NPASS Compound

Structure

NPC476024 OpenBabel07101718272D 35 35 0 0 1 0 0 0 0 0999 V2000 -5.1962 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 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 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -8.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -10.0000 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 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 -4.3301 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -9.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -9.0000 0.0000 C 0 0 1 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 -2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -8.5000 0.0000 O 0 0 0 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 -2.5981 -7.5000 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 1.7321 3.0000 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 6 35 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 26 1 0 0 0 0 16 23 1 0 0 0 0 16 25 2 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 2 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 31 1 6 0 0 0 27 32 2 0 0 0 0 27 35 1 0 0 0 0 28 33 2 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	533.233
LogP:	5.122
LogD:	4.773
LogS:	-4.935
# Rotatable Bonds:	16
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.136
Synthetic Accessibility Score:	3.672
Fsp3:	0.552
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.89
MDCK Permeability:	2.301555468875449e-05
Pgp-inhibitor:	0.572
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.295
20% Bioavailability (F20%):	0.402
30% Bioavailability (F30%):	0.147

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	95.11883544921875%
Volume Distribution (VD):	0.245
Pgp-substrate:	0.5403692126274109%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.235
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.219
CYP2C9-inhibitor:	0.93
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.76
CYP2D6-substrate:	0.655
CYP3A4-inhibitor:	0.854
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	7.017
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.477
Drug-inuced Liver Injury (DILI):	0.319
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.556
Skin Sensitization:	0.942
Carcinogencity:	0.034
Eye Corrosion:	0.004
Eye Irritation:	0.089
Respiratory Toxicity:	0.249

Download Data

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

Natural Product: NPC476024

Natural Product ID:	NPC476024
*Common Name:**	Methyl 2-[2,5-Dihydroxy-3-[(2E,6E,13S)-13-Hydroxy-3,7,11,15-Tetramethyl-12-Oxohexadeca-2,6,14-Trienyl]Phenyl]Acetate
IUPAC Name:	methyl 2-[2,5-dihydroxy-3-[(2E,6E,13S)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-2,6,14-trienyl]phenyl]acetate
Synonyms:
Standard InCHIKey:	JKCSXRZMRFNFHN-NNHMOVLLSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-19(2)15-26(31)28(33)22(5)12-8-11-20(3)9-7-10-21(4)13-14-23-16-25(30)17-24(29(23)34)18-27(32)35-6/h9,13,15-17,22,26,30-31,34H,7-8,10-12,14,18H2,1-6H3/b20-9+,21-13+/t22?,26-/m0/s1
SMILES:	COC(=O)Cc1cc(O)cc(c1O)C/C=C(/CC/C=C(/CCCC(C(=O)[C@H](C=C(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522279
PubChem CID:	25136227
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	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	23.0	ug.mL-1	PMID[556384]
NPT1	Others	Radical scavenging activity		RC50	=	0.3	ug ml-1	PMID[556384]

☑ 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 NPC476024 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	255
0.1-0.2	1034
0.2-0.3	2815
0.3-0.4	7033
0.4-0.5	12210
0.5-0.6	5732
0.6-0.7	11589
0.7-0.8	1959
0.8-0.85	54
0.85-0.9	10
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9835	High Similarity	NPC474944
0.9677	High Similarity	NPC123
0.9677	High Similarity	NPC163169
0.9512	High Similarity	NPC476022
0.9512	High Similarity	NPC474945
0.8947	High Similarity	NPC475028
0.8947	High Similarity	NPC476025
0.8815	High Similarity	NPC475044
0.8815	High Similarity	NPC475063
0.8722	High Similarity	NPC475011
0.8672	High Similarity	NPC477213
0.8667	High Similarity	NPC474943
0.8667	High Similarity	NPC475005
0.8603	High Similarity	NPC475045
0.856	High Similarity	NPC476020
0.8538	High Similarity	NPC477212
0.8538	High Similarity	NPC319422
0.8538	High Similarity	NPC477214
0.8538	High Similarity	NPC477211
0.8455	Intermediate Similarity	NPC474114
0.8455	Intermediate Similarity	NPC474050
0.8455	Intermediate Similarity	NPC473931
0.8444	Intermediate Similarity	NPC475029
0.8444	Intermediate Similarity	NPC476018
0.8438	Intermediate Similarity	NPC475192
0.8374	Intermediate Similarity	NPC28784
0.8374	Intermediate Similarity	NPC296144
0.837	Intermediate Similarity	NPC204582
0.8333	Intermediate Similarity	NPC473744
0.8308	Intermediate Similarity	NPC474803
0.8306	Intermediate Similarity	NPC114918
0.8284	Intermediate Similarity	NPC474246
0.8284	Intermediate Similarity	NPC474143
0.8273	Intermediate Similarity	NPC3218
0.8248	Intermediate Similarity	NPC475111
0.8217	Intermediate Similarity	NPC31936
0.816	Intermediate Similarity	NPC197513
0.8148	Intermediate Similarity	NPC473777
0.8143	Intermediate Similarity	NPC241349
0.8143	Intermediate Similarity	NPC220496
0.8143	Intermediate Similarity	NPC32749
0.8143	Intermediate Similarity	NPC147542
0.8143	Intermediate Similarity	NPC42262
0.8143	Intermediate Similarity	NPC37992
0.8143	Intermediate Similarity	NPC327916
0.813	Intermediate Similarity	NPC208229
0.8092	Intermediate Similarity	NPC477153
0.8085	Intermediate Similarity	NPC272907
0.8085	Intermediate Similarity	NPC471444
0.8085	Intermediate Similarity	NPC2681
0.8074	Intermediate Similarity	NPC475880
0.8071	Intermediate Similarity	NPC111422
0.8071	Intermediate Similarity	NPC299405
0.8071	Intermediate Similarity	NPC475012
0.8071	Intermediate Similarity	NPC29771
0.8071	Intermediate Similarity	NPC306835
0.8071	Intermediate Similarity	NPC476477
0.8071	Intermediate Similarity	NPC216312
0.8071	Intermediate Similarity	NPC256463
0.8071	Intermediate Similarity	NPC471602
0.8049	Intermediate Similarity	NPC282855
0.8049	Intermediate Similarity	NPC26013
0.8043	Intermediate Similarity	NPC279463
0.8029	Intermediate Similarity	NPC49742
0.8029	Intermediate Similarity	NPC239855
0.8	Intermediate Similarity	NPC474175
0.8	Intermediate Similarity	NPC5568
0.7984	Intermediate Similarity	NPC473767
0.797	Intermediate Similarity	NPC472592
0.797	Intermediate Similarity	NPC127975
0.7967	Intermediate Similarity	NPC279887
0.7967	Intermediate Similarity	NPC68260
0.7958	Intermediate Similarity	NPC257003
0.7956	Intermediate Similarity	NPC110609
0.7956	Intermediate Similarity	NPC246693
0.7956	Intermediate Similarity	NPC242358
0.7956	Intermediate Similarity	NPC302844
0.7956	Intermediate Similarity	NPC476389
0.7951	Intermediate Similarity	NPC317592
0.7951	Intermediate Similarity	NPC469913
0.7945	Intermediate Similarity	NPC94781
0.7939	Intermediate Similarity	NPC472892
0.7937	Intermediate Similarity	NPC62546
0.7937	Intermediate Similarity	NPC162113
0.7929	Intermediate Similarity	NPC470722
0.7929	Intermediate Similarity	NPC156888
0.7929	Intermediate Similarity	NPC470721
0.7929	Intermediate Similarity	NPC6100
0.7923	Intermediate Similarity	NPC473136
0.7923	Intermediate Similarity	NPC478121
0.792	Intermediate Similarity	NPC228609
0.7919	Intermediate Similarity	NPC474824
0.7919	Intermediate Similarity	NPC218870
0.7919	Intermediate Similarity	NPC470408
0.7919	Intermediate Similarity	NPC182921
0.7917	Intermediate Similarity	NPC126707
0.7917	Intermediate Similarity	NPC477409
0.7907	Intermediate Similarity	NPC206205
0.7907	Intermediate Similarity	NPC273282
0.7907	Intermediate Similarity	NPC474890
0.7907	Intermediate Similarity	NPC161943
0.7902	Intermediate Similarity	NPC474300
0.7899	Intermediate Similarity	NPC477280
0.7899	Intermediate Similarity	NPC19719
0.7899	Intermediate Similarity	NPC477281
0.7895	Intermediate Similarity	NPC184219
0.7895	Intermediate Similarity	NPC117794
0.7891	Intermediate Similarity	NPC83718
0.7887	Intermediate Similarity	NPC469911
0.7883	Intermediate Similarity	NPC258073
0.7879	Intermediate Similarity	NPC49441
0.7879	Intermediate Similarity	NPC67300
0.7872	Intermediate Similarity	NPC475974
0.7868	Intermediate Similarity	NPC59654
0.7868	Intermediate Similarity	NPC278928
0.7863	Intermediate Similarity	NPC164852
0.7847	Intermediate Similarity	NPC354984
0.7847	Intermediate Similarity	NPC476473
0.7842	Intermediate Similarity	NPC477210
0.7836	Intermediate Similarity	NPC87985
0.7836	Intermediate Similarity	NPC287473
0.7836	Intermediate Similarity	NPC240744
0.7836	Intermediate Similarity	NPC167055
0.7832	Intermediate Similarity	NPC244923
0.7832	Intermediate Similarity	NPC477278
0.7832	Intermediate Similarity	NPC477277
0.7829	Intermediate Similarity	NPC160199
0.7829	Intermediate Similarity	NPC325295
0.7829	Intermediate Similarity	NPC76308
0.7826	Intermediate Similarity	NPC327204
0.7826	Intermediate Similarity	NPC323379
0.7823	Intermediate Similarity	NPC473719
0.782	Intermediate Similarity	NPC275145
0.782	Intermediate Similarity	NPC273683
0.7815	Intermediate Similarity	NPC474861
0.781	Intermediate Similarity	NPC253488
0.7808	Intermediate Similarity	NPC474991
0.7801	Intermediate Similarity	NPC474849
0.7801	Intermediate Similarity	NPC149372
0.7801	Intermediate Similarity	NPC474771
0.7801	Intermediate Similarity	NPC178467
0.7801	Intermediate Similarity	NPC194579
0.7801	Intermediate Similarity	NPC475957
0.7801	Intermediate Similarity	NPC65837
0.7795	Intermediate Similarity	NPC190212
0.7794	Intermediate Similarity	NPC24869
0.7793	Intermediate Similarity	NPC274085
0.7793	Intermediate Similarity	NPC89664
0.7786	Intermediate Similarity	NPC70680
0.7786	Intermediate Similarity	NPC130899
0.7786	Intermediate Similarity	NPC61153
0.7786	Intermediate Similarity	NPC70859
0.7786	Intermediate Similarity	NPC233350
0.7786	Intermediate Similarity	NPC142027
0.7786	Intermediate Similarity	NPC27407
0.7786	Intermediate Similarity	NPC182217
0.7786	Intermediate Similarity	NPC283590
0.7785	Intermediate Similarity	NPC205918
0.7778	Intermediate Similarity	NPC473751
0.7778	Intermediate Similarity	NPC204579
0.7778	Intermediate Similarity	NPC110211
0.777	Intermediate Similarity	NPC280753
0.777	Intermediate Similarity	NPC78307
0.777	Intermediate Similarity	NPC129889
0.777	Intermediate Similarity	NPC307006
0.777	Intermediate Similarity	NPC44378
0.777	Intermediate Similarity	NPC471749
0.777	Intermediate Similarity	NPC120171
0.7769	Intermediate Similarity	NPC63126
0.7762	Intermediate Similarity	NPC477279
0.7762	Intermediate Similarity	NPC315578
0.7761	Intermediate Similarity	NPC474237
0.7761	Intermediate Similarity	NPC181334
0.7761	Intermediate Similarity	NPC231767
0.7761	Intermediate Similarity	NPC85565
0.776	Intermediate Similarity	NPC473524
0.7755	Intermediate Similarity	NPC127046
0.7754	Intermediate Similarity	NPC476847
0.7746	Intermediate Similarity	NPC112135
0.7746	Intermediate Similarity	NPC212693
0.7746	Intermediate Similarity	NPC94248
0.7746	Intermediate Similarity	NPC472403
0.7746	Intermediate Similarity	NPC191835
0.7744	Intermediate Similarity	NPC477151
0.7744	Intermediate Similarity	NPC121168
0.7744	Intermediate Similarity	NPC297193
0.7744	Intermediate Similarity	NPC132518
0.774	Intermediate Similarity	NPC84786
0.774	Intermediate Similarity	NPC258856
0.774	Intermediate Similarity	NPC75295
0.7737	Intermediate Similarity	NPC271832
0.773	Intermediate Similarity	NPC472308
0.7724	Intermediate Similarity	NPC477207
0.7721	Intermediate Similarity	NPC209959
0.7718	Intermediate Similarity	NPC56204
0.7718	Intermediate Similarity	NPC475407
0.7718	Intermediate Similarity	NPC315520
0.7717	Intermediate Similarity	NPC26615
0.7714	Intermediate Similarity	NPC68517
0.7714	Intermediate Similarity	NPC474394

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 NPC476024 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	803
0.2-0.3	1742
0.3-0.4	2674
0.4-0.5	2060
0.5-0.6	1105
0.6-0.7	505
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7462	Intermediate Similarity	NPD2629	Approved
0.7431	Intermediate Similarity	NPD2935	Discontinued
0.7415	Intermediate Similarity	NPD6190	Approved
0.7379	Intermediate Similarity	NPD6005	Phase 3
0.7379	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6002	Phase 3
0.7379	Intermediate Similarity	NPD6004	Phase 3
0.7379	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9545	Approved
0.7353	Intermediate Similarity	NPD1608	Approved
0.7279	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7254	Intermediate Similarity	NPD6663	Approved
0.7214	Intermediate Similarity	NPD5736	Approved
0.7197	Intermediate Similarity	NPD7075	Discontinued
0.7186	Intermediate Similarity	NPD8150	Discontinued
0.7185	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7635	Approved
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD17	Approved
0.7132	Intermediate Similarity	NPD1778	Approved
0.7123	Intermediate Similarity	NPD7033	Discontinued
0.712	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9495	Approved
0.7095	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4060	Phase 1
0.708	Intermediate Similarity	NPD3496	Discontinued
0.7075	Intermediate Similarity	NPD6099	Approved
0.7075	Intermediate Similarity	NPD6100	Approved
0.7071	Intermediate Similarity	NPD1470	Approved
0.707	Intermediate Similarity	NPD5402	Approved
0.7054	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5048	Discontinued
0.7029	Intermediate Similarity	NPD1201	Approved
0.7027	Intermediate Similarity	NPD5763	Approved
0.7027	Intermediate Similarity	NPD5762	Approved
0.7021	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3019	Approved
0.7007	Intermediate Similarity	NPD2932	Approved
0.7006	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4628	Phase 3
0.7	Intermediate Similarity	NPD3400	Discontinued
0.7	Intermediate Similarity	NPD1283	Approved
0.6994	Remote Similarity	NPD7473	Discontinued
0.6978	Remote Similarity	NPD9269	Phase 2
0.6968	Remote Similarity	NPD3226	Approved
0.6963	Remote Similarity	NPD9493	Approved
0.6947	Remote Similarity	NPD4750	Phase 3
0.6944	Remote Similarity	NPD6798	Discontinued
0.6943	Remote Similarity	NPD6801	Discontinued
0.6943	Remote Similarity	NPD37	Approved
0.6935	Remote Similarity	NPD844	Approved
0.6934	Remote Similarity	NPD9268	Approved
0.6923	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4380	Phase 2
0.6918	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD845	Approved
0.6909	Remote Similarity	NPD5844	Phase 1
0.6908	Remote Similarity	NPD3300	Phase 2
0.6901	Remote Similarity	NPD6085	Phase 2
0.6901	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6233	Phase 2
0.6892	Remote Similarity	NPD2799	Discontinued
0.6892	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6671	Approved
0.6887	Remote Similarity	NPD8166	Discontinued
0.6884	Remote Similarity	NPD4626	Approved
0.688	Remote Similarity	NPD288	Approved
0.6879	Remote Similarity	NPD6696	Suspended
0.6879	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6653	Approved
0.6863	Remote Similarity	NPD7390	Discontinued
0.6859	Remote Similarity	NPD7458	Discontinued
0.6855	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2861	Phase 2
0.6849	Remote Similarity	NPD943	Approved
0.6849	Remote Similarity	NPD2979	Phase 3
0.6846	Remote Similarity	NPD5406	Approved
0.6846	Remote Similarity	NPD5404	Approved
0.6846	Remote Similarity	NPD5408	Approved
0.6846	Remote Similarity	NPD5405	Approved
0.6845	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2313	Discontinued
0.6828	Remote Similarity	NPD7985	Registered
0.6828	Remote Similarity	NPD3268	Approved
0.6828	Remote Similarity	NPD3764	Approved
0.6826	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4966	Approved
0.6813	Remote Similarity	NPD4965	Approved
0.6813	Remote Similarity	NPD4967	Phase 2
0.681	Remote Similarity	NPD6232	Discontinued
0.681	Remote Similarity	NPD7229	Phase 3
0.6809	Remote Similarity	NPD1755	Approved
0.6807	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2346	Discontinued
0.68	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2801	Approved
0.6786	Remote Similarity	NPD1281	Approved
0.6783	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5647	Approved
0.6781	Remote Similarity	NPD4248	Discontinued
0.6779	Remote Similarity	NPD1510	Phase 2
0.6779	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7411	Suspended
0.6757	Remote Similarity	NPD6651	Approved
0.6753	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6799	Approved
0.6752	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3817	Phase 2
0.6744	Remote Similarity	NPD6647	Phase 2
0.6742	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD74	Approved
0.6742	Remote Similarity	NPD9266	Approved
0.6741	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1759	Phase 1
0.6738	Remote Similarity	NPD1481	Phase 2
0.6735	Remote Similarity	NPD825	Approved
0.6735	Remote Similarity	NPD1240	Approved
0.6735	Remote Similarity	NPD826	Approved
0.673	Remote Similarity	NPD1934	Approved
0.6728	Remote Similarity	NPD6234	Discontinued
0.6727	Remote Similarity	NPD6166	Phase 2
0.6727	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6685	Approved
0.6716	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1164	Approved
0.6713	Remote Similarity	NPD2797	Approved
0.6712	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3882	Suspended
0.6706	Remote Similarity	NPD8313	Approved
0.6706	Remote Similarity	NPD8312	Approved
0.6705	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1237	Approved
0.6692	Remote Similarity	NPD2067	Discontinued
0.6691	Remote Similarity	NPD5691	Approved
0.6689	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7266	Discontinued
0.6688	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7236	Approved
0.6687	Remote Similarity	NPD8455	Phase 2
0.6687	Remote Similarity	NPD5494	Approved
0.6686	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD7305	Phase 1
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD940	Approved
0.6667	Remote Similarity	NPD1758	Phase 1
0.6667	Remote Similarity	NPD1535	Discovery
0.6667	Remote Similarity	NPD1809	Phase 2
0.6647	Remote Similarity	NPD7228	Approved
0.6646	Remote Similarity	NPD6959	Discontinued
0.6645	Remote Similarity	NPD1549	Phase 2
0.6644	Remote Similarity	NPD1607	Approved
0.6642	Remote Similarity	NPD255	Approved
0.6642	Remote Similarity	NPD256	Approved
0.6641	Remote Similarity	NPD3020	Approved
0.663	Remote Similarity	NPD7435	Discontinued
0.6624	Remote Similarity	NPD5403	Approved
0.6623	Remote Similarity	NPD4477	Approved
0.6623	Remote Similarity	NPD2438	Suspended
0.6623	Remote Similarity	NPD6032	Approved
0.6623	Remote Similarity	NPD9570	Approved
0.6623	Remote Similarity	NPD4476	Approved
0.6622	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3091	Approved
0.6615	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5765	Approved
0.6606	Remote Similarity	NPD5711	Approved
0.6606	Remote Similarity	NPD5710	Approved
0.6606	Remote Similarity	NPD3787	Discontinued
0.6605	Remote Similarity	NPD7768	Phase 2
0.6604	Remote Similarity	NPD6599	Discontinued
0.6601	Remote Similarity	NPD2800	Approved
0.66	Remote Similarity	NPD7097	Phase 1
0.6597	Remote Similarity	NPD6362	Approved
0.6597	Remote Similarity	NPD3094	Phase 2
0.6596	Remote Similarity	NPD3026	Approved
0.6596	Remote Similarity	NPD3023	Approved
0.6588	Remote Similarity	NPD7251	Discontinued
0.6581	Remote Similarity	NPD6667	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