NPASS Compound

Natural Product: NPC326930

Natural Product ID	NPC326930
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hyponine F
IUPAC Name	n.a.
Synonyms	Hyponine F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL525633
PubChem CID	44583773
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 108113 0 0 0 0 0 0 0 0999 V2000 -5.7999 1.6908 1.1570 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4714 1.3954 1.6974 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0749 1.6703 2.8562 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5487 0.7502 0.8630 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2310 0.4528 1.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4884 -0.2121 0.2458 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4853 0.8330 -0.8558 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7869 1.3640 -1.0300 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4890 1.2960 -2.2004 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9574 0.7314 -3.1851 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8446 1.8839 -2.2769 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5877 1.9949 -0.6323 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1664 2.9985 0.1673 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4702 4.2795 -0.2608 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1994 4.5483 -1.4659 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0645 5.2404 0.6389 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3810 5.0109 1.9541 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9224 6.1835 2.4384 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9054 7.0702 1.3818 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3864 6.4710 0.3257 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7997 1.6574 -0.1609 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7788 0.6592 0.9866 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0354 -0.4879 0.5021 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5392 -0.7466 -0.7753 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6513 -2.0784 -0.9864 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0906 -2.7339 0.1509 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5433 -2.7364 -0.2030 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2823 -1.4371 -0.0676 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4870 -1.5778 0.6494 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7381 -1.5830 0.1509 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7776 -1.4463 -1.0835 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9894 -1.7324 0.9330 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1253 -3.7637 0.6169 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5930 -4.9390 0.1182 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5113 -5.1347 -1.1217 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1894 -5.9697 1.0310 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1286 -1.7446 1.2717 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3864 -1.8790 1.8829 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5403 -2.0450 3.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4618 -2.0713 3.9235 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8711 -2.1877 3.8885 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0100 -2.3760 -2.3342 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0553 -2.6136 -1.1867 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0635 -1.7941 -0.8273 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3865 -2.0028 -0.9492 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8089 -3.0706 -1.4582 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4637 -1.0856 -0.5309 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7805 0.1166 -1.0520 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1860 0.8157 -2.1978 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7328 0.7616 -2.4155 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9176 1.2872 -1.2687 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 1.8346 -0.3275 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5528 1.1704 -1.2441 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4605 1.8411 -3.5230 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9284 0.4381 -3.5004 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8368 0.7724 -0.4460 N 0 0 0 0 0 0 0 0 0 0 0 0 7.5355 0.3101 0.5795 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2301 -0.9151 1.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1987 -1.5934 0.5610 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5018 1.2353 2.3224 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0963 0.1911 1.0761 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9952 1.0784 0.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6246 1.4964 1.8712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8199 2.7490 0.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8681 1.4246 1.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3994 -0.1771 2.2432 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1932 0.3678 -1.8218 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9892 2.4300 -3.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6246 1.1080 -2.1264 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9667 2.6264 -1.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4484 2.4814 -1.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2538 4.1174 2.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2820 6.3444 3.4567 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2651 8.0834 1.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2799 2.5697 0.2118 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2621 -3.7358 0.3896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6089 -3.1865 -1.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6913 -1.2700 -1.0925 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8710 -1.6095 0.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0017 -2.8049 1.2875 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0206 -1.1187 1.8383 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9493 -6.5774 0.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7129 -5.4103 1.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4089 -6.5683 1.5360 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6267 -1.7979 2.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4387 -1.2258 3.8122 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4526 -3.0282 3.4497 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6920 -2.3965 4.9612 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7344 -2.0118 -3.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9136 -1.8333 -2.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0620 -3.4691 -2.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1187 -3.0613 -2.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0911 -3.5232 -0.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4413 1.9281 -2.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3943 -0.1865 -2.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9747 2.7395 -3.1500 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3870 2.0173 -3.5665 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9185 1.5332 -4.4640 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 0.2415 -3.2615 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5027 -0.4654 -3.9510 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9274 1.2875 -4.2141 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3630 0.8893 1.0090 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8168 -1.2684 1.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9049 -2.5864 0.9389 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2121 2.3117 2.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1212 0.6558 3.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4551 1.3686 2.9508 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5816 0.4652 1.8662 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 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 12 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 27 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 26 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 25 42 1 6 25 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 2 0 51 53 1 0 50 54 1 0 49 55 1 0 48 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 22 60 1 0 22 61 1 1 28 6 1 0 59 47 1 0 23 6 1 0 20 16 1 0 53 21 1 0 37 23 1 0 1 62 1 0 1 63 1 0 1 64 1 0 5 65 1 0 5 66 1 0 7 67 1 6 11 68 1 0 11 69 1 0 11 70 1 0 12 71 1 6 17 72 1 0 18 73 1 0 19 74 1 0 21 75 1 1 26 76 1 1 27 77 1 6 28 78 1 6 32 79 1 0 32 80 1 0 32 81 1 0 36 82 1 0 36 83 1 0 36 84 1 0 37 85 1 1 41 86 1 0 41 87 1 0 41 88 1 0 42 89 1 0 42 90 1 0 42 91 1 0 43 92 1 0 43 93 1 0 49 94 1 0 50 95 1 0 54 96 1 0 54 97 1 0 54 98 1 0 55 99 1 0 55100 1 0 55101 1 0 57102 1 0 58103 1 0 59104 1 0 60105 1 0 60106 1 0 60107 1 0 61108 1 0 M END

Standard InCHIKey	ALJJHPQWUBVQNM-KSTPHJKESA-N
Standard InCHI	InChI=1S/C41H47NO19/c1-18-19(2)35(48)60-32-30(59-37(50)26-13-11-15-52-26)34(58-24(7)47)40(17-53-20(3)43)33(57-23(6)46)29(55-21(4)44)27-31(56-22(5)45)41(40,39(32,9)51)61-38(27,8)16-54-36(49)25-12-10-14-42-28(18)25/h10-15,18-19,27,29-34,51H,16-17H2,1-9H3/t18?,19?,27-,29-,30+,31-,32+,33-,34+,38+,39+,40-,41+/m1/s1
SMILES	CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)c3ccco3)[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)c1c(C(C(C(=O)O3)C)C)nccc1)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	857.27	Volume:	810.09 ? Van der Waals volume.
Dense:	1.058	LogP:	0.98 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.409 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.958 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	42.0
TPSA:	265.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.293	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.697	Fsp³:	0.585
MCE-18:	221.538 ? 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:	0.648	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.158 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.013	Promiscuous compounds:	0.341

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.401	MDCK Permeability:	-4.918
Pgp-inhibitor:	0.065	Pgp-substrate:	0.06
PAMPA:	0.863 ? 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%):	0.003	30% Bioavailability (F30%):	0.05
50% Bioavailability (F50%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323	MRP1:	1.0
Plasma Protein Binding (PPB):	37.702%	Volume Distribution (VD):	-0.423
Fu:	57.779% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.954	BCRP inhibitor:	0.0
BSEP inhibitor:	0.945

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.014	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.485 ? 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):

0.542

Half-life (T1/2):

1.451

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.048
Human Hepatotoxicity (H-HT):	0.389	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.988	Rat Oral Acute Toxicity:	0.467
Maximum Recommended Daily Dose:	0.772	Skin Sensitization:	1.0
Carcinogencity:	0.847	Eye Corrosion:	0.0
Eye Irritation:	0.063	Respiratory Toxicity:	0.135
Drug-induced Neurotoxicity:	0.311	Ototoxicity:	0.578
Hematotoxicity:	0.928	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.983	RPMI-8226 Immunitoxicity:	0.451
A549 Cytotoxicity:	0.647	Hek293 Cytotoxicity:	0.195
BCF:	0.529 ? 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:	3.2 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.634 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.408 ? 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]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0040-4039(99)00339-1]
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]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10746886]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	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]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[23252270]
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]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	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]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[535601]
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]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8328267]
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]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	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]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Phytochemistry, 2000, 53, 715-722.]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1152	Tripterygium hypoglaucum	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	2

Activity Type	# Activity
Cell line	2
Organism	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell line	H9	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[16989518]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	35.2	ug.mL-1	PMID[16989518]

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 NPC326930 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	24617
0.1-0.2	24450
0.2-0.3	633
0.3-0.4	78
0.4-0.5	12
0.5-0.6	19
0.6-0.7	23
0.7-0.8	0
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC475301
0.8876	High Similarity	NPC76565
0.8876	High Similarity	NPC601313
0.8526	High Similarity	NPC475600
0.82	Intermediate Similarity	NPC328928
0.8061	Intermediate Similarity	NPC476110
0.8021	Intermediate Similarity	NPC53255
0.8021	Intermediate Similarity	NPC85879
0.7959	Intermediate Similarity	NPC87152
0.7959	Intermediate Similarity	NPC475631
0.7941	Intermediate Similarity	NPC483853
0.7941	Intermediate Similarity	NPC608314
0.7857	Intermediate Similarity	NPC475303
0.77	Intermediate Similarity	NPC475596
0.7596	Intermediate Similarity	NPC327769
0.7525	Intermediate Similarity	NPC13603
0.7431	Intermediate Similarity	NPC483856
0.7347	Intermediate Similarity	NPC475498
0.7273	Intermediate Similarity	NPC473833
0.7273	Intermediate Similarity	NPC483854
0.7216	Intermediate Similarity	NPC35208
0.7207	Intermediate Similarity	NPC482915
0.713	Intermediate Similarity	NPC475426
0.7115	Intermediate Similarity	NPC475644
0.7041	Intermediate Similarity	NPC250807
0.7041	Intermediate Similarity	NPC57797
0.6857	Remote Similarity	NPC324619
0.6827	Remote Similarity	NPC122968
0.6827	Remote Similarity	NPC228377
0.68	Remote Similarity	NPC475137
0.6792	Remote Similarity	NPC30456
0.6792	Remote Similarity	NPC488904
0.6667	Remote Similarity	NPC475533
0.6604	Remote Similarity	NPC471977
0.6602	Remote Similarity	NPC146824
0.6455	Remote Similarity	NPC477787
0.6422	Remote Similarity	NPC473689
0.6422	Remote Similarity	NPC292416
0.6355	Remote Similarity	NPC328186
0.6339	Remote Similarity	NPC471979
0.6296	Remote Similarity	NPC470486
0.6275	Remote Similarity	NPC470306
0.6216	Remote Similarity	NPC475406
0.6216	Remote Similarity	NPC244839
0.6216	Remote Similarity	NPC600583
0.6161	Remote Similarity	NPC319880
0.6161	Remote Similarity	NPC320324
0.6147	Remote Similarity	NPC316841
0.6	Remote Similarity	NPC475315
0.5965	Remote Similarity	NPC327904
0.5965	Remote Similarity	NPC38959
0.5804	Remote Similarity	NPC471190
0.5738	Remote Similarity	NPC483855
0.5701	Remote Similarity	NPC471016
0.569	Remote Similarity	NPC170751
0.5586	Remote Similarity	NPC475362
0.5575	Remote Similarity	NPC328154
0.5565	Remote Similarity	NPC600607
0.5517	Remote Similarity	NPC601643
0.5385	Remote Similarity	NPC253482
0.5321	Remote Similarity	NPC473850
0.5299	Remote Similarity	NPC611166
0.5259	Remote Similarity	NPC600224
0.5259	Remote Similarity	NPC604935
0.5221	Remote Similarity	NPC473506
0.5172	Remote Similarity	NPC477788
0.5135	Remote Similarity	NPC471014
0.5126	Remote Similarity	NPC475648

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC326930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5088
0.1-0.2	4031
0.2-0.3	31
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