NPASS Compound

Structure

CID326479 OpenBabel06191716192D 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 2 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 2 0 0 0 0 0 0 0 0 0 -8.1585 4.1610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 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 4 17 1 0 0 0 0 5 18 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 3 1 6 0 0 0 16 21 1 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 6 1 6 0 0 0 19 20 1 0 0 0 0 19 32 1 0 0 0 0 20 7 1 1 0 0 0 20 27 1 0 0 0 0 21 8 1 1 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:	594.34
Volume:	618.098
LogP:	4.78
LogD:	3.229
LogS:	-3.804
# Rotatable Bonds:	12
TPSA:	164.38
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.221
Synthetic Accessibility Score:	5.293
Fsp3:	0.576
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:	-5.681
MDCK Permeability:	2.3102800241758814e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	98.19654083251953%
Volume Distribution (VD):	0.31
Pgp-substrate:	1.803685188293457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.99
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.445

ADMET: Excretion

Clearance (CL):	1.429
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.302
Drug-inuced Liver Injury (DILI):	0.341
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.122
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.031
Carcinogencity:	0.2
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.697

Download Data

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

Natural Product: NPC326479

Natural Product ID:	NPC326479
*Common Name:**	DEEUSUJLZQQESV-BQUSTMGCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DEEUSUJLZQQESV-BQUSTMGCSA-N
Standard InCHI:	InChI=1S/C33H46N4O6/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/h15-16,19-21,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-/t16-,19-,20-,21-,26+,27+/m1/s1
SMILES:	CC[C@H]1C(=N[C@H]([C@@H]1C)CC1=N/C(=Cc2[nH]c(c(c2CCC(=O)O)C)C[C@@H]2N=C([C@@H]([C@H]2CC)C)O)/C(=C1C)CCC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3121625
PubChem CID:	NA
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	=	57.0	%	PMID[515790]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	37.0	%	PMID[515790]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	43.0	%	PMID[515790]

☑ 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 NPC326479 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	227
0.1-0.2	1697
0.2-0.3	16898
0.3-0.4	16775
0.4-0.5	3500
0.5-0.6	2754
0.6-0.7	777
0.7-0.8	63
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC46359
0.9167	High Similarity	NPC26491
0.8944	High Similarity	NPC287795
0.7717	Intermediate Similarity	NPC195457
0.7514	Intermediate Similarity	NPC219336
0.7461	Intermediate Similarity	NPC187255
0.7458	Intermediate Similarity	NPC183662
0.7458	Intermediate Similarity	NPC15573
0.7458	Intermediate Similarity	NPC217372
0.7401	Intermediate Similarity	NPC267885
0.7377	Intermediate Similarity	NPC175474
0.7363	Intermediate Similarity	NPC235684
0.7345	Intermediate Similarity	NPC203468
0.7345	Intermediate Similarity	NPC110500
0.7345	Intermediate Similarity	NPC149155
0.7318	Intermediate Similarity	NPC126709
0.7318	Intermediate Similarity	NPC248041
0.7318	Intermediate Similarity	NPC283219
0.7314	Intermediate Similarity	NPC78020
0.7306	Intermediate Similarity	NPC257175
0.7283	Intermediate Similarity	NPC321708
0.7278	Intermediate Similarity	NPC469896
0.7273	Intermediate Similarity	NPC85702
0.7263	Intermediate Similarity	NPC111275
0.7231	Intermediate Similarity	NPC469743
0.7167	Intermediate Similarity	NPC14113
0.7167	Intermediate Similarity	NPC84827
0.7167	Intermediate Similarity	NPC145885
0.7159	Intermediate Similarity	NPC160105
0.7158	Intermediate Similarity	NPC52557
0.7151	Intermediate Similarity	NPC285469
0.7127	Intermediate Similarity	NPC55772
0.7127	Intermediate Similarity	NPC213468
0.7121	Intermediate Similarity	NPC473493
0.7113	Intermediate Similarity	NPC473376
0.7098	Intermediate Similarity	NPC476874
0.7097	Intermediate Similarity	NPC196251
0.7097	Intermediate Similarity	NPC63199
0.7097	Intermediate Similarity	NPC111602
0.7097	Intermediate Similarity	NPC102338
0.7095	Intermediate Similarity	NPC314603
0.7088	Intermediate Similarity	NPC91179
0.7083	Intermediate Similarity	NPC195461
0.7083	Intermediate Similarity	NPC81654
0.7083	Intermediate Similarity	NPC249150
0.7083	Intermediate Similarity	NPC49196
0.7083	Intermediate Similarity	NPC313985
0.7083	Intermediate Similarity	NPC79129
0.7081	Intermediate Similarity	NPC62749
0.7068	Intermediate Similarity	NPC50503
0.7068	Intermediate Similarity	NPC171317
0.7059	Intermediate Similarity	NPC314333
0.7059	Intermediate Similarity	NPC329858
0.7053	Intermediate Similarity	NPC11445
0.7031	Intermediate Similarity	NPC293917
0.7005	Intermediate Similarity	NPC213629
0.7	Intermediate Similarity	NPC195239
0.7	Intermediate Similarity	NPC157828
0.6994	Remote Similarity	NPC207726
0.6989	Remote Similarity	NPC16667
0.6989	Remote Similarity	NPC315555
0.6971	Remote Similarity	NPC67056
0.697	Remote Similarity	NPC478158
0.6952	Remote Similarity	NPC472323
0.6947	Remote Similarity	NPC472210
0.6947	Remote Similarity	NPC269886
0.6947	Remote Similarity	NPC472295
0.6947	Remote Similarity	NPC247735
0.6947	Remote Similarity	NPC81802
0.6923	Remote Similarity	NPC162730
0.6923	Remote Similarity	NPC137589
0.6923	Remote Similarity	NPC474116
0.6923	Remote Similarity	NPC476073
0.6911	Remote Similarity	NPC220151
0.6911	Remote Similarity	NPC19692
0.6891	Remote Similarity	NPC306376
0.6891	Remote Similarity	NPC131887
0.6889	Remote Similarity	NPC280548
0.6884	Remote Similarity	NPC271862
0.6882	Remote Similarity	NPC472119
0.6878	Remote Similarity	NPC472112
0.6872	Remote Similarity	NPC49954
0.6872	Remote Similarity	NPC474561
0.6869	Remote Similarity	NPC54420
0.6869	Remote Similarity	NPC477065
0.6865	Remote Similarity	NPC71037
0.6857	Remote Similarity	NPC268676
0.6857	Remote Similarity	NPC27324
0.6856	Remote Similarity	NPC241024
0.6854	Remote Similarity	NPC476118
0.6839	Remote Similarity	NPC262898
0.6832	Remote Similarity	NPC54744
0.6816	Remote Similarity	NPC470508
0.6811	Remote Similarity	NPC15840
0.6806	Remote Similarity	NPC472113
0.6806	Remote Similarity	NPC55493
0.6806	Remote Similarity	NPC472292
0.6804	Remote Similarity	NPC67288
0.6802	Remote Similarity	NPC476098
0.68	Remote Similarity	NPC75540
0.68	Remote Similarity	NPC212376
0.68	Remote Similarity	NPC70922
0.68	Remote Similarity	NPC80597
0.68	Remote Similarity	NPC162860
0.68	Remote Similarity	NPC211572
0.6798	Remote Similarity	NPC478157
0.6791	Remote Similarity	NPC472294
0.6788	Remote Similarity	NPC472293
0.6788	Remote Similarity	NPC179701
0.6782	Remote Similarity	NPC75634
0.678	Remote Similarity	NPC281049
0.678	Remote Similarity	NPC477714
0.6776	Remote Similarity	NPC472586
0.6769	Remote Similarity	NPC100321
0.6768	Remote Similarity	NPC475847
0.6768	Remote Similarity	NPC185742
0.6766	Remote Similarity	NPC234999
0.6765	Remote Similarity	NPC74969
0.6762	Remote Similarity	NPC469720
0.676	Remote Similarity	NPC21174
0.676	Remote Similarity	NPC271797
0.6758	Remote Similarity	NPC6982
0.6754	Remote Similarity	NPC243716
0.6753	Remote Similarity	NPC227582
0.6751	Remote Similarity	NPC193761
0.675	Remote Similarity	NPC258062
0.675	Remote Similarity	NPC127677
0.6749	Remote Similarity	NPC229348
0.6743	Remote Similarity	NPC73952
0.6743	Remote Similarity	NPC259644
0.6743	Remote Similarity	NPC469760
0.6743	Remote Similarity	NPC469786
0.6743	Remote Similarity	NPC469765
0.6743	Remote Similarity	NPC469763
0.6743	Remote Similarity	NPC25008
0.674	Remote Similarity	NPC317430
0.6736	Remote Similarity	NPC276517
0.6735	Remote Similarity	NPC128265
0.6735	Remote Similarity	NPC199851
0.6735	Remote Similarity	NPC254240
0.6735	Remote Similarity	NPC214428
0.6735	Remote Similarity	NPC294909
0.6735	Remote Similarity	NPC252338
0.6735	Remote Similarity	NPC312870
0.6729	Remote Similarity	NPC475619
0.6721	Remote Similarity	NPC472123
0.672	Remote Similarity	NPC94752
0.6718	Remote Similarity	NPC473640
0.6717	Remote Similarity	NPC98715
0.6716	Remote Similarity	NPC107077
0.6716	Remote Similarity	NPC223791
0.6706	Remote Similarity	NPC129412
0.6706	Remote Similarity	NPC114033
0.6706	Remote Similarity	NPC58268
0.6706	Remote Similarity	NPC101130
0.6704	Remote Similarity	NPC282231
0.6702	Remote Similarity	NPC228835
0.6701	Remote Similarity	NPC475506
0.6701	Remote Similarity	NPC245916
0.67	Remote Similarity	NPC225821
0.67	Remote Similarity	NPC475778
0.67	Remote Similarity	NPC87856
0.67	Remote Similarity	NPC151976
0.67	Remote Similarity	NPC46225
0.6685	Remote Similarity	NPC329688
0.6685	Remote Similarity	NPC189812
0.6684	Remote Similarity	NPC472296
0.6684	Remote Similarity	NPC113626
0.6684	Remote Similarity	NPC17059
0.6684	Remote Similarity	NPC472297
0.6683	Remote Similarity	NPC469928
0.6683	Remote Similarity	NPC132211
0.6683	Remote Similarity	NPC2395
0.6683	Remote Similarity	NPC203614
0.6683	Remote Similarity	NPC204491
0.6667	Remote Similarity	NPC280290
0.6667	Remote Similarity	NPC194640
0.6667	Remote Similarity	NPC141377
0.6667	Remote Similarity	NPC272483
0.6667	Remote Similarity	NPC155143
0.6667	Remote Similarity	NPC235885
0.6667	Remote Similarity	NPC472443
0.6667	Remote Similarity	NPC267965
0.6667	Remote Similarity	NPC141454
0.6651	Remote Similarity	NPC33949
0.665	Remote Similarity	NPC213308
0.665	Remote Similarity	NPC477715
0.665	Remote Similarity	NPC82370
0.665	Remote Similarity	NPC277350
0.665	Remote Similarity	NPC315491
0.665	Remote Similarity	NPC45459
0.6649	Remote Similarity	NPC472444
0.6649	Remote Similarity	NPC474121
0.6649	Remote Similarity	NPC143533
0.6648	Remote Similarity	NPC279918
0.6648	Remote Similarity	NPC63751
0.6634	Remote Similarity	NPC313640
0.6632	Remote Similarity	NPC478077
0.6632	Remote Similarity	NPC160381
0.6632	Remote Similarity	NPC99428

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 NPC326479 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	439
0.2-0.3	1047
0.3-0.4	2526
0.4-0.5	3265
0.5-0.6	1516
0.6-0.7	170
0.7-0.8	28
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
0.8704	High Similarity	NPD7866	Approved
0.8614	High Similarity	NPD7865	Approved
0.8528	High Similarity	NPD7864	Approved
0.8415	Intermediate Similarity	NPD7863	Approved
0.8137	Intermediate Similarity	NPD7882	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD2844	Phase 3
0.8011	Intermediate Similarity	NPD7946	Pre-registration
0.7946	Intermediate Similarity	NPD8098	Approved
0.766	Intermediate Similarity	NPD56	Approved
0.766	Intermediate Similarity	NPD8283	Approved
0.766	Intermediate Similarity	NPD8282	Approved
0.7656	Intermediate Similarity	NPD8096	Phase 3
0.7656	Intermediate Similarity	NPD8097	Phase 3
0.7632	Intermediate Similarity	NPD8399	Phase 1
0.7632	Intermediate Similarity	NPD8423	Phase 2
0.756	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2094	Phase 2
0.7486	Intermediate Similarity	NPD2095	Phase 2
0.7486	Intermediate Similarity	NPD2092	Phase 2
0.7458	Intermediate Similarity	NPD7869	Discontinued
0.7444	Intermediate Similarity	NPD2096	Phase 2
0.7444	Intermediate Similarity	NPD2091	Phase 2
0.7389	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD482	Approved
0.732	Intermediate Similarity	NPD7941	Phase 3
0.7303	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8160	Phase 2
0.7182	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD750	Phase 2
0.7093	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4600	Approved
0.7083	Intermediate Similarity	NPD4601	Approved
0.7059	Intermediate Similarity	NPD4499	Approved
0.7031	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3178	Discontinued
0.6939	Remote Similarity	NPD5426	Phase 3
0.6935	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7470	Discontinued
0.6875	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5140	Approved
0.6854	Remote Similarity	NPD5138	Approved
0.6825	Remote Similarity	NPD1534	Approved
0.6805	Remote Similarity	NPD1592	Phase 3
0.6802	Remote Similarity	NPD8072	Approved
0.6776	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8386	Phase 2
0.6754	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5003	Discontinued
0.6751	Remote Similarity	NPD8073	Approved
0.6735	Remote Similarity	NPD4500	Approved
0.6735	Remote Similarity	NPD4501	Approved
0.6734	Remote Similarity	NPD7957	Phase 1
0.6734	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.67	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5901	Discontinued
0.665	Remote Similarity	NPD484	Approved
0.6649	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4427	Phase 2
0.6632	Remote Similarity	NPD6665	Discontinued
0.6631	Remote Similarity	NPD6595	Phase 3
0.6627	Remote Similarity	NPD8062	Discontinued
0.6615	Remote Similarity	NPD2565	Phase 2
0.6615	Remote Similarity	NPD2564	Approved
0.6612	Remote Similarity	NPD1326	Approved
0.6612	Remote Similarity	NPD1575	Approved
0.6612	Remote Similarity	NPD1573	Approved
0.6612	Remote Similarity	NPD1325	Approved
0.6599	Remote Similarity	NPD6999	Discontinued
0.6599	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD8431	Approved
0.6592	Remote Similarity	NPD2214	Approved
0.6592	Remote Similarity	NPD2213	Approved
0.6567	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4602	Approved
0.6561	Remote Similarity	NPD5596	Phase 2
0.6553	Remote Similarity	NPD7970	Approved
0.6553	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7778	Approved
0.6548	Remote Similarity	NPD7777	Approved
0.6548	Remote Similarity	NPD53	Approved
0.6548	Remote Similarity	NPD4397	Phase 1
0.6537	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2144	Approved
0.652	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8272	Phase 2
0.6515	Remote Similarity	NPD8396	Approved
0.6515	Remote Similarity	NPD8395	Approved
0.6508	Remote Similarity	NPD3038	Discontinued
0.6502	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7665	Phase 2
0.6502	Remote Similarity	NPD7666	Phase 3
0.65	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1631	Approved
0.6471	Remote Similarity	NPD5471	Phase 3
0.6453	Remote Similarity	NPD8322	Phase 2
0.645	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4948	Discontinued
0.6421	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6664	Approved
0.6413	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7711	Discontinued
0.6396	Remote Similarity	NPD7619	Phase 3
0.6396	Remote Similarity	NPD7944	Discontinued
0.6396	Remote Similarity	NPD7618	Phase 3
0.6392	Remote Similarity	NPD7234	Approved
0.6392	Remote Similarity	NPD7233	Approved
0.6387	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6178	Phase 3
0.635	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4463	Approved
0.6348	Remote Similarity	NPD4462	Approved
0.6337	Remote Similarity	NPD2896	Discontinued
0.6324	Remote Similarity	NPD7001	Phase 3
0.6322	Remote Similarity	NPD5020	Approved
0.6322	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1630	Approved
0.6318	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD8641	Approved
0.631	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD2920	Discontinued
0.6303	Remote Similarity	NPD7878	Phase 2
0.6301	Remote Similarity	NPD7790	Approved
0.6301	Remote Similarity	NPD7953	Approved
0.6301	Remote Similarity	NPD7791	Approved
0.6301	Remote Similarity	NPD7789	Approved
0.6301	Remote Similarity	NPD7951	Approved
0.6301	Remote Similarity	NPD7950	Approved
0.6301	Remote Similarity	NPD7952	Approved
0.6298	Remote Similarity	NPD4852	Phase 2
0.6296	Remote Similarity	NPD6164	Phase 2
0.6296	Remote Similarity	NPD7730	Approved
0.6296	Remote Similarity	NPD7731	Approved
0.6296	Remote Similarity	NPD6165	Phase 2
0.6286	Remote Similarity	NPD3717	Discontinued
0.6283	Remote Similarity	NPD5897	Approved
0.6283	Remote Similarity	NPD5899	Approved
0.6283	Remote Similarity	NPD5898	Approved
0.6275	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD8094	Discontinued
0.6263	Remote Similarity	NPD6642	Approved
0.6263	Remote Similarity	NPD6641	Approved
0.6263	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2916	Discontinued
0.6262	Remote Similarity	NPD6376	Discontinued
0.6256	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5818	Discontinued
0.625	Remote Similarity	NPD7948	Phase 1
0.625	Remote Similarity	NPD6451	Discontinued
0.625	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4918	Discontinued
0.6244	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5065	Approved
0.6239	Remote Similarity	NPD7824	Approved
0.6238	Remote Similarity	NPD2912	Approved
0.6238	Remote Similarity	NPD2911	Approved
0.6237	Remote Similarity	NPD5611	Phase 2
0.6236	Remote Similarity	NPD4703	Approved
0.6236	Remote Similarity	NPD4702	Approved
0.6232	Remote Similarity	NPD4506	Discontinued
0.623	Remote Similarity	NPD1587	Approved
0.6222	Remote Similarity	NPD510	Phase 1
0.622	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8093	Discontinued
0.6204	Remote Similarity	NPD7271	Approved
0.6198	Remote Similarity	NPD1643	Phase 3
0.6198	Remote Similarity	NPD5473	Discontinued
0.6198	Remote Similarity	NPD6452	Discontinued
0.6197	Remote Similarity	NPD6770	Approved
0.6195	Remote Similarity	NPD8169	Discontinued
0.6195	Remote Similarity	NPD3947	Discontinued
0.6186	Remote Similarity	NPD7482	Phase 2
0.6186	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7483	Phase 2
0.6186	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD2510	Approved
0.6184	Remote Similarity	NPD2509	Approved
0.6173	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD8403	Phase 1
0.6162	Remote Similarity	NPD8026	Phase 1
0.6162	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4520	Approved
0.615	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6176	Phase 1

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