NPASS Compound

Natural Product: NPC46616

Natural Product ID	NPC46616
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WENLQSBQPMFCOA-YWNVIYJKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5319325
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

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 94 99 0 0 0 0 0 0 0 0999 V2000 4.1676 2.4530 -3.2318 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1271 1.8318 -2.4271 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7798 1.1677 -1.2358 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4871 1.1114 -0.8302 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0739 0.4782 0.3252 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0536 -0.1151 1.0787 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4007 -0.0736 0.6848 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7758 0.5625 -0.4665 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0458 0.6585 -0.9331 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1593 0.1330 -0.3295 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8708 -0.9067 -1.2049 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9679 -1.5018 -0.4014 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3588 -0.7717 0.8193 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9509 0.6443 0.9232 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1498 1.5894 1.0046 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0237 1.2315 2.0192 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1626 1.1059 -0.1197 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8859 -1.4627 1.9602 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0728 -1.6965 -1.2591 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9743 -1.8295 -1.7136 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6542 0.4859 0.6538 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9896 -0.8810 0.4912 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6988 -1.2009 -0.9374 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6816 -1.1653 -1.0771 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1318 -0.1765 -0.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5875 -0.2796 -0.1145 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3340 -0.4278 -1.2612 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7300 -0.5300 -1.2517 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3833 -0.4801 -0.0423 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6412 -0.3302 1.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2743 -0.2337 1.0787 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3539 -0.2880 2.3036 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7542 -0.1408 3.5776 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7458 -0.5771 -0.0051 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6555 0.5050 -0.0588 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5725 0.3166 -1.2164 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5221 -0.8545 -0.9594 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.3050 -0.5250 0.2680 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6837 0.5902 1.0667 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2310 0.4523 2.4939 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8461 -0.7762 3.0255 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3187 0.5044 1.1672 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5939 -0.0983 -0.1059 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7442 -2.0006 -0.8113 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3174 1.4661 -1.4970 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4337 -0.6795 -2.4512 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7041 -0.7240 -3.6615 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3957 -0.5389 1.0642 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0701 0.6361 1.9388 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3328 0.7735 1.9591 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6705 2.8005 -4.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3489 1.7699 -3.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7416 3.3015 -2.6352 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7389 1.6054 -1.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 -0.6178 1.9867 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1274 -0.5561 1.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9355 -0.4037 0.6073 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3098 -0.3235 -2.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6490 -2.5505 -0.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4823 -0.8196 0.9169 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3655 0.8417 1.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6355 1.5484 0.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7546 2.6158 1.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9426 1.3092 1.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6763 -0.8302 2.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3406 -0.8250 -1.6299 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2509 -2.0304 -2.6478 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0799 1.1916 0.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4880 -1.6626 1.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1040 -2.1935 -1.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1245 -0.4586 -1.6260 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8520 0.8351 -0.5301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8712 -0.4733 -2.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7476 -0.1169 2.0376 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9478 -0.8704 3.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5060 -0.3022 4.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3296 0.8885 3.6263 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0623 1.4327 -0.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0412 0.0640 -2.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2031 -0.9733 -1.8089 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4361 -1.4528 0.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0411 1.5882 0.7205 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9411 1.3014 3.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3560 0.4402 2.4822 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1667 -1.2279 2.4518 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5451 0.3046 -1.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6274 -2.3757 -1.7224 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7757 2.2542 -1.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3728 -0.9372 -4.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9284 -1.5241 -3.6517 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2404 0.2794 -3.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8353 -1.3838 1.6040 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4642 1.5999 1.5584 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3962 0.4789 3.0050 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 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 14 17 1 0 13 18 1 0 12 19 1 0 11 20 1 0 5 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 28 46 1 0 46 47 1 0 25 48 1 0 48 49 1 0 49 50 1 0 8 3 1 0 17 10 1 0 50 21 1 0 48 22 1 0 31 26 1 0 42 35 1 0 1 51 1 0 1 52 1 0 1 53 1 0 4 54 1 0 6 55 1 0 7 56 1 0 10 57 1 1 11 58 1 6 12 59 1 1 13 60 1 1 14 61 1 1 15 62 1 0 15 63 1 0 16 64 1 0 18 65 1 0 19 66 1 0 20 67 1 0 21 68 1 0 22 69 1 0 23 70 1 0 23 71 1 0 25 72 1 0 27 73 1 0 31 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 35 78 1 6 36 79 1 6 37 80 1 6 38 81 1 1 39 82 1 6 40 83 1 0 40 84 1 0 41 85 1 0 43 86 1 0 44 87 1 0 45 88 1 0 47 89 1 0 47 90 1 0 47 91 1 0 48 92 1 0 49 93 1 0 49 94 1 0 M END

Standard InCHIKey	WENLQSBQPMFCOA-YWNVIYJKSA-N
Standard InCHI	InChI=1S/C33H44O17/c1-42-18-6-13(4-5-17(18)47-32-27(40)25(38)23(36)21(9-34)48-32)29-15-11-46-30(16(15)12-45-29)14-7-19(43-2)31(20(8-14)44-3)50-33-28(41)26(39)24(37)22(10-35)49-33/h4-8,15-16,21-30,32-41H,9-12H2,1-3H3/t15?,16?,21-,22-,23-,24-,25+,26+,27-,28-,29?,30?,32-,33+/m1/s1
SMILES	COc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C1C2COC(c3cc(c(c(c3)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)OC)C2CO1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	712.26	Volume:	661.6 ? Van der Waals volume.
Dense:	1.077	LogP:	-0.965 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.109 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.911 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	33.0
TPSA:	244.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.127	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.172	Fsp³:	0.636
MCE-18:	140.111 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.514	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.03 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.221 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.123	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.982	MDCK Permeability:	-5.176
Pgp-inhibitor:	0.0	Pgp-substrate:	0.085
PAMPA:	0.872 ? 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):	0.924
20% Bioavailability (F20%):	0.016	30% Bioavailability (F30%):	0.945
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178	MRP1:	0.027
Plasma Protein Binding (PPB):	65.47%	Volume Distribution (VD):	-0.379
Fu:	33.799% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.044
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.027
HLM stability:	0.002 ? 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):

1.23

Half-life (T1/2):

5.688

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.029
Human Hepatotoxicity (H-HT):	0.882	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.978	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.011	Skin Sensitization:	0.998
Carcinogencity:	0.062	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.999
Hematotoxicity:	0.46	Drug-induced Nephrotoxicity:	0.886
Genotoxicity:	0.929	RPMI-8226 Immunitoxicity:	0.277
A549 Cytotoxicity:	0.345	Hek293 Cytotoxicity:	0.261
BCF:	0.776 ? 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:	3.278 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.889 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.844 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
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[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	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	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]
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]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

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

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 NPC46616 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	14910
0.1-0.2	30605
0.2-0.3	3398
0.3-0.4	659
0.4-0.5	205
0.5-0.6	51
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9138	High Similarity	NPC276753
0.9138	High Similarity	NPC205796
0.8983	High Similarity	NPC246947
0.8621	High Similarity	NPC95392
0.8621	High Similarity	NPC84013
0.8621	High Similarity	NPC55715
0.8621	High Similarity	NPC35877
0.8308	Intermediate Similarity	NPC286235
0.791	Intermediate Similarity	NPC38041
0.791	Intermediate Similarity	NPC22150
0.791	Intermediate Similarity	NPC279298
0.7761	Intermediate Similarity	NPC51328
0.7761	Intermediate Similarity	NPC55158
0.7692	Intermediate Similarity	NPC216129
0.7692	Intermediate Similarity	NPC130449
0.7692	Intermediate Similarity	NPC248132
0.7313	Intermediate Similarity	NPC486102
0.7059	Intermediate Similarity	NPC486104
0.7027	Intermediate Similarity	NPC486098
0.6806	Remote Similarity	NPC471063
0.68	Remote Similarity	NPC186316
0.6716	Remote Similarity	NPC486107
0.6623	Remote Similarity	NPC478055
0.6486	Remote Similarity	NPC486100
0.6486	Remote Similarity	NPC486101
0.6375	Remote Similarity	NPC486097
0.6203	Remote Similarity	NPC185307
0.6	Remote Similarity	NPC486099
0.5949	Remote Similarity	NPC39657
0.5938	Remote Similarity	NPC166040
0.5926	Remote Similarity	NPC112861
0.5802	Remote Similarity	NPC470950
0.5789	Remote Similarity	NPC18979
0.5769	Remote Similarity	NPC605526
0.5735	Remote Similarity	NPC479029
0.5732	Remote Similarity	NPC470235
0.5714	Remote Similarity	NPC299144
0.5714	Remote Similarity	NPC486109
0.5714	Remote Similarity	NPC486108
0.5714	Remote Similarity	NPC486106
0.5672	Remote Similarity	NPC472024
0.5672	Remote Similarity	NPC270849
0.5667	Remote Similarity	NPC222127
0.5667	Remote Similarity	NPC82862
0.5641	Remote Similarity	NPC486105
0.5588	Remote Similarity	NPC26653
0.5588	Remote Similarity	NPC80600
0.5571	Remote Similarity	NPC302378
0.5538	Remote Similarity	NPC69513
0.5507	Remote Similarity	NPC248355
0.5465	Remote Similarity	NPC11411
0.5455	Remote Similarity	NPC48863
0.5455	Remote Similarity	NPC251981
0.5455	Remote Similarity	NPC13745
0.5441	Remote Similarity	NPC162093
0.5429	Remote Similarity	NPC55040
0.5373	Remote Similarity	NPC215833
0.5362	Remote Similarity	NPC210478
0.5357	Remote Similarity	NPC129417
0.5342	Remote Similarity	NPC37468
0.5342	Remote Similarity	NPC604095
0.5325	Remote Similarity	NPC158635
0.5325	Remote Similarity	NPC229882
0.5294	Remote Similarity	NPC49074
0.5254	Remote Similarity	NPC121783
0.5254	Remote Similarity	NPC34902
0.5254	Remote Similarity	NPC18449
0.5238	Remote Similarity	NPC217854
0.5176	Remote Similarity	NPC283995
0.5167	Remote Similarity	NPC228907
0.5147	Remote Similarity	NPC9912
0.5139	Remote Similarity	NPC232673
0.5135	Remote Similarity	NPC479030
0.5122	Remote Similarity	NPC217635
0.5119	Remote Similarity	NPC486103
0.5077	Remote Similarity	NPC25817
0.5077	Remote Similarity	NPC152722
0.5068	Remote Similarity	NPC470236
0.506	Remote Similarity	NPC43508

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC46616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4294
0.1-0.2	4716
0.2-0.3	130
0.3-0.4	9
0.4-0.5	1
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