NPASS Compound

Natural Product: NPC40302

Natural Product ID	NPC40302
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2,3,5-Tribromo-6-(3,5-Dibromo-2-Hydroxyphenoxy)Phenol
IUPAC Name	2,3,5-tribromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL148503
PubChem CID	10348509
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers [CHEMONTID:0001845] Bromodiphenyl ethers

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 25 26 0 0 0 0 0 0 0 0999 V2000 -4.3484 -2.5718 -1.1496 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.2620 -1.2422 -0.2941 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9758 -1.4861 0.0842 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1380 -0.5594 0.7094 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1362 -0.9726 1.0230 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3166 -0.4064 0.6087 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1034 0.3297 1.4635 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6284 0.5514 3.3280 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.2715 0.8795 0.9885 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6441 0.6934 -0.3170 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8550 -0.0516 -1.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7022 -0.5941 -0.7238 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8933 -1.3500 -1.5931 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4546 -0.2612 -2.9986 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.2744 1.4748 -0.9350 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.6851 0.6719 0.9413 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0078 0.9606 0.5658 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7850 0.0031 -0.0480 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7283 2.6935 0.9109 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.9451 1.6720 1.5542 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 -2.4847 -0.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8718 1.4600 1.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2282 -2.2872 -1.7763 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8029 0.2336 -0.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1218 2.6439 1.4177 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 1 0 5 6 1 0 6 7 2 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 11 14 1 0 10 15 1 0 4 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 16 20 1 0 18 2 1 0 12 6 1 0 3 21 1 0 9 22 1 0 13 23 1 0 18 24 1 0 20 25 1 0 M END

Standard InCHIKey	OBMWDTFRQJRRIM-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C12H5Br5O3/c13-4-1-6(15)10(18)8(2-4)20-12-7(16)3-5(14)9(17)11(12)19/h1-3,18-19H
SMILES	Brc1cc(Oc2c(Br)cc(c(c2O)Br)Br)c(c(c1)Br)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	591.62	Volume:	305.965 ? Van der Waals volume.
Dense:	1.934	LogP:	5.083 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.181 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.641 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	12.0
TPSA:	49.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.38	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.852	Fsp³:	0.0
MCE-18:	15.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.932	Fluc inhibitor:	0.343 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.317 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.998	Promiscuous compounds:	0.436

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.041	MDCK Permeability:	-4.65
Pgp-inhibitor:	0.459	Pgp-substrate:	0.0
PAMPA:	0.771 ? 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):	0.129
20% Bioavailability (F20%):	0.007	30% Bioavailability (F30%):	0.087
50% Bioavailability (F50%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.526	MRP1:	0.961
Plasma Protein Binding (PPB):	97.312%	Volume Distribution (VD):	-0.211
Fu:	1.054% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.983
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.085
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.027 ? 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):

5.67

Half-life (T1/2):

1.972

ADMET: Toxicity

hERG Blockers:	0.117	hERG Blockers (10um):	0.708
Human Hepatotoxicity (H-HT):	0.233	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.096	Rat Oral Acute Toxicity:	0.926
Maximum Recommended Daily Dose:	0.995	Skin Sensitization:	0.993
Carcinogencity:	0.793	Eye Corrosion:	0.984
Eye Irritation:	0.999	Respiratory Toxicity:	0.556
Drug-induced Neurotoxicity:	0.615	Ototoxicity:	0.06
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	0.073
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.63	Hek293 Cytotoxicity:	0.453
BCF:	1.805 ? 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:	5.648 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.203 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.087 ? 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
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10075800]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10650102]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO8481	Phyllospongia dendyi	Species	Thorectidae	Eukaryota	n.a.	Palau	n.a.	PMID[15043436]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17311456]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	Mandapam Coast, Tamilnadu, India	n.a.	PMID[22704923]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	Niphates recondita	Weizhou Island, Beibuwan Bay, Guangxi,China	n.a.	PMID[24387683]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25863431]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27399938]
NPO40870	Lamellodysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27399938]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28530828]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28841316]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31265296]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31990554]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32966070]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9463111]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9514013]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8481	Phyllospongia dendyi	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28504	Calothrix brevissima	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3308	Calycadenia fremontii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12931	Carex pumila	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8395.1	Crepis foetida subsp. rhoeadifolia	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13038	Fomes hartigii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9147	Frasera albomarginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10944	Mantella baroni	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2431	Penicilliopsis zonata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9355	Polygonatum orientale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9977	Polygonum sieboldi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12364	Polyides rotundus	Species	Polyideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12708	Rothia indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6781	Senecio acanthifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5958	Senegalia modesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5472	Spongia foliascens	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40870	Lamellodysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3308	Calycadenia fremontii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9147	Frasera albomarginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28504	Calothrix brevissima	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13038	Fomes hartigii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12708	Rothia indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9355	Polygonatum orientale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5958	Senegalia modesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12364	Polyides rotundus	Species	Polyideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12931	Carex pumila	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8395.1	Crepis foetida subsp. rhoeadifolia	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9977	Polygonum sieboldi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6781	Senecio acanthifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2431	Penicilliopsis zonata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5472	Spongia foliascens	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10944	Mantella baroni	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8481	Phyllospongia dendyi	Species	Thorectidae	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
Inhibition	2
IC50	8
IZ	4
EC50	1
MNTD	1

Activity Type	# Activity
Individual protein	6
Others	4
Organism	4
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1119	Individual protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	=	6200.0	nM	PMID[15267244]
NPT2784	Individual protein	GMP synthase [glutamine-hydrolyzing]	Homo sapiens	Inhibition	=	70.0	%	PMID[7494145]
NPT41	Individual protein	Aldose reductase	Homo sapiens	Inhibition	=	25.0	%	PMID[14613323]
NPT57	Individual protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[19323567]
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	2200.0	nM	PMID[15267244]
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	2500.0	nM	PMID[7494145]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	0.0	mm	PMID[17311456]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	7.0	mm	PMID[17311456]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	8.0	mm	PMID[17311456]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.0	mm	PMID[17311456]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	50.0	ug.mL-1	PMID[27399938]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	MNTD	=	50.0	ug ml-1	PMID[27399938]
NPT2	Others	Unspecified	n.a.	IC50	>	100000.0	nM	PMID[15267244]
NPT2	Others	Unspecified	n.a.	IC50	=	33500.0	nM	PMID[15043436]
NPT2	Others	Unspecified	n.a.	IC50	=	4200.0	nM	PMID[15043436]
NPT2	Others	Unspecified	n.a.	EC50	=	7.8	%	PMID[7494145]

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 NPC40302 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	43359
0.1-0.2	6375
0.2-0.3	84
0.3-0.4	19
0.4-0.5	6
0.5-0.6	9
0.6-0.7	5
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
0.7	Intermediate Similarity	NPC196371
0.6829	Remote Similarity	NPC104124
0.6667	Remote Similarity	NPC137922
0.6585	Remote Similarity	NPC601831
0.6585	Remote Similarity	NPC603923
0.6364	Remote Similarity	NPC63317
0.5957	Remote Similarity	NPC483502
0.5745	Remote Similarity	NPC131940
0.5682	Remote Similarity	NPC44270
0.5682	Remote Similarity	NPC175520
0.5625	Remote Similarity	NPC230013
0.5625	Remote Similarity	NPC81149
0.5333	Remote Similarity	NPC295879
0.5319	Remote Similarity	NPC170824
0.5306	Remote Similarity	NPC88733

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC40302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7525
0.1-0.2	1595
0.2-0.3	26
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
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	NPD911	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