NPASS Compound

Natural Product: NPC548009

Natural Product ID	NPC548009
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-pyrano[2,3-h]chromen-4-one
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-pyrano[2,3-h]chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 62 66 0 0 0 0 0 0 0 0999 V2000 -3.1013 1.0069 2.5144 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9446 -0.2427 2.4001 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2367 -1.2986 1.8364 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8901 -1.0184 0.5411 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7872 -1.7467 0.0292 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6278 -1.1245 -0.4096 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4272 -0.9702 0.4315 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5364 -1.4031 1.8118 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5733 -0.8895 2.6144 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7808 -1.2819 3.9053 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9508 -2.2270 4.4805 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1313 -2.6427 5.7746 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0752 -2.7565 3.7324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2571 -2.3259 2.4012 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4869 -0.3367 -0.1028 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5362 0.1033 -1.3209 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6822 0.7537 -1.7980 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8305 0.9397 -0.9211 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9173 1.5512 -1.3603 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0238 2.0689 -2.7377 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2072 1.3934 -3.4423 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3294 3.5664 -2.7321 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8994 1.8620 -3.5212 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7496 1.2240 -3.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6688 1.0681 -3.9651 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5551 0.4369 -3.5034 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5286 0.2789 -4.3819 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4848 -0.0410 -2.1990 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6379 -0.6751 -1.7350 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5988 -0.8168 -2.5112 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1566 -1.1994 -0.2658 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6646 -2.4841 0.0449 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1711 -0.2134 0.2065 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1063 0.9912 -0.5341 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2271 0.0438 1.6638 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2915 -0.6594 2.2798 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4075 1.5360 3.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1933 1.6555 1.6185 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0409 0.6828 2.6757 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2136 -0.5466 3.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6115 0.0717 0.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2275 -0.1535 2.1815 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5870 -0.8656 4.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8524 -3.5191 6.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7583 -3.4971 4.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0532 -2.7924 1.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7813 0.5673 0.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7566 1.6835 -0.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6464 2.0522 -4.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7973 0.5005 -3.9573 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9998 1.1380 -2.7255 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9158 3.8451 -1.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9023 3.8494 -3.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3768 4.1264 -2.7418 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7310 1.4365 -4.9620 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3123 -0.2166 -5.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0273 -1.0832 -1.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7604 -2.5470 1.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1793 -0.6427 -0.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7074 0.9997 -1.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4642 1.1153 1.8326 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3133 -0.3309 3.2339 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 2 0 9 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 7 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 26 28 2 0 28 29 1 0 29 30 2 0 4 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 2 1 0 29 6 1 0 14 8 1 0 28 16 1 0 24 17 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 1 4 41 1 1 9 42 1 0 10 43 1 0 12 44 1 0 13 45 1 0 14 46 1 0 18 47 1 0 19 48 1 0 21 49 1 0 21 50 1 0 21 51 1 0 22 52 1 0 22 53 1 0 22 54 1 0 25 55 1 0 27 56 1 0 31 57 1 6 32 58 1 0 33 59 1 6 34 60 1 0 35 61 1 6 36 62 1 0 M END

Standard InCHIKey	FRKNVAWDQIICIE-QJAGZXCNSA-N
Standard InCHI	InChI=1S/C26H26O10/c1-11-18(29)20(31)21(32)25(33-11)35-24-19(30)17-15(28)10-16-14(8-9-26(2,3)36-16)23(17)34-22(24)12-4-6-13(27)7-5-12/h4-11,18,20-21,25,27-29,31-32H,1-3H3/t11-,18-,20+,21-,25-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=C(C3=CC=C(O)C=C3)OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)[C@@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.15	Volume:	479.644 ? Van der Waals volume.
Dense:	1.039	LogP:	2.97 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.71 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.222 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	29.0
TPSA:	159.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.363	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.314	Fsp³:	0.346
MCE-18:	110.314 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.69	Fluc inhibitor:	0.31 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.897 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.872 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.113	Promiscuous compounds:	0.247

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.828	MDCK Permeability:	-5.001
Pgp-inhibitor:	0.012	Pgp-substrate:	0.209
PAMPA:	0.988 ? 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%):	0.292	30% Bioavailability (F30%):	0.972
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.198
Plasma Protein Binding (PPB):	94.676%	Volume Distribution (VD):	-0.043
Fu:	4.589% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.982	BCRP inhibitor:	0.682
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.364
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.75
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.944 ? 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):

3.085

Half-life (T1/2):

3.827

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.487
Human Hepatotoxicity (H-HT):	0.412	Drug-induced Liver Injury (DILI):	0.803
AMES Toxicity:	0.588	Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.341	Skin Sensitization:	0.863
Carcinogencity:	0.207	Eye Corrosion:	0.0
Eye Irritation:	0.503	Respiratory Toxicity:	0.172
Drug-induced Neurotoxicity:	0.03	Ototoxicity:	0.802
Hematotoxicity:	0.082	Drug-induced Nephrotoxicity:	0.328
Genotoxicity:	0.489	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.109	Hek293 Cytotoxicity:	0.417
BCF:	1.204 ? 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:	3.802 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.214 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.621 ? 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
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	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

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 NPC548009 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	17086
0.1-0.2	28810
0.2-0.3	3109
0.3-0.4	516
0.4-0.5	260
0.5-0.6	66
0.6-0.7	10
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
0.6548	Remote Similarity	NPC249281
0.6404	Remote Similarity	NPC66087
0.6395	Remote Similarity	NPC46420
0.6292	Remote Similarity	NPC116458
0.6292	Remote Similarity	NPC246943
0.6235	Remote Similarity	NPC111929
0.6235	Remote Similarity	NPC320283
0.6235	Remote Similarity	NPC41121
0.6082	Remote Similarity	NPC5319
0.6044	Remote Similarity	NPC276377
0.5816	Remote Similarity	NPC72016
0.5783	Remote Similarity	NPC293852
0.5778	Remote Similarity	NPC59534
0.573	Remote Similarity	NPC297987
0.5729	Remote Similarity	NPC150164
0.5714	Remote Similarity	NPC166757
0.567	Remote Similarity	NPC186816
0.5667	Remote Similarity	NPC271692
0.5618	Remote Similarity	NPC127546
0.5618	Remote Similarity	NPC57625
0.5618	Remote Similarity	NPC173637
0.5618	Remote Similarity	NPC317489
0.5618	Remote Similarity	NPC223424
0.5618	Remote Similarity	NPC600591
0.5591	Remote Similarity	NPC605784
0.5444	Remote Similarity	NPC77672
0.5444	Remote Similarity	NPC133671
0.5444	Remote Similarity	NPC135391
0.5444	Remote Similarity	NPC78263
0.5444	Remote Similarity	NPC250069
0.5417	Remote Similarity	NPC278419
0.5417	Remote Similarity	NPC179198
0.5385	Remote Similarity	NPC8573
0.5361	Remote Similarity	NPC480466
0.5347	Remote Similarity	NPC32641
0.5347	Remote Similarity	NPC256188
0.5347	Remote Similarity	NPC35119
0.5333	Remote Similarity	NPC331652
0.5326	Remote Similarity	NPC349108
0.5319	Remote Similarity	NPC478514
0.5312	Remote Similarity	NPC265115
0.5306	Remote Similarity	NPC173582
0.5306	Remote Similarity	NPC265885
0.5306	Remote Similarity	NPC181465
0.5306	Remote Similarity	NPC215710
0.5306	Remote Similarity	NPC473438
0.5306	Remote Similarity	NPC253788
0.5275	Remote Similarity	NPC476405
0.5275	Remote Similarity	NPC108831
0.5275	Remote Similarity	NPC182634
0.5263	Remote Similarity	NPC223747
0.5217	Remote Similarity	NPC158674
0.5213	Remote Similarity	NPC611303
0.5172	Remote Similarity	NPC170492
0.5165	Remote Similarity	NPC135599
0.5165	Remote Similarity	NPC73855
0.5165	Remote Similarity	NPC113968
0.5165	Remote Similarity	NPC328940
0.5165	Remote Similarity	NPC277174
0.5165	Remote Similarity	NPC606877
0.5161	Remote Similarity	NPC305811
0.5161	Remote Similarity	NPC24043
0.5161	Remote Similarity	NPC27640
0.5161	Remote Similarity	NPC488080
0.5161	Remote Similarity	NPC169977
0.5146	Remote Similarity	NPC64755
0.5111	Remote Similarity	NPC288084
0.5102	Remote Similarity	NPC251417
0.51	Remote Similarity	NPC65563
0.51	Remote Similarity	NPC470949
0.5054	Remote Similarity	NPC265530
0.5054	Remote Similarity	NPC136042
0.5053	Remote Similarity	NPC168584
0.5053	Remote Similarity	NPC219904
0.505	Remote Similarity	NPC473571
0.505	Remote Similarity	NPC110941

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC548009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4571
0.1-0.2	4517
0.2-0.3	54
0.3-0.4	4
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
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
0.6082	Remote Similarity	NPD7804	Clinical (unspecified phase)

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