NPASS Compound

Natural Product: NPC471980

Natural Product ID	NPC471980
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DHSWGWBPMGBLTM-QHLYSJRZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3314704
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 86 91 0 0 0 0 0 0 0 0999 V2000 -0.6941 -4.0051 -1.4839 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2203 -2.6276 -1.0760 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0966 -2.7006 0.3930 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9988 -1.6313 0.8863 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5793 -0.2295 0.4002 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9205 -0.0467 0.5276 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3206 1.1060 -0.3231 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7571 1.4593 -0.0290 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6410 0.3166 -0.2804 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1367 -1.0555 -0.1262 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6580 -1.2582 0.0185 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3232 -2.4146 0.9250 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1586 -3.5301 0.6476 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7291 -4.1801 1.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5045 -3.7833 2.9295 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5907 -5.3266 1.5339 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8565 -5.7814 0.2578 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6473 -6.8320 0.1089 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2096 -7.4864 1.1189 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9766 -7.0732 2.4124 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1595 -5.9847 2.6031 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1773 -1.6517 -1.2229 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6376 -1.8280 -1.3600 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7516 -1.7465 0.9513 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4887 2.2303 -0.3108 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0614 2.7617 -1.4700 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2272 2.1788 -2.5386 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9203 3.9146 -1.4975 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2341 4.5483 -0.3167 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0661 5.6688 -0.3195 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5795 6.1519 -1.4896 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2771 5.5330 -2.6727 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4489 4.4189 -2.6620 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1223 0.2071 1.9998 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3898 0.3843 2.4374 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3034 0.6336 1.2561 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3866 1.3908 0.7051 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6049 1.2073 -0.4947 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1113 2.2765 1.5665 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0895 3.0852 1.5023 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0246 3.5679 0.5258 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1281 3.1684 -0.7712 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0572 3.6962 -1.6701 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9195 4.6745 -1.2275 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8662 5.1219 0.0740 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9388 4.5762 0.9215 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9844 -2.3023 -1.9385 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0317 -4.4611 -2.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6989 -4.0239 -1.8952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -4.7441 -0.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4541 -3.6720 0.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0461 -1.7868 0.6114 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9653 -1.6194 1.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9030 -0.0736 -0.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3520 0.7437 -1.3987 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9484 1.9272 0.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0141 2.2719 -0.7976 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1759 0.4823 -1.2717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5151 0.4166 0.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2343 -2.1997 1.9775 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4181 -5.2756 -0.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8533 -8.3476 0.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4335 -7.6061 3.2261 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9691 -5.6497 3.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6846 -2.9147 -1.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6101 -1.4108 -1.6569 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9120 -1.6240 -2.1904 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4478 -1.1305 1.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8599 4.2172 0.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3108 6.1634 0.6018 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2374 7.0347 -1.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6975 5.9364 -3.5832 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2244 3.9469 -3.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5978 1.2106 2.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5600 -0.4711 2.6645 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4971 1.0900 3.1303 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6835 2.2616 2.6651 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2917 3.5783 2.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4907 2.4119 -1.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0694 3.3210 -2.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6232 5.0574 -1.9531 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5653 5.8891 0.3668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9352 4.9586 1.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2027 -3.1257 -2.6835 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9117 -2.1706 -1.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7619 -1.4145 -2.6021 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 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 11 22 1 0 10 23 1 0 10 24 1 0 7 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 6 34 1 0 34 35 1 0 5 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 2 3 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 2 47 1 0 22 2 1 0 12 3 1 0 11 6 1 0 21 16 1 0 33 28 1 0 46 41 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 7 55 1 0 8 56 1 0 8 57 1 0 9 58 1 0 9 59 1 0 12 60 1 0 17 61 1 0 19 62 1 0 20 63 1 0 21 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 29 69 1 0 30 70 1 0 31 71 1 0 32 72 1 0 33 73 1 0 34 74 1 0 34 75 1 0 35 76 1 0 39 77 1 0 40 78 1 0 42 79 1 0 43 80 1 0 44 81 1 0 45 82 1 0 46 83 1 0 47 84 1 0 47 85 1 0 47 86 1 0 M END

Standard InCHIKey	DHSWGWBPMGBLTM-QHLYSJRZSA-N
Standard InCHI	InChI=1S/C37H39NO9/c1-34(2)27-21-29(44-30(40)17-16-24-11-6-4-7-12-24)36(23-39)28(45-32(41)25-13-8-5-9-14-25)18-19-35(3,43)37(36,47-34)31(27)46-33(42)26-15-10-20-38-22-26/h4-17,20,22,27-29,31,39,43H,18-19,21,23H2,1-3H3/b17-16-/t27-,28+,29-,31-,35+,36+,37+/m1/s1
SMILES	CC1(C2CC(C3(C(CCC(C3(C2OC(=O)C4=CN=CC=C4)O1)(C)O)OC(=O)C5=CC=CC=C5)CO)OC(=O)C=CC6=CC=CC=C6)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	641.26	Volume:	653.004 ? Van der Waals volume.
Dense:	0.982	LogP:	4.22 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.645 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.334 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	36.0
TPSA:	141.48 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.204	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.754	Fsp³:	0.405
MCE-18:	176.923 ? 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:	0.928	Fluc inhibitor:	0.349 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.081 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.636 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.026	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.423	MDCK Permeability:	-4.974
Pgp-inhibitor:	0.915	Pgp-substrate:	0.086
PAMPA:	0.961 ? 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%):	0.094	30% Bioavailability (F30%):	0.288
50% Bioavailability (F50%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185	MRP1:	1.0
Plasma Protein Binding (PPB):	88.771%	Volume Distribution (VD):	-0.279
Fu:	14.566% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.338
OATP1B3 inhibitor:	0.875	BCRP inhibitor:	0.004
BSEP inhibitor:	0.988

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.976
CYP2C9-inhibitor:	0.117	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.582
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.972
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.982 ? 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):

1.217

Half-life (T1/2):

1.337

ADMET: Toxicity

hERG Blockers:	0.261	hERG Blockers (10um):	0.76
Human Hepatotoxicity (H-HT):	0.059	Drug-induced Liver Injury (DILI):	0.44
AMES Toxicity:	0.082	Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.35	Skin Sensitization:	0.97
Carcinogencity:	0.253	Eye Corrosion:	0.0
Eye Irritation:	0.02	Respiratory Toxicity:	0.025
Drug-induced Neurotoxicity:	0.647	Ototoxicity:	0.719
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.185
Genotoxicity:	0.007	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.044	Hek293 Cytotoxicity:	0.743
BCF:	1.166 ? 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:	4.244 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.478 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.172 ? 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
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	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	2

Activity Type	# Activity
Cell line	2

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
NPT927	Cell line	PBMC	Homo sapiens	IC50	=	57610.0	nM	PMID[8496701]
NPT927	Cell line	PBMC	Homo sapiens	IC50	=	24650.0	nM	PMID[8496701]

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 NPC471980 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	10945
0.1-0.2	35754
0.2-0.3	2648
0.3-0.4	381
0.4-0.5	99
0.5-0.6	25
0.6-0.7	4
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
0.6905	Remote Similarity	NPC127720
0.6771	Remote Similarity	NPC483880
0.6771	Remote Similarity	NPC156941
0.6162	Remote Similarity	NPC6981
0.5918	Remote Similarity	NPC96801
0.5918	Remote Similarity	NPC150698
0.5914	Remote Similarity	NPC610927
0.5914	Remote Similarity	NPC611111
0.5876	Remote Similarity	NPC483885
0.58	Remote Similarity	NPC483891
0.5743	Remote Similarity	NPC294579
0.5743	Remote Similarity	NPC144779
0.5684	Remote Similarity	NPC301368
0.5684	Remote Similarity	NPC84815
0.5652	Remote Similarity	NPC609309
0.5625	Remote Similarity	NPC127026
0.5625	Remote Similarity	NPC483890
0.5521	Remote Similarity	NPC56953
0.5521	Remote Similarity	NPC184817
0.5417	Remote Similarity	NPC125106
0.5417	Remote Similarity	NPC472573
0.5376	Remote Similarity	NPC476970
0.5361	Remote Similarity	NPC188865
0.5354	Remote Similarity	NPC483869
0.5248	Remote Similarity	NPC176413
0.5248	Remote Similarity	NPC294512
0.5149	Remote Similarity	NPC86800
0.5106	Remote Similarity	NPC210591
0.505	Remote Similarity	NPC476974

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471980 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3504
0.1-0.2	5504
0.2-0.3	138
0.3-0.4	4
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