NPASS Compound

Natural Product: NPC559507

Natural Product ID	NPC559507
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},3~{S},4~{R},5~{S},6~{S})-6-[2-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-4-[7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-4-oxo-chromen-2-yl]phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{S},3~{S},4~{R},5~{S},6~{S})-6-[2-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-4-[7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-4-oxo-chromen-2-yl]phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
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 91 96 0 0 0 0 0 0 0 0999 V2000 11.1280 -0.5910 1.1587 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0478 0.0503 1.1597 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4873 0.3300 2.4005 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4457 0.4621 -0.1225 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2481 1.1605 0.0537 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6176 1.1281 -1.2227 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2663 1.3810 -1.0660 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3617 0.3792 -0.7771 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7010 -0.9329 -0.5568 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7442 -1.9140 -0.2626 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1055 -3.2326 -0.0422 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4219 -1.5888 -0.1855 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4243 -2.4899 0.0993 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6978 -3.6890 0.3078 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0921 -2.0358 0.1522 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7998 -0.7193 -0.0770 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5482 -0.1494 -0.0478 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 1.1852 -0.3371 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0374 1.7351 -0.2992 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1380 0.9961 0.0222 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4180 1.4840 0.0733 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8950 2.7454 -0.2272 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1869 3.5050 0.9181 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0654 4.5403 0.5076 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0233 5.6736 1.4333 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2745 5.6327 2.4358 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7964 6.8003 1.2269 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4692 3.9139 0.5678 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3610 4.5805 -0.2388 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2947 2.5159 0.0226 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4606 1.9737 -0.4708 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1754 2.5768 -1.0173 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1322 1.3265 -1.6581 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9422 -0.3758 0.3227 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0391 -1.1368 0.6494 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0456 -2.4793 0.9411 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0520 -3.1854 0.2531 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5175 -4.2859 0.9172 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1805 -5.1995 -0.0490 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7052 -6.2893 0.3179 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2184 -4.8358 -1.3829 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4190 -5.0240 1.6645 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4312 -5.4605 0.7714 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8776 -4.1289 2.7369 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2257 -4.5306 4.0243 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3446 -2.7274 2.4395 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6288 -1.7765 3.2051 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 -0.9006 0.2802 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7805 0.1021 -0.3439 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0542 -0.2817 -0.4034 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9901 0.6771 -0.6906 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3742 2.0980 -2.0718 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8608 2.2300 -3.3616 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7955 1.5804 -2.2343 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5546 2.5185 -2.9592 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3882 1.3679 -0.8538 C 0 0 2 0 0 0 0 0 0 0 0 0 11.6632 0.8699 -0.9982 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5913 -0.4112 3.1093 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2170 -0.4045 -0.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8162 0.0982 -1.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7435 -1.2370 -0.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3902 -3.8348 -0.7886 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2988 -2.7217 0.3723 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0806 1.8150 -0.5968 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 2.7986 -0.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1096 3.3137 -0.7778 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8150 4.8428 -0.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7165 7.6641 1.7367 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7668 3.8859 1.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2256 4.6156 0.2435 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8664 1.9047 0.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7521 1.2730 0.1902 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3486 3.3371 -1.7762 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1956 1.4439 -2.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0976 -3.0171 0.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3192 -4.0542 1.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4617 -5.4983 -2.1182 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8655 -5.9161 2.1194 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6448 -6.3254 0.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7636 -4.1047 2.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7648 -5.3825 4.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4001 -2.5406 2.6551 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1507 -0.9400 3.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5086 -1.9609 0.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7111 1.7170 -0.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3975 3.1250 -1.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9364 2.6031 -3.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7345 0.6374 -2.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3478 3.4388 -2.6665 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3781 2.3680 -0.3432 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6088 -0.0923 -1.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 10 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 24 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 20 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 38 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 34 48 2 0 16 49 1 0 49 50 1 0 50 51 2 0 6 52 1 0 52 53 1 0 52 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 56 4 1 0 51 8 1 0 50 12 1 0 48 17 1 0 32 22 1 0 46 36 1 0 3 58 1 0 4 59 1 6 6 60 1 6 9 61 1 0 11 62 1 0 15 63 1 0 18 64 1 0 19 65 1 0 22 66 1 6 24 67 1 6 27 68 1 0 28 69 1 1 29 70 1 0 30 71 1 1 31 72 1 0 32 73 1 6 33 74 1 0 36 75 1 6 38 76 1 1 41 77 1 0 42 78 1 1 43 79 1 0 44 80 1 1 45 81 1 0 46 82 1 6 47 83 1 0 48 84 1 0 51 85 1 0 52 86 1 1 53 87 1 0 54 88 1 6 55 89 1 0 56 90 1 1 57 91 1 0 M END

Standard InCHIKey	NNXAVSQPQYOEPA-OEEMMNGVSA-N
Standard InCHI	InChI=1S/C33H34O24/c34-9-4-8(51-31-22(42)16(36)19(39)25(55-31)28(45)46)5-14-15(9)10(35)6-12(52-14)7-1-2-11(53-32-23(43)17(37)20(40)26(56-32)29(47)48)13(3-7)54-33-24(44)18(38)21(41)27(57-33)30(49)50/h1-6,16-27,31-34,36-44H,(H,45,46)(H,47,48)(H,49,50)/t16-,17+,18-,19-,20-,21-,22+,23-,24+,25-,26-,27+,31+,32+,33+/m0/s1
SMILES	O=C(O)[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@@H](O)[C@@H]5O)C(O[C@@H]5O[C@@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)=C4)OC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	814.14	Volume:	709.95 ? Van der Waals volume.
Dense:	1.147	LogP:	-1.641 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.294 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.027 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	39.0
TPSA:	399.79 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.091	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.458	Fsp³:	0.455
MCE-18:	163.125 ? 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:	0.487	Fluc inhibitor:	0.382 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.913 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.654 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.461	Promiscuous compounds:	0.548

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.602	MDCK Permeability:	-4.775
Pgp-inhibitor:	0.0	Pgp-substrate:	0.981
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):	0.581
20% Bioavailability (F20%):	0.006	30% Bioavailability (F30%):	0.116
50% Bioavailability (F50%):	0.704

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	62.084%	Volume Distribution (VD):	-0.275
Fu:	32.743% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.001	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.007
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):

-0.169

Half-life (T1/2):

7.723

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.5	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.845	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.993
Hematotoxicity:	0.105	Drug-induced Nephrotoxicity:	0.987
Genotoxicity:	0.946	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.014	Hek293 Cytotoxicity:	0.008
BCF:	0.11 ? 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:	2.716 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.151 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.414 ? 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
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	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 NPC559507 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	21625
0.1-0.2	25824
0.2-0.3	1793
0.3-0.4	444
0.4-0.5	126
0.5-0.6	36
0.6-0.7	6
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
0.8312	Intermediate Similarity	NPC608742
0.7949	Intermediate Similarity	NPC282169
0.7949	Intermediate Similarity	NPC20505
0.6364	Remote Similarity	NPC600989
0.6322	Remote Similarity	NPC607707
0.6279	Remote Similarity	NPC237435
0.6207	Remote Similarity	NPC243930
0.6207	Remote Similarity	NPC43211
0.6082	Remote Similarity	NPC253685
0.5843	Remote Similarity	NPC115760
0.5843	Remote Similarity	NPC610187
0.5795	Remote Similarity	NPC101191
0.5789	Remote Similarity	NPC46202
0.573	Remote Similarity	NPC135277
0.573	Remote Similarity	NPC210094
0.5714	Remote Similarity	NPC195202
0.567	Remote Similarity	NPC229409
0.5625	Remote Similarity	NPC64051
0.5568	Remote Similarity	NPC95090
0.5568	Remote Similarity	NPC27408
0.5517	Remote Similarity	NPC473043
0.5506	Remote Similarity	NPC181712
0.5495	Remote Similarity	NPC601144
0.5455	Remote Similarity	NPC19709
0.5393	Remote Similarity	NPC189142
0.5393	Remote Similarity	NPC77660
0.5341	Remote Similarity	NPC331652
0.5326	Remote Similarity	NPC22832
0.5281	Remote Similarity	NPC261866
0.5281	Remote Similarity	NPC39360
0.5281	Remote Similarity	NPC29763
0.5281	Remote Similarity	NPC210003
0.5275	Remote Similarity	NPC27942
0.5269	Remote Similarity	NPC311830
0.5248	Remote Similarity	NPC479765
0.5217	Remote Similarity	NPC609451
0.5213	Remote Similarity	NPC190003
0.5172	Remote Similarity	NPC604322
0.5161	Remote Similarity	NPC264735
0.5128	Remote Similarity	NPC33265
0.5106	Remote Similarity	NPC88023
0.5106	Remote Similarity	NPC309025
0.5054	Remote Similarity	NPC235260
0.5054	Remote Similarity	NPC49344
0.5054	Remote Similarity	NPC155763

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC559507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4046
0.1-0.2	5022
0.2-0.3	72
0.3-0.4	6
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
0.6279	Remote Similarity	NPD4338	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