NPASS Compound

Structure

CID107919 OpenBabel06191715452D 24 27 0 0 1 0 0 0 0 0999 V2000 3.0035 -0.3314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0251 0.9597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 -1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 -0.9742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 0.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4612 0.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6176 -1.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4871 -0.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4761 0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9224 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4613 -0.8436 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6873 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5309 1.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5309 0.4871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8436 0.4871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9483 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9486 1.3056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4469 -0.8209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3494 1.9338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4276 -0.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 4 1 0 0 0 0 3 13 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 19 1 1 0 0 0 14 20 1 1 0 0 0 15 17 1 6 0 0 0 15 18 1 0 0 0 0 16 17 1 1 0 0 0 16 23 1 0 0 0 0 17 1 1 6 0 0 0 18 19 1 1 0 0 0 19 7 1 1 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	355.411
LogP:	1.818
LogD:	1.902
LogS:	-3.599
# Rotatable Bonds:	2
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	5.921
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.31
MDCK Permeability:	7.1631093305768445e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.097
Human Intestinal Absorption (HIA):	0.078
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.456
Plasma Protein Binding (PPB):	79.69457244873047%
Volume Distribution (VD):	0.927
Pgp-substrate:	8.32837200164795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.274
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	4.265
Half-life (T1/2):	0.737

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.526
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.547
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.935
Carcinogencity:	0.051
Eye Corrosion:	0.2
Eye Irritation:	0.908
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC107919

Natural Product ID:	NPC107919
*Common Name:**	Aphidicolin
IUPAC Name:	n.a.
Synonyms:	Aphidicolin
Standard InCHIKey:	NOFOAYPPHIUXJR-APNQCZIXSA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
SMILES:	OC[C@@]1(O)CC[C@]23C[C@H]1C[C@@H]2CC[C@@H]1[C@]3(C)CC[C@H]([C@@]1(C)CO)O
Synthetic Gene Cluster:	BGC0000676;
ChEMBL Identifier:	CHEMBL29711
PubChem CID:	457964
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002931] Aphidicolane and stemodane diterpenoids

*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
NPO40656	Rhizopus arrhizus ATCC 11145 + Streptomyces sp. NRRL 5691	Species Co-culture	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1667410]
NPO30964	Cephalosporium aphidicola	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[21812410]
NPO23794	Tolypocladium inflatum	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21812410]
NPO40710	Pyrenula sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24926891]
NPO40144	Garcinia schomburgkiana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27409517]
NPO40466	Botryotinia fuckeliana MCCC 3A00494	Strain	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31403790]
NPO23794	Tolypocladium inflatum	Species	Ophiocordycipitaceae	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
EC50	9
ED50	1
IC50	43
LD50	1
MIC	1
Others	27
Potency	18

Activity Type	# Activity
Cell Line	17
CELL-LINE	1
Individual Protein	32
NON-MOLECULAR	1
Organism	19
Others	27
SINGLE PROTEIN	1
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4228	Individual Protein	Human herpesvirus 6 DNA polymerase	Human herpesvirus 6A (strain Uganda-1102) (HHV-6 variant A) (Human Blymphotropic virus)	IC50	=	400.0	nM	PMID[520685]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	IC50	=	3000.0	nM	PMID[520685]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	84.0	%	PMID[520686]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	0.0	%	PMID[520686]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	EC50	=	2000.0	nM	PMID[520688]
NPT4229	Individual Protein	Human herpesvirus 5 DNA polymerase	Human cytomegalovirus (strain AD169) (HHV-5) (Human herpesvirus 5)	IC50	=	400.0	nM	PMID[520689]
NPT4230	Individual Protein	Human herpesvirus 1 DNA polymerase	Herpes simplex virus (type 1 / strain 17)	IC50	=	500.0	nM	PMID[520689]
NPT4231	Individual Protein	DNA polymerase	Varicella-zoster virus (strain Dumas) (HHV-3) (Human herpesvirus 3)	IC50	=	600.0	nM	PMID[520689]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	IC50	=	2600.0	nM	PMID[520689]
NPT4231	Individual Protein	DNA polymerase	Varicella-zoster virus (strain Dumas) (HHV-3) (Human herpesvirus 3)	IC50	=	2600.0	nM	PMID[520689]
NPT4232	Individual Protein	DNA polymerase delta subunit 1	Homo sapiens	IC50	>	40000.0	nM	PMID[520689]
NPT4229	Individual Protein	Human herpesvirus 5 DNA polymerase	Human cytomegalovirus (strain AD169) (HHV-5) (Human herpesvirus 5)	IC50	=	487.0	nM	PMID[520691]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	73.06	%	PMID[520692]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	216.53	%	PMID[520692]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	275.5	%	PMID[520692]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	350.13	%	PMID[520692]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	200.0	ug.mL-1	PMID[520693]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.13	ug ml-1	PMID[520694]
NPT4233	Individual Protein	DNA polymerase catalytic subunit	Human herpesvirus 1 (strain KOS) (HHV-1) (Human herpes simplex virus1)	IC50	=	438.0	nM	PMID[520695]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	IC50	=	2600.0	nM	PMID[520697]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	580.0	nM	PMID[520699]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	794.3	nM	PMID[520700]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	5623.4	nM	PMID[520700]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	>	150000.0	nM	PMID[520700]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	1995.3	nM	PMID[520700]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	=	38639.0	nM	PMID[520700]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	=	28620.0	nM	PMID[520700]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	631.0	nM	PMID[520700]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	IC50	=	16000.0	nM	PMID[520702]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	IC50	>	100000.0	nM	PMID[520702]
NPT4234	Individual Protein	DNA polymerase gamma subunit 1	Homo sapiens	IC50	>	100000.0	nM	PMID[520702]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[520701]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	730.8	nM	PMID[520700]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	8.45	%	PMID[520703]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CD50	=	20.0	ug ml-1	PMID[520704]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Activity	=	0.01	mg/ml	PMID[520705]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	131.0	nM	PMID[520701]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	104.1	nM	PMID[520701]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[520701]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	>	100000.0	nM	PMID[520708]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	9000.0	nM	PMID[520708]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	IC50	>	200000.0	nM	PMID[520710]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	IC50	=	2400.0	nM	PMID[520712]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	24400.0	nM	PMID[520715]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	IC50	=	4300.0	nM	PMID[520716]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Reduction	=	100.0	%	PMID[520684]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MAC	=	0.005	ug ml-1	PMID[520684]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MAC	=	0.02	uM	PMID[520684]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	0.2	ug.mL-1	PMID[520684]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	590.0	nM	PMID[520684]
NPT317	Uncleic Acid	Nucleic Acid		Inhibition	=	50.0	%	PMID[520687]
NPT317	Uncleic Acid	Nucleic Acid		EC50	=	5000.0	nM	PMID[520688]
NPT2	Others	Unspecified		IC50	=	400.0	nM	PMID[520690]
NPT2	Others	Unspecified		IC50	=	500.0	nM	PMID[520690]
NPT2	Others	Unspecified		IC50	=	600.0	nM	PMID[520690]
NPT2	Others	Unspecified		IC50	=	2600.0	nM	PMID[520690]
NPT2	Others	Unspecified		IC50	=	438.0	nM	PMID[520691]
NPT2	Others	Unspecified		IC50	=	473.0	nM	PMID[520691]
NPT2	Others	Unspecified		IC50	=	2600.0	nM	PMID[520691]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	100.0	%	PMID[520693]
NPT2	Others	Unspecified		IC50	=	2600.0	nM	PMID[520695]
NPT2	Others	Unspecified		IC50	=	473.0	nM	PMID[520695]
NPT2	Others	Unspecified		IC50	=	487.0	nM	PMID[520695]
NPT2	Others	Unspecified		IC50	=	487.0	nM	PMID[520696]
NPT2	Others	Unspecified		IC50	=	473.0	nM	PMID[520696]
NPT2	Others	Unspecified		IC50	=	487.0	nM	PMID[520697]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	438.0	nM	PMID[520697]
NPT2	Others	Unspecified		IC50	=	473.0	nM	PMID[520697]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	100.0	%	PMID[520699]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MAC	=	0.02	uM/L	PMID[520699]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	794.3	nM	PMID[520701]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	2238.7	nM	PMID[520700]
NPT2	Others	Unspecified		EC50	=	1731.0	nM	PMID[520700]
NPT2	Others	Unspecified		EC50	=	839.0	nM	PMID[520700]
NPT2	Others	Unspecified		Potency	=	206.0	nM	PMID[520700]
NPT2	Others	Unspecified		EC50	>	150000.0	nM	PMID[520700]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	585.8	nM	PMID[520700]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	522.1	nM	PMID[520700]
NPT2	Others	Unspecified		Potency	n.a.	517.4	nM	PMID[520700]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	13.47	%	PMID[520703]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	100.0	%	PMID[520704]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	=	5.0	ug.mL-1	PMID[520704]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MAC	=	0.005	mg/ml	PMID[520705]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Activity	=	100.0	%	PMID[520705]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[520701]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[520701]
NPT2	Others	Unspecified		IC50	=	7170.0	nM	PMID[520707]
NPT2	Others	Unspecified		IC50	=	1960.0	nM	PMID[520707]
NPT2	Others	Unspecified		IC50	=	19600.0	nM	PMID[520708]
NPT2	Others	Unspecified		EC50	=	136.0	nM	PMID[520700]
NPT2	Others	Unspecified		IC50	=	19600.0	nM	PMID[520710]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LD50	=	22.0	uM	PMID[520710]
NPT2	Others	Unspecified		IC50	=	7300.0	nM	PMID[520711]
NPT22036	CELL-LINE	HL	Homo sapiens	Activity	=	92.3	%	PMID[520713]
NPT5310	Organism	Chlamydophila pneumoniae	Chlamydophila pneumoniae	Inhibition	=	-3.8	%	PMID[520713]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	23.34	%	PMID[520714]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	10.95	%	PMID[520717]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.18	%	PMID[520718]

☑ 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 NPC107919 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	370
0.1-0.2	4158
0.2-0.3	15832
0.3-0.4	9755
0.4-0.5	4775
0.5-0.6	4538
0.6-0.7	2444
0.7-0.8	627
0.8-0.85	89
0.85-0.9	70
0.9-0.95	37
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC470830
0.9394	High Similarity	NPC299948
0.9394	High Similarity	NPC241085
0.9275	High Similarity	NPC243027
0.9275	High Similarity	NPC158208
0.9275	High Similarity	NPC196136
0.9275	High Similarity	NPC317242
0.9265	High Similarity	NPC153719
0.9254	High Similarity	NPC231945
0.9143	High Similarity	NPC163597
0.913	High Similarity	NPC192501
0.913	High Similarity	NPC228994
0.913	High Similarity	NPC10476
0.9118	High Similarity	NPC157777
0.9118	High Similarity	NPC131506
0.9104	High Similarity	NPC66407
0.9091	High Similarity	NPC473230
0.9091	High Similarity	NPC48079
0.9091	High Similarity	NPC475884
0.9091	High Similarity	NPC63190
0.9077	High Similarity	NPC472946
0.9062	High Similarity	NPC114891
0.9014	High Similarity	NPC192046
0.9014	High Similarity	NPC302578
0.9014	High Similarity	NPC128951
0.9014	High Similarity	NPC105208
0.9014	High Similarity	NPC11907
0.9014	High Similarity	NPC185915
0.9014	High Similarity	NPC133596
0.9014	High Similarity	NPC477227
0.8986	High Similarity	NPC472341
0.8986	High Similarity	NPC470610
0.8986	High Similarity	NPC473238
0.8971	High Similarity	NPC192192
0.8955	High Similarity	NPC472741
0.8939	High Similarity	NPC142712
0.8906	High Similarity	NPC71460
0.8906	High Similarity	NPC148174
0.8906	High Similarity	NPC218585
0.8889	High Similarity	NPC67657
0.8889	High Similarity	NPC18857
0.8889	High Similarity	NPC147993
0.8873	High Similarity	NPC470145
0.8857	High Similarity	NPC304499
0.8857	High Similarity	NPC48795
0.8841	High Similarity	NPC157422
0.8841	High Similarity	NPC470071
0.8841	High Similarity	NPC252182
0.8841	High Similarity	NPC1340
0.8841	High Similarity	NPC100586
0.8841	High Similarity	NPC127094
0.8841	High Similarity	NPC187471
0.8841	High Similarity	NPC109457
0.8824	High Similarity	NPC99264
0.8824	High Similarity	NPC129829
0.8824	High Similarity	NPC254037
0.8824	High Similarity	NPC470833
0.8788	High Similarity	NPC473276
0.8788	High Similarity	NPC474380
0.8788	High Similarity	NPC243469
0.8788	High Similarity	NPC41577
0.8788	High Similarity	NPC260116
0.8788	High Similarity	NPC190827
0.8788	High Similarity	NPC475943
0.8767	High Similarity	NPC477282
0.8767	High Similarity	NPC287452
0.8767	High Similarity	NPC81074
0.875	High Similarity	NPC64081
0.875	High Similarity	NPC474574
0.8732	High Similarity	NPC270306
0.8732	High Similarity	NPC231680
0.8732	High Similarity	NPC91387
0.8696	High Similarity	NPC251201
0.8696	High Similarity	NPC63588
0.8696	High Similarity	NPC232925
0.8696	High Similarity	NPC282454
0.8657	High Similarity	NPC44122
0.8636	High Similarity	NPC159654
0.8636	High Similarity	NPC167995
0.8636	High Similarity	NPC118937
0.8636	High Similarity	NPC281540
0.8636	High Similarity	NPC69149
0.8611	High Similarity	NPC477602
0.8611	High Similarity	NPC91573
0.8611	High Similarity	NPC477601
0.8611	High Similarity	NPC473916
0.8592	High Similarity	NPC478130
0.8571	High Similarity	NPC473279
0.8571	High Similarity	NPC127283
0.8571	High Similarity	NPC478103
0.8571	High Similarity	NPC195530
0.8571	High Similarity	NPC8004
0.8551	High Similarity	NPC477820
0.8438	Intermediate Similarity	NPC476735
0.8421	Intermediate Similarity	NPC60018
0.8421	Intermediate Similarity	NPC154043
0.8421	Intermediate Similarity	NPC202688
0.8421	Intermediate Similarity	NPC475388
0.8406	Intermediate Similarity	NPC474756
0.8406	Intermediate Similarity	NPC475893
0.84	Intermediate Similarity	NPC16449
0.8333	Intermediate Similarity	NPC477508
0.8333	Intermediate Similarity	NPC95804
0.8333	Intermediate Similarity	NPC185547
0.8312	Intermediate Similarity	NPC478054
0.8312	Intermediate Similarity	NPC85095
0.8312	Intermediate Similarity	NPC211135
0.8312	Intermediate Similarity	NPC216420
0.8289	Intermediate Similarity	NPC12933
0.8281	Intermediate Similarity	NPC135438
0.8267	Intermediate Similarity	NPC269333
0.8261	Intermediate Similarity	NPC204233
0.8243	Intermediate Similarity	NPC171658
0.8243	Intermediate Similarity	NPC476233
0.8243	Intermediate Similarity	NPC264602
0.8235	Intermediate Similarity	NPC80463
0.8219	Intermediate Similarity	NPC3403
0.8205	Intermediate Similarity	NPC320824
0.8194	Intermediate Similarity	NPC232112
0.8182	Intermediate Similarity	NPC317066
0.8182	Intermediate Similarity	NPC30166
0.8158	Intermediate Similarity	NPC13554
0.8154	Intermediate Similarity	NPC47663
0.8133	Intermediate Similarity	NPC301707
0.8133	Intermediate Similarity	NPC31828
0.8133	Intermediate Similarity	NPC102708
0.8133	Intermediate Similarity	NPC471769
0.8108	Intermediate Similarity	NPC93662
0.8108	Intermediate Similarity	NPC4209
0.8108	Intermediate Similarity	NPC278091
0.8108	Intermediate Similarity	NPC78067
0.8101	Intermediate Similarity	NPC266651
0.8101	Intermediate Similarity	NPC290612
0.8082	Intermediate Similarity	NPC472945
0.8082	Intermediate Similarity	NPC472944
0.8082	Intermediate Similarity	NPC475458
0.8077	Intermediate Similarity	NPC470070
0.8077	Intermediate Similarity	NPC207013
0.8077	Intermediate Similarity	NPC111582
0.8077	Intermediate Similarity	NPC477285
0.8056	Intermediate Similarity	NPC111234
0.8056	Intermediate Similarity	NPC156277
0.8056	Intermediate Similarity	NPC320549
0.8056	Intermediate Similarity	NPC151018
0.8056	Intermediate Similarity	NPC58057
0.8052	Intermediate Similarity	NPC190940
0.803	Intermediate Similarity	NPC95958
0.8026	Intermediate Similarity	NPC220379
0.8	Intermediate Similarity	NPC475172
0.8	Intermediate Similarity	NPC236588
0.8	Intermediate Similarity	NPC23884
0.8	Intermediate Similarity	NPC317913
0.8	Intermediate Similarity	NPC155531
0.8	Intermediate Similarity	NPC215968
0.8	Intermediate Similarity	NPC212453
0.8	Intermediate Similarity	NPC207010
0.8	Intermediate Similarity	NPC475031
0.8	Intermediate Similarity	NPC121981
0.7975	Intermediate Similarity	NPC255882
0.7973	Intermediate Similarity	NPC195155
0.7973	Intermediate Similarity	NPC185536
0.7973	Intermediate Similarity	NPC472952
0.7973	Intermediate Similarity	NPC104387
0.7973	Intermediate Similarity	NPC212879
0.7973	Intermediate Similarity	NPC231256
0.7973	Intermediate Similarity	NPC230704
0.7973	Intermediate Similarity	NPC174964
0.7973	Intermediate Similarity	NPC97534
0.7973	Intermediate Similarity	NPC139765
0.7973	Intermediate Similarity	NPC273366
0.7973	Intermediate Similarity	NPC472950
0.7973	Intermediate Similarity	NPC240235
0.7973	Intermediate Similarity	NPC70982
0.7973	Intermediate Similarity	NPC178383
0.7973	Intermediate Similarity	NPC212733
0.7973	Intermediate Similarity	NPC131584
0.7971	Intermediate Similarity	NPC477603
0.7949	Intermediate Similarity	NPC286719
0.7949	Intermediate Similarity	NPC121121
0.7949	Intermediate Similarity	NPC477286
0.7949	Intermediate Similarity	NPC477599
0.7945	Intermediate Similarity	NPC253805
0.7941	Intermediate Similarity	NPC209686
0.7941	Intermediate Similarity	NPC292419
0.7941	Intermediate Similarity	NPC249078
0.7941	Intermediate Similarity	NPC290791
0.7941	Intermediate Similarity	NPC236099
0.7922	Intermediate Similarity	NPC102253
0.7922	Intermediate Similarity	NPC322313
0.7922	Intermediate Similarity	NPC470609
0.7922	Intermediate Similarity	NPC22403
0.7922	Intermediate Similarity	NPC236237
0.7917	Intermediate Similarity	NPC45296
0.7901	Intermediate Similarity	NPC210658
0.7901	Intermediate Similarity	NPC477600
0.7901	Intermediate Similarity	NPC263802
0.7901	Intermediate Similarity	NPC43912
0.7901	Intermediate Similarity	NPC140446
0.7901	Intermediate Similarity	NPC161928
0.7901	Intermediate Similarity	NPC202937

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 NPC107919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	4213
0.2-0.3	3206
0.3-0.4	792
0.4-0.5	235
0.5-0.6	195
0.6-0.7	98
0.7-0.8	17
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4267	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD4787	Phase 1
0.8108	Intermediate Similarity	NPD6117	Approved
0.8056	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6116	Phase 1
0.7922	Intermediate Similarity	NPD7525	Registered
0.7895	Intermediate Similarity	NPD6697	Approved
0.7895	Intermediate Similarity	NPD6118	Approved
0.7895	Intermediate Similarity	NPD6115	Approved
0.7895	Intermediate Similarity	NPD6114	Approved
0.7838	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5360	Phase 3
0.75	Intermediate Similarity	NPD3703	Phase 2
0.7432	Intermediate Similarity	NPD4244	Approved
0.7432	Intermediate Similarity	NPD4245	Approved
0.7432	Intermediate Similarity	NPD4789	Approved
0.7297	Intermediate Similarity	NPD3698	Phase 2
0.725	Intermediate Similarity	NPD6928	Phase 2
0.7222	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4758	Discontinued
0.7051	Intermediate Similarity	NPD7339	Approved
0.7051	Intermediate Similarity	NPD6942	Approved
0.7045	Intermediate Similarity	NPD8171	Discontinued
0.7024	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5364	Discontinued
0.7	Intermediate Similarity	NPD3671	Phase 1
0.6962	Remote Similarity	NPD6933	Approved
0.6933	Remote Similarity	NPD6705	Phase 1
0.6914	Remote Similarity	NPD7645	Phase 2
0.6883	Remote Similarity	NPD6081	Approved
0.6849	Remote Similarity	NPD371	Approved
0.6829	Remote Similarity	NPD4748	Discontinued
0.6818	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6700	Approved
0.675	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6703	Approved
0.6742	Remote Similarity	NPD6702	Approved
0.6719	Remote Similarity	NPD385	Approved
0.6719	Remote Similarity	NPD384	Approved
0.6709	Remote Similarity	NPD6924	Approved
0.6709	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD4224	Phase 2
0.6625	Remote Similarity	NPD3702	Approved
0.6588	Remote Similarity	NPD4788	Approved
0.6556	Remote Similarity	NPD8034	Phase 2
0.6556	Remote Similarity	NPD8035	Phase 2
0.6517	Remote Similarity	NPD5328	Approved
0.6512	Remote Similarity	NPD4786	Approved
0.6477	Remote Similarity	NPD7524	Approved
0.6456	Remote Similarity	NPD4243	Approved
0.6456	Remote Similarity	NPD5777	Approved
0.6429	Remote Similarity	NPD6931	Approved
0.6429	Remote Similarity	NPD6930	Phase 2
0.6395	Remote Similarity	NPD6695	Phase 3
0.6383	Remote Similarity	NPD7920	Phase 3
0.6383	Remote Similarity	NPD4755	Approved
0.6383	Remote Similarity	NPD7919	Phase 3
0.6374	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6327	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8088	Phase 1
0.631	Remote Similarity	NPD6929	Approved
0.6304	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD4784	Approved
0.6296	Remote Similarity	NPD4785	Approved
0.6292	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3667	Approved
0.6265	Remote Similarity	NPD6932	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD7152	Approved
0.625	Remote Similarity	NPD7151	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD7150	Approved
0.625	Remote Similarity	NPD8418	Phase 2
0.625	Remote Similarity	NPD4700	Approved
0.6235	Remote Similarity	NPD7509	Discontinued
0.6203	Remote Similarity	NPD6922	Approved
0.6203	Remote Similarity	NPD6923	Approved
0.6186	Remote Similarity	NPD4159	Approved
0.618	Remote Similarity	NPD8308	Discontinued
0.617	Remote Similarity	NPD7991	Discontinued
0.6154	Remote Similarity	NPD4753	Phase 2
0.6146	Remote Similarity	NPD7638	Approved
0.6125	Remote Similarity	NPD7144	Approved
0.6125	Remote Similarity	NPD7143	Approved
0.6122	Remote Similarity	NPD5224	Approved
0.6122	Remote Similarity	NPD5211	Phase 2
0.6122	Remote Similarity	NPD4633	Approved
0.6122	Remote Similarity	NPD5226	Approved
0.6122	Remote Similarity	NPD5225	Approved
0.6118	Remote Similarity	NPD6683	Phase 2
0.6111	Remote Similarity	NPD7750	Discontinued
0.6105	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5222	Approved
0.6105	Remote Similarity	NPD5221	Approved
0.6105	Remote Similarity	NPD4697	Phase 3
0.61	Remote Similarity	NPD5739	Approved
0.61	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD7128	Approved
0.61	Remote Similarity	NPD6675	Approved
0.6098	Remote Similarity	NPD1810	Approved
0.6098	Remote Similarity	NPD1811	Approved
0.6082	Remote Similarity	NPD7640	Approved
0.6082	Remote Similarity	NPD7639	Approved
0.6071	Remote Similarity	NPD5776	Phase 2
0.6071	Remote Similarity	NPD6925	Approved
0.6067	Remote Similarity	NPD6893	Approved
0.6061	Remote Similarity	NPD5174	Approved
0.6061	Remote Similarity	NPD386	Approved
0.6061	Remote Similarity	NPD388	Approved
0.6061	Remote Similarity	NPD5175	Approved
0.6047	Remote Similarity	NPD7514	Phase 3
0.6042	Remote Similarity	NPD5173	Approved
0.6024	Remote Similarity	NPD5275	Approved
0.6024	Remote Similarity	NPD4190	Phase 3
0.6022	Remote Similarity	NPD7515	Phase 2
0.602	Remote Similarity	NPD5223	Approved
0.6019	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD5141	Approved
0.598	Remote Similarity	NPD7320	Approved
0.598	Remote Similarity	NPD6881	Approved
0.598	Remote Similarity	NPD6899	Approved
0.596	Remote Similarity	NPD7632	Discontinued
0.5957	Remote Similarity	NPD6399	Phase 3
0.5955	Remote Similarity	NPD3133	Approved
0.5955	Remote Similarity	NPD3665	Phase 1
0.5955	Remote Similarity	NPD3666	Approved
0.5941	Remote Similarity	NPD4768	Approved
0.5941	Remote Similarity	NPD6920	Discontinued
0.5941	Remote Similarity	NPD4767	Approved
0.593	Remote Similarity	NPD4195	Approved
0.5926	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7327	Approved
0.5926	Remote Similarity	NPD7328	Approved
0.5922	Remote Similarity	NPD6372	Approved
0.5922	Remote Similarity	NPD6373	Approved
0.5905	Remote Similarity	NPD8297	Approved
0.59	Remote Similarity	NPD4754	Approved
0.5882	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD5697	Approved
0.5876	Remote Similarity	NPD6083	Phase 2
0.5876	Remote Similarity	NPD6084	Phase 2
0.5872	Remote Similarity	NPD7516	Approved
0.5865	Remote Similarity	NPD7290	Approved
0.5865	Remote Similarity	NPD6883	Approved
0.5865	Remote Similarity	NPD7102	Approved
0.5862	Remote Similarity	NPD7332	Phase 2
0.5851	Remote Similarity	NPD7087	Discontinued
0.5849	Remote Similarity	NPD8133	Approved
0.5833	Remote Similarity	NPD7115	Discovery
0.5833	Remote Similarity	NPD4629	Approved
0.5833	Remote Similarity	NPD5210	Approved
0.5825	Remote Similarity	NPD4730	Approved
0.5825	Remote Similarity	NPD4729	Approved
0.5825	Remote Similarity	NPD5128	Approved
0.5824	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD8294	Approved
0.5818	Remote Similarity	NPD8377	Approved
0.5814	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6847	Approved
0.581	Remote Similarity	NPD6649	Approved
0.581	Remote Similarity	NPD8130	Phase 1
0.581	Remote Similarity	NPD6650	Approved
0.581	Remote Similarity	NPD6617	Approved
0.581	Remote Similarity	NPD6869	Approved
0.5795	Remote Similarity	NPD6902	Approved
0.5795	Remote Similarity	NPD6898	Phase 1
0.5778	Remote Similarity	NPD3668	Phase 3
0.5769	Remote Similarity	NPD6012	Approved
0.5769	Remote Similarity	NPD6014	Approved
0.5769	Remote Similarity	NPD6013	Approved
0.5766	Remote Similarity	NPD8378	Approved
0.5766	Remote Similarity	NPD8380	Approved
0.5766	Remote Similarity	NPD8296	Approved
0.5766	Remote Similarity	NPD8379	Approved
0.5766	Remote Similarity	NPD8335	Approved
0.5766	Remote Similarity	NPD8033	Approved
0.5755	Remote Similarity	NPD6882	Approved
0.5741	Remote Similarity	NPD6940	Discontinued
0.5732	Remote Similarity	NPD2687	Approved
0.5732	Remote Similarity	NPD2254	Approved
0.5732	Remote Similarity	NPD2686	Approved
0.573	Remote Similarity	NPD4221	Approved
0.573	Remote Similarity	NPD4223	Phase 3
0.5729	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD5250	Approved
0.5714	Remote Similarity	NPD5249	Phase 3
0.5714	Remote Similarity	NPD5247	Approved
0.5714	Remote Similarity	NPD5251	Approved
0.5714	Remote Similarity	NPD5248	Approved
0.5714	Remote Similarity	NPD5329	Approved
0.5701	Remote Similarity	NPD4632	Approved
0.5673	Remote Similarity	NPD8174	Phase 2

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