NPASS Compound

Natural Product: NPC258130

Natural Product ID	NPC258130
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	N'-[N-(2Alpha,3Beta-Dihydroxy-12-Oleanen-28-Oyl)-L-Alanyl]-Glycine
IUPAC Name	2-[[(2S)-2-[[(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carbonyl]amino]propanoyl]amino]acetic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451140
PubChem CID	44570740
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 99103 0 0 0 0 0 0 0 0999 V2000 4.4949 1.0542 -3.4341 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0737 0.4333 -2.1505 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1618 1.3292 -1.7162 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3571 0.8617 -1.6223 N 0 0 0 0 0 0 0 0 0 0 0 0 8.4861 1.6715 -1.2032 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3064 2.2274 0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1756 2.9527 0.6692 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1523 1.9481 0.8470 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9740 2.6656 -1.3975 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0051 0.3276 -1.2191 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7203 -0.6313 -0.4290 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5349 -0.4953 0.4571 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0147 -0.5286 1.8703 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5195 -1.8722 2.2326 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6369 -3.0264 1.9087 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0689 -3.5130 3.2572 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4549 -4.2165 1.3879 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5162 -2.7602 0.9945 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5495 -1.5536 0.1389 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1272 -1.0657 0.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6856 -1.8574 -0.7026 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1105 -1.5785 -0.9511 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5626 -0.3812 -0.1956 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9553 0.0712 -0.5528 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1688 0.4535 -1.9611 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8615 -1.1359 -0.2673 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3046 -0.8315 -0.3878 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7437 0.5474 -0.0484 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7557 1.4212 0.6104 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9893 2.8480 0.0810 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1236 1.5366 2.1031 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3257 1.0974 0.4736 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4368 2.2996 0.2689 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9849 2.0172 0.3353 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5281 0.7098 -0.1920 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0558 0.9477 -1.6265 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3723 0.1826 0.6435 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9033 -0.1446 2.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6982 1.2162 0.8072 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9852 0.9051 0.1669 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3215 1.1942 -1.1721 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0007 -1.8254 0.3422 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5164 -1.7508 -0.4255 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4986 0.6442 -3.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1694 0.7490 -4.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5309 2.1580 -3.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4692 -0.5597 -2.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6283 2.4550 -1.9775 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4043 1.0522 -1.2011 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8471 2.5843 1.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7023 3.3563 -1.6187 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8780 0.1821 1.9328 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2574 -0.2266 2.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7383 -1.8175 3.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5483 -2.1064 1.8271 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8632 -3.8569 3.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2527 -4.2323 3.0926 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6088 -2.6110 3.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5388 -4.2002 0.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9234 -5.1307 1.7404 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4341 -4.1896 1.8973 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3713 -3.6819 0.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5628 -2.7670 1.5979 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7944 -1.9057 -0.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2941 -2.7829 -1.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3739 -1.5902 -2.0284 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6752 -2.4636 -0.5262 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6467 -0.7102 0.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1427 0.0479 -2.3721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4157 0.0265 -2.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2022 1.5339 -2.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6457 -1.4027 0.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6174 -1.9750 -0.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6096 -1.0327 -1.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6480 0.4246 0.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1134 2.9648 0.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7136 2.9515 -0.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5942 3.6060 0.7621 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3917 2.2045 2.6101 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1605 1.8973 2.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0491 0.4873 2.4957 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9808 0.6608 1.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7011 2.8696 -0.6459 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6799 3.0036 1.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5790 2.1961 1.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4838 2.8610 -0.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1112 1.5084 -1.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8120 1.6789 -2.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9740 0.0472 -2.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1455 -1.2031 2.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1061 0.0881 2.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7732 0.4305 2.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9021 1.4522 1.8938 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3307 2.1770 0.3856 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0863 1.0586 -0.9049 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7642 1.5882 0.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4884 0.5400 -1.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1253 -2.6453 -0.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 -2.1448 -1.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 3 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 3 9 1 0 2 10 1 0 10 11 2 3 12 11 1 6 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 6 35 37 1 0 37 38 1 1 37 39 1 0 39 40 1 0 28 41 1 0 27 42 1 0 11 43 1 0 40 12 1 0 19 12 1 0 37 20 1 0 35 23 1 0 32 24 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 5 48 1 0 5 49 1 0 8 50 1 0 9 51 1 0 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 16 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 19 64 1 6 21 65 1 0 22 66 1 0 22 67 1 0 23 68 1 1 25 69 1 0 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 27 74 1 6 28 75 1 1 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 31 81 1 0 32 82 1 1 33 83 1 0 33 84 1 0 34 85 1 0 34 86 1 0 36 87 1 0 36 88 1 0 36 89 1 0 38 90 1 0 38 91 1 0 38 92 1 0 39 93 1 0 39 94 1 0 40 95 1 0 40 96 1 0 41 97 1 0 42 98 1 0 43 99 1 0 M END

Standard InCHIKey	UEBMLYZEQXVMQL-QKPILCRPSA-N
Standard InCHI	InChI=1S/C35H56N2O6/c1-20(28(42)36-19-26(39)40)37-29(43)35-15-13-30(2,3)17-22(35)21-9-10-25-32(6)18-23(38)27(41)31(4,5)24(32)11-12-34(25,8)33(21,7)14-16-35/h9,20,22-25,27,38,41H,10-19H2,1-8H3,(H,36,42)(H,37,43)(H,39,40)/t20-,22-,23+,24-,25+,27-,32-,33+,34+,35-/m0/s1
SMILES	C[C@@H](C(=NCC(=O)O)O)N=C([C@@]12CCC(C)(C)C[C@H]2C2=CC[C@@H]3[C@@]4(C)C[C@H]([C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]2(C)CC1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	600.41	Volume:	635.323 ? Van der Waals volume.
Dense:	0.945	LogP:	3.333 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.049 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.818 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	29.0
TPSA:	142.94 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.138	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.504	Fsp³:	0.857
MCE-18:	112.462 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.866	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.092 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.007	Promiscuous compounds:	0.125

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.606	MDCK Permeability:	-5.113
Pgp-inhibitor:	0.0	Pgp-substrate:	0.024
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):	0.0
20% Bioavailability (F20%):	0.29	30% Bioavailability (F30%):	0.017
50% Bioavailability (F50%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037	MRP1:	0.999
Plasma Protein Binding (PPB):	79.443%	Volume Distribution (VD):	-0.259
Fu:	17.61% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.0
BSEP inhibitor:	0.01

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.283	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.465	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.018
HLM stability:	0.924 ? 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):

0.535

Half-life (T1/2):

1.747

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.273	Rat Oral Acute Toxicity:	0.397
Maximum Recommended Daily Dose:	0.737	Skin Sensitization:	0.999
Carcinogencity:	0.456	Eye Corrosion:	0.0
Eye Irritation:	0.129	Respiratory Toxicity:	0.836
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.947
Hematotoxicity:	0.284	Drug-induced Nephrotoxicity:	0.914
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.004
A549 Cytotoxicity:	0.002	Hek293 Cytotoxicity:	0.025
BCF:	0.66 ? 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:	3.652 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.389 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.52 ? 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
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	Whole plant	n.a.	steroidal saponins	PMID[16933867]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[18409040]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[18579374]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25068579]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25900014]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37939623]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38810900]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[8541643]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24497	Holothuria leucospilota	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15173	Concha meretricis seu cyclinae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2831	Cornu saigae tataricae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29390	Semen juglandis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5939	Semen sojae praeparata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22659	Codonopsis subglobosa	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30421	Codonopsis tangshen	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741.1	Codonopsis pilosula var. modesta	Varieties	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24497	Holothuria leucospilota	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29390	Semen juglandis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30421	Codonopsis tangshen	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22659	Codonopsis subglobosa	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15173	Concha meretricis seu cyclinae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24497	Holothuria leucospilota	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2831	Cornu saigae tataricae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5939	Semen sojae praeparata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741.1	Codonopsis pilosula var. modesta	Varieties	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22659	Codonopsis subglobosa	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29390	Semen juglandis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30421	Codonopsis tangshen	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22659	Codonopsis subglobosa	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24497	Holothuria leucospilota	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22659	Codonopsis subglobosa	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741.1	Codonopsis pilosula var. modesta	Varieties	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23234	Ageratum conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19048	Pinellia ternata	Species	Araceae	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	2

Activity Type	# Activity
Organism	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
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	134.5	%	PMID[19135380]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	184.8	%	PMID[19135380]

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 NPC258130 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	23501
0.1-0.2	23678
0.2-0.3	2102
0.3-0.4	493
0.4-0.5	76
0.5-0.6	5
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	Natural Product ID
0.5556	Remote Similarity	NPC136313
0.5301	Remote Similarity	NPC84319
0.5301	Remote Similarity	NPC52021
0.5301	Remote Similarity	NPC599947
0.5125	Remote Similarity	NPC478657

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC258130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6234
0.1-0.2	2858
0.2-0.3	56
0.3-0.4	2
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