NPASS Compound

Natural Product: NPC549595

Natural Product ID	NPC549595
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-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},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-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},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 92 97 0 0 0 0 0 0 0 0999 V2000 10.5030 0.0276 -2.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6437 -0.9288 -1.4866 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4439 -0.3571 -0.2318 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5451 -1.2574 0.4103 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6030 -1.6615 -0.3862 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3149 -1.5739 -0.4350 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5891 -0.2714 -0.6536 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2080 -0.4872 -0.6431 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4954 0.4156 0.0836 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1322 0.1656 0.1316 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1702 1.1330 -0.0018 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3904 2.4798 -0.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3863 3.4216 -0.3090 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6620 4.7723 -0.4880 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9155 3.0221 -0.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9703 3.9074 -0.3793 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 5.1084 -0.5379 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2490 3.3952 -0.3139 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5185 2.0572 -0.1375 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8734 1.5288 -0.0710 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9779 2.3293 -0.1215 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2735 1.7875 -0.0643 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4679 0.4465 0.0429 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6913 -0.1684 0.1060 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9505 0.4177 0.0997 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6742 0.0363 1.1946 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9883 -1.2833 1.3109 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8670 -2.1905 1.7373 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3680 -3.5144 1.8111 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6918 -1.8787 0.1041 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.0355 -1.5413 0.1080 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0663 -1.4256 -1.1851 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9604 -2.2055 -1.5497 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6944 0.0270 -1.1698 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.8384 0.8409 -1.3114 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3411 -0.3837 0.0953 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0796 0.1705 0.0379 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4767 1.2693 -0.0313 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2151 1.6893 -0.0840 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1887 0.7773 0.0407 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0867 0.3804 1.5180 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2090 0.9364 2.4205 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3996 1.1240 1.4171 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2061 0.7734 2.4895 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0450 0.9182 0.0698 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8362 2.1014 -0.7151 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4734 -2.3259 0.9815 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2101 -1.6958 1.9863 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4477 -2.8299 -0.0364 C 0 0 2 0 0 0 0 0 0 0 0 0 11.7783 -2.5187 0.3042 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2104 -2.3080 -1.4233 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3379 -3.1726 -2.0955 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1506 0.6064 -1.5618 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8582 0.7971 -2.7629 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1244 -0.4888 -3.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6335 -0.9258 -1.9774 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1742 -0.7127 1.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9697 -2.3127 -1.2685 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7482 -2.0520 0.4328 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7719 -0.0350 -1.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7119 1.4380 -0.2554 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4155 2.8427 -0.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4856 5.1915 -1.3976 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0719 4.0999 -0.4093 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9184 3.4070 -0.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1197 2.4580 -0.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9181 1.5325 0.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7532 -1.3542 2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5470 -1.9595 2.7904 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0241 -2.2513 1.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6637 -4.1214 2.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6079 -2.9703 0.1662 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1169 -0.5822 0.3981 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8197 -1.5713 -1.9953 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6719 -1.8330 -2.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0009 0.2301 -2.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5676 1.7315 -0.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4920 -1.4516 0.1800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2303 -0.4870 0.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4157 -0.2678 0.1782 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3127 -0.6805 1.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3126 0.5556 2.2437 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1691 2.2023 1.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7058 0.3979 3.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1291 0.9178 0.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6654 2.8583 -0.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8855 -3.1109 1.4947 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8130 -0.8337 2.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4042 -3.9390 -0.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9093 -2.4861 1.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1591 -2.3162 -2.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1620 -4.0044 -1.5799 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 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 23 36 1 0 36 37 2 0 19 38 1 0 38 39 1 0 39 40 2 0 9 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 4 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 51 2 1 0 45 7 1 0 40 11 1 0 39 15 1 0 37 20 1 0 34 25 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 6 4 57 1 1 6 58 1 0 6 59 1 0 7 60 1 6 9 61 1 6 12 62 1 0 14 63 1 0 18 64 1 0 21 65 1 0 22 66 1 0 25 67 1 1 27 68 1 1 28 69 1 0 28 70 1 0 29 71 1 0 30 72 1 1 31 73 1 0 32 74 1 6 33 75 1 0 34 76 1 6 35 77 1 0 36 78 1 0 37 79 1 0 40 80 1 0 41 81 1 1 42 82 1 0 43 83 1 1 44 84 1 0 45 85 1 1 46 86 1 0 47 87 1 1 48 88 1 0 49 89 1 6 50 90 1 0 51 91 1 6 52 92 1 0 M END

Standard InCHIKey	LBYRFTLMNPBSBD-BCRVAMIHSA-N
Standard InCHI	InChI=1S/C33H40O19/c1-11-22(37)25(40)28(43)31(47-11)46-10-20-24(39)27(42)30(45)33(52-20)49-14-6-15(35)21-16(36)8-17(50-18(21)7-14)12-2-4-13(5-3-12)48-32-29(44)26(41)23(38)19(9-34)51-32/h2-8,11,19-20,22-35,37-45H,9-10H2,1H3/t11-,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@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C=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:	740.22	Volume:	673.908 ? Van der Waals volume.
Dense:	1.098	LogP:	0.651 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.227 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.265 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	308.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.101	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.229	Fsp³:	0.545
MCE-18:	147.118 ? 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:	0.635	Fluc inhibitor:	0.358 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.913 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.548 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.211	Promiscuous compounds:	0.368

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.9	MDCK Permeability:	-4.927
Pgp-inhibitor:	0.0	Pgp-substrate:	0.862
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):	0.999
20% Bioavailability (F20%):	0.397	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.007
Plasma Protein Binding (PPB):	79.534%	Volume Distribution (VD):	-0.104
Fu:	16.263% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.105
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:	0.341
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.902
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):

0.641

Half-life (T1/2):

5.73

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.7	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	0.998
Carcinogencity:	0.028	Eye Corrosion:	0.0
Eye Irritation:	0.021	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.992
Hematotoxicity:	0.139	Drug-induced Nephrotoxicity:	0.948
Genotoxicity:	0.735	RPMI-8226 Immunitoxicity:	0.349
A549 Cytotoxicity:	0.604	Hek293 Cytotoxicity:	0.275
BCF:	0.35 ? 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:	3.09 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.808 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.799 ? 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
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27666	Sophora tetraptera	Species	Fabaceae	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 NPC549595 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	18987
0.1-0.2	25860
0.2-0.3	3802
0.3-0.4	751
0.4-0.5	266
0.5-0.6	112
0.6-0.7	51
0.7-0.8	1
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8795	High Similarity	NPC22062
0.8795	High Similarity	NPC473634
0.8795	High Similarity	NPC138811
0.8235	Intermediate Similarity	NPC44931
0.7978	Intermediate Similarity	NPC209296
0.7931	Intermediate Similarity	NPC210073
0.7526	Intermediate Similarity	NPC311850
0.747	Intermediate Similarity	NPC95090
0.747	Intermediate Similarity	NPC27408
0.7444	Intermediate Similarity	NPC204693
0.7391	Intermediate Similarity	NPC473623
0.7312	Intermediate Similarity	NPC488089
0.73	Intermediate Similarity	NPC68592
0.7113	Intermediate Similarity	NPC11468
0.7059	Intermediate Similarity	NPC298666
0.7053	Intermediate Similarity	NPC475382
0.7048	Intermediate Similarity	NPC262222
0.6979	Remote Similarity	NPC101636
0.6941	Remote Similarity	NPC39360
0.6941	Remote Similarity	NPC29763
0.6941	Remote Similarity	NPC210003
0.6893	Remote Similarity	NPC198199
0.6765	Remote Similarity	NPC488083
0.6742	Remote Similarity	NPC22832
0.6742	Remote Similarity	NPC243930
0.6735	Remote Similarity	NPC135358
0.6733	Remote Similarity	NPC473644
0.6698	Remote Similarity	NPC120952
0.6667	Remote Similarity	NPC67105
0.6667	Remote Similarity	NPC189142
0.6667	Remote Similarity	NPC77660
0.6667	Remote Similarity	NPC607707
0.6632	Remote Similarity	NPC46202
0.6628	Remote Similarity	NPC331652
0.6596	Remote Similarity	NPC65003
0.6569	Remote Similarity	NPC480441
0.6569	Remote Similarity	NPC25523
0.6562	Remote Similarity	NPC65711
0.6552	Remote Similarity	NPC261866
0.6526	Remote Similarity	NPC186816
0.6489	Remote Similarity	NPC275454
0.6489	Remote Similarity	NPC227508
0.6465	Remote Similarity	NPC298171
0.6404	Remote Similarity	NPC181712
0.6374	Remote Similarity	NPC601144
0.6364	Remote Similarity	NPC58053
0.6364	Remote Similarity	NPC19709
0.6364	Remote Similarity	NPC143851
0.6354	Remote Similarity	NPC115674
0.6304	Remote Similarity	NPC311830
0.6289	Remote Similarity	NPC64051
0.625	Remote Similarity	NPC473043
0.6222	Remote Similarity	NPC186807
0.6211	Remote Similarity	NPC187379
0.618	Remote Similarity	NPC289667
0.617	Remote Similarity	NPC211594
0.6168	Remote Similarity	NPC488086
0.6162	Remote Similarity	NPC483707
0.6162	Remote Similarity	NPC229409
0.6132	Remote Similarity	NPC488087
0.6122	Remote Similarity	NPC475366
0.61	Remote Similarity	NPC270675
0.61	Remote Similarity	NPC195685
0.6082	Remote Similarity	NPC479405
0.6082	Remote Similarity	NPC303913
0.604	Remote Similarity	NPC195257
0.6022	Remote Similarity	NPC80188
0.602	Remote Similarity	NPC479404
0.5978	Remote Similarity	NPC27942
0.5957	Remote Similarity	NPC220169
0.5938	Remote Similarity	NPC8856
0.5938	Remote Similarity	NPC251417
0.5922	Remote Similarity	NPC472994
0.59	Remote Similarity	NPC479403
0.5895	Remote Similarity	NPC190003
0.5865	Remote Similarity	NPC14187
0.5825	Remote Similarity	NPC287889
0.5789	Remote Similarity	NPC116458
0.5789	Remote Similarity	NPC246943
0.5789	Remote Similarity	NPC605784
0.5745	Remote Similarity	NPC285197
0.5741	Remote Similarity	NPC277532
0.5714	Remote Similarity	NPC244875
0.5714	Remote Similarity	NPC295613
0.5714	Remote Similarity	NPC473657
0.5701	Remote Similarity	NPC472993
0.5591	Remote Similarity	NPC277205
0.5591	Remote Similarity	NPC37919
0.5591	Remote Similarity	NPC323593
0.5591	Remote Similarity	NPC203500
0.5579	Remote Similarity	NPC609451
0.5534	Remote Similarity	NPC124155
0.5534	Remote Similarity	NPC32641
0.5534	Remote Similarity	NPC256188
0.5534	Remote Similarity	NPC35119
0.5532	Remote Similarity	NPC105025
0.5521	Remote Similarity	NPC486578
0.5521	Remote Similarity	NPC605067
0.551	Remote Similarity	NPC172807
0.5495	Remote Similarity	NPC488088
0.5484	Remote Similarity	NPC45618
0.5481	Remote Similarity	NPC142142
0.5446	Remote Similarity	NPC473512
0.5446	Remote Similarity	NPC129827
0.5429	Remote Similarity	NPC477629
0.5426	Remote Similarity	NPC93337
0.5426	Remote Similarity	NPC297987
0.5426	Remote Similarity	NPC146792
0.5426	Remote Similarity	NPC136042
0.5417	Remote Similarity	NPC191306
0.54	Remote Similarity	NPC603300
0.5392	Remote Similarity	NPC257566
0.5392	Remote Similarity	NPC122809
0.5385	Remote Similarity	NPC473327
0.5368	Remote Similarity	NPC84362
0.5368	Remote Similarity	NPC73511
0.5347	Remote Similarity	NPC173582
0.5347	Remote Similarity	NPC265885
0.5347	Remote Similarity	NPC181465
0.5347	Remote Similarity	NPC215710
0.5347	Remote Similarity	NPC473438
0.5347	Remote Similarity	NPC253788
0.534	Remote Similarity	NPC64425
0.5333	Remote Similarity	NPC479766
0.5333	Remote Similarity	NPC134819
0.5319	Remote Similarity	NPC108831
0.5319	Remote Similarity	NPC238376
0.5319	Remote Similarity	NPC182634
0.5312	Remote Similarity	NPC201292
0.5306	Remote Similarity	NPC88023
0.5306	Remote Similarity	NPC309025
0.53	Remote Similarity	NPC254540
0.5294	Remote Similarity	NPC203259
0.5294	Remote Similarity	NPC33054
0.5294	Remote Similarity	NPC102028
0.5294	Remote Similarity	NPC176740
0.5294	Remote Similarity	NPC471725
0.5294	Remote Similarity	NPC134532
0.5294	Remote Similarity	NPC156869
0.5294	Remote Similarity	NPC602582
0.5288	Remote Similarity	NPC470443
0.5283	Remote Similarity	NPC479765
0.5263	Remote Similarity	NPC168822
0.5263	Remote Similarity	NPC234739
0.5258	Remote Similarity	NPC307938
0.5258	Remote Similarity	NPC611303
0.5222	Remote Similarity	NPC191154
0.5213	Remote Similarity	NPC160515
0.5208	Remote Similarity	NPC58716
0.5208	Remote Similarity	NPC45638
0.5208	Remote Similarity	NPC610763
0.5204	Remote Similarity	NPC608742
0.5196	Remote Similarity	NPC39834
0.5192	Remote Similarity	NPC284277
0.5192	Remote Similarity	NPC240306
0.5192	Remote Similarity	NPC475497
0.5158	Remote Similarity	NPC249281
0.5158	Remote Similarity	NPC83283
0.5152	Remote Similarity	NPC99957
0.5152	Remote Similarity	NPC602805
0.5146	Remote Similarity	NPC65563
0.5146	Remote Similarity	NPC470949
0.514	Remote Similarity	NPC473073
0.51	Remote Similarity	NPC276377
0.51	Remote Similarity	NPC601586
0.5096	Remote Similarity	NPC473571
0.5096	Remote Similarity	NPC110941
0.5089	Remote Similarity	NPC470715
0.506	Remote Similarity	NPC29353
0.5052	Remote Similarity	NPC46420
0.5052	Remote Similarity	NPC271692
0.5051	Remote Similarity	NPC181616
0.5051	Remote Similarity	NPC601710
0.5049	Remote Similarity	NPC47923
0.5048	Remote Similarity	NPC488073
0.5048	Remote Similarity	NPC126784
0.5048	Remote Similarity	NPC241423
0.5046	Remote Similarity	NPC253685
0.5046	Remote Similarity	NPC602448
0.5045	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 NPC549595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5028
0.1-0.2	4016
0.2-0.3	93
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
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
0.7978	Intermediate Similarity	NPD7054	Phase 4
0.6275	Remote Similarity	NPD7808	Phase 3
0.62	Remote Similarity	NPD7251	Phase 2
0.6117	Remote Similarity	NPD7472	Pre-clinical
0.5294	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