NPASS Compound

Natural Product: NPC476110

Natural Product ID	NPC476110
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Mayteine
IUPAC Name	n.a.
Synonyms	Mayteine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL526919
PubChem CID	3086511
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives

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 111116 0 0 0 0 0 0 0 0999 V2000 4.4094 -0.2017 1.3798 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3433 0.0575 0.2304 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8881 1.1435 -0.6177 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5484 1.3008 -1.1335 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3829 1.3610 -2.4012 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3720 1.4076 -0.4214 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0653 1.5765 -0.9118 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1415 2.0637 0.1509 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2076 1.4218 0.2965 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4148 -0.0078 -0.0958 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9709 -0.9497 0.9379 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2451 -2.1736 1.3025 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1615 -2.3826 0.7908 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6605 -0.8813 0.6632 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1014 -0.6013 -0.6058 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6086 0.2888 -1.5468 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0643 0.5256 -2.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7522 -0.4050 -1.9010 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3667 -1.7691 -1.2741 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2999 -2.8093 -0.5887 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6333 -3.0870 -1.0752 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7841 -2.5773 -0.4321 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9761 -2.6725 -1.0931 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8379 -3.2128 -2.2722 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3236 -2.3220 -0.7833 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9050 -1.2037 -0.2751 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2938 -1.2019 -0.1266 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1124 -2.1905 -0.4318 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5660 -3.3288 -0.9417 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2200 -3.3864 -1.1092 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5233 -4.0770 -0.9196 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0885 -0.3702 1.8140 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6461 -0.0334 2.9690 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8511 -0.1581 3.1760 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1852 0.5280 4.1016 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8328 -3.4085 1.1458 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1265 -4.3490 2.0862 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8352 -4.0798 3.2564 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7598 -5.6357 1.7606 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4957 -0.1881 1.9667 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7859 -0.0759 2.3708 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6367 -0.7117 1.7569 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1628 0.7733 3.5088 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4931 0.0416 -1.1845 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7090 -1.2870 -1.6179 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6520 -1.5332 -2.6191 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3018 -0.5697 -3.1265 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8406 -2.9457 -3.0400 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2351 2.2402 -0.2517 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1294 3.0095 0.4015 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0421 3.0161 1.6316 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1222 3.7699 -0.3579 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0639 4.5836 0.2257 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9986 5.2952 -0.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0063 5.2013 -1.8906 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0653 4.3874 -2.4894 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1453 3.6889 -1.7368 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1758 3.4623 -0.0286 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1867 4.4665 0.8273 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 4.0856 1.8243 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1471 5.8984 0.6274 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1854 2.4797 0.1369 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9463 -0.0121 2.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1448 -1.2616 1.4185 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5451 0.4995 1.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2472 0.5766 0.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6307 1.2165 -1.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0629 2.3385 -1.7348 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7000 2.1072 1.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4317 1.4964 1.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9357 -1.4090 0.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0378 -2.0783 2.4189 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7821 -2.9183 1.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7124 -0.8810 0.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7310 0.5303 -3.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6791 -0.3293 -3.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4841 1.5257 -3.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7498 -0.7543 -2.8165 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8064 -4.2420 -0.9347 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7420 -3.0087 -2.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2079 -2.1025 -0.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2085 -4.1580 -1.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7426 -4.3077 -1.5190 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3431 -4.8234 -0.1499 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1352 -4.4934 -1.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5744 -3.8228 -1.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0252 -0.1702 4.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6692 1.4676 3.7452 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4092 0.6767 5.0016 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 -6.0595 2.6648 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4585 -5.4831 0.9222 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9418 -6.3290 1.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3005 1.2357 4.0287 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8040 0.1671 4.2034 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8298 1.6242 3.1856 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3446 0.6702 -2.0086 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4523 0.2779 -0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3126 -3.4793 -2.1776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4928 -2.9741 -3.9391 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8422 -3.3762 -3.2115 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0481 4.6487 1.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7378 5.9384 -0.0153 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7403 5.7607 -2.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1032 4.3391 -3.5861 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4141 3.0524 -2.2587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7508 5.9775 -0.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8558 6.1993 1.4508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7398 6.5447 0.6253 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4112 2.5225 0.9269 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2122 2.4814 0.5027 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0268 3.3121 -0.5514 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 2 0 4 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 1 0 15 16 1 0 16 17 1 0 16 18 1 0 15 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 20 31 1 0 14 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 12 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 11 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 10 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 9 49 1 0 49 50 1 0 50 51 2 0 50 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 8 58 1 0 58 59 1 0 59 60 2 0 59 61 1 0 3 62 1 0 26 2 1 0 16 7 1 0 15 10 1 0 20 13 1 0 30 25 1 0 57 52 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 0 3 67 1 0 7 68 1 0 8 69 1 0 9 70 1 0 11 71 1 0 12 72 1 0 13 73 1 0 14 74 1 0 17 75 1 0 17 76 1 0 17 77 1 0 18 78 1 0 21 79 1 0 21 80 1 0 28 81 1 0 29 82 1 0 30 83 1 0 31 84 1 0 31 85 1 0 31 86 1 0 35 87 1 0 35 88 1 0 35 89 1 0 39 90 1 0 39 91 1 0 39 92 1 0 43 93 1 0 43 94 1 0 43 95 1 0 44 96 1 0 44 97 1 0 48 98 1 0 48 99 1 0 48100 1 0 53101 1 0 54102 1 0 55103 1 0 56104 1 0 57105 1 0 61106 1 0 61107 1 0 61108 1 0 62109 1 0 62110 1 0 62111 1 0 M END

Standard InCHIKey	PPRQMPUDIUVHQX-PDVUZMAKSA-N
Standard InCHI	InChI=1S/C43H49NO18/c1-20-21(2)37(50)60-34-32(57-24(5)47)36(61-38(51)27-14-11-10-12-15-27)42(19-54-22(3)45)35(59-26(7)49)31(56-23(4)46)29-33(58-25(6)48)43(42,41(34,9)53)62-40(29,8)18-55-39(52)28-16-13-17-44-30(20)28/h10-17,20-21,29,31-36,53H,18-19H2,1-9H3/t20?,21?,29-,31-,32+,33-,34+,35-,36+,40+,41+,42-,43+/m1/s1
SMILES	CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C6=CC=CC=C6)OC(=O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	867.29	Volume:	833.255 ? Van der Waals volume.
Dense:	1.041	LogP:	1.339 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.715 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.114 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	43.0
TPSA:	252.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.587	Fsp³:	0.558
MCE-18:	220.896 ? 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:	0.148	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.194 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.017	Promiscuous compounds:	0.016

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.195	MDCK Permeability:	-4.733
Pgp-inhibitor:	0.875	Pgp-substrate:	0.608
PAMPA:	0.987 ? 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):	0.001
20% Bioavailability (F20%):	0.003	30% Bioavailability (F30%):	0.558
50% Bioavailability (F50%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	1.0
Plasma Protein Binding (PPB):	60.847%	Volume Distribution (VD):	-0.407
Fu:	36.678% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.341
OATP1B3 inhibitor:	0.862	BCRP inhibitor:	0.0
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.005
CYP3A4-inhibitor:	0.117	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	1.0
HLM stability:	0.97 ? 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):

0.05

Half-life (T1/2):

1.601

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.191
Human Hepatotoxicity (H-HT):	0.364	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.76	Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.362	Skin Sensitization:	0.994
Carcinogencity:	0.769	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.664	Ototoxicity:	0.904
Hematotoxicity:	0.147	Drug-induced Nephrotoxicity:	0.938
Genotoxicity:	0.95	RPMI-8226 Immunitoxicity:	0.121
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.299
BCF:	0.661 ? 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:	3.573 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.738 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.108 ? 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]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[12713415]
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]
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043435]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
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]
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17555350]
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]
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22559947]
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.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25119	Euonymus laxiflorus	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[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25119	Euonymus laxiflorus	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
Inhibition	6
EC50	1
Activity	8
ED50	2

Activity Type	# Activity
Cell line	14
Organism	3

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	Inhibition	=	-9.0	%	PMID[18163582]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	2.0	%	PMID[23985009]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	55.0	%	PMID[23985009]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	14.0	%	PMID[23985009]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	36.0	%	PMID[20584605]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	14.3	pg/ml	PMID[17896816]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	14.7	pg/ml	PMID[17896816]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	22.0	pg/ml	PMID[19654408]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	24.6	pg/ml	PMID[19654408]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	1245.2	pg/ml	PMID[17190448]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	1576.2	pg/ml	PMID[16792402]
NPT91	Cell line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[19651910]
NPT407	Cell line	COLO 205	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[23999046]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	>	50.0	microg/cm2	PMID[22686608]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	146.0	%	PMID[17908946]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	112.0	%	DOI[10.1021/np50070a027]

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 NPC476110 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Natural Product ID

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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