NPASS Compound

Natural Product: NPC173352

Natural Product ID	NPC173352
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Radicicol
IUPAC Name	n.a.
Synonyms	Monorden; Radicicol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL414883
PubChem CID	6323491
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

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 42 44 0 0 0 0 0 0 0 0999 V2000 -1.8797 -3.1784 -1.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7906 -1.7263 -0.5359 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7951 -0.9450 -1.2980 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0182 0.4689 -0.8998 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4566 0.6766 -0.5240 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3219 0.6468 0.4276 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2863 1.8909 1.1623 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2157 2.6426 1.2154 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0270 2.1943 0.4991 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0636 2.9447 0.5534 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3079 2.6084 -0.1200 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2706 3.3944 0.0478 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3980 1.3980 -0.9509 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2717 0.3816 -0.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7744 -0.7203 0.3422 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3862 -1.1249 0.4478 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0428 -1.3195 1.6183 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4529 -1.3084 -0.6056 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6899 -1.5989 0.9459 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1452 -2.7151 1.5913 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0432 -1.3943 0.9174 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5404 -0.2952 0.2795 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6354 0.5734 -0.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2812 1.9716 -1.1746 Cl 0 0 0 0 0 0 0 0 0 0 0 0 5.8985 -0.0143 0.2039 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1024 -3.8037 -0.6524 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8618 -3.5435 -0.7232 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9266 -3.1762 -2.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0608 -1.8480 0.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7892 -1.4887 -1.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5541 -1.0157 -2.4146 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8056 1.2935 -1.6147 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5205 -0.2631 1.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1656 2.2383 1.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1475 3.5469 1.7366 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0241 1.2923 -0.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0676 3.8812 1.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4557 0.8944 -1.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8183 1.6622 -1.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1731 -3.5916 1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7284 -2.1016 1.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2953 0.5715 0.9355 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 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 15 19 1 0 19 20 1 0 19 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 22 25 1 0 18 2 1 0 6 4 1 0 23 14 1 0 1 26 1 0 1 27 1 0 1 28 1 0 2 29 1 1 3 30 1 0 3 31 1 0 4 32 1 6 6 33 1 1 7 34 1 0 8 35 1 0 9 36 1 0 10 37 1 0 13 38 1 0 13 39 1 0 20 40 1 0 21 41 1 0 25 42 1 0 M END

Standard InCHIKey	WYZWZEOGROVVHK-GTMNPGAYSA-N
Standard InCHI	InChI=1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2+,5-3-/t9-,14-,15-/m1/s1
SMILES	C[C@@H]1C[C@H]2O[C@@H]2/C=CC=CC(=O)Cc2c(C(=O)O1)c(O)cc(c2Cl)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	364.07	Volume:	343.712 ? Van der Waals volume.
Dense:	1.059	LogP:	2.134 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.385 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.138 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	23.0
TPSA:	96.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.542	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.541	Fsp³:	0.333
MCE-18:	64.917 ? 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:	0.711	Fluc inhibitor:	0.942 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.351 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.272 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.463	Promiscuous compounds:	0.444

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.311	MDCK Permeability:	-4.816
Pgp-inhibitor:	0.177	Pgp-substrate:	0.15
PAMPA:	0.494 ? 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%):	0.007	30% Bioavailability (F30%):	0.364
50% Bioavailability (F50%):	0.819

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.957
Plasma Protein Binding (PPB):	98.476%	Volume Distribution (VD):	-0.152
Fu:	1.351% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.962
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.234
BSEP inhibitor:	0.958

ADMET: Metabolism

CYP1A2-inhibitor:	0.045	CYP1A2-substrate:	0.741
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.12	CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.851 ? 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):

6.599

Half-life (T1/2):

1.177

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.276
Human Hepatotoxicity (H-HT):	0.872	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.96	Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.962	Skin Sensitization:	1.0
Carcinogencity:	0.844	Eye Corrosion:	0.024
Eye Irritation:	0.931	Respiratory Toxicity:	0.834
Drug-induced Neurotoxicity:	0.905	Ototoxicity:	0.228
Hematotoxicity:	0.142	Drug-induced Nephrotoxicity:	0.945
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.377
A549 Cytotoxicity:	0.954	Hek293 Cytotoxicity:	0.858
BCF:	1.304 ? 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:	4.132 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.195 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.833 ? 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
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444718]
NPO27821.1	Pochonia chlamydosporia	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12828470]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499313]
NPO40515	Chaetomium chiversii	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499313]
NPO11145	Chaetomium chiversii	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18052326]
NPO32692	paraphaeosphaeria quadriseptata	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18052326]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24495105]
NPO40381	Trichobotrys effusa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[24797798]
NPO40532	Hypoestes forsskaolii	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30839211]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11145	Chaetomium chiversii	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40381	Trichobotrys effusa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40532	Hypoestes forsskaolii	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11145	Chaetomium chiversii	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	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
Kd	15
IC50	44
EC50	5
Tm	22
Ki	8
ED50	1
Inhibition	8
Thermal melting change	59
Activity	10
Delta Tm	2
GI50	6
MIC90	2
MIC	8
MIC80	6
In vitro activity	2
Worm movement inhibition	1

Activity Type	# Activity
Individual protein	113
Cell line	22
Single protein	11
Organism	32
Unchecked	2
Protein family	8
Non-molecular	2
Others	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	=	27.0	nM	PMID[18426954]
NPT1265	Individual protein	Serine/threonine-protein kinase PIM1	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1700	Individual protein	Serine/threonine-protein kinase PIM2	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1701	Individual protein	Serine/threonine-protein kinase PIM3	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT3221	Individual protein	Serine/threonine-protein kinase GAK	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1692	Individual protein	Mitogen-activated protein kinase 6	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1616	Individual protein	MAP kinase p38 beta	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1437	Individual protein	Tyrosine-protein kinase FES	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1431	Individual protein	Mitogen-activated protein kinase kinase kinase 5	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT3331	Individual protein	Serine/threonine-protein kinase MST2	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1706	Individual protein	Serine/threonine-protein kinase 2	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1707	Individual protein	Serine/threonine-protein kinase 10	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1691	Individual protein	Dual specificity mitogen-activated protein kinase kinase 6	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1684	Individual protein	Casein kinase I gamma 1	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1702	Individual protein	Serine/threonine-protein kinase PLK4	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1697	Individual protein	Serine/threonine-protein kinase PAK6	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1581	Individual protein	Carbonyl reductase [NADPH] 1	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT1581	Individual protein	Carbonyl reductase [NADPH] 1	Homo sapiens	Tm	=	4.6	degrees C	PMID[19097799]
NPT1581	Individual protein	Carbonyl reductase [NADPH] 1	Homo sapiens	IC50	=	3270.0	nM	PMID[18271521]
NPT1581	Individual protein	Carbonyl reductase [NADPH] 1	Homo sapiens	Ki	=	520.0	nM	PMID[18393465]
NPT1429	Individual protein	Heat shock protein HSP 90-beta	Homo sapiens	ED50	=	45.0	nM	PMID[24801877]
NPT1429	Individual protein	Heat shock protein HSP 90-beta	Homo sapiens	IC50	=	20.0	nM	PMID[24801877]
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	13.0	%	PMID[21930377]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	Inhibition	=	30.7	%	PMID[19097799]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	Inhibition	=	84.9	%	PMID[19097799]
NPT272	Individual protein	Kappa opioid receptor	Homo sapiens	Inhibition	=	-56.0	%	PMID[23910985]
NPT271	Individual protein	Delta opioid receptor	Homo sapiens	Inhibition	=	-27.8	%	PMID[15646539]
NPT1429	Individual protein	Heat shock protein HSP 90-beta	Homo sapiens	Kd	=	2.2	nM	PMID[12444692]
NPT1429	Individual protein	Heat shock protein HSP 90-beta	Homo sapiens	IC50	=	19.0	nM	PMID[18077363]
NPT1443	Individual protein	Pyruvate dehydrogenase kinase isoform 1	Homo sapiens	IC50	=	400000.0	nM	PMID[20100877]
NPT1671	Individual protein	AMP-activated protein kinase, alpha-2 subunit	Homo sapiens	Thermal melting change	=	-0.3	degrees C	PMID[18077363]
NPT1672	Individual protein	CaM kinase I delta	Homo sapiens	Thermal melting change	=	0.0	degrees C	PMID[18077363]
NPT1673	Individual protein	CaM kinase I gamma	Homo sapiens	Thermal melting change	=	0.6	degrees C	PMID[18077363]
NPT1674	Individual protein	CaM kinase II alpha	Homo sapiens	Thermal melting change	=	0.0	degrees C	PMID[18077363]
NPT1630	Individual protein	CaM kinase II beta	Homo sapiens	Thermal melting change	=	0.1	degrees C	PMID[18077363]
NPT1675	Individual protein	CaM kinase II delta	Homo sapiens	Thermal melting change	=	-0.4	degrees C	PMID[18077363]
NPT1676	Individual protein	CaM kinase II gamma	Homo sapiens	Thermal melting change	=	0.0	degrees C	PMID[18077363]
NPT1677	Individual protein	CaM kinase IV	Homo sapiens	Thermal melting change	=	-0.1	degrees C	PMID[18077363]
NPT1678	Individual protein	CaM-kinase kinase beta	Homo sapiens	Thermal melting change	=	-0.1	degrees C	PMID[18077363]
NPT1371	Individual protein	Cyclin-dependent kinase 2	Homo sapiens	Thermal melting change	=	0.5	degrees C	PMID[18077363]
NPT1571	Individual protein	Cyclin-dependent kinase 6	Homo sapiens	Thermal melting change	=	-0.5	degrees C	PMID[18077363]
NPT1679	Individual protein	Cyclin-dependent kinase-like 1	Homo sapiens	Thermal melting change	=	-0.2	degrees C	PMID[18077363]
NPT1680	Individual protein	Serine/threonine-protein kinase Chk2	Homo sapiens	Thermal melting change	=	1.6	degrees C	PMID[18077363]
NPT1682	Individual protein	Dual specificity protein kinase CLK2	Homo sapiens	Thermal melting change	=	0.1	degrees C	PMID[18077363]
NPT1683	Individual protein	Dual specificity protein kinase CLK3	Homo sapiens	Thermal melting change	=	0.0	degrees C	PMID[18077363]
NPT1684	Individual protein	Casein kinase I gamma 1	Homo sapiens	Thermal melting change	=	0.3	degrees C	PMID[18077363]
NPT1685	Individual protein	Casein kinase I gamma 2	Homo sapiens	Thermal melting change	=	0.0	degrees C	PMID[18077363]
NPT1686	Individual protein	Casein kinase I isoform gamma-3	Homo sapiens	Thermal melting change	=	0.1	degrees C	PMID[18077363]
NPT1687	Individual protein	Death-associated protein kinase 3	Homo sapiens	Thermal melting change	=	-0.3	degrees C	PMID[18077363]
NPT1688	Individual protein	Myotonin-protein kinase	Homo sapiens	Thermal melting change	=	-0.9	degrees C	PMID[18077363]
NPT1689	Individual protein	Tyrosine-protein kinase JAK1	Homo sapiens	Thermal melting change	=	-0.2	degrees C	PMID[18077363]
NPT1690	Individual protein	Dual specificity mitogen-activated protein kinase kinase 2	Homo sapiens	Thermal melting change	=	0.0	degrees C	PMID[18077363]
NPT1691	Individual protein	Dual specificity mitogen-activated protein kinase kinase 6	Homo sapiens	Thermal melting change	=	0.0	degrees C	PMID[18077363]
NPT1431	Individual protein	Mitogen-activated protein kinase kinase kinase 5	Homo sapiens	Thermal melting change	=	-0.2	degrees C	PMID[18077363]
NPT1616	Individual protein	MAP kinase p38 beta	Homo sapiens	Thermal melting change	=	0.7	degrees C	PMID[18077363]
NPT281	Individual protein	MAP kinase ERK1	Homo sapiens	Thermal melting change	=	0.0	degrees C	PMID[18077363]
NPT1692	Individual protein	Mitogen-activated protein kinase 6	Homo sapiens	Thermal melting change	=	0.4	degrees C	PMID[18077363]
NPT1693	Individual protein	Serine/threonine-protein kinase MST4	Homo sapiens	Thermal melting change	=	-0.2	degrees C	PMID[18077363]
NPT1658	Individual protein	Serine/threonine-protein kinase NEK2	Homo sapiens	Thermal melting change	=	0.2	degrees C	PMID[18077363]
NPT1657	Individual protein	Serine/threonine-protein kinase NEK6	Homo sapiens	Thermal melting change	=	-0.6	degrees C	PMID[18077363]
NPT1694	Individual protein	Serine/threonine-protein kinase OSR1	Homo sapiens	Thermal melting change	=	1.4	degrees C	PMID[18077363]
NPT1695	Individual protein	Serine/threonine-protein kinase PAK 4	Homo sapiens	Thermal melting change	=	1.3	degrees C	PMID[18077363]
NPT1696	Individual protein	Serine/threonine-protein kinase PAK7	Homo sapiens	Thermal melting change	=	0.6	degrees C	PMID[18077363]
NPT1697	Individual protein	Serine/threonine-protein kinase PAK6	Homo sapiens	Thermal melting change	=	0.3	degrees C	PMID[18077363]
NPT1698	Individual protein	Serine/threonine-protein kinase PCTAIRE-1	Homo sapiens	Thermal melting change	=	0.2	degrees C	PMID[18077363]
NPT1699	Individual protein	3-phosphoinositide dependent protein kinase-1	Homo sapiens	Thermal melting change	=	0.2	degrees C	PMID[18077363]
NPT1265	Individual protein	Serine/threonine-protein kinase PIM1	Homo sapiens	Thermal melting change	=	-0.1	degrees C	PMID[18077363]
NPT1700	Individual protein	Serine/threonine-protein kinase PIM2	Homo sapiens	Thermal melting change	=	0.1	degrees C	PMID[18077363]
NPT1701	Individual protein	Serine/threonine-protein kinase PIM3	Homo sapiens	Thermal melting change	=	0.5	degrees C	PMID[18077363]
NPT1702	Individual protein	Serine/threonine-protein kinase PLK4	Homo sapiens	Thermal melting change	=	0.5	degrees C	PMID[18077363]
NPT1703	Individual protein	cAMP-dependent protein kinase alpha-catalytic subunit	Homo sapiens	Thermal melting change	=	0.7	degrees C	PMID[18077363]
NPT1704	Individual protein	Serine/threonine-protein kinase RIO2	Homo sapiens	Thermal melting change	=	-0.5	degrees C	PMID[18077363]
NPT1705	Individual protein	Ribosomal protein S6 kinase alpha 3	Homo sapiens	Thermal melting change	=	0.2	degrees C	PMID[18077363]
NPT1705	Individual protein	Ribosomal protein S6 kinase alpha 3	Homo sapiens	Thermal melting change	=	0.9	degrees C	PMID[18077363]
NPT1706	Individual protein	Serine/threonine-protein kinase 2	Homo sapiens	Thermal melting change	=	0.4	degrees C	PMID[18077363]
NPT1707	Individual protein	Serine/threonine-protein kinase 10	Homo sapiens	Thermal melting change	=	-0.4	degrees C	PMID[18077363]
NPT1708	Individual protein	Serine/threonine-protein kinase 16	Homo sapiens	Thermal melting change	=	0.3	degrees C	PMID[18077363]
NPT1709	Individual protein	Serine/threonine-protein kinase 17A	Homo sapiens	Thermal melting change	=	1.0	degrees C	PMID[18077363]
NPT1710	Individual protein	Serine/threonine-protein kinase 38	Homo sapiens	Thermal melting change	=	0.3	degrees C	PMID[18077363]
NPT1693	Individual protein	Serine/threonine-protein kinase MST4	Homo sapiens	Thermal melting change	=	0.9	degrees C	PMID[18077363]
NPT1711	Individual protein	Serine/threonine-protein kinase MST1	Homo sapiens	Thermal melting change	=	0.3	degrees C	PMID[18077363]
NPT1712	Individual protein	TRAF2- and NCK-interacting kinase	Homo sapiens	Thermal melting change	=	-0.3	degrees C	PMID[18077363]
NPT1713	Individual protein	PDZ-binding kinase	Homo sapiens	Thermal melting change	=	0.2	degrees C	PMID[18077363]
NPT1715	Individual protein	Serine/threonine-protein kinase VRK2	Homo sapiens	Thermal melting change	=	0.2	degrees C	PMID[18077363]
NPT1717	Individual protein	Serine/threonine-protein kinase 25	Homo sapiens	Thermal melting change	=	-0.6	degrees C	PMID[18077363]
NPT1443	Individual protein	Pyruvate dehydrogenase kinase isoform 1	Homo sapiens	IC50	=	230000.0	nM	PMID[28199108]
NPT1510	Individual protein	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens	IC50	=	16040.0	nM	PMID[32330741]
NPT1510	Individual protein	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens	IC50	=	16040.0	nM	PMID[34792334]
NPT6257	Individual protein	Tyrosine-protein kinase SRC	Rattus norvegicus	IC50	=	180.0	nM	PMID[8864235]
NPT22961	Single protein	Inactive serine/threonine-protein kinase VRK3	Homo sapiens	Thermal melting change	=	-0.4	degrees C	PMID[18077363]
NPT946	Individual protein	ATP-citrate synthase	Homo sapiens	Inhibition	=	50.0	%	PMID[30195238]
NPT946	Individual protein	ATP-citrate synthase	Homo sapiens	Ki	=	13000.0	nM	PMID[37428122]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	-1.22	%	PMID[23089527]
NPT831	Individual protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Thermal melting change	=	0.2	degrees C	PMID[18077363]
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	Kd	=	19.0	nM	PMID[22559947]
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	Kd	=	2.7	nM	PMID[22559947]
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	IC50	=	150.0	nM	PMID[23659371]
NPT6291	Individual protein	Heat shock protein HSP 90 (HSC82)	Saccharomyces cerevisiae S288c	IC50	=	200.0	nM	DOI[10.6019/CHEMBL1201861]
NPT22938	Single protein	Carbonyl reductase [NADPH] 3	Homo sapiens	Tm	<	2.0	degrees C	PMID[19097799]
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	IC50	=	16.0	nM	PMID[12713401]
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	IC50	=	530.0	nM	PMID[8277313]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	17.41	%	PMID[24063567]
NPT28102	Single protein	Virulence sensor histidine kinase phoQ	Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)	Kd	=	715000.0	nM	PMID[21235241]
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	Kd	=	4.2	nM	PMID[22758788]
NPT6365	Individual protein	Pyruvate dehydrogenase kinase isoform 3	Homo sapiens	IC50	=	230000.0	nM	PMID[15711537]
NPT591	Individual protein	Glycogen synthase kinase-3 beta	Homo sapiens	Thermal melting change	=	-0.3	degrees C	PMID[18077363]
NPT28102	Single protein	Virulence sensor histidine kinase phoQ	Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)	Activity	=	86.0	%	PMID[29110989]
NPT28103	Single protein	Histidine protein kinase DivJ	Caulobacter vibrioides (strain ATCC 19089 / CB15) (Caulobactercrescentus)	Activity	=	123.0	%	PMID[29110989]
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	Kd	=	1.2	nM	PMID[30839211]
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	Kd	=	1.8	nM	PMID[33661631]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	IC50	<	200.0	nM	PMID[18060775]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	IC50	=	150.0	nM	PMID[25651042]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	EC50	=	25.0	nM	PMID[11975483]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	Tm	=	5.1	degrees C	PMID[19097799]
NPT4501	Individual protein	Heat shock protein HSP 90 (HSP82)	Saccharomyces cerevisiae S288c	Kd	=	19.0	nM	PMID[22037378]
NPT945	Individual protein	ATP-citrate synthase	Rattus norvegicus	Ki	=	7000.0	nM	PMID[7853008]
NPT945	Individual protein	ATP-citrate synthase	Rattus norvegicus	Ki	=	13000.0	nM	PMID[17363259]
NPT22960	Single protein	Serine/threonine-protein kinase VRK1	Homo sapiens	Thermal melting change	=	-0.2	degrees C	PMID[18077363]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	Ki	=	20000.0	nM	PMID[28199108]
NPT28104	Single protein	Cell cycle histidine kinase CckA	Caulobacter vibrioides	Delta Tm	=	0.9	degrees C	PMID[29110989]
NPT28104	Single protein	Cell cycle histidine kinase CckA	Caulobacter vibrioides	IC50	=	184000.0	nM	PMID[29110989]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	Kd	=	19.0	nM	PMID[31663736]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	Delta Tm	=	21.32	degrees C	PMID[31928863]
NPT945	Individual protein	ATP-citrate synthase	Rattus norvegicus	Ki	=	7000.0	nM	PMID[37428122]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6581	Cell line	3Y1 cell line	n.a.	IC50	=	700.0	nM	PMID[18194870]
NPT1294	Cell line	NRK	Rattus norvegicus	IC50	=	290.0	nM	PMID[18027905]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	130.0	nM	PMID[26264503]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	=	58.0	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	=	76.0	nM	PMID[21084196]
NPT81	Cell line	A549	Homo sapiens	GI50	=	110.0	nM	PMID[22907036]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	89.2	nM	PubChem BioAssay data set
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	=	3.64	nM	PMID[17328523]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	30.0	nM	PMID[16933872]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	23.0	nM	PMID[22037378]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	47.7	nM	PMID[17958396]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	=	37.5	nM	PMID[19524332]
NPT81	Cell line	A549	Homo sapiens	GI50	=	1430.0	nM	PMID[18710917]
NPT1182	Cell line	J774.A1	Mus musculus	IC50	=	2350.0	nM	PMID[28835791]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	100.0	nM	PMID[28749671]
NPT81	Cell line	A549	Homo sapiens	IC50	=	100.0	nM	PMID[28749671]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	400.0	nM	PMID[28749671]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	80.0	%	PMID[31761383]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7200.0	nM	PMID[24576210]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC90	=	46800.0	nM	PMID[24576210]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5600.0	nM	PMID[24576210]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC90	=	60200.0	nM	PMID[11325232]
NPT25805	Organism	Phytophthora litchii	Phytophthora litchii	IC50	=	1400.0	nM	PMID[28749671]
NPT1532	Organism	Mucor racemosus	Mucor racemosus	MIC	=	0.39	ug.mL-1	PMID[32692166]
NPT28438	Unchecked	Unchecked	n.a.	Kd	=	2.0	nM	PMID[35298171]
NPT28438	Unchecked	Unchecked	n.a.	EC50	=	1097000.0	nM	PMID[37688544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	59.0	nM	PMID[12773056]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	110.0	nM	PMID[12773056]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Activity	=	-75.0	%	PMID[22998443]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Activity	=	-76.0	%	DrugMatrix in vitro pharmacology data
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Activity	=	-94.0	%	DrugMatrix in vitro pharmacology data
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Activity	=	-100.0	%	DrugMatrix in vitro pharmacology data
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	200.0	nM	PMID[12502314]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	620.0	nM	PMID[28835791]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	290.0	nM	PMID[28835791]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	300000.0	nM	PMID[29110989]
NPT20	Organism	Candida albicans	Candida albicans	MIC80	=	1.0	ug.mL-1	PMID[35298171]
NPT28810	Protein family	Heat shock protein HSP90	Homo sapiens	IC50	=	20.0	nM	PMID[32652407]
NPT20	Organism	Candida albicans	Candida albicans	MIC80	=	0.5	ug.mL-1	PMID[35298171]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	98.0	%	PMID[18163584]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	9100.0	nM	DrugMatrix in vitro pharmacology data
NPT20950	Cell line	Erythrocyte	n.a.	Activity	=	0.0	%	PMID[29110989]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	300000.0	nM	PMID[29110989]
NPT769	Organism	Mucor mucedo	Mucor mucedo	MIC	=	0.39	ug.mL-1	PMID[32692166]
NPT2254	Organism	Schistosoma mansoni	Schistosoma mansoni	In vitro activity	n.a.	n.a.	n.a.	Using ChEMBL to complement schistosome drug discovery
NPT2254	Organism	Schistosoma mansoni	Schistosoma mansoni	EC50	=	1828.0	nM	Using ChEMBL to complement schistosome drug discovery
NPT2	Others	Unspecified	n.a.	IC50	<	100.0	nM	PMID[17664328]
NPT2	Others	Unspecified	n.a.	EC50	=	0.8	nM	PMID[23398362]
NPT2	Others	Unspecified	n.a.	IC50	=	27.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	IC50	=	0.27	nM	Open TG-GATES in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	IC50	=	190.0	nM	PMID[18809945]
NPT2	Others	Unspecified	n.a.	Kd	=	3.04	nM	PMID[7623030]
NPT2	Others	Unspecified	n.a.	Kd	=	19.0	nM	PMID[23659371]
NPT2	Others	Unspecified	n.a.	IC50	=	127000.0	nM	PMID[25646964]
NPT22036	Cell line	HL	Homo sapiens	Activity	=	0.6	%	PMID[29043803]
NPT28105	Organism	Caulobacter vibrioides	Caulobacter vibrioides	MIC	>	300000.0	nM	PMID[29110989]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	0.39	ug.mL-1	PMID[32692166]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2254	Organism	Schistosoma mansoni	Schistosoma mansoni	Worm movement inhibition	=	82.43	%	Using ChEMBL to complement schistosome drug discovery

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference
Homo sapiens	Liver	Drug metabolism	=	83.0	%	PMID[25141341]

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference
-	Candida albicans	LD99	=	12.0	mg/ml	PMID[18077363]
-	Phaeosphaeria nodorum	LD99	=	12.0	mg/ml	PMID[19928832]

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 NPC173352 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	12369
0.1-0.2	36099
0.2-0.3	1325
0.3-0.4	42
0.4-0.5	8
0.5-0.6	6
0.6-0.7	8
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
0.7164	Intermediate Similarity	NPC481128
0.6984	Remote Similarity	NPC210966
0.697	Remote Similarity	NPC28669
0.6923	Remote Similarity	NPC58653
0.6515	Remote Similarity	NPC489258
0.6364	Remote Similarity	NPC474096
0.6364	Remote Similarity	NPC481130
0.6324	Remote Similarity	NPC474061
0.6154	Remote Similarity	NPC298401
0.5857	Remote Similarity	NPC481129
0.5797	Remote Similarity	NPC473696
0.5479	Remote Similarity	NPC489257
0.5352	Remote Similarity	NPC470081
0.5139	Remote Similarity	NPC610827
0.5135	Remote Similarity	NPC600804

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC173352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2841
0.1-0.2	6247
0.2-0.3	62
0.3-0.4	0
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