NPASS Compound

Natural Product: NPC167383

Natural Product ID	NPC167383
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oleanolic Acid 28-O-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510111
PubChem CID	14189384
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 102107 0 0 0 0 0 0 0 0999 V2000 7.6323 -0.6349 0.6952 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3306 0.6925 1.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1011 1.5230 -0.2155 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0744 1.0887 -1.0021 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8052 1.4262 -0.6298 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0672 0.2628 -0.2540 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9873 -0.1340 -0.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6636 0.5599 -1.9882 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1657 -1.3587 -0.6302 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1180 -2.5063 -0.7026 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3901 -3.8018 -0.6493 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4983 -3.8686 -1.8389 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5298 -2.7518 -1.9984 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0012 -1.4102 -1.5537 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1582 -0.6238 -1.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8383 0.0886 -1.9256 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0174 0.9337 -1.6307 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6838 0.2855 -0.4268 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7094 0.2976 0.6787 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5620 -0.6212 0.3411 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7179 -0.1862 1.0778 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8196 -1.1745 0.8277 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8880 -1.9756 0.9018 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1127 1.6501 0.9872 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3835 -0.1532 1.9582 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6136 0.7026 2.2607 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5562 0.3673 1.1321 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0562 0.8129 -0.1926 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2299 2.2800 -0.4699 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9653 0.1058 -1.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4100 0.3831 -1.0130 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9265 0.3270 0.3714 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9777 0.7072 1.4515 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1874 2.1169 1.9215 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3309 -0.1813 2.6637 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0228 1.2192 0.4621 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7970 -5.2099 -1.8251 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4088 -3.8895 -3.0749 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6709 2.4646 0.4299 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7534 3.4915 0.4585 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1071 3.0036 0.0747 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6195 3.6784 -1.0493 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8328 3.9629 1.7871 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4661 3.1713 0.1892 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0545 -0.6744 -0.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4356 0.6513 1.6606 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2202 1.0766 1.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0434 1.3556 -0.8314 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3159 1.8553 -1.5561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7778 -2.4882 -1.5904 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7911 -2.4550 0.1815 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8739 -3.9810 0.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1393 -4.6177 -0.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4698 -3.0466 -1.5531 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2595 -2.7743 -3.1063 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3699 -0.9314 -2.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5243 0.0801 -2.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6954 1.0358 -2.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6695 1.9846 -1.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8022 -0.7996 -0.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5530 -0.1463 2.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0761 0.7916 0.7546 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7270 -0.7093 1.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7151 -2.1325 1.3793 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8242 -2.4078 0.5682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1130 -2.7410 0.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9461 -1.8403 2.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8741 2.4308 1.1569 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6003 1.5320 1.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4314 2.0334 0.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8385 -1.1762 1.8059 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7451 -0.0981 2.8330 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3897 1.7517 2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0482 0.2913 3.1947 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5390 -0.7613 1.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5677 2.6368 -1.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0881 2.9319 0.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2644 2.5216 -0.8606 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7002 0.3890 -2.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7990 -0.9815 -1.1281 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7603 1.3275 -1.5292 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9491 -0.4116 -1.6173 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4023 -0.6814 0.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5567 2.8062 1.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0041 2.1372 2.7057 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2931 2.5229 2.4588 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8394 -1.1562 2.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4401 -0.2586 2.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0681 0.3741 3.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0212 1.8470 -0.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1970 -5.4039 -2.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5867 -5.9888 -1.7793 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1903 -5.3397 -0.8881 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7237 -4.1639 -3.9252 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2311 -4.6024 -2.9638 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7330 -2.8478 -3.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5021 2.0298 1.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4879 4.3638 -0.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8697 3.1515 0.8939 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1613 4.5708 -1.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7563 3.9138 2.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5453 4.1012 0.5379 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 9 7 1 6 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 1 19 24 1 1 19 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 32 36 1 0 12 37 1 0 12 38 1 0 5 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 41 3 1 0 22 9 1 0 33 27 1 0 14 9 1 0 20 15 1 0 28 18 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 6 5 49 1 6 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 13 55 1 0 14 56 1 6 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 6 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 6 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 31 82 1 0 32 83 1 1 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 0 35 88 1 0 35 89 1 0 36 90 1 0 37 91 1 0 37 92 1 0 37 93 1 0 38 94 1 0 38 95 1 0 38 96 1 0 39 97 1 1 40 98 1 6 41 99 1 1 42100 1 0 43101 1 0 44102 1 0 M END

Standard InCHIKey	KMKFOIBUKYMVRJ-YHFBEQRYSA-N
Standard InCHI	InChI=1S/C36H58O8/c1-31(2)14-16-36(30(42)44-29-28(41)27(40)26(39)22(19-37)43-29)17-15-34(6)20(21(36)18-31)8-9-24-33(5)12-11-25(38)32(3,4)23(33)10-13-35(24,34)7/h8,21-29,37-41H,9-19H2,1-7H3/t21-,22+,23-,24+,25-,26+,27-,28+,29-,33-,34+,35+,36-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@@]23CCC(C[C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.41	Volume:	644.922 ? Van der Waals volume.
Dense:	0.959	LogP:	3.065 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.25 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.87 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.231	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.196	Fsp³:	0.917
MCE-18:	128.058 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.965	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.189	Promiscuous compounds:	0.106

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.626	MDCK Permeability:	-5.109
Pgp-inhibitor:	0.001	Pgp-substrate:	0.019
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):	0.076
20% Bioavailability (F20%):	0.902	30% Bioavailability (F30%):	0.985
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973	MRP1:	0.354
Plasma Protein Binding (PPB):	85.14%	Volume Distribution (VD):	-0.362
Fu:	9.922% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.055
BSEP inhibitor:	0.11

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.857	CYP2C19-substrate:	0.195
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.025	CYP3A4-substrate:	0.052
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.904
HLM stability:	0.619 ? 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):

1.414

Half-life (T1/2):

2.164

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.057
Human Hepatotoxicity (H-HT):	0.712	Drug-induced Liver Injury (DILI):	0.567
AMES Toxicity:	0.792	Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.12	Skin Sensitization:	0.998
Carcinogencity:	0.662	Eye Corrosion:	0.0
Eye Irritation:	0.019	Respiratory Toxicity:	0.142
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.959
Hematotoxicity:	0.481	Drug-induced Nephrotoxicity:	0.949
Genotoxicity:	0.695	RPMI-8226 Immunitoxicity:	0.098
A549 Cytotoxicity:	0.678	Hek293 Cytotoxicity:	0.343
BCF:	1.895 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.017 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.601 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.841 ? 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
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19254038]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[21417387]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[21417387]
NPO18815	Lobophytum cristatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954851]
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28098996]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117520]
NPO20986	Eucalyptus torquata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34705324]
NPO11459	Parmelia formosana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10387	Mandragora vernalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9554	Parthenium ligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO881	Aster praealtus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18475	Achlya bisexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12033	Trimusculus peruvianus	Species	Trimusculidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15071	Lissoclinum perforatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9437	Acacia aneura	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO773	Siphonaria maura	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13487	Rhizosolenia setigera	Species	Rhizosoleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1620	Dictyopteris prolifera	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11921	Actinosynnema pretiosum	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8098	Strongylocentrotus lividus	Species	Strongylocentrotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9437	Acacia aneura	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1931	Lycorea ceres	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17308	Anaptychia heterochroa	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16664	Salix sachalinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8494	Pteris longipes	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15071	Lissoclinum perforatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9554	Parthenium ligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18815	Lobophytum cristatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10373	Senna pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1620	Dictyopteris prolifera	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20986	Eucalyptus torquata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3067	Frullania nisquallensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10972	Lysimachia patungensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13487	Rhizosolenia setigera	Species	Rhizosoleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO881	Aster praealtus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11921	Actinosynnema pretiosum	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16415	Drypetes paxii	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10387	Mandragora vernalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18475	Achlya bisexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6196	Aralia armata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO156	Silene nutans	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8750	Lychnis githago	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11459	Parmelia formosana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8913	Ramariopsis helvola	Species	Clavariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO773	Siphonaria maura	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12033	Trimusculus peruvianus	Species	Trimusculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1532	Chrysanthemum ircutianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Inhibition	1

Activity Type	# Activity
Individual protein	2
Cell line	1
Others	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2681	Individual protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	293000.0	nM	PMID[18517260]
NPT677	Individual protein	Coagulation factor III	Homo sapiens	IC50	=	0.035	nM	PMID[28109788]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[30808589]
NPT2	Others	Unspecified	n.a.	Inhibition	=	43.6	%	PMID[21417387]
NPT2	Others	Unspecified	n.a.	IC50	=	9640.0	nM	PMID[21417387]
NPT2	Others	Unspecified	n.a.	IC50	=	75000.0	nM	PMID[21417387]

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 NPC167383 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	20261
0.1-0.2	23488
0.2-0.3	4509
0.3-0.4	1073
0.4-0.5	334
0.5-0.6	110
0.6-0.7	61
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8904	High Similarity	NPC237503
0.7927	Intermediate Similarity	NPC29069
0.7867	Intermediate Similarity	NPC191763
0.7792	Intermediate Similarity	NPC46388
0.7595	Intermediate Similarity	NPC306746
0.7381	Intermediate Similarity	NPC214484
0.7286	Intermediate Similarity	NPC246708
0.7222	Intermediate Similarity	NPC104071
0.7209	Intermediate Similarity	NPC48499
0.7143	Intermediate Similarity	NPC209894
0.7045	Intermediate Similarity	NPC235405
0.7045	Intermediate Similarity	NPC475516
0.6966	Remote Similarity	NPC249848
0.6966	Remote Similarity	NPC107966
0.6957	Remote Similarity	NPC473459
0.6951	Remote Similarity	NPC37739
0.6951	Remote Similarity	NPC199457
0.6889	Remote Similarity	NPC295371
0.6889	Remote Similarity	NPC473884
0.6889	Remote Similarity	NPC39211
0.6889	Remote Similarity	NPC157868
0.6867	Remote Similarity	NPC68419
0.6813	Remote Similarity	NPC469946
0.6778	Remote Similarity	NPC150400
0.6739	Remote Similarity	NPC192791
0.6739	Remote Similarity	NPC223301
0.6739	Remote Similarity	NPC242840
0.6739	Remote Similarity	NPC171544
0.6739	Remote Similarity	NPC112352
0.6667	Remote Similarity	NPC30735
0.6667	Remote Similarity	NPC137917
0.6667	Remote Similarity	NPC604133
0.6596	Remote Similarity	NPC40775
0.6596	Remote Similarity	NPC10607
0.6596	Remote Similarity	NPC251768
0.6596	Remote Similarity	NPC159309
0.6596	Remote Similarity	NPC102439
0.6596	Remote Similarity	NPC46665
0.6596	Remote Similarity	NPC86222
0.6591	Remote Similarity	NPC90856
0.6526	Remote Similarity	NPC475591
0.6526	Remote Similarity	NPC63159
0.6526	Remote Similarity	NPC236870
0.6526	Remote Similarity	NPC235438
0.6506	Remote Similarity	NPC605954
0.6471	Remote Similarity	NPC310014
0.6471	Remote Similarity	NPC269315
0.6458	Remote Similarity	NPC222580
0.6458	Remote Similarity	NPC297263
0.6327	Remote Similarity	NPC281148
0.6327	Remote Similarity	NPC104372
0.6327	Remote Similarity	NPC114484
0.6279	Remote Similarity	NPC7870
0.6279	Remote Similarity	NPC75747
0.6263	Remote Similarity	NPC301449
0.6263	Remote Similarity	NPC601290
0.625	Remote Similarity	NPC101475
0.6237	Remote Similarity	NPC473373
0.62	Remote Similarity	NPC80986
0.6164	Remote Similarity	NPC235341
0.6139	Remote Similarity	NPC31838
0.6139	Remote Similarity	NPC481078
0.6139	Remote Similarity	NPC187290
0.6129	Remote Similarity	NPC139894
0.6122	Remote Similarity	NPC609763
0.6092	Remote Similarity	NPC48249
0.6056	Remote Similarity	NPC290598
0.6056	Remote Similarity	NPC30590
0.6047	Remote Similarity	NPC116794
0.604	Remote Similarity	NPC481030
0.6023	Remote Similarity	NPC271138
0.6023	Remote Similarity	NPC110139
0.6023	Remote Similarity	NPC108709
0.5979	Remote Similarity	NPC309714
0.5978	Remote Similarity	NPC1046
0.5941	Remote Similarity	NPC481079
0.5938	Remote Similarity	NPC473343
0.5934	Remote Similarity	NPC47063
0.5918	Remote Similarity	NPC305267
0.5918	Remote Similarity	NPC480475
0.5914	Remote Similarity	NPC475208
0.5905	Remote Similarity	NPC79643
0.5889	Remote Similarity	NPC128925
0.5889	Remote Similarity	NPC256798
0.587	Remote Similarity	NPC204458
0.587	Remote Similarity	NPC189884
0.587	Remote Similarity	NPC138334
0.5849	Remote Similarity	NPC481031
0.5843	Remote Similarity	NPC102914
0.5816	Remote Similarity	NPC109588
0.58	Remote Similarity	NPC475504
0.5794	Remote Similarity	NPC135904
0.5794	Remote Similarity	NPC123199
0.5778	Remote Similarity	NPC220984
0.5769	Remote Similarity	NPC75287
0.5769	Remote Similarity	NPC136313
0.5758	Remote Similarity	NPC11551
0.5741	Remote Similarity	NPC475160
0.5741	Remote Similarity	NPC100639
0.5741	Remote Similarity	NPC470218
0.5741	Remote Similarity	NPC473714
0.5728	Remote Similarity	NPC295823
0.5728	Remote Similarity	NPC96641
0.5728	Remote Similarity	NPC174720
0.5728	Remote Similarity	NPC163183
0.5728	Remote Similarity	NPC241909
0.5728	Remote Similarity	NPC475467
0.5699	Remote Similarity	NPC269095
0.5696	Remote Similarity	NPC488519
0.5682	Remote Similarity	NPC190837
0.5658	Remote Similarity	NPC470588
0.5644	Remote Similarity	NPC31193
0.5638	Remote Similarity	NPC78046
0.5636	Remote Similarity	NPC481080
0.5612	Remote Similarity	NPC475171
0.5586	Remote Similarity	NPC476068
0.5579	Remote Similarity	NPC179434
0.5577	Remote Similarity	NPC480473
0.5577	Remote Similarity	NPC69811
0.5577	Remote Similarity	NPC480474
0.5567	Remote Similarity	NPC58448
0.5556	Remote Similarity	NPC75417
0.5526	Remote Similarity	NPC253807
0.5526	Remote Similarity	NPC158662
0.5514	Remote Similarity	NPC60557
0.5514	Remote Similarity	NPC76972
0.5514	Remote Similarity	NPC469782
0.5514	Remote Similarity	NPC67857
0.5514	Remote Similarity	NPC204414
0.5487	Remote Similarity	NPC41061
0.5487	Remote Similarity	NPC227551
0.5487	Remote Similarity	NPC258617
0.5463	Remote Similarity	NPC192600
0.5439	Remote Similarity	NPC293330
0.5439	Remote Similarity	NPC65105
0.5439	Remote Similarity	NPC43550
0.5437	Remote Similarity	NPC64715
0.5413	Remote Similarity	NPC475899
0.5395	Remote Similarity	NPC34177
0.5395	Remote Similarity	NPC196753
0.5391	Remote Similarity	NPC305981
0.5391	Remote Similarity	NPC481081
0.5375	Remote Similarity	NPC214756
0.537	Remote Similarity	NPC475287
0.5368	Remote Similarity	NPC238935
0.5366	Remote Similarity	NPC49776
0.5366	Remote Similarity	NPC63118
0.5366	Remote Similarity	NPC474436
0.5364	Remote Similarity	NPC155410
0.5347	Remote Similarity	NPC160415
0.5345	Remote Similarity	NPC261506
0.5345	Remote Similarity	NPC298034
0.5345	Remote Similarity	NPC71065
0.5345	Remote Similarity	NPC4328
0.5319	Remote Similarity	NPC607754
0.5316	Remote Similarity	NPC40552
0.5315	Remote Similarity	NPC191827
0.531	Remote Similarity	NPC57484
0.5309	Remote Similarity	NPC481361
0.53	Remote Similarity	NPC263756
0.53	Remote Similarity	NPC161674
0.53	Remote Similarity	NPC213674
0.5294	Remote Similarity	NPC164389
0.5275	Remote Similarity	NPC65590
0.5275	Remote Similarity	NPC125923
0.5268	Remote Similarity	NPC488560
0.525	Remote Similarity	NPC162107
0.525	Remote Similarity	NPC46912
0.5243	Remote Similarity	NPC68175
0.5238	Remote Similarity	NPC294360
0.521	Remote Similarity	NPC250247
0.5195	Remote Similarity	NPC311078
0.519	Remote Similarity	NPC267517
0.5185	Remote Similarity	NPC11242
0.5179	Remote Similarity	NPC471550
0.5146	Remote Similarity	NPC101744
0.5133	Remote Similarity	NPC25663
0.5128	Remote Similarity	NPC135849
0.5109	Remote Similarity	NPC479080
0.5096	Remote Similarity	NPC148417
0.5091	Remote Similarity	NPC300419
0.5088	Remote Similarity	NPC487505
0.5065	Remote Similarity	NPC474989

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC167383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7309
0.1-0.2	1762
0.2-0.3	74
0.3-0.4	4
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