NPASS Compound

Structure

CID70677 OpenBabel06191715412D 38 38 0 0 0 0 0 0 0 0999 V2000 0.0000 16.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 17.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 13.0000 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 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 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 -1.7321 16.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 14.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 11.5000 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 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 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 -2.5981 2.5000 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 -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 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 -0.8660 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 28 2 0 0 0 0 14 29 1 0 0 0 0 15 29 2 0 0 0 0 16 30 1 0 0 0 0 17 30 2 0 0 0 0 18 31 1 0 0 0 0 19 31 2 0 0 0 0 20 32 1 0 0 0 0 21 32 2 0 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 33 2 0 0 0 0 24 34 1 0 0 0 0 25 26 1 0 0 0 0 25 35 2 0 0 0 0 26 36 2 0 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 34 36 1 0 0 0 0 35 37 1 0 0 0 0 36 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.12
Volume:	339.978
LogP:	0.932
LogD:	0.168
LogS:	-1.109
# Rotatable Bonds:	6
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	3.769
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.126
MDCK Permeability:	4.651509880204685e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.53
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.564
Plasma Protein Binding (PPB):	70.60958099365234%
Volume Distribution (VD):	1.466
Pgp-substrate:	28.50745391845703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.094
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.227
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	4.335
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.124
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.381
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.151
Carcinogencity:	0.365
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC70677

Natural Product ID:	NPC70677
*Common Name:**	2-Hexaprenyl-Hydroquinone
IUPAC Name:	2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaenyl]benzene-1,4-diol
Synonyms:	2-Hexaprenyl-Hydroquinone
Standard InCHIKey:	GYXOFGKCNHUEPR-LAAQXVIISA-N
Standard InCHI:	InChI=1S/C36H54O2/c1-28(2)13-8-14-29(3)15-9-16-30(4)17-10-18-31(5)19-11-20-32(6)21-12-22-33(7)23-24-34-27-35(37)25-26-36(34)38/h13,15,17,19,21,23,25-27,37-38H,8-12,14,16,18,20,22,24H2,1-7H3/b29-15+,30-17+,31-19+,32-21+,33-23+
SMILES:	C/C(=CCC/C(=C/CC/C(=C/Cc1cc(O)ccc1O)/C)/C)/CC/C=C(/CC/C=C(/CCC=C(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460440
PubChem CID:	5353837
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 [CHEMONTID:0001937] Polyprenyl quinols

*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
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342624]
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO812	Populus heterophylla	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO812	Populus heterophylla	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO812	Populus heterophylla	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3178	Dalbergia latifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.63	ppm	PMID[469672]
NPT1221	Organism	Gambusia affinis	Gambusia affinis	LC50	>	100.0	ppm	PMID[469672]

☑ 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 NPC70677 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
1.0	High Similarity	NPC130756
1.0	High Similarity	NPC12931
0.9892	High Similarity	NPC260775
0.9787	High Similarity	NPC129373
0.9787	High Similarity	NPC248396
0.9787	High Similarity	NPC48730
0.9785	High Similarity	NPC152097
0.9574	High Similarity	NPC475078
0.9479	High Similarity	NPC80800
0.9479	High Similarity	NPC477685
0.9381	High Similarity	NPC108497
0.9355	High Similarity	NPC29373
0.9293	High Similarity	NPC155072
0.9192	High Similarity	NPC47284
0.9149	High Similarity	NPC306884
0.9149	High Similarity	NPC162314
0.9149	High Similarity	NPC3358
0.9149	High Similarity	NPC94139
0.9149	High Similarity	NPC210497
0.9149	High Similarity	NPC147284
0.91	High Similarity	NPC469913
0.91	High Similarity	NPC53740
0.901	High Similarity	NPC474352
0.901	High Similarity	NPC320439
0.899	High Similarity	NPC269212
0.898	High Similarity	NPC130103
0.8936	High Similarity	NPC192
0.8925	High Similarity	NPC27974
0.89	High Similarity	NPC475580
0.8889	High Similarity	NPC12221
0.8889	High Similarity	NPC252105
0.8854	High Similarity	NPC245187
0.8842	High Similarity	NPC231150
0.8835	High Similarity	NPC98392
0.8835	High Similarity	NPC26013
0.8835	High Similarity	NPC282855
0.8824	High Similarity	NPC233320
0.8817	High Similarity	NPC307235
0.8817	High Similarity	NPC407
0.88	High Similarity	NPC233827
0.88	High Similarity	NPC235762
0.88	High Similarity	NPC471228
0.8788	High Similarity	NPC72729
0.8788	High Similarity	NPC174911
0.8776	High Similarity	NPC79241
0.8776	High Similarity	NPC88420
0.8776	High Similarity	NPC6597
0.8776	High Similarity	NPC474073
0.8763	High Similarity	NPC32714
0.8762	High Similarity	NPC177962
0.8762	High Similarity	NPC62867
0.875	High Similarity	NPC208229
0.8738	High Similarity	NPC279887
0.8738	High Similarity	NPC68260
0.8737	High Similarity	NPC55561
0.8713	High Similarity	NPC130817
0.8713	High Similarity	NPC272029
0.8713	High Similarity	NPC475225
0.871	High Similarity	NPC155393
0.8687	High Similarity	NPC33675
0.8687	High Similarity	NPC299762
0.8673	High Similarity	NPC312132
0.8673	High Similarity	NPC259512
0.8667	High Similarity	NPC228609
0.8667	High Similarity	NPC469912
0.8667	High Similarity	NPC77772
0.8667	High Similarity	NPC54373
0.8667	High Similarity	NPC266937
0.8667	High Similarity	NPC470770
0.866	High Similarity	NPC76938
0.866	High Similarity	NPC152415
0.8654	High Similarity	NPC473524
0.8641	High Similarity	NPC232523
0.8641	High Similarity	NPC158253
0.8641	High Similarity	NPC204901
0.8632	High Similarity	NPC177420
0.8632	High Similarity	NPC280347
0.8614	High Similarity	NPC196479
0.8614	High Similarity	NPC146798
0.8614	High Similarity	NPC249828
0.8614	High Similarity	NPC53051
0.8614	High Similarity	NPC168303
0.8614	High Similarity	NPC71002
0.8614	High Similarity	NPC242342
0.8614	High Similarity	NPC85479
0.8614	High Similarity	NPC24404
0.8614	High Similarity	NPC313030
0.8614	High Similarity	NPC106396
0.8614	High Similarity	NPC94351
0.8614	High Similarity	NPC302219
0.8614	High Similarity	NPC222522
0.8602	High Similarity	NPC286904
0.8602	High Similarity	NPC150837
0.86	High Similarity	NPC166761
0.8585	High Similarity	NPC302371
0.8571	High Similarity	NPC471535
0.8557	High Similarity	NPC55903
0.8544	High Similarity	NPC99836
0.8544	High Similarity	NPC54765
0.8544	High Similarity	NPC67250
0.8544	High Similarity	NPC12640
0.8544	High Similarity	NPC201662
0.8542	High Similarity	NPC312304
0.8529	High Similarity	NPC93831
0.8526	High Similarity	NPC113460
0.8526	High Similarity	NPC25493
0.8515	High Similarity	NPC24407
0.8515	High Similarity	NPC192032
0.8515	High Similarity	NPC72947
0.8515	High Similarity	NPC284011
0.8515	High Similarity	NPC137415
0.8515	High Similarity	NPC294186
0.8515	High Similarity	NPC166313
0.8515	High Similarity	NPC11280
0.8515	High Similarity	NPC147310
0.8505	High Similarity	NPC28784
0.8505	High Similarity	NPC296144
0.8491	Intermediate Similarity	NPC275627
0.8462	Intermediate Similarity	NPC66834
0.8454	Intermediate Similarity	NPC306074
0.8447	Intermediate Similarity	NPC138942
0.8447	Intermediate Similarity	NPC37802
0.844	Intermediate Similarity	NPC141001
0.8438	Intermediate Similarity	NPC318325
0.8438	Intermediate Similarity	NPC123273
0.8438	Intermediate Similarity	NPC242240
0.8426	Intermediate Similarity	NPC197513
0.8426	Intermediate Similarity	NPC474050
0.8426	Intermediate Similarity	NPC474114
0.8426	Intermediate Similarity	NPC473931
0.8426	Intermediate Similarity	NPC114918
0.8421	Intermediate Similarity	NPC23167
0.8416	Intermediate Similarity	NPC225506
0.8416	Intermediate Similarity	NPC10588
0.8416	Intermediate Similarity	NPC294741
0.8411	Intermediate Similarity	NPC474920
0.84	Intermediate Similarity	NPC77492
0.84	Intermediate Similarity	NPC156313
0.8384	Intermediate Similarity	NPC274678
0.8384	Intermediate Similarity	NPC26244
0.8384	Intermediate Similarity	NPC222146
0.8381	Intermediate Similarity	NPC95344
0.8365	Intermediate Similarity	NPC310456
0.835	Intermediate Similarity	NPC218879
0.835	Intermediate Similarity	NPC288411
0.835	Intermediate Similarity	NPC244513
0.835	Intermediate Similarity	NPC323810
0.835	Intermediate Similarity	NPC227458
0.8333	Intermediate Similarity	NPC76400
0.8333	Intermediate Similarity	NPC19680
0.8317	Intermediate Similarity	NPC122005
0.8317	Intermediate Similarity	NPC128723
0.8317	Intermediate Similarity	NPC252821
0.8316	Intermediate Similarity	NPC197783
0.8302	Intermediate Similarity	NPC19808
0.8302	Intermediate Similarity	NPC33728
0.83	Intermediate Similarity	NPC473388
0.8288	Intermediate Similarity	NPC206205
0.8286	Intermediate Similarity	NPC61033
0.8286	Intermediate Similarity	NPC54844
0.8286	Intermediate Similarity	NPC305603
0.8283	Intermediate Similarity	NPC289769
0.8283	Intermediate Similarity	NPC316301
0.8283	Intermediate Similarity	NPC151715
0.8283	Intermediate Similarity	NPC128062
0.8283	Intermediate Similarity	NPC27323
0.8273	Intermediate Similarity	NPC69539
0.8269	Intermediate Similarity	NPC117115
0.8269	Intermediate Similarity	NPC134829
0.8269	Intermediate Similarity	NPC471350
0.8265	Intermediate Similarity	NPC204210
0.8265	Intermediate Similarity	NPC270547
0.8265	Intermediate Similarity	NPC304541
0.8257	Intermediate Similarity	NPC471534
0.8252	Intermediate Similarity	NPC168829
0.8252	Intermediate Similarity	NPC168393
0.8247	Intermediate Similarity	NPC98772
0.8247	Intermediate Similarity	NPC258219
0.8241	Intermediate Similarity	NPC166995
0.8241	Intermediate Similarity	NPC228452
0.8241	Intermediate Similarity	NPC98372
0.8229	Intermediate Similarity	NPC184169
0.8224	Intermediate Similarity	NPC132720
0.8224	Intermediate Similarity	NPC296683
0.8218	Intermediate Similarity	NPC109955
0.8214	Intermediate Similarity	NPC323074
0.8211	Intermediate Similarity	NPC248817
0.8211	Intermediate Similarity	NPC175313
0.8208	Intermediate Similarity	NPC241549
0.8208	Intermediate Similarity	NPC174981
0.8208	Intermediate Similarity	NPC306295
0.8208	Intermediate Similarity	NPC169450
0.82	Intermediate Similarity	NPC8392
0.8198	Intermediate Similarity	NPC187993
0.8198	Intermediate Similarity	NPC320864
0.8198	Intermediate Similarity	NPC269414
0.8198	Intermediate Similarity	NPC238176
0.819	Intermediate Similarity	NPC109691
0.819	Intermediate Similarity	NPC39097
0.819	Intermediate Similarity	NPC39664

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 NPC70677 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
0.9175	High Similarity	NPD289	Clinical (unspecified phase)
0.8958	High Similarity	NPD844	Approved
0.8673	High Similarity	NPD288	Approved
0.8585	High Similarity	NPD7635	Approved
0.8519	High Similarity	NPD6671	Approved
0.8469	Intermediate Similarity	NPD2933	Approved
0.8469	Intermediate Similarity	NPD2934	Approved
0.8384	Intermediate Similarity	NPD2860	Approved
0.8384	Intermediate Similarity	NPD2859	Approved
0.8367	Intermediate Similarity	NPD845	Approved
0.8317	Intermediate Similarity	NPD3020	Approved
0.8283	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD940	Approved
0.8155	Intermediate Similarity	NPD846	Approved
0.8131	Intermediate Similarity	NPD4750	Phase 3
0.8105	Intermediate Similarity	NPD111	Approved
0.802	Intermediate Similarity	NPD1809	Phase 2
0.7963	Intermediate Similarity	NPD3022	Approved
0.7963	Intermediate Similarity	NPD3021	Approved
0.785	Intermediate Similarity	NPD1445	Approved
0.785	Intermediate Similarity	NPD1444	Approved
0.7778	Intermediate Similarity	NPD2342	Discontinued
0.7742	Intermediate Similarity	NPD9088	Approved
0.7714	Intermediate Similarity	NPD1242	Phase 1
0.7636	Intermediate Similarity	NPD1792	Phase 2
0.7607	Intermediate Similarity	NPD3496	Discontinued
0.7524	Intermediate Similarity	NPD9273	Approved
0.7523	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6696	Suspended
0.7456	Intermediate Similarity	NPD9614	Approved
0.7456	Intermediate Similarity	NPD497	Approved
0.7456	Intermediate Similarity	NPD9618	Approved
0.7407	Intermediate Similarity	NPD9500	Approved
0.7383	Intermediate Similarity	NPD3028	Approved
0.7368	Intermediate Similarity	NPD496	Approved
0.7368	Intermediate Similarity	NPD495	Approved
0.7368	Intermediate Similarity	NPD2234	Approved
0.7368	Intermediate Similarity	NPD498	Approved
0.7368	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2228	Approved
0.7368	Intermediate Similarity	NPD2229	Approved
0.735	Intermediate Similarity	NPD3091	Approved
0.7339	Intermediate Similarity	NPD9610	Approved
0.7339	Intermediate Similarity	NPD9608	Approved
0.7328	Intermediate Similarity	NPD7340	Approved
0.7317	Intermediate Similarity	NPD2861	Phase 2
0.7312	Intermediate Similarity	NPD9087	Approved
0.7304	Intermediate Similarity	NPD1793	Approved
0.7304	Intermediate Similarity	NPD1791	Approved
0.7281	Intermediate Similarity	NPD9379	Approved
0.7281	Intermediate Similarity	NPD9377	Approved
0.7273	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD9613	Approved
0.7265	Intermediate Similarity	NPD9616	Approved
0.7265	Intermediate Similarity	NPD9615	Approved
0.7255	Intermediate Similarity	NPD9295	Approved
0.725	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4626	Approved
0.7227	Intermediate Similarity	NPD3019	Approved
0.7227	Intermediate Similarity	NPD2932	Approved
0.7227	Intermediate Similarity	NPD4059	Approved
0.7217	Intermediate Similarity	NPD1398	Phase 1
0.7203	Intermediate Similarity	NPD316	Approved
0.719	Intermediate Similarity	NPD2232	Approved
0.719	Intermediate Similarity	NPD2230	Approved
0.719	Intermediate Similarity	NPD2233	Approved
0.7179	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7143	Intermediate Similarity	NPD290	Approved
0.7131	Intermediate Similarity	NPD4749	Approved
0.713	Intermediate Similarity	NPD7843	Approved
0.712	Intermediate Similarity	NPD600	Approved
0.712	Intermediate Similarity	NPD596	Approved
0.7107	Intermediate Similarity	NPD3092	Approved
0.7105	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD709	Approved
0.7083	Intermediate Similarity	NPD4589	Approved
0.7083	Intermediate Similarity	NPD9294	Approved
0.708	Intermediate Similarity	NPD2684	Approved
0.7059	Intermediate Similarity	NPD5304	Approved
0.7059	Intermediate Similarity	NPD5303	Approved
0.7059	Intermediate Similarity	NPD7330	Discontinued
0.7025	Intermediate Similarity	NPD1980	Approved
0.7025	Intermediate Similarity	NPD1983	Approved
0.7025	Intermediate Similarity	NPD1981	Approved
0.7018	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3094	Phase 2
0.7009	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1201	Approved
0.696	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD839	Approved
0.6953	Remote Similarity	NPD840	Approved
0.6949	Remote Similarity	NPD7157	Approved
0.6942	Remote Similarity	NPD1778	Approved
0.6942	Remote Similarity	NPD9381	Approved
0.6942	Remote Similarity	NPD2286	Discontinued
0.6942	Remote Similarity	NPD3095	Discontinued
0.6942	Remote Similarity	NPD1751	Approved
0.6942	Remote Similarity	NPD9384	Approved
0.6935	Remote Similarity	NPD5310	Approved
0.6935	Remote Similarity	NPD5311	Approved
0.693	Remote Similarity	NPD9266	Approved
0.693	Remote Similarity	NPD74	Approved
0.6929	Remote Similarity	NPD4625	Phase 3
0.6923	Remote Similarity	NPD5283	Phase 1
0.6917	Remote Similarity	NPD1759	Phase 1
0.6911	Remote Similarity	NPD2235	Phase 2
0.6911	Remote Similarity	NPD2231	Phase 2
0.6905	Remote Similarity	NPD5736	Approved
0.69	Remote Similarity	NPD9089	Approved
0.6894	Remote Similarity	NPD2935	Discontinued
0.6891	Remote Similarity	NPD9493	Approved
0.6891	Remote Similarity	NPD7636	Approved
0.688	Remote Similarity	NPD3055	Approved
0.688	Remote Similarity	NPD3053	Approved
0.688	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5691	Approved
0.686	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD9622	Approved
0.6855	Remote Similarity	NPD1755	Approved
0.6842	Remote Similarity	NPD9267	Approved
0.6842	Remote Similarity	NPD9263	Approved
0.6842	Remote Similarity	NPD9264	Approved
0.6838	Remote Similarity	NPD821	Approved
0.6833	Remote Similarity	NPD1758	Phase 1
0.6833	Remote Similarity	NPD16	Approved
0.6833	Remote Similarity	NPD856	Approved
0.6829	Remote Similarity	NPD1611	Approved
0.6825	Remote Similarity	NPD6584	Phase 3
0.6807	Remote Similarity	NPD256	Approved
0.6807	Remote Similarity	NPD255	Approved
0.6803	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9093	Approved
0.6797	Remote Similarity	NPD3027	Phase 3
0.6777	Remote Similarity	NPD1548	Phase 1
0.6769	Remote Similarity	NPD4060	Phase 1
0.6748	Remote Similarity	NPD3143	Discontinued
0.6746	Remote Similarity	NPD1470	Approved
0.6726	Remote Similarity	NPD9244	Approved
0.6724	Remote Similarity	NPD5451	Approved
0.6723	Remote Similarity	NPD475	Phase 2
0.6721	Remote Similarity	NPD1357	Approved
0.672	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4908	Phase 1
0.6719	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4817	Approved
0.6696	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4818	Approved
0.6695	Remote Similarity	NPD1138	Approved
0.6694	Remote Similarity	NPD317	Approved
0.6694	Remote Similarity	NPD1610	Phase 2
0.6694	Remote Similarity	NPD422	Phase 1
0.6694	Remote Similarity	NPD1535	Discovery
0.6694	Remote Similarity	NPD318	Approved
0.6693	Remote Similarity	NPD2194	Approved
0.6693	Remote Similarity	NPD858	Approved
0.6693	Remote Similarity	NPD9620	Approved
0.6693	Remote Similarity	NPD9621	Approved
0.6693	Remote Similarity	NPD602	Approved
0.6693	Remote Similarity	NPD9619	Approved
0.6693	Remote Similarity	NPD599	Approved
0.6693	Remote Similarity	NPD2195	Approved
0.6693	Remote Similarity	NPD859	Approved
0.6692	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD6387	Discontinued
0.6667	Remote Similarity	NPD2667	Approved
0.6667	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2668	Approved
0.6641	Remote Similarity	NPD6346	Approved
0.6641	Remote Similarity	NPD3637	Approved
0.6641	Remote Similarity	NPD3636	Approved
0.6641	Remote Similarity	NPD1712	Approved
0.6641	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3635	Approved
0.6641	Remote Similarity	NPD2238	Phase 2
0.6641	Remote Similarity	NPD2237	Approved
0.664	Remote Similarity	NPD1481	Phase 2
0.664	Remote Similarity	NPD2562	Approved
0.664	Remote Similarity	NPD2561	Approved
0.664	Remote Similarity	NPD3070	Discontinued
0.6637	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD601	Approved
0.6615	Remote Similarity	NPD598	Approved
0.6615	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD597	Approved
0.6614	Remote Similarity	NPD1131	Approved
0.6614	Remote Similarity	NPD1129	Approved
0.6614	Remote Similarity	NPD1133	Approved
0.6614	Remote Similarity	NPD1134	Approved
0.6614	Remote Similarity	NPD1135	Approved
0.6614	Remote Similarity	NPD2797	Approved
0.6613	Remote Similarity	NPD3026	Approved
0.6613	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