NPASS Compound

Natural Product: NPC77869

Natural Product ID	NPC77869
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HHRPSKAYQPDDGQ-KOJUQBNKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11972297
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 72 76 0 0 0 0 0 0 0 0999 V2000 -6.2573 -1.5475 -2.2662 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5790 -1.5188 -1.7987 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8693 -1.0936 -0.5166 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8066 -0.7030 0.2700 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5089 -0.7299 -0.1872 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2089 -1.1592 -1.4823 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8098 -1.1748 -1.9436 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4920 -1.5942 -3.2192 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1597 -1.6000 -3.6255 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7985 -1.9635 -4.7529 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2140 -1.1795 -2.7224 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -1.1422 -3.0268 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0673 -0.7173 -2.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6994 -0.3115 -0.8672 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6258 -0.3298 -0.5174 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5591 -0.7637 -1.4520 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8350 -0.7952 -1.1654 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0916 0.1271 0.7897 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6892 1.5193 0.7346 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7564 2.5659 1.3208 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6908 2.2308 2.8153 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4236 0.7308 2.9164 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7495 0.5772 3.8609 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8559 1.2251 3.3278 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0668 0.1618 1.6986 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2569 2.9948 3.4638 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3746 3.7946 1.1179 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8439 1.5044 1.5123 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6665 0.1312 0.0714 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9920 0.2618 -0.3418 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8085 1.2822 0.3806 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9609 0.6944 1.1653 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8073 -0.2191 0.3028 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9079 -0.8582 -0.7382 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4363 -2.2153 -1.1266 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6875 -2.0806 -1.6774 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6235 -0.9962 -0.1716 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8065 0.5324 -0.3159 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5624 0.0229 2.3066 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3546 2.1988 -0.5392 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4963 -1.5623 -4.3178 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1778 -1.0615 -0.0398 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0934 -1.8913 -3.2787 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4039 -1.8239 -2.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0554 -0.3709 1.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6802 -0.4296 0.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2534 -1.9220 -3.9152 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0835 -0.7417 -2.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8501 -0.6212 1.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9306 1.8481 -0.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2630 2.5159 0.8720 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7091 2.4556 3.2167 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2940 0.2280 3.4007 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5414 1.0526 4.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0417 -0.5017 3.9762 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5340 1.4641 3.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1284 3.6811 4.0973 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0467 4.5268 1.6600 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0674 0.6051 1.8468 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0386 0.4577 -1.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1931 1.8721 1.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6223 1.5394 1.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2296 -0.9973 0.9353 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8990 -0.2206 -1.6399 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6944 -2.6756 -1.8299 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4715 -2.8121 -0.1759 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7693 -1.2021 -2.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5713 0.5674 0.3133 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3422 -0.9109 2.1373 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2679 2.4844 -0.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4816 -1.6845 -4.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5617 -1.7315 0.5990 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 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 14 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 12 41 1 0 3 42 1 0 6 1 1 0 17 7 1 0 25 18 1 0 37 30 1 0 16 11 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 8 47 1 0 13 48 1 0 18 49 1 1 19 50 1 6 20 51 1 6 21 52 1 1 22 53 1 1 23 54 1 0 23 55 1 0 24 56 1 0 26 57 1 0 27 58 1 0 28 59 1 0 30 60 1 6 31 61 1 1 32 62 1 1 33 63 1 1 34 64 1 6 35 65 1 0 35 66 1 0 36 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	HHRPSKAYQPDDGQ-KOJUQBNKSA-N
Standard InCHI	InChI=1S/C27H30O15/c28-7-15-19(33)21(35)23(37)26(40-15)18-14(41-27-24(38)22(36)20(34)16(8-29)42-27)6-12(32)17-11(31)5-13(39-25(17)18)9-1-3-10(30)4-2-9/h1-6,15-16,19-24,26-30,32-38H,7-8H2/t15-,16+,19+,20+,21-,22-,23-,24+,26+,27+/m0/s1
SMILES	c1cc(ccc1c1cc(=O)c2c(cc(c(c2o1)[C@@H]1[C@H]([C@H]([C@@H]([C@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	-0.538 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.628 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.071 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	260.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.142	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.732	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.645	Fluc inhibitor:	0.157 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.886 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.621 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.244	Promiscuous compounds:	0.371

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.775	MDCK Permeability:	-4.899
Pgp-inhibitor:	0.0	Pgp-substrate:	0.855
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):	0.909
20% Bioavailability (F20%):	0.684	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.247
Plasma Protein Binding (PPB):	82.538%	Volume Distribution (VD):	0.023
Fu:	16.02% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.026
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.124
HLM stability:	0.002 ? 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):

2.012

Half-life (T1/2):

5.314

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.052
Human Hepatotoxicity (H-HT):	0.79	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.954	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.036	Skin Sensitization:	1.0
Carcinogencity:	0.084	Eye Corrosion:	0.0
Eye Irritation:	0.113	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.961
Hematotoxicity:	0.258	Drug-induced Nephrotoxicity:	0.787
Genotoxicity:	0.967	RPMI-8226 Immunitoxicity:	0.194
A549 Cytotoxicity:	0.468	Hek293 Cytotoxicity:	0.491
BCF:	0.281 ? 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:	2.693 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.414 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.519 ? 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
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15739361]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[23845552]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	seeds	n.a.	n.a.	PMID[23999046]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29254897]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37120447]
NPO30626	Trigonella foenum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2433	Vitex lucens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23807	Trollius macropetalus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31536	Crataegus oxyacantha	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2433	Vitex lucens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30626	Trigonella foenum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23807	Trollius macropetalus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31536	Crataegus oxyacantha	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24515	Crataegus rhipidophylla	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2433	Vitex lucens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23807	Trollius macropetalus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31536	Crataegus oxyacantha	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23807	Trollius macropetalus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23807	Trollius macropetalus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2433	Vitex lucens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24515	Crataegus rhipidophylla	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	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 NPC77869 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	22852
0.1-0.2	23432
0.2-0.3	2382
0.3-0.4	888
0.4-0.5	230
0.5-0.6	60
0.6-0.7	11
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
0.6705	Remote Similarity	NPC472607
0.6627	Remote Similarity	NPC39360
0.6627	Remote Similarity	NPC29763
0.6627	Remote Similarity	NPC210003
0.6484	Remote Similarity	NPC607513
0.6463	Remote Similarity	NPC209846
0.6383	Remote Similarity	NPC124155
0.6344	Remote Similarity	NPC606547
0.6163	Remote Similarity	NPC259152
0.6092	Remote Similarity	NPC105025
0.6087	Remote Similarity	NPC603300
0.5977	Remote Similarity	NPC93337
0.5977	Remote Similarity	NPC146792
0.593	Remote Similarity	NPC112701
0.5909	Remote Similarity	NPC10807
0.5909	Remote Similarity	NPC161881
0.587	Remote Similarity	NPC190393
0.5862	Remote Similarity	NPC83283
0.581	Remote Similarity	NPC132111
0.5795	Remote Similarity	NPC189142
0.5795	Remote Similarity	NPC77660
0.5789	Remote Similarity	NPC183672
0.5682	Remote Similarity	NPC261866
0.5632	Remote Similarity	NPC117418
0.5632	Remote Similarity	NPC328740
0.5632	Remote Similarity	NPC289774
0.5618	Remote Similarity	NPC95090
0.5618	Remote Similarity	NPC27408
0.5618	Remote Similarity	NPC323593
0.5618	Remote Similarity	NPC203500
0.5618	Remote Similarity	NPC607327
0.5568	Remote Similarity	NPC331652
0.5556	Remote Similarity	NPC610763
0.5543	Remote Similarity	NPC601144
0.5506	Remote Similarity	NPC143851
0.5484	Remote Similarity	NPC326592
0.5484	Remote Similarity	NPC311830
0.5484	Remote Similarity	NPC109594
0.5444	Remote Similarity	NPC297987
0.5444	Remote Similarity	NPC111341
0.5376	Remote Similarity	NPC601710
0.5361	Remote Similarity	NPC47923
0.5326	Remote Similarity	NPC27942
0.5326	Remote Similarity	NPC201292
0.5319	Remote Similarity	NPC607707
0.5312	Remote Similarity	NPC44947
0.5248	Remote Similarity	NPC150767
0.5217	Remote Similarity	NPC186807
0.5217	Remote Similarity	NPC58716
0.5217	Remote Similarity	NPC45638
0.5213	Remote Similarity	NPC22832
0.5213	Remote Similarity	NPC243930
0.5165	Remote Similarity	NPC58053
0.5165	Remote Similarity	NPC77672
0.5165	Remote Similarity	NPC45618
0.5165	Remote Similarity	NPC133671
0.5165	Remote Similarity	NPC135391
0.5165	Remote Similarity	NPC78263
0.5165	Remote Similarity	NPC250069
0.5158	Remote Similarity	NPC88023
0.5158	Remote Similarity	NPC116458
0.5158	Remote Similarity	NPC246943
0.5158	Remote Similarity	NPC309025
0.5158	Remote Similarity	NPC602805
0.5109	Remote Similarity	NPC8573
0.5109	Remote Similarity	NPC277205
0.5109	Remote Similarity	NPC37919
0.5106	Remote Similarity	NPC168584
0.5106	Remote Similarity	NPC191306
0.5054	Remote Similarity	NPC84265
0.5054	Remote Similarity	NPC602537

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC77869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5567
0.1-0.2	3497
0.2-0.3	65
0.3-0.4	18
0.4-0.5	3
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