NPASS Compound

Natural Product: NPC552411

Natural Product ID	NPC552411
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~{R},6~{S})-6-[4-[7-[(2~{S},3~{S},4~{S},5~{S},6~{S})-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-4-oxo-chromen-2-yl]-2-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{S},3~{S},4~{R},5~{R},6~{S})-6-[4-[7-[(2~{S},3~{S},4~{S},5~{S},6~{S})-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-4-oxo-chromen-2-yl]-2-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-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 92 97 0 0 0 0 0 0 0 0999 V2000 11.2416 0.0826 1.0285 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0310 0.2577 0.7537 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6336 1.5019 0.2909 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0685 -0.8346 0.9242 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7696 -0.4740 0.4916 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8862 -1.3020 1.2630 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5714 -1.0939 0.9017 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6791 -0.1492 1.3210 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 0.8408 2.2060 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2972 1.8267 2.6669 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7129 2.8231 3.5422 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9891 1.8427 2.2562 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1015 2.8231 2.6868 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5098 3.6938 3.4615 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8111 2.7402 2.2027 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3565 1.7692 1.3402 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0080 1.6913 0.8447 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8987 2.7162 0.9999 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2151 2.6319 0.5695 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7077 1.5138 -0.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0012 1.3714 -0.4933 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9303 2.4074 -0.5363 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7143 2.5290 0.6076 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5008 3.6651 0.5907 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3014 3.8317 1.8177 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2197 2.9861 2.7259 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1274 4.9191 1.9471 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3426 3.7913 -0.6622 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1758 4.8808 -0.6238 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4445 3.7370 -1.8854 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4131 4.6712 -1.7010 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7694 2.3639 -1.7967 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9373 2.2495 -2.9034 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8007 0.4364 -0.2108 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2996 -0.6778 -0.8185 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -1.8158 -1.1385 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0068 -2.3105 -2.3541 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2803 -3.3778 -2.8106 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0483 -3.9393 -4.0109 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3657 -5.0287 -4.5120 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0986 -4.4917 -1.8400 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0889 -5.3226 -2.3411 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 -3.9704 -0.5032 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6332 -4.9842 0.4223 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7710 -2.9432 -0.1062 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4422 -2.4856 1.1494 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5043 0.5495 0.2238 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2557 0.8748 0.9760 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4986 0.8933 1.3945 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3713 -0.0971 0.9402 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3848 -2.6938 1.0623 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3563 -3.6380 1.0228 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2592 -2.8178 -0.1906 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6902 -2.1899 -1.2826 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5462 -2.0546 0.1771 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3348 -2.8748 0.9983 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0408 2.3447 0.7287 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9868 -1.1156 2.0108 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0533 -0.8992 2.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1463 0.8480 2.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6074 3.2736 3.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1055 3.5021 2.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5811 3.6547 1.4811 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8643 3.4731 0.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3546 3.3788 -0.5765 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7893 4.5414 0.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6795 5.1094 2.7911 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9697 2.8605 -0.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1540 5.2797 -1.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9731 3.9042 -2.8250 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8341 4.7658 -2.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5402 1.5928 -1.7773 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0219 1.3827 -3.3694 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4769 -1.6401 -1.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3078 -3.0005 -3.1911 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1172 -3.1383 -4.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 -4.2592 -3.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4071 -4.8494 -4.6150 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0185 -5.0997 -1.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9165 -6.0755 -1.7166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7223 -3.4562 -0.5869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5467 -5.3663 0.5761 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7538 -3.4185 -0.1884 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2141 -2.5533 1.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7698 -0.2498 0.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9911 -0.8435 0.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0369 -2.9638 1.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7194 -3.3198 0.3303 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4908 -3.8650 -0.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2897 -1.5369 -1.6879 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1491 -1.8086 -0.7037 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2722 -3.7975 0.6397 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 1 0 38 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 34 47 2 0 16 48 1 0 48 49 1 0 49 50 2 0 6 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 53 55 1 0 55 56 1 0 55 4 1 0 50 8 1 0 49 12 1 0 47 17 1 0 32 22 1 0 45 36 1 0 3 57 1 0 4 58 1 1 6 59 1 1 9 60 1 0 11 61 1 0 15 62 1 0 18 63 1 0 19 64 1 0 22 65 1 6 24 66 1 6 27 67 1 0 28 68 1 6 29 69 1 0 30 70 1 6 31 71 1 0 32 72 1 1 33 73 1 0 36 74 1 6 38 75 1 6 39 76 1 0 39 77 1 0 40 78 1 0 41 79 1 1 42 80 1 0 43 81 1 6 44 82 1 0 45 83 1 1 46 84 1 0 47 85 1 0 50 86 1 0 51 87 1 1 52 88 1 0 53 89 1 6 54 90 1 0 55 91 1 6 56 92 1 0 M END

Standard InCHIKey	QYCABSAOUAGOCG-CRKBAIEZSA-N
Standard InCHI	InChI=1S/C33H36O23/c34-7-16-18(37)19(38)24(43)32(54-16)53-14-3-8(1-2-12(14)52-33-26(45)21(40)23(42)28(56-33)30(48)49)13-6-11(36)17-10(35)4-9(5-15(17)51-13)50-31-25(44)20(39)22(41)27(55-31)29(46)47/h1-6,16,18-28,31-35,37-45H,7H2,(H,46,47)(H,48,49)/t16-,18-,19+,20+,21-,22+,23+,24-,25+,26-,27+,28+,31-,32-,33-/m1/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](CO)[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:	800.16	Volume:	703.796 ? Van der Waals volume.
Dense:	1.137	LogP:	-1.447 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.02 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.31 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	38.0
TPSA:	382.72 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	23.0

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:	5.427	Fsp³:	0.485
MCE-18:	158.939 ? 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:	0.465	Fluc inhibitor:	0.385 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.929 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.65 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.404	Promiscuous compounds:	0.538

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.562	MDCK Permeability:	-4.881
Pgp-inhibitor:	0.0	Pgp-substrate:	0.958
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):	0.93
20% Bioavailability (F20%):	0.008	30% Bioavailability (F30%):	0.634
50% Bioavailability (F50%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.925
Plasma Protein Binding (PPB):	63.59%	Volume Distribution (VD):	-0.238
Fu:	30.25% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.271
OATP1B3 inhibitor:	0.985	BCRP inhibitor:	0.001
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:	0.08
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):

0.008

Half-life (T1/2):

7.963

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.462	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.777	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	0.998
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.854
Genotoxicity:	0.422	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.003	Hek293 Cytotoxicity:	0.012
BCF:	0.162 ? 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:	2.742 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.375 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.453 ? 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
NPO14201	Riccia fluitans	Species	Ricciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14201	Riccia fluitans	Species	Ricciaceae	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 NPC552411 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	21463
0.1-0.2	25288
0.2-0.3	2253
0.3-0.4	573
0.4-0.5	190
0.5-0.6	64
0.6-0.7	17
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
0.7586	Intermediate Similarity	NPC607707
0.7471	Intermediate Similarity	NPC243930
0.7273	Intermediate Similarity	NPC608742
0.6966	Remote Similarity	NPC282169
0.6966	Remote Similarity	NPC20505
0.6818	Remote Similarity	NPC95090
0.6818	Remote Similarity	NPC27408
0.6703	Remote Similarity	NPC601144
0.6629	Remote Similarity	NPC189142
0.6629	Remote Similarity	NPC77660
0.6535	Remote Similarity	NPC253685
0.6522	Remote Similarity	NPC22832
0.6517	Remote Similarity	NPC261866
0.6517	Remote Similarity	NPC39360
0.6517	Remote Similarity	NPC29763
0.6517	Remote Similarity	NPC210003
0.6452	Remote Similarity	NPC311830
0.6413	Remote Similarity	NPC609451
0.6277	Remote Similarity	NPC88023
0.6277	Remote Similarity	NPC309025
0.5941	Remote Similarity	NPC46202
0.5851	Remote Similarity	NPC186807
0.5825	Remote Similarity	NPC229409
0.5806	Remote Similarity	NPC58053
0.5784	Remote Similarity	NPC64051
0.5699	Remote Similarity	NPC473043
0.5684	Remote Similarity	NPC181712
0.5657	Remote Similarity	NPC600989
0.5638	Remote Similarity	NPC289667
0.5638	Remote Similarity	NPC19709
0.5638	Remote Similarity	NPC143851
0.5625	Remote Similarity	NPC182045
0.56	Remote Similarity	NPC8856
0.5579	Remote Similarity	NPC277205
0.5579	Remote Similarity	NPC37919
0.5567	Remote Similarity	NPC237435
0.5567	Remote Similarity	NPC285197
0.5532	Remote Similarity	NPC331652
0.5521	Remote Similarity	NPC45638
0.551	Remote Similarity	NPC43211
0.5464	Remote Similarity	NPC27942
0.5464	Remote Similarity	NPC201292
0.5455	Remote Similarity	NPC602805
0.5446	Remote Similarity	NPC606546
0.5417	Remote Similarity	NPC93337
0.5417	Remote Similarity	NPC136042
0.5417	Remote Similarity	NPC323593
0.5417	Remote Similarity	NPC203500
0.54	Remote Similarity	NPC190003
0.5361	Remote Similarity	NPC84362
0.5361	Remote Similarity	NPC105025
0.5354	Remote Similarity	NPC486578
0.5354	Remote Similarity	NPC601710
0.5354	Remote Similarity	NPC605067
0.5278	Remote Similarity	NPC475382
0.5258	Remote Similarity	NPC297987
0.5258	Remote Similarity	NPC168822
0.5253	Remote Similarity	NPC191306
0.5253	Remote Similarity	NPC307938
0.5248	Remote Similarity	NPC601586
0.5238	Remote Similarity	NPC115674
0.5204	Remote Similarity	NPC58716
0.52	Remote Similarity	NPC115760
0.52	Remote Similarity	NPC284960
0.52	Remote Similarity	NPC80188
0.52	Remote Similarity	NPC610187
0.5155	Remote Similarity	NPC110349
0.5155	Remote Similarity	NPC45618
0.5152	Remote Similarity	NPC101191
0.5149	Remote Similarity	NPC220169
0.5149	Remote Similarity	NPC605784
0.5146	Remote Similarity	NPC251417
0.5143	Remote Similarity	NPC22062
0.5143	Remote Similarity	NPC65003
0.5143	Remote Similarity	NPC473634
0.5143	Remote Similarity	NPC138811
0.5138	Remote Similarity	NPC195257
0.5102	Remote Similarity	NPC146792
0.51	Remote Similarity	NPC135277
0.51	Remote Similarity	NPC210094
0.5054	Remote Similarity	NPC191154
0.5051	Remote Similarity	NPC610763
0.5047	Remote Similarity	NPC64425
0.5043	Remote Similarity	NPC277532

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC552411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4447
0.1-0.2	4617
0.2-0.3	67
0.3-0.4	14
0.4-0.5	4
0.5-0.6	1
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
0.5567	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