NPASS Compound

Natural Product: NPC242885

Natural Product ID	NPC242885
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(-)-Dihydroguaiareticacid
IUPAC Name	4-[(2R,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
Synonyms	(-)-Dihydroguaiareticacid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL375927
PubChem CID	11602375
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

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 50 51 0 0 0 0 0 0 0 0999 V2000 -1.0054 1.3027 0.8140 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7321 0.4159 -0.3530 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5456 -0.8626 -0.2070 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0067 -0.5530 -0.1594 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7774 -0.4983 -1.3018 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1200 -0.2117 -1.2332 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7679 0.0343 -0.0405 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9961 -0.0193 1.1169 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6431 -0.3088 1.0403 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6478 0.2280 2.3152 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9291 0.1924 3.5460 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1235 0.3233 0.0251 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6934 0.1673 -0.6513 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7849 -0.7453 -1.8557 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4935 -0.3872 0.4969 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9095 -0.6010 0.0954 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3333 -1.8022 -0.4449 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6531 -1.9958 -0.8172 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5808 -0.9819 -0.6542 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1770 0.2427 -0.1099 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8686 0.3800 0.2391 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1141 1.2540 0.0500 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6646 2.4769 0.6038 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9217 -1.1511 -1.0224 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8981 0.8063 1.7951 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4377 2.2481 0.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0928 1.6008 0.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1696 0.9317 -1.2593 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3484 -1.5806 -1.0094 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2989 -1.3612 0.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3262 -0.6824 -2.2702 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7474 -0.1643 -2.1329 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0513 -0.3487 1.9387 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6708 -0.8564 3.7961 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0338 0.8428 3.4602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5266 0.5902 4.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6365 0.3444 -0.8381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1731 1.1233 -0.9480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1381 -0.4310 -2.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8407 -0.7311 -2.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6080 -1.8236 -1.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3727 0.1609 1.4269 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0807 -1.4224 0.6881 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6471 -2.6275 -0.5932 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0049 -2.9297 -1.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5568 1.3266 0.6598 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8197 2.8764 -0.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5137 3.2137 0.5082 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2805 2.3911 1.6191 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3021 -0.3969 -1.6072 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 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 7 12 1 0 2 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 19 24 1 0 9 4 1 0 21 16 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 6 3 29 1 0 3 30 1 0 5 31 1 0 6 32 1 0 9 33 1 0 11 34 1 0 11 35 1 0 11 36 1 0 12 37 1 0 13 38 1 6 14 39 1 0 14 40 1 0 14 41 1 0 15 42 1 0 15 43 1 0 17 44 1 0 18 45 1 0 21 46 1 0 23 47 1 0 23 48 1 0 23 49 1 0 24 50 1 0 M END

Standard InCHIKey	ADFOLUXMYYCTRR-ZIAGYGMSSA-N
Standard InCHI	InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14-/m1/s1
SMILES	C[C@H](Cc1ccc(c(c1)OC)O)[C@H](C)Cc1ccc(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	330.18	Volume:	356.705 ? Van der Waals volume.
Dense:	0.926	LogP:	3.442 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.124 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.914 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	12.0
TPSA:	58.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.8	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.864	Fsp³:	0.4
MCE-18:	28.0 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.5	Fluc inhibitor:	0.064 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.057 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.649	Promiscuous compounds:	0.241

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.067	MDCK Permeability:	-4.742
Pgp-inhibitor:	0.301	Pgp-substrate:	0.262
PAMPA:	0.002 ? 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):	0.002
20% Bioavailability (F20%):	0.742	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.563
Plasma Protein Binding (PPB):	88.36%	Volume Distribution (VD):	-0.177
Fu:	13.562% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.875
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.059	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.012	CYP2D6-substrate:	0.94
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.989 ? 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):

7.649

Half-life (T1/2):

1.208

ADMET: Toxicity

hERG Blockers:	0.236	hERG Blockers (10um):	0.747
Human Hepatotoxicity (H-HT):	0.53	Drug-induced Liver Injury (DILI):	0.291
AMES Toxicity:	0.511	Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.3	Skin Sensitization:	0.842
Carcinogencity:	0.375	Eye Corrosion:	0.609
Eye Irritation:	0.99	Respiratory Toxicity:	0.615
Drug-induced Neurotoxicity:	0.491	Ototoxicity:	0.307
Hematotoxicity:	0.225	Drug-induced Nephrotoxicity:	0.528
Genotoxicity:	0.1	RPMI-8226 Immunitoxicity:	0.126
A549 Cytotoxicity:	0.482	Hek293 Cytotoxicity:	0.562
BCF:	1.729 ? 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:	4.267 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.282 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.791 ? 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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO18777	Endiandra anthropophagorum	Species	Lauraceae	Eukaryota	n.a.	Australian	n.a.	PMID[17583952]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO18777	Endiandra anthropophagorum	Species	Lauraceae	Eukaryota	n.a.	Australian rainforest	n.a.	PMID[19138858]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO27465	Sinularia erecta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27142697]
NPO40344	Schisandra bicolor var. tuberculata	Strain	Schisandraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28333453]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO16221	Dolichos kilimandscharicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27593	Silene dioica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27777	Artemisia phaeolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27339	Lactarius blennius	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27635	Laurencia dendroidea	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26934	Naucleopsis mello-barretoi	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27570	Paederia foetida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27465	Sinularia erecta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27130	Tsuga sieboldii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5146	Tuta absoluta	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27593	Silene dioica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18777	Endiandra anthropophagorum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27777	Artemisia phaeolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5146	Tuta absoluta	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26934	Naucleopsis mello-barretoi	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27465	Sinularia erecta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16221	Dolichos kilimandscharicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27570	Paederia foetida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27635	Laurencia dendroidea	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27130	Tsuga sieboldii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27339	Lactarius blennius	Species	Russulaceae	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	8
Kinact	4
Ki	6
Ratio Ki	8
Activity	9
MIC	5
GI	2
EC50	2

Activity Type	# Activity
Individual protein	13
Cell line	11
Organism	9
Others	8
Non-molecular	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	IC50	=	35000.0	nM	PMID[17583952]
NPT1144	Individual protein	Carbonic anhydrase VB	Homo sapiens	Kinact	=	71.0	nM	PMID[19962903]
NPT1143	Individual protein	Carbonic anhydrase VA	Homo sapiens	Kinact	=	85.0	nM	PMID[19962903]
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Kinact	=	230.0	uM	PMID[19962903]
NPT3155	Individual protein	PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)	Mycobacterium tuberculosis	Ki	=	9100.0	nM	PMID[21332115]
NPT3156	Individual protein	Uncharacterized protein Rv1284/MT1322	Mycobacterium tuberculosis	Ki	=	850.0	nM	PMID[21332115]
NPT1148	Individual protein	Carbonic anhydrase	Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Ki	=	620.0	nM	PMID[21332115]
NPT3157	Individual protein	Carbonic anhydrase 2	Cryptococcus neoformans var. grubii	Ki	=	810.0	nM	PMID[21332115]
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	=	230000.0	nM	PMID[21332115]
NPT1588	Individual protein	Estradiol 17-beta-dehydrogenase 2	Homo sapiens	IC50	=	940.0	nM	PMID[28319389]
NPT1587	Individual protein	Estradiol 17-beta-dehydrogenase 1	Homo sapiens	IC50	=	7700.0	nM	PMID[28319389]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Kinact	=	307.0	uM	PMID[19962903]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	=	307000.0	nM	PMID[21332115]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	IC50	=	7490.0	nM	PMID[19138858]
NPT81	Cell line	A549	Homo sapiens	IC50	=	31200.0	nM	PMID[19138858]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	26000.0	nM	PMID[27210431]
NPT165	Cell line	HeLa	Homo sapiens	EC50	=	22000.0	nM	PMID[28754364]
NPT116	Cell line	HL-60	Homo sapiens	EC50	=	26000.0	nM	PMID[28754364]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	>	15.0	%	PMID[28333453]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	80.8	%	PMID[28333453]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	85.1	%	PMID[28333453]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	79.2	%	PMID[28333453]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	50000000.0	nM	PMID[27210431]
NPT962	Organism	Alternaria alternata	Alternaria alternata	Activity	=	32.0	%	PMID[27210431]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	49.9	%	PMID[27210431]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1560000.0	nM	PMID[27210431]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	MIC	=	390000.0	nM	PMID[27210431]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	22000.0	nM	PMID[27210431]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1600000.0	nM	PMID[28844400]
NPT20967	Cell line	Platelet	n.a.	Activity	=	76.4	%	PMID[24387347]
NPT2600	Organism	Fusarium solani	Fusarium solani	Activity	=	36.5	%	PMID[27210431]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3130000.0	nM	PMID[27210431]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	GI	=	18.4	%	PMID[27210431]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	GI	=	14.9	%	PMID[27210431]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	33.7	n.a.	PMID[21332115]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	361.2	n.a.	PMID[21332115]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	495.2	n.a.	PMID[21332115]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	379.0	n.a.	PMID[21332115]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	25.3	n.a.	PMID[21332115]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	270.6	n.a.	PMID[21332115]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	371.0	n.a.	PMID[21332115]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	284.0	n.a.	PMID[21332115]
NPT2637	Organism	Colletotrichum lagenarium	Colletotrichum lagenarium	Activity	=	33.8	%	PMID[27210431]

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
-	Culex pipiens	LD50	=	3.52	10'-5M	PMID[27210431]

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 NPC242885 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	22005
0.1-0.2	20820
0.2-0.3	5979
0.3-0.4	698
0.4-0.5	212
0.5-0.6	89
0.6-0.7	22
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC165133
1.0	High Similarity	NPC95614
1.0	High Similarity	NPC232316
0.8378	Intermediate Similarity	NPC56214
0.8158	Intermediate Similarity	NPC227217
0.8158	Intermediate Similarity	NPC117780
0.7949	Intermediate Similarity	NPC127587
0.7895	Intermediate Similarity	NPC487676
0.7576	Intermediate Similarity	NPC156840
0.7297	Intermediate Similarity	NPC85488
0.7209	Intermediate Similarity	NPC274356
0.7209	Intermediate Similarity	NPC101748
0.6944	Remote Similarity	NPC8547
0.6818	Remote Similarity	NPC487680
0.675	Remote Similarity	NPC31344
0.675	Remote Similarity	NPC317769
0.6739	Remote Similarity	NPC284464
0.6667	Remote Similarity	NPC257124
0.6486	Remote Similarity	NPC221049
0.6486	Remote Similarity	NPC140359
0.6364	Remote Similarity	NPC603109
0.6316	Remote Similarity	NPC471693
0.6316	Remote Similarity	NPC193544
0.625	Remote Similarity	NPC299406
0.62	Remote Similarity	NPC291101
0.62	Remote Similarity	NPC266197
0.6154	Remote Similarity	NPC255675
0.6136	Remote Similarity	NPC5428
0.6136	Remote Similarity	NPC607444
0.6	Remote Similarity	NPC487677
0.6	Remote Similarity	NPC57490
0.6	Remote Similarity	NPC487675
0.6	Remote Similarity	NPC603326
0.6	Remote Similarity	NPC603989
0.5854	Remote Similarity	NPC197757
0.5854	Remote Similarity	NPC17943
0.5833	Remote Similarity	NPC275950
0.5769	Remote Similarity	NPC161249
0.5745	Remote Similarity	NPC68779
0.5745	Remote Similarity	NPC108598
0.5745	Remote Similarity	NPC173308
0.5745	Remote Similarity	NPC181079
0.5714	Remote Similarity	NPC7097
0.5676	Remote Similarity	NPC293619
0.5641	Remote Similarity	NPC160380
0.5641	Remote Similarity	NPC38996
0.5581	Remote Similarity	NPC194416
0.5581	Remote Similarity	NPC177291
0.5581	Remote Similarity	NPC203133
0.5581	Remote Similarity	NPC312675
0.5581	Remote Similarity	NPC262156
0.5581	Remote Similarity	NPC127937
0.5581	Remote Similarity	NPC184651
0.5581	Remote Similarity	NPC113865
0.5556	Remote Similarity	NPC487679
0.5556	Remote Similarity	NPC487678
0.5526	Remote Similarity	NPC32163
0.55	Remote Similarity	NPC76451
0.5455	Remote Similarity	NPC117214
0.5455	Remote Similarity	NPC66518
0.5455	Remote Similarity	NPC476968
0.5435	Remote Similarity	NPC232275
0.54	Remote Similarity	NPC253481
0.54	Remote Similarity	NPC253722
0.54	Remote Similarity	NPC475875
0.5385	Remote Similarity	NPC23646
0.5385	Remote Similarity	NPC46880
0.5385	Remote Similarity	NPC485397
0.5333	Remote Similarity	NPC51840
0.5333	Remote Similarity	NPC82679
0.5319	Remote Similarity	NPC114298
0.5294	Remote Similarity	NPC273657
0.5283	Remote Similarity	NPC487681
0.5283	Remote Similarity	NPC476345
0.5283	Remote Similarity	NPC606339
0.5263	Remote Similarity	NPC246358
0.5263	Remote Similarity	NPC165106
0.5263	Remote Similarity	NPC203719
0.525	Remote Similarity	NPC36108
0.525	Remote Similarity	NPC233731
0.525	Remote Similarity	NPC610203
0.5217	Remote Similarity	NPC78974
0.5208	Remote Similarity	NPC164386
0.5208	Remote Similarity	NPC4181
0.5208	Remote Similarity	NPC201777
0.5208	Remote Similarity	NPC604524
0.52	Remote Similarity	NPC313081
0.5192	Remote Similarity	NPC102908
0.5192	Remote Similarity	NPC187998
0.5192	Remote Similarity	NPC257582
0.5192	Remote Similarity	NPC241522
0.5185	Remote Similarity	NPC106739
0.5185	Remote Similarity	NPC67247
0.5185	Remote Similarity	NPC610284
0.5128	Remote Similarity	NPC309203
0.5128	Remote Similarity	NPC604189
0.5122	Remote Similarity	NPC16651
0.5122	Remote Similarity	NPC181969
0.5116	Remote Similarity	NPC282703
0.5116	Remote Similarity	NPC184733
0.5116	Remote Similarity	NPC128208
0.5116	Remote Similarity	NPC129570
0.5116	Remote Similarity	NPC63238
0.5116	Remote Similarity	NPC602603
0.5106	Remote Similarity	NPC473853
0.5106	Remote Similarity	NPC98631
0.5106	Remote Similarity	NPC5018
0.5106	Remote Similarity	NPC206615
0.5106	Remote Similarity	NPC74817
0.5106	Remote Similarity	NPC470212
0.5106	Remote Similarity	NPC481914
0.5102	Remote Similarity	NPC266705
0.5102	Remote Similarity	NPC29008
0.5094	Remote Similarity	NPC110699
0.5094	Remote Similarity	NPC106920
0.5094	Remote Similarity	NPC300776
0.5094	Remote Similarity	NPC15811
0.5094	Remote Similarity	NPC176814
0.5094	Remote Similarity	NPC4982
0.5094	Remote Similarity	NPC106055
0.5094	Remote Similarity	NPC606629
0.5094	Remote Similarity	NPC610652
0.5091	Remote Similarity	NPC471505

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC242885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3533
0.1-0.2	5156
0.2-0.3	435
0.3-0.4	20
0.4-0.5	3
0.5-0.6	2
0.6-0.7	1
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
0.6667	Remote Similarity	NPD228	Phase 0
0.5263	Remote Similarity	NPD5283	Phase 2
0.5238	Remote Similarity	NPD824	Phase 4

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