NPASS Compound

Natural Product: NPC83670

Natural Product ID	NPC83670
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OQZUBZJEVMCTGO-UJRRQQMQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102086065
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid and derivatives [CHEMONTID:0003539] Galloyl esters

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 52 54 0 0 0 0 0 0 0 0999 V2000 6.3496 -1.2523 -0.2004 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5809 -1.4584 0.3728 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8143 -0.9231 1.6178 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8184 -0.2033 2.2486 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6000 -0.0120 1.6564 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3412 -0.5384 0.4086 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0605 -0.3493 -0.2376 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8778 -0.8502 -1.3745 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0230 0.3626 0.3446 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7905 0.5378 -0.2908 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4680 2.0062 -0.5504 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2428 1.9982 -1.4422 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8697 1.3288 -0.6534 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5623 0.3028 -1.5062 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7180 -0.2435 -0.9086 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8332 0.4433 -0.5292 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8746 1.6842 -0.7140 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 -0.2069 0.0871 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1029 0.4994 0.4624 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2053 -0.0754 1.0424 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2206 -1.4342 1.2713 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1126 -2.1653 0.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0009 -1.5709 0.3150 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1057 -3.5436 1.1246 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3131 -2.0821 1.8589 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3225 0.6510 1.4161 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4473 0.8450 0.5596 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6291 -0.0153 0.5037 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2697 -1.2891 0.0656 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0595 3.2917 -1.7936 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5301 2.6717 -1.1251 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0477 -1.1139 2.2229 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1810 -1.6842 -1.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3476 -2.0263 -0.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0551 0.1935 3.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8134 0.5496 2.1407 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7909 0.0378 -1.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1550 2.4536 0.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5144 1.4114 -2.3425 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6139 2.1265 -0.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9058 0.7927 -2.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8943 -0.5250 -1.8121 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1458 1.5804 0.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1443 -2.1538 0.0326 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0481 -4.1690 0.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2609 -1.8895 1.5586 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2042 1.6335 1.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0002 -0.1401 1.5480 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0251 -1.7869 -0.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1577 3.4690 -2.7330 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5919 3.5776 -0.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8794 -0.7464 1.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 21 25 1 0 20 26 1 0 13 27 1 0 27 28 1 0 28 29 1 0 12 30 1 0 11 31 1 0 3 32 1 0 6 1 1 0 28 10 1 0 23 18 1 0 1 33 1 0 2 34 1 0 4 35 1 0 5 36 1 0 10 37 1 6 11 38 1 1 12 39 1 6 13 40 1 1 14 41 1 0 14 42 1 0 19 43 1 0 23 44 1 0 24 45 1 0 25 46 1 0 26 47 1 0 28 48 1 1 29 49 1 0 30 50 1 0 31 51 1 0 32 52 1 0 M END

Standard InCHIKey	OQZUBZJEVMCTGO-UJRRQQMQSA-N
Standard InCHI	InChI=1S/C20H20O12/c21-10-3-1-8(2-4-10)19(28)32-17-16(26)15(25)13(31-20(17)29)7-30-18(27)9-5-11(22)14(24)12(23)6-9/h1-6,13,15-17,20-26,29H,7H2/t13-,15-,16+,17-,20-/m1/s1
SMILES	c1cc(ccc1C(=O)O[C@@H]1[C@H]([C@@H]([C@@H](COC(=O)c2cc(c(c(c2)O)O)O)O[C@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	452.1	Volume:	413.198 ? Van der Waals volume.
Dense:	1.094	LogP:	0.795 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.102 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.995 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	20.0
TPSA:	203.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.223	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.811	Fsp³:	0.3
MCE-18:	74.462 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.459	Fluc inhibitor:	0.458 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.066 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.399 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.325	Promiscuous compounds:	0.944

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.488	MDCK Permeability:	-5.071
Pgp-inhibitor:	0.0	Pgp-substrate:	0.022
PAMPA:	0.994 ? 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):	0.006
20% Bioavailability (F20%):	0.963	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.995
Plasma Protein Binding (PPB):	78.233%	Volume Distribution (VD):	-0.209
Fu:	22.851% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.816
BSEP inhibitor:	0.027

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:	0.441
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.981
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.035 ? 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):

6.393

Half-life (T1/2):

2.082

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.837
Human Hepatotoxicity (H-HT):	0.05	Drug-induced Liver Injury (DILI):	0.748
AMES Toxicity:	0.457	Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.223	Skin Sensitization:	0.999
Carcinogencity:	0.304	Eye Corrosion:	0.004
Eye Irritation:	0.978	Respiratory Toxicity:	0.032
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.848
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.02
Genotoxicity:	0.895	RPMI-8226 Immunitoxicity:	0.007
A549 Cytotoxicity:	0.913	Hek293 Cytotoxicity:	0.327
BCF:	0.518 ? 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:	3.267 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.407 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.93 ? 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
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11524125]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11524125]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22080044]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25050371]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607351]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33170684]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35508595]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39769283]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24605	Monochaetia compta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23975	Osteophloeum platyspermum	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5064	Derris uliginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23698	Gardneria insularis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25647	Taraxacum bicorne	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24230	Petriella sordida	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6157	Dahlstedtia araripensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29226.1	Ficus cordata subsp. salicifolia	Subspecies	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22144	Daphne lancifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21967	Astragalus asper	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25862	Lafoensia glyptocarpa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14279.1	Ficus sarmentosa var. thunbergii	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	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

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

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 NPC83670 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	14756
0.1-0.2	31035
0.2-0.3	3789
0.3-0.4	209
0.4-0.5	57
0.5-0.6	11
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.86	High Similarity	NPC482667
0.6119	Remote Similarity	NPC90905
0.5893	Remote Similarity	NPC226738
0.5862	Remote Similarity	NPC229036
0.5522	Remote Similarity	NPC4013
0.541	Remote Similarity	NPC44260
0.541	Remote Similarity	NPC120621
0.5254	Remote Similarity	NPC225036
0.5246	Remote Similarity	NPC239019
0.5246	Remote Similarity	NPC247629
0.5246	Remote Similarity	NPC75945
0.5082	Remote Similarity	NPC190587
0.507	Remote Similarity	NPC140151

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC83670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4041
0.1-0.2	4932
0.2-0.3	174
0.3-0.4	1
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