NPASS Compound

Structure

NPC234730 OpenBabel07101719522D 29 33 0 0 0 0 0 0 0 0999 V2000 -0.1932 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 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 6.5418 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 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 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -5.0000 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 5.9540 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 11 2 0 0 0 0 4 13 1 0 0 0 0 5 11 1 0 0 0 0 5 15 2 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 18 2 0 0 0 0 8 14 1 0 0 0 0 8 16 2 0 0 0 0 9 13 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 10 29 1 0 0 0 0 11 14 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 19 2 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.11
Volume:	384.089
LogP:	3.733
LogD:	3.286
LogS:	-6.414
# Rotatable Bonds:	4
TPSA:	72.45
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	2.617
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.118
MDCK Permeability:	7.857289165258408e-05
Pgp-inhibitor:	0.426
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	86.2671890258789%
Volume Distribution (VD):	0.911
Pgp-substrate:	3.2049126625061035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.8
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.962
CYP2C19-substrate:	0.422
CYP2C9-inhibitor:	0.646
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.472
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	11.766
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.126
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.711
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.814
Skin Sensitization:	0.346
Carcinogencity:	0.888
Eye Corrosion:	0.003
Eye Irritation:	0.067
Respiratory Toxicity:	0.636

Download Data

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

Natural Product: NPC234730

Natural Product ID:	NPC234730
*Common Name:**	Deoxydehydropodophyllotoxin
IUPAC Name:	5-(3,4,5-trimethoxyphenyl)-8H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
Synonyms:	Deoxydehydropodophyllotoxin
Standard InCHIKey:	SSVGOUAYPDYOAE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H18O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h4-8H,9-10H2,1-3H3
SMILES:	COc1cc(cc(c1OC)OC)c1c2cc3c(cc2cc2COC(=O)c12)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518677
PubChem CID:	10500814
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO17947	Hyptis verticillata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277312]
NPO17947	Hyptis verticillata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17947	Hyptis verticillata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17947	Hyptis verticillata	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
ED50	11
Others	5

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	7
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[570891]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	6.2	ug ml-1	PMID[570891]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	16.7	ug ml-1	PMID[570891]
NPT2049	Cell Line	HT	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[570891]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	11.6	ug ml-1	PMID[570891]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	18.8	ug ml-1	PMID[570891]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[570891]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	11.4	ug ml-1	PMID[570891]
NPT140	Organism	Artemia	Artemia	LC50	>	500.0	ug.mL-1	PMID[570891]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[570891]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[570891]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[570891]

☑ 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 NPC234730 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	429
0.1-0.2	1791
0.2-0.3	3800
0.3-0.4	10136
0.4-0.5	8624
0.5-0.6	3534
0.6-0.7	7368
0.7-0.8	6697
0.8-0.85	249
0.85-0.9	51
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC474043
0.9799	High Similarity	NPC473900
0.9536	High Similarity	NPC239113
0.9536	High Similarity	NPC115123
0.9423	High Similarity	NPC474042
0.9423	High Similarity	NPC174734
0.9351	High Similarity	NPC78944
0.9346	High Similarity	NPC19600
0.9329	High Similarity	NPC127827
0.9324	High Similarity	NPC65574
0.9324	High Similarity	NPC304687
0.9324	High Similarity	NPC80230
0.9324	High Similarity	NPC101755
0.9324	High Similarity	NPC104024
0.9304	High Similarity	NPC117911
0.9286	High Similarity	NPC125713
0.9267	High Similarity	NPC475722
0.9231	High Similarity	NPC116838
0.9231	High Similarity	NPC22130
0.92	High Similarity	NPC262455
0.92	High Similarity	NPC177476
0.9167	High Similarity	NPC15212
0.9167	High Similarity	NPC209411
0.9167	High Similarity	NPC239890
0.915	High Similarity	NPC54179
0.9139	High Similarity	NPC149505
0.9133	High Similarity	NPC40654
0.9133	High Similarity	NPC262804
0.9133	High Similarity	NPC181464
0.9079	High Similarity	NPC13985
0.9079	High Similarity	NPC210642
0.9073	High Similarity	NPC24193
0.9057	High Similarity	NPC471923
0.9045	High Similarity	NPC191352
0.9045	High Similarity	NPC258322
0.9018	High Similarity	NPC196771
0.9	High Similarity	NPC475453
0.9	High Similarity	NPC473531
0.8987	High Similarity	NPC198796
0.8903	High Similarity	NPC273578
0.8903	High Similarity	NPC103197
0.8903	High Similarity	NPC30009
0.8896	High Similarity	NPC104353
0.8896	High Similarity	NPC118332
0.8867	High Similarity	NPC475000
0.8859	High Similarity	NPC151423
0.8859	High Similarity	NPC40237
0.8859	High Similarity	NPC210354
0.8859	High Similarity	NPC176586
0.8834	High Similarity	NPC473697
0.8834	High Similarity	NPC312006
0.8834	High Similarity	NPC20114
0.8834	High Similarity	NPC471921
0.8834	High Similarity	NPC114550
0.8834	High Similarity	NPC292712
0.8834	High Similarity	NPC129930
0.8834	High Similarity	NPC474075
0.8834	High Similarity	NPC471922
0.8834	High Similarity	NPC471920
0.8805	High Similarity	NPC319749
0.879	High Similarity	NPC32373
0.879	High Similarity	NPC237946
0.8782	High Similarity	NPC348849
0.8782	High Similarity	NPC178195
0.878	High Similarity	NPC184624
0.8765	High Similarity	NPC79322
0.875	High Similarity	NPC193779
0.875	High Similarity	NPC61141
0.875	High Similarity	NPC280778
0.8742	High Similarity	NPC92693
0.8742	High Similarity	NPC65784
0.8742	High Similarity	NPC191158
0.8742	High Similarity	NPC474770
0.8742	High Similarity	NPC218841
0.8742	High Similarity	NPC177644
0.8734	High Similarity	NPC115281
0.8734	High Similarity	NPC19947
0.8734	High Similarity	NPC143328
0.8734	High Similarity	NPC207584
0.8734	High Similarity	NPC163527
0.8734	High Similarity	NPC181168
0.871	High Similarity	NPC303519
0.8679	High Similarity	NPC325122
0.8671	High Similarity	NPC301897
0.8671	High Similarity	NPC109765
0.8642	High Similarity	NPC477884
0.8625	High Similarity	NPC150943
0.8625	High Similarity	NPC470637
0.8625	High Similarity	NPC119910
0.8625	High Similarity	NPC91634
0.8625	High Similarity	NPC268718
0.8625	High Similarity	NPC96593
0.8623	High Similarity	NPC35266
0.8616	High Similarity	NPC202495
0.8599	High Similarity	NPC245948
0.8589	High Similarity	NPC320471
0.8589	High Similarity	NPC83049
0.8589	High Similarity	NPC118162
0.8571	High Similarity	NPC288149
0.8571	High Similarity	NPC275690
0.8571	High Similarity	NPC161609
0.8571	High Similarity	NPC115624
0.8571	High Similarity	NPC152424
0.8571	High Similarity	NPC100465
0.8562	High Similarity	NPC474158
0.8553	High Similarity	NPC474288
0.8543	High Similarity	NPC218092
0.8543	High Similarity	NPC246474
0.8543	High Similarity	NPC162851
0.8537	High Similarity	NPC311912
0.8535	High Similarity	NPC220577
0.8526	High Similarity	NPC261322
0.8506	High Similarity	NPC87295
0.8503	High Similarity	NPC193377
0.8485	Intermediate Similarity	NPC88557
0.8471	Intermediate Similarity	NPC477700
0.8471	Intermediate Similarity	NPC32079
0.8466	Intermediate Similarity	NPC116759
0.8466	Intermediate Similarity	NPC14294
0.8462	Intermediate Similarity	NPC293757
0.8462	Intermediate Similarity	NPC145569
0.8462	Intermediate Similarity	NPC474965
0.8462	Intermediate Similarity	NPC174512
0.8462	Intermediate Similarity	NPC216223
0.8462	Intermediate Similarity	NPC477695
0.8462	Intermediate Similarity	NPC85141
0.8462	Intermediate Similarity	NPC668
0.8462	Intermediate Similarity	NPC477698
0.8456	Intermediate Similarity	NPC72796
0.8456	Intermediate Similarity	NPC211386
0.8456	Intermediate Similarity	NPC44245
0.8438	Intermediate Similarity	NPC261484
0.8438	Intermediate Similarity	NPC477380
0.8431	Intermediate Similarity	NPC86455
0.8431	Intermediate Similarity	NPC137920
0.8431	Intermediate Similarity	NPC125134
0.8424	Intermediate Similarity	NPC471180
0.8421	Intermediate Similarity	NPC114120
0.8421	Intermediate Similarity	NPC167045
0.8415	Intermediate Similarity	NPC222531
0.8408	Intermediate Similarity	NPC300983
0.8405	Intermediate Similarity	NPC76687
0.8405	Intermediate Similarity	NPC19948
0.84	Intermediate Similarity	NPC11453
0.8385	Intermediate Similarity	NPC82733
0.8385	Intermediate Similarity	NPC76458
0.8385	Intermediate Similarity	NPC477885
0.8383	Intermediate Similarity	NPC178737
0.8377	Intermediate Similarity	NPC18211
0.8375	Intermediate Similarity	NPC202249
0.8375	Intermediate Similarity	NPC188962
0.8375	Intermediate Similarity	NPC478238
0.8375	Intermediate Similarity	NPC42871
0.8365	Intermediate Similarity	NPC308555
0.8365	Intermediate Similarity	NPC477377
0.8365	Intermediate Similarity	NPC144162
0.8364	Intermediate Similarity	NPC306475
0.8354	Intermediate Similarity	NPC475865
0.8354	Intermediate Similarity	NPC164082
0.8333	Intermediate Similarity	NPC15764
0.8333	Intermediate Similarity	NPC68619
0.8333	Intermediate Similarity	NPC477881
0.8333	Intermediate Similarity	NPC72455
0.8324	Intermediate Similarity	NPC286301
0.8324	Intermediate Similarity	NPC313063
0.8323	Intermediate Similarity	NPC155063
0.8322	Intermediate Similarity	NPC205915
0.8313	Intermediate Similarity	NPC185498
0.8302	Intermediate Similarity	NPC475229
0.8302	Intermediate Similarity	NPC474414
0.8302	Intermediate Similarity	NPC477378
0.8302	Intermediate Similarity	NPC477699
0.8302	Intermediate Similarity	NPC56184
0.8293	Intermediate Similarity	NPC108767
0.8291	Intermediate Similarity	NPC316989
0.8289	Intermediate Similarity	NPC470962
0.8282	Intermediate Similarity	NPC139876
0.828	Intermediate Similarity	NPC252281
0.828	Intermediate Similarity	NPC477375
0.828	Intermediate Similarity	NPC327352
0.828	Intermediate Similarity	NPC198129
0.8274	Intermediate Similarity	NPC471181
0.8272	Intermediate Similarity	NPC310206
0.8269	Intermediate Similarity	NPC321958
0.8269	Intermediate Similarity	NPC321696
0.8263	Intermediate Similarity	NPC41853
0.8261	Intermediate Similarity	NPC254163
0.8258	Intermediate Similarity	NPC143092
0.825	Intermediate Similarity	NPC65591
0.825	Intermediate Similarity	NPC68882
0.825	Intermediate Similarity	NPC178574
0.8239	Intermediate Similarity	NPC474975
0.8232	Intermediate Similarity	NPC296540
0.8232	Intermediate Similarity	NPC309335
0.8228	Intermediate Similarity	NPC477374
0.8228	Intermediate Similarity	NPC477376
0.8228	Intermediate Similarity	NPC322426
0.8224	Intermediate Similarity	NPC196420
0.8221	Intermediate Similarity	NPC113055
0.8217	Intermediate Similarity	NPC24257

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 NPC234730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	978
0.2-0.3	1651
0.3-0.4	2769
0.4-0.5	1876
0.5-0.6	964
0.6-0.7	410
0.7-0.8	114
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.879	High Similarity	NPD4967	Phase 2
0.879	High Similarity	NPD4966	Approved
0.879	High Similarity	NPD4965	Approved
0.8758	High Similarity	NPD6980	Clinical (unspecified phase)
0.8679	High Similarity	NPD6234	Discontinued
0.8599	High Similarity	NPD37	Approved
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7228	Approved
0.8263	Intermediate Similarity	NPD5844	Phase 1
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.8232	Intermediate Similarity	NPD7199	Phase 2
0.8133	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7240	Approved
0.7977	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5494	Approved
0.7812	Intermediate Similarity	NPD2533	Approved
0.7812	Intermediate Similarity	NPD2532	Approved
0.7812	Intermediate Similarity	NPD2534	Approved
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD919	Approved
0.7674	Intermediate Similarity	NPD3818	Discontinued
0.7651	Intermediate Similarity	NPD7819	Suspended
0.7643	Intermediate Similarity	NPD2438	Suspended
0.7635	Intermediate Similarity	NPD3705	Approved
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD3817	Phase 2
0.758	Intermediate Similarity	NPD3748	Approved
0.7548	Intermediate Similarity	NPD2979	Phase 3
0.7545	Intermediate Similarity	NPD1465	Phase 2
0.7527	Intermediate Similarity	NPD5005	Approved
0.7527	Intermediate Similarity	NPD5006	Approved
0.7517	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD6959	Discontinued
0.7459	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7768	Phase 2
0.7456	Intermediate Similarity	NPD3882	Suspended
0.7442	Intermediate Similarity	NPD7229	Phase 3
0.744	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3764	Approved
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7458	Discontinued
0.7405	Intermediate Similarity	NPD4420	Approved
0.7394	Intermediate Similarity	NPD7680	Approved
0.7389	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD7074	Phase 3
0.7384	Intermediate Similarity	NPD1247	Approved
0.7381	Intermediate Similarity	NPD1934	Approved
0.7368	Intermediate Similarity	NPD1283	Approved
0.7365	Intermediate Similarity	NPD7028	Phase 2
0.7365	Intermediate Similarity	NPD6599	Discontinued
0.736	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3750	Approved
0.7346	Intermediate Similarity	NPD4628	Phase 3
0.7346	Intermediate Similarity	NPD7003	Approved
0.7337	Intermediate Similarity	NPD2801	Approved
0.7337	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7054	Approved
0.7329	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7411	Suspended
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7315	Intermediate Similarity	NPD1651	Approved
0.7312	Intermediate Similarity	NPD2531	Phase 2
0.731	Intermediate Similarity	NPD3749	Approved
0.7294	Intermediate Similarity	NPD5353	Approved
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.7289	Intermediate Similarity	NPD920	Approved
0.7288	Intermediate Similarity	NPD7472	Approved
0.7284	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1243	Approved
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7257	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6166	Phase 2
0.7247	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5711	Approved
0.7241	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD8455	Phase 2
0.7229	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD6386	Approved
0.7219	Intermediate Similarity	NPD6385	Approved
0.7212	Intermediate Similarity	NPD6799	Approved
0.7209	Intermediate Similarity	NPD7075	Discontinued
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7205	Intermediate Similarity	NPD2796	Approved
0.7202	Intermediate Similarity	NPD3226	Approved
0.72	Intermediate Similarity	NPD5691	Approved
0.7178	Intermediate Similarity	NPD6674	Discontinued
0.7176	Intermediate Similarity	NPD6801	Discontinued
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7808	Phase 3
0.716	Intermediate Similarity	NPD2346	Discontinued
0.7159	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6797	Phase 2
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7251	Discontinued
0.711	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2935	Discontinued
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD5408	Approved
0.7099	Intermediate Similarity	NPD5406	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7093	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8127	Discontinued
0.7066	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4380	Phase 2
0.7044	Intermediate Similarity	NPD8032	Phase 2
0.7039	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4110	Phase 3
0.703	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3027	Phase 3
0.7018	Intermediate Similarity	NPD6873	Phase 2
0.7006	Intermediate Similarity	NPD7390	Discontinued
0.7006	Intermediate Similarity	NPD1511	Approved
0.7005	Intermediate Similarity	NPD7827	Phase 1
0.6994	Remote Similarity	NPD1551	Phase 2
0.6994	Remote Similarity	NPD5402	Approved
0.6983	Remote Similarity	NPD7177	Discontinued
0.6964	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7999	Approved
0.6954	Remote Similarity	NPD5536	Phase 2
0.6954	Remote Similarity	NPD7783	Phase 2
0.6954	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3787	Discontinued
0.6943	Remote Similarity	NPD7435	Discontinued
0.6941	Remote Similarity	NPD1653	Approved
0.6933	Remote Similarity	NPD1510	Phase 2
0.6933	Remote Similarity	NPD2799	Discontinued
0.6928	Remote Similarity	NPD4626	Approved
0.6928	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD7039	Approved
0.6923	Remote Similarity	NPD1876	Approved
0.6923	Remote Similarity	NPD7038	Approved
0.6923	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1512	Approved
0.6918	Remote Similarity	NPD4625	Phase 3
0.6914	Remote Similarity	NPD6971	Discontinued
0.6914	Remote Similarity	NPD1607	Approved
0.6913	Remote Similarity	NPD5283	Phase 1
0.6903	Remote Similarity	NPD2981	Phase 2
0.6903	Remote Similarity	NPD3972	Approved
0.6894	Remote Similarity	NPD4307	Phase 2
0.6889	Remote Similarity	NPD3751	Discontinued
0.6889	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6190	Approved
0.6882	Remote Similarity	NPD5403	Approved
0.6875	Remote Similarity	NPD6778	Approved
0.6875	Remote Similarity	NPD6779	Approved
0.6875	Remote Similarity	NPD6781	Approved
0.6875	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6782	Approved
0.6875	Remote Similarity	NPD6780	Approved
0.6875	Remote Similarity	NPD6776	Approved
0.6875	Remote Similarity	NPD6798	Discontinued
0.6875	Remote Similarity	NPD6777	Approved
0.6864	Remote Similarity	NPD5401	Approved
0.6859	Remote Similarity	NPD2983	Phase 2
0.6859	Remote Similarity	NPD2982	Phase 2
0.6857	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6832	Phase 2
0.6852	Remote Similarity	NPD447	Suspended
0.6848	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7266	Discontinued
0.6836	Remote Similarity	NPD6746	Phase 2
0.6832	Remote Similarity	NPD6233	Phase 2
0.6826	Remote Similarity	NPD8166	Discontinued
0.6821	Remote Similarity	NPD7871	Phase 2
0.6821	Remote Similarity	NPD7870	Phase 2
0.6807	Remote Similarity	NPD1549	Phase 2
0.6805	Remote Similarity	NPD4357	Discontinued
0.6804	Remote Similarity	NPD6823	Phase 2
0.68	Remote Similarity	NPD5978	Approved
0.68	Remote Similarity	NPD5977	Approved
0.68	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4288	Approved
0.6795	Remote Similarity	NPD1608	Approved
0.6792	Remote Similarity	NPD3018	Phase 2
0.679	Remote Similarity	NPD1240	Approved
0.679	Remote Similarity	NPD4060	Phase 1
0.6788	Remote Similarity	NPD6099	Approved
0.6788	Remote Similarity	NPD6100	Approved
0.677	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7698	Approved
0.6769	Remote Similarity	NPD7696	Phase 3

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