NPASS Compound

Natural Product: NPC528069

Natural Product ID	NPC528069
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-[(2~{S},3~{S},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-[4-[(2~{S},3~{S},4~{R},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
IUPAC Name	5-hydroxy-7-[(2~{S},3~{S},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-[4-[(2~{S},3~{S},4~{R},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 91 96 0 0 0 0 0 0 0 0999 V2000 8.7475 -1.3132 -3.4274 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7482 -1.6453 -1.9515 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4931 -1.6606 -1.3997 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0459 -0.4211 -0.9371 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9687 -0.4018 0.4503 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6258 -0.2461 0.8290 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4182 -0.2698 2.3146 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0639 -0.1487 2.5805 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5269 1.1082 2.2637 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1775 1.0499 2.6484 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1856 0.7825 1.7262 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3743 0.5090 0.3989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3019 0.2466 -0.4647 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9918 0.2492 -0.0278 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1304 -0.0538 -0.8963 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0017 -0.4113 -2.2126 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0891 -0.7024 -3.0326 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9576 -1.0266 -4.2277 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3500 -0.6207 -2.4724 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4741 -0.8956 -3.2186 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3162 -1.2617 -4.5686 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7138 -0.8073 -2.6335 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8416 -0.4397 -1.2853 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1302 -0.3851 -0.8121 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5769 -0.0294 0.4519 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1938 -1.0322 1.1524 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5312 -1.2014 0.9831 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9686 -2.6453 1.0956 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1086 -0.5995 -0.2782 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6564 -1.3634 -1.3485 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7447 0.8665 -0.3992 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.4984 1.1338 -1.7376 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5042 1.1746 0.4185 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7853 2.2538 -0.0426 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7054 -0.1782 -0.5893 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4246 -0.2562 -1.1439 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3667 0.0065 -0.4203 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1889 0.5254 1.3110 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1516 0.7850 2.1728 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2046 2.2044 3.0302 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3446 2.9625 3.8052 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3474 1.6538 3.8692 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1213 2.6723 4.3940 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2265 0.7924 2.9808 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9137 1.5309 2.0589 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8190 0.7405 -1.4487 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2468 1.9171 -0.9459 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2538 0.6326 -1.0499 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3869 1.0424 0.2718 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7214 -0.7916 -1.1595 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9660 -1.3902 0.0602 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4116 -0.4307 -3.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2049 -2.1363 -4.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7236 -1.1955 -3.8341 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1413 -2.7022 -1.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9943 -0.2938 -1.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3559 0.7721 0.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9608 -0.9952 0.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6930 -1.3017 2.7003 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6279 1.2559 1.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3735 0.4820 -0.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5047 0.0353 -1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0156 -0.4754 -2.6475 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9894 -1.9223 -4.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5583 -1.0286 -3.2471 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6918 0.2772 1.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0402 -0.6632 1.8374 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3950 -3.1792 1.8995 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8404 -3.2181 0.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0382 -2.7420 1.3950 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2093 -0.6664 -0.2674 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2798 -2.0803 -1.6120 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6071 1.4807 -0.0839 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6575 0.8115 -2.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8241 1.3848 1.4576 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2197 2.0183 -0.8355 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7786 0.1008 0.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2099 0.5321 1.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3023 1.0019 3.2267 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6839 2.8921 2.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7237 2.4371 4.3552 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9225 1.0791 4.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5679 2.2938 5.2120 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9447 0.2821 3.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1888 2.4254 2.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7031 0.8345 -2.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9225 2.4645 -0.4587 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9097 1.3200 -1.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5194 0.2821 0.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6758 -0.7933 -1.7320 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0761 -2.3612 -0.0563 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 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 20 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 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 23 35 1 0 35 36 2 0 36 37 1 0 14 38 1 0 38 39 2 0 9 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 4 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 2 1 0 44 7 1 0 39 11 1 0 37 15 1 0 36 19 1 0 33 25 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 6 4 56 1 6 6 57 1 0 6 58 1 0 7 59 1 1 9 60 1 6 12 61 1 0 13 62 1 0 16 63 1 0 21 64 1 0 22 65 1 0 25 66 1 1 27 67 1 1 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 1 30 72 1 0 31 73 1 1 32 74 1 0 33 75 1 1 34 76 1 0 35 77 1 0 38 78 1 0 39 79 1 0 40 80 1 6 41 81 1 0 42 82 1 1 43 83 1 0 44 84 1 1 45 85 1 0 46 86 1 6 47 87 1 0 48 88 1 6 49 89 1 0 50 90 1 6 51 91 1 0 M END

Standard InCHIKey	NFAJQBFPJPNCER-YMPHNIROSA-N
Standard InCHI	InChI=1S/C33H40O18/c1-11-22(36)25(39)28(42)31(46-11)45-10-20-24(38)27(41)30(44)33(51-20)48-14-5-3-13(4-6-14)18-9-17(35)21-16(34)7-15(8-19(21)50-18)49-32-29(43)26(40)23(37)12(2)47-32/h3-9,11-12,20,22-34,36-44H,10H2,1-2H3/t11-,12+,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=C(C4=CC(=O)C5=C(O)C=C(O[C@@H]6O[C@H](C)[C@H](O)[C@H](O)[C@@H]6O)C=C5O4)C=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:	724.22	Volume:	665.118 ? Van der Waals volume.
Dense:	1.089	LogP:	1.166 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.543 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.421 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	36.0
TPSA:	287.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.114	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.214	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:	0.657	Fluc inhibitor:	0.522 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.959 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.526 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.189	Promiscuous compounds:	0.352

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.59	MDCK Permeability:	-5.059
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
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):	0.877
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.541
Plasma Protein Binding (PPB):	84.495%	Volume Distribution (VD):	-0.07
Fu:	13.075% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.228
OATP1B3 inhibitor:	0.64	BCRP inhibitor:	0.001
BSEP inhibitor:	0.004

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:	0.753
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.863
HLM stability:	0.024 ? 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):

0.829

Half-life (T1/2):

4.97

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.185
Human Hepatotoxicity (H-HT):	0.435	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.99	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.06	Skin Sensitization:	0.999
Carcinogencity:	0.033	Eye Corrosion:	0.0
Eye Irritation:	0.055	Respiratory Toxicity:	0.106
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.987
Hematotoxicity:	0.778	Drug-induced Nephrotoxicity:	0.944
Genotoxicity:	0.726	RPMI-8226 Immunitoxicity:	0.444
A549 Cytotoxicity:	0.955	Hek293 Cytotoxicity:	0.716
BCF:	0.295 ? 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:	3.111 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.615 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.713 ? 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
NPO56355	Sesbania rostrata	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 NPC528069 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	18061
0.1-0.2	27668
0.2-0.3	3152
0.3-0.4	557
0.4-0.5	269
0.5-0.6	95
0.6-0.7	39
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC22062
0.9359	High Similarity	NPC473634
0.9359	High Similarity	NPC138811
0.875	High Similarity	NPC44931
0.8452	Intermediate Similarity	NPC209296
0.8415	Intermediate Similarity	NPC210073
0.7882	Intermediate Similarity	NPC204693
0.7816	Intermediate Similarity	NPC473623
0.7727	Intermediate Similarity	NPC488089
0.75	Intermediate Similarity	NPC11468
0.7363	Intermediate Similarity	NPC101636
0.725	Intermediate Similarity	NPC331652
0.7083	Intermediate Similarity	NPC473644
0.7079	Intermediate Similarity	NPC186816
0.7045	Intermediate Similarity	NPC67105
0.701	Intermediate Similarity	NPC311850
0.7	Intermediate Similarity	NPC46202
0.6951	Remote Similarity	NPC19709
0.6854	Remote Similarity	NPC227508
0.6829	Remote Similarity	NPC473043
0.6809	Remote Similarity	NPC298171
0.68	Remote Similarity	NPC68592
0.6786	Remote Similarity	NPC181712
0.6739	Remote Similarity	NPC65711
0.6702	Remote Similarity	NPC475382
0.6667	Remote Similarity	NPC95090
0.6667	Remote Similarity	NPC27408
0.663	Remote Similarity	NPC64051
0.6571	Remote Similarity	NPC262222
0.6569	Remote Similarity	NPC298666
0.6556	Remote Similarity	NPC187379
0.6517	Remote Similarity	NPC211594
0.6489	Remote Similarity	NPC483707
0.6489	Remote Similarity	NPC229409
0.6471	Remote Similarity	NPC488086
0.6452	Remote Similarity	NPC475366
0.6436	Remote Similarity	NPC488087
0.6421	Remote Similarity	NPC270675
0.6421	Remote Similarity	NPC195685
0.6413	Remote Similarity	NPC303913
0.6408	Remote Similarity	NPC198199
0.6322	Remote Similarity	NPC27942
0.6275	Remote Similarity	NPC488083
0.6237	Remote Similarity	NPC65003
0.6226	Remote Similarity	NPC120952
0.6224	Remote Similarity	NPC472994
0.6224	Remote Similarity	NPC135358
0.6222	Remote Similarity	NPC190003
0.6163	Remote Similarity	NPC39360
0.6163	Remote Similarity	NPC29763
0.6163	Remote Similarity	NPC210003
0.6022	Remote Similarity	NPC295613
0.6022	Remote Similarity	NPC473657
0.6	Remote Similarity	NPC22832
0.6	Remote Similarity	NPC243930
0.6	Remote Similarity	NPC115674
0.598	Remote Similarity	NPC472993
0.5957	Remote Similarity	NPC275454
0.5934	Remote Similarity	NPC607707
0.5922	Remote Similarity	NPC480441
0.5922	Remote Similarity	NPC25523
0.5909	Remote Similarity	NPC189142
0.5909	Remote Similarity	NPC77660
0.5806	Remote Similarity	NPC172807
0.5795	Remote Similarity	NPC261866
0.5795	Remote Similarity	NPC108831
0.5795	Remote Similarity	NPC238376
0.5795	Remote Similarity	NPC182634
0.5758	Remote Similarity	NPC142142
0.5755	Remote Similarity	NPC488088
0.5729	Remote Similarity	NPC473512
0.5729	Remote Similarity	NPC129827
0.5714	Remote Similarity	NPC611303
0.57	Remote Similarity	NPC195257
0.57	Remote Similarity	NPC477629
0.5682	Remote Similarity	NPC160515
0.5657	Remote Similarity	NPC473327
0.5652	Remote Similarity	NPC80188
0.5652	Remote Similarity	NPC601144
0.5625	Remote Similarity	NPC173582
0.5625	Remote Similarity	NPC265885
0.5625	Remote Similarity	NPC181465
0.5625	Remote Similarity	NPC215710
0.5625	Remote Similarity	NPC473438
0.5625	Remote Similarity	NPC253788
0.5618	Remote Similarity	NPC58053
0.5618	Remote Similarity	NPC249281
0.5618	Remote Similarity	NPC143851
0.56	Remote Similarity	NPC479766
0.5591	Remote Similarity	NPC311830
0.5591	Remote Similarity	NPC220169
0.5579	Remote Similarity	NPC254540
0.5567	Remote Similarity	NPC203259
0.5567	Remote Similarity	NPC479405
0.5567	Remote Similarity	NPC33054
0.5567	Remote Similarity	NPC176740
0.5567	Remote Similarity	NPC471725
0.5567	Remote Similarity	NPC134532
0.5567	Remote Similarity	NPC602582
0.5556	Remote Similarity	NPC470443
0.5545	Remote Similarity	NPC479765
0.5532	Remote Similarity	NPC276377
0.551	Remote Similarity	NPC479404
0.5495	Remote Similarity	NPC186807
0.5495	Remote Similarity	NPC46420
0.5495	Remote Similarity	NPC271692
0.5484	Remote Similarity	NPC608742
0.5464	Remote Similarity	NPC39834
0.5455	Remote Similarity	NPC284277
0.5455	Remote Similarity	NPC475497
0.5444	Remote Similarity	NPC289667
0.5426	Remote Similarity	NPC99957
0.5417	Remote Similarity	NPC8856
0.5417	Remote Similarity	NPC251417
0.5408	Remote Similarity	NPC65563
0.5408	Remote Similarity	NPC470949
0.54	Remote Similarity	NPC479403
0.5392	Remote Similarity	NPC473073
0.5385	Remote Similarity	NPC158674
0.5385	Remote Similarity	NPC29353
0.5354	Remote Similarity	NPC473571
0.5354	Remote Similarity	NPC110941
0.5347	Remote Similarity	NPC32641
0.5347	Remote Similarity	NPC256188
0.534	Remote Similarity	NPC287889
0.5319	Remote Similarity	NPC181616
0.53	Remote Similarity	NPC126784
0.53	Remote Similarity	NPC241423
0.5263	Remote Similarity	NPC116458
0.5263	Remote Similarity	NPC246943
0.5263	Remote Similarity	NPC605784
0.5253	Remote Similarity	NPC475155
0.5253	Remote Similarity	NPC150164
0.5243	Remote Similarity	NPC80068
0.5243	Remote Similarity	NPC476472
0.5243	Remote Similarity	NPC294815
0.5243	Remote Similarity	NPC16194
0.5238	Remote Similarity	NPC244875
0.5238	Remote Similarity	NPC14187
0.52	Remote Similarity	NPC257566
0.5196	Remote Similarity	NPC72016
0.5196	Remote Similarity	NPC35119
0.5196	Remote Similarity	NPC606657
0.5152	Remote Similarity	NPC15358
0.5143	Remote Similarity	NPC179862
0.5138	Remote Similarity	NPC277532
0.5109	Remote Similarity	NPC348541
0.5102	Remote Similarity	NPC487212
0.5053	Remote Similarity	NPC282169
0.5053	Remote Similarity	NPC285197
0.505	Remote Similarity	NPC122809

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC528069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4715
0.1-0.2	4342
0.2-0.3	82
0.3-0.4	4
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
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	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD7054	Phase 4
0.6429	Remote Similarity	NPD7808	Phase 3
0.6354	Remote Similarity	NPD7251	Phase 2
0.6263	Remote Similarity	NPD7472	Pre-clinical
0.5567	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