NPASS Compound

Natural Product: NPC475315

Natural Product ID	NPC475315
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hypoglaunine A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503359
PubChem CID	44583768
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 109114 0 0 0 0 0 0 0 0999 V2000 -1.9850 5.0570 -2.0963 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9510 3.9712 -1.9526 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1293 4.0188 -2.6029 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1546 2.9140 -1.1205 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2282 1.8275 -0.9146 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2444 1.8037 0.4532 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6365 2.0974 0.6746 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6709 1.7072 -0.0502 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4538 1.0361 -1.0877 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1495 1.9251 0.1824 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8855 2.0892 -1.0593 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2443 3.0976 0.9750 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5105 0.7323 1.0584 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1282 1.0488 2.4704 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6825 -0.0362 0.7825 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8993 0.5332 0.5071 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0472 -0.1795 0.2376 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0016 -1.5113 0.2381 N 0 0 0 0 0 0 0 0 0 0 0 0 6.8315 -2.1076 0.5027 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6634 -1.4481 0.7761 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4480 -2.2215 1.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5424 -3.1588 1.9415 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2204 -2.0579 0.5082 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0329 -2.7580 0.7635 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8681 -2.2893 -0.0692 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6312 -0.9847 -0.1766 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5632 -0.5955 0.4856 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1533 0.5930 1.2858 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0320 0.9317 2.4617 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0697 0.1795 1.9064 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5486 -0.3369 -0.6139 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8338 0.6262 -1.5309 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7381 1.0023 -2.5520 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5527 0.7153 -3.8858 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5368 0.0893 -4.2503 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5670 1.1508 -4.9114 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8369 0.3085 -0.2493 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7834 1.5876 0.3254 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0096 2.1956 0.6712 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0882 1.5564 0.4474 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0899 3.5045 1.2645 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0394 4.3403 1.5783 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5950 5.4771 2.1220 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9575 5.2890 2.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1948 4.1167 1.6046 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9353 -1.6363 -1.2930 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3644 -1.7586 -1.4076 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1058 -1.8038 -2.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5365 -1.7424 -3.6114 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5846 -1.9259 -2.4290 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3295 -2.9033 -0.8137 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4440 -2.8655 0.3783 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9214 -1.7550 1.3420 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2582 -1.8559 2.5592 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9647 -2.0779 3.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2247 -2.1913 3.6928 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3037 -2.1947 5.0565 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3297 -3.8958 -0.4973 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4242 -5.1210 -1.0841 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5804 -5.4201 -1.9706 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4732 -6.1056 -0.7213 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2396 -2.7833 -1.4880 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6367 5.9864 -1.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9623 4.6959 -1.7332 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0786 5.2232 -3.2021 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6036 2.1428 -1.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2098 2.6738 1.0256 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6461 2.9232 -1.0571 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3308 1.1575 -1.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1613 2.4224 -1.8632 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3383 3.8934 0.3708 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6386 -0.0408 0.7853 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0425 1.4779 2.9713 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3881 1.8742 2.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7540 0.1657 3.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9795 1.6445 0.4972 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9763 0.3544 0.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7405 -3.2106 0.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7898 -2.8119 1.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2700 -3.8332 0.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2830 2.0146 2.5241 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5118 0.7600 3.4602 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9497 0.3484 2.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2379 0.8115 2.6381 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0367 0.0280 -2.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5557 1.2310 -4.4197 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6227 0.3463 -5.6426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2357 2.1201 -5.2894 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3780 0.5165 -1.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4782 -0.3143 0.4112 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9914 4.1545 1.4325 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0615 6.3476 2.4819 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6857 6.0077 2.4834 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6574 -1.5267 -2.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8959 -2.2409 -1.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.9848 -2.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9039 -2.6582 -3.1989 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7397 -3.4256 -1.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3894 -3.8344 0.8658 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0062 -1.8577 1.5224 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9447 -1.6116 5.7691 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7383 -1.8605 5.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3669 -3.2517 5.3992 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4071 -5.8085 -1.2505 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1856 -7.1321 -1.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6657 -6.1161 0.3659 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3321 -2.5021 -1.6092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2336 -3.8743 -1.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7369 -2.2263 -2.2729 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 10 12 1 0 10 13 1 0 13 14 1 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 27 26 1 6 27 28 1 0 28 29 1 0 28 30 1 1 27 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 31 37 1 1 37 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 31 46 1 0 46 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 46 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 2 0 55 57 1 0 51 58 1 0 58 59 1 0 59 60 2 0 59 61 1 0 25 62 1 6 32 5 1 0 45 41 1 0 28 6 1 0 20 15 1 0 52 25 1 0 53 27 1 0 1 63 1 0 1 64 1 0 1 65 1 0 5 66 1 6 6 67 1 1 11 68 1 0 11 69 1 0 11 70 1 0 12 71 1 0 13 72 1 0 14 73 1 0 14 74 1 0 14 75 1 0 16 76 1 0 17 77 1 0 19 78 1 0 24 79 1 0 24 80 1 0 29 81 1 0 29 82 1 0 29 83 1 0 30 84 1 0 32 85 1 6 36 86 1 0 36 87 1 0 36 88 1 0 37 89 1 0 37 90 1 0 42 91 1 0 43 92 1 0 44 93 1 0 46 94 1 6 50 95 1 0 50 96 1 0 50 97 1 0 51 98 1 6 52 99 1 1 53100 1 1 57101 1 0 57102 1 0 57103 1 0 61104 1 0 61105 1 0 61106 1 0 62107 1 0 62108 1 0 62109 1 0 M END

Standard InCHIKey	ZWMDSFIGEYLEIP-PEWXIWONSA-N
Standard InCHI	InChI=1S/C41H47NO20/c1-18-24-12-13-42-15-25(24)34(48)54-16-37(7)27-28(56-19(2)43)32(59-22(5)46)40(17-55-35(49)26-11-10-14-53-26)33(60-23(6)47)29(57-20(3)44)31(61-36(50)38(18,8)51)39(9,52)41(40,62-37)30(27)58-21(4)45/h10-15,18,27-33,51-52H,16-17H2,1-9H3/t18?,27-,28-,29+,30-,31+,32-,33+,37+,38?,39+,40-,41+/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H]2OC(=O)C(C)(O)C(C)c3ccncc3C(=O)OC[C@@]3(O[C@@]4([C@@]2(C)O)[C@]([C@H]1OC(=O)C)(COC(=O)c1ccco1)[C@H](OC(=O)C)[C@@H]([C@@H]3[C@H]4OC(=O)C)OC(=O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	873.27	Volume:	818.88 ? Van der Waals volume.
Dense:	1.066	LogP:	0.543 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.887 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.071 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	42.0
TPSA:	286.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.277	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.818	Fsp³:	0.585
MCE-18:	230.4 ? 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:	0.497	Fluc inhibitor:	0.011 ? 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:	0.137 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.01	Promiscuous compounds:	0.299

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.38	MDCK Permeability:	-4.908
Pgp-inhibitor:	0.352	Pgp-substrate:	0.884
PAMPA:	0.996 ? 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%):	0.452	30% Bioavailability (F30%):	0.945
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	32.682%	Volume Distribution (VD):	-0.456
Fu:	61.118% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.963	BCRP inhibitor:	0.0
BSEP inhibitor:	0.422

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:	0.803
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.586 ? 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):

1.101

Half-life (T1/2):

1.558

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.19	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.963	Rat Oral Acute Toxicity:	0.552
Maximum Recommended Daily Dose:	0.697	Skin Sensitization:	1.0
Carcinogencity:	0.747	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.026
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.556
Hematotoxicity:	0.775	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.487
A549 Cytotoxicity:	0.062	Hek293 Cytotoxicity:	0.038
BCF:	0.41 ? 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:	3.074 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.542 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.946 ? 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	7
EC50	2

Activity Type	# Activity
Cell line	7
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[19487444]
NPT179	Cell line	A2780	Homo sapiens	IC50	>	1000.0	nM	PMID[25734623]
NPT180	Cell line	HCT-8	Homo sapiens	IC50	>	1000.0	nM	PMID[1433213]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	>	1000.0	nM	PubChem BioAssay data set
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	>	1000.0	nM	PMID[25237727]
NPT81	Cell line	A549	Homo sapiens	IC50	>	1000.0	nM	PMID[18183025]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	0.13	ug.mL-1	PMID[16872140]

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 NPC475315 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	25127
0.1-0.2	23973
0.2-0.3	642
0.3-0.4	46
0.4-0.5	26
0.5-0.6	37
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8842	High Similarity	NPC324619
0.8632	High Similarity	NPC475533
0.7282	Intermediate Similarity	NPC328154
0.7143	Intermediate Similarity	NPC470306
0.6381	Remote Similarity	NPC471015
0.619	Remote Similarity	NPC471016
0.6	Remote Similarity	NPC326930
0.5982	Remote Similarity	NPC13603
0.5946	Remote Similarity	NPC475301
0.5909	Remote Similarity	NPC53255
0.5909	Remote Similarity	NPC85879
0.5888	Remote Similarity	NPC471014
0.5888	Remote Similarity	NPC76565
0.5888	Remote Similarity	NPC601313
0.5872	Remote Similarity	NPC146824
0.5841	Remote Similarity	NPC600224
0.5794	Remote Similarity	NPC250807
0.5794	Remote Similarity	NPC57797
0.5702	Remote Similarity	NPC604935
0.5678	Remote Similarity	NPC471979
0.562	Remote Similarity	NPC469748
0.5593	Remote Similarity	NPC328928
0.5586	Remote Similarity	NPC473833
0.5556	Remote Similarity	NPC244839
0.5536	Remote Similarity	NPC475601
0.5505	Remote Similarity	NPC475408
0.5424	Remote Similarity	NPC600583
0.5299	Remote Similarity	NPC476110
0.525	Remote Similarity	NPC319880
0.525	Remote Similarity	NPC320324
0.525	Remote Similarity	NPC477787
0.5214	Remote Similarity	NPC87152
0.5214	Remote Similarity	NPC475600
0.5214	Remote Similarity	NPC475631
0.521	Remote Similarity	NPC473689
0.521	Remote Similarity	NPC292416
0.5207	Remote Similarity	NPC38959
0.5128	Remote Similarity	NPC475303
0.5128	Remote Similarity	NPC122968
0.5128	Remote Similarity	NPC328186
0.5128	Remote Similarity	NPC228377
0.5082	Remote Similarity	NPC327904
0.5042	Remote Similarity	NPC475596
0.5041	Remote Similarity	NPC475406

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5348
0.1-0.2	3781
0.2-0.3	21
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