NPASS Compound

Natural Product: NPC486578

Natural Product ID	NPC486578
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VBEKXFGLMJWWNF-XMHBHJPISA-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 56 59 0 0 0 0 0 0 0 0999 V2000 -8.3060 -2.7466 2.0334 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9123 -2.6062 1.9210 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4165 -1.5086 1.2214 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2686 -0.5808 0.6518 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7745 0.4974 -0.0356 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4019 0.6543 -0.1581 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5071 -0.2503 0.3961 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0497 -1.3232 1.0811 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2193 -0.0875 0.2714 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6636 0.9334 -0.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2130 0.9757 -0.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4701 -0.0361 0.1916 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9048 -0.0530 0.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6318 0.9319 -0.4541 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9191 1.9493 -1.0825 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4747 1.9337 -1.0486 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5986 2.9611 -1.7313 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0063 0.9917 -0.5155 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9042 0.0778 0.0445 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7724 -0.5805 -1.0219 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5390 -1.6868 -0.3294 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7563 -1.3739 1.1198 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7477 0.0781 1.4466 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1365 0.6513 1.1803 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2824 1.9324 1.6538 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7566 0.8096 0.8640 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8808 -2.1167 1.9451 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7526 -1.9439 -0.9924 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0133 -1.1617 -2.0257 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4527 1.8809 -0.9640 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8418 1.7108 -0.8330 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6022 2.5581 -1.3534 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0097 2.9817 -1.6648 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5691 1.4666 -0.6322 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4881 -3.7340 2.5433 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7595 -1.9775 2.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8353 -2.7831 1.0722 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3545 -0.6754 0.7301 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3973 -2.0610 1.5344 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.8206 0.6947 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4271 -0.8619 0.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9395 2.7548 -1.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1102 3.4643 -2.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3956 -0.7339 0.5643 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4292 0.1770 -1.4826 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9029 -2.6033 -0.3758 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7803 -1.7690 1.3822 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6135 0.1654 2.5652 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2892 0.6921 0.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9023 -0.0595 1.5507 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0926 2.6428 0.9993 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6993 -2.9536 1.4121 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6108 -1.6871 -1.9439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9321 -0.5374 -2.8044 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1758 3.0383 -2.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6845 2.4026 -0.2412 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 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 14 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 22 27 1 0 21 28 1 0 20 29 1 0 10 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 5 34 1 0 8 3 1 0 16 11 1 0 26 19 1 0 31 6 1 0 1 35 1 0 1 36 1 0 1 37 1 0 4 38 1 0 8 39 1 0 12 40 1 0 13 41 1 0 16 42 1 0 17 43 1 0 19 44 1 1 20 45 1 6 21 46 1 1 22 47 1 1 23 48 1 1 24 49 1 0 24 50 1 0 25 51 1 0 27 52 1 0 28 53 1 0 29 54 1 0 33 55 1 0 34 56 1 0 M END

Standard InCHIKey	VBEKXFGLMJWWNF-XMHBHJPISA-N
Standard InCHI	InChI=1S/C22H22O12/c1-31-9-5-11(25)15-13(6-9)32-21(19(29)17(15)27)8-2-3-12(10(24)4-8)33-22-20(30)18(28)16(26)14(7-23)34-22/h2-6,14,16,18,20,22-26,28-30H,7H2,1H3/t14-,16-,18+,20-,22-/m1/s1
SMILES	COc1cc(c2c(c1)oc(c1ccc(c(c1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)c(c2=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	478.11	Volume:	439.233 ? Van der Waals volume.
Dense:	1.089	LogP:	0.758 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.462 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.189 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	199.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.254	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.981	Fsp³:	0.318
MCE-18:	90.31 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.674	Fluc inhibitor:	0.32 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.94 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.922 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.12	Promiscuous compounds:	0.786

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.307	MDCK Permeability:	-5.322
Pgp-inhibitor:	0.006	Pgp-substrate:	0.049
PAMPA:	0.937 ? 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):	0.908
20% Bioavailability (F20%):	0.025	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.073
Plasma Protein Binding (PPB):	82.331%	Volume Distribution (VD):	-0.209
Fu:	14.827% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.921
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.202	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.738
HLM stability:	0.847 ? 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):

3.063

Half-life (T1/2):

3.588

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.098
Human Hepatotoxicity (H-HT):	0.564	Drug-induced Liver Injury (DILI):	0.973
AMES Toxicity:	0.873	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.064	Skin Sensitization:	0.975
Carcinogencity:	0.365	Eye Corrosion:	0.0
Eye Irritation:	0.644	Respiratory Toxicity:	0.046
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.788
Hematotoxicity:	0.234	Drug-induced Nephrotoxicity:	0.319
Genotoxicity:	0.698	RPMI-8226 Immunitoxicity:	0.102
A549 Cytotoxicity:	0.289	Hek293 Cytotoxicity:	0.258
BCF:	0.522 ? 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:	3.136 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.519 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.736 ? 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
NPO40956	Woodfordia uniflora	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32639158]

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
MIC	3

Activity Type	# Activity
Organism	3

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
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	104600.0	nM	PMID[32639158]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	52300.0	nM	PMID[32639158]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	104600.0	nM	PMID[32639158]

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 NPC486578 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	19643
0.1-0.2	25692
0.2-0.3	3084
0.3-0.4	947
0.4-0.5	306
0.5-0.6	134
0.6-0.7	37
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC285197
0.8182	Intermediate Similarity	NPC601586
0.7895	Intermediate Similarity	NPC21100
0.7867	Intermediate Similarity	NPC277205
0.7867	Intermediate Similarity	NPC37919
0.7632	Intermediate Similarity	NPC323593
0.7632	Intermediate Similarity	NPC203500
0.7468	Intermediate Similarity	NPC22832
0.7108	Intermediate Similarity	NPC251417
0.7051	Intermediate Similarity	NPC254306
0.6914	Remote Similarity	NPC307938
0.675	Remote Similarity	NPC95090
0.675	Remote Similarity	NPC27408
0.6747	Remote Similarity	NPC607707
0.6714	Remote Similarity	NPC200740
0.6667	Remote Similarity	NPC245014
0.663	Remote Similarity	NPC135358
0.6627	Remote Similarity	NPC243930
0.6627	Remote Similarity	NPC605067
0.6627	Remote Similarity	NPC609478
0.6625	Remote Similarity	NPC289667
0.6625	Remote Similarity	NPC238376
0.6585	Remote Similarity	NPC117260
0.6552	Remote Similarity	NPC275454
0.6463	Remote Similarity	NPC84265
0.6463	Remote Similarity	NPC84362
0.6429	Remote Similarity	NPC197285
0.642	Remote Similarity	NPC108831
0.642	Remote Similarity	NPC182634
0.6353	Remote Similarity	NPC311830
0.631	Remote Similarity	NPC191306
0.631	Remote Similarity	NPC60735
0.631	Remote Similarity	NPC26230
0.631	Remote Similarity	NPC611303
0.6235	Remote Similarity	NPC120099
0.6235	Remote Similarity	NPC21666
0.6235	Remote Similarity	NPC601144
0.6145	Remote Similarity	NPC297987
0.6145	Remote Similarity	NPC136042
0.6145	Remote Similarity	NPC189142
0.6145	Remote Similarity	NPC77660
0.6071	Remote Similarity	NPC73511
0.6044	Remote Similarity	NPC131745
0.6024	Remote Similarity	NPC261866
0.6024	Remote Similarity	NPC39360
0.6024	Remote Similarity	NPC29763
0.6024	Remote Similarity	NPC210003
0.5952	Remote Similarity	NPC282987
0.5922	Remote Similarity	NPC470719
0.5833	Remote Similarity	NPC58053
0.5824	Remote Similarity	NPC67105
0.5814	Remote Similarity	NPC472459
0.5795	Remote Similarity	NPC116458
0.5795	Remote Similarity	NPC246943
0.5795	Remote Similarity	NPC605784
0.5765	Remote Similarity	NPC609879
0.57	Remote Similarity	NPC480796
0.5698	Remote Similarity	NPC22195
0.5698	Remote Similarity	NPC186807
0.5698	Remote Similarity	NPC21190
0.5684	Remote Similarity	NPC209296
0.5682	Remote Similarity	NPC284960
0.5652	Remote Similarity	NPC227508
0.5638	Remote Similarity	NPC64425
0.5618	Remote Similarity	NPC136761
0.56	Remote Similarity	NPC166753
0.5581	Remote Similarity	NPC64305
0.5581	Remote Similarity	NPC234739
0.5568	Remote Similarity	NPC609451
0.5567	Remote Similarity	NPC80068
0.5541	Remote Similarity	NPC87125
0.5524	Remote Similarity	NPC198199
0.5521	Remote Similarity	NPC606657
0.5517	Remote Similarity	NPC46420
0.5517	Remote Similarity	NPC271692
0.5517	Remote Similarity	NPC181712
0.5506	Remote Similarity	NPC229729
0.5465	Remote Similarity	NPC143851
0.5455	Remote Similarity	NPC252933
0.5444	Remote Similarity	NPC88023
0.5444	Remote Similarity	NPC309025
0.5437	Remote Similarity	NPC277532
0.5429	Remote Similarity	NPC295625
0.5421	Remote Similarity	NPC470720
0.5408	Remote Similarity	NPC256760
0.5405	Remote Similarity	NPC152042
0.5402	Remote Similarity	NPC197896
0.5402	Remote Similarity	NPC313163
0.5402	Remote Similarity	NPC158674
0.5385	Remote Similarity	NPC203050
0.5385	Remote Similarity	NPC469931
0.5385	Remote Similarity	NPC225434
0.537	Remote Similarity	NPC120952
0.5366	Remote Similarity	NPC191154
0.5354	Remote Similarity	NPC287889
0.5341	Remote Similarity	NPC58716
0.5341	Remote Similarity	NPC45638
0.5333	Remote Similarity	NPC143799
0.5333	Remote Similarity	NPC605755
0.5327	Remote Similarity	NPC470717
0.5325	Remote Similarity	NPC93376
0.5301	Remote Similarity	NPC134819
0.5287	Remote Similarity	NPC210042
0.5287	Remote Similarity	NPC45618
0.5287	Remote Similarity	NPC476405
0.5281	Remote Similarity	NPC42773
0.5281	Remote Similarity	NPC182045
0.5281	Remote Similarity	NPC45522
0.5281	Remote Similarity	NPC60966
0.5281	Remote Similarity	NPC325555
0.5281	Remote Similarity	NPC226304
0.5281	Remote Similarity	NPC201292
0.5275	Remote Similarity	NPC307518
0.5275	Remote Similarity	NPC602805
0.5269	Remote Similarity	NPC8856
0.5263	Remote Similarity	NPC183672
0.5248	Remote Similarity	NPC244875
0.5227	Remote Similarity	NPC93337
0.5227	Remote Similarity	NPC168822
0.5227	Remote Similarity	NPC146792
0.5222	Remote Similarity	NPC219904
0.5222	Remote Similarity	NPC80140
0.5222	Remote Similarity	NPC488071
0.5217	Remote Similarity	NPC488072
0.5217	Remote Similarity	NPC267254
0.5204	Remote Similarity	NPC35119
0.5195	Remote Similarity	NPC54394
0.5195	Remote Similarity	NPC270620
0.5192	Remote Similarity	NPC480441
0.5192	Remote Similarity	NPC470715
0.5192	Remote Similarity	NPC25523
0.5192	Remote Similarity	NPC164704
0.5169	Remote Similarity	NPC24043
0.5169	Remote Similarity	NPC105025
0.5169	Remote Similarity	NPC488080
0.5169	Remote Similarity	NPC169977
0.5169	Remote Similarity	NPC603655
0.5169	Remote Similarity	NPC610763
0.5165	Remote Similarity	NPC101026
0.5165	Remote Similarity	NPC148710
0.5165	Remote Similarity	NPC80188
0.5165	Remote Similarity	NPC488077
0.5165	Remote Similarity	NPC601710
0.5161	Remote Similarity	NPC477848
0.5155	Remote Similarity	NPC240306
0.5128	Remote Similarity	NPC223579
0.5119	Remote Similarity	NPC473241
0.5114	Remote Similarity	NPC249281
0.5114	Remote Similarity	NPC77672
0.5114	Remote Similarity	NPC44558
0.5114	Remote Similarity	NPC133671
0.5114	Remote Similarity	NPC19709
0.5114	Remote Similarity	NPC135391
0.5114	Remote Similarity	NPC78263
0.5114	Remote Similarity	NPC250069
0.5111	Remote Similarity	NPC27942
0.5111	Remote Similarity	NPC599850
0.5109	Remote Similarity	NPC150442
0.5104	Remote Similarity	NPC233994
0.5104	Remote Similarity	NPC22062
0.5104	Remote Similarity	NPC473634
0.5104	Remote Similarity	NPC138811
0.51	Remote Similarity	NPC195257
0.51	Remote Similarity	NPC475382
0.5098	Remote Similarity	NPC14187
0.5094	Remote Similarity	NPC470716
0.5094	Remote Similarity	NPC255799
0.5063	Remote Similarity	NPC25292
0.5056	Remote Similarity	NPC145038
0.5056	Remote Similarity	NPC56077
0.5056	Remote Similarity	NPC281131
0.5056	Remote Similarity	NPC253662
0.5056	Remote Similarity	NPC179950
0.5056	Remote Similarity	NPC88789
0.5056	Remote Similarity	NPC491374
0.5055	Remote Similarity	NPC479402
0.5053	Remote Similarity	NPC187379
0.5052	Remote Similarity	NPC169733
0.5051	Remote Similarity	NPC124155
0.5051	Remote Similarity	NPC32641
0.5051	Remote Similarity	NPC256188

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486578 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4908
0.1-0.2	4146
0.2-0.3	79
0.3-0.4	10
0.4-0.5	6
0.5-0.6	1
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
0.5684	Remote Similarity	NPD7054	Phase 4

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