NPASS Compound

Structure

NPC291062 OpenBabel07101719512D 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 1 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:	360.23
Volume:	399.854
LogP:	4.119
LogD:	3.33
LogS:	-3.604
# 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:	0.191
Synthetic Accessibility Score:	3.03
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.895
MDCK Permeability:	2.845657400030177e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	100.08025360107422%
Volume Distribution (VD):	4.995
Pgp-substrate:	0.8916434645652771%

ADMET: Metabolism

CYP1A2-inhibitor:	0.67
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.53
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.849
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.251
CYP3A4-substrate:	0.098

ADMET: Excretion

Clearance (CL):	6.626
Half-life (T1/2):	0.958

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.004
AMES Toxicity:	0.376
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.107
Skin Sensitization:	0.975
Carcinogencity:	0.467
Eye Corrosion:	0.007
Eye Irritation:	0.905
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC291062

Natural Product ID:	NPC291062
*Common Name:**	Sorgoleone-360
IUPAC Name:	2-hydroxy-5-methoxy-3-[(8Z,11Z)-pentadeca-8,11-dienyl]cyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	XBZLKENMOXIMDN-AFJQJTPPSA-N
Standard InCHI:	InChI=1S/C22H32O4/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/h5-6,8-9,17,24H,3-4,7,10-16H2,1-2H3/b6-5-,9-8-
SMILES:	CCC/C=CC/C=CCCCCCCCC1=C(O)C(=O)C=C(C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269077
PubChem CID:	76308647
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]
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]
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]
NPO26371	Sorghum bicolor	Species	Poaceae	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	1

Activity Type	# Activity
Individual Protein	1

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	=	104.0	nM	PMID[495940]

☑ 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 NPC291062 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
1.0	High Similarity	NPC94743
0.9846	High Similarity	NPC262673
0.9692	High Similarity	NPC146376
0.9692	High Similarity	NPC125578
0.9692	High Similarity	NPC263382
0.9559	High Similarity	NPC264178
0.9538	High Similarity	NPC243272
0.9538	High Similarity	NPC474619
0.9385	High Similarity	NPC16119
0.9254	High Similarity	NPC94488
0.9231	High Similarity	NPC98897
0.9077	High Similarity	NPC7029
0.9077	High Similarity	NPC34622
0.9077	High Similarity	NPC474400
0.8923	High Similarity	NPC53109
0.8923	High Similarity	NPC151728
0.8923	High Similarity	NPC477830
0.8923	High Similarity	NPC57463
0.8923	High Similarity	NPC143168
0.8551	High Similarity	NPC134385
0.8462	Intermediate Similarity	NPC473494
0.8378	Intermediate Similarity	NPC473536
0.8358	Intermediate Similarity	NPC477707
0.8308	Intermediate Similarity	NPC320421
0.8243	Intermediate Similarity	NPC477708
0.7879	Intermediate Similarity	NPC299369
0.7879	Intermediate Similarity	NPC200831
0.7879	Intermediate Similarity	NPC224103
0.7778	Intermediate Similarity	NPC263997
0.7778	Intermediate Similarity	NPC6185
0.7778	Intermediate Similarity	NPC241512
0.7778	Intermediate Similarity	NPC132228
0.7778	Intermediate Similarity	NPC8518
0.7761	Intermediate Similarity	NPC139056
0.7733	Intermediate Similarity	NPC147438
0.7692	Intermediate Similarity	NPC317796
0.7647	Intermediate Similarity	NPC274927
0.7647	Intermediate Similarity	NPC106851
0.7639	Intermediate Similarity	NPC251429
0.7564	Intermediate Similarity	NPC231739
0.7538	Intermediate Similarity	NPC474805
0.7532	Intermediate Similarity	NPC26504
0.7467	Intermediate Similarity	NPC474539
0.7432	Intermediate Similarity	NPC469914
0.7429	Intermediate Similarity	NPC40082
0.7385	Intermediate Similarity	NPC137396
0.7353	Intermediate Similarity	NPC281230
0.7353	Intermediate Similarity	NPC192843
0.7349	Intermediate Similarity	NPC77971
0.7333	Intermediate Similarity	NPC477455
0.7317	Intermediate Similarity	NPC477785
0.7317	Intermediate Similarity	NPC477786
0.7317	Intermediate Similarity	NPC477784
0.7286	Intermediate Similarity	NPC143857
0.7286	Intermediate Similarity	NPC251042
0.7286	Intermediate Similarity	NPC174447
0.7286	Intermediate Similarity	NPC229252
0.7286	Intermediate Similarity	NPC122521
0.7286	Intermediate Similarity	NPC235242
0.7284	Intermediate Similarity	NPC55869
0.7284	Intermediate Similarity	NPC99308
0.7284	Intermediate Similarity	NPC474085
0.7262	Intermediate Similarity	NPC472009
0.7262	Intermediate Similarity	NPC203795
0.7231	Intermediate Similarity	NPC477458
0.7231	Intermediate Similarity	NPC22329
0.7215	Intermediate Similarity	NPC471061
0.7215	Intermediate Similarity	NPC283087
0.7206	Intermediate Similarity	NPC477201
0.7195	Intermediate Similarity	NPC103486
0.7195	Intermediate Similarity	NPC47450
0.7183	Intermediate Similarity	NPC201939
0.7176	Intermediate Similarity	NPC472007
0.7162	Intermediate Similarity	NPC473213
0.716	Intermediate Similarity	NPC108955
0.7143	Intermediate Similarity	NPC474680
0.7143	Intermediate Similarity	NPC470177
0.7143	Intermediate Similarity	NPC32037
0.7126	Intermediate Similarity	NPC474209
0.7126	Intermediate Similarity	NPC471399
0.7126	Intermediate Similarity	NPC475823
0.7123	Intermediate Similarity	NPC176215
0.7123	Intermediate Similarity	NPC296436
0.7093	Intermediate Similarity	NPC472008
0.7093	Intermediate Similarity	NPC53454
0.7089	Intermediate Similarity	NPC110725
0.7077	Intermediate Similarity	NPC220191
0.7073	Intermediate Similarity	NPC225515
0.7067	Intermediate Similarity	NPC477452
0.7051	Intermediate Similarity	NPC474321
0.7051	Intermediate Similarity	NPC227396
0.7045	Intermediate Similarity	NPC146852
0.7042	Intermediate Similarity	NPC243532
0.7037	Intermediate Similarity	NPC475681
0.7027	Intermediate Similarity	NPC137163
0.7027	Intermediate Similarity	NPC197089
0.7027	Intermediate Similarity	NPC83965
0.6986	Remote Similarity	NPC328089
0.6986	Remote Similarity	NPC68343
0.6974	Remote Similarity	NPC10758
0.6974	Remote Similarity	NPC474060
0.6974	Remote Similarity	NPC143396
0.6974	Remote Similarity	NPC250928
0.6966	Remote Similarity	NPC61275
0.6962	Remote Similarity	NPC175079
0.6951	Remote Similarity	NPC74086
0.6951	Remote Similarity	NPC91332
0.6951	Remote Similarity	NPC162741
0.6941	Remote Similarity	NPC90287
0.6941	Remote Similarity	NPC133652
0.6933	Remote Similarity	NPC298249
0.6914	Remote Similarity	NPC478122
0.6914	Remote Similarity	NPC475994
0.6912	Remote Similarity	NPC25417
0.6912	Remote Similarity	NPC290563
0.6912	Remote Similarity	NPC129710
0.6912	Remote Similarity	NPC154245
0.6912	Remote Similarity	NPC281972
0.6912	Remote Similarity	NPC424
0.6912	Remote Similarity	NPC85813
0.6912	Remote Similarity	NPC88966
0.6912	Remote Similarity	NPC87564
0.6912	Remote Similarity	NPC32467
0.6912	Remote Similarity	NPC261831
0.6912	Remote Similarity	NPC6095
0.6905	Remote Similarity	NPC105803
0.6892	Remote Similarity	NPC61473
0.6883	Remote Similarity	NPC173321
0.6883	Remote Similarity	NPC318766
0.6875	Remote Similarity	NPC470525
0.6875	Remote Similarity	NPC1254
0.6867	Remote Similarity	NPC474353
0.6867	Remote Similarity	NPC275766
0.6867	Remote Similarity	NPC286229
0.6857	Remote Similarity	NPC268185
0.6854	Remote Similarity	NPC193396
0.6854	Remote Similarity	NPC32944
0.6842	Remote Similarity	NPC134593
0.6842	Remote Similarity	NPC476614
0.6835	Remote Similarity	NPC160540
0.6835	Remote Similarity	NPC122244
0.6829	Remote Similarity	NPC27817
0.6829	Remote Similarity	NPC471740
0.6824	Remote Similarity	NPC474251
0.6813	Remote Similarity	NPC279313
0.679	Remote Similarity	NPC211279
0.6782	Remote Similarity	NPC476079
0.6782	Remote Similarity	NPC103743
0.6782	Remote Similarity	NPC471738
0.6782	Remote Similarity	NPC113370
0.6778	Remote Similarity	NPC263780
0.6765	Remote Similarity	NPC36061
0.6765	Remote Similarity	NPC139029
0.6765	Remote Similarity	NPC70387
0.6765	Remote Similarity	NPC294548
0.6765	Remote Similarity	NPC139545
0.6765	Remote Similarity	NPC1813
0.6765	Remote Similarity	NPC321062
0.6765	Remote Similarity	NPC39633
0.6765	Remote Similarity	NPC309606
0.6761	Remote Similarity	NPC34416
0.6747	Remote Similarity	NPC2482
0.6744	Remote Similarity	NPC469993
0.6744	Remote Similarity	NPC307112
0.6742	Remote Similarity	NPC265856
0.6742	Remote Similarity	NPC166554
0.6742	Remote Similarity	NPC472325
0.6742	Remote Similarity	NPC223093
0.6714	Remote Similarity	NPC325977
0.6714	Remote Similarity	NPC18951
0.6712	Remote Similarity	NPC320305
0.6712	Remote Similarity	NPC138056
0.6712	Remote Similarity	NPC115752
0.6712	Remote Similarity	NPC328776
0.6712	Remote Similarity	NPC254449
0.6712	Remote Similarity	NPC473212
0.6712	Remote Similarity	NPC15130
0.6712	Remote Similarity	NPC321838
0.6711	Remote Similarity	NPC22101
0.6711	Remote Similarity	NPC26500
0.6711	Remote Similarity	NPC330426
0.6711	Remote Similarity	NPC148192
0.6711	Remote Similarity	NPC99619
0.6711	Remote Similarity	NPC271921
0.6711	Remote Similarity	NPC104537
0.6711	Remote Similarity	NPC127091
0.6709	Remote Similarity	NPC474705
0.6707	Remote Similarity	NPC471409
0.6707	Remote Similarity	NPC275494
0.6707	Remote Similarity	NPC478246
0.6707	Remote Similarity	NPC248624
0.6707	Remote Similarity	NPC478247
0.6707	Remote Similarity	NPC74410
0.6707	Remote Similarity	NPC192006
0.6707	Remote Similarity	NPC189485
0.6707	Remote Similarity	NPC30321
0.6707	Remote Similarity	NPC23778
0.6706	Remote Similarity	NPC53733
0.6706	Remote Similarity	NPC288281
0.6705	Remote Similarity	NPC185059

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 NPC291062 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
0.9385	High Similarity	NPD6108	Clinical (unspecified phase)
0.8923	High Similarity	NPD2664	Clinical (unspecified phase)
0.8806	High Similarity	NPD3704	Approved
0.863	High Similarity	NPD4756	Discovery
0.7879	Intermediate Similarity	NPD8779	Phase 3
0.75	Intermediate Similarity	NPD7331	Phase 2
0.7375	Intermediate Similarity	NPD4695	Discontinued
0.6986	Remote Similarity	NPD3197	Phase 1
0.6951	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3194	Approved
0.6912	Remote Similarity	NPD3196	Approved
0.6912	Remote Similarity	NPD3195	Phase 2
0.6912	Remote Similarity	NPD4266	Approved
0.6892	Remote Similarity	NPD7341	Phase 2
0.6765	Remote Similarity	NPD3172	Approved
0.6706	Remote Similarity	NPD6110	Phase 1
0.6703	Remote Similarity	NPD5282	Discontinued
0.6571	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7154	Phase 3
0.6477	Remote Similarity	NPD5690	Phase 2
0.6471	Remote Similarity	NPD28	Approved
0.6471	Remote Similarity	NPD29	Approved
0.6444	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5363	Approved
0.6364	Remote Similarity	NPD5329	Approved
0.6333	Remote Similarity	NPD6672	Approved
0.6333	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD6083	Phase 2
0.6316	Remote Similarity	NPD6084	Phase 2
0.631	Remote Similarity	NPD3617	Approved
0.6292	Remote Similarity	NPD5279	Phase 3
0.6279	Remote Similarity	NPD5369	Approved
0.6277	Remote Similarity	NPD5210	Approved
0.6277	Remote Similarity	NPD5695	Phase 3
0.6277	Remote Similarity	NPD4629	Approved
0.6264	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD4197	Approved
0.6211	Remote Similarity	NPD5221	Approved
0.6211	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5222	Approved
0.6196	Remote Similarity	NPD5785	Approved
0.6176	Remote Similarity	NPD3173	Approved
0.6146	Remote Similarity	NPD5173	Approved
0.6136	Remote Similarity	NPD5362	Discontinued
0.6129	Remote Similarity	NPD6079	Approved
0.6111	Remote Similarity	NPD4694	Approved
0.6111	Remote Similarity	NPD5280	Approved
0.6087	Remote Similarity	NPD6080	Approved
0.6087	Remote Similarity	NPD6904	Approved
0.6087	Remote Similarity	NPD6101	Approved
0.6087	Remote Similarity	NPD6673	Approved
0.6087	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5696	Approved
0.6081	Remote Similarity	NPD6109	Phase 1
0.6078	Remote Similarity	NPD6899	Approved
0.6078	Remote Similarity	NPD6881	Approved
0.6067	Remote Similarity	NPD3133	Approved
0.6067	Remote Similarity	NPD3665	Phase 1
0.6067	Remote Similarity	NPD4786	Approved
0.6067	Remote Similarity	NPD3666	Approved
0.6029	Remote Similarity	NPD622	Approved
0.6023	Remote Similarity	NPD4269	Approved
0.6023	Remote Similarity	NPD3667	Approved
0.6023	Remote Similarity	NPD6435	Approved
0.6023	Remote Similarity	NPD4221	Approved
0.6023	Remote Similarity	NPD4223	Phase 3
0.6023	Remote Similarity	NPD4270	Approved
0.6023	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD46	Approved
0.6022	Remote Similarity	NPD6698	Approved
0.602	Remote Similarity	NPD5286	Approved
0.602	Remote Similarity	NPD5285	Approved
0.602	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD1696	Phase 3
0.6	Remote Similarity	NPD7748	Approved
0.598	Remote Similarity	NPD5697	Approved
0.5978	Remote Similarity	NPD4518	Approved
0.5977	Remote Similarity	NPD5368	Approved
0.5977	Remote Similarity	NPD4252	Approved
0.597	Remote Similarity	NPD9090	Phase 3
0.5962	Remote Similarity	NPD7102	Approved
0.5962	Remote Similarity	NPD7290	Approved
0.5962	Remote Similarity	NPD6883	Approved
0.596	Remote Similarity	NPD5223	Approved
0.5957	Remote Similarity	NPD7515	Phase 2
0.5957	Remote Similarity	NPD6050	Approved
0.5957	Remote Similarity	NPD5694	Approved
0.5957	Remote Similarity	NPD6411	Approved
0.5952	Remote Similarity	NPD8039	Approved
0.5934	Remote Similarity	NPD4623	Approved
0.5934	Remote Similarity	NPD4519	Discontinued
0.5934	Remote Similarity	NPD3618	Phase 1
0.5934	Remote Similarity	NPD5786	Approved
0.5934	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6011	Approved
0.5921	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5328	Approved
0.5909	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6650	Approved
0.5905	Remote Similarity	NPD6617	Approved
0.5905	Remote Similarity	NPD6847	Approved
0.5905	Remote Similarity	NPD8130	Phase 1
0.5905	Remote Similarity	NPD6649	Approved
0.5905	Remote Similarity	NPD6869	Approved
0.59	Remote Similarity	NPD5224	Approved
0.59	Remote Similarity	NPD5211	Phase 2
0.59	Remote Similarity	NPD5226	Approved
0.59	Remote Similarity	NPD4633	Approved
0.59	Remote Similarity	NPD5225	Approved
0.5895	Remote Similarity	NPD6399	Phase 3
0.5895	Remote Similarity	NPD5778	Approved
0.5895	Remote Similarity	NPD5779	Approved
0.5882	Remote Similarity	NPD6402	Approved
0.5882	Remote Similarity	NPD7128	Approved
0.5882	Remote Similarity	NPD6675	Approved
0.5882	Remote Similarity	NPD5739	Approved
0.5876	Remote Similarity	NPD4697	Phase 3
0.5875	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6012	Approved
0.5865	Remote Similarity	NPD6014	Approved
0.5865	Remote Similarity	NPD6013	Approved
0.5851	Remote Similarity	NPD5692	Phase 3
0.5849	Remote Similarity	NPD6882	Approved
0.5849	Remote Similarity	NPD8297	Approved
0.5842	Remote Similarity	NPD5174	Approved
0.5842	Remote Similarity	NPD5175	Approved
0.5816	Remote Similarity	NPD7902	Approved
0.5816	Remote Similarity	NPD4755	Approved
0.5795	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5281	Approved
0.5789	Remote Similarity	NPD5284	Approved
0.5789	Remote Similarity	NPD5693	Phase 1
0.5784	Remote Similarity	NPD5141	Approved
0.5773	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7320	Approved
0.5761	Remote Similarity	NPD4688	Approved
0.5761	Remote Similarity	NPD4689	Approved
0.5761	Remote Similarity	NPD7521	Approved
0.5761	Remote Similarity	NPD7146	Approved
0.5761	Remote Similarity	NPD4690	Approved
0.5761	Remote Similarity	NPD5205	Approved
0.5761	Remote Similarity	NPD7334	Approved
0.5761	Remote Similarity	NPD6684	Approved
0.5761	Remote Similarity	NPD6098	Approved
0.5761	Remote Similarity	NPD4693	Phase 3
0.5761	Remote Similarity	NPD6409	Approved
0.5761	Remote Similarity	NPD6422	Discontinued
0.5761	Remote Similarity	NPD4138	Approved
0.5761	Remote Similarity	NPD5330	Approved
0.5747	Remote Similarity	NPD4268	Approved
0.5747	Remote Similarity	NPD4271	Approved
0.5743	Remote Similarity	NPD5091	Approved
0.5735	Remote Similarity	NPD4222	Approved
0.5735	Remote Similarity	NPD3174	Discontinued
0.5735	Remote Similarity	NPD39	Approved
0.5714	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.57	Remote Similarity	NPD4700	Approved
0.5699	Remote Similarity	NPD4250	Approved
0.5699	Remote Similarity	NPD3573	Approved
0.5699	Remote Similarity	NPD4251	Approved
0.5688	Remote Similarity	NPD6868	Approved
0.5682	Remote Similarity	NPD4195	Approved
0.5673	Remote Similarity	NPD5701	Approved
0.567	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD4691	Approved
0.5652	Remote Similarity	NPD1694	Approved
0.5647	Remote Similarity	NPD4058	Approved
0.5638	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6903	Approved
0.5625	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7983	Approved
0.5619	Remote Similarity	NPD4729	Approved
0.5619	Remote Similarity	NPD5168	Approved
0.5619	Remote Similarity	NPD4730	Approved
0.5618	Remote Similarity	NPD4820	Approved
0.5618	Remote Similarity	NPD4821	Approved
0.5618	Remote Similarity	NPD4819	Approved
0.5618	Remote Similarity	NPD4822	Approved
0.5607	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD5332	Approved
0.5604	Remote Similarity	NPD5331	Approved
0.5604	Remote Similarity	NPD4788	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data