NPASS Compound

Natural Product: NPC252314

Natural Product ID	NPC252314
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OHBOUGPDFDVOIW-CAQYPJOUSA-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] [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 87 91 0 0 0 0 0 0 0 0999 V2000 -2.0450 -3.3913 -1.3979 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7068 -3.0896 0.0189 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9003 -2.6185 0.7956 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6311 -1.5216 1.7616 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8900 -0.3335 1.2693 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9483 -0.6928 0.1535 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5789 -0.3783 -1.1581 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8516 1.0118 -1.2118 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4346 1.5751 -2.3680 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6806 0.7613 -3.2994 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7536 2.9896 -2.5375 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3162 0.1524 0.1852 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5080 -0.5335 0.7883 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7224 -1.9433 0.3476 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6215 -2.3702 -0.6463 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5514 -2.1722 0.2499 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0891 -2.4400 1.5388 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2159 -2.7989 1.5244 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5529 -4.2298 1.3659 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8512 -2.3142 2.8309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7843 -3.7379 -0.9378 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0487 -4.2605 -2.1639 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1688 -3.5120 -3.1579 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1988 -5.7180 -2.3470 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6533 0.2338 0.4067 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4224 0.9401 1.3175 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0839 0.8934 2.5249 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5838 1.7202 0.9490 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3071 2.3968 1.9056 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4186 3.1507 1.5997 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8458 3.2513 0.3067 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1456 2.5865 -0.6794 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0375 1.8399 -0.3449 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7206 0.5770 -1.1017 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 1.9101 -1.3999 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5991 2.7485 -0.4969 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2803 2.3182 -2.7814 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6032 0.8214 1.0387 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5150 2.0279 1.6685 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6519 2.0705 2.5788 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2784 3.2177 1.4135 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2654 3.2595 0.4547 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0033 4.3914 0.1981 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7531 5.5297 0.9216 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7622 5.5411 1.9066 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0407 4.3631 2.1276 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8783 -1.1778 2.3310 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1476 -3.1917 -1.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9585 -4.4892 -1.6584 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4855 -2.8710 -2.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4074 -4.0810 0.4799 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3404 -3.4592 1.4193 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7037 -2.4060 0.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0989 -1.9895 2.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1825 -0.0356 2.1143 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5368 -0.8849 -1.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8781 -0.5592 -2.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2569 3.3807 -3.4659 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8418 3.1134 -2.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3710 3.6122 -1.7083 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1449 1.0713 0.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4247 -0.4161 1.8904 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7143 -2.2116 0.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7181 -1.7146 -1.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4149 -4.2938 0.6368 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 -4.9081 1.0826 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9958 -4.6676 2.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8153 -1.8375 2.6457 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1391 -1.7118 3.4331 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0798 -3.2058 3.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9428 -5.9771 -3.1264 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4090 -6.2537 -1.3854 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2285 -6.1530 -2.7138 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0219 2.3605 2.9599 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9552 3.6670 2.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7362 3.8517 0.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5054 2.6839 -1.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5199 1.3353 -1.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8167 1.6466 -3.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0110 3.3548 -2.9959 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3880 2.1341 -2.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4775 2.3537 -0.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7618 4.3995 -0.5481 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3486 6.4119 0.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5919 6.4488 2.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2817 4.4359 2.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1887 -1.9886 2.8062 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 6 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 6 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 17 18 1 0 18 19 1 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 13 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 12 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 16 2 1 0 33 28 1 0 46 41 1 0 16 6 1 0 18 14 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 1 3 52 1 0 3 53 1 0 4 54 1 1 5 55 1 1 7 56 1 0 7 57 1 0 11 58 1 0 11 59 1 0 11 60 1 0 12 61 1 1 13 62 1 1 14 63 1 6 15 64 1 6 19 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 20 70 1 0 24 71 1 0 24 72 1 0 24 73 1 0 29 74 1 0 30 75 1 0 31 76 1 0 32 77 1 0 33 78 1 0 37 79 1 0 37 80 1 0 37 81 1 0 42 82 1 0 43 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 47 87 1 0 M END

Standard InCHIKey	OHBOUGPDFDVOIW-CAQYPJOUSA-N
Standard InCHI	InChI=1S/C35H40O12/c1-19-17-25(39)28(46-32(41)24-15-11-8-12-16-24)34(18-42-20(2)36)30(44-22(4)38)27(45-31(40)23-13-9-7-10-14-23)26-29(43-21(3)37)35(19,34)47-33(26,5)6/h7-16,19,25-30,39H,17-18H2,1-6H3/t19-,25+,26-,27-,28+,29-,30-,34+,35-/m1/s1
SMILES	C[C@@H]1C[C@@H]([C@@H]([C@@]2(COC(=O)C)[C@@H]([C@@H]([C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1ccccc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.25	Volume:	647.615 ? Van der Waals volume.
Dense:	1.007	LogP:	3.188 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.039 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.885 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	31.0
TPSA:	160.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.327	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.938	Fsp³:	0.514
MCE-18:	167.774 ? 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:	0.6	Fluc inhibitor:	0.011 ? 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:	0.129 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.047	Promiscuous compounds:	0.079

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.599	MDCK Permeability:	-5.008
Pgp-inhibitor:	0.492	Pgp-substrate:	0.038
PAMPA:	0.656 ? 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%):	0.003	30% Bioavailability (F30%):	0.015
50% Bioavailability (F50%):	0.832

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992	MRP1:	1.0
Plasma Protein Binding (PPB):	84.331%	Volume Distribution (VD):	-0.283
Fu:	16.988% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.902	BCRP inhibitor:	0.0
BSEP inhibitor:	0.447

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.344	CYP3A4-substrate:	0.009
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):

1.253

Half-life (T1/2):

1.289

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.358
Human Hepatotoxicity (H-HT):	0.036	Drug-induced Liver Injury (DILI):	0.897
AMES Toxicity:	0.915	Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.188	Skin Sensitization:	0.999
Carcinogencity:	0.814	Eye Corrosion:	0.0
Eye Irritation:	0.513	Respiratory Toxicity:	0.056
Drug-induced Neurotoxicity:	0.765	Ototoxicity:	0.165
Hematotoxicity:	0.186	Drug-induced Nephrotoxicity:	0.605
Genotoxicity:	0.23	RPMI-8226 Immunitoxicity:	0.163
A549 Cytotoxicity:	0.827	Hek293 Cytotoxicity:	0.811
BCF:	0.577 ? 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:	3.473 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.822 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.357 ? 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	=	85.91	%	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 NPC252314 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	9757
0.1-0.2	37046
0.2-0.3	2347
0.3-0.4	511
0.4-0.5	136
0.5-0.6	38
0.6-0.7	17
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
0.7143	Intermediate Similarity	NPC483845
0.7042	Intermediate Similarity	NPC137718
0.7042	Intermediate Similarity	NPC148062
0.6944	Remote Similarity	NPC473088
0.6901	Remote Similarity	NPC147880
0.6761	Remote Similarity	NPC51314
0.6667	Remote Similarity	NPC90257
0.6667	Remote Similarity	NPC69357
0.6622	Remote Similarity	NPC41481
0.6533	Remote Similarity	NPC479043
0.6494	Remote Similarity	NPC483849
0.6456	Remote Similarity	NPC479040
0.64	Remote Similarity	NPC483844
0.6389	Remote Similarity	NPC241951
0.6301	Remote Similarity	NPC473060
0.6184	Remote Similarity	NPC306146
0.6184	Remote Similarity	NPC483841
0.6154	Remote Similarity	NPC483848
0.6133	Remote Similarity	NPC147217
0.6104	Remote Similarity	NPC11685
0.589	Remote Similarity	NPC475429
0.589	Remote Similarity	NPC211137
0.5811	Remote Similarity	NPC607964
0.5732	Remote Similarity	NPC603877
0.5696	Remote Similarity	NPC57628
0.5696	Remote Similarity	NPC266265
0.5696	Remote Similarity	NPC472569
0.5696	Remote Similarity	NPC16912
0.561	Remote Similarity	NPC481486
0.5526	Remote Similarity	NPC90614
0.5513	Remote Similarity	NPC483842
0.55	Remote Similarity	NPC472570
0.5467	Remote Similarity	NPC66761
0.5467	Remote Similarity	NPC483843
0.5467	Remote Similarity	NPC476094
0.5465	Remote Similarity	NPC473115
0.5455	Remote Similarity	NPC17877
0.5385	Remote Similarity	NPC4341
0.5385	Remote Similarity	NPC479047
0.5385	Remote Similarity	NPC291638
0.5366	Remote Similarity	NPC472568
0.5325	Remote Similarity	NPC483862
0.5316	Remote Similarity	NPC483846
0.5301	Remote Similarity	NPC481489
0.5263	Remote Similarity	NPC481047
0.5263	Remote Similarity	NPC481045
0.5256	Remote Similarity	NPC483902
0.525	Remote Similarity	NPC473758
0.525	Remote Similarity	NPC471100
0.525	Remote Similarity	NPC605884
0.5238	Remote Similarity	NPC481488
0.519	Remote Similarity	NPC191082
0.5128	Remote Similarity	NPC475759
0.5128	Remote Similarity	NPC483847
0.5063	Remote Similarity	NPC281717
0.5062	Remote Similarity	NPC254558
0.5062	Remote Similarity	NPC471104
0.5062	Remote Similarity	NPC471107

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC252314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3093
0.1-0.2	5852
0.2-0.3	204
0.3-0.4	1
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