NPASS Compound

Structure

CID93593 OpenBabel06191715432D 25 29 0 0 0 0 0 0 0 0999 V2000 -7.0132 4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 3.1910 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 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 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 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 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 -4.4152 1.6910 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 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 2.6910 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 1 0 0 0 0 3 12 2 0 0 0 0 4 17 2 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 21 1 0 0 0 0 7 12 1 0 0 0 0 7 16 2 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	337.13
Volume:	339.396
LogP:	4.158
LogD:	3.602
LogS:	-5.267
# Rotatable Bonds:	2
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.841
Synthetic Accessibility Score:	2.733
Fsp3:	0.3
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:	-5.446
MDCK Permeability:	2.980570752697531e-05
Pgp-inhibitor:	0.955
Pgp-substrate:	0.147
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.062
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.558
Plasma Protein Binding (PPB):	96.5334701538086%
Volume Distribution (VD):	0.839
Pgp-substrate:	2.0622692108154297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.614
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.919
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.682

ADMET: Excretion

Clearance (CL):	12.989
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.344
Human Hepatotoxicity (H-HT):	0.729
Drug-inuced Liver Injury (DILI):	0.464
AMES Toxicity:	0.818
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.656
Skin Sensitization:	0.757
Carcinogencity:	0.938
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC93593

Natural Product ID:	NPC93593
*Common Name:**	Dihydroberberine
IUPAC Name:	n.a.
Synonyms:	Dihydroberberine
Standard InCHIKey:	FZAGOOYMTPGPGF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3
SMILES:	COc1c(OC)ccc2c1CN1CCc3c(C1=C2)cc1c(c3)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL11848
PubChem CID:	10217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	5
Others	15

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	12
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	CC50	=	155000.0	nM	PMID[522382]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[522383]
NPT3003	Individual Protein	Cholesterol esterase	Bos taurus	IC50	=	8.0	ug.mL-1	PMID[522386]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.12	ug.mL-1	PMID[522381]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.171	ug.mL-1	PMID[522381]
NPT32	Organism	Mus musculus	Mus musculus	T-C	=	-0.2	day	PMID[522381]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	93000.0	nM	PMID[522382]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.7	n.a.	PMID[522382]
NPT35	Others	n.a.		Solubility	<	1000.0	ug.mL-1	PMID[522384]
NPT35	Others	n.a.		Stability	=	17.0	%	PMID[522384]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	F	=	2.65	%	PMID[522384]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.0	%	PMID[522384]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.0	%	PMID[522384]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	17.0	%	PMID[522384]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	12.0	%	PMID[522384]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	11.0	%	PMID[522384]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.0	%	PMID[522384]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	ID50	=	0.65	uM	PMID[522385]
NPT27	Others	Unspecified		TD50	=	41.0	uM	PMID[522385]
NPT27	Others	Unspecified		TI	=	63.0	n.a.	PMID[522385]

☑ 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 NPC93593 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	313
0.1-0.2	1653
0.2-0.3	9097
0.3-0.4	8740
0.4-0.5	7165
0.5-0.6	11728
0.6-0.7	3076
0.7-0.8	642
0.8-0.85	196
0.85-0.9	69
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC216459
0.9333	High Similarity	NPC41178
0.9333	High Similarity	NPC138487
0.9272	High Similarity	NPC146288
0.9189	High Similarity	NPC475959
0.9145	High Similarity	NPC234392
0.9145	High Similarity	NPC31311
0.8947	High Similarity	NPC210148
0.8947	High Similarity	NPC233029
0.8917	High Similarity	NPC238530
0.8917	High Similarity	NPC232514
0.8917	High Similarity	NPC276944
0.8867	High Similarity	NPC106295
0.8867	High Similarity	NPC210437
0.8867	High Similarity	NPC51957
0.8867	High Similarity	NPC16107
0.8867	High Similarity	NPC476144
0.8846	High Similarity	NPC266753
0.8846	High Similarity	NPC306902
0.8846	High Similarity	NPC160298
0.8846	High Similarity	NPC232924
0.8846	High Similarity	NPC477559
0.8828	High Similarity	NPC7018
0.8808	High Similarity	NPC7467
0.8788	High Similarity	NPC116007
0.8742	High Similarity	NPC476432
0.8742	High Similarity	NPC24264
0.8716	High Similarity	NPC328750
0.8716	High Similarity	NPC474915
0.8716	High Similarity	NPC188163
0.8716	High Similarity	NPC213206
0.8701	High Similarity	NPC148898
0.8688	High Similarity	NPC247389
0.8679	High Similarity	NPC167546
0.8679	High Similarity	NPC16805
0.8679	High Similarity	NPC302527
0.8679	High Similarity	NPC225774
0.8679	High Similarity	NPC306669
0.8662	High Similarity	NPC111485
0.8649	High Similarity	NPC314682
0.8625	High Similarity	NPC219341
0.8618	High Similarity	NPC476151
0.86	High Similarity	NPC476567
0.86	High Similarity	NPC128019
0.86	High Similarity	NPC136860
0.859	High Similarity	NPC78733
0.8589	High Similarity	NPC2314
0.8571	High Similarity	NPC210918
0.8571	High Similarity	NPC298979
0.8563	High Similarity	NPC83511
0.8562	High Similarity	NPC59907
0.8562	High Similarity	NPC37144
0.8554	High Similarity	NPC179704
0.8553	High Similarity	NPC24954
0.8544	High Similarity	NPC477080
0.8519	High Similarity	NPC241055
0.8509	High Similarity	NPC304659
0.8509	High Similarity	NPC86144
0.8506	High Similarity	NPC477565
0.8506	High Similarity	NPC103379
0.8476	Intermediate Similarity	NPC4669
0.8471	Intermediate Similarity	NPC469817
0.8471	Intermediate Similarity	NPC5238
0.8471	Intermediate Similarity	NPC249797
0.8471	Intermediate Similarity	NPC278799
0.8471	Intermediate Similarity	NPC127674
0.8471	Intermediate Similarity	NPC2413
0.8471	Intermediate Similarity	NPC276588
0.8471	Intermediate Similarity	NPC110416
0.8471	Intermediate Similarity	NPC184026
0.8471	Intermediate Similarity	NPC204828
0.8471	Intermediate Similarity	NPC207757
0.8471	Intermediate Similarity	NPC193949
0.8471	Intermediate Similarity	NPC39701
0.8471	Intermediate Similarity	NPC172765
0.8471	Intermediate Similarity	NPC54379
0.8471	Intermediate Similarity	NPC189266
0.8471	Intermediate Similarity	NPC295691
0.8471	Intermediate Similarity	NPC76079
0.8462	Intermediate Similarity	NPC476580
0.8447	Intermediate Similarity	NPC168409
0.8434	Intermediate Similarity	NPC118633
0.8434	Intermediate Similarity	NPC294790
0.8434	Intermediate Similarity	NPC148693
0.8428	Intermediate Similarity	NPC106786
0.8415	Intermediate Similarity	NPC149090
0.8415	Intermediate Similarity	NPC19520
0.8414	Intermediate Similarity	NPC160193
0.8397	Intermediate Similarity	NPC326316
0.8397	Intermediate Similarity	NPC476568
0.8397	Intermediate Similarity	NPC81733
0.8387	Intermediate Similarity	NPC219162
0.8385	Intermediate Similarity	NPC59567
0.8385	Intermediate Similarity	NPC189470
0.8378	Intermediate Similarity	NPC11147
0.8373	Intermediate Similarity	NPC287588
0.8366	Intermediate Similarity	NPC130926
0.8366	Intermediate Similarity	NPC185838
0.8366	Intermediate Similarity	NPC145304
0.8354	Intermediate Similarity	NPC6152
0.8354	Intermediate Similarity	NPC244112
0.8354	Intermediate Similarity	NPC75958
0.8333	Intermediate Similarity	NPC231198
0.8333	Intermediate Similarity	NPC223125
0.8323	Intermediate Similarity	NPC24233
0.8323	Intermediate Similarity	NPC114364
0.8323	Intermediate Similarity	NPC320223
0.8323	Intermediate Similarity	NPC476571
0.8323	Intermediate Similarity	NPC135538
0.8323	Intermediate Similarity	NPC147390
0.8323	Intermediate Similarity	NPC246587
0.8323	Intermediate Similarity	NPC130941
0.8323	Intermediate Similarity	NPC428
0.8313	Intermediate Similarity	NPC229166
0.8313	Intermediate Similarity	NPC128560
0.8313	Intermediate Similarity	NPC199465
0.8302	Intermediate Similarity	NPC57512
0.8284	Intermediate Similarity	NPC249405
0.8284	Intermediate Similarity	NPC299990
0.8284	Intermediate Similarity	NPC73492
0.8276	Intermediate Similarity	NPC172403
0.8269	Intermediate Similarity	NPC211296
0.8261	Intermediate Similarity	NPC215829
0.8261	Intermediate Similarity	NPC97072
0.8258	Intermediate Similarity	NPC253883
0.8258	Intermediate Similarity	NPC191376
0.8258	Intermediate Similarity	NPC321505
0.8258	Intermediate Similarity	NPC90844
0.8258	Intermediate Similarity	NPC179825
0.8258	Intermediate Similarity	NPC95075
0.825	Intermediate Similarity	NPC476572
0.8239	Intermediate Similarity	NPC99659
0.8239	Intermediate Similarity	NPC325871
0.8228	Intermediate Similarity	NPC223124
0.8221	Intermediate Similarity	NPC247972
0.8217	Intermediate Similarity	NPC88249
0.8217	Intermediate Similarity	NPC220858
0.8217	Intermediate Similarity	NPC192768
0.8217	Intermediate Similarity	NPC97221
0.8217	Intermediate Similarity	NPC151895
0.82	Intermediate Similarity	NPC416184
0.8198	Intermediate Similarity	NPC312531
0.8193	Intermediate Similarity	NPC65403
0.8182	Intermediate Similarity	NPC266176
0.8182	Intermediate Similarity	NPC82533
0.8182	Intermediate Similarity	NPC158148
0.8182	Intermediate Similarity	NPC290759
0.8176	Intermediate Similarity	NPC2295
0.8176	Intermediate Similarity	NPC118419
0.8176	Intermediate Similarity	NPC477564
0.8176	Intermediate Similarity	NPC248642
0.8166	Intermediate Similarity	NPC126284
0.8166	Intermediate Similarity	NPC27887
0.8161	Intermediate Similarity	NPC302001
0.8153	Intermediate Similarity	NPC92541
0.8144	Intermediate Similarity	NPC228040
0.814	Intermediate Similarity	NPC169387
0.814	Intermediate Similarity	NPC477259
0.8133	Intermediate Similarity	NPC311991
0.8133	Intermediate Similarity	NPC152212
0.8129	Intermediate Similarity	NPC156576
0.8121	Intermediate Similarity	NPC474324
0.8121	Intermediate Similarity	NPC57812
0.8121	Intermediate Similarity	NPC100566
0.8118	Intermediate Similarity	NPC32413
0.8118	Intermediate Similarity	NPC474506
0.8107	Intermediate Similarity	NPC23219
0.8101	Intermediate Similarity	NPC274026
0.8098	Intermediate Similarity	NPC60186
0.8095	Intermediate Similarity	NPC187678
0.8092	Intermediate Similarity	NPC474904
0.8086	Intermediate Similarity	NPC216816
0.8084	Intermediate Similarity	NPC470739
0.8084	Intermediate Similarity	NPC225597
0.8084	Intermediate Similarity	NPC303581
0.8084	Intermediate Similarity	NPC477640
0.8084	Intermediate Similarity	NPC67978
0.8075	Intermediate Similarity	NPC126519
0.8075	Intermediate Similarity	NPC203784
0.8075	Intermediate Similarity	NPC247639
0.8075	Intermediate Similarity	NPC170503
0.8075	Intermediate Similarity	NPC25084
0.8072	Intermediate Similarity	NPC58766
0.8072	Intermediate Similarity	NPC475686
0.8072	Intermediate Similarity	NPC475845
0.807	Intermediate Similarity	NPC275132
0.807	Intermediate Similarity	NPC116284
0.8061	Intermediate Similarity	NPC264850
0.8061	Intermediate Similarity	NPC13916
0.8059	Intermediate Similarity	NPC258695
0.8059	Intermediate Similarity	NPC470879
0.8059	Intermediate Similarity	NPC244554
0.8059	Intermediate Similarity	NPC267408
0.805	Intermediate Similarity	NPC476579
0.8049	Intermediate Similarity	NPC320104
0.8049	Intermediate Similarity	NPC233650
0.8047	Intermediate Similarity	NPC112575
0.8046	Intermediate Similarity	NPC281581
0.8038	Intermediate Similarity	NPC207824
0.8038	Intermediate Similarity	NPC60538

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 NPC93593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	743
0.2-0.3	1039
0.3-0.4	1642
0.4-0.5	2851
0.5-0.6	1861
0.6-0.7	660
0.7-0.8	151
0.8-0.85	6
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8867	High Similarity	NPD4584	Approved
0.8716	High Similarity	NPD4664	Clinical (unspecified phase)
0.8506	High Similarity	NPD6030	Approved
0.8506	High Similarity	NPD6031	Approved
0.8421	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD4017	Approved
0.8026	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7298	Approved
0.7987	Intermediate Similarity	NPD5718	Phase 2
0.787	Intermediate Similarity	NPD8252	Approved
0.787	Intermediate Similarity	NPD8251	Approved
0.787	Intermediate Similarity	NPD8099	Discontinued
0.7866	Intermediate Similarity	NPD6788	Approved
0.7824	Intermediate Similarity	NPD8156	Discontinued
0.7812	Intermediate Similarity	NPD3640	Phase 3
0.7812	Intermediate Similarity	NPD3639	Approved
0.7812	Intermediate Similarity	NPD3641	Approved
0.7811	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4772	Phase 2
0.773	Intermediate Similarity	NPD4773	Phase 2
0.7725	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7802	Discontinued
0.7662	Intermediate Similarity	NPD2492	Phase 1
0.7647	Intermediate Similarity	NPD4481	Phase 3
0.7633	Intermediate Similarity	NPD6071	Discontinued
0.7613	Intermediate Similarity	NPD6896	Approved
0.7613	Intermediate Similarity	NPD6895	Approved
0.761	Intermediate Similarity	NPD5241	Discontinued
0.7605	Intermediate Similarity	NPD7831	Phase 2
0.7605	Intermediate Similarity	NPD7833	Phase 2
0.7605	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2563	Approved
0.759	Intermediate Similarity	NPD2560	Approved
0.7582	Intermediate Similarity	NPD4420	Approved
0.7582	Intermediate Similarity	NPD4475	Approved
0.7582	Intermediate Similarity	NPD4474	Approved
0.7578	Intermediate Similarity	NPD1424	Approved
0.7574	Intermediate Similarity	NPD6107	Approved
0.7557	Intermediate Similarity	NPD8053	Approved
0.7557	Intermediate Similarity	NPD8054	Approved
0.7544	Intermediate Similarity	NPD2898	Approved
0.753	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4010	Discontinued
0.7529	Intermediate Similarity	NPD3051	Approved
0.7526	Intermediate Similarity	NPD3816	Phase 1
0.7526	Intermediate Similarity	NPD3815	Phase 1
0.7514	Intermediate Similarity	NPD5005	Approved
0.7514	Intermediate Similarity	NPD5006	Approved
0.75	Intermediate Similarity	NPD7281	Phase 3
0.75	Intermediate Similarity	NPD7280	Phase 3
0.75	Intermediate Similarity	NPD5604	Discontinued
0.7485	Intermediate Similarity	NPD2970	Approved
0.7485	Intermediate Similarity	NPD5978	Approved
0.7485	Intermediate Similarity	NPD2969	Approved
0.7485	Intermediate Similarity	NPD5977	Approved
0.7473	Intermediate Similarity	NPD5582	Discontinued
0.7442	Intermediate Similarity	NPD27	Approved
0.7442	Intermediate Similarity	NPD2489	Approved
0.7438	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6297	Approved
0.7429	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4166	Phase 2
0.7425	Intermediate Similarity	NPD2978	Approved
0.7425	Intermediate Similarity	NPD2977	Approved
0.741	Intermediate Similarity	NPD7110	Phase 1
0.741	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3124	Discontinued
0.7394	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5177	Phase 3
0.7371	Intermediate Similarity	NPD3885	Approved
0.7365	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3349	Phase 2
0.7329	Intermediate Similarity	NPD6748	Discontinued
0.7317	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4859	Phase 1
0.7314	Intermediate Similarity	NPD5313	Approved
0.7314	Intermediate Similarity	NPD5312	Approved
0.7312	Intermediate Similarity	NPD5457	Discontinued
0.7308	Intermediate Similarity	NPD3110	Approved
0.7308	Intermediate Similarity	NPD3109	Approved
0.7301	Intermediate Similarity	NPD2421	Approved
0.7301	Intermediate Similarity	NPD2420	Approved
0.7296	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4727	Phase 1
0.7273	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4162	Approved
0.7267	Intermediate Similarity	NPD4237	Approved
0.7267	Intermediate Similarity	NPD4236	Phase 3
0.7263	Intermediate Similarity	NPD6853	Approved
0.7263	Intermediate Similarity	NPD6851	Approved
0.7256	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7124	Phase 2
0.7228	Intermediate Similarity	NPD6493	Phase 3
0.7222	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5677	Discontinued
0.72	Intermediate Similarity	NPD5938	Phase 3
0.72	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7598	Phase 2
0.7189	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6688	Approved
0.7184	Intermediate Similarity	NPD6687	Approved
0.7175	Intermediate Similarity	NPD3920	Phase 2
0.7169	Intermediate Similarity	NPD5976	Discontinued
0.7167	Intermediate Similarity	NPD6618	Phase 2
0.716	Intermediate Similarity	NPD3060	Approved
0.7159	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3705	Approved
0.7151	Intermediate Similarity	NPD7034	Discontinued
0.7143	Intermediate Similarity	NPD7906	Approved
0.7143	Intermediate Similarity	NPD7291	Discontinued
0.7135	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2674	Phase 3
0.7128	Intermediate Similarity	NPD6612	Phase 2
0.7126	Intermediate Similarity	NPD4210	Discontinued
0.7125	Intermediate Similarity	NPD4108	Discontinued
0.7124	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3763	Approved
0.712	Intermediate Similarity	NPD3924	Approved
0.712	Intermediate Similarity	NPD3923	Approved
0.712	Intermediate Similarity	NPD3922	Approved
0.712	Intermediate Similarity	NPD3921	Approved
0.7117	Intermediate Similarity	NPD5754	Discontinued
0.7117	Intermediate Similarity	NPD6331	Phase 2
0.7111	Intermediate Similarity	NPD7310	Approved
0.7111	Intermediate Similarity	NPD2968	Approved
0.7111	Intermediate Similarity	NPD7313	Approved
0.7111	Intermediate Similarity	NPD2971	Approved
0.7111	Intermediate Similarity	NPD7311	Approved
0.7111	Intermediate Similarity	NPD7312	Approved
0.7099	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4055	Discovery
0.7086	Intermediate Similarity	NPD4083	Discontinued
0.7083	Intermediate Similarity	NPD6357	Discontinued
0.7078	Intermediate Similarity	NPD4098	Discontinued
0.7074	Intermediate Similarity	NPD8095	Phase 1
0.7073	Intermediate Similarity	NPD3301	Approved
0.7072	Intermediate Similarity	NPD7309	Approved
0.7069	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3384	Approved
0.7059	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3383	Approved
0.7059	Intermediate Similarity	NPD3382	Approved
0.7056	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7400	Phase 3
0.7041	Intermediate Similarity	NPD6876	Approved
0.7041	Intermediate Similarity	NPD6875	Approved
0.7037	Intermediate Similarity	NPD3656	Approved
0.7033	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7247	Discontinued
0.7032	Intermediate Similarity	NPD7905	Discontinued
0.703	Intermediate Similarity	NPD3845	Phase 1
0.7025	Intermediate Similarity	NPD3531	Approved
0.7025	Intermediate Similarity	NPD3532	Approved
0.7025	Intermediate Similarity	NPD3530	Approved
0.7022	Intermediate Similarity	NPD5600	Discontinued
0.7021	Intermediate Similarity	NPD6877	Discontinued
0.702	Intermediate Similarity	NPD2667	Approved
0.702	Intermediate Similarity	NPD2668	Approved
0.7017	Intermediate Similarity	NPD4577	Approved
0.7017	Intermediate Similarity	NPD4578	Approved
0.7011	Intermediate Similarity	NPD6037	Discontinued
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7006	Intermediate Similarity	NPD6090	Discontinued
0.7	Intermediate Similarity	NPD2653	Approved
0.7	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4663	Approved
0.6993	Remote Similarity	NPD2232	Approved
0.6993	Remote Similarity	NPD2230	Approved
0.6993	Remote Similarity	NPD2233	Approved
0.6989	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4005	Discontinued
0.6973	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3983	Phase 3
0.6971	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5160	Discontinued
0.6964	Remote Similarity	NPD1914	Approved
0.6962	Remote Similarity	NPD3145	Approved
0.6962	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3144	Approved
0.6959	Remote Similarity	NPD5720	Discontinued
0.6957	Remote Similarity	NPD7119	Phase 2
0.6948	Remote Similarity	NPD1421	Approved
0.6948	Remote Similarity	NPD1420	Approved
0.6946	Remote Similarity	NPD4123	Phase 3
0.6943	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3296	Phase 1
0.6941	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1375	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data