NPASS Compound

Structure

NPC476025 OpenBabel07101718312D 35 35 0 0 1 0 0 0 0 0999 V2000 -2.3660 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -4.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1340 -3.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 -1.9641 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 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 -0.2321 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -2.8301 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1340 -3.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 -1.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 5.1340 -1.9641 0.0000 C 0 0 1 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1340 -1.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1340 -0.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 20 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 6 29 1 0 0 0 0 7 34 1 0 0 0 0 8 29 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 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 15 1 0 0 0 0 14 24 2 0 0 0 0 15 26 2 0 0 0 0 16 29 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 31 1 1 0 0 0 26 35 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 33 2 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	533.233
LogP:	5.2
LogD:	4.9
LogS:	-5.186
# Rotatable Bonds:	17
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	3.977
Fsp3:	0.552
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.787
MDCK Permeability:	1.8705417460296303e-05
Pgp-inhibitor:	0.973
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.774

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	97.95569610595703%
Volume Distribution (VD):	0.143
Pgp-substrate:	0.550631046295166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.165
CYP1A2-substrate:	0.307
CYP2C19-inhibitor:	0.83
CYP2C19-substrate:	0.763
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.734
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.425

ADMET: Excretion

Clearance (CL):	6.371
Half-life (T1/2):	0.75

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.64
Drug-inuced Liver Injury (DILI):	0.491
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.839
Carcinogencity:	0.11
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.244

Download Data

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

Natural Product: NPC476025

Natural Product ID:	NPC476025
*Common Name:**	Nahocol A
IUPAC Name:	methyl 2-[5-hydroxy-2-[(6E,13S)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxyphenyl]acetate
Synonyms:
Standard InCHIKey:	KXTOXZSIGCDGHF-WCCLQZQWSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-8-29(6,35-26-15-14-24(30)18-23(26)19-27(32)34-7)16-10-12-21(4)11-9-13-22(5)28(33)25(31)17-20(2)3/h8,12,14-15,17-18,22,25,30-31H,1,9-11,13,16,19H2,2-7H3/b21-12+/t22?,25-,29?/m0/s1
SMILES:	CC(CCCC(=CCCC(C)(C=C)OC1=C(C=C(C=C1)O)CC(=O)OC)C)C(=O)C(C=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522327
PubChem CID:	10767278
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
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[566103]
NPT2	Others	Unspecified		IC50	>	200.0	ug.mL-1	PMID[566103]
NPT1	Others	Radical scavenging activity		RC50	=	11.35	ug ml-1	PMID[566103]

☑ 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 NPC476025 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	293
0.1-0.2	1201
0.2-0.3	3239
0.3-0.4	7235
0.4-0.5	11243
0.5-0.6	4442
0.6-0.7	8345
0.7-0.8	6586
0.8-0.85	88
0.85-0.9	14
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475028
0.985	High Similarity	NPC475044
0.985	High Similarity	NPC475063
0.9771	High Similarity	NPC475011
0.9699	High Similarity	NPC475005
0.9699	High Similarity	NPC474943
0.9627	High Similarity	NPC475045
0.9474	High Similarity	NPC475029
0.9474	High Similarity	NPC476018
0.9058	High Similarity	NPC475012
0.8947	High Similarity	NPC476024
0.8889	High Similarity	NPC474143
0.8889	High Similarity	NPC474246
0.8815	High Similarity	NPC475880
0.8797	High Similarity	NPC474944
0.8722	High Similarity	NPC477213
0.8676	High Similarity	NPC163169
0.8676	High Similarity	NPC123
0.8593	High Similarity	NPC319422
0.8593	High Similarity	NPC477214
0.8593	High Similarity	NPC477211
0.8593	High Similarity	NPC477212
0.8561	High Similarity	NPC477210
0.8531	High Similarity	NPC164599
0.8519	High Similarity	NPC476022
0.8519	High Similarity	NPC474945
0.8467	Intermediate Similarity	NPC59654
0.837	Intermediate Similarity	NPC474237
0.8357	Intermediate Similarity	NPC470871
0.8333	Intermediate Similarity	NPC271832
0.8286	Intermediate Similarity	NPC317601
0.8286	Intermediate Similarity	NPC329427
0.8276	Intermediate Similarity	NPC184053
0.8261	Intermediate Similarity	NPC201419
0.8231	Intermediate Similarity	NPC89664
0.8231	Intermediate Similarity	NPC274085
0.8231	Intermediate Similarity	NPC477409
0.8227	Intermediate Similarity	NPC129889
0.8227	Intermediate Similarity	NPC307006
0.8224	Intermediate Similarity	NPC301233
0.8219	Intermediate Similarity	NPC229916
0.8219	Intermediate Similarity	NPC474154
0.8194	Intermediate Similarity	NPC98395
0.8188	Intermediate Similarity	NPC142087
0.8188	Intermediate Similarity	NPC95034
0.8168	Intermediate Similarity	NPC322358
0.8163	Intermediate Similarity	NPC474599
0.8146	Intermediate Similarity	NPC475890
0.8138	Intermediate Similarity	NPC147379
0.8133	Intermediate Similarity	NPC228012
0.8125	Intermediate Similarity	NPC470721
0.8125	Intermediate Similarity	NPC6100
0.8125	Intermediate Similarity	NPC156888
0.8125	Intermediate Similarity	NPC470722
0.8121	Intermediate Similarity	NPC474422
0.8116	Intermediate Similarity	NPC475236
0.8108	Intermediate Similarity	NPC469683
0.8108	Intermediate Similarity	NPC10302
0.8108	Intermediate Similarity	NPC105381
0.8082	Intermediate Similarity	NPC477535
0.8067	Intermediate Similarity	NPC61284
0.8067	Intermediate Similarity	NPC66991
0.8067	Intermediate Similarity	NPC98009
0.8067	Intermediate Similarity	NPC113428
0.8067	Intermediate Similarity	NPC210320
0.8056	Intermediate Similarity	NPC71638
0.8056	Intermediate Similarity	NPC64230
0.8054	Intermediate Similarity	NPC98356
0.8052	Intermediate Similarity	NPC99381
0.8042	Intermediate Similarity	NPC34456
0.8041	Intermediate Similarity	NPC476310
0.8041	Intermediate Similarity	NPC469615
0.8041	Intermediate Similarity	NPC473090
0.8041	Intermediate Similarity	NPC472006
0.8041	Intermediate Similarity	NPC51106
0.8041	Intermediate Similarity	NPC476164
0.8039	Intermediate Similarity	NPC474843
0.8026	Intermediate Similarity	NPC37348
0.8014	Intermediate Similarity	NPC79372
0.8013	Intermediate Similarity	NPC215711
0.8013	Intermediate Similarity	NPC73411
0.8	Intermediate Similarity	NPC187826
0.8	Intermediate Similarity	NPC470397
0.8	Intermediate Similarity	NPC308799
0.8	Intermediate Similarity	NPC286038
0.8	Intermediate Similarity	NPC107625
0.8	Intermediate Similarity	NPC232295
0.8	Intermediate Similarity	NPC240147
0.8	Intermediate Similarity	NPC317383
0.8	Intermediate Similarity	NPC121243
0.8	Intermediate Similarity	NPC474131
0.8	Intermediate Similarity	NPC473744
0.7987	Intermediate Similarity	NPC84721
0.7987	Intermediate Similarity	NPC469642
0.7987	Intermediate Similarity	NPC193200
0.7987	Intermediate Similarity	NPC213900
0.7975	Intermediate Similarity	NPC164937
0.7974	Intermediate Similarity	NPC48671
0.7974	Intermediate Similarity	NPC295650
0.7973	Intermediate Similarity	NPC474385
0.7971	Intermediate Similarity	NPC221798
0.7961	Intermediate Similarity	NPC4423
0.7961	Intermediate Similarity	NPC77325
0.7959	Intermediate Similarity	NPC37992
0.7959	Intermediate Similarity	NPC147542
0.7959	Intermediate Similarity	NPC241349
0.7959	Intermediate Similarity	NPC32749
0.7959	Intermediate Similarity	NPC327916
0.7959	Intermediate Similarity	NPC477537
0.7959	Intermediate Similarity	NPC220496
0.7959	Intermediate Similarity	NPC42262
0.7958	Intermediate Similarity	NPC258073
0.7958	Intermediate Similarity	NPC473777
0.7956	Intermediate Similarity	NPC302211
0.7956	Intermediate Similarity	NPC204535
0.7956	Intermediate Similarity	NPC46586
0.7956	Intermediate Similarity	NPC49441
0.7949	Intermediate Similarity	NPC282390
0.7949	Intermediate Similarity	NPC281137
0.7947	Intermediate Similarity	NPC472969
0.7947	Intermediate Similarity	NPC472036
0.7945	Intermediate Similarity	NPC148738
0.7945	Intermediate Similarity	NPC327612
0.7945	Intermediate Similarity	NPC221046
0.7945	Intermediate Similarity	NPC319870
0.7945	Intermediate Similarity	NPC265335
0.7945	Intermediate Similarity	NPC73078
0.7941	Intermediate Similarity	NPC473875
0.7941	Intermediate Similarity	NPC475529
0.7937	Intermediate Similarity	NPC471823
0.7935	Intermediate Similarity	NPC326910
0.7935	Intermediate Similarity	NPC237560
0.7933	Intermediate Similarity	NPC118059
0.7933	Intermediate Similarity	NPC470554
0.7933	Intermediate Similarity	NPC133060
0.7933	Intermediate Similarity	NPC288910
0.7931	Intermediate Similarity	NPC278832
0.7931	Intermediate Similarity	NPC64157
0.7929	Intermediate Similarity	NPC121104
0.7926	Intermediate Similarity	NPC32152
0.7922	Intermediate Similarity	NPC183536
0.7922	Intermediate Similarity	NPC34965
0.7922	Intermediate Similarity	NPC281272
0.7919	Intermediate Similarity	NPC316691
0.7911	Intermediate Similarity	NPC3629
0.7908	Intermediate Similarity	NPC469619
0.7908	Intermediate Similarity	NPC140133
0.7908	Intermediate Similarity	NPC474735
0.7908	Intermediate Similarity	NPC61258
0.7908	Intermediate Similarity	NPC469670
0.7905	Intermediate Similarity	NPC471444
0.7905	Intermediate Similarity	NPC257003
0.7905	Intermediate Similarity	NPC67650
0.7905	Intermediate Similarity	NPC253722
0.7905	Intermediate Similarity	NPC1704
0.7905	Intermediate Similarity	NPC253481
0.7905	Intermediate Similarity	NPC31751
0.7902	Intermediate Similarity	NPC302844
0.7902	Intermediate Similarity	NPC470160
0.7902	Intermediate Similarity	NPC118253
0.7902	Intermediate Similarity	NPC269421
0.7902	Intermediate Similarity	NPC476389
0.7902	Intermediate Similarity	NPC474635
0.7899	Intermediate Similarity	NPC474130
0.7898	Intermediate Similarity	NPC57072
0.7898	Intermediate Similarity	NPC231475
0.7898	Intermediate Similarity	NPC152904
0.7895	Intermediate Similarity	NPC191634
0.7895	Intermediate Similarity	NPC471642
0.7895	Intermediate Similarity	NPC476394
0.7895	Intermediate Similarity	NPC471641
0.7895	Intermediate Similarity	NPC240253
0.7895	Intermediate Similarity	NPC240622
0.7895	Intermediate Similarity	NPC98809
0.7891	Intermediate Similarity	NPC299405
0.7891	Intermediate Similarity	NPC471602
0.7891	Intermediate Similarity	NPC216312
0.7891	Intermediate Similarity	NPC268691
0.7891	Intermediate Similarity	NPC322021
0.7891	Intermediate Similarity	NPC256463
0.7891	Intermediate Similarity	NPC470399
0.7891	Intermediate Similarity	NPC306835
0.7891	Intermediate Similarity	NPC111422
0.7891	Intermediate Similarity	NPC473988
0.7891	Intermediate Similarity	NPC29771
0.7891	Intermediate Similarity	NPC476477
0.7887	Intermediate Similarity	NPC196621
0.7887	Intermediate Similarity	NPC86774
0.7887	Intermediate Similarity	NPC109778
0.7887	Intermediate Similarity	NPC470725
0.7887	Intermediate Similarity	NPC327457
0.7885	Intermediate Similarity	NPC20530
0.7885	Intermediate Similarity	NPC163635
0.7885	Intermediate Similarity	NPC10754
0.7885	Intermediate Similarity	NPC154341
0.7885	Intermediate Similarity	NPC215917
0.7881	Intermediate Similarity	NPC208507
0.7881	Intermediate Similarity	NPC472033
0.7881	Intermediate Similarity	NPC470910
0.7881	Intermediate Similarity	NPC472333

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 NPC476025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	856
0.2-0.3	1758
0.3-0.4	2440
0.4-0.5	1951
0.5-0.6	1163
0.6-0.7	573
0.7-0.8	145
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8222	Intermediate Similarity	NPD1608	Approved
0.8056	Intermediate Similarity	NPD7033	Discontinued
0.8054	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD17	Approved
0.8	Intermediate Similarity	NPD1778	Approved
0.7972	Intermediate Similarity	NPD6355	Discontinued
0.7945	Intermediate Similarity	NPD6002	Phase 3
0.7945	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6005	Phase 3
0.7945	Intermediate Similarity	NPD6004	Phase 3
0.7945	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3496	Discontinued
0.7895	Intermediate Similarity	NPD6671	Approved
0.7877	Intermediate Similarity	NPD6100	Approved
0.7877	Intermediate Similarity	NPD6099	Approved
0.7838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD6798	Discontinued
0.7722	Intermediate Similarity	NPD7075	Discontinued
0.7708	Intermediate Similarity	NPD6233	Phase 2
0.7703	Intermediate Similarity	NPD5763	Approved
0.7703	Intermediate Similarity	NPD5762	Approved
0.7697	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2861	Phase 2
0.7671	Intermediate Similarity	NPD6653	Approved
0.7655	Intermediate Similarity	NPD4060	Phase 1
0.7643	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3268	Approved
0.7635	Intermediate Similarity	NPD2935	Discontinued
0.7606	Intermediate Similarity	NPD5647	Approved
0.7571	Intermediate Similarity	NPD1481	Phase 2
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD2797	Approved
0.7533	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2801	Approved
0.7532	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7819	Suspended
0.7516	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD1535	Discovery
0.7484	Intermediate Similarity	NPD3817	Phase 2
0.7468	Intermediate Similarity	NPD6801	Discontinued
0.7468	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD1934	Approved
0.7468	Intermediate Similarity	NPD2533	Approved
0.7467	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6696	Suspended
0.7464	Intermediate Similarity	NPD9545	Approved
0.745	Intermediate Similarity	NPD2799	Discontinued
0.7448	Intermediate Similarity	NPD7095	Approved
0.7439	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6166	Phase 2
0.7439	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3882	Suspended
0.7436	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3787	Discontinued
0.7417	Intermediate Similarity	NPD1549	Phase 2
0.7413	Intermediate Similarity	NPD6362	Approved
0.7412	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5585	Approved
0.741	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6032	Approved
0.7399	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7985	Registered
0.7397	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2313	Discontinued
0.7383	Intermediate Similarity	NPD7097	Phase 1
0.7375	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD447	Suspended
0.7351	Intermediate Similarity	NPD2346	Discontinued
0.7351	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4062	Phase 3
0.7342	Intermediate Similarity	NPD6599	Discontinued
0.7324	Intermediate Similarity	NPD9717	Approved
0.732	Intermediate Similarity	NPD3750	Approved
0.7317	Intermediate Similarity	NPD7229	Phase 3
0.7308	Intermediate Similarity	NPD1512	Approved
0.7305	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7411	Suspended
0.7292	Intermediate Similarity	NPD3266	Approved
0.7292	Intermediate Similarity	NPD3267	Approved
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2796	Approved
0.7285	Intermediate Similarity	NPD1551	Phase 2
0.7284	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7251	Discontinued
0.7273	Intermediate Similarity	NPD4749	Approved
0.7262	Intermediate Similarity	NPD7074	Phase 3
0.726	Intermediate Similarity	NPD6832	Phase 2
0.725	Intermediate Similarity	NPD6844	Discontinued
0.7248	Intermediate Similarity	NPD4618	Approved
0.7248	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4622	Approved
0.7248	Intermediate Similarity	NPD5124	Phase 1
0.7248	Intermediate Similarity	NPD230	Phase 1
0.7246	Intermediate Similarity	NPD3818	Discontinued
0.7246	Intermediate Similarity	NPD3751	Discontinued
0.7244	Intermediate Similarity	NPD5401	Approved
0.7244	Intermediate Similarity	NPD3146	Approved
0.7244	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7808	Phase 3
0.7233	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD3225	Approved
0.7222	Intermediate Similarity	NPD1283	Approved
0.7219	Intermediate Similarity	NPD4308	Phase 3
0.7219	Intermediate Similarity	NPD6797	Phase 2
0.7219	Intermediate Similarity	NPD1510	Phase 2
0.7214	Intermediate Similarity	NPD1894	Discontinued
0.7208	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4110	Phase 3
0.7205	Intermediate Similarity	NPD8455	Phase 2
0.7202	Intermediate Similarity	NPD7054	Approved
0.7195	Intermediate Similarity	NPD5494	Approved
0.7193	Intermediate Similarity	NPD8312	Approved
0.7193	Intermediate Similarity	NPD8313	Approved
0.7192	Intermediate Similarity	NPD2237	Approved
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7181	Intermediate Similarity	NPD1240	Approved
0.7181	Intermediate Similarity	NPD2979	Phase 3
0.7179	Intermediate Similarity	NPD1511	Approved
0.7172	Intermediate Similarity	NPD1203	Approved
0.7171	Intermediate Similarity	NPD4476	Approved
0.7171	Intermediate Similarity	NPD4477	Approved
0.7169	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8150	Discontinued
0.7162	Intermediate Similarity	NPD411	Approved
0.7161	Intermediate Similarity	NPD3887	Approved
0.716	Intermediate Similarity	NPD7472	Approved
0.7153	Intermediate Similarity	NPD4359	Approved
0.7152	Intermediate Similarity	NPD5689	Approved
0.7152	Intermediate Similarity	NPD5688	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7133	Intermediate Similarity	NPD1611	Approved
0.7133	Intermediate Similarity	NPD1091	Approved
0.7124	Intermediate Similarity	NPD2344	Approved
0.7124	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4965	Approved
0.7117	Intermediate Similarity	NPD4966	Approved
0.7117	Intermediate Similarity	NPD7768	Phase 2
0.7117	Intermediate Similarity	NPD4967	Phase 2
0.7115	Intermediate Similarity	NPD6667	Approved
0.7115	Intermediate Similarity	NPD6666	Approved
0.7114	Intermediate Similarity	NPD8032	Phase 2
0.7113	Intermediate Similarity	NPD4626	Approved
0.7101	Intermediate Similarity	NPD1241	Discontinued
0.7099	Intermediate Similarity	NPD7972	Discontinued
0.709	Intermediate Similarity	NPD968	Approved
0.7089	Intermediate Similarity	NPD6273	Approved
0.7086	Intermediate Similarity	NPD1607	Approved
0.7078	Intermediate Similarity	NPD2424	Discontinued
0.7078	Intermediate Similarity	NPD2897	Discontinued
0.7078	Intermediate Similarity	NPD5958	Discontinued
0.7078	Intermediate Similarity	NPD4534	Discontinued
0.7073	Intermediate Similarity	NPD3749	Approved
0.7071	Intermediate Similarity	NPD7340	Approved
0.7067	Intermediate Similarity	NPD4140	Approved
0.7067	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1613	Approved
0.7063	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2354	Approved
0.705	Intermediate Similarity	NPD2629	Approved
0.7048	Intermediate Similarity	NPD8127	Discontinued
0.7048	Intermediate Similarity	NPD6959	Discontinued
0.7047	Intermediate Similarity	NPD3764	Approved
0.7047	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD920	Approved
0.7042	Intermediate Similarity	NPD5691	Approved
0.7037	Intermediate Similarity	NPD290	Approved
0.7032	Intermediate Similarity	NPD2800	Approved
0.703	Intermediate Similarity	NPD6234	Discontinued
0.7029	Intermediate Similarity	NPD7843	Approved
0.7027	Intermediate Similarity	NPD2614	Approved
0.7024	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7644	Approved
0.7019	Intermediate Similarity	NPD4972	Discontinued
0.7014	Intermediate Similarity	NPD1610	Phase 2
0.7014	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1281	Approved
0.7007	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2798	Approved

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