NPASS Compound

Structure

CID60413 OpenBabel06191715392D 40 41 0 0 0 0 0 0 0 0999 V2000 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 21 2 0 0 0 0 17 25 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 32 2 0 0 0 0 23 33 2 0 0 0 0 24 37 1 0 0 0 0 25 40 1 0 0 0 0 26 28 2 0 0 0 0 26 34 1 0 0 0 0 27 29 2 0 0 0 0 27 38 1 0 0 0 0 28 31 1 0 0 0 0 29 30 1 0 0 0 0 30 35 2 0 0 0 0 30 39 1 0 0 0 0 31 36 2 0 0 0 0 31 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	167.09
Volume:	176.332
LogP:	-0.949
LogD:	0.114
LogS:	-1.682
# Rotatable Bonds:	3
TPSA:	63.32
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	3.549
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.185
MDCK Permeability:	0.0024929537903517485
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.158
30% Bioavailability (F30%):	0.767

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.815
Plasma Protein Binding (PPB):	15.134969711303711%
Volume Distribution (VD):	0.372
Pgp-substrate:	76.72105407714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.466
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	11.353
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.315
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.399
Carcinogencity:	0.895
Eye Corrosion:	0.006
Eye Irritation:	0.063
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC60413

Natural Product ID:	NPC60413
*Common Name:**	Gustastatin
IUPAC Name:	[3-methoxy-4-methoxycarbonyl-5-(2-oxoheptyl)phenyl] 2-hydroxy-4-methoxy-6-(2-oxoheptyl)benzoate
Synonyms:	Gustastatin
Standard InCHIKey:	FHOVJOXBAHBKGJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C31H40O9/c1-6-8-10-12-22(32)14-20-16-24(37-3)18-26(34)28(20)31(36)40-25-17-21(15-23(33)13-11-9-7-2)29(30(35)39-5)27(19-25)38-4/h16-19,34H,6-15H2,1-5H3
SMILES:	CCCCCC(=O)Cc1cc(cc(c1C(=O)Oc1cc(CC(=O)CCCCC)c(c(c1)OC)C(=O)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481267
PubChem CID:	11757435
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO13075	Gustavia hexapetala	Species	Lecythidaceae	Eukaryota	n.a.	Peru	1979	PMID[15217278]
NPO31410	Cupania cinerea	Species	Sapindaceae	Eukaryota	n.a.	bark	n.a.	PMID[21438586]
NPO13075	Gustavia hexapetala	Species	Lecythidaceae	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
GI50	7
IC50	3

Activity Type	# Activity
Cell Line	8
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI50	>	10.0	ug.mL-1	PMID[501356]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[501356]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	6.4	ug.mL-1	PMID[501356]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	7.9	ug.mL-1	PMID[501356]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	5.1	ug.mL-1	PMID[501356]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[501356]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	5.2	ug.mL-1	PMID[501356]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90000.0	nM	PMID[501357]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	9000.0	nM	PMID[501357]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	19400.0	nM	PMID[501357]

☑ 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 NPC60413 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	363
0.1-0.2	1589
0.2-0.3	3748
0.3-0.4	8885
0.4-0.5	9688
0.5-0.6	3557
0.6-0.7	5451
0.7-0.8	5989
0.8-0.85	2458
0.85-0.9	889
0.9-0.95	74
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC6923
0.972	High Similarity	NPC237208
0.965	High Similarity	NPC134621
0.965	High Similarity	NPC29577
0.958	High Similarity	NPC66404
0.958	High Similarity	NPC95123
0.9524	High Similarity	NPC133856
0.9514	High Similarity	NPC312789
0.9456	High Similarity	NPC309979
0.9456	High Similarity	NPC307780
0.9441	High Similarity	NPC105648
0.9388	High Similarity	NPC291049
0.9388	High Similarity	NPC233267
0.9384	High Similarity	NPC12305
0.9371	High Similarity	NPC220106
0.9333	High Similarity	NPC89625
0.9333	High Similarity	NPC149618
0.932	High Similarity	NPC240253
0.932	High Similarity	NPC471641
0.932	High Similarity	NPC471642
0.932	High Similarity	NPC105415
0.932	High Similarity	NPC240622
0.9315	High Similarity	NPC267509
0.9306	High Similarity	NPC250755
0.9257	High Similarity	NPC473978
0.9247	High Similarity	NPC32470
0.9241	High Similarity	NPC310340
0.9226	High Similarity	NPC267153
0.92	High Similarity	NPC273483
0.9161	High Similarity	NPC284007
0.9145	High Similarity	NPC146211
0.9133	High Similarity	NPC227166
0.9128	High Similarity	NPC476684
0.9122	High Similarity	NPC125801
0.9116	High Similarity	NPC472034
0.911	High Similarity	NPC472006
0.911	High Similarity	NPC471643
0.911	High Similarity	NPC471639
0.9103	High Similarity	NPC275734
0.9103	High Similarity	NPC67650
0.9103	High Similarity	NPC1704
0.9097	High Similarity	NPC57380
0.9097	High Similarity	NPC93739
0.9091	High Similarity	NPC143050
0.9085	High Similarity	NPC263483
0.9067	High Similarity	NPC295036
0.9067	High Similarity	NPC470107
0.9067	High Similarity	NPC194379
0.906	High Similarity	NPC172329
0.906	High Similarity	NPC2569
0.9054	High Similarity	NPC472033
0.9054	High Similarity	NPC225173
0.9054	High Similarity	NPC163846
0.9054	High Similarity	NPC473927
0.9041	High Similarity	NPC471644
0.9041	High Similarity	NPC49108
0.9041	High Similarity	NPC471640
0.902	High Similarity	NPC54928
0.9007	High Similarity	NPC478148
0.9	High Similarity	NPC158338
0.9	High Similarity	NPC97028
0.9	High Similarity	NPC288036
0.9	High Similarity	NPC97029
0.9	High Similarity	NPC100985
0.9	High Similarity	NPC65589
0.8993	High Similarity	NPC472036
0.8993	High Similarity	NPC259632
0.8986	High Similarity	NPC473692
0.8981	High Similarity	NPC8070
0.898	High Similarity	NPC51106
0.898	High Similarity	NPC469542
0.898	High Similarity	NPC478202
0.8973	High Similarity	NPC313123
0.8973	High Similarity	NPC16455
0.8973	High Similarity	NPC478217
0.8973	High Similarity	NPC307990
0.8958	High Similarity	NPC135837
0.8951	High Similarity	NPC182496
0.8951	High Similarity	NPC180905
0.8947	High Similarity	NPC217447
0.894	High Similarity	NPC475460
0.894	High Similarity	NPC158866
0.8933	High Similarity	NPC27221
0.8933	High Similarity	NPC37139
0.8933	High Similarity	NPC256672
0.8933	High Similarity	NPC7025
0.8926	High Similarity	NPC107625
0.8926	High Similarity	NPC470322
0.8926	High Similarity	NPC154217
0.8926	High Similarity	NPC181388
0.8917	High Similarity	NPC300984
0.8917	High Similarity	NPC474350
0.8912	High Similarity	NPC474385
0.8912	High Similarity	NPC96692
0.8912	High Similarity	NPC469579
0.8897	High Similarity	NPC191835
0.8889	High Similarity	NPC472799
0.8889	High Similarity	NPC475895
0.8889	High Similarity	NPC242712
0.8889	High Similarity	NPC210942
0.8889	High Similarity	NPC169990
0.8882	High Similarity	NPC106372
0.8882	High Similarity	NPC149526
0.8882	High Similarity	NPC232645
0.8882	High Similarity	NPC474417
0.8882	High Similarity	NPC58668
0.8882	High Similarity	NPC72958
0.8874	High Similarity	NPC10027
0.8874	High Similarity	NPC65775
0.8867	High Similarity	NPC7943
0.8867	High Similarity	NPC22005
0.8867	High Similarity	NPC123202
0.8861	High Similarity	NPC7752
0.8859	High Similarity	NPC1886
0.8859	High Similarity	NPC178627
0.8859	High Similarity	NPC469935
0.8859	High Similarity	NPC196137
0.8851	High Similarity	NPC36181
0.8851	High Similarity	NPC73028
0.8851	High Similarity	NPC84266
0.8844	High Similarity	NPC478201
0.8844	High Similarity	NPC472035
0.8844	High Similarity	NPC475730
0.8836	High Similarity	NPC92655
0.8836	High Similarity	NPC472368
0.8836	High Similarity	NPC124269
0.8831	High Similarity	NPC20541
0.8831	High Similarity	NPC471800
0.8831	High Similarity	NPC38898
0.8828	High Similarity	NPC472364
0.8828	High Similarity	NPC65837
0.8828	High Similarity	NPC473391
0.8828	High Similarity	NPC474771
0.8828	High Similarity	NPC474849
0.8828	High Similarity	NPC70380
0.8828	High Similarity	NPC178467
0.8828	High Similarity	NPC476333
0.8828	High Similarity	NPC149372
0.8828	High Similarity	NPC194579
0.8828	High Similarity	NPC472367
0.8824	High Similarity	NPC474843
0.8824	High Similarity	NPC87708
0.8824	High Similarity	NPC40356
0.8824	High Similarity	NPC142308
0.8824	High Similarity	NPC207624
0.8824	High Similarity	NPC154683
0.8816	High Similarity	NPC325983
0.8816	High Similarity	NPC473466
0.8816	High Similarity	NPC474660
0.8816	High Similarity	NPC227122
0.8816	High Similarity	NPC150928
0.8808	High Similarity	NPC35150
0.8808	High Similarity	NPC106328
0.8808	High Similarity	NPC221352
0.8808	High Similarity	NPC153417
0.8805	High Similarity	NPC30027
0.88	High Similarity	NPC130176
0.88	High Similarity	NPC99454
0.88	High Similarity	NPC138978
0.88	High Similarity	NPC24136
0.88	High Similarity	NPC153758
0.88	High Similarity	NPC196114
0.88	High Similarity	NPC187282
0.88	High Similarity	NPC290133
0.8792	High Similarity	NPC210425
0.8792	High Similarity	NPC112791
0.8792	High Similarity	NPC470296
0.8792	High Similarity	NPC196459
0.8792	High Similarity	NPC94794
0.8792	High Similarity	NPC280404
0.8792	High Similarity	NPC277426
0.8792	High Similarity	NPC188632
0.8792	High Similarity	NPC86373
0.8792	High Similarity	NPC87609
0.879	High Similarity	NPC303565
0.8784	High Similarity	NPC94076
0.8784	High Similarity	NPC182255
0.8782	High Similarity	NPC474373
0.8782	High Similarity	NPC238381
0.8776	High Similarity	NPC165172
0.8776	High Similarity	NPC140890
0.8776	High Similarity	NPC230902
0.8776	High Similarity	NPC472366
0.8776	High Similarity	NPC19476
0.8776	High Similarity	NPC241975
0.8774	High Similarity	NPC4547
0.8767	High Similarity	NPC478200
0.8767	High Similarity	NPC212693
0.8767	High Similarity	NPC472602
0.8767	High Similarity	NPC94248
0.8767	High Similarity	NPC188879
0.8767	High Similarity	NPC475974
0.8767	High Similarity	NPC33144
0.8766	High Similarity	NPC329844
0.8766	High Similarity	NPC214632
0.8758	High Similarity	NPC312549
0.8758	High Similarity	NPC209142
0.8758	High Similarity	NPC193976
0.8758	High Similarity	NPC70016
0.8758	High Similarity	NPC115324

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 NPC60413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	1004
0.2-0.3	1663
0.3-0.4	2569
0.4-0.5	1846
0.5-0.6	1115
0.6-0.7	431
0.7-0.8	147
0.8-0.85	41
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9139	High Similarity	NPD7819	Suspended
0.8966	High Similarity	NPD970	Clinical (unspecified phase)
0.8758	High Similarity	NPD7411	Suspended
0.871	High Similarity	NPD8443	Clinical (unspecified phase)
0.8609	High Similarity	NPD4378	Clinical (unspecified phase)
0.8599	High Similarity	NPD7075	Discontinued
0.8591	High Similarity	NPD3750	Approved
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8509	High Similarity	NPD7852	Clinical (unspecified phase)
0.8506	High Similarity	NPD3226	Approved
0.8487	Intermediate Similarity	NPD2534	Approved
0.8487	Intermediate Similarity	NPD2533	Approved
0.8487	Intermediate Similarity	NPD2532	Approved
0.8483	Intermediate Similarity	NPD1240	Approved
0.8481	Intermediate Similarity	NPD3749	Approved
0.8457	Intermediate Similarity	NPD7473	Discontinued
0.8456	Intermediate Similarity	NPD1549	Phase 2
0.8438	Intermediate Similarity	NPD6959	Discontinued
0.8421	Intermediate Similarity	NPD6799	Approved
0.8408	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6232	Discontinued
0.8378	Intermediate Similarity	NPD1510	Phase 2
0.8367	Intermediate Similarity	NPD1607	Approved
0.8366	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD3817	Phase 2
0.8345	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8322	Intermediate Similarity	NPD2796	Approved
0.8302	Intermediate Similarity	NPD7768	Phase 2
0.8301	Intermediate Similarity	NPD1511	Approved
0.8291	Intermediate Similarity	NPD2801	Approved
0.8278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD3748	Approved
0.8228	Intermediate Similarity	NPD6801	Discontinued
0.82	Intermediate Similarity	NPD2935	Discontinued
0.82	Intermediate Similarity	NPD1551	Phase 2
0.8194	Intermediate Similarity	NPD1512	Approved
0.8187	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3882	Suspended
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8158	Intermediate Similarity	NPD1243	Approved
0.8137	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4380	Phase 2
0.8095	Intermediate Similarity	NPD3268	Approved
0.8084	Intermediate Similarity	NPD7074	Phase 3
0.8082	Intermediate Similarity	NPD6832	Phase 2
0.8079	Intermediate Similarity	NPD6100	Approved
0.8079	Intermediate Similarity	NPD6099	Approved
0.8061	Intermediate Similarity	NPD6166	Phase 2
0.8061	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2800	Approved
0.8024	Intermediate Similarity	NPD7054	Approved
0.8024	Intermediate Similarity	NPD5844	Phase 1
0.8013	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD1203	Approved
0.8	Intermediate Similarity	NPD6651	Approved
0.7987	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7472	Approved
0.7964	Intermediate Similarity	NPD3818	Discontinued
0.7929	Intermediate Similarity	NPD5953	Discontinued
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD920	Approved
0.7911	Intermediate Similarity	NPD5403	Approved
0.7908	Intermediate Similarity	NPD2346	Discontinued
0.7901	Intermediate Similarity	NPD5402	Approved
0.7895	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7251	Discontinued
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4628	Phase 3
0.7836	Intermediate Similarity	NPD7808	Phase 3
0.7836	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7390	Discontinued
0.7831	Intermediate Similarity	NPD5711	Approved
0.7831	Intermediate Similarity	NPD5710	Approved
0.7824	Intermediate Similarity	NPD6797	Phase 2
0.7811	Intermediate Similarity	NPD7286	Phase 2
0.7793	Intermediate Similarity	NPD9717	Approved
0.7793	Intermediate Similarity	NPD1608	Approved
0.7792	Intermediate Similarity	NPD2344	Approved
0.7785	Intermediate Similarity	NPD5401	Approved
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7758	Intermediate Similarity	NPD919	Approved
0.7755	Intermediate Similarity	NPD2797	Approved
0.7755	Intermediate Similarity	NPD3267	Approved
0.7755	Intermediate Similarity	NPD3266	Approved
0.7724	Intermediate Similarity	NPD422	Phase 1
0.7719	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5494	Approved
0.7697	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3926	Phase 2
0.7665	Intermediate Similarity	NPD7199	Phase 2
0.7632	Intermediate Similarity	NPD943	Approved
0.7619	Intermediate Similarity	NPD7229	Phase 3
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD411	Approved
0.7595	Intermediate Similarity	NPD2309	Approved
0.7586	Intermediate Similarity	NPD17	Approved
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD447	Suspended
0.7582	Intermediate Similarity	NPD230	Phase 1
0.7582	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4288	Approved
0.7574	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3225	Approved
0.7562	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7033	Discontinued
0.7548	Intermediate Similarity	NPD4308	Phase 3
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7472	Intermediate Similarity	NPD4287	Approved
0.7472	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2798	Approved
0.7456	Intermediate Similarity	NPD1247	Approved
0.7455	Intermediate Similarity	NPD37	Approved
0.7452	Intermediate Similarity	NPD1471	Phase 3
0.744	Intermediate Similarity	NPD6234	Discontinued
0.7434	Intermediate Similarity	NPD4625	Phase 3
0.7425	Intermediate Similarity	NPD4965	Approved
0.7425	Intermediate Similarity	NPD4966	Approved
0.7425	Intermediate Similarity	NPD4967	Phase 2
0.7407	Intermediate Similarity	NPD6273	Approved
0.7403	Intermediate Similarity	NPD4060	Phase 1
0.7391	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1296	Phase 2
0.7365	Intermediate Similarity	NPD1201	Approved
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.736	Intermediate Similarity	NPD8434	Phase 2
0.7358	Intermediate Similarity	NPD2654	Approved
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7341	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1283	Approved
0.7329	Intermediate Similarity	NPD9545	Approved
0.7325	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7003	Approved
0.731	Intermediate Similarity	NPD9493	Approved
0.729	Intermediate Similarity	NPD4307	Phase 2
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1470	Approved
0.7278	Intermediate Similarity	NPD4477	Approved
0.7278	Intermediate Similarity	NPD4476	Approved
0.7273	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD4749	Approved
0.7263	Intermediate Similarity	NPD8151	Discontinued
0.7248	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1933	Approved
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7241	Intermediate Similarity	NPD7177	Discontinued
0.7241	Intermediate Similarity	NPD3751	Discontinued
0.7241	Intermediate Similarity	NPD7228	Approved
0.7237	Intermediate Similarity	NPD1019	Discontinued
0.723	Intermediate Similarity	NPD4626	Approved
0.7226	Intermediate Similarity	NPD8032	Phase 2
0.7225	Intermediate Similarity	NPD2403	Approved
0.7211	Intermediate Similarity	NPD1548	Phase 1
0.7209	Intermediate Similarity	NPD3787	Discontinued
0.7209	Intermediate Similarity	NPD6808	Phase 2
0.72	Intermediate Similarity	NPD3972	Approved
0.719	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7783	Phase 2
0.7181	Intermediate Similarity	NPD7435	Discontinued
0.7176	Intermediate Similarity	NPD6971	Discontinued
0.7175	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1164	Approved
0.7167	Intermediate Similarity	NPD8150	Discontinued
0.7161	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1281	Approved
0.7126	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4360	Phase 2
0.712	Intermediate Similarity	NPD4363	Phase 3
0.7114	Intermediate Similarity	NPD1778	Approved
0.7111	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1876	Approved
0.7097	Intermediate Similarity	NPD7095	Approved
0.7086	Intermediate Similarity	NPD1481	Phase 2
0.7083	Intermediate Similarity	NPD5889	Approved
0.7083	Intermediate Similarity	NPD5890	Approved
0.7081	Intermediate Similarity	NPD4361	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