NPASS Compound

Natural Product: NPC549862

Natural Product ID	NPC549862
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dimethoxyphenyl)-5-methoxy-7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{S},3~{R},4~{R},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dimethoxyphenyl)-5-methoxy-7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{S},3~{R},4~{R},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-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 78 82 0 0 0 0 0 0 0 0999 V2000 -7.4269 4.9938 1.5732 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0490 3.8384 1.0695 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2908 2.7277 0.7508 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9274 2.7457 0.9237 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1620 1.6208 0.6005 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7577 0.4857 0.1076 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9228 -0.6661 -0.2165 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4387 -1.8383 -0.7114 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6364 -2.9069 -1.0086 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0655 -3.9984 -1.4632 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2798 -2.7774 -0.7968 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 -3.8049 -1.0683 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9130 -4.9952 -1.5705 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1202 -6.1038 -1.8835 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 -3.6518 -0.8482 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5160 -2.4549 -0.3436 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8379 -2.4150 -0.1651 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6088 -1.3430 0.3190 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5429 -1.0509 -0.6703 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4733 -0.0857 -0.3000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5642 -0.1266 -1.3482 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5818 0.7683 -1.1534 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2294 2.0968 -1.1472 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9884 2.7004 -2.1813 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2262 2.1047 -2.1857 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9861 2.2401 -0.9141 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8288 3.3758 -0.9086 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1607 2.2044 0.3250 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7306 2.9744 1.3368 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7491 2.7147 0.1354 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7733 4.0957 -0.0579 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1328 -0.4197 1.0222 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6055 0.3850 2.0415 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7643 -1.8545 1.4083 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1085 -2.7487 0.4095 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2480 -1.8156 1.6070 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8221 -3.0515 2.0247 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4165 -1.4601 -0.0854 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7788 -1.5793 -0.2941 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6133 -0.6114 -0.0379 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1048 0.4799 -0.0588 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8949 1.5953 0.2579 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2677 1.5945 0.0903 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8647 0.4079 -0.4221 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1197 5.8310 1.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9261 4.7622 2.5434 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6472 5.3543 0.8507 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4523 3.6301 1.3096 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0993 1.7252 0.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4930 -1.9387 -0.8761 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7913 -6.9601 -2.1084 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5159 -5.8436 -2.7860 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4788 -6.4350 -1.0312 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3971 -4.4914 -1.0811 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9401 -0.5028 0.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0708 0.9255 -0.2624 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0281 -1.1527 -1.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1299 -0.0942 -2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1486 2.2921 -1.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8282 2.6238 -2.9874 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1133 1.0597 -2.5368 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6981 1.3649 -0.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1031 3.5448 0.0256 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0894 1.1696 0.7178 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4313 2.4400 1.7589 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1196 2.4112 0.9725 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0831 4.5634 0.4848 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2195 -0.3008 1.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3308 0.5528 2.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2289 -2.0958 2.3823 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5830 -3.5661 0.5068 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0537 -1.0803 2.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3683 -3.5557 1.2959 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0559 -0.5222 0.3043 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6363 -0.3699 -0.4381 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4866 0.2878 -1.4591 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5921 -0.4779 0.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9643 0.4584 -0.4476 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 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 2 0 16 17 1 0 17 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 25 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 20 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 16 38 1 0 38 39 2 0 39 40 1 0 6 41 1 0 41 42 2 0 42 43 1 0 43 44 1 0 42 3 1 0 40 7 1 0 39 11 1 0 36 18 1 0 30 23 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 5 49 1 0 8 50 1 0 14 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 18 55 1 1 20 56 1 1 21 57 1 0 21 58 1 0 23 59 1 6 25 60 1 0 25 61 1 0 26 62 1 1 27 63 1 0 28 64 1 1 29 65 1 0 30 66 1 1 31 67 1 0 32 68 1 6 33 69 1 0 34 70 1 1 35 71 1 0 36 72 1 1 37 73 1 0 38 74 1 0 41 75 1 0 44 76 1 0 44 77 1 0 44 78 1 0 M END

Standard InCHIKey	SIWCLUVDCVTJDC-GETFLKSSSA-N
Standard InCHI	InChI=1S/C29H34O15/c1-37-16-5-4-12(6-18(16)38-2)17-9-14(30)22-19(39-3)7-13(8-20(22)43-17)42-29-27(36)25(34)24(33)21(44-29)11-41-28-26(35)23(32)15(31)10-40-28/h4-9,15,21,23-29,31-36H,10-11H2,1-3H3/t15-,21-,23-,24-,25+,26-,27+,28+,29-/m1/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(OC)C=C(O[C@@H]4O[C@H](CO[C@@H]5OC[C@@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@@H]4O)C=C3O2)C=C1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.19	Volume:	578.119 ? Van der Waals volume.
Dense:	1.076	LogP:	0.825 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.262 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.844 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	216.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.171	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.565	Fsp³:	0.483
MCE-18:	114.349 ? 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:	0.623	Fluc inhibitor:	0.262 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.895 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.646 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.031	Promiscuous compounds:	0.187

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.059	MDCK Permeability:	-5.253
Pgp-inhibitor:	0.001	Pgp-substrate:	0.976
PAMPA:	0.996 ? 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):	0.977
20% Bioavailability (F20%):	0.758	30% Bioavailability (F30%):	0.981
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.564
Plasma Protein Binding (PPB):	78.832%	Volume Distribution (VD):	-0.221
Fu:	18.879% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.891
BSEP inhibitor:	0.346

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.089
HLM stability:	0.0 ? 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):

1.622

Half-life (T1/2):

4.213

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.103
Human Hepatotoxicity (H-HT):	0.361	Drug-induced Liver Injury (DILI):	0.829
AMES Toxicity:	0.886	Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.059	Skin Sensitization:	0.981
Carcinogencity:	0.125	Eye Corrosion:	0.0
Eye Irritation:	0.146	Respiratory Toxicity:	0.019
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.948
Hematotoxicity:	0.549	Drug-induced Nephrotoxicity:	0.716
Genotoxicity:	0.131	RPMI-8226 Immunitoxicity:	0.231
A549 Cytotoxicity:	0.329	Hek293 Cytotoxicity:	0.394
BCF:	0.196 ? 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:	2.925 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.413 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.599 ? 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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23424	Dirca palustris	Species	Thymelaeaceae	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 NPC549862 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	22697
0.1-0.2	23791
0.2-0.3	2538
0.3-0.4	619
0.4-0.5	169
0.5-0.6	33
0.6-0.7	2
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475497
0.95	High Similarity	NPC284277
0.8765	High Similarity	NPC473657
0.8571	High Similarity	NPC475366
0.8313	Intermediate Similarity	NPC295613
0.8214	Intermediate Similarity	NPC15358
0.8118	Intermediate Similarity	NPC473512
0.7701	Intermediate Similarity	NPC129827
0.686	Remote Similarity	NPC182045
0.6087	Remote Similarity	NPC293004
0.5957	Remote Similarity	NPC52353
0.5824	Remote Similarity	NPC610763
0.5778	Remote Similarity	NPC110349
0.5714	Remote Similarity	NPC22062
0.5714	Remote Similarity	NPC473634
0.5714	Remote Similarity	NPC138811
0.5696	Remote Similarity	NPC70853
0.5684	Remote Similarity	NPC194483
0.567	Remote Similarity	NPC51774
0.5657	Remote Similarity	NPC204693
0.551	Remote Similarity	NPC236191
0.549	Remote Similarity	NPC483707
0.549	Remote Similarity	NPC209296
0.5474	Remote Similarity	NPC243930
0.5474	Remote Similarity	NPC284960
0.5455	Remote Similarity	NPC301683
0.5437	Remote Similarity	NPC488089
0.5417	Remote Similarity	NPC607707
0.5385	Remote Similarity	NPC231194
0.5377	Remote Similarity	NPC244875
0.534	Remote Similarity	NPC473623
0.534	Remote Similarity	NPC51326
0.5306	Remote Similarity	NPC211594
0.53	Remote Similarity	NPC44931
0.53	Remote Similarity	NPC142996
0.5248	Remote Similarity	NPC210073
0.5152	Remote Similarity	NPC172807
0.5146	Remote Similarity	NPC488074
0.51	Remote Similarity	NPC254540
0.5096	Remote Similarity	NPC65711
0.5052	Remote Similarity	NPC609451
0.5051	Remote Similarity	NPC61791
0.5047	Remote Similarity	NPC101636

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC549862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5288
0.1-0.2	3795
0.2-0.3	53
0.3-0.4	8
0.4-0.5	2
0.5-0.6	3
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
0.6566	Remote Similarity	NPD7472	Pre-clinical
0.549	Remote Similarity	NPD7054	Phase 4
0.5056	Remote Similarity	NPD3817	Phase 3
0.5046	Remote Similarity	NPD7808	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