NPASS Compound

Structure

NPC137163 OpenBabel07101718322D 31 31 0 0 1 0 0 0 0 0999 V2000 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 5.5000 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 9.1603 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 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 6.9282 4.0000 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 7.7942 4.5000 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 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 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 0.0000 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 8.6603 4.0000 0.0000 C 0 0 1 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 -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 9.5263 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 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 27 1 0 0 0 0 6 27 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 13 15 1 0 0 0 0 13 20 2 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 28 2 0 0 0 0 25 29 2 0 0 0 0 26 27 1 0 0 0 0 26 30 1 6 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	483.697
LogP:	5.466
LogD:	4.325
LogS:	-3.403
# Rotatable Bonds:	11
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	3.794
Fsp3:	0.481
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.971
MDCK Permeability:	2.7853637220687233e-05
Pgp-inhibitor:	0.948
Pgp-substrate:	0.715
Human Intestinal Absorption (HIA):	0.605
20% Bioavailability (F20%):	0.833
30% Bioavailability (F30%):	0.136

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	99.3228530883789%
Volume Distribution (VD):	0.445
Pgp-substrate:	0.5632067322731018%

ADMET: Metabolism

CYP1A2-inhibitor:	0.188
CYP1A2-substrate:	0.592
CYP2C19-inhibitor:	0.166
CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.201
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.859
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	6.716
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.876
Drug-inuced Liver Injury (DILI):	0.003
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.958
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.188
Respiratory Toxicity:	0.89

Download Data

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

Natural Product: NPC137163

Natural Product ID:	NPC137163
*Common Name:**	Capilloquinone
IUPAC Name:	2-[(2E,6E,10E,14S)-14,15-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10-trienyl]-5-methylcyclohexa-2,5-diene-1,4-dione
Synonyms:	Capilloquinone
Standard InCHIKey:	BIWLGTXOHXWEFP-WJJHDEEPSA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-19(10-8-12-21(3)14-16-26(30)27(5,6)31)9-7-11-20(2)13-15-23-18-24(28)22(4)17-25(23)29/h9,12-13,17-18,26,30-31H,7-8,10-11,14-16H2,1-6H3/b19-9+,20-13+,21-12+/t26-/m0/s1
SMILES:	C/C(=CCC/C(=C/CC1=CC(=O)C(=CC1=O)C)/C)/CC/C=C(/CC[C@@H](C(O)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095580
PubChem CID:	46210742
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
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087604]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20155971]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964704]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	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
ED50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	9.8	uM	PMID[506430]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	39.6	%	PMID[506430]

☑ 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 NPC137163 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	143
0.1-0.2	1568
0.2-0.3	7951
0.3-0.4	17688
0.4-0.5	7974
0.5-0.6	5971
0.6-0.7	1297
0.7-0.8	99
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9016	High Similarity	NPC278202
0.873	High Similarity	NPC64971
0.8696	High Similarity	NPC160540
0.8361	Intermediate Similarity	NPC281590
0.8095	Intermediate Similarity	NPC52012
0.7812	Intermediate Similarity	NPC268185
0.7692	Intermediate Similarity	NPC477784
0.7692	Intermediate Similarity	NPC477786
0.7692	Intermediate Similarity	NPC477785
0.7681	Intermediate Similarity	NPC83965
0.7612	Intermediate Similarity	NPC260573
0.7606	Intermediate Similarity	NPC469914
0.76	Intermediate Similarity	NPC325946
0.7571	Intermediate Similarity	NPC193029
0.7571	Intermediate Similarity	NPC96962
0.7571	Intermediate Similarity	NPC106613
0.7571	Intermediate Similarity	NPC473357
0.7568	Intermediate Similarity	NPC114236
0.7541	Intermediate Similarity	NPC20934
0.7541	Intermediate Similarity	NPC288381
0.7541	Intermediate Similarity	NPC225974
0.7532	Intermediate Similarity	NPC472948
0.75	Intermediate Similarity	NPC318766
0.75	Intermediate Similarity	NPC227135
0.75	Intermediate Similarity	NPC478122
0.75	Intermediate Similarity	NPC231739
0.746	Intermediate Similarity	NPC217188
0.7429	Intermediate Similarity	NPC472072
0.7368	Intermediate Similarity	NPC471061
0.7353	Intermediate Similarity	NPC475251
0.7286	Intermediate Similarity	NPC474304
0.7286	Intermediate Similarity	NPC176215
0.7286	Intermediate Similarity	NPC296436
0.7286	Intermediate Similarity	NPC474329
0.7284	Intermediate Similarity	NPC187529
0.7273	Intermediate Similarity	NPC475994
0.725	Intermediate Similarity	NPC161045
0.7237	Intermediate Similarity	NPC250621
0.7222	Intermediate Similarity	NPC273508
0.7222	Intermediate Similarity	NPC117804
0.7222	Intermediate Similarity	NPC209327
0.7215	Intermediate Similarity	NPC474980
0.7179	Intermediate Similarity	NPC291260
0.7162	Intermediate Similarity	NPC95863
0.7162	Intermediate Similarity	NPC67076
0.7162	Intermediate Similarity	NPC319163
0.716	Intermediate Similarity	NPC9868
0.7143	Intermediate Similarity	NPC40049
0.7143	Intermediate Similarity	NPC203403
0.7143	Intermediate Similarity	NPC7029
0.7125	Intermediate Similarity	NPC212083
0.7123	Intermediate Similarity	NPC10758
0.7123	Intermediate Similarity	NPC250928
0.7108	Intermediate Similarity	NPC300779
0.7105	Intermediate Similarity	NPC474885
0.7101	Intermediate Similarity	NPC269737
0.7101	Intermediate Similarity	NPC321838
0.7089	Intermediate Similarity	NPC470947
0.7089	Intermediate Similarity	NPC470945
0.7089	Intermediate Similarity	NPC103634
0.7089	Intermediate Similarity	NPC74086
0.7089	Intermediate Similarity	NPC470946
0.7083	Intermediate Similarity	NPC269985
0.7073	Intermediate Similarity	NPC79573
0.7073	Intermediate Similarity	NPC11804
0.7067	Intermediate Similarity	NPC29542
0.7067	Intermediate Similarity	NPC323437
0.7067	Intermediate Similarity	NPC201562
0.7067	Intermediate Similarity	NPC186042
0.7059	Intermediate Similarity	NPC166554
0.7059	Intermediate Similarity	NPC265856
0.7059	Intermediate Similarity	NPC475931
0.7051	Intermediate Similarity	NPC192006
0.7051	Intermediate Similarity	NPC326753
0.7042	Intermediate Similarity	NPC471200
0.7042	Intermediate Similarity	NPC61473
0.7037	Intermediate Similarity	NPC11620
0.7027	Intermediate Similarity	NPC291062
0.7027	Intermediate Similarity	NPC203819
0.7027	Intermediate Similarity	NPC94743
0.7027	Intermediate Similarity	NPC107848
0.7024	Intermediate Similarity	NPC476707
0.7024	Intermediate Similarity	NPC476706
0.7024	Intermediate Similarity	NPC476708
0.7015	Intermediate Similarity	NPC323436
0.7015	Intermediate Similarity	NPC283502
0.7013	Intermediate Similarity	NPC477708
0.7013	Intermediate Similarity	NPC1973
0.7013	Intermediate Similarity	NPC470525
0.7013	Intermediate Similarity	NPC167873
0.7011	Intermediate Similarity	NPC472977
0.7011	Intermediate Similarity	NPC472976
0.7	Intermediate Similarity	NPC6663
0.7	Intermediate Similarity	NPC143168
0.7	Intermediate Similarity	NPC116797
0.7	Intermediate Similarity	NPC477830
0.7	Intermediate Similarity	NPC53109
0.7	Intermediate Similarity	NPC67254
0.7	Intermediate Similarity	NPC477707
0.7	Intermediate Similarity	NPC470298
0.6988	Remote Similarity	NPC472009
0.6988	Remote Similarity	NPC164393
0.6986	Remote Similarity	NPC125578
0.6986	Remote Similarity	NPC146376
0.6986	Remote Similarity	NPC263382
0.6986	Remote Similarity	NPC310210
0.6984	Remote Similarity	NPC228776
0.6977	Remote Similarity	NPC146852
0.6974	Remote Similarity	NPC147438
0.6974	Remote Similarity	NPC474321
0.6974	Remote Similarity	NPC227814
0.6974	Remote Similarity	NPC144995
0.6974	Remote Similarity	NPC470299
0.6974	Remote Similarity	NPC78527
0.6951	Remote Similarity	NPC70424
0.6951	Remote Similarity	NPC472265
0.6951	Remote Similarity	NPC243618
0.6951	Remote Similarity	NPC476412
0.6944	Remote Similarity	NPC267027
0.6933	Remote Similarity	NPC474884
0.6923	Remote Similarity	NPC82666
0.6923	Remote Similarity	NPC97173
0.6923	Remote Similarity	NPC197659
0.6923	Remote Similarity	NPC476007
0.6914	Remote Similarity	NPC103486
0.6914	Remote Similarity	NPC279186
0.6914	Remote Similarity	NPC474291
0.6912	Remote Similarity	NPC320421
0.6905	Remote Similarity	NPC90652
0.6905	Remote Similarity	NPC472007
0.6897	Remote Similarity	NPC61275
0.6892	Remote Similarity	NPC472947
0.6892	Remote Similarity	NPC16964
0.6892	Remote Similarity	NPC236208
0.6892	Remote Similarity	NPC94488
0.6892	Remote Similarity	NPC262673
0.6885	Remote Similarity	NPC191337
0.6883	Remote Similarity	NPC474011
0.6883	Remote Similarity	NPC329852
0.6883	Remote Similarity	NPC199445
0.6883	Remote Similarity	NPC472256
0.6875	Remote Similarity	NPC2482
0.6875	Remote Similarity	NPC233377
0.6875	Remote Similarity	NPC471514
0.6867	Remote Similarity	NPC137033
0.6867	Remote Similarity	NPC32037
0.6867	Remote Similarity	NPC77971
0.6867	Remote Similarity	NPC477747
0.6867	Remote Similarity	NPC477746
0.686	Remote Similarity	NPC471399
0.686	Remote Similarity	NPC469464
0.686	Remote Similarity	NPC477684
0.6857	Remote Similarity	NPC207007
0.6857	Remote Similarity	NPC68679
0.6857	Remote Similarity	NPC228574
0.6857	Remote Similarity	NPC321867
0.6857	Remote Similarity	NPC294304
0.6849	Remote Similarity	NPC82337
0.6849	Remote Similarity	NPC243272
0.6849	Remote Similarity	NPC251429
0.6842	Remote Similarity	NPC275098
0.6835	Remote Similarity	NPC279532
0.6835	Remote Similarity	NPC62336
0.6829	Remote Similarity	NPC62214
0.6829	Remote Similarity	NPC251475
0.6829	Remote Similarity	NPC16488
0.6829	Remote Similarity	NPC169941
0.6829	Remote Similarity	NPC44261
0.6824	Remote Similarity	NPC476704
0.6824	Remote Similarity	NPC470417
0.6824	Remote Similarity	NPC106051
0.6824	Remote Similarity	NPC472008
0.6824	Remote Similarity	NPC158778
0.6818	Remote Similarity	NPC189677
0.6818	Remote Similarity	NPC473172
0.6812	Remote Similarity	NPC122239
0.68	Remote Similarity	NPC173321
0.68	Remote Similarity	NPC280256
0.68	Remote Similarity	NPC286154
0.6795	Remote Similarity	NPC263582
0.6795	Remote Similarity	NPC469646
0.6795	Remote Similarity	NPC26504
0.679	Remote Similarity	NPC136150
0.679	Remote Similarity	NPC275766
0.679	Remote Similarity	NPC112868
0.6786	Remote Similarity	NPC196381
0.6786	Remote Similarity	NPC472974
0.6786	Remote Similarity	NPC473168
0.6786	Remote Similarity	NPC179591
0.6786	Remote Similarity	NPC183736
0.6782	Remote Similarity	NPC472978
0.6782	Remote Similarity	NPC476705
0.6782	Remote Similarity	NPC472010
0.6782	Remote Similarity	NPC477749
0.6782	Remote Similarity	NPC142838
0.6774	Remote Similarity	NPC8610
0.6774	Remote Similarity	NPC262558
0.6769	Remote Similarity	NPC137396
0.6765	Remote Similarity	NPC192843
0.6765	Remote Similarity	NPC71755

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 NPC137163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	126
0.1-0.2	2235
0.2-0.3	4288
0.3-0.4	1855
0.4-0.5	351
0.5-0.6	267
0.6-0.7	25
0.7-0.8	3
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
0.7681	Intermediate Similarity	NPD7331	Phase 2
0.7089	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7341	Phase 2
0.7037	Intermediate Similarity	NPD6110	Phase 1
0.7	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD368	Approved
0.6712	Remote Similarity	NPD3704	Approved
0.6667	Remote Similarity	NPD3197	Phase 1
0.6548	Remote Similarity	NPD3666	Approved
0.6548	Remote Similarity	NPD3665	Phase 1
0.6548	Remote Similarity	NPD3133	Approved
0.6522	Remote Similarity	NPD8779	Phase 3
0.6486	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6698	Approved
0.6477	Remote Similarity	NPD46	Approved
0.6471	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5363	Approved
0.6463	Remote Similarity	NPD4695	Discontinued
0.642	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD6079	Approved
0.6395	Remote Similarity	NPD5279	Phase 3
0.6395	Remote Similarity	NPD3618	Phase 1
0.6386	Remote Similarity	NPD5369	Approved
0.6375	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD5328	Approved
0.6353	Remote Similarity	NPD4786	Approved
0.6351	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3667	Approved
0.6296	Remote Similarity	NPD4756	Discovery
0.6292	Remote Similarity	NPD7838	Discovery
0.6279	Remote Similarity	NPD1696	Phase 3
0.6265	Remote Similarity	NPD4821	Approved
0.6265	Remote Similarity	NPD4819	Approved
0.6265	Remote Similarity	NPD5368	Approved
0.6265	Remote Similarity	NPD4822	Approved
0.6265	Remote Similarity	NPD4820	Approved
0.6232	Remote Similarity	NPD342	Phase 1
0.6197	Remote Similarity	NPD6109	Phase 1
0.6196	Remote Similarity	NPD5210	Approved
0.6196	Remote Similarity	NPD4629	Approved
0.617	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4202	Approved
0.6145	Remote Similarity	NPD4195	Approved
0.6129	Remote Similarity	NPD5221	Approved
0.6129	Remote Similarity	NPD5222	Approved
0.6129	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD6924	Approved
0.6125	Remote Similarity	NPD6926	Approved
0.6118	Remote Similarity	NPD4221	Approved
0.6118	Remote Similarity	NPD6435	Approved
0.6118	Remote Similarity	NPD4269	Approved
0.6118	Remote Similarity	NPD4223	Phase 3
0.6118	Remote Similarity	NPD4270	Approved
0.6111	Remote Similarity	NPD5785	Approved
0.6105	Remote Similarity	NPD5285	Approved
0.6105	Remote Similarity	NPD5286	Approved
0.6105	Remote Similarity	NPD4696	Approved
0.6094	Remote Similarity	NPD4265	Approved
0.6092	Remote Similarity	NPD5329	Approved
0.6087	Remote Similarity	NPD7748	Approved
0.6071	Remote Similarity	NPD4252	Approved
0.6064	Remote Similarity	NPD6084	Phase 2
0.6064	Remote Similarity	NPD6083	Phase 2
0.6064	Remote Similarity	NPD4755	Approved
0.6064	Remote Similarity	NPD5173	Approved
0.6049	Remote Similarity	NPD8264	Approved
0.6047	Remote Similarity	NPD5332	Approved
0.6047	Remote Similarity	NPD7154	Phase 3
0.6047	Remote Similarity	NPD5362	Discontinued
0.6047	Remote Similarity	NPD5331	Approved
0.6042	Remote Similarity	NPD5223	Approved
0.6026	Remote Similarity	NPD6922	Approved
0.6026	Remote Similarity	NPD6923	Approved
0.6024	Remote Similarity	NPD4268	Approved
0.6024	Remote Similarity	NPD4271	Approved
0.6023	Remote Similarity	NPD5690	Phase 2
0.6023	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD4225	Approved
0.6	Remote Similarity	NPD6101	Approved
0.5979	Remote Similarity	NPD5225	Approved
0.5979	Remote Similarity	NPD4633	Approved
0.5979	Remote Similarity	NPD5226	Approved
0.5979	Remote Similarity	NPD5224	Approved
0.5979	Remote Similarity	NPD5211	Phase 2
0.5977	Remote Similarity	NPD4197	Approved
0.5974	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4697	Phase 3
0.5949	Remote Similarity	NPD7144	Approved
0.5949	Remote Similarity	NPD7143	Approved
0.5938	Remote Similarity	NPD4700	Approved
0.593	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5174	Approved
0.5918	Remote Similarity	NPD5175	Approved
0.5914	Remote Similarity	NPD5282	Discontinued
0.5909	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD6932	Approved
0.5902	Remote Similarity	NPD5783	Phase 3
0.59	Remote Similarity	NPD6412	Phase 2
0.5895	Remote Similarity	NPD7902	Approved
0.5882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7525	Registered
0.5882	Remote Similarity	NPD4634	Approved
0.5876	Remote Similarity	NPD5344	Discontinued
0.5875	Remote Similarity	NPD7150	Approved
0.5875	Remote Similarity	NPD7151	Approved
0.5875	Remote Similarity	NPD7152	Approved
0.587	Remote Similarity	NPD6411	Approved
0.587	Remote Similarity	NPD7983	Approved
0.5862	Remote Similarity	NPD4788	Approved
0.5859	Remote Similarity	NPD5141	Approved
0.5857	Remote Similarity	NPD4266	Approved
0.5857	Remote Similarity	NPD3195	Phase 2
0.5857	Remote Similarity	NPD3194	Approved
0.5857	Remote Similarity	NPD3196	Approved
0.5854	Remote Similarity	NPD7339	Approved
0.5854	Remote Similarity	NPD6942	Approved
0.5851	Remote Similarity	NPD5695	Phase 3
0.5846	Remote Similarity	NPD39	Approved
0.5843	Remote Similarity	NPD7334	Approved
0.5843	Remote Similarity	NPD5280	Approved
0.5843	Remote Similarity	NPD4690	Approved
0.5843	Remote Similarity	NPD4623	Approved
0.5843	Remote Similarity	NPD4689	Approved
0.5843	Remote Similarity	NPD7146	Approved
0.5843	Remote Similarity	NPD4693	Phase 3
0.5843	Remote Similarity	NPD6684	Approved
0.5843	Remote Similarity	NPD5786	Approved
0.5843	Remote Similarity	NPD4694	Approved
0.5843	Remote Similarity	NPD6409	Approved
0.5843	Remote Similarity	NPD4519	Discontinued
0.5843	Remote Similarity	NPD4688	Approved
0.5843	Remote Similarity	NPD7521	Approved
0.5843	Remote Similarity	NPD4138	Approved
0.5843	Remote Similarity	NPD5205	Approved
0.5843	Remote Similarity	NPD5330	Approved
0.5842	Remote Similarity	NPD6899	Approved
0.5842	Remote Similarity	NPD6881	Approved
0.5833	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD3173	Approved
0.5806	Remote Similarity	NPD5779	Approved
0.5806	Remote Similarity	NPD6399	Phase 3
0.5806	Remote Similarity	NPD5778	Approved
0.5802	Remote Similarity	NPD4732	Discontinued
0.58	Remote Similarity	NPD7128	Approved
0.58	Remote Similarity	NPD5739	Approved
0.58	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6675	Approved
0.5795	Remote Similarity	NPD3668	Phase 3
0.5783	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD7524	Approved
0.5769	Remote Similarity	NPD8297	Approved
0.5765	Remote Similarity	NPD6683	Phase 2
0.5765	Remote Similarity	NPD7645	Phase 2
0.5758	Remote Similarity	NPD4754	Approved
0.5753	Remote Similarity	NPD287	Approved
0.575	Remote Similarity	NPD4691	Approved
0.5747	Remote Similarity	NPD5209	Approved
0.5743	Remote Similarity	NPD5697	Approved
0.5733	Remote Similarity	NPD4192	Approved
0.5733	Remote Similarity	NPD4191	Approved
0.5733	Remote Similarity	NPD4194	Approved
0.5733	Remote Similarity	NPD4193	Approved
0.5728	Remote Similarity	NPD7102	Approved
0.5728	Remote Similarity	NPD6371	Approved
0.5728	Remote Similarity	NPD7290	Approved
0.5728	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD5737	Approved
0.5714	Remote Similarity	NPD5776	Phase 2
0.5714	Remote Similarity	NPD3172	Approved
0.5714	Remote Similarity	NPD6925	Approved
0.5714	Remote Similarity	NPD4632	Approved
0.5714	Remote Similarity	NPD6672	Approved
0.5714	Remote Similarity	NPD6903	Approved
0.5714	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4518	Approved
0.5701	Remote Similarity	NPD7115	Discovery
0.5699	Remote Similarity	NPD5284	Approved
0.5699	Remote Similarity	NPD7637	Suspended
0.5699	Remote Similarity	NPD5281	Approved
0.5698	Remote Similarity	NPD7332	Phase 2
0.5698	Remote Similarity	NPD7509	Discontinued
0.5698	Remote Similarity	NPD6931	Approved
0.5698	Remote Similarity	NPD7514	Phase 3
0.5698	Remote Similarity	NPD6930	Phase 2
0.5694	Remote Similarity	NPD4219	Approved
0.5686	Remote Similarity	NPD5128	Approved
0.5686	Remote Similarity	NPD4730	Approved
0.5686	Remote Similarity	NPD7320	Approved
0.5686	Remote Similarity	NPD6686	Approved
0.5686	Remote Similarity	NPD6011	Approved
0.5686	Remote Similarity	NPD4729	Approved
0.5684	Remote Similarity	NPD1698	Clinical (unspecified phase)

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