NPASS Compound

Natural Product: NPC245789

Natural Product ID	NPC245789
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ROQLTZUOXIQBDO-JZWLZXDTSA-O
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	443915
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0001361] Anthocyanins [CHEMONTID:0002996] Anthocyanidin-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 61 64 0 0 0 0 0 0 0 0999 V2000 -2.3892 1.2100 -2.3359 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7734 1.9260 -3.4836 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0763 2.2410 -3.7448 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0228 1.8313 -2.8375 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6403 1.1324 -1.7189 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3162 0.8029 -1.4373 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0425 0.0552 -0.2114 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7939 -0.3412 0.2019 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6642 -1.0433 1.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7982 -1.3442 2.1408 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7237 -2.0355 3.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8589 -2.3223 4.0489 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1017 -1.9100 3.6073 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1648 -1.2153 2.4271 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0209 -0.9203 1.6747 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0680 -0.2735 0.5735 O 0 0 0 0 0 3 0 0 0 0 0 0 -6.2187 -2.2155 4.3719 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4832 -2.4634 3.7815 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6798 -0.0580 -0.5239 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6523 -0.3554 -0.2988 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1045 -1.2739 -1.4323 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5882 -1.5469 -1.3641 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3030 -0.2117 -1.2252 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7332 0.4401 0.0368 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5780 1.5938 0.4494 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8771 1.1546 0.7640 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2330 0.2732 1.7420 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3453 -0.2243 2.4651 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6382 -0.1444 2.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5752 0.5222 1.0811 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8001 0.2622 1.1935 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1951 1.4155 0.0927 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4263 0.8197 -0.2931 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6619 -0.3690 -1.1003 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9901 -2.0820 -2.5886 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3807 -2.4582 -1.2835 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3439 2.1541 -3.1083 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4233 2.9542 -4.8956 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3499 0.9880 -2.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9968 2.2274 -4.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3947 0.8175 -1.0158 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7256 -1.3895 1.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7815 -2.8698 4.9730 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1191 -0.8756 2.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1252 -1.9136 4.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1942 -2.2086 4.7321 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8161 -0.9137 0.6254 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9016 -0.7916 -2.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8753 -2.1771 -0.5146 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1051 0.4499 -2.0965 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7338 -0.3335 0.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1080 2.0649 1.3376 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6784 2.3406 -0.3717 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7724 -1.2385 1.9114 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9362 0.1310 3.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9184 1.9400 -0.4175 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1593 0.1099 -1.8099 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5231 -1.5774 -3.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3968 -3.0164 -2.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7608 2.9858 -2.7059 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9550 2.4915 -5.6494 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 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 13 17 1 0 11 18 1 0 8 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 24 33 1 0 23 34 1 0 22 35 1 0 21 36 1 0 4 37 1 0 3 38 1 0 6 1 1 0 16 7 2 0 33 20 1 0 15 10 1 0 1 39 1 0 2 40 1 0 5 41 1 0 9 42 1 0 12 43 1 0 14 44 1 0 17 45 1 0 18 46 1 0 20 47 1 1 21 48 1 6 22 49 1 1 23 50 1 6 24 51 1 1 25 52 1 0 25 53 1 0 29 54 1 0 29 55 1 0 32 56 1 0 34 57 1 0 35 58 1 0 36 59 1 0 37 60 1 0 38 61 1 0 M CHG 1 16 1 M END

Standard InCHIKey	ROQLTZUOXIQBDO-JZWLZXDTSA-O
Standard InCHI	InChI=1S/C24H22O14/c25-10-4-13(27)11-6-16(23(36-15(11)5-10)9-1-2-12(26)14(28)3-9)37-24-22(34)21(33)20(32)17(38-24)8-35-19(31)7-18(29)30/h1-6,17,20-22,24,32-34H,7-8H2,(H4-,25,26,27,28,29,30)/p+1/t17-,20-,21+,22-,24-/m1/s1
SMILES	c1cc(c(cc1c1c(cc2c(cc(cc2[o+]1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)CC(=O)O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	535.11	Volume:	487.451 ? Van der Waals volume.
Dense:	1.098	LogP:	-0.293 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.074 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.472 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	25.0
TPSA:	234.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.407	Fsp³:	0.292
MCE-18:	93.032 ? 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:	0.698	Fluc inhibitor:	0.169 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.965 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.864 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.246	Promiscuous compounds:	0.809

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.506	MDCK Permeability:	-5.012
Pgp-inhibitor:	0.0	Pgp-substrate:	0.04
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):	0.006
20% Bioavailability (F20%):	0.482	30% Bioavailability (F30%):	0.952
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.197
Plasma Protein Binding (PPB):	79.336%	Volume Distribution (VD):	-0.147
Fu:	19.756% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.013
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.13	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.019
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.218 ? 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):

1.854

Half-life (T1/2):

3.696

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.007
Human Hepatotoxicity (H-HT):	0.982	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.993	Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.859	Skin Sensitization:	1.0
Carcinogencity:	1.0	Eye Corrosion:	0.0
Eye Irritation:	0.997	Respiratory Toxicity:	0.748
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.027
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.002
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.006
A549 Cytotoxicity:	0.006	Hek293 Cytotoxicity:	0.386
BCF:	0.298 ? 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:	2.836 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.168 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.446 ? 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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO22093	Miliusa sinensis	Species	Annonaceae	Eukaryota	dried leaves, twigs, and flowers	Vietnam	n.a.	PMID[16420055]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17238120]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18405608]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18661821]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21417376]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21627108]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[7700984]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO127	Phragmites australis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8002	Solanum olgae	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4787	Capuronianthus mahafalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5641	Dendroctonus frontalis	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2832	Hazunta membranacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10756	Callitris drummondii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6604	Melanothamnus afaqhusainii	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO978	Panzerina lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4728	Streptomyces tsukubensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4706	Streptomyces vinaceusdrappus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1899	Aria rostellata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2143	Rubus adenotrichos	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO127	Phragmites australis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO127	Phragmites australis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10017	Echium pininana	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO978	Panzerina lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22093	Miliusa sinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8002	Solanum olgae	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6604	Melanothamnus afaqhusainii	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5641	Dendroctonus frontalis	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2832	Hazunta membranacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4787	Capuronianthus mahafalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10756	Callitris drummondii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2143	Rubus adenotrichos	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4728	Streptomyces tsukubensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20306	Cheiropteris palmatopedata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO127	Phragmites australis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22537	Anthelia juratzkana	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1899	Aria rostellata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4706	Streptomyces vinaceusdrappus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19841	Potamilla occelata	Species	Sabellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22273	Angelica pubescens	Species	Apiaceae	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 NPC245789 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	14916
0.1-0.2	32540
0.2-0.3	2002
0.3-0.4	366
0.4-0.5	22
0.5-0.6	10
0.6-0.7	3
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
0.6707	Remote Similarity	NPC168579
0.6322	Remote Similarity	NPC473480
0.6	Remote Similarity	NPC15538
0.5882	Remote Similarity	NPC138227
0.5814	Remote Similarity	NPC37793
0.5495	Remote Similarity	NPC76176
0.5435	Remote Similarity	NPC125755
0.5435	Remote Similarity	NPC161700
0.52	Remote Similarity	NPC473621
0.5165	Remote Similarity	NPC277867
0.5146	Remote Similarity	NPC229409
0.5109	Remote Similarity	NPC603591
0.5055	Remote Similarity	NPC280945

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC245789 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4482
0.1-0.2	4628
0.2-0.3	35
0.3-0.4	5
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