NPASS Compound

Natural Product: NPC479044

Natural Product ID	NPC479044
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OFAIHLUXGCZDTK-CKRPIROTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 91 0 0 0 0 0 0 0 0999 V2000 -2.2772 -3.1206 -3.9037 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7791 -3.9125 -2.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 -3.6450 -1.4809 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5004 -4.4841 -0.3545 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9867 -2.2051 -1.1777 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6845 -1.4569 -1.9028 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3285 -1.5736 -0.1169 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4563 -0.2102 0.1085 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2894 -0.0725 1.3947 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3195 1.3167 1.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8024 2.3739 0.9783 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6035 3.6251 1.8348 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6431 2.0193 0.1133 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4873 2.9365 0.0830 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9550 2.6846 -1.3766 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4943 1.3250 -1.5469 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7082 0.2051 -0.9178 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1700 0.5846 0.2363 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5604 0.2406 1.4928 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7787 0.9141 1.6851 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5468 0.6779 2.8086 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0984 -0.1620 3.6374 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8386 1.3671 3.0480 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7106 -0.6857 -0.4106 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8992 -1.9376 -0.9293 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1363 -2.2658 -1.8973 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8928 -2.8754 -0.4446 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7249 -2.5463 0.5978 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6809 -3.4542 1.0580 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8169 -4.6933 0.4877 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9733 -5.0189 -0.5644 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0140 -4.1103 -1.0279 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4083 2.7651 -2.0230 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8726 4.1973 -2.1712 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3070 2.1905 -3.4393 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1858 2.0077 -1.2186 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1730 4.3239 0.0613 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9007 5.2584 0.7340 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9001 4.9440 1.4180 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5056 6.6833 0.6594 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8480 -1.0558 2.2779 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5918 -2.1952 2.6157 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7081 -2.3060 2.0783 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9946 -3.1422 3.5602 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9711 -2.2761 -4.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 -3.7353 -4.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2809 -2.6722 -3.6972 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8457 -3.6748 -2.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7352 -4.9862 -2.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9153 -4.0316 -1.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5591 -4.1243 -0.2243 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5191 -5.5352 -0.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9774 -4.2737 0.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0792 0.2862 -0.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3180 -0.4165 1.0558 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4264 1.5530 2.0675 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9375 1.4480 2.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6921 2.6767 0.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4601 3.5886 2.5808 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 3.6044 2.4451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8129 4.5484 1.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3372 2.8190 0.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6517 3.4421 -1.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5884 1.3079 -1.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5208 1.1057 -2.6481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1518 -0.3779 -1.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8610 -0.8517 1.3974 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0137 0.2965 2.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7481 1.9128 4.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0986 2.0201 2.2145 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5890 0.5525 3.2302 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6925 -1.5958 1.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3231 -3.1822 1.8726 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5689 -5.4152 0.8457 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0932 -5.9955 -1.0007 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4020 -4.4471 -1.8487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3904 4.3330 -3.1645 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6356 4.4821 -1.4098 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0161 4.9022 -2.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0954 2.6690 -4.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4960 1.1089 -3.4585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6674 2.4743 -3.9077 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1327 7.3438 1.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5538 6.8300 1.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4690 7.0334 -0.4120 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7314 -3.7045 4.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3958 -3.9331 3.0222 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2449 -2.6213 4.2080 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 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 17 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 15 33 1 0 33 34 1 0 33 35 1 0 33 36 1 0 14 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 9 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 18 8 1 0 32 27 1 0 18 13 1 0 13 36 1 6 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 4 53 1 0 8 54 1 6 9 55 1 6 10 56 1 0 10 57 1 0 11 58 1 6 12 59 1 0 12 60 1 0 12 61 1 0 14 62 1 1 15 63 1 6 16 64 1 0 16 65 1 0 17 66 1 6 19 67 1 0 19 68 1 0 23 69 1 0 23 70 1 0 23 71 1 0 28 72 1 0 29 73 1 0 30 74 1 0 31 75 1 0 32 76 1 0 34 77 1 0 34 78 1 0 34 79 1 0 35 80 1 0 35 81 1 0 35 82 1 0 40 83 1 0 40 84 1 0 40 85 1 0 44 86 1 0 44 87 1 0 44 88 1 0 M END

Standard InCHIKey	OFAIHLUXGCZDTK-CKRPIROTSA-N
Standard InCHI	InChI=1S/C33H44O11/c1-9-18(2)29(37)43-28-25(40-21(5)35)15-19(3)33-27(41-22(6)36)24(31(7,8)44-33)16-26(32(28,33)17-39-20(4)34)42-30(38)23-13-11-10-12-14-23/h10-14,18-19,24-28H,9,15-17H2,1-8H3/t18?,19-,24-,25+,26-,27-,28+,32-,33-/m1/s1
SMILES	CCC(C)C(=O)O[C@H]1[C@H](C[C@@H](C)[C@@]23[C@@H]([C@@H](C[C@H]([C@]12COC(=O)C)OC(=O)c1ccccc1)C(C)(C)O3)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	616.29	Volume:	620.699 ? Van der Waals volume.
Dense:	0.993	LogP:	3.073 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.074 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.059 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	25.0
TPSA:	140.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.291	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.017	Fsp³:	0.667
MCE-18:	149.6 ? 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:	0.626	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.037 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.238	Promiscuous compounds:	0.204

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.025	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.996	Pgp-substrate:	0.195
PAMPA:	0.126 ? 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%):	0.008	30% Bioavailability (F30%):	0.465
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114	MRP1:	1.0
Plasma Protein Binding (PPB):	79.765%	Volume Distribution (VD):	-0.422
Fu:	20.104% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.143
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.077	CYP3A4-substrate:	0.015
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.97 ? 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):

2.399

Half-life (T1/2):

0.852

ADMET: Toxicity

hERG Blockers:	0.067	hERG Blockers (10um):	0.492
Human Hepatotoxicity (H-HT):	0.158	Drug-induced Liver Injury (DILI):	0.766
AMES Toxicity:	0.373	Rat Oral Acute Toxicity:	0.131
Maximum Recommended Daily Dose:	0.147	Skin Sensitization:	0.973
Carcinogencity:	0.682	Eye Corrosion:	0.002
Eye Irritation:	0.166	Respiratory Toxicity:	0.043
Drug-induced Neurotoxicity:	0.372	Ototoxicity:	0.355
Hematotoxicity:	0.085	Drug-induced Nephrotoxicity:	0.451
Genotoxicity:	0.057	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.18	Hek293 Cytotoxicity:	0.349
BCF:	0.723 ? 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:	3.827 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.528 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.104 ? 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
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	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	=	88.34	%	PMID[31713425]

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 NPC479044 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	17242
0.1-0.2	30625
0.2-0.3	1481
0.3-0.4	349
0.4-0.5	77
0.5-0.6	44
0.6-0.7	25
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9194	High Similarity	NPC479047
0.9194	High Similarity	NPC291638
0.8594	High Similarity	NPC4341
0.8182	Intermediate Similarity	NPC43241
0.803	Intermediate Similarity	NPC191082
0.7714	Intermediate Similarity	NPC184747
0.7647	Intermediate Similarity	NPC139067
0.7647	Intermediate Similarity	NPC177340
0.7143	Intermediate Similarity	NPC67777
0.7101	Intermediate Similarity	NPC17877
0.7027	Intermediate Similarity	NPC479042
0.7015	Intermediate Similarity	NPC195647
0.6761	Remote Similarity	NPC147880
0.6757	Remote Similarity	NPC97667
0.6712	Remote Similarity	NPC41481
0.6709	Remote Similarity	NPC75600
0.6709	Remote Similarity	NPC483884
0.662	Remote Similarity	NPC473060
0.6575	Remote Similarity	NPC471107
0.6575	Remote Similarity	NPC471100
0.6575	Remote Similarity	NPC605884
0.6533	Remote Similarity	NPC95265
0.6522	Remote Similarity	NPC473081
0.6522	Remote Similarity	NPC200592
0.6522	Remote Similarity	NPC610542
0.6438	Remote Similarity	NPC27377
0.6438	Remote Similarity	NPC148062
0.64	Remote Similarity	NPC479043
0.6351	Remote Similarity	NPC254558
0.6316	Remote Similarity	NPC70716
0.6301	Remote Similarity	NPC48017
0.6164	Remote Similarity	NPC51314
0.6056	Remote Similarity	NPC270498
0.6026	Remote Similarity	NPC473112
0.6026	Remote Similarity	NPC607428
0.6	Remote Similarity	NPC147217
0.6	Remote Similarity	NPC137718
0.5946	Remote Similarity	NPC483902
0.5946	Remote Similarity	NPC472577
0.5921	Remote Similarity	NPC171207
0.5867	Remote Similarity	NPC246480
0.5823	Remote Similarity	NPC473613
0.5714	Remote Similarity	NPC473673
0.5694	Remote Similarity	NPC474608
0.5658	Remote Similarity	NPC90257
0.5658	Remote Similarity	NPC483845
0.5658	Remote Similarity	NPC69357
0.5632	Remote Similarity	NPC294512
0.5625	Remote Similarity	NPC473085
0.5595	Remote Similarity	NPC610134
0.557	Remote Similarity	NPC266265
0.55	Remote Similarity	NPC96903
0.5455	Remote Similarity	NPC483883
0.5455	Remote Similarity	NPC151585
0.5443	Remote Similarity	NPC472574
0.5443	Remote Similarity	NPC92293
0.5443	Remote Similarity	NPC483844
0.5422	Remote Similarity	NPC14499
0.5393	Remote Similarity	NPC483868
0.5366	Remote Similarity	NPC483849
0.5366	Remote Similarity	NPC481489
0.5357	Remote Similarity	NPC479040
0.5333	Remote Similarity	NPC481047
0.5333	Remote Similarity	NPC481045
0.5281	Remote Similarity	NPC176413
0.5281	Remote Similarity	NPC483885
0.5281	Remote Similarity	NPC479045
0.527	Remote Similarity	NPC283375
0.527	Remote Similarity	NPC183122
0.527	Remote Similarity	NPC481066
0.5244	Remote Similarity	NPC483848
0.519	Remote Similarity	NPC483842
0.5185	Remote Similarity	NPC11685
0.5185	Remote Similarity	NPC16912
0.5128	Remote Similarity	NPC70973
0.5119	Remote Similarity	NPC481488
0.5062	Remote Similarity	NPC306146
0.5062	Remote Similarity	NPC483841
0.506	Remote Similarity	NPC481490
0.5059	Remote Similarity	NPC88593
0.5057	Remote Similarity	NPC479041

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3510
0.1-0.2	5453
0.2-0.3	187
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