NPASS Compound

Natural Product: NPC472719

Natural Product ID	NPC472719
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VHAOZWPEPOPZFA-SDTZFMSQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581710
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 127132 0 0 0 0 0 0 0 0999 V2000 6.6257 3.6893 1.7352 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2799 2.6021 2.3042 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8203 1.6866 1.2259 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8328 1.1888 0.4092 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3022 0.0585 -0.2695 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3534 -0.3969 -1.1639 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8565 -1.6559 -0.9341 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1066 -1.7861 0.4020 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0820 -0.9407 0.4063 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7541 -1.4273 0.3411 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9805 -0.7567 -0.4018 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9724 -0.0027 -0.6495 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3298 -0.5315 -0.2375 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1633 -0.7423 1.2892 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3261 -0.1071 1.9776 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3348 -0.1065 0.9044 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5368 0.3182 -0.3131 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4776 0.1973 -1.4428 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0580 0.8406 -2.6336 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8289 0.8285 -1.2382 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4446 0.5891 0.0743 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4667 0.9022 1.1477 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8795 2.3056 1.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9977 0.8296 2.5482 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3572 1.5103 2.6009 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2439 0.7910 1.6347 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8182 1.1642 0.2373 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9920 2.5804 -0.1292 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7266 0.3448 -0.7009 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1498 0.8381 -0.4859 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0203 0.2921 -1.4218 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5734 0.3668 0.8789 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6773 0.8831 1.9625 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1415 2.2402 2.4507 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9039 -0.0652 3.1588 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9066 0.6188 1.1606 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8574 -1.5103 0.8274 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2188 0.3845 -2.1109 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4014 -0.6207 -3.1165 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5173 -1.6328 -3.5594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6446 -1.8045 -3.2014 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0192 -2.5986 -4.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2268 -3.5496 -4.9916 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4054 -2.4895 -5.0593 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1286 1.4406 -0.0062 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7565 -2.8856 -0.1353 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5229 -3.6553 0.9369 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9378 -3.2029 0.7996 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6229 -3.5774 1.9556 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3503 -5.0178 0.8245 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4335 -3.3020 -0.1855 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5686 0.3715 -1.0375 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9018 1.8447 -0.9878 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8165 2.4346 0.3803 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0552 2.4311 1.0375 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0894 2.5007 -1.9104 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6432 -0.3617 -0.5664 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7869 4.5004 2.2819 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1305 2.9942 2.8966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6127 2.0617 3.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3789 0.8770 1.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5741 -0.6654 0.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2062 -1.9022 -1.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7343 -2.3386 -0.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8553 -1.3748 1.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5368 -1.5519 1.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5704 -1.5360 -0.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0417 -1.8190 1.5358 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7049 -0.2542 1.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1223 0.8259 2.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6290 -0.8341 2.7936 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2105 1.3671 -0.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5994 -0.8604 -1.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1643 1.8313 -2.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4931 0.3332 -2.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8790 1.9000 -1.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6297 -0.5292 0.1456 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7602 2.6482 -0.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5018 3.0337 1.6231 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8730 2.3900 1.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1257 -0.1661 2.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2689 1.3604 3.2116 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3019 2.5930 2.4613 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7305 1.3636 3.6575 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9665 -0.3064 1.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6769 3.1629 0.5445 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4683 2.7044 -1.1495 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0746 3.1952 -0.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4967 0.6018 -1.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6749 -0.7236 -0.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2406 1.9270 -0.5096 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2287 0.9744 -2.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4369 -0.7549 0.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3354 2.8716 2.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7589 2.7282 1.6455 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8756 2.1424 3.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2312 -0.9348 3.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9705 -0.3646 3.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6585 0.4539 4.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4553 -0.2019 1.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0982 -2.2570 1.2135 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6786 -1.5941 1.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1506 -1.8876 -0.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6176 1.2870 -2.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2492 0.8962 -2.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8398 -0.0480 -4.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3867 -1.1929 -2.8355 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5463 -4.2792 -5.7202 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7954 -3.6507 -4.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7258 -1.4351 -5.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0812 -2.8461 -4.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5667 -3.1241 -5.9302 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1718 1.6932 0.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6885 2.1941 -0.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4893 1.4645 0.8801 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2170 -3.0065 -1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1447 -3.2692 1.9146 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3915 -3.8382 -0.0183 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5892 -2.8830 2.6600 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1405 -5.5406 1.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2566 -4.1028 0.3552 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4473 0.1109 -2.1082 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9456 1.9591 -1.3449 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4735 3.5082 0.3297 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6569 1.7574 0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5811 3.2307 -2.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7200 -1.2155 -1.0954 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 12 11 1 1 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 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 32 36 1 0 16 37 1 6 12 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 42 44 1 0 12 45 1 0 10 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 51 1 0 5 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 54 3 1 0 48 8 1 0 17 13 1 0 27 21 1 0 22 16 1 0 33 26 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 1 5 62 1 1 7 63 1 0 7 64 1 0 8 65 1 1 10 66 1 1 13 67 1 6 14 68 1 0 14 69 1 0 15 70 1 0 15 71 1 0 17 72 1 1 18 73 1 6 19 74 1 0 20 75 1 0 20 76 1 0 21 77 1 6 23 78 1 0 23 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 26 85 1 6 28 86 1 0 28 87 1 0 28 88 1 0 29 89 1 0 29 90 1 0 30 91 1 1 31 92 1 0 32 93 1 6 34 94 1 0 34 95 1 0 34 96 1 0 35 97 1 0 35 98 1 0 35 99 1 0 36100 1 0 37101 1 0 37102 1 0 37103 1 0 38104 1 0 38105 1 0 39106 1 0 39107 1 0 43108 1 0 43109 1 0 44110 1 0 44111 1 0 44112 1 0 45113 1 0 45114 1 0 45115 1 0 46116 1 6 47117 1 1 48118 1 6 49119 1 0 50120 1 0 51121 1 0 52122 1 6 53123 1 6 54124 1 6 55125 1 0 56126 1 0 57127 1 0 M END

Standard InCHIKey	VHAOZWPEPOPZFA-SDTZFMSQSA-N
Standard InCHI	InChI=1S/C42H70O15/c1-19(2)21(44)10-14-42(8,57-37-34(52)32(50)30(48)25(56-37)18-54-36-33(51)31(49)29(47)24(17-43)55-36)20-9-12-41(7)28(20)22(45)15-27-39(5)16-23(46)35(53)38(3,4)26(39)11-13-40(27,41)6/h20,22-37,43,45-53H,1,9-18H2,2-8H3/t20-,22+,23+,24+,25+,26-,27+,28-,29+,30+,31-,32-,33+,34+,35-,36+,37-,39-,40+,41+,42-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@]([C@H]3CC[C@@]4([C@@H]3[C@H](O)C[C@H]3[C@@]4(C)CC[C@@H]4[C@]3(C)C[C@@H](O)[C@@H](C4(C)C)O)C)(CCC(=O)C(=C)C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	814.47	Volume:	810.23 ? Van der Waals volume.
Dense:	1.005	LogP:	1.476 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.024 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.229 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	34.0
TPSA:	256.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.126	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.113	Fsp³:	0.929
MCE-18:	138.667 ? 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:	0.749	Fluc inhibitor:	0.0 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.177	Promiscuous compounds:	0.307

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.295	MDCK Permeability:	-5.089
Pgp-inhibitor:	0.0	Pgp-substrate:	0.15
PAMPA:	0.999 ? 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):	0.873
20% Bioavailability (F20%):	0.92	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151	MRP1:	0.179
Plasma Protein Binding (PPB):	75.388%	Volume Distribution (VD):	-0.423
Fu:	18.365% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.004
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.006
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.96
HLM stability:	0.02 ? 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):

0.708

Half-life (T1/2):

2.767

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.019
Human Hepatotoxicity (H-HT):	0.358	Drug-induced Liver Injury (DILI):	0.241
AMES Toxicity:	0.87	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	0.999
Carcinogencity:	0.084	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.997
Hematotoxicity:	0.642	Drug-induced Nephrotoxicity:	0.956
Genotoxicity:	0.108	RPMI-8226 Immunitoxicity:	0.157
A549 Cytotoxicity:	0.627	Hek293 Cytotoxicity:	0.237
BCF:	0.948 ? 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:	3.293 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.602 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.738 ? 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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	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	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT38	Individual protein	Signal transducer and activator of transcription 3	Homo sapiens	IC50	=	270.0	nM	PMID[12027734]

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 NPC472719 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	20366
0.1-0.2	24317
0.2-0.3	4541
0.3-0.4	563
0.4-0.5	41
0.5-0.6	24
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC207845
0.7333	Intermediate Similarity	NPC472717
0.7113	Intermediate Similarity	NPC472718
0.6591	Remote Similarity	NPC8431
0.6264	Remote Similarity	NPC274833
0.617	Remote Similarity	NPC69737
0.5816	Remote Similarity	NPC152584
0.5773	Remote Similarity	NPC213190
0.5743	Remote Similarity	NPC208650
0.573	Remote Similarity	NPC66654
0.5686	Remote Similarity	NPC476360
0.5686	Remote Similarity	NPC476361
0.5631	Remote Similarity	NPC220427
0.5607	Remote Similarity	NPC135369
0.5566	Remote Similarity	NPC246124
0.5481	Remote Similarity	NPC65167
0.5472	Remote Similarity	NPC159005
0.5463	Remote Similarity	NPC180183
0.5327	Remote Similarity	NPC14946
0.5327	Remote Similarity	NPC63368
0.531	Remote Similarity	NPC146868
0.5273	Remote Similarity	NPC472716
0.5213	Remote Similarity	NPC31907
0.52	Remote Similarity	NPC181467
0.5158	Remote Similarity	NPC160734
0.5149	Remote Similarity	NPC131479
0.5133	Remote Similarity	NPC241381
0.513	Remote Similarity	NPC488294
0.5053	Remote Similarity	NPC43912
0.5045	Remote Similarity	NPC6931

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7019
0.1-0.2	2048
0.2-0.3	79
0.3-0.4	4
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