NPASS Compound

Structure

NPC276962 OpenBabel07101719142D 30 31 0 0 1 0 0 0 0 0999 V2000 -5.7650 -5.3990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5403 -4.1742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0567 -1.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6275 -2.3117 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 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4368 -0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7297 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4028 -1.0870 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 -1.8320 -0.7588 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 -6.2133 -3.7259 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9885 -2.5012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5062 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 -1.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6616 -2.0529 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9545 -2.7600 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 -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 1 0 0 0 0 0 0 0 0 0 -4.2814 -3.2083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 27 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 16 25 2 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 18 28 2 0 0 0 0 21 24 2 0 0 0 0 22 26 2 0 0 0 0 23 26 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 6 1 6 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.28
Volume:	466.351
LogP:	7.301
LogD:	5.46
LogS:	-5.752
# Rotatable Bonds:	9
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	3.967
Fsp3:	0.519
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831
MDCK Permeability:	2.1958554498269223e-05
Pgp-inhibitor:	0.576
Pgp-substrate:	0.126
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.769

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.829
Plasma Protein Binding (PPB):	100.62743377685547%
Volume Distribution (VD):	1.845
Pgp-substrate:	0.8252996802330017%

ADMET: Metabolism

CYP1A2-inhibitor:	0.672
CYP1A2-substrate:	0.78
CYP2C19-inhibitor:	0.747
CYP2C19-substrate:	0.843
CYP2C9-inhibitor:	0.499
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.976
CYP2D6-substrate:	0.79
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	4.737
Half-life (T1/2):	0.305

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.968
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.924
Carcinogencity:	0.082
Eye Corrosion:	0.01
Eye Irritation:	0.252
Respiratory Toxicity:	0.847

Download Data

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

Natural Product: NPC276962

Natural Product ID:	NPC276962
*Common Name:**	Sargachromano N
IUPAC Name:	(2Z,7E)-10-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydrochromen-2-yl]-3,7-dimethyl-2-(2-methylprop-1-enyl)deca-2,7-dienal
Synonyms:	Sargachromano N; Sargachromanol N
Standard InCHIKey:	VYQSISDGHVLRPS-VIVBUFDOSA-N
Standard InCHI:	InChI=1S/C27H38O3/c1-19(2)15-24(18-28)21(4)11-7-9-20(3)10-8-13-27(6)14-12-23-17-25(29)16-22(5)26(23)30-27/h10,15-18,29H,7-9,11-14H2,1-6H3/b20-10+,24-21-/t27-/m1/s1
SMILES:	O=C/C(=C(CCC/C(=C/CC[C@]1(C)CCc2c(O1)c(C)cc(c2)O)/C)/C)/C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463952
PubChem CID:	11269878
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	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	2
MIC	6
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	200.0	ug.mL-1	PMID[505588]
NPT1	Others	Radical scavenging activity		Activity	=	89.2	%	PMID[505587]
NPT2	Others	Unspecified		IC50	=	45000.0	nM	PMID[505588]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[505588]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[505588]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[505588]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[505588]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[505588]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[505588]

☑ 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 NPC276962 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	251
0.1-0.2	1499
0.2-0.3	4132
0.3-0.4	11702
0.4-0.5	7071
0.5-0.6	5139
0.6-0.7	10383
0.7-0.8	2400
0.8-0.85	65
0.85-0.9	35
0.9-0.95	17
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC190086
0.9831	High Similarity	NPC147896
0.9322	High Similarity	NPC32152
0.9274	High Similarity	NPC59654
0.9274	High Similarity	NPC271832
0.925	High Similarity	NPC476165
0.9244	High Similarity	NPC232295
0.9244	High Similarity	NPC474131
0.9231	High Similarity	NPC69539
0.9153	High Similarity	NPC187993
0.9153	High Similarity	NPC238176
0.9024	High Similarity	NPC474237
0.9016	High Similarity	NPC204535
0.9016	High Similarity	NPC46586
0.8943	High Similarity	NPC474130
0.8898	High Similarity	NPC475880
0.8898	High Similarity	NPC196621
0.8852	High Similarity	NPC45663
0.8828	High Similarity	NPC474246
0.8828	High Similarity	NPC474143
0.8824	High Similarity	NPC473718
0.881	High Similarity	NPC95034
0.881	High Similarity	NPC142087
0.878	High Similarity	NPC48623
0.878	High Similarity	NPC168707
0.876	High Similarity	NPC317601
0.876	High Similarity	NPC329427
0.871	High Similarity	NPC302211
0.8636	High Similarity	NPC278832
0.8636	High Similarity	NPC64157
0.8615	High Similarity	NPC118253
0.8607	High Similarity	NPC283616
0.8607	High Similarity	NPC139047
0.8571	High Similarity	NPC474920
0.856	High Similarity	NPC49441
0.8537	High Similarity	NPC51341
0.8516	High Similarity	NPC477212
0.8516	High Similarity	NPC319422
0.8516	High Similarity	NPC477214
0.8516	High Similarity	NPC477211
0.8485	Intermediate Similarity	NPC477210
0.845	Intermediate Similarity	NPC81261
0.8444	Intermediate Similarity	NPC76312
0.8425	Intermediate Similarity	NPC61685
0.8417	Intermediate Similarity	NPC98372
0.84	Intermediate Similarity	NPC131868
0.84	Intermediate Similarity	NPC473875
0.8394	Intermediate Similarity	NPC329493
0.8394	Intermediate Similarity	NPC474154
0.8387	Intermediate Similarity	NPC471449
0.8359	Intermediate Similarity	NPC477213
0.8347	Intermediate Similarity	NPC296144
0.8347	Intermediate Similarity	NPC28784
0.8346	Intermediate Similarity	NPC265793
0.8333	Intermediate Similarity	NPC27578
0.8333	Intermediate Similarity	NPC251259
0.8333	Intermediate Similarity	NPC289624
0.8333	Intermediate Similarity	NPC251549
0.8319	Intermediate Similarity	NPC26013
0.8319	Intermediate Similarity	NPC98392
0.8319	Intermediate Similarity	NPC282855
0.8308	Intermediate Similarity	NPC201419
0.8305	Intermediate Similarity	NPC233320
0.8296	Intermediate Similarity	NPC130976
0.8293	Intermediate Similarity	NPC290470
0.8293	Intermediate Similarity	NPC242580
0.8293	Intermediate Similarity	NPC236070
0.8293	Intermediate Similarity	NPC126759
0.8293	Intermediate Similarity	NPC154256
0.8281	Intermediate Similarity	NPC248557
0.8279	Intermediate Similarity	NPC473931
0.8279	Intermediate Similarity	NPC474114
0.8279	Intermediate Similarity	NPC474050
0.8258	Intermediate Similarity	NPC153019
0.825	Intermediate Similarity	NPC208229
0.825	Intermediate Similarity	NPC471535
0.8235	Intermediate Similarity	NPC68260
0.8235	Intermediate Similarity	NPC279887
0.8231	Intermediate Similarity	NPC473993
0.8222	Intermediate Similarity	NPC194847
0.8222	Intermediate Similarity	NPC21797
0.8203	Intermediate Similarity	NPC261992
0.8197	Intermediate Similarity	NPC90903
0.8182	Intermediate Similarity	NPC275627
0.8175	Intermediate Similarity	NPC14177
0.8168	Intermediate Similarity	NPC47288
0.8168	Intermediate Similarity	NPC176590
0.8145	Intermediate Similarity	NPC163398
0.8134	Intermediate Similarity	NPC211352
0.8125	Intermediate Similarity	NPC188997
0.811	Intermediate Similarity	NPC129176
0.811	Intermediate Similarity	NPC475529
0.8095	Intermediate Similarity	NPC98748
0.8095	Intermediate Similarity	NPC476020
0.8088	Intermediate Similarity	NPC474610
0.808	Intermediate Similarity	NPC183154
0.808	Intermediate Similarity	NPC263754
0.8065	Intermediate Similarity	NPC301321
0.8062	Intermediate Similarity	NPC248786
0.8047	Intermediate Similarity	NPC475839
0.8031	Intermediate Similarity	NPC31314
0.8015	Intermediate Similarity	NPC475011
0.8	Intermediate Similarity	NPC4012
0.7986	Intermediate Similarity	NPC475044
0.7986	Intermediate Similarity	NPC475063
0.7985	Intermediate Similarity	NPC258073
0.7984	Intermediate Similarity	NPC41851
0.7984	Intermediate Similarity	NPC114918
0.7984	Intermediate Similarity	NPC87563
0.7971	Intermediate Similarity	NPC475005
0.7971	Intermediate Similarity	NPC474943
0.797	Intermediate Similarity	NPC206028
0.797	Intermediate Similarity	NPC472795
0.797	Intermediate Similarity	NPC472796
0.7969	Intermediate Similarity	NPC96423
0.7969	Intermediate Similarity	NPC212559
0.7969	Intermediate Similarity	NPC322569
0.7966	Intermediate Similarity	NPC108497
0.7956	Intermediate Similarity	NPC115861
0.7943	Intermediate Similarity	NPC474599
0.7941	Intermediate Similarity	NPC27394
0.7939	Intermediate Similarity	NPC133407
0.7939	Intermediate Similarity	NPC131397
0.7939	Intermediate Similarity	NPC87113
0.7939	Intermediate Similarity	NPC28476
0.7939	Intermediate Similarity	NPC224657
0.7939	Intermediate Similarity	NPC320847
0.7939	Intermediate Similarity	NPC476254
0.7934	Intermediate Similarity	NPC241549
0.7926	Intermediate Similarity	NPC2190
0.7917	Intermediate Similarity	NPC469913
0.7914	Intermediate Similarity	NPC79372
0.7914	Intermediate Similarity	NPC475045
0.791	Intermediate Similarity	NPC325003
0.791	Intermediate Similarity	NPC245395
0.791	Intermediate Similarity	NPC278787
0.7903	Intermediate Similarity	NPC35344
0.7903	Intermediate Similarity	NPC141003
0.7895	Intermediate Similarity	NPC38604
0.7895	Intermediate Similarity	NPC211179
0.7891	Intermediate Similarity	NPC193193
0.7887	Intermediate Similarity	NPC469642
0.7883	Intermediate Similarity	NPC476018
0.7883	Intermediate Similarity	NPC475029
0.7883	Intermediate Similarity	NPC281169
0.7883	Intermediate Similarity	NPC291119
0.7879	Intermediate Similarity	NPC128321
0.7874	Intermediate Similarity	NPC212743
0.7868	Intermediate Similarity	NPC470871
0.7857	Intermediate Similarity	NPC33717
0.7852	Intermediate Similarity	NPC141549
0.7846	Intermediate Similarity	NPC150026
0.7846	Intermediate Similarity	NPC325301
0.7846	Intermediate Similarity	NPC477151
0.7846	Intermediate Similarity	NPC132518
0.7842	Intermediate Similarity	NPC265335
0.7842	Intermediate Similarity	NPC475028
0.7842	Intermediate Similarity	NPC476025
0.784	Intermediate Similarity	NPC114144
0.784	Intermediate Similarity	NPC161696
0.7836	Intermediate Similarity	NPC472797
0.7836	Intermediate Similarity	NPC93962
0.7836	Intermediate Similarity	NPC97326
0.7829	Intermediate Similarity	NPC100108
0.7829	Intermediate Similarity	NPC277798
0.7829	Intermediate Similarity	NPC218753
0.7823	Intermediate Similarity	NPC199462
0.7823	Intermediate Similarity	NPC26615
0.782	Intermediate Similarity	NPC156298
0.7817	Intermediate Similarity	NPC264706
0.7817	Intermediate Similarity	NPC284881
0.7817	Intermediate Similarity	NPC474444
0.7817	Intermediate Similarity	NPC316691
0.7817	Intermediate Similarity	NPC93433
0.7803	Intermediate Similarity	NPC81641
0.7803	Intermediate Similarity	NPC252962
0.7803	Intermediate Similarity	NPC279118
0.7797	Intermediate Similarity	NPC48730
0.7797	Intermediate Similarity	NPC248396
0.7797	Intermediate Similarity	NPC129373
0.7795	Intermediate Similarity	NPC238075
0.7794	Intermediate Similarity	NPC472798
0.7794	Intermediate Similarity	NPC312560
0.7787	Intermediate Similarity	NPC75440
0.7786	Intermediate Similarity	NPC475012
0.7786	Intermediate Similarity	NPC96940
0.7786	Intermediate Similarity	NPC472794
0.7786	Intermediate Similarity	NPC473049
0.7778	Intermediate Similarity	NPC220935
0.7778	Intermediate Similarity	NPC211565
0.7778	Intermediate Similarity	NPC11089
0.7778	Intermediate Similarity	NPC7569
0.7778	Intermediate Similarity	NPC283169
0.7778	Intermediate Similarity	NPC249425
0.777	Intermediate Similarity	NPC98804
0.7769	Intermediate Similarity	NPC212965
0.7769	Intermediate Similarity	NPC30416
0.7762	Intermediate Similarity	NPC471600
0.7761	Intermediate Similarity	NPC53986
0.7761	Intermediate Similarity	NPC274717

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 NPC276962 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1010
0.2-0.3	1578
0.3-0.4	2696
0.4-0.5	1786
0.5-0.6	1174
0.6-0.7	574
0.7-0.8	82
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8983	High Similarity	NPD6671	Approved
0.84	Intermediate Similarity	NPD3496	Discontinued
0.8293	Intermediate Similarity	NPD7340	Approved
0.8197	Intermediate Similarity	NPD1398	Phase 1
0.814	Intermediate Similarity	NPD6696	Suspended
0.7955	Intermediate Similarity	NPD2861	Phase 2
0.7917	Intermediate Similarity	NPD968	Approved
0.791	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4626	Approved
0.7812	Intermediate Similarity	NPD5691	Approved
0.7795	Intermediate Similarity	NPD7644	Approved
0.7794	Intermediate Similarity	NPD4060	Phase 1
0.7786	Intermediate Similarity	NPD4749	Approved
0.777	Intermediate Similarity	NPD2935	Discontinued
0.7704	Intermediate Similarity	NPD4625	Phase 3
0.7676	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2424	Discontinued
0.7647	Intermediate Similarity	NPD7985	Registered
0.7634	Intermediate Similarity	NPD1611	Approved
0.7615	Intermediate Similarity	NPD1778	Approved
0.7537	Intermediate Similarity	NPD2797	Approved
0.7519	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD6100	Approved
0.7518	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2684	Approved
0.7465	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD2237	Approved
0.7419	Intermediate Similarity	NPD290	Approved
0.7405	Intermediate Similarity	NPD5585	Approved
0.7402	Intermediate Similarity	NPD7635	Approved
0.7402	Intermediate Similarity	NPD7843	Approved
0.7376	Intermediate Similarity	NPD7097	Phase 1
0.7372	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD422	Phase 1
0.7368	Intermediate Similarity	NPD1610	Phase 2
0.7364	Intermediate Similarity	NPD7157	Approved
0.7357	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5124	Phase 1
0.7355	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6584	Phase 3
0.7353	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1241	Discontinued
0.7343	Intermediate Similarity	NPD2346	Discontinued
0.7319	Intermediate Similarity	NPD7095	Approved
0.7313	Intermediate Similarity	NPD2233	Approved
0.7313	Intermediate Similarity	NPD2231	Phase 2
0.7313	Intermediate Similarity	NPD2230	Approved
0.7313	Intermediate Similarity	NPD2235	Phase 2
0.7313	Intermediate Similarity	NPD2232	Approved
0.731	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6090	Discontinued
0.7273	Intermediate Similarity	NPD6032	Approved
0.7266	Intermediate Similarity	NPD2313	Discontinued
0.7266	Intermediate Similarity	NPD3268	Approved
0.7259	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD9697	Approved
0.7241	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1535	Discovery
0.7239	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6355	Discontinued
0.723	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3691	Phase 2
0.7226	Intermediate Similarity	NPD3690	Phase 2
0.7222	Intermediate Similarity	NPD5763	Approved
0.7222	Intermediate Similarity	NPD5762	Approved
0.7206	Intermediate Similarity	NPD8651	Approved
0.7203	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD3134	Approved
0.7197	Intermediate Similarity	NPD1548	Phase 1
0.7192	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5929	Approved
0.7188	Intermediate Similarity	NPD228	Approved
0.7185	Intermediate Similarity	NPD1608	Approved
0.7185	Intermediate Similarity	NPD1481	Phase 2
0.7183	Intermediate Similarity	NPD6653	Approved
0.7174	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD844	Approved
0.7163	Intermediate Similarity	NPD4140	Approved
0.7163	Intermediate Similarity	NPD1613	Approved
0.7163	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4476	Approved
0.7153	Intermediate Similarity	NPD4477	Approved
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1651	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7132	Intermediate Similarity	NPD5327	Phase 3
0.7132	Intermediate Similarity	NPD4359	Approved
0.7132	Intermediate Similarity	NPD6583	Phase 3
0.7132	Intermediate Similarity	NPD6582	Phase 2
0.7132	Intermediate Similarity	NPD5535	Approved
0.7132	Intermediate Similarity	NPD821	Approved
0.7124	Intermediate Similarity	NPD6844	Discontinued
0.7123	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6832	Phase 2
0.7111	Intermediate Similarity	NPD1091	Approved
0.7103	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6002	Phase 3
0.7103	Intermediate Similarity	NPD6005	Phase 3
0.7103	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6004	Phase 3
0.7099	Intermediate Similarity	NPD2557	Approved
0.7095	Intermediate Similarity	NPD6667	Approved
0.7095	Intermediate Similarity	NPD6666	Approved
0.7092	Intermediate Similarity	NPD6233	Phase 2
0.7083	Intermediate Similarity	NPD4308	Phase 3
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.708	Intermediate Similarity	NPD3225	Approved
0.708	Intermediate Similarity	NPD1283	Approved
0.7078	Intermediate Similarity	NPD7819	Suspended
0.7068	Intermediate Similarity	NPD1894	Discontinued
0.7063	Intermediate Similarity	NPD2157	Approved
0.7063	Intermediate Similarity	NPD6353	Approved
0.7059	Intermediate Similarity	NPD9717	Approved
0.705	Intermediate Similarity	NPD1712	Approved
0.705	Intermediate Similarity	NPD9494	Approved
0.7034	Intermediate Similarity	NPD1551	Phase 2
0.7032	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1203	Approved
0.7015	Intermediate Similarity	NPD3445	Approved
0.7015	Intermediate Similarity	NPD6382	Discontinued
0.7015	Intermediate Similarity	NPD3444	Approved
0.7015	Intermediate Similarity	NPD3443	Approved
0.7013	Intermediate Similarity	NPD1934	Approved
0.7008	Intermediate Similarity	NPD1358	Approved
0.7	Intermediate Similarity	NPD845	Approved
0.7	Intermediate Similarity	NPD600	Approved
0.7	Intermediate Similarity	NPD596	Approved
0.6993	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD5735	Approved
0.6992	Remote Similarity	NPD5536	Phase 2
0.6986	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2344	Approved
0.6978	Remote Similarity	NPD2798	Approved
0.6974	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1653	Approved
0.6972	Remote Similarity	NPD7477	Discontinued
0.6968	Remote Similarity	NPD2801	Approved
0.6967	Remote Similarity	NPD288	Approved
0.6963	Remote Similarity	NPD17	Approved
0.6954	Remote Similarity	NPD2676	Approved
0.6954	Remote Similarity	NPD2675	Approved
0.695	Remote Similarity	NPD3027	Phase 3
0.6949	Remote Similarity	NPD9295	Approved
0.6947	Remote Similarity	NPD5283	Phase 1
0.6947	Remote Similarity	NPD594	Approved
0.6947	Remote Similarity	NPD592	Approved
0.6943	Remote Similarity	NPD7075	Discontinued
0.6939	Remote Similarity	NPD1549	Phase 2
0.6928	Remote Similarity	NPD3226	Approved
0.6923	Remote Similarity	NPD2238	Phase 2
0.6923	Remote Similarity	NPD2979	Phase 3
0.6918	Remote Similarity	NPD6959	Discontinued
0.6912	Remote Similarity	NPD3847	Discontinued
0.6906	Remote Similarity	NPD4098	Discontinued
0.6906	Remote Similarity	NPD3266	Approved
0.6906	Remote Similarity	NPD6362	Approved
0.6906	Remote Similarity	NPD3267	Approved
0.6901	Remote Similarity	NPD411	Approved
0.6899	Remote Similarity	NPD4750	Phase 3
0.6897	Remote Similarity	NPD4536	Approved
0.6897	Remote Similarity	NPD4538	Approved
0.6897	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6674	Discontinued
0.6889	Remote Similarity	NPD3049	Approved
0.6887	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2532	Approved
0.6887	Remote Similarity	NPD2534	Approved
0.6887	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1578	Phase 2
0.6887	Remote Similarity	NPD2533	Approved
0.6885	Remote Similarity	NPD1809	Phase 2
0.6885	Remote Similarity	NPD2860	Approved
0.6885	Remote Similarity	NPD2859	Approved
0.6883	Remote Similarity	NPD4380	Phase 2
0.6879	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7768	Phase 2
0.6875	Remote Similarity	NPD4618	Approved
0.6875	Remote Similarity	NPD4622	Approved
0.6871	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7030	Discontinued
0.6871	Remote Similarity	NPD5844	Phase 1
0.687	Remote Similarity	NPD1138	Approved
0.6861	Remote Similarity	NPD1281	Approved
0.6861	Remote Similarity	NPD776	Approved
0.6859	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4624	Approved
0.6855	Remote Similarity	NPD3020	Approved
0.6853	Remote Similarity	NPD4870	Approved
0.6853	Remote Similarity	NPD8032	Phase 2
0.6853	Remote Similarity	NPD839	Approved
0.6853	Remote Similarity	NPD840	Approved
0.6849	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6559	Discontinued

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