NPASS Compound

Natural Product: NPC31034

Natural Product ID	NPC31034
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pedunculagin
IUPAC Name	n.a.
Synonyms	Pedunculagin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506204
PubChem CID	442688
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 80 86 0 0 0 0 0 0 0 0999 V2000 1.4391 4.3943 -1.9380 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7550 3.2788 -1.5116 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3703 3.7563 -0.7312 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1920 2.7585 -0.4039 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4052 3.1861 0.3450 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2737 2.0176 0.3733 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7986 1.6171 -0.8302 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5038 2.3623 -1.8350 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6346 0.4326 -1.0412 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1150 0.3449 -2.3752 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8517 -0.7647 -2.7317 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3032 -0.8073 -4.0525 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1207 -1.7621 -1.8375 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6417 -1.6414 -0.5610 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9010 -0.5441 -0.1599 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5327 -0.5492 1.2435 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3273 -0.5182 1.7940 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9931 -0.2609 1.2034 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3068 -1.2502 0.9632 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5142 0.9380 0.9403 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4813 1.6302 0.4751 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5265 1.1260 -0.4687 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4480 2.3981 -0.6138 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7308 1.8668 -0.9138 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5403 1.5200 0.1397 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9815 1.7776 1.3027 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8412 0.9406 0.2590 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7389 1.6583 1.0660 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9729 1.1969 1.4285 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8585 1.8903 2.2143 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3013 -0.0519 0.9475 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4407 -0.7635 0.1606 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2200 -0.2799 -0.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4024 -1.1132 -1.1104 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1297 -1.4596 -0.9633 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0304 -0.9173 -0.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7402 -1.4996 0.9306 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3181 0.1298 -0.3725 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5851 -2.4016 -1.8516 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3047 -2.9632 -2.8577 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5984 -2.6020 -3.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1573 -1.6858 -2.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4771 -1.2762 -2.3037 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4183 -3.1220 -4.0257 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7343 -3.9030 -3.7269 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8610 -2.0133 -0.2544 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5511 -0.6201 1.2671 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1796 -0.6549 3.1894 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2183 -0.8141 4.0290 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1252 -0.9527 5.4039 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4845 -0.8387 3.4379 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6340 -0.7112 2.1020 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8961 -0.7342 1.5502 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5858 -1.0032 4.3116 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8924 -2.6553 0.3955 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8610 -2.8498 -2.2490 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2313 4.5111 -1.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2620 2.7326 -2.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4829 2.1752 -1.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2317 3.5620 1.3512 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9445 3.9259 -0.2674 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9154 1.1270 -3.1023 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0421 -1.4346 -4.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0518 2.2848 1.2260 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0886 1.1064 -1.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 2.9201 0.3973 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4201 2.6527 1.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0305 1.6196 3.1743 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5286 -2.6654 -1.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6375 -0.2962 -2.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1410 -2.5412 -4.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2369 -4.7659 -3.8604 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4293 -2.6086 0.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6283 -1.5674 1.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1589 -0.6483 3.5852 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4248 -0.1281 5.9452 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6920 -0.2709 1.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2411 -0.2429 4.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1765 -2.8964 1.0586 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6442 -3.7880 -1.9876 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 11 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 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 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 29 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 35 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 41 44 1 0 40 45 1 0 32 46 1 0 31 47 1 0 17 48 1 0 48 49 2 0 49 50 1 0 49 51 1 0 51 52 2 0 52 53 1 0 51 54 1 0 14 55 1 0 13 56 1 0 23 2 1 0 33 27 1 0 42 34 1 0 21 4 1 0 38 22 1 0 15 9 1 0 52 16 1 0 1 57 1 0 2 58 1 0 4 59 1 6 5 60 1 0 5 61 1 0 10 62 1 0 12 63 1 0 21 64 1 1 22 65 1 6 23 66 1 1 28 67 1 0 30 68 1 0 39 69 1 0 43 70 1 0 44 71 1 0 45 72 1 0 46 73 1 0 47 74 1 0 48 75 1 0 50 76 1 0 53 77 1 0 54 78 1 0 55 79 1 0 56 80 1 0 M END

Standard InCHIKey	IYMHVUYNBVWXKH-ZITZVVOASA-N
Standard InCHI	InChI=1S/C34H24O22/c35-10-1-6-15(23(43)19(10)39)16-7(2-11(36)20(40)24(16)44)31(48)54-27-14(5-52-30(6)47)53-34(51)29-28(27)55-32(49)8-3-12(37)21(41)25(45)17(8)18-9(33(50)56-29)4-13(38)22(42)26(18)46/h1-4,14,27-29,34-46,51H,5H2/t14-,27-,28+,29-,34?/m1/s1
SMILES	OC1O[C@@H]2COC(=O)c3cc(O)c(c(c3c3c(C(=O)O[C@H]2[C@H]2[C@H]1OC(=O)c1cc(O)c(c(c1c1c(C(=O)O2)cc(c(c1O)O)O)O)O)cc(O)c(c3O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	784.08	Volume:	687.926 ? Van der Waals volume.
Dense:	1.14	LogP:	-1.394 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-1.719 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.376 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	49.0
TPSA:	377.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.066	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.422	Fsp³:	0.176
MCE-18:	165.0 ? 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:	0.982	Fluc inhibitor:	0.044 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.335 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.66 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.547	Promiscuous compounds:	0.999

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.551	MDCK Permeability:	-4.967
Pgp-inhibitor:	0.0	Pgp-substrate:	0.025
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):	0.012
20% Bioavailability (F20%):	0.223	30% Bioavailability (F30%):	0.64
50% Bioavailability (F50%):	0.701

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	67.281%	Volume Distribution (VD):	-0.206
Fu:	25.539% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	0.969	BCRP inhibitor:	0.014
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.049
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.044 ? 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):

5.65

Half-life (T1/2):

4.474

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.918
Human Hepatotoxicity (H-HT):	0.654	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.996	Rat Oral Acute Toxicity:	0.178
Maximum Recommended Daily Dose:	0.893	Skin Sensitization:	1.0
Carcinogencity:	0.425	Eye Corrosion:	0.003
Eye Irritation:	0.996	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	0.146
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.002
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.144
BCF:	0.13 ? 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:	3.172 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.096 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.016 ? 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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/np50028a032]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10993241]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36431782]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36560643]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39138188]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39527985]
NPO28472	Quercus petraea	Species	Fagaceae	Eukaryota	Barks	n.a.	n.a.	PMID[7807126]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834152]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28472	Quercus petraea	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28472	Quercus petraea	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3129	Geum japonicum	Species	Rosaceae	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

Activity Type	# Activity
IC50	6
Ki	2
ED50	5
Ratio Ki	1
APTT	4
TT	4
PT	4
Activity	11
Inhibition	6

Activity Type	# Activity
Individual protein	6
Cell line	4
Organism	6
Non-molecular	1
Others	13
Tissue	13

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT326	Individual protein	Squalene monooxygenase	Rattus norvegicus	IC50	=	2000.0	nM	PMID[11520216]
NPT2533	Individual protein	Coagulation factor X	Homo sapiens	IC50	=	560.0	nM	PMID[9834152]
NPT2533	Individual protein	Coagulation factor X	Homo sapiens	Ki	=	990.0	nM	PMID[9834152]
NPT2534	Individual protein	Thrombin	Bos taurus	IC50	=	150.0	nM	PMID[9834152]
NPT2534	Individual protein	Thrombin	Bos taurus	IC50	=	180.0	nM	PMID[9834152]
NPT2534	Individual protein	Thrombin	Bos taurus	Ki	=	42.0	nM	PMID[9834152]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT672	Cell line	TE-671	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[1431932]
NPT180	Cell line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[1431932]
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[1431932]
NPT91	Cell line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[1431932]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	2.74	ug ml-1	PMID[1431932]
NPT1308	Tissue	Blood	Homo sapiens	Activity	=	0.2	n.a.	PMID[7807126]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	58.8	%	PMID[20144544]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	81.1	%	PMID[20144544]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	14.6	%	PMID[20144544]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	30.9	%	PMID[20144544]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	14.8	%	PMID[20144544]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	9.4	%	PMID[20144544]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	23.0	n.a.	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	=	60.2	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	=	33.5	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	=	15.2	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	>	300.0	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	>	300.0	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	>	300.0	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	=	35.3	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	=	12.6	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	=	10.2	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	=	43.7	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	=	22.7	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	=	13.5	s	PMID[9834152]
NPT2	Others	Unspecified	n.a.	Activity	=	80.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	4.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	17.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	15.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	51.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	88.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	73.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	41.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	7.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	Activity	=	10.0	%	PMID[2413172]
NPT2	Others	Unspecified	n.a.	IC50	=	7800.0	nM	PMID[7494143]
NPT2	Others	Unspecified	n.a.	IC50	=	12000.0	nM	PMID[7494143]

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
-	Rattus norvegicus	LD50	>	100.0	mg.kg-1	PMID[9834152]
-	Mus musculus	LD50	>	100.0	mg.kg-1	PMID[9834152]

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 NPC31034 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	20959
0.1-0.2	28059
0.2-0.3	701
0.3-0.4	72
0.4-0.5	37
0.5-0.6	24
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9038	High Similarity	NPC175793
0.9038	High Similarity	NPC159913
0.7015	Intermediate Similarity	NPC237202
0.6981	Remote Similarity	NPC239019
0.6981	Remote Similarity	NPC247629
0.6393	Remote Similarity	NPC488888
0.5949	Remote Similarity	NPC483711
0.5897	Remote Similarity	NPC269046
0.5875	Remote Similarity	NPC469650
0.5763	Remote Similarity	NPC135222
0.5763	Remote Similarity	NPC474010
0.5714	Remote Similarity	NPC47521
0.5663	Remote Similarity	NPC488887
0.5663	Remote Similarity	NPC488886
0.5625	Remote Similarity	NPC43918
0.5625	Remote Similarity	NPC261411
0.5625	Remote Similarity	NPC190204
0.56	Remote Similarity	NPC601554
0.5538	Remote Similarity	NPC469651
0.5402	Remote Similarity	NPC469652
0.5402	Remote Similarity	NPC486025
0.5402	Remote Similarity	NPC486024
0.5373	Remote Similarity	NPC302170
0.5303	Remote Similarity	NPC291957
0.5286	Remote Similarity	NPC26536
0.5286	Remote Similarity	NPC142707
0.5286	Remote Similarity	NPC317671
0.5286	Remote Similarity	NPC49983
0.5286	Remote Similarity	NPC217781
0.5111	Remote Similarity	NPC486110

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC31034 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5363
0.1-0.2	3769
0.2-0.3	17
0.3-0.4	1
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