NPASS Compound

Natural Product: NPC74845

Natural Product ID	NPC74845
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	10-Oxooctadecanoic Acid
IUPAC Name	10-oxooctadecanoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1994343
PubChem CID	361941
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

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 55 54 0 0 0 0 0 0 0 0999 V2000 -8.2545 -1.0344 -0.4968 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9962 0.4389 -0.5294 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5428 0.7837 -0.1944 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1613 0.3197 1.1503 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8062 0.5621 1.6677 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6124 -0.0508 1.0823 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2554 0.1815 -0.3324 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9249 -0.4629 -0.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7708 0.0661 0.0308 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8255 0.9887 0.8090 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5864 -0.5640 -0.1823 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5983 0.1369 0.6741 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9835 -0.4279 0.5244 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5112 -0.3372 -0.8675 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8952 -0.9180 -0.9780 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8332 -0.1593 -0.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2530 -0.7179 -0.1711 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1197 0.0800 0.7703 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0869 1.4952 0.3662 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2660 2.3523 0.7233 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0963 1.9127 -0.5187 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3559 -1.1557 -0.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0912 -1.5048 0.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7464 -1.5860 -1.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6919 0.9498 0.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1589 0.7853 -1.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9180 0.5498 -1.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5475 1.9248 -0.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3327 -0.8150 1.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9379 0.7528 1.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8049 0.2349 2.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6105 1.6883 1.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6890 0.1772 1.7150 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6944 -1.1820 1.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2899 1.2303 -0.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9991 -0.3774 -1.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7520 -0.3264 -1.7926 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9933 -1.5586 -0.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8526 -0.4621 -1.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5748 -1.6287 0.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5793 1.2399 0.5639 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2993 -0.0494 1.7453 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9757 -1.4409 0.9370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6299 0.1829 1.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8225 -0.7720 -1.6220 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6006 0.7492 -1.1619 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2509 -0.9226 -2.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8508 -1.9927 -0.6448 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5645 -0.2777 0.9994 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8868 0.8932 -0.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2250 -1.7950 0.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6287 -0.6352 -1.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7010 0.0383 1.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1578 -0.3186 0.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9332 2.7588 -1.0445 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 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 1 22 1 0 1 23 1 0 1 24 1 0 2 25 1 0 2 26 1 0 3 27 1 0 3 28 1 0 4 29 1 0 4 30 1 0 5 31 1 0 5 32 1 0 6 33 1 0 6 34 1 0 7 35 1 0 7 36 1 0 8 37 1 0 8 38 1 0 11 39 1 0 11 40 1 0 12 41 1 0 12 42 1 0 13 43 1 0 13 44 1 0 14 45 1 0 14 46 1 0 15 47 1 0 15 48 1 0 16 49 1 0 16 50 1 0 17 51 1 0 17 52 1 0 18 53 1 0 18 54 1 0 21 55 1 0 M END

Standard InCHIKey	BGKROBBCCGUUCF-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H34O3/c1-2-3-4-5-8-11-14-17(19)15-12-9-6-7-10-13-16-18(20)21/h2-16H2,1H3,(H,20,21)
SMILES	CCCCCCCCC(=O)CCCCCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	298.25	Volume:	340.982 ? Van der Waals volume.
Dense:	0.875	LogP:	5.62 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.487 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.645 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	2.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.382	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.939	Fsp³:	0.889
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.018	Fluc inhibitor:	0.231 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.993	Promiscuous compounds:	0.783

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.138	MDCK Permeability:	-4.775
Pgp-inhibitor:	0.0	Pgp-substrate:	0.017
PAMPA:	0.528 ? 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):	0.336
20% Bioavailability (F20%):	0.215	30% Bioavailability (F30%):	0.261
50% Bioavailability (F50%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.979
Plasma Protein Binding (PPB):	96.448%	Volume Distribution (VD):	0.153
Fu:	2.78% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.076
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.021
BSEP inhibitor:	0.268

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.996
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.197
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.53
CYP2D6-inhibitor:	0.987	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.998	CYP2C8-inhibitor:	1.0
HLM stability:	0.004 ? 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):

3.831

Half-life (T1/2):

0.727

ADMET: Toxicity

hERG Blockers:	0.125	hERG Blockers (10um):	0.374
Human Hepatotoxicity (H-HT):	0.412	Drug-induced Liver Injury (DILI):	0.144
AMES Toxicity:	0.052	Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.198	Skin Sensitization:	0.924
Carcinogencity:	0.222	Eye Corrosion:	0.982
Eye Irritation:	0.997	Respiratory Toxicity:	0.911
Drug-induced Neurotoxicity:	0.04	Ototoxicity:	0.352
Hematotoxicity:	0.309	Drug-induced Nephrotoxicity:	0.375
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.025	Hek293 Cytotoxicity:	0.033
BCF:	0.823 ? 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:	3.714 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.337 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.592 ? 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
NPO6508	Dendrilla cactos	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10218	Gracilariopsis longissima	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4629	Angelica tschimganica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24	Gypsophila patrinii	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3722	Litoria subglandulosa	Species	Hylidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO932	Myrceugenia exsucca	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23535	Naganishia albida	Species	Filobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5554	Quercus lanceaefolia	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3722	Litoria subglandulosa	Species	Hylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23535	Naganishia albida	Species	Filobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6508	Dendrilla cactos	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5554	Quercus lanceaefolia	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4629	Angelica tschimganica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10218	Gracilariopsis longissima	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO932	Myrceugenia exsucca	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24	Gypsophila patrinii	Species	Caryophyllaceae	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
GI50	58

Activity Type	# Activity
Cell line	58

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
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	25644.84	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	25292.98	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	30269.13	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	33265.96	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	18879.91	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	4092.61	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	19678.86	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	31332.86	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	15452.54	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	23933.16	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	18879.91	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	18836.49	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	14757.07	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	26915.35	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	25061.09	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	24831.33	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	17258.38	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	25292.98	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	61094.2	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	33342.64	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	16180.8	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	47533.52	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	39719.15	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	17298.16	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	25468.3	nM	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	34197.94	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	32136.61	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	24603.68	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	16710.91	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	50234.26	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	14791.08	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	25941.79	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	36140.99	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	19724.23	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	37153.52	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	21577.44	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	23933.16	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	28379.19	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	22961.49	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	27039.58	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	21330.45	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	20090.93	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	34514.37	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	26424.09	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	18663.8	nM	PubChem BioAssay data set
NPT577	Cell line	RXF 631	Homo sapiens	GI50	n.a.	20989.4	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	22908.68	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	20137.24	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	28575.91	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	27164.39	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	23014.42	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	36057.86	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	27415.74	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	21777.1	nM	PubChem BioAssay data set
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	19186.69	nM	PubChem BioAssay data set

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 NPC74845 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	35117
0.1-0.2	13222
0.2-0.3	1181
0.3-0.4	175
0.4-0.5	86
0.5-0.6	34
0.6-0.7	21
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC18712
0.7714	Intermediate Similarity	NPC477201
0.7576	Intermediate Similarity	NPC40082
0.7407	Intermediate Similarity	NPC171736
0.7407	Intermediate Similarity	NPC301585
0.7407	Intermediate Similarity	NPC261080
0.7407	Intermediate Similarity	NPC132565
0.7407	Intermediate Similarity	NPC209970
0.7407	Intermediate Similarity	NPC216630
0.7407	Intermediate Similarity	NPC201844
0.7407	Intermediate Similarity	NPC301696
0.7407	Intermediate Similarity	NPC196924
0.7407	Intermediate Similarity	NPC307783
0.7407	Intermediate Similarity	NPC154186
0.7407	Intermediate Similarity	NPC149184
0.7407	Intermediate Similarity	NPC279026
0.7407	Intermediate Similarity	NPC113928
0.7407	Intermediate Similarity	NPC14227
0.7037	Intermediate Similarity	NPC155263
0.6757	Remote Similarity	NPC106851
0.6757	Remote Similarity	NPC282788
0.6757	Remote Similarity	NPC274927
0.641	Remote Similarity	NPC251042
0.641	Remote Similarity	NPC174447
0.641	Remote Similarity	NPC122521
0.6296	Remote Similarity	NPC214610
0.6296	Remote Similarity	NPC118968
0.6296	Remote Similarity	NPC183424
0.6296	Remote Similarity	NPC294085
0.6071	Remote Similarity	NPC175342
0.6061	Remote Similarity	NPC424
0.6061	Remote Similarity	NPC36061
0.6061	Remote Similarity	NPC69510
0.6061	Remote Similarity	NPC77272
0.6061	Remote Similarity	NPC8219
0.6061	Remote Similarity	NPC290563
0.6061	Remote Similarity	NPC139029
0.6061	Remote Similarity	NPC281972
0.6061	Remote Similarity	NPC261831
0.6061	Remote Similarity	NPC87564
0.5926	Remote Similarity	NPC268826
0.5882	Remote Similarity	NPC95145
0.5882	Remote Similarity	NPC325642
0.5882	Remote Similarity	NPC65174
0.5758	Remote Similarity	NPC281245
0.5714	Remote Similarity	NPC87394
0.5714	Remote Similarity	NPC235242
0.5714	Remote Similarity	NPC324004
0.5714	Remote Similarity	NPC328497
0.5714	Remote Similarity	NPC602547
0.5625	Remote Similarity	NPC55023
0.5625	Remote Similarity	NPC21844
0.5588	Remote Similarity	NPC129972
0.5588	Remote Similarity	NPC301528
0.5588	Remote Similarity	NPC71317
0.5588	Remote Similarity	NPC92114
0.5588	Remote Similarity	NPC163746
0.5588	Remote Similarity	NPC103286
0.5556	Remote Similarity	NPC225318
0.5556	Remote Similarity	NPC174368
0.5556	Remote Similarity	NPC154245
0.5556	Remote Similarity	NPC85813
0.5556	Remote Similarity	NPC223697
0.5556	Remote Similarity	NPC6095
0.5484	Remote Similarity	NPC604140
0.5357	Remote Similarity	NPC134782
0.5357	Remote Similarity	NPC79887
0.5357	Remote Similarity	NPC606898
0.5349	Remote Similarity	NPC325977
0.5349	Remote Similarity	NPC143396
0.5294	Remote Similarity	NPC314679
0.5278	Remote Similarity	NPC321062
0.5152	Remote Similarity	NPC180534
0.5152	Remote Similarity	NPC611531

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC74845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5983
0.1-0.2	2838
0.2-0.3	265
0.3-0.4	41
0.4-0.5	12
0.5-0.6	4
0.6-0.7	3
0.7-0.8	3
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
0.7407	Intermediate Similarity	NPD2270	Pre-clinical
0.7407	Intermediate Similarity	NPD633	Phase 3
0.7407	Intermediate Similarity	NPD9448	Phase 2
0.6296	Remote Similarity	NPD9655	Phase 4
0.6061	Remote Similarity	NPD3195	Phase 2
0.6061	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5556	Remote Similarity	NPD4266	Phase 2
0.5208	Remote Similarity	NPD5368	Phase 2
0.5152	Remote Similarity	NPD622	Pre-clinical

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