NPASS Compound

Natural Product: NPC478664

Natural Product ID	NPC478664
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CFCMMYICHMLDCC-RMIBZTJPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	16051958
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0003305] Aminosaccharides [CHEMONTID:0000282] Aminoglycosides [CHEMONTID:0001675] Aminocyclitol glycosides

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 86 87 0 0 0 0 0 0 0 0999 V2000 -1.2766 -3.7891 -2.7854 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4780 -2.6748 -2.1487 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2836 -1.3929 -2.3257 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5228 -0.4173 -3.1658 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0321 0.0065 -4.1853 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3399 -0.8468 -0.9305 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1716 -1.5709 -0.2920 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4541 -2.8995 -0.7727 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9636 -1.2076 -0.9129 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0965 -0.9658 -0.1572 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4865 0.4728 -0.4618 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7484 0.8976 0.2693 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8418 -0.0500 -0.0724 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4400 -1.4915 0.2859 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2495 -1.8439 -0.5743 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9885 -3.1933 -0.3824 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5345 -2.3031 0.0146 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1195 0.2602 0.4843 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3691 0.3432 1.8767 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3690 0.3979 2.6861 N 0 0 0 0 0 0 0 0 0 0 0 0 7.6749 0.3690 2.4341 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0895 2.1581 -0.1942 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3975 1.3723 -0.0798 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4729 2.7320 -0.4199 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9786 3.0636 -1.5685 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9930 3.7635 0.4715 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5276 -1.1509 -0.2538 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0104 0.0328 0.3272 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4164 0.3577 -0.0480 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3869 -0.3771 0.8895 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1860 0.3344 2.2365 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7280 0.5161 2.5037 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3943 1.9844 2.7309 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1390 2.0693 3.3376 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8594 -0.1497 1.7060 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8784 -0.2966 3.2435 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6772 -0.0743 0.4615 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7753 0.1553 -1.4062 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0560 1.0539 -2.2692 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5257 -1.6662 -2.8882 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6116 0.0075 -0.1905 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0044 0.3810 -0.0060 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.2900 1.0359 1.3249 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3957 1.3083 -1.1328 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9175 -1.0385 -0.1627 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6598 -3.4140 -3.7722 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1699 -3.9589 -2.1469 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6901 -4.7211 -2.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5275 -2.6016 -2.5961 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4665 -0.0675 -2.9091 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1483 0.2626 -0.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1888 -1.5907 0.8044 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9134 -1.1152 0.9095 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6859 0.5322 -1.5469 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4758 0.9017 1.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9337 -0.0613 -1.1885 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1884 -1.4762 1.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5063 -1.6096 -1.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2350 -3.3400 0.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2962 -3.2318 0.2276 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9629 0.4474 -0.1355 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4773 0.4601 3.7219 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2571 1.2145 2.3436 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0583 -0.4641 2.9394 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6721 2.6200 0.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5987 1.0058 0.4454 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3371 2.4074 -2.2683 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5534 4.6432 0.5141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1296 3.5717 1.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3600 0.8917 0.0788 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6495 1.4542 0.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1732 -1.4439 0.9463 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6646 1.3464 2.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5684 0.0626 3.5512 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1326 2.3590 3.4795 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4779 2.6104 1.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1973 1.9537 4.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4740 0.3180 3.7219 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3527 -0.7233 0.7752 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8464 -0.8136 -1.7180 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9917 0.6451 -3.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6487 2.0037 -2.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1001 1.2879 -1.8035 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4749 -1.3886 -3.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8351 -0.9122 0.0788 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8391 -0.7820 0.0883 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 3 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 0 13 18 1 0 18 19 1 0 19 20 2 3 19 21 1 0 12 22 1 0 11 23 1 0 23 24 1 0 24 25 2 3 24 26 1 0 6 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 38 39 1 0 3 40 1 6 41 42 1 0 42 43 2 0 42 44 2 0 42 45 1 0 8 2 1 0 15 10 1 0 35 28 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 6 4 50 1 0 6 51 1 6 7 52 1 1 10 53 1 1 11 54 1 6 12 55 1 1 13 56 1 6 14 57 1 1 15 58 1 6 16 59 1 0 17 60 1 0 18 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 23 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 28 70 1 6 29 71 1 1 30 72 1 1 31 73 1 6 32 74 1 1 33 75 1 0 33 76 1 0 34 77 1 0 36 78 1 0 37 79 1 0 38 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 40 84 1 0 41 85 1 0 45 86 1 0 M END

Standard InCHIKey	CFCMMYICHMLDCC-RMIBZTJPSA-N
Standard InCHI	InChI=1S/C21H39N7O12.H2O4S/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35;1-5(2,3)4/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28);(H2,1,2,3,4)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;/m0./s1
SMILES	C[C@H]1[C@](C=O)([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)NC(=N)N)O)NC(=N)N)O[C@H]1[C@H]([C@@H]([C@H]([C@H](CO)O1)O)O)NC)O.OS(=O)(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	581.27	Volume:	520.653 ? Van der Waals volume.
Dense:	1.116	LogP:	-2.133 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.942 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.443 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	20.0
TPSA:	331.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	16.0	Rings:	3.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.068	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.73	Fsp³:	0.857
MCE-18:	77.538 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.191	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.103 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.047	Promiscuous compounds:	0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.138	MDCK Permeability:	-5.235
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
PAMPA:	1.0 ? 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):	1.0
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.0
Plasma Protein Binding (PPB):	16.98%	Volume Distribution (VD):	-0.687
Fu:	69.372% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.422
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

0.38

Half-life (T1/2):

2.819

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.099
Human Hepatotoxicity (H-HT):	0.639	Drug-induced Liver Injury (DILI):	0.56
AMES Toxicity:	0.804	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.028	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.957
Hematotoxicity:	0.252	Drug-induced Nephrotoxicity:	0.981
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.162
A549 Cytotoxicity:	0.098	Hek293 Cytotoxicity:	0.119
BCF:	0.018 ? 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:	2.313 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.2 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.143 ? 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
NPO3487	Croton sonderianus	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[1812213]
NPO5910	Phoma medicaginis	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795903]
NPO40010	Alectoria sarmentosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964789]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358636]
NPO3487	Croton sonderianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5910	Phoma medicaginis	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3487	Croton sonderianus	Species	Euphorbiaceae	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	8
IZ	37
MIC	72
Activity	5
IC50	2

Activity Type	# Activity
Individual protein	4
Organism	116
Single protein	1
Others	1
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[10841789]
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	109.18	%	PMID[23571415]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	87.18	%	PMID[23571415]
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	6.993	%	DOI[10.6019/CHEMBL4495564]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT871	Organism	Salmonella enterica subsp. enterica serovar Gallinarum	Salmonella enterica subsp. enterica serovar Gallinarum	MIC	=	50.0	ug.mL-1	PMID[9784149]
NPT871	Organism	Salmonella enterica subsp. enterica serovar Gallinarum	Salmonella enterica subsp. enterica serovar Gallinarum	MIC	=	50.0	ug.mL-1	PMID[7381508]
NPT871	Organism	Salmonella enterica subsp. enterica serovar Gallinarum	Salmonella enterica subsp. enterica serovar Gallinarum	MIC	=	50.0	ug.mL-1	DOI[10.1021/np50046a022]
NPT871	Organism	Salmonella enterica subsp. enterica serovar Gallinarum	Salmonella enterica subsp. enterica serovar Gallinarum	Activity	=	50.0	ug ml-1	PMID[7964789]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	4.0	mm	PMID[15787461]
NPT871	Organism	Salmonella enterica subsp. enterica serovar Gallinarum	Salmonella enterica subsp. enterica serovar Gallinarum	MIC	=	3.12	ug.mL-1	PMID[16562847]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	=	7.5	ug.mL-1	PMID[25237727]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	=	5.0	ug.mL-1	PMID[25237727]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	28.67	mm	PMID[25978960]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	6.25	ug.mL-1	PMID[25978960]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-5.98	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.09	%	DOI[10.6019/CHEMBL4495565]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[16298529]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	DOI[10.1021/np50067a002]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	>	12.0	mm	PMID[1812213]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	7.0	mm	PMID[1812213]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	1.56	ug.mL-1	PMID[9784149]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	1.56	ug.mL-1	PMID[9784149]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[9784149]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	2.5	ug.mL-1	PMID[7381508]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	1.25	ug.mL-1	PMID[7381508]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	16.0	mm	DOI[10.1021/np50037a043]
NPT4789	Organism	Escherichia coli B	Escherichia coli B	IZ	=	17.0	mm	DOI[10.1021/np50037a043]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	1.25	ug.mL-1	DOI[10.1021/np50046a022]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	2.5	ug.mL-1	DOI[10.1021/np50046a022]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	2.5	ug ml-1	PMID[7964789]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	Activity	=	1.25	ug ml-1	PMID[7964789]
NPT2642	Organism	Bacillus pumilus	Bacillus pumilus	MIC	=	0.94	ug.mL-1	PMID[8450316]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.75	ug.mL-1	PMID[8450316]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	13.0	mm	PMID[8496706]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[8496706]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	3.12	ug.mL-1	PMID[16562847]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	12.5	ug.mL-1	PMID[16562847]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	DOI[10.1007/s00044-010-9462-7]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	2.2	mm	DOI[10.1007/s00044-010-9462-7]
NPT4585	Organism	Mycobacterium diernhoferi	Mycobacterium diernhoferi	MIC	<	0.52	ug.mL-1	PMID[24460410]
NPT610	Others	Molecular identity unknown	n.a.	MIC	=	0.1	ug.mL-1	PMID[24460410]
NPT4584	Organism	Nocardia sp.	Nocardia sp.	MIC	<	0.52	ug.mL-1	PMID[24460410]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	MIC	=	64.0	ug.mL-1	PMID[24856180]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	=	5.0	ug.mL-1	PMID[25237727]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	5.0	ug.mL-1	PMID[25237727]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	MIC	=	2140.0	nM	PMID[25791454]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	27.33	mm	PMID[25978960]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	28.67	mm	PMID[25978960]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	6.25	ug.mL-1	PMID[25978960]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	6.25	ug.mL-1	PMID[25978960]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	=	30.0	mm	PMID[26083682]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	4.5	ug.mL-1	PMID[25981688]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	5.0	ug.mL-1	PMID[25981688]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.0	ug.mL-1	PMID[31306907]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	14.0	mm	PMID[16298529]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.3	ug.mL-1	DOI[10.1021/np50067a002]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	3.0	mm	PMID[1812213]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	7.0	mm	PMID[1812213]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7.0	mm	PMID[1812213]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	7.0	mm	PMID[1812213]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[9784149]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	6.25	ug.mL-1	PMID[9784149]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[9784149]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	PMID[7381508]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug.mL-1	PMID[7381508]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	DOI[10.1021/np50046a022]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug.mL-1	DOI[10.1021/np50046a022]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	5.0	ug ml-1	PMID[7964789]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	5.0	ug ml-1	PMID[7964789]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	3.0	mm	PMID[9358636]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	15.0	ug.mL-1	PMID[8450316]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.75	ug.mL-1	PMID[8450316]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	9.0	mm	PMID[8496706]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[8496706]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	16.0	mm	PMID[18234501]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	14.0	mm	PMID[18234501]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	4.0	mm	PMID[15787461]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IZ	=	4.0	mm	PMID[15787461]
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	4.0	mm	PMID[15787461]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	6.25	ug.mL-1	PMID[16562847]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[16562847]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	1.56	ug.mL-1	PMID[16562847]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	16.0	ug.mL-1	PMID[20053565]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	5.0	ug.mL-1	PMID[19795903]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1.56	ug.mL-1	DOI[10.1007/s00044-010-9462-7]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	3.13	ug.mL-1	DOI[10.1007/s00044-010-9462-7]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	DOI[10.1007/s00044-010-9462-7]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	5.3	mm	DOI[10.1007/s00044-010-9462-7]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	IZ	=	4.6	mm	DOI[10.1007/s00044-010-9462-7]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	2.8	mm	DOI[10.1007/s00044-010-9462-7]
NPT2631	Organism	Chromobacterium violaceum	Chromobacterium violaceum	MIC	=	2.1	ug.mL-1	PMID[24460410]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[24856180]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	=	64.0	ug.mL-1	PMID[24856180]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[24856180]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	64.0	ug.mL-1	PMID[24856180]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	=	10.0	ug.mL-1	PMID[25237727]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1070.0	nM	PMID[25791454]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2140.0	nM	PMID[25791454]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	1070.0	nM	PMID[25791454]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	6.25	ug.mL-1	PMID[25978960]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	30.33	mm	PMID[25978960]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	8.5	ug.mL-1	PMID[25981688]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	10.0	ug.mL-1	PMID[25981688]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[31306907]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[31306907]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	16.0	ug.mL-1	PMID[31306907]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	4.0	ug.mL-1	PMID[31306907]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	16.0	ug.mL-1	PMID[31306907]
NPT1209	Organism	Pseudomonas fluorescens	Pseudomonas fluorescens	IZ	=	18.0	mm	PMID[16298529]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	5.0	mm	PMID[9358636]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	4.0	mm	PMID[15787461]
NPT1232	Organism	Eurotium repens	Eurotium repens	IZ	=	4.0	mm	PMID[15787461]
NPT1233	Organism	Mycotypha microspora	Mycotypha microspora	IZ	=	4.0	mm	PMID[15787461]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	16.0	ug.mL-1	PMID[20053565]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	8.0	ug.mL-1	PMID[20053565]
NPT6293	Organism	Mycobacterium sp.	Mycobacterium sp.	MIC	=	2.1	ug.mL-1	PMID[24460410]
NPT3598	Organism	Bacillus	Bacillus	MIC	=	64.0	ug.mL-1	PMID[24856180]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	5.0	ug.mL-1	PMID[25237727]

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 NPC478664 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	31812
0.1-0.2	17929
0.2-0.3	111
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC487063
1.0	High Similarity	NPC489233
0.9385	High Similarity	NPC478574
0.9385	High Similarity	NPC94319
0.8429	Intermediate Similarity	NPC121479
0.7714	Intermediate Similarity	NPC57436

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7163
0.1-0.2	1956
0.2-0.3	26
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4826	Approved
0.9385	High Similarity	NPD4827	Approved
0.9385	High Similarity	NPD4828	Phase 4
0.8429	Intermediate Similarity	NPD35	Approved
0.7714	Intermediate Similarity	NPD4833	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