NPASS Compound

Natural Product: NPC477613

Natural Product ID	NPC477613
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(2S,5R,6R)-4,5-dihydroxy-3-[(2S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
IUPAC Name	3-[(2S,5R,6R)-4,5-dihydroxy-3-[(2S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms	Mauritianin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44391816
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 92 97 0 0 0 0 0 0 0 0999 V2000 -2.4249 4.9439 1.9551 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6819 5.6676 0.8609 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7057 6.2441 -0.0887 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6413 5.5117 -1.4254 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5544 4.0324 -1.0028 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2072 3.7855 -0.4905 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7843 4.8491 0.2883 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0022 2.6914 0.3249 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0522 1.8614 0.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4630 0.4863 -0.2189 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0464 -0.4405 0.7059 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4322 -0.4148 0.4677 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9677 0.7165 1.2739 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1484 1.9379 1.0517 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0390 2.9776 0.6882 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9085 0.3358 2.6287 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0715 -1.7445 0.7234 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4193 -1.6728 0.4857 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0846 -2.8796 0.6943 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7553 -3.3832 -0.5440 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0994 -2.7645 -0.8011 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8247 -2.3499 0.4365 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8551 -1.7217 1.4109 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9556 -2.7468 1.7719 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5507 -1.1581 2.6245 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7971 -1.3929 0.1573 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0126 -1.6465 -1.6472 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7971 -4.7755 -0.5657 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8715 0.3848 -0.1895 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5574 -0.6587 -0.7903 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0305 -1.7133 -0.1065 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6578 -2.6591 -0.8307 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8366 -2.6256 -2.1057 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4959 -3.6384 -2.7958 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6740 -3.5805 -4.1490 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2000 -2.5098 -4.8568 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5387 -1.4883 -4.1849 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3673 -1.5615 -2.8221 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7072 -0.5362 -2.1811 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2656 0.4474 -2.8014 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0549 -0.3990 -4.8938 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3404 -4.6017 -4.8555 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9187 -1.8980 1.3173 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2364 -3.1585 1.8427 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2243 -3.4404 3.1768 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8903 -2.4704 4.0806 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5736 -1.2240 3.6039 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5915 -0.9491 2.2209 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8724 -2.7422 5.4501 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9275 3.3262 -2.1326 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4952 5.9192 -2.0625 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9785 6.1461 0.4037 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5244 5.0451 1.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2170 3.8472 1.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0623 5.2412 2.9701 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2144 6.5581 1.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4507 7.2916 -0.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5774 5.7171 -1.9535 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3144 3.9082 -0.2020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4496 3.7862 -1.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5088 2.2232 -0.9205 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1614 0.0378 -1.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6204 -0.1847 -0.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0452 0.9135 0.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7387 2.2598 2.0318 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8614 3.2581 -0.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7209 -0.1798 2.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6444 -2.4532 -0.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8006 -2.1250 1.7295 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3263 -3.6266 1.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0942 -3.0821 -1.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7183 -3.5142 -1.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2852 -3.2219 0.9661 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2280 -0.9363 0.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5182 -0.7276 2.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8889 -0.3961 3.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6831 -1.9884 3.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5710 -1.5458 0.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5585 -1.9125 -2.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7525 -5.0239 -0.7445 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8704 -4.4779 -2.2541 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3360 -2.4578 -5.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4851 -0.1768 -5.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6072 -5.4186 -4.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5045 -3.9480 1.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4708 -4.4194 3.5699 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3110 -0.4603 4.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3501 0.0461 1.9130 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7942 -3.7328 5.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2184 3.1917 -2.7781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0990 5.2520 -2.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5928 6.1136 -0.3877 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 21 27 1 0 20 28 1 0 10 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 37 41 1 0 35 42 1 0 31 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 46 49 1 0 5 50 1 0 4 51 1 0 3 52 1 0 7 2 1 0 14 9 1 0 24 19 1 0 39 30 1 0 38 33 1 0 48 43 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 1 3 57 1 6 4 58 1 0 5 59 1 0 6 60 1 6 9 61 1 0 10 62 1 6 12 63 1 6 13 64 1 6 14 65 1 0 15 66 1 0 16 67 1 0 17 68 1 0 17 69 1 0 19 70 1 1 20 71 1 0 21 72 1 6 22 73 1 1 23 74 1 0 25 75 1 0 25 76 1 0 25 77 1 0 26 78 1 0 27 79 1 0 28 80 1 0 34 81 1 0 36 82 1 0 41 83 1 0 42 84 1 0 44 85 1 0 45 86 1 0 47 87 1 0 48 88 1 0 49 89 1 0 50 90 1 0 51 91 1 0 52 92 1 0 M END

Standard InCHIKey	WRXVPTMENPZUIZ-GKTZZTRGSA-N
Standard InCHI	InChI=1S/C33H40O19/c1-10-19(37)23(41)26(44)31(47-10)46-9-17-21(39)25(43)30(52-32-27(45)24(42)20(38)11(2)48-32)33(50-17)51-29-22(40)18-15(36)7-14(35)8-16(18)49-28(29)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10?,11-,17-,19+,20+,21+,23+,24?,25?,26?,27?,30?,31-,32+,33+/m1/s1
SMILES	C[C@@H]1[C@@H](C(C([C@@H](O1)OC2[C@@H](O[C@@H]([C@@H](C2O)O)CO[C@H]3C([C@H]([C@H](C(O3)C)O)O)O)OC4=C(OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.22	Volume:	673.908 ? Van der Waals volume.
Dense:	1.098	LogP:	0.766 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.325 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.679 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	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:	0.113	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.308	Fsp³:	0.545
MCE-18:	150.706 ? 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:	0.622	Fluc inhibitor:	0.221 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.674 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.695 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.237	Promiscuous compounds:	0.384

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.616	MDCK Permeability:	-4.961
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.012
20% Bioavailability (F20%):	0.278	30% Bioavailability (F30%):	0.891
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.147
Plasma Protein Binding (PPB):	81.703%	Volume Distribution (VD):	-0.087
Fu:	16.459% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.701
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.506
BSEP inhibitor:	0.234

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:	0.006
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.013 ? 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):

0.868

Half-life (T1/2):

4.872

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.469
Human Hepatotoxicity (H-HT):	0.24	Drug-induced Liver Injury (DILI):	0.448
AMES Toxicity:	0.661	Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.333	Skin Sensitization:	0.344
Carcinogencity:	0.019	Eye Corrosion:	0.0
Eye Irritation:	0.098	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.991
Hematotoxicity:	0.009	Drug-induced Nephrotoxicity:	0.017
Genotoxicity:	0.655	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.243	Hek293 Cytotoxicity:	0.911
BCF:	0.393 ? 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:	2.958 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.865 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.827 ? 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
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2765	Oxytropis falcata	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

Activity Type	# Activity
Inhibition	1

Activity Type	# Activity
Cell line	1

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
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	<	5	%	PMID[22775441]

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 NPC477613 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	19498
0.1-0.2	26286
0.2-0.3	3215
0.3-0.4	440
0.4-0.5	167
0.5-0.6	80
0.6-0.7	72
0.7-0.8	1
0.8-0.85	12
0.85-0.9	2
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12013
1.0	High Similarity	NPC11432
0.9405	High Similarity	NPC602448
0.9286	High Similarity	NPC221342
0.9286	High Similarity	NPC476470
0.9157	High Similarity	NPC122467
0.8539	High Similarity	NPC89052
0.8519	High Similarity	NPC476215
0.8295	Intermediate Similarity	NPC89127
0.8202	Intermediate Similarity	NPC292929
0.8182	Intermediate Similarity	NPC142142
0.8118	Intermediate Similarity	NPC173582
0.8118	Intermediate Similarity	NPC265885
0.8118	Intermediate Similarity	NPC181465
0.8118	Intermediate Similarity	NPC215710
0.8118	Intermediate Similarity	NPC163242
0.8118	Intermediate Similarity	NPC272068
0.8118	Intermediate Similarity	NPC473438
0.8118	Intermediate Similarity	NPC253788
0.8065	Intermediate Similarity	NPC303694
0.7835	Intermediate Similarity	NPC480445
0.7766	Intermediate Similarity	NPC173837
0.7765	Intermediate Similarity	NPC95866
0.767	Intermediate Similarity	NPC473554
0.75	Intermediate Similarity	NPC25523
0.7442	Intermediate Similarity	NPC170052
0.7442	Intermediate Similarity	NPC135846
0.7416	Intermediate Similarity	NPC203259
0.7416	Intermediate Similarity	NPC33054
0.7416	Intermediate Similarity	NPC155877
0.7416	Intermediate Similarity	NPC176740
0.7416	Intermediate Similarity	NPC471725
0.7416	Intermediate Similarity	NPC134532
0.7416	Intermediate Similarity	NPC602582
0.74	Intermediate Similarity	NPC162394
0.7353	Intermediate Similarity	NPC192539
0.7327	Intermediate Similarity	NPC480444
0.7222	Intermediate Similarity	NPC304741
0.72	Intermediate Similarity	NPC488734
0.72	Intermediate Similarity	NPC488735
0.72	Intermediate Similarity	NPC488739
0.72	Intermediate Similarity	NPC488732
0.72	Intermediate Similarity	NPC488738
0.7188	Intermediate Similarity	NPC203145
0.7111	Intermediate Similarity	NPC470405
0.7075	Intermediate Similarity	NPC487499
0.7	Intermediate Similarity	NPC471079
0.6977	Remote Similarity	NPC216496
0.6972	Remote Similarity	NPC487502
0.6947	Remote Similarity	NPC476472
0.6947	Remote Similarity	NPC294815
0.6947	Remote Similarity	NPC16194
0.6947	Remote Similarity	NPC220173
0.6923	Remote Similarity	NPC488737
0.6923	Remote Similarity	NPC39834
0.6915	Remote Similarity	NPC473327
0.6905	Remote Similarity	NPC111929
0.6905	Remote Similarity	NPC320283
0.6905	Remote Similarity	NPC41121
0.6857	Remote Similarity	NPC480443
0.68	Remote Similarity	NPC480441
0.6778	Remote Similarity	NPC254855
0.6778	Remote Similarity	NPC94610
0.6768	Remote Similarity	NPC189564
0.6731	Remote Similarity	NPC488740
0.6731	Remote Similarity	NPC488736
0.6731	Remote Similarity	NPC488733
0.6702	Remote Similarity	NPC240306
0.6667	Remote Similarity	NPC65563
0.6667	Remote Similarity	NPC470949
0.6604	Remote Similarity	NPC209550
0.6596	Remote Similarity	NPC255157
0.6596	Remote Similarity	NPC470444
0.6596	Remote Similarity	NPC259896
0.6596	Remote Similarity	NPC473571
0.6596	Remote Similarity	NPC110941
0.6596	Remote Similarity	NPC186816
0.6579	Remote Similarity	NPC487500
0.6545	Remote Similarity	NPC231787
0.6522	Remote Similarity	NPC487501
0.6489	Remote Similarity	NPC156869
0.6444	Remote Similarity	NPC224530
0.6392	Remote Similarity	NPC32641
0.6392	Remote Similarity	NPC256188
0.6383	Remote Similarity	NPC67326
0.633	Remote Similarity	NPC480442
0.6327	Remote Similarity	NPC603079
0.6316	Remote Similarity	NPC249560
0.63	Remote Similarity	NPC218161
0.6273	Remote Similarity	NPC25946
0.6263	Remote Similarity	NPC76831
0.625	Remote Similarity	NPC127546
0.625	Remote Similarity	NPC57625
0.625	Remote Similarity	NPC173637
0.625	Remote Similarity	NPC317489
0.625	Remote Similarity	NPC223424
0.625	Remote Similarity	NPC600591
0.6224	Remote Similarity	NPC35119
0.6214	Remote Similarity	NPC292019
0.6214	Remote Similarity	NPC202908
0.6146	Remote Similarity	NPC605592
0.614	Remote Similarity	NPC30011
0.614	Remote Similarity	NPC72554
0.6111	Remote Similarity	NPC474522
0.6106	Remote Similarity	NPC275977
0.6105	Remote Similarity	NPC187379
0.6105	Remote Similarity	NPC139320
0.6087	Remote Similarity	NPC259957
0.6067	Remote Similarity	NPC77672
0.6067	Remote Similarity	NPC133671
0.6067	Remote Similarity	NPC135391
0.6067	Remote Similarity	NPC78263
0.6067	Remote Similarity	NPC250069
0.6064	Remote Similarity	NPC116864
0.6064	Remote Similarity	NPC244776
0.6058	Remote Similarity	NPC219043
0.602	Remote Similarity	NPC126784
0.602	Remote Similarity	NPC241423
0.6	Remote Similarity	NPC241781
0.5978	Remote Similarity	NPC48093
0.5977	Remote Similarity	NPC54802
0.5977	Remote Similarity	NPC197304
0.5941	Remote Similarity	NPC471669
0.5932	Remote Similarity	NPC97817
0.5918	Remote Similarity	NPC129264
0.5909	Remote Similarity	NPC288084
0.5872	Remote Similarity	NPC298666
0.5859	Remote Similarity	NPC470125
0.5851	Remote Similarity	NPC223747
0.5842	Remote Similarity	NPC97119
0.5818	Remote Similarity	NPC156785
0.5806	Remote Similarity	NPC159579
0.5806	Remote Similarity	NPC219904
0.5789	Remote Similarity	NPC21359
0.5789	Remote Similarity	NPC460984
0.5784	Remote Similarity	NPC85751
0.5784	Remote Similarity	NPC19240
0.5778	Remote Similarity	NPC135599
0.5778	Remote Similarity	NPC73855
0.5778	Remote Similarity	NPC113968
0.5778	Remote Similarity	NPC328940
0.5778	Remote Similarity	NPC277174
0.5778	Remote Similarity	NPC606877
0.5758	Remote Similarity	NPC35167
0.5755	Remote Similarity	NPC48984
0.5743	Remote Similarity	NPC270448
0.5714	Remote Similarity	NPC104677
0.57	Remote Similarity	NPC61904
0.57	Remote Similarity	NPC153755
0.567	Remote Similarity	NPC473682
0.5652	Remote Similarity	NPC265530
0.5644	Remote Similarity	NPC470443
0.5638	Remote Similarity	NPC129217
0.5631	Remote Similarity	NPC470447
0.5619	Remote Similarity	NPC214621
0.5619	Remote Similarity	NPC34267
0.5591	Remote Similarity	NPC46420
0.5566	Remote Similarity	NPC11468
0.5556	Remote Similarity	NPC471748
0.5545	Remote Similarity	NPC296018
0.5543	Remote Similarity	NPC249281
0.5484	Remote Similarity	NPC145038
0.5484	Remote Similarity	NPC56077
0.5484	Remote Similarity	NPC281131
0.5484	Remote Similarity	NPC64305
0.5484	Remote Similarity	NPC253662
0.5484	Remote Similarity	NPC179950
0.5484	Remote Similarity	NPC88789
0.5484	Remote Similarity	NPC491374
0.5481	Remote Similarity	NPC473073
0.5481	Remote Similarity	NPC473071
0.5474	Remote Similarity	NPC175107
0.5472	Remote Similarity	NPC14187
0.5464	Remote Similarity	NPC276377
0.5455	Remote Similarity	NPC258044
0.5455	Remote Similarity	NPC217387
0.5455	Remote Similarity	NPC29958
0.5455	Remote Similarity	NPC609888
0.5437	Remote Similarity	NPC482026
0.5429	Remote Similarity	NPC287889
0.5429	Remote Similarity	NPC470449
0.5417	Remote Similarity	NPC85707
0.5413	Remote Similarity	NPC473644
0.54	Remote Similarity	NPC44931
0.5397	Remote Similarity	NPC33083
0.5391	Remote Similarity	NPC175429
0.5385	Remote Similarity	NPC221288
0.5385	Remote Similarity	NPC276222
0.5385	Remote Similarity	NPC274618
0.5385	Remote Similarity	NPC194836
0.5385	Remote Similarity	NPC118284
0.5385	Remote Similarity	NPC91493
0.5385	Remote Similarity	NPC605081
0.5385	Remote Similarity	NPC608147
0.5377	Remote Similarity	NPC223426
0.5368	Remote Similarity	NPC472459
0.5364	Remote Similarity	NPC311850
0.5361	Remote Similarity	NPC136761
0.5347	Remote Similarity	NPC65003

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5584
0.1-0.2	3512
0.2-0.3	43
0.3-0.4	6
0.4-0.5	2
0.5-0.6	2
0.6-0.7	0
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
0.7416	Intermediate Similarity	NPD6797	Phase 2
0.5631	Remote Similarity	NPD7251	Phase 2
0.5278	Remote Similarity	NPD7808	Phase 3

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