NPASS Compound

Structure

NPC304846 OpenBabel07101719242D 22 25 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 6 1 0 0 0 0 2 5 2 0 0 0 0 2 7 1 0 0 0 0 3 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 4 1 1 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 6 0 0 0 10 12 1 0 0 0 0 10 16 1 1 0 0 0 11 13 1 0 0 0 0 11 17 1 1 0 0 0 12 13 1 0 0 0 0 12 18 1 6 0 0 0 13 19 1 1 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	309.08
Volume:	278.457
LogP:	-0.852
LogD:	-0.11
LogS:	-1.011
# Rotatable Bonds:	0
TPSA:	128.48
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	4.16
Fsp3:	0.5
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:	-5.579
MDCK Permeability:	1.1730328878911678e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.826
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.454

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	62.980560302734375%
Volume Distribution (VD):	0.556
Pgp-substrate:	46.390499114990234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.359
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.285
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	2.715
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.035
Carcinogencity:	0.25
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC304846

Natural Product ID:	NPC304846
*Common Name:**	7-Deoxypancratistatin
IUPAC Name:	(1R,2S,3S,4S,4aR,11bR)-1,2,3,4-tetrahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
Synonyms:	7-Deoxypancratistatin
Standard InCHIKey:	GVGWJJOWWDRYOF-DZDPUUJWSA-N
Standard InCHI:	InChI=1S/C14H15NO7/c16-10-8-4-1-6-7(22-3-21-6)2-5(4)14(20)15-9(8)11(17)13(19)12(10)18/h1-2,8-13,16-19H,3H2,(H,15,20)/t8-,9-,10-,11+,12+,13+/m1/s1
SMILES:	c1c2c(cc3c1OCO3)C(=N[C@@H]1[C@@H]2[C@H]([C@@H]([C@H]([C@H]1O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL98481
PubChem CID:	443741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004129] Phenanthridine- and phenanthridone-type amaryllidaceae 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
NPO33168	amaryllidaceae isoquinoline	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1336040]

☑ 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	6
Others	15

Activity Type	# Activity
Cell Line	3
Organism	12
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Inhibition	=	0.44	ug ml-1	PMID[538012]
NPT397	Cell Line	NCI-H460	Homo sapiens	Inhibition	=	0.29	ug ml-1	PMID[538012]
NPT575	Cell Line	KM-20L2	Homo sapiens	Inhibition	=	0.22	ug ml-1	PMID[538012]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	IC50	=	0.48	ug.mL-1	PMID[538013]
NPT4327	Organism	Yellow fever virus	Yellow fever virus	IC50	=	0.4	ug.mL-1	PMID[538013]
NPT4328	Organism	Dengue virus type 4	Dengue virus 4	IC50	=	0.67	ug.mL-1	PMID[538013]
NPT27	Others	Unspecified		TI	=	5.9	n.a.	PMID[538013]
NPT27	Others	Unspecified		TI	=	6.6	n.a.	PMID[538013]
NPT27	Others	Unspecified		TI	=	3.7	n.a.	PMID[538013]
NPT341	Organism	Punta Toro virus	Punta Toro virus	IC50	=	0.66	ug.mL-1	PMID[538013]
NPT4329	Organism	Rift Valley fever virus	Rift Valley fever virus	IC50	=	5.1	ug.mL-1	PMID[538013]
NPT4330	Organism	Sandfly fever sicilian virus	Sandfly fever sicilian virus	IC50	=	1.7	ug.mL-1	PMID[538013]
NPT27	Others	Unspecified		TI	=	4.3	n.a.	PMID[538013]
NPT27	Others	Unspecified		TI	=	2.7	n.a.	PMID[538013]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	Activity	=	60.0	%	PMID[538013]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	Activity	=	80.0	%	PMID[538013]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	28.0	day	PMID[538013]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	Activity	=	9.5	day	PMID[538013]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	Activity	=	15.0	day	PMID[538013]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	Activity	=	13.6	day	PMID[538013]

☑ 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 NPC304846 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	325
0.1-0.2	1314
0.2-0.3	4691
0.3-0.4	11685
0.4-0.5	7289
0.5-0.6	11271
0.6-0.7	5244
0.7-0.8	851
0.8-0.85	10
0.85-0.9	6
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC89199
0.987	High Similarity	NPC54125
0.9503	High Similarity	NPC1291
0.9503	High Similarity	NPC115343
0.95	High Similarity	NPC289743
0.95	High Similarity	NPC110374
0.9448	High Similarity	NPC474607
0.939	High Similarity	NPC474650
0.9359	High Similarity	NPC69360
0.9268	High Similarity	NPC475794
0.9074	High Similarity	NPC182257
0.8772	High Similarity	NPC474661
0.8772	High Similarity	NPC475919
0.8675	High Similarity	NPC474953
0.8506	High Similarity	NPC77572
0.8383	Intermediate Similarity	NPC198741
0.8361	Intermediate Similarity	NPC475768
0.8304	Intermediate Similarity	NPC187678
0.8035	Intermediate Similarity	NPC474051
0.8025	Intermediate Similarity	NPC254610
0.8023	Intermediate Similarity	NPC311991
0.8	Intermediate Similarity	NPC15919
0.7929	Intermediate Similarity	NPC4304
0.7907	Intermediate Similarity	NPC100566
0.7907	Intermediate Similarity	NPC181653
0.7907	Intermediate Similarity	NPC190332
0.7874	Intermediate Similarity	NPC477115
0.7829	Intermediate Similarity	NPC2314
0.7778	Intermediate Similarity	NPC34780
0.7778	Intermediate Similarity	NPC9867
0.7733	Intermediate Similarity	NPC320104
0.7714	Intermediate Similarity	NPC474475
0.7701	Intermediate Similarity	NPC252960
0.7697	Intermediate Similarity	NPC294790
0.7697	Intermediate Similarity	NPC118633
0.7697	Intermediate Similarity	NPC148693
0.7688	Intermediate Similarity	NPC180306
0.767	Intermediate Similarity	NPC65403
0.767	Intermediate Similarity	NPC470739
0.767	Intermediate Similarity	NPC477640
0.767	Intermediate Similarity	NPC225597
0.7667	Intermediate Similarity	NPC248642
0.7657	Intermediate Similarity	NPC475686
0.7657	Intermediate Similarity	NPC58766
0.7644	Intermediate Similarity	NPC476002
0.764	Intermediate Similarity	NPC237044
0.763	Intermediate Similarity	NPC218614
0.7627	Intermediate Similarity	NPC228040
0.7624	Intermediate Similarity	NPC156576
0.7619	Intermediate Similarity	NPC474560
0.7598	Intermediate Similarity	NPC474325
0.7584	Intermediate Similarity	NPC304675
0.7571	Intermediate Similarity	NPC231371
0.7569	Intermediate Similarity	NPC275132
0.7558	Intermediate Similarity	NPC329837
0.7557	Intermediate Similarity	NPC290759
0.7557	Intermediate Similarity	NPC158148
0.7557	Intermediate Similarity	NPC82533
0.7557	Intermediate Similarity	NPC266176
0.7556	Intermediate Similarity	NPC244554
0.7556	Intermediate Similarity	NPC474745
0.7556	Intermediate Similarity	NPC126284
0.7556	Intermediate Similarity	NPC99179
0.7552	Intermediate Similarity	NPC474595
0.7543	Intermediate Similarity	NPC68328
0.7541	Intermediate Similarity	NPC214116
0.7527	Intermediate Similarity	NPC475981
0.7527	Intermediate Similarity	NPC474746
0.7514	Intermediate Similarity	NPC205167
0.7514	Intermediate Similarity	NPC249274
0.75	Intermediate Similarity	NPC77359
0.7485	Intermediate Similarity	NPC16436
0.7473	Intermediate Similarity	NPC476575
0.7469	Intermediate Similarity	NPC160607
0.7469	Intermediate Similarity	NPC312770
0.7469	Intermediate Similarity	NPC41473
0.7469	Intermediate Similarity	NPC204848
0.7469	Intermediate Similarity	NPC14600
0.7468	Intermediate Similarity	NPC470706
0.7455	Intermediate Similarity	NPC103637
0.7455	Intermediate Similarity	NPC36531
0.7455	Intermediate Similarity	NPC63628
0.7455	Intermediate Similarity	NPC230538
0.7455	Intermediate Similarity	NPC229172
0.7455	Intermediate Similarity	NPC178466
0.7425	Intermediate Similarity	NPC166506
0.7425	Intermediate Similarity	NPC197352
0.7425	Intermediate Similarity	NPC110763
0.7425	Intermediate Similarity	NPC189239
0.7423	Intermediate Similarity	NPC299583
0.7423	Intermediate Similarity	NPC474039
0.7414	Intermediate Similarity	NPC97072
0.7414	Intermediate Similarity	NPC215829
0.741	Intermediate Similarity	NPC324962
0.7403	Intermediate Similarity	NPC114364
0.7403	Intermediate Similarity	NPC320223
0.7391	Intermediate Similarity	NPC58585
0.7389	Intermediate Similarity	NPC229166
0.7389	Intermediate Similarity	NPC329969
0.7389	Intermediate Similarity	NPC128560
0.7389	Intermediate Similarity	NPC49353
0.7389	Intermediate Similarity	NPC199465
0.7386	Intermediate Similarity	NPC238530
0.7386	Intermediate Similarity	NPC232514
0.7386	Intermediate Similarity	NPC276944
0.738	Intermediate Similarity	NPC117717
0.7378	Intermediate Similarity	NPC477837
0.7378	Intermediate Similarity	NPC477838
0.7374	Intermediate Similarity	NPC57272
0.7365	Intermediate Similarity	NPC121661
0.7365	Intermediate Similarity	NPC239254
0.7365	Intermediate Similarity	NPC73467
0.7365	Intermediate Similarity	NPC172171
0.7356	Intermediate Similarity	NPC111485
0.7356	Intermediate Similarity	NPC59028
0.7356	Intermediate Similarity	NPC92191
0.7351	Intermediate Similarity	NPC230098
0.7348	Intermediate Similarity	NPC474470
0.7346	Intermediate Similarity	NPC264956
0.7345	Intermediate Similarity	NPC90984
0.734	Intermediate Similarity	NPC29472
0.7337	Intermediate Similarity	NPC471032
0.7337	Intermediate Similarity	NPC470935
0.733	Intermediate Similarity	NPC189782
0.7329	Intermediate Similarity	NPC219671
0.7329	Intermediate Similarity	NPC259742
0.7329	Intermediate Similarity	NPC147616
0.7329	Intermediate Similarity	NPC106739
0.7329	Intermediate Similarity	NPC104077
0.7329	Intermediate Similarity	NPC471505
0.7323	Intermediate Similarity	NPC474594
0.7321	Intermediate Similarity	NPC475868
0.7318	Intermediate Similarity	NPC75958
0.7314	Intermediate Similarity	NPC165797
0.7312	Intermediate Similarity	NPC296742
0.7312	Intermediate Similarity	NPC112676
0.731	Intermediate Similarity	NPC127402
0.7306	Intermediate Similarity	NPC159101
0.7305	Intermediate Similarity	NPC265154
0.7305	Intermediate Similarity	NPC474808
0.7303	Intermediate Similarity	NPC301189
0.7303	Intermediate Similarity	NPC57812
0.7303	Intermediate Similarity	NPC298186
0.7303	Intermediate Similarity	NPC474324
0.7301	Intermediate Similarity	NPC184938
0.7301	Intermediate Similarity	NPC174191
0.7301	Intermediate Similarity	NPC18576
0.7301	Intermediate Similarity	NPC101624
0.7299	Intermediate Similarity	NPC156348
0.7299	Intermediate Similarity	NPC206736
0.7299	Intermediate Similarity	NPC195766
0.7297	Intermediate Similarity	NPC69213
0.7296	Intermediate Similarity	NPC469977
0.7296	Intermediate Similarity	NPC147247
0.7296	Intermediate Similarity	NPC246974
0.7289	Intermediate Similarity	NPC472711
0.7288	Intermediate Similarity	NPC247972
0.7284	Intermediate Similarity	NPC196937
0.7278	Intermediate Similarity	NPC252286
0.7278	Intermediate Similarity	NPC115144
0.7278	Intermediate Similarity	NPC277857
0.7278	Intermediate Similarity	NPC473960
0.7278	Intermediate Similarity	NPC154971
0.7278	Intermediate Similarity	NPC226540
0.7273	Intermediate Similarity	NPC156376
0.7273	Intermediate Similarity	NPC6369
0.7273	Intermediate Similarity	NPC30951
0.7267	Intermediate Similarity	NPC275027
0.7263	Intermediate Similarity	NPC475845
0.7263	Intermediate Similarity	NPC66573
0.7262	Intermediate Similarity	NPC313414
0.7262	Intermediate Similarity	NPC187774
0.7262	Intermediate Similarity	NPC5462
0.7262	Intermediate Similarity	NPC472712
0.7262	Intermediate Similarity	NPC472713
0.7262	Intermediate Similarity	NPC473046
0.7262	Intermediate Similarity	NPC118385
0.7258	Intermediate Similarity	NPC224293
0.7258	Intermediate Similarity	NPC57036
0.7258	Intermediate Similarity	NPC474009
0.7256	Intermediate Similarity	NPC197166
0.7253	Intermediate Similarity	NPC283999
0.7246	Intermediate Similarity	NPC184684
0.7246	Intermediate Similarity	NPC133934
0.7246	Intermediate Similarity	NPC184641
0.7246	Intermediate Similarity	NPC191231
0.7243	Intermediate Similarity	NPC135772
0.7241	Intermediate Similarity	NPC37205
0.7241	Intermediate Similarity	NPC160931
0.7241	Intermediate Similarity	NPC146288
0.7239	Intermediate Similarity	NPC47181
0.7235	Intermediate Similarity	NPC475959
0.7235	Intermediate Similarity	NPC59907
0.7235	Intermediate Similarity	NPC37144
0.7233	Intermediate Similarity	NPC157740
0.7233	Intermediate Similarity	NPC191302
0.7233	Intermediate Similarity	NPC99798
0.7229	Intermediate Similarity	NPC177868
0.7229	Intermediate Similarity	NPC284464
0.7228	Intermediate Similarity	NPC312918

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 NPC304846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	642
0.2-0.3	1194
0.3-0.4	2629
0.4-0.5	2379
0.5-0.6	1503
0.6-0.7	543
0.7-0.8	67
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8272	Intermediate Similarity	NPD4005	Discontinued
0.8046	Intermediate Similarity	NPD7007	Discovery
0.7824	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4663	Approved
0.7544	Intermediate Similarity	NPD2977	Approved
0.7544	Intermediate Similarity	NPD2978	Approved
0.7455	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5772	Approved
0.7442	Intermediate Similarity	NPD5773	Approved
0.7418	Intermediate Similarity	NPD4578	Approved
0.7418	Intermediate Similarity	NPD4577	Approved
0.7401	Intermediate Similarity	NPD2969	Approved
0.7401	Intermediate Similarity	NPD2970	Approved
0.7378	Intermediate Similarity	NPD1375	Discontinued
0.7351	Intermediate Similarity	NPD7906	Approved
0.7349	Intermediate Similarity	NPD6331	Phase 2
0.7345	Intermediate Similarity	NPD3051	Approved
0.7337	Intermediate Similarity	NPD7526	Approved
0.7337	Intermediate Similarity	NPD52	Approved
0.7337	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4237	Approved
0.7289	Intermediate Similarity	NPD4236	Phase 3
0.7277	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD27	Approved
0.7263	Intermediate Similarity	NPD2489	Approved
0.7216	Intermediate Similarity	NPD5604	Discontinued
0.7202	Intermediate Similarity	NPD5241	Discontinued
0.7176	Intermediate Similarity	NPD4123	Phase 3
0.7168	Intermediate Similarity	NPD4675	Approved
0.7168	Intermediate Similarity	NPD4678	Approved
0.7166	Intermediate Similarity	NPD6841	Approved
0.7166	Intermediate Similarity	NPD6843	Phase 3
0.7166	Intermediate Similarity	NPD6842	Approved
0.7135	Intermediate Similarity	NPD7312	Approved
0.7135	Intermediate Similarity	NPD7311	Approved
0.7135	Intermediate Similarity	NPD7313	Approved
0.7135	Intermediate Similarity	NPD7310	Approved
0.7119	Intermediate Similarity	NPD4055	Discovery
0.7117	Intermediate Similarity	NPD2238	Phase 2
0.7108	Intermediate Similarity	NPD2161	Phase 2
0.7101	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7309	Approved
0.7086	Intermediate Similarity	NPD37	Approved
0.7048	Intermediate Similarity	NPD4108	Discontinued
0.7015	Intermediate Similarity	NPD7827	Phase 1
0.7006	Intermediate Similarity	NPD2560	Approved
0.7006	Intermediate Similarity	NPD2563	Approved
0.6994	Remote Similarity	NPD2122	Discontinued
0.6978	Remote Similarity	NPD4481	Phase 3
0.6977	Remote Similarity	NPD4739	Approved
0.6966	Remote Similarity	NPD4965	Approved
0.6966	Remote Similarity	NPD4967	Phase 2
0.6966	Remote Similarity	NPD4966	Approved
0.6964	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3705	Approved
0.6959	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2674	Phase 3
0.6949	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5090	Approved
0.6932	Remote Similarity	NPD4772	Phase 2
0.6932	Remote Similarity	NPD5089	Approved
0.6932	Remote Similarity	NPD4773	Phase 2
0.6915	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3692	Discontinued
0.689	Remote Similarity	NPD3144	Approved
0.689	Remote Similarity	NPD3145	Approved
0.6889	Remote Similarity	NPD6234	Discontinued
0.6882	Remote Similarity	NPD5177	Phase 3
0.6882	Remote Similarity	NPD3060	Approved
0.6882	Remote Similarity	NPD6674	Discontinued
0.6879	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7296	Approved
0.6869	Remote Similarity	NPD4002	Approved
0.6869	Remote Similarity	NPD4004	Approved
0.6868	Remote Similarity	NPD6071	Discontinued
0.6854	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2494	Approved
0.6853	Remote Similarity	NPD2493	Approved
0.6853	Remote Similarity	NPD3450	Approved
0.6853	Remote Similarity	NPD3452	Approved
0.6848	Remote Similarity	NPD839	Approved
0.6848	Remote Similarity	NPD840	Approved
0.6834	Remote Similarity	NPD4583	Approved
0.6834	Remote Similarity	NPD4582	Approved
0.6829	Remote Similarity	NPD3027	Phase 3
0.6826	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2974	Approved
0.6821	Remote Similarity	NPD2975	Approved
0.6821	Remote Similarity	NPD2973	Approved
0.6807	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1613	Approved
0.6802	Remote Similarity	NPD2677	Approved
0.6802	Remote Similarity	NPD4580	Approved
0.6798	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4584	Approved
0.6782	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD600	Approved
0.6768	Remote Similarity	NPD596	Approved
0.676	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD8053	Approved
0.6737	Remote Similarity	NPD8054	Approved
0.6734	Remote Similarity	NPD5005	Approved
0.6734	Remote Similarity	NPD5006	Approved
0.6727	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7228	Approved
0.6707	Remote Similarity	NPD1712	Approved
0.6705	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2219	Phase 1
0.6704	Remote Similarity	NPD3383	Approved
0.6704	Remote Similarity	NPD3382	Approved
0.6704	Remote Similarity	NPD3384	Approved
0.6701	Remote Similarity	NPD4420	Approved
0.6687	Remote Similarity	NPD5109	Approved
0.6687	Remote Similarity	NPD5111	Phase 2
0.6687	Remote Similarity	NPD5110	Phase 2
0.6686	Remote Similarity	NPD4162	Approved
0.6685	Remote Similarity	NPD7315	Approved
0.6684	Remote Similarity	NPD5582	Discontinued
0.6667	Remote Similarity	NPD1357	Approved
0.6667	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6746	Phase 2
0.6667	Remote Similarity	NPD4210	Discontinued
0.6667	Remote Similarity	NPD1669	Approved
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD1653	Approved
0.6667	Remote Similarity	NPD3687	Approved
0.6667	Remote Similarity	NPD3686	Approved
0.6649	Remote Similarity	NPD2488	Approved
0.6649	Remote Similarity	NPD2490	Approved
0.6648	Remote Similarity	NPD6072	Discontinued
0.6647	Remote Similarity	NPD1753	Discontinued
0.6632	Remote Similarity	NPD7549	Discontinued
0.6631	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7199	Phase 2
0.6629	Remote Similarity	NPD4357	Discontinued
0.6628	Remote Similarity	NPD7153	Discontinued
0.6627	Remote Similarity	NPD2157	Approved
0.6614	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3620	Phase 2
0.6607	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1558	Phase 1
0.6606	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2230	Approved
0.6605	Remote Similarity	NPD2233	Approved
0.6605	Remote Similarity	NPD2232	Approved
0.6598	Remote Similarity	NPD2843	Phase 2
0.6598	Remote Similarity	NPD2845	Phase 2
0.6598	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8156	Discontinued
0.6595	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7047	Phase 3
0.6582	Remote Similarity	NPD7125	Discontinued
0.6576	Remote Similarity	NPD4666	Phase 3
0.6571	Remote Similarity	NPD7124	Phase 2
0.6567	Remote Similarity	NPD6823	Phase 2
0.6566	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8252	Approved
0.6543	Remote Similarity	NPD8099	Discontinued
0.6543	Remote Similarity	NPD8251	Approved
0.6541	Remote Similarity	NPD6107	Approved
0.6538	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1774	Approved
0.6529	Remote Similarity	NPD817	Approved
0.6529	Remote Similarity	NPD4097	Suspended
0.6529	Remote Similarity	NPD823	Approved
0.6527	Remote Similarity	NPD1024	Discontinued
0.6524	Remote Similarity	NPD2922	Phase 1
0.6522	Remote Similarity	NPD5709	Phase 3
0.6522	Remote Similarity	NPD9384	Approved
0.6522	Remote Similarity	NPD9381	Approved
0.6517	Remote Similarity	NPD4727	Phase 1
0.651	Remote Similarity	NPD2971	Approved
0.651	Remote Similarity	NPD7280	Phase 3
0.651	Remote Similarity	NPD7281	Phase 3
0.651	Remote Similarity	NPD2968	Approved
0.6505	Remote Similarity	NPD4010	Discontinued
0.6497	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7240	Approved
0.6489	Remote Similarity	NPD3489	Phase 3
0.6482	Remote Similarity	NPD4604	Approved
0.6482	Remote Similarity	NPD4605	Approved
0.6473	Remote Similarity	NPD7801	Approved
0.6471	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7831	Phase 2
0.6467	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7833	Phase 2
0.6464	Remote Similarity	NPD3778	Approved
0.6463	Remote Similarity	NPD3685	Discontinued
0.6461	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD8151	Discontinued

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