NPASS Compound

Natural Product: NPC509531

Natural Product ID	NPC509531
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-7-methoxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-[4-[(2~{S},3~{S},4~{R},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]chromen-4-one
IUPAC Name	5-hydroxy-7-methoxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-[4-[(2~{S},3~{S},4~{R},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]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 98103 0 0 0 0 0 0 0 0999 V2000 6.2007 -3.5453 6.2695 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0163 -3.2852 5.5762 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9374 -2.1669 4.7294 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0019 -1.3084 4.5632 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8939 -0.2258 3.7280 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9207 0.6820 3.5091 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6775 -0.0401 3.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5197 1.0327 2.2073 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4710 1.8119 2.0481 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3063 1.2246 1.5355 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2445 2.3018 0.6996 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8439 2.3166 -0.5712 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5910 3.4871 -0.6956 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7353 3.8597 -2.0330 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0355 4.6667 -2.1050 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0379 3.8108 -1.6903 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9849 2.6383 -2.9292 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3928 3.1215 -4.1613 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6721 1.8858 -3.0062 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8282 0.5519 -3.3023 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9035 2.1022 -1.6865 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0241 3.1548 -1.8234 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3153 0.3408 1.7635 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9957 0.4119 1.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4965 1.5317 0.5476 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7537 1.5527 -0.0414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5464 0.4087 -0.0241 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7826 0.4046 -0.5974 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4663 1.4246 -1.2392 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6740 1.6038 -0.5613 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5374 2.4833 -1.2003 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0842 3.9075 -1.1187 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0161 4.7035 -1.8059 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9084 2.0265 -2.5809 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5921 2.9485 -3.5678 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1822 0.7211 -2.8344 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4111 0.2570 -4.1307 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6967 0.9917 -2.6911 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9449 -0.1683 -2.9675 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0891 -0.7484 0.5791 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7522 -1.9366 0.6745 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 -2.3886 0.2669 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8443 -2.6618 1.3370 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7126 -3.6919 1.1377 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6818 -3.8409 2.3169 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5204 -4.9077 2.0112 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0821 -5.0471 0.9405 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0015 -5.8234 0.2360 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8542 -4.8894 0.0991 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6796 -5.0705 0.8312 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8616 -3.5922 -0.6523 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8303 -3.5411 -1.6334 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1970 -0.7075 1.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5142 -0.6980 2.6123 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6184 -0.9001 3.2378 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7351 -1.9997 4.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4590 -2.6365 6.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0026 -3.6890 5.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0755 -4.4406 6.8976 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9311 -1.4733 5.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5024 0.9105 4.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6034 1.4658 -0.6511 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8869 4.4277 -2.4023 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2161 4.9964 -3.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9674 5.5151 -1.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5959 4.2268 -1.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8094 2.0324 -2.5030 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1726 2.4931 -4.9010 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0587 2.3630 -3.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7335 0.2370 -3.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3390 1.1687 -1.5469 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5972 3.0561 -2.7164 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0452 2.4458 0.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1120 2.4591 -0.5124 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9848 2.3996 -1.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4905 2.4330 -0.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0868 4.1150 -1.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0370 4.2338 -0.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8338 4.7945 -1.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0106 1.8203 -2.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1452 2.7753 -4.3861 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4760 0.0091 -2.0557 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3122 0.6219 -4.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3492 1.7625 -3.4080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0093 0.1587 -3.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5138 -1.6232 -0.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3411 -3.4807 0.2505 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1226 -4.0487 3.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2804 -2.9250 2.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2520 -4.6317 1.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8870 -5.5664 1.9021 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1321 -6.7132 0.6640 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8592 -5.6968 -0.6731 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4963 -6.0603 0.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8675 -3.5056 -1.1585 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4911 -3.3675 -2.5385 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -1.5980 1.6393 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8899 -2.6456 4.1960 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 5 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 14 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 10 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 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 31 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 27 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 44 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 40 53 2 0 23 54 1 0 54 55 1 0 55 56 2 0 56 3 1 0 55 7 1 0 21 12 1 0 53 24 1 0 38 29 1 0 51 42 1 0 1 57 1 0 1 58 1 0 1 59 1 0 4 60 1 0 6 61 1 0 12 62 1 1 14 63 1 6 15 64 1 0 15 65 1 0 16 66 1 0 17 67 1 1 18 68 1 0 19 69 1 6 20 70 1 0 21 71 1 1 22 72 1 0 25 73 1 0 26 74 1 0 29 75 1 6 31 76 1 1 32 77 1 0 32 78 1 0 33 79 1 0 34 80 1 1 35 81 1 0 36 82 1 1 37 83 1 0 38 84 1 6 39 85 1 0 42 86 1 6 44 87 1 6 45 88 1 0 45 89 1 0 46 90 1 0 47 91 1 1 48 92 1 0 49 93 1 6 50 94 1 0 51 95 1 6 52 96 1 0 53 97 1 0 56 98 1 0 M END

Standard InCHIKey	HFRTYTQYRCHGFE-OKILWLJFSA-N
Standard InCHI	InChI=1S/C34H42O22/c1-49-11-5-12(38)19-15(6-11)50-30(31(23(19)42)56-34-29(48)26(45)22(41)18(9-37)55-34)10-2-3-13(51-32-27(46)24(43)20(39)16(7-35)53-32)14(4-10)52-33-28(47)25(44)21(40)17(8-36)54-33/h2-6,16-18,20-22,24-29,32-41,43-48H,7-9H2,1H3/t16-,17+,18-,20+,21+,22-,24+,25-,26+,27-,28+,29-,32+,33+,34-/m0/s1
SMILES	COC1=CC(O)=C2C(=O)C(O[C@@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]3O)=C(C3=CC=C(O[C@@H]4O[C@@H](CO)[C@@H](O)[C@@H](O)[C@@H]4O)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	802.22	Volume:	717.575 ? Van der Waals volume.
Dense:	1.118	LogP:	-0.621 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.767 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.595 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	36.0
TPSA:	357.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.367	Fsp³:	0.559
MCE-18:	153.34 ? 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:	0.668	Fluc inhibitor:	0.308 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.705 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.628 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.156	Promiscuous compounds:	0.565

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.087	MDCK Permeability:	-4.864
Pgp-inhibitor:	0.0	Pgp-substrate:	0.722
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):	1.0
20% Bioavailability (F20%):	0.651	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.01
Plasma Protein Binding (PPB):	75.81%	Volume Distribution (VD):	-0.107
Fu:	18.529% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.362
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:	0.066
HLM stability:	0.003 ? 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):

0.779

Half-life (T1/2):

4.351

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.008
Human Hepatotoxicity (H-HT):	0.857	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.996	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.026	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.49	Drug-induced Nephrotoxicity:	0.97
Genotoxicity:	0.498	RPMI-8226 Immunitoxicity:	0.328
A549 Cytotoxicity:	0.8	Hek293 Cytotoxicity:	0.129
BCF:	0.461 ? 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:	3.04 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.956 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.868 ? 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
NPO55573	Anthyllis onobrychioides	Species	Fabaceae	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 NPC509531 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	19841
0.1-0.2	25952
0.2-0.3	2671
0.3-0.4	839
0.4-0.5	345
0.5-0.6	119
0.6-0.7	62
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
0.8	Intermediate Similarity	NPC289667
0.7625	Intermediate Similarity	NPC607707
0.7436	Intermediate Similarity	NPC297987
0.7436	Intermediate Similarity	NPC136042
0.7342	Intermediate Similarity	NPC84362
0.7143	Intermediate Similarity	NPC251417
0.7073	Intermediate Similarity	NPC243930
0.6988	Remote Similarity	NPC116458
0.6988	Remote Similarity	NPC246943
0.6988	Remote Similarity	NPC605784
0.6867	Remote Similarity	NPC486578
0.6829	Remote Similarity	NPC472459
0.6747	Remote Similarity	NPC488071
0.6747	Remote Similarity	NPC611303
0.6707	Remote Similarity	NPC46420
0.6707	Remote Similarity	NPC271692
0.6706	Remote Similarity	NPC488072
0.6667	Remote Similarity	NPC21666
0.6585	Remote Similarity	NPC64305
0.6585	Remote Similarity	NPC95090
0.6585	Remote Similarity	NPC27408
0.6585	Remote Similarity	NPC158674
0.6556	Remote Similarity	NPC64425
0.6548	Remote Similarity	NPC285197
0.6506	Remote Similarity	NPC24043
0.6471	Remote Similarity	NPC22832
0.6471	Remote Similarity	NPC120099
0.6429	Remote Similarity	NPC277532
0.6386	Remote Similarity	NPC277205
0.6386	Remote Similarity	NPC37919
0.6353	Remote Similarity	NPC609451
0.6322	Remote Similarity	NPC203050
0.6322	Remote Similarity	NPC225434
0.6322	Remote Similarity	NPC601586
0.631	Remote Similarity	NPC603655
0.6265	Remote Similarity	NPC249281
0.6235	Remote Similarity	NPC325555
0.6235	Remote Similarity	NPC226304
0.6224	Remote Similarity	NPC48984
0.6216	Remote Similarity	NPC236769
0.619	Remote Similarity	NPC323593
0.619	Remote Similarity	NPC203500
0.6163	Remote Similarity	NPC60735
0.6163	Remote Similarity	NPC26230
0.6092	Remote Similarity	NPC101026
0.6092	Remote Similarity	NPC488077
0.6092	Remote Similarity	NPC609478
0.6071	Remote Similarity	NPC261866
0.6071	Remote Similarity	NPC77672
0.6071	Remote Similarity	NPC133671
0.6071	Remote Similarity	NPC135391
0.6071	Remote Similarity	NPC78263
0.6071	Remote Similarity	NPC250069
0.6064	Remote Similarity	NPC35119
0.6047	Remote Similarity	NPC42773
0.6047	Remote Similarity	NPC45522
0.6023	Remote Similarity	NPC88023
0.6023	Remote Similarity	NPC311830
0.6023	Remote Similarity	NPC309025
0.6022	Remote Similarity	NPC240306
0.6	Remote Similarity	NPC145038
0.6	Remote Similarity	NPC56077
0.6	Remote Similarity	NPC281131
0.6	Remote Similarity	NPC253662
0.6	Remote Similarity	NPC179950
0.6	Remote Similarity	NPC88789
0.6	Remote Similarity	NPC189142
0.6	Remote Similarity	NPC77660
0.6	Remote Similarity	NPC491374
0.5934	Remote Similarity	NPC480466
0.593	Remote Similarity	NPC186807
0.593	Remote Similarity	NPC488080
0.593	Remote Similarity	NPC169977
0.593	Remote Similarity	NPC73511
0.5922	Remote Similarity	NPC295625
0.5918	Remote Similarity	NPC14187
0.5905	Remote Similarity	NPC470720
0.5895	Remote Similarity	NPC32641
0.5895	Remote Similarity	NPC256188
0.5895	Remote Similarity	NPC606657
0.5882	Remote Similarity	NPC19388
0.5882	Remote Similarity	NPC58053
0.5882	Remote Similarity	NPC240431
0.5882	Remote Similarity	NPC39360
0.5882	Remote Similarity	NPC55786
0.5882	Remote Similarity	NPC29763
0.5882	Remote Similarity	NPC470716
0.5882	Remote Similarity	NPC210003
0.5862	Remote Similarity	NPC117260
0.5862	Remote Similarity	NPC599850
0.5842	Remote Similarity	NPC480441
0.5842	Remote Similarity	NPC470715
0.5842	Remote Similarity	NPC25523
0.5842	Remote Similarity	NPC164704
0.5833	Remote Similarity	NPC5319
0.5833	Remote Similarity	NPC486577
0.5824	Remote Similarity	NPC480463
0.5823	Remote Similarity	NPC99671
0.581	Remote Similarity	NPC470719
0.581	Remote Similarity	NPC470717
0.5795	Remote Similarity	NPC307938
0.5778	Remote Similarity	NPC276377
0.573	Remote Similarity	NPC148710
0.573	Remote Similarity	NPC601144
0.57	Remote Similarity	NPC121703
0.5682	Remote Similarity	NPC182045
0.5667	Remote Similarity	NPC206123
0.5638	Remote Similarity	NPC150164
0.5579	Remote Similarity	NPC186816
0.5568	Remote Similarity	NPC22195
0.5568	Remote Similarity	NPC27640
0.5568	Remote Similarity	NPC21190
0.5568	Remote Similarity	NPC45638
0.5556	Remote Similarity	NPC605067
0.5506	Remote Similarity	NPC201292
0.55	Remote Similarity	NPC135358
0.5467	Remote Similarity	NPC262094
0.5463	Remote Similarity	NPC488079
0.5455	Remote Similarity	NPC93337
0.5455	Remote Similarity	NPC8573
0.5455	Remote Similarity	NPC234739
0.5444	Remote Similarity	NPC219904
0.5435	Remote Similarity	NPC267254
0.5417	Remote Similarity	NPC131745
0.5408	Remote Similarity	NPC72016
0.5395	Remote Similarity	NPC76376
0.5393	Remote Similarity	NPC181712
0.5393	Remote Similarity	NPC105025
0.5385	Remote Similarity	NPC284960
0.5368	Remote Similarity	NPC275454
0.5361	Remote Similarity	NPC488073
0.5349	Remote Similarity	NPC288084
0.5341	Remote Similarity	NPC238376
0.5333	Remote Similarity	NPC59534
0.5333	Remote Similarity	NPC21100
0.5326	Remote Similarity	NPC223747
0.5326	Remote Similarity	NPC602805
0.5321	Remote Similarity	NPC488078
0.5319	Remote Similarity	NPC473682
0.5312	Remote Similarity	NPC156869
0.53	Remote Similarity	NPC76831
0.5288	Remote Similarity	NPC477895
0.5287	Remote Similarity	NPC67037
0.5287	Remote Similarity	NPC255615
0.5281	Remote Similarity	NPC197896
0.5281	Remote Similarity	NPC313163
0.5275	Remote Similarity	NPC168584
0.5256	Remote Similarity	NPC270620
0.5238	Remote Similarity	NPC191154
0.5222	Remote Similarity	NPC245014
0.5222	Remote Similarity	NPC349108
0.5213	Remote Similarity	NPC265115
0.5204	Remote Similarity	NPC153755
0.52	Remote Similarity	NPC142142
0.519	Remote Similarity	NPC206604
0.5176	Remote Similarity	NPC134819
0.5172	Remote Similarity	NPC34531
0.5169	Remote Similarity	NPC110349
0.5169	Remote Similarity	NPC44558
0.5169	Remote Similarity	NPC108831
0.5169	Remote Similarity	NPC143851
0.5169	Remote Similarity	NPC182634
0.5165	Remote Similarity	NPC60966
0.5152	Remote Similarity	NPC483414
0.5152	Remote Similarity	NPC483415
0.5125	Remote Similarity	NPC78326
0.5111	Remote Similarity	NPC168822
0.5111	Remote Similarity	NPC265530
0.5109	Remote Similarity	NPC175107
0.5109	Remote Similarity	NPC80140
0.5106	Remote Similarity	NPC355481
0.5104	Remote Similarity	NPC29958
0.5104	Remote Similarity	NPC139320
0.5104	Remote Similarity	NPC609888
0.51	Remote Similarity	NPC483416
0.5089	Remote Similarity	NPC175429
0.5065	Remote Similarity	NPC103904
0.5056	Remote Similarity	NPC111929
0.5056	Remote Similarity	NPC320283
0.5056	Remote Similarity	NPC473043
0.5056	Remote Similarity	NPC41121
0.5055	Remote Similarity	NPC305811
0.5055	Remote Similarity	NPC84265
0.5055	Remote Similarity	NPC610763
0.5052	Remote Similarity	NPC267680
0.5052	Remote Similarity	NPC471748
0.5051	Remote Similarity	NPC46202
0.5043	Remote Similarity	NPC223860

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC509531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5142
0.1-0.2	3917
0.2-0.3	75
0.3-0.4	9
0.4-0.5	4
0.5-0.6	2
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
0.6354	Remote Similarity	NPD7808	Phase 3
0.5833	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5455	Remote Similarity	NPD7251	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