NPASS Compound

Natural Product: NPC296954

Natural Product ID	NPC296954
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Samioside
IUPAC Name	[(2R,3R,4R,5R,6R)-4-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-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	samioside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL469152
PubChem CID	10350153
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 3D 97101 0 0 0 0 0 0 0 0999 V2000 -6.2707 0.6378 -1.1791 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0203 1.0426 -1.6452 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9849 0.7758 -0.5629 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9741 -0.5511 -0.2784 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4630 -1.4061 -1.2502 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4040 -1.8304 -2.1467 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7391 -3.1492 -2.1392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6422 -4.1212 -2.4318 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1300 -5.5311 -2.4043 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6245 -6.1258 -3.5448 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0593 -7.4272 -3.4565 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0193 -8.1506 -2.2835 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5155 -7.5161 -1.1626 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0740 -6.2219 -1.2141 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4442 -8.1825 0.0542 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4485 -9.4528 -2.1717 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1997 -0.8431 -1.8708 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6417 0.2691 -0.9797 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6612 1.3558 -0.9805 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3189 2.5038 -0.2629 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1626 3.7556 -0.8555 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3526 3.7986 -2.1039 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7999 4.9594 -0.0937 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6034 4.9084 1.1919 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2442 6.0685 1.9876 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0900 7.3067 1.4436 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7455 8.4161 2.1961 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5486 8.2814 3.5418 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7003 7.0439 4.0994 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0398 5.9446 3.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5096 6.8577 5.4685 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1969 9.3856 4.3426 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3722 0.6437 -1.3868 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5884 0.2625 -0.4580 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1515 1.4135 0.0890 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1733 1.1045 0.9876 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6979 0.3696 2.2052 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2860 0.3592 0.2683 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8918 0.2786 -1.1904 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6062 -0.5668 -1.1956 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8968 -1.6751 -0.3761 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8465 -0.2531 -2.0147 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5207 0.9204 0.4959 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3287 -0.0013 1.1127 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7697 0.4386 2.3630 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7748 -0.4421 2.7445 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4009 -0.9964 1.5157 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6349 -0.2717 0.4098 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4994 -1.0942 -0.7074 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1310 -2.3581 1.4319 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8829 -0.7103 1.4200 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1188 0.6418 1.5148 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2905 -1.8814 -2.0026 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2170 -0.1392 -0.5627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7601 0.4329 -2.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0448 2.1335 -1.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3793 1.3004 0.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1312 -2.3122 -0.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5663 -3.2763 -2.8948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2243 -3.4570 -1.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8803 -4.0541 -1.6315 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2001 -3.9757 -3.4423 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6584 -5.5613 -4.4699 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4568 -7.9170 -4.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6743 -5.7244 -0.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8851 -9.0443 0.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0819 -9.8090 -2.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4834 -0.3849 -2.8349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5320 -0.2053 0.0375 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7618 1.6880 -2.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7079 5.8724 -0.6577 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7133 3.9379 1.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2349 7.4686 0.3845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6370 9.3717 1.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1625 4.9603 3.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7956 7.5863 6.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6664 10.2646 4.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0986 -0.2781 0.3840 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6141 2.0704 1.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0085 0.9015 3.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2418 -0.6007 2.2428 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6088 0.2520 2.2758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2485 -0.7051 0.6477 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5737 1.3151 -1.5052 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3134 -0.8876 -2.1914 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6217 -2.1617 -0.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3894 0.4857 -2.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8086 -0.9824 1.2635 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4049 -1.2692 3.3970 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5520 0.1003 3.3425 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1410 0.6874 0.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5981 -0.4863 -1.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9051 -2.8465 1.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2713 -1.0634 0.4434 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3894 -1.2741 2.2269 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3734 0.9172 2.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2169 -2.3144 -1.1084 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 39 42 1 0 38 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 6 47 51 1 0 51 52 1 0 17 53 1 0 19 3 1 0 30 25 1 0 40 34 1 0 48 44 1 0 14 9 1 0 1 54 1 0 2 55 1 0 2 56 1 0 3 57 1 1 5 58 1 1 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 6 18 69 1 1 19 70 1 6 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 1 37 80 1 0 37 81 1 0 37 82 1 0 38 83 1 1 39 84 1 6 40 85 1 6 41 86 1 0 42 87 1 0 44 88 1 1 46 89 1 0 46 90 1 0 48 91 1 6 49 92 1 0 50 93 1 0 51 94 1 0 51 95 1 0 52 96 1 0 53 97 1 0 M END

Standard InCHIKey	MYTQIOQLRFFFEC-HQQSBTJXSA-N
Standard InCHI	InChI=1S/C34H44O19/c1-15-27(52-33-30(45)34(46,13-36)14-48-33)24(42)25(43)32(49-15)53-29-26(44)31(47-9-8-17-3-6-19(38)21(40)11-17)50-22(12-35)28(29)51-23(41)7-4-16-2-5-18(37)20(39)10-16/h2-7,10-11,15,22,24-33,35-40,42-46H,8-9,12-14H2,1H3/b7-4+/t15-,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)O)O[C@@H]1OC[C@]([C@H]1O)(O)CO)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.25	Volume:	699.76 ? Van der Waals volume.
Dense:	1.081	LogP:	0.372 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.979 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.448 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	31.0
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:	0.057	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.377	Fsp³:	0.559
MCE-18:	130.547 ? 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:	0.68	Fluc inhibitor:	0.632 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.111 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.591 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.316	Promiscuous compounds:	0.517

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.768	MDCK Permeability:	-5.161
Pgp-inhibitor:	0.0	Pgp-substrate:	0.149
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):	0.995
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:	0.092
Plasma Protein Binding (PPB):	64.774%	Volume Distribution (VD):	-0.288
Fu:	31.336% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
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:	0.013
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.966 ? 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):

2.04

Half-life (T1/2):

4.026

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.233
Human Hepatotoxicity (H-HT):	0.621	Drug-induced Liver Injury (DILI):	0.904
AMES Toxicity:	0.986	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.098	Skin Sensitization:	1.0
Carcinogencity:	0.123	Eye Corrosion:	0.0
Eye Irritation:	0.046	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.997
Hematotoxicity:	0.094	Drug-induced Nephrotoxicity:	0.329
Genotoxicity:	0.939	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.854
BCF:	0.626 ? 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:	3.318 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.097 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.374 ? 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
NPO1073	Phlomis samia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520237]
NPO1073	Phlomis samia	Species	Lamiaceae	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
Activity	1
IC50	1
IZ	9
MIC	6

Activity Type	# Activity
Others	2
Organism	15

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
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	IZ	=	10.0	mm	PMID[25237727]
NPT554	Organism	Candida glabrata	Candida glabrata	IZ	=	11.0	mm	PMID[24582402]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	=	890.0	ug.mL-1	PMID[20553004]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	11.0	mm	PMID[12502314]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	8.0	mm	PMID[24582402]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	790.0	ug.mL-1	PMID[20553004]
NPT1	Others	Radical scavenging activity	n.a.	Activity	=	70.0	%	PMID[2809611]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	23800.0	nM	PMID[25237727]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[16038563]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	16.0	mm	PMID[16038563]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	15.0	mm	PMID[25237727]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	10.0	mm	PMID[12502314]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	460.0	ug.mL-1	PMID[20553004]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	480.0	ug.mL-1	PMID[20553004]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	520.0	ug.mL-1	PMID[20553004]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	850.0	ug.mL-1	PMID[20452770]
NPT186	Organism	Candida tropicalis	Candida tropicalis	IZ	=	10.0	mm	PMID[20553004]

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 NPC296954 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	14459
0.1-0.2	32497
0.2-0.3	2522
0.3-0.4	281
0.4-0.5	41
0.5-0.6	23
0.6-0.7	22
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8519	High Similarity	NPC483705
0.814	Intermediate Similarity	NPC269141
0.7556	Intermediate Similarity	NPC112
0.7442	Intermediate Similarity	NPC472350
0.7442	Intermediate Similarity	NPC197316
0.7442	Intermediate Similarity	NPC89105
0.7128	Intermediate Similarity	NPC300894
0.7128	Intermediate Similarity	NPC23845
0.6932	Remote Similarity	NPC483706
0.6923	Remote Similarity	NPC263829
0.6742	Remote Similarity	NPC40305
0.6667	Remote Similarity	NPC610636
0.6627	Remote Similarity	NPC886
0.6526	Remote Similarity	NPC252292
0.6495	Remote Similarity	NPC96795
0.6495	Remote Similarity	NPC264632
0.6392	Remote Similarity	NPC100998
0.6374	Remote Similarity	NPC171134
0.6354	Remote Similarity	NPC105005
0.6264	Remote Similarity	NPC46137
0.6196	Remote Similarity	NPC328273
0.619	Remote Similarity	NPC229505
0.6186	Remote Similarity	NPC298257
0.6186	Remote Similarity	NPC175214
0.617	Remote Similarity	NPC76406
0.6105	Remote Similarity	NPC611289
0.6078	Remote Similarity	NPC196063
0.6078	Remote Similarity	NPC604195
0.602	Remote Similarity	NPC205864
0.602	Remote Similarity	NPC247032
0.5895	Remote Similarity	NPC321184
0.5825	Remote Similarity	NPC106818
0.5758	Remote Similarity	NPC34587
0.5743	Remote Similarity	NPC34927
0.5728	Remote Similarity	NPC141455
0.5684	Remote Similarity	NPC321638
0.5648	Remote Similarity	NPC94871
0.5607	Remote Similarity	NPC470934
0.5607	Remote Similarity	NPC87403
0.5567	Remote Similarity	NPC134405
0.5495	Remote Similarity	NPC488390
0.5474	Remote Similarity	NPC260425
0.5474	Remote Similarity	NPC81515
0.5463	Remote Similarity	NPC64195
0.5408	Remote Similarity	NPC68092
0.5377	Remote Similarity	NPC476384
0.5204	Remote Similarity	NPC205195
0.5161	Remote Similarity	NPC473285
0.5149	Remote Similarity	NPC476377
0.5135	Remote Similarity	NPC306890
0.5091	Remote Similarity	NPC471062
0.5089	Remote Similarity	NPC473427
0.5051	Remote Similarity	NPC64141

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC296954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5269
0.1-0.2	3821
0.2-0.3	58
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
0.7442	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