NPASS Compound

Structure

NPC475012 OpenBabel07101718242D 34 35 0 0 1 0 0 0 0 0999 V2000 2.7024 -0.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1085 -2.2565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7484 -0.5623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3986 0.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7024 -0.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2024 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2024 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2024 1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2024 0.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7024 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 -1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7024 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9345 1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8005 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4394 -1.5134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7024 -1.9487 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 1.2024 -1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9345 0.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0685 2.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0685 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6665 0.9173 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 4.2024 -1.0827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.0685 3.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6665 1.9173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5326 0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0685 -0.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 29 1 0 0 0 0 7 33 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 24 2 0 0 0 0 12 26 2 0 0 0 0 13 29 1 0 0 0 0 14 19 2 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 18 27 1 0 0 0 0 21 28 1 0 0 0 0 22 15 1 1 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 0 0 0 0 25 14 1 6 0 0 0 25 28 1 0 0 0 0 26 34 1 0 0 0 0 27 31 2 0 0 0 0 27 33 1 0 0 0 0 28 32 2 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.27
Volume:	513.25
LogP:	5.65
LogD:	4.756
LogS:	-5.496
# Rotatable Bonds:	12
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.307
Synthetic Accessibility Score:	4.311
Fsp3:	0.448
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.957
MDCK Permeability:	1.5814161088201217e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.14
30% Bioavailability (F30%):	0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	98.67212677001953%
Volume Distribution (VD):	1.064
Pgp-substrate:	0.837959885597229%

ADMET: Metabolism

CYP1A2-inhibitor:	0.262
CYP1A2-substrate:	0.732
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.94
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.921
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.968
CYP3A4-substrate:	0.713

ADMET: Excretion

Clearance (CL):	7.008
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.31
Human Hepatotoxicity (H-HT):	0.747
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.921
Carcinogencity:	0.635
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.765

Download Data

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

Natural Product: NPC475012

Natural Product ID:	NPC475012
*Common Name:**	Methyl 2-(2-((E)-3,7-Dimethyl-8-((1R,5R)-3-Methyl-5-(2-Methylprop-1-Enyl)-4-Oxocyclopent-2-Enyl)Octa-1,6-Dien-3-Yloxy)-5-Hydroxyphenyl)Acetate
IUPAC Name:	methyl 2-[2-[(6E)-3,7-dimethyl-8-[(1R,5R)-3-methyl-5-(2-methylprop-1-enyl)-4-oxocyclopent-2-en-1-yl]octa-1,6-dien-3-yl]oxy-5-hydroxyphenyl]acetate
Synonyms:
Standard InCHIKey:	GWQBAQDVEGIWJQ-MKJZMKQJSA-N
Standard InCHI:	InChI=1S/C29H38O5/c1-8-29(6,34-26-12-11-24(30)17-23(26)18-27(31)33-7)13-9-10-20(4)15-22-16-21(5)28(32)25(22)14-19(2)3/h8,10-12,14,16-17,22,25,30H,1,9,13,15,18H2,2-7H3/b20-10+/t22-,25+,29?/m1/s1
SMILES:	CC1=CC(C(C1=O)C=C(C)C)CC(=CCCC(C)(C=C)OC2=C(C=C(C=C2)O)CC(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491815
PubChem CID:	25136076
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
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
Others	1

Activity Type	# Activity
Individual Protein	1
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	=	50.0	ug.mL-1	PMID[573626]
NPT2	Others	Unspecified		IC50	>	200.0	ug.mL-1	PMID[573626]
NPT1	Others	Radical scavenging activity		RC50	=	11.72	ug ml-1	PMID[573626]

☑ 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 NPC475012 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	305
0.1-0.2	1360
0.2-0.3	3286
0.3-0.4	7746
0.4-0.5	10560
0.5-0.6	4423
0.6-0.7	8159
0.7-0.8	6707
0.8-0.85	134
0.85-0.9	6
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.927	High Similarity	NPC475045
0.9203	High Similarity	NPC475044
0.9203	High Similarity	NPC475063
0.9197	High Similarity	NPC475005
0.9197	High Similarity	NPC474943
0.9118	High Similarity	NPC475011
0.9058	High Similarity	NPC475028
0.9058	High Similarity	NPC476025
0.8978	High Similarity	NPC476018
0.8978	High Similarity	NPC475029
0.8613	High Similarity	NPC196621
0.8394	Intermediate Similarity	NPC95034
0.8394	Intermediate Similarity	NPC142087
0.8357	Intermediate Similarity	NPC317601
0.8357	Intermediate Similarity	NPC329427
0.8321	Intermediate Similarity	NPC475236
0.8299	Intermediate Similarity	NPC89664
0.8299	Intermediate Similarity	NPC274085
0.8269	Intermediate Similarity	NPC164937
0.8264	Intermediate Similarity	NPC327612
0.8264	Intermediate Similarity	NPC73078
0.8264	Intermediate Similarity	NPC148738
0.8264	Intermediate Similarity	NPC319870
0.8252	Intermediate Similarity	NPC246177
0.8252	Intermediate Similarity	NPC317045
0.8214	Intermediate Similarity	NPC123
0.8214	Intermediate Similarity	NPC163169
0.8188	Intermediate Similarity	NPC474944
0.8182	Intermediate Similarity	NPC298900
0.8175	Intermediate Similarity	NPC221798
0.8175	Intermediate Similarity	NPC474237
0.8138	Intermediate Similarity	NPC98395
0.8133	Intermediate Similarity	NPC66991
0.8133	Intermediate Similarity	NPC113428
0.8133	Intermediate Similarity	NPC61284
0.8129	Intermediate Similarity	NPC121104
0.8129	Intermediate Similarity	NPC71525
0.8125	Intermediate Similarity	NPC21797
0.8125	Intermediate Similarity	NPC278832
0.8125	Intermediate Similarity	NPC194847
0.8125	Intermediate Similarity	NPC223616
0.8125	Intermediate Similarity	NPC64157
0.8117	Intermediate Similarity	NPC159692
0.8106	Intermediate Similarity	NPC322358
0.8099	Intermediate Similarity	NPC118253
0.8099	Intermediate Similarity	NPC251549
0.8095	Intermediate Similarity	NPC184053
0.8095	Intermediate Similarity	NPC164599
0.8092	Intermediate Similarity	NPC475890
0.8092	Intermediate Similarity	NPC295036
0.8085	Intermediate Similarity	NPC86774
0.8085	Intermediate Similarity	NPC109778
0.8085	Intermediate Similarity	NPC327457
0.8082	Intermediate Similarity	NPC473988
0.8071	Intermediate Similarity	NPC476024
0.8071	Intermediate Similarity	NPC2596
0.8071	Intermediate Similarity	NPC201419
0.8067	Intermediate Similarity	NPC286038
0.8067	Intermediate Similarity	NPC308799
0.8067	Intermediate Similarity	NPC472033
0.8056	Intermediate Similarity	NPC291119
0.8056	Intermediate Similarity	NPC281169
0.8054	Intermediate Similarity	NPC469642
0.8054	Intermediate Similarity	NPC113397
0.8054	Intermediate Similarity	NPC213900
0.8052	Intermediate Similarity	NPC84721
0.8052	Intermediate Similarity	NPC477691
0.8042	Intermediate Similarity	NPC472591
0.8029	Intermediate Similarity	NPC291189
0.8029	Intermediate Similarity	NPC69403
0.8029	Intermediate Similarity	NPC132518
0.8029	Intermediate Similarity	NPC477151
0.8029	Intermediate Similarity	NPC49441
0.8028	Intermediate Similarity	NPC474246
0.8028	Intermediate Similarity	NPC474143
0.8027	Intermediate Similarity	NPC147542
0.8027	Intermediate Similarity	NPC32749
0.8027	Intermediate Similarity	NPC469911
0.8027	Intermediate Similarity	NPC42262
0.8027	Intermediate Similarity	NPC327916
0.8027	Intermediate Similarity	NPC37992
0.8027	Intermediate Similarity	NPC326065
0.8027	Intermediate Similarity	NPC241349
0.8027	Intermediate Similarity	NPC220496
0.8026	Intermediate Similarity	NPC266499
0.8026	Intermediate Similarity	NPC223988
0.8013	Intermediate Similarity	NPC472036
0.8	Intermediate Similarity	NPC474542
0.8	Intermediate Similarity	NPC472034
0.8	Intermediate Similarity	NPC477211
0.8	Intermediate Similarity	NPC319422
0.8	Intermediate Similarity	NPC477214
0.8	Intermediate Similarity	NPC477212
0.8	Intermediate Similarity	NPC312789
0.7987	Intermediate Similarity	NPC316691
0.7987	Intermediate Similarity	NPC472006
0.7987	Intermediate Similarity	NPC34965
0.7987	Intermediate Similarity	NPC469615
0.7987	Intermediate Similarity	NPC477690
0.7987	Intermediate Similarity	NPC183536
0.7987	Intermediate Similarity	NPC474599
0.7987	Intermediate Similarity	NPC473090
0.7986	Intermediate Similarity	NPC477210
0.7986	Intermediate Similarity	NPC265793
0.7985	Intermediate Similarity	NPC240664
0.7974	Intermediate Similarity	NPC470107
0.7974	Intermediate Similarity	NPC158866
0.7973	Intermediate Similarity	NPC90411
0.7973	Intermediate Similarity	NPC145673
0.7973	Intermediate Similarity	NPC257003
0.7973	Intermediate Similarity	NPC471444
0.7971	Intermediate Similarity	NPC477152
0.7961	Intermediate Similarity	NPC186397
0.7961	Intermediate Similarity	NPC37135
0.7961	Intermediate Similarity	NPC107636
0.7959	Intermediate Similarity	NPC216312
0.7959	Intermediate Similarity	NPC29771
0.7959	Intermediate Similarity	NPC299405
0.7959	Intermediate Similarity	NPC306835
0.7959	Intermediate Similarity	NPC476477
0.7959	Intermediate Similarity	NPC79372
0.7959	Intermediate Similarity	NPC256463
0.7959	Intermediate Similarity	NPC471602
0.7959	Intermediate Similarity	NPC111422
0.7958	Intermediate Similarity	NPC475880
0.7958	Intermediate Similarity	NPC285776
0.7958	Intermediate Similarity	NPC7569
0.7956	Intermediate Similarity	NPC476165
0.7947	Intermediate Similarity	NPC299011
0.7947	Intermediate Similarity	NPC107625
0.7947	Intermediate Similarity	NPC237208
0.7945	Intermediate Similarity	NPC130976
0.7945	Intermediate Similarity	NPC187826
0.7945	Intermediate Similarity	NPC98804
0.7945	Intermediate Similarity	NPC477534
0.7943	Intermediate Similarity	NPC2401
0.7935	Intermediate Similarity	NPC77430
0.7935	Intermediate Similarity	NPC290927
0.7933	Intermediate Similarity	NPC95123
0.7933	Intermediate Similarity	NPC471305
0.7933	Intermediate Similarity	NPC469683
0.7933	Intermediate Similarity	NPC71739
0.7933	Intermediate Similarity	NPC295696
0.7933	Intermediate Similarity	NPC66404
0.7933	Intermediate Similarity	NPC169942
0.7933	Intermediate Similarity	NPC471600
0.7931	Intermediate Similarity	NPC22222
0.7931	Intermediate Similarity	NPC281513
0.7931	Intermediate Similarity	NPC161856
0.7931	Intermediate Similarity	NPC51087
0.7929	Intermediate Similarity	NPC474945
0.7929	Intermediate Similarity	NPC476022
0.7922	Intermediate Similarity	NPC48671
0.7922	Intermediate Similarity	NPC221085
0.7919	Intermediate Similarity	NPC474385
0.7919	Intermediate Similarity	NPC474154
0.7917	Intermediate Similarity	NPC283823
0.7917	Intermediate Similarity	NPC159418
0.7917	Intermediate Similarity	NPC470871
0.7914	Intermediate Similarity	NPC145134
0.7905	Intermediate Similarity	NPC51181
0.7905	Intermediate Similarity	NPC183642
0.7905	Intermediate Similarity	NPC310370
0.7902	Intermediate Similarity	NPC125153
0.7902	Intermediate Similarity	NPC15083
0.7902	Intermediate Similarity	NPC470976
0.7902	Intermediate Similarity	NPC470977
0.7902	Intermediate Similarity	NPC141549
0.7902	Intermediate Similarity	NPC196979
0.7902	Intermediate Similarity	NPC258073
0.7899	Intermediate Similarity	NPC46634
0.7898	Intermediate Similarity	NPC181960
0.7898	Intermediate Similarity	NPC196448
0.7898	Intermediate Similarity	NPC476930
0.7895	Intermediate Similarity	NPC472969
0.7895	Intermediate Similarity	NPC142863
0.7891	Intermediate Similarity	NPC221046
0.7891	Intermediate Similarity	NPC62735
0.7891	Intermediate Similarity	NPC265335
0.7887	Intermediate Similarity	NPC474289
0.7887	Intermediate Similarity	NPC271832
0.7887	Intermediate Similarity	NPC59654
0.7883	Intermediate Similarity	NPC322569
0.7881	Intermediate Similarity	NPC287275
0.7881	Intermediate Similarity	NPC134621
0.7881	Intermediate Similarity	NPC212697
0.7881	Intermediate Similarity	NPC184649
0.7881	Intermediate Similarity	NPC131766
0.7881	Intermediate Similarity	NPC311144
0.7881	Intermediate Similarity	NPC98926
0.7881	Intermediate Similarity	NPC303185
0.7881	Intermediate Similarity	NPC29577
0.7872	Intermediate Similarity	NPC37512
0.7871	Intermediate Similarity	NPC474843
0.7871	Intermediate Similarity	NPC207624
0.7871	Intermediate Similarity	NPC131121
0.7871	Intermediate Similarity	NPC271681
0.7871	Intermediate Similarity	NPC142308
0.7871	Intermediate Similarity	NPC281272
0.7868	Intermediate Similarity	NPC61779

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 NPC475012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	897
0.2-0.3	1661
0.3-0.4	2436
0.4-0.5	2011
0.5-0.6	1203
0.6-0.7	520
0.7-0.8	139
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
0.8162	Intermediate Similarity	NPD1608	Approved
0.8095	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD3496	Discontinued
0.7941	Intermediate Similarity	NPD17	Approved
0.7905	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3268	Approved
0.7832	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6099	Approved
0.7823	Intermediate Similarity	NPD2935	Discontinued
0.7823	Intermediate Similarity	NPD6100	Approved
0.781	Intermediate Similarity	NPD1778	Approved
0.7792	Intermediate Similarity	NPD3226	Approved
0.7763	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2799	Discontinued
0.7733	Intermediate Similarity	NPD4628	Phase 3
0.773	Intermediate Similarity	NPD2797	Approved
0.7707	Intermediate Similarity	NPD7819	Suspended
0.7707	Intermediate Similarity	NPD2801	Approved
0.7704	Intermediate Similarity	NPD6671	Approved
0.7671	Intermediate Similarity	NPD447	Suspended
0.7664	Intermediate Similarity	NPD9545	Approved
0.7651	Intermediate Similarity	NPD2346	Discontinued
0.7651	Intermediate Similarity	NPD6002	Phase 3
0.7651	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6004	Phase 3
0.7651	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6005	Phase 3
0.7647	Intermediate Similarity	NPD2534	Approved
0.7647	Intermediate Similarity	NPD2533	Approved
0.7647	Intermediate Similarity	NPD2532	Approved
0.7643	Intermediate Similarity	NPD9717	Approved
0.7635	Intermediate Similarity	NPD7033	Discontinued
0.7616	Intermediate Similarity	NPD3750	Approved
0.7586	Intermediate Similarity	NPD2313	Discontinued
0.7574	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6355	Discontinued
0.7547	Intermediate Similarity	NPD5402	Approved
0.7535	Intermediate Similarity	NPD6696	Suspended
0.7533	Intermediate Similarity	NPD2344	Approved
0.7532	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1481	Phase 2
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD6653	Approved
0.75	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD6799	Approved
0.7468	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1551	Phase 2
0.7466	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD411	Approved
0.7466	Intermediate Similarity	NPD3764	Approved
0.7453	Intermediate Similarity	NPD3749	Approved
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7448	Intermediate Similarity	NPD6832	Phase 2
0.7447	Intermediate Similarity	NPD1535	Discovery
0.7432	Intermediate Similarity	NPD230	Phase 1
0.7431	Intermediate Similarity	NPD5647	Approved
0.7413	Intermediate Similarity	NPD3225	Approved
0.74	Intermediate Similarity	NPD4308	Phase 3
0.7389	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1549	Phase 2
0.7365	Intermediate Similarity	NPD5844	Phase 1
0.7365	Intermediate Similarity	NPD1240	Approved
0.7362	Intermediate Similarity	NPD5494	Approved
0.7358	Intermediate Similarity	NPD7411	Suspended
0.7357	Intermediate Similarity	NPD5585	Approved
0.7355	Intermediate Similarity	NPD1511	Approved
0.7349	Intermediate Similarity	NPD7473	Discontinued
0.7338	Intermediate Similarity	NPD2309	Approved
0.7329	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3817	Phase 2
0.7324	Intermediate Similarity	NPD422	Phase 1
0.732	Intermediate Similarity	NPD2800	Approved
0.7315	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1934	Approved
0.731	Intermediate Similarity	NPD2798	Approved
0.7308	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4626	Approved
0.7303	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5763	Approved
0.7303	Intermediate Similarity	NPD5762	Approved
0.7299	Intermediate Similarity	NPD1241	Discontinued
0.7296	Intermediate Similarity	NPD6599	Discontinued
0.7285	Intermediate Similarity	NPD3748	Approved
0.7285	Intermediate Similarity	NPD1510	Phase 2
0.7284	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7267	Intermediate Similarity	NPD1607	Approved
0.7266	Intermediate Similarity	NPD9493	Approved
0.7261	Intermediate Similarity	NPD1512	Approved
0.7248	Intermediate Similarity	NPD4060	Phase 1
0.7241	Intermediate Similarity	NPD6362	Approved
0.7237	Intermediate Similarity	NPD2796	Approved
0.7235	Intermediate Similarity	NPD7685	Pre-registration
0.7233	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7458	Discontinued
0.7226	Intermediate Similarity	NPD6190	Approved
0.7225	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD4749	Approved
0.7215	Intermediate Similarity	NPD920	Approved
0.7212	Intermediate Similarity	NPD8127	Discontinued
0.7205	Intermediate Similarity	NPD6844	Discontinued
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.7193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1019	Discontinued
0.7186	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6233	Phase 2
0.7181	Intermediate Similarity	NPD8032	Phase 2
0.7172	Intermediate Similarity	NPD1283	Approved
0.7169	Intermediate Similarity	NPD6232	Discontinued
0.7162	Intermediate Similarity	NPD7095	Approved
0.716	Intermediate Similarity	NPD1465	Phase 2
0.7159	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6273	Approved
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD9494	Approved
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4307	Phase 2
0.7114	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7114	Intermediate Similarity	NPD7985	Registered
0.7113	Intermediate Similarity	NPD5691	Approved
0.7108	Intermediate Similarity	NPD7199	Phase 2
0.7107	Intermediate Similarity	NPD5403	Approved
0.7103	Intermediate Similarity	NPD4359	Approved
0.7101	Intermediate Similarity	NPD7177	Discontinued
0.7101	Intermediate Similarity	NPD3751	Discontinued
0.7099	Intermediate Similarity	NPD6801	Discontinued
0.7097	Intermediate Similarity	NPD1243	Approved
0.7089	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4622	Approved
0.7086	Intermediate Similarity	NPD4618	Approved
0.7083	Intermediate Similarity	NPD1611	Approved
0.7081	Intermediate Similarity	NPD4380	Phase 2
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7054	Approved
0.7059	Intermediate Similarity	NPD7286	Phase 2
0.7055	Intermediate Similarity	NPD5761	Phase 2
0.7055	Intermediate Similarity	NPD5760	Phase 2
0.7055	Intermediate Similarity	NPD1876	Approved
0.7051	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4110	Phase 3
0.7051	Intermediate Similarity	NPD7003	Approved
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1894	Discontinued
0.7037	Intermediate Similarity	NPD6386	Approved
0.7037	Intermediate Similarity	NPD3134	Approved
0.7037	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6385	Approved
0.7034	Intermediate Similarity	NPD3972	Approved
0.7032	Intermediate Similarity	NPD2424	Discontinued
0.7027	Intermediate Similarity	NPD2237	Approved
0.7024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7340	Approved
0.702	Intermediate Similarity	NPD2979	Phase 3
0.7018	Intermediate Similarity	NPD7074	Phase 3
0.7018	Intermediate Similarity	NPD7472	Approved
0.7013	Intermediate Similarity	NPD4477	Approved
0.7013	Intermediate Similarity	NPD6032	Approved
0.7013	Intermediate Similarity	NPD4476	Approved
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.7006	Intermediate Similarity	NPD2354	Approved
0.7	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5689	Approved
0.6993	Remote Similarity	NPD5688	Approved
0.6993	Remote Similarity	NPD7097	Phase 1
0.6986	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6166	Phase 2
0.6981	Remote Similarity	NPD5401	Approved
0.698	Remote Similarity	NPD4908	Phase 1
0.698	Remote Similarity	NPD2614	Approved
0.6977	Remote Similarity	NPD5953	Discontinued
0.6974	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5124	Phase 1
0.6972	Remote Similarity	NPD7644	Approved
0.6966	Remote Similarity	NPD1281	Approved
0.6966	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5710	Approved
0.6964	Remote Similarity	NPD3787	Discontinued
0.6964	Remote Similarity	NPD5711	Approved
0.6963	Remote Similarity	NPD9697	Approved
0.6962	Remote Similarity	NPD7440	Discontinued
0.6962	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1653	Approved
0.6943	Remote Similarity	NPD8166	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