NPASS Compound

Natural Product: NPC96795

Natural Product ID	NPC96795
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5R,6S)-4,5-Dihydroxy-6-Methyl-3-[(2S,3R,4R,5S)-3,4,5-Trihydroxyoxan-2-Yl]Oxyoxan-2-Yl]Oxy-6-[2-(3,4-Dihydroxyphenyl)Ethoxy]-5-Hydroxy-2-(Hydroxymethyl)Oxan-3-Yl] (E)-3-(3,4-Dihydroxyphenyl)Prop-2-Enoate
IUPAC Name	[(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL595544
PubChem CID	14034194
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 97101 0 0 0 0 0 0 0 0999 V2000 3.7981 -1.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6805 -4.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9410 -6.2437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3505 -6.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6110 -8.2339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4619 -9.1981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0524 -8.6851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7919 -7.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 -9.6493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7224 -10.6753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4133 -0.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 1.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8672 0.3967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2768 0.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4258 -0.0544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8354 0.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0958 1.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9468 2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5372 2.3870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2072 4.3772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5054 2.4489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1700 4.5883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 6.4004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 4.7046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 6.1818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4996 6.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8882 4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3986 7.0297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7496 7.9939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 5.5525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 7.3646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2597 -1.5910 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8626 -0.0826 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6849 -2.1132 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8482 0.6575 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3114 -2.7335 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8972 -3.0288 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9856 -3.7279 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1577 -4.5060 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2033 -5.0270 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4996 -5.7926 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0205 -8.7470 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3824 -6.6949 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5062 -9.1362 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5733 -11.6395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0865 1.9801 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8547 2.7954 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1567 2.7954 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7887 -1.1012 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1653 -1.5316 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9844 -0.5056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2792 3.2039 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6168 4.8902 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7658 3.9261 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5302 1.9190 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1805 7.3646 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0235 7.8099 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0026 4.9908 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8991 6.9134 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6635 6.7262 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5182 3.9308 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5247 1.7929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8814 2.5425 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0116 7.6798 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6346 6.5448 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 7.6590 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1102 5.3933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4666 2.7555 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7909 5.4514 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8986 7.0297 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4996 9.2929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7286 5.0395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1825 8.4616 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5706 2.4621 0.0000 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 12 16 1 0 5 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 28 32 1 0 18 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 39 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 46 47 1 0 47 48 1 0 46 49 1 0 45 50 1 0 39 51 1 0 38 52 1 0 17 53 1 0 19 3 1 0 30 25 1 0 40 34 1 0 47 42 1 0 14 9 1 0 1 54 1 0 2 55 1 0 2 56 1 0 3 57 1 6 5 58 1 6 7 59 1 0 7 60 1 0 8 61 1 0 8 62 1 0 10 63 1 0 11 64 1 0 14 65 1 0 15 66 1 0 16 67 1 0 17 68 1 1 18 69 1 6 19 70 1 1 23 71 1 0 24 72 1 0 26 73 1 0 27 74 1 0 30 75 1 0 31 76 1 0 32 77 1 0 34 78 1 1 36 79 1 6 37 80 1 0 37 81 1 0 37 82 1 0 38 83 1 1 39 84 1 6 40 85 1 6 42 86 1 1 44 87 1 0 44 88 1 0 45 89 1 1 46 90 1 6 47 91 1 6 48 92 1 0 49 93 1 0 50 94 1 0 51 95 1 0 52 96 1 0 53 97 1 0 M END

Standard InCHIKey	UDHCHDJLZGYDDM-JPCQEIDESA-N
Standard InCHI	InChI=1S/C34H44O19/c1-14-24(42)26(44)31(53-32-27(45)25(43)21(40)13-48-32)34(49-14)52-30-28(46)33(47-9-8-16-3-6-18(37)20(39)11-16)50-22(12-35)29(30)51-23(41)7-4-15-2-5-17(36)19(38)10-15/h2-7,10-11,14,21-22,24-40,42-46H,8-9,12-13H2,1H3/b7-4+/t14-,21-,22+,24-,25+,26+,27+,28+,29+,30+,31+,32-,33+,34-/m0/s1
SMILES	OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O[C@@H]1OC[C@@H]([C@H]([C@H]1O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.25	Volume:	699.76 ? Van der Waals volume.
Dense:	1.081	LogP:	-0.064 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.888 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.031 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	32.0
TPSA:	304.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.06	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.319	Fsp³:	0.559
MCE-18:	128.377 ? 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:	0.702	Fluc inhibitor:	0.659 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.112 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.6 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.336	Promiscuous compounds:	0.41

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.785	MDCK Permeability:	-5.118
Pgp-inhibitor:	0.0	Pgp-substrate:	0.474
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):	0.987
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.063
Plasma Protein Binding (PPB):	60.299%	Volume Distribution (VD):	-0.312
Fu:	34.25% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.006
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.915 ? 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):

1.347

Half-life (T1/2):

4.421

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.317
Human Hepatotoxicity (H-HT):	0.369	Drug-induced Liver Injury (DILI):	0.701
AMES Toxicity:	0.96	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.016	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.0
Eye Irritation:	0.017	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.071	Drug-induced Nephrotoxicity:	0.268
Genotoxicity:	0.396	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.995	Hek293 Cytotoxicity:	0.628
BCF:	0.561 ? 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:	3.283 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.039 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.348 ? 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
NPO33377	teucrium chamaedris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19674906]

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	5
IC50	4

Activity Type	# Activity
Others	2
Non-molecular	7

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	54.7	%	PMID[19674906]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.5	n.a.	PMID[19674906]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	1.5	n.a.	PMID[19674906]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	2.0	n.a.	PMID[19674906]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	16300.0	nM	PMID[19674906]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	34600.0	nM	PMID[19674906]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	44800.0	nM	PMID[19674906]
NPT1	Others	Radical scavenging activity	n.a.	Activity	=	1.4	n.a.	Open TG-GATES in vivo data: Biochemistry
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	16500.0	nM	PMID[18980381]

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 NPC96795 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	14802
0.1-0.2	30833
0.2-0.3	3720
0.3-0.4	395
0.4-0.5	44
0.5-0.6	27
0.6-0.7	23
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC264632
0.8587	High Similarity	NPC94871
0.837	Intermediate Similarity	NPC64195
0.7917	Intermediate Similarity	NPC229505
0.7872	Intermediate Similarity	NPC471062
0.7812	Intermediate Similarity	NPC473427
0.7674	Intermediate Similarity	NPC472350
0.7674	Intermediate Similarity	NPC197316
0.7674	Intermediate Similarity	NPC89105
0.7282	Intermediate Similarity	NPC257970
0.7204	Intermediate Similarity	NPC476397
0.7174	Intermediate Similarity	NPC269141
0.6966	Remote Similarity	NPC483706
0.6915	Remote Similarity	NPC205864
0.6915	Remote Similarity	NPC247032
0.6889	Remote Similarity	NPC483705
0.6832	Remote Similarity	NPC306890
0.6737	Remote Similarity	NPC252292
0.6667	Remote Similarity	NPC112
0.6636	Remote Similarity	NPC470927
0.6598	Remote Similarity	NPC100998
0.6562	Remote Similarity	NPC298257
0.6562	Remote Similarity	NPC175214
0.6559	Remote Similarity	NPC76406
0.6495	Remote Similarity	NPC296954
0.6484	Remote Similarity	NPC46137
0.6316	Remote Similarity	NPC611289
0.6279	Remote Similarity	NPC886
0.6277	Remote Similarity	NPC68092
0.625	Remote Similarity	NPC476398
0.6224	Remote Similarity	NPC105005
0.6196	Remote Similarity	NPC260425
0.6139	Remote Similarity	NPC300894
0.6139	Remote Similarity	NPC23845
0.6082	Remote Similarity	NPC263829
0.596	Remote Similarity	NPC34587
0.5941	Remote Similarity	NPC34927
0.5882	Remote Similarity	NPC610636
0.5865	Remote Similarity	NPC476384
0.5865	Remote Similarity	NPC106818
0.5851	Remote Similarity	NPC81515
0.5773	Remote Similarity	NPC134405
0.5648	Remote Similarity	NPC87403
0.5534	Remote Similarity	NPC119537
0.55	Remote Similarity	NPC476377
0.5463	Remote Similarity	NPC476380
0.5463	Remote Similarity	NPC476381
0.5421	Remote Similarity	NPC476375
0.5408	Remote Similarity	NPC64141
0.5408	Remote Similarity	NPC40305
0.5408	Remote Similarity	NPC171134
0.5385	Remote Similarity	NPC287597
0.537	Remote Similarity	NPC196063
0.537	Remote Similarity	NPC604195
0.5253	Remote Similarity	NPC205195
0.5213	Remote Similarity	NPC473285
0.5135	Remote Similarity	NPC470933
0.513	Remote Similarity	NPC476386
0.51	Remote Similarity	NPC321638
0.5093	Remote Similarity	NPC259347
0.5046	Remote Similarity	NPC476382
0.5045	Remote Similarity	NPC476378

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC96795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5402
0.1-0.2	3691
0.2-0.3	55
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
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
0.7674	Intermediate Similarity	NPD7266	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