NPASS Compound

Natural Product: NPC26065

Natural Product ID	NPC26065
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NXKDUDYUASKXAY-FQSUSTAMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5317394
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 88 92 0 0 0 0 0 0 0 0999 V2000 5.3147 -1.1299 -1.5414 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1560 -0.9057 -0.6202 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6807 -0.4946 0.7089 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6145 0.9736 0.9938 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1818 1.4066 0.9310 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3888 0.6158 -0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1312 0.0810 -1.2038 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7895 0.9443 -2.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2315 -0.8165 -2.0697 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9277 -0.0790 -2.4260 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2798 0.2355 -1.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0466 1.2887 -0.3914 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4337 2.5189 -1.1475 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3430 1.7750 0.8550 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1595 1.7386 0.8418 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7233 0.4600 0.2183 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0672 -0.5830 1.1295 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1663 0.2283 0.4457 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5565 -1.1285 0.9634 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9311 -1.0715 1.6559 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4786 -2.4961 1.6947 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8143 -0.5852 3.0582 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8534 -0.2656 0.7907 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3698 -0.4164 -0.6072 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0633 0.3886 -0.7911 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5647 1.8076 -0.8171 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4506 -0.1428 -2.0242 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9804 -0.5649 -1.9171 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2179 0.4698 -1.1761 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3334 1.7216 -1.9719 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9625 -1.0536 0.8690 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2847 -1.9937 1.8249 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3486 -2.3429 2.5755 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6152 -2.6044 2.0257 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9568 -1.8997 -1.0142 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9723 -0.2704 -1.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0309 -1.6556 -2.4934 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6656 -1.9174 -0.4981 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0433 -0.9786 1.5018 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2856 1.5963 0.3933 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0124 1.0894 2.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7759 1.2354 1.9763 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1622 2.4922 0.8164 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0682 -0.3007 0.5020 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5184 1.6734 -1.8629 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0953 1.3819 -2.9730 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3923 0.2382 -2.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7599 -1.1543 -2.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9224 -1.6520 -1.4076 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1436 0.7692 -3.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3616 -0.8194 -3.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3715 -0.7216 -0.5606 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5429 2.7604 -1.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0230 3.4771 -0.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2108 2.5925 -2.1922 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7616 1.3594 1.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5575 2.8836 1.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6305 2.6449 0.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4685 1.6639 1.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1820 -1.5959 0.7865 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5438 -0.3482 2.1384 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0367 -0.4176 1.3901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5210 0.9652 1.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9593 -1.6209 1.6969 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6097 -1.8424 0.0885 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0196 -3.1345 0.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5721 -2.4904 1.5012 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3536 -2.9379 2.7167 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3896 0.3602 3.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2519 -1.2878 3.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7514 -0.4653 3.3418 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7985 0.7704 1.1217 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8971 -0.6603 0.8188 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2868 -1.4377 -0.9684 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1518 0.0624 -1.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5703 1.9844 -0.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8914 2.5131 -0.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5928 2.1032 -1.9107 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9246 -1.1193 -2.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6248 0.4944 -2.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6681 -0.6406 -3.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8545 -1.5711 -1.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0603 2.6448 -1.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2930 1.9260 -2.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7218 1.5012 -2.9123 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3830 -2.1151 1.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6161 -3.7022 1.8656 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9915 -2.4055 3.0699 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 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 3 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 7 2 1 0 29 11 1 0 12 6 1 0 29 16 1 0 25 18 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 10 50 1 0 10 51 1 0 11 52 1 0 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 17 60 1 0 17 61 1 0 17 62 1 0 18 63 1 1 19 64 1 0 19 65 1 0 21 66 1 0 21 67 1 0 21 68 1 0 22 69 1 0 22 70 1 0 22 71 1 0 23 72 1 0 23 73 1 0 24 74 1 0 24 75 1 0 26 76 1 0 26 77 1 0 26 78 1 0 27 79 1 0 27 80 1 0 28 81 1 0 28 82 1 0 30 83 1 0 30 84 1 0 30 85 1 0 34 86 1 0 34 87 1 0 34 88 1 0 M END

Standard InCHIKey	NXKDUDYUASKXAY-FQSUSTAMSA-N
Standard InCHI	InChI=1S/C32H54O2/c1-21-23(34-22(2)33)10-11-24-29(21,6)13-12-25-30(24,7)17-19-32(9)26-20-27(3,4)14-15-28(26,5)16-18-31(25,32)8/h21,23-26H,10-20H2,1-9H3/t21-,23?,24?,25?,26+,28+,29+,30-,31+,32?/m0/s1
SMILES	C[C@H]1C(CCC2[C@]1(C)CCC1[C@@]2(C)CCC2(C)[C@@H]3CC(C)(C)CC[C@]3(C)CC[C@]12C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.41	Volume:	534.19 ? Van der Waals volume.
Dense:	0.881	LogP:	5.426 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.559 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.367 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.358	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.814	Fsp³:	0.969
MCE-18:	105.238 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.704	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.829	Promiscuous compounds:	0.098

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75	MDCK Permeability:	-4.823
Pgp-inhibitor:	0.997	Pgp-substrate:	0.001
PAMPA:	0.031 ? 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):	0.0
20% Bioavailability (F20%):	0.371	30% Bioavailability (F30%):	0.068
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999	MRP1:	0.997
Plasma Protein Binding (PPB):	97.673%	Volume Distribution (VD):	0.106
Fu:	2.676% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.044
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.528
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.318	CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.868	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

9.412

Half-life (T1/2):

0.179

ADMET: Toxicity

hERG Blockers:	0.335	hERG Blockers (10um):	0.772
Human Hepatotoxicity (H-HT):	0.738	Drug-induced Liver Injury (DILI):	0.171
AMES Toxicity:	0.07	Rat Oral Acute Toxicity:	0.326
Maximum Recommended Daily Dose:	0.619	Skin Sensitization:	0.875
Carcinogencity:	0.892	Eye Corrosion:	0.421
Eye Irritation:	0.687	Respiratory Toxicity:	0.33
Drug-induced Neurotoxicity:	0.318	Ototoxicity:	0.437
Hematotoxicity:	0.129	Drug-induced Nephrotoxicity:	0.297
Genotoxicity:	0.139	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.26	Hek293 Cytotoxicity:	0.615
BCF:	2.881 ? 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:	5.276 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.076 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.268 ? 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
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/P19890001079]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18396905]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18396905]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[21435874]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	Cupules	n.a.	n.a.	PMID[25098388]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30931559]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO22811	Bischofia javanica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7414	Elephantopus scaber	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2545	Aster scaber	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3392	Agastache rugosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6625	Euphoria longan	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18536	Vaccinium bracteatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27772	Flos inulae	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6625	Euphoria longan	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3392	Agastache rugosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22811	Bischofia javanica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18536	Vaccinium bracteatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29215	Millettia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7414	Elephantopus scaber	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18536	Vaccinium bracteatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2545	Aster scaber	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15156	Euphorbia tithymaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7414	Elephantopus scaber	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3392	Agastache rugosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6625	Euphoria longan	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27772	Flos inulae	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29215	Millettia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22811	Bischofia javanica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22811	Bischofia javanica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7414	Elephantopus scaber	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18536	Vaccinium bracteatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15156	Euphorbia tithymaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2545	Aster scaber	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29215	Millettia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22811	Bischofia javanica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7414	Elephantopus scaber	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6625	Euphoria longan	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18536	Vaccinium bracteatum	Species	Ericaceae	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 NPC26065 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	25537
0.1-0.2	21782
0.2-0.3	2406
0.3-0.4	113
0.4-0.5	12
0.5-0.6	7
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	Natural Product ID
0.5741	Remote Similarity	NPC178541
0.5686	Remote Similarity	NPC307063
0.5667	Remote Similarity	NPC243594
0.5294	Remote Similarity	NPC290791
0.5294	Remote Similarity	NPC292419
0.5185	Remote Similarity	NPC225467
0.5091	Remote Similarity	NPC267753

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC26065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7242
0.1-0.2	1871
0.2-0.3	37
0.3-0.4	0
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