NPASS Compound

Structure

NPC474944 OpenBabel07101718192D 35 35 0 0 1 0 0 0 0 0999 V2000 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 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 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -2.5981 -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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 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 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -7.7942 1.5000 0.0000 C 0 0 2 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -3.4641 0.0000 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 -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 8 1 0 0 0 0 7 9 1 0 0 0 0 8 21 2 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 19 2 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 16 26 2 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 18 24 1 0 0 0 0 18 28 1 0 0 0 0 22 27 1 0 0 0 0 23 29 2 0 0 0 0 24 29 1 0 0 0 0 25 30 1 1 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 28 33 2 0 0 0 0 28 35 1 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	533.233
LogP:	3.81
LogD:	3.671
LogS:	-4.792
# Rotatable Bonds:	15
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	4.074
Fsp3:	0.517
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.793
MDCK Permeability:	1.5138548405957408e-05
Pgp-inhibitor:	0.567
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.632
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.631

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	96.00949096679688%
Volume Distribution (VD):	0.395
Pgp-substrate:	0.9155968427658081%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.383
CYP2C19-inhibitor:	0.288
CYP2C19-substrate:	0.496
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.737
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	13.927
Half-life (T1/2):	0.961

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.858
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.258
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.51
Carcinogencity:	0.068
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC474944

Natural Product ID:	NPC474944
*Common Name:**	Methyl 2-[2,5-Dihydroxy-3-[(2Z,10E,13S)-13-Hydroxy-3,7,11,15-Tetramethyl-6-Oxohexadeca-2,10,14-Trienyl]Phenyl]Acetate
IUPAC Name:	methyl 2-[2,5-dihydroxy-3-[(2Z,10E,13S)-13-hydroxy-3,7,11,15-tetramethyl-6-oxohexadeca-2,10,14-trienyl]phenyl]acetate
Synonyms:
Standard InCHIKey:	LNFJRIGXMMFYGW-AEFLQGNMSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-19(2)14-25(30)15-21(4)8-7-9-22(5)27(32)13-11-20(3)10-12-23-16-26(31)17-24(29(23)34)18-28(33)35-6/h8,10,14,16-17,22,25,30-31,34H,7,9,11-13,15,18H2,1-6H3/b20-10-,21-8+/t22?,25-/m1/s1
SMILES:	CC(CCC=C(C)CC(C=C(C)C)O)C(=O)CCC(=CCC1=C(C(=CC(=C1)O)CC(=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489385
PubChem CID:	25136228
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[572965]
NPT1	Others	Radical scavenging activity		RC50	=	0.1	ug ml-1	PMID[572965]

☑ 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 NPC474944 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	248
0.1-0.2	1000
0.2-0.3	2748
0.3-0.4	6761
0.4-0.5	12418
0.5-0.6	5600
0.6-0.7	11411
0.7-0.8	2407
0.8-0.85	87
0.85-0.9	11
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9835	High Similarity	NPC476024
0.9669	High Similarity	NPC476022
0.9669	High Similarity	NPC474945
0.9516	High Similarity	NPC123
0.9516	High Similarity	NPC163169
0.8855	High Similarity	NPC475011
0.8797	High Similarity	NPC476025
0.8797	High Similarity	NPC475028
0.8667	High Similarity	NPC475063
0.8667	High Similarity	NPC475044
0.8595	High Similarity	NPC474050
0.8595	High Similarity	NPC473931
0.8595	High Similarity	NPC474114
0.8571	High Similarity	NPC475029
0.8571	High Similarity	NPC476018
0.8571	High Similarity	NPC475192
0.8519	High Similarity	NPC475005
0.8519	High Similarity	NPC474943
0.8516	High Similarity	NPC477213
0.8512	High Similarity	NPC296144
0.8512	High Similarity	NPC28784
0.8496	Intermediate Similarity	NPC204582
0.8462	Intermediate Similarity	NPC473744
0.8456	Intermediate Similarity	NPC475045
0.8443	Intermediate Similarity	NPC114918
0.84	Intermediate Similarity	NPC476020
0.8394	Intermediate Similarity	NPC3218
0.8385	Intermediate Similarity	NPC319422
0.8385	Intermediate Similarity	NPC477211
0.8385	Intermediate Similarity	NPC477212
0.8385	Intermediate Similarity	NPC477214
0.837	Intermediate Similarity	NPC475111
0.8293	Intermediate Similarity	NPC197513
0.8271	Intermediate Similarity	NPC473777
0.8264	Intermediate Similarity	NPC208229
0.8261	Intermediate Similarity	NPC37992
0.8261	Intermediate Similarity	NPC42262
0.8261	Intermediate Similarity	NPC147542
0.8261	Intermediate Similarity	NPC241349
0.8261	Intermediate Similarity	NPC220496
0.8261	Intermediate Similarity	NPC327916
0.8261	Intermediate Similarity	NPC32749
0.8217	Intermediate Similarity	NPC477153
0.8201	Intermediate Similarity	NPC272907
0.8201	Intermediate Similarity	NPC2681
0.8201	Intermediate Similarity	NPC471444
0.8188	Intermediate Similarity	NPC306835
0.8188	Intermediate Similarity	NPC471602
0.8188	Intermediate Similarity	NPC256463
0.8188	Intermediate Similarity	NPC476477
0.8188	Intermediate Similarity	NPC216312
0.8188	Intermediate Similarity	NPC111422
0.8188	Intermediate Similarity	NPC299405
0.8188	Intermediate Similarity	NPC29771
0.8188	Intermediate Similarity	NPC475012
0.8182	Intermediate Similarity	NPC26013
0.8182	Intermediate Similarity	NPC282855
0.8162	Intermediate Similarity	NPC279463
0.8154	Intermediate Similarity	NPC474803
0.8148	Intermediate Similarity	NPC239855
0.8148	Intermediate Similarity	NPC49742
0.8134	Intermediate Similarity	NPC474143
0.8134	Intermediate Similarity	NPC474246
0.8125	Intermediate Similarity	NPC474175
0.811	Intermediate Similarity	NPC473767
0.8099	Intermediate Similarity	NPC279887
0.8099	Intermediate Similarity	NPC68260
0.8092	Intermediate Similarity	NPC472592
0.8083	Intermediate Similarity	NPC317592
0.8083	Intermediate Similarity	NPC469913
0.8074	Intermediate Similarity	NPC242358
0.8074	Intermediate Similarity	NPC476389
0.8074	Intermediate Similarity	NPC302844
0.8074	Intermediate Similarity	NPC246693
0.8074	Intermediate Similarity	NPC110609
0.8071	Intermediate Similarity	NPC257003
0.8065	Intermediate Similarity	NPC62546
0.8065	Intermediate Similarity	NPC162113
0.8062	Intermediate Similarity	NPC31936
0.8049	Intermediate Similarity	NPC228609
0.8047	Intermediate Similarity	NPC478121
0.8031	Intermediate Similarity	NPC273282
0.8031	Intermediate Similarity	NPC206205
0.8031	Intermediate Similarity	NPC474890
0.8031	Intermediate Similarity	NPC161943
0.8028	Intermediate Similarity	NPC126707
0.8027	Intermediate Similarity	NPC474824
0.8027	Intermediate Similarity	NPC218870
0.8027	Intermediate Similarity	NPC470408
0.8027	Intermediate Similarity	NPC182921
0.8016	Intermediate Similarity	NPC83718
0.8015	Intermediate Similarity	NPC117794
0.8015	Intermediate Similarity	NPC184219
0.8014	Intermediate Similarity	NPC474300
0.8	Intermediate Similarity	NPC258073
0.8	Intermediate Similarity	NPC469911
0.8	Intermediate Similarity	NPC67300
0.8	Intermediate Similarity	NPC49441
0.7986	Intermediate Similarity	NPC475974
0.7984	Intermediate Similarity	NPC164852
0.7958	Intermediate Similarity	NPC476473
0.7955	Intermediate Similarity	NPC87985
0.7955	Intermediate Similarity	NPC167055
0.7955	Intermediate Similarity	NPC240744
0.7953	Intermediate Similarity	NPC160199
0.7953	Intermediate Similarity	NPC325295
0.7953	Intermediate Similarity	NPC76308
0.7939	Intermediate Similarity	NPC275145
0.7926	Intermediate Similarity	NPC475880
0.792	Intermediate Similarity	NPC190212
0.7919	Intermediate Similarity	NPC474861
0.7917	Intermediate Similarity	NPC474991
0.7914	Intermediate Similarity	NPC474771
0.7914	Intermediate Similarity	NPC65837
0.7914	Intermediate Similarity	NPC474849
0.7914	Intermediate Similarity	NPC149372
0.7914	Intermediate Similarity	NPC178467
0.7914	Intermediate Similarity	NPC194579
0.7902	Intermediate Similarity	NPC89664
0.7902	Intermediate Similarity	NPC274085
0.7899	Intermediate Similarity	NPC142027
0.7899	Intermediate Similarity	NPC27407
0.7895	Intermediate Similarity	NPC110211
0.7895	Intermediate Similarity	NPC204579
0.7895	Intermediate Similarity	NPC473751
0.7886	Intermediate Similarity	NPC473524
0.7879	Intermediate Similarity	NPC181334
0.7879	Intermediate Similarity	NPC474237
0.7879	Intermediate Similarity	NPC85565
0.7872	Intermediate Similarity	NPC315578
0.7868	Intermediate Similarity	NPC476847
0.7863	Intermediate Similarity	NPC121168
0.7863	Intermediate Similarity	NPC297193
0.7863	Intermediate Similarity	NPC477151
0.7863	Intermediate Similarity	NPC132518
0.7862	Intermediate Similarity	NPC127046
0.7862	Intermediate Similarity	NPC5568
0.7857	Intermediate Similarity	NPC191835
0.7857	Intermediate Similarity	NPC472403
0.7857	Intermediate Similarity	NPC112135
0.7857	Intermediate Similarity	NPC212693
0.7857	Intermediate Similarity	NPC94248
0.7847	Intermediate Similarity	NPC258856
0.7847	Intermediate Similarity	NPC84786
0.7847	Intermediate Similarity	NPC75295
0.7842	Intermediate Similarity	NPC472308
0.784	Intermediate Similarity	NPC26615
0.7836	Intermediate Similarity	NPC209959
0.7833	Intermediate Similarity	NPC13426
0.7829	Intermediate Similarity	NPC182240
0.7826	Intermediate Similarity	NPC474394
0.7826	Intermediate Similarity	NPC202225
0.7826	Intermediate Similarity	NPC293454
0.7823	Intermediate Similarity	NPC315520
0.782	Intermediate Similarity	NPC123704
0.782	Intermediate Similarity	NPC131799
0.782	Intermediate Similarity	NPC127975
0.7817	Intermediate Similarity	NPC472605
0.7817	Intermediate Similarity	NPC164599
0.7817	Intermediate Similarity	NPC472604
0.7817	Intermediate Similarity	NPC472603
0.7812	Intermediate Similarity	NPC269414
0.7808	Intermediate Similarity	NPC94781
0.7805	Intermediate Similarity	NPC31274
0.7803	Intermediate Similarity	NPC174991
0.7803	Intermediate Similarity	NPC471187
0.7801	Intermediate Similarity	NPC474655
0.7801	Intermediate Similarity	NPC26924
0.7801	Intermediate Similarity	NPC295339
0.7795	Intermediate Similarity	NPC322358
0.7793	Intermediate Similarity	NPC473023
0.7793	Intermediate Similarity	NPC120536
0.7793	Intermediate Similarity	NPC191899
0.7793	Intermediate Similarity	NPC246229
0.7786	Intermediate Similarity	NPC70380
0.7786	Intermediate Similarity	NPC25168
0.7786	Intermediate Similarity	NPC470721
0.7786	Intermediate Similarity	NPC71256
0.7786	Intermediate Similarity	NPC477592
0.7786	Intermediate Similarity	NPC6100
0.7786	Intermediate Similarity	NPC322332
0.7786	Intermediate Similarity	NPC305060
0.7786	Intermediate Similarity	NPC156888
0.7786	Intermediate Similarity	NPC470722
0.7786	Intermediate Similarity	NPC98804
0.7786	Intermediate Similarity	NPC472892
0.7778	Intermediate Similarity	NPC229894
0.7778	Intermediate Similarity	NPC103910
0.7778	Intermediate Similarity	NPC477409
0.7769	Intermediate Similarity	NPC473136
0.7762	Intermediate Similarity	NPC474154
0.7762	Intermediate Similarity	NPC474961
0.7761	Intermediate Similarity	NPC227741
0.7761	Intermediate Similarity	NPC49647
0.7761	Intermediate Similarity	NPC136342
0.7761	Intermediate Similarity	NPC295202
0.776	Intermediate Similarity	NPC54373
0.776	Intermediate Similarity	NPC469912
0.7755	Intermediate Similarity	NPC247219
0.7754	Intermediate Similarity	NPC472591

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 NPC474944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	788
0.2-0.3	1708
0.3-0.4	2681
0.4-0.5	2053
0.5-0.6	1150
0.6-0.7	506
0.7-0.8	43
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
0.7535	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7481	Intermediate Similarity	NPD9545	Approved
0.7463	Intermediate Similarity	NPD1608	Approved
0.7379	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2532	Approved
0.7365	Intermediate Similarity	NPD2534	Approved
0.7357	Intermediate Similarity	NPD6663	Approved
0.7319	Intermediate Similarity	NPD5736	Approved
0.7308	Intermediate Similarity	NPD2629	Approved
0.7293	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7635	Approved
0.7286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6190	Approved
0.7239	Intermediate Similarity	NPD1778	Approved
0.7239	Intermediate Similarity	NPD17	Approved
0.7236	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7211	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3496	Discontinued
0.7174	Intermediate Similarity	NPD1470	Approved
0.7172	Intermediate Similarity	NPD6100	Approved
0.7172	Intermediate Similarity	NPD6099	Approved
0.7165	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5048	Discontinued
0.7132	Intermediate Similarity	NPD1201	Approved
0.7122	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2932	Approved
0.7111	Intermediate Similarity	NPD3019	Approved
0.7103	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1283	Approved
0.7097	Intermediate Similarity	NPD7819	Suspended
0.7097	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3400	Discontinued
0.7095	Intermediate Similarity	NPD4628	Phase 3
0.7095	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7473	Discontinued
0.708	Intermediate Similarity	NPD9269	Phase 2
0.707	Intermediate Similarity	NPD7075	Discontinued
0.7068	Intermediate Similarity	NPD9493	Approved
0.7066	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD3226	Approved
0.7054	Intermediate Similarity	NPD4750	Phase 3
0.7049	Intermediate Similarity	NPD844	Approved
0.7037	Intermediate Similarity	NPD9268	Approved
0.7032	Intermediate Similarity	NPD37	Approved
0.7025	Intermediate Similarity	NPD845	Approved
0.702	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD4380	Phase 2
0.7006	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6085	Phase 2
0.7	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5844	Phase 1
0.6992	Remote Similarity	NPD6671	Approved
0.6992	Remote Similarity	NPD288	Approved
0.6987	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2799	Discontinued
0.6985	Remote Similarity	NPD4626	Approved
0.698	Remote Similarity	NPD8166	Discontinued
0.6978	Remote Similarity	NPD6696	Suspended
0.6968	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6653	Approved
0.6954	Remote Similarity	NPD7390	Discontinued
0.695	Remote Similarity	NPD2861	Phase 2
0.6948	Remote Similarity	NPD7458	Discontinued
0.6944	Remote Similarity	NPD4060	Phase 1
0.6944	Remote Similarity	NPD2979	Phase 3
0.6944	Remote Similarity	NPD943	Approved
0.6943	Remote Similarity	NPD5402	Approved
0.6943	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.694	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5408	Approved
0.6939	Remote Similarity	NPD5405	Approved
0.6939	Remote Similarity	NPD5404	Approved
0.6939	Remote Similarity	NPD5406	Approved
0.6935	Remote Similarity	NPD9495	Approved
0.6923	Remote Similarity	NPD2313	Discontinued
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD7985	Registered
0.6923	Remote Similarity	NPD3764	Approved
0.6908	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1755	Approved
0.6901	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4967	Phase 2
0.6899	Remote Similarity	NPD4965	Approved
0.6899	Remote Similarity	NPD4966	Approved
0.6894	Remote Similarity	NPD6232	Discontinued
0.6894	Remote Similarity	NPD7229	Phase 3
0.6892	Remote Similarity	NPD5763	Approved
0.6892	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5762	Approved
0.6892	Remote Similarity	NPD2346	Discontinued
0.6884	Remote Similarity	NPD1281	Approved
0.6879	Remote Similarity	NPD2801	Approved
0.6879	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5647	Approved
0.6871	Remote Similarity	NPD1510	Phase 2
0.6859	Remote Similarity	NPD7411	Suspended
0.685	Remote Similarity	NPD6647	Phase 2
0.6849	Remote Similarity	NPD6651	Approved
0.6846	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9266	Approved
0.6846	Remote Similarity	NPD74	Approved
0.6842	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1759	Phase 1
0.6835	Remote Similarity	NPD1481	Phase 2
0.6828	Remote Similarity	NPD825	Approved
0.6828	Remote Similarity	NPD1240	Approved
0.6828	Remote Similarity	NPD826	Approved
0.6822	Remote Similarity	NPD6685	Approved
0.6818	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1934	Approved
0.6815	Remote Similarity	NPD6801	Discontinued
0.6813	Remote Similarity	NPD6234	Discontinued
0.6809	Remote Similarity	NPD2797	Approved
0.6809	Remote Similarity	NPD1164	Approved
0.6806	Remote Similarity	NPD6798	Discontinued
0.6806	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5691	Approved
0.6786	Remote Similarity	NPD8313	Approved
0.6786	Remote Similarity	NPD8312	Approved
0.6784	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7266	Discontinued
0.6779	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3300	Phase 2
0.6774	Remote Similarity	NPD1809	Phase 2
0.6774	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD940	Approved
0.6772	Remote Similarity	NPD8455	Phase 2
0.6772	Remote Similarity	NPD846	Approved
0.677	Remote Similarity	NPD5494	Approved
0.6769	Remote Similarity	NPD9264	Approved
0.6769	Remote Similarity	NPD9267	Approved
0.6769	Remote Similarity	NPD9263	Approved
0.6765	Remote Similarity	NPD1758	Phase 1
0.6763	Remote Similarity	NPD1535	Discovery
0.6759	Remote Similarity	NPD6233	Phase 2
0.6757	Remote Similarity	NPD7305	Phase 1
0.6757	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3020	Approved
0.6741	Remote Similarity	NPD256	Approved
0.6741	Remote Similarity	NPD255	Approved
0.6735	Remote Similarity	NPD1607	Approved
0.6733	Remote Similarity	NPD1549	Phase 2
0.6728	Remote Similarity	NPD6959	Discontinued
0.6727	Remote Similarity	NPD7228	Approved
0.6726	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5765	Approved
0.6719	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3091	Approved
0.6711	Remote Similarity	NPD4476	Approved
0.6711	Remote Similarity	NPD6032	Approved
0.6711	Remote Similarity	NPD9570	Approved
0.6711	Remote Similarity	NPD4477	Approved
0.6711	Remote Similarity	NPD2438	Suspended
0.6707	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3026	Approved
0.6691	Remote Similarity	NPD3023	Approved
0.669	Remote Similarity	NPD6362	Approved
0.669	Remote Similarity	NPD3094	Phase 2
0.6689	Remote Similarity	NPD2800	Approved
0.6689	Remote Similarity	NPD7097	Phase 1
0.6687	Remote Similarity	NPD5711	Approved
0.6687	Remote Similarity	NPD5710	Approved
0.6687	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6666	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6667	Approved
0.6667	Remote Similarity	NPD5124	Phase 1
0.6667	Remote Similarity	NPD3022	Approved
0.6647	Remote Similarity	NPD7074	Phase 3
0.6646	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3750	Approved
0.6645	Remote Similarity	NPD7003	Approved
0.6644	Remote Similarity	NPD4248	Discontinued
0.6644	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1611	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