NPASS Compound

Structure

CID262673 OpenBabel06191716062D 26 26 0 0 0 0 0 0 0 0999 V2000 -8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 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 -8.6603 -4.0000 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 -7.7942 -2.5000 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 -6.9282 -1.0000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 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 -1.5000 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 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 0.8660 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 0.0000 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 -2.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 26 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 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 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 20 2 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 22 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 22 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	397.217
LogP:	3.651
LogD:	2.973
LogS:	-3.619
# Rotatable Bonds:	12
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	3.185
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.935
MDCK Permeability:	2.0529276298475452e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	100.55330657958984%
Volume Distribution (VD):	0.931
Pgp-substrate:	0.6492051482200623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.524
CYP1A2-substrate:	0.866
CYP2C19-inhibitor:	0.495
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.86
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.338
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	6.549
Half-life (T1/2):	0.961

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.003
AMES Toxicity:	0.576
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.205
Skin Sensitization:	0.971
Carcinogencity:	0.757
Eye Corrosion:	0.008
Eye Irritation:	0.905
Respiratory Toxicity:	0.876

Download Data

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

Natural Product: NPC262673

Natural Product ID:	NPC262673
*Common Name:**	Sorgoleone
IUPAC Name:	2-hydroxy-5-methoxy-3-[(8Z,11Z)-pentadeca-8,11,14-trienyl]cyclohexa-2,5-diene-1,4-dione
Synonyms:	Sorgoleone
Standard InCHIKey:	FGWRUVXUQWGLOX-AFJQJTPPSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-21(24)19(23)17-20(26-2)22(18)25/h3,5-6,8-9,17,24H,1,4,7,10-16H2,2H3/b6-5-,9-8-
SMILES:	C=CC/C=CC/C=CCCCCCCCC1=C(O)C(=O)C=C(C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463021
PubChem CID:	6475682
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*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
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542343]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14519932]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	roots	n.a.	n.a.	PMID[14664512]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25172742]
NPO28287	Magnaporthe oryzae	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26258762]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677276]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3641	Polyporus tuberaster	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16391	Protea neriifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO318	Glycosmis trichanthera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4567	Senecio chrysocoma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6773	Bryoria implexa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28287	Magnaporthe oryzae	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4284	Individual Protein	Photosystem Q(B) protein	Spinacia oleracea	IC50	=	65.0	nM	PMID[537035]
NPT2	Others	Unspecified		IC50	=	100.0	nM	PMID[537032]
NPT2	Others	Unspecified		IC50	=	90.0	nM	PMID[537033]

☑ 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 NPC262673 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	160
0.1-0.2	1473
0.2-0.3	8053
0.3-0.4	17861
0.4-0.5	9581
0.5-0.6	4529
0.6-0.7	924
0.7-0.8	86
0.8-0.85	5
0.85-0.9	4
0.9-0.95	12
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC94743
0.9846	High Similarity	NPC291062
0.9688	High Similarity	NPC243272
0.9538	High Similarity	NPC146376
0.9538	High Similarity	NPC125578
0.9538	High Similarity	NPC263382
0.9412	High Similarity	NPC264178
0.9394	High Similarity	NPC94488
0.9385	High Similarity	NPC474619
0.9231	High Similarity	NPC16119
0.9219	High Similarity	NPC474400
0.9219	High Similarity	NPC34622
0.9077	High Similarity	NPC98897
0.9062	High Similarity	NPC477830
0.9062	High Similarity	NPC57463
0.9062	High Similarity	NPC53109
0.9062	High Similarity	NPC143168
0.9062	High Similarity	NPC151728
0.8923	High Similarity	NPC7029
0.8676	High Similarity	NPC134385
0.8594	High Similarity	NPC473494
0.8493	Intermediate Similarity	NPC473536
0.8438	Intermediate Similarity	NPC320421
0.8209	Intermediate Similarity	NPC477707
0.8108	Intermediate Similarity	NPC477708
0.7879	Intermediate Similarity	NPC139056
0.7875	Intermediate Similarity	NPC132228
0.7875	Intermediate Similarity	NPC8518
0.7875	Intermediate Similarity	NPC241512
0.7875	Intermediate Similarity	NPC6185
0.7875	Intermediate Similarity	NPC263997
0.7838	Intermediate Similarity	NPC147438
0.7812	Intermediate Similarity	NPC317796
0.7746	Intermediate Similarity	NPC251429
0.7727	Intermediate Similarity	NPC299369
0.7727	Intermediate Similarity	NPC200831
0.7727	Intermediate Similarity	NPC224103
0.7656	Intermediate Similarity	NPC474805
0.7632	Intermediate Similarity	NPC26504
0.7536	Intermediate Similarity	NPC40082
0.75	Intermediate Similarity	NPC106851
0.75	Intermediate Similarity	NPC137396
0.75	Intermediate Similarity	NPC274927
0.7463	Intermediate Similarity	NPC192843
0.7463	Intermediate Similarity	NPC281230
0.7436	Intermediate Similarity	NPC231739
0.7391	Intermediate Similarity	NPC251042
0.7391	Intermediate Similarity	NPC235242
0.7391	Intermediate Similarity	NPC122521
0.7391	Intermediate Similarity	NPC174447
0.7375	Intermediate Similarity	NPC99308
0.7375	Intermediate Similarity	NPC55869
0.7375	Intermediate Similarity	NPC474085
0.7349	Intermediate Similarity	NPC203795
0.7349	Intermediate Similarity	NPC472009
0.7344	Intermediate Similarity	NPC22329
0.7333	Intermediate Similarity	NPC474539
0.7308	Intermediate Similarity	NPC283087
0.7297	Intermediate Similarity	NPC469914
0.7284	Intermediate Similarity	NPC103486
0.7284	Intermediate Similarity	NPC47450
0.7262	Intermediate Similarity	NPC472007
0.725	Intermediate Similarity	NPC108955
0.7229	Intermediate Similarity	NPC32037
0.7229	Intermediate Similarity	NPC474680
0.7229	Intermediate Similarity	NPC77971
0.7229	Intermediate Similarity	NPC470177
0.7209	Intermediate Similarity	NPC474209
0.7209	Intermediate Similarity	NPC475823
0.72	Intermediate Similarity	NPC477455
0.7195	Intermediate Similarity	NPC477785
0.7195	Intermediate Similarity	NPC477784
0.7195	Intermediate Similarity	NPC477786
0.7188	Intermediate Similarity	NPC220191
0.7179	Intermediate Similarity	NPC110725
0.7176	Intermediate Similarity	NPC53454
0.7176	Intermediate Similarity	NPC472008
0.716	Intermediate Similarity	NPC225515
0.7143	Intermediate Similarity	NPC143857
0.7143	Intermediate Similarity	NPC229252
0.7125	Intermediate Similarity	NPC475681
0.7123	Intermediate Similarity	NPC197089
0.7089	Intermediate Similarity	NPC471061
0.7077	Intermediate Similarity	NPC477458
0.7067	Intermediate Similarity	NPC143396
0.7067	Intermediate Similarity	NPC474060
0.7067	Intermediate Similarity	NPC250928
0.7067	Intermediate Similarity	NPC10758
0.7059	Intermediate Similarity	NPC477201
0.7051	Intermediate Similarity	NPC175079
0.7042	Intermediate Similarity	NPC201939
0.7037	Intermediate Similarity	NPC91332
0.7037	Intermediate Similarity	NPC162741
0.7027	Intermediate Similarity	NPC298249
0.7027	Intermediate Similarity	NPC473213
0.7024	Intermediate Similarity	NPC133652
0.7024	Intermediate Similarity	NPC90287
0.7015	Intermediate Similarity	NPC129710
0.7011	Intermediate Similarity	NPC471399
0.7	Intermediate Similarity	NPC475994
0.7	Intermediate Similarity	NPC478122
0.6988	Remote Similarity	NPC105803
0.6986	Remote Similarity	NPC176215
0.6986	Remote Similarity	NPC296436
0.6974	Remote Similarity	NPC173321
0.6974	Remote Similarity	NPC318766
0.6962	Remote Similarity	NPC1254
0.6962	Remote Similarity	NPC470525
0.6951	Remote Similarity	NPC275766
0.6951	Remote Similarity	NPC474353
0.6933	Remote Similarity	NPC477452
0.6933	Remote Similarity	NPC476614
0.6932	Remote Similarity	NPC193396
0.6932	Remote Similarity	NPC32944
0.6932	Remote Similarity	NPC146852
0.6923	Remote Similarity	NPC227396
0.6923	Remote Similarity	NPC122244
0.6923	Remote Similarity	NPC474321
0.6914	Remote Similarity	NPC27817
0.6905	Remote Similarity	NPC474251
0.6901	Remote Similarity	NPC243532
0.6892	Remote Similarity	NPC83965
0.6892	Remote Similarity	NPC137163
0.6889	Remote Similarity	NPC279313
0.6875	Remote Similarity	NPC211279
0.6866	Remote Similarity	NPC139029
0.6866	Remote Similarity	NPC1813
0.6866	Remote Similarity	NPC36061
0.6866	Remote Similarity	NPC294548
0.6857	Remote Similarity	NPC34416
0.6854	Remote Similarity	NPC61275
0.6849	Remote Similarity	NPC328089
0.6849	Remote Similarity	NPC68343
0.6829	Remote Similarity	NPC74086
0.6824	Remote Similarity	NPC307112
0.6818	Remote Similarity	NPC265856
0.6818	Remote Similarity	NPC166554
0.6818	Remote Similarity	NPC223093
0.6812	Remote Similarity	NPC325977
0.6806	Remote Similarity	NPC15130
0.6806	Remote Similarity	NPC473212
0.6806	Remote Similarity	NPC115752
0.6806	Remote Similarity	NPC138056
0.6806	Remote Similarity	NPC254449
0.679	Remote Similarity	NPC30321
0.679	Remote Similarity	NPC23778
0.679	Remote Similarity	NPC74410
0.679	Remote Similarity	NPC189485
0.679	Remote Similarity	NPC248624
0.6786	Remote Similarity	NPC288281
0.6765	Remote Similarity	NPC6095
0.6765	Remote Similarity	NPC281972
0.6765	Remote Similarity	NPC424
0.6765	Remote Similarity	NPC32467
0.6765	Remote Similarity	NPC290563
0.6765	Remote Similarity	NPC87564
0.6765	Remote Similarity	NPC85813
0.6765	Remote Similarity	NPC88966
0.6765	Remote Similarity	NPC25417
0.6765	Remote Similarity	NPC261831
0.6765	Remote Similarity	NPC154245
0.6757	Remote Similarity	NPC474329
0.6757	Remote Similarity	NPC61473
0.6757	Remote Similarity	NPC474304
0.675	Remote Similarity	NPC180886
0.675	Remote Similarity	NPC40353
0.675	Remote Similarity	NPC92080
0.6747	Remote Similarity	NPC475833
0.6747	Remote Similarity	NPC286229
0.6747	Remote Similarity	NPC116797
0.6744	Remote Similarity	NPC94666
0.6744	Remote Similarity	NPC261721
0.6742	Remote Similarity	NPC32552
0.6742	Remote Similarity	NPC45579
0.6742	Remote Similarity	NPC26865
0.6739	Remote Similarity	NPC134083
0.6739	Remote Similarity	NPC20066
0.6716	Remote Similarity	NPC281245
0.6714	Remote Similarity	NPC268185
0.6712	Remote Similarity	NPC473211
0.6712	Remote Similarity	NPC473210
0.6711	Remote Similarity	NPC134593
0.6711	Remote Similarity	NPC218477
0.6709	Remote Similarity	NPC160540
0.6707	Remote Similarity	NPC471740
0.6707	Remote Similarity	NPC19900
0.6707	Remote Similarity	NPC113363
0.6706	Remote Similarity	NPC469809
0.6705	Remote Similarity	NPC142159
0.6705	Remote Similarity	NPC95364
0.6703	Remote Similarity	NPC91408
0.6703	Remote Similarity	NPC295347
0.6702	Remote Similarity	NPC469851
0.6667	Remote Similarity	NPC166770
0.6667	Remote Similarity	NPC84790
0.6667	Remote Similarity	NPC82666
0.6667	Remote Similarity	NPC15325
0.6667	Remote Similarity	NPC158411
0.6667	Remote Similarity	NPC113370
0.6667	Remote Similarity	NPC263780

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 NPC262673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	2164
0.2-0.3	4165
0.3-0.4	2020
0.4-0.5	404
0.5-0.6	235
0.6-0.7	18
0.7-0.8	4
0.8-0.85	0
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD6108	Clinical (unspecified phase)
0.9062	High Similarity	NPD2664	Clinical (unspecified phase)
0.8939	High Similarity	NPD3704	Approved
0.875	High Similarity	NPD4756	Discovery
0.7727	Intermediate Similarity	NPD8779	Phase 3
0.7468	Intermediate Similarity	NPD4695	Discontinued
0.7361	Intermediate Similarity	NPD7331	Phase 2
0.6866	Remote Similarity	NPD3172	Approved
0.6849	Remote Similarity	NPD3197	Phase 1
0.6829	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5282	Discontinued
0.6765	Remote Similarity	NPD3194	Approved
0.6765	Remote Similarity	NPD4266	Approved
0.6765	Remote Similarity	NPD3196	Approved
0.6765	Remote Similarity	NPD3195	Phase 2
0.6757	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6110	Phase 1
0.6552	Remote Similarity	NPD5690	Phase 2
0.6395	Remote Similarity	NPD7154	Phase 3
0.6386	Remote Similarity	NPD3617	Approved
0.6364	Remote Similarity	NPD5279	Phase 3
0.6344	Remote Similarity	NPD4629	Approved
0.6344	Remote Similarity	NPD5210	Approved
0.6344	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD4753	Phase 2
0.6333	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD29	Approved
0.6324	Remote Similarity	NPD28	Approved
0.6322	Remote Similarity	NPD4197	Approved
0.6277	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5221	Approved
0.6277	Remote Similarity	NPD5222	Approved
0.6269	Remote Similarity	NPD3173	Approved
0.625	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD5363	Approved
0.6222	Remote Similarity	NPD5737	Approved
0.6222	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD6083	Phase 2
0.6211	Remote Similarity	NPD5173	Approved
0.6211	Remote Similarity	NPD6084	Phase 2
0.618	Remote Similarity	NPD5280	Approved
0.618	Remote Similarity	NPD4694	Approved
0.6163	Remote Similarity	NPD5369	Approved
0.6146	Remote Similarity	NPD5696	Approved
0.6136	Remote Similarity	NPD3666	Approved
0.6136	Remote Similarity	NPD3133	Approved
0.6136	Remote Similarity	NPD3665	Phase 1
0.6119	Remote Similarity	NPD622	Approved
0.6092	Remote Similarity	NPD4223	Phase 3
0.6092	Remote Similarity	NPD3667	Approved
0.6092	Remote Similarity	NPD4221	Approved
0.6087	Remote Similarity	NPD5785	Approved
0.6082	Remote Similarity	NPD4696	Approved
0.6082	Remote Similarity	NPD5285	Approved
0.6082	Remote Similarity	NPD5286	Approved
0.6067	Remote Similarity	NPD1696	Phase 3
0.6061	Remote Similarity	NPD9090	Phase 3
0.6044	Remote Similarity	NPD4518	Approved
0.604	Remote Similarity	NPD5697	Approved
0.6023	Remote Similarity	NPD5362	Discontinued
0.6022	Remote Similarity	NPD6079	Approved
0.6022	Remote Similarity	NPD5694	Approved
0.602	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD4623	Approved
0.598	Remote Similarity	NPD6011	Approved
0.598	Remote Similarity	NPD6881	Approved
0.598	Remote Similarity	NPD6899	Approved
0.5978	Remote Similarity	NPD6101	Approved
0.5978	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6080	Approved
0.5978	Remote Similarity	NPD6904	Approved
0.5978	Remote Similarity	NPD6673	Approved
0.596	Remote Similarity	NPD5211	Phase 2
0.596	Remote Similarity	NPD5225	Approved
0.596	Remote Similarity	NPD5226	Approved
0.596	Remote Similarity	NPD4633	Approved
0.596	Remote Similarity	NPD5224	Approved
0.5955	Remote Similarity	NPD4786	Approved
0.5946	Remote Similarity	NPD6109	Phase 1
0.5938	Remote Similarity	NPD4697	Phase 3
0.5922	Remote Similarity	NPD6012	Approved
0.5922	Remote Similarity	NPD6014	Approved
0.5922	Remote Similarity	NPD6013	Approved
0.5914	Remote Similarity	NPD6698	Approved
0.5914	Remote Similarity	NPD5692	Phase 3
0.5914	Remote Similarity	NPD46	Approved
0.5909	Remote Similarity	NPD4270	Approved
0.5909	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4269	Approved
0.5909	Remote Similarity	NPD6435	Approved
0.59	Remote Similarity	NPD5174	Approved
0.59	Remote Similarity	NPD5175	Approved
0.5895	Remote Similarity	NPD7748	Approved
0.5876	Remote Similarity	NPD4755	Approved
0.5865	Remote Similarity	NPD6883	Approved
0.5865	Remote Similarity	NPD7290	Approved
0.5865	Remote Similarity	NPD7102	Approved
0.5862	Remote Similarity	NPD4252	Approved
0.5862	Remote Similarity	NPD5368	Approved
0.5851	Remote Similarity	NPD5284	Approved
0.5851	Remote Similarity	NPD5281	Approved
0.5851	Remote Similarity	NPD7515	Phase 2
0.5851	Remote Similarity	NPD6411	Approved
0.5851	Remote Similarity	NPD6050	Approved
0.5851	Remote Similarity	NPD5693	Phase 1
0.5842	Remote Similarity	NPD5141	Approved
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8039	Approved
0.5824	Remote Similarity	NPD5205	Approved
0.5824	Remote Similarity	NPD5786	Approved
0.5824	Remote Similarity	NPD4690	Approved
0.5824	Remote Similarity	NPD4688	Approved
0.5824	Remote Similarity	NPD4689	Approved
0.5824	Remote Similarity	NPD4138	Approved
0.5824	Remote Similarity	NPD4693	Phase 3
0.5821	Remote Similarity	NPD4222	Approved
0.5821	Remote Similarity	NPD3174	Discontinued
0.5818	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6847	Approved
0.581	Remote Similarity	NPD6649	Approved
0.581	Remote Similarity	NPD8130	Phase 1
0.581	Remote Similarity	NPD6650	Approved
0.581	Remote Similarity	NPD6617	Approved
0.581	Remote Similarity	NPD6869	Approved
0.5806	Remote Similarity	NPD5328	Approved
0.58	Remote Similarity	NPD5091	Approved
0.5789	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5779	Approved
0.5789	Remote Similarity	NPD6399	Phase 3
0.5789	Remote Similarity	NPD5778	Approved
0.5784	Remote Similarity	NPD6402	Approved
0.5784	Remote Similarity	NPD6675	Approved
0.5784	Remote Similarity	NPD7128	Approved
0.5784	Remote Similarity	NPD5739	Approved
0.5778	Remote Similarity	NPD3668	Phase 3
0.5761	Remote Similarity	NPD3573	Approved
0.5758	Remote Similarity	NPD4700	Approved
0.5755	Remote Similarity	NPD6882	Approved
0.5755	Remote Similarity	NPD8297	Approved
0.575	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD4195	Approved
0.5732	Remote Similarity	NPD4691	Approved
0.573	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5701	Approved
0.5714	Remote Similarity	NPD1694	Approved
0.5714	Remote Similarity	NPD4058	Approved
0.5714	Remote Similarity	NPD7902	Approved
0.5682	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4729	Approved
0.5673	Remote Similarity	NPD7320	Approved
0.5673	Remote Similarity	NPD5168	Approved
0.5673	Remote Similarity	NPD4730	Approved
0.5652	Remote Similarity	NPD6409	Approved
0.5652	Remote Similarity	NPD7146	Approved
0.5652	Remote Similarity	NPD6684	Approved
0.5652	Remote Similarity	NPD5330	Approved
0.5652	Remote Similarity	NPD7334	Approved
0.5652	Remote Similarity	NPD6098	Approved
0.5652	Remote Similarity	NPD6422	Discontinued
0.5652	Remote Similarity	NPD4249	Approved
0.5652	Remote Similarity	NPD7521	Approved
0.5632	Remote Similarity	NPD4268	Approved
0.5632	Remote Similarity	NPD4271	Approved
0.5625	Remote Similarity	NPD4202	Approved
0.5625	Remote Similarity	NPD5133	Approved
0.5619	Remote Similarity	NPD6373	Approved
0.5619	Remote Similarity	NPD6372	Approved
0.561	Remote Similarity	NPD4137	Phase 3
0.5606	Remote Similarity	NPD9091	Suspended
0.5606	Remote Similarity	NPD9297	Discontinued

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