NPASS Compound

Natural Product: NPC317237

Natural Product ID	NPC317237
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Haematoxylin
IUPAC Name	7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1479103
PubChem CID	10603
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

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 36 39 0 0 0 0 0 0 0 0999 V2000 1.4953 -2.0400 0.0217 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1705 -0.7160 0.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4828 -0.4773 0.3898 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9682 0.7929 0.3365 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1250 1.7864 -0.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7938 1.5493 -0.4014 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2754 0.2686 -0.3543 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0217 -0.3556 -0.6204 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0845 -1.6653 0.1685 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9221 -2.5902 -0.4643 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0536 -1.8318 -0.9247 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3473 -0.5917 -0.3454 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2390 0.2541 -0.1534 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4551 1.4543 0.4012 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7381 1.8488 0.7728 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8210 1.0180 0.5820 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6143 -0.2289 0.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7196 -1.0636 -0.1789 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0868 1.4477 0.9657 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1956 -1.4313 1.5148 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6297 3.0880 -0.1093 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2873 1.0476 0.6763 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8938 -2.7257 0.7946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6593 -2.4432 -1.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1540 -1.2706 0.7023 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2483 2.4160 -0.7096 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0983 -0.6706 -1.6998 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3167 -3.2524 0.3330 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4858 -3.2131 -1.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6048 2.0992 0.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8476 2.8373 1.2183 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6539 -0.7372 -0.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4392 2.3660 0.6594 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3707 -2.0470 2.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0053 3.8908 0.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9731 1.1863 -0.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 16 19 1 0 9 20 1 0 5 21 1 0 4 22 1 0 9 1 1 0 7 2 1 0 13 8 1 0 17 12 1 0 1 23 1 0 1 24 1 0 3 25 1 0 6 26 1 0 8 27 1 0 10 28 1 0 10 29 1 0 14 30 1 0 15 31 1 0 18 32 1 0 19 33 1 0 20 34 1 0 21 35 1 0 22 36 1 0 M END

Standard InCHIKey	WZUVPPKBWHMQCE-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2
SMILES	C1C2=CC(=C(C=C2C3C1(COC4=C3C=CC(=C4O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	302.08	Volume:	287.989 ? Van der Waals volume.
Dense:	1.049	LogP:	1.295 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.662 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	20.0
TPSA:	110.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.469	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.858	Fsp³:	0.25
MCE-18:	81.6 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.456	Fluc inhibitor:	0.945 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.456 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.151 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.422	Promiscuous compounds:	0.346

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.268	MDCK Permeability:	-4.837
Pgp-inhibitor:	0.0	Pgp-substrate:	0.031
PAMPA:	0.538 ? 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):	0.006
20% Bioavailability (F20%):	0.938	30% Bioavailability (F30%):	0.966
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148	MRP1:	0.9
Plasma Protein Binding (PPB):	70.655%	Volume Distribution (VD):	0.029
Fu:	27.581% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.029
BSEP inhibitor:	0.019

ADMET: Metabolism

CYP1A2-inhibitor:	0.041	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.692	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.505	CYP2D6-substrate:	0.752
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.484
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.104
HLM stability:	0.116 ? 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):

19.807

Half-life (T1/2):

2.376

ADMET: Toxicity

hERG Blockers:	0.1	hERG Blockers (10um):	0.607
Human Hepatotoxicity (H-HT):	0.539	Drug-induced Liver Injury (DILI):	0.217
AMES Toxicity:	0.618	Rat Oral Acute Toxicity:	0.46
Maximum Recommended Daily Dose:	0.515	Skin Sensitization:	0.961
Carcinogencity:	0.611	Eye Corrosion:	0.005
Eye Irritation:	0.932	Respiratory Toxicity:	0.584
Drug-induced Neurotoxicity:	0.036	Ototoxicity:	0.764
Hematotoxicity:	0.087	Drug-induced Nephrotoxicity:	0.091
Genotoxicity:	0.221	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.646	Hek293 Cytotoxicity:	0.208
BCF:	1.141 ? 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:	3.55 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.816 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.292 ? 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
NPO31133	Haematoxylum campechianum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12751322]

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	97
IC50	14
AC50	3
EC50	6

Activity Type	# Activity
Individual protein	98
Protein complex	1
Organism	2
Protein-protein interaction	2
Others	17

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	1584.9	nM	PubChem BioAssay data set
NPT2741	Individual protein	Pyruvate kinase	Leishmania mexicana	Potency	=	8912.5	nM	PubChem BioAssay data set
NPT2628	Individual protein	Luciferase	Photuris pennsylvanica	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT3	Individual protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	707.9	nM	PubChem BioAssay data set
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT151	Individual protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	1122.0	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	25929.0	nM	PubChem BioAssay data set
NPT2865	Individual protein	Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase	Plasmodium berghei	IC50	=	4740.0	nM	PubChem BioAssay data set
NPT1139	Individual protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	398.1	nM	PubChem BioAssay data set
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	7943.3	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT2630	Individual protein	mRNA interferase MazF	Escherichia coli K-12	EC50	=	72800.0	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	177.8	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT2865	Individual protein	Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase	Plasmodium berghei	IC50	=	25900.0	nM	PubChem BioAssay data set
NPT2630	Individual protein	mRNA interferase MazF	Escherichia coli K-12	EC50	=	30100.0	nM	PubChem BioAssay data set
NPT2865	Individual protein	Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase	Plasmodium berghei	IC50	=	29500.0	nM	PubChem BioAssay data set
NPT2971	Individual protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	14581.0	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	580.5	nM	PubChem BioAssay data set
NPT1853	Individual protein	Putative uncharacterized protein	Trypanosoma brucei brucei (strain 927/4 GUTat10.1)	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT1854	Individual protein	Phosphoglycerate kinase	Trypanosoma brucei brucei (strain 927/4 GUTat10.1)	Potency	n.a.	5798.8	nM	PubChem BioAssay data set
NPT2852	Individual protein	Prion protein	Homo sapiens	IC50	=	13956.0	nM	PubChem BioAssay data set
NPT2970	Individual protein	Fibrinogen beta chain	Homo sapiens	IC50	>	83295.0	nM	PubChem BioAssay data set
NPT2970	Individual protein	Fibrinogen beta chain	Homo sapiens	IC50	=	9328.0	nM	PubChem BioAssay data set
NPT1040	Individual protein	Human immunodeficiency virus type 1 Tat protein	Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1)	IC50	n.a.	11696.0	nM	PubChem BioAssay data set
NPT50	Individual protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	251.2	nM	PubChem BioAssay data set
NPT50	Individual protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	891.3	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT55	Individual protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	6294.6	nM	PubChem BioAssay data set
NPT55	Individual protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	19905.4	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT1509	Protein complex	Cyclin-dependent kinase 5/CDK5 activator 1	Homo sapiens	AC50	=	17507.0	nM	PubChem BioAssay data set
NPT801	Individual protein	Intestinal alkaline phosphatase	Homo sapiens	EC50	=	50000.0	nM	PubChem BioAssay data set
NPT905	Individual protein	Glucose-6-phosphate 1-dehydrogenase	Homo sapiens	IC50	=	66500.0	nM	PubChem BioAssay data set
NPT803	Individual protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	7079.5	nM	PubChem BioAssay data set
NPT917	Individual protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	IC50	n.a.	17360.0	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	26854.5	nM	PubChem BioAssay data set
NPT803	Individual protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	33807.8	nM	PubChem BioAssay data set
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	707.9	nM	PubChem BioAssay data set
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT57	Individual protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	IC50	=	3439.26	nM	PubChem BioAssay data set
NPT524	Individual protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT61	Individual protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT798	Individual protein	Alkaline phosphatase placental-like	Homo sapiens	EC50	=	60400.0	nM	PubChem BioAssay data set
NPT802	Individual protein	Alkaline phosphatase, tissue-nonspecific isozyme	Homo sapiens	EC50	=	85700.0	nM	PubChem BioAssay data set
NPT7	Individual protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT7	Individual protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	8912.5	nM	PubChem BioAssay data set
NPT698	Individual protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT484	Individual protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	8492.1	nM	PubChem BioAssay data set
NPT444	Individual protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT831	Individual protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	29934.9	nM	PubChem BioAssay data set
NPT446	Individual protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT93	Individual protein	Survival motor neuron protein	Homo sapiens	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	2818.4	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	3981.1	nM	PubChem BioAssay data set
NPT583	Individual protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	4466.8	nM	PubChem BioAssay data set
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	5011.9	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT60	Individual protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT59	Individual protein	DNA polymerase beta	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT63	Individual protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT799	Individual protein	Intestinal alkaline phosphatase	Mus musculus	EC50	n.a.	62100.0	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	7943.3	nM	PubChem BioAssay data set
NPT534	Individual protein	Phosphoglycerate kinase, glycosomal	Trypanosoma brucei brucei	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT821	Individual protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT755	Individual protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	63095.7	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	23778.1	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT47	Individual protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT53	Individual protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	2511.9	nM	PubChem BioAssay data set
NPT3835	Individual protein	Mannose-6-phosphate isomerase	Homo sapiens	IC50	=	26374.0	nM	PubChem BioAssay data set
NPT864	Individual protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	125.9	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT62	Individual protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	849.2	nM	PubChem BioAssay data set
NPT443	Individual protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT62	Individual protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	4775.5	nM	PubChem BioAssay data set
NPT4	Individual protein	Large T antigen	Simian virus 40	IC50	n.a.	4660.0	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	3162.3	nM	PubChem BioAssay data set
NPT62	Individual protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	425.6	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT52	Individual protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	IC50	=	340000.0	nM	PMID[34726055]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2616.9	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	20596.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	=	6080.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	=	19550.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2511.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1995.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	17782.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1258.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3981.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	n.a.	460.0	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 NPC317237 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	27635
0.1-0.2	20671
0.2-0.3	1529
0.3-0.4	11
0.4-0.5	3
0.5-0.6	4
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC44530
0.7115	Intermediate Similarity	NPC155392
0.7115	Intermediate Similarity	NPC274721
0.6923	Remote Similarity	NPC277951
0.5263	Remote Similarity	NPC302701
0.5263	Remote Similarity	NPC269091
0.5246	Remote Similarity	NPC211758
0.5161	Remote Similarity	NPC87794

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC317237 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5211
0.1-0.2	3860
0.2-0.3	79
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