NPASS Compound

Structure

CID302371 OpenBabel06191716112D 22 22 0 0 0 0 0 0 0 0999 V2000 6.9282 -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 -2.5981 -2.5000 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 6.0622 0.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 -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 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 0.0000 -1.0000 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 1.7321 -1.0000 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 -0.0000 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 15 19 2 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.2
Volume:	341.812
LogP:	5.336
LogD:	3.939
LogS:	-3.713
# Rotatable Bonds:	8
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	2.933
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	2.3377664547297172e-05
Pgp-inhibitor:	0.194
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	99.02864837646484%
Volume Distribution (VD):	6.272
Pgp-substrate:	2.434192657470703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.54
CYP2C19-inhibitor:	0.549
CYP2C19-substrate:	0.218
CYP2C9-inhibitor:	0.358
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.735
CYP3A4-inhibitor:	0.327
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	12.497
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.305
AMES Toxicity:	0.556
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.927
Carcinogencity:	0.217
Eye Corrosion:	0.004
Eye Irritation:	0.858
Respiratory Toxicity:	0.525

Download Data

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

Natural Product: NPC302371

Natural Product ID:	NPC302371
*Common Name:**	2-[(E)-Hept-1-Enyl]-3-(Hydroxymethyl)-5-(3-Methylbut-2-Enyl)Benzene-1,4-Diol
IUPAC Name:	2-[(E)-hept-1-enyl]-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol
Synonyms:
Standard InCHIKey:	DLFLMSMGNSXYFJ-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C19H28O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h8-10,12,20-22H,4-7,11,13H2,1-3H3/b9-8+
SMILES:	CCCCC/C=C/c1c(CO)c(c(CC=C(C)C)cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813662
PubChem CID:	53388784
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002801] Prenylated hydroquinones

*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
NPO30824	Eurotium repens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667972]

☑ 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	6
Others	5

Activity Type	# Activity
Individual Protein	6
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Activity	=	62.2	%	PMID[528402]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[528402]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[528402]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	<	40.0	%	PMID[528402]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	<	40.0	%	PMID[528402]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	IC50	=	5400.0	nM	PMID[528402]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.8	ug.mL-1	PMID[528403]
NPT1666	Organism	Plasmodium falciparum D6	Plasmodium falciparum D6	IC50	=	3.0	ug.mL-1	PMID[528403]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	19.0	ug.mL-1	PMID[528403]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	11.97	ug.mL-1	PMID[528403]
NPT554	Organism	Candida glabrata	Candida glabrata	IC50	=	7.17	ug.mL-1	PMID[528403]

☑ 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 NPC302371 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	275
0.1-0.2	1474
0.2-0.3	4066
0.3-0.4	13214
0.4-0.5	6793
0.5-0.6	9734
0.6-0.7	5463
0.7-0.8	1374
0.8-0.85	233
0.85-0.9	57
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC132720
0.9231	High Similarity	NPC272029
0.9151	High Similarity	NPC66834
0.9048	High Similarity	NPC475225
0.9027	High Similarity	NPC151197
0.8991	High Similarity	NPC469912
0.8962	High Similarity	NPC47284
0.8952	High Similarity	NPC108497
0.8952	High Similarity	NPC471228
0.8952	High Similarity	NPC235762
0.8942	High Similarity	NPC174911
0.8909	High Similarity	NPC228452
0.8879	High Similarity	NPC53740
0.8857	High Similarity	NPC477685
0.885	High Similarity	NPC320864
0.8839	High Similarity	NPC474486
0.8796	High Similarity	NPC474352
0.8785	High Similarity	NPC471350
0.8785	High Similarity	NPC117115
0.8774	High Similarity	NPC269212
0.8762	High Similarity	NPC129373
0.8762	High Similarity	NPC248396
0.8762	High Similarity	NPC48730
0.8761	High Similarity	NPC92
0.8761	High Similarity	NPC469663
0.875	High Similarity	NPC152097
0.875	High Similarity	NPC88420
0.8692	High Similarity	NPC475580
0.8684	High Similarity	NPC477136
0.8679	High Similarity	NPC80800
0.8673	High Similarity	NPC35797
0.8673	High Similarity	NPC192948
0.8667	High Similarity	NPC260775
0.8661	High Similarity	NPC263753
0.8649	High Similarity	NPC77772
0.8649	High Similarity	NPC470770
0.8649	High Similarity	NPC266937
0.8624	High Similarity	NPC151477
0.8624	High Similarity	NPC320439
0.8596	High Similarity	NPC38893
0.8596	High Similarity	NPC219112
0.8596	High Similarity	NPC308828
0.8596	High Similarity	NPC477137
0.8596	High Similarity	NPC308311
0.8585	High Similarity	NPC130103
0.8585	High Similarity	NPC130756
0.8585	High Similarity	NPC72729
0.8585	High Similarity	NPC70677
0.8585	High Similarity	NPC12931
0.8584	High Similarity	NPC268160
0.8571	High Similarity	NPC62867
0.8571	High Similarity	NPC46940
0.8571	High Similarity	NPC177962
0.8571	High Similarity	NPC475078
0.8571	High Similarity	NPC79241
0.8571	High Similarity	NPC6597
0.8571	High Similarity	NPC474073
0.8559	High Similarity	NPC224870
0.8547	High Similarity	NPC100108
0.8547	High Similarity	NPC129176
0.8547	High Similarity	NPC277798
0.8534	High Similarity	NPC469644
0.8532	High Similarity	NPC67250
0.8532	High Similarity	NPC21594
0.8532	High Similarity	NPC155072
0.8532	High Similarity	NPC469913
0.8522	High Similarity	NPC172219
0.8522	High Similarity	NPC304510
0.8519	High Similarity	NPC238696
0.8519	High Similarity	NPC130817
0.8509	High Similarity	NPC147179
0.8509	High Similarity	NPC232165
0.8505	High Similarity	NPC252105
0.8496	Intermediate Similarity	NPC319803
0.8496	Intermediate Similarity	NPC296144
0.8496	Intermediate Similarity	NPC261343
0.8496	Intermediate Similarity	NPC28784
0.8491	Intermediate Similarity	NPC33675
0.8491	Intermediate Similarity	NPC128723
0.8491	Intermediate Similarity	NPC299762
0.8482	Intermediate Similarity	NPC54373
0.8482	Intermediate Similarity	NPC95716
0.8476	Intermediate Similarity	NPC259512
0.8476	Intermediate Similarity	NPC312132
0.8468	Intermediate Similarity	NPC58865
0.8468	Intermediate Similarity	NPC473524
0.8462	Intermediate Similarity	NPC245187
0.8455	Intermediate Similarity	NPC204901
0.8455	Intermediate Similarity	NPC232523
0.8455	Intermediate Similarity	NPC158253
0.8448	Intermediate Similarity	NPC154030
0.8448	Intermediate Similarity	NPC471671
0.8448	Intermediate Similarity	NPC469609
0.844	Intermediate Similarity	NPC37802
0.8426	Intermediate Similarity	NPC233827
0.8421	Intermediate Similarity	NPC474050
0.8421	Intermediate Similarity	NPC471534
0.8421	Intermediate Similarity	NPC107240
0.8421	Intermediate Similarity	NPC474114
0.8421	Intermediate Similarity	NPC473931
0.8421	Intermediate Similarity	NPC249270
0.8407	Intermediate Similarity	NPC228425
0.8407	Intermediate Similarity	NPC473521
0.8407	Intermediate Similarity	NPC250323
0.8378	Intermediate Similarity	NPC68260
0.8378	Intermediate Similarity	NPC262365
0.8378	Intermediate Similarity	NPC279887
0.8376	Intermediate Similarity	NPC121866
0.8365	Intermediate Similarity	NPC29373
0.8364	Intermediate Similarity	NPC201662
0.8364	Intermediate Similarity	NPC54765
0.8364	Intermediate Similarity	NPC12640
0.8364	Intermediate Similarity	NPC99836
0.8349	Intermediate Similarity	NPC227458
0.8349	Intermediate Similarity	NPC323810
0.8349	Intermediate Similarity	NPC218879
0.8349	Intermediate Similarity	NPC244513
0.8348	Intermediate Similarity	NPC246760
0.8348	Intermediate Similarity	NPC84999
0.8333	Intermediate Similarity	NPC715
0.8333	Intermediate Similarity	NPC12221
0.8333	Intermediate Similarity	NPC117846
0.8319	Intermediate Similarity	NPC260323
0.8319	Intermediate Similarity	NPC224527
0.8319	Intermediate Similarity	NPC176279
0.8319	Intermediate Similarity	NPC151537
0.8305	Intermediate Similarity	NPC325544
0.8305	Intermediate Similarity	NPC477037
0.8305	Intermediate Similarity	NPC318581
0.8304	Intermediate Similarity	NPC19808
0.8304	Intermediate Similarity	NPC186385
0.8304	Intermediate Similarity	NPC33728
0.8304	Intermediate Similarity	NPC282855
0.8304	Intermediate Similarity	NPC299568
0.8304	Intermediate Similarity	NPC26013
0.8304	Intermediate Similarity	NPC98392
0.8291	Intermediate Similarity	NPC48781
0.8291	Intermediate Similarity	NPC9592
0.8291	Intermediate Similarity	NPC63010
0.8288	Intermediate Similarity	NPC305603
0.8288	Intermediate Similarity	NPC61033
0.8279	Intermediate Similarity	NPC227741
0.8279	Intermediate Similarity	NPC136342
0.8279	Intermediate Similarity	NPC295202
0.8279	Intermediate Similarity	NPC49647
0.8276	Intermediate Similarity	NPC141001
0.8273	Intermediate Similarity	NPC138942
0.8269	Intermediate Similarity	NPC231150
0.8261	Intermediate Similarity	NPC470837
0.8261	Intermediate Similarity	NPC195922
0.8257	Intermediate Similarity	NPC168393
0.8246	Intermediate Similarity	NPC98372
0.8241	Intermediate Similarity	NPC211885
0.8241	Intermediate Similarity	NPC294741
0.8241	Intermediate Similarity	NPC225506
0.8235	Intermediate Similarity	NPC45663
0.823	Intermediate Similarity	NPC208229
0.823	Intermediate Similarity	NPC141782
0.823	Intermediate Similarity	NPC13482
0.8224	Intermediate Similarity	NPC77492
0.822	Intermediate Similarity	NPC38181
0.822	Intermediate Similarity	NPC323074
0.822	Intermediate Similarity	NPC160235
0.822	Intermediate Similarity	NPC20230
0.8214	Intermediate Similarity	NPC174981
0.8214	Intermediate Similarity	NPC11554
0.8214	Intermediate Similarity	NPC241549
0.8214	Intermediate Similarity	NPC95344
0.8208	Intermediate Similarity	NPC222146
0.8205	Intermediate Similarity	NPC470760
0.8205	Intermediate Similarity	NPC299180
0.8198	Intermediate Similarity	NPC310456
0.8197	Intermediate Similarity	NPC131799
0.8197	Intermediate Similarity	NPC4286
0.8197	Intermediate Similarity	NPC76119
0.819	Intermediate Similarity	NPC306884
0.819	Intermediate Similarity	NPC147284
0.819	Intermediate Similarity	NPC3358
0.819	Intermediate Similarity	NPC210497
0.819	Intermediate Similarity	NPC94139
0.819	Intermediate Similarity	NPC283169
0.819	Intermediate Similarity	NPC469719
0.819	Intermediate Similarity	NPC162314
0.8182	Intermediate Similarity	NPC288411
0.8182	Intermediate Similarity	NPC471187
0.8173	Intermediate Similarity	NPC47950
0.8173	Intermediate Similarity	NPC312304
0.8173	Intermediate Similarity	NPC192
0.8167	Intermediate Similarity	NPC168707
0.8167	Intermediate Similarity	NPC48623
0.816	Intermediate Similarity	NPC325003
0.8158	Intermediate Similarity	NPC275627
0.8158	Intermediate Similarity	NPC165770
0.8158	Intermediate Similarity	NPC4493
0.8158	Intermediate Similarity	NPC225679
0.8158	Intermediate Similarity	NPC476632
0.8158	Intermediate Similarity	NPC308689
0.8151	Intermediate Similarity	NPC223451
0.8151	Intermediate Similarity	NPC260832
0.8151	Intermediate Similarity	NPC135467

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 NPC302371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	992
0.2-0.3	1502
0.3-0.4	2986
0.4-0.5	1772
0.5-0.6	1186
0.6-0.7	379
0.7-0.8	59
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8909	High Similarity	NPD7635	Approved
0.8585	High Similarity	NPD289	Clinical (unspecified phase)
0.8558	High Similarity	NPD844	Approved
0.8476	Intermediate Similarity	NPD288	Approved
0.8304	Intermediate Similarity	NPD4750	Phase 3
0.8288	Intermediate Similarity	NPD2342	Discontinued
0.819	Intermediate Similarity	NPD845	Approved
0.7983	Intermediate Similarity	NPD3091	Approved
0.7949	Intermediate Similarity	NPD497	Approved
0.787	Intermediate Similarity	NPD1809	Phase 2
0.7863	Intermediate Similarity	NPD496	Approved
0.7863	Intermediate Similarity	NPD498	Approved
0.7863	Intermediate Similarity	NPD495	Approved
0.7851	Intermediate Similarity	NPD4626	Approved
0.7838	Intermediate Similarity	NPD940	Approved
0.7838	Intermediate Similarity	NPD846	Approved
0.7823	Intermediate Similarity	NPD6696	Suspended
0.7818	Intermediate Similarity	NPD3020	Approved
0.7778	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD3094	Phase 2
0.7731	Intermediate Similarity	NPD6671	Approved
0.7724	Intermediate Similarity	NPD3092	Approved
0.7712	Intermediate Similarity	NPD1398	Phase 1
0.7706	Intermediate Similarity	NPD2860	Approved
0.7706	Intermediate Similarity	NPD2859	Approved
0.7698	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7340	Approved
0.7656	Intermediate Similarity	NPD4625	Phase 3
0.7623	Intermediate Similarity	NPD5691	Approved
0.7615	Intermediate Similarity	NPD2933	Approved
0.7615	Intermediate Similarity	NPD2934	Approved
0.7611	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3095	Discontinued
0.7542	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD3022	Approved
0.7521	Intermediate Similarity	NPD3021	Approved
0.7462	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2932	Approved
0.7419	Intermediate Similarity	NPD2286	Discontinued
0.7419	Intermediate Similarity	NPD4059	Approved
0.7419	Intermediate Similarity	NPD3019	Approved
0.7417	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD1444	Approved
0.7414	Intermediate Similarity	NPD1445	Approved
0.7373	Intermediate Similarity	NPD1792	Phase 2
0.7368	Intermediate Similarity	NPD4097	Suspended
0.7323	Intermediate Similarity	NPD4749	Approved
0.7302	Intermediate Similarity	NPD1611	Approved
0.7281	Intermediate Similarity	NPD1242	Phase 1
0.7273	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD111	Approved
0.7258	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD2861	Phase 2
0.7231	Intermediate Similarity	NPD5736	Approved
0.7222	Intermediate Similarity	NPD3496	Discontinued
0.7218	Intermediate Similarity	NPD4060	Phase 1
0.7213	Intermediate Similarity	NPD9618	Approved
0.7213	Intermediate Similarity	NPD9614	Approved
0.72	Intermediate Similarity	NPD4093	Discontinued
0.7176	Intermediate Similarity	NPD600	Approved
0.7176	Intermediate Similarity	NPD596	Approved
0.7174	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1201	Approved
0.7155	Intermediate Similarity	NPD9500	Approved
0.7143	Intermediate Similarity	NPD1751	Approved
0.7119	Intermediate Similarity	NPD968	Approved
0.7109	Intermediate Similarity	NPD2233	Approved
0.7109	Intermediate Similarity	NPD2230	Approved
0.7109	Intermediate Similarity	NPD2232	Approved
0.7105	Intermediate Similarity	NPD9273	Approved
0.708	Intermediate Similarity	NPD2935	Discontinued
0.7077	Intermediate Similarity	NPD1129	Approved
0.7077	Intermediate Similarity	NPD1134	Approved
0.7077	Intermediate Similarity	NPD1131	Approved
0.7077	Intermediate Similarity	NPD1133	Approved
0.7077	Intermediate Similarity	NPD1135	Approved
0.7068	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1651	Approved
0.7059	Intermediate Similarity	NPD290	Approved
0.704	Intermediate Similarity	NPD9613	Approved
0.704	Intermediate Similarity	NPD9616	Approved
0.704	Intermediate Similarity	NPD9615	Approved
0.7015	Intermediate Similarity	NPD840	Approved
0.7015	Intermediate Similarity	NPD839	Approved
0.7015	Intermediate Similarity	NPD6663	Approved
0.7008	Intermediate Similarity	NPD4589	Approved
0.7	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD2684	Approved
0.6993	Remote Similarity	NPD6090	Discontinued
0.6992	Remote Similarity	NPD2229	Approved
0.6992	Remote Similarity	NPD2234	Approved
0.6992	Remote Similarity	NPD2228	Approved
0.6992	Remote Similarity	NPD3027	Phase 3
0.6984	Remote Similarity	NPD316	Approved
0.6984	Remote Similarity	NPD5303	Approved
0.6984	Remote Similarity	NPD5304	Approved
0.6967	Remote Similarity	NPD228	Approved
0.6963	Remote Similarity	NPD2238	Phase 2
0.6963	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3620	Phase 2
0.696	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5405	Approved
0.6957	Remote Similarity	NPD5408	Approved
0.6957	Remote Similarity	NPD5404	Approved
0.6957	Remote Similarity	NPD5406	Approved
0.6947	Remote Similarity	NPD1470	Approved
0.6935	Remote Similarity	NPD1793	Approved
0.6935	Remote Similarity	NPD1791	Approved
0.6923	Remote Similarity	NPD9088	Approved
0.6917	Remote Similarity	NPD4908	Phase 1
0.6905	Remote Similarity	NPD7644	Approved
0.6899	Remote Similarity	NPD1610	Phase 2
0.6894	Remote Similarity	NPD2194	Approved
0.6894	Remote Similarity	NPD3690	Phase 2
0.6894	Remote Similarity	NPD3691	Phase 2
0.6894	Remote Similarity	NPD2195	Approved
0.6894	Remote Similarity	NPD4624	Approved
0.6889	Remote Similarity	NPD6405	Approved
0.6889	Remote Similarity	NPD6407	Approved
0.6884	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7743	Approved
0.6884	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7742	Approved
0.688	Remote Similarity	NPD709	Approved
0.688	Remote Similarity	NPD7157	Approved
0.6875	Remote Similarity	NPD5126	Approved
0.6875	Remote Similarity	NPD1778	Approved
0.6875	Remote Similarity	NPD5125	Phase 3
0.6861	Remote Similarity	NPD2157	Approved
0.6853	Remote Similarity	NPD7390	Discontinued
0.685	Remote Similarity	NPD7330	Discontinued
0.6842	Remote Similarity	NPD3637	Approved
0.6842	Remote Similarity	NPD2237	Approved
0.6842	Remote Similarity	NPD3636	Approved
0.6842	Remote Similarity	NPD3635	Approved
0.6842	Remote Similarity	NPD1712	Approved
0.6838	Remote Similarity	NPD4140	Approved
0.6827	Remote Similarity	NPD9294	Approved
0.6822	Remote Similarity	NPD3026	Approved
0.6822	Remote Similarity	NPD3023	Approved
0.6818	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7985	Registered
0.6803	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3024	Approved
0.6797	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3025	Approved
0.6794	Remote Similarity	NPD1669	Approved
0.6794	Remote Similarity	NPD5327	Phase 3
0.6791	Remote Similarity	NPD2606	Approved
0.6791	Remote Similarity	NPD2605	Approved
0.6788	Remote Similarity	NPD5735	Approved
0.6786	Remote Similarity	NPD5763	Approved
0.6786	Remote Similarity	NPD5762	Approved
0.6779	Remote Similarity	NPD5929	Approved
0.6774	Remote Similarity	NPD7843	Approved
0.6774	Remote Similarity	NPD1138	Approved
0.6769	Remote Similarity	NPD1281	Approved
0.6767	Remote Similarity	NPD602	Approved
0.6767	Remote Similarity	NPD599	Approved
0.6767	Remote Similarity	NPD858	Approved
0.6767	Remote Similarity	NPD859	Approved
0.6759	Remote Similarity	NPD2675	Approved
0.6759	Remote Similarity	NPD2676	Approved
0.6744	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD9381	Approved
0.6744	Remote Similarity	NPD9384	Approved
0.6741	Remote Similarity	NPD5156	Approved
0.6741	Remote Similarity	NPD5155	Approved
0.6736	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7041	Phase 2
0.6735	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5283	Phase 1
0.6719	Remote Similarity	NPD1548	Phase 1
0.6719	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2235	Phase 2
0.6718	Remote Similarity	NPD2231	Phase 2
0.6715	Remote Similarity	NPD2979	Phase 3
0.6715	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1613	Approved
0.6714	Remote Similarity	NPD6099	Approved
0.6714	Remote Similarity	NPD6100	Approved
0.6696	Remote Similarity	NPD9295	Approved
0.6695	Remote Similarity	NPD3028	Approved
0.6694	Remote Similarity	NPD1137	Approved
0.6694	Remote Similarity	NPD1139	Approved
0.6693	Remote Similarity	NPD9493	Approved
0.6693	Remote Similarity	NPD7636	Approved
0.6692	Remote Similarity	NPD1981	Approved
0.6692	Remote Similarity	NPD1164	Approved
0.6692	Remote Similarity	NPD3143	Discontinued
0.6692	Remote Similarity	NPD1980	Approved
0.6692	Remote Similarity	NPD1983	Approved
0.6691	Remote Similarity	NPD3555	Approved
0.6691	Remote Similarity	NPD3553	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