NPASS Compound

Structure

CID178919 OpenBabel06191715552D 46 46 0 0 1 0 0 0 0 0999 V2000 3.2964 -0.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3293 0.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0024 1.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5349 -6.6172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1625 -6.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0133 -3.8191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3141 -2.1133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1668 2.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4608 1.6133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6276 -5.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3008 -6.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6124 -2.2981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 -5.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1777 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 -2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3116 -0.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1777 -5.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6713 -2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5240 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -5.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 -1.5321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7017 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8356 -4.9115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9848 -1.7057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6865 -2.7057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -4.4115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3445 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 0.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -5.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7017 -4.4115 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 -2.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -4.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 1.6736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 -4.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -0.2660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -6.0851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 -0.2660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6865 -1.7057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.9115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 21 1 0 0 0 0 13 35 1 0 0 0 0 14 36 1 0 0 0 0 15 37 1 0 0 0 0 16 22 1 0 0 0 0 22 12 1 6 0 0 0 23 17 1 6 0 0 0 23 32 1 0 0 0 0 23 36 1 0 0 0 0 24 18 1 6 0 0 0 24 33 1 0 0 0 0 24 35 1 0 0 0 0 25 22 1 6 0 0 0 25 34 1 0 0 0 0 25 37 1 0 0 0 0 26 19 1 1 0 0 0 26 29 1 0 0 0 0 26 44 1 0 0 0 0 27 20 1 1 0 0 0 27 30 1 0 0 0 0 27 46 1 0 0 0 0 28 21 1 1 0 0 0 28 31 1 0 0 0 0 28 45 1 0 0 0 0 29 35 1 0 0 0 0 29 38 2 0 0 0 0 30 36 1 0 0 0 0 30 39 2 0 0 0 0 31 37 1 0 0 0 0 31 40 2 0 0 0 0 32 41 2 0 0 0 0 32 44 1 0 0 0 0 33 42 2 0 0 0 0 33 45 1 0 0 0 0 34 43 2 0 0 0 0 34 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	653.43
Volume:	684.347
LogP:	4.049
LogD:	2.223
LogS:	-3.698
# Rotatable Bonds:	7
TPSA:	139.83
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	5.199
Fsp3:	0.824
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.18
MDCK Permeability:	3.790035771089606e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.908
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.396

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	90.32715606689453%
Volume Distribution (VD):	1.26
Pgp-substrate:	3.017411470413208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	5.968
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.018
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.012

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC178919

Natural Product ID:	NPC178919
*Common Name:**	Enniatin B1
IUPAC Name:	(3S,6R,9S,12R,15S,18R)-3-[(2S)-butan-2-yl]-4,10,16-trimethyl-6,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms:	Enniatin B1
Standard InCHIKey:	UQCSETXJXJTMKO-UMURLBKASA-N
Standard InCHI:	InChI=1S/C34H59N3O9/c1-16-22(12)25-34(43)46-27(20(8)9)30(39)36(14)23(17(2)3)32(41)44-26(19(6)7)29(38)35(13)24(18(4)5)33(42)45-28(21(10)11)31(40)37(25)15/h17-28H,16H2,1-15H3/t22-,23-,24-,25-,26+,27+,28+/m0/s1
SMILES:	CC[C@@H]([C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446318
PubChem CID:	11262300
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO40136	Fusarium sp. F31	Strain	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165149]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562855]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17286429]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090694]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175613]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO41427	Fusarium tricinctum + Streptomyces lividans/Bacillus subtilis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[35518011]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014349]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	0totodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2408	Millettia laurentii	Species	Fabaceae	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	NP ID	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	3
MIC	10
Others	1

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	75.0	ug.mL-1	PMID[538415]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Activity	=	25.0	ug ml-1	PMID[538415]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	2.0	ug.mL-1	PMID[538416]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	6.25	ug.mL-1	PMID[538416]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	9.0	ug.mL-1	PMID[538416]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	25.0	ug.mL-1	PMID[538416]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	15.0	ug.mL-1	PMID[538416]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64.0	ug.mL-1	PMID[538417]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[538417]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	8.0	ug.mL-1	PMID[538417]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	4.0	ug.mL-1	PMID[538417]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[538417]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	MIC	=	16.0	ug.mL-1	PMID[538417]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC178919 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	16035
0.2-0.3	19575
0.3-0.4	5656
0.4-0.5	818
0.5-0.6	231
0.6-0.7	52
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC263281
0.9437	High Similarity	NPC477145
0.9437	High Similarity	NPC473741
0.9403	High Similarity	NPC212866
0.9403	High Similarity	NPC29598
0.9254	High Similarity	NPC10716
0.7975	Intermediate Similarity	NPC246005
0.7471	Intermediate Similarity	NPC62263
0.7471	Intermediate Similarity	NPC471098
0.7471	Intermediate Similarity	NPC173763
0.7363	Intermediate Similarity	NPC220234
0.7356	Intermediate Similarity	NPC476019
0.7356	Intermediate Similarity	NPC474576
0.7241	Intermediate Similarity	NPC474593
0.7241	Intermediate Similarity	NPC475801
0.7128	Intermediate Similarity	NPC124554
0.7128	Intermediate Similarity	NPC301148
0.7128	Intermediate Similarity	NPC5864
0.6989	Remote Similarity	NPC475440
0.6979	Remote Similarity	NPC124549
0.6979	Remote Similarity	NPC323720
0.6875	Remote Similarity	NPC198344
0.6771	Remote Similarity	NPC475149
0.6771	Remote Similarity	NPC471097
0.6768	Remote Similarity	NPC171734
0.6768	Remote Similarity	NPC67009
0.6742	Remote Similarity	NPC322966
0.6735	Remote Similarity	NPC475637
0.6706	Remote Similarity	NPC84128
0.6706	Remote Similarity	NPC53858
0.6562	Remote Similarity	NPC13175
0.6562	Remote Similarity	NPC475791
0.6458	Remote Similarity	NPC475758
0.642	Remote Similarity	NPC141325
0.6375	Remote Similarity	NPC478256
0.6344	Remote Similarity	NPC315237
0.6341	Remote Similarity	NPC138435
0.625	Remote Similarity	NPC473597
0.6237	Remote Similarity	NPC477538
0.619	Remote Similarity	NPC476130
0.619	Remote Similarity	NPC476324
0.6173	Remote Similarity	NPC476291
0.6092	Remote Similarity	NPC476137
0.6092	Remote Similarity	NPC476156
0.6092	Remote Similarity	NPC476117
0.6092	Remote Similarity	NPC476243
0.6076	Remote Similarity	NPC326651
0.6076	Remote Similarity	NPC325117
0.6076	Remote Similarity	NPC322319
0.6071	Remote Similarity	NPC86064
0.6071	Remote Similarity	NPC327272
0.6049	Remote Similarity	NPC193280
0.6049	Remote Similarity	NPC314273
0.6023	Remote Similarity	NPC476302
0.6	Remote Similarity	NPC188785
0.5977	Remote Similarity	NPC31756
0.5976	Remote Similarity	NPC476285
0.5972	Remote Similarity	NPC325180
0.5972	Remote Similarity	NPC35816
0.5952	Remote Similarity	NPC43219
0.5952	Remote Similarity	NPC476248
0.5926	Remote Similarity	NPC472536
0.5926	Remote Similarity	NPC103391
0.5893	Remote Similarity	NPC477238
0.5862	Remote Similarity	NPC233108
0.5833	Remote Similarity	NPC63191
0.5833	Remote Similarity	NPC471202
0.5824	Remote Similarity	NPC95478
0.5824	Remote Similarity	NPC145748
0.5824	Remote Similarity	NPC155670
0.5824	Remote Similarity	NPC472351
0.5765	Remote Similarity	NPC208657
0.5761	Remote Similarity	NPC227051
0.5747	Remote Similarity	NPC472594
0.5714	Remote Similarity	NPC477237
0.5714	Remote Similarity	NPC235078
0.5667	Remote Similarity	NPC23984
0.5667	Remote Similarity	NPC470783
0.5663	Remote Similarity	NPC224700
0.5663	Remote Similarity	NPC322274
0.5663	Remote Similarity	NPC320663
0.563	Remote Similarity	NPC152850
0.563	Remote Similarity	NPC89923
0.563	Remote Similarity	NPC71933
0.563	Remote Similarity	NPC239990
0.563	Remote Similarity	NPC105114
0.5625	Remote Similarity	NPC477729
0.56	Remote Similarity	NPC47076
0.56	Remote Similarity	NPC134504

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC178919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	3497
0.2-0.3	3982
0.3-0.4	1101
0.4-0.5	319
0.5-0.6	79
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9403	High Similarity	NPD7840	Approved
0.6429	Remote Similarity	NPD8144	Approved
0.6429	Remote Similarity	NPD8143	Approved
0.6375	Remote Similarity	NPD2697	Approved
0.6375	Remote Similarity	NPD2695	Approved
0.6375	Remote Similarity	NPD2696	Approved
0.6375	Remote Similarity	NPD2694	Approved
0.622	Remote Similarity	NPD6704	Discontinued
0.6186	Remote Similarity	NPD3713	Approved
0.6186	Remote Similarity	NPD3714	Approved
0.6186	Remote Similarity	NPD3715	Approved
0.6164	Remote Similarity	NPD4281	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7759	Phase 2
0.6044	Remote Similarity	NPD7760	Phase 2
0.5976	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD9660	Approved
0.5859	Remote Similarity	NPD8038	Phase 2
0.5854	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7763	Phase 2
0.5843	Remote Similarity	NPD7762	Phase 2
0.5814	Remote Similarity	NPD1452	Discontinued
0.5784	Remote Similarity	NPD8301	Approved
0.5784	Remote Similarity	NPD8300	Approved
0.5783	Remote Similarity	NPD3726	Approved
0.5783	Remote Similarity	NPD3725	Approved
0.5783	Remote Similarity	NPD9649	Approved
0.5753	Remote Similarity	NPD9202	Approved
0.575	Remote Similarity	NPD9648	Approved
0.5747	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD9659	Approved
0.5729	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7535	Discontinued
0.5714	Remote Similarity	NPD1458	Approved
0.5714	Remote Similarity	NPD1459	Approved
0.5672	Remote Similarity	NPD9456	Approved
0.5672	Remote Similarity	NPD9457	Approved
0.5663	Remote Similarity	NPD8278	Approved
0.5657	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD11	Approved
0.5632	Remote Similarity	NPD376	Approved
0.5632	Remote Similarity	NPD1453	Phase 1
0.5616	Remote Similarity	NPD2693	Approved
0.5616	Remote Similarity	NPD2692	Approved
0.5616	Remote Similarity	NPD9203	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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