NPASS Compound

Structure

NPC260775 OpenBabel07101719512D 28 28 0 0 0 0 0 0 0 0999 V2000 -8.6603 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 5.0000 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 -5.1962 -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 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -9.5263 3.5000 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 -6.9282 2.0000 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 -4.3301 0.5000 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 -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 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 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 -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 -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 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 21 2 0 0 0 0 12 22 1 0 0 0 0 13 22 2 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 23 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 25 2 0 0 0 0 18 26 2 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 26 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.29
Volume:	448.821
LogP:	7.212
LogD:	5.46
LogS:	-3.638
# Rotatable Bonds:	11
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	2.962
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.89
MDCK Permeability:	2.279214641021099e-05
Pgp-inhibitor:	0.09
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.762
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	97.8150863647461%
Volume Distribution (VD):	0.704
Pgp-substrate:	0.5897306799888611%

ADMET: Metabolism

CYP1A2-inhibitor:	0.826
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.632
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.604
CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.936
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.563
CYP3A4-substrate:	0.142

ADMET: Excretion

Clearance (CL):	5.985
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.347
Drug-inuced Liver Injury (DILI):	0.005
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.968
Carcinogencity:	0.015
Eye Corrosion:	0.247
Eye Irritation:	0.928
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC260775

Natural Product ID:	NPC260775
*Common Name:**	Geranylgeranylhydroquinone
IUPAC Name:	2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]benzene-1,4-diol
Synonyms:	Geranylgeranylhydroquinone
Standard InCHIKey:	FIPAQYYZFDCRDD-FPFQZNTGSA-N
Standard InCHI:	InChI=1S/C26H38O2/c1-20(2)9-6-10-21(3)11-7-12-22(4)13-8-14-23(5)15-16-24-19-25(27)17-18-26(24)28/h9,11,13,15,17-19,27-28H,6-8,10,12,14,16H2,1-5H3/b21-11+,22-13+,23-15+
SMILES:	C/C(=CCC/C(=C/Cc1cc(O)ccc1O)/C)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479513
PubChem CID:	6441038
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
NPO32602	lactarius lignyotus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7673933]

☑ 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	24

Activity Type	# Activity
Cell Line	13
CELL-LINE	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	300.0	ug.mL-1	PMID[469888]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	55.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	38.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	20.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	17.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	85.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	52.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	32.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	95.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	36.0	%	PMID[469889]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	42.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	100.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	74.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	83.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	49.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	92.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	67.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	61.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	96.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	91.0	%	PMID[469889]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	86.0	%	PMID[469889]

☑ 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 NPC260775 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	233
0.1-0.2	1679
0.2-0.3	5183
0.3-0.4	13889
0.4-0.5	6023
0.5-0.6	10238
0.6-0.7	4155
0.7-0.8	979
0.8-0.85	174
0.85-0.9	105
0.9-0.95	27
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC48730
0.9892	High Similarity	NPC70677
0.9892	High Similarity	NPC248396
0.9892	High Similarity	NPC129373
0.9892	High Similarity	NPC12931
0.9892	High Similarity	NPC130756
0.9891	High Similarity	NPC152097
0.9677	High Similarity	NPC475078
0.9579	High Similarity	NPC477685
0.9579	High Similarity	NPC80800
0.9479	High Similarity	NPC108497
0.9457	High Similarity	NPC29373
0.9388	High Similarity	NPC155072
0.9286	High Similarity	NPC47284
0.9247	High Similarity	NPC162314
0.9247	High Similarity	NPC94139
0.9247	High Similarity	NPC147284
0.9247	High Similarity	NPC306884
0.9247	High Similarity	NPC3358
0.9247	High Similarity	NPC210497
0.9192	High Similarity	NPC53740
0.9192	High Similarity	NPC469913
0.91	High Similarity	NPC320439
0.91	High Similarity	NPC474352
0.9082	High Similarity	NPC269212
0.9072	High Similarity	NPC130103
0.9032	High Similarity	NPC192
0.9022	High Similarity	NPC27974
0.899	High Similarity	NPC475580
0.898	High Similarity	NPC252105
0.898	High Similarity	NPC12221
0.8947	High Similarity	NPC245187
0.8936	High Similarity	NPC231150
0.8922	High Similarity	NPC26013
0.8922	High Similarity	NPC282855
0.8922	High Similarity	NPC98392
0.8913	High Similarity	NPC407
0.8913	High Similarity	NPC307235
0.8911	High Similarity	NPC233320
0.8889	High Similarity	NPC235762
0.8889	High Similarity	NPC233827
0.8889	High Similarity	NPC471228
0.8878	High Similarity	NPC72729
0.8878	High Similarity	NPC174911
0.8866	High Similarity	NPC88420
0.8866	High Similarity	NPC79241
0.8866	High Similarity	NPC6597
0.8866	High Similarity	NPC474073
0.8854	High Similarity	NPC32714
0.8846	High Similarity	NPC62867
0.8846	High Similarity	NPC177962
0.8835	High Similarity	NPC208229
0.883	High Similarity	NPC55561
0.8824	High Similarity	NPC68260
0.8824	High Similarity	NPC279887
0.8804	High Similarity	NPC155393
0.88	High Similarity	NPC272029
0.88	High Similarity	NPC475225
0.88	High Similarity	NPC130817
0.8776	High Similarity	NPC299762
0.8776	High Similarity	NPC33675
0.8763	High Similarity	NPC312132
0.8763	High Similarity	NPC259512
0.875	High Similarity	NPC228609
0.875	High Similarity	NPC469912
0.875	High Similarity	NPC54373
0.875	High Similarity	NPC77772
0.875	High Similarity	NPC470770
0.875	High Similarity	NPC76938
0.875	High Similarity	NPC152415
0.875	High Similarity	NPC266937
0.8738	High Similarity	NPC473524
0.8725	High Similarity	NPC158253
0.8725	High Similarity	NPC232523
0.8725	High Similarity	NPC204901
0.8723	High Similarity	NPC177420
0.8723	High Similarity	NPC280347
0.87	High Similarity	NPC24404
0.87	High Similarity	NPC302219
0.87	High Similarity	NPC222522
0.87	High Similarity	NPC94351
0.87	High Similarity	NPC196479
0.87	High Similarity	NPC71002
0.87	High Similarity	NPC168303
0.87	High Similarity	NPC313030
0.87	High Similarity	NPC85479
0.87	High Similarity	NPC53051
0.87	High Similarity	NPC242342
0.87	High Similarity	NPC106396
0.87	High Similarity	NPC146798
0.87	High Similarity	NPC249828
0.8696	High Similarity	NPC286904
0.8696	High Similarity	NPC150837
0.8687	High Similarity	NPC166761
0.8667	High Similarity	NPC302371
0.8654	High Similarity	NPC471535
0.8646	High Similarity	NPC55903
0.8632	High Similarity	NPC312304
0.8627	High Similarity	NPC99836
0.8627	High Similarity	NPC12640
0.8627	High Similarity	NPC67250
0.8627	High Similarity	NPC201662
0.8627	High Similarity	NPC54765
0.8617	High Similarity	NPC113460
0.8617	High Similarity	NPC25493
0.8614	High Similarity	NPC93831
0.86	High Similarity	NPC137415
0.86	High Similarity	NPC11280
0.86	High Similarity	NPC147310
0.86	High Similarity	NPC166313
0.86	High Similarity	NPC294186
0.86	High Similarity	NPC24407
0.86	High Similarity	NPC284011
0.86	High Similarity	NPC72947
0.86	High Similarity	NPC192032
0.8585	High Similarity	NPC296144
0.8585	High Similarity	NPC28784
0.8571	High Similarity	NPC275627
0.8544	High Similarity	NPC66834
0.8542	High Similarity	NPC306074
0.8529	High Similarity	NPC37802
0.8529	High Similarity	NPC138942
0.8526	High Similarity	NPC242240
0.8526	High Similarity	NPC123273
0.8526	High Similarity	NPC318325
0.8519	High Similarity	NPC141001
0.8511	High Similarity	NPC23167
0.8505	High Similarity	NPC197513
0.8505	High Similarity	NPC473931
0.8505	High Similarity	NPC114918
0.8505	High Similarity	NPC474114
0.8505	High Similarity	NPC474050
0.85	High Similarity	NPC10588
0.85	High Similarity	NPC294741
0.85	High Similarity	NPC225506
0.8491	Intermediate Similarity	NPC474920
0.8485	Intermediate Similarity	NPC77492
0.8485	Intermediate Similarity	NPC156313
0.8469	Intermediate Similarity	NPC274678
0.8469	Intermediate Similarity	NPC222146
0.8469	Intermediate Similarity	NPC26244
0.8462	Intermediate Similarity	NPC95344
0.8447	Intermediate Similarity	NPC310456
0.8431	Intermediate Similarity	NPC244513
0.8431	Intermediate Similarity	NPC227458
0.8431	Intermediate Similarity	NPC218879
0.8431	Intermediate Similarity	NPC323810
0.8431	Intermediate Similarity	NPC288411
0.8421	Intermediate Similarity	NPC19680
0.8411	Intermediate Similarity	NPC76400
0.8404	Intermediate Similarity	NPC197783
0.84	Intermediate Similarity	NPC252821
0.84	Intermediate Similarity	NPC128723
0.84	Intermediate Similarity	NPC122005
0.8384	Intermediate Similarity	NPC473388
0.8381	Intermediate Similarity	NPC19808
0.8381	Intermediate Similarity	NPC33728
0.8367	Intermediate Similarity	NPC27323
0.8367	Intermediate Similarity	NPC151715
0.8367	Intermediate Similarity	NPC316301
0.8367	Intermediate Similarity	NPC128062
0.8367	Intermediate Similarity	NPC289769
0.8365	Intermediate Similarity	NPC305603
0.8365	Intermediate Similarity	NPC61033
0.8364	Intermediate Similarity	NPC206205
0.8351	Intermediate Similarity	NPC270547
0.8351	Intermediate Similarity	NPC304541
0.8351	Intermediate Similarity	NPC204210
0.835	Intermediate Similarity	NPC117115
0.835	Intermediate Similarity	NPC134829
0.835	Intermediate Similarity	NPC471350
0.8349	Intermediate Similarity	NPC69539
0.8333	Intermediate Similarity	NPC258219
0.8333	Intermediate Similarity	NPC168393
0.8333	Intermediate Similarity	NPC471534
0.8333	Intermediate Similarity	NPC98772
0.8333	Intermediate Similarity	NPC168829
0.8318	Intermediate Similarity	NPC228452
0.8318	Intermediate Similarity	NPC98372
0.8318	Intermediate Similarity	NPC166995
0.8316	Intermediate Similarity	NPC184169
0.8302	Intermediate Similarity	NPC296683
0.8302	Intermediate Similarity	NPC132720
0.83	Intermediate Similarity	NPC109955
0.8298	Intermediate Similarity	NPC248817
0.8298	Intermediate Similarity	NPC175313
0.8288	Intermediate Similarity	NPC323074
0.8286	Intermediate Similarity	NPC306295
0.8286	Intermediate Similarity	NPC169450
0.8286	Intermediate Similarity	NPC174981
0.8286	Intermediate Similarity	NPC241549
0.8283	Intermediate Similarity	NPC8392
0.8273	Intermediate Similarity	NPC269414
0.8273	Intermediate Similarity	NPC320864
0.8273	Intermediate Similarity	NPC187993
0.8273	Intermediate Similarity	NPC238176
0.8269	Intermediate Similarity	NPC118286
0.8269	Intermediate Similarity	NPC39097
0.8269	Intermediate Similarity	NPC302681
0.8269	Intermediate Similarity	NPC470700

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 NPC260775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1062
0.2-0.3	1429
0.3-0.4	2978
0.4-0.5	1873
0.5-0.6	1104
0.6-0.7	387
0.7-0.8	63
0.8-0.85	11
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9271	High Similarity	NPD289	Clinical (unspecified phase)
0.9053	High Similarity	NPD844	Approved
0.8763	High Similarity	NPD288	Approved
0.8667	High Similarity	NPD7635	Approved
0.8598	High Similarity	NPD6671	Approved
0.8557	High Similarity	NPD2933	Approved
0.8557	High Similarity	NPD2934	Approved
0.8469	Intermediate Similarity	NPD2859	Approved
0.8469	Intermediate Similarity	NPD2860	Approved
0.8454	Intermediate Similarity	NPD845	Approved
0.84	Intermediate Similarity	NPD3020	Approved
0.8367	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD940	Approved
0.8235	Intermediate Similarity	NPD846	Approved
0.8208	Intermediate Similarity	NPD4750	Phase 3
0.8191	Intermediate Similarity	NPD111	Approved
0.81	Intermediate Similarity	NPD1809	Phase 2
0.8037	Intermediate Similarity	NPD3022	Approved
0.8037	Intermediate Similarity	NPD3021	Approved
0.7925	Intermediate Similarity	NPD1444	Approved
0.7925	Intermediate Similarity	NPD1445	Approved
0.785	Intermediate Similarity	NPD2342	Discontinued
0.7826	Intermediate Similarity	NPD9088	Approved
0.7788	Intermediate Similarity	NPD1242	Phase 1
0.7706	Intermediate Similarity	NPD1792	Phase 2
0.7672	Intermediate Similarity	NPD3496	Discontinued
0.7596	Intermediate Similarity	NPD9273	Approved
0.7593	Intermediate Similarity	NPD968	Approved
0.7568	Intermediate Similarity	NPD228	Approved
0.7568	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6696	Suspended
0.7522	Intermediate Similarity	NPD9618	Approved
0.7522	Intermediate Similarity	NPD9614	Approved
0.7522	Intermediate Similarity	NPD497	Approved
0.7477	Intermediate Similarity	NPD9500	Approved
0.7453	Intermediate Similarity	NPD3028	Approved
0.7434	Intermediate Similarity	NPD495	Approved
0.7434	Intermediate Similarity	NPD498	Approved
0.7434	Intermediate Similarity	NPD496	Approved
0.7434	Intermediate Similarity	NPD2229	Approved
0.7434	Intermediate Similarity	NPD2234	Approved
0.7434	Intermediate Similarity	NPD2228	Approved
0.7434	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3091	Approved
0.7407	Intermediate Similarity	NPD9610	Approved
0.7407	Intermediate Similarity	NPD9608	Approved
0.7391	Intermediate Similarity	NPD9087	Approved
0.7391	Intermediate Similarity	NPD7340	Approved
0.7377	Intermediate Similarity	NPD2861	Phase 2
0.7368	Intermediate Similarity	NPD1793	Approved
0.7368	Intermediate Similarity	NPD1791	Approved
0.7345	Intermediate Similarity	NPD9377	Approved
0.7345	Intermediate Similarity	NPD9379	Approved
0.7333	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9616	Approved
0.7328	Intermediate Similarity	NPD9613	Approved
0.7328	Intermediate Similarity	NPD9615	Approved
0.7327	Intermediate Similarity	NPD9295	Approved
0.7311	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4626	Approved
0.7288	Intermediate Similarity	NPD3019	Approved
0.7288	Intermediate Similarity	NPD2932	Approved
0.7288	Intermediate Similarity	NPD4059	Approved
0.7281	Intermediate Similarity	NPD1398	Phase 1
0.7265	Intermediate Similarity	NPD316	Approved
0.725	Intermediate Similarity	NPD2233	Approved
0.725	Intermediate Similarity	NPD2230	Approved
0.725	Intermediate Similarity	NPD2232	Approved
0.7241	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD290	Approved
0.7203	Intermediate Similarity	NPD4093	Discontinued
0.719	Intermediate Similarity	NPD4749	Approved
0.7177	Intermediate Similarity	NPD600	Approved
0.7177	Intermediate Similarity	NPD596	Approved
0.7168	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3092	Approved
0.7158	Intermediate Similarity	NPD9294	Approved
0.7155	Intermediate Similarity	NPD709	Approved
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD4589	Approved
0.7119	Intermediate Similarity	NPD5304	Approved
0.7119	Intermediate Similarity	NPD5303	Approved
0.7119	Intermediate Similarity	NPD7330	Discontinued
0.7083	Intermediate Similarity	NPD1983	Approved
0.7083	Intermediate Similarity	NPD1980	Approved
0.7083	Intermediate Similarity	NPD1981	Approved
0.708	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3094	Phase 2
0.7069	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7843	Approved
0.7025	Intermediate Similarity	NPD1201	Approved
0.7016	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7157	Approved
0.7008	Intermediate Similarity	NPD840	Approved
0.7008	Intermediate Similarity	NPD839	Approved
0.7	Intermediate Similarity	NPD9381	Approved
0.7	Intermediate Similarity	NPD2286	Discontinued
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD1751	Approved
0.7	Intermediate Similarity	NPD3095	Discontinued
0.7	Intermediate Similarity	NPD9384	Approved
0.6992	Remote Similarity	NPD5311	Approved
0.6992	Remote Similarity	NPD5310	Approved
0.6991	Remote Similarity	NPD74	Approved
0.6991	Remote Similarity	NPD9266	Approved
0.6984	Remote Similarity	NPD4625	Phase 3
0.6983	Remote Similarity	NPD5283	Phase 1
0.6975	Remote Similarity	NPD1759	Phase 1
0.697	Remote Similarity	NPD9089	Approved
0.6967	Remote Similarity	NPD2235	Phase 2
0.6967	Remote Similarity	NPD2231	Phase 2
0.696	Remote Similarity	NPD5736	Approved
0.6949	Remote Similarity	NPD7636	Approved
0.6949	Remote Similarity	NPD9493	Approved
0.6947	Remote Similarity	NPD2935	Discontinued
0.6935	Remote Similarity	NPD3053	Approved
0.6935	Remote Similarity	NPD3055	Approved
0.6935	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5691	Approved
0.6917	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1755	Approved
0.6911	Remote Similarity	NPD9622	Approved
0.6903	Remote Similarity	NPD9264	Approved
0.6903	Remote Similarity	NPD9267	Approved
0.6903	Remote Similarity	NPD9263	Approved
0.6897	Remote Similarity	NPD821	Approved
0.6891	Remote Similarity	NPD1758	Phase 1
0.6891	Remote Similarity	NPD856	Approved
0.6891	Remote Similarity	NPD16	Approved
0.6885	Remote Similarity	NPD1611	Approved
0.688	Remote Similarity	NPD6584	Phase 3
0.6869	Remote Similarity	NPD9093	Approved
0.6864	Remote Similarity	NPD255	Approved
0.6864	Remote Similarity	NPD256	Approved
0.686	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3027	Phase 3
0.6833	Remote Similarity	NPD1548	Phase 1
0.6822	Remote Similarity	NPD4060	Phase 1
0.6803	Remote Similarity	NPD3143	Discontinued
0.68	Remote Similarity	NPD1470	Approved
0.6786	Remote Similarity	NPD9244	Approved
0.6783	Remote Similarity	NPD5451	Approved
0.678	Remote Similarity	NPD475	Phase 2
0.6777	Remote Similarity	NPD1357	Approved
0.6774	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4908	Phase 1
0.6772	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4817	Approved
0.6757	Remote Similarity	NPD4818	Approved
0.6754	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1138	Approved
0.675	Remote Similarity	NPD318	Approved
0.675	Remote Similarity	NPD317	Approved
0.6748	Remote Similarity	NPD1535	Discovery
0.6748	Remote Similarity	NPD1610	Phase 2
0.6748	Remote Similarity	NPD422	Phase 1
0.6746	Remote Similarity	NPD599	Approved
0.6746	Remote Similarity	NPD859	Approved
0.6746	Remote Similarity	NPD858	Approved
0.6746	Remote Similarity	NPD9620	Approved
0.6746	Remote Similarity	NPD2194	Approved
0.6746	Remote Similarity	NPD602	Approved
0.6746	Remote Similarity	NPD9621	Approved
0.6746	Remote Similarity	NPD2195	Approved
0.6746	Remote Similarity	NPD9619	Approved
0.6744	Remote Similarity	NPD6663	Approved
0.6723	Remote Similarity	NPD6387	Discontinued
0.6721	Remote Similarity	NPD2668	Approved
0.6721	Remote Similarity	NPD2667	Approved
0.672	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2561	Approved
0.6694	Remote Similarity	NPD2562	Approved
0.6694	Remote Similarity	NPD1481	Phase 2
0.6694	Remote Similarity	NPD3070	Discontinued
0.6693	Remote Similarity	NPD3636	Approved
0.6693	Remote Similarity	NPD3635	Approved
0.6693	Remote Similarity	NPD2237	Approved
0.6693	Remote Similarity	NPD3637	Approved
0.6693	Remote Similarity	NPD1712	Approved
0.6693	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2238	Phase 2
0.6692	Remote Similarity	NPD6346	Approved
0.6667	Remote Similarity	NPD1131	Approved
0.6667	Remote Similarity	NPD1133	Approved
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD9568	Approved
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1129	Approved
0.6667	Remote Similarity	NPD597	Approved
0.6667	Remote Similarity	NPD1135	Approved
0.6667	Remote Similarity	NPD3026	Approved
0.6667	Remote Similarity	NPD1139	Approved
0.6667	Remote Similarity	NPD601	Approved
0.6667	Remote Similarity	NPD3421	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