NPASS Compound

Structure

NPC469938 OpenBabel07101719152D 39 41 0 0 1 0 0 0 0 0999 V2000 2.2142 4.0121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 -1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2653 -1.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9200 1.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6328 2.5568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2361 3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5162 -0.7122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8470 -1.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2071 0.2388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8689 -1.2475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2290 0.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5817 -0.0885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 2.8532 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5599 -0.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2727 0.8626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0511 2.6453 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.2946 1.0705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7202 3.3884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 0.3273 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9418 1.6057 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 -2.9855 2.0215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4112 4.3395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6984 3.1805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 7 21 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 22 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 24 2 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 35 1 0 0 0 0 19 22 1 0 0 0 0 20 28 1 0 0 0 0 21 4 1 6 0 0 0 21 26 1 0 0 0 0 23 24 1 0 0 0 0 24 35 1 0 0 0 0 25 19 1 6 0 0 0 25 29 1 0 0 0 0 25 34 1 0 0 0 0 26 31 1 6 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 27 33 1 0 0 0 0 28 35 1 0 0 0 0 29 33 2 3 0 0 0 29 36 1 0 0 0 0 30 32 2 3 0 0 0 30 37 1 0 0 0 0 31 38 2 0 0 0 0 31 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.32
Volume:	571.846
LogP:	4.344
LogD:	3.281
LogS:	-3.74
# Rotatable Bonds:	15
TPSA:	103.67
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	3.954
Fsp3:	0.452
Lipinski Rule-of-5:	Accepted
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:	-5.93
MDCK Permeability:	1.386016720061889e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	94.54813385009766%
Volume Distribution (VD):	1.193
Pgp-substrate:	2.621680974960327%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.246
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.776
CYP2C9-substrate:	0.726
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.312
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.7

ADMET: Excretion

Clearance (CL):	3.537
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.827
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.012
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC469938

Natural Product ID:	NPC469938
*Common Name:**	Ixorapeptide Ii
IUPAC Name:	(2S,3S)-2-[[2-[[(2S)-2-(dimethylamino)-3-phenylpropanoyl]amino]-3-indol-1-yl-4-methylpentanoyl]amino]-3-methylpentanoic acid
Synonyms:	Ixorapeptide Ii
Standard InCHIKey:	DPHRDZLCFBXNED-FSSQJUNMSA-N
Standard InCHI:	InChI=1S/C31H42N4O4/c1-7-21(4)26(31(38)39)32-30(37)27(28(20(2)3)35-18-17-23-15-11-12-16-24(23)35)33-29(36)25(34(5)6)19-22-13-9-8-10-14-22/h8-18,20-21,25-28H,7,19H2,1-6H3,(H,32,37)(H,33,36)(H,38,39)/t21-,25-,26-,27?,28?/m0/s1
SMILES:	CC[C@@H]([C@@H](C(=O)O)N=C(C(C(n1ccc2c1cccc2)C(C)C)N=C([C@@H](N(C)C)Cc1ccccc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1288092
PubChem CID:	50925590
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO6876	Ixora coccinea	Species	Rubiaceae	Eukaryota	aerial parts	collected on the campus of Kaohsiung Medical University, Taiwan	2007-Oct	PMID[21106454]
NPO6876	Ixora coccinea	Species	Rubiaceae	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
IC50	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.21	ug.mL-1	PMID[473590]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.27	ug.mL-1	PMID[473590]
NPT2	Others	Unspecified		Ratio IC50	=	73.0	n.a.	PMID[473590]

☑ 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 NPC469938 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	249
0.1-0.2	1868
0.2-0.3	13860
0.3-0.4	18560
0.4-0.5	3056
0.5-0.6	2756
0.6-0.7	1762
0.7-0.8	546
0.8-0.85	35
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8772	High Similarity	NPC94752
0.8466	Intermediate Similarity	NPC117244
0.8466	Intermediate Similarity	NPC473763
0.8352	Intermediate Similarity	NPC213629
0.8343	Intermediate Similarity	NPC293917
0.8249	Intermediate Similarity	NPC321708
0.8229	Intermediate Similarity	NPC228835
0.8208	Intermediate Similarity	NPC126709
0.8208	Intermediate Similarity	NPC213468
0.8208	Intermediate Similarity	NPC248041
0.8208	Intermediate Similarity	NPC283219
0.8201	Intermediate Similarity	NPC75634
0.8198	Intermediate Similarity	NPC267885
0.8166	Intermediate Similarity	NPC160105
0.815	Intermediate Similarity	NPC14113
0.815	Intermediate Similarity	NPC84827
0.815	Intermediate Similarity	NPC145885
0.814	Intermediate Similarity	NPC149155
0.814	Intermediate Similarity	NPC110500
0.814	Intermediate Similarity	NPC203468
0.8138	Intermediate Similarity	NPC478158
0.8136	Intermediate Similarity	NPC235684
0.8118	Intermediate Similarity	NPC473376
0.8108	Intermediate Similarity	NPC476874
0.8087	Intermediate Similarity	NPC171317
0.8081	Intermediate Similarity	NPC314603
0.8032	Intermediate Similarity	NPC54420
0.8	Intermediate Similarity	NPC11126
0.7989	Intermediate Similarity	NPC472323
0.7989	Intermediate Similarity	NPC473640
0.7977	Intermediate Similarity	NPC477976
0.7966	Intermediate Similarity	NPC143533
0.7957	Intermediate Similarity	NPC475506
0.7953	Intermediate Similarity	NPC474561
0.7953	Intermediate Similarity	NPC49954
0.7952	Intermediate Similarity	NPC25008
0.7952	Intermediate Similarity	NPC469765
0.7952	Intermediate Similarity	NPC469763
0.7952	Intermediate Similarity	NPC73952
0.7952	Intermediate Similarity	NPC469786
0.7952	Intermediate Similarity	NPC469760
0.7952	Intermediate Similarity	NPC259644
0.7947	Intermediate Similarity	NPC162860
0.7927	Intermediate Similarity	NPC478157
0.7917	Intermediate Similarity	NPC129721
0.7914	Intermediate Similarity	NPC155143
0.7907	Intermediate Similarity	NPC78020
0.7907	Intermediate Similarity	NPC63751
0.7904	Intermediate Similarity	NPC80597
0.7904	Intermediate Similarity	NPC212376
0.7904	Intermediate Similarity	NPC70922
0.7904	Intermediate Similarity	NPC75540
0.7904	Intermediate Similarity	NPC211572
0.7898	Intermediate Similarity	NPC248462
0.7897	Intermediate Similarity	NPC281049
0.7892	Intermediate Similarity	NPC474916
0.7889	Intermediate Similarity	NPC17059
0.7853	Intermediate Similarity	NPC15840
0.7849	Intermediate Similarity	NPC100321
0.7841	Intermediate Similarity	NPC64436
0.7833	Intermediate Similarity	NPC62749
0.7821	Intermediate Similarity	NPC165495
0.7819	Intermediate Similarity	NPC193761
0.7819	Intermediate Similarity	NPC57398
0.7811	Intermediate Similarity	NPC469762
0.7797	Intermediate Similarity	NPC219336
0.7784	Intermediate Similarity	NPC54744
0.7778	Intermediate Similarity	NPC282231
0.7778	Intermediate Similarity	NPC280290
0.776	Intermediate Similarity	NPC107077
0.776	Intermediate Similarity	NPC223791
0.7751	Intermediate Similarity	NPC469785
0.7749	Intermediate Similarity	NPC323927
0.7742	Intermediate Similarity	NPC262898
0.774	Intermediate Similarity	NPC217372
0.774	Intermediate Similarity	NPC183662
0.774	Intermediate Similarity	NPC59269
0.774	Intermediate Similarity	NPC15573
0.7733	Intermediate Similarity	NPC194640
0.7733	Intermediate Similarity	NPC311276
0.7732	Intermediate Similarity	NPC31385
0.7732	Intermediate Similarity	NPC110602
0.7732	Intermediate Similarity	NPC75726
0.7722	Intermediate Similarity	NPC472119
0.7719	Intermediate Similarity	NPC279918
0.7711	Intermediate Similarity	NPC319232
0.7711	Intermediate Similarity	NPC24370
0.7709	Intermediate Similarity	NPC113626
0.7701	Intermediate Similarity	NPC201700
0.7688	Intermediate Similarity	NPC179701
0.768	Intermediate Similarity	NPC15102
0.764	Intermediate Similarity	NPC111275
0.7637	Intermediate Similarity	NPC478077
0.7634	Intermediate Similarity	NPC289299
0.7634	Intermediate Similarity	NPC57994
0.763	Intermediate Similarity	NPC478182
0.7626	Intermediate Similarity	NPC477714
0.7619	Intermediate Similarity	NPC40070
0.7612	Intermediate Similarity	NPC64216
0.7611	Intermediate Similarity	NPC233936
0.7611	Intermediate Similarity	NPC71037
0.7606	Intermediate Similarity	NPC149708
0.7605	Intermediate Similarity	NPC470111
0.7598	Intermediate Similarity	NPC55772
0.7593	Intermediate Similarity	NPC150259
0.759	Intermediate Similarity	NPC314372
0.759	Intermediate Similarity	NPC320968
0.7586	Intermediate Similarity	NPC477975
0.7582	Intermediate Similarity	NPC62510
0.7557	Intermediate Similarity	NPC194411
0.7556	Intermediate Similarity	NPC91179
0.7556	Intermediate Similarity	NPC469896
0.7554	Intermediate Similarity	NPC175474
0.7543	Intermediate Similarity	NPC56233
0.7543	Intermediate Similarity	NPC54988
0.7542	Intermediate Similarity	NPC68354
0.7542	Intermediate Similarity	NPC326575
0.7542	Intermediate Similarity	NPC234987
0.7541	Intermediate Similarity	NPC474707
0.754	Intermediate Similarity	NPC195239
0.754	Intermediate Similarity	NPC157828
0.7529	Intermediate Similarity	NPC40779
0.7526	Intermediate Similarity	NPC470497
0.7515	Intermediate Similarity	NPC24678
0.7515	Intermediate Similarity	NPC105818
0.7513	Intermediate Similarity	NPC238457
0.75	Intermediate Similarity	NPC11445
0.75	Intermediate Similarity	NPC133261
0.75	Intermediate Similarity	NPC472116
0.7488	Intermediate Similarity	NPC220852
0.7488	Intermediate Similarity	NPC323752
0.7487	Intermediate Similarity	NPC477715
0.7486	Intermediate Similarity	NPC472122
0.7486	Intermediate Similarity	NPC24594
0.7485	Intermediate Similarity	NPC314102
0.7485	Intermediate Similarity	NPC251722
0.7473	Intermediate Similarity	NPC472104
0.7473	Intermediate Similarity	NPC472097
0.7473	Intermediate Similarity	NPC243716
0.747	Intermediate Similarity	NPC190296
0.7462	Intermediate Similarity	NPC153980
0.7462	Intermediate Similarity	NPC6865
0.7462	Intermediate Similarity	NPC207020
0.7459	Intermediate Similarity	NPC65215
0.7459	Intermediate Similarity	NPC24864
0.7459	Intermediate Similarity	NPC173028
0.7457	Intermediate Similarity	NPC293487
0.7447	Intermediate Similarity	NPC294693
0.7444	Intermediate Similarity	NPC248454
0.7442	Intermediate Similarity	NPC51054
0.7432	Intermediate Similarity	NPC258480
0.743	Intermediate Similarity	NPC275305
0.743	Intermediate Similarity	NPC37423
0.7426	Intermediate Similarity	NPC473317
0.7421	Intermediate Similarity	NPC470499
0.7421	Intermediate Similarity	NPC265576
0.7421	Intermediate Similarity	NPC102008
0.7421	Intermediate Similarity	NPC212213
0.7416	Intermediate Similarity	NPC478028
0.7414	Intermediate Similarity	NPC131718
0.7411	Intermediate Similarity	NPC72956
0.7405	Intermediate Similarity	NPC204565
0.7396	Intermediate Similarity	NPC477974
0.7396	Intermediate Similarity	NPC300183
0.7391	Intermediate Similarity	NPC472107
0.7391	Intermediate Similarity	NPC79062
0.7389	Intermediate Similarity	NPC203754
0.7389	Intermediate Similarity	NPC150048
0.7389	Intermediate Similarity	NPC155444
0.7387	Intermediate Similarity	NPC313640
0.7381	Intermediate Similarity	NPC28945
0.7381	Intermediate Similarity	NPC285343
0.7377	Intermediate Similarity	NPC48938
0.7374	Intermediate Similarity	NPC471194
0.7374	Intermediate Similarity	NPC471193
0.7368	Intermediate Similarity	NPC227582
0.7363	Intermediate Similarity	NPC472105
0.7363	Intermediate Similarity	NPC187827
0.7363	Intermediate Similarity	NPC300688
0.7358	Intermediate Similarity	NPC471313
0.7358	Intermediate Similarity	NPC471311
0.7356	Intermediate Similarity	NPC135141
0.7356	Intermediate Similarity	NPC92796
0.7351	Intermediate Similarity	NPC315555
0.7351	Intermediate Similarity	NPC66210
0.7349	Intermediate Similarity	NPC469767
0.7349	Intermediate Similarity	NPC469761
0.7349	Intermediate Similarity	NPC469783
0.7349	Intermediate Similarity	NPC469779
0.7349	Intermediate Similarity	NPC469784
0.7349	Intermediate Similarity	NPC469780
0.7349	Intermediate Similarity	NPC469768
0.7348	Intermediate Similarity	NPC151939
0.7346	Intermediate Similarity	NPC478029
0.7345	Intermediate Similarity	NPC478183
0.7345	Intermediate Similarity	NPC41717
0.7343	Intermediate Similarity	NPC326363
0.7341	Intermediate Similarity	NPC285469
0.734	Intermediate Similarity	NPC47190
0.7337	Intermediate Similarity	NPC472294

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 NPC469938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	450
0.2-0.3	894
0.3-0.4	1499
0.4-0.5	2309
0.5-0.6	2407
0.6-0.7	1175
0.7-0.8	251
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD5728	Clinical (unspecified phase)
0.8512	High Similarity	NPD750	Phase 2
0.8483	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.8427	Intermediate Similarity	NPD7944	Discontinued
0.8343	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8251	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD2095	Phase 2
0.8171	Intermediate Similarity	NPD2092	Phase 2
0.8171	Intermediate Similarity	NPD2094	Phase 2
0.814	Intermediate Similarity	NPD482	Approved
0.8125	Intermediate Similarity	NPD2091	Phase 2
0.8125	Intermediate Similarity	NPD2096	Phase 2
0.8092	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8032	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD4326	Phase 2
0.8012	Intermediate Similarity	NPD4640	Approved
0.8012	Intermediate Similarity	NPD4639	Approved
0.8012	Intermediate Similarity	NPD4638	Approved
0.7989	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7968	Intermediate Similarity	NPD8072	Approved
0.7965	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD7470	Discontinued
0.7955	Intermediate Similarity	NPD6452	Discontinued
0.7944	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD8073	Approved
0.7914	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD7957	Phase 1
0.7875	Intermediate Similarity	NPD2896	Discontinued
0.7853	Intermediate Similarity	NPD5898	Approved
0.7853	Intermediate Similarity	NPD5897	Approved
0.7853	Intermediate Similarity	NPD5899	Approved
0.7846	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD8272	Phase 2
0.7826	Intermediate Similarity	NPD7619	Phase 3
0.7826	Intermediate Similarity	NPD7618	Phase 3
0.7821	Intermediate Similarity	NPD6178	Phase 3
0.7812	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6595	Phase 3
0.774	Intermediate Similarity	NPD8122	Approved
0.774	Intermediate Similarity	NPD8123	Approved
0.7737	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6665	Discontinued
0.7717	Intermediate Similarity	NPD5505	Discontinued
0.7713	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8431	Approved
0.7692	Intermediate Similarity	NPD3961	Discontinued
0.7667	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6999	Discontinued
0.766	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7469	Discontinued
0.765	Intermediate Similarity	NPD7233	Approved
0.765	Intermediate Similarity	NPD7234	Approved
0.7641	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4602	Approved
0.7629	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5065	Approved
0.7626	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8408	Discontinued
0.7606	Intermediate Similarity	NPD4397	Phase 1
0.7605	Intermediate Similarity	NPD1661	Suspended
0.7605	Intermediate Similarity	NPD4703	Approved
0.7605	Intermediate Similarity	NPD4702	Approved
0.7604	Intermediate Similarity	NPD7001	Phase 3
0.76	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD4076	Approved
0.7598	Intermediate Similarity	NPD4079	Approved
0.7586	Intermediate Similarity	NPD2915	Discontinued
0.7582	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2882	Phase 1
0.7563	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7970	Approved
0.756	Intermediate Similarity	NPD3576	Approved
0.756	Intermediate Similarity	NPD3575	Approved
0.7554	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD8093	Discontinued
0.7543	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3506	Approved
0.7542	Intermediate Similarity	NPD2144	Approved
0.7542	Intermediate Similarity	NPD3505	Approved
0.7542	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4427	Phase 2
0.7526	Intermediate Similarity	NPD7665	Phase 2
0.7526	Intermediate Similarity	NPD7666	Phase 3
0.7515	Intermediate Similarity	NPD4805	Approved
0.7514	Intermediate Similarity	NPD6281	Approved
0.7514	Intermediate Similarity	NPD3038	Discontinued
0.7513	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5862	Discovery
0.75	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD5017	Discontinued
0.7486	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2809	Approved
0.7473	Intermediate Similarity	NPD4949	Discontinued
0.747	Intermediate Similarity	NPD3717	Discontinued
0.7461	Intermediate Similarity	NPD6987	Phase 1
0.7451	Intermediate Similarity	NPD7711	Discontinued
0.7443	Intermediate Similarity	NPD5611	Phase 2
0.7443	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4957	Phase 2
0.743	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD53	Approved
0.7421	Intermediate Similarity	NPD7777	Approved
0.7421	Intermediate Similarity	NPD7778	Approved
0.7418	Intermediate Similarity	NPD4399	Phase 2
0.7415	Intermediate Similarity	NPD7730	Approved
0.7415	Intermediate Similarity	NPD7731	Approved
0.7414	Intermediate Similarity	NPD2511	Approved
0.7407	Intermediate Similarity	NPD3385	Approved
0.7407	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4948	Discontinued
0.7405	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD7271	Approved
0.7396	Intermediate Similarity	NPD4547	Phase 3
0.7396	Intermediate Similarity	NPD7817	Phase 1
0.7394	Intermediate Similarity	NPD4804	Approved
0.7391	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5555	Phase 1
0.738	Intermediate Similarity	NPD4918	Discontinued
0.738	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD1037	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5901	Discontinued
0.7371	Intermediate Similarity	NPD8026	Phase 1
0.7366	Intermediate Similarity	NPD4334	Discontinued
0.7366	Intermediate Similarity	NPD7603	Discontinued
0.7365	Intermediate Similarity	NPD2006	Phase 2
0.7365	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5255	Approved
0.7351	Intermediate Similarity	NPD5809	Phase 3
0.7348	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4181	Approved
0.7343	Intermediate Similarity	NPD7824	Approved
0.7337	Intermediate Similarity	NPD8094	Discontinued
0.7333	Intermediate Similarity	NPD4128	Approved
0.7333	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8129	Discovery
0.733	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1631	Approved
0.733	Intermediate Similarity	NPD6846	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3475	Approved
0.7329	Intermediate Similarity	NPD3476	Approved
0.7326	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7951	Approved
0.7321	Intermediate Similarity	NPD7950	Approved
0.7321	Intermediate Similarity	NPD7789	Approved
0.7321	Intermediate Similarity	NPD7790	Approved
0.7321	Intermediate Similarity	NPD7953	Approved
0.7321	Intermediate Similarity	NPD7791	Approved
0.7321	Intermediate Similarity	NPD7952	Approved
0.7314	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD8325	Phase 3
0.7313	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD8326	Phase 3
0.7312	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8021	Approved
0.7312	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8020	Approved
0.7306	Intermediate Similarity	NPD7727	Phase 2
0.7305	Intermediate Similarity	NPD5020	Approved
0.7302	Intermediate Similarity	NPD2717	Phase 2
0.7296	Intermediate Similarity	NPD8322	Phase 2
0.7295	Intermediate Similarity	NPD7781	Approved
0.7295	Intermediate Similarity	NPD7780	Approved
0.7293	Intermediate Similarity	NPD4075	Phase 2
0.7293	Intermediate Similarity	NPD5104	Approved
0.7293	Intermediate Similarity	NPD5471	Phase 3
0.7293	Intermediate Similarity	NPD5501	Discontinued
0.7289	Intermediate Similarity	NPD786	Approved
0.7288	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5426	Phase 3
0.7282	Intermediate Similarity	NPD8114	Approved
0.7282	Intermediate Similarity	NPD8115	Approved
0.7278	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7948	Phase 1
0.7277	Intermediate Similarity	NPD6664	Approved
0.7273	Intermediate Similarity	NPD5315	Discontinued
0.7267	Intermediate Similarity	NPD510	Phase 1
0.7267	Intermediate Similarity	NPD3654	Approved
0.7263	Intermediate Similarity	NPD1573	Approved
0.7263	Intermediate Similarity	NPD1575	Approved
0.7262	Intermediate Similarity	NPD4047	Discontinued
0.7254	Intermediate Similarity	NPD4601	Approved
0.7254	Intermediate Similarity	NPD484	Approved
0.7254	Intermediate Similarity	NPD4600	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data