NPASS Compound

Structure

CID19948 OpenBabel06191715342D 32 36 0 0 0 0 0 0 0 0999 V2000 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6705 2.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5659 1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 2.4182 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 28 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 29 1 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 24 2 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 30 1 0 0 0 0 16 31 1 0 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 20 25 2 0 0 0 0 21 23 2 0 0 0 0 21 30 1 0 0 0 0 22 32 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 32 1 0 0 0 0 26 27 2 0 0 0 0 26 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.14
Volume:	439.21
LogP:	5.996
LogD:	4.341
LogS:	-6.776
# Rotatable Bonds:	8
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	2.347
Fsp3:	0.192
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.985
MDCK Permeability:	4.2739160562632605e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.122

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	100.70064544677734%
Volume Distribution (VD):	0.928
Pgp-substrate:	1.7920732498168945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.971
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	12.188
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.132
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.742
Skin Sensitization:	0.155
Carcinogencity:	0.802
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC19948

Natural Product ID:	NPC19948
*Common Name:**	3-[2-(1,3-Benzodioxol-5-Yl)-7-Methoxy-1-Benzofuran-5-Yl]Propylbenzoate
IUPAC Name:	3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propyl benzoate
Synonyms:
Standard InCHIKey:	XHOCRIAOIUVTRF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H22O6/c1-28-24-13-17(6-5-11-29-26(27)18-7-3-2-4-8-18)12-20-15-22(32-25(20)24)19-9-10-21-23(14-19)31-16-30-21/h2-4,7-10,12-15H,5-6,11,16H2,1H3
SMILES:	COc1cc(CCCOC(=O)c2ccccc2)cc2c1oc(c2)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469154
PubChem CID:	44577199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO4885	Styrax officinalis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4885	Styrax officinalis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4885	Styrax officinalis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4885	Styrax officinalis	Species	Styracaceae	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
MIC	4
Others	1

Activity Type	# Activity
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	800.0	ug.mL-1	PMID[486793]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	800.0	ug.mL-1	PMID[486793]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	800.0	ug.mL-1	PMID[486793]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	800.0	ug.mL-1	PMID[486793]
NPT2	Others	Unspecified		FC	>	0.6	n.a.	PMID[486794]

☑ 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 NPC19948 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	442
0.1-0.2	1894
0.2-0.3	4239
0.3-0.4	9810
0.4-0.5	8483
0.5-0.6	3954
0.6-0.7	7062
0.7-0.8	6281
0.8-0.85	486
0.85-0.9	33
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC15764
0.974	High Similarity	NPC139876
0.9677	High Similarity	NPC309335
0.9677	High Similarity	NPC296540
0.9608	High Similarity	NPC3273
0.9545	High Similarity	NPC261484
0.9484	High Similarity	NPC82733
0.9484	High Similarity	NPC76458
0.9427	High Similarity	NPC99968
0.9304	High Similarity	NPC109238
0.9172	High Similarity	NPC261090
0.9141	High Similarity	NPC135370
0.8981	High Similarity	NPC60211
0.8916	High Similarity	NPC62640
0.8882	High Similarity	NPC65784
0.8812	High Similarity	NPC115123
0.8812	High Similarity	NPC239113
0.8802	High Similarity	NPC72455
0.8797	High Similarity	NPC118332
0.878	High Similarity	NPC187923
0.875	High Similarity	NPC268008
0.8735	High Similarity	NPC41853
0.8688	High Similarity	NPC54179
0.8675	High Similarity	NPC167479
0.865	High Similarity	NPC78944
0.8642	High Similarity	NPC19600
0.8614	High Similarity	NPC471923
0.8608	High Similarity	NPC127827
0.8599	High Similarity	NPC24257
0.8599	High Similarity	NPC153620
0.8589	High Similarity	NPC250076
0.8589	High Similarity	NPC125713
0.8581	High Similarity	NPC27220
0.858	High Similarity	NPC109765
0.8563	High Similarity	NPC473531
0.8563	High Similarity	NPC475453
0.8553	High Similarity	NPC475722
0.8545	High Similarity	NPC116838
0.8545	High Similarity	NPC302741
0.8545	High Similarity	NPC22130
0.8529	High Similarity	NPC66804
0.8528	High Similarity	NPC202495
0.8521	High Similarity	NPC157522
0.8521	High Similarity	NPC475964
0.8519	High Similarity	NPC284353
0.8512	High Similarity	NPC211309
0.8509	High Similarity	NPC308555
0.8503	High Similarity	NPC210460
0.8503	High Similarity	NPC155264
0.8503	High Similarity	NPC67450
0.8503	High Similarity	NPC193881
0.8485	Intermediate Similarity	NPC15212
0.8485	Intermediate Similarity	NPC216092
0.8476	Intermediate Similarity	NPC474043
0.8476	Intermediate Similarity	NPC68619
0.8466	Intermediate Similarity	NPC155063
0.8457	Intermediate Similarity	NPC279930
0.8424	Intermediate Similarity	NPC131557
0.8424	Intermediate Similarity	NPC243509
0.8415	Intermediate Similarity	NPC310206
0.8412	Intermediate Similarity	NPC20114
0.8412	Intermediate Similarity	NPC114550
0.8412	Intermediate Similarity	NPC473697
0.8412	Intermediate Similarity	NPC292712
0.8412	Intermediate Similarity	NPC471922
0.8412	Intermediate Similarity	NPC129930
0.8412	Intermediate Similarity	NPC474075
0.8412	Intermediate Similarity	NPC471920
0.8412	Intermediate Similarity	NPC312006
0.8412	Intermediate Similarity	NPC471921
0.8405	Intermediate Similarity	NPC234730
0.8405	Intermediate Similarity	NPC254163
0.8405	Intermediate Similarity	NPC80489
0.8395	Intermediate Similarity	NPC68882
0.8383	Intermediate Similarity	NPC179464
0.8375	Intermediate Similarity	NPC24193
0.8373	Intermediate Similarity	NPC258322
0.8373	Intermediate Similarity	NPC34376
0.8373	Intermediate Similarity	NPC191352
0.8364	Intermediate Similarity	NPC257914
0.8364	Intermediate Similarity	NPC238405
0.8364	Intermediate Similarity	NPC104459
0.8364	Intermediate Similarity	NPC33320
0.8364	Intermediate Similarity	NPC113055
0.8363	Intermediate Similarity	NPC316539
0.8363	Intermediate Similarity	NPC474568
0.8363	Intermediate Similarity	NPC65885
0.8363	Intermediate Similarity	NPC184624
0.8343	Intermediate Similarity	NPC186392
0.8333	Intermediate Similarity	NPC475996
0.8333	Intermediate Similarity	NPC104353
0.8333	Intermediate Similarity	NPC477884
0.8333	Intermediate Similarity	NPC279768
0.8323	Intermediate Similarity	NPC78612
0.8323	Intermediate Similarity	NPC18284
0.8323	Intermediate Similarity	NPC273021
0.8323	Intermediate Similarity	NPC300983
0.8323	Intermediate Similarity	NPC474305
0.8323	Intermediate Similarity	NPC234536
0.8323	Intermediate Similarity	NPC198796
0.8314	Intermediate Similarity	NPC193377
0.8313	Intermediate Similarity	NPC181464
0.8303	Intermediate Similarity	NPC258644
0.8293	Intermediate Similarity	NPC478238
0.8284	Intermediate Similarity	NPC174734
0.8284	Intermediate Similarity	NPC298071
0.8284	Intermediate Similarity	NPC474042
0.8282	Intermediate Similarity	NPC137813
0.8282	Intermediate Similarity	NPC144162
0.8274	Intermediate Similarity	NPC110257
0.8274	Intermediate Similarity	NPC45943
0.8274	Intermediate Similarity	NPC100425
0.8274	Intermediate Similarity	NPC65846
0.8274	Intermediate Similarity	NPC132054
0.8266	Intermediate Similarity	NPC8127
0.8266	Intermediate Similarity	NPC196771
0.8266	Intermediate Similarity	NPC49667
0.8263	Intermediate Similarity	NPC239890
0.8263	Intermediate Similarity	NPC469889
0.8263	Intermediate Similarity	NPC209411
0.8261	Intermediate Similarity	NPC475848
0.8261	Intermediate Similarity	NPC474306
0.8253	Intermediate Similarity	NPC325122
0.8246	Intermediate Similarity	NPC144288
0.8246	Intermediate Similarity	NPC476641
0.8246	Intermediate Similarity	NPC52598
0.8242	Intermediate Similarity	NPC473900
0.8239	Intermediate Similarity	NPC213900
0.8232	Intermediate Similarity	NPC244371
0.8232	Intermediate Similarity	NPC478213
0.8228	Intermediate Similarity	NPC137920
0.8228	Intermediate Similarity	NPC125134
0.8228	Intermediate Similarity	NPC86455
0.8225	Intermediate Similarity	NPC179015
0.8225	Intermediate Similarity	NPC173149
0.8218	Intermediate Similarity	NPC47191
0.8218	Intermediate Similarity	NPC35266
0.8218	Intermediate Similarity	NPC267549
0.8214	Intermediate Similarity	NPC61141
0.8214	Intermediate Similarity	NPC125991
0.8214	Intermediate Similarity	NPC272722
0.8208	Intermediate Similarity	NPC236327
0.8208	Intermediate Similarity	NPC287243
0.8208	Intermediate Similarity	NPC290304
0.8204	Intermediate Similarity	NPC74749
0.8204	Intermediate Similarity	NPC19554
0.8204	Intermediate Similarity	NPC269906
0.8204	Intermediate Similarity	NPC43971
0.8204	Intermediate Similarity	NPC474770
0.8202	Intermediate Similarity	NPC205721
0.8199	Intermediate Similarity	NPC117463
0.8187	Intermediate Similarity	NPC117911
0.8182	Intermediate Similarity	NPC471746
0.8182	Intermediate Similarity	NPC10205
0.8176	Intermediate Similarity	NPC113093
0.8171	Intermediate Similarity	NPC275690
0.8171	Intermediate Similarity	NPC161609
0.8171	Intermediate Similarity	NPC153008
0.8171	Intermediate Similarity	NPC148497
0.8171	Intermediate Similarity	NPC292460
0.8166	Intermediate Similarity	NPC223006
0.8166	Intermediate Similarity	NPC134047
0.8166	Intermediate Similarity	NPC272750
0.8166	Intermediate Similarity	NPC173729
0.8161	Intermediate Similarity	NPC156635
0.8161	Intermediate Similarity	NPC296018
0.8161	Intermediate Similarity	NPC154741
0.8161	Intermediate Similarity	NPC67629
0.8161	Intermediate Similarity	NPC79736
0.8161	Intermediate Similarity	NPC107244
0.816	Intermediate Similarity	NPC474975
0.8155	Intermediate Similarity	NPC216916
0.8155	Intermediate Similarity	NPC319749
0.8155	Intermediate Similarity	NPC264293
0.8155	Intermediate Similarity	NPC94155
0.815	Intermediate Similarity	NPC82217
0.815	Intermediate Similarity	NPC476640
0.815	Intermediate Similarity	NPC216842
0.8148	Intermediate Similarity	NPC472839
0.8144	Intermediate Similarity	NPC50430
0.814	Intermediate Similarity	NPC51404
0.8133	Intermediate Similarity	NPC301897
0.8133	Intermediate Similarity	NPC471405
0.8129	Intermediate Similarity	NPC474948
0.8129	Intermediate Similarity	NPC42230
0.8129	Intermediate Similarity	NPC79322
0.8125	Intermediate Similarity	NPC472836
0.8121	Intermediate Similarity	NPC273578
0.8121	Intermediate Similarity	NPC186507
0.8121	Intermediate Similarity	NPC57211
0.8118	Intermediate Similarity	NPC41689
0.8118	Intermediate Similarity	NPC36320
0.8118	Intermediate Similarity	NPC280893
0.8118	Intermediate Similarity	NPC475953
0.8114	Intermediate Similarity	NPC297807
0.8114	Intermediate Similarity	NPC476773
0.8114	Intermediate Similarity	NPC98546
0.8113	Intermediate Similarity	NPC28326
0.811	Intermediate Similarity	NPC472535
0.811	Intermediate Similarity	NPC98028

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 NPC19948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	963
0.2-0.3	1722
0.3-0.4	2636
0.4-0.5	1931
0.5-0.6	981
0.6-0.7	397
0.7-0.8	124
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8428	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD919	Approved
0.8354	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD1247	Approved
0.8072	Intermediate Similarity	NPD3817	Phase 2
0.8059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5494	Approved
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7919	Intermediate Similarity	NPD3818	Discontinued
0.7917	Intermediate Similarity	NPD3882	Suspended
0.7874	Intermediate Similarity	NPD5844	Phase 1
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD920	Approved
0.7735	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD4967	Phase 2
0.7706	Intermediate Similarity	NPD4965	Approved
0.7706	Intermediate Similarity	NPD4966	Approved
0.7688	Intermediate Similarity	NPD6232	Discontinued
0.7684	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6799	Approved
0.7661	Intermediate Similarity	NPD7075	Discontinued
0.7657	Intermediate Similarity	NPD7473	Discontinued
0.764	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6801	Discontinued
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6166	Phase 2
0.76	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7808	Phase 3
0.7588	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6797	Phase 2
0.756	Intermediate Similarity	NPD7458	Discontinued
0.7547	Intermediate Similarity	NPD1933	Approved
0.7546	Intermediate Similarity	NPD1243	Approved
0.7542	Intermediate Similarity	NPD7251	Discontinued
0.7529	Intermediate Similarity	NPD1934	Approved
0.7529	Intermediate Similarity	NPD37	Approved
0.7528	Intermediate Similarity	NPD7074	Phase 3
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7485	Intermediate Similarity	NPD2801	Approved
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7472	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7054	Approved
0.7471	Intermediate Similarity	NPD7411	Suspended
0.7471	Intermediate Similarity	NPD6385	Approved
0.7471	Intermediate Similarity	NPD6386	Approved
0.7468	Intermediate Similarity	NPD6798	Discontinued
0.7457	Intermediate Similarity	NPD3749	Approved
0.743	Intermediate Similarity	NPD7472	Approved
0.7425	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7366	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8313	Approved
0.7363	Intermediate Similarity	NPD8312	Approved
0.7362	Intermediate Similarity	NPD2796	Approved
0.7356	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3226	Approved
0.7349	Intermediate Similarity	NPD3887	Approved
0.7341	Intermediate Similarity	NPD5402	Approved
0.7318	Intermediate Similarity	NPD7228	Approved
0.7318	Intermediate Similarity	NPD2163	Approved
0.7317	Intermediate Similarity	NPD2344	Approved
0.7317	Intermediate Similarity	NPD1471	Phase 3
0.7303	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2799	Discontinued
0.7299	Intermediate Similarity	NPD7768	Phase 2
0.7283	Intermediate Similarity	NPD1465	Phase 2
0.7278	Intermediate Similarity	NPD1512	Approved
0.7253	Intermediate Similarity	NPD7685	Pre-registration
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7246	Intermediate Similarity	NPD6190	Approved
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD3751	Discontinued
0.7222	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3146	Approved
0.7212	Intermediate Similarity	NPD2346	Discontinued
0.7212	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2353	Approved
0.7205	Intermediate Similarity	NPD6233	Phase 2
0.7195	Intermediate Similarity	NPD3748	Approved
0.7191	Intermediate Similarity	NPD7229	Phase 3
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.716	Intermediate Similarity	NPD1511	Approved
0.7158	Intermediate Similarity	NPD7240	Approved
0.7152	Intermediate Similarity	NPD2935	Discontinued
0.7151	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7135	Intermediate Similarity	NPD6959	Discontinued
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD5403	Approved
0.7127	Intermediate Similarity	NPD7177	Discontinued
0.7119	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5401	Approved
0.7118	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD447	Suspended
0.7115	Intermediate Similarity	NPD3705	Approved
0.711	Intermediate Similarity	NPD4380	Phase 2
0.7098	Intermediate Similarity	NPD4107	Approved
0.7097	Intermediate Similarity	NPD17	Approved
0.7095	Intermediate Similarity	NPD6808	Phase 2
0.7083	Intermediate Similarity	NPD4420	Approved
0.7076	Intermediate Similarity	NPD5049	Phase 3
0.7065	Intermediate Similarity	NPD6765	Approved
0.7065	Intermediate Similarity	NPD6764	Approved
0.7055	Intermediate Similarity	NPD4060	Phase 1
0.7052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2354	Approved
0.7037	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6280	Approved
0.7029	Intermediate Similarity	NPD6279	Approved
0.7019	Intermediate Similarity	NPD6832	Phase 2
0.7018	Intermediate Similarity	NPD2532	Approved
0.7018	Intermediate Similarity	NPD2534	Approved
0.7018	Intermediate Similarity	NPD2533	Approved
0.7013	Intermediate Similarity	NPD5536	Phase 2
0.7012	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7028	Phase 2
0.699	Remote Similarity	NPD7435	Discontinued
0.6982	Remote Similarity	NPD3750	Approved
0.6982	Remote Similarity	NPD7003	Approved
0.6977	Remote Similarity	NPD6273	Approved
0.6975	Remote Similarity	NPD7095	Approved
0.6974	Remote Similarity	NPD4482	Phase 3
0.6973	Remote Similarity	NPD7038	Approved
0.6973	Remote Similarity	NPD7039	Approved
0.6964	Remote Similarity	NPD1549	Phase 2
0.6962	Remote Similarity	NPD1608	Approved
0.6951	Remote Similarity	NPD2979	Phase 3
0.6949	Remote Similarity	NPD5353	Approved
0.6949	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5005	Approved
0.6939	Remote Similarity	NPD5006	Approved
0.6923	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6785	Approved
0.6915	Remote Similarity	NPD6784	Approved
0.6909	Remote Similarity	NPD230	Phase 1
0.6905	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1653	Approved
0.6894	Remote Similarity	NPD2798	Approved
0.6886	Remote Similarity	NPD1510	Phase 2
0.6882	Remote Similarity	NPD4110	Phase 3
0.6882	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6873	Phase 2
0.6864	Remote Similarity	NPD2897	Discontinued
0.6862	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3972	Approved
0.6852	Remote Similarity	NPD9494	Approved
0.6848	Remote Similarity	NPD4307	Phase 2
0.6845	Remote Similarity	NPD2438	Suspended
0.6837	Remote Similarity	NPD6781	Approved
0.6837	Remote Similarity	NPD6778	Approved
0.6837	Remote Similarity	NPD6776	Approved
0.6837	Remote Similarity	NPD6782	Approved
0.6837	Remote Similarity	NPD6780	Approved
0.6837	Remote Similarity	NPD6779	Approved
0.6837	Remote Similarity	NPD6777	Approved
0.6832	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3266	Approved
0.6832	Remote Similarity	NPD3267	Approved
0.6826	Remote Similarity	NPD7097	Phase 1
0.6824	Remote Similarity	NPD6674	Discontinued
0.6816	Remote Similarity	NPD8151	Discontinued
0.6809	Remote Similarity	NPD2968	Approved
0.6809	Remote Similarity	NPD2971	Approved
0.6805	Remote Similarity	NPD7266	Discontinued
0.6798	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1281	Approved
0.6788	Remote Similarity	NPD4062	Phase 3
0.6788	Remote Similarity	NPD8032	Phase 2
0.6786	Remote Similarity	NPD7033	Discontinued
0.6784	Remote Similarity	NPD7871	Phase 2
0.6784	Remote Similarity	NPD7870	Phase 2
0.6784	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7874	Approved
0.6769	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5977	Approved
0.676	Remote Similarity	NPD5978	Approved
0.6753	Remote Similarity	NPD1241	Discontinued
0.6749	Remote Similarity	NPD7783	Phase 2
0.6749	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1240	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