NPASS Compound

Natural Product: NPC21836

Natural Product ID	NPC21836
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZPEADZHVGOCGKH-YQTDNFGYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6326020
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 66 68 0 0 0 0 0 0 0 0999 V2000 8.5408 2.1710 -0.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5764 1.3156 0.7071 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4245 0.5785 1.0032 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2951 0.6738 0.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1400 -0.0166 0.4828 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1401 -0.8680 1.5710 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2774 -0.9993 2.3765 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4165 -0.2799 2.0957 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5724 -0.3737 2.8636 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9847 0.1585 -0.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8315 -0.4588 -0.2488 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7687 -0.1771 -1.2030 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9430 0.6382 -2.1413 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5191 -0.7727 -1.1472 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5222 -0.5396 -2.0269 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8663 -1.8511 -2.7136 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9601 -2.3869 -1.8545 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4146 -3.4724 -0.9536 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4168 -4.0282 -0.1542 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5256 -1.3500 -1.1786 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -0.1825 -1.3688 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6006 0.7067 -2.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8897 1.9114 -2.5068 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6786 0.4284 -0.1560 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9084 0.6875 0.4166 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1120 2.1631 0.6994 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1829 2.3641 1.7503 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1263 1.1740 1.6572 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3147 -0.0560 2.0393 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9859 -1.2893 1.4741 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3158 -1.3468 1.8862 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9950 0.0499 1.6618 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1935 1.3862 2.5192 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9229 3.5034 1.4498 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9380 2.7444 1.1641 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2951 -1.6473 -4.0216 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2943 1.5349 -1.3046 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6760 2.8682 -0.2882 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4830 2.7154 -0.5501 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3181 1.3567 -0.6119 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 -1.4488 1.8180 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2465 -1.6763 3.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8861 -1.2770 3.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0795 0.8577 -1.2246 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7097 -1.1524 0.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3053 0.1893 -2.8294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0249 -2.5639 -2.7180 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7521 -2.8389 -2.5125 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9707 -4.2549 -1.6099 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5886 -3.0287 -0.3404 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6378 -3.3465 0.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6384 0.2526 -3.3353 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5961 0.9882 -1.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3224 1.9004 -3.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7839 0.3576 -0.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4438 2.7120 -0.2052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7590 2.3872 2.7742 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5320 1.0957 0.6242 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3624 -0.1405 3.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4329 -2.1879 1.7885 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0234 -1.2249 0.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.9243 1.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2656 2.3155 2.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6858 3.3248 0.8465 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7598 2.3382 2.0514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5656 -1.6876 -4.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 1 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 27 34 1 0 26 35 1 0 16 36 1 0 8 3 1 0 21 15 1 0 32 25 1 0 1 37 1 0 1 38 1 0 1 39 1 0 4 40 1 0 6 41 1 0 7 42 1 0 9 43 1 0 10 44 1 0 11 45 1 0 15 46 1 6 16 47 1 6 17 48 1 6 18 49 1 0 18 50 1 0 19 51 1 0 22 52 1 0 22 53 1 0 23 54 1 0 25 55 1 6 26 56 1 6 27 57 1 1 28 58 1 6 29 59 1 1 30 60 1 0 30 61 1 0 31 62 1 0 33 63 1 0 34 64 1 0 35 65 1 0 36 66 1 0 M END

Standard InCHIKey	ZPEADZHVGOCGKH-YQTDNFGYSA-N
Standard InCHI	InChI=1S/C22H30O14/c1-32-12-6-10(2-4-11(12)26)3-5-15(27)34-20-17(29)14(8-24)35-22(20,9-25)36-21-19(31)18(30)16(28)13(7-23)33-21/h2-6,13-14,16-21,23-26,28-31H,7-9H2,1H3/b5-3+/t13-,14-,16-,17-,18+,19-,20+,21-,22+/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)O[C@H]1[C@@H]([C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.16	Volume:	473.28 ? Van der Waals volume.
Dense:	1.095	LogP:	-0.467 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.152 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.768 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	19.0
TPSA:	225.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	3.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.118	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.604	Fsp³:	0.591
MCE-18:	84.343 ? 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:	0
Colloidal aggregators:	0.745	Fluc inhibitor:	0.48 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.213 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.273 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.228	Promiscuous compounds:	0.262

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.543	MDCK Permeability:	-5.21
Pgp-inhibitor:	0.0	Pgp-substrate:	0.129
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):	0.901
20% Bioavailability (F20%):	0.602	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.004
Plasma Protein Binding (PPB):	60.416%	Volume Distribution (VD):	-0.425
Fu:	40.673% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.081
BSEP inhibitor:	0.03

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.024	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.006
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.963
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):

1.237

Half-life (T1/2):

2.608

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.191
Human Hepatotoxicity (H-HT):	0.52	Drug-induced Liver Injury (DILI):	0.649
AMES Toxicity:	0.802	Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.026	Skin Sensitization:	1.0
Carcinogencity:	0.036	Eye Corrosion:	0.0
Eye Irritation:	0.318	Respiratory Toxicity:	0.027
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.948
Hematotoxicity:	0.247	Drug-induced Nephrotoxicity:	0.706
Genotoxicity:	0.048	RPMI-8226 Immunitoxicity:	0.188
A549 Cytotoxicity:	0.253	Hek293 Cytotoxicity:	0.123
BCF:	0.248 ? 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:	2.645 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.398 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.49 ? 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
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	roots	n.a.	n.a.	PMID[16989524]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711347]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18771240]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22863942]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24042007]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	root	n.a.	PMID[24317429]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38415909]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38838926]
NPO3457	Streptomyces diastaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8904845]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3457	Streptomyces diastaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21068	Centaurea sulphurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19599	Pogostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16807	Cyclamen purpurascens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5811	Pityrodia lepidota	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20448	Trifolium caucasicum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11115	Aspilia mossambicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21581	Polygala arillata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21508	Tilia tomentosa	Species	Malvaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21581	Polygala arillata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16807	Cyclamen purpurascens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21581	Polygala arillata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21068	Centaurea sulphurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3457	Streptomyces diastaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21508	Tilia tomentosa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19599	Pogostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11816.1	Vigna unguiculata subsp. unguiculata	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11115	Aspilia mossambicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21581	Polygala arillata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21453	Variolaria amara	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6135	Ehretia philippinensis	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20448	Trifolium caucasicum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16807	Cyclamen purpurascens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5811	Pityrodia lepidota	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
NPO27260	Polygala tenuifolia	n.a.	n.a.	1.783 Â± 0.030	n.a.	n.a.	mg/g	PMID[38838926]

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 NPC21836 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	12633
0.1-0.2	30814
0.2-0.3	5000
0.3-0.4	1133
0.4-0.5	227
0.5-0.6	32
0.6-0.7	13
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8406	Intermediate Similarity	NPC297342
0.84	Intermediate Similarity	NPC83743
0.8267	Intermediate Similarity	NPC262182
0.7206	Intermediate Similarity	NPC157554
0.7089	Intermediate Similarity	NPC90896
0.7073	Intermediate Similarity	NPC300262
0.6747	Remote Similarity	NPC80732
0.6706	Remote Similarity	NPC173343
0.6667	Remote Similarity	NPC283839
0.6628	Remote Similarity	NPC3460
0.6456	Remote Similarity	NPC225307
0.6353	Remote Similarity	NPC216819
0.6341	Remote Similarity	NPC226005
0.6322	Remote Similarity	NPC287615
0.6322	Remote Similarity	NPC199311
0.625	Remote Similarity	NPC307110
0.622	Remote Similarity	NPC472612
0.618	Remote Similarity	NPC472611
0.6044	Remote Similarity	NPC261122
0.5978	Remote Similarity	NPC28651
0.5955	Remote Similarity	NPC125823
0.5955	Remote Similarity	NPC7145
0.5955	Remote Similarity	NPC143480
0.5843	Remote Similarity	NPC229548
0.5778	Remote Similarity	NPC203664
0.5761	Remote Similarity	NPC201148
0.5747	Remote Similarity	NPC476865
0.573	Remote Similarity	NPC192763
0.5529	Remote Similarity	NPC199928
0.5517	Remote Similarity	NPC476868
0.5484	Remote Similarity	NPC210611
0.5417	Remote Similarity	NPC232880
0.5402	Remote Similarity	NPC476869
0.5393	Remote Similarity	NPC289967
0.5349	Remote Similarity	NPC28637
0.5312	Remote Similarity	NPC179914
0.5278	Remote Similarity	NPC11724
0.5256	Remote Similarity	NPC202700
0.5227	Remote Similarity	NPC173150
0.52	Remote Similarity	NPC470933
0.5195	Remote Similarity	NPC100389
0.5182	Remote Similarity	NPC246024
0.5169	Remote Similarity	NPC478887
0.5106	Remote Similarity	NPC34587
0.5104	Remote Similarity	NPC100998
0.5104	Remote Similarity	NPC34927
0.5098	Remote Similarity	NPC306890
0.5057	Remote Similarity	NPC156692
0.5055	Remote Similarity	NPC478883
0.5054	Remote Similarity	NPC89693
0.5052	Remote Similarity	NPC232992

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC21836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4376
0.1-0.2	4613
0.2-0.3	149
0.3-0.4	11
0.4-0.5	1
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