NPASS Compound

Natural Product: NPC316539

Natural Product ID	NPC316539
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Saccharumoside A
IUPAC Name	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[(2R,3S)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate
Synonyms	Saccharumoside A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1923078
PubChem CID	56834589
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 88 92 0 0 0 0 0 0 0 0999 V2000 9.2488 3.7841 0.5900 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5502 2.6932 1.3973 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4701 1.7069 0.7294 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9210 1.1218 -0.5294 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6459 0.3824 -0.3239 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4449 1.0905 -0.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2366 0.4501 -0.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7943 0.8964 -0.3048 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5654 1.9020 -1.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8900 1.3543 -2.6285 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1462 -0.4130 -0.6967 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8676 -1.3046 0.1677 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2114 -0.8963 0.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4222 -1.5981 0.1395 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6307 -0.9740 -0.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3826 -2.9400 0.4244 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5111 -3.7428 0.5422 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7005 -0.4678 -0.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9280 -0.5040 -1.6813 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5302 -0.5613 -1.6411 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0866 -0.5817 -0.4163 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6705 -0.5457 0.7598 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0227 -0.4907 0.6522 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0148 -0.5685 1.9593 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6396 -0.5347 3.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4459 -0.6380 -0.3106 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3989 -0.6753 -1.3205 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2289 0.4100 -1.2405 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5033 0.2324 -0.8147 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6776 0.2421 0.6981 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0078 0.0431 1.0445 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0937 0.8143 0.7428 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8974 1.8550 0.0643 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4522 0.5057 1.1559 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7518 -0.6200 1.8938 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0493 -0.9089 2.2833 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0825 -0.0697 1.9399 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8081 1.0661 1.2001 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4986 1.3332 0.8217 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8646 1.8967 0.8655 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5617 3.0551 0.1100 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4047 -0.3539 2.3308 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2770 -0.9007 -1.3899 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3808 -1.8282 -2.1624 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1244 -2.0115 -1.3777 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3311 -2.9667 -2.0330 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0213 -3.0461 -2.3870 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2864 -0.4797 -2.2873 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5686 4.3178 1.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6357 2.2055 1.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0704 3.1077 2.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7257 0.9173 1.4630 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4249 2.2076 0.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8054 1.8849 -1.3119 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6531 0.3347 -0.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4331 2.1484 -0.6530 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4825 1.2698 0.6682 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1115 2.8498 -1.2264 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4826 2.1289 -1.4050 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8556 1.5581 -2.7688 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4831 -0.6509 -1.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5996 -1.4391 0.0332 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8070 -3.9048 1.6216 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2437 -4.7934 0.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4007 -3.4116 -0.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3968 -0.4878 -2.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0250 -0.5878 -2.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6120 -0.4638 1.5616 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0346 -1.4972 3.5290 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4475 0.2439 3.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1070 -0.1511 3.9448 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9179 -0.6015 -2.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0642 1.1730 -1.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2320 1.1564 1.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0850 -0.6035 1.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9190 -1.2692 2.1530 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2802 -1.7876 2.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3010 2.2346 0.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2258 2.8376 -0.9116 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4950 3.6840 0.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8234 3.6457 0.6935 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7000 -1.3332 2.3330 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7689 -1.5269 -0.5898 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1289 -1.3071 -3.1291 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3307 -2.3369 -0.3512 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8430 -3.6574 -2.4799 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1062 -3.2833 -3.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1016 -1.0247 -2.2115 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 8 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 11 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 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 2 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 37 42 1 0 29 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 15 5 1 0 23 18 1 0 45 27 1 0 13 7 2 0 39 34 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 6 56 1 0 8 57 1 1 9 58 1 0 9 59 1 0 10 60 1 0 11 61 1 6 15 62 1 0 17 63 1 0 17 64 1 0 17 65 1 0 19 66 1 0 20 67 1 0 23 68 1 0 25 69 1 0 25 70 1 0 25 71 1 0 27 72 1 6 29 73 1 6 30 74 1 0 30 75 1 0 35 76 1 0 36 77 1 0 39 78 1 0 41 79 1 0 41 80 1 0 41 81 1 0 42 82 1 0 43 83 1 1 44 84 1 6 45 85 1 1 46 86 1 0 47 87 1 0 48 88 1 0 M END

Standard InCHIKey	VGTBWTHKJXOATF-DIGBNQJTSA-N
Standard InCHI	InChI=1S/C34H40O14/c1-42-24-14-19(6-8-22(24)37)33(41)45-16-27-28(38)29(39)30(40)34(47-27)46-23-9-7-18(13-25(23)43-2)31-21(15-36)20-11-17(5-4-10-35)12-26(44-3)32(20)48-31/h6-9,11-14,21,27-31,34-40H,4-5,10,15-16H2,1-3H3/t21-,27-,28-,29+,30-,31+,34-/m1/s1
SMILES	OCCCc1cc2[C@@H](CO)[C@@H](Oc2c(c1)OC)c1ccc(c(c1)OC)O[C@@H]1O[C@H](COC(=O)c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	672.24	Volume:	650.536 ? Van der Waals volume.
Dense:	1.033	LogP:	1.932 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.256 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.567 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	29.0
TPSA:	203.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.143	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.473	Fsp³:	0.441
MCE-18:	108.429 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.748	Fluc inhibitor:	0.222 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.063 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.685 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.044	Promiscuous compounds:	0.109

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.014	MDCK Permeability:	-5.313
Pgp-inhibitor:	0.153	Pgp-substrate:	0.482
PAMPA:	0.466 ? 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):	0.098
20% Bioavailability (F20%):	0.627	30% Bioavailability (F30%):	0.9
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.657
Plasma Protein Binding (PPB):	69.986%	Volume Distribution (VD):	-0.388
Fu:	25.766% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.54
BSEP inhibitor:	0.969

ADMET: Metabolism

CYP1A2-inhibitor:	0.926	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.047	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.956	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.017	CYP3A4-substrate:	0.998
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):

2.128

Half-life (T1/2):

2.524

ADMET: Toxicity

hERG Blockers:	0.074	hERG Blockers (10um):	0.338
Human Hepatotoxicity (H-HT):	0.622	Drug-induced Liver Injury (DILI):	0.882
AMES Toxicity:	0.444	Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.036	Skin Sensitization:	0.963
Carcinogencity:	0.253	Eye Corrosion:	0.0
Eye Irritation:	0.219	Respiratory Toxicity:	0.03
Drug-induced Neurotoxicity:	0.027	Ototoxicity:	0.926
Hematotoxicity:	0.154	Drug-induced Nephrotoxicity:	0.817
Genotoxicity:	0.064	RPMI-8226 Immunitoxicity:	0.22
A549 Cytotoxicity:	0.471	Hek293 Cytotoxicity:	0.39
BCF:	0.622 ? 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:	3.41 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.066 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.224 ? 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
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	bark	n.a.	PMID[22032697]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	bark	n.a.	n.a.	PMID[22032697]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14559	Acer saccharum	Species	Sapindaceae	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	2

Activity Type	# Activity
Cell line	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
NPT393	Cell line	HCT-116	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[22032697]
NPT492	Cell line	Caco-2	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[22032697]

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 NPC316539 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	14001
0.1-0.2	31720
0.2-0.3	3595
0.3-0.4	424
0.4-0.5	90
0.5-0.6	24
0.6-0.7	4
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
0.6854	Remote Similarity	NPC79429
0.6854	Remote Similarity	NPC217635
0.6111	Remote Similarity	NPC327032
0.6042	Remote Similarity	NPC275284
0.5882	Remote Similarity	NPC29799
0.5882	Remote Similarity	NPC263367
0.5882	Remote Similarity	NPC54743
0.5758	Remote Similarity	NPC224674
0.5758	Remote Similarity	NPC64475
0.5729	Remote Similarity	NPC471667
0.5673	Remote Similarity	NPC479449
0.566	Remote Similarity	NPC98624
0.5638	Remote Similarity	NPC199539
0.5591	Remote Similarity	NPC311803
0.5579	Remote Similarity	NPC5786
0.5529	Remote Similarity	NPC230219
0.55	Remote Similarity	NPC114505
0.55	Remote Similarity	NPC213074
0.5446	Remote Similarity	NPC15956
0.5361	Remote Similarity	NPC476301
0.5312	Remote Similarity	NPC102851
0.5263	Remote Similarity	NPC197708
0.5253	Remote Similarity	NPC43508
0.5146	Remote Similarity	NPC31325
0.5096	Remote Similarity	NPC269559
0.5089	Remote Similarity	NPC228357
0.505	Remote Similarity	NPC193473
0.505	Remote Similarity	NPC600128

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC316539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3834
0.1-0.2	5194
0.2-0.3	113
0.3-0.4	9
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