NPASS Compound

Natural Product: NPC475533

Natural Product ID	NPC475533
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hypoglaunine D
IUPAC Name	n.a.
Synonyms	Hypoglaunine D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL507563
PubChem CID	44583770
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 108113 0 0 0 0 0 0 0 0999 V2000 4.9686 -0.2001 -0.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7846 0.5644 0.7535 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2165 1.9751 0.6163 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9706 1.9680 -0.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1428 1.8672 -1.5001 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6817 2.0291 0.1912 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6209 1.7407 -0.7838 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7206 2.2056 -0.5366 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7968 1.2527 -1.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7598 -0.1248 -0.6291 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6155 -1.0746 -1.4462 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2261 -2.5358 -1.1883 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7992 -2.8752 -1.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1398 -1.5841 -1.8197 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3623 -0.7082 -0.6197 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6926 0.2038 -0.4205 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9057 0.3457 1.1060 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8405 -0.1141 -1.0966 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3768 -1.5824 0.5212 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0346 -2.8180 0.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3462 -3.2702 0.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4772 -2.5345 0.4353 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8234 -2.0660 1.6473 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8400 -2.4343 2.4890 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8657 -1.3301 2.2965 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6071 -0.2155 1.9801 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4794 0.2406 3.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6410 -0.3192 4.2418 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9288 -1.3840 4.5171 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0976 -1.8585 3.6081 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7705 -3.7845 1.0963 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1412 -2.0415 -2.0897 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5722 -2.2530 -3.3866 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7886 -2.0262 -4.3282 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9317 -2.7378 -3.6609 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9675 -3.0993 -0.1232 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9761 -4.0375 -0.2672 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2512 -4.4145 -1.4329 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7507 -4.6259 0.8488 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7421 -0.7400 -2.7827 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9434 -0.5112 -3.4436 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9960 -0.6115 -2.7954 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9342 -0.1575 -4.8886 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4512 -0.1646 0.7299 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9707 0.6329 1.7163 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4163 0.7684 2.9963 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4061 0.0729 3.3408 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7559 1.6926 3.9205 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1339 1.9008 5.2408 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2828 2.8333 5.7830 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4141 3.1541 4.7535 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7311 2.4585 3.6781 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0240 1.8817 -0.9285 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6932 2.5191 -1.9479 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2018 2.5561 -3.1070 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0070 3.1922 -1.7651 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9478 3.4306 -1.2384 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3486 4.5700 -0.6009 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5264 4.5562 0.6364 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5596 5.8018 -1.4264 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1539 2.9426 -0.0367 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9999 -0.6729 -0.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9999 0.5580 -1.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2340 -0.9611 -0.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9739 0.9400 0.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9124 2.3510 1.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0158 1.9389 -1.7506 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9291 2.4111 0.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5529 1.2859 -2.2133 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6874 -1.0563 -1.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6644 -3.0422 -2.1112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5064 -3.7496 -1.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6843 -1.3257 -2.7308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4511 -0.4243 1.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9706 0.4609 1.3253 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4576 1.3173 1.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 0.0879 -2.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4922 -4.2263 0.7415 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6107 -3.7742 -0.9262 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0781 1.1531 2.8050 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3514 0.1186 4.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5129 -2.7824 3.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4230 -3.2558 1.7790 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0029 -4.2926 1.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2338 -4.5684 0.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9391 -3.3001 -4.6255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3241 -3.4192 -2.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5934 -1.8363 -3.7814 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7847 -4.8083 0.4850 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3435 -5.6315 1.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8307 -3.9483 1.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2108 -1.0508 -5.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7168 0.6309 -5.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9274 0.2453 -5.1774 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5568 0.0420 0.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4627 -1.2152 1.1272 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9454 1.4265 5.7647 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3162 3.2102 6.7990 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3841 3.8715 4.8677 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9059 4.2125 -2.2097 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2684 3.3223 -0.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8165 2.6909 -2.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2532 6.7137 -0.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6413 5.8584 -1.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9663 5.7362 -2.3645 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7456 3.9460 0.0835 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2516 2.7449 -1.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1633 2.9452 0.4469 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 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 9 53 1 0 53 54 1 0 54 55 2 0 54 56 1 0 8 57 1 0 57 58 1 0 58 59 2 0 58 60 1 0 3 61 1 0 26 2 1 0 16 7 1 0 15 10 1 0 20 13 1 0 30 25 1 0 52 48 1 0 1 62 1 0 1 63 1 0 1 64 1 0 2 65 1 0 3 66 1 0 7 67 1 0 8 68 1 0 9 69 1 0 11 70 1 0 12 71 1 0 13 72 1 0 14 73 1 0 17 74 1 0 17 75 1 0 17 76 1 0 18 77 1 0 21 78 1 0 21 79 1 0 27 80 1 0 28 81 1 0 30 82 1 0 31 83 1 0 31 84 1 0 31 85 1 0 35 86 1 0 35 87 1 0 35 88 1 0 39 89 1 0 39 90 1 0 39 91 1 0 43 92 1 0 43 93 1 0 43 94 1 0 44 95 1 0 44 96 1 0 49 97 1 0 50 98 1 0 51 99 1 0 56100 1 0 56101 1 0 56102 1 0 60103 1 0 60104 1 0 60105 1 0 61106 1 0 61107 1 0 61108 1 0 M END

Standard InCHIKey	KQXBVFVORGQCER-PWIKAHHMSA-N
Standard InCHI	InChI=1S/C41H47NO19/c1-18-19(2)35(48)60-32-30(56-21(4)44)34(59-24(7)47)40(17-54-37(50)27-11-10-14-52-27)33(58-23(6)46)29(55-20(3)43)28-31(57-22(5)45)41(40,39(32,9)51)61-38(28,8)16-53-36(49)26-15-42-13-12-25(18)26/h10-15,18-19,28-34,51H,16-17H2,1-9H3/t18?,19?,28-,29-,30+,31-,32+,33-,34+,38+,39+,40-,41+/m1/s1
SMILES	CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1C=CN=C5)C)OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C6=CC=CO6)OC(=O)C)OC(=O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	857.27	Volume:	810.09 ? Van der Waals volume.
Dense:	1.058	LogP:	1.028 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.356 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.759 ? 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:	7.734	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:	0.025	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.07 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.014	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152	MDCK Permeability:	-4.822
Pgp-inhibitor:	0.079	Pgp-substrate:	0.896
PAMPA:	0.998 ? 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):	0.004
20% Bioavailability (F20%):	0.188	30% Bioavailability (F30%):	0.723
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	54.688%	Volume Distribution (VD):	-0.43
Fu:	41.566% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.06
OATP1B3 inhibitor:	0.641	BCRP inhibitor:	0.0
BSEP inhibitor:	0.927

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.443
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.99 ? 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):

0.341

Half-life (T1/2):

1.558

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.12
Human Hepatotoxicity (H-HT):	0.375	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.805	Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.792	Skin Sensitization:	0.984
Carcinogencity:	0.958	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.262	Ototoxicity:	0.906
Hematotoxicity:	0.149	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.996	RPMI-8226 Immunitoxicity:	0.167
A549 Cytotoxicity:	0.02	Hek293 Cytotoxicity:	0.149
BCF:	0.593 ? 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:	3.415 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.666 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.993 ? 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

Activity Type	# Activity
Cell line	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	=	22.2	ug.mL-1	PMID[19583252]

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 NPC475533 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	25742
0.1-0.2	23287
0.2-0.3	704
0.3-0.4	50
0.4-0.5	21
0.5-0.6	36
0.6-0.7	14
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
0.8632	High Similarity	NPC475315
0.8352	Intermediate Similarity	NPC470306
0.7624	Intermediate Similarity	NPC324619
0.6733	Remote Similarity	NPC471014
0.6667	Remote Similarity	NPC326930
0.6604	Remote Similarity	NPC475301
0.6569	Remote Similarity	NPC471016
0.6569	Remote Similarity	NPC76565
0.6569	Remote Similarity	NPC601313
0.6471	Remote Similarity	NPC475408
0.6262	Remote Similarity	NPC53255
0.6262	Remote Similarity	NPC85879
0.6239	Remote Similarity	NPC328154
0.6226	Remote Similarity	NPC473833
0.6195	Remote Similarity	NPC328928
0.6154	Remote Similarity	NPC250807
0.6154	Remote Similarity	NPC57797
0.5893	Remote Similarity	NPC476110
0.5893	Remote Similarity	NPC13603
0.5893	Remote Similarity	NPC600224
0.5862	Remote Similarity	NPC471979
0.5804	Remote Similarity	NPC87152
0.5804	Remote Similarity	NPC475600
0.5804	Remote Similarity	NPC475631
0.5798	Remote Similarity	NPC469748
0.578	Remote Similarity	NPC146824
0.5752	Remote Similarity	NPC604935
0.5739	Remote Similarity	NPC244839
0.5714	Remote Similarity	NPC475303
0.5614	Remote Similarity	NPC475596
0.5603	Remote Similarity	NPC600583
0.5586	Remote Similarity	NPC475601
0.55	Remote Similarity	NPC475426
0.5462	Remote Similarity	NPC327769
0.5462	Remote Similarity	NPC483853
0.5462	Remote Similarity	NPC608314
0.5439	Remote Similarity	NPC122968
0.5439	Remote Similarity	NPC328186
0.5439	Remote Similarity	NPC228377
0.5424	Remote Similarity	NPC319880
0.5424	Remote Similarity	NPC320324
0.5413	Remote Similarity	NPC35208
0.5405	Remote Similarity	NPC471015
0.5378	Remote Similarity	NPC38959
0.5294	Remote Similarity	NPC477787
0.5268	Remote Similarity	NPC475498
0.5259	Remote Similarity	NPC316841
0.525	Remote Similarity	NPC327904
0.5159	Remote Similarity	NPC483856
0.5126	Remote Similarity	NPC473689
0.5126	Remote Similarity	NPC292416
0.5042	Remote Similarity	NPC475644
0.5039	Remote Similarity	NPC483854

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5351
0.1-0.2	3774
0.2-0.3	25
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