NPASS Compound

Structure

NPC474810 OpenBabel07101719512D 32 32 0 0 0 0 0 0 0 0999 V2000 0.0000 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -0.8660 -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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 21 2 0 0 0 0 13 22 1 0 0 0 0 14 22 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 24 29 2 0 0 0 0 24 32 1 0 0 0 0 25 26 2 0 0 0 0 25 28 1 0 0 0 0 26 30 1 0 0 0 0 27 28 2 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.29
Volume:	498.357
LogP:	7.109
LogD:	5.116
LogS:	-2.471
# Rotatable Bonds:	13
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	3.154
Fsp3:	0.464
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.903
MDCK Permeability:	2.296257298439741e-05
Pgp-inhibitor:	0.76
Pgp-substrate:	0.433
Human Intestinal Absorption (HIA):	0.357
20% Bioavailability (F20%):	0.702
30% Bioavailability (F30%):	0.543

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	96.7233657836914%
Volume Distribution (VD):	0.515
Pgp-substrate:	0.9194486141204834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.863
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.565
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.608
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.798
CYP2D6-substrate:	0.775
CYP3A4-inhibitor:	0.418
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	3.019
Half-life (T1/2):	0.571

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.501
Skin Sensitization:	0.973
Carcinogencity:	0.023
Eye Corrosion:	0.011
Eye Irritation:	0.897
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC474810

Natural Product ID:	NPC474810
*Common Name:**	2-Acetoxy-3-Geranylgeranyl-1,4-Dihydroxybenzene
IUPAC Name:	[3,6-dihydroxy-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]phenyl] acetate
Synonyms:
Standard InCHIKey:	VLLSMOKWYCNDEY-MLAGYPMBSA-N
Standard InCHI:	InChI=1S/C28H40O4/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-15-23(5)16-17-25-26(30)18-19-27(31)28(25)32-24(6)29/h10,12,14,16,18-19,30-31H,7-9,11,13,15,17H2,1-6H3/b21-12+,22-14+,23-16+
SMILES:	CC(=CCC/C(=C/CC/C(=C/CC/C(=C/Cc1c(ccc(c1OC(=O)C)O)O)/C)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483629
PubChem CID:	14487954
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575963]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1294697]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607355]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809609]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	3
MIC	8

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.5	ug.mL-1	PMID[462958]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.9	ug.mL-1	PMID[462958]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[462957]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[462957]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	>	100.0	ug.mL-1	PMID[462957]
NPT4678	Organism	Hafnia alvei	Hafnia alvei	MIC	>	100.0	ug.mL-1	PMID[462957]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	100.0	ug.mL-1	PMID[462957]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[462957]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50.0	ug.mL-1	PMID[462957]
NPT1843	Organism	Aeromonas hydrophila	Aeromonas hydrophila	MIC	>	100.0	ug.mL-1	PMID[462957]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.9	ug.mL-1	PMID[462958]

☑ 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 NPC474810 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	320
0.1-0.2	1583
0.2-0.3	5359
0.3-0.4	12450
0.4-0.5	5241
0.5-0.6	4868
0.6-0.7	7716
0.7-0.8	4502
0.8-0.85	549
0.85-0.9	94
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC142530
0.9841	High Similarity	NPC147317
0.969	High Similarity	NPC252095
0.9609	High Similarity	NPC474635
0.9394	High Similarity	NPC105493
0.9394	High Similarity	NPC476171
0.937	High Similarity	NPC474670
0.937	High Similarity	NPC474821
0.9302	High Similarity	NPC220935
0.9291	High Similarity	NPC474632
0.9147	High Similarity	NPC474616
0.9147	High Similarity	NPC474636
0.9141	High Similarity	NPC112596
0.913	High Similarity	NPC475896
0.9118	High Similarity	NPC469564
0.9104	High Similarity	NPC76336
0.9104	High Similarity	NPC20511
0.9104	High Similarity	NPC139548
0.9104	High Similarity	NPC148835
0.9104	High Similarity	NPC52086
0.9104	High Similarity	NPC95162
0.9091	High Similarity	NPC277021
0.9058	High Similarity	NPC292256
0.9051	High Similarity	NPC256555
0.9051	High Similarity	NPC34245
0.9051	High Similarity	NPC110067
0.9051	High Similarity	NPC7439
0.9051	High Similarity	NPC91492
0.9037	High Similarity	NPC13067
0.903	High Similarity	NPC126682
0.903	High Similarity	NPC82271
0.9008	High Similarity	NPC474617
0.8992	High Similarity	NPC476006
0.8976	High Similarity	NPC474864
0.8976	High Similarity	NPC246967
0.8939	High Similarity	NPC82503
0.8929	High Similarity	NPC170239
0.8929	High Similarity	NPC97937
0.8929	High Similarity	NPC275125
0.8923	High Similarity	NPC216836
0.8897	High Similarity	NPC164148
0.8897	High Similarity	NPC43500
0.8881	High Similarity	NPC92830
0.8872	High Similarity	NPC137949
0.8864	High Similarity	NPC214860
0.8855	High Similarity	NPC266691
0.8855	High Similarity	NPC19694
0.8837	High Similarity	NPC183446
0.8828	High Similarity	NPC135414
0.8824	High Similarity	NPC38874
0.8815	High Similarity	NPC134968
0.8815	High Similarity	NPC472337
0.8815	High Similarity	NPC201357
0.8815	High Similarity	NPC281521
0.8815	High Similarity	NPC255147
0.8806	High Similarity	NPC94236
0.8806	High Similarity	NPC37196
0.8806	High Similarity	NPC26673
0.8803	High Similarity	NPC30688
0.8803	High Similarity	NPC113790
0.8803	High Similarity	NPC176903
0.8797	High Similarity	NPC73738
0.8794	High Similarity	NPC178129
0.8788	High Similarity	NPC10225
0.8788	High Similarity	NPC158477
0.8788	High Similarity	NPC58164
0.8788	High Similarity	NPC45824
0.8786	High Similarity	NPC125617
0.8777	High Similarity	NPC236419
0.8777	High Similarity	NPC230157
0.8777	High Similarity	NPC6568
0.8768	High Similarity	NPC300611
0.8759	High Similarity	NPC19869
0.875	High Similarity	NPC472334
0.875	High Similarity	NPC471719
0.875	High Similarity	NPC472336
0.8741	High Similarity	NPC21184
0.8741	High Similarity	NPC111635
0.8741	High Similarity	NPC294522
0.8741	High Similarity	NPC205727
0.8741	High Similarity	NPC120426
0.8741	High Similarity	NPC474600
0.8732	High Similarity	NPC139839
0.8731	High Similarity	NPC161203
0.8731	High Similarity	NPC319969
0.8722	High Similarity	NPC234488
0.8722	High Similarity	NPC299221
0.8722	High Similarity	NPC51840
0.8722	High Similarity	NPC311680
0.8705	High Similarity	NPC472335
0.8705	High Similarity	NPC472332
0.8692	High Similarity	NPC140521
0.8686	High Similarity	NPC474282
0.8686	High Similarity	NPC474521
0.8686	High Similarity	NPC107551
0.8686	High Similarity	NPC176051
0.8686	High Similarity	NPC103976
0.8686	High Similarity	NPC326797
0.8686	High Similarity	NPC102904
0.8686	High Similarity	NPC474886
0.8686	High Similarity	NPC474540
0.8686	High Similarity	NPC474530
0.8686	High Similarity	NPC276490
0.8667	High Similarity	NPC168059
0.8667	High Similarity	NPC241341
0.8667	High Similarity	NPC233018
0.8667	High Similarity	NPC269528
0.8667	High Similarity	NPC229442
0.8667	High Similarity	NPC36437
0.8662	High Similarity	NPC476347
0.8662	High Similarity	NPC231149
0.8643	High Similarity	NPC138212
0.8636	High Similarity	NPC50368
0.8636	High Similarity	NPC210355
0.8636	High Similarity	NPC470699
0.8626	High Similarity	NPC249836
0.8623	High Similarity	NPC245207
0.8623	High Similarity	NPC319647
0.8623	High Similarity	NPC25966
0.8623	High Similarity	NPC127218
0.8621	High Similarity	NPC264875
0.8621	High Similarity	NPC163598
0.8621	High Similarity	NPC120774
0.8615	High Similarity	NPC95168
0.8613	High Similarity	NPC286843
0.8605	High Similarity	NPC285289
0.8603	High Similarity	NPC310854
0.8603	High Similarity	NPC106215
0.8603	High Similarity	NPC309744
0.8601	High Similarity	NPC476348
0.8601	High Similarity	NPC187398
0.8593	High Similarity	NPC202762
0.8593	High Similarity	NPC127624
0.8593	High Similarity	NPC86655
0.8593	High Similarity	NPC137669
0.8593	High Similarity	NPC245120
0.8593	High Similarity	NPC6451
0.8592	High Similarity	NPC205361
0.8583	High Similarity	NPC474612
0.8582	High Similarity	NPC185127
0.8582	High Similarity	NPC471763
0.8582	High Similarity	NPC476399
0.8582	High Similarity	NPC244799
0.8582	High Similarity	NPC240722
0.8582	High Similarity	NPC229231
0.8571	High Similarity	NPC474623
0.8571	High Similarity	NPC109275
0.8571	High Similarity	NPC474651
0.8571	High Similarity	NPC63179
0.8561	High Similarity	NPC103823
0.8561	High Similarity	NPC245060
0.8561	High Similarity	NPC254759
0.8561	High Similarity	NPC214406
0.8561	High Similarity	NPC44748
0.8561	High Similarity	NPC181361
0.8561	High Similarity	NPC28730
0.8561	High Similarity	NPC160283
0.8561	High Similarity	NPC78974
0.8561	High Similarity	NPC223136
0.8561	High Similarity	NPC18924
0.8552	High Similarity	NPC213197
0.855	High Similarity	NPC228972
0.855	High Similarity	NPC78446
0.855	High Similarity	NPC122792
0.854	High Similarity	NPC112246
0.854	High Similarity	NPC121812
0.854	High Similarity	NPC234865
0.854	High Similarity	NPC474206
0.854	High Similarity	NPC112939
0.854	High Similarity	NPC195022
0.854	High Similarity	NPC470356
0.854	High Similarity	NPC94750
0.8531	High Similarity	NPC15577
0.8529	High Similarity	NPC475840
0.8519	High Similarity	NPC474356
0.8519	High Similarity	NPC469907
0.8519	High Similarity	NPC12275
0.8519	High Similarity	NPC45715
0.8519	High Similarity	NPC232275
0.8519	High Similarity	NPC472597
0.8507	High Similarity	NPC48315
0.8507	High Similarity	NPC123127
0.8507	High Similarity	NPC27239
0.8504	High Similarity	NPC471498
0.8504	High Similarity	NPC471503
0.8503	High Similarity	NPC62903
0.8503	High Similarity	NPC7178
0.85	High Similarity	NPC471389
0.8496	Intermediate Similarity	NPC236760
0.8496	Intermediate Similarity	NPC82679
0.8496	Intermediate Similarity	NPC159968
0.8496	Intermediate Similarity	NPC282000
0.8496	Intermediate Similarity	NPC293054
0.8496	Intermediate Similarity	NPC236791
0.8496	Intermediate Similarity	NPC124452
0.8496	Intermediate Similarity	NPC246620
0.8496	Intermediate Similarity	NPC169474
0.8496	Intermediate Similarity	NPC74817
0.8496	Intermediate Similarity	NPC324112
0.8489	Intermediate Similarity	NPC292882

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 NPC474810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	916
0.2-0.3	2124
0.3-0.4	2726
0.4-0.5	1564
0.5-0.6	930
0.6-0.7	502
0.7-0.8	89
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8433	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1653	Approved
0.8358	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3027	Phase 3
0.8188	Intermediate Similarity	NPD1613	Approved
0.8188	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD422	Phase 1
0.8013	Intermediate Similarity	NPD2801	Approved
0.797	Intermediate Similarity	NPD3496	Discontinued
0.7923	Intermediate Similarity	NPD6671	Approved
0.7872	Intermediate Similarity	NPD447	Suspended
0.7794	Intermediate Similarity	NPD4749	Approved
0.7786	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD228	Approved
0.7712	Intermediate Similarity	NPD1934	Approved
0.7687	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1511	Approved
0.7619	Intermediate Similarity	NPD1652	Phase 2
0.7613	Intermediate Similarity	NPD3817	Phase 2
0.7589	Intermediate Similarity	NPD4625	Phase 3
0.7571	Intermediate Similarity	NPD3018	Phase 2
0.7564	Intermediate Similarity	NPD3882	Suspended
0.7552	Intermediate Similarity	NPD4060	Phase 1
0.755	Intermediate Similarity	NPD1512	Approved
0.7548	Intermediate Similarity	NPD1465	Phase 2
0.7548	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5844	Phase 1
0.7518	Intermediate Similarity	NPD1091	Approved
0.7518	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD1778	Approved
0.7482	Intermediate Similarity	NPD6696	Suspended
0.7481	Intermediate Similarity	NPD1548	Phase 1
0.7468	Intermediate Similarity	NPD6234	Discontinued
0.7455	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6653	Approved
0.7423	Intermediate Similarity	NPD7054	Approved
0.7415	Intermediate Similarity	NPD6100	Approved
0.7415	Intermediate Similarity	NPD6099	Approved
0.7413	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2983	Phase 2
0.741	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2982	Phase 2
0.7391	Intermediate Similarity	NPD1610	Phase 2
0.7391	Intermediate Similarity	NPD1611	Approved
0.7389	Intermediate Similarity	NPD5402	Approved
0.7379	Intermediate Similarity	NPD5124	Phase 1
0.7379	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7472	Approved
0.7378	Intermediate Similarity	NPD7074	Phase 3
0.7375	Intermediate Similarity	NPD7199	Phase 2
0.7365	Intermediate Similarity	NPD5762	Approved
0.7365	Intermediate Similarity	NPD5763	Approved
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7357	Intermediate Similarity	NPD3225	Approved
0.7349	Intermediate Similarity	NPD7549	Discontinued
0.7346	Intermediate Similarity	NPD6166	Phase 2
0.7346	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7095	Approved
0.7338	Intermediate Similarity	NPD2981	Phase 2
0.7338	Intermediate Similarity	NPD3686	Approved
0.7338	Intermediate Similarity	NPD3687	Approved
0.7324	Intermediate Similarity	NPD2861	Phase 2
0.731	Intermediate Similarity	NPD1558	Phase 1
0.7308	Intermediate Similarity	NPD290	Approved
0.7305	Intermediate Similarity	NPD2797	Approved
0.7284	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3705	Approved
0.7261	Intermediate Similarity	NPD37	Approved
0.7256	Intermediate Similarity	NPD3818	Discontinued
0.7256	Intermediate Similarity	NPD7228	Approved
0.7254	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6233	Phase 2
0.7233	Intermediate Similarity	NPD4967	Phase 2
0.7233	Intermediate Similarity	NPD4965	Approved
0.7233	Intermediate Similarity	NPD4966	Approved
0.7222	Intermediate Similarity	NPD6232	Discontinued
0.7219	Intermediate Similarity	NPD3750	Approved
0.7214	Intermediate Similarity	NPD1608	Approved
0.7214	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7473	Discontinued
0.719	Intermediate Similarity	NPD6799	Approved
0.7188	Intermediate Similarity	NPD7075	Discontinued
0.7186	Intermediate Similarity	NPD7251	Discontinued
0.7181	Intermediate Similarity	NPD1551	Phase 2
0.7181	Intermediate Similarity	NPD2935	Discontinued
0.7179	Intermediate Similarity	NPD3111	Phase 1
0.7172	Intermediate Similarity	NPD3268	Approved
0.7171	Intermediate Similarity	NPD2219	Phase 1
0.7164	Intermediate Similarity	NPD7843	Approved
0.7164	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7132	Intermediate Similarity	NPD7157	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6797	Phase 2
0.7122	Intermediate Similarity	NPD4626	Approved
0.7121	Intermediate Similarity	NPD2684	Approved
0.7111	Intermediate Similarity	NPD5283	Phase 1
0.7107	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD968	Approved
0.7095	Intermediate Similarity	NPD2653	Approved
0.7092	Intermediate Similarity	NPD1481	Phase 2
0.7083	Intermediate Similarity	NPD2237	Approved
0.7078	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4750	Phase 3
0.7067	Intermediate Similarity	NPD6032	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD6190	Approved
0.7055	Intermediate Similarity	NPD7985	Registered
0.7055	Intermediate Similarity	NPD1296	Phase 2
0.7055	Intermediate Similarity	NPD1048	Approved
0.7055	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7055	Intermediate Similarity	NPD411	Approved
0.7054	Intermediate Similarity	NPD846	Approved
0.7054	Intermediate Similarity	NPD940	Approved
0.7051	Intermediate Similarity	NPD5403	Approved
0.7039	Intermediate Similarity	NPD6674	Discontinued
0.7032	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7644	Approved
0.7025	Intermediate Similarity	NPD4675	Approved
0.7025	Intermediate Similarity	NPD4678	Approved
0.7023	Intermediate Similarity	NPD9697	Approved
0.702	Intermediate Similarity	NPD6005	Phase 3
0.702	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6002	Phase 3
0.702	Intermediate Similarity	NPD6004	Phase 3
0.702	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3540	Phase 1
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD5677	Discontinued
0.6994	Remote Similarity	NPD5494	Approved
0.6993	Remote Similarity	NPD4110	Phase 3
0.6993	Remote Similarity	NPD8651	Approved
0.6993	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9269	Phase 2
0.6968	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4357	Discontinued
0.6957	Remote Similarity	NPD7340	Approved
0.6954	Remote Similarity	NPD3539	Phase 1
0.6943	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3022	Approved
0.694	Remote Similarity	NPD3021	Approved
0.6933	Remote Similarity	NPD919	Approved
0.6929	Remote Similarity	NPD1357	Approved
0.6929	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD5585	Approved
0.6923	Remote Similarity	NPD2534	Approved
0.6923	Remote Similarity	NPD5401	Approved
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD291	Approved
0.6923	Remote Similarity	NPD2532	Approved
0.6918	Remote Similarity	NPD6832	Phase 2
0.6918	Remote Similarity	NPD6599	Discontinued
0.6917	Remote Similarity	NPD1358	Approved
0.6914	Remote Similarity	NPD7768	Phase 2
0.6913	Remote Similarity	NPD1933	Approved
0.6913	Remote Similarity	NPD4340	Discontinued
0.6908	Remote Similarity	NPD1375	Discontinued
0.6906	Remote Similarity	NPD5536	Phase 2
0.6892	Remote Similarity	NPD2674	Phase 3
0.6887	Remote Similarity	NPD4308	Phase 3
0.6887	Remote Similarity	NPD3748	Approved
0.6883	Remote Similarity	NPD4628	Phase 3
0.6879	Remote Similarity	NPD2675	Approved
0.6879	Remote Similarity	NPD2676	Approved
0.6871	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD1398	Phase 1
0.6859	Remote Similarity	NPD1774	Approved
0.685	Remote Similarity	NPD9296	Approved
0.6849	Remote Similarity	NPD9494	Approved
0.6848	Remote Similarity	NPD8127	Discontinued
0.6846	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2677	Approved
0.6832	Remote Similarity	NPD6801	Discontinued
0.6828	Remote Similarity	NPD3267	Approved
0.6828	Remote Similarity	NPD987	Approved
0.6828	Remote Similarity	NPD3266	Approved
0.6828	Remote Similarity	NPD6362	Approved
0.6821	Remote Similarity	NPD6111	Discontinued
0.6821	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7097	Phase 1
0.6818	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3688	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