NPASS Compound

Natural Product: NPC473689

Natural Product ID	NPC473689
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Wilfordine
IUPAC Name	n.a.
Synonyms	Wilfordine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449308
PubChem CID	442556
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

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 112117 0 0 0 0 0 0 0 0999 V2000 5.8792 -0.6575 -0.2182 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6209 -0.6274 -0.9819 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6099 -0.5495 -2.2446 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3692 -0.6824 -0.3592 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1739 -0.6480 -1.1759 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9995 -0.7095 -0.2237 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0640 0.4673 0.6979 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2698 0.6153 1.4164 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2485 0.7383 2.7994 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1257 0.7128 3.3944 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4520 0.8994 3.6420 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8467 1.8160 0.0225 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9678 2.1913 -0.7382 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8160 3.2021 -0.3867 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5332 3.8108 0.6925 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9749 3.5698 -1.1862 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8171 4.6049 -0.7940 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9176 4.9622 -1.5334 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2333 4.2899 -2.7208 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4007 3.2730 -3.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2994 2.9193 -2.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4698 1.9065 -0.7001 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7109 0.6897 -1.5003 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3471 -0.6267 -0.9015 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2592 -0.7824 0.1796 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8008 -2.0269 0.1523 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8983 -2.8287 -0.6885 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4069 -3.1998 -0.0577 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0654 -1.9885 0.5569 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4054 -2.2620 0.8847 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7914 -2.4660 2.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8858 -2.4025 3.0410 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1817 -2.7504 2.6180 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1790 -3.8256 -1.0531 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5624 -5.1348 -0.9404 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2053 -5.7651 0.0853 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3733 -5.7882 -1.9938 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4803 -1.7978 -1.7667 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4091 -1.7821 -2.8096 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1763 -2.2416 -4.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0534 -2.7182 -4.3727 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2642 -2.1579 -5.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9440 -2.4920 1.5839 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2254 -2.0374 -0.4022 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0680 -1.2581 0.4574 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3931 -1.0163 0.2431 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9543 -1.4875 -0.7601 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1629 -0.2158 1.1694 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5039 -0.6061 1.2876 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3686 0.0406 2.1186 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8645 1.1012 2.8422 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5807 1.4676 2.7227 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7131 0.8246 1.8934 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3041 1.2985 1.8316 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1882 2.7707 1.8415 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8682 3.3977 1.8492 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9277 3.2351 0.7736 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4609 4.2312 0.0942 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4339 2.0152 0.3715 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1827 3.0854 3.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1029 4.8111 1.9580 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1178 0.9033 -2.9039 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0918 0.7211 -1.7591 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5926 0.0336 -0.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6856 -0.2792 0.8049 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3657 -1.6370 -0.1934 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2961 -1.5675 -1.7882 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1940 0.1881 -1.8583 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2413 0.3636 1.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6311 1.9701 3.9150 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3372 0.5097 3.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3161 0.3112 4.5810 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8469 2.5265 0.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5409 5.1144 0.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5572 5.7537 -1.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1078 4.5785 -3.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6632 2.7566 -4.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7005 2.1056 -2.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5862 2.8513 -1.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4004 -3.6673 -1.1951 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2283 -3.9349 0.7200 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5102 -1.8435 1.5022 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9111 -2.0199 2.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4151 -3.7922 2.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2322 -2.7630 3.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7241 -6.3518 -2.7022 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8829 -5.0011 -2.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1709 -6.4243 -1.5647 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4417 -2.2233 -2.2143 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5869 -1.0821 -5.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8965 -2.5247 -6.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1128 -2.7637 -4.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7581 -1.6641 2.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3137 -3.3274 1.8845 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9932 -2.8361 1.8274 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6488 -3.0614 -0.3583 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2896 -1.7293 -1.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8882 -1.4555 0.6996 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3906 -0.2878 2.1843 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5524 1.6180 3.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7970 0.8010 2.6995 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8514 0.9192 0.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8161 3.1882 1.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7399 3.1364 2.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9279 3.3892 3.9725 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9948 2.0124 3.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3141 3.7367 3.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6788 5.1152 1.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3484 0.0263 -3.3175 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6794 1.6987 -2.8085 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 1.4153 -3.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5967 1.0785 -1.0110 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 6 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 7 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 12 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 28 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 27 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 26 43 1 1 26 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 2 0 57 59 1 0 56 60 1 0 56 61 1 0 23 62 1 0 23 63 1 6 29 6 1 0 53 48 1 0 24 6 1 0 21 16 1 0 59 22 1 0 38 24 1 0 1 64 1 0 1 65 1 0 1 66 1 0 5 67 1 0 5 68 1 0 7 69 1 1 11 70 1 0 11 71 1 0 11 72 1 0 12 73 1 1 17 74 1 0 18 75 1 0 19 76 1 0 20 77 1 0 21 78 1 0 22 79 1 6 27 80 1 6 28 81 1 1 29 82 1 1 33 83 1 0 33 84 1 0 33 85 1 0 37 86 1 0 37 87 1 0 37 88 1 0 38 89 1 6 42 90 1 0 42 91 1 0 42 92 1 0 43 93 1 0 43 94 1 0 43 95 1 0 44 96 1 0 44 97 1 0 49 98 1 0 50 99 1 0 51100 1 0 54101 1 0 54102 1 0 55103 1 0 55104 1 0 60105 1 0 60106 1 0 60107 1 0 61108 1 0 62109 1 0 62110 1 0 62111 1 0 63112 1 0 M END

Standard InCHIKey	XQDBHSNYTFRCNJ-OURLNJDISA-N
Standard InCHI	InChI=1S/C43H49NO19/c1-21(45)55-20-42-34(59-24(4)48)30(57-22(2)46)29-32(58-23(3)47)43(42)41(8,54)33(31(35(42)60-25(5)49)61-36(50)26-13-10-9-11-14-26)62-38(52)39(6,53)17-16-28-27(15-12-18-44-28)37(51)56-19-40(29,7)63-43/h9-15,18,29-35,53-54H,16-17,19-20H2,1-8H3/t29-,30-,31+,32-,33+,34-,35+,39?,40+,41+,42-,43+/m1/s1
SMILES	CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)c3ccccc3)[C@H]3[C@]([C@@]42O[C@@]([C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)[C@H]4OC(=O)C)(C)COC(=O)c1cccnc1CCC(C(=O)O3)(C)O)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	883.29	Volume:	842.046 ? Van der Waals volume.
Dense:	1.049	LogP:	0.928 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.413 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.11 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	44.0
TPSA:	272.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.279	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.62	Fsp³:	0.558
MCE-18:	226.836 ? 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:	0.492	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.224 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.012	Promiscuous compounds:	0.174

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.481	MDCK Permeability:	-4.837
Pgp-inhibitor:	0.092	Pgp-substrate:	0.49
PAMPA:	0.992 ? 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%):	0.001	30% Bioavailability (F30%):	0.029
50% Bioavailability (F50%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052	MRP1:	1.0
Plasma Protein Binding (PPB):	44.905%	Volume Distribution (VD):	-0.399
Fu:	49.093% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.0
BSEP inhibitor:	0.68

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.058	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.84
HLM stability:	0.014 ? 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):

0.495

Half-life (T1/2):

1.535

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.046
Human Hepatotoxicity (H-HT):	0.358	Drug-induced Liver Injury (DILI):	0.852
AMES Toxicity:	0.992	Rat Oral Acute Toxicity:	0.492
Maximum Recommended Daily Dose:	0.714	Skin Sensitization:	1.0
Carcinogencity:	0.751	Eye Corrosion:	0.0
Eye Irritation:	0.033	Respiratory Toxicity:	0.091
Drug-induced Neurotoxicity:	0.255	Ototoxicity:	0.613
Hematotoxicity:	0.886	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.445
A549 Cytotoxicity:	0.467	Hek293 Cytotoxicity:	0.176
BCF:	0.51 ? 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:	3.238 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.571 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.136 ? 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]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713421]
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]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[14738378]
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]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
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.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	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]
NPO1333	Maytenus chiapensis	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]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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
EC50	3
Activity	2

Activity Type	# Activity
Cell line	2
Organism	5

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
NPT759	Cell line	H9	Homo sapiens	IC50	=	20.0	ug.mL-1	PMID[19487444]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	=	2.3	10'-4 ug/cm2	PMID[24920381]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	109.0	%	PMID[22413887]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	93.0	%	Open TG-GATES in vivo data: Biochemistry
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	<	0.1	ug.mL-1	PMID[9514009]

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 NPC473689 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	19653
0.1-0.2	28834
0.2-0.3	1073
0.3-0.4	201
0.4-0.5	27
0.5-0.6	27
0.6-0.7	21
0.7-0.8	0
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC292416
0.9681	High Similarity	NPC475406
0.875	High Similarity	NPC122968
0.875	High Similarity	NPC228377
0.8723	High Similarity	NPC146824
0.8571	High Similarity	NPC13603
0.8137	Intermediate Similarity	NPC253482
0.8	Intermediate Similarity	NPC328186
0.7788	Intermediate Similarity	NPC475648
0.7745	Intermediate Similarity	NPC316841
0.7619	Intermediate Similarity	NPC244839
0.7573	Intermediate Similarity	NPC475600
0.7551	Intermediate Similarity	NPC250807
0.7551	Intermediate Similarity	NPC57797
0.7547	Intermediate Similarity	NPC319880
0.7547	Intermediate Similarity	NPC320324
0.7477	Intermediate Similarity	NPC38959
0.7451	Intermediate Similarity	NPC53255
0.7451	Intermediate Similarity	NPC85879
0.7315	Intermediate Similarity	NPC327904
0.7282	Intermediate Similarity	NPC475362
0.7009	Intermediate Similarity	NPC476110
0.6937	Remote Similarity	NPC471979
0.6916	Remote Similarity	NPC87152
0.6916	Remote Similarity	NPC475631
0.6822	Remote Similarity	NPC475303
0.6818	Remote Similarity	NPC601643
0.6786	Remote Similarity	NPC327769
0.6757	Remote Similarity	NPC477787
0.6697	Remote Similarity	NPC475596
0.6606	Remote Similarity	NPC328154
0.6577	Remote Similarity	NPC483894
0.6525	Remote Similarity	NPC483854
0.6518	Remote Similarity	NPC600583
0.6476	Remote Similarity	NPC76565
0.6476	Remote Similarity	NPC601313
0.6471	Remote Similarity	NPC482915
0.6429	Remote Similarity	NPC483893
0.6422	Remote Similarity	NPC326930
0.6195	Remote Similarity	NPC475644
0.6068	Remote Similarity	NPC483853
0.6068	Remote Similarity	NPC608314
0.6	Remote Similarity	NPC483892
0.5965	Remote Similarity	NPC483895
0.5948	Remote Similarity	NPC237702
0.5929	Remote Similarity	NPC475301
0.5913	Remote Similarity	NPC30456
0.5913	Remote Similarity	NPC488904
0.5877	Remote Similarity	NPC471977
0.5862	Remote Similarity	NPC600607
0.5826	Remote Similarity	NPC324619
0.578	Remote Similarity	NPC473850
0.5726	Remote Similarity	NPC483856
0.5586	Remote Similarity	NPC471016
0.5574	Remote Similarity	NPC475426
0.547	Remote Similarity	NPC470486
0.547	Remote Similarity	NPC477788
0.5462	Remote Similarity	NPC611166
0.5405	Remote Similarity	NPC470306
0.5385	Remote Similarity	NPC607403
0.5351	Remote Similarity	NPC475498
0.5328	Remote Similarity	NPC328928
0.5221	Remote Similarity	NPC35208
0.521	Remote Similarity	NPC475315
0.5154	Remote Similarity	NPC483855
0.5128	Remote Similarity	NPC475601
0.5126	Remote Similarity	NPC475533
0.5041	Remote Similarity	NPC471190
0.5041	Remote Similarity	NPC600224
0.5041	Remote Similarity	NPC604935

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4058
0.1-0.2	5045
0.2-0.3	45
0.3-0.4	2
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