	Remote Similarity	NPC297263
0.5246	Remote Similarity	NPC606553
0.5231	Remote Similarity	NPC43550
0.5227	Remote Similarity	NPC70809
0.521	Remote Similarity	NPC119794
0.5207	Remote Similarity	NPC488564
0.5203	Remote Similarity	NPC288205
0.5203	Remote Similarity	NPC51465
0.5191	Remote Similarity	NPC305981
0.5175	Remote Similarity	NPC127056
0.5167	Remote Similarity	NPC37134
0.5164	Remote Similarity	NPC31838
0.5161	Remote Similarity	NPC610461
0.5159	Remote Similarity	NPC219180
0.5159	Remote Similarity	NPC609305
0.5154	Remote Similarity	NPC258617
0.5152	Remote Similarity	NPC261506
0.5152	Remote Similarity	NPC309223
0.5152	Remote Similarity	NPC4328
0.5138	Remote Similarity	NPC128925
0.5135	Remote Similarity	NPC90856
0.5135	Remote Similarity	NPC214484
0.5133	Remote Similarity	NPC136877
0.513	Remote Similarity	NPC39211
0.512	Remote Similarity	NPC151543
0.5118	Remote Similarity	NPC475160
0.5118	Remote Similarity	NPC473714
0.5089	Remote Similarity	NPC164194
0.5089	Remote Similarity	NPC1046
0.5086	Remote Similarity	NPC76497
0.5085	Remote Similarity	NPC251768
0.5085	Remote Similarity	NPC104400
0.5085	Remote Similarity	NPC305267
0.5085	Remote Similarity	NPC10320
0.5082	Remote Similarity	NPC295823
0.5082	Remote Similarity	NPC174720
0.5082	Remote Similarity	NPC475467
0.5079	Remote Similarity	NPC471384
0.5079	Remote Similarity	NPC165204
0.5075	Remote Similarity	NPC224381
0.5075	Remote Similarity	NPC220160
0.507	Remote Similarity	NPC484831
0.5043	Remote Similarity	NPC173583
0.5043	Remote Similarity	NPC485579
0.5042	Remote Similarity	NPC162574
0.5041	Remote Similarity	NPC78034
0.5039	Remote Similarity	NPC481080
0.5037	Remote Similarity	NPC250247

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7191
0.1-0.2	1896
0.2-0.3	55
0.3-0.4	8
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