NPASS Compound

Natural Product: NPC324619

Natural Product ID	NPC324619
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hypoglaunine B
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508310
PubChem CID	44583769
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 5.8955 0.6819 1.7565 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8228 0.3164 0.6917 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4349 -0.7580 -0.1455 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9546 -1.9031 -0.6386 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8625 -2.7024 -1.3565 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1434 -2.4321 -1.5931 N 0 0 0 0 0 0 0 0 0 0 0 0 7.6358 -1.3022 -1.1148 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7890 -0.4938 -0.4092 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6477 -2.5300 -0.6412 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2453 -2.8006 -1.8541 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7382 -2.9019 0.2634 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4900 -3.4698 0.1928 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2601 -3.0102 -0.3743 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6930 -2.5393 0.7952 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0625 -2.3418 0.3368 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3669 -1.2381 -0.6641 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4547 -0.0826 -0.3512 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5755 1.1227 -1.2360 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4657 2.1693 -0.9687 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7919 1.5746 -1.2187 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8310 0.0462 -1.2405 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1132 -0.7367 -0.4384 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1801 -1.2487 0.9115 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0304 -0.5339 2.0418 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8786 -0.3632 3.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 -0.8925 2.9533 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5814 0.4351 4.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0606 -1.9828 -1.1506 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9011 -0.2838 -2.7128 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0146 -0.2664 -0.5719 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9140 1.7534 -0.3058 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2185 1.5691 -0.7890 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2248 1.3589 -2.0141 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4352 1.6006 0.0205 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4127 2.7513 0.9615 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4994 1.8262 -0.9115 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8033 2.8574 0.1599 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3257 4.1182 0.2893 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5080 4.6935 -0.7822 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6573 4.7785 1.5288 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1823 6.0533 1.5966 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3816 6.3805 2.9149 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9581 5.2611 3.6110 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5441 4.3518 2.7652 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7091 0.8646 -2.5950 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8013 1.2578 -3.3525 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7192 1.8811 -2.7785 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9371 0.9789 -4.8023 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9401 0.3792 0.9903 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3140 0.8052 0.7675 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0120 1.2845 1.8534 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4525 1.3356 2.9694 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4178 1.7430 1.7286 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6974 -0.8426 -0.4590 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7033 -0.9247 -1.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4630 -1.3846 -2.5102 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0610 -0.4575 -0.9988 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5661 -3.5393 -0.2568 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6009 -4.2923 0.2612 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1231 -3.8629 1.3460 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1009 -5.5331 -0.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4103 -4.2346 -1.0458 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4626 1.5691 1.4699 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3693 0.8015 2.7293 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5190 -0.2210 1.8649 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0033 -0.0930 1.2413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5018 -3.6725 -1.7854 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6922 -1.0301 -1.2832 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2327 0.4552 -0.0193 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7512 -4.5348 -0.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2773 -3.7659 1.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6123 -3.1744 1.6505 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7163 -2.2387 1.2529 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2937 -1.6041 -1.7064 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5080 1.6809 -0.9125 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7271 2.9098 -1.8125 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1902 1.9465 -2.1785 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2166 -1.6225 0.9754 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9483 1.4744 4.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1080 -0.0125 5.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5017 0.3703 4.4854 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1569 -1.0125 -3.0708 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8021 0.5752 -3.4005 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8757 -0.8192 -2.8930 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8464 0.0443 0.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3890 3.2647 1.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6668 3.5032 0.5894 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0150 2.4157 1.9571 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1617 2.4077 -1.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4210 6.7347 0.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7812 7.3093 3.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9992 5.2292 4.7022 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4854 1.8435 -5.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9676 0.8034 -5.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5798 0.0866 -4.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4640 1.1784 1.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1371 -0.4576 1.7252 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0820 0.8389 1.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6554 2.4180 2.5758 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6016 2.2507 0.7588 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0394 0.6585 -1.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3039 -0.7640 0.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8438 -0.8019 -1.6815 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0320 -5.3487 -0.9600 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3304 -5.9952 -1.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3759 -6.2491 0.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4774 -4.7617 -1.5348 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7707 -4.9616 -0.3238 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0404 -3.9731 -1.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 4 9 1 0 9 10 2 0 9 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 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 22 28 1 0 21 29 1 0 21 30 1 0 20 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 34 36 1 0 19 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 18 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 17 49 1 0 49 50 1 0 50 51 1 0 51 52 2 0 51 53 1 0 16 54 1 0 54 55 1 0 55 56 2 0 55 57 1 0 15 58 1 0 58 59 1 0 59 60 2 0 59 61 1 0 13 62 1 0 34 2 1 0 8 3 1 0 28 13 1 0 23 14 1 0 22 17 1 0 44 40 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 0 5 67 1 0 7 68 1 0 8 69 1 0 12 70 1 0 12 71 1 0 14 72 1 0 15 73 1 0 16 74 1 0 18 75 1 0 19 76 1 0 20 77 1 0 23 78 1 0 27 79 1 0 27 80 1 0 27 81 1 0 29 82 1 0 29 83 1 0 29 84 1 0 30 85 1 0 35 86 1 0 35 87 1 0 35 88 1 0 36 89 1 0 41 90 1 0 42 91 1 0 43 92 1 0 48 93 1 0 48 94 1 0 48 95 1 0 49 96 1 0 49 97 1 0 53 98 1 0 53 99 1 0 53100 1 0 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	JXQXTWWCCNHEQZ-PEWXIWONSA-N
Standard InCHI	InChI=1S/C41H47NO20/c1-18-24-12-13-42-15-25(24)34(48)55-16-37(7)27-28(56-20(3)44)32(58-22(5)46)40(17-54-19(2)43)33(59-23(6)47)29(60-35(49)26-11-10-14-53-26)31(61-36(50)38(18,8)51)39(9,52)41(40,62-37)30(27)57-21(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	CC1C2=C(C=NC=C2)C(=O)OCC3(C4C(C(C5(C(C(C(C(C5(C4OC(=O)C)O3)(C)O)OC(=O)C1(C)O)OC(=O)C6=CC=CO6)OC(=O)C)COC(=O)C)OC(=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:	0.667 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.0 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.374 ? 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:	7.83	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:	0.002	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.074 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.013	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.396	MDCK Permeability:	-4.909
Pgp-inhibitor:	0.006	Pgp-substrate:	0.981
PAMPA:	1.0 ? 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):	0.075
20% Bioavailability (F20%):	0.474	30% Bioavailability (F30%):	0.974
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	32.556%	Volume Distribution (VD):	-0.506
Fu:	63.988% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.048
OATP1B3 inhibitor:	0.718	BCRP inhibitor:	0.0
BSEP inhibitor:	0.815

ADMET: Metabolism

CYP1A2-inhibitor:	0.016	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:	0.823
CYP3A4-inhibitor:	0.33	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.984 ? 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):

0.442

Half-life (T1/2):

1.714

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.06
Human Hepatotoxicity (H-HT):	0.329	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.87	Rat Oral Acute Toxicity:	0.211
Maximum Recommended Daily Dose:	0.56	Skin Sensitization:	0.986
Carcinogencity:	0.884	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.217	Ototoxicity:	0.91
Hematotoxicity:	0.134	Drug-induced Nephrotoxicity:	0.95
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.185
A549 Cytotoxicity:	0.004	Hek293 Cytotoxicity:	0.089
BCF:	0.42 ? 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:	3.15 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.467 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.655 ? 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	=	0.1	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 NPC324619 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	23922
0.2-0.3	667
0.3-0.4	66
0.4-0.5	24
0.5-0.6	40
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8842	High Similarity	NPC475315
0.8081	Intermediate Similarity	NPC328154
0.7624	Intermediate Similarity	NPC475533
0.7245	Intermediate Similarity	NPC470306
0.6857	Remote Similarity	NPC326930
0.6822	Remote Similarity	NPC13603
0.6762	Remote Similarity	NPC53255
0.6762	Remote Similarity	NPC85879
0.633	Remote Similarity	NPC475301
0.6286	Remote Similarity	NPC471016
0.6174	Remote Similarity	NPC471979
0.6132	Remote Similarity	NPC471014
0.5981	Remote Similarity	NPC76565
0.5981	Remote Similarity	NPC601313
0.5963	Remote Similarity	NPC146824
0.5948	Remote Similarity	NPC328928
0.5888	Remote Similarity	NPC250807
0.5888	Remote Similarity	NPC57797
0.5872	Remote Similarity	NPC471015
0.5841	Remote Similarity	NPC475600
0.5826	Remote Similarity	NPC473689
0.5826	Remote Similarity	NPC292416
0.5789	Remote Similarity	NPC600224
0.5789	Remote Similarity	NPC604935
0.5752	Remote Similarity	NPC122968
0.5752	Remote Similarity	NPC228377
0.5641	Remote Similarity	NPC475406
0.5596	Remote Similarity	NPC475408
0.5574	Remote Similarity	NPC469748
0.5517	Remote Similarity	NPC476110
0.5508	Remote Similarity	NPC244839
0.55	Remote Similarity	NPC327769
0.55	Remote Similarity	NPC483853
0.55	Remote Similarity	NPC608314
0.5487	Remote Similarity	NPC475601
0.5462	Remote Similarity	NPC477787
0.5431	Remote Similarity	NPC87152
0.5431	Remote Similarity	NPC475631
0.5378	Remote Similarity	NPC600583
0.5345	Remote Similarity	NPC475303
0.5345	Remote Similarity	NPC328186
0.5333	Remote Similarity	NPC319880
0.5333	Remote Similarity	NPC320324
0.5289	Remote Similarity	NPC38959
0.5254	Remote Similarity	NPC475596
0.5197	Remote Similarity	NPC483856
0.5169	Remote Similarity	NPC316841
0.5164	Remote Similarity	NPC327904
0.5126	Remote Similarity	NPC483895
0.5078	Remote Similarity	NPC483854
0.5043	Remote Similarity	NPC475498
0.5039	Remote Similarity	NPC482915

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC324619 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5430
0.1-0.2	3698
0.2-0.3	22
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