NPASS Compound

Structure

NPC78575 OpenBabel07101718292D 23 26 0 0 1 0 0 0 0 0999 V2000 -3.3637 -0.5350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4977 -2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8437 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5348 -0.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0776 1.7258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8003 1.0347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1177 1.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0081 -0.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1695 -1.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1786 0.6341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4977 -1.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6317 -0.5350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3844 -0.5350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3844 0.1851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1786 -0.9839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6034 -0.2172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6317 0.1851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0081 0.5452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5633 0.0632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8806 0.4739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4977 0.6851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0081 1.5452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 19 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 12 17 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 9 1 1 0 0 0 15 23 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 6 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 20 7 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	338.712
LogP:	5.229
LogD:	3.58
LogS:	-4.216
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	5.401
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.642
MDCK Permeability:	2.1071533410577103e-05
Pgp-inhibitor:	0.173
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.179
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.413
Plasma Protein Binding (PPB):	98.16820526123047%
Volume Distribution (VD):	3.003
Pgp-substrate:	2.135444402694702%

ADMET: Metabolism

CYP1A2-inhibitor:	0.125
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.314
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.315
CYP2D6-substrate:	0.689
CYP3A4-inhibitor:	0.339
CYP3A4-substrate:	0.391

ADMET: Excretion

Clearance (CL):	11.644
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.094
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.674
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.942
Carcinogencity:	0.492
Eye Corrosion:	0.004
Eye Irritation:	0.826
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC78575

Natural Product ID:	NPC78575
*Common Name:**	Brussonol
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FTWYPGDUWLQFCC-FTRWYGJKSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-11(2)12-8-13-14(18(22)17(12)21)10-20-7-5-6-19(3,4)16(20)9-15(13)23-20/h8,11,15-16,21-22H,5-7,9-10H2,1-4H3/t15-,16-,20-/m0/s1
SMILES:	CC(c1cc2[C@@H]3C[C@@H]4[C@@](O3)(Cc2c(c1O)O)CCCC4(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252752
PubChem CID:	76311952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[15969497]
NPO13465	Salvia broussonetii	Species	Lamiaceae	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
EC50	1
LD50	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	LD50	=	50.64	ug ml-1	PMID[510622]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LD50	=	19.97	ug ml-1	PMID[510622]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	7.0	%	PMID[510622]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	EC50	>	100.0	microg/cm2	PMID[510622]

☑ 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 NPC78575 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	386
0.1-0.2	1360
0.2-0.3	3151
0.3-0.4	7001
0.4-0.5	11437
0.5-0.6	7548
0.6-0.7	9312
0.7-0.8	2359
0.8-0.85	124
0.85-0.9	14
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC99795
0.9453	High Similarity	NPC59239
0.936	High Similarity	NPC124030
0.9225	High Similarity	NPC312341
0.8915	High Similarity	NPC471077
0.8889	High Similarity	NPC474115
0.8881	High Similarity	NPC68292
0.8797	High Similarity	NPC227719
0.8692	High Similarity	NPC470724
0.8672	High Similarity	NPC471794
0.8652	High Similarity	NPC191899
0.8652	High Similarity	NPC246229
0.8593	High Similarity	NPC471942
0.8582	High Similarity	NPC84786
0.8571	High Similarity	NPC473845
0.8571	High Similarity	NPC196193
0.8561	High Similarity	NPC201069
0.8521	High Similarity	NPC474991
0.8516	High Similarity	NPC470414
0.8504	High Similarity	NPC469644
0.8489	Intermediate Similarity	NPC265075
0.8485	Intermediate Similarity	NPC186889
0.8473	Intermediate Similarity	NPC470726
0.8462	Intermediate Similarity	NPC127046
0.8462	Intermediate Similarity	NPC473451
0.8456	Intermediate Similarity	NPC187616
0.8456	Intermediate Similarity	NPC193026
0.8456	Intermediate Similarity	NPC49603
0.8444	Intermediate Similarity	NPC321086
0.8438	Intermediate Similarity	NPC135467
0.8438	Intermediate Similarity	NPC260832
0.8433	Intermediate Similarity	NPC470727
0.8425	Intermediate Similarity	NPC471671
0.8397	Intermediate Similarity	NPC146355
0.8397	Intermediate Similarity	NPC131747
0.8397	Intermediate Similarity	NPC257682
0.8387	Intermediate Similarity	NPC471179
0.8382	Intermediate Similarity	NPC474453
0.838	Intermediate Similarity	NPC126707
0.838	Intermediate Similarity	NPC472457
0.838	Intermediate Similarity	NPC90645
0.8356	Intermediate Similarity	NPC160196
0.8346	Intermediate Similarity	NPC16030
0.8346	Intermediate Similarity	NPC476536
0.8346	Intermediate Similarity	NPC304510
0.8346	Intermediate Similarity	NPC172219
0.8345	Intermediate Similarity	NPC183380
0.8345	Intermediate Similarity	NPC32630
0.8333	Intermediate Similarity	NPC177160
0.8333	Intermediate Similarity	NPC470733
0.8333	Intermediate Similarity	NPC10737
0.8333	Intermediate Similarity	NPC209985
0.8333	Intermediate Similarity	NPC263367
0.8333	Intermediate Similarity	NPC477939
0.8333	Intermediate Similarity	NPC156502
0.8333	Intermediate Similarity	NPC29799
0.8333	Intermediate Similarity	NPC54743
0.8322	Intermediate Similarity	NPC233980
0.8321	Intermediate Similarity	NPC311256
0.832	Intermediate Similarity	NPC317869
0.831	Intermediate Similarity	NPC164183
0.8309	Intermediate Similarity	NPC228843
0.8309	Intermediate Similarity	NPC165612
0.8298	Intermediate Similarity	NPC186033
0.8288	Intermediate Similarity	NPC2745
0.8284	Intermediate Similarity	NPC45774
0.8284	Intermediate Similarity	NPC282703
0.8284	Intermediate Similarity	NPC129570
0.8284	Intermediate Similarity	NPC11258
0.8284	Intermediate Similarity	NPC128208
0.8284	Intermediate Similarity	NPC184733
0.8284	Intermediate Similarity	NPC223912
0.8284	Intermediate Similarity	NPC21867
0.8281	Intermediate Similarity	NPC469609
0.8281	Intermediate Similarity	NPC154030
0.8271	Intermediate Similarity	NPC100414
0.8271	Intermediate Similarity	NPC325294
0.8271	Intermediate Similarity	NPC321822
0.8271	Intermediate Similarity	NPC43000
0.8268	Intermediate Similarity	NPC38893
0.8268	Intermediate Similarity	NPC469663
0.8268	Intermediate Similarity	NPC477137
0.8268	Intermediate Similarity	NPC92
0.8268	Intermediate Similarity	NPC308311
0.8264	Intermediate Similarity	NPC474397
0.8252	Intermediate Similarity	NPC469557
0.8244	Intermediate Similarity	NPC321402
0.8243	Intermediate Similarity	NPC188578
0.8243	Intermediate Similarity	NPC80918
0.8239	Intermediate Similarity	NPC47633
0.8239	Intermediate Similarity	NPC102044
0.8239	Intermediate Similarity	NPC474104
0.8239	Intermediate Similarity	NPC85264
0.8235	Intermediate Similarity	NPC277804
0.8231	Intermediate Similarity	NPC157783
0.8227	Intermediate Similarity	NPC35216
0.8227	Intermediate Similarity	NPC71046
0.8219	Intermediate Similarity	NPC195561
0.8219	Intermediate Similarity	NPC158784
0.8214	Intermediate Similarity	NPC475757
0.8214	Intermediate Similarity	NPC474640
0.8209	Intermediate Similarity	NPC108164
0.8207	Intermediate Similarity	NPC473876
0.8203	Intermediate Similarity	NPC477136
0.8201	Intermediate Similarity	NPC126101
0.8201	Intermediate Similarity	NPC472800
0.8201	Intermediate Similarity	NPC327735
0.8201	Intermediate Similarity	NPC234952
0.8189	Intermediate Similarity	NPC35797
0.8189	Intermediate Similarity	NPC192948
0.8188	Intermediate Similarity	NPC16485
0.8182	Intermediate Similarity	NPC469795
0.8182	Intermediate Similarity	NPC63879
0.8182	Intermediate Similarity	NPC473108
0.8182	Intermediate Similarity	NPC45257
0.8182	Intermediate Similarity	NPC93323
0.8182	Intermediate Similarity	NPC12641
0.8182	Intermediate Similarity	NPC280092
0.8176	Intermediate Similarity	NPC106669
0.8176	Intermediate Similarity	NPC475227
0.8176	Intermediate Similarity	NPC200645
0.8175	Intermediate Similarity	NPC321502
0.8175	Intermediate Similarity	NPC181049
0.8175	Intermediate Similarity	NPC18842
0.8175	Intermediate Similarity	NPC207400
0.8163	Intermediate Similarity	NPC302915
0.8162	Intermediate Similarity	NPC174495
0.8162	Intermediate Similarity	NPC145305
0.8162	Intermediate Similarity	NPC92164
0.8162	Intermediate Similarity	NPC257582
0.8162	Intermediate Similarity	NPC64201
0.8162	Intermediate Similarity	NPC153739
0.8162	Intermediate Similarity	NPC143483
0.8162	Intermediate Similarity	NPC241522
0.8162	Intermediate Similarity	NPC42300
0.8162	Intermediate Similarity	NPC242807
0.8162	Intermediate Similarity	NPC187998
0.8162	Intermediate Similarity	NPC77040
0.8156	Intermediate Similarity	NPC184797
0.8156	Intermediate Similarity	NPC309124
0.8154	Intermediate Similarity	NPC282255
0.8154	Intermediate Similarity	NPC3239
0.8148	Intermediate Similarity	NPC472968
0.8138	Intermediate Similarity	NPC21776
0.8138	Intermediate Similarity	NPC101376
0.8138	Intermediate Similarity	NPC16269
0.8129	Intermediate Similarity	NPC473413
0.8125	Intermediate Similarity	NPC221318
0.8125	Intermediate Similarity	NPC219112
0.8125	Intermediate Similarity	NPC308828
0.8116	Intermediate Similarity	NPC26394
0.8112	Intermediate Similarity	NPC258083
0.8108	Intermediate Similarity	NPC325860
0.8106	Intermediate Similarity	NPC152946
0.8102	Intermediate Similarity	NPC115207
0.8102	Intermediate Similarity	NPC158079
0.8102	Intermediate Similarity	NPC7171
0.8102	Intermediate Similarity	NPC228346
0.8102	Intermediate Similarity	NPC27843
0.8102	Intermediate Similarity	NPC161557
0.8102	Intermediate Similarity	NPC40432
0.8099	Intermediate Similarity	NPC263261
0.8099	Intermediate Similarity	NPC247291
0.8099	Intermediate Similarity	NPC87725
0.8099	Intermediate Similarity	NPC471414
0.8088	Intermediate Similarity	NPC470747
0.8088	Intermediate Similarity	NPC475875
0.8085	Intermediate Similarity	NPC70682
0.8085	Intermediate Similarity	NPC184613
0.8085	Intermediate Similarity	NPC6300
0.8085	Intermediate Similarity	NPC230124
0.8085	Intermediate Similarity	NPC236306
0.8085	Intermediate Similarity	NPC114171
0.8085	Intermediate Similarity	NPC260741
0.8085	Intermediate Similarity	NPC232164
0.8085	Intermediate Similarity	NPC473739
0.8082	Intermediate Similarity	NPC474795
0.8082	Intermediate Similarity	NPC474940
0.8082	Intermediate Similarity	NPC159697
0.8082	Intermediate Similarity	NPC130959
0.8082	Intermediate Similarity	NPC212142
0.8082	Intermediate Similarity	NPC303013
0.8077	Intermediate Similarity	NPC176893
0.8074	Intermediate Similarity	NPC21563
0.8071	Intermediate Similarity	NPC470802
0.806	Intermediate Similarity	NPC476653
0.806	Intermediate Similarity	NPC4286
0.806	Intermediate Similarity	NPC76119
0.806	Intermediate Similarity	NPC293801
0.8058	Intermediate Similarity	NPC478085
0.8058	Intermediate Similarity	NPC209199
0.8056	Intermediate Similarity	NPC133251
0.8056	Intermediate Similarity	NPC50250
0.8047	Intermediate Similarity	NPC147179
0.8043	Intermediate Similarity	NPC175067
0.8043	Intermediate Similarity	NPC303144
0.8043	Intermediate Similarity	NPC4940
0.8043	Intermediate Similarity	NPC230219
0.8043	Intermediate Similarity	NPC204215
0.8043	Intermediate Similarity	NPC472798

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 NPC78575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	804
0.2-0.3	1626
0.3-0.4	2839
0.4-0.5	1938
0.5-0.6	1114
0.6-0.7	450
0.7-0.8	61
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8175	Intermediate Similarity	NPD3620	Phase 2
0.8175	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD6696	Suspended
0.7958	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3092	Approved
0.7847	Intermediate Similarity	NPD6674	Discontinued
0.781	Intermediate Similarity	NPD2861	Phase 2
0.7794	Intermediate Similarity	NPD3094	Phase 2
0.777	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3091	Approved
0.7724	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD4625	Phase 3
0.766	Intermediate Similarity	NPD1613	Approved
0.766	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD5126	Approved
0.7612	Intermediate Similarity	NPD5125	Phase 3
0.7606	Intermediate Similarity	NPD5735	Approved
0.7578	Intermediate Similarity	NPD3021	Approved
0.7578	Intermediate Similarity	NPD3022	Approved
0.7571	Intermediate Similarity	NPD3027	Phase 3
0.7554	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7635	Approved
0.7518	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6234	Discontinued
0.7444	Intermediate Similarity	NPD7340	Approved
0.7438	Intermediate Similarity	NPD27	Approved
0.7438	Intermediate Similarity	NPD2489	Approved
0.7431	Intermediate Similarity	NPD4097	Suspended
0.7429	Intermediate Similarity	NPD5736	Approved
0.7413	Intermediate Similarity	NPD4060	Phase 1
0.7394	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5327	Phase 3
0.7391	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2969	Approved
0.7375	Intermediate Similarity	NPD2970	Approved
0.7372	Intermediate Similarity	NPD3705	Approved
0.7357	Intermediate Similarity	NPD4624	Approved
0.7353	Intermediate Similarity	NPD3095	Discontinued
0.7353	Intermediate Similarity	NPD4059	Approved
0.7351	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1398	Phase 1
0.7333	Intermediate Similarity	NPD7741	Discontinued
0.7315	Intermediate Similarity	NPD8166	Discontinued
0.7312	Intermediate Similarity	NPD3051	Approved
0.731	Intermediate Similarity	NPD6353	Approved
0.7292	Intermediate Similarity	NPD4140	Approved
0.7289	Intermediate Similarity	NPD7310	Approved
0.7289	Intermediate Similarity	NPD7313	Approved
0.7289	Intermediate Similarity	NPD7311	Approved
0.7289	Intermediate Similarity	NPD4577	Approved
0.7289	Intermediate Similarity	NPD7312	Approved
0.7289	Intermediate Similarity	NPD4578	Approved
0.7287	Intermediate Similarity	NPD2342	Discontinued
0.7279	Intermediate Similarity	NPD6099	Approved
0.7279	Intermediate Similarity	NPD6100	Approved
0.7254	Intermediate Similarity	NPD4908	Phase 1
0.7246	Intermediate Similarity	NPD7309	Approved
0.7246	Intermediate Similarity	NPD1610	Phase 2
0.7244	Intermediate Similarity	NPD37	Approved
0.7241	Intermediate Similarity	NPD3657	Discovery
0.7239	Intermediate Similarity	NPD7228	Approved
0.723	Intermediate Similarity	NPD7266	Discontinued
0.7226	Intermediate Similarity	NPD4626	Approved
0.7226	Intermediate Similarity	NPD3019	Approved
0.7226	Intermediate Similarity	NPD2932	Approved
0.7222	Intermediate Similarity	NPD6663	Approved
0.7215	Intermediate Similarity	NPD4966	Approved
0.7215	Intermediate Similarity	NPD4967	Phase 2
0.7215	Intermediate Similarity	NPD4965	Approved
0.7214	Intermediate Similarity	NPD8651	Approved
0.7197	Intermediate Similarity	NPD228	Approved
0.7197	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1809	Phase 2
0.7176	Intermediate Similarity	NPD4750	Phase 3
0.716	Intermediate Similarity	NPD4663	Approved
0.7153	Intermediate Similarity	NPD5691	Approved
0.7118	Intermediate Similarity	NPD7906	Approved
0.7114	Intermediate Similarity	NPD5762	Approved
0.7114	Intermediate Similarity	NPD5763	Approved
0.7111	Intermediate Similarity	NPD6671	Approved
0.709	Intermediate Similarity	NPD5283	Phase 1
0.7029	Intermediate Similarity	NPD1357	Approved
0.7013	Intermediate Similarity	NPD3645	Discontinued
0.7008	Intermediate Similarity	NPD3020	Approved
0.6984	Remote Similarity	NPD288	Approved
0.6981	Remote Similarity	NPD5929	Approved
0.6974	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD289	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2238	Phase 2
0.6937	Remote Similarity	NPD2563	Approved
0.6937	Remote Similarity	NPD2560	Approved
0.6918	Remote Similarity	NPD1934	Approved
0.6905	Remote Similarity	NPD844	Approved
0.6903	Remote Similarity	NPD2532	Approved
0.6903	Remote Similarity	NPD2534	Approved
0.6903	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2533	Approved
0.6901	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6071	Discontinued
0.6886	Remote Similarity	NPD5844	Phase 1
0.6883	Remote Similarity	NPD5058	Phase 3
0.688	Remote Similarity	NPD845	Approved
0.6867	Remote Similarity	NPD5588	Approved
0.6863	Remote Similarity	NPD4110	Phase 3
0.6863	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6331	Phase 2
0.6861	Remote Similarity	NPD7157	Approved
0.6861	Remote Similarity	NPD4198	Discontinued
0.6853	Remote Similarity	NPD1283	Approved
0.6846	Remote Similarity	NPD2157	Approved
0.6842	Remote Similarity	NPD7037	Approved
0.6839	Remote Similarity	NPD2490	Approved
0.6839	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7041	Phase 2
0.6839	Remote Similarity	NPD2488	Approved
0.6835	Remote Similarity	NPD1548	Phase 1
0.6831	Remote Similarity	NPD2232	Approved
0.6831	Remote Similarity	NPD2233	Approved
0.6831	Remote Similarity	NPD2230	Approved
0.6829	Remote Similarity	NPD8127	Discontinued
0.6825	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2677	Approved
0.6818	Remote Similarity	NPD6190	Approved
0.6807	Remote Similarity	NPD4481	Phase 3
0.6806	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7985	Registered
0.6803	Remote Similarity	NPD3764	Approved
0.6803	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4536	Approved
0.68	Remote Similarity	NPD4538	Approved
0.68	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6232	Discontinued
0.6786	Remote Similarity	NPD1651	Approved
0.6783	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5124	Phase 1
0.6779	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2860	Approved
0.6772	Remote Similarity	NPD2859	Approved
0.6766	Remote Similarity	NPD7473	Discontinued
0.6765	Remote Similarity	NPD7240	Approved
0.6763	Remote Similarity	NPD7644	Approved
0.6761	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1753	Discontinued
0.6755	Remote Similarity	NPD7743	Approved
0.6755	Remote Similarity	NPD7742	Approved
0.6753	Remote Similarity	NPD7003	Approved
0.6753	Remote Similarity	NPD4628	Phase 3
0.6748	Remote Similarity	NPD7833	Phase 2
0.6748	Remote Similarity	NPD7831	Phase 2
0.6748	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1751	Approved
0.6738	Remote Similarity	NPD9381	Approved
0.6738	Remote Similarity	NPD2286	Discontinued
0.6738	Remote Similarity	NPD1778	Approved
0.6738	Remote Similarity	NPD9384	Approved
0.6735	Remote Similarity	NPD7095	Approved
0.6731	Remote Similarity	NPD2421	Approved
0.6731	Remote Similarity	NPD2420	Approved
0.6727	Remote Similarity	NPD7199	Phase 2
0.6727	Remote Similarity	NPD6959	Discontinued
0.6718	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2684	Approved
0.6712	Remote Similarity	NPD3635	Approved
0.6712	Remote Similarity	NPD3636	Approved
0.6712	Remote Similarity	NPD3637	Approved
0.6711	Remote Similarity	NPD2979	Phase 3
0.6711	Remote Similarity	NPD1558	Phase 1
0.6693	Remote Similarity	NPD2934	Approved
0.6693	Remote Similarity	NPD2933	Approved
0.6691	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3023	Approved
0.669	Remote Similarity	NPD3026	Approved
0.6689	Remote Similarity	NPD41	Approved
0.6689	Remote Similarity	NPD5886	Approved
0.6688	Remote Similarity	NPD5177	Phase 3
0.6688	Remote Similarity	NPD4236	Phase 3
0.6688	Remote Similarity	NPD4237	Approved
0.6687	Remote Similarity	NPD7028	Phase 2
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2494	Approved
0.6685	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD4582	Approved
0.6667	Remote Similarity	NPD4666	Phase 3
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD2605	Approved
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD4721	Approved
0.6667	Remote Similarity	NPD4093	Discontinued
0.6667	Remote Similarity	NPD4726	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