NPASS Compound

Structure

CID207726 OpenBabel06191716002D 29 31 0 0 1 0 0 0 0 0999 V2000 -3.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5136 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 3.1488 0.0000 C 0 0 0 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 -1.6150 4.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 3.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7816 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 2.1488 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 -7.6476 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0495 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1835 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4811 4.0975 0.0000 C 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 -1.9563 0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9756 3.1270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 -1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 24 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 15 4 1 1 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 13 1 1 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 27 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 25 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	260.03
Volume:	242.021
LogP:	1.708
LogD:	1.59
LogS:	-3.527
# Rotatable Bonds:	0
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	2.421
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.069
MDCK Permeability:	6.545800715684891e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.84
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	89.3957290649414%
Volume Distribution (VD):	0.612
Pgp-substrate:	13.477760314941406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.595
CYP2D6-inhibitor:	0.188
CYP2D6-substrate:	0.277
CYP3A4-inhibitor:	0.162
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	12.302
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.627
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.961
Carcinogencity:	0.045
Eye Corrosion:	0.024
Eye Irritation:	0.952
Respiratory Toxicity:	0.1

Download Data

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

Natural Product: NPC207726

Natural Product ID:	NPC207726
*Common Name:**	Tardioxopiperazine B
IUPAC Name:	(3S,6S)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-7-(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]piperazine-2,5-dione
Synonyms:
Standard InCHIKey:	QNQMVKRHUCFRIY-KXBFYZLASA-N
Standard InCHI:	InChI=1S/C24H31N3O2/c1-7-24(5,6)21-18(13-19-23(29)25-15(4)22(28)26-19)17-10-8-9-16(20(17)27-21)12-11-14(2)3/h7-11,15,19,27H,1,12-13H2,2-6H3,(H,25,29)(H,26,28)/t15-,19-/m0/s1
SMILES:	C=CC(C)(C)c1c(C[C@H]2C(=N[C@@H](C)C(=N2)O)O)c2cccc(CC=C(C)C)c2[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249257
PubChem CID:	10810597
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
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00010a040]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17896816]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17965475]
NPO10055	Stichoneuron caudatum	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24606395]
NPO6417	Lecanora grumosa	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4946	Antidesma venosum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7499	Mammillaria krameri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11458	Hymenoxys subintegra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6874	Desmodium floribundum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6189	Rhamnus nipalensis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10055	Stichoneuron caudatum	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8748	Dacrydium nidulum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1387	Lactarius violascens	Species	Russulaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	899000.0	nM	PMID[447763]

☑ 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 NPC207726 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	360
0.1-0.2	2178
0.2-0.3	16108
0.3-0.4	16086
0.4-0.5	3627
0.5-0.6	2557
0.6-0.7	1254
0.7-0.8	456
0.8-0.85	44
0.85-0.9	17
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC67056
0.9662	High Similarity	NPC16667
0.9658	High Similarity	NPC285469
0.9533	High Similarity	NPC470508
0.9346	High Similarity	NPC280548
0.9211	High Similarity	NPC194640
0.9184	High Similarity	NPC187951
0.9167	High Similarity	NPC472586
0.8994	High Similarity	NPC472443
0.894	High Similarity	NPC38736
0.8926	High Similarity	NPC37548
0.8861	High Similarity	NPC34508
0.8846	High Similarity	NPC474561
0.8846	High Similarity	NPC49954
0.8827	High Similarity	NPC472444
0.8774	High Similarity	NPC282231
0.871	High Similarity	NPC279918
0.8696	High Similarity	NPC293472
0.8693	High Similarity	NPC470507
0.8675	High Similarity	NPC124005
0.8671	High Similarity	NPC63751
0.8667	High Similarity	NPC129042
0.8658	High Similarity	NPC242556
0.8642	High Similarity	NPC270009
0.8634	High Similarity	NPC288785
0.8599	High Similarity	NPC472587
0.8537	High Similarity	NPC192270
0.8516	High Similarity	NPC141353
0.8491	Intermediate Similarity	NPC54988
0.8491	Intermediate Similarity	NPC160105
0.8434	Intermediate Similarity	NPC165495
0.8397	Intermediate Similarity	NPC184476
0.8354	Intermediate Similarity	NPC248454
0.8354	Intermediate Similarity	NPC473320
0.8354	Intermediate Similarity	NPC59269
0.8333	Intermediate Similarity	NPC6982
0.8333	Intermediate Similarity	NPC471458
0.8282	Intermediate Similarity	NPC314603
0.8282	Intermediate Similarity	NPC472123
0.8269	Intermediate Similarity	NPC469765
0.8269	Intermediate Similarity	NPC469760
0.8269	Intermediate Similarity	NPC259644
0.8269	Intermediate Similarity	NPC469763
0.8269	Intermediate Similarity	NPC73952
0.8269	Intermediate Similarity	NPC469786
0.8269	Intermediate Similarity	NPC25008
0.8263	Intermediate Similarity	NPC19679
0.8235	Intermediate Similarity	NPC46413
0.8232	Intermediate Similarity	NPC189812
0.8232	Intermediate Similarity	NPC329688
0.8219	Intermediate Similarity	NPC22079
0.8217	Intermediate Similarity	NPC80597
0.8217	Intermediate Similarity	NPC70922
0.8217	Intermediate Similarity	NPC212376
0.8217	Intermediate Similarity	NPC75540
0.8217	Intermediate Similarity	NPC211572
0.821	Intermediate Similarity	NPC201700
0.821	Intermediate Similarity	NPC317430
0.8176	Intermediate Similarity	NPC204565
0.8176	Intermediate Similarity	NPC317030
0.8155	Intermediate Similarity	NPC163055
0.8137	Intermediate Similarity	NPC271734
0.8129	Intermediate Similarity	NPC173028
0.8129	Intermediate Similarity	NPC65215
0.8113	Intermediate Similarity	NPC299594
0.8113	Intermediate Similarity	NPC469762
0.8084	Intermediate Similarity	NPC219336
0.805	Intermediate Similarity	NPC469785
0.8047	Intermediate Similarity	NPC139291
0.8047	Intermediate Similarity	NPC472108
0.8041	Intermediate Similarity	NPC475450
0.8036	Intermediate Similarity	NPC91179
0.8025	Intermediate Similarity	NPC311276
0.8024	Intermediate Similarity	NPC15573
0.8024	Intermediate Similarity	NPC183662
0.8024	Intermediate Similarity	NPC217372
0.8012	Intermediate Similarity	NPC474707
0.8	Intermediate Similarity	NPC129721
0.8	Intermediate Similarity	NPC314372
0.7988	Intermediate Similarity	NPC233936
0.7988	Intermediate Similarity	NPC154293
0.7976	Intermediate Similarity	NPC72980
0.7976	Intermediate Similarity	NPC213468
0.7974	Intermediate Similarity	NPC2949
0.7964	Intermediate Similarity	NPC267885
0.7953	Intermediate Similarity	NPC15102
0.795	Intermediate Similarity	NPC230869
0.7943	Intermediate Similarity	NPC474177
0.7917	Intermediate Similarity	NPC151939
0.791	Intermediate Similarity	NPC232130
0.7905	Intermediate Similarity	NPC473587
0.7904	Intermediate Similarity	NPC203468
0.7904	Intermediate Similarity	NPC110500
0.7904	Intermediate Similarity	NPC149155
0.7898	Intermediate Similarity	NPC133366
0.7892	Intermediate Similarity	NPC158129
0.7874	Intermediate Similarity	NPC314333
0.7871	Intermediate Similarity	NPC190296
0.787	Intermediate Similarity	NPC126709
0.787	Intermediate Similarity	NPC133261
0.787	Intermediate Similarity	NPC248041
0.7852	Intermediate Similarity	NPC475428
0.7844	Intermediate Similarity	NPC97525
0.7838	Intermediate Similarity	NPC473762
0.7831	Intermediate Similarity	NPC194411
0.7829	Intermediate Similarity	NPC325252
0.7824	Intermediate Similarity	NPC300688
0.7824	Intermediate Similarity	NPC469896
0.7821	Intermediate Similarity	NPC32200
0.7818	Intermediate Similarity	NPC109447
0.7811	Intermediate Similarity	NPC326575
0.7811	Intermediate Similarity	NPC68354
0.7809	Intermediate Similarity	NPC229332
0.7806	Intermediate Similarity	NPC63157
0.7806	Intermediate Similarity	NPC473868
0.7805	Intermediate Similarity	NPC40779
0.7803	Intermediate Similarity	NPC235684
0.78	Intermediate Similarity	NPC179365
0.7799	Intermediate Similarity	NPC33421
0.7799	Intermediate Similarity	NPC105818
0.7799	Intermediate Similarity	NPC24678
0.7791	Intermediate Similarity	NPC472294
0.7791	Intermediate Similarity	NPC255229
0.7791	Intermediate Similarity	NPC81229
0.7784	Intermediate Similarity	NPC473342
0.7784	Intermediate Similarity	NPC477167
0.7771	Intermediate Similarity	NPC469470
0.7771	Intermediate Similarity	NPC78020
0.7771	Intermediate Similarity	NPC95783
0.7771	Intermediate Similarity	NPC469501
0.7765	Intermediate Similarity	NPC283219
0.7763	Intermediate Similarity	NPC198988
0.7751	Intermediate Similarity	NPC134586
0.7748	Intermediate Similarity	NPC473930
0.7742	Intermediate Similarity	NPC59084
0.7733	Intermediate Similarity	NPC472109
0.7733	Intermediate Similarity	NPC472110
0.7719	Intermediate Similarity	NPC198339
0.7714	Intermediate Similarity	NPC213629
0.7714	Intermediate Similarity	NPC321708
0.7714	Intermediate Similarity	NPC175474
0.7712	Intermediate Similarity	NPC218268
0.7706	Intermediate Similarity	NPC211997
0.7706	Intermediate Similarity	NPC14113
0.7706	Intermediate Similarity	NPC145885
0.7706	Intermediate Similarity	NPC84827
0.7703	Intermediate Similarity	NPC250361
0.7692	Intermediate Similarity	NPC37423
0.7692	Intermediate Similarity	NPC275305
0.7688	Intermediate Similarity	NPC190007
0.7688	Intermediate Similarity	NPC228835
0.7683	Intermediate Similarity	NPC131718
0.7677	Intermediate Similarity	NPC88097
0.7674	Intermediate Similarity	NPC302191
0.7673	Intermediate Similarity	NPC21605
0.7671	Intermediate Similarity	NPC41174
0.767	Intermediate Similarity	NPC329858
0.7667	Intermediate Similarity	NPC470499
0.7667	Intermediate Similarity	NPC52557
0.7661	Intermediate Similarity	NPC88363
0.7658	Intermediate Similarity	NPC470440
0.7658	Intermediate Similarity	NPC159856
0.7657	Intermediate Similarity	NPC17059
0.7647	Intermediate Similarity	NPC472122
0.7647	Intermediate Similarity	NPC24594
0.7644	Intermediate Similarity	NPC94943
0.7644	Intermediate Similarity	NPC476319
0.7628	Intermediate Similarity	NPC469779
0.7628	Intermediate Similarity	NPC469783
0.7628	Intermediate Similarity	NPC469761
0.7628	Intermediate Similarity	NPC469780
0.7628	Intermediate Similarity	NPC469768
0.7628	Intermediate Similarity	NPC469767
0.7628	Intermediate Similarity	NPC469784
0.7627	Intermediate Similarity	NPC243716
0.76	Intermediate Similarity	NPC94752
0.759	Intermediate Similarity	NPC476118
0.7586	Intermediate Similarity	NPC165201
0.7582	Intermediate Similarity	NPC470497
0.758	Intermediate Similarity	NPC469766
0.7574	Intermediate Similarity	NPC470498
0.7572	Intermediate Similarity	NPC314394
0.7571	Intermediate Similarity	NPC472112
0.7569	Intermediate Similarity	NPC306376
0.7564	Intermediate Similarity	NPC104483
0.7564	Intermediate Similarity	NPC73767
0.7562	Intermediate Similarity	NPC471957
0.7562	Intermediate Similarity	NPC477134
0.7558	Intermediate Similarity	NPC176199
0.7558	Intermediate Similarity	NPC215795
0.7558	Intermediate Similarity	NPC11126
0.7556	Intermediate Similarity	NPC11445
0.7548	Intermediate Similarity	NPC84911
0.7548	Intermediate Similarity	NPC125746
0.7543	Intermediate Similarity	NPC473189
0.7543	Intermediate Similarity	NPC188387
0.7543	Intermediate Similarity	NPC163421
0.7532	Intermediate Similarity	NPC20144
0.7529	Intermediate Similarity	NPC212535
0.7529	Intermediate Similarity	NPC176127

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 NPC207726 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	510
0.2-0.3	955
0.3-0.4	1490
0.4-0.5	3067
0.5-0.6	2269
0.6-0.7	545
0.7-0.8	112
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8758	High Similarity	NPD8386	Phase 2
0.85	High Similarity	NPD1326	Approved
0.85	High Similarity	NPD1325	Approved
0.8385	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6595	Phase 3
0.8086	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD8431	Approved
0.8059	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4463	Approved
0.8025	Intermediate Similarity	NPD4462	Approved
0.7917	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2144	Approved
0.7904	Intermediate Similarity	NPD482	Approved
0.7874	Intermediate Similarity	NPD4499	Approved
0.787	Intermediate Similarity	NPD4079	Approved
0.787	Intermediate Similarity	NPD4076	Approved
0.7857	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3100	Discontinued
0.7836	Intermediate Similarity	NPD2094	Phase 2
0.7836	Intermediate Similarity	NPD2095	Phase 2
0.7836	Intermediate Similarity	NPD2092	Phase 2
0.7821	Intermediate Similarity	NPD5254	Discontinued
0.7816	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3505	Approved
0.7811	Intermediate Similarity	NPD3506	Approved
0.7806	Intermediate Similarity	NPD1592	Phase 3
0.7791	Intermediate Similarity	NPD2091	Phase 2
0.7791	Intermediate Similarity	NPD2096	Phase 2
0.7778	Intermediate Similarity	NPD3038	Discontinued
0.7744	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5065	Approved
0.7688	Intermediate Similarity	NPD2172	Phase 1
0.7677	Intermediate Similarity	NPD786	Approved
0.7665	Intermediate Similarity	NPD2844	Phase 3
0.7647	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6158	Phase 2
0.764	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD750	Phase 2
0.7627	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5140	Approved
0.759	Intermediate Similarity	NPD5138	Approved
0.7571	Intermediate Similarity	NPD2564	Approved
0.7571	Intermediate Similarity	NPD2565	Phase 2
0.7562	Intermediate Similarity	NPD4703	Approved
0.7562	Intermediate Similarity	NPD4702	Approved
0.756	Intermediate Similarity	NPD4640	Approved
0.756	Intermediate Similarity	NPD4638	Approved
0.756	Intermediate Similarity	NPD4639	Approved
0.756	Intermediate Similarity	NPD5021	Discontinued
0.7557	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2882	Phase 1
0.7516	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4600	Approved
0.7486	Intermediate Similarity	NPD4601	Approved
0.7485	Intermediate Similarity	NPD4128	Approved
0.7484	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1722	Approved
0.7456	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2382	Approved
0.7442	Intermediate Similarity	NPD2380	Approved
0.7442	Intermediate Similarity	NPD2381	Approved
0.7442	Intermediate Similarity	NPD5100	Phase 3
0.7439	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3654	Approved
0.7421	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5901	Discontinued
0.7418	Intermediate Similarity	NPD7948	Phase 1
0.7391	Intermediate Similarity	NPD1683	Approved
0.7363	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4948	Discontinued
0.736	Intermediate Similarity	NPD3961	Discontinued
0.7355	Intermediate Similarity	NPD3385	Approved
0.7341	Intermediate Similarity	NPD4075	Phase 2
0.7337	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1262	Discovery
0.7312	Intermediate Similarity	NPD8073	Approved
0.7308	Intermediate Similarity	NPD4880	Discontinued
0.7308	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7957	Phase 1
0.7287	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6492	Phase 2
0.7273	Intermediate Similarity	NPD8072	Approved
0.7263	Intermediate Similarity	NPD2383	Phase 1
0.7262	Intermediate Similarity	NPD1404	Approved
0.7262	Intermediate Similarity	NPD1403	Approved
0.7258	Intermediate Similarity	NPD4511	Phase 1
0.7256	Intermediate Similarity	NPD3835	Phase 3
0.7256	Intermediate Similarity	NPD3833	Phase 3
0.7251	Intermediate Similarity	NPD2640	Approved
0.7251	Intermediate Similarity	NPD2641	Approved
0.7251	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4326	Phase 2
0.7246	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5913	Phase 3
0.7234	Intermediate Similarity	NPD5426	Phase 3
0.7232	Intermediate Similarity	NPD5596	Phase 2
0.7228	Intermediate Similarity	NPD5003	Discontinued
0.7225	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6452	Discontinued
0.7213	Intermediate Similarity	NPD4602	Approved
0.7211	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4181	Approved
0.7193	Intermediate Similarity	NPD2639	Approved
0.7193	Intermediate Similarity	NPD2642	Approved
0.7181	Intermediate Similarity	NPD2920	Discontinued
0.7176	Intermediate Similarity	NPD3323	Discontinued
0.7175	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2837	Discontinued
0.7167	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1038	Approved
0.7151	Intermediate Similarity	NPD3814	Phase 1
0.7151	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8272	Phase 2
0.7135	Intermediate Similarity	NPD2915	Discontinued
0.7135	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1534	Approved
0.712	Intermediate Similarity	NPD7619	Phase 3
0.712	Intermediate Similarity	NPD7618	Phase 3
0.7112	Intermediate Similarity	NPD4501	Approved
0.7112	Intermediate Similarity	NPD4500	Approved
0.7105	Intermediate Similarity	NPD3003	Approved
0.7104	Intermediate Similarity	NPD3404	Approved
0.7102	Intermediate Similarity	NPD6159	Phase 2
0.7099	Intermediate Similarity	NPD4047	Discontinued
0.7099	Intermediate Similarity	NPD3717	Discontinued
0.7097	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD802	Phase 2
0.7045	Intermediate Similarity	NPD5104	Approved
0.7044	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5020	Approved
0.703	Intermediate Similarity	NPD4547	Phase 3
0.7027	Intermediate Similarity	NPD7944	Discontinued
0.7026	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD484	Approved
0.701	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7470	Discontinued
0.7006	Intermediate Similarity	NPD7865	Approved
0.7	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3525	Discontinued
0.699	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7935	Phase 2
0.6989	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2580	Discontinued
0.6979	Remote Similarity	NPD8322	Phase 2
0.6974	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3609	Approved
0.6971	Remote Similarity	NPD3610	Approved
0.6968	Remote Similarity	NPD1768	Approved
0.6944	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5106	Approved
0.6944	Remote Similarity	NPD5105	Approved
0.6933	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1661	Suspended
0.6927	Remote Similarity	NPD5898	Approved
0.6927	Remote Similarity	NPD5897	Approved
0.6927	Remote Similarity	NPD5473	Discontinued
0.6927	Remote Similarity	NPD5899	Approved
0.6923	Remote Similarity	NPD6217	Discontinued
0.6919	Remote Similarity	NPD1685	Approved
0.6919	Remote Similarity	NPD1684	Approved
0.6919	Remote Similarity	NPD8026	Phase 1
0.6914	Remote Similarity	NPD680	Discontinued
0.6911	Remote Similarity	NPD4886	Phase 2
0.691	Remote Similarity	NPD8123	Approved
0.691	Remote Similarity	NPD8122	Approved
0.6902	Remote Similarity	NPD5117	Phase 2
0.6901	Remote Similarity	NPD5255	Approved
0.6894	Remote Similarity	NPD6554	Approved
0.6894	Remote Similarity	NPD45	Approved
0.6889	Remote Similarity	NPD4204	Approved
0.6889	Remote Similarity	NPD4203	Approved
0.6888	Remote Similarity	NPD8093	Discontinued
0.6882	Remote Similarity	NPD2150	Discontinued
0.6878	Remote Similarity	NPD2176	Approved
0.6878	Remote Similarity	NPD2177	Approved
0.6878	Remote Similarity	NPD8395	Approved
0.6878	Remote Similarity	NPD2175	Phase 3
0.6878	Remote Similarity	NPD8396	Approved
0.6872	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1528	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