NPASS Compound

Natural Product: NPC296164

Natural Product ID	NPC296164
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2,3-Diacetyl Maslinic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-diacetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508614
PubChem CID	14010966
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 92 96 0 0 0 0 0 0 0 0999 V2000 -5.9202 4.2531 -0.7756 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4395 3.0891 0.0110 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8616 2.9337 1.1889 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5504 2.1598 -0.4759 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0873 1.0348 0.2885 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6038 1.2225 0.4114 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8888 -0.0372 0.9503 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2428 -0.1091 2.3770 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3146 -1.1292 0.0530 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7801 -1.4357 0.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4659 -0.1840 -0.4806 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8255 -0.3361 -0.6947 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4964 -0.3025 -1.8812 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8214 -0.1115 -2.9214 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9635 -0.4760 -2.0222 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3608 -2.0435 1.2111 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9509 -2.4443 -1.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4731 -2.3687 0.1333 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0258 -2.0332 -0.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4911 -0.9544 0.8963 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4181 0.1827 0.6468 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0931 1.4851 1.1280 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4116 1.6760 0.4661 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2667 0.7194 0.2453 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9270 -0.6533 0.6649 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4476 -1.7540 -0.2488 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8382 -0.8240 1.9009 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9681 0.1125 1.9887 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5649 0.7569 0.7949 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5894 1.0606 -0.3252 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8992 0.6078 -1.6815 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3362 0.2840 -1.9805 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8620 1.0724 -3.2022 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5138 -1.1645 -2.3901 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3000 0.5885 -0.8948 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7978 0.0166 0.3863 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1558 2.0583 1.3343 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7034 3.1084 0.8466 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1193 2.1195 2.2890 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3673 -1.6310 2.2293 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8146 3.9444 -1.3400 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1730 5.0944 -0.1183 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1250 4.6030 -1.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5945 1.1244 1.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5165 1.9947 1.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1484 1.5477 -0.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2088 0.4472 2.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4997 0.5308 2.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4006 -1.0924 2.8216 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0992 -0.7359 -0.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0183 -0.0247 -1.5125 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2569 -1.2529 -1.2647 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2323 -0.7513 -3.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5018 0.4465 -1.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6662 -1.3649 2.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2511 -2.6523 0.9160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6388 -2.7713 1.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0333 -2.4360 -1.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3010 -2.1921 -1.9870 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7456 -3.4736 -0.7353 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7585 -2.9502 -0.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7035 -3.0598 0.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4985 -2.9699 -0.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0317 -1.5461 -1.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4390 0.2953 -0.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5829 2.3411 0.8361 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1684 1.5663 2.2338 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 2.7083 0.1499 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3496 -2.6763 0.4206 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5431 -1.7404 -0.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8804 -1.9526 -1.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2461 -0.6605 2.8515 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1980 -1.8686 2.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8175 -0.4403 2.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7640 0.9254 2.7713 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6452 2.1988 -0.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6387 1.4172 -2.4526 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2857 -0.2182 -2.1018 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3633 0.7030 -4.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5776 2.1469 -3.0754 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9554 0.9263 -3.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9829 -1.7825 -1.5859 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1183 -1.3159 -3.2832 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5233 -1.6439 -2.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2568 0.0430 -1.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5914 1.6540 -0.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5485 0.1759 1.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5952 -1.0439 0.2656 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2812 2.9253 2.8912 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3080 -1.0109 3.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2561 -2.3169 2.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4717 -2.3655 2.2998 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 10 16 1 0 10 17 1 0 9 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 35 36 1 0 29 37 1 1 37 38 2 0 37 39 1 0 20 40 1 1 11 5 1 0 25 20 1 0 36 29 1 0 21 7 1 0 30 24 1 0 1 41 1 0 1 42 1 0 1 43 1 0 5 44 1 1 6 45 1 0 6 46 1 0 8 47 1 0 8 48 1 0 8 49 1 0 9 50 1 6 11 51 1 6 15 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 21 65 1 6 22 66 1 0 22 67 1 0 23 68 1 0 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 30 76 1 6 31 77 1 0 31 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 35 85 1 0 35 86 1 0 36 87 1 0 36 88 1 0 39 89 1 0 40 90 1 0 40 91 1 0 40 92 1 0 M END

Standard InCHIKey	BZDICYRSPZNHNV-LULZRBEKSA-N
Standard InCHI	InChI=1S/C34H52O6/c1-20(35)39-24-19-31(7)25(30(5,6)27(24)40-21(2)36)12-13-33(9)26(31)11-10-22-23-18-29(3,4)14-16-34(23,28(37)38)17-15-32(22,33)8/h10,23-27H,11-19H2,1-9H3,(H,37,38)/t23-,24+,25-,26+,27-,31-,32+,33+,34-/m0/s1
SMILES	CC(=O)O[C@@H]1C[C@@]2(C)[C@H](C([C@H]1OC(=O)C)(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	556.38	Volume:	596.033 ? Van der Waals volume.
Dense:	0.933	LogP:	3.038 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.974 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.559 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	29.0
TPSA:	89.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.289	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.889	Fsp³:	0.853
MCE-18:	110.667 ? 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:	0.948	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? 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:	0.411	Promiscuous compounds:	0.19

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.169	MDCK Permeability:	-4.864
Pgp-inhibitor:	0.992	Pgp-substrate:	0.0
PAMPA:	0.901 ? 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):	0.018
20% Bioavailability (F20%):	0.977	30% Bioavailability (F30%):	0.948
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.899
Plasma Protein Binding (PPB):	90.98%	Volume Distribution (VD):	-0.398
Fu:	7.708% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.973	BCRP inhibitor:	0.009
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.018	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.954	CYP3A4-substrate:	0.985
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.283 ? 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):

3.631

Half-life (T1/2):

0.745

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.093
Human Hepatotoxicity (H-HT):	0.689	Drug-induced Liver Injury (DILI):	0.714
AMES Toxicity:	0.177	Rat Oral Acute Toxicity:	0.35
Maximum Recommended Daily Dose:	0.274	Skin Sensitization:	0.896
Carcinogencity:	0.792	Eye Corrosion:	0.019
Eye Irritation:	0.29	Respiratory Toxicity:	0.475
Drug-induced Neurotoxicity:	0.039	Ototoxicity:	0.486
Hematotoxicity:	0.443	Drug-induced Nephrotoxicity:	0.57
Genotoxicity:	0.512	RPMI-8226 Immunitoxicity:	0.02
A549 Cytotoxicity:	0.063	Hek293 Cytotoxicity:	0.125
BCF:	1.516 ? 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:	4.525 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.193 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.659 ? 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

Activity Type	# Activity
IC50	6
Ki	2
Activity	20
Ratio IC50	3
EC50	21

Activity Type	# Activity
Individual protein	4
Cell line	42
Others	5
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2681	Individual protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	13182.57	nM	PubChem BioAssay data set
NPT2681	Individual protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	13300.0	nM	DrugMatrix in vivo data: Pathology
NPT67	Individual protein	Cholinesterase	Equus caballus	Ki	>	10000.0	nM	DrugMatrix in vivo data: Pathology
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Ki	>	10000.0	nM	PMID[20000780]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[25530833]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	20.0	%	PMID[15387645]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	0.0	%	PMID[16038541]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	100.0	%	PubChem BioAssay data set
NPT169	Cell line	B16-F10	Mus musculus	Activity	<	10.0	%	PMID[19114678]
NPT169	Cell line	B16-F10	Mus musculus	IC50	=	44100.0	nM	PMID[16499331]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	1.5	%	PMID[22276679]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	7.1	%	PMID[15043442]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	88.9	%	PMID[10843574]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	61.6	%	DOI[10.1007/s00044-012-0377-3]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	59.3	%	PMID[16472241]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	52.9	%	PMID[7473549]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	29.6	%	PMID[18303848]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	8.7	%	PMID[8126698]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	9.7	%	PMID[17875998]
NPT169	Cell line	B16-F10	Mus musculus	Activity	=	31.4	%	PMID[18675491]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	69140.0	nM	PMID[24582402]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	50160.0	nM	PMID[24953027]
NPT169	Cell line	B16-F10	Mus musculus	Ratio IC50	=	0.8	n.a.	PMID[27128174]
NPT139	Cell line	HT-29	Homo sapiens	Ratio IC50	=	0.5	n.a.	PMID[21621880]
NPT65	Cell line	HepG2	Homo sapiens	Ratio IC50	=	2.0	n.a.	PMID[23835482]
NPT179	Cell line	A2780	Homo sapiens	EC50	=	10500.0	nM	PMID[27149037]
NPT139	Cell line	HT-29	Homo sapiens	EC50	=	25500.0	nM	PMID[29529499]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	1600.0	nM	PMID[29529499]
NPT81	Cell line	A549	Homo sapiens	EC50	=	18900.0	nM	PMID[27149037]
NPT1216	Cell line	FaDu	Homo sapiens	EC50	=	21300.0	nM	PMID[29529499]
NPT886	Cell line	NIH3T3	Mus musculus	EC50	=	12200.0	nM	PMID[27149037]
NPT1215	Cell line	8505C	Homo sapiens	EC50	=	5700.0	nM	PMID[31330447]
NPT179	Cell line	A2780	Homo sapiens	EC50	=	17300.0	nM	PMID[31330447]
NPT81	Cell line	A549	Homo sapiens	EC50	=	4200.0	nM	PMID[31330447]
NPT579	Cell line	DLD-1	Homo sapiens	EC50	=	17000.0	nM	PMID[31330447]
NPT139	Cell line	HT-29	Homo sapiens	EC50	=	8500.0	nM	PMID[31330447]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	8500.0	nM	PMID[31330447]
NPT886	Cell line	NIH3T3	Mus musculus	EC50	=	10400.0	nM	PMID[31330447]
NPT1216	Cell line	FaDu	Homo sapiens	EC50	=	17800.0	nM	PMID[27149037]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	16600.0	nM	PMID[27149037]
NPT24664	Cell line	518A2	Homo sapiens	EC50	=	14600.0	nM	PMID[31330447]
NPT24664	Cell line	518A2	Homo sapiens	EC50	=	23100.0	nM	PMID[27149037]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	44100.0	nM	PMID[27128174]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	DrugMatrix in vivo data: Pathology
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Activity	=	59.6	%	PMID[26035018]

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 NPC296164 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	22975
0.2-0.3	2630
0.3-0.4	465
0.4-0.5	188
0.5-0.6	83
0.6-0.7	10
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
0.7761	Intermediate Similarity	NPC120840
0.7027	Intermediate Similarity	NPC481362
0.6301	Remote Similarity	NPC200752
0.6267	Remote Similarity	NPC488521
0.625	Remote Similarity	NPC156981
0.6232	Remote Similarity	NPC604575
0.6164	Remote Similarity	NPC158141
0.6133	Remote Similarity	NPC608622
0.6111	Remote Similarity	NPC480946
0.6111	Remote Similarity	NPC130577
0.6111	Remote Similarity	NPC142415
0.6111	Remote Similarity	NPC102683
0.5974	Remote Similarity	NPC96580
0.5904	Remote Similarity	NPC283849
0.5904	Remote Similarity	NPC606107
0.5867	Remote Similarity	NPC298554
0.5833	Remote Similarity	NPC280654
0.5811	Remote Similarity	NPC270768
0.5811	Remote Similarity	NPC59263
0.5811	Remote Similarity	NPC210106
0.5811	Remote Similarity	NPC275809
0.5811	Remote Similarity	NPC84319
0.5811	Remote Similarity	NPC52021
0.5811	Remote Similarity	NPC599947
0.5747	Remote Similarity	NPC284807
0.5747	Remote Similarity	NPC473538
0.5733	Remote Similarity	NPC231063
0.5733	Remote Similarity	NPC282395
0.5733	Remote Similarity	NPC481360
0.5733	Remote Similarity	NPC110308
0.5696	Remote Similarity	NPC474727
0.5682	Remote Similarity	NPC191410
0.5618	Remote Similarity	NPC171007
0.5618	Remote Similarity	NPC190849
0.5618	Remote Similarity	NPC475472
0.5618	Remote Similarity	NPC475611
0.56	Remote Similarity	NPC282616
0.56	Remote Similarity	NPC37038
0.5595	Remote Similarity	NPC204407
0.5584	Remote Similarity	NPC485589
0.5581	Remote Similarity	NPC286347
0.5556	Remote Similarity	NPC23241
0.5529	Remote Similarity	NPC28198
0.5529	Remote Similarity	NPC476123
0.5526	Remote Similarity	NPC106112
0.5526	Remote Similarity	NPC261935
0.5517	Remote Similarity	NPC100383
0.55	Remote Similarity	NPC485588
0.5435	Remote Similarity	NPC605663
0.5426	Remote Similarity	NPC610795
0.5385	Remote Similarity	NPC22676
0.5385	Remote Similarity	NPC164194
0.5385	Remote Similarity	NPC474963
0.5376	Remote Similarity	NPC132126
0.5319	Remote Similarity	NPC127056
0.5309	Remote Similarity	NPC485586
0.5263	Remote Similarity	NPC488561
0.5256	Remote Similarity	NPC291028
0.5244	Remote Similarity	NPC230151
0.5244	Remote Similarity	NPC600880
0.5222	Remote Similarity	NPC294112
0.5213	Remote Similarity	NPC25605
0.5213	Remote Similarity	NPC56713
0.5204	Remote Similarity	NPC180550
0.5204	Remote Similarity	NPC35405
0.52	Remote Similarity	NPC481235
0.5195	Remote Similarity	NPC307282
0.5195	Remote Similarity	NPC182797
0.5195	Remote Similarity	NPC64872
0.5195	Remote Similarity	NPC25906
0.5195	Remote Similarity	NPC52169
0.5195	Remote Similarity	NPC488562
0.5181	Remote Similarity	NPC54909
0.5181	Remote Similarity	NPC233012
0.5158	Remote Similarity	NPC109079
0.5155	Remote Similarity	NPC469945
0.5128	Remote Similarity	NPC130278
0.5119	Remote Similarity	NPC93744
0.5119	Remote Similarity	NPC476888
0.5116	Remote Similarity	NPC476890
0.5116	Remote Similarity	NPC476889
0.5106	Remote Similarity	NPC136877
0.5104	Remote Similarity	NPC472949
0.5104	Remote Similarity	NPC6377
0.5104	Remote Similarity	NPC208381
0.5065	Remote Similarity	NPC198664
0.5062	Remote Similarity	NPC324063
0.506	Remote Similarity	NPC601365
0.5059	Remote Similarity	NPC603645
0.5054	Remote Similarity	NPC270667
0.5053	Remote Similarity	NPC59804
0.5052	Remote Similarity	NPC22956
0.5051	Remote Similarity	NPC601567
0.5051	Remote Similarity	NPC606631
0.505	Remote Similarity	NPC119794

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC296164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6352
0.1-0.2	2766
0.2-0.3	20
0.3-0.4	10
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