NPASS Compound

Structure

NPC474561 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7988 1.0657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4679 0.3226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8206 0.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1589 -0.6285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -1.7024 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 -0.0000 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 2 1 6 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 18 1 0 0 0 0 14 8 1 1 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.16
Volume:	311.671
LogP:	2.576
LogD:	2.83
LogS:	-3.331
# Rotatable Bonds:	4
TPSA:	73.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	3.267
Fsp3:	0.412
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:	-4.727
MDCK Permeability:	7.652844942640513e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.734

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.718
Plasma Protein Binding (PPB):	83.58838653564453%
Volume Distribution (VD):	0.784
Pgp-substrate:	14.72330093383789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.139
CYP1A2-substrate:	0.28
CYP2C19-inhibitor:	0.486
CYP2C19-substrate:	0.237
CYP2C9-inhibitor:	0.362
CYP2C9-substrate:	0.566
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.54
CYP3A4-inhibitor:	0.803
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	4.574
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.261
Drug-inuced Liver Injury (DILI):	0.143
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.766
Maximum Recommended Daily Dose:	0.743
Skin Sensitization:	0.07
Carcinogencity:	0.119
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.299

Download Data

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

Natural Product: NPC474561

Natural Product ID:	NPC474561
*Common Name:**	Cyclo-(D-Ile-L-Trp)
IUPAC Name:	(3R,6S)-3-[(2S)-butan-2-yl]-6-(1H-indol-3-ylmethyl)piperazine-2,5-dione
Synonyms:
Standard InCHIKey:	PGCNHGBQEYFZEX-NZVBXONLSA-N
Standard InCHI:	InChI=1S/C17H21N3O2/c1-3-10(2)15-17(22)19-14(16(21)20-15)8-11-9-18-13-7-5-4-6-12(11)13/h4-7,9-10,14-15,18H,3,8H2,1-2H3,(H,19,22)(H,20,21)/t10-,14-,15+/m0/s1
SMILES:	CCC(C)C1C(=O)NC(C(=O)N1)CC2=CNC3=CC=CC=C32
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472229
PubChem CID:	44575417
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
NPO33398	penicillium brevi-compactum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730251]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	=	167.0	%	PMID[525222]

☑ 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 NPC474561 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	386
0.1-0.2	3328
0.2-0.3	19011
0.3-0.4	12602
0.4-0.5	3064
0.5-0.6	2133
0.6-0.7	1336
0.7-0.8	624
0.8-0.85	129
0.85-0.9	57
0.9-0.95	20
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC49954
0.9801	High Similarity	NPC282231
0.9735	High Similarity	NPC279918
0.9675	High Similarity	NPC63751
0.961	High Similarity	NPC160105
0.9608	High Similarity	NPC194640
0.9484	High Similarity	NPC54988
0.9367	High Similarity	NPC314603
0.9313	High Similarity	NPC248454
0.9313	High Similarity	NPC59269
0.9276	High Similarity	NPC469760
0.9276	High Similarity	NPC73952
0.9276	High Similarity	NPC469786
0.9276	High Similarity	NPC469765
0.9276	High Similarity	NPC259644
0.9276	High Similarity	NPC25008
0.9276	High Similarity	NPC469763
0.9216	High Similarity	NPC80597
0.9216	High Similarity	NPC211572
0.9216	High Similarity	NPC75540
0.9216	High Similarity	NPC212376
0.9216	High Similarity	NPC70922
0.9156	High Similarity	NPC285469
0.9097	High Similarity	NPC469762
0.9085	High Similarity	NPC163055
0.9032	High Similarity	NPC469785
0.9024	High Similarity	NPC233936
0.9007	High Similarity	NPC314372
0.8987	High Similarity	NPC311276
0.8938	High Similarity	NPC201700
0.8924	High Similarity	NPC16667
0.8896	High Similarity	NPC267885
0.8874	High Similarity	NPC190296
0.8846	High Similarity	NPC207726
0.8834	High Similarity	NPC149155
0.8834	High Similarity	NPC110500
0.8834	High Similarity	NPC203468
0.8802	High Similarity	NPC165495
0.8797	High Similarity	NPC230869
0.8788	High Similarity	NPC248041
0.8788	High Similarity	NPC126709
0.8774	High Similarity	NPC105818
0.8774	High Similarity	NPC24678
0.8765	High Similarity	NPC194411
0.8757	High Similarity	NPC317030
0.875	High Similarity	NPC40779
0.875	High Similarity	NPC15102
0.8727	High Similarity	NPC68354
0.8706	High Similarity	NPC213629
0.8704	High Similarity	NPC78020
0.8698	High Similarity	NPC474707
0.8698	High Similarity	NPC235684
0.869	High Similarity	NPC228835
0.8679	High Similarity	NPC67056
0.8675	High Similarity	NPC283219
0.8675	High Similarity	NPC213468
0.8663	High Similarity	NPC477167
0.8663	High Similarity	NPC473342
0.865	High Similarity	NPC280548
0.8647	High Similarity	NPC204565
0.8636	High Similarity	NPC159856
0.8625	High Similarity	NPC131718
0.8618	High Similarity	NPC469779
0.8618	High Similarity	NPC469784
0.8618	High Similarity	NPC469768
0.8618	High Similarity	NPC469780
0.8618	High Similarity	NPC469761
0.8618	High Similarity	NPC469783
0.8618	High Similarity	NPC469767
0.8614	High Similarity	NPC151939
0.8614	High Similarity	NPC14113
0.8614	High Similarity	NPC145885
0.8614	High Similarity	NPC84827
0.8606	High Similarity	NPC275305
0.8606	High Similarity	NPC37423
0.8596	High Similarity	NPC321708
0.8596	High Similarity	NPC173028
0.8596	High Similarity	NPC65215
0.859	High Similarity	NPC37548
0.8588	High Similarity	NPC94752
0.8562	High Similarity	NPC469766
0.8553	High Similarity	NPC73767
0.8547	High Similarity	NPC95783
0.8543	High Similarity	NPC84911
0.8538	High Similarity	NPC17059
0.8526	High Similarity	NPC471957
0.8512	High Similarity	NPC300688
0.8485	Intermediate Similarity	NPC470498
0.8477	Intermediate Similarity	NPC29886
0.8477	Intermediate Similarity	NPC261195
0.8477	Intermediate Similarity	NPC96102
0.8466	Intermediate Similarity	NPC470508
0.8452	Intermediate Similarity	NPC176199
0.8452	Intermediate Similarity	NPC11126
0.8452	Intermediate Similarity	NPC215795
0.8447	Intermediate Similarity	NPC135141
0.8447	Intermediate Similarity	NPC92796
0.8447	Intermediate Similarity	NPC318065
0.8447	Intermediate Similarity	NPC206819
0.8431	Intermediate Similarity	NPC110126
0.8421	Intermediate Similarity	NPC163421
0.8421	Intermediate Similarity	NPC105127
0.8421	Intermediate Similarity	NPC188387
0.8418	Intermediate Similarity	NPC470499
0.8418	Intermediate Similarity	NPC53947
0.8405	Intermediate Similarity	NPC102423
0.84	Intermediate Similarity	NPC474177
0.8385	Intermediate Similarity	NPC129721
0.8375	Intermediate Similarity	NPC470507
0.8375	Intermediate Similarity	NPC38736
0.8354	Intermediate Similarity	NPC187951
0.8352	Intermediate Similarity	NPC133366
0.8344	Intermediate Similarity	NPC143872
0.8343	Intermediate Similarity	NPC55772
0.8343	Intermediate Similarity	NPC477166
0.8343	Intermediate Similarity	NPC304187
0.8333	Intermediate Similarity	NPC242556
0.8324	Intermediate Similarity	NPC470497
0.8323	Intermediate Similarity	NPC34508
0.8323	Intermediate Similarity	NPC141353
0.8323	Intermediate Similarity	NPC313791
0.8323	Intermediate Similarity	NPC472123
0.8315	Intermediate Similarity	NPC473640
0.8315	Intermediate Similarity	NPC171317
0.8314	Intermediate Similarity	NPC314002
0.8284	Intermediate Similarity	NPC111275
0.8268	Intermediate Similarity	NPC293917
0.8268	Intermediate Similarity	NPC100321
0.8266	Intermediate Similarity	NPC171171
0.8258	Intermediate Similarity	NPC229332
0.8258	Intermediate Similarity	NPC279081
0.8256	Intermediate Similarity	NPC204717
0.8253	Intermediate Similarity	NPC317430
0.825	Intermediate Similarity	NPC216713
0.8246	Intermediate Similarity	NPC71037
0.8239	Intermediate Similarity	NPC99666
0.8228	Intermediate Similarity	NPC288838
0.8221	Intermediate Similarity	NPC56765
0.8221	Intermediate Similarity	NPC41257
0.8212	Intermediate Similarity	NPC82295
0.8208	Intermediate Similarity	NPC280290
0.8202	Intermediate Similarity	NPC11445
0.8199	Intermediate Similarity	NPC200214
0.8198	Intermediate Similarity	NPC220765
0.8177	Intermediate Similarity	NPC475506
0.8166	Intermediate Similarity	NPC189812
0.8166	Intermediate Similarity	NPC329688
0.8166	Intermediate Similarity	NPC472586
0.816	Intermediate Similarity	NPC286427
0.8156	Intermediate Similarity	NPC262898
0.8156	Intermediate Similarity	NPC227582
0.8146	Intermediate Similarity	NPC22079
0.8146	Intermediate Similarity	NPC195239
0.8146	Intermediate Similarity	NPC157828
0.8141	Intermediate Similarity	NPC230002
0.8132	Intermediate Similarity	NPC155143
0.8132	Intermediate Similarity	NPC476874
0.8132	Intermediate Similarity	NPC193761
0.8129	Intermediate Similarity	NPC219336
0.8129	Intermediate Similarity	NPC270009
0.8129	Intermediate Similarity	NPC472443
0.8125	Intermediate Similarity	NPC321911
0.8125	Intermediate Similarity	NPC124005
0.8122	Intermediate Similarity	NPC106771
0.8122	Intermediate Similarity	NPC205254
0.8122	Intermediate Similarity	NPC23420
0.8122	Intermediate Similarity	NPC303820
0.8118	Intermediate Similarity	NPC288785
0.8114	Intermediate Similarity	NPC46580
0.8101	Intermediate Similarity	NPC179701
0.8092	Intermediate Similarity	NPC469358
0.8092	Intermediate Similarity	NPC472108
0.8092	Intermediate Similarity	NPC48938
0.8092	Intermediate Similarity	NPC139291
0.8084	Intermediate Similarity	NPC109447
0.8084	Intermediate Similarity	NPC49217
0.8081	Intermediate Similarity	NPC91179
0.8077	Intermediate Similarity	NPC52909
0.8077	Intermediate Similarity	NPC475935
0.8077	Intermediate Similarity	NPC94211
0.807	Intermediate Similarity	NPC217372
0.807	Intermediate Similarity	NPC183662
0.807	Intermediate Similarity	NPC15573
0.8063	Intermediate Similarity	NPC179787
0.8063	Intermediate Similarity	NPC201380
0.8063	Intermediate Similarity	NPC469811
0.8057	Intermediate Similarity	NPC315555
0.8057	Intermediate Similarity	NPC62749
0.8049	Intermediate Similarity	NPC216643
0.8043	Intermediate Similarity	NPC473376
0.8037	Intermediate Similarity	NPC471458
0.8035	Intermediate Similarity	NPC192270
0.8025	Intermediate Similarity	NPC470233
0.8022	Intermediate Similarity	NPC252338
0.8011	Intermediate Similarity	NPC314957
0.8	Intermediate Similarity	NPC325252
0.8	Intermediate Similarity	NPC63545
0.7989	Intermediate Similarity	NPC472110
0.7989	Intermediate Similarity	NPC307963
0.7989	Intermediate Similarity	NPC472109

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 NPC474561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	543
0.2-0.3	1060
0.3-0.4	1399
0.4-0.5	2664
0.5-0.6	2078
0.6-0.7	954
0.7-0.8	213
0.8-0.85	28
0.85-0.9	15
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9487	High Similarity	NPD4184	Clinical (unspecified phase)
0.908	High Similarity	NPD6595	Phase 3
0.8834	High Similarity	NPD482	Approved
0.8817	High Similarity	NPD8110	Clinical (unspecified phase)
0.8788	High Similarity	NPD4076	Approved
0.8788	High Similarity	NPD4079	Approved
0.878	High Similarity	NPD749	Clinical (unspecified phase)
0.8757	High Similarity	NPD8431	Approved
0.875	High Similarity	NPD6610	Clinical (unspecified phase)
0.8743	High Similarity	NPD5728	Clinical (unspecified phase)
0.8743	High Similarity	NPD2092	Phase 2
0.8743	High Similarity	NPD2094	Phase 2
0.8743	High Similarity	NPD2095	Phase 2
0.8727	High Similarity	NPD3506	Approved
0.8727	High Similarity	NPD3505	Approved
0.869	High Similarity	NPD2096	Phase 2
0.869	High Similarity	NPD2091	Phase 2
0.8675	High Similarity	NPD786	Approved
0.8614	High Similarity	NPD6203	Clinical (unspecified phase)
0.8614	High Similarity	NPD2144	Approved
0.8606	High Similarity	NPD5065	Approved
0.859	High Similarity	NPD3100	Discontinued
0.8571	High Similarity	NPD3038	Discontinued
0.8562	High Similarity	NPD1722	Approved
0.8545	High Similarity	NPD750	Phase 2
0.8477	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD1325	Approved
0.8313	Intermediate Similarity	NPD1326	Approved
0.8295	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD4128	Approved
0.8268	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD7948	Phase 1
0.8253	Intermediate Similarity	NPD4640	Approved
0.8253	Intermediate Similarity	NPD4638	Approved
0.8253	Intermediate Similarity	NPD4639	Approved
0.8225	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD4075	Phase 2
0.8218	Intermediate Similarity	NPD3961	Discontinued
0.8187	Intermediate Similarity	NPD4462	Approved
0.8187	Intermediate Similarity	NPD4463	Approved
0.8187	Intermediate Similarity	NPD2172	Phase 1
0.8187	Intermediate Similarity	NPD8072	Approved
0.8187	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD8073	Approved
0.8129	Intermediate Similarity	NPD8386	Phase 2
0.8098	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7957	Phase 1
0.8072	Intermediate Similarity	NPD3323	Discontinued
0.807	Intermediate Similarity	NPD4181	Approved
0.8063	Intermediate Similarity	NPD4702	Approved
0.8063	Intermediate Similarity	NPD4703	Approved
0.8054	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD8272	Phase 2
0.8036	Intermediate Similarity	NPD2641	Approved
0.8036	Intermediate Similarity	NPD2640	Approved
0.8011	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD1038	Approved
0.7975	Intermediate Similarity	NPD2837	Discontinued
0.7952	Intermediate Similarity	NPD1404	Approved
0.7952	Intermediate Similarity	NPD1403	Approved
0.7946	Intermediate Similarity	NPD5901	Discontinued
0.7929	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD7470	Discontinued
0.787	Intermediate Similarity	NPD2639	Approved
0.787	Intermediate Similarity	NPD2642	Approved
0.7853	Intermediate Similarity	NPD6217	Discontinued
0.7849	Intermediate Similarity	NPD5426	Phase 3
0.7836	Intermediate Similarity	NPD3609	Approved
0.7836	Intermediate Similarity	NPD3610	Approved
0.7833	Intermediate Similarity	NPD3404	Approved
0.7831	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD484	Approved
0.7799	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD8026	Phase 1
0.779	Intermediate Similarity	NPD802	Phase 2
0.776	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1592	Phase 3
0.7749	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7619	Phase 3
0.7747	Intermediate Similarity	NPD7618	Phase 3
0.7722	Intermediate Similarity	NPD4499	Approved
0.7719	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD3717	Discontinued
0.7701	Intermediate Similarity	NPD5100	Phase 3
0.7692	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5254	Discontinued
0.765	Intermediate Similarity	NPD7944	Discontinued
0.7647	Intermediate Similarity	NPD5138	Approved
0.7647	Intermediate Similarity	NPD5140	Approved
0.7644	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5117	Phase 2
0.7622	Intermediate Similarity	NPD1661	Suspended
0.7616	Intermediate Similarity	NPD5021	Discontinued
0.7597	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD991	Phase 2
0.7597	Intermediate Similarity	NPD2118	Approved
0.7597	Intermediate Similarity	NPD2119	Approved
0.759	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5105	Approved
0.7584	Intermediate Similarity	NPD5106	Approved
0.7579	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5255	Approved
0.7571	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6664	Approved
0.7564	Intermediate Similarity	NPD3476	Approved
0.7564	Intermediate Similarity	NPD3475	Approved
0.7556	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD706	Phase 1
0.7545	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD2928	Phase 2
0.7538	Intermediate Similarity	NPD5612	Discontinued
0.7529	Intermediate Similarity	NPD3116	Approved
0.7529	Intermediate Similarity	NPD3117	Approved
0.7515	Intermediate Similarity	NPD4547	Phase 3
0.7514	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2844	Phase 3
0.7514	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3654	Approved
0.75	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2006	Phase 2
0.7485	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6158	Phase 2
0.7474	Intermediate Similarity	NPD8093	Discontinued
0.747	Intermediate Similarity	NPD2430	Phase 2
0.7458	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2580	Discontinued
0.7455	Intermediate Similarity	NPD1683	Approved
0.7455	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4601	Approved
0.7447	Intermediate Similarity	NPD4600	Approved
0.7446	Intermediate Similarity	NPD4615	Phase 2
0.7444	Intermediate Similarity	NPD6178	Phase 3
0.7439	Intermediate Similarity	NPD3813	Approved
0.7436	Intermediate Similarity	NPD8094	Discontinued
0.7432	Intermediate Similarity	NPD6281	Approved
0.7421	Intermediate Similarity	NPD4030	Approved
0.7421	Intermediate Similarity	NPD4028	Approved
0.7421	Intermediate Similarity	NPD3385	Approved
0.7421	Intermediate Similarity	NPD4029	Approved
0.7414	Intermediate Similarity	NPD5862	Discovery
0.7413	Intermediate Similarity	NPD7271	Approved
0.7407	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD2380	Approved
0.7401	Intermediate Similarity	NPD2381	Approved
0.7401	Intermediate Similarity	NPD2382	Approved
0.7396	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1392	Approved
0.7391	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8123	Approved
0.736	Intermediate Similarity	NPD8122	Approved
0.7354	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3112	Approved
0.7353	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3115	Approved
0.7353	Intermediate Similarity	NPD3113	Approved
0.7353	Intermediate Similarity	NPD3114	Approved
0.7346	Intermediate Similarity	NPD2896	Discontinued
0.734	Intermediate Similarity	NPD7731	Approved
0.734	Intermediate Similarity	NPD7730	Approved
0.7333	Intermediate Similarity	NPD3178	Discontinued
0.7333	Intermediate Similarity	NPD5066	Phase 2
0.7333	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5067	Phase 2
0.733	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5818	Discontinued
0.7318	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4511	Phase 1
0.731	Intermediate Similarity	NPD7970	Approved
0.731	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4326	Phase 2
0.731	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3825	Phase 3
0.7302	Intermediate Similarity	NPD6999	Discontinued
0.7302	Intermediate Similarity	NPD3814	Phase 1
0.7296	Intermediate Similarity	NPD3330	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