NPASS Compound

Natural Product: NPC512974

Natural Product ID	NPC512974
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2~{R},3~{R},4~{R},5~{R},6~{R})-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-[[(2~{S},3~{R},4~{R},5~{S})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-3-yl] (~{Z})-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate
IUPAC Name	[(2~{R},3~{R},4~{R},5~{R},6~{R})-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-[[(2~{S},3~{R},4~{R},5~{S})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-3-yl] (~{Z})-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate
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 2D 100104 0 0 0 0 0 0 0 0999 V2000 -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5625 -2.8190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -6.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3300 -6.1603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1809 -7.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5691 -5.8255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 -5.8255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -4.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8191 -7.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9681 -6.1603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 -8.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4786 -8.9366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5691 -8.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8296 -9.9008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -8.6017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2981 -7.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -8.6017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 -9.1148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3777 -9.6278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7872 -10.1408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0477 -11.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4572 -12.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6063 -11.1669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0158 -11.6799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3458 -9.6897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4949 -8.7255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9363 -9.1766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -5.6473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4095 -4.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -3.7189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7077 -2.7548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1172 -3.2678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3777 -1.7906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7872 -1.2775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9363 -2.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6863 -0.9427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6758 -3.7189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1758 -3.7189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2663 -4.2320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0163 -5.5310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 4.0981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.0981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -3.7189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2648 -7.7918 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0095 -8.0131 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4786 -5.3124 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2858 -4.0878 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3314 -4.6087 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8773 -3.3665 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9681 -8.0887 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3777 -6.6734 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -9.9008 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7391 -10.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5726 -8.8391 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3195 -10.8649 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6386 -8.9366 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -10.0789 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7869 -6.9417 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4551 -10.5243 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6492 -7.7783 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8647 -11.0373 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8907 -8.2182 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8986 -12.5822 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7177 -13.6083 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1649 -10.7157 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2344 -7.2483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6758 -7.6994 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6595 -3.3841 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5944 -2.5699 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3755 -4.9770 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6425 -4.3862 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9363 -0.3134 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0372 0.0215 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3458 -2.7548 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1863 -0.9427 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9636 -4.6601 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9258 -5.0180 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3355 -5.0130 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9931 -5.6510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5625 -2.3772 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 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 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 12 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 2 0 26 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 5 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 53 3 1 0 39 11 1 0 49 42 1 0 22 14 1 0 37 30 1 0 1 55 1 0 1 56 1 0 1 57 1 0 4 58 1 0 6 59 1 0 7 60 1 0 11 61 1 1 12 62 1 6 14 63 1 6 16 64 1 1 17 65 1 0 17 66 1 0 17 67 1 0 18 68 1 6 19 69 1 0 20 70 1 1 21 71 1 0 22 72 1 1 23 73 1 0 24 74 1 1 25 75 1 0 26 76 1 6 28 77 1 0 28 78 1 0 29 79 1 0 29 80 1 0 31 81 1 0 32 82 1 0 34 83 1 0 36 84 1 0 37 85 1 0 39 86 1 6 40 87 1 0 40 88 1 0 42 89 1 1 44 90 1 0 44 91 1 0 45 92 1 1 46 93 1 0 47 94 1 6 48 95 1 0 49 96 1 6 50 97 1 0 51 98 1 0 52 99 1 0 54100 1 0 M END

Standard InCHIKey	RNIOTCRMLGGHMI-SESRLYTQSA-N
Standard InCHI	InChI=1S/C35H46O19/c1-15-25(41)27(43)29(45)35(51-15)54-32-30(46)34(48-10-9-17-3-6-18(36)20(38)11-17)52-23(14-50-33-28(44)26(42)21(39)13-49-33)31(32)53-24(40)8-5-16-4-7-19(37)22(12-16)47-2/h3-8,11-12,15,21,23,25-39,41-46H,9-10,13-14H2,1-2H3/b8-5-/t15-,21-,23+,25-,26+,27+,28+,29+,30+,31+,32+,33-,34+,35-/m0/s1
SMILES	COC1=CC(/C=CC(=O)O[C@H]2[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](OCCC3=CC=C(O)C(O)=C3)O[C@@H]2CO[C@@H]2OC[C@H](O)[C@@H](O)[C@H]2O)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.26	Volume:	717.056 ? Van der Waals volume.
Dense:	1.074	LogP:	-0.82 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.33 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.01 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	32.0
TPSA:	293.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.058	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.298	Fsp³:	0.571
MCE-18:	127.636 ? 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:	1
Colloidal aggregators:	0.706	Fluc inhibitor:	0.663 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.139 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.432 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.171	Promiscuous compounds:	0.318

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.303	MDCK Permeability:	-5.31
Pgp-inhibitor:	0.0	Pgp-substrate:	0.643
PAMPA:	0.999 ? 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):	0.72
20% Bioavailability (F20%):	0.943	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.094
Plasma Protein Binding (PPB):	68.339%	Volume Distribution (VD):	-0.304
Fu:	27.734% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.051
BSEP inhibitor:	0.012

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:	0.71
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.175 ? 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):

1.499

Half-life (T1/2):

3.627

ADMET: Toxicity

hERG Blockers:	0.041	hERG Blockers (10um):	0.362
Human Hepatotoxicity (H-HT):	0.244	Drug-induced Liver Injury (DILI):	0.165
AMES Toxicity:	0.942	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.009	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.017	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.995
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.382
Genotoxicity:	0.015	RPMI-8226 Immunitoxicity:	0.147
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.762
BCF:	0.662 ? 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:	3.301 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.966 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.203 ? 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
NPO52625	Scrophularia nodosa L.	Genus	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC512974 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	14234
0.1-0.2	30334
0.2-0.3	4596
0.3-0.4	563
0.4-0.5	70
0.5-0.6	19
0.6-0.7	23
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8539	High Similarity	NPC205864
0.8539	High Similarity	NPC247032
0.837	Intermediate Similarity	NPC259347
0.8039	Intermediate Similarity	NPC257970
0.7957	Intermediate Similarity	NPC100998
0.7938	Intermediate Similarity	NPC470933
0.7857	Intermediate Similarity	NPC470934
0.7778	Intermediate Similarity	NPC76406
0.7368	Intermediate Similarity	NPC298257
0.7368	Intermediate Similarity	NPC175214
0.7358	Intermediate Similarity	NPC470927
0.7312	Intermediate Similarity	NPC611289
0.7308	Intermediate Similarity	NPC476386
0.7263	Intermediate Similarity	NPC34587
0.7245	Intermediate Similarity	NPC300894
0.7245	Intermediate Similarity	NPC23845
0.7216	Intermediate Similarity	NPC34927
0.7184	Intermediate Similarity	NPC94871
0.6827	Remote Similarity	NPC64195
0.6765	Remote Similarity	NPC106818
0.6667	Remote Similarity	NPC87403
0.6667	Remote Similarity	NPC252292
0.6632	Remote Similarity	NPC472350
0.6632	Remote Similarity	NPC197316
0.6632	Remote Similarity	NPC89105
0.6571	Remote Similarity	NPC471062
0.6542	Remote Similarity	NPC473427
0.6509	Remote Similarity	NPC476398
0.6481	Remote Similarity	NPC229505
0.6316	Remote Similarity	NPC260425
0.6316	Remote Similarity	NPC81515
0.6275	Remote Similarity	NPC600370
0.6238	Remote Similarity	NPC269141
0.6168	Remote Similarity	NPC476380
0.6147	Remote Similarity	NPC306890
0.6132	Remote Similarity	NPC476384
0.6126	Remote Similarity	NPC188393
0.6117	Remote Similarity	NPC119537
0.6082	Remote Similarity	NPC46137
0.6	Remote Similarity	NPC96795
0.6	Remote Similarity	NPC264632
0.5962	Remote Similarity	NPC112
0.5888	Remote Similarity	NPC476382
0.5872	Remote Similarity	NPC476381
0.5728	Remote Similarity	NPC263829
0.57	Remote Similarity	NPC64141
0.5495	Remote Similarity	NPC196063
0.5495	Remote Similarity	NPC604195
0.549	Remote Similarity	NPC483705
0.5392	Remote Similarity	NPC483706
0.537	Remote Similarity	NPC476397
0.531	Remote Similarity	NPC476378
0.5288	Remote Similarity	NPC68092
0.5273	Remote Similarity	NPC232992
0.5268	Remote Similarity	NPC476375
0.5229	Remote Similarity	NPC296954
0.5196	Remote Similarity	NPC235294
0.5143	Remote Similarity	NPC134405
0.5135	Remote Similarity	NPC610636
0.5044	Remote Similarity	NPC141455

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC512974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4555
0.1-0.2	4489
0.2-0.3	103
0.3-0.4	2
0.4-0.5	0
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
0.6632	Remote Similarity	NPD7266	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