NPASS Compound

Structure

NPC470989 OpenBabel07101718292D 36 37 0 0 1 0 0 0 0 0999 V2000 -3.3729 4.8684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0594 -4.8684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -4.8684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7459 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 4.3816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 -3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0594 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 -4.3816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7459 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0594 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9026 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.2162 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9026 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0594 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5891 -0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7459 -1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0594 0.9737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 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 8 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 14 2 0 0 0 0 13 18 1 0 0 0 0 15 20 1 0 0 0 0 15 29 2 0 0 0 0 16 17 2 0 0 0 0 16 36 1 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 30 2 0 0 0 0 20 25 1 0 0 0 0 20 27 2 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 26 2 0 0 0 0 22 27 1 0 0 0 0 23 24 2 0 0 0 0 23 28 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 27 34 1 0 0 0 0 28 35 2 0 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.11
Volume:	275.834
LogP:	-0.579
LogD:	-0.278
LogS:	-0.942
# Rotatable Bonds:	7
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	3.36
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.051
MDCK Permeability:	0.007850416004657745
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.356
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919
Plasma Protein Binding (PPB):	12.84471321105957%
Volume Distribution (VD):	0.476
Pgp-substrate:	69.14775848388672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.215
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.17
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	6.353
Half-life (T1/2):	0.923

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.388
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.067
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.157
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC470989

Natural Product ID:	NPC470989
*Common Name:**	3-[1-[3-Acetyl-2,4,6-Trihydroxy-5-(3-Methylbut-2-Enyl)Phenyl]-2-Oxoheptyl]-5-Ethyl-4-Hydroxy-6-Methylpyran-2-One
IUPAC Name:	3-[1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]-2-oxoheptyl]-5-ethyl-4-hydroxy-6-methylpyran-2-one
Synonyms:
Standard InCHIKey:	MLHCHYFNKPHMMY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H36O8/c1-7-9-10-11-19(30)21(23-24(31)17(8-2)16(6)36-28(23)35)22-26(33)18(13-12-14(3)4)25(32)20(15(5)29)27(22)34/h12,21,31-34H,7-11,13H2,1-6H3
SMILES:	CCCCCC(=O)C(c1c(=O)oc(c(c1O)CC)C)c1c(O)c(CC=C(C)C)c(c(c1O)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334821
PubChem CID:	71717009
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	=	8.0	ug.mL-1	PMID[455126]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[455126]

☑ 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 NPC470989 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	359
0.1-0.2	1549
0.2-0.3	3829
0.3-0.4	8700
0.4-0.5	10585
0.5-0.6	4372
0.6-0.7	6112
0.7-0.8	5052
0.8-0.85	1695
0.85-0.9	363
0.9-0.95	62
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470985
0.9769	High Similarity	NPC470984
0.9692	High Similarity	NPC470988
0.9615	High Similarity	NPC185624
0.9462	High Similarity	NPC21378
0.9462	High Similarity	NPC470987
0.9338	High Similarity	NPC470986
0.9197	High Similarity	NPC19476
0.9197	High Similarity	NPC241975
0.9124	High Similarity	NPC219584
0.9124	High Similarity	NPC199458
0.9124	High Similarity	NPC470083
0.9124	High Similarity	NPC183639
0.9051	High Similarity	NPC474624
0.9051	High Similarity	NPC138047
0.9051	High Similarity	NPC131782
0.8936	High Similarity	NPC307895
0.8936	High Similarity	NPC470553
0.8913	High Similarity	NPC322301
0.8913	High Similarity	NPC255801
0.8873	High Similarity	NPC288910
0.8873	High Similarity	NPC470554
0.8873	High Similarity	NPC118059
0.8873	High Similarity	NPC133060
0.8865	High Similarity	NPC470556
0.8865	High Similarity	NPC112829
0.8811	High Similarity	NPC181388
0.8811	High Similarity	NPC470910
0.8803	High Similarity	NPC474939
0.8803	High Similarity	NPC470909
0.8803	High Similarity	NPC96216
0.8803	High Similarity	NPC184738
0.8803	High Similarity	NPC33653
0.8794	High Similarity	NPC470555
0.8786	High Similarity	NPC472343
0.8768	High Similarity	NPC50455
0.8759	High Similarity	NPC16197
0.8741	High Similarity	NPC469935
0.8741	High Similarity	NPC178627
0.8741	High Similarity	NPC1886
0.8741	High Similarity	NPC196137
0.8732	High Similarity	NPC472344
0.8732	High Similarity	NPC294432
0.8731	High Similarity	NPC470981
0.8723	High Similarity	NPC477272
0.8723	High Similarity	NPC221173
0.8705	High Similarity	NPC470983
0.8705	High Similarity	NPC470982
0.8705	High Similarity	NPC194579
0.8686	High Similarity	NPC285054
0.8686	High Similarity	NPC15834
0.8686	High Similarity	NPC215875
0.8681	High Similarity	NPC154217
0.8681	High Similarity	NPC470322
0.8671	High Similarity	NPC87609
0.8671	High Similarity	NPC188632
0.8671	High Similarity	NPC470296
0.8671	High Similarity	NPC112791
0.8671	High Similarity	NPC196459
0.8671	High Similarity	NPC94794
0.8662	High Similarity	NPC476508
0.8633	High Similarity	NPC474726
0.8633	High Similarity	NPC101752
0.8633	High Similarity	NPC475955
0.863	High Similarity	NPC469932
0.8623	High Similarity	NPC175943
0.8621	High Similarity	NPC177995
0.8621	High Similarity	NPC474108
0.8611	High Similarity	NPC71184
0.8611	High Similarity	NPC206212
0.8601	High Similarity	NPC36181
0.8592	High Similarity	NPC472603
0.8582	High Similarity	NPC470669
0.8582	High Similarity	NPC474487
0.8582	High Similarity	NPC470671
0.8582	High Similarity	NPC470672
0.8582	High Similarity	NPC131130
0.8582	High Similarity	NPC474504
0.8582	High Similarity	NPC328983
0.8582	High Similarity	NPC470668
0.8571	High Similarity	NPC321387
0.8571	High Similarity	NPC327059
0.8571	High Similarity	NPC158866
0.8571	High Similarity	NPC174999
0.8562	High Similarity	NPC469933
0.8562	High Similarity	NPC208303
0.8562	High Similarity	NPC161864
0.8552	High Similarity	NPC25844
0.854	High Similarity	NPC279566
0.8531	High Similarity	NPC316560
0.8531	High Similarity	NPC316911
0.8531	High Similarity	NPC111201
0.8521	High Similarity	NPC472601
0.8521	High Similarity	NPC472600
0.8521	High Similarity	NPC240305
0.8521	High Similarity	NPC275903
0.8521	High Similarity	NPC477956
0.8519	High Similarity	NPC329205
0.8519	High Similarity	NPC316625
0.8511	High Similarity	NPC191835
0.8507	High Similarity	NPC475733
0.8496	Intermediate Similarity	NPC472029
0.8496	Intermediate Similarity	NPC65761
0.8493	Intermediate Similarity	NPC297886
0.8493	Intermediate Similarity	NPC249942
0.8493	Intermediate Similarity	NPC285748
0.8493	Intermediate Similarity	NPC140120
0.8489	Intermediate Similarity	NPC108113
0.8489	Intermediate Similarity	NPC93756
0.8483	Intermediate Similarity	NPC469953
0.8483	Intermediate Similarity	NPC75694
0.8478	Intermediate Similarity	NPC27490
0.8477	Intermediate Similarity	NPC263483
0.8472	Intermediate Similarity	NPC297600
0.8472	Intermediate Similarity	NPC321148
0.8472	Intermediate Similarity	NPC321629
0.8472	Intermediate Similarity	NPC472006
0.8472	Intermediate Similarity	NPC478202
0.8472	Intermediate Similarity	NPC323884
0.8472	Intermediate Similarity	NPC326193
0.8472	Intermediate Similarity	NPC159721
0.8467	Intermediate Similarity	NPC469934
0.8467	Intermediate Similarity	NPC186628
0.8462	Intermediate Similarity	NPC307990
0.8462	Intermediate Similarity	NPC158634
0.8462	Intermediate Similarity	NPC16455
0.8462	Intermediate Similarity	NPC253822
0.8462	Intermediate Similarity	NPC82920
0.8462	Intermediate Similarity	NPC472605
0.8462	Intermediate Similarity	NPC164697
0.8462	Intermediate Similarity	NPC472604
0.8462	Intermediate Similarity	NPC471587
0.8462	Intermediate Similarity	NPC289660
0.8451	Intermediate Similarity	NPC32360
0.8451	Intermediate Similarity	NPC54820
0.8451	Intermediate Similarity	NPC112789
0.8451	Intermediate Similarity	NPC88269
0.8451	Intermediate Similarity	NPC477056
0.8451	Intermediate Similarity	NPC272844
0.8451	Intermediate Similarity	NPC19622
0.8451	Intermediate Similarity	NPC477055
0.8451	Intermediate Similarity	NPC180501
0.8451	Intermediate Similarity	NPC254168
0.8451	Intermediate Similarity	NPC268178
0.8451	Intermediate Similarity	NPC248995
0.8451	Intermediate Similarity	NPC268052
0.8446	Intermediate Similarity	NPC470908
0.8446	Intermediate Similarity	NPC474735
0.844	Intermediate Similarity	NPC156910
0.844	Intermediate Similarity	NPC70380
0.844	Intermediate Similarity	NPC71256
0.8435	Intermediate Similarity	NPC145467
0.8435	Intermediate Similarity	NPC37139
0.8435	Intermediate Similarity	NPC472345
0.8429	Intermediate Similarity	NPC125920
0.8429	Intermediate Similarity	NPC103842
0.8429	Intermediate Similarity	NPC290803
0.8425	Intermediate Similarity	NPC57470
0.8425	Intermediate Similarity	NPC473023
0.8421	Intermediate Similarity	NPC91105
0.8417	Intermediate Similarity	NPC10971
0.8417	Intermediate Similarity	NPC37299
0.8417	Intermediate Similarity	NPC180261
0.8414	Intermediate Similarity	NPC313039
0.8414	Intermediate Similarity	NPC473976
0.8414	Intermediate Similarity	NPC42540
0.8414	Intermediate Similarity	NPC109812
0.8414	Intermediate Similarity	NPC198459
0.8414	Intermediate Similarity	NPC11700
0.8414	Intermediate Similarity	NPC151607
0.8414	Intermediate Similarity	NPC131043
0.8409	Intermediate Similarity	NPC229649
0.8406	Intermediate Similarity	NPC250057
0.8406	Intermediate Similarity	NPC324482
0.8403	Intermediate Similarity	NPC82913
0.8403	Intermediate Similarity	NPC322112
0.8403	Intermediate Similarity	NPC55832
0.8403	Intermediate Similarity	NPC26051
0.8403	Intermediate Similarity	NPC52789
0.8403	Intermediate Similarity	NPC268204
0.8403	Intermediate Similarity	NPC282300
0.84	Intermediate Similarity	NPC471695
0.8394	Intermediate Similarity	NPC73203
0.8392	Intermediate Similarity	NPC139554
0.8392	Intermediate Similarity	NPC64664
0.8392	Intermediate Similarity	NPC473209
0.8392	Intermediate Similarity	NPC270913
0.8392	Intermediate Similarity	NPC217186
0.8392	Intermediate Similarity	NPC55018
0.8392	Intermediate Similarity	NPC303633
0.8392	Intermediate Similarity	NPC23257
0.8392	Intermediate Similarity	NPC216978
0.8392	Intermediate Similarity	NPC220062
0.8392	Intermediate Similarity	NPC472515
0.8392	Intermediate Similarity	NPC156872
0.8392	Intermediate Similarity	NPC96565
0.8392	Intermediate Similarity	NPC53181
0.8392	Intermediate Similarity	NPC283429
0.8392	Intermediate Similarity	NPC301217
0.8389	Intermediate Similarity	NPC312549

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 NPC470989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	1010
0.2-0.3	1828
0.3-0.4	2676
0.4-0.5	1883
0.5-0.6	987
0.6-0.7	304
0.7-0.8	97
0.8-0.85	34
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8489	Intermediate Similarity	NPD6651	Approved
0.8483	Intermediate Similarity	NPD2534	Approved
0.8483	Intermediate Similarity	NPD2533	Approved
0.8483	Intermediate Similarity	NPD2532	Approved
0.8451	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2800	Approved
0.8231	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7819	Suspended
0.8117	Intermediate Similarity	NPD7075	Discontinued
0.8105	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7473	Discontinued
0.8026	Intermediate Similarity	NPD7411	Suspended
0.7986	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1510	Phase 2
0.7961	Intermediate Similarity	NPD4380	Phase 2
0.7959	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1240	Approved
0.7922	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6232	Discontinued
0.7891	Intermediate Similarity	NPD1243	Approved
0.7862	Intermediate Similarity	NPD2799	Discontinued
0.7857	Intermediate Similarity	NPD6801	Discontinued
0.7847	Intermediate Similarity	NPD1607	Approved
0.7838	Intermediate Similarity	NPD3750	Approved
0.7821	Intermediate Similarity	NPD7768	Phase 2
0.7812	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5710	Approved
0.7799	Intermediate Similarity	NPD5711	Approved
0.7755	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1549	Phase 2
0.7692	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2935	Discontinued
0.7687	Intermediate Similarity	NPD2796	Approved
0.7683	Intermediate Similarity	NPD5953	Discontinued
0.7682	Intermediate Similarity	NPD6799	Approved
0.7682	Intermediate Similarity	NPD7390	Discontinued
0.7658	Intermediate Similarity	NPD3749	Approved
0.7647	Intermediate Similarity	NPD920	Approved
0.7613	Intermediate Similarity	NPD6599	Discontinued
0.76	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD943	Approved
0.758	Intermediate Similarity	NPD2801	Approved
0.7569	Intermediate Similarity	NPD2313	Discontinued
0.7569	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1511	Approved
0.7561	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3226	Approved
0.7547	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD230	Phase 1
0.7533	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.7516	Intermediate Similarity	NPD6959	Discontinued
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1512	Approved
0.7465	Intermediate Similarity	NPD1164	Approved
0.7455	Intermediate Similarity	NPD7286	Phase 2
0.745	Intermediate Similarity	NPD5405	Approved
0.745	Intermediate Similarity	NPD5404	Approved
0.745	Intermediate Similarity	NPD1551	Phase 2
0.745	Intermediate Similarity	NPD5406	Approved
0.745	Intermediate Similarity	NPD5408	Approved
0.7415	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5124	Phase 1
0.7405	Intermediate Similarity	NPD1934	Approved
0.74	Intermediate Similarity	NPD2344	Approved
0.7391	Intermediate Similarity	NPD9545	Approved
0.7375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3882	Suspended
0.7372	Intermediate Similarity	NPD9493	Approved
0.7338	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6099	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7329	Intermediate Similarity	NPD3764	Approved
0.7329	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD5403	Approved
0.7305	Intermediate Similarity	NPD422	Phase 1
0.7292	Intermediate Similarity	NPD2798	Approved
0.7289	Intermediate Similarity	NPD3818	Discontinued
0.7285	Intermediate Similarity	NPD2346	Discontinued
0.7278	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9717	Approved
0.7246	Intermediate Similarity	NPD7054	Approved
0.7239	Intermediate Similarity	NPD5494	Approved
0.7222	Intermediate Similarity	NPD1203	Approved
0.7222	Intermediate Similarity	NPD1470	Approved
0.7222	Intermediate Similarity	NPD2797	Approved
0.7208	Intermediate Similarity	NPD2309	Approved
0.7205	Intermediate Similarity	NPD5402	Approved
0.7202	Intermediate Similarity	NPD7074	Phase 3
0.7202	Intermediate Similarity	NPD7472	Approved
0.7192	Intermediate Similarity	NPD6832	Phase 2
0.7179	Intermediate Similarity	NPD5401	Approved
0.7178	Intermediate Similarity	NPD919	Approved
0.7176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD9269	Phase 2
0.7118	Intermediate Similarity	NPD7251	Discontinued
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7107	Intermediate Similarity	NPD7458	Discontinued
0.7092	Intermediate Similarity	NPD9268	Approved
0.7078	Intermediate Similarity	NPD2654	Approved
0.7076	Intermediate Similarity	NPD7808	Phase 3
0.7063	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6797	Phase 2
0.7041	Intermediate Similarity	NPD5844	Phase 1
0.7037	Intermediate Similarity	NPD74	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7019	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1608	Approved
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3266	Approved
0.6986	Remote Similarity	NPD3267	Approved
0.6983	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1296	Phase 2
0.6963	Remote Similarity	NPD9264	Approved
0.6963	Remote Similarity	NPD9267	Approved
0.6963	Remote Similarity	NPD9263	Approved
0.6963	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD447	Suspended
0.6946	Remote Similarity	NPD7229	Phase 3
0.6928	Remote Similarity	NPD7033	Discontinued
0.6928	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD7003	Approved
0.689	Remote Similarity	NPD4288	Approved
0.6886	Remote Similarity	NPD1247	Approved
0.6882	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4363	Phase 3
0.6872	Remote Similarity	NPD4360	Phase 2
0.6871	Remote Similarity	NPD37	Approved
0.6867	Remote Similarity	NPD411	Approved
0.6867	Remote Similarity	NPD6234	Discontinued
0.6848	Remote Similarity	NPD4967	Phase 2
0.6848	Remote Similarity	NPD4966	Approved
0.6848	Remote Similarity	NPD4965	Approved
0.6846	Remote Similarity	NPD4908	Phase 1
0.6845	Remote Similarity	NPD8151	Discontinued
0.6839	Remote Similarity	NPD8313	Approved
0.6839	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6004	Phase 3
0.6839	Remote Similarity	NPD8312	Approved
0.6839	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6005	Phase 3
0.6839	Remote Similarity	NPD6002	Phase 3
0.6836	Remote Similarity	NPD4287	Approved
0.6836	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4361	Phase 2
0.6824	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8434	Phase 2
0.6806	Remote Similarity	NPD17	Approved
0.6803	Remote Similarity	NPD3225	Approved
0.6772	Remote Similarity	NPD6190	Approved
0.6765	Remote Similarity	NPD2403	Approved
0.6757	Remote Similarity	NPD7435	Discontinued
0.6755	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4750	Phase 3
0.6738	Remote Similarity	NPD9281	Approved
0.6735	Remote Similarity	NPD4749	Approved
0.6732	Remote Similarity	NPD6355	Discontinued
0.672	Remote Similarity	NPD8319	Approved
0.672	Remote Similarity	NPD8320	Phase 1
0.6716	Remote Similarity	NPD846	Approved
0.6716	Remote Similarity	NPD940	Approved
0.6712	Remote Similarity	NPD1610	Phase 2
0.6709	Remote Similarity	NPD8166	Discontinued
0.669	Remote Similarity	NPD4626	Approved
0.6689	Remote Similarity	NPD1283	Approved
0.6687	Remote Similarity	NPD2296	Approved
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5353	Approved
0.6687	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7199	Phase 2
0.6686	Remote Similarity	NPD7228	Approved
0.6685	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6535	Approved
0.6685	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4307	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