NPASS Compound

Structure

NPC474943 OpenBabel07101718192D 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 6.1340 -3.6962 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 1.6340 0.6340 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 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 0 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 3.6340 -2.8301 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 -1.9641 0.0000 C 0 0 1 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 3.1340 -3.6962 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 2.1340 -1.9641 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 2 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 2 0 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 1 1 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.28
Volume:	530.597
LogP:	4.351
LogD:	4.505
LogS:	-5.156
# Rotatable Bonds:	16
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	4.139
Fsp3:	0.483
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.689
MDCK Permeability:	2.2530077330884524e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	99.7867660522461%
Volume Distribution (VD):	0.247
Pgp-substrate:	0.8610196113586426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.479
CYP2C19-inhibitor:	0.779
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.696
CYP2D6-substrate:	0.715
CYP3A4-inhibitor:	0.962
CYP3A4-substrate:	0.515

ADMET: Excretion

Clearance (CL):	8.974
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.197
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.887
Carcinogencity:	0.677
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.4

Download Data

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

Natural Product: NPC474943

Natural Product ID:	NPC474943
*Common Name:**	Methyl 2-[5-Hydroxy-2-[(6E,10E,12S)-12-Hydroxy-3,7,11,15-Tetramethyl-13-Oxohexadeca-1,6,10,14-Tetraen-3-Yl]Oxyphenyl]Acetate
IUPAC Name:	methyl 2-[5-hydroxy-2-[(6E,10E,12S)-12-hydroxy-3,7,11,15-tetramethyl-13-oxohexadeca-1,6,10,14-tetraen-3-yl]oxyphenyl]acetate
Synonyms:
Standard InCHIKey:	WLJSTXIKNUMBDH-XWFSAHJLSA-N
Standard InCHI:	InChI=1S/C29H40O6/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/h8,12-15,17-18,28,30,33H,1,9-11,16,19H2,2-7H3/b21-12+,22-13+/t28-,29?/m0/s1
SMILES:	COC(=O)Cc1cc(O)ccc1OC(CC/C=C(/CC/C=C(/[C@@H](C(=O)C=C(C)C)O)C)C)(C=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489369
PubChem CID:	25136073
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[493169]
NPT2	Others	Unspecified		IC50	>	200.0	ug.mL-1	PMID[493169]
NPT1	Others	Radical scavenging activity		RC50	=	14.71	ug ml-1	PMID[493169]

☑ 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 NPC474943 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	294
0.1-0.2	1280
0.2-0.3	3419
0.3-0.4	7692
0.4-0.5	10707
0.5-0.6	4340
0.6-0.7	7754
0.7-0.8	7039
0.8-0.85	149
0.85-0.9	12
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475005
0.9924	High Similarity	NPC475045
0.985	High Similarity	NPC475044
0.985	High Similarity	NPC475063
0.9699	High Similarity	NPC476025
0.9699	High Similarity	NPC475028
0.9474	High Similarity	NPC475029
0.9474	High Similarity	NPC475011
0.9474	High Similarity	NPC476018
0.9197	High Similarity	NPC475012
0.8815	High Similarity	NPC163169
0.8815	High Similarity	NPC123
0.8667	High Similarity	NPC476024
0.8613	High Similarity	NPC474246
0.8613	High Similarity	NPC474143
0.8603	High Similarity	NPC59654
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
0.854	High Similarity	NPC475880
0.8531	High Similarity	NPC164599
0.8519	High Similarity	NPC474944
0.8489	Intermediate Similarity	NPC470871
0.8467	Intermediate Similarity	NPC271832
0.8444	Intermediate Similarity	NPC477213
0.8417	Intermediate Similarity	NPC317601
0.8417	Intermediate Similarity	NPC329427
0.8403	Intermediate Similarity	NPC184053
0.8394	Intermediate Similarity	NPC201419
0.8382	Intermediate Similarity	NPC476022
0.8382	Intermediate Similarity	NPC474945
0.8356	Intermediate Similarity	NPC274085
0.8356	Intermediate Similarity	NPC89664
0.8356	Intermediate Similarity	NPC477409
0.8345	Intermediate Similarity	NPC474154
0.8344	Intermediate Similarity	NPC301233
0.8322	Intermediate Similarity	NPC98395
0.8321	Intermediate Similarity	NPC142087
0.8321	Intermediate Similarity	NPC95034
0.8311	Intermediate Similarity	NPC210320
0.8299	Intermediate Similarity	NPC98356
0.8288	Intermediate Similarity	NPC473090
0.8255	Intermediate Similarity	NPC73411
0.8255	Intermediate Similarity	NPC215711
0.8252	Intermediate Similarity	NPC121243
0.8252	Intermediate Similarity	NPC240147
0.8248	Intermediate Similarity	NPC475236
0.8235	Intermediate Similarity	NPC221798
0.8231	Intermediate Similarity	NPC105381
0.8231	Intermediate Similarity	NPC10302
0.8231	Intermediate Similarity	NPC469683
0.8227	Intermediate Similarity	NPC129889
0.8227	Intermediate Similarity	NPC307006
0.8219	Intermediate Similarity	NPC229916
0.8219	Intermediate Similarity	NPC474385
0.8207	Intermediate Similarity	NPC477535
0.8188	Intermediate Similarity	NPC472969
0.8188	Intermediate Similarity	NPC472036
0.817	Intermediate Similarity	NPC99381
0.8168	Intermediate Similarity	NPC322358
0.8163	Intermediate Similarity	NPC472006
0.8163	Intermediate Similarity	NPC469615
0.8163	Intermediate Similarity	NPC476164
0.8163	Intermediate Similarity	NPC476310
0.8163	Intermediate Similarity	NPC51106
0.8158	Intermediate Similarity	NPC34965
0.8158	Intermediate Similarity	NPC183536
0.8158	Intermediate Similarity	NPC474843
0.8146	Intermediate Similarity	NPC475890
0.8146	Intermediate Similarity	NPC37348
0.8133	Intermediate Similarity	NPC471641
0.8133	Intermediate Similarity	NPC228012
0.8133	Intermediate Similarity	NPC240622
0.8133	Intermediate Similarity	NPC240253
0.8133	Intermediate Similarity	NPC98809
0.8133	Intermediate Similarity	NPC476394
0.8133	Intermediate Similarity	NPC471642
0.8129	Intermediate Similarity	NPC2596
0.8129	Intermediate Similarity	NPC231475
0.8129	Intermediate Similarity	NPC57072
0.8129	Intermediate Similarity	NPC473744
0.8121	Intermediate Similarity	NPC474422
0.8121	Intermediate Similarity	NPC107625
0.8121	Intermediate Similarity	NPC308799
0.8121	Intermediate Similarity	NPC472033
0.8112	Intermediate Similarity	NPC281169
0.8112	Intermediate Similarity	NPC161856
0.8112	Intermediate Similarity	NPC298900
0.8112	Intermediate Similarity	NPC70680
0.8112	Intermediate Similarity	NPC291119
0.8112	Intermediate Similarity	NPC51087
0.8112	Intermediate Similarity	NPC233350
0.8112	Intermediate Similarity	NPC182217
0.8108	Intermediate Similarity	NPC277426
0.8108	Intermediate Similarity	NPC213900
0.8108	Intermediate Similarity	NPC210425
0.8108	Intermediate Similarity	NPC469642
0.8108	Intermediate Similarity	NPC86373
0.8108	Intermediate Similarity	NPC280404
0.8105	Intermediate Similarity	NPC84721
0.8105	Intermediate Similarity	NPC193200
0.8102	Intermediate Similarity	NPC474237
0.8088	Intermediate Similarity	NPC69403
0.8088	Intermediate Similarity	NPC132518
0.8088	Intermediate Similarity	NPC291189
0.8088	Intermediate Similarity	NPC49441
0.8088	Intermediate Similarity	NPC477151
0.8085	Intermediate Similarity	NPC473777
0.8082	Intermediate Similarity	NPC477537
0.8079	Intermediate Similarity	NPC77325
0.8079	Intermediate Similarity	NPC4423
0.8069	Intermediate Similarity	NPC221046
0.8067	Intermediate Similarity	NPC98009
0.8067	Intermediate Similarity	NPC61284
0.8067	Intermediate Similarity	NPC66991
0.8067	Intermediate Similarity	NPC140722
0.8067	Intermediate Similarity	NPC92054
0.8067	Intermediate Similarity	NPC113428
0.8067	Intermediate Similarity	NPC4958
0.8067	Intermediate Similarity	NPC83975
0.8065	Intermediate Similarity	NPC474441
0.8065	Intermediate Similarity	NPC474398
0.8065	Intermediate Similarity	NPC474401
0.8065	Intermediate Similarity	NPC281137
0.8065	Intermediate Similarity	NPC476026
0.8065	Intermediate Similarity	NPC282390
0.8058	Intermediate Similarity	NPC71525
0.8058	Intermediate Similarity	NPC121104
0.8056	Intermediate Similarity	NPC71638
0.8056	Intermediate Similarity	NPC64157
0.8056	Intermediate Similarity	NPC278832
0.8056	Intermediate Similarity	NPC64230
0.8054	Intermediate Similarity	NPC472034
0.8052	Intermediate Similarity	NPC473241
0.8052	Intermediate Similarity	NPC326910
0.8052	Intermediate Similarity	NPC237560
0.805	Intermediate Similarity	NPC471823
0.8042	Intermediate Similarity	NPC34456
0.8042	Intermediate Similarity	NPC68517
0.8039	Intermediate Similarity	NPC19380
0.8039	Intermediate Similarity	NPC146277
0.8039	Intermediate Similarity	NPC281272
0.8028	Intermediate Similarity	NPC118253
0.8028	Intermediate Similarity	NPC302844
0.8028	Intermediate Similarity	NPC470160
0.8027	Intermediate Similarity	NPC244923
0.8027	Intermediate Similarity	NPC257003
0.8027	Intermediate Similarity	NPC471444
0.8027	Intermediate Similarity	NPC67650
0.8027	Intermediate Similarity	NPC475730
0.8027	Intermediate Similarity	NPC1704
0.8026	Intermediate Similarity	NPC469619
0.8026	Intermediate Similarity	NPC61258
0.8026	Intermediate Similarity	NPC469670
0.8025	Intermediate Similarity	NPC3629
0.8015	Intermediate Similarity	NPC476165
0.8014	Intermediate Similarity	NPC268691
0.8014	Intermediate Similarity	NPC471602
0.8014	Intermediate Similarity	NPC111422
0.8014	Intermediate Similarity	NPC216312
0.8014	Intermediate Similarity	NPC109778
0.8014	Intermediate Similarity	NPC327457
0.8014	Intermediate Similarity	NPC476820
0.8014	Intermediate Similarity	NPC274891
0.8014	Intermediate Similarity	NPC299405
0.8014	Intermediate Similarity	NPC29771
0.8014	Intermediate Similarity	NPC476477
0.8014	Intermediate Similarity	NPC26241
0.8014	Intermediate Similarity	NPC86774
0.8014	Intermediate Similarity	NPC256463
0.8014	Intermediate Similarity	NPC476819
0.8014	Intermediate Similarity	NPC306835
0.8014	Intermediate Similarity	NPC474875
0.8014	Intermediate Similarity	NPC295492
0.8014	Intermediate Similarity	NPC473988
0.8014	Intermediate Similarity	NPC303683
0.8014	Intermediate Similarity	NPC205751
0.8013	Intermediate Similarity	NPC152904
0.8	Intermediate Similarity	NPC470896
0.8	Intermediate Similarity	NPC470397
0.8	Intermediate Similarity	NPC154341
0.8	Intermediate Similarity	NPC473275
0.8	Intermediate Similarity	NPC286038
0.8	Intermediate Similarity	NPC317383
0.8	Intermediate Similarity	NPC187826
0.7987	Intermediate Similarity	NPC280923
0.7987	Intermediate Similarity	NPC113397
0.7987	Intermediate Similarity	NPC470216
0.7987	Intermediate Similarity	NPC33653
0.7987	Intermediate Similarity	NPC184738
0.7987	Intermediate Similarity	NPC86485
0.7986	Intermediate Similarity	NPC142027
0.7986	Intermediate Similarity	NPC27407
0.7986	Intermediate Similarity	NPC139519
0.7986	Intermediate Similarity	NPC204579
0.7986	Intermediate Similarity	NPC110211
0.7975	Intermediate Similarity	NPC164937
0.7974	Intermediate Similarity	NPC75695

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 NPC474943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	859
0.2-0.3	1804
0.3-0.4	2413
0.4-0.5	1966
0.5-0.6	1149
0.6-0.7	544
0.7-0.8	148
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8209	Intermediate Similarity	NPD3496	Discontinued
0.8052	Intermediate Similarity	NPD5402	Approved
0.8014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1778	Approved
0.7959	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1608	Approved
0.7931	Intermediate Similarity	NPD7033	Discontinued
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7834	Intermediate Similarity	NPD7075	Discontinued
0.7815	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD6671	Approved
0.7758	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2801	Approved
0.7756	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2935	Discontinued
0.7748	Intermediate Similarity	NPD6799	Approved
0.7737	Intermediate Similarity	NPD17	Approved
0.7733	Intermediate Similarity	NPD6190	Approved
0.7724	Intermediate Similarity	NPD6355	Discontinued
0.7721	Intermediate Similarity	NPD9545	Approved
0.7708	Intermediate Similarity	NPD6233	Phase 2
0.7707	Intermediate Similarity	NPD3817	Phase 2
0.7703	Intermediate Similarity	NPD6004	Phase 3
0.7703	Intermediate Similarity	NPD6005	Phase 3
0.7703	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6002	Phase 3
0.7667	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD3882	Suspended
0.7658	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7819	Suspended
0.7639	Intermediate Similarity	NPD6798	Discontinued
0.7639	Intermediate Similarity	NPD3268	Approved
0.7635	Intermediate Similarity	NPD6099	Approved
0.7635	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD3226	Approved
0.7603	Intermediate Similarity	NPD447	Suspended
0.7597	Intermediate Similarity	NPD5403	Approved
0.7584	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2532	Approved
0.7582	Intermediate Similarity	NPD2533	Approved
0.7582	Intermediate Similarity	NPD2534	Approved
0.758	Intermediate Similarity	NPD1934	Approved
0.758	Intermediate Similarity	NPD6801	Discontinued
0.7571	Intermediate Similarity	NPD1481	Phase 2
0.7571	Intermediate Similarity	NPD9717	Approved
0.7551	Intermediate Similarity	NPD6653	Approved
0.7546	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6166	Phase 2
0.7546	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD2797	Approved
0.7533	Intermediate Similarity	NPD1549	Phase 2
0.7532	Intermediate Similarity	NPD1512	Approved
0.753	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1551	Phase 2
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD1535	Discovery
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD5647	Approved
0.7468	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD6844	Discontinued
0.7467	Intermediate Similarity	NPD2346	Discontinued
0.7467	Intermediate Similarity	NPD5762	Approved
0.7467	Intermediate Similarity	NPD5763	Approved
0.7465	Intermediate Similarity	NPD3225	Approved
0.7455	Intermediate Similarity	NPD3751	Discontinued
0.7452	Intermediate Similarity	NPD6599	Discontinued
0.745	Intermediate Similarity	NPD2799	Discontinued
0.744	Intermediate Similarity	NPD7808	Phase 3
0.7434	Intermediate Similarity	NPD3750	Approved
0.7431	Intermediate Similarity	NPD2861	Phase 2
0.7425	Intermediate Similarity	NPD6797	Phase 2
0.7423	Intermediate Similarity	NPD3787	Discontinued
0.7415	Intermediate Similarity	NPD4060	Phase 1
0.7413	Intermediate Similarity	NPD1203	Approved
0.7412	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7054	Approved
0.741	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7411	Suspended
0.7403	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1511	Approved
0.74	Intermediate Similarity	NPD2796	Approved
0.7397	Intermediate Similarity	NPD411	Approved
0.7391	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD422	Phase 1
0.7375	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD7074	Phase 3
0.7365	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7472	Approved
0.7353	Intermediate Similarity	NPD1241	Discontinued
0.7351	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3818	Discontinued
0.7347	Intermediate Similarity	NPD4062	Phase 3
0.7343	Intermediate Similarity	NPD6696	Suspended
0.7342	Intermediate Similarity	NPD4380	Phase 2
0.7333	Intermediate Similarity	NPD1510	Phase 2
0.7333	Intermediate Similarity	NPD4308	Phase 3
0.7329	Intermediate Similarity	NPD7095	Approved
0.7297	Intermediate Similarity	NPD1240	Approved
0.7292	Intermediate Similarity	NPD3266	Approved
0.7292	Intermediate Similarity	NPD6362	Approved
0.7292	Intermediate Similarity	NPD3267	Approved
0.7286	Intermediate Similarity	NPD5585	Approved
0.7285	Intermediate Similarity	NPD6032	Approved
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3887	Approved
0.7248	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5124	Phase 1
0.7244	Intermediate Similarity	NPD3146	Approved
0.7244	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1019	Discontinued
0.7237	Intermediate Similarity	NPD2344	Approved
0.7234	Intermediate Similarity	NPD4626	Approved
0.7222	Intermediate Similarity	NPD7768	Phase 2
0.7215	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1653	Approved
0.7214	Intermediate Similarity	NPD1894	Discontinued
0.72	Intermediate Similarity	NPD1607	Approved
0.7195	Intermediate Similarity	NPD5494	Approved
0.7194	Intermediate Similarity	NPD9493	Approved
0.7193	Intermediate Similarity	NPD8312	Approved
0.7193	Intermediate Similarity	NPD8313	Approved
0.7192	Intermediate Similarity	NPD9494	Approved
0.719	Intermediate Similarity	NPD2424	Discontinued
0.7188	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7178	Intermediate Similarity	NPD3749	Approved
0.7168	Intermediate Similarity	NPD8150	Discontinued
0.7163	Intermediate Similarity	NPD5691	Approved
0.7162	Intermediate Similarity	NPD3764	Approved
0.7162	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7985	Registered
0.7161	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD6959	Discontinued
0.7152	Intermediate Similarity	NPD7097	Phase 1
0.7143	Intermediate Similarity	NPD2800	Approved
0.7133	Intermediate Similarity	NPD1091	Approved
0.7133	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7229	Phase 3
0.7108	Intermediate Similarity	NPD6232	Discontinued
0.7105	Intermediate Similarity	NPD3748	Approved
0.7101	Intermediate Similarity	NPD7286	Phase 2
0.7099	Intermediate Similarity	NPD8455	Phase 2
0.709	Intermediate Similarity	NPD968	Approved
0.7089	Intermediate Similarity	NPD6273	Approved
0.7088	Intermediate Similarity	NPD7435	Discontinued
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6386	Approved
0.7081	Intermediate Similarity	NPD6385	Approved
0.7076	Intermediate Similarity	NPD6559	Discontinued
0.7076	Intermediate Similarity	NPD7685	Pre-registration
0.7067	Intermediate Similarity	NPD4307	Phase 2
0.7063	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD4477	Approved
0.7059	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4476	Approved
0.7051	Intermediate Similarity	NPD2309	Approved
0.7048	Intermediate Similarity	NPD8127	Discontinued
0.7048	Intermediate Similarity	NPD1247	Approved
0.7041	Intermediate Similarity	NPD7177	Discontinued
0.7041	Intermediate Similarity	NPD2163	Approved
0.7037	Intermediate Similarity	NPD290	Approved
0.7034	Intermediate Similarity	NPD4359	Approved
0.7034	Intermediate Similarity	NPD4749	Approved
0.7032	Intermediate Similarity	NPD1652	Phase 2
0.703	Intermediate Similarity	NPD919	Approved
0.7025	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4618	Approved
0.702	Intermediate Similarity	NPD4340	Discontinued
0.702	Intermediate Similarity	NPD4622	Approved
0.7019	Intermediate Similarity	NPD4972	Discontinued
0.7018	Intermediate Similarity	NPD5953	Discontinued
0.7014	Intermediate Similarity	NPD1611	Approved
0.7013	Intermediate Similarity	NPD2353	Approved
0.7013	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD7440	Discontinued
0.7006	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1465	Phase 2
0.6994	Remote Similarity	NPD7972	Discontinued
0.6987	Remote Similarity	NPD4110	Phase 3
0.6987	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1283	Approved
0.6981	Remote Similarity	NPD5049	Phase 3

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