NPASS Compound

Natural Product: NPC568908

Natural Product ID	NPC568908
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3,5,7-trihydroxy-2-[4-hydroxy-3-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]chromen-4-one
IUPAC Name	3,5,7-trihydroxy-2-[4-hydroxy-3-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]chromen-4-one
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 52 55 0 0 0 0 0 0 0 0999 V2000 5.3671 1.2514 -1.9931 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8057 0.5522 -0.7804 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4644 0.8881 -0.6776 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7703 0.0555 0.1956 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3212 -1.0265 -0.5323 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0428 -1.3752 -0.8084 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0990 -0.6804 -0.3927 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3666 -1.0648 -0.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5680 -0.3624 -0.2735 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5296 0.7775 0.4768 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3596 1.3893 0.9207 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7577 1.3675 0.8203 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7382 2.4188 1.5116 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9205 0.7820 0.3939 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1508 1.3395 0.7160 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1356 2.5057 1.4826 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3196 0.7476 0.2851 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3063 -0.4090 -0.4742 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5154 -0.9536 -0.8754 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0913 -0.9698 -0.7990 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9058 -0.3682 -0.3612 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -0.8698 -0.6492 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5063 -2.2113 -1.4513 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4211 -2.9393 -1.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8537 -2.5376 -1.5801 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9828 -3.2379 -1.9999 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5917 -0.3861 1.3700 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7735 -0.3695 2.5104 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8030 0.4013 1.6482 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5314 1.4256 2.5862 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4728 1.0435 0.4854 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8317 0.7208 0.3969 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6021 1.7195 -2.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0918 2.0521 -1.6758 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9405 0.5449 -2.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9806 -0.5347 -0.8598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9241 0.6588 0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1199 0.1955 0.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2032 2.3971 0.8141 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8837 2.6280 2.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2588 1.2079 0.5537 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0247 -0.4801 -1.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0413 -1.8638 -1.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5062 -2.5714 -1.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5430 -3.8434 -2.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6264 -3.6687 -1.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8726 -1.4514 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5997 0.5756 2.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5850 -0.2321 2.1646 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3936 1.8743 2.7829 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3980 2.1612 0.5064 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1559 0.7257 -0.5514 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 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 10 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 15 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 21 22 1 0 8 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 4 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 2 1 0 25 6 1 0 22 9 1 0 21 14 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 6 4 37 1 1 7 38 1 0 11 39 1 0 16 40 1 0 17 41 1 0 19 42 1 0 20 43 1 0 23 44 1 0 24 45 1 0 26 46 1 0 27 47 1 6 28 48 1 0 29 49 1 1 30 50 1 0 31 51 1 1 32 52 1 0 M END

Standard InCHIKey	KCPGPFNOACHSRM-XNFUJFQVSA-N
Standard InCHI	InChI=1S/C21H20O11/c1-7-15(25)17(27)19(29)21(30-7)32-12-4-8(2-3-10(12)23)20-18(28)16(26)14-11(24)5-9(22)6-13(14)31-20/h2-7,15,17,19,21-25,27-29H,1H3/t7-,15-,17+,19+,21-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=CC(C3=C(O)C(=O)C4=C(O)C=C(O)C=C4O3)=CC=C2O)[C@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	448.1	Volume:	413.147 ? Van der Waals volume.
Dense:	1.085	LogP:	1.291 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.541 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.063 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	190.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.028	Fsp³:	0.286
MCE-18:	91.0 ? 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:	0.615	Fluc inhibitor:	0.314 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.906 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.823 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.23	Promiscuous compounds:	0.903

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.167	MDCK Permeability:	-4.976
Pgp-inhibitor:	0.001	Pgp-substrate:	0.46
PAMPA:	0.987 ? 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):	0.574
20% Bioavailability (F20%):	0.242	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.233
Plasma Protein Binding (PPB):	90.793%	Volume Distribution (VD):	-0.28
Fu:	6.046% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.993
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.119	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.119
CYP2C9-inhibitor:	0.042	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.011	CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.982 ? 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):

2.827

Half-life (T1/2):

4.217

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.289
Human Hepatotoxicity (H-HT):	0.442	Drug-induced Liver Injury (DILI):	0.926
AMES Toxicity:	0.791	Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.303	Skin Sensitization:	0.956
Carcinogencity:	0.157	Eye Corrosion:	0.005
Eye Irritation:	0.978	Respiratory Toxicity:	0.291
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.492
Hematotoxicity:	0.088	Drug-induced Nephrotoxicity:	0.164
Genotoxicity:	0.932	RPMI-8226 Immunitoxicity:	0.162
A549 Cytotoxicity:	0.64	Hek293 Cytotoxicity:	0.56
BCF:	0.765 ? 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:	3.324 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.405 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.794 ? 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
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22989532]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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

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

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 NPC568908 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	20231
0.1-0.2	26074
0.2-0.3	2523
0.3-0.4	620
0.4-0.5	266
0.5-0.6	99
0.6-0.7	28
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8514	High Similarity	NPC197285
0.725	Intermediate Similarity	NPC223747
0.6875	Remote Similarity	NPC21100
0.6747	Remote Similarity	NPC601586
0.6709	Remote Similarity	NPC108831
0.6709	Remote Similarity	NPC182634
0.6707	Remote Similarity	NPC601710
0.662	Remote Similarity	NPC125062
0.6582	Remote Similarity	NPC111929
0.6582	Remote Similarity	NPC320283
0.6582	Remote Similarity	NPC41121
0.6512	Remote Similarity	NPC187379
0.65	Remote Similarity	NPC127546
0.65	Remote Similarity	NPC57625
0.65	Remote Similarity	NPC254306
0.65	Remote Similarity	NPC476405
0.65	Remote Similarity	NPC173637
0.65	Remote Similarity	NPC317489
0.65	Remote Similarity	NPC238376
0.65	Remote Similarity	NPC223424
0.65	Remote Similarity	NPC600591
0.6471	Remote Similarity	NPC4390
0.6304	Remote Similarity	NPC476472
0.6304	Remote Similarity	NPC294815
0.6304	Remote Similarity	NPC16194
0.619	Remote Similarity	NPC219904
0.6163	Remote Similarity	NPC203050
0.6163	Remote Similarity	NPC225434
0.6044	Remote Similarity	NPC153755
0.6024	Remote Similarity	NPC265530
0.5976	Remote Similarity	NPC135599
0.5976	Remote Similarity	NPC73855
0.5976	Remote Similarity	NPC113968
0.5976	Remote Similarity	NPC328940
0.5976	Remote Similarity	NPC277174
0.5976	Remote Similarity	NPC606877
0.5729	Remote Similarity	NPC287889
0.5714	Remote Similarity	NPC173582
0.5714	Remote Similarity	NPC265885
0.5714	Remote Similarity	NPC181465
0.5714	Remote Similarity	NPC215710
0.5714	Remote Similarity	NPC473438
0.5714	Remote Similarity	NPC253788
0.566	Remote Similarity	NPC192539
0.5652	Remote Similarity	NPC203259
0.5652	Remote Similarity	NPC33054
0.5652	Remote Similarity	NPC176740
0.5652	Remote Similarity	NPC471725
0.5652	Remote Similarity	NPC134532
0.5652	Remote Similarity	NPC602582
0.5647	Remote Similarity	NPC323593
0.5647	Remote Similarity	NPC203500
0.5625	Remote Similarity	NPC220173
0.5581	Remote Similarity	NPC84265
0.5568	Remote Similarity	NPC606560
0.5556	Remote Similarity	NPC89052
0.5543	Remote Similarity	NPC67105
0.5529	Remote Similarity	NPC77672
0.5529	Remote Similarity	NPC133671
0.5529	Remote Similarity	NPC135391
0.5529	Remote Similarity	NPC78263
0.5529	Remote Similarity	NPC250069
0.5506	Remote Similarity	NPC136761
0.55	Remote Similarity	NPC268668
0.5465	Remote Similarity	NPC145038
0.5465	Remote Similarity	NPC282987
0.5465	Remote Similarity	NPC56077
0.5465	Remote Similarity	NPC281131
0.5465	Remote Similarity	NPC253662
0.5465	Remote Similarity	NPC179950
0.5465	Remote Similarity	NPC277205
0.5465	Remote Similarity	NPC37919
0.5465	Remote Similarity	NPC88789
0.5465	Remote Similarity	NPC491374
0.5455	Remote Similarity	NPC191306
0.5455	Remote Similarity	NPC60735
0.5455	Remote Similarity	NPC26230
0.5455	Remote Similarity	NPC285197
0.5446	Remote Similarity	NPC219043
0.5446	Remote Similarity	NPC173837
0.5417	Remote Similarity	NPC473327
0.5405	Remote Similarity	NPC28274
0.5402	Remote Similarity	NPC245014
0.5393	Remote Similarity	NPC486578
0.5393	Remote Similarity	NPC609478
0.5385	Remote Similarity	NPC116864
0.5385	Remote Similarity	NPC244776
0.5385	Remote Similarity	NPC477848
0.5341	Remote Similarity	NPC325555
0.5341	Remote Similarity	NPC226304
0.5319	Remote Similarity	NPC605592
0.5287	Remote Similarity	NPC609879
0.5281	Remote Similarity	NPC307938
0.5281	Remote Similarity	NPC175107
0.5278	Remote Similarity	NPC179271
0.5275	Remote Similarity	NPC476215
0.5269	Remote Similarity	NPC609888
0.5263	Remote Similarity	NPC54394
0.5263	Remote Similarity	NPC159103
0.5243	Remote Similarity	NPC217520
0.5233	Remote Similarity	NPC331652
0.5227	Remote Similarity	NPC305811
0.5227	Remote Similarity	NPC46420
0.5222	Remote Similarity	NPC120099
0.5222	Remote Similarity	NPC601144
0.5217	Remote Similarity	NPC95866
0.5213	Remote Similarity	NPC39834
0.5211	Remote Similarity	NPC116775
0.5176	Remote Similarity	NPC288084
0.5172	Remote Similarity	NPC249281
0.5172	Remote Similarity	NPC143851
0.5165	Remote Similarity	NPC88023
0.5165	Remote Similarity	NPC309025
0.5143	Remote Similarity	NPC139571
0.5139	Remote Similarity	NPC20791
0.5128	Remote Similarity	NPC252933
0.5128	Remote Similarity	NPC133953
0.5116	Remote Similarity	NPC67037
0.5116	Remote Similarity	NPC255615
0.5114	Remote Similarity	NPC64305
0.5106	Remote Similarity	NPC471079
0.5067	Remote Similarity	NPC219330
0.5056	Remote Similarity	NPC271692
0.5055	Remote Similarity	NPC101026
0.5055	Remote Similarity	NPC488077
0.5053	Remote Similarity	NPC67326
0.5053	Remote Similarity	NPC163242
0.5053	Remote Similarity	NPC272068
0.5053	Remote Similarity	NPC227508

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC568908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5421
0.1-0.2	3671
0.2-0.3	44
0.3-0.4	9
0.4-0.5	3
0.5-0.6	2
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
0.5652	Remote Similarity	NPD6797	Phase 2
0.5139	Remote Similarity	NPD1512	Phase 3

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