NPASS Compound

Natural Product: NPC488917

Natural Product ID	NPC488917
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BWHLAESNTRTMKH-QJFGSGHOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 90 93 0 0 0 0 0 0 0 0999 V2000 -1.0365 -4.9880 2.4929 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1051 -3.5141 2.5291 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3582 -2.9329 3.6093 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8971 -2.7489 1.3987 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9655 -1.4063 1.4587 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7531 -0.5351 0.2858 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6392 -0.7521 -0.2991 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7053 -1.7022 -1.4539 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4585 -2.6270 -1.6459 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8075 -2.0186 -1.4501 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7983 -2.9193 -0.7832 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.6459 -0.8669 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9273 0.0703 -0.5438 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4786 1.4838 -0.9951 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5214 1.9230 0.0673 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8752 0.8831 0.8718 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5271 0.8491 2.1588 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9199 1.1277 3.3406 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2773 1.4372 3.3591 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6781 1.0652 4.6161 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5486 2.8569 -0.3696 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4784 4.1765 -0.0168 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3402 4.6256 0.7621 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6234 4.9962 -0.5846 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8093 1.1266 -2.2879 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7497 0.9600 -3.4268 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8123 2.2026 -2.7620 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0577 0.0685 -1.9254 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0990 -0.3294 -1.1372 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2593 -0.4830 -0.4371 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2954 -0.2587 0.8030 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5491 -0.9194 -1.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3385 -1.8091 -2.7584 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8925 -2.4712 -1.3801 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8786 -2.4511 -2.3309 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6822 -1.7042 -3.2948 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1336 -3.2423 -2.2865 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5900 -1.0912 0.6926 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6854 -0.2463 0.9907 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7182 0.7792 0.3104 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6240 -0.6312 2.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6996 -0.0035 2.3591 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2371 1.2105 1.8130 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2103 1.6885 0.5402 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6686 2.9565 0.1592 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1906 3.7983 1.1134 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2442 3.3596 2.4203 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7893 2.1218 2.7615 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0369 -5.4617 2.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4003 -5.3746 3.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6805 -5.3420 1.5052 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9460 -1.1222 1.9415 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2149 -1.0506 2.2336 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9288 0.2427 -0.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8333 -1.1540 -2.4149 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3430 -3.0166 -2.7127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3214 -3.6118 -1.0997 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6889 -3.1803 -1.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3592 -3.9425 -0.5832 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2753 -2.4881 0.1202 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1233 0.2141 0.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3376 2.1374 -1.1468 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1768 2.5693 0.7425 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1655 1.1771 1.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4804 0.0893 5.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7762 1.1025 4.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4233 1.9168 5.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5664 6.0444 -0.2326 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 4.5042 -0.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5968 5.0048 -1.6975 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7121 0.5145 -3.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9637 1.9954 -3.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1705 0.4787 -4.2692 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2100 2.0074 -2.3860 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6844 2.0899 -3.8843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1999 3.2080 -2.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3068 -0.1605 -0.7858 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8098 -1.9431 -0.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4656 -0.8589 -2.1870 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9545 -2.4644 -3.3678 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 -2.7517 -1.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8778 -4.2283 -1.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5088 -3.4753 -3.3062 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4389 -1.5708 2.5874 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3299 -0.4470 3.2045 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9036 1.0791 -0.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6175 3.2808 -0.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5573 4.7892 0.8635 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6635 4.0390 3.1710 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8502 1.8242 3.7818 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 6 5 1 1 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 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 14 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 13 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 10 33 1 6 8 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 7 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 16 6 1 0 48 43 1 0 12 6 1 0 12 28 1 6 1 49 1 0 1 50 1 0 1 51 1 0 5 52 1 0 5 53 1 0 7 54 1 6 8 55 1 6 9 56 1 0 9 57 1 0 11 58 1 0 11 59 1 0 11 60 1 0 13 61 1 1 14 62 1 6 15 63 1 1 16 64 1 1 20 65 1 0 20 66 1 0 20 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 32 77 1 0 32 78 1 0 32 79 1 0 33 80 1 0 37 81 1 0 37 82 1 0 37 83 1 0 41 84 1 0 42 85 1 0 44 86 1 0 45 87 1 0 46 88 1 0 47 89 1 0 48 90 1 0 M END

Standard InCHIKey	BWHLAESNTRTMKH-QJFGSGHOSA-N
Standard InCHI	InChI=1S/C34H42O14/c1-18(35)42-17-33-28(47-25(40)15-14-23-12-10-9-11-13-23)24(43-19(2)36)16-32(8,41)34(33)29(45-21(4)38)26(31(6,7)48-34)27(44-20(3)37)30(33)46-22(5)39/h9-15,24,26-30,41H,16-17H2,1-8H3/b15-14-/t24-,26+,27-,28-,29+,30+,32-,33-,34-/m0/s1
SMILES	CC(=O)OC[C@]12[C@H]([C@H](C[C@@](C)([C@]32[C@@H]([C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)C(C)(C)O3)OC(=O)C)O)OC(=O)C)OC(=O)/C=Cc1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	674.26	Volume:	659.093 ? Van der Waals volume.
Dense:	1.023	LogP:	2.607 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.796 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.492 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	27.0
TPSA:	187.26 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.228	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.152	Fsp³:	0.588
MCE-18:	163.074 ? 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:	0.265	Fluc inhibitor:	0.317 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.273 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.069	Promiscuous compounds:	0.328

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.114	MDCK Permeability:	-4.723
Pgp-inhibitor:	0.992	Pgp-substrate:	0.023
PAMPA:	0.22 ? 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%):	0.155	30% Bioavailability (F30%):	0.415
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.81	MRP1:	0.996
Plasma Protein Binding (PPB):	78.672%	Volume Distribution (VD):	-0.44
Fu:	19.637% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.915	BCRP inhibitor:	0.001
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.624
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.162
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.024	CYP3A4-substrate:	0.093
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.763 ? 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):

1.352

Half-life (T1/2):

1.371

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.1
Human Hepatotoxicity (H-HT):	0.228	Drug-induced Liver Injury (DILI):	0.315
AMES Toxicity:	0.897	Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.232	Skin Sensitization:	1.0
Carcinogencity:	0.254	Eye Corrosion:	0.02
Eye Irritation:	0.741	Respiratory Toxicity:	0.044
Drug-induced Neurotoxicity:	0.123	Ototoxicity:	0.119
Hematotoxicity:	0.046	Drug-induced Nephrotoxicity:	0.743
Genotoxicity:	0.38	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.423	Hek293 Cytotoxicity:	0.464
BCF:	0.611 ? 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:	3.479 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.047 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.568 ? 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	1

Activity Type	# Activity
Cell line	1

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[31556299]

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 NPC488917 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	10936
0.1-0.2	35355
0.2-0.3	3161
0.3-0.4	282
0.4-0.5	80
0.5-0.6	22
0.6-0.7	12
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
0.7273	Intermediate Similarity	NPC488912
0.7273	Intermediate Similarity	NPC488910
0.7273	Intermediate Similarity	NPC488908
0.7273	Intermediate Similarity	NPC488906
0.72	Intermediate Similarity	NPC16912
0.6923	Remote Similarity	NPC481489
0.6753	Remote Similarity	NPC472569
0.6753	Remote Similarity	NPC11685
0.6753	Remote Similarity	NPC472570
0.6625	Remote Similarity	NPC481488
0.642	Remote Similarity	NPC488920
0.6341	Remote Similarity	NPC488919
0.6264	Remote Similarity	NPC6981
0.6173	Remote Similarity	NPC488909
0.6173	Remote Similarity	NPC488905
0.6125	Remote Similarity	NPC488918
0.6125	Remote Similarity	NPC488913
0.5783	Remote Similarity	NPC476970
0.5714	Remote Similarity	NPC488907
0.5581	Remote Similarity	NPC476971
0.5476	Remote Similarity	NPC97667
0.5455	Remote Similarity	NPC125106
0.5455	Remote Similarity	NPC472573
0.5412	Remote Similarity	NPC488914
0.5357	Remote Similarity	NPC57628
0.5294	Remote Similarity	NPC95265
0.5287	Remote Similarity	NPC481486
0.5263	Remote Similarity	NPC488902
0.5263	Remote Similarity	NPC488903
0.5238	Remote Similarity	NPC473110
0.5233	Remote Similarity	NPC282239
0.5222	Remote Similarity	NPC610134
0.5172	Remote Similarity	NPC479042
0.5122	Remote Similarity	NPC281717
0.5122	Remote Similarity	NPC483886
0.5119	Remote Similarity	NPC471104
0.5116	Remote Similarity	NPC70716
0.5057	Remote Similarity	NPC472568
0.5056	Remote Similarity	NPC472571

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3714
0.1-0.2	5319
0.2-0.3	117
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