NPASS Compound

Structure

NPC474542 OpenBabel07101718312D 31 33 0 0 1 0 0 0 0 0999 V2000 -2.7650 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9613 3.2711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2213 -1.3272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 -1.7096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 5.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2107 -0.5951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 0.3926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4336 -1.2244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 2.0096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4181 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3334 3.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8314 1.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9627 3.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4487 3.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4521 2.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1808 1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 4.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3998 3.6376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 29 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 15 2 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 19 2 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 30 1 0 0 0 0 17 22 1 0 0 0 0 17 25 1 1 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 21 2 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 6 0 0 0 22 24 1 0 0 0 0 23 27 2 0 0 0 0 24 28 2 0 0 0 0 24 31 1 0 0 0 0 25 4 1 6 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.2
Volume:	446.936
LogP:	5.164
LogD:	4.172
LogS:	-4.927
# Rotatable Bonds:	8
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	4.22
Fsp3:	0.44
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	2.1341247702366672e-05
Pgp-inhibitor:	0.164
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	96.23609161376953%
Volume Distribution (VD):	0.321
Pgp-substrate:	1.243890404701233%

ADMET: Metabolism

CYP1A2-inhibitor:	0.522
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.505
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.831
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	6.12
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.851
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.668
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.179
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.35

Download Data

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

Natural Product: NPC474542

Natural Product ID:	NPC474542
*Common Name:**	Fukanedone E
IUPAC Name:	(3S,4R,5R)-3-(2-hydroxy-4-methoxybenzoyl)-4,5-dimethyl-5-[(E)-4-methyl-5-(4-methylfuran-2-yl)pent-3-enyl]oxolan-2-one
Synonyms:	fukanedone E
Standard InCHIKey:	LHLJDPNWUZLDDY-YFWWFAMISA-N
Standard InCHI:	InChI=1S/C25H30O6/c1-15(11-19-12-16(2)14-30-19)7-6-10-25(4)17(3)22(24(28)31-25)23(27)20-9-8-18(29-5)13-21(20)26/h7-9,12-14,17,22,26H,6,10-11H2,1-5H3/b15-7+/t17-,22+,25-/m1/s1
SMILES:	COc1ccc(c(c1)O)C(=O)[C@H]1C(=O)O[C@]([C@@H]1C)(C)CC/C=C(/Cc1occ(c1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471594
PubChem CID:	21593959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15467238]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787437]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378364]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	76200.0	nM	PMID[497537]

☑ 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 NPC474542 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	333
0.1-0.2	1562
0.2-0.3	3608
0.3-0.4	8782
0.4-0.5	10042
0.5-0.6	4320
0.6-0.7	6145
0.7-0.8	6172
0.8-0.85	1593
0.85-0.9	139
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9145	High Similarity	NPC156244
0.9097	High Similarity	NPC296957
0.9097	High Similarity	NPC260902
0.9085	High Similarity	NPC67654
0.9032	High Similarity	NPC247677
0.9032	High Similarity	NPC160015
0.8974	High Similarity	NPC269495
0.8974	High Similarity	NPC270044
0.8917	High Similarity	NPC476349
0.8917	High Similarity	NPC476350
0.8917	High Similarity	NPC40583
0.8889	High Similarity	NPC120220
0.8874	High Similarity	NPC230943
0.8861	High Similarity	NPC115432
0.8861	High Similarity	NPC49009
0.8861	High Similarity	NPC260296
0.8844	High Similarity	NPC187826
0.8834	High Similarity	NPC472584
0.8831	High Similarity	NPC191104
0.8831	High Similarity	NPC155882
0.8824	High Similarity	NPC135325
0.8816	High Similarity	NPC299011
0.8812	High Similarity	NPC155640
0.8812	High Similarity	NPC91288
0.8808	High Similarity	NPC302181
0.8805	High Similarity	NPC14822
0.8797	High Similarity	NPC244750
0.8782	High Similarity	NPC122365
0.8782	High Similarity	NPC213608
0.8782	High Similarity	NPC1477
0.8776	High Similarity	NPC474726
0.8776	High Similarity	NPC475955
0.8766	High Similarity	NPC226644
0.8766	High Similarity	NPC88445
0.8766	High Similarity	NPC37226
0.8766	High Similarity	NPC296030
0.8766	High Similarity	NPC39929
0.8765	High Similarity	NPC320789
0.8758	High Similarity	NPC136641
0.8758	High Similarity	NPC130581
0.8758	High Similarity	NPC12148
0.875	High Similarity	NPC316535
0.875	High Similarity	NPC184649
0.875	High Similarity	NPC303185
0.875	High Similarity	NPC311144
0.8742	High Similarity	NPC202981
0.8742	High Similarity	NPC53192
0.8742	High Similarity	NPC95472
0.8742	High Similarity	NPC239270
0.8742	High Similarity	NPC303210
0.8742	High Similarity	NPC169
0.8734	High Similarity	NPC65504
0.8725	High Similarity	NPC124269
0.8718	High Similarity	NPC207624
0.8718	High Similarity	NPC5871
0.8718	High Similarity	NPC41326
0.8718	High Similarity	NPC263676
0.8707	High Similarity	NPC236974
0.8707	High Similarity	NPC144027
0.8704	High Similarity	NPC323137
0.8701	High Similarity	NPC39195
0.8693	High Similarity	NPC300267
0.8693	High Similarity	NPC477955
0.8693	High Similarity	NPC210826
0.8693	High Similarity	NPC51641
0.8688	High Similarity	NPC304387
0.8688	High Similarity	NPC92589
0.8684	High Similarity	NPC113770
0.8658	High Similarity	NPC188879
0.8654	High Similarity	NPC58668
0.8654	High Similarity	NPC193976
0.8654	High Similarity	NPC23668
0.8654	High Similarity	NPC290671
0.8654	High Similarity	NPC170169
0.8654	High Similarity	NPC116604
0.8654	High Similarity	NPC115324
0.8654	High Similarity	NPC106372
0.865	High Similarity	NPC476459
0.8645	High Similarity	NPC221868
0.8645	High Similarity	NPC37208
0.8645	High Similarity	NPC317492
0.8642	High Similarity	NPC329215
0.8642	High Similarity	NPC204088
0.8642	High Similarity	NPC259007
0.8636	High Similarity	NPC113428
0.8636	High Similarity	NPC304443
0.8636	High Similarity	NPC61284
0.8636	High Similarity	NPC74539
0.8636	High Similarity	NPC17816
0.8636	High Similarity	NPC308200
0.8627	High Similarity	NPC271288
0.8627	High Similarity	NPC469953
0.8627	High Similarity	NPC311741
0.8627	High Similarity	NPC234629
0.8625	High Similarity	NPC304839
0.8625	High Similarity	NPC220582
0.8618	High Similarity	NPC472006
0.8609	High Similarity	NPC16455
0.8609	High Similarity	NPC307990
0.8609	High Similarity	NPC284550
0.8609	High Similarity	NPC129853
0.8609	High Similarity	NPC76445
0.8608	High Similarity	NPC148938
0.8608	High Similarity	NPC198490
0.8608	High Similarity	NPC99199
0.86	High Similarity	NPC470399
0.8599	High Similarity	NPC142308
0.8591	High Similarity	NPC213603
0.8591	High Similarity	NPC470397
0.8591	High Similarity	NPC470398
0.8591	High Similarity	NPC156910
0.8591	High Similarity	NPC240593
0.859	High Similarity	NPC167576
0.859	High Similarity	NPC29777
0.859	High Similarity	NPC471115
0.859	High Similarity	NPC472406
0.859	High Similarity	NPC472421
0.859	High Similarity	NPC230713
0.859	High Similarity	NPC78335
0.8589	High Similarity	NPC53640
0.8581	High Similarity	NPC168085
0.8581	High Similarity	NPC272194
0.8581	High Similarity	NPC145467
0.8581	High Similarity	NPC266572
0.8581	High Similarity	NPC266743
0.858	High Similarity	NPC109180
0.858	High Similarity	NPC471286
0.8571	High Similarity	NPC470322
0.8571	High Similarity	NPC154217
0.8571	High Similarity	NPC25844
0.8571	High Similarity	NPC308799
0.8571	High Similarity	NPC203817
0.8571	High Similarity	NPC472033
0.8562	High Similarity	NPC472877
0.8562	High Similarity	NPC131043
0.8562	High Similarity	NPC105381
0.8562	High Similarity	NPC473976
0.8562	High Similarity	NPC109812
0.8562	High Similarity	NPC106985
0.8562	High Similarity	NPC225884
0.8562	High Similarity	NPC313039
0.8562	High Similarity	NPC198459
0.8562	High Similarity	NPC10302
0.8562	High Similarity	NPC166138
0.8562	High Similarity	NPC18585
0.8553	High Similarity	NPC109967
0.8553	High Similarity	NPC129053
0.8553	High Similarity	NPC321372
0.8553	High Similarity	NPC469936
0.8553	High Similarity	NPC470625
0.8553	High Similarity	NPC78554
0.8553	High Similarity	NPC474609
0.8553	High Similarity	NPC474738
0.8553	High Similarity	NPC13879
0.8553	High Similarity	NPC475797
0.8553	High Similarity	NPC171870
0.8544	High Similarity	NPC183874
0.8544	High Similarity	NPC131725
0.8544	High Similarity	NPC72370
0.8544	High Similarity	NPC235333
0.8544	High Similarity	NPC42458
0.8544	High Similarity	NPC158261
0.8544	High Similarity	NPC472462
0.8543	High Similarity	NPC37206
0.8543	High Similarity	NPC261234
0.8543	High Similarity	NPC316480
0.8543	High Similarity	NPC477956
0.8543	High Similarity	NPC137009
0.8543	High Similarity	NPC23257
0.8535	High Similarity	NPC316960
0.8535	High Similarity	NPC474744
0.8535	High Similarity	NPC148945
0.8535	High Similarity	NPC318424
0.8535	High Similarity	NPC474772
0.8535	High Similarity	NPC472423
0.8535	High Similarity	NPC317715
0.8535	High Similarity	NPC78835
0.8535	High Similarity	NPC209142
0.8535	High Similarity	NPC312549
0.8535	High Similarity	NPC204561
0.8535	High Similarity	NPC309512
0.8535	High Similarity	NPC471229
0.8535	High Similarity	NPC472580
0.8528	High Similarity	NPC291110
0.8526	High Similarity	NPC164205
0.8526	High Similarity	NPC473016
0.8526	High Similarity	NPC471114
0.8526	High Similarity	NPC104236
0.8526	High Similarity	NPC214493
0.8526	High Similarity	NPC178202
0.8516	High Similarity	NPC97716
0.8516	High Similarity	NPC237635
0.8516	High Similarity	NPC79469
0.8516	High Similarity	NPC201731
0.8516	High Similarity	NPC24673
0.8516	High Similarity	NPC104406
0.8506	High Similarity	NPC196137
0.8506	High Similarity	NPC1886
0.8506	High Similarity	NPC209040
0.8506	High Similarity	NPC472034

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 NPC474542 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	919
0.2-0.3	1719
0.3-0.4	2574
0.4-0.5	2041
0.5-0.6	1110
0.6-0.7	325
0.7-0.8	135
0.8-0.85	29
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD920	Approved
0.8616	High Similarity	NPD3749	Approved
0.8506	High Similarity	NPD642	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD1551	Phase 2
0.8323	Intermediate Similarity	NPD6799	Approved
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8302	Intermediate Similarity	NPD7411	Suspended
0.8301	Intermediate Similarity	NPD1243	Approved
0.8289	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD2344	Approved
0.8278	Intermediate Similarity	NPD1510	Phase 2
0.8272	Intermediate Similarity	NPD7075	Discontinued
0.8269	Intermediate Similarity	NPD2534	Approved
0.8269	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD2532	Approved
0.8269	Intermediate Similarity	NPD2533	Approved
0.8255	Intermediate Similarity	NPD1240	Approved
0.8239	Intermediate Similarity	NPD6599	Discontinued
0.8235	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2796	Approved
0.821	Intermediate Similarity	NPD3882	Suspended
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2800	Approved
0.8153	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1607	Approved
0.8129	Intermediate Similarity	NPD3750	Approved
0.811	Intermediate Similarity	NPD919	Approved
0.8098	Intermediate Similarity	NPD7768	Phase 2
0.8084	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2309	Approved
0.8039	Intermediate Similarity	NPD2799	Discontinued
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1934	Approved
0.7901	Intermediate Similarity	NPD4380	Phase 2
0.7882	Intermediate Similarity	NPD3818	Discontinued
0.7866	Intermediate Similarity	NPD2801	Approved
0.7849	Intermediate Similarity	NPD5953	Discontinued
0.7844	Intermediate Similarity	NPD5494	Approved
0.7818	Intermediate Similarity	NPD3817	Phase 2
0.7811	Intermediate Similarity	NPD3926	Phase 2
0.7806	Intermediate Similarity	NPD3748	Approved
0.7798	Intermediate Similarity	NPD1247	Approved
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.775	Intermediate Similarity	NPD1511	Approved
0.7733	Intermediate Similarity	NPD7286	Phase 2
0.7719	Intermediate Similarity	NPD7473	Discontinued
0.7716	Intermediate Similarity	NPD5403	Approved
0.7703	Intermediate Similarity	NPD9717	Approved
0.7684	Intermediate Similarity	NPD8434	Phase 2
0.7677	Intermediate Similarity	NPD6651	Approved
0.7673	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1203	Approved
0.7657	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1512	Approved
0.7647	Intermediate Similarity	NPD6232	Discontinued
0.7632	Intermediate Similarity	NPD6832	Phase 2
0.7605	Intermediate Similarity	NPD5402	Approved
0.7598	Intermediate Similarity	NPD4287	Approved
0.7593	Intermediate Similarity	NPD5401	Approved
0.7588	Intermediate Similarity	NPD6959	Discontinued
0.758	Intermediate Similarity	NPD7033	Discontinued
0.7572	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6166	Phase 2
0.7558	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5761	Phase 2
0.7545	Intermediate Similarity	NPD5760	Phase 2
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD6808	Phase 2
0.7544	Intermediate Similarity	NPD5711	Approved
0.7532	Intermediate Similarity	NPD3764	Approved
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD3268	Approved
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD2296	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7486	Intermediate Similarity	NPD7074	Phase 3
0.7483	Intermediate Similarity	NPD9545	Approved
0.7458	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2797	Approved
0.7429	Intermediate Similarity	NPD7054	Approved
0.7429	Intermediate Similarity	NPD5844	Phase 1
0.7421	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD6100	Approved
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.74	Intermediate Similarity	NPD422	Phase 1
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2654	Approved
0.7389	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD2798	Approved
0.7386	Intermediate Similarity	NPD1729	Discontinued
0.7386	Intermediate Similarity	NPD7472	Approved
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7381	Intermediate Similarity	NPD6280	Approved
0.7381	Intermediate Similarity	NPD6279	Approved
0.7378	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6005	Phase 3
0.7375	Intermediate Similarity	NPD1471	Phase 3
0.7375	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6002	Phase 3
0.7375	Intermediate Similarity	NPD6004	Phase 3
0.7375	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4308	Phase 3
0.7351	Intermediate Similarity	NPD1608	Approved
0.7347	Intermediate Similarity	NPD9493	Approved
0.7345	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6797	Phase 2
0.7341	Intermediate Similarity	NPD7229	Phase 3
0.7337	Intermediate Similarity	NPD1465	Phase 2
0.7325	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD411	Approved
0.7308	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7251	Discontinued
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7278	Intermediate Similarity	NPD5124	Phase 1
0.7278	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1019	Discontinued
0.7267	Intermediate Similarity	NPD6234	Discontinued
0.7263	Intermediate Similarity	NPD7808	Phase 3
0.7257	Intermediate Similarity	NPD2403	Approved
0.7251	Intermediate Similarity	NPD4967	Phase 2
0.7251	Intermediate Similarity	NPD4965	Approved
0.7251	Intermediate Similarity	NPD4966	Approved
0.725	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3267	Approved
0.7208	Intermediate Similarity	NPD3266	Approved
0.7207	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4361	Phase 2
0.7202	Intermediate Similarity	NPD7458	Discontinued
0.7193	Intermediate Similarity	NPD4288	Approved
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3972	Approved
0.7107	Intermediate Similarity	NPD4307	Phase 2
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1296	Phase 2
0.7076	Intermediate Similarity	NPD37	Approved
0.7074	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1933	Approved
0.7059	Intermediate Similarity	NPD4363	Phase 3
0.7059	Intermediate Similarity	NPD4360	Phase 2
0.7051	Intermediate Similarity	NPD5647	Approved
0.7037	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8312	Approved
0.7033	Intermediate Similarity	NPD8313	Approved
0.7032	Intermediate Similarity	NPD1876	Approved
0.7032	Intermediate Similarity	NPD3225	Approved
0.703	Intermediate Similarity	NPD7003	Approved
0.7024	Intermediate Similarity	NPD6273	Approved
0.702	Intermediate Similarity	NPD1548	Phase 1
0.7017	Intermediate Similarity	NPD6764	Approved
0.7017	Intermediate Similarity	NPD6765	Approved
0.7006	Intermediate Similarity	NPD9494	Approved
0.6988	Remote Similarity	NPD3887	Approved
0.6988	Remote Similarity	NPD2354	Approved
0.6987	Remote Similarity	NPD1164	Approved
0.6983	Remote Similarity	NPD7228	Approved
0.6983	Remote Similarity	NPD3751	Discontinued
0.6981	Remote Similarity	NPD6798	Discontinued
0.6968	Remote Similarity	NPD4749	Approved
0.6928	Remote Similarity	NPD1778	Approved
0.6923	Remote Similarity	NPD6104	Discontinued
0.6914	Remote Similarity	NPD6971	Discontinued
0.6913	Remote Similarity	NPD1241	Discontinued
0.691	Remote Similarity	NPD5242	Approved
0.6905	Remote Similarity	NPD7390	Discontinued
0.6894	Remote Similarity	NPD4060	Phase 1
0.689	Remote Similarity	NPD5404	Approved
0.689	Remote Similarity	NPD4477	Approved
0.689	Remote Similarity	NPD5408	Approved
0.689	Remote Similarity	NPD5406	Approved
0.689	Remote Similarity	NPD4476	Approved
0.689	Remote Similarity	NPD5405	Approved
0.6875	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1699	Clinical (unspecified phase)

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