NPASS Compound

Structure

NPC470988 OpenBabel07101718292D 30 31 0 0 1 0 0 0 0 0999 V2000 -1.6779 -2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5507 2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3896 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8727 -3.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7117 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7117 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5507 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 0.4844 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.0338 -2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8727 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 -0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8727 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -3.3906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 -1.4531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 0.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7117 -1.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 -1.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 1.4531 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 7 1 0 0 0 0 2 10 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 15 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 24 2 0 0 0 0 13 14 2 0 0 0 0 13 30 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 2 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.24
Volume:	522.325
LogP:	6.238
LogD:	2.648
LogS:	-3.675
# Rotatable Bonds:	11
TPSA:	145.27
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	3.882
Fsp3:	0.464
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.006
MDCK Permeability:	1.5536863429588266e-05
Pgp-inhibitor:	0.838
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.272
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	99.41936492919922%
Volume Distribution (VD):	0.311
Pgp-substrate:	0.975485622882843%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.546
CYP2C19-substrate:	0.626
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.388
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	1.582
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.803
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.861
Skin Sensitization:	0.833
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.173
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC470988

Natural Product ID:	NPC470988
*Common Name:**	3-[1-[3-Acetyl-2,4,6-Trihydroxy-5-(3-Methylbut-2-Enyl)Phenyl]Ethyl]-5-Ethyl-4-Hydroxy-6-Methylpyran-2-One
IUPAC Name:	3-[1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]ethyl]-5-ethyl-4-hydroxy-6-methylpyran-2-one
Synonyms:
Standard InCHIKey:	LVDPVGRUFHBLMZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H28O7/c1-7-14-13(6)30-23(29)17(19(14)25)11(4)16-20(26)15(9-8-10(2)3)21(27)18(12(5)24)22(16)28/h8,11,25-28H,7,9H2,1-6H3
SMILES:	CCC1=C(OC(=O)C(=C1O)C(C)C2=C(C(=C(C(=C2O)CC=C(C)C)O)C(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334820
PubChem CID:	71720684
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
NPO25148.1	Helichrysum italicum	Under-species	n.a.	n.a.	Flowered aerial parts	Arzana, Sardinia	2010-Jul	PMID[23265253]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[564888]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[564888]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[564888]

☑ 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 NPC470988 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	346
0.1-0.2	1549
0.2-0.3	3891
0.3-0.4	9007
0.4-0.5	10183
0.5-0.6	4210
0.6-0.7	6189
0.7-0.8	4926
0.8-0.85	1576
0.85-0.9	697
0.9-0.95	98
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC470984
0.9764	High Similarity	NPC185624
0.9762	High Similarity	NPC470987
0.9762	High Similarity	NPC21378
0.9692	High Similarity	NPC470985
0.9692	High Similarity	NPC470989
0.9474	High Similarity	NPC470986
0.9398	High Similarity	NPC183639
0.9398	High Similarity	NPC199458
0.9328	High Similarity	NPC241975
0.9328	High Similarity	NPC19476
0.9323	High Similarity	NPC131782
0.9323	High Similarity	NPC474624
0.9323	High Similarity	NPC138047
0.9254	High Similarity	NPC470083
0.9254	High Similarity	NPC219584
0.9124	High Similarity	NPC470556
0.9058	High Similarity	NPC96216
0.9058	High Similarity	NPC470553
0.9058	High Similarity	NPC470909
0.9058	High Similarity	NPC474939
0.9058	High Similarity	NPC307895
0.9051	High Similarity	NPC470555
0.9044	High Similarity	NPC472343
0.903	High Similarity	NPC50455
0.9	High Similarity	NPC470981
0.8993	High Similarity	NPC288910
0.8993	High Similarity	NPC118059
0.8993	High Similarity	NPC1886
0.8993	High Similarity	NPC470554
0.8993	High Similarity	NPC196137
0.8993	High Similarity	NPC133060
0.8986	High Similarity	NPC294432
0.8986	High Similarity	NPC472344
0.8986	High Similarity	NPC112829
0.8978	High Similarity	NPC221173
0.8963	High Similarity	NPC470982
0.8963	High Similarity	NPC470983
0.8947	High Similarity	NPC285054
0.8929	High Similarity	NPC154217
0.8929	High Similarity	NPC470910
0.8929	High Similarity	NPC470322
0.8929	High Similarity	NPC181388
0.8921	High Similarity	NPC470296
0.8921	High Similarity	NPC188632
0.8921	High Similarity	NPC87609
0.8921	High Similarity	NPC94794
0.8921	High Similarity	NPC184738
0.8921	High Similarity	NPC112791
0.8921	High Similarity	NPC33653
0.8921	High Similarity	NPC196459
0.8897	High Similarity	NPC255801
0.8897	High Similarity	NPC322301
0.8889	High Similarity	NPC101752
0.8881	High Similarity	NPC175943
0.8865	High Similarity	NPC474108
0.8865	High Similarity	NPC177995
0.8857	High Similarity	NPC71184
0.8857	High Similarity	NPC178627
0.8857	High Similarity	NPC469935
0.8857	High Similarity	NPC206212
0.8849	High Similarity	NPC36181
0.8841	High Similarity	NPC472603
0.8841	High Similarity	NPC477272
0.8832	High Similarity	NPC470668
0.8832	High Similarity	NPC470669
0.8832	High Similarity	NPC470671
0.8832	High Similarity	NPC474504
0.8832	High Similarity	NPC131130
0.8832	High Similarity	NPC474487
0.8832	High Similarity	NPC470672
0.8824	High Similarity	NPC174999
0.8824	High Similarity	NPC194579
0.8811	High Similarity	NPC158866
0.8806	High Similarity	NPC15834
0.8806	High Similarity	NPC215875
0.8803	High Similarity	NPC161864
0.8803	High Similarity	NPC208303
0.8794	High Similarity	NPC25844
0.8769	High Similarity	NPC475733
0.8768	High Similarity	NPC472600
0.8768	High Similarity	NPC472601
0.876	High Similarity	NPC472029
0.876	High Similarity	NPC65761
0.8759	High Similarity	NPC191835
0.875	High Similarity	NPC474726
0.875	High Similarity	NPC475955
0.8741	High Similarity	NPC93756
0.8741	High Similarity	NPC469932
0.8741	High Similarity	NPC16197
0.8741	High Similarity	NPC108113
0.8732	High Similarity	NPC297886
0.8732	High Similarity	NPC249942
0.8732	High Similarity	NPC285748
0.8732	High Similarity	NPC140120
0.8731	High Similarity	NPC27490
0.8723	High Similarity	NPC469953
0.8714	High Similarity	NPC478202
0.8714	High Similarity	NPC159721
0.8705	High Similarity	NPC472605
0.8705	High Similarity	NPC307990
0.8705	High Similarity	NPC16455
0.8705	High Similarity	NPC472604
0.8705	High Similarity	NPC158634
0.8696	High Similarity	NPC88269
0.8696	High Similarity	NPC32360
0.8696	High Similarity	NPC19622
0.8696	High Similarity	NPC268052
0.8696	High Similarity	NPC112789
0.8686	High Similarity	NPC156910
0.8686	High Similarity	NPC70380
0.8682	High Similarity	NPC91105
0.8681	High Similarity	NPC470908
0.8681	High Similarity	NPC321387
0.8681	High Similarity	NPC474735
0.8681	High Similarity	NPC327059
0.8676	High Similarity	NPC290803
0.8676	High Similarity	NPC125920
0.8676	High Similarity	NPC103842
0.8671	High Similarity	NPC469933
0.8671	High Similarity	NPC37139
0.8667	High Similarity	NPC10971
0.8662	High Similarity	NPC57470
0.8657	High Similarity	NPC324482
0.8657	High Similarity	NPC250057
0.8652	High Similarity	NPC42540
0.8652	High Similarity	NPC151607
0.8652	High Similarity	NPC11700
0.8643	High Similarity	NPC111201
0.8643	High Similarity	NPC476508
0.8643	High Similarity	NPC82913
0.8643	High Similarity	NPC282300
0.8633	High Similarity	NPC303633
0.8633	High Similarity	NPC216978
0.8633	High Similarity	NPC217186
0.8633	High Similarity	NPC55018
0.8633	High Similarity	NPC270913
0.8633	High Similarity	NPC283429
0.8633	High Similarity	NPC220062
0.8633	High Similarity	NPC53181
0.8633	High Similarity	NPC301217
0.8633	High Similarity	NPC473209
0.8633	High Similarity	NPC23257
0.8633	High Similarity	NPC275903
0.8633	High Similarity	NPC139554
0.8633	High Similarity	NPC477956
0.8633	High Similarity	NPC240305
0.8633	High Similarity	NPC96565
0.8623	High Similarity	NPC212693
0.8623	High Similarity	NPC472602
0.8623	High Similarity	NPC153979
0.8623	High Similarity	NPC332594
0.8623	High Similarity	NPC33144
0.8623	High Similarity	NPC94248
0.8623	High Similarity	NPC478200
0.8621	High Similarity	NPC312549
0.8621	High Similarity	NPC209142
0.8621	High Similarity	NPC290671
0.8613	High Similarity	NPC13575
0.8613	High Similarity	NPC60667
0.8613	High Similarity	NPC158481
0.8613	High Similarity	NPC472599
0.8613	High Similarity	NPC156967
0.8613	High Similarity	NPC156092
0.8611	High Similarity	NPC104236
0.8611	High Similarity	NPC19238
0.8611	High Similarity	NPC164205
0.8605	High Similarity	NPC215392
0.8603	High Similarity	NPC475645
0.8601	High Similarity	NPC180477
0.8592	High Similarity	NPC473692
0.8592	High Similarity	NPC271288
0.8592	High Similarity	NPC312789
0.8592	High Similarity	NPC75694
0.8592	High Similarity	NPC326500
0.8582	High Similarity	NPC204469
0.8582	High Similarity	NPC296158
0.8582	High Similarity	NPC186628
0.8582	High Similarity	NPC84772
0.8582	High Similarity	NPC297600
0.8582	High Similarity	NPC472610
0.8582	High Similarity	NPC472006
0.8582	High Similarity	NPC471731
0.8571	High Similarity	NPC48624
0.8571	High Similarity	NPC313123
0.8571	High Similarity	NPC471587
0.8571	High Similarity	NPC259166
0.8571	High Similarity	NPC241100
0.8571	High Similarity	NPC219917
0.8571	High Similarity	NPC53649
0.8571	High Similarity	NPC213659
0.8571	High Similarity	NPC11056
0.8571	High Similarity	NPC80962
0.8571	High Similarity	NPC204985
0.8571	High Similarity	NPC82920
0.8571	High Similarity	NPC1704
0.8571	High Similarity	NPC289660
0.8571	High Similarity	NPC253822
0.8571	High Similarity	NPC270883
0.8571	High Similarity	NPC159275

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 NPC470988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	1013
0.2-0.3	1773
0.3-0.4	2679
0.4-0.5	1868
0.5-0.6	1037
0.6-0.7	316
0.7-0.8	100
0.8-0.85	35
0.85-0.9	9
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD970	Clinical (unspecified phase)
0.8592	High Similarity	NPD2534	Approved
0.8592	High Similarity	NPD2533	Approved
0.8592	High Similarity	NPD2532	Approved
0.85	High Similarity	NPD2800	Approved
0.8467	Intermediate Similarity	NPD6651	Approved
0.8462	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1510	Phase 2
0.8188	Intermediate Similarity	NPD1240	Approved
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD7411	Suspended
0.8112	Intermediate Similarity	NPD1243	Approved
0.8092	Intermediate Similarity	NPD7075	Discontinued
0.8079	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1607	Approved
0.8056	Intermediate Similarity	NPD3750	Approved
0.8054	Intermediate Similarity	NPD4380	Phase 2
0.8013	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD2799	Discontinued
0.7947	Intermediate Similarity	NPD6801	Discontinued
0.7931	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1549	Phase 2
0.7908	Intermediate Similarity	NPD7768	Phase 2
0.7902	Intermediate Similarity	NPD2935	Discontinued
0.7902	Intermediate Similarity	NPD2796	Approved
0.7898	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6799	Approved
0.7885	Intermediate Similarity	NPD5710	Approved
0.7885	Intermediate Similarity	NPD5711	Approved
0.7848	Intermediate Similarity	NPD7473	Discontinued
0.7815	Intermediate Similarity	NPD6599	Discontinued
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.777	Intermediate Similarity	NPD7390	Discontinued
0.777	Intermediate Similarity	NPD1511	Approved
0.7742	Intermediate Similarity	NPD3749	Approved
0.774	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD920	Approved
0.7708	Intermediate Similarity	NPD3748	Approved
0.7703	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD1164	Approved
0.7676	Intermediate Similarity	NPD943	Approved
0.7667	Intermediate Similarity	NPD1512	Approved
0.7662	Intermediate Similarity	NPD2801	Approved
0.766	Intermediate Similarity	NPD2313	Discontinued
0.766	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD5404	Approved
0.7655	Intermediate Similarity	NPD5406	Approved
0.7655	Intermediate Similarity	NPD5405	Approved
0.7655	Intermediate Similarity	NPD1551	Phase 2
0.7655	Intermediate Similarity	NPD5408	Approved
0.7628	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD230	Phase 1
0.7622	Intermediate Similarity	NPD5124	Phase 1
0.7622	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD3817	Phase 2
0.7612	Intermediate Similarity	NPD9545	Approved
0.76	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1934	Approved
0.7595	Intermediate Similarity	NPD6959	Discontinued
0.7594	Intermediate Similarity	NPD9493	Approved
0.7556	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5953	Discontinued
0.7535	Intermediate Similarity	NPD3268	Approved
0.7531	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD2798	Approved
0.7464	Intermediate Similarity	NPD9717	Approved
0.7455	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3882	Suspended
0.7429	Intermediate Similarity	NPD1203	Approved
0.7429	Intermediate Similarity	NPD2797	Approved
0.7423	Intermediate Similarity	NPD7286	Phase 2
0.7415	Intermediate Similarity	NPD6100	Approved
0.7415	Intermediate Similarity	NPD6099	Approved
0.7413	Intermediate Similarity	NPD3764	Approved
0.7403	Intermediate Similarity	NPD3226	Approved
0.7386	Intermediate Similarity	NPD5403	Approved
0.7365	Intermediate Similarity	NPD2346	Discontinued
0.7365	Intermediate Similarity	NPD2344	Approved
0.7358	Intermediate Similarity	NPD919	Approved
0.7347	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7312	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD2654	Approved
0.7266	Intermediate Similarity	NPD1201	Approved
0.7256	Intermediate Similarity	NPD3818	Discontinued
0.7255	Intermediate Similarity	NPD5401	Approved
0.7252	Intermediate Similarity	NPD9266	Approved
0.7252	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6166	Phase 2
0.7214	Intermediate Similarity	NPD1608	Approved
0.7214	Intermediate Similarity	NPD9269	Phase 2
0.7212	Intermediate Similarity	NPD5844	Phase 1
0.7212	Intermediate Similarity	NPD7054	Approved
0.7186	Intermediate Similarity	NPD6559	Discontinued
0.7183	Intermediate Similarity	NPD3267	Approved
0.7183	Intermediate Similarity	NPD3266	Approved
0.7183	Intermediate Similarity	NPD1470	Approved
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7176	Intermediate Similarity	NPD9263	Approved
0.7176	Intermediate Similarity	NPD9264	Approved
0.7176	Intermediate Similarity	NPD9267	Approved
0.7176	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9268	Approved
0.7172	Intermediate Similarity	NPD1296	Phase 2
0.7172	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2309	Approved
0.717	Intermediate Similarity	NPD5402	Approved
0.7169	Intermediate Similarity	NPD7074	Phase 3
0.7169	Intermediate Similarity	NPD7472	Approved
0.7153	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6797	Phase 2
0.7114	Intermediate Similarity	NPD7033	Discontinued
0.7114	Intermediate Similarity	NPD4308	Phase 3
0.7107	Intermediate Similarity	NPD1465	Phase 2
0.7105	Intermediate Similarity	NPD7003	Approved
0.7083	Intermediate Similarity	NPD7251	Discontinued
0.7063	Intermediate Similarity	NPD4288	Approved
0.7055	Intermediate Similarity	NPD411	Approved
0.7051	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7808	Phase 3
0.7034	Intermediate Similarity	NPD4908	Phase 1
0.7029	Intermediate Similarity	NPD4363	Phase 3
0.7029	Intermediate Similarity	NPD4360	Phase 2
0.7027	Intermediate Similarity	NPD447	Suspended
0.702	Intermediate Similarity	NPD6005	Phase 3
0.702	Intermediate Similarity	NPD6002	Phase 3
0.702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6004	Phase 3
0.702	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD17	Approved
0.6993	Remote Similarity	NPD3225	Approved
0.6989	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4361	Phase 2
0.6981	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1247	Approved
0.6949	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4750	Phase 3
0.6939	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD9281	Approved
0.6923	Remote Similarity	NPD4749	Approved
0.6923	Remote Similarity	NPD940	Approved
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD846	Approved
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7229	Phase 3
0.6901	Remote Similarity	NPD1610	Phase 2
0.6897	Remote Similarity	NPD4287	Approved
0.6879	Remote Similarity	NPD4626	Approved
0.6879	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD1283	Approved
0.687	Remote Similarity	NPD9261	Approved
0.6867	Remote Similarity	NPD3926	Phase 2
0.6859	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3972	Approved
0.6846	Remote Similarity	NPD4307	Phase 2
0.6832	Remote Similarity	NPD37	Approved
0.6829	Remote Similarity	NPD6234	Discontinued
0.6826	Remote Similarity	NPD2403	Approved
0.6818	Remote Similarity	NPD5909	Discontinued
0.6813	Remote Similarity	NPD6585	Discontinued
0.681	Remote Similarity	NPD4965	Approved
0.681	Remote Similarity	NPD4967	Phase 2
0.681	Remote Similarity	NPD4966	Approved
0.6803	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6355	Discontinued
0.68	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1019	Discontinued
0.6779	Remote Similarity	NPD520	Approved
0.6774	Remote Similarity	NPD8166	Discontinued
0.6772	Remote Similarity	NPD5049	Phase 3
0.677	Remote Similarity	NPD5890	Approved
0.677	Remote Similarity	NPD5889	Approved
0.6765	Remote Similarity	NPD1729	Discontinued
0.6757	Remote Similarity	NPD4625	Phase 3
0.6748	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7199	Phase 2
0.6746	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1930	Approved
0.6742	Remote Similarity	NPD1929	Approved
0.6742	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1548	Phase 1
0.6733	Remote Similarity	NPD4060	Phase 1

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