NPASS Compound

Natural Product: NPC509827

Natural Product ID	NPC509827
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-methoxy-3-[(2~{S},3~{R},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-8-methoxy-3-[(2~{S},3~{R},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-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 76 80 0 0 0 0 0 0 0 0999 V2000 2.1274 3.3191 0.0513 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0830 2.2630 -0.8879 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8062 0.9935 -0.4383 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8717 0.1867 -0.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1769 0.6596 -0.1260 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3336 -0.0532 0.1733 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8348 0.4072 1.3971 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9274 -0.3476 1.8118 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9000 0.5202 2.5643 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5294 -1.2183 0.7721 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7432 -1.6902 1.2414 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6942 -0.4351 -0.5165 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6177 0.5853 -0.4008 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3498 0.1384 -0.9318 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9084 -0.6079 -2.0242 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5868 -1.0707 0.3866 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2770 -1.5530 0.4622 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9758 -2.8329 0.9130 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2461 -0.6960 0.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 0.5787 -0.3896 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4878 1.3624 -0.7609 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7775 1.0164 -0.7348 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7598 2.0085 -1.1929 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0544 1.7584 -1.5211 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9161 2.7996 -1.9056 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4701 4.1022 -1.9591 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3092 5.1532 -2.3388 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1597 4.3801 -1.6311 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3602 3.3525 -1.2664 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0804 -0.2176 -0.2939 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3739 -0.7205 -0.1842 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0768 -0.7303 1.0200 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1431 -2.0425 1.5516 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0638 -2.8490 0.9521 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6064 -3.5109 -0.3297 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 -4.3167 -0.0273 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4443 -2.2647 0.7709 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1314 -3.1002 -0.1200 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3291 -0.8957 0.1139 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5655 -0.3239 -0.0307 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4156 -0.0957 1.0282 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9373 -0.1416 2.3503 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0591 -1.1030 0.1136 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3231 -2.2543 0.5222 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1275 3.4569 0.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3687 4.2854 -0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8736 3.1885 0.8426 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0978 -1.1308 0.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4950 -1.0430 2.5940 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7397 -0.0799 2.9915 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3425 1.3331 1.9840 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3812 0.9609 3.4591 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8562 -2.0829 0.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0704 -2.3838 0.6034 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0690 -1.1494 -1.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1661 1.4636 -0.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4070 1.1910 -1.2725 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3943 -0.0336 -2.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3379 -1.7592 0.6997 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6536 -3.4532 1.2801 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4386 0.7527 -1.5130 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9401 2.5733 -2.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2433 5.2004 -1.9609 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7492 5.3837 -1.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3218 3.5769 -1.0073 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4236 -0.1964 1.7730 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2208 -3.7230 1.6677 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4574 -4.1385 -0.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3132 -2.7509 -1.0939 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5448 -5.1503 -0.5955 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0040 -2.1964 1.7127 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0973 -3.1373 0.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8178 -1.0488 -0.8403 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8719 0.1305 0.7729 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3790 0.9372 0.7007 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6817 0.5096 2.3740 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 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 4 16 1 0 16 17 2 0 17 18 1 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 26 28 1 0 28 29 2 0 22 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 30 43 1 0 43 44 2 0 20 3 1 0 29 23 1 0 41 32 1 0 14 6 1 0 43 19 1 0 1 45 1 0 1 46 1 0 1 47 1 0 6 48 1 1 8 49 1 1 9 50 1 0 9 51 1 0 9 52 1 0 10 53 1 6 11 54 1 0 12 55 1 6 13 56 1 0 14 57 1 6 15 58 1 0 16 59 1 0 18 60 1 0 24 61 1 0 25 62 1 0 27 63 1 0 28 64 1 0 29 65 1 0 32 66 1 1 34 67 1 1 35 68 1 0 35 69 1 0 36 70 1 0 37 71 1 1 38 72 1 0 39 73 1 6 40 74 1 0 41 75 1 6 42 76 1 0 M END

Standard InCHIKey	LSHYTUQCUQMUJP-SBHXOCJNSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-16(32)19(35)21(37)27(40-9)41-13-7-12(31)15-18(34)26(44-28-22(38)20(36)17(33)14(8-29)42-28)23(43-25(15)24(13)39-2)10-3-5-11(30)6-4-10/h3-7,9,14,16-17,19-22,27-33,35-38H,8H2,1-2H3/t9-,14-,16+,17+,19+,20-,21-,22-,27+,28+/m1/s1
SMILES	COC1=C(O[C@@H]2O[C@H](C)[C@H](O)[C@H](O)[C@H]2O)C=C(O)C2=C1OC(C1=CC=C(O)C=C1)=C(O[C@@H]1O[C@H](CO)[C@H](O)[C@@H](O)[C@H]1O)C2=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	1.053 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.471 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.629 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.141	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.772	Fsp³:	0.464
MCE-18:	122.073 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.57	Fluc inhibitor:	0.251 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.722 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.563 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.106	Promiscuous compounds:	0.515

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.429	MDCK Permeability:	-5.212
Pgp-inhibitor:	0.0	Pgp-substrate:	0.898
PAMPA:	1.0 ? 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):	0.883
20% Bioavailability (F20%):	0.842	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.613
Plasma Protein Binding (PPB):	84.047%	Volume Distribution (VD):	-0.019
Fu:	15.05% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.891
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.074
BSEP inhibitor:	0.001

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:	0.529
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.322 ? 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):

1.925

Half-life (T1/2):

3.91

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.094
Human Hepatotoxicity (H-HT):	0.707	Drug-induced Liver Injury (DILI):	0.948
AMES Toxicity:	0.968	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.018	Skin Sensitization:	1.0
Carcinogencity:	0.135	Eye Corrosion:	0.0
Eye Irritation:	0.029	Respiratory Toxicity:	0.014
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.96
Hematotoxicity:	0.431	Drug-induced Nephrotoxicity:	0.598
Genotoxicity:	0.829	RPMI-8226 Immunitoxicity:	0.18
A549 Cytotoxicity:	0.908	Hek293 Cytotoxicity:	0.761
BCF:	0.322 ? 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:	2.882 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.476 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.579 ? 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
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37218075]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37513254]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27806	Gossypium hirsutum	Species	Malvaceae	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 NPC509827 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	18777
0.1-0.2	27090
0.2-0.3	2791
0.3-0.4	769
0.4-0.5	260
0.5-0.6	124
0.6-0.7	29
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8148	Intermediate Similarity	NPC480466
0.759	Intermediate Similarity	NPC480463
0.7439	Intermediate Similarity	NPC116458
0.7439	Intermediate Similarity	NPC246943
0.7059	Intermediate Similarity	NPC265115
0.7037	Intermediate Similarity	NPC8573
0.6951	Remote Similarity	NPC46420
0.6829	Remote Similarity	NPC297987
0.6747	Remote Similarity	NPC24043
0.6707	Remote Similarity	NPC249281
0.6628	Remote Similarity	NPC605784
0.6588	Remote Similarity	NPC168584
0.6552	Remote Similarity	NPC355481
0.6548	Remote Similarity	NPC488080
0.6548	Remote Similarity	NPC169977
0.6506	Remote Similarity	NPC77672
0.6506	Remote Similarity	NPC133671
0.6506	Remote Similarity	NPC135391
0.6506	Remote Similarity	NPC78263
0.6506	Remote Similarity	NPC250069
0.6386	Remote Similarity	NPC111929
0.6386	Remote Similarity	NPC320283
0.6386	Remote Similarity	NPC41121
0.6279	Remote Similarity	NPC59534
0.6277	Remote Similarity	NPC35119
0.6211	Remote Similarity	NPC5319
0.618	Remote Similarity	NPC276377
0.6163	Remote Similarity	NPC271692
0.6105	Remote Similarity	NPC32641
0.6105	Remote Similarity	NPC256188
0.6047	Remote Similarity	NPC136042
0.6044	Remote Similarity	NPC251417
0.6023	Remote Similarity	NPC488071
0.6022	Remote Similarity	NPC150164
0.6	Remote Similarity	NPC66087
0.5977	Remote Similarity	NPC84362
0.5952	Remote Similarity	NPC288084
0.593	Remote Similarity	NPC289667
0.5909	Remote Similarity	NPC472459
0.5909	Remote Similarity	NPC599850
0.5895	Remote Similarity	NPC240306
0.5895	Remote Similarity	NPC64425
0.5867	Remote Similarity	NPC605144
0.5862	Remote Similarity	NPC145038
0.5862	Remote Similarity	NPC56077
0.5862	Remote Similarity	NPC281131
0.5862	Remote Similarity	NPC253662
0.5862	Remote Similarity	NPC179950
0.5862	Remote Similarity	NPC88789
0.5862	Remote Similarity	NPC491374
0.5824	Remote Similarity	NPC203050
0.5824	Remote Similarity	NPC488072
0.5824	Remote Similarity	NPC225434
0.5806	Remote Similarity	NPC139320
0.5795	Remote Similarity	NPC27640
0.5795	Remote Similarity	NPC349108
0.5789	Remote Similarity	NPC186816
0.5778	Remote Similarity	NPC148710
0.5747	Remote Similarity	NPC127546
0.5747	Remote Similarity	NPC57625
0.5747	Remote Similarity	NPC173637
0.5747	Remote Similarity	NPC317489
0.5747	Remote Similarity	NPC223424
0.5747	Remote Similarity	NPC600591
0.573	Remote Similarity	NPC42773
0.573	Remote Similarity	NPC45522
0.5728	Remote Similarity	NPC25523
0.5714	Remote Similarity	NPC223747
0.5698	Remote Similarity	NPC93099
0.5682	Remote Similarity	NPC64305
0.5682	Remote Similarity	NPC158674
0.5667	Remote Similarity	NPC611303
0.5618	Remote Similarity	NPC305811
0.5618	Remote Similarity	NPC105025
0.5612	Remote Similarity	NPC72016
0.5604	Remote Similarity	NPC101026
0.5604	Remote Similarity	NPC120099
0.5604	Remote Similarity	NPC488077
0.5568	Remote Similarity	NPC39360
0.5568	Remote Similarity	NPC29763
0.5568	Remote Similarity	NPC210003
0.5556	Remote Similarity	NPC325555
0.5556	Remote Similarity	NPC226304
0.5506	Remote Similarity	NPC93337
0.5506	Remote Similarity	NPC265530
0.5506	Remote Similarity	NPC323593
0.5506	Remote Similarity	NPC203500
0.5495	Remote Similarity	NPC219904
0.5464	Remote Similarity	NPC470444
0.5464	Remote Similarity	NPC473571
0.5464	Remote Similarity	NPC110941
0.5455	Remote Similarity	NPC331652
0.5417	Remote Similarity	NPC173582
0.5417	Remote Similarity	NPC265885
0.5417	Remote Similarity	NPC181465
0.5417	Remote Similarity	NPC215710
0.5417	Remote Similarity	NPC163242
0.5417	Remote Similarity	NPC272068
0.5417	Remote Similarity	NPC473438
0.5417	Remote Similarity	NPC253788
0.5393	Remote Similarity	NPC19388
0.5393	Remote Similarity	NPC240431
0.5393	Remote Similarity	NPC55786
0.5393	Remote Similarity	NPC476405
0.5393	Remote Similarity	NPC108831
0.5393	Remote Similarity	NPC182634
0.5376	Remote Similarity	NPC206123
0.5368	Remote Similarity	NPC473682
0.5368	Remote Similarity	NPC278419
0.5368	Remote Similarity	NPC179198
0.5354	Remote Similarity	NPC483415
0.5341	Remote Similarity	NPC67037
0.5341	Remote Similarity	NPC255615
0.534	Remote Similarity	NPC14187
0.5326	Remote Similarity	NPC60735
0.5326	Remote Similarity	NPC26230
0.5288	Remote Similarity	NPC203145
0.5281	Remote Similarity	NPC135599
0.5281	Remote Similarity	NPC73855
0.5281	Remote Similarity	NPC113968
0.5281	Remote Similarity	NPC328940
0.5281	Remote Similarity	NPC277174
0.5281	Remote Similarity	NPC606877
0.5275	Remote Similarity	NPC603655
0.5269	Remote Similarity	NPC21666
0.5269	Remote Similarity	NPC609478
0.5258	Remote Similarity	NPC471748
0.5238	Remote Similarity	NPC189564
0.5225	Remote Similarity	NPC470720
0.5222	Remote Similarity	NPC210042
0.5222	Remote Similarity	NPC44558
0.5222	Remote Similarity	NPC83283
0.5204	Remote Similarity	NPC65563
0.5204	Remote Similarity	NPC183672
0.5204	Remote Similarity	NPC470949
0.5204	Remote Similarity	NPC605592
0.5165	Remote Similarity	NPC259152
0.5158	Remote Similarity	NPC170052
0.5158	Remote Similarity	NPC135846
0.5155	Remote Similarity	NPC29958
0.5149	Remote Similarity	NPC483416
0.5143	Remote Similarity	NPC121703
0.514	Remote Similarity	NPC480441
0.514	Remote Similarity	NPC164704
0.5138	Remote Similarity	NPC483158
0.5138	Remote Similarity	NPC483157
0.5135	Remote Similarity	NPC470717
0.5109	Remote Similarity	NPC610763
0.5098	Remote Similarity	NPC142142
0.5096	Remote Similarity	NPC602448
0.5093	Remote Similarity	NPC277532
0.5054	Remote Similarity	NPC117260
0.5054	Remote Similarity	NPC201292
0.5053	Remote Similarity	NPC311830
0.5053	Remote Similarity	NPC607707
0.5052	Remote Similarity	NPC472607
0.5051	Remote Similarity	NPC156869
0.505	Remote Similarity	NPC483414
0.5049	Remote Similarity	NPC470447

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC509827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5361
0.1-0.2	3700
0.2-0.3	76
0.3-0.4	7
0.4-0.5	5
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
0.6211	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