NPASS Compound

Structure

NPC470669 OpenBabel07101718302D 25 26 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -3.9641 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 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -2.2321 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 -1.8660 -0.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 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 1.7321 -2.0000 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 1.7321 -0.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 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 3.4641 -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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 13 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 21 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 13 2 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 11 21 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 24 2 0 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	374.001
LogP:	5.767
LogD:	4.922
LogS:	-3.953
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	3.933
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.718
MDCK Permeability:	2.2712605641572736e-05
Pgp-inhibitor:	0.885
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	100.27685546875%
Volume Distribution (VD):	3.214
Pgp-substrate:	2.736598253250122%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.508
CYP2C19-inhibitor:	0.842
CYP2C19-substrate:	0.456
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.944
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	9.384
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.686
Drug-inuced Liver Injury (DILI):	0.486
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.539
Skin Sensitization:	0.856
Carcinogencity:	0.639
Eye Corrosion:	0.003
Eye Irritation:	0.424
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC470669

Natural Product ID:	NPC470669
*Common Name:**	Empetrikarinen B
IUPAC Name:	1-[5,7-dihydroxy-2-methyl-2-(4-methylpent-3-enyl)chromen-8-yl]-2-methylbutan-1-one
Synonyms:	Empetrikarinen B
Standard InCHIKey:	UAJYKGPSRWOQCL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H28O4/c1-6-14(4)19(24)18-17(23)12-16(22)15-9-11-21(5,25-20(15)18)10-7-8-13(2)3/h8-9,11-12,14,22-23H,6-7,10H2,1-5H3
SMILES:	CCC(C)C(=O)C1=C(C=C(C2=C1OC(C=C2)(C)CCC=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152492
PubChem CID:	71461985
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000350] Butyrophenones

*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
NPO33078	hypericum empetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23030826]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15000.0	nM	PMID[572482]

☑ 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 NPC470669 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	367
0.1-0.2	1571
0.2-0.3	4160
0.3-0.4	10969
0.4-0.5	7371
0.5-0.6	3828
0.6-0.7	6247
0.7-0.8	5102
0.8-0.85	1726
0.85-0.9	905
0.9-0.95	428
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470668
0.9776	High Similarity	NPC23257
0.9704	High Similarity	NPC471587
0.9701	High Similarity	NPC470671
0.9701	High Similarity	NPC470672
0.9701	High Similarity	NPC474487
0.9701	High Similarity	NPC131130
0.9701	High Similarity	NPC474504
0.9699	High Similarity	NPC174999
0.9632	High Similarity	NPC64908
0.9632	High Similarity	NPC118840
0.9632	High Similarity	NPC156590
0.9632	High Similarity	NPC147688
0.9632	High Similarity	NPC282300
0.9632	High Similarity	NPC205006
0.963	High Similarity	NPC55018
0.963	High Similarity	NPC220062
0.963	High Similarity	NPC96565
0.963	High Similarity	NPC216978
0.963	High Similarity	NPC303633
0.963	High Similarity	NPC301217
0.9624	High Similarity	NPC151113
0.9624	High Similarity	NPC101752
0.9621	High Similarity	NPC108113
0.9621	High Similarity	NPC93756
0.9562	High Similarity	NPC226636
0.9562	High Similarity	NPC62840
0.9562	High Similarity	NPC59739
0.9562	High Similarity	NPC293852
0.9562	High Similarity	NPC11561
0.9562	High Similarity	NPC299080
0.9562	High Similarity	NPC78803
0.9562	High Similarity	NPC214236
0.9562	High Similarity	NPC217083
0.9559	High Similarity	NPC159275
0.9559	High Similarity	NPC305355
0.9559	High Similarity	NPC477272
0.9559	High Similarity	NPC150522
0.9559	High Similarity	NPC235239
0.9559	High Similarity	NPC261227
0.9559	High Similarity	NPC241100
0.9559	High Similarity	NPC475680
0.9559	High Similarity	NPC270883
0.9559	High Similarity	NPC172986
0.9556	High Similarity	NPC201395
0.9552	High Similarity	NPC156910
0.9552	High Similarity	NPC187826
0.9549	High Similarity	NPC125920
0.9545	High Similarity	NPC10971
0.9496	High Similarity	NPC329678
0.9493	High Similarity	NPC219915
0.9493	High Similarity	NPC38219
0.9489	High Similarity	NPC110969
0.9489	High Similarity	NPC103362
0.9485	High Similarity	NPC53181
0.9485	High Similarity	NPC217186
0.9485	High Similarity	NPC18260
0.9485	High Similarity	NPC139554
0.9485	High Similarity	NPC78913
0.9478	High Similarity	NPC60667
0.9424	High Similarity	NPC234629
0.9424	High Similarity	NPC311741
0.9424	High Similarity	NPC131568
0.9424	High Similarity	NPC326500
0.9424	High Similarity	NPC131579
0.942	High Similarity	NPC144499
0.942	High Similarity	NPC200694
0.942	High Similarity	NPC204469
0.9416	High Similarity	NPC69769
0.9407	High Similarity	NPC13408
0.9403	High Similarity	NPC144027
0.9403	High Similarity	NPC236974
0.9398	High Similarity	NPC25937
0.9394	High Similarity	NPC270369
0.9394	High Similarity	NPC5515
0.9357	High Similarity	NPC88964
0.9357	High Similarity	NPC470647
0.9357	High Similarity	NPC312973
0.9357	High Similarity	NPC142405
0.9357	High Similarity	NPC474161
0.9357	High Similarity	NPC54577
0.9357	High Similarity	NPC477955
0.9357	High Similarity	NPC67805
0.9357	High Similarity	NPC475052
0.9357	High Similarity	NPC83357
0.9357	High Similarity	NPC246948
0.9357	High Similarity	NPC301276
0.9357	High Similarity	NPC476088
0.9357	High Similarity	NPC111786
0.9357	High Similarity	NPC20488
0.9357	High Similarity	NPC195621
0.9357	High Similarity	NPC154217
0.9357	High Similarity	NPC124729
0.9357	High Similarity	NPC267375
0.9357	High Similarity	NPC285630
0.9357	High Similarity	NPC176229
0.9357	High Similarity	NPC214774
0.9357	High Similarity	NPC127059
0.9353	High Similarity	NPC212932
0.9353	High Similarity	NPC81697
0.9353	High Similarity	NPC85162
0.9353	High Similarity	NPC478086
0.9353	High Similarity	NPC106985
0.9353	High Similarity	NPC9117
0.9353	High Similarity	NPC11700
0.9353	High Similarity	NPC278249
0.9353	High Similarity	NPC87609
0.9353	High Similarity	NPC166138
0.9353	High Similarity	NPC190637
0.9353	High Similarity	NPC24821
0.9353	High Similarity	NPC188632
0.9353	High Similarity	NPC214166
0.9353	High Similarity	NPC94794
0.9353	High Similarity	NPC18585
0.9353	High Similarity	NPC196459
0.9353	High Similarity	NPC112791
0.9353	High Similarity	NPC316816
0.9353	High Similarity	NPC293053
0.9353	High Similarity	NPC125894
0.9353	High Similarity	NPC107177
0.9353	High Similarity	NPC223812
0.9353	High Similarity	NPC470296
0.9353	High Similarity	NPC77794
0.9348	High Similarity	NPC470555
0.9348	High Similarity	NPC14871
0.9343	High Similarity	NPC473076
0.9343	High Similarity	NPC472343
0.9343	High Similarity	NPC240305
0.9338	High Similarity	NPC317119
0.9338	High Similarity	NPC131782
0.9338	High Similarity	NPC153979
0.9338	High Similarity	NPC474624
0.9338	High Similarity	NPC138047
0.9333	High Similarity	NPC46869
0.9333	High Similarity	NPC13575
0.9323	High Similarity	NPC473584
0.9323	High Similarity	NPC475589
0.9323	High Similarity	NPC31872
0.9291	High Similarity	NPC104406
0.9291	High Similarity	NPC296998
0.9291	High Similarity	NPC166757
0.9291	High Similarity	NPC473077
0.9291	High Similarity	NPC79469
0.9291	High Similarity	NPC97716
0.9291	High Similarity	NPC23728
0.9291	High Similarity	NPC297886
0.9291	High Similarity	NPC283234
0.9291	High Similarity	NPC201731
0.9291	High Similarity	NPC14001
0.9291	High Similarity	NPC24673
0.9291	High Similarity	NPC249942
0.9291	High Similarity	NPC237635
0.9291	High Similarity	NPC110303
0.9286	High Similarity	NPC178627
0.9286	High Similarity	NPC257236
0.9286	High Similarity	NPC273538
0.9286	High Similarity	NPC278175
0.9286	High Similarity	NPC271288
0.9286	High Similarity	NPC469953
0.9286	High Similarity	NPC196137
0.9286	High Similarity	NPC319752
0.9286	High Similarity	NPC209040
0.9286	High Similarity	NPC1886
0.9286	High Similarity	NPC473013
0.9286	High Similarity	NPC473014
0.9286	High Similarity	NPC235217
0.9286	High Similarity	NPC473015
0.9286	High Similarity	NPC216538
0.9286	High Similarity	NPC469935
0.9281	High Similarity	NPC32739
0.9281	High Similarity	NPC161506
0.9281	High Similarity	NPC306829
0.9281	High Similarity	NPC36181
0.9281	High Similarity	NPC227579
0.9281	High Similarity	NPC78
0.9281	High Similarity	NPC66515
0.9281	High Similarity	NPC166482
0.9281	High Similarity	NPC64915
0.9281	High Similarity	NPC220998
0.9281	High Similarity	NPC177354
0.9281	High Similarity	NPC125855
0.9281	High Similarity	NPC182852
0.9281	High Similarity	NPC167624
0.9281	High Similarity	NPC228504
0.9281	High Similarity	NPC148757
0.9281	High Similarity	NPC166934
0.9281	High Similarity	NPC473042
0.9281	High Similarity	NPC107572
0.9281	High Similarity	NPC324134
0.9281	High Similarity	NPC37496
0.9281	High Similarity	NPC194432
0.9281	High Similarity	NPC324436
0.9281	High Similarity	NPC223500
0.9281	High Similarity	NPC328164
0.9281	High Similarity	NPC40833
0.9281	High Similarity	NPC76372
0.9281	High Similarity	NPC1089
0.9281	High Similarity	NPC265040
0.9281	High Similarity	NPC76338
0.9281	High Similarity	NPC10937

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 NPC470669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	963
0.2-0.3	1597
0.3-0.4	2690
0.4-0.5	1819
0.5-0.6	1157
0.6-0.7	409
0.7-0.8	137
0.8-0.85	27
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD7410	Clinical (unspecified phase)
0.9286	High Similarity	NPD4378	Clinical (unspecified phase)
0.8921	High Similarity	NPD1550	Clinical (unspecified phase)
0.8921	High Similarity	NPD1552	Clinical (unspecified phase)
0.8897	High Similarity	NPD1240	Approved
0.8857	High Similarity	NPD1549	Phase 2
0.8777	High Similarity	NPD1510	Phase 2
0.8768	High Similarity	NPD1607	Approved
0.8725	High Similarity	NPD8443	Clinical (unspecified phase)
0.8714	High Similarity	NPD2796	Approved
0.8662	High Similarity	NPD2800	Approved
0.8658	High Similarity	NPD2393	Clinical (unspecified phase)
0.8649	High Similarity	NPD7411	Suspended
0.8633	High Similarity	NPD6651	Approved
0.8592	High Similarity	NPD970	Clinical (unspecified phase)
0.8581	High Similarity	NPD4380	Phase 2
0.8552	High Similarity	NPD1511	Approved
0.8487	Intermediate Similarity	NPD7075	Discontinued
0.8467	Intermediate Similarity	NPD6801	Discontinued
0.8435	Intermediate Similarity	NPD1512	Approved
0.8425	Intermediate Similarity	NPD6799	Approved
0.8411	Intermediate Similarity	NPD7819	Suspended
0.8411	Intermediate Similarity	NPD2801	Approved
0.8411	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1243	Approved
0.8345	Intermediate Similarity	NPD3750	Approved
0.8344	Intermediate Similarity	NPD1934	Approved
0.8276	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD2799	Discontinued
0.8247	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD7768	Phase 2
0.8182	Intermediate Similarity	NPD3882	Suspended
0.8165	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD920	Approved
0.8129	Intermediate Similarity	NPD3749	Approved
0.8125	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2533	Approved
0.8121	Intermediate Similarity	NPD2532	Approved
0.8121	Intermediate Similarity	NPD2534	Approved
0.8108	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6959	Discontinued
0.8088	Intermediate Similarity	NPD422	Phase 1
0.8069	Intermediate Similarity	NPD1551	Phase 2
0.8069	Intermediate Similarity	NPD2935	Discontinued
0.8069	Intermediate Similarity	NPD6099	Approved
0.8069	Intermediate Similarity	NPD6100	Approved
0.8037	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD9717	Approved
0.8014	Intermediate Similarity	NPD2344	Approved
0.8	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7986	Intermediate Similarity	NPD1203	Approved
0.7973	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD3268	Approved
0.7958	Intermediate Similarity	NPD2313	Discontinued
0.7937	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6166	Phase 2
0.7917	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5124	Phase 1
0.7914	Intermediate Similarity	NPD5953	Discontinued
0.7911	Intermediate Similarity	NPD5494	Approved
0.7901	Intermediate Similarity	NPD7286	Phase 2
0.7895	Intermediate Similarity	NPD5403	Approved
0.7888	Intermediate Similarity	NPD7473	Discontinued
0.7857	Intermediate Similarity	NPD2797	Approved
0.784	Intermediate Similarity	NPD3818	Discontinued
0.7832	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6232	Discontinued
0.7801	Intermediate Similarity	NPD2798	Approved
0.78	Intermediate Similarity	NPD2309	Approved
0.7791	Intermediate Similarity	NPD7054	Approved
0.7785	Intermediate Similarity	NPD2654	Approved
0.7763	Intermediate Similarity	NPD5401	Approved
0.7755	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7033	Discontinued
0.7744	Intermediate Similarity	NPD7472	Approved
0.7744	Intermediate Similarity	NPD7074	Phase 3
0.7736	Intermediate Similarity	NPD919	Approved
0.7724	Intermediate Similarity	NPD943	Approved
0.7708	Intermediate Similarity	NPD1296	Phase 2
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD6832	Phase 2
0.7692	Intermediate Similarity	NPD4908	Phase 1
0.7677	Intermediate Similarity	NPD3226	Approved
0.7664	Intermediate Similarity	NPD1548	Phase 1
0.7651	Intermediate Similarity	NPD6559	Discontinued
0.7651	Intermediate Similarity	NPD7251	Discontinued
0.764	Intermediate Similarity	NPD1247	Approved
0.7635	Intermediate Similarity	NPD4308	Phase 3
0.7616	Intermediate Similarity	NPD4628	Phase 3
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3266	Approved
0.7606	Intermediate Similarity	NPD3267	Approved
0.7605	Intermediate Similarity	NPD7808	Phase 3
0.7589	Intermediate Similarity	NPD4749	Approved
0.7582	Intermediate Similarity	NPD7390	Discontinued
0.7572	Intermediate Similarity	NPD4360	Phase 2
0.7572	Intermediate Similarity	NPD4363	Phase 3
0.7571	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1610	Phase 2
0.7547	Intermediate Similarity	NPD5402	Approved
0.7536	Intermediate Similarity	NPD9545	Approved
0.7535	Intermediate Similarity	NPD3225	Approved
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.753	Intermediate Similarity	NPD1729	Discontinued
0.7529	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4361	Phase 2
0.7518	Intermediate Similarity	NPD1608	Approved
0.7518	Intermediate Similarity	NPD9493	Approved
0.7517	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD5711	Approved
0.747	Intermediate Similarity	NPD5844	Phase 1
0.7468	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD411	Approved
0.7439	Intermediate Similarity	NPD3926	Phase 2
0.7432	Intermediate Similarity	NPD447	Suspended
0.7426	Intermediate Similarity	NPD1241	Discontinued
0.7394	Intermediate Similarity	NPD3972	Approved
0.7394	Intermediate Similarity	NPD2403	Approved
0.7386	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4307	Phase 2
0.7357	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6104	Discontinued
0.7329	Intermediate Similarity	NPD4288	Approved
0.7329	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD230	Phase 1
0.731	Intermediate Similarity	NPD1019	Discontinued
0.7305	Intermediate Similarity	NPD17	Approved
0.7296	Intermediate Similarity	NPD6585	Discontinued
0.7285	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1465	Phase 2
0.7261	Intermediate Similarity	NPD5049	Phase 3
0.7255	Intermediate Similarity	NPD2424	Discontinued
0.7241	Intermediate Similarity	NPD1164	Approved
0.7233	Intermediate Similarity	NPD7458	Discontinued
0.723	Intermediate Similarity	NPD3764	Approved
0.7226	Intermediate Similarity	NPD2354	Approved
0.7222	Intermediate Similarity	NPD2296	Approved
0.7215	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1933	Approved
0.7197	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6004	Phase 3
0.719	Intermediate Similarity	NPD1471	Phase 3
0.719	Intermediate Similarity	NPD6002	Phase 3
0.719	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6005	Phase 3
0.719	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7229	Phase 3
0.7161	Intermediate Similarity	NPD7003	Approved
0.7153	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5889	Approved
0.7143	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD5890	Approved
0.7133	Intermediate Similarity	NPD3142	Approved
0.7133	Intermediate Similarity	NPD3140	Approved
0.7125	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5405	Approved
0.7124	Intermediate Similarity	NPD5406	Approved
0.7124	Intermediate Similarity	NPD5404	Approved
0.7124	Intermediate Similarity	NPD5408	Approved
0.7123	Intermediate Similarity	NPD1470	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7121	Intermediate Similarity	NPD940	Approved
0.712	Intermediate Similarity	NPD7584	Approved
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7101	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1652	Phase 2
0.7086	Intermediate Similarity	NPD6355	Discontinued
0.7083	Intermediate Similarity	NPD1535	Discovery
0.7078	Intermediate Similarity	NPD2353	Approved
0.7078	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6671	Approved
0.7062	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9266	Approved
0.7059	Intermediate Similarity	NPD74	Approved
0.7055	Intermediate Similarity	NPD5761	Phase 2
0.7055	Intermediate Similarity	NPD5760	Phase 2
0.7055	Intermediate Similarity	NPD1876	Approved
0.7041	Intermediate Similarity	NPD3446	Phase 1
0.7025	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1613	Approved
0.702	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4060	Phase 1
0.7013	Intermediate Similarity	NPD4477	Approved
0.7013	Intermediate Similarity	NPD4476	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