NPASS Compound

Structure

CID46359 OpenBabel06191715382D 43 46 0 0 1 0 0 0 0 0999 V2000 -7.4541 5.7433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2613 -0.5402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3099 4.7400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8798 3.6997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2631 5.1555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4250 -0.7677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 2.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9250 -1.6337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5311 3.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3790 4.0677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3099 1.2198 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 -1.9305 0.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6189 3.7889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9017 3.4918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1585 4.1610 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 -2.9250 0.0984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0311 2.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7226 1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5700 3.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2925 3.6610 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3317 1.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6189 2.1709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4250 -2.4997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5311 3.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4949 2.5783 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 -2.5886 1.6810 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5700 2.4799 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.5004 2.6828 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9250 -3.3657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4250 -2.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0311 4.7120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0311 2.9799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9949 1.7123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 30 1 0 0 0 0 12 31 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 28 2 0 0 0 0 15 29 1 0 0 0 0 16 21 2 0 0 0 0 16 26 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 18 25 2 0 0 0 0 19 20 2 0 0 0 0 19 32 1 0 0 0 0 20 27 1 0 0 0 0 21 33 1 0 0 0 0 22 28 1 0 0 0 0 23 29 2 0 0 0 0 24 34 2 0 0 0 0 25 35 1 0 0 0 0 26 13 1 1 0 0 0 26 36 1 0 0 0 0 27 14 1 6 0 0 0 27 37 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 30 38 2 0 0 0 0 30 39 1 0 0 0 0 31 40 2 0 0 0 0 31 41 1 0 0 0 0 32 37 2 0 0 0 0 32 42 1 0 0 0 0 33 36 2 0 0 0 0 33 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.31
Volume:	612.825
LogP:	5.841
LogD:	2.533
LogS:	-3.394
# Rotatable Bonds:	12
TPSA:	178.22
# H-Bond Aceptor:	10
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.123
Synthetic Accessibility Score:	3.912
Fsp3:	0.394
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.916
MDCK Permeability:	2.881812861232902e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	99.38778686523438%
Volume Distribution (VD):	0.17
Pgp-substrate:	1.8779356479644775%

ADMET: Metabolism

CYP1A2-inhibitor:	0.377
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.54
CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	2.206
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.513
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.041
Carcinogencity:	0.261
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC46359

Natural Product ID:	NPC46359
*Common Name:**	Urobilin
IUPAC Name:	3-[(2Z)-2-[[3-(2-carboxyethyl)-5-[[(2S)-3-ethyl-4-methyl-5-oxo-1,2-dihydropyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-2-yl]methylidene]-5-[[(2S)-4-ethyl-3-methyl-5-oxo-1,2-dihydropyrrol-2-yl]methyl]-4-methylpyrrol-3-yl]propanoic acid
Synonyms:
Standard InCHIKey:	KDCCOOGTVSRCHX-UYMYUHGCSA-N
Standard InCHI:	InChI=1S/C33H42N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h15,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-/t26-,27-/m0/s1
SMILES:	CCC1=C(C)C(=N[C@H]1Cc1c(C)c(CCC(=O)O)c(/C=C2/C(=C(C)C(=N2)C[C@H]2C(=C(CC)C(=N2)O)C)CCC(=O)O)[nH]1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3121626
PubChem CID:	6433298
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001455] Tetrapyrroles and derivatives [CHEMONTID:0001593] Bilirubins

*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

☑ 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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	48.0	%	PMID[531696]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	79.0	%	PMID[531696]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	42.0	%	PMID[531696]

☑ 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 NPC46359 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	235
0.1-0.2	1824
0.2-0.3	13391
0.3-0.4	19790
0.4-0.5	3784
0.5-0.6	2787
0.6-0.7	824
0.7-0.8	56
0.8-0.85	1
0.85-0.9	0
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC326479
0.9481	High Similarity	NPC26491
0.9245	High Similarity	NPC287795
0.7581	Intermediate Similarity	NPC195457
0.7472	Intermediate Similarity	NPC219336
0.7416	Intermediate Similarity	NPC183662
0.7416	Intermediate Similarity	NPC217372
0.7416	Intermediate Similarity	NPC15573
0.736	Intermediate Similarity	NPC267885
0.7322	Intermediate Similarity	NPC235684
0.7303	Intermediate Similarity	NPC203468
0.7303	Intermediate Similarity	NPC110500
0.7303	Intermediate Similarity	NPC149155
0.7278	Intermediate Similarity	NPC126709
0.7278	Intermediate Similarity	NPC248041
0.7278	Intermediate Similarity	NPC283219
0.7273	Intermediate Similarity	NPC78020
0.7245	Intermediate Similarity	NPC187255
0.7243	Intermediate Similarity	NPC321708
0.7243	Intermediate Similarity	NPC175474
0.7238	Intermediate Similarity	NPC469896
0.7236	Intermediate Similarity	NPC85702
0.7127	Intermediate Similarity	NPC14113
0.7127	Intermediate Similarity	NPC111275
0.7127	Intermediate Similarity	NPC145885
0.7127	Intermediate Similarity	NPC84827
0.712	Intermediate Similarity	NPC306376
0.711	Intermediate Similarity	NPC285469
0.7092	Intermediate Similarity	NPC257175
0.7088	Intermediate Similarity	NPC55772
0.7085	Intermediate Similarity	NPC473493
0.7059	Intermediate Similarity	NPC196251
0.7059	Intermediate Similarity	NPC63199
0.7059	Intermediate Similarity	NPC111602
0.7059	Intermediate Similarity	NPC102338
0.7049	Intermediate Similarity	NPC91179
0.7031	Intermediate Similarity	NPC131887
0.7031	Intermediate Similarity	NPC52557
0.7022	Intermediate Similarity	NPC160105
0.702	Intermediate Similarity	NPC469743
0.7006	Intermediate Similarity	NPC476118
0.6995	Remote Similarity	NPC213468
0.699	Remote Similarity	NPC473376
0.6974	Remote Similarity	NPC476874
0.6961	Remote Similarity	NPC314603
0.6959	Remote Similarity	NPC49196
0.6959	Remote Similarity	NPC313985
0.6959	Remote Similarity	NPC195461
0.6959	Remote Similarity	NPC79129
0.6959	Remote Similarity	NPC81654
0.6959	Remote Similarity	NPC249150
0.6954	Remote Similarity	NPC207726
0.6952	Remote Similarity	NPC62749
0.6949	Remote Similarity	NPC16667
0.6943	Remote Similarity	NPC50503
0.6943	Remote Similarity	NPC171317
0.6939	Remote Similarity	NPC476098
0.6935	Remote Similarity	NPC478158
0.6935	Remote Similarity	NPC271862
0.6932	Remote Similarity	NPC67056
0.6931	Remote Similarity	NPC329858
0.6931	Remote Similarity	NPC314333
0.6907	Remote Similarity	NPC241024
0.6906	Remote Similarity	NPC6982
0.6905	Remote Similarity	NPC268676
0.6905	Remote Similarity	NPC27324
0.6897	Remote Similarity	NPC74969
0.6891	Remote Similarity	NPC141454
0.6878	Remote Similarity	NPC213629
0.6875	Remote Similarity	NPC276517
0.6875	Remote Similarity	NPC19692
0.6875	Remote Similarity	NPC220151
0.6866	Remote Similarity	NPC82370
0.6862	Remote Similarity	NPC315555
0.6859	Remote Similarity	NPC55493
0.6856	Remote Similarity	NPC67288
0.6851	Remote Similarity	NPC280548
0.6842	Remote Similarity	NPC83111
0.6839	Remote Similarity	NPC11445
0.6825	Remote Similarity	NPC472323
0.6823	Remote Similarity	NPC247735
0.6823	Remote Similarity	NPC269886
0.6823	Remote Similarity	NPC472210
0.6823	Remote Similarity	NPC472295
0.6823	Remote Similarity	NPC81802
0.6821	Remote Similarity	NPC293917
0.6821	Remote Similarity	NPC37548
0.6811	Remote Similarity	NPC472443
0.6804	Remote Similarity	NPC262898
0.6802	Remote Similarity	NPC137589
0.68	Remote Similarity	NPC127677
0.68	Remote Similarity	NPC258062
0.6791	Remote Similarity	NPC472444
0.6788	Remote Similarity	NPC202812
0.6788	Remote Similarity	NPC195239
0.6788	Remote Similarity	NPC157828
0.6786	Remote Similarity	NPC45459
0.6786	Remote Similarity	NPC213308
0.6786	Remote Similarity	NPC315491
0.6778	Remote Similarity	NPC470508
0.6777	Remote Similarity	NPC33949
0.6776	Remote Similarity	NPC475619
0.6772	Remote Similarity	NPC160381
0.6768	Remote Similarity	NPC98715
0.6765	Remote Similarity	NPC478157
0.6761	Remote Similarity	NPC212376
0.6761	Remote Similarity	NPC211572
0.6761	Remote Similarity	NPC80597
0.6761	Remote Similarity	NPC70922
0.6761	Remote Similarity	NPC75540
0.6754	Remote Similarity	NPC472112
0.6753	Remote Similarity	NPC179701
0.6753	Remote Similarity	NPC245916
0.6751	Remote Similarity	NPC300183
0.675	Remote Similarity	NPC477065
0.675	Remote Similarity	NPC225821
0.675	Remote Similarity	NPC54420
0.675	Remote Similarity	NPC46225
0.6749	Remote Similarity	NPC207020
0.6749	Remote Similarity	NPC151976
0.6749	Remote Similarity	NPC87856
0.674	Remote Similarity	NPC474561
0.674	Remote Similarity	NPC49954
0.6738	Remote Similarity	NPC71037
0.6732	Remote Similarity	NPC330009
0.6732	Remote Similarity	NPC132211
0.6732	Remote Similarity	NPC203614
0.6732	Remote Similarity	NPC204491
0.6732	Remote Similarity	NPC469928
0.6731	Remote Similarity	NPC2395
0.6724	Remote Similarity	NPC187951
0.6723	Remote Similarity	NPC141353
0.672	Remote Similarity	NPC280290
0.6718	Remote Similarity	NPC227582
0.6717	Remote Similarity	NPC193761
0.6717	Remote Similarity	NPC476073
0.6717	Remote Similarity	NPC162730
0.6717	Remote Similarity	NPC474116
0.6716	Remote Similarity	NPC229348
0.6716	Remote Similarity	NPC267965
0.6716	Remote Similarity	NPC54744
0.6714	Remote Similarity	NPC235885
0.6705	Remote Similarity	NPC73952
0.6705	Remote Similarity	NPC469760
0.6705	Remote Similarity	NPC259644
0.6705	Remote Similarity	NPC469765
0.6705	Remote Similarity	NPC469763
0.6705	Remote Similarity	NPC25008
0.6705	Remote Similarity	NPC469786
0.6701	Remote Similarity	NPC474121
0.6701	Remote Similarity	NPC252338
0.6701	Remote Similarity	NPC294909
0.6701	Remote Similarity	NPC199851
0.6701	Remote Similarity	NPC128265
0.6701	Remote Similarity	NPC254240
0.6701	Remote Similarity	NPC312870
0.6685	Remote Similarity	NPC34508
0.6684	Remote Similarity	NPC15840
0.6684	Remote Similarity	NPC472113
0.6684	Remote Similarity	NPC472292
0.6683	Remote Similarity	NPC162860
0.6683	Remote Similarity	NPC165599
0.6667	Remote Similarity	NPC75634
0.6667	Remote Similarity	NPC38736
0.6667	Remote Similarity	NPC470507
0.6667	Remote Similarity	NPC472119
0.6667	Remote Similarity	NPC282231
0.6667	Remote Similarity	NPC472293
0.6651	Remote Similarity	NPC469720
0.665	Remote Similarity	NPC476114
0.6649	Remote Similarity	NPC472586
0.6649	Remote Similarity	NPC17059
0.6649	Remote Similarity	NPC45850
0.6633	Remote Similarity	NPC156704
0.6632	Remote Similarity	NPC243716
0.6631	Remote Similarity	NPC270009
0.663	Remote Similarity	NPC271797
0.663	Remote Similarity	NPC21174
0.663	Remote Similarity	NPC194640
0.6616	Remote Similarity	NPC214428
0.6615	Remote Similarity	NPC46413
0.6615	Remote Similarity	NPC209917
0.6612	Remote Similarity	NPC63751
0.6611	Remote Similarity	NPC279918
0.6604	Remote Similarity	NPC319232
0.6604	Remote Similarity	NPC24370
0.6604	Remote Similarity	NPC214142
0.6601	Remote Similarity	NPC107077
0.6601	Remote Similarity	NPC284102
0.6601	Remote Similarity	NPC223791
0.6599	Remote Similarity	NPC102008
0.6599	Remote Similarity	NPC473640
0.6597	Remote Similarity	NPC94752
0.6595	Remote Similarity	NPC161861
0.6595	Remote Similarity	NPC472123
0.6592	Remote Similarity	NPC212742
0.6592	Remote Similarity	NPC469762
0.6591	Remote Similarity	NPC24678
0.6591	Remote Similarity	NPC105818
0.659	Remote Similarity	NPC242556

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 NPC46359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	463
0.2-0.3	1027
0.3-0.4	2312
0.4-0.5	3407
0.5-0.6	1578
0.6-0.7	178
0.7-0.8	26
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.865	High Similarity	NPD7866	Approved
0.8563	High Similarity	NPD7865	Approved
0.8476	Intermediate Similarity	NPD7864	Approved
0.8364	Intermediate Similarity	NPD7863	Approved
0.8204	Intermediate Similarity	NPD2844	Phase 3
0.8167	Intermediate Similarity	NPD7946	Pre-registration
0.8086	Intermediate Similarity	NPD7882	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8098	Approved
0.7708	Intermediate Similarity	NPD8097	Phase 3
0.7708	Intermediate Similarity	NPD8096	Phase 3
0.7619	Intermediate Similarity	NPD8282	Approved
0.7619	Intermediate Similarity	NPD8283	Approved
0.7619	Intermediate Similarity	NPD56	Approved
0.7592	Intermediate Similarity	NPD8399	Phase 1
0.7592	Intermediate Similarity	NPD8423	Phase 2
0.7412	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD2092	Phase 2
0.7348	Intermediate Similarity	NPD2095	Phase 2
0.7348	Intermediate Similarity	NPD2094	Phase 2
0.7318	Intermediate Similarity	NPD7869	Discontinued
0.7308	Intermediate Similarity	NPD2091	Phase 2
0.7308	Intermediate Similarity	NPD2096	Phase 2
0.7303	Intermediate Similarity	NPD482	Approved
0.7263	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD8160	Phase 2
0.7198	Intermediate Similarity	NPD3178	Discontinued
0.7107	Intermediate Similarity	NPD7941	Phase 3
0.7056	Intermediate Similarity	NPD750	Phase 2
0.7049	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5140	Approved
0.7006	Intermediate Similarity	NPD5138	Approved
0.6964	Remote Similarity	NPD1592	Phase 3
0.6959	Remote Similarity	NPD4600	Approved
0.6959	Remote Similarity	NPD4601	Approved
0.6954	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7470	Discontinued
0.6931	Remote Similarity	NPD4499	Approved
0.6904	Remote Similarity	NPD5901	Discontinued
0.69	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD1326	Approved
0.6851	Remote Similarity	NPD1325	Approved
0.6821	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD484	Approved
0.6771	Remote Similarity	NPD6665	Discontinued
0.6739	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8396	Approved
0.6735	Remote Similarity	NPD8395	Approved
0.6734	Remote Similarity	NPD5426	Phase 3
0.6733	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8386	Phase 2
0.6719	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5003	Discontinued
0.6717	Remote Similarity	NPD8073	Approved
0.6702	Remote Similarity	NPD1534	Approved
0.6702	Remote Similarity	NPD5596	Phase 2
0.6701	Remote Similarity	NPD4501	Approved
0.6701	Remote Similarity	NPD4500	Approved
0.67	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8072	Approved
0.6667	Remote Similarity	NPD2564	Approved
0.6667	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2565	Phase 2
0.665	Remote Similarity	NPD6999	Discontinued
0.665	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4948	Discontinued
0.6634	Remote Similarity	NPD7665	Phase 2
0.6634	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7666	Phase 3
0.6617	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7957	Phase 1
0.6602	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7778	Approved
0.6599	Remote Similarity	NPD7777	Approved
0.6599	Remote Similarity	NPD53	Approved
0.6596	Remote Similarity	NPD6595	Phase 3
0.6591	Remote Similarity	NPD4463	Approved
0.6591	Remote Similarity	NPD4462	Approved
0.6584	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5020	Approved
0.6562	Remote Similarity	NPD8431	Approved
0.6557	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7970	Approved
0.6508	Remote Similarity	NPD5897	Approved
0.6508	Remote Similarity	NPD5898	Approved
0.6508	Remote Similarity	NPD5899	Approved
0.6507	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8062	Discontinued
0.6489	Remote Similarity	NPD2144	Approved
0.6488	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5065	Approved
0.6465	Remote Similarity	NPD7948	Phase 1
0.6464	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD2214	Approved
0.6464	Remote Similarity	NPD2213	Approved
0.6458	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7001	Phase 3
0.6453	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD1631	Approved
0.6447	Remote Similarity	NPD4602	Approved
0.6447	Remote Similarity	NPD4427	Phase 2
0.6436	Remote Similarity	NPD5471	Phase 3
0.6432	Remote Similarity	NPD4397	Phase 1
0.6429	Remote Similarity	NPD7878	Phase 2
0.6425	Remote Similarity	NPD4852	Phase 2
0.6422	Remote Similarity	NPD8322	Phase 2
0.6421	Remote Similarity	NPD6452	Discontinued
0.6419	Remote Similarity	NPD6164	Phase 2
0.6419	Remote Similarity	NPD6165	Phase 2
0.6418	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8272	Phase 2
0.6404	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6642	Approved
0.6402	Remote Similarity	NPD6641	Approved
0.6398	Remote Similarity	NPD1573	Approved
0.6398	Remote Similarity	NPD1575	Approved
0.639	Remote Similarity	NPD6376	Discontinued
0.6387	Remote Similarity	NPD3038	Discontinued
0.6386	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7618	Phase 3
0.6364	Remote Similarity	NPD7944	Discontinued
0.6364	Remote Similarity	NPD7619	Phase 3
0.6355	Remote Similarity	NPD2920	Discontinued
0.6346	Remote Similarity	NPD8093	Discontinued
0.6335	Remote Similarity	NPD1643	Phase 3
0.6324	Remote Similarity	NPD3947	Discontinued
0.6316	Remote Similarity	NPD8094	Discontinued
0.6311	Remote Similarity	NPD2916	Discontinued
0.6308	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD2896	Discontinued
0.63	Remote Similarity	NPD6664	Approved
0.6293	Remote Similarity	NPD8403	Phase 1
0.6287	Remote Similarity	NPD2911	Approved
0.6287	Remote Similarity	NPD2912	Approved
0.6284	Remote Similarity	NPD1630	Approved
0.6281	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.628	Remote Similarity	NPD4506	Discontinued
0.6277	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7233	Approved
0.6276	Remote Similarity	NPD7234	Approved
0.627	Remote Similarity	NPD5088	Discontinued
0.6269	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6770	Approved
0.6244	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6178	Phase 3
0.6237	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7232	Discontinued
0.6232	Remote Similarity	NPD2509	Approved
0.6232	Remote Similarity	NPD2510	Approved
0.623	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5818	Discontinued
0.6222	Remote Similarity	NPD3835	Phase 3
0.6222	Remote Similarity	NPD3833	Phase 3
0.6221	Remote Similarity	NPD7711	Discontinued
0.6203	Remote Similarity	NPD5611	Phase 2
0.62	Remote Similarity	NPD8641	Approved
0.6199	Remote Similarity	NPD7791	Approved
0.6199	Remote Similarity	NPD7952	Approved
0.6199	Remote Similarity	NPD7951	Approved
0.6199	Remote Similarity	NPD7789	Approved
0.6199	Remote Similarity	NPD7790	Approved
0.6199	Remote Similarity	NPD7950	Approved
0.6199	Remote Similarity	NPD7953	Approved
0.6198	Remote Similarity	NPD1587	Approved
0.6195	Remote Similarity	NPD6176	Phase 1
0.6193	Remote Similarity	NPD7730	Approved
0.6193	Remote Similarity	NPD7731	Approved
0.6188	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6158	Phase 2
0.6186	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD3379	Phase 2
0.6165	Remote Similarity	NPD3380	Phase 3
0.6161	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD6249	Phase 2
0.6158	Remote Similarity	NPD3814	Phase 1
0.6158	Remote Similarity	NPD6248	Phase 2
0.6158	Remote Similarity	NPD3425	Discontinued
0.6154	Remote Similarity	NPD6487	Approved
0.6154	Remote Similarity	NPD721	Approved
0.6154	Remote Similarity	NPD6486	Approved
0.6154	Remote Similarity	NPD3607	Clinical (unspecified phase)

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