NPASS Compound

Natural Product: NPC482300

Natural Product ID	NPC482300
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RDGMYUPKWFNGGC-PISILSIWSA-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 89 91 0 0 0 0 0 0 0 0999 V2000 -1.6129 3.5579 3.3366 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1953 2.2767 2.5378 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5149 1.8209 1.9548 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9554 0.5949 2.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2082 0.0550 1.6258 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2860 1.1105 1.4584 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7560 -0.8982 2.7017 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1755 -0.7087 0.3653 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7005 -1.8018 0.2461 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4885 -0.1758 -0.8713 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0079 -0.4418 -0.7049 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0829 0.5073 -1.2888 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5183 1.4268 -2.1192 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4040 0.4862 -0.9781 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6449 0.6808 0.4840 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6228 -0.2610 1.1136 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8090 0.3812 2.4700 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0983 -0.0698 3.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8275 1.8426 2.1363 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9463 2.0622 0.9486 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2972 2.7333 1.4979 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6175 3.8471 1.0090 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3841 2.8852 -0.0152 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4151 3.0436 -0.8429 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2876 2.1848 -0.7084 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4956 4.1571 -1.8336 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8343 -0.4617 0.4661 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3056 -1.7495 0.2205 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6010 -2.7056 0.6018 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5815 -1.9866 -0.4605 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0577 -3.2522 -0.7143 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2543 -3.5084 -1.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0078 -2.4348 -1.7518 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5681 -1.1484 -1.5176 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3556 -0.9302 -0.8723 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0129 -0.6363 -1.5664 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9158 -0.6064 -2.6108 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1849 0.5214 -3.0408 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5294 -1.8311 -3.1884 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7289 -1.8215 -0.8539 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4440 -2.7001 0.1314 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4201 -2.2703 1.3003 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1730 -4.1283 -0.2109 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9628 -0.8373 -1.9878 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6733 -0.3761 -3.0499 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9937 0.8154 -3.0985 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0283 -1.3668 -4.1147 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4340 4.0698 2.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8782 3.2666 4.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7538 4.2673 3.3315 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8781 1.5047 3.2183 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0746 2.5604 1.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3204 -0.0762 2.7507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9873 1.9020 0.7556 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1758 0.6061 1.0296 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5938 1.5016 2.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9527 -1.4709 3.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2431 -0.3022 3.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5323 -1.5645 2.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6770 0.9308 -0.9041 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8994 -0.3803 0.4473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5359 1.5482 -2.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8236 2.1598 -2.5738 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 1.3466 -1.4979 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3136 0.4163 1.0683 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1327 -1.2576 1.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9606 0.0654 3.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0751 0.2573 4.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1250 -1.1717 3.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9538 0.4059 2.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8836 2.1195 1.9891 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4888 2.3968 3.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4694 4.4036 -2.1753 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0963 3.9098 -2.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8745 5.0425 -1.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4735 -4.1073 -0.4036 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6270 -4.4969 -1.5501 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9531 -2.6208 -2.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1932 -0.3205 -1.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0401 0.0684 -0.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5606 -1.6635 -3.5403 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4891 -2.6511 -2.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 -2.1780 -4.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9914 -4.5930 -0.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0152 -4.7228 0.7156 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1992 -4.1350 -0.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0527 -1.7928 -4.4715 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5489 -2.2044 -3.6024 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6102 -0.9223 -4.9258 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 5 7 1 0 5 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 20 23 1 6 23 24 1 0 24 25 2 0 24 26 1 0 16 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 14 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 11 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 10 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 21 2 1 0 35 30 1 0 20 15 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 1 3 52 1 0 4 53 1 0 6 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 7 59 1 0 10 60 1 6 11 61 1 1 13 62 1 0 13 63 1 0 14 64 1 6 15 65 1 1 16 66 1 1 17 67 1 1 18 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 19 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 31 76 1 0 32 77 1 0 33 78 1 0 34 79 1 0 35 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 43 84 1 0 43 85 1 0 43 86 1 0 47 87 1 0 47 88 1 0 47 89 1 0 M END

Standard InCHIKey	RDGMYUPKWFNGGC-PISILSIWSA-N
Standard InCHI	InChI=1S/C35H42O12/c1-18-15-16-34(8,9)32(41)30(45-23(6)38)29(44-22(5)37)20(3)28(43-21(4)36)26-27(46-33(42)25-13-11-10-12-14-25)19(2)17-35(26,31(18)40)47-24(7)39/h10-16,18-19,26-30H,3,17H2,1-2,4-9H3/b16-15+/t18-,19-,26+,27-,28-,29-,30+,35+/m0/s1
SMILES	C[C@H]1/C=C/C(C)(C)C(=O)[C@@H]([C@H](C(=C)[C@@H]([C@H]2[C@H]([C@@H](C)C[C@@]2(C1=O)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.27	Volume:	662.092 ? Van der Waals volume.
Dense:	0.988	LogP:	2.44 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.766 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.286 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	30.0
TPSA:	165.64 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.247	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.582	Fsp³:	0.514
MCE-18:	104.698 ? 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:	0.732	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.033 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.321	Promiscuous compounds:	0.151

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.13	MDCK Permeability:	-4.649
Pgp-inhibitor:	1.0	Pgp-substrate:	0.003
PAMPA:	0.783 ? 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%):	0.974	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	87.63%	Volume Distribution (VD):	-0.103
Fu:	13.966% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.172
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.182	CYP3A4-substrate:	1.0
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):

5.209

Half-life (T1/2):

0.443

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.086
Human Hepatotoxicity (H-HT):	0.567	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.419	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.192	Skin Sensitization:	0.98
Carcinogencity:	0.503	Eye Corrosion:	0.0
Eye Irritation:	0.075	Respiratory Toxicity:	0.025
Drug-induced Neurotoxicity:	0.291	Ototoxicity:	0.385
Hematotoxicity:	0.525	Drug-induced Nephrotoxicity:	0.944
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.145
A549 Cytotoxicity:	0.287	Hek293 Cytotoxicity:	0.269
BCF:	0.729 ? 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:	3.755 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.549 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.167 ? 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
NPO40845	Euphorbia glomerulans	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30860373]

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
Ratio IC50	1
IC50	3

Activity Type	# Activity
Cell line	2
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	6.8	n.a.	PMID[30860373]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	IC50	=	9600.0	nM	PMID[30860373]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	IC50	>	100000.0	nM	PMID[30860373]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[30860373]

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 NPC482300 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	12714
0.1-0.2	34907
0.2-0.3	1785
0.3-0.4	334
0.4-0.5	60
0.5-0.6	33
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC482315
0.8841	High Similarity	NPC86772
0.831	Intermediate Similarity	NPC482314
0.7917	Intermediate Similarity	NPC482308
0.7703	Intermediate Similarity	NPC475262
0.7467	Intermediate Similarity	NPC482304
0.7313	Intermediate Similarity	NPC105725
0.7273	Intermediate Similarity	NPC482310
0.7273	Intermediate Similarity	NPC482302
0.7237	Intermediate Similarity	NPC272523
0.7051	Intermediate Similarity	NPC482272
0.7013	Intermediate Similarity	NPC265459
0.7013	Intermediate Similarity	NPC482265
0.6974	Remote Similarity	NPC482307
0.6842	Remote Similarity	NPC473497
0.6795	Remote Similarity	NPC290833
0.6582	Remote Similarity	NPC482249
0.642	Remote Similarity	NPC482301
0.6341	Remote Similarity	NPC482252
0.625	Remote Similarity	NPC276652
0.6207	Remote Similarity	NPC482258
0.6173	Remote Similarity	NPC482153
0.6173	Remote Similarity	NPC82467
0.6098	Remote Similarity	NPC482316
0.5976	Remote Similarity	NPC482270
0.5949	Remote Similarity	NPC196683
0.5904	Remote Similarity	NPC482311
0.5862	Remote Similarity	NPC482250
0.5833	Remote Similarity	NPC482312
0.5802	Remote Similarity	NPC42234
0.5783	Remote Similarity	NPC482309
0.5714	Remote Similarity	NPC482303
0.5714	Remote Similarity	NPC482248
0.5714	Remote Similarity	NPC482254
0.5647	Remote Similarity	NPC474303
0.5581	Remote Similarity	NPC475413
0.5581	Remote Similarity	NPC482263
0.5556	Remote Similarity	NPC482353
0.5542	Remote Similarity	NPC325805
0.5529	Remote Similarity	NPC285221
0.5529	Remote Similarity	NPC482347
0.5465	Remote Similarity	NPC475660
0.5465	Remote Similarity	NPC482269
0.5435	Remote Similarity	NPC187494
0.5412	Remote Similarity	NPC194769
0.5357	Remote Similarity	NPC472250
0.5349	Remote Similarity	NPC270364
0.5349	Remote Similarity	NPC118799
0.5287	Remote Similarity	NPC482268
0.5287	Remote Similarity	NPC482267
0.5222	Remote Similarity	NPC317191
0.519	Remote Similarity	NPC470188
0.5172	Remote Similarity	NPC482251
0.5165	Remote Similarity	NPC470190
0.5114	Remote Similarity	NPC205389
0.5059	Remote Similarity	NPC482313
0.5057	Remote Similarity	NPC601407

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3788
0.1-0.2	5234
0.2-0.3	128
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