NPASS Compound

Natural Product: NPC597248

Natural Product ID	NPC597248
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)-3-[(2~{R},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-3-[(2~{R},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)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 94 99 0 0 0 0 0 0 0 0999 V2000 4.0213 1.0569 -1.6080 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8563 -0.0548 -1.0480 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9345 -0.8155 -0.5601 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1969 -0.2269 -0.7379 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6356 0.7151 0.2681 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9247 1.9315 -0.0230 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6361 3.0591 0.2465 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6606 4.2231 0.5173 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8702 4.4250 -0.6138 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5214 2.9988 1.4610 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8039 3.0754 2.6546 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4541 1.8184 1.4218 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7882 2.2060 1.3290 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0679 1.0090 0.1501 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8874 -0.0994 0.0850 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7472 -2.0094 0.0350 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7996 -2.8771 0.5676 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1271 -2.7954 0.2774 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0766 -3.6288 0.8739 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6970 -4.5834 1.7941 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6514 -5.4086 2.3821 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3541 -4.6781 2.0955 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4295 -3.8376 1.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4820 -2.4243 0.1400 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4455 -1.7591 -0.2931 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1693 -2.2593 -0.1461 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0206 -1.5796 -0.5972 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1953 -2.1735 -0.3986 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4093 -1.6681 -0.7596 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3111 -1.5598 0.3289 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2557 -0.6350 -0.0110 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5029 -0.7102 0.8519 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3642 0.2757 0.3793 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5538 0.3330 1.0682 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6577 0.0141 0.2869 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8308 0.8651 -0.7907 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3119 0.8872 -1.1063 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5670 1.7209 -2.1804 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3831 2.2678 -0.5161 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1415 3.1255 -1.3301 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5955 2.5909 0.9335 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2839 3.9194 1.2127 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6724 1.6663 1.7396 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2766 1.5719 3.0038 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6863 -0.6320 -1.4345 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1225 0.4409 -2.1608 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4314 -1.9188 -2.1414 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5312 -2.7720 -2.0147 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1468 -2.5910 -1.7449 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4494 -3.7439 -1.0244 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1741 -0.3641 -1.2111 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4720 0.1443 -1.3602 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6317 1.3795 -1.9829 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5841 -0.5364 -0.9118 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2813 0.4638 1.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2546 3.4345 -0.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0969 4.0690 1.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3053 5.1187 0.6421 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4933 4.5354 -1.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1606 3.9251 1.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5625 4.0103 2.8630 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2575 1.1699 2.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2734 1.5583 0.7593 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2927 1.7146 -0.7117 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1400 -0.2783 -0.8389 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4489 -2.1049 -0.4520 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1278 -3.5452 0.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3934 -6.2863 2.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0596 -5.4270 2.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3695 -3.9397 1.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0463 -3.2163 0.3380 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3291 -0.6567 -1.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8078 0.3736 0.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2428 -0.5683 1.9194 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9691 -1.7266 0.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5160 -0.4464 1.8630 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3234 0.5151 -1.7186 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8650 1.2321 -0.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5914 -0.1752 -1.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9133 1.4899 -2.9090 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2879 2.3748 -0.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7357 4.0469 -1.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6657 2.3578 1.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7060 3.9506 2.0212 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6946 2.1867 1.8765 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7212 0.6944 3.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7961 -0.4454 -1.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0057 1.2296 -1.5829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3581 -1.7169 -3.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3720 -3.6376 -2.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4807 -2.7699 -2.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4024 -4.5675 -1.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6699 0.1877 -1.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4493 1.4908 -2.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 7 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 3 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 20 22 1 0 22 23 2 0 16 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 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 36 37 1 0 37 38 1 0 36 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 31 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 27 51 2 0 51 52 1 0 52 53 1 0 52 54 2 0 54 2 1 0 14 5 1 0 23 17 1 0 54 25 1 0 49 29 1 0 43 34 1 0 5 55 1 1 7 56 1 6 8 57 1 0 8 58 1 0 9 59 1 0 10 60 1 6 11 61 1 0 12 62 1 1 13 63 1 0 14 64 1 6 15 65 1 0 18 66 1 0 19 67 1 0 21 68 1 0 22 69 1 0 23 70 1 0 26 71 1 0 29 72 1 6 31 73 1 1 32 74 1 0 32 75 1 0 34 76 1 1 36 77 1 6 37 78 1 0 37 79 1 0 38 80 1 0 39 81 1 6 40 82 1 0 41 83 1 1 42 84 1 0 43 85 1 1 44 86 1 0 45 87 1 1 46 88 1 0 47 89 1 6 48 90 1 0 49 91 1 6 50 92 1 0 51 93 1 0 53 94 1 0 M END

Standard InCHIKey	HLPZWKGCSQDNGN-GKACCPRBSA-N
Standard InCHI	InChI=1S/C33H40O21/c34-7-15-19(38)23(42)26(45)31(51-15)48-9-17-21(40)25(44)27(46)32(53-17)49-12-5-13(37)18-14(6-12)50-29(10-1-3-11(36)4-2-10)30(22(18)41)54-33-28(47)24(43)20(39)16(8-35)52-33/h1-6,15-17,19-21,23-28,31-40,42-47H,7-9H2/t15-,16-,17+,19+,20+,21+,23-,24-,25-,26+,27-,28+,31+,32+,33-/m0/s1
SMILES	O=C1C(O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C(C2=CC=C(O)C=C2)OC2=CC(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@@H]3O)=CC(O)=C12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	772.21	Volume:	691.488 ? Van der Waals volume.
Dense:	1.117	LogP:	-0.617 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.4 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.892 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	348.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.32	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:	0	PAINS Alert:	0
Colloidal aggregators:	0.627	Fluc inhibitor:	0.284 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.727 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.634 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.226	Promiscuous compounds:	0.571

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.142	MDCK Permeability:	-4.695
Pgp-inhibitor:	0.0	Pgp-substrate:	0.941
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):	0.989
20% Bioavailability (F20%):	0.714	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.088
Plasma Protein Binding (PPB):	78.524%	Volume Distribution (VD):	-0.092
Fu:	20.029% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.975
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.032
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:	0.62
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):

0.992

Half-life (T1/2):

5.039

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.028
Human Hepatotoxicity (H-HT):	0.587	Drug-induced Liver Injury (DILI):	0.967
AMES Toxicity:	0.974	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.147	Drug-induced Nephrotoxicity:	0.865
Genotoxicity:	0.677	RPMI-8226 Immunitoxicity:	0.189
A549 Cytotoxicity:	0.719	Hek293 Cytotoxicity:	0.351
BCF:	0.286 ? 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:	2.519 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.278 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.278 ? 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
NPO59741	Nerisyrenia camporum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO51288	Nerisyrenia linearifolia	Species	Brassicaceae	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 NPC597248 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	24353
0.1-0.2	21371
0.2-0.3	2950
0.3-0.4	606
0.4-0.5	296
0.5-0.6	96
0.6-0.7	82
0.7-0.8	1
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8554	High Similarity	NPC186816
0.8442	Intermediate Similarity	NPC297987
0.8043	Intermediate Similarity	NPC25523
0.7927	Intermediate Similarity	NPC116458
0.7927	Intermediate Similarity	NPC246943
0.7531	Intermediate Similarity	NPC136042
0.7407	Intermediate Similarity	NPC289667
0.7386	Intermediate Similarity	NPC156869
0.7292	Intermediate Similarity	NPC480441
0.7222	Intermediate Similarity	NPC64425
0.7195	Intermediate Similarity	NPC249281
0.7093	Intermediate Similarity	NPC605784
0.7079	Intermediate Similarity	NPC173582
0.7079	Intermediate Similarity	NPC265885
0.7079	Intermediate Similarity	NPC181465
0.7079	Intermediate Similarity	NPC215710
0.7079	Intermediate Similarity	NPC473438
0.7079	Intermediate Similarity	NPC253788
0.7065	Intermediate Similarity	NPC35119
0.7024	Intermediate Similarity	NPC46420
0.7024	Intermediate Similarity	NPC84362
0.7011	Intermediate Similarity	NPC276377
0.6966	Remote Similarity	NPC471079
0.6907	Remote Similarity	NPC189564
0.6889	Remote Similarity	NPC44931
0.6889	Remote Similarity	NPC275454
0.6882	Remote Similarity	NPC32641
0.6882	Remote Similarity	NPC256188
0.6848	Remote Similarity	NPC488073
0.6813	Remote Similarity	NPC479405
0.6813	Remote Similarity	NPC150164
0.6809	Remote Similarity	NPC142142
0.6804	Remote Similarity	NPC121703
0.6786	Remote Similarity	NPC77672
0.6786	Remote Similarity	NPC133671
0.6786	Remote Similarity	NPC135391
0.6786	Remote Similarity	NPC78263
0.6786	Remote Similarity	NPC250069
0.6739	Remote Similarity	NPC479404
0.6706	Remote Similarity	NPC323593
0.6706	Remote Similarity	NPC203500
0.67	Remote Similarity	NPC277532
0.663	Remote Similarity	NPC65563
0.663	Remote Similarity	NPC470949
0.6628	Remote Similarity	NPC24043
0.6588	Remote Similarity	NPC39360
0.6588	Remote Similarity	NPC29763
0.6588	Remote Similarity	NPC210003
0.6559	Remote Similarity	NPC473571
0.6559	Remote Similarity	NPC110941
0.6531	Remote Similarity	NPC14187
0.6522	Remote Similarity	NPC67105
0.6489	Remote Similarity	NPC240306
0.6484	Remote Similarity	NPC251417
0.6465	Remote Similarity	NPC203145
0.6452	Remote Similarity	NPC203259
0.6452	Remote Similarity	NPC33054
0.6452	Remote Similarity	NPC210073
0.6452	Remote Similarity	NPC176740
0.6452	Remote Similarity	NPC471725
0.6452	Remote Similarity	NPC134532
0.6452	Remote Similarity	NPC602582
0.6436	Remote Similarity	NPC164704
0.6421	Remote Similarity	NPC479403
0.6354	Remote Similarity	NPC72016
0.6344	Remote Similarity	NPC67326
0.6337	Remote Similarity	NPC292019
0.6337	Remote Similarity	NPC202908
0.6327	Remote Similarity	NPC292929
0.6322	Remote Similarity	NPC277205
0.6322	Remote Similarity	NPC37919
0.6263	Remote Similarity	NPC602448
0.625	Remote Similarity	NPC470443
0.625	Remote Similarity	NPC271692
0.625	Remote Similarity	NPC488080
0.625	Remote Similarity	NPC169977
0.6168	Remote Similarity	NPC470720
0.6154	Remote Similarity	NPC470716
0.6136	Remote Similarity	NPC145038
0.6136	Remote Similarity	NPC8573
0.6136	Remote Similarity	NPC56077
0.6136	Remote Similarity	NPC281131
0.6136	Remote Similarity	NPC64305
0.6136	Remote Similarity	NPC253662
0.6136	Remote Similarity	NPC179950
0.6136	Remote Similarity	NPC88789
0.6136	Remote Similarity	NPC189142
0.6136	Remote Similarity	NPC77660
0.6136	Remote Similarity	NPC491374
0.6122	Remote Similarity	NPC486577
0.6117	Remote Similarity	NPC470715
0.6082	Remote Similarity	NPC65711
0.6075	Remote Similarity	NPC470717
0.6064	Remote Similarity	NPC139320
0.6061	Remote Similarity	NPC476472
0.6061	Remote Similarity	NPC294815
0.6061	Remote Similarity	NPC473073
0.6061	Remote Similarity	NPC16194
0.6047	Remote Similarity	NPC288084
0.6	Remote Similarity	NPC472459
0.6	Remote Similarity	NPC101636
0.6	Remote Similarity	NPC39834
0.6	Remote Similarity	NPC470449
0.6	Remote Similarity	NPC227508
0.5979	Remote Similarity	NPC126784
0.5979	Remote Similarity	NPC241423
0.5979	Remote Similarity	NPC488074
0.5979	Remote Similarity	NPC64051
0.5938	Remote Similarity	NPC22062
0.5938	Remote Similarity	NPC473634
0.5938	Remote Similarity	NPC303913
0.5938	Remote Similarity	NPC138811
0.5934	Remote Similarity	NPC307938
0.5934	Remote Similarity	NPC488071
0.5876	Remote Similarity	NPC129264
0.5859	Remote Similarity	NPC209296
0.5859	Remote Similarity	NPC473327
0.5851	Remote Similarity	NPC116864
0.5851	Remote Similarity	NPC244776
0.5843	Remote Similarity	NPC261866
0.5833	Remote Similarity	NPC470405
0.5816	Remote Similarity	NPC470125
0.5784	Remote Similarity	NPC135358
0.5778	Remote Similarity	NPC158674
0.5761	Remote Similarity	NPC285197
0.5761	Remote Similarity	NPC611303
0.5758	Remote Similarity	NPC12013
0.5758	Remote Similarity	NPC11432
0.5758	Remote Similarity	NPC477613
0.5745	Remote Similarity	NPC203050
0.5745	Remote Similarity	NPC170052
0.5745	Remote Similarity	NPC225434
0.5745	Remote Similarity	NPC135846
0.5743	Remote Similarity	NPC85751
0.5743	Remote Similarity	NPC76831
0.5743	Remote Similarity	NPC19240
0.573	Remote Similarity	NPC111929
0.573	Remote Similarity	NPC320283
0.573	Remote Similarity	NPC41121
0.57	Remote Similarity	NPC270448
0.5699	Remote Similarity	NPC601144
0.5688	Remote Similarity	NPC298666
0.5686	Remote Similarity	NPC298171
0.5676	Remote Similarity	NPC209550
0.5667	Remote Similarity	NPC19388
0.5667	Remote Similarity	NPC240431
0.5667	Remote Similarity	NPC55786
0.5667	Remote Similarity	NPC108831
0.5667	Remote Similarity	NPC182634
0.5652	Remote Similarity	NPC42773
0.5652	Remote Similarity	NPC45522
0.5652	Remote Similarity	NPC599850
0.5644	Remote Similarity	NPC270675
0.5644	Remote Similarity	NPC195685
0.5638	Remote Similarity	NPC311830
0.5625	Remote Similarity	NPC473682
0.5625	Remote Similarity	NPC192539
0.5612	Remote Similarity	NPC304741
0.5604	Remote Similarity	NPC197896
0.5604	Remote Similarity	NPC95090
0.5604	Remote Similarity	NPC313163
0.5604	Remote Similarity	NPC27408
0.5596	Remote Similarity	NPC295625
0.5591	Remote Similarity	NPC168584
0.5591	Remote Similarity	NPC60735
0.5591	Remote Similarity	NPC26230
0.5588	Remote Similarity	NPC80068
0.5588	Remote Similarity	NPC470447
0.5579	Remote Similarity	NPC488072
0.5579	Remote Similarity	NPC601586
0.5577	Remote Similarity	NPC214621
0.5577	Remote Similarity	NPC34267
0.5567	Remote Similarity	NPC29958
0.5556	Remote Similarity	NPC331652
0.5545	Remote Similarity	NPC473623
0.5545	Remote Similarity	NPC229409
0.5536	Remote Similarity	NPC138990
0.5534	Remote Similarity	NPC221342
0.5534	Remote Similarity	NPC476470
0.5532	Remote Similarity	NPC22832
0.5532	Remote Similarity	NPC120099
0.5532	Remote Similarity	NPC486578
0.551	Remote Similarity	NPC471748
0.55	Remote Similarity	NPC153755
0.549	Remote Similarity	NPC488089
0.5484	Remote Similarity	NPC27942
0.5484	Remote Similarity	NPC325555
0.5484	Remote Similarity	NPC226304
0.5481	Remote Similarity	NPC470446
0.5481	Remote Similarity	NPC470450
0.5481	Remote Similarity	NPC472994
0.5455	Remote Similarity	NPC473512
0.5455	Remote Similarity	NPC129827
0.5455	Remote Similarity	NPC102028
0.5446	Remote Similarity	NPC488078
0.5444	Remote Similarity	NPC67037
0.5444	Remote Similarity	NPC255615
0.5429	Remote Similarity	NPC470455
0.5421	Remote Similarity	NPC219043
0.5408	Remote Similarity	NPC480466

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC597248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5932
0.1-0.2	3149
0.2-0.3	58
0.3-0.4	4
0.4-0.5	3
0.5-0.6	1
0.6-0.7	2
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
0.7283	Intermediate Similarity	NPD7251	Phase 2
0.6633	Remote Similarity	NPD7808	Phase 3
0.6452	Remote Similarity	NPD6797	Phase 2
0.5859	Remote Similarity	NPD7054	Phase 4

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