NPASS Compound

Natural Product: NPC21359

Natural Product ID	NPC21359
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Quercetin 3-O-[2-O-(6-O-E-Feruloyl)-Beta-D-Glucopyranosyl]-Beta-D-Galactopyranoside
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5R,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500570
PubChem CID	10463057
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 95100 0 0 0 0 0 0 0 0999 V2000 -5.2113 4.2708 1.3230 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5458 3.9636 2.5241 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3605 2.4640 2.5539 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6030 2.1141 1.4409 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2939 0.7393 1.5006 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0061 0.1409 0.2916 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8778 -0.7778 -0.3023 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7821 -0.4317 -1.2575 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6125 -1.3683 -1.7772 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6110 -2.6066 -1.4283 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7112 -3.0045 -0.4698 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8294 -2.1205 0.1157 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0352 -2.5043 0.9698 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6506 -4.3166 -0.0443 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7222 -4.7040 0.9380 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5119 -5.2422 -0.5946 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4122 -4.8419 -1.5541 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4790 -3.5380 -1.9833 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2787 -5.8046 -2.0987 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9394 0.8936 -1.7873 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0264 1.8786 -1.6425 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2662 3.1669 -2.1549 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4362 3.4640 -2.8199 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3788 2.4673 -2.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1065 1.2198 -2.4606 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5695 2.7254 -3.6409 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7271 4.7089 -3.3434 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2369 0.6523 2.5745 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9787 0.8015 3.8838 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7693 2.0674 3.8505 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0042 3.1042 4.4037 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1345 0.8351 4.9883 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4369 -0.4465 2.4770 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0964 -0.1958 2.2985 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3332 -0.6264 1.0128 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5909 -0.1519 0.7790 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3985 -1.0903 -0.1317 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6811 -0.4573 -0.2493 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7156 -0.9640 -0.9831 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5681 -2.0458 -1.6071 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0306 -0.3057 -1.0923 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0066 -0.8145 -1.8040 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3174 -0.1992 -1.9376 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6119 0.9789 -1.3012 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8886 1.5384 -1.4544 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8628 0.9468 -2.2235 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5610 -0.2354 -2.8597 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3123 -0.7950 -2.7177 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5571 -0.8269 -3.6378 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3812 -2.0401 -4.3412 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1313 1.5164 -2.3666 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3980 0.2779 1.9446 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1278 -0.4823 3.2132 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7174 -1.0235 3.2652 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2125 -1.0830 4.5384 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0478 -1.5009 3.4314 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3679 1.6596 2.1808 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9322 5.1600 0.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5383 4.4177 2.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1090 4.3464 3.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3970 2.0303 2.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2091 0.2069 1.9146 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8574 -5.1232 0.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4893 -6.2893 -0.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1785 -3.1980 -2.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6740 -6.4477 -1.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0713 1.7701 -1.1730 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5530 3.9694 -2.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8858 0.4739 -2.6145 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4751 2.5439 -3.2703 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4364 5.3062 -2.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5809 1.5607 2.4654 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6709 -0.0923 3.9362 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6365 1.9180 4.5635 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3158 3.3522 5.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4381 1.5230 4.7641 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1579 0.8784 2.3037 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4579 0.7687 0.1298 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 -2.0603 0.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8907 -1.2038 -1.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1783 0.6162 -0.5675 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8230 -1.7630 -2.3303 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9276 1.5213 -0.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1100 2.4726 -0.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0759 -1.7349 -3.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7671 -2.7366 -3.7600 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3996 -2.4330 -4.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9127 -1.8453 -5.3436 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6962 1.6989 -1.5596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4798 0.0532 1.6998 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2351 0.2271 4.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7860 -2.0597 2.8118 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4654 -1.8302 4.5469 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0785 -2.1598 2.6939 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2030 2.1121 1.9494 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 2 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 11 14 1 0 14 15 1 0 14 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 8 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 5 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 47 49 1 0 49 50 1 0 46 51 1 0 36 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 30 3 1 0 54 34 1 0 12 7 1 0 25 20 1 0 48 43 1 0 18 10 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 6 5 62 1 1 15 63 1 0 16 64 1 0 18 65 1 0 19 66 1 0 21 67 1 0 22 68 1 0 25 69 1 0 26 70 1 0 27 71 1 0 28 72 1 6 29 73 1 1 30 74 1 1 31 75 1 0 32 76 1 0 34 77 1 1 36 78 1 6 37 79 1 0 37 80 1 0 41 81 1 0 42 82 1 0 44 83 1 0 45 84 1 0 48 85 1 0 50 86 1 0 50 87 1 0 50 88 1 0 51 89 1 0 52 90 1 6 53 91 1 1 54 92 1 6 55 93 1 0 56 94 1 0 57 95 1 0 M END

Standard InCHIKey	HUHCPMKLCPDUEY-XLXDBILHSA-N
Standard InCHI	InChI=1S/C37H38O20/c1-51-21-8-14(2-5-18(21)41)3-7-25(44)52-13-24-28(46)30(48)32(50)36(55-24)57-35-31(49)27(45)23(12-38)54-37(35)56-34-29(47)26-20(43)10-16(39)11-22(26)53-33(34)15-4-6-17(40)19(42)9-15/h2-11,23-24,27-28,30-32,35-43,45-46,48-50H,12-13H2,1H3/b7-3+/t23-,24-,27+,28-,30+,31+,32-,35-,36+,37+/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@H]1O)O)O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	802.2	Volume:	738.7 ? Van der Waals volume.
Dense:	1.086	LogP:	0.815 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.124 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.454 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	38.0
TPSA:	325.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.051	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.125	Fsp³:	0.351
MCE-18:	142.8 ? 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:	1
Colloidal aggregators:	0.722	Fluc inhibitor:	0.499 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.852 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.166	Promiscuous compounds:	0.574

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.44	MDCK Permeability:	-5.309
Pgp-inhibitor:	0.0	Pgp-substrate:	0.043
PAMPA:	0.985 ? 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):	0.992
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.036
Plasma Protein Binding (PPB):	86.317%	Volume Distribution (VD):	-0.199
Fu:	11.086% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.345
BSEP inhibitor:	0.001

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:	0.001	CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.103
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.779 ? 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):

1.459

Half-life (T1/2):

4.281

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.188
Human Hepatotoxicity (H-HT):	0.486	Drug-induced Liver Injury (DILI):	0.974
AMES Toxicity:	0.95	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.111	Skin Sensitization:	1.0
Carcinogencity:	0.099	Eye Corrosion:	0.0
Eye Irritation:	0.343	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.933
Hematotoxicity:	0.035	Drug-induced Nephrotoxicity:	0.53
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.139
A549 Cytotoxicity:	0.977	Hek293 Cytotoxicity:	0.852
BCF:	0.584 ? 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:	3.347 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.898 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.241 ? 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
NPO32921	hedyotis diffusa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170670]
NPO32921	hedyotis diffusa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20004577]

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	3

Activity Type	# Activity
Others	3

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
NPT2	Others	Unspecified	n.a.	Activity	=	62.7	%	PMID[17346076]
NPT2	Others	Unspecified	n.a.	Activity	=	72.9	%	PMID[15261272]
NPT2	Others	Unspecified	n.a.	Activity	=	75.0	%	PMID[8627602]

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 NPC21359 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	19007
0.1-0.2	26010
0.2-0.3	3765
0.3-0.4	658
0.4-0.5	213
0.5-0.6	132
0.6-0.7	55
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC460984
0.9327	High Similarity	NPC25946
0.7377	Intermediate Similarity	NPC487501
0.7288	Intermediate Similarity	NPC473554
0.7105	Intermediate Similarity	NPC470713
0.6972	Remote Similarity	NPC223426
0.6961	Remote Similarity	NPC254855
0.6961	Remote Similarity	NPC94610
0.6909	Remote Similarity	NPC81042
0.6746	Remote Similarity	NPC487500
0.6698	Remote Similarity	NPC155877
0.6696	Remote Similarity	NPC139571
0.6695	Remote Similarity	NPC488078
0.6667	Remote Similarity	NPC217520
0.6667	Remote Similarity	NPC480472
0.664	Remote Similarity	NPC249560
0.6636	Remote Similarity	NPC255157
0.6636	Remote Similarity	NPC259896
0.661	Remote Similarity	NPC162394
0.656	Remote Similarity	NPC487502
0.6518	Remote Similarity	NPC218161
0.6486	Remote Similarity	NPC85751
0.6486	Remote Similarity	NPC19240
0.6486	Remote Similarity	NPC220173
0.6471	Remote Similarity	NPC488740
0.6471	Remote Similarity	NPC488736
0.6471	Remote Similarity	NPC488733
0.646	Remote Similarity	NPC214621
0.646	Remote Similarity	NPC34267
0.6435	Remote Similarity	NPC477895
0.641	Remote Similarity	NPC470718
0.6381	Remote Similarity	NPC170052
0.6381	Remote Similarity	NPC135846
0.6364	Remote Similarity	NPC488737
0.6348	Remote Similarity	NPC470416
0.6306	Remote Similarity	NPC122467
0.629	Remote Similarity	NPC480470
0.6239	Remote Similarity	NPC470712
0.6198	Remote Similarity	NPC470717
0.6167	Remote Similarity	NPC474093
0.6167	Remote Similarity	NPC104910
0.6148	Remote Similarity	NPC480444
0.6148	Remote Similarity	NPC470720
0.6147	Remote Similarity	NPC163242
0.6147	Remote Similarity	NPC272068
0.6121	Remote Similarity	NPC89052
0.6091	Remote Similarity	NPC304741
0.6091	Remote Similarity	NPC156869
0.6087	Remote Similarity	NPC602448
0.6066	Remote Similarity	NPC470719
0.6033	Remote Similarity	NPC488734
0.6033	Remote Similarity	NPC295625
0.6033	Remote Similarity	NPC488735
0.6033	Remote Similarity	NPC488739
0.6033	Remote Similarity	NPC488732
0.6033	Remote Similarity	NPC488738
0.6019	Remote Similarity	NPC95866
0.6017	Remote Similarity	NPC219043
0.6016	Remote Similarity	NPC488079
0.6	Remote Similarity	NPC292929
0.5982	Remote Similarity	NPC253521
0.5982	Remote Similarity	NPC113836
0.5969	Remote Similarity	NPC30011
0.5913	Remote Similarity	NPC471669
0.5913	Remote Similarity	NPC89127
0.5882	Remote Similarity	NPC48984
0.5872	Remote Similarity	NPC116864
0.5872	Remote Similarity	NPC244776
0.5856	Remote Similarity	NPC470405
0.5846	Remote Similarity	NPC72554
0.5833	Remote Similarity	NPC303694
0.5789	Remote Similarity	NPC12013
0.5789	Remote Similarity	NPC11432
0.5789	Remote Similarity	NPC477613
0.5776	Remote Similarity	NPC76831
0.5766	Remote Similarity	NPC33083
0.575	Remote Similarity	NPC173837
0.5726	Remote Similarity	NPC480445
0.5726	Remote Similarity	NPC36138
0.5714	Remote Similarity	NPC241781
0.5702	Remote Similarity	NPC153755
0.5692	Remote Similarity	NPC275977
0.568	Remote Similarity	NPC156785
0.5672	Remote Similarity	NPC97817
0.5669	Remote Similarity	NPC192539
0.5667	Remote Similarity	NPC488075
0.563	Remote Similarity	NPC483765
0.562	Remote Similarity	NPC292019
0.562	Remote Similarity	NPC202908
0.5596	Remote Similarity	NPC224530
0.5588	Remote Similarity	NPC475179
0.5575	Remote Similarity	NPC67326
0.5573	Remote Similarity	NPC231787
0.5565	Remote Similarity	NPC61904
0.5526	Remote Similarity	NPC203259
0.5526	Remote Similarity	NPC33054
0.5526	Remote Similarity	NPC176740
0.5526	Remote Similarity	NPC471725
0.5526	Remote Similarity	NPC134532
0.5526	Remote Similarity	NPC602582
0.5517	Remote Similarity	NPC480471
0.5517	Remote Similarity	NPC488076
0.5514	Remote Similarity	NPC145038
0.5514	Remote Similarity	NPC56077
0.5514	Remote Similarity	NPC281131
0.5514	Remote Similarity	NPC253662
0.5514	Remote Similarity	NPC179950
0.5514	Remote Similarity	NPC88789
0.5514	Remote Similarity	NPC491374
0.5508	Remote Similarity	NPC477629
0.55	Remote Similarity	NPC96605
0.55	Remote Similarity	NPC280642
0.5496	Remote Similarity	NPC487499
0.5495	Remote Similarity	NPC476215
0.5492	Remote Similarity	NPC480796
0.5487	Remote Similarity	NPC29958
0.5478	Remote Similarity	NPC470444
0.547	Remote Similarity	NPC473327
0.5462	Remote Similarity	NPC199172
0.5462	Remote Similarity	NPC221342
0.5462	Remote Similarity	NPC476470
0.5455	Remote Similarity	NPC120099
0.5447	Remote Similarity	NPC164704
0.5439	Remote Similarity	NPC471748
0.5431	Remote Similarity	NPC488073
0.5431	Remote Similarity	NPC240306
0.5424	Remote Similarity	NPC221288
0.5424	Remote Similarity	NPC97119
0.5424	Remote Similarity	NPC194836
0.5424	Remote Similarity	NPC91493
0.5424	Remote Similarity	NPC605081
0.5417	Remote Similarity	NPC483767
0.5417	Remote Similarity	NPC483769
0.5417	Remote Similarity	NPC483768
0.5417	Remote Similarity	NPC483766
0.5378	Remote Similarity	NPC476472
0.5378	Remote Similarity	NPC294815
0.5378	Remote Similarity	NPC16194
0.5366	Remote Similarity	NPC472993
0.5364	Remote Similarity	NPC175107
0.5357	Remote Similarity	NPC203050
0.5357	Remote Similarity	NPC225434
0.5339	Remote Similarity	NPC37668
0.5333	Remote Similarity	NPC260504
0.5333	Remote Similarity	NPC89809
0.5323	Remote Similarity	NPC480441
0.5323	Remote Similarity	NPC470715
0.5315	Remote Similarity	NPC609478
0.5303	Remote Similarity	NPC35924
0.5299	Remote Similarity	NPC470125
0.5268	Remote Similarity	NPC136761
0.5263	Remote Similarity	NPC473682
0.5259	Remote Similarity	NPC223860
0.5254	Remote Similarity	NPC477628
0.5246	Remote Similarity	NPC478277
0.5246	Remote Similarity	NPC478276
0.5246	Remote Similarity	NPC478275
0.5246	Remote Similarity	NPC92815
0.5234	Remote Similarity	NPC67037
0.5234	Remote Similarity	NPC255615
0.5225	Remote Similarity	NPC60735
0.5225	Remote Similarity	NPC26230
0.5217	Remote Similarity	NPC609888
0.5214	Remote Similarity	NPC35167
0.5167	Remote Similarity	NPC205824
0.5161	Remote Similarity	NPC189564
0.5135	Remote Similarity	NPC472459
0.5128	Remote Similarity	NPC605592
0.5124	Remote Similarity	NPC473071
0.5115	Remote Similarity	NPC209550
0.5086	Remote Similarity	NPC471079
0.5085	Remote Similarity	NPC129264
0.5085	Remote Similarity	NPC144097
0.5083	Remote Similarity	NPC104883
0.5083	Remote Similarity	NPC488679
0.5077	Remote Similarity	NPC474522
0.5044	Remote Similarity	NPC226005
0.5043	Remote Similarity	NPC173582
0.5043	Remote Similarity	NPC265885
0.5043	Remote Similarity	NPC181465
0.5043	Remote Similarity	NPC215710
0.5043	Remote Similarity	NPC473438
0.5043	Remote Similarity	NPC253788
0.5042	Remote Similarity	NPC154741
0.5042	Remote Similarity	NPC488074
0.5041	Remote Similarity	NPC101399
0.5041	Remote Similarity	NPC142142
0.5041	Remote Similarity	NPC217822
0.5041	Remote Similarity	NPC11847
0.5041	Remote Similarity	NPC198938
0.5041	Remote Similarity	NPC472991
0.5041	Remote Similarity	NPC603079

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC21359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4936
0.1-0.2	4156
0.2-0.3	48
0.3-0.4	8
0.4-0.5	1
0.5-0.6	1
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
0.5526	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