NPASS Compound

Natural Product: NPC470713

Natural Product ID	NPC470713
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Allivictoside B
IUPAC Name	[(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-4-oxo-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms	Allivictoside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2206198
PubChem CID	71455938
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 94 99 0 0 0 0 0 0 0 0999 V2000 7.2819 3.7445 2.6527 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9000 4.8052 1.8285 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9622 4.6275 0.8299 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6310 5.7192 0.0534 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7002 5.5773 -0.9501 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1008 4.3328 -1.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4179 3.2395 -0.4110 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3509 3.4083 0.5849 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8000 1.9585 -0.6485 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9079 1.7174 -1.5836 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3421 0.3867 -1.7421 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4749 0.1410 -2.6484 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6890 -0.6925 -0.9439 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1200 -1.9745 -1.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1675 -2.9601 -1.6559 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3069 -2.9435 -0.6770 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6971 -2.7546 0.6978 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4341 -3.3321 0.7598 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4867 -2.5276 0.0709 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3953 -3.4430 -0.1484 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5579 -3.6201 0.8285 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7166 -2.9349 0.8882 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5592 -3.2042 1.9185 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3373 -4.0634 2.8381 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2965 -4.2297 3.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0433 -5.1605 4.8175 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8858 -5.9022 4.8256 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9211 -5.7427 3.8365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1815 -4.8120 2.8565 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2907 -4.5769 1.8339 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7883 -5.1878 1.7391 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2480 -6.4553 3.7978 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0132 -5.3179 5.8089 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1202 -1.9308 -0.0723 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5811 -1.6645 -1.2928 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0045 -0.6497 -2.1284 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0414 0.1775 -1.7471 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6129 -0.0633 -0.5174 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1714 -1.0833 0.2995 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4498 1.1877 -2.6016 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4272 2.1439 -2.4057 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9115 3.5635 -2.6532 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9083 4.4458 -1.8872 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2912 4.1592 -2.3802 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5697 2.7552 -2.7762 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5309 2.0053 -3.2387 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3526 1.9564 -1.7556 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4146 2.7039 -1.2610 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1749 4.5155 -1.3378 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7472 4.0830 -0.5429 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6270 3.7573 -2.2149 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5836 -3.4822 1.6809 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6808 -4.8365 1.3696 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2878 -2.0276 -0.9119 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6429 -2.5325 -2.8979 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2013 6.9732 0.2393 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5691 2.8512 2.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4351 3.4757 3.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1700 4.0420 3.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4230 6.4210 -1.5751 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3783 4.2902 -1.9747 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6393 2.5724 1.2178 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1126 1.1291 0.0164 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 2.4894 -2.2435 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4089 -1.8670 -1.9755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7024 -3.9438 -1.8011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7912 -3.9509 -0.6633 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6008 -1.7203 1.0177 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2254 -1.7662 0.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2032 -3.6356 3.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7310 -6.6174 5.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2174 -7.4057 4.1856 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6539 -6.0937 5.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7978 -2.2924 -1.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5133 -0.5007 -3.1006 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4405 0.5696 -0.1796 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6641 -1.2124 1.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7861 2.1122 -1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0558 3.8412 -3.7176 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6275 5.4949 -2.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5386 4.8976 -3.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2887 2.8399 -3.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6906 1.6329 -0.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8422 1.0808 -2.2771 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6359 2.4963 -0.3175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9374 5.0358 -1.6461 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6055 3.9569 -0.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4684 4.7418 -2.2028 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2084 -3.3204 2.7306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6178 -3.0516 1.6319 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6121 -5.0660 1.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2053 -2.3500 -0.7166 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6253 -2.4042 -2.9177 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0963 7.2481 -0.1059 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 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 3 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 28 32 1 0 26 33 1 0 22 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 44 49 1 0 43 50 1 0 42 51 1 0 17 52 1 0 52 53 1 0 16 54 1 0 15 55 1 0 4 56 1 0 8 3 1 0 19 14 1 0 30 21 1 0 29 24 1 0 39 34 1 0 46 41 1 0 1 57 1 0 1 58 1 0 1 59 1 0 5 60 1 0 6 61 1 0 8 62 1 0 9 63 1 0 10 64 1 0 14 65 1 0 15 66 1 0 16 67 1 0 17 68 1 0 19 69 1 0 25 70 1 0 27 71 1 0 32 72 1 0 33 73 1 0 35 74 1 0 36 75 1 0 38 76 1 0 39 77 1 0 41 78 1 0 42 79 1 0 43 80 1 0 44 81 1 0 45 82 1 0 47 83 1 0 47 84 1 0 48 85 1 0 49 86 1 0 50 87 1 0 51 88 1 0 52 89 1 0 52 90 1 0 53 91 1 0 54 92 1 0 55 93 1 0 56 94 1 0 M END

Standard InCHIKey	KRHUTRQVXQQDBB-FOPGHQQOSA-N
Standard InCHI	InChI=1S/C37H38O19/c1-50-21-10-15(2-8-19(21)41)3-9-25(43)55-35-31(48)28(45)24(14-39)54-37(35)56-34-29(46)26-20(42)11-17(40)12-22(26)52-33(34)16-4-6-18(7-5-16)51-36-32(49)30(47)27(44)23(13-38)53-36/h2-12,23-24,27-28,30-32,35-42,44-45,47-49H,13-14H2,1H3/b9-3+/t23-,24-,27-,28-,30+,31+,32-,35-,36-,37+/m1/s1
SMILES	COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)OC6C(C(C(C(O6)CO)O)O)O)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	786.2	Volume:	729.91 ? Van der Waals volume.
Dense:	1.077	LogP:	0.366 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.005 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.827 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	38.0
TPSA:	304.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.066	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.038	Fsp³:	0.351
MCE-18:	139.4 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.643	Fluc inhibitor:	0.365 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.842 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.962 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.349	Promiscuous compounds:	0.604

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.37	MDCK Permeability:	-5.157
Pgp-inhibitor:	0.0	Pgp-substrate:	0.884
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%):	0.948	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.91
Plasma Protein Binding (PPB):	80.345%	Volume Distribution (VD):	-0.134
Fu:	17.054% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.857
BSEP inhibitor:	0.032

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.511	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:	0.996
HLM stability:	0.002 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.331

Half-life (T1/2):

3.633

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.316
Human Hepatotoxicity (H-HT):	0.562	Drug-induced Liver Injury (DILI):	0.844
AMES Toxicity:	0.844	Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.528	Skin Sensitization:	0.788
Carcinogencity:	0.147	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.025
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.979
Hematotoxicity:	0.008	Drug-induced Nephrotoxicity:	0.089
Genotoxicity:	0.657	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.276	Hek293 Cytotoxicity:	0.953
BCF:	0.567 ? 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:	3.367 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.285 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.299 ? 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
NPO3860.1	Allium victorialis	Under-species	n.a.	n.a.	Leaves	Taeback, GangWon province, Korea	2011-Jan	PMID[23149227]

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

Activity Type	# Activity
Activity	1
IC50	1

Activity Type	# Activity
Cell line	2

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
NPT34	Cell line	BV-2	Mus musculus	Activity	=	107.1	%	PubChem BioAssay data set
NPT34	Cell line	BV-2	Mus musculus	IC50	=	20670.0	nM	PMID[10650083]

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 NPC470713 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	17982
0.1-0.2	27390
0.2-0.3	3224
0.3-0.4	798
0.4-0.5	276
0.5-0.6	133
0.6-0.7	40
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8866	High Similarity	NPC470712
0.8515	High Similarity	NPC295625
0.8173	Intermediate Similarity	NPC470717
0.8137	Intermediate Similarity	NPC470718
0.8095	Intermediate Similarity	NPC470720
0.783	Intermediate Similarity	NPC470719
0.7596	Intermediate Similarity	NPC470715
0.7321	Intermediate Similarity	NPC25946
0.7264	Intermediate Similarity	NPC164704
0.7105	Intermediate Similarity	NPC21359
0.7105	Intermediate Similarity	NPC460984
0.6771	Remote Similarity	NPC472459
0.6762	Remote Similarity	NPC76831
0.6737	Remote Similarity	NPC64305
0.6635	Remote Similarity	NPC477628
0.6481	Remote Similarity	NPC483767
0.6481	Remote Similarity	NPC483769
0.6481	Remote Similarity	NPC483768
0.6481	Remote Similarity	NPC483766
0.6465	Remote Similarity	NPC120099
0.6337	Remote Similarity	NPC203050
0.6337	Remote Similarity	NPC225434
0.633	Remote Similarity	NPC218161
0.63	Remote Similarity	NPC224530
0.63	Remote Similarity	NPC609478
0.625	Remote Similarity	NPC219043
0.625	Remote Similarity	NPC48984
0.6228	Remote Similarity	NPC470716
0.62	Remote Similarity	NPC60735
0.62	Remote Similarity	NPC26230
0.6176	Remote Similarity	NPC170052
0.6176	Remote Similarity	NPC135846
0.6126	Remote Similarity	NPC483765
0.6122	Remote Similarity	NPC77672
0.6122	Remote Similarity	NPC133671
0.6122	Remote Similarity	NPC135391
0.6122	Remote Similarity	NPC78263
0.6122	Remote Similarity	NPC250069
0.6116	Remote Similarity	NPC480470
0.608	Remote Similarity	NPC249560
0.6075	Remote Similarity	NPC64425
0.6055	Remote Similarity	NPC205824
0.6055	Remote Similarity	NPC221288
0.6055	Remote Similarity	NPC194836
0.6055	Remote Similarity	NPC91493
0.6055	Remote Similarity	NPC605081
0.6053	Remote Similarity	NPC217520
0.6017	Remote Similarity	NPC162394
0.6	Remote Similarity	NPC85751
0.6	Remote Similarity	NPC19240
0.6	Remote Similarity	NPC220173
0.5983	Remote Similarity	NPC474093
0.5983	Remote Similarity	NPC104910
0.5966	Remote Similarity	NPC488078
0.5965	Remote Similarity	NPC477895
0.5963	Remote Similarity	NPC104883
0.5963	Remote Similarity	NPC488679
0.5962	Remote Similarity	NPC254855
0.5962	Remote Similarity	NPC94610
0.595	Remote Similarity	NPC480472
0.5948	Remote Similarity	NPC139571
0.5941	Remote Similarity	NPC325555
0.5941	Remote Similarity	NPC226304
0.59	Remote Similarity	NPC145038
0.59	Remote Similarity	NPC56077
0.59	Remote Similarity	NPC281131
0.59	Remote Similarity	NPC253662
0.59	Remote Similarity	NPC179950
0.59	Remote Similarity	NPC88789
0.59	Remote Similarity	NPC491374
0.5877	Remote Similarity	NPC470416
0.5841	Remote Similarity	NPC214621
0.5841	Remote Similarity	NPC34267
0.5833	Remote Similarity	NPC488079
0.5794	Remote Similarity	NPC163242
0.5794	Remote Similarity	NPC272068
0.5769	Remote Similarity	NPC487501
0.5752	Remote Similarity	NPC223426
0.5741	Remote Similarity	NPC304741
0.5702	Remote Similarity	NPC81042
0.5644	Remote Similarity	NPC19388
0.5644	Remote Similarity	NPC240431
0.5644	Remote Similarity	NPC55786
0.5636	Remote Similarity	NPC61904
0.5635	Remote Similarity	NPC473554
0.5625	Remote Similarity	NPC101399
0.5625	Remote Similarity	NPC217822
0.5625	Remote Similarity	NPC11847
0.5625	Remote Similarity	NPC198938
0.5596	Remote Similarity	NPC155877
0.5577	Remote Similarity	NPC219904
0.5545	Remote Similarity	NPC255157
0.5545	Remote Similarity	NPC259896
0.5526	Remote Similarity	NPC260504
0.5526	Remote Similarity	NPC89809
0.5505	Remote Similarity	NPC470405
0.55	Remote Similarity	NPC288084
0.5495	Remote Similarity	NPC253521
0.5495	Remote Similarity	NPC113836
0.549	Remote Similarity	NPC289667
0.549	Remote Similarity	NPC143851
0.5484	Remote Similarity	NPC192539
0.5481	Remote Similarity	NPC216496
0.5472	Remote Similarity	NPC223747
0.5439	Remote Similarity	NPC477629
0.5429	Remote Similarity	NPC175107
0.5424	Remote Similarity	NPC173837
0.5414	Remote Similarity	NPC475179
0.5391	Remote Similarity	NPC292929
0.5391	Remote Similarity	NPC231787
0.5385	Remote Similarity	NPC488080
0.5385	Remote Similarity	NPC169977
0.5366	Remote Similarity	NPC156785
0.5366	Remote Similarity	NPC474522
0.5357	Remote Similarity	NPC470125
0.5357	Remote Similarity	NPC472992
0.5357	Remote Similarity	NPC153755
0.5351	Remote Similarity	NPC472991
0.5345	Remote Similarity	NPC602448
0.5333	Remote Similarity	NPC21100
0.5327	Remote Similarity	NPC136761
0.5315	Remote Similarity	NPC156869
0.5308	Remote Similarity	NPC223860
0.5299	Remote Similarity	NPC96605
0.5299	Remote Similarity	NPC280642
0.5294	Remote Similarity	NPC67037
0.5294	Remote Similarity	NPC255615
0.5283	Remote Similarity	NPC191306
0.5273	Remote Similarity	NPC139320
0.5263	Remote Similarity	NPC35119
0.5259	Remote Similarity	NPC36138
0.5243	Remote Similarity	NPC111929
0.5243	Remote Similarity	NPC320283
0.5243	Remote Similarity	NPC41121
0.5234	Remote Similarity	NPC101026
0.5234	Remote Similarity	NPC488077
0.5224	Remote Similarity	NPC487500
0.5191	Remote Similarity	NPC30011
0.5191	Remote Similarity	NPC72554
0.5189	Remote Similarity	NPC42773
0.5189	Remote Similarity	NPC45522
0.5185	Remote Similarity	NPC206123
0.5185	Remote Similarity	NPC309025
0.5182	Remote Similarity	NPC473682
0.5169	Remote Similarity	NPC478277
0.5169	Remote Similarity	NPC478276
0.5169	Remote Similarity	NPC478275
0.5169	Remote Similarity	NPC92815
0.5159	Remote Similarity	NPC241781
0.5145	Remote Similarity	NPC33083
0.5143	Remote Similarity	NPC297987
0.5143	Remote Similarity	NPC265530
0.5138	Remote Similarity	NPC476215
0.5135	Remote Similarity	NPC29958
0.5133	Remote Similarity	NPC129264
0.5133	Remote Similarity	NPC470444
0.513	Remote Similarity	NPC32641
0.513	Remote Similarity	NPC256188
0.513	Remote Similarity	NPC473327
0.5126	Remote Similarity	NPC89052
0.5094	Remote Similarity	NPC24043
0.5093	Remote Similarity	NPC21666
0.5093	Remote Similarity	NPC197285
0.5093	Remote Similarity	NPC601710
0.5089	Remote Similarity	NPC471748
0.5088	Remote Similarity	NPC240306
0.5049	Remote Similarity	NPC34531
0.5048	Remote Similarity	NPC127546
0.5048	Remote Similarity	NPC57625
0.5048	Remote Similarity	NPC173637
0.5048	Remote Similarity	NPC317489
0.5048	Remote Similarity	NPC223424
0.5048	Remote Similarity	NPC600591
0.5046	Remote Similarity	NPC88023
0.5046	Remote Similarity	NPC478887
0.5043	Remote Similarity	NPC476472
0.5043	Remote Similarity	NPC294815
0.5043	Remote Similarity	NPC16194
0.5043	Remote Similarity	NPC89127
0.5041	Remote Similarity	NPC480796
0.5039	Remote Similarity	NPC199172
0.5038	Remote Similarity	NPC275977
0.5038	Remote Similarity	NPC487502
0.5037	Remote Similarity	NPC97817

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4871
0.1-0.2	4224
0.2-0.3	46
0.3-0.4	7
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
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
		NPD

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