NPASS Compound

Natural Product: NPC511323

Natural Product ID	NPC511323
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-hydroxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-[4-hydroxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-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 93 98 0 0 0 0 0 0 0 0999 V2000 -10.3791 -1.0932 -0.0295 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1341 0.3039 -0.5124 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2612 0.3615 -1.5879 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9630 0.0898 -1.0923 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0836 -0.2137 -2.0313 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3658 -1.3176 -2.1688 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3639 -1.6965 -1.1247 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4091 -0.7071 -0.8774 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6415 -1.0625 0.2505 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4920 -0.3258 0.2550 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2112 -0.7991 0.2069 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9509 -2.1387 0.1487 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3608 -2.6152 0.0998 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6401 -3.9533 0.0415 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4061 -1.6901 0.1116 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7198 -2.1168 0.0646 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9526 -3.3415 0.0116 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7015 -1.1497 0.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4251 0.1983 0.1384 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4539 1.2421 0.1553 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0832 2.5826 0.2113 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0503 3.5638 0.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4035 3.2726 0.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3652 4.2660 0.2102 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7899 1.9654 0.1374 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0605 1.4961 0.0967 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2965 2.0792 0.0977 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0636 1.7166 -1.0148 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3487 0.3842 -1.1063 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8823 -0.0885 -2.4768 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5144 0.1125 -2.6346 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7733 -0.4964 -0.0529 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5399 -1.6860 -0.0404 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8907 0.0858 1.3374 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6608 -0.1392 1.9723 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1093 1.5828 1.3020 C 0 0 1 0 0 0 0 0 0 0 0 0 11.4468 1.8128 0.9961 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7847 0.9700 0.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1610 0.5599 0.1819 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1857 -0.3280 0.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1279 0.0979 0.2168 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5574 -0.7914 1.4286 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8890 -0.9253 2.6422 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6731 -1.7904 1.3866 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8416 -1.3069 1.9737 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8720 -2.4218 0.0455 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3335 -3.7554 0.0589 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4527 1.3221 -0.3345 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5862 2.0715 -1.1143 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6643 2.1762 -0.0126 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1408 2.7301 -1.1777 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6891 1.2385 0.6078 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7289 1.9936 1.0970 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4536 -1.2207 0.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1664 -1.7914 -0.8688 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8170 -1.3449 0.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1020 0.7170 -0.8729 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1022 -0.6852 -0.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0298 -2.2008 -2.4192 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7369 -1.1858 -3.1270 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7058 -2.4866 -1.6890 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5323 -2.1591 0.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7300 -2.8581 0.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6502 -4.5782 0.8225 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7313 -1.4807 0.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0442 2.8285 0.2401 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7955 4.6186 0.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7136 4.6863 1.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3354 3.1818 0.1282 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4530 0.2704 -1.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0950 -1.1466 -2.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3911 0.5585 -3.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2611 0.1626 -3.5896 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7340 -0.8393 -0.2833 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4997 -2.1195 -0.9131 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6648 -0.3947 1.9312 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7138 -0.7662 2.7216 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7617 2.0821 2.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0420 1.3092 1.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0979 -0.0559 0.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3582 1.1331 0.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8693 0.2641 1.3706 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5369 -0.0557 2.9725 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3545 -2.6336 2.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5552 -0.5952 2.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9659 -2.6274 -0.0780 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0388 -3.9900 -0.8368 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9622 1.0677 0.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7305 3.0355 -0.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3323 2.9657 0.6892 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0993 2.5190 -1.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1812 0.6630 1.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8823 2.8267 0.5882 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 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 13 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 25 38 2 0 19 39 1 0 39 40 1 0 40 41 2 0 9 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 4 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 52 2 1 0 46 7 1 0 41 11 1 0 40 15 1 0 38 20 1 0 36 27 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 6 4 58 1 1 6 59 1 0 6 60 1 0 7 61 1 6 9 62 1 6 12 63 1 0 14 64 1 0 18 65 1 0 21 66 1 0 22 67 1 0 24 68 1 0 27 69 1 1 29 70 1 6 30 71 1 0 30 72 1 0 31 73 1 0 32 74 1 6 33 75 1 0 34 76 1 1 35 77 1 0 36 78 1 1 37 79 1 0 38 80 1 0 41 81 1 0 42 82 1 6 43 83 1 0 44 84 1 1 45 85 1 0 46 86 1 6 47 87 1 0 48 88 1 1 49 89 1 0 50 90 1 1 51 91 1 0 52 92 1 1 53 93 1 0 M END

Standard InCHIKey	AORLKLDMGIQAME-ZYJCAUGESA-N
Standard InCHI	InChI=1S/C33H40O20/c1-10-22(38)25(41)28(44)31(48-10)47-9-20-24(40)27(43)29(45)32(53-20)49-12-5-14(36)21-15(37)7-16(50-18(21)6-12)11-2-3-13(35)17(4-11)51-33-30(46)26(42)23(39)19(8-34)52-33/h2-7,10,19-20,22-36,38-46H,8-9H2,1H3/t10-,19+,20+,22-,23+,24+,25-,26-,27-,28-,29+,30+,31+,32+,33+/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C=C(C5=CC=C(O)C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)=C5)OC4=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.21	Volume:	682.698 ? Van der Waals volume.
Dense:	1.108	LogP:	-0.061 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.906 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.984 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	328.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.099	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.335	Fsp³:	0.545
MCE-18:	150.706 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.643	Fluc inhibitor:	0.36 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.971 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.585 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.194	Promiscuous compounds:	0.469

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.838	MDCK Permeability:	-4.921
Pgp-inhibitor:	0.0	Pgp-substrate:	0.93
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):	0.941
20% Bioavailability (F20%):	0.331	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.012
Plasma Protein Binding (PPB):	76.688%	Volume Distribution (VD):	-0.054
Fu:	18.322% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.238
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:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.126
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):

0.596

Half-life (T1/2):

6.638

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.088
Human Hepatotoxicity (H-HT):	0.471	Drug-induced Liver Injury (DILI):	0.963
AMES Toxicity:	0.906	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	0.995
Carcinogencity:	0.007	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.09	Drug-induced Nephrotoxicity:	0.692
Genotoxicity:	0.281	RPMI-8226 Immunitoxicity:	0.233
A549 Cytotoxicity:	0.174	Hek293 Cytotoxicity:	0.17
BCF:	0.364 ? 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:	2.726 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.407 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.517 ? 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
NPO4134	Campanula persicifolia	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4134	Campanula persicifolia	Species	Campanulaceae	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 NPC511323 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	23492
0.1-0.2	22154
0.2-0.3	3126
0.3-0.4	662
0.4-0.5	254
0.5-0.6	112
0.6-0.7	39
0.7-0.8	1
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
0.8023	Intermediate Similarity	NPC601144
0.7889	Intermediate Similarity	NPC44931
0.7802	Intermediate Similarity	NPC210073
0.7528	Intermediate Similarity	NPC311830
0.7474	Intermediate Similarity	NPC209296
0.7419	Intermediate Similarity	NPC22062
0.7419	Intermediate Similarity	NPC473634
0.7419	Intermediate Similarity	NPC138811
0.697	Remote Similarity	NPC195257
0.6667	Remote Similarity	NPC39360
0.6667	Remote Similarity	NPC29763
0.6667	Remote Similarity	NPC210003
0.6598	Remote Similarity	NPC67105
0.6593	Remote Similarity	NPC189142
0.6593	Remote Similarity	NPC77660
0.6569	Remote Similarity	NPC101636
0.6514	Remote Similarity	NPC298666
0.6514	Remote Similarity	NPC198199
0.65	Remote Similarity	NPC65711
0.6489	Remote Similarity	NPC601710
0.6465	Remote Similarity	NPC186816
0.6449	Remote Similarity	NPC311850
0.6374	Remote Similarity	NPC331652
0.6355	Remote Similarity	NPC480441
0.6355	Remote Similarity	NPC25523
0.6354	Remote Similarity	NPC601586
0.6339	Remote Similarity	NPC120952
0.6316	Remote Similarity	NPC22832
0.6316	Remote Similarity	NPC243930
0.6304	Remote Similarity	NPC19709
0.6275	Remote Similarity	NPC473623
0.6273	Remote Similarity	NPC68592
0.625	Remote Similarity	NPC607707
0.6237	Remote Similarity	NPC95090
0.6237	Remote Similarity	NPC27408
0.6214	Remote Similarity	NPC488089
0.62	Remote Similarity	NPC65003
0.6139	Remote Similarity	NPC204693
0.6139	Remote Similarity	NPC115674
0.6129	Remote Similarity	NPC261866
0.61	Remote Similarity	NPC275454
0.61	Remote Similarity	NPC227508
0.6095	Remote Similarity	NPC298171
0.6082	Remote Similarity	NPC602805
0.6078	Remote Similarity	NPC64051
0.6075	Remote Similarity	NPC11468
0.6	Remote Similarity	NPC475382
0.5962	Remote Similarity	NPC229409
0.5948	Remote Similarity	NPC262222
0.5905	Remote Similarity	NPC270675
0.5905	Remote Similarity	NPC195685
0.5862	Remote Similarity	NPC192539
0.5851	Remote Similarity	NPC473043
0.5849	Remote Similarity	NPC476472
0.5849	Remote Similarity	NPC294815
0.5849	Remote Similarity	NPC16194
0.5818	Remote Similarity	NPC472993
0.5804	Remote Similarity	NPC488083
0.5769	Remote Similarity	NPC46202
0.5769	Remote Similarity	NPC475366
0.5766	Remote Similarity	NPC473644
0.5758	Remote Similarity	NPC116458
0.5758	Remote Similarity	NPC246943
0.5758	Remote Similarity	NPC605784
0.5743	Remote Similarity	NPC8856
0.5743	Remote Similarity	NPC251417
0.5741	Remote Similarity	NPC472994
0.5741	Remote Similarity	NPC135358
0.5728	Remote Similarity	NPC479405
0.5728	Remote Similarity	NPC303913
0.57	Remote Similarity	NPC190003
0.5688	Remote Similarity	NPC14187
0.5673	Remote Similarity	NPC479404
0.5612	Remote Similarity	NPC27942
0.5567	Remote Similarity	NPC146792
0.5567	Remote Similarity	NPC277205
0.5567	Remote Similarity	NPC37919
0.5567	Remote Similarity	NPC323593
0.5567	Remote Similarity	NPC203500
0.5566	Remote Similarity	NPC479403
0.5556	Remote Similarity	NPC285197
0.551	Remote Similarity	NPC58716
0.549	Remote Similarity	NPC4390
0.5421	Remote Similarity	NPC470443
0.5408	Remote Similarity	NPC297987
0.5408	Remote Similarity	NPC136042
0.537	Remote Similarity	NPC32641
0.537	Remote Similarity	NPC256188
0.537	Remote Similarity	NPC35119
0.5354	Remote Similarity	NPC84362
0.5354	Remote Similarity	NPC181712
0.5347	Remote Similarity	NPC197285
0.5347	Remote Similarity	NPC486578
0.5333	Remote Similarity	NPC173582
0.5333	Remote Similarity	NPC265885
0.5333	Remote Similarity	NPC181465
0.5333	Remote Similarity	NPC215710
0.5333	Remote Similarity	NPC473438
0.5333	Remote Similarity	NPC253788
0.5321	Remote Similarity	NPC142142
0.5306	Remote Similarity	NPC45618
0.5306	Remote Similarity	NPC108831
0.5306	Remote Similarity	NPC238376
0.5306	Remote Similarity	NPC182634
0.5299	Remote Similarity	NPC488086
0.5283	Remote Similarity	NPC473512
0.5283	Remote Similarity	NPC203259
0.5283	Remote Similarity	NPC129827
0.5283	Remote Similarity	NPC33054
0.5283	Remote Similarity	NPC176740
0.5283	Remote Similarity	NPC471725
0.5283	Remote Similarity	NPC134532
0.5283	Remote Similarity	NPC156869
0.5283	Remote Similarity	NPC602582
0.5281	Remote Similarity	NPC137062
0.5259	Remote Similarity	NPC488087
0.5253	Remote Similarity	NPC93337
0.5248	Remote Similarity	NPC191306
0.5248	Remote Similarity	NPC307938
0.5243	Remote Similarity	NPC469931
0.5238	Remote Similarity	NPC187379
0.5234	Remote Similarity	NPC473571
0.5234	Remote Similarity	NPC110941
0.52	Remote Similarity	NPC105025
0.52	Remote Similarity	NPC45638
0.5196	Remote Similarity	NPC181616
0.5196	Remote Similarity	NPC605067
0.5196	Remote Similarity	NPC606560
0.5192	Remote Similarity	NPC172807
0.5185	Remote Similarity	NPC488073
0.5185	Remote Similarity	NPC126784
0.5185	Remote Similarity	NPC241423
0.5172	Remote Similarity	NPC277532
0.5152	Remote Similarity	NPC289667
0.5152	Remote Similarity	NPC58053
0.5152	Remote Similarity	NPC249281
0.5152	Remote Similarity	NPC143851
0.5149	Remote Similarity	NPC201292
0.5143	Remote Similarity	NPC254540
0.514	Remote Similarity	NPC65563
0.514	Remote Similarity	NPC470949
0.5135	Remote Similarity	NPC473073
0.51	Remote Similarity	NPC168822
0.5098	Remote Similarity	NPC609451
0.5096	Remote Similarity	NPC276377
0.5093	Remote Similarity	NPC122809
0.5091	Remote Similarity	NPC483707
0.5091	Remote Similarity	NPC473327
0.5053	Remote Similarity	NPC191154
0.505	Remote Similarity	NPC186807
0.505	Remote Similarity	NPC46420
0.505	Remote Similarity	NPC271692
0.505	Remote Similarity	NPC610763
0.5049	Remote Similarity	NPC80188
0.5048	Remote Similarity	NPC211594
0.5046	Remote Similarity	NPC240306
0.5046	Remote Similarity	NPC64425
0.5044	Remote Similarity	NPC253685
0.5043	Remote Similarity	NPC189564

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC511323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5801
0.1-0.2	3279
0.2-0.3	58
0.3-0.4	6
0.4-0.5	1
0.5-0.6	3
0.6-0.7	1
0.7-0.8	1
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
0.7474	Intermediate Similarity	NPD7054	Phase 4
0.6154	Remote Similarity	NPD7251	Phase 2
0.578	Remote Similarity	NPD7472	Pre-clinical
0.578	Remote Similarity	NPD7808	Phase 3
0.5283	Remote Similarity	NPD6797	Phase 2

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