NPASS Compound

Natural Product: NPC185291

Natural Product ID	NPC185291
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FCMBHJYOOLTZKM-ZAMFQLPESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101720866
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 122128 0 0 0 0 0 0 0 0999 V2000 -10.8752 -0.0771 0.9755 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4926 0.2108 0.3797 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5604 1.0472 -0.8338 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5212 2.0809 -1.0038 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6416 2.3149 0.1914 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4362 0.9453 0.8506 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7079 0.6698 1.4021 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1878 -0.0343 -0.0730 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0945 -0.8285 0.1902 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4221 -2.2798 0.3481 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1435 -3.0104 0.7048 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4799 -4.4486 0.9550 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3869 -4.5331 2.0226 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2345 -2.8921 -0.3613 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8491 -1.5328 -0.3703 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0180 -0.7172 -0.8702 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6867 0.5801 -1.1570 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6726 -1.3397 -1.0308 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6630 -0.9663 -0.1496 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6755 -2.0903 -0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7482 -1.7321 0.0662 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1945 -0.5663 -0.8442 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8936 -1.0516 -2.2229 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3324 0.5592 -0.3599 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8471 1.8478 -0.8634 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1749 2.0987 -0.1669 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1507 1.0788 -0.6834 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5742 1.5299 -2.0500 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6260 -0.3106 -0.6111 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4430 -1.2353 -1.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8568 -0.9972 -1.1699 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3260 0.0135 -0.4523 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7723 0.0932 -0.2233 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1792 -0.2758 1.1842 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6784 -0.5855 1.1171 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8951 -2.0481 0.7799 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3635 0.2532 0.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6843 1.5741 -0.1117 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2619 1.4242 -0.6776 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4316 2.6007 -0.3176 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1030 2.3932 0.2715 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4490 1.0790 0.1464 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1402 0.5450 1.5575 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4554 1.3551 -2.1507 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8170 2.1327 -2.8866 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3253 0.4498 -2.7169 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3142 -0.3295 2.4353 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6606 0.0850 3.4379 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6705 -0.5412 2.6118 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1397 0.3680 -0.5700 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7927 1.4018 0.3710 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5785 0.7504 -1.9677 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2927 -2.4360 1.4251 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3527 3.0950 1.1011 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0740 3.3293 -1.3490 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6237 0.2240 -1.9843 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8822 -1.0919 1.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1403 0.6994 1.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5692 -0.1112 0.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0903 -0.8031 0.0871 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5639 1.5706 -0.8283 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8458 1.8183 -1.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7034 2.8099 -0.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7429 0.9831 1.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6396 -0.4762 1.1394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8098 -2.7509 -0.5718 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7174 -2.5068 1.5973 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5625 -4.9739 1.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9844 -4.8932 0.0932 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8205 -5.4090 2.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7134 -1.2964 0.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3808 -1.2687 -1.7897 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0093 0.8117 -2.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1139 -0.9254 0.8636 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9366 -2.8129 0.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7809 -2.7354 -1.0615 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8784 -1.4298 1.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3689 -2.6131 -0.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1773 -1.2900 -2.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2205 -0.4265 -3.0381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4137 -2.0496 -2.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4685 0.5798 0.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8932 1.9526 -1.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1667 2.6542 -0.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4469 3.1341 -0.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9728 2.0688 0.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2724 2.3992 -1.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7634 1.9578 -2.6696 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0237 0.7337 -2.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8592 -0.6900 0.4307 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2025 -2.2786 -1.1369 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2057 -1.1237 -2.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5730 -1.7393 -1.5670 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3148 -0.6645 -0.8702 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6724 -1.2309 1.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0521 0.5117 1.9211 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8780 -2.1222 0.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0856 -2.3567 0.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8923 -2.6148 1.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3916 0.4908 0.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5331 -0.2843 -0.8709 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2924 2.2106 -0.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5993 2.0912 0.8584 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3769 3.2740 -1.2287 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0543 3.2440 0.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1748 2.6606 1.3763 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4435 3.2416 -0.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7672 1.1332 2.2963 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4149 -0.4969 1.6972 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1144 0.7076 1.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8115 0.6390 -3.6066 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0633 -0.8972 3.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7572 0.9854 0.7260 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0250 2.3389 -0.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1033 1.5671 1.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7478 1.0082 -2.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2494 1.6570 -1.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2331 -0.0546 -2.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9915 -3.0734 1.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8778 3.8098 0.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8536 3.1894 -1.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4045 -0.7132 -1.7531 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 18 19 1 0 19 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 31 32 2 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 6 35 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 1 39 44 1 6 44 45 2 0 44 46 1 0 35 47 1 0 47 48 2 0 47 49 1 0 24 50 1 0 50 51 1 0 50 52 1 0 10 53 1 0 5 54 1 0 4 55 1 0 3 56 1 0 7 2 1 0 16 9 1 0 50 19 1 0 29 22 1 0 42 32 1 0 42 27 1 0 39 33 1 0 1 57 1 0 1 58 1 0 1 59 1 0 2 60 1 6 3 61 1 1 4 62 1 6 5 63 1 6 6 64 1 1 9 65 1 1 10 66 1 6 11 67 1 1 12 68 1 0 12 69 1 0 13 70 1 0 15 71 1 1 16 72 1 6 17 73 1 0 19 74 1 1 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 23 79 1 0 23 80 1 0 23 81 1 0 24 82 1 1 25 83 1 0 25 84 1 0 26 85 1 0 26 86 1 0 28 87 1 0 28 88 1 0 28 89 1 0 29 90 1 1 30 91 1 0 30 92 1 0 31 93 1 0 33 94 1 6 34 95 1 0 34 96 1 0 36 97 1 0 36 98 1 0 36 99 1 0 37100 1 0 37101 1 0 38102 1 0 38103 1 0 40104 1 0 40105 1 0 41106 1 0 41107 1 0 43108 1 0 43109 1 0 43110 1 0 46111 1 0 49112 1 0 51113 1 0 51114 1 0 51115 1 0 52116 1 0 52117 1 0 52118 1 0 53119 1 0 54120 1 0 55121 1 0 56122 1 0 M END

Standard InCHIKey	FCMBHJYOOLTZKM-ZAMFQLPESA-N
Standard InCHI	InChI=1S/C42H66O14/c1-20-27(44)29(46)30(47)33(53-20)56-32-28(45)23(19-43)54-34(31(32)48)55-26-11-12-39(5)24(37(26,2)3)10-13-41(7)25(39)9-8-21-22-18-38(4,35(49)50)14-16-42(22,36(51)52)17-15-40(21,41)6/h8,20,22-34,43-48H,9-19H2,1-7H3,(H,49,50)(H,51,52)/t20-,22-,23+,24-,25+,26-,27-,28+,29+,30+,31+,32-,33-,34-,38+,39-,40+,41+,42-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](CO)O[C@H]([C@@H]1O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4C[C@@](C)(CC[C@@]4(CC[C@@]32C)C(=O)O)C(=O)O)C1(C)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	794.45	Volume:	790.246 ? Van der Waals volume.
Dense:	1.005	LogP:	1.35 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.955 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.858 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	40.0
TPSA:	232.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.817	Fsp³:	0.905
MCE-18:	154.0 ? 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:	0.911	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.207	Promiscuous compounds:	0.121

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.085	MDCK Permeability:	-5.202
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.003
20% Bioavailability (F20%):	0.039	30% Bioavailability (F30%):	0.199
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.485
Plasma Protein Binding (PPB):	74.813%	Volume Distribution (VD):	-0.556
Fu:	20.501% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.98	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? 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):

0.392

Half-life (T1/2):

3.906

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.758	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.44	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.017	Skin Sensitization:	1.0
Carcinogencity:	0.257	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.155
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.994
Hematotoxicity:	0.478	Drug-induced Nephrotoxicity:	0.948
Genotoxicity:	0.586	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.069	Hek293 Cytotoxicity:	0.07
BCF:	0.452 ? 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:	3.631 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.418 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.365 ? 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
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	bark	n.a.	DOI[10.1021/np50040a042]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2832544]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	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 NPC185291 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	22786
0.1-0.2	22709
0.2-0.3	2965
0.3-0.4	919
0.4-0.5	380
0.5-0.6	55
0.6-0.7	28
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	Natural Product ID
0.7419	Intermediate Similarity	NPC270667
0.7347	Intermediate Similarity	NPC114304
0.7113	Intermediate Similarity	NPC114441
0.7111	Intermediate Similarity	NPC606107
0.71	Intermediate Similarity	NPC180550
0.71	Intermediate Similarity	NPC35405
0.701	Intermediate Similarity	NPC25605
0.6923	Remote Similarity	NPC324875
0.6923	Remote Similarity	NPC292677
0.6635	Remote Similarity	NPC257468
0.6531	Remote Similarity	NPC164194
0.65	Remote Similarity	NPC56713
0.6452	Remote Similarity	NPC204407
0.6436	Remote Similarity	NPC109079
0.6429	Remote Similarity	NPC166422
0.6429	Remote Similarity	NPC219180
0.6429	Remote Similarity	NPC251263
0.64	Remote Similarity	NPC12288
0.6355	Remote Similarity	NPC276093
0.6321	Remote Similarity	NPC481082
0.6321	Remote Similarity	NPC164419
0.6316	Remote Similarity	NPC54636
0.6275	Remote Similarity	NPC127056
0.6226	Remote Similarity	NPC258885
0.6214	Remote Similarity	NPC472949
0.6186	Remote Similarity	NPC161717
0.6082	Remote Similarity	NPC31839
0.6075	Remote Similarity	NPC139044
0.6053	Remote Similarity	NPC471384
0.6042	Remote Similarity	NPC283849
0.604	Remote Similarity	NPC211798
0.6036	Remote Similarity	NPC475486
0.6019	Remote Similarity	NPC174679
0.6019	Remote Similarity	NPC279554
0.6	Remote Similarity	NPC22956
0.5963	Remote Similarity	NPC79718
0.5926	Remote Similarity	NPC471383
0.5922	Remote Similarity	NPC136877
0.5918	Remote Similarity	NPC286347
0.5913	Remote Similarity	NPC323341
0.5913	Remote Similarity	NPC133818
0.5905	Remote Similarity	NPC6377
0.5905	Remote Similarity	NPC488561
0.5905	Remote Similarity	NPC208381
0.5876	Remote Similarity	NPC57362
0.5868	Remote Similarity	NPC111466
0.5865	Remote Similarity	NPC108748
0.5856	Remote Similarity	NPC323359
0.5826	Remote Similarity	NPC151543
0.5804	Remote Similarity	NPC488564
0.5714	Remote Similarity	NPC474589
0.5714	Remote Similarity	NPC59804
0.5688	Remote Similarity	NPC104400
0.5688	Remote Similarity	NPC10320
0.5676	Remote Similarity	NPC119794
0.5625	Remote Similarity	NPC114484
0.5565	Remote Similarity	NPC62725
0.5556	Remote Similarity	NPC28198
0.5556	Remote Similarity	NPC476123
0.5534	Remote Similarity	NPC191410
0.5528	Remote Similarity	NPC471385
0.5481	Remote Similarity	NPC473481
0.5481	Remote Similarity	NPC475472
0.5455	Remote Similarity	NPC274507
0.5413	Remote Similarity	NPC80843
0.5391	Remote Similarity	NPC488209
0.5385	Remote Similarity	NPC476992
0.5364	Remote Similarity	NPC469945
0.5321	Remote Similarity	NPC488516
0.5315	Remote Similarity	NPC124296
0.5288	Remote Similarity	NPC284807
0.5268	Remote Similarity	NPC159309
0.5268	Remote Similarity	NPC86222
0.5253	Remote Similarity	NPC484195
0.5243	Remote Similarity	NPC100383
0.5243	Remote Similarity	NPC242611
0.5225	Remote Similarity	NPC223301
0.5225	Remote Similarity	NPC171544
0.5221	Remote Similarity	NPC40085
0.5203	Remote Similarity	NPC488211
0.5197	Remote Similarity	NPC302543
0.5192	Remote Similarity	NPC471967
0.5175	Remote Similarity	NPC275668
0.5175	Remote Similarity	NPC73829
0.5164	Remote Similarity	NPC475140
0.5161	Remote Similarity	NPC476068
0.5143	Remote Similarity	NPC294112
0.5138	Remote Similarity	NPC309780
0.5049	Remote Similarity	NPC177246
0.5046	Remote Similarity	NPC476882

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC185291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6806
0.1-0.2	2269
0.2-0.3	64
0.3-0.4	9
0.4-0.5	2
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