NPASS Compound

Natural Product: NPC47448

Natural Product ID	NPC47448
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GPJJFVDRSCVAGP-USGKZMIQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5322134
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 87 91 0 0 0 0 0 0 0 0999 V2000 2.1483 -2.6695 2.9214 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0450 -1.6943 2.6620 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7882 -0.8781 3.5819 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3524 -1.6892 1.4906 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6689 -0.7690 1.2761 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3320 -0.9205 -0.1092 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2016 -0.6998 -1.0778 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1768 -1.8888 -1.9101 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1779 -3.1876 -1.1972 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1616 -3.4274 -0.6271 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9731 -4.4773 0.4868 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9599 -2.2748 -0.1546 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2558 -2.2717 -0.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1336 -1.5657 0.0477 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7738 -0.1251 -0.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3498 0.2025 -0.2810 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8970 1.4233 0.1965 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5966 2.5729 -0.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7880 2.4518 -1.6817 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1202 3.7992 0.1308 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8961 3.9499 1.4785 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4347 5.1465 2.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1905 6.2210 1.1856 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4088 6.0885 -0.1639 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8728 4.8776 -0.6820 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3620 0.4809 1.0640 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7275 -2.3030 1.2720 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4470 -3.6638 1.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1007 -1.6955 2.5763 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3860 -2.5840 1.1391 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1635 -1.6090 -2.1595 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8843 -4.1536 -1.6212 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4355 -1.5779 -2.4959 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5933 -1.4428 -3.8370 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6067 -1.5944 -4.5915 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9092 -1.1177 -4.4682 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0036 -0.2546 -0.4619 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6477 0.9035 -0.8544 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1663 1.5934 -1.7859 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8901 1.3347 -0.1945 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4725 2.4364 -0.5972 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7022 2.9933 -0.0489 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3611 2.3780 0.9751 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5391 2.9159 1.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0610 4.0691 0.9873 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3861 4.6730 -0.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2265 4.1641 -0.5655 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1385 -2.2173 2.6629 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9957 -3.6280 2.3840 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1999 -2.8966 4.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2317 0.2469 1.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3764 -0.8904 2.0979 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4645 0.0898 -1.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5306 -1.9800 -2.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3625 -3.9668 -2.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0364 -3.3546 -0.5245 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0092 -4.9399 0.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1382 -4.0228 1.4793 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7466 -5.2662 0.3941 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5469 -3.3109 -1.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1922 -1.7576 -0.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4515 0.2583 -0.8749 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3243 0.4029 -1.3808 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0761 3.1364 2.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2580 5.2680 3.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1728 7.1563 1.6236 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2114 6.9413 -0.7954 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0458 4.7721 -1.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2771 0.1455 1.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9259 -3.8216 0.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2534 -3.6689 1.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7463 -4.4885 1.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7722 -2.4421 3.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2058 -1.6965 2.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6265 -0.7664 2.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5109 -2.0819 -2.9379 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2703 -4.7049 -2.1650 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4372 -2.0088 -4.8326 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5800 -0.6115 -3.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7949 -0.4114 -5.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3354 0.7718 0.6071 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9948 2.9941 -1.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0194 1.4593 1.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0614 2.4259 2.3036 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9759 4.4932 1.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7707 5.5881 -0.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6943 4.6434 -1.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 15 26 1 0 14 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 13 31 1 0 10 32 1 6 8 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 7 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 16 6 1 0 25 20 1 0 47 42 1 0 12 6 1 0 30 12 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 0 5 52 1 0 7 53 1 6 8 54 1 6 9 55 1 0 9 56 1 0 11 57 1 0 11 58 1 0 11 59 1 0 13 60 1 0 14 61 1 0 15 62 1 0 16 63 1 6 21 64 1 0 22 65 1 0 23 66 1 0 24 67 1 0 25 68 1 0 26 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 31 76 1 0 32 77 1 0 36 78 1 0 36 79 1 0 36 80 1 0 40 81 1 0 41 82 1 0 43 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 47 87 1 0 M END

Standard InCHIKey	GPJJFVDRSCVAGP-USGKZMIQSA-N
Standard InCHI	InChI=1S/C35H40O12/c1-20(36)43-19-34-29(45-25(38)17-16-22-12-8-6-9-13-22)24(44-21(2)37)18-33(5,42)35(34)28(40)26(32(3,4)47-35)27(39)30(34)46-31(41)23-14-10-7-11-15-23/h6-17,24,26-30,39-40,42H,18-19H2,1-5H3/b17-16+/t24-,26?,27?,28?,29-,30+,33-,34?,35?/m0/s1
SMILES	CC(=O)OCC12[C@H]([C@H](C[C@@](C)(C32C(C(C([C@H]1OC(=O)c1ccccc1)O)C(C)(C)O3)O)O)OC(=O)C)OC(=O)/C=C/c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.25	Volume:	647.615 ? Van der Waals volume.
Dense:	1.007	LogP:	3.417 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.168 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.419 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	31.0
TPSA:	175.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.216	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.032	Fsp³:	0.486
MCE-18:	172.5 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.804	Fluc inhibitor:	0.332 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.646 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.029	Promiscuous compounds:	0.09

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.51	MDCK Permeability:	-5.017
Pgp-inhibitor:	0.999	Pgp-substrate:	0.131
PAMPA:	0.86 ? 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):	0.002
20% Bioavailability (F20%):	0.827	30% Bioavailability (F30%):	0.983
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.963
Plasma Protein Binding (PPB):	87.597%	Volume Distribution (VD):	-0.084
Fu:	14.479% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.0
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.743
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.898
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.44 ? 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):

4.711

Half-life (T1/2):

1.216

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.431
Human Hepatotoxicity (H-HT):	0.182	Drug-induced Liver Injury (DILI):	0.682
AMES Toxicity:	0.699	Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.441	Skin Sensitization:	0.979
Carcinogencity:	0.315	Eye Corrosion:	0.0
Eye Irritation:	0.094	Respiratory Toxicity:	0.025
Drug-induced Neurotoxicity:	0.399	Ototoxicity:	0.412
Hematotoxicity:	0.07	Drug-induced Nephrotoxicity:	0.526
Genotoxicity:	0.498	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.156	Hek293 Cytotoxicity:	0.598
BCF:	0.607 ? 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:	3.517 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.333 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.695 ? 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

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 NPC47448 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	11061
0.1-0.2	35022
0.2-0.3	3106
0.3-0.4	537
0.4-0.5	89
0.5-0.6	32
0.6-0.7	8
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
0.7949	Intermediate Similarity	NPC481487
0.6867	Remote Similarity	NPC488920
0.6867	Remote Similarity	NPC488908
0.6867	Remote Similarity	NPC488906
0.6588	Remote Similarity	NPC472571
0.6548	Remote Similarity	NPC488915
0.631	Remote Similarity	NPC106895
0.6067	Remote Similarity	NPC483860
0.6047	Remote Similarity	NPC481490
0.5843	Remote Similarity	NPC488917
0.573	Remote Similarity	NPC488912
0.573	Remote Similarity	NPC488910
0.5682	Remote Similarity	NPC472568
0.5667	Remote Similarity	NPC488919
0.5495	Remote Similarity	NPC470159
0.5495	Remote Similarity	NPC483878
0.5435	Remote Similarity	NPC70403
0.5435	Remote Similarity	NPC177940
0.5417	Remote Similarity	NPC476973
0.5333	Remote Similarity	NPC488909
0.5333	Remote Similarity	NPC488905
0.5319	Remote Similarity	NPC488916
0.5319	Remote Similarity	NPC610134
0.5294	Remote Similarity	NPC97947
0.5281	Remote Similarity	NPC11685
0.5281	Remote Similarity	NPC16912
0.5281	Remote Similarity	NPC472570
0.5275	Remote Similarity	NPC488907
0.5275	Remote Similarity	NPC476972
0.5269	Remote Similarity	NPC473109
0.5269	Remote Similarity	NPC605086
0.5253	Remote Similarity	NPC96801
0.5253	Remote Similarity	NPC150698
0.5248	Remote Similarity	NPC294579
0.5248	Remote Similarity	NPC144779
0.5222	Remote Similarity	NPC95265
0.5222	Remote Similarity	NPC97667
0.5213	Remote Similarity	NPC174982
0.5165	Remote Similarity	NPC282239
0.5109	Remote Similarity	NPC481489
0.5109	Remote Similarity	NPC479042

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC47448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4025
0.1-0.2	5007
0.2-0.3	118
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