NPASS Compound

Natural Product: NPC472901

Natural Product ID	NPC472901
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UWWGFPDRXDYTKI-FSNJYKGBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3593737
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 109114 0 0 0 0 0 0 0 0999 V2000 -4.8242 4.8513 2.6035 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0842 4.8686 1.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4239 3.7023 0.5326 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1344 2.5350 1.2357 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5745 1.3976 0.5346 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8115 0.3161 0.9715 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9560 -0.1997 0.0080 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5718 0.2718 0.4991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4608 -0.2018 -0.3791 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3303 0.8129 -1.4946 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5928 -1.6051 -0.8589 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9926 -1.9907 -1.3030 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8746 -1.6597 -0.1268 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1238 -2.4557 -0.0088 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1655 -2.2031 -1.0480 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7661 -2.1067 1.3455 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7858 -3.9315 0.1202 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5738 -4.6076 -0.8289 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3394 -4.2130 -0.2171 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0988 -3.4854 -1.5230 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3756 -1.3783 -2.6005 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4877 -1.9687 -1.7966 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8395 -1.8794 -1.0480 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9636 -0.5571 -0.4579 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7872 -0.1869 0.4664 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7707 -1.1572 1.5958 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2183 1.1438 0.9550 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7167 1.2717 0.7122 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0660 -0.2106 0.4487 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4461 -0.3979 0.0549 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3245 0.6069 -0.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7201 0.5392 -0.4549 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3419 1.9416 -0.2533 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6587 1.9744 -0.7538 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3716 2.2114 0.6713 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6516 3.6809 0.9984 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0674 1.2706 1.5975 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5383 -0.3157 0.2327 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3190 -1.1472 -0.5911 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9945 -1.7565 -0.1917 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7776 -1.9750 -2.1103 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0369 1.2747 0.6959 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6627 2.6443 0.8220 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8784 3.7236 0.0988 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0338 3.6611 -1.2825 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9145 2.9948 2.1413 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6489 0.5696 -0.3501 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3600 5.2146 3.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2431 5.7991 0.8571 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0168 4.7297 1.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8028 3.7689 -0.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3097 1.5572 -0.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2012 0.3801 -0.9287 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6489 1.3790 0.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4989 -0.0207 1.5630 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2101 0.4002 -2.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2468 1.4764 -1.5619 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5003 1.5357 -1.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4297 -2.2684 0.0475 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2741 -2.0083 0.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0044 -1.2524 -1.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1987 -2.1173 -0.5932 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3021 -3.0605 -1.7718 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6753 -1.5197 1.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1374 -3.0501 1.8551 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0277 -1.7129 2.0641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9899 -4.3688 1.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0667 -5.2965 -1.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2404 -5.2982 -0.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6358 -3.9319 0.5797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3208 -3.9354 -2.1291 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0306 -3.6625 -2.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2405 -1.9646 -3.0154 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4872 -0.3158 -2.6738 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5373 -1.6471 -3.3144 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4805 -3.0661 -2.0645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5361 -1.4588 -2.7526 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9861 -2.7606 -0.4292 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0130 0.1812 -1.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4194 -2.0542 1.4114 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2186 -0.6933 2.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1961 -1.5355 1.9203 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6491 2.0116 0.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1170 1.1772 2.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8642 1.8794 -0.1792 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2622 1.6506 1.5778 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9606 -0.6600 1.4807 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8758 1.5932 0.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8548 0.3008 -1.5460 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6346 2.7294 -0.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7725 3.7615 0.9915 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2982 4.2989 0.1548 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2088 3.9329 1.9690 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8408 0.6664 1.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6595 1.8069 2.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3774 0.6181 2.1867 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9811 -0.5384 -1.2486 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8659 -1.8544 0.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6792 -1.7388 -1.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8371 -1.9604 0.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2725 -2.5773 0.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3191 -1.9205 -1.2164 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 -2.6720 -2.7436 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2385 0.7560 1.6640 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6596 2.5934 0.3195 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2947 4.6966 0.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7867 3.0431 -1.5255 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3979 2.3916 2.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2929 -0.0819 0.0536 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 6 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 14 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 12 21 1 6 11 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 32 38 1 0 38 39 1 0 30 40 1 0 23 41 1 0 5 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 44 3 1 0 13 7 1 0 29 24 1 0 35 33 1 0 25 9 1 0 20 12 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 6 5 52 1 6 7 53 1 6 8 54 1 0 8 55 1 0 10 56 1 0 10 57 1 0 10 58 1 0 11 59 1 1 13 60 1 1 15 61 1 0 15 62 1 0 15 63 1 0 16 64 1 0 16 65 1 0 16 66 1 0 17 67 1 1 18 68 1 0 19 69 1 0 19 70 1 0 20 71 1 0 20 72 1 0 21 73 1 0 21 74 1 0 21 75 1 0 22 76 1 0 22 77 1 0 23 78 1 1 24 79 1 6 26 80 1 0 26 81 1 0 26 82 1 0 27 83 1 0 27 84 1 0 28 85 1 0 28 86 1 0 29 87 1 1 31 88 1 0 32 89 1 6 33 90 1 6 36 91 1 0 36 92 1 0 36 93 1 0 37 94 1 0 37 95 1 0 37 96 1 0 39 97 1 0 39 98 1 0 39 99 1 0 40100 1 0 40101 1 0 40102 1 0 41103 1 0 42104 1 1 43105 1 6 44106 1 1 45107 1 0 46108 1 0 47109 1 0 M END

Standard InCHIKey	UWWGFPDRXDYTKI-FSNJYKGBSA-N
Standard InCHI	InChI=1S/C37H62O10/c1-18(14-21(44-9)31-34(4,5)47-31)19-10-13-36(7)26(19)20(39)15-24-35(6)12-11-25(40)33(2,3)30(35)22(16-37(24,36)8)45-32-29(43)28(42)27(41)23(17-38)46-32/h14,19-32,38-43H,10-13,15-17H2,1-9H3/b18-14+/t19-,20-,21+,22+,23-,24-,25+,26+,27-,28+,29-,30+,31+,32-,35-,36-,37-/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2C[C@]3(C)[C@@H]([C@@]4([C@@H]2C(C)(C)[C@@H](O)CC4)C)C[C@H]([C@H]2[C@@]3(C)CC[C@@H]2/C(=C/[C@@H]([C@@H]2OC2(C)C)OC)/C)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.43	Volume:	682.435 ? Van der Waals volume.
Dense:	0.977	LogP:	2.18 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.581 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.003 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	161.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.135	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.844	Fsp³:	0.946
MCE-18:	128.0 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.842	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.205	Promiscuous compounds:	0.273

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.802	MDCK Permeability:	-5.228
Pgp-inhibitor:	0.005	Pgp-substrate:	0.876
PAMPA:	0.996 ? 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):	0.286
20% Bioavailability (F20%):	0.938	30% Bioavailability (F30%):	0.976
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.342	MRP1:	0.835
Plasma Protein Binding (PPB):	74.904%	Volume Distribution (VD):	-0.354
Fu:	19.093% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.012
BSEP inhibitor:	0.059

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.036	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.061	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.967
HLM stability:	0.024 ? 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):

3.242

Half-life (T1/2):

2.329

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.064
Human Hepatotoxicity (H-HT):	0.671	Drug-induced Liver Injury (DILI):	0.811
AMES Toxicity:	0.936	Rat Oral Acute Toxicity:	0.528
Maximum Recommended Daily Dose:	0.196	Skin Sensitization:	1.0
Carcinogencity:	0.414	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.38
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.987
Hematotoxicity:	0.912	Drug-induced Nephrotoxicity:	0.936
Genotoxicity:	0.943	RPMI-8226 Immunitoxicity:	0.37
A549 Cytotoxicity:	0.976	Hek293 Cytotoxicity:	0.81
BCF:	1.602 ? 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:	3.443 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.788 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.09 ? 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
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[12880307]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Stems	n.a.	n.a.	PMID[17663584]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[18186611]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Steamed Roots	n.a.	n.a.	PMID[26200131]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21891	Panax notoginseng	Species	Araliaceae	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
Activity	1
IC50	5

Activity Type	# Activity
Cell line	5
Non-molecular	1

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
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	11.6	%	PMID[26200131]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[10924160]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[26034885]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[21666868]
NPT660	Cell line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[18303848]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[26200131]

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 NPC472901 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	21571
0.1-0.2	23551
0.2-0.3	4312
0.3-0.4	359
0.4-0.5	26
0.5-0.6	20
0.6-0.7	12
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
0.7632	Intermediate Similarity	NPC136816
0.7632	Intermediate Similarity	NPC7341
0.7436	Intermediate Similarity	NPC472899
0.7436	Intermediate Similarity	NPC472898
0.7	Intermediate Similarity	NPC609286
0.6875	Remote Similarity	NPC472989
0.6707	Remote Similarity	NPC309425
0.6591	Remote Similarity	NPC288694
0.6543	Remote Similarity	NPC131466
0.6429	Remote Similarity	NPC114874
0.6386	Remote Similarity	NPC47566
0.6386	Remote Similarity	NPC129372
0.6322	Remote Similarity	NPC472987
0.6296	Remote Similarity	NPC140446
0.6279	Remote Similarity	NPC274833
0.6265	Remote Similarity	NPC82955
0.6087	Remote Similarity	NPC601606
0.5978	Remote Similarity	NPC127801
0.5934	Remote Similarity	NPC472252
0.5934	Remote Similarity	NPC245280
0.5889	Remote Similarity	NPC473020
0.5889	Remote Similarity	NPC229801
0.5806	Remote Similarity	NPC152584
0.5806	Remote Similarity	NPC231340
0.5729	Remote Similarity	NPC208594
0.5579	Remote Similarity	NPC16520
0.5579	Remote Similarity	NPC211879
0.5579	Remote Similarity	NPC189852
0.5579	Remote Similarity	NPC155010
0.5532	Remote Similarity	NPC307167
0.54	Remote Similarity	NPC160816
0.5152	Remote Similarity	NPC286969
0.5102	Remote Similarity	NPC210759
0.5057	Remote Similarity	NPC280825
0.5057	Remote Similarity	NPC473198
0.5053	Remote Similarity	NPC473199
0.5049	Remote Similarity	NPC305418

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7475
0.1-0.2	1610
0.2-0.3	61
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