NPASS Compound

Natural Product: NPC473060

Natural Product ID	NPC473060
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SFGLNYILNHSTSJ-CEVVBJQHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3608653
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic 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 96 0 0 0 0 0 0 0 0999 V2000 0.5563 -4.3881 1.4293 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1631 -2.9460 1.7038 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3412 -2.3018 2.3386 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6953 -0.9060 1.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1035 -0.5286 0.6348 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3464 -0.7228 0.6603 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6019 -2.2590 0.6627 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4090 -2.8123 -0.6917 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6761 -2.2314 -1.3993 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2741 -0.8370 -1.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1736 -0.0783 -0.4031 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0357 1.2885 -0.4590 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9771 2.2342 -0.1215 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0563 1.7481 0.2802 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8478 3.6780 -0.1831 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8824 4.4880 0.2374 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8336 5.8556 0.1985 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7065 6.4922 -0.2802 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6561 5.7052 -0.7079 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7276 4.3260 -0.6595 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0729 -0.9288 -2.4229 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0709 -0.4416 -3.7227 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1252 0.0600 -4.1945 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1213 -0.4774 -4.6061 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6427 -2.4862 -0.3017 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0071 -2.2810 0.8928 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9504 -3.9974 -0.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9788 -1.8132 -0.4611 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5568 -4.1594 -0.8914 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2416 -4.9151 -1.6905 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1932 -4.3992 -2.3116 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0103 -6.3636 -1.8327 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9994 -0.2840 1.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8037 1.0671 2.2642 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 1.5704 3.4278 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0215 0.8545 4.2288 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1788 3.0049 3.7701 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6476 0.6059 0.0621 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5197 0.6882 -1.0022 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7980 -0.4481 -1.4591 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0890 1.8699 -1.5815 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8943 3.1386 -1.1244 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4550 4.2455 -1.7213 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2563 4.1019 -2.8342 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4719 2.8320 -3.3191 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8961 1.7371 -2.7003 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3933 -0.0777 3.0415 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3807 0.6796 3.6397 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5859 0.6475 3.2384 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1116 1.5882 4.7955 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2551 -5.0597 1.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4789 -4.4547 0.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9169 -4.8077 2.4345 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5938 -3.0815 2.5559 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3130 -2.4389 3.4686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2749 -2.9144 2.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8103 -0.7804 1.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5470 -1.3586 -0.0123 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4739 -2.4668 -1.2596 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8409 -2.7828 -2.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0813 -0.3623 -2.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2511 -0.1895 -0.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7788 4.0167 0.6176 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6431 6.4923 0.5276 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6460 7.5845 -0.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2267 6.1833 -1.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0727 3.6837 -0.9921 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0578 -0.7066 -4.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1818 0.5182 -5.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9140 -1.2163 -5.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0495 -4.1830 -0.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4426 -4.5570 0.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8176 -4.3915 -1.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0053 -1.1138 -1.3490 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3197 -1.2929 0.4723 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8177 -2.5237 -0.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1907 -6.8678 -0.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8614 -6.8738 -2.3142 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8806 -6.5835 -2.4741 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7489 -0.9729 2.8040 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0887 -0.4156 1.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3022 3.4527 3.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0669 3.6012 3.5078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0252 3.1165 4.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2722 3.2762 -0.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2928 5.2415 -1.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7214 4.9510 -3.3394 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0973 2.7118 -4.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1089 0.7689 -3.1360 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0514 1.6477 5.0471 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5932 2.5608 4.6009 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6450 1.1657 5.6956 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 10 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 9 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 8 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 6 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 5 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 4 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 7 2 1 0 11 6 1 0 26 7 1 0 20 15 1 0 46 41 1 0 1 51 1 0 1 52 1 0 1 53 1 0 2 54 1 0 3 55 1 0 3 56 1 0 4 57 1 0 5 58 1 0 8 59 1 0 9 60 1 0 10 61 1 0 11 62 1 0 16 63 1 0 17 64 1 0 18 65 1 0 19 66 1 0 20 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 28 76 1 0 32 77 1 0 32 78 1 0 32 79 1 0 33 80 1 0 33 81 1 0 37 82 1 0 37 83 1 0 37 84 1 0 42 85 1 0 43 86 1 0 44 87 1 0 45 88 1 0 46 89 1 0 50 90 1 0 50 91 1 0 50 92 1 0 M END

Standard InCHIKey	SFGLNYILNHSTSJ-CEVVBJQHSA-N
Standard InCHI	InChI=1S/C37H42O13/c1-20-18-27(45-22(3)39)30(48-33(42)25-14-10-8-11-15-25)36(19-44-21(2)38)32(49-34(43)26-16-12-9-13-17-26)29(46-23(4)40)28-31(47-24(5)41)37(20,36)50-35(28,6)7/h8-17,20,27-32H,18-19H2,1-7H3/t20-,27+,28-,29-,30+,31-,32-,36+,37-/m1/s1
SMILES	CC1CC(C(C2(C13C(C(C(C2OC(=O)C4=CC=CC=C4)OC(=O)C)C(O3)(C)C)OC(=O)C)COC(=O)C)OC(=O)C5=CC=CC=C5)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	694.26	Volume:	688.361 ? Van der Waals volume.
Dense:	1.009	LogP:	3.757 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.371 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.444 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	32.0
TPSA:	167.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.273	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.985	Fsp³:	0.514
MCE-18:	171.321 ? 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:	0.282	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.355 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.138	Promiscuous compounds:	0.014

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.042	MDCK Permeability:	-4.613
Pgp-inhibitor:	1.0	Pgp-substrate:	0.257
PAMPA:	0.315 ? 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):	0.009
20% Bioavailability (F20%):	0.053	30% Bioavailability (F30%):	0.969
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053	MRP1:	0.988
Plasma Protein Binding (PPB):	84.346%	Volume Distribution (VD):	-0.319
Fu:	17.49% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.07
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.865	CYP3A4-substrate:	0.0
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):

0.388

Half-life (T1/2):

1.15

ADMET: Toxicity

hERG Blockers:	0.061	hERG Blockers (10um):	0.616
Human Hepatotoxicity (H-HT):	0.035	Drug-induced Liver Injury (DILI):	0.863
AMES Toxicity:	0.22	Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.175	Skin Sensitization:	0.177
Carcinogencity:	0.429	Eye Corrosion:	0.0
Eye Irritation:	0.008	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.417	Ototoxicity:	0.694
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.099
Genotoxicity:	0.083	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.012	Hek293 Cytotoxicity:	0.477
BCF:	0.983 ? 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:	4.032 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.991 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.551 ? 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	=	76.2	%	PubChem BioAssay data set

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 NPC473060 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	19193
0.1-0.2	28810
0.2-0.3	1283
0.3-0.4	383
0.4-0.5	103
0.5-0.6	39
0.6-0.7	28
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9016	High Similarity	NPC148062
0.8852	High Similarity	NPC147880
0.8689	High Similarity	NPC51314
0.8413	Intermediate Similarity	NPC137718
0.8308	Intermediate Similarity	NPC479043
0.7846	Intermediate Similarity	NPC147217
0.7619	Intermediate Similarity	NPC481047
0.7619	Intermediate Similarity	NPC481045
0.7424	Intermediate Similarity	NPC90257
0.7424	Intermediate Similarity	NPC69357
0.7361	Intermediate Similarity	NPC479040
0.7206	Intermediate Similarity	NPC254558
0.7206	Intermediate Similarity	NPC471107
0.6912	Remote Similarity	NPC483845
0.6912	Remote Similarity	NPC479047
0.6912	Remote Similarity	NPC291638
0.6857	Remote Similarity	NPC483844
0.6714	Remote Similarity	NPC471100
0.6714	Remote Similarity	NPC605884
0.662	Remote Similarity	NPC479044
0.6575	Remote Similarity	NPC483848
0.6528	Remote Similarity	NPC16912
0.6528	Remote Similarity	NPC609924
0.6522	Remote Similarity	NPC472577
0.6429	Remote Similarity	NPC4341
0.6301	Remote Similarity	NPC252314
0.6301	Remote Similarity	NPC472569
0.6301	Remote Similarity	NPC472570
0.6267	Remote Similarity	NPC483849
0.6267	Remote Similarity	NPC481050
0.6267	Remote Similarity	NPC609221
0.6197	Remote Similarity	NPC191082
0.6111	Remote Similarity	NPC43241
0.6087	Remote Similarity	NPC66761
0.6087	Remote Similarity	NPC483843
0.6087	Remote Similarity	NPC476094
0.6081	Remote Similarity	NPC57628
0.6081	Remote Similarity	NPC11685
0.6056	Remote Similarity	NPC483902
0.6053	Remote Similarity	NPC481489
0.6027	Remote Similarity	NPC473088
0.5974	Remote Similarity	NPC483887
0.5974	Remote Similarity	NPC158020
0.5915	Remote Similarity	NPC90614
0.5897	Remote Similarity	NPC608007
0.589	Remote Similarity	NPC177340
0.5789	Remote Similarity	NPC184747
0.5769	Remote Similarity	NPC481488
0.5714	Remote Similarity	NPC195647
0.5694	Remote Similarity	NPC483862
0.5676	Remote Similarity	NPC139067
0.5634	Remote Similarity	NPC475429
0.5634	Remote Similarity	NPC211137
0.5616	Remote Similarity	NPC17877
0.557	Remote Similarity	NPC481486
0.5493	Remote Similarity	NPC200592
0.5493	Remote Similarity	NPC610542
0.5479	Remote Similarity	NPC241951
0.5467	Remote Similarity	NPC67777
0.5467	Remote Similarity	NPC483842
0.5405	Remote Similarity	NPC483886
0.5395	Remote Similarity	NPC473758
0.5325	Remote Similarity	NPC41481
0.5316	Remote Similarity	NPC282239
0.5278	Remote Similarity	NPC473081
0.5256	Remote Similarity	NPC481059
0.5238	Remote Similarity	NPC473115
0.5238	Remote Similarity	NPC75600
0.5238	Remote Similarity	NPC483884
0.52	Remote Similarity	NPC281717
0.519	Remote Similarity	NPC97667
0.5139	Remote Similarity	NPC481066
0.5128	Remote Similarity	NPC306146
0.5128	Remote Similarity	NPC483841
0.5125	Remote Similarity	NPC471102
0.5068	Remote Similarity	NPC270498
0.5065	Remote Similarity	NPC483846
0.5065	Remote Similarity	NPC27377
0.5065	Remote Similarity	NPC472572
0.506	Remote Similarity	NPC488899

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4256
0.1-0.2	4731
0.2-0.3	163
0.3-0.4	0
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