NPASS Compound

Natural Product: NPC85349

Natural Product ID	NPC85349
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GQKXCBCSVYJUMI-WACKOAQBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6569946
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000036] Nitrobenzenes

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 2.6026 -1.6350 0.2091 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4969 -0.2516 0.7011 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5830 0.2972 1.2618 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8562 -0.3813 1.4225 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9991 0.2704 1.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2110 -0.3553 1.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3224 -1.6062 1.7699 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1832 -2.2674 2.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9816 -1.6236 2.0008 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5784 -2.2266 1.9472 N 0 0 0 0 0 0 0 0 0 0 0 0 9.7086 -1.5727 1.5190 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7243 -3.3446 2.4770 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3138 0.5829 0.6572 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1486 0.2778 0.1668 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1095 1.1075 0.0989 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7973 0.3568 -1.0425 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1913 0.7203 -1.2402 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5271 1.8296 -1.9765 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4564 2.6967 -2.5914 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8410 2.1939 -2.1791 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0791 3.2149 -2.8592 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8312 1.4338 -1.6351 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2701 1.7942 -1.8309 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4473 0.3167 -0.8947 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4611 -0.4555 -0.3418 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1906 -1.6148 0.4269 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1819 0.0113 -0.7300 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6529 -0.9512 -0.5344 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2238 -1.0033 -0.4650 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1335 -1.7125 -0.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6920 -1.8769 0.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1633 -2.3348 0.9354 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5559 1.3190 1.6355 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9386 1.2700 0.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1158 0.1615 0.8543 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2473 -3.2376 2.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0773 -2.1525 2.3457 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3700 1.6039 1.0797 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 2.1561 -0.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 0.9107 0.9946 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1371 0.4027 -1.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2526 3.5228 -1.8736 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5428 2.1516 -2.8120 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8842 3.1515 -3.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5673 1.6081 -2.8715 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8839 1.0863 -1.1993 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4729 2.8404 -1.4973 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0920 -1.7103 0.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6831 -1.4813 1.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5904 -2.5400 -0.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0178 -1.9000 0.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0569 -1.0533 -1.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 7 10 1 0 10 11 1 0 10 12 2 0 2 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 22 24 2 0 24 25 1 0 25 26 1 0 24 27 1 0 16 28 1 0 28 29 1 0 9 4 1 0 29 14 1 0 27 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 3 33 1 0 5 34 1 0 6 35 1 0 8 36 1 0 9 37 1 0 13 38 1 0 15 39 1 0 15 40 1 0 16 41 1 6 19 42 1 0 19 43 1 0 19 44 1 0 23 45 1 0 23 46 1 0 23 47 1 0 26 48 1 0 26 49 1 0 26 50 1 0 29 51 1 0 29 52 1 0 M CHG 2 10 1 11 -1 M END

Standard InCHIKey	GQKXCBCSVYJUMI-WACKOAQBSA-N
Standard InCHI	InChI=1S/C22H23NO6/c1-13(9-16-5-7-18(8-6-16)23(25)26)10-17-11-19(28-12-17)21-14(2)20(24)15(3)22(27-4)29-21/h5-10,19H,11-12H2,1-4H3/b13-9+,17-10-/t19-/m1/s1
SMILES	C/C(=Cc1ccc(cc1)N(=O)=O)/C=C1/C[C@H](c2c(C)c(=O)c(C)c(OC)o2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	397.15	Volume:	403.409 ? Van der Waals volume.
Dense:	0.984	LogP:	3.625 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.352 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.112 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	91.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.538	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.834	Fsp³:	0.318
MCE-18:	64.138 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	0.715 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.05 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.986 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.052	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87	MDCK Permeability:	-4.653
Pgp-inhibitor:	0.356	Pgp-substrate:	0.141
PAMPA:	0.171 ? 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):	0.0
20% Bioavailability (F20%):	0.004	30% Bioavailability (F30%):	0.035
50% Bioavailability (F50%):	0.633

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	95.775%	Volume Distribution (VD):	0.112
Fu:	3.397% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.817
OATP1B3 inhibitor:	0.724	BCRP inhibitor:	0.029
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.392
CYP2C19-inhibitor:	0.964	CYP2C19-substrate:	0.496
CYP2C9-inhibitor:	0.969	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.863	CYP2D6-substrate:	0.339
CYP3A4-inhibitor:	0.973	CYP3A4-substrate:	0.987
CYP2B6-substrate:	0.277	CYP2C8-inhibitor:	0.956
HLM stability:	0.145 ? 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):

5.673

Half-life (T1/2):

0.606

ADMET: Toxicity

hERG Blockers:	0.068	hERG Blockers (10um):	0.541
Human Hepatotoxicity (H-HT):	0.956	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.991	Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.98	Skin Sensitization:	1.0
Carcinogencity:	0.942	Eye Corrosion:	0.0
Eye Irritation:	0.938	Respiratory Toxicity:	0.55
Drug-induced Neurotoxicity:	0.119	Ototoxicity:	0.339
Hematotoxicity:	0.618	Drug-induced Nephrotoxicity:	0.768
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.208
A549 Cytotoxicity:	0.338	Hek293 Cytotoxicity:	0.873
BCF:	1.883 ? 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:	4.197 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.881 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.188 ? 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
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880174]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800631]
NPO10867	Graphis elongata	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7883	Albugo candida	Species	Albuginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1937	Andropogon nardus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7365	Clibadium pentaneuron	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12481	Croton californicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5219	Dendrobium rotundatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2805	Distolasterias nipon	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9020	Eriostemon fitzgeraldii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO729	Espeletia marcana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11355	Homarus americanus	Species	Nephropidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12309	Malva crispa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6787	Neoalsomitra integrifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3202	Nolina erumpens	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8547	Petasites niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3900	Phellinus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9937	Piptolepis leptospermoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24849	Rhinella paracnemis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12535	Solanum toxicarium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9320	Weddellina squamulosa	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9227	Xylaria berteri	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10867	Graphis elongata	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8547	Petasites niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6787	Neoalsomitra integrifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5219	Dendrobium rotundatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO729	Espeletia marcana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2805	Distolasterias nipon	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24849	Rhinella paracnemis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7883	Albugo candida	Species	Albuginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3900	Phellinus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7365	Clibadium pentaneuron	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11355	Homarus americanus	Species	Nephropidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9020	Eriostemon fitzgeraldii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12481	Croton californicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12309	Malva crispa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12535	Solanum toxicarium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3202	Nolina erumpens	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9227	Xylaria berteri	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1937	Andropogon nardus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9320	Weddellina squamulosa	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9937	Piptolepis leptospermoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1526	Ratibida latipalearis	Species	Asteraceae	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 NPC85349 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	23123
0.1-0.2	26662
0.2-0.3	71
0.3-0.4	1
0.4-0.5	0
0.5-0.6	2
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	Natural Product ID
0.5275	Remote Similarity	NPC600891
0.5275	Remote Similarity	NPC605338

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85349 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4094
0.1-0.2	5028
0.2-0.3	28
0.3-0.4	0
0.4-0.5	0
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