NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.05
Volume:	232.234
LogP:	2.388
LogD:	2.711
LogS:	-3.957
# Rotatable Bonds:	0
TPSA:	34.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	2.377
Fsp3:	0.0
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:	-4.571
MDCK Permeability:	2.3805641831131652e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	94.16344451904297%
Volume Distribution (VD):	0.676
Pgp-substrate:	2.7387518882751465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.387
CYP2C19-inhibitor:	0.63
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.519
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	5.11
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.927
Drug-inuced Liver Injury (DILI):	0.773
AMES Toxicity:	0.973
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.069
Carcinogencity:	0.979
Eye Corrosion:	0.003
Eye Irritation:	0.703
Respiratory Toxicity:	0.611

Download Data

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

Natural Product: NPC478185

Natural Product ID:	NPC478185
*Common Name:**	9-Fluoro-6H-indolo[3,2,1-de][1,5]naphthyridine-6-one
IUPAC Name:	13-fluoro-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
Synonyms:
Standard InCHIKey:	QHFNPWGDQLOQIW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H7FN2O/c15-8-1-2-9-10-5-6-16-11-3-4-13(18)17(14(10)11)12(9)7-8/h1-7H
SMILES:	C1=CC2=C(C=C1F)N3C(=O)C=CC4=NC=CC2=C43
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11506957
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003805] Indolonaphthyridine alkaloids

*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
NPO6026	Zanthoxylum chiloperone	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309303]
NPO6026	Zanthoxylum chiloperone	Species	Rutaceae	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	13100	nM	PMID[16309303]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	13100	nM	PMID[16309303]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	13100	nM	PMID[16309303]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	13100	nM	PMID[16309303]

☑ 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 NPC478185 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	872
0.1-0.2	7831
0.2-0.3	16060
0.3-0.4	12424
0.4-0.5	1917
0.5-0.6	2149
0.6-0.7	1179
0.7-0.8	230
0.8-0.85	22
0.85-0.9	4
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC293487
0.9539	High Similarity	NPC478182
0.9416	High Similarity	NPC478183
0.9412	High Similarity	NPC478184
0.9295	High Similarity	NPC32534
0.9172	High Similarity	NPC91895
0.9	High Similarity	NPC478186
0.8951	High Similarity	NPC12649
0.8896	High Similarity	NPC24864
0.8805	High Similarity	NPC56233
0.8333	Intermediate Similarity	NPC470111
0.8269	Intermediate Similarity	NPC63545
0.8239	Intermediate Similarity	NPC281094
0.8229	Intermediate Similarity	NPC198673
0.8217	Intermediate Similarity	NPC179787
0.8217	Intermediate Similarity	NPC469811
0.8217	Intermediate Similarity	NPC201380
0.8182	Intermediate Similarity	NPC238499
0.8165	Intermediate Similarity	NPC321911
0.816	Intermediate Similarity	NPC225018
0.8125	Intermediate Similarity	NPC325903
0.8113	Intermediate Similarity	NPC40070
0.8098	Intermediate Similarity	NPC122141
0.8045	Intermediate Similarity	NPC168911
0.8045	Intermediate Similarity	NPC212213
0.8045	Intermediate Similarity	NPC239954
0.8037	Intermediate Similarity	NPC477591
0.7975	Intermediate Similarity	NPC236711
0.7975	Intermediate Similarity	NPC470440
0.7967	Intermediate Similarity	NPC211813
0.7923	Intermediate Similarity	NPC200836
0.7923	Intermediate Similarity	NPC53144
0.7898	Intermediate Similarity	NPC277157
0.7871	Intermediate Similarity	NPC314102
0.7871	Intermediate Similarity	NPC251722
0.7861	Intermediate Similarity	NPC191415
0.7848	Intermediate Similarity	NPC20144
0.784	Intermediate Similarity	NPC470233
0.7838	Intermediate Similarity	NPC46358
0.7816	Intermediate Similarity	NPC102755
0.7802	Intermediate Similarity	NPC81535
0.7798	Intermediate Similarity	NPC114637
0.7784	Intermediate Similarity	NPC317105
0.7778	Intermediate Similarity	NPC469529
0.7771	Intermediate Similarity	NPC470204
0.7756	Intermediate Similarity	NPC150259
0.7754	Intermediate Similarity	NPC82548
0.7754	Intermediate Similarity	NPC287208
0.7725	Intermediate Similarity	NPC470203
0.7713	Intermediate Similarity	NPC174672
0.7713	Intermediate Similarity	NPC174758
0.7706	Intermediate Similarity	NPC65080
0.7672	Intermediate Similarity	NPC85273
0.765	Intermediate Similarity	NPC474916
0.7644	Intermediate Similarity	NPC11126
0.7636	Intermediate Similarity	NPC476219
0.7633	Intermediate Similarity	NPC274229
0.7627	Intermediate Similarity	NPC308931
0.7627	Intermediate Similarity	NPC99939
0.7625	Intermediate Similarity	NPC190296
0.7624	Intermediate Similarity	NPC326422
0.7619	Intermediate Similarity	NPC194881
0.761	Intermediate Similarity	NPC115611
0.76	Intermediate Similarity	NPC73994
0.7595	Intermediate Similarity	NPC169433
0.759	Intermediate Similarity	NPC51054
0.7586	Intermediate Similarity	NPC240088
0.7586	Intermediate Similarity	NPC473380
0.758	Intermediate Similarity	NPC96102
0.7576	Intermediate Similarity	NPC200214
0.7558	Intermediate Similarity	NPC82331
0.7547	Intermediate Similarity	NPC73767
0.7547	Intermediate Similarity	NPC110126
0.7547	Intermediate Similarity	NPC104483
0.7545	Intermediate Similarity	NPC129721
0.7543	Intermediate Similarity	NPC265710
0.754	Intermediate Similarity	NPC317701
0.7532	Intermediate Similarity	NPC84911
0.7532	Intermediate Similarity	NPC105127
0.7531	Intermediate Similarity	NPC159856
0.7531	Intermediate Similarity	NPC314372
0.753	Intermediate Similarity	NPC476297
0.7529	Intermediate Similarity	NPC280852
0.7516	Intermediate Similarity	NPC198988
0.7515	Intermediate Similarity	NPC472260
0.75	Intermediate Similarity	NPC16659
0.75	Intermediate Similarity	NPC97343
0.7486	Intermediate Similarity	NPC62749
0.7485	Intermediate Similarity	NPC143872
0.7485	Intermediate Similarity	NPC288838
0.7474	Intermediate Similarity	NPC274982
0.7472	Intermediate Similarity	NPC467063
0.7472	Intermediate Similarity	NPC21429
0.7472	Intermediate Similarity	NPC228835
0.7471	Intermediate Similarity	NPC471579
0.7471	Intermediate Similarity	NPC317054
0.7468	Intermediate Similarity	NPC29886
0.7468	Intermediate Similarity	NPC261195
0.7443	Intermediate Similarity	NPC248462
0.7438	Intermediate Similarity	NPC88097
0.7436	Intermediate Similarity	NPC82295
0.7423	Intermediate Similarity	NPC86288
0.7423	Intermediate Similarity	NPC285731
0.7421	Intermediate Similarity	NPC65408
0.7416	Intermediate Similarity	NPC48938
0.7412	Intermediate Similarity	NPC242116
0.7396	Intermediate Similarity	NPC92796
0.7396	Intermediate Similarity	NPC135141
0.7394	Intermediate Similarity	NPC57398
0.7391	Intermediate Similarity	NPC469783
0.7391	Intermediate Similarity	NPC469779
0.7391	Intermediate Similarity	NPC284635
0.7391	Intermediate Similarity	NPC469768
0.7391	Intermediate Similarity	NPC469761
0.7391	Intermediate Similarity	NPC469784
0.7391	Intermediate Similarity	NPC469780
0.7391	Intermediate Similarity	NPC279081
0.7391	Intermediate Similarity	NPC469767
0.7391	Intermediate Similarity	NPC230002
0.7386	Intermediate Similarity	NPC28848
0.7386	Intermediate Similarity	NPC14325
0.7383	Intermediate Similarity	NPC91958
0.7374	Intermediate Similarity	NPC284678
0.7368	Intermediate Similarity	NPC238457
0.7363	Intermediate Similarity	NPC324091
0.7358	Intermediate Similarity	NPC325252
0.7353	Intermediate Similarity	NPC44773
0.7353	Intermediate Similarity	NPC279918
0.7353	Intermediate Similarity	NPC215584
0.7349	Intermediate Similarity	NPC105818
0.7349	Intermediate Similarity	NPC53947
0.7349	Intermediate Similarity	NPC24678
0.7348	Intermediate Similarity	NPC17059
0.7346	Intermediate Similarity	NPC469766
0.7341	Intermediate Similarity	NPC63751
0.7333	Intermediate Similarity	NPC471957
0.733	Intermediate Similarity	NPC151635
0.733	Intermediate Similarity	NPC474958
0.7326	Intermediate Similarity	NPC42372
0.7325	Intermediate Similarity	NPC256893
0.7318	Intermediate Similarity	NPC470205
0.7312	Intermediate Similarity	NPC167710
0.731	Intermediate Similarity	NPC282231
0.7299	Intermediate Similarity	NPC194411
0.7294	Intermediate Similarity	NPC56765
0.7294	Intermediate Similarity	NPC318065
0.7294	Intermediate Similarity	NPC206819
0.7293	Intermediate Similarity	NPC94752
0.7288	Intermediate Similarity	NPC284775
0.7288	Intermediate Similarity	NPC157583
0.7288	Intermediate Similarity	NPC237188
0.7288	Intermediate Similarity	NPC83774
0.7283	Intermediate Similarity	NPC216550
0.7273	Intermediate Similarity	NPC469938
0.7267	Intermediate Similarity	NPC162689
0.7267	Intermediate Similarity	NPC265100
0.7267	Intermediate Similarity	NPC143603
0.7267	Intermediate Similarity	NPC54102
0.7262	Intermediate Similarity	NPC138842
0.7262	Intermediate Similarity	NPC469760
0.7262	Intermediate Similarity	NPC73952
0.7262	Intermediate Similarity	NPC25008
0.7262	Intermediate Similarity	NPC469763
0.7262	Intermediate Similarity	NPC259644
0.7262	Intermediate Similarity	NPC469765
0.7262	Intermediate Similarity	NPC469786
0.7261	Intermediate Similarity	NPC22079
0.7258	Intermediate Similarity	NPC128244
0.7251	Intermediate Similarity	NPC255229
0.7251	Intermediate Similarity	NPC81229
0.7238	Intermediate Similarity	NPC133003
0.7237	Intermediate Similarity	NPC48564
0.7237	Intermediate Similarity	NPC265605
0.7237	Intermediate Similarity	NPC182570
0.7235	Intermediate Similarity	NPC216643
0.7234	Intermediate Similarity	NPC237414
0.7228	Intermediate Similarity	NPC476460
0.7228	Intermediate Similarity	NPC473763
0.7228	Intermediate Similarity	NPC117244
0.7219	Intermediate Similarity	NPC211572
0.7219	Intermediate Similarity	NPC80597
0.7219	Intermediate Similarity	NPC75540
0.7219	Intermediate Similarity	NPC212376
0.7219	Intermediate Similarity	NPC70922
0.7216	Intermediate Similarity	NPC161861
0.7212	Intermediate Similarity	NPC469525
0.7207	Intermediate Similarity	NPC61011
0.7202	Intermediate Similarity	NPC216713
0.7198	Intermediate Similarity	NPC17273
0.7198	Intermediate Similarity	NPC141612
0.7198	Intermediate Similarity	NPC135601
0.7193	Intermediate Similarity	NPC80681
0.7191	Intermediate Similarity	NPC234987
0.7191	Intermediate Similarity	NPC64436
0.7191	Intermediate Similarity	NPC59269
0.7189	Intermediate Similarity	NPC324149
0.7184	Intermediate Similarity	NPC54988
0.7184	Intermediate Similarity	NPC49954
0.7184	Intermediate Similarity	NPC474561
0.7182	Intermediate Similarity	NPC165495

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 NPC478185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	452
0.1-0.2	711
0.2-0.3	1003
0.3-0.4	2402
0.4-0.5	1971
0.5-0.6	1687
0.6-0.7	813
0.7-0.8	106
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8012	Intermediate Similarity	NPD2837	Discontinued
0.7989	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4547	Phase 3
0.7937	Intermediate Similarity	NPD2430	Phase 2
0.7879	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4326	Phase 2
0.7831	Intermediate Similarity	NPD5400	Approved
0.7829	Intermediate Similarity	NPD715	Phase 3
0.7809	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3385	Approved
0.7751	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD2333	Discontinued
0.7751	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD2915	Discontinued
0.7688	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1722	Approved
0.7667	Intermediate Similarity	NPD4922	Phase 2
0.7661	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1661	Suspended
0.763	Intermediate Similarity	NPD4075	Phase 2
0.7627	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2006	Phase 2
0.7625	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3476	Approved
0.7597	Intermediate Similarity	NPD3475	Approved
0.7584	Intermediate Similarity	NPD6721	Phase 1
0.758	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7394	Phase 2
0.7529	Intermediate Similarity	NPD2720	Phase 1
0.7529	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7402	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5555	Phase 1
0.7527	Intermediate Similarity	NPD5017	Discontinued
0.7516	Intermediate Similarity	NPD2118	Approved
0.7516	Intermediate Similarity	NPD2119	Approved
0.75	Intermediate Similarity	NPD3100	Discontinued
0.75	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5809	Phase 3
0.7486	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7564	Discontinued
0.7472	Intermediate Similarity	NPD5892	Approved
0.7446	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4638	Approved
0.7442	Intermediate Similarity	NPD4639	Approved
0.7442	Intermediate Similarity	NPD4640	Approved
0.744	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD786	Approved
0.7429	Intermediate Similarity	NPD5104	Approved
0.7421	Intermediate Similarity	NPD201	Phase 2
0.7421	Intermediate Similarity	NPD45	Approved
0.7421	Intermediate Similarity	NPD200	Phase 2
0.7421	Intermediate Similarity	NPD6554	Approved
0.7419	Intermediate Similarity	NPD3654	Approved
0.7416	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6771	Discontinued
0.7401	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4902	Discontinued
0.7389	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6217	Discontinued
0.7381	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1683	Approved
0.7378	Intermediate Similarity	NPD7469	Discontinued
0.7377	Intermediate Similarity	NPD3430	Approved
0.7377	Intermediate Similarity	NPD3431	Approved
0.7371	Intermediate Similarity	NPD4883	Approved
0.7363	Intermediate Similarity	NPD3321	Discontinued
0.7351	Intermediate Similarity	NPD4848	Phase 1
0.7348	Intermediate Similarity	NPD3961	Discontinued
0.7342	Intermediate Similarity	NPD4028	Approved
0.7342	Intermediate Similarity	NPD3944	Approved
0.7342	Intermediate Similarity	NPD4029	Approved
0.7342	Intermediate Similarity	NPD3942	Approved
0.7342	Intermediate Similarity	NPD4030	Approved
0.7333	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2751	Phase 1
0.7321	Intermediate Similarity	NPD976	Approved
0.7321	Intermediate Similarity	NPD975	Approved
0.7321	Intermediate Similarity	NPD977	Approved
0.732	Intermediate Similarity	NPD7164	Discontinued
0.731	Intermediate Similarity	NPD5315	Discontinued
0.731	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4047	Discontinued
0.7299	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7618	Phase 3
0.7297	Intermediate Similarity	NPD7619	Phase 3
0.7294	Intermediate Similarity	NPD5418	Discontinued
0.7292	Intermediate Similarity	NPD6521	Phase 3
0.7292	Intermediate Similarity	NPD6520	Phase 3
0.729	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD991	Phase 2
0.7288	Intermediate Similarity	NPD7111	Discontinued
0.7283	Intermediate Similarity	NPD5505	Discontinued
0.7283	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6787	Phase 2
0.7278	Intermediate Similarity	NPD6178	Phase 3
0.7278	Intermediate Similarity	NPD4957	Phase 2
0.7273	Intermediate Similarity	NPD5065	Approved
0.7273	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4128	Approved
0.7267	Intermediate Similarity	NPD3323	Discontinued
0.7263	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3362	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4988	Discontinued
0.724	Intermediate Similarity	NPD3905	Phase 3
0.7239	Intermediate Similarity	NPD5020	Approved
0.7237	Intermediate Similarity	NPD268	Approved
0.7237	Intermediate Similarity	NPD271	Approved
0.7237	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6999	Discontinued
0.7234	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2880	Discontinued
0.7216	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5473	Discontinued
0.7207	Intermediate Similarity	NPD3927	Phase 2
0.7204	Intermediate Similarity	NPD7944	Discontinued
0.7202	Intermediate Similarity	NPD6459	Phase 2
0.72	Intermediate Similarity	NPD4024	Phase 3
0.7191	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4181	Approved
0.7175	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3583	Phase 2
0.7166	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2408	Discontinued
0.7158	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1255	Approved
0.7143	Intermediate Similarity	NPD1256	Approved
0.7143	Intermediate Similarity	NPD1254	Approved
0.7143	Intermediate Similarity	NPD5862	Discovery
0.7143	Intermediate Similarity	NPD5075	Discontinued
0.7143	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1253	Approved
0.7135	Intermediate Similarity	NPD1658	Discontinued
0.712	Intermediate Similarity	NPD2881	Approved
0.712	Intermediate Similarity	NPD2879	Approved
0.7119	Intermediate Similarity	NPD750	Phase 2
0.7113	Intermediate Similarity	NPD7666	Phase 3
0.7113	Intermediate Similarity	NPD2443	Approved
0.7113	Intermediate Similarity	NPD2442	Approved
0.7113	Intermediate Similarity	NPD7665	Phase 2
0.7112	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5508	Phase 1
0.7111	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5444	Phase 1
0.7102	Intermediate Similarity	NPD5436	Phase 1
0.7101	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4315	Phase 2
0.7095	Intermediate Similarity	NPD3506	Approved
0.7095	Intermediate Similarity	NPD3505	Approved
0.7093	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6446	Discontinued
0.7083	Intermediate Similarity	NPD1183	Approved
0.7079	Intermediate Similarity	NPD7006	Approved
0.7076	Intermediate Similarity	NPD2580	Discontinued
0.7076	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5864	Phase 2
0.7059	Intermediate Similarity	NPD2717	Phase 2
0.7056	Intermediate Similarity	NPD4076	Approved
0.7056	Intermediate Similarity	NPD1893	Phase 2
0.7056	Intermediate Similarity	NPD4079	Approved
0.7056	Intermediate Similarity	NPD1892	Phase 2
0.7049	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1343	Approved
0.7045	Intermediate Similarity	NPD2640	Approved
0.7045	Intermediate Similarity	NPD2641	Approved
0.7041	Intermediate Similarity	NPD2172	Phase 1
0.7039	Intermediate Similarity	NPD6044	Discontinued
0.7039	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6206	Phase 1
0.7033	Intermediate Similarity	NPD3318	Approved
0.7033	Intermediate Similarity	NPD3320	Approved
0.7033	Intermediate Similarity	NPD3319	Phase 1
0.7029	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4334	Discontinued
0.7027	Intermediate Similarity	NPD5016	Approved
0.7026	Intermediate Similarity	NPD6474	Phase 2
0.7026	Intermediate Similarity	NPD2357	Approved
0.7024	Intermediate Similarity	NPD4703	Approved
0.7024	Intermediate Similarity	NPD4702	Approved
0.7024	Intermediate Similarity	NPD1270	Approved
0.7012	Intermediate Similarity	NPD2075	Approved
0.7012	Intermediate Similarity	NPD2068	Approved
0.7012	Intermediate Similarity	NPD2072	Approved
0.7012	Intermediate Similarity	NPD2071	Approved
0.7012	Intermediate Similarity	NPD2070	Approved
0.7012	Intermediate Similarity	NPD2069	Approved
0.7012	Intermediate Similarity	NPD2074	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