NPASS Compound

Natural Product: NPC473115

Natural Product ID	NPC473115
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AXUHZRWXOLLLLV-WRMVGDBRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3609879
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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 92 97 0 0 0 0 0 0 0 0999 V2000 -1.8272 -5.3953 -2.1610 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5697 -4.1793 -1.3683 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2853 -4.2849 -0.1457 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6314 -2.9180 -1.9304 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3879 -1.7541 -1.1858 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6337 -0.8529 -1.1545 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2883 0.2904 -0.2587 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0444 -0.2245 1.0337 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7748 0.1366 2.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7047 0.9773 1.9437 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5482 -0.3723 3.4739 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3235 0.0429 4.5205 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1196 -0.4385 5.8175 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1158 -1.3482 6.0345 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3359 -1.7690 4.9952 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5462 -1.2819 3.6969 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1632 1.1205 -0.7859 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0871 0.2921 -1.1526 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4687 -0.8456 -1.9395 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3208 -0.2274 -2.8989 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6165 -0.4292 -2.5875 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2071 -1.5815 -3.3916 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5061 0.7729 -2.8762 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4954 -1.5871 -2.8159 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3206 -2.6331 -2.1509 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2738 -0.6525 -3.6764 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9580 0.8010 -3.4779 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9188 1.1973 -2.0345 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2890 1.1817 -1.5953 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9619 2.2970 -1.2069 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3586 3.4064 -1.2306 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3980 2.2127 -0.7572 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7585 0.0203 0.1245 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9893 -0.7184 0.0385 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6855 -1.0289 1.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1270 -0.6132 2.2726 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9201 -1.7448 1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4636 -2.0031 2.5410 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6350 -2.6674 2.7195 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3404 -3.1184 1.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8318 -2.8778 0.4024 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6553 -2.2104 0.2246 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8741 2.1069 0.1756 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0544 3.4505 -0.0998 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4865 3.7978 -1.2238 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7502 4.4888 0.8991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2754 4.1931 2.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0116 5.1694 3.0912 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1957 6.4774 2.7346 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6729 6.8340 1.4870 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9439 5.8122 0.5818 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9091 -5.6137 -2.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3888 -6.2828 -1.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3025 -5.3153 -3.1347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1491 -2.0087 -0.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5174 -1.3911 -0.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1485 0.9925 -0.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1156 0.7503 4.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7284 -0.1146 6.6472 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9444 -1.7335 7.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5541 -2.4829 5.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8854 -1.6667 2.9336 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4901 1.6016 -1.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0421 -1.2320 -4.0700 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7371 -2.3214 -2.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4861 -2.0527 -4.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9766 1.4665 -3.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8523 1.3003 -1.9901 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4327 0.4806 -3.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1759 -2.1554 -3.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3226 -3.5847 -2.7693 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0213 -2.9472 -1.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4097 -2.3674 -2.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3663 -0.8252 -3.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1931 -0.8559 -4.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8458 1.3570 -3.9163 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1090 1.1694 -4.0836 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6097 2.2550 -1.9723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6642 1.1488 -0.6606 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9897 2.6086 -1.6275 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5812 2.8145 0.1459 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2108 -0.4755 0.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0890 1.0069 0.5736 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9163 -1.6522 3.4137 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9853 -2.8254 3.7406 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2754 -3.6477 1.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2936 -2.0380 -0.7672 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1162 3.1633 2.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3857 4.9253 4.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0189 7.2618 3.4462 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8281 7.8611 1.2284 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3147 6.1051 -0.3857 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 20 21 1 0 21 22 1 0 21 23 1 0 19 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 18 33 1 1 33 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 17 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 19 5 1 0 42 37 1 0 51 46 1 0 21 6 1 0 16 11 1 0 28 18 1 0 1 52 1 0 1 53 1 0 1 54 1 0 5 55 1 1 6 56 1 1 7 57 1 1 12 58 1 0 13 59 1 0 14 60 1 0 15 61 1 0 16 62 1 0 17 63 1 6 22 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 23 69 1 0 24 70 1 6 25 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 27 76 1 0 27 77 1 0 28 78 1 6 32 79 1 0 32 80 1 0 32 81 1 0 33 82 1 0 33 83 1 0 38 84 1 0 39 85 1 0 40 86 1 0 42 87 1 0 47 88 1 0 48 89 1 0 49 90 1 0 50 91 1 0 51 92 1 0 M END

Standard InCHIKey	AXUHZRWXOLLLLV-WRMVGDBRSA-N
Standard InCHI	InChI=1S/C39H41NO11/c1-23-18-19-29(47-24(2)41)38(22-46-34(43)28-17-12-20-40-21-28)33(50-36(45)27-15-10-7-11-16-27)31(49-35(44)26-13-8-6-9-14-26)30-32(48-25(3)42)39(23,38)51-37(30,4)5/h6-17,20-21,23,29-33H,18-19,22H2,1-5H3/t23-,29+,30-,31-,32-,33-,38+,39-/m1/s1
SMILES	CC(=O)O[C@@H]1[C@H]2[C@@H](OC(=O)c3ccccc3)[C@H]([C@]3([C@@]1(OC2(C)C)[C@H](C)CC[C@@H]3OC(=O)C)COC(=O)c1cccnc1)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	699.27	Volume:	702.54 ? Van der Waals volume.
Dense:	0.995	LogP:	3.335 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.119 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.032 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	37.0
TPSA:	153.62 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.215	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.841	Fsp³:	0.436
MCE-18:	180.107 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.67	Fluc inhibitor:	0.027 ? 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:	0.449 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.02	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.362	MDCK Permeability:	-4.803
Pgp-inhibitor:	1.0	Pgp-substrate:	0.174
PAMPA:	0.064 ? 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%):	0.001	30% Bioavailability (F30%):	0.03
50% Bioavailability (F50%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.355	MRP1:	1.0
Plasma Protein Binding (PPB):	94.56%	Volume Distribution (VD):	-0.528
Fu:	6.061% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.195
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.995
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.959
CYP3A4-inhibitor:	0.097	CYP3A4-substrate:	0.328
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

2.65

Half-life (T1/2):

0.894

ADMET: Toxicity

hERG Blockers:	0.099	hERG Blockers (10um):	0.527
Human Hepatotoxicity (H-HT):	0.115	Drug-induced Liver Injury (DILI):	0.896
AMES Toxicity:	0.14	Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.125	Skin Sensitization:	0.97
Carcinogencity:	0.728	Eye Corrosion:	0.0
Eye Irritation:	0.065	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.236	Ototoxicity:	0.344
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.452
Genotoxicity:	0.196	RPMI-8226 Immunitoxicity:	0.031
A549 Cytotoxicity:	0.097	Hek293 Cytotoxicity:	0.296
BCF:	0.963 ? 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:	4.241 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.601 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.371 ? 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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	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
Activity	1

Activity Type	# Activity
Cell line	1

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
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	79.0	%	PMID[18387711]

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 NPC473115 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	15899
0.1-0.2	31980
0.2-0.3	1480
0.3-0.4	314
0.4-0.5	134
0.5-0.6	27
0.6-0.7	19
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
0.7432	Intermediate Similarity	NPC483845
0.7407	Intermediate Similarity	NPC6576
0.725	Intermediate Similarity	NPC4421
0.7037	Intermediate Similarity	NPC212768
0.6974	Remote Similarity	NPC90257
0.6974	Remote Similarity	NPC69357
0.679	Remote Similarity	NPC483849
0.6747	Remote Similarity	NPC488900
0.6747	Remote Similarity	NPC488899
0.6742	Remote Similarity	NPC488902
0.6742	Remote Similarity	NPC488903
0.6709	Remote Similarity	NPC483844
0.6667	Remote Similarity	NPC211137
0.6463	Remote Similarity	NPC483848
0.6447	Remote Similarity	NPC475429
0.642	Remote Similarity	NPC481059
0.631	Remote Similarity	NPC483887
0.631	Remote Similarity	NPC158020
0.6234	Remote Similarity	NPC66761
0.6234	Remote Similarity	NPC483843
0.6049	Remote Similarity	NPC147217
0.6026	Remote Similarity	NPC476094
0.6023	Remote Similarity	NPC473089
0.5926	Remote Similarity	NPC48017
0.5862	Remote Similarity	NPC608007
0.5783	Remote Similarity	NPC473758
0.5732	Remote Similarity	NPC246480
0.5667	Remote Similarity	NPC301368
0.5667	Remote Similarity	NPC84815
0.5663	Remote Similarity	NPC137718
0.5663	Remote Similarity	NPC148062
0.561	Remote Similarity	NPC51314
0.5604	Remote Similarity	NPC75600
0.5604	Remote Similarity	NPC180668
0.5604	Remote Similarity	NPC483884
0.5542	Remote Similarity	NPC147880
0.5476	Remote Similarity	NPC483842
0.5465	Remote Similarity	NPC252314
0.5422	Remote Similarity	NPC17877
0.5385	Remote Similarity	NPC610927
0.5349	Remote Similarity	NPC306146
0.5349	Remote Similarity	NPC483841
0.5275	Remote Similarity	NPC479040
0.5269	Remote Similarity	NPC10904
0.5238	Remote Similarity	NPC473060
0.5233	Remote Similarity	NPC473088
0.5208	Remote Similarity	NPC479046
0.5114	Remote Similarity	NPC479043
0.5106	Remote Similarity	NPC148896
0.505	Remote Similarity	NPC6981

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3210
0.1-0.2	5812
0.2-0.3	124
0.3-0.4	4
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