NPASS Compound

Natural Product: NPC605569

Natural Product ID	NPC605569
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OXRCQEMNONCHMK-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL74644
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002596] 4'-O-methylated flavonoids

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 47 49 0 0 0 0 0 0 0 0999 V2000 7.4563 -0.8665 -1.2591 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6298 0.2468 -0.9326 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2747 0.0541 -0.7065 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6853 -1.1887 -0.7858 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3087 -1.3380 -0.5490 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5175 -0.2795 -0.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0834 -0.3285 0.0695 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4072 0.8089 0.1388 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8598 0.9276 0.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5048 2.1513 0.4537 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8421 2.3021 0.7242 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4502 3.5712 0.7701 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0055 4.1557 -0.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6359 5.4906 -0.2646 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9435 3.4971 -1.4277 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5696 1.1542 0.9503 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9749 -0.1117 0.9070 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6793 -1.2696 1.1290 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2797 -1.9315 0.0831 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0515 -3.1923 0.2961 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1716 -1.4601 -1.0684 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6264 -0.2000 0.6302 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0031 -1.4209 0.5787 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6543 -2.4639 0.7822 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3764 -1.4658 0.2931 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9546 -2.7283 0.2640 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4393 -3.2747 1.5121 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1767 0.9598 -0.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5002 1.1436 -0.3935 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0334 -1.2892 -2.1996 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5030 -0.5636 -1.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4233 -1.6442 -0.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2973 -2.0257 -1.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8975 -2.3122 -0.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9254 3.0458 0.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0646 5.7400 -1.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9218 6.2830 0.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4754 5.4180 0.4587 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6237 1.2177 1.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4005 -4.0838 0.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8679 -3.2882 -0.4606 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5461 -3.1179 1.2820 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6308 -3.2209 2.2594 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6949 -4.3348 1.3252 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3329 -2.7376 1.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5484 1.8220 0.0797 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9064 2.1485 -0.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 2 0 11 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 2 0 17 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 26 27 1 0 6 28 1 0 28 29 2 0 29 3 1 0 25 7 2 0 22 9 1 0 1 30 1 0 1 31 1 0 1 32 1 0 4 33 1 0 5 34 1 0 10 35 1 0 14 36 1 0 14 37 1 0 14 38 1 0 16 39 1 0 20 40 1 0 20 41 1 0 20 42 1 0 27 43 1 0 27 44 1 0 27 45 1 0 28 46 1 0 29 47 1 0 M END

Standard InCHIKey	OXRCQEMNONCHMK-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C21H18O8/c1-11(22)27-15-9-16(28-12(2)23)18-17(10-15)29-20(21(26-4)19(18)24)13-5-7-14(25-3)8-6-13/h5-10H,1-4H3
SMILES	COc1ccc(-c2oc3cc(OC(C)=O)cc(OC(C)=O)c3c(=O)c2OC)cc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	398.1	Volume:	390.06 ? Van der Waals volume.
Dense:	1.021	LogP:	2.217 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.579 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.715 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	20.0
TPSA:	101.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.476	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.4	Fsp³:	0.19
MCE-18:	20.0 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.059	Fluc inhibitor:	0.435 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.971 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.721 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.34	Promiscuous compounds:	0.244

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.676	MDCK Permeability:	-4.426
Pgp-inhibitor:	0.998	Pgp-substrate:	0.125
PAMPA:	0.194 ? 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):	0.028
20% Bioavailability (F20%):	0.079	30% Bioavailability (F30%):	0.529
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035	MRP1:	0.928
Plasma Protein Binding (PPB):	93.398%	Volume Distribution (VD):	0.046
Fu:	8.739% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.07
OATP1B3 inhibitor:	0.939	BCRP inhibitor:	0.189
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.662	CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.033	CYP2C19-substrate:	0.194
CYP2C9-inhibitor:	0.083	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.027
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.998
HLM stability:	0.893 ? 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):

3.65

Half-life (T1/2):

0.523

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.214
Human Hepatotoxicity (H-HT):	0.357	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.544	Rat Oral Acute Toxicity:	0.479
Maximum Recommended Daily Dose:	0.355	Skin Sensitization:	0.71
Carcinogencity:	0.603	Eye Corrosion:	0.613
Eye Irritation:	0.947	Respiratory Toxicity:	0.398
Drug-induced Neurotoxicity:	0.203	Ototoxicity:	0.065
Hematotoxicity:	0.439	Drug-induced Nephrotoxicity:	0.052
Genotoxicity:	0.768	RPMI-8226 Immunitoxicity:	0.04
A549 Cytotoxicity:	0.347	Hek293 Cytotoxicity:	0.229
BCF:	0.824 ? 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:	3.798 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.767 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.481 ? 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
NPO40145	Gardenia ternifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28488862]
NPO40145	Gardenia ternifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Potency	18
Activity	3
GI50	48

Activity Type	# Activity
Individual protein	15
Cell line	52
Unchecked	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PubChem BioAssay data set
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT11	Individual protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	6309.6	nM	PubChem BioAssay data set
NPT161	Individual protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	8912.5	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	20596.2	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT50	Individual protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PubChem BioAssay data set
NPT7	Individual protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	63095.7	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	18356.4	nM	PubChem BioAssay data set
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	46451.5	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	16069.41	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	10351.42	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	16865.53	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	12676.52	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	14487.72	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	16982.44	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	4036.45	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	20701.41	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	18323.14	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	2118.36	nM	PubChem BioAssay data set
NPT137	Cell line	L1210	Mus musculus	Activity	n.a.	n.a.	n.a.	PMID[469554]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	20183.66	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	19724.23	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	21978.6	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	15922.09	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	16749.43	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	20749.14	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	14454.4	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	25351.29	nM	PubChem BioAssay data set
NPT517	Cell line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	15000.0	nM	PMID[9632366]
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	9772.37	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	18238.96	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	28840.32	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	12445.15	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	21037.78	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	15381.55	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	14962.36	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	21727.01	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	21777.1	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	19010.78	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	26485.0	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	13740.42	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	12050.36	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	15488.17	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	17947.34	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	14157.94	nM	PubChem BioAssay data set
NPT1317	Cell line	CCRF S-180	Mus musculus	Activity	n.a.	n.a.	n.a.	PMID[469554]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	23334.58	nM	PubChem BioAssay data set
NPT71	Cell line	HEK293	Homo sapiens	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	12502.59	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	16180.8	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	18071.74	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	4187.94	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	13489.63	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	20796.97	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	13931.57	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	19678.86	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	15885.47	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	17021.59	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	14655.48	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	19588.45	nM	PubChem BioAssay data set
NPT21830	Cell line	CA-755	n.a.	Activity	n.a.	n.a.	n.a.	PMID[469554]
NPT28438	Unchecked	Unchecked	n.a.	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT28438	Unchecked	Unchecked	n.a.	Potency	n.a.	20596.2	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 NPC605569 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	31529
0.1-0.2	16027
0.2-0.3	1880
0.3-0.4	331
0.4-0.5	62
0.5-0.6	18
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8776	High Similarity	NPC474037
0.8	Intermediate Similarity	NPC472535
0.7959	Intermediate Similarity	NPC72452
0.7321	Intermediate Similarity	NPC177839
0.7193	Intermediate Similarity	NPC474170
0.7193	Intermediate Similarity	NPC474388
0.6604	Remote Similarity	NPC61546
0.6429	Remote Similarity	NPC310259
0.6182	Remote Similarity	NPC69752
0.614	Remote Similarity	NPC90582
0.6102	Remote Similarity	NPC605582
0.5902	Remote Similarity	NPC608137
0.5893	Remote Similarity	NPC602291
0.589	Remote Similarity	NPC117478
0.5811	Remote Similarity	NPC481404
0.5614	Remote Similarity	NPC101294
0.56	Remote Similarity	NPC321478
0.5593	Remote Similarity	NPC262094
0.5574	Remote Similarity	NPC153758
0.5484	Remote Similarity	NPC179126
0.5397	Remote Similarity	NPC34725
0.5375	Remote Similarity	NPC473516
0.5323	Remote Similarity	NPC470216
0.5246	Remote Similarity	NPC59951
0.5246	Remote Similarity	NPC110070
0.5246	Remote Similarity	NPC276905
0.5125	Remote Similarity	NPC475214
0.5085	Remote Similarity	NPC608197
0.5082	Remote Similarity	NPC203891

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5281
0.1-0.2	3786
0.2-0.3	78
0.3-0.4	4
0.4-0.5	1
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