NPASS Compound

Structure

NPC59269 OpenBabel07101718192D 28 32 0 0 1 0 0 0 0 0999 V2000 -4.2793 2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6176 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6176 -1.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 1.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7515 -0.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7515 -2.4328 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 2.6254 0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 2.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 -1.4328 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 2.9344 -0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8855 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8855 -1.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6473 0.5352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 -2.2418 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 1.3383 1.4863 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 2.6453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 17 2 0 0 0 0 8 18 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 9 1 1 0 0 0 19 21 1 0 0 0 0 19 25 1 0 0 0 0 20 10 1 1 0 0 0 20 22 1 0 0 0 0 20 26 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 25 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	381.489
LogP:	2.932
LogD:	3.177
LogS:	-4.396
# Rotatable Bonds:	4
TPSA:	89.78
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	3.094
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.947
MDCK Permeability:	5.941044946666807e-06
Pgp-inhibitor:	0.034
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.858
20% Bioavailability (F20%):	0.488
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	93.36234283447266%
Volume Distribution (VD):	0.705
Pgp-substrate:	7.848701477050781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.464
CYP1A2-substrate:	0.301
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.698
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.673
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	3.932
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.392
Human Hepatotoxicity (H-HT):	0.393
Drug-inuced Liver Injury (DILI):	0.474
AMES Toxicity:	0.629
Rat Oral Acute Toxicity:	0.867
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.373
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.605

Download Data

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

Natural Product: NPC59269

Natural Product ID:	NPC59269
*Common Name:**	Fellutanine A
IUPAC Name:	(3S,6S)-3,6-bis(1H-indol-3-ylmethyl)piperazine-2,5-dione
Synonyms:	Cyclo(-Trp-Trp)
Standard InCHIKey:	DNHODRZUCGXYKU-PMACEKPBSA-N
Standard InCHI:	InChI=1S/C22H20N4O2/c27-21-19(9-13-11-23-17-7-3-1-5-15(13)17)25-22(28)20(26-21)10-14-12-24-18-8-4-2-6-16(14)18/h1-8,11-12,19-20,23-24H,9-10H2,(H,25,28)(H,26,27)/t19-,20-/m0/s1
SMILES:	c1ccc2c(c1)c(C[C@H]1C(=N[C@@H](Cc3c[nH]c4ccccc34)C(=N1)O)O)c[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL191011
PubChem CID:	7091706
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids 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
NPO19211	Penicillium fellutanum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843594]
NPO19211	Penicillium fellutanum	Species	Aspergillaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3579	Individual Protein	Calpain 1	Homo sapiens	Inhibition	=	0.0	%	PMID[470853]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[470856]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	100000.0	nM	PMID[470856]
NPT27	Others	Unspecified		LogP app	=	-5.04	n.a.	PMID[470854]
NPT35	Others	n.a.		LogP	=	2.04	n.a.	PMID[470854]

☑ 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 NPC59269 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	465
0.1-0.2	4500
0.2-0.3	19185
0.3-0.4	11496
0.4-0.5	2892
0.5-0.6	2034
0.6-0.7	1301
0.7-0.8	655
0.8-0.85	113
0.85-0.9	47
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC63751
0.9398	High Similarity	NPC15102
0.9313	High Similarity	NPC49954
0.9313	High Similarity	NPC474561
0.9304	High Similarity	NPC279918
0.9245	High Similarity	NPC282231
0.9118	High Similarity	NPC321708
0.9074	High Similarity	NPC160105
0.9074	High Similarity	NPC54988
0.9068	High Similarity	NPC194640
0.8882	High Similarity	NPC135141
0.8882	High Similarity	NPC92796
0.8855	High Similarity	NPC314603
0.881	High Similarity	NPC248454
0.875	High Similarity	NPC73952
0.875	High Similarity	NPC25008
0.875	High Similarity	NPC469786
0.875	High Similarity	NPC259644
0.875	High Similarity	NPC469763
0.875	High Similarity	NPC469765
0.875	High Similarity	NPC469760
0.8715	High Similarity	NPC23420
0.8715	High Similarity	NPC205254
0.8715	High Similarity	NPC303820
0.8715	High Similarity	NPC106771
0.8704	High Similarity	NPC469762
0.8696	High Similarity	NPC70922
0.8696	High Similarity	NPC80597
0.8696	High Similarity	NPC212376
0.8696	High Similarity	NPC75540
0.8696	High Similarity	NPC211572
0.8671	High Similarity	NPC288838
0.8667	High Similarity	NPC52909
0.8667	High Similarity	NPC475935
0.8667	High Similarity	NPC94211
0.8642	High Similarity	NPC469785
0.8642	High Similarity	NPC285469
0.8625	High Similarity	NPC53947
0.8619	High Similarity	NPC193761
0.8605	High Similarity	NPC163055
0.8571	High Similarity	NPC213629
0.8547	High Similarity	NPC227582
0.8514	High Similarity	NPC17059
0.8494	Intermediate Similarity	NPC311276
0.8491	Intermediate Similarity	NPC314372
0.8476	Intermediate Similarity	NPC216643
0.8471	Intermediate Similarity	NPC203468
0.8471	Intermediate Similarity	NPC149155
0.8471	Intermediate Similarity	NPC110500
0.8452	Intermediate Similarity	NPC201700
0.8439	Intermediate Similarity	NPC233936
0.8434	Intermediate Similarity	NPC16667
0.8427	Intermediate Similarity	NPC477167
0.8427	Intermediate Similarity	NPC473342
0.8424	Intermediate Similarity	NPC230869
0.8421	Intermediate Similarity	NPC267885
0.8407	Intermediate Similarity	NPC252338
0.8402	Intermediate Similarity	NPC194411
0.8372	Intermediate Similarity	NPC68354
0.8365	Intermediate Similarity	NPC190296
0.8354	Intermediate Similarity	NPC207726
0.8352	Intermediate Similarity	NPC94752
0.8343	Intermediate Similarity	NPC78020
0.8343	Intermediate Similarity	NPC165495
0.8324	Intermediate Similarity	NPC248041
0.8324	Intermediate Similarity	NPC126709
0.8324	Intermediate Similarity	NPC283219
0.8295	Intermediate Similarity	NPC99939
0.8295	Intermediate Similarity	NPC308931
0.8289	Intermediate Similarity	NPC314957
0.8282	Intermediate Similarity	NPC105818
0.8282	Intermediate Similarity	NPC24678
0.8274	Intermediate Similarity	NPC40779
0.8266	Intermediate Similarity	NPC151939
0.8263	Intermediate Similarity	NPC131718
0.8261	Intermediate Similarity	NPC159856
0.8256	Intermediate Similarity	NPC275305
0.8256	Intermediate Similarity	NPC37423
0.8249	Intermediate Similarity	NPC235684
0.8218	Intermediate Similarity	NPC213468
0.8212	Intermediate Similarity	NPC95783
0.8204	Intermediate Similarity	NPC67056
0.8202	Intermediate Similarity	NPC317030
0.8197	Intermediate Similarity	NPC171317
0.8197	Intermediate Similarity	NPC473640
0.8197	Intermediate Similarity	NPC131887
0.8187	Intermediate Similarity	NPC280548
0.8182	Intermediate Similarity	NPC325903
0.8171	Intermediate Similarity	NPC300688
0.8166	Intermediate Similarity	NPC317105
0.8161	Intermediate Similarity	NPC14113
0.8161	Intermediate Similarity	NPC145885
0.8161	Intermediate Similarity	NPC84827
0.8152	Intermediate Similarity	NPC74413
0.8152	Intermediate Similarity	NPC293917
0.8152	Intermediate Similarity	NPC100321
0.8146	Intermediate Similarity	NPC474707
0.8136	Intermediate Similarity	NPC228835
0.8135	Intermediate Similarity	NPC477715
0.8125	Intermediate Similarity	NPC469783
0.8125	Intermediate Similarity	NPC469779
0.8125	Intermediate Similarity	NPC469768
0.8125	Intermediate Similarity	NPC469780
0.8125	Intermediate Similarity	NPC469767
0.8125	Intermediate Similarity	NPC469784
0.8125	Intermediate Similarity	NPC469761
0.8122	Intermediate Similarity	NPC304187
0.8122	Intermediate Similarity	NPC477166
0.8122	Intermediate Similarity	NPC99666
0.8118	Intermediate Similarity	NPC476073
0.8115	Intermediate Similarity	NPC75726
0.8115	Intermediate Similarity	NPC31385
0.8115	Intermediate Similarity	NPC75634
0.8115	Intermediate Similarity	NPC110602
0.8114	Intermediate Similarity	NPC215795
0.8114	Intermediate Similarity	NPC176199
0.811	Intermediate Similarity	NPC37548
0.8101	Intermediate Similarity	NPC96102
0.8101	Intermediate Similarity	NPC204565
0.8098	Intermediate Similarity	NPC143872
0.8095	Intermediate Similarity	NPC318065
0.8095	Intermediate Similarity	NPC206819
0.8093	Intermediate Similarity	NPC477714
0.8075	Intermediate Similarity	NPC469766
0.8065	Intermediate Similarity	NPC475506
0.8063	Intermediate Similarity	NPC73767
0.8059	Intermediate Similarity	NPC102423
0.8056	Intermediate Similarity	NPC173028
0.8056	Intermediate Similarity	NPC65215
0.8053	Intermediate Similarity	NPC478158
0.805	Intermediate Similarity	NPC84911
0.805	Intermediate Similarity	NPC105127
0.8049	Intermediate Similarity	NPC471957
0.8042	Intermediate Similarity	NPC54420
0.8042	Intermediate Similarity	NPC323927
0.8035	Intermediate Similarity	NPC470498
0.8034	Intermediate Similarity	NPC472294
0.8031	Intermediate Similarity	NPC478157
0.8021	Intermediate Similarity	NPC155143
0.8021	Intermediate Similarity	NPC476874
0.8021	Intermediate Similarity	NPC260900
0.8012	Intermediate Similarity	NPC470508
0.8011	Intermediate Similarity	NPC55772
0.8011	Intermediate Similarity	NPC11126
0.8	Intermediate Similarity	NPC280852
0.8	Intermediate Similarity	NPC470499
0.7989	Intermediate Similarity	NPC477611
0.7989	Intermediate Similarity	NPC163421
0.7989	Intermediate Similarity	NPC188387
0.7987	Intermediate Similarity	NPC261195
0.7987	Intermediate Similarity	NPC29886
0.7978	Intermediate Similarity	NPC48938
0.7976	Intermediate Similarity	NPC141353
0.7969	Intermediate Similarity	NPC72956
0.7966	Intermediate Similarity	NPC91179
0.7958	Intermediate Similarity	NPC162860
0.7955	Intermediate Similarity	NPC111275
0.795	Intermediate Similarity	NPC110126
0.7947	Intermediate Similarity	NPC166492
0.7947	Intermediate Similarity	NPC473362
0.7946	Intermediate Similarity	NPC77555
0.7944	Intermediate Similarity	NPC62749
0.7941	Intermediate Similarity	NPC122141
0.7939	Intermediate Similarity	NPC469811
0.7937	Intermediate Similarity	NPC473376
0.7929	Intermediate Similarity	NPC129721
0.7927	Intermediate Similarity	NPC6865
0.7927	Intermediate Similarity	NPC153980
0.7923	Intermediate Similarity	NPC324149
0.7921	Intermediate Similarity	NPC71037
0.7919	Intermediate Similarity	NPC317430
0.7917	Intermediate Similarity	NPC38736
0.7917	Intermediate Similarity	NPC470507
0.7914	Intermediate Similarity	NPC470497
0.7904	Intermediate Similarity	NPC216713
0.7903	Intermediate Similarity	NPC67288
0.7903	Intermediate Similarity	NPC265576
0.7901	Intermediate Similarity	NPC279081
0.7892	Intermediate Similarity	NPC321911
0.7892	Intermediate Similarity	NPC187951
0.7889	Intermediate Similarity	NPC314002
0.7886	Intermediate Similarity	NPC313791
0.7886	Intermediate Similarity	NPC34508
0.7886	Intermediate Similarity	NPC472123
0.7882	Intermediate Similarity	NPC41257
0.7882	Intermediate Similarity	NPC475990
0.7882	Intermediate Similarity	NPC56765
0.788	Intermediate Similarity	NPC474177
0.7879	Intermediate Similarity	NPC63545
0.7877	Intermediate Similarity	NPC220765
0.7876	Intermediate Similarity	NPC82370
0.7866	Intermediate Similarity	NPC242556
0.7861	Intermediate Similarity	NPC49217
0.7849	Intermediate Similarity	NPC229332
0.7848	Intermediate Similarity	NPC82295
0.7845	Intermediate Similarity	NPC171171
0.7842	Intermediate Similarity	NPC475070
0.7841	Intermediate Similarity	NPC329688
0.7841	Intermediate Similarity	NPC189812
0.7838	Intermediate Similarity	NPC133366

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 NPC59269 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	603
0.2-0.3	1029
0.3-0.4	1558
0.4-0.5	2587
0.5-0.6	1983
0.6-0.7	938
0.7-0.8	194
0.8-0.85	23
0.85-0.9	5
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9509	High Similarity	NPD6595	Phase 3
0.9281	High Similarity	NPD6610	Clinical (unspecified phase)
0.9036	High Similarity	NPD6203	Clinical (unspecified phase)
0.8963	High Similarity	NPD4184	Clinical (unspecified phase)
0.8837	High Similarity	NPD8431	Approved
0.8706	High Similarity	NPD8464	Clinical (unspecified phase)
0.858	High Similarity	NPD5065	Approved
0.8571	High Similarity	NPD8110	Clinical (unspecified phase)
0.8562	High Similarity	NPD4374	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD482	Approved
0.8444	Intermediate Similarity	NPD7948	Phase 1
0.843	Intermediate Similarity	NPD4079	Approved
0.843	Intermediate Similarity	NPD4076	Approved
0.8391	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD2092	Phase 2
0.8391	Intermediate Similarity	NPD2094	Phase 2
0.8391	Intermediate Similarity	NPD2095	Phase 2
0.8372	Intermediate Similarity	NPD3505	Approved
0.8372	Intermediate Similarity	NPD3506	Approved
0.8343	Intermediate Similarity	NPD2091	Phase 2
0.8343	Intermediate Similarity	NPD2096	Phase 2
0.8314	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD2144	Approved
0.8235	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8226	Intermediate Similarity	NPD5426	Phase 3
0.8211	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD786	Approved
0.8168	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD4128	Approved
0.8125	Intermediate Similarity	NPD3038	Discontinued
0.811	Intermediate Similarity	NPD3100	Discontinued
0.8101	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD750	Phase 2
0.8075	Intermediate Similarity	NPD1722	Approved
0.8061	Intermediate Similarity	NPD2172	Phase 1
0.8021	Intermediate Similarity	NPD8073	Approved
0.8011	Intermediate Similarity	NPD8386	Phase 2
0.8	Intermediate Similarity	NPD3961	Discontinued
0.7989	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7957	Phase 1
0.7979	Intermediate Similarity	NPD8072	Approved
0.7977	Intermediate Similarity	NPD1325	Approved
0.7977	Intermediate Similarity	NPD1326	Approved
0.7969	Intermediate Similarity	NPD7470	Discontinued
0.7964	Intermediate Similarity	NPD2837	Discontinued
0.7952	Intermediate Similarity	NPD4462	Approved
0.7952	Intermediate Similarity	NPD4463	Approved
0.7944	Intermediate Similarity	NPD6217	Discontinued
0.7937	Intermediate Similarity	NPD5901	Discontinued
0.7931	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4638	Approved
0.7919	Intermediate Similarity	NPD4640	Approved
0.7919	Intermediate Similarity	NPD4639	Approved
0.7917	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4075	Phase 2
0.7865	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4181	Approved
0.7849	Intermediate Similarity	NPD3323	Discontinued
0.7826	Intermediate Similarity	NPD3404	Approved
0.7824	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8026	Phase 1
0.7772	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD2639	Approved
0.7759	Intermediate Similarity	NPD2642	Approved
0.7744	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7619	Phase 3
0.7742	Intermediate Similarity	NPD7944	Discontinued
0.7742	Intermediate Similarity	NPD7618	Phase 3
0.7708	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5106	Approved
0.768	Intermediate Similarity	NPD5105	Approved
0.7677	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD6999	Discontinued
0.7672	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD8272	Phase 2
0.7638	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4703	Approved
0.7619	Intermediate Similarity	NPD4702	Approved
0.7614	Intermediate Similarity	NPD5021	Discontinued
0.7609	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4886	Phase 2
0.76	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1038	Approved
0.759	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD8093	Discontinued
0.7542	Intermediate Similarity	NPD2928	Phase 2
0.7539	Intermediate Similarity	NPD484	Approved
0.7538	Intermediate Similarity	NPD5612	Discontinued
0.7529	Intermediate Similarity	NPD1404	Approved
0.7529	Intermediate Similarity	NPD1403	Approved
0.7528	Intermediate Similarity	NPD3609	Approved
0.7528	Intermediate Similarity	NPD3610	Approved
0.7527	Intermediate Similarity	NPD1895	Discontinued
0.7514	Intermediate Similarity	NPD2641	Approved
0.7514	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2640	Approved
0.7513	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7271	Approved
0.75	Intermediate Similarity	NPD5818	Discontinued
0.7487	Intermediate Similarity	NPD8322	Phase 2
0.7485	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6158	Phase 2
0.7459	Intermediate Similarity	NPD706	Phase 1
0.7449	Intermediate Similarity	NPD7666	Phase 3
0.7449	Intermediate Similarity	NPD7665	Phase 2
0.7446	Intermediate Similarity	NPD6178	Phase 3
0.7443	Intermediate Similarity	NPD5140	Approved
0.7443	Intermediate Similarity	NPD5138	Approved
0.744	Intermediate Similarity	NPD3813	Approved
0.744	Intermediate Similarity	NPD5254	Discontinued
0.7437	Intermediate Similarity	NPD8094	Discontinued
0.7436	Intermediate Similarity	NPD7001	Phase 3
0.7427	Intermediate Similarity	NPD7730	Approved
0.7427	Intermediate Similarity	NPD7731	Approved
0.7425	Intermediate Similarity	NPD1592	Phase 3
0.7419	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5862	Discovery
0.7416	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4326	Phase 2
0.7412	Intermediate Similarity	NPD4547	Phase 3
0.7407	Intermediate Similarity	NPD802	Phase 2
0.74	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7970	Approved
0.7398	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7780	Approved
0.7391	Intermediate Similarity	NPD7781	Approved
0.7387	Intermediate Similarity	NPD3330	Phase 1
0.7386	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6664	Approved
0.7379	Intermediate Similarity	NPD7711	Discontinued
0.7377	Intermediate Similarity	NPD6452	Discontinued
0.7366	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8122	Approved
0.7363	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8123	Approved
0.7356	Intermediate Similarity	NPD7824	Approved
0.7354	Intermediate Similarity	NPD4615	Phase 2
0.7353	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4499	Approved
0.734	Intermediate Similarity	NPD5117	Phase 2
0.7337	Intermediate Similarity	NPD1707	Approved
0.7337	Intermediate Similarity	NPD1708	Approved
0.7333	Intermediate Similarity	NPD7952	Approved
0.7333	Intermediate Similarity	NPD7951	Approved
0.7333	Intermediate Similarity	NPD7950	Approved
0.7333	Intermediate Similarity	NPD7953	Approved
0.7333	Intermediate Similarity	NPD7789	Approved
0.7333	Intermediate Similarity	NPD7791	Approved
0.7333	Intermediate Similarity	NPD7790	Approved
0.733	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3833	Phase 3
0.7326	Intermediate Similarity	NPD3835	Phase 3
0.7323	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4511	Phase 1
0.7317	Intermediate Similarity	NPD3385	Approved
0.7312	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1661	Suspended
0.7308	Intermediate Similarity	NPD5100	Phase 3
0.7306	Intermediate Similarity	NPD8396	Approved
0.7306	Intermediate Similarity	NPD8395	Approved
0.7306	Intermediate Similarity	NPD3814	Phase 1
0.7297	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7603	Discontinued
0.7293	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1262	Discovery
0.7278	Intermediate Similarity	NPD2006	Phase 2
0.7278	Intermediate Similarity	NPD5436	Phase 1
0.7273	Intermediate Similarity	NPD5255	Approved
0.7268	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2430	Phase 2
0.7267	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD991	Phase 2
0.726	Intermediate Similarity	NPD6165	Phase 2
0.726	Intermediate Similarity	NPD6164	Phase 2
0.7259	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1683	Approved
0.7251	Intermediate Similarity	NPD7469	Discontinued
0.7249	Intermediate Similarity	NPD6281	Approved
0.7243	Intermediate Similarity	NPD8408	Discontinued
0.7241	Intermediate Similarity	NPD7823	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