NPASS Compound

Structure

NPC129042 OpenBabel07101719132D 34 36 0 0 0 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 4.1835 2.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9156 2.8512 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 5.0495 1.3512 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 4.1835 0.8512 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 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 1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0495 2.3512 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 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 -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 0 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 9 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 19 2 0 0 0 0 7 29 1 0 0 0 0 8 29 1 0 0 0 0 9 29 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 23 1 0 0 0 0 16 24 2 0 0 0 0 19 27 1 0 0 0 0 19 30 1 0 0 0 0 21 25 2 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 26 2 0 0 0 0 24 28 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 32 1 0 0 0 0 27 31 2 0 0 0 0 27 33 1 0 0 0 0 28 30 2 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	457.27
Volume:	506.04
LogP:	7.184
LogD:	5.001
LogS:	-2.115
# Rotatable Bonds:	7
TPSA:	81.51
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	3.879
Fsp3:	0.31
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:	-5.526
MDCK Permeability:	1.0733367162174545e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.066
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.614

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	88.56285095214844%
Volume Distribution (VD):	1.24
Pgp-substrate:	2.9783823490142822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.845
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.287
CYP2D6-inhibitor:	0.785
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	3.966
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.911
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.625
Skin Sensitization:	0.496
Carcinogencity:	0.64
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC129042

Natural Product ID:	NPC129042
*Common Name:**	(Z)-3-((5,7-Bis(3-Methylbut-2-Enyl)-2-(2-Methylbut-3-En-2-Yl)-1H-Indol-3-Yl)Methylene)-6-Methylenepiperazine-2,5-Dione
IUPAC Name:	(3Z)-3-[[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methylidene]-6-methylidenepiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	VSBQPALPNZDMGB-JLPGSUDCSA-N
Standard InCHI:	InChI=1S/C29H35N3O2/c1-9-29(7,8)26-23(16-24-28(34)30-19(6)27(33)31-24)22-15-20(12-10-17(2)3)14-21(25(22)32-26)13-11-18(4)5/h9-11,14-16,32H,1,6,12-13H2,2-5,7-8H3,(H,30,34)(H,31,33)/b24-16-
SMILES:	C=CC(c1[nH]c2c(c1/C=c/1 c(O)c(=C)nc1O)cc(cc2CC=C(C)C)CC=C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251475
PubChem CID:	23425627
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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]

☑ 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

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	43000.0	nM	PMID[542402]
NPT2	Others	Unspecified		IC50	=	2400.0	nM	PMID[542403]

☑ 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 NPC129042 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	532
0.1-0.2	4045
0.2-0.3	17106
0.3-0.4	14758
0.4-0.5	2947
0.5-0.6	1985
0.6-0.7	1156
0.7-0.8	159
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC124005
0.9514	High Similarity	NPC184476
0.9444	High Similarity	NPC38736
0.9437	High Similarity	NPC187951
0.9429	High Similarity	NPC242556
0.9195	High Similarity	NPC472587
0.9189	High Similarity	NPC473320
0.9167	High Similarity	NPC37548
0.9067	High Similarity	NPC271734
0.8919	High Similarity	NPC471458
0.8919	High Similarity	NPC470507
0.8867	High Similarity	NPC67056
0.88	High Similarity	NPC299594
0.8774	High Similarity	NPC6982
0.875	High Similarity	NPC16667
0.8718	High Similarity	NPC34508
0.8667	High Similarity	NPC207726
0.8636	High Similarity	NPC470508
0.8608	High Similarity	NPC288785
0.859	High Similarity	NPC280548
0.85	High Similarity	NPC270009
0.8487	Intermediate Similarity	NPC285469
0.8395	Intermediate Similarity	NPC192270
0.838	Intermediate Similarity	NPC475450
0.838	Intermediate Similarity	NPC179365
0.8344	Intermediate Similarity	NPC105818
0.8344	Intermediate Similarity	NPC24678
0.8323	Intermediate Similarity	NPC293472
0.831	Intermediate Similarity	NPC22079
0.8272	Intermediate Similarity	NPC472443
0.8239	Intermediate Similarity	NPC473587
0.8232	Intermediate Similarity	NPC472444
0.8204	Intermediate Similarity	NPC46413
0.8182	Intermediate Similarity	NPC475428
0.8169	Intermediate Similarity	NPC473762
0.8129	Intermediate Similarity	NPC141353
0.8101	Intermediate Similarity	NPC194640
0.8086	Intermediate Similarity	NPC472586
0.8079	Intermediate Similarity	NPC159856
0.8069	Intermediate Similarity	NPC473930
0.8054	Intermediate Similarity	NPC2949
0.8028	Intermediate Similarity	NPC250361
0.8	Intermediate Similarity	NPC41174
0.7974	Intermediate Similarity	NPC477134
0.7961	Intermediate Similarity	NPC314372
0.7947	Intermediate Similarity	NPC190296
0.7911	Intermediate Similarity	NPC92796
0.7911	Intermediate Similarity	NPC135141
0.7888	Intermediate Similarity	NPC474561
0.7888	Intermediate Similarity	NPC49954
0.7885	Intermediate Similarity	NPC73952
0.7885	Intermediate Similarity	NPC469786
0.7885	Intermediate Similarity	NPC469765
0.7885	Intermediate Similarity	NPC25008
0.7885	Intermediate Similarity	NPC259644
0.7885	Intermediate Similarity	NPC469760
0.7885	Intermediate Similarity	NPC469763
0.7871	Intermediate Similarity	NPC33421
0.7853	Intermediate Similarity	NPC470498
0.7838	Intermediate Similarity	NPC198988
0.7834	Intermediate Similarity	NPC80597
0.7834	Intermediate Similarity	NPC75540
0.7834	Intermediate Similarity	NPC212376
0.7834	Intermediate Similarity	NPC70922
0.7834	Intermediate Similarity	NPC211572
0.7831	Intermediate Similarity	NPC215795
0.7831	Intermediate Similarity	NPC176199
0.7815	Intermediate Similarity	NPC469768
0.7815	Intermediate Similarity	NPC469784
0.7815	Intermediate Similarity	NPC469767
0.7815	Intermediate Similarity	NPC469761
0.7815	Intermediate Similarity	NPC469779
0.7815	Intermediate Similarity	NPC59084
0.7815	Intermediate Similarity	NPC469783
0.7815	Intermediate Similarity	NPC469780
0.7812	Intermediate Similarity	NPC282231
0.7791	Intermediate Similarity	NPC194411
0.7785	Intermediate Similarity	NPC325252
0.7784	Intermediate Similarity	NPC32200
0.7784	Intermediate Similarity	NPC198339
0.7778	Intermediate Similarity	NPC470509
0.7771	Intermediate Similarity	NPC68354
0.7763	Intermediate Similarity	NPC469766
0.7763	Intermediate Similarity	NPC473868
0.7763	Intermediate Similarity	NPC63157
0.775	Intermediate Similarity	NPC279918
0.7748	Intermediate Similarity	NPC312092
0.7742	Intermediate Similarity	NPC21605
0.7736	Intermediate Similarity	NPC469762
0.773	Intermediate Similarity	NPC201700
0.773	Intermediate Similarity	NPC215519
0.773	Intermediate Similarity	NPC154293
0.773	Intermediate Similarity	NPC63751
0.7727	Intermediate Similarity	NPC470440
0.7673	Intermediate Similarity	NPC469785
0.7669	Intermediate Similarity	NPC160105
0.7667	Intermediate Similarity	NPC218268
0.7657	Intermediate Similarity	NPC133366
0.7654	Intermediate Similarity	NPC311276
0.7651	Intermediate Similarity	NPC37423
0.7651	Intermediate Similarity	NPC275305
0.7639	Intermediate Similarity	NPC122718
0.7632	Intermediate Similarity	NPC88097
0.7632	Intermediate Similarity	NPC104483
0.7632	Intermediate Similarity	NPC73767
0.7628	Intermediate Similarity	NPC471957
0.7616	Intermediate Similarity	NPC125746
0.7616	Intermediate Similarity	NPC84911
0.7602	Intermediate Similarity	NPC476319
0.76	Intermediate Similarity	NPC474177
0.759	Intermediate Similarity	NPC97525
0.7582	Intermediate Similarity	NPC115611
0.758	Intermediate Similarity	NPC2272
0.7578	Intermediate Similarity	NPC206819
0.7578	Intermediate Similarity	NPC318065
0.7572	Intermediate Similarity	NPC173028
0.7572	Intermediate Similarity	NPC65215
0.7571	Intermediate Similarity	NPC232130
0.7561	Intermediate Similarity	NPC54988
0.7561	Intermediate Similarity	NPC49217
0.756	Intermediate Similarity	NPC248454
0.755	Intermediate Similarity	NPC29886
0.755	Intermediate Similarity	NPC96102
0.755	Intermediate Similarity	NPC261195
0.7546	Intermediate Similarity	NPC40779
0.7544	Intermediate Similarity	NPC190007
0.7531	Intermediate Similarity	NPC131718
0.7518	Intermediate Similarity	NPC81561
0.7516	Intermediate Similarity	NPC110126
0.7516	Intermediate Similarity	NPC286427
0.7516	Intermediate Similarity	NPC76982
0.7515	Intermediate Similarity	NPC88363
0.7514	Intermediate Similarity	NPC317030
0.7514	Intermediate Similarity	NPC204565
0.75	Intermediate Similarity	NPC105127
0.75	Intermediate Similarity	NPC94943
0.7485	Intermediate Similarity	NPC314603
0.7484	Intermediate Similarity	NPC20144
0.7471	Intermediate Similarity	NPC91179
0.7471	Intermediate Similarity	NPC34271
0.7469	Intermediate Similarity	NPC475990
0.7469	Intermediate Similarity	NPC41257
0.7457	Intermediate Similarity	NPC474707
0.7456	Intermediate Similarity	NPC59269
0.7455	Intermediate Similarity	NPC109447
0.7452	Intermediate Similarity	NPC143872
0.7447	Intermediate Similarity	NPC148140
0.7442	Intermediate Similarity	NPC165495
0.744	Intermediate Similarity	NPC189812
0.744	Intermediate Similarity	NPC329688
0.7439	Intermediate Similarity	NPC8104
0.7439	Intermediate Similarity	NPC90723
0.7439	Intermediate Similarity	NPC476118
0.7429	Intermediate Similarity	NPC206967
0.7423	Intermediate Similarity	NPC215584
0.7423	Intermediate Similarity	NPC44773
0.7421	Intermediate Similarity	NPC53947
0.7421	Intermediate Similarity	NPC148592
0.7416	Intermediate Similarity	NPC205403
0.7412	Intermediate Similarity	NPC72980
0.7412	Intermediate Similarity	NPC11126
0.7412	Intermediate Similarity	NPC6093
0.7412	Intermediate Similarity	NPC213468
0.7399	Intermediate Similarity	NPC473189
0.7389	Intermediate Similarity	NPC204141
0.7384	Intermediate Similarity	NPC19679
0.7384	Intermediate Similarity	NPC212535
0.7384	Intermediate Similarity	NPC163055
0.7375	Intermediate Similarity	NPC216713
0.7371	Intermediate Similarity	NPC246700
0.7368	Intermediate Similarity	NPC300688
0.7362	Intermediate Similarity	NPC56765
0.7355	Intermediate Similarity	NPC284635
0.7355	Intermediate Similarity	NPC238499
0.7355	Intermediate Similarity	NPC279081
0.7353	Intermediate Similarity	NPC151939
0.7342	Intermediate Similarity	NPC288838
0.7341	Intermediate Similarity	NPC165201
0.7341	Intermediate Similarity	NPC228835
0.7333	Intermediate Similarity	NPC21174
0.7333	Intermediate Similarity	NPC102423
0.7333	Intermediate Similarity	NPC162799
0.7333	Intermediate Similarity	NPC271797
0.7333	Intermediate Similarity	NPC473747
0.7329	Intermediate Similarity	NPC200214
0.7329	Intermediate Similarity	NPC200743
0.7326	Intermediate Similarity	NPC302191
0.7321	Intermediate Similarity	NPC158129
0.7308	Intermediate Similarity	NPC277157
0.7305	Intermediate Similarity	NPC317430
0.7299	Intermediate Similarity	NPC280290
0.7296	Intermediate Similarity	NPC179787
0.7296	Intermediate Similarity	NPC201380
0.7289	Intermediate Similarity	NPC115232
0.7289	Intermediate Similarity	NPC71132
0.7285	Intermediate Similarity	NPC82295
0.7278	Intermediate Similarity	NPC472123
0.7278	Intermediate Similarity	NPC229332
0.7278	Intermediate Similarity	NPC313791
0.7273	Intermediate Similarity	NPC214106

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 NPC129042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	704
0.2-0.3	886
0.3-0.4	2177
0.4-0.5	2696
0.5-0.6	1958
0.6-0.7	417
0.7-0.8	24
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8467	Intermediate Similarity	NPD4463	Approved
0.8467	Intermediate Similarity	NPD4462	Approved
0.8158	Intermediate Similarity	NPD3100	Discontinued
0.805	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1326	Approved
0.8012	Intermediate Similarity	NPD1325	Approved
0.7987	Intermediate Similarity	NPD2172	Phase 1
0.7939	Intermediate Similarity	NPD8386	Phase 2
0.7895	Intermediate Similarity	NPD5254	Discontinued
0.7881	Intermediate Similarity	NPD1592	Phase 3
0.784	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3506	Approved
0.7771	Intermediate Similarity	NPD3505	Approved
0.7756	Intermediate Similarity	NPD3833	Phase 3
0.7756	Intermediate Similarity	NPD3835	Phase 3
0.773	Intermediate Similarity	NPD5021	Discontinued
0.7725	Intermediate Similarity	NPD4076	Approved
0.7725	Intermediate Similarity	NPD4079	Approved
0.7665	Intermediate Similarity	NPD2144	Approved
0.7632	Intermediate Similarity	NPD786	Approved
0.7616	Intermediate Similarity	NPD1262	Discovery
0.76	Intermediate Similarity	NPD4880	Discontinued
0.759	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1683	Approved
0.755	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4128	Approved
0.7532	Intermediate Similarity	NPD1722	Approved
0.7531	Intermediate Similarity	NPD1404	Approved
0.7531	Intermediate Similarity	NPD1403	Approved
0.7529	Intermediate Similarity	NPD3038	Discontinued
0.7515	Intermediate Similarity	NPD2641	Approved
0.7515	Intermediate Similarity	NPD2640	Approved
0.75	Intermediate Similarity	NPD3654	Approved
0.7486	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2642	Approved
0.7455	Intermediate Similarity	NPD2639	Approved
0.744	Intermediate Similarity	NPD5065	Approved
0.7439	Intermediate Similarity	NPD5140	Approved
0.7439	Intermediate Similarity	NPD5138	Approved
0.7419	Intermediate Similarity	NPD5020	Approved
0.7419	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3385	Approved
0.7414	Intermediate Similarity	NPD3961	Discontinued
0.741	Intermediate Similarity	NPD4640	Approved
0.741	Intermediate Similarity	NPD4638	Approved
0.741	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4639	Approved
0.7399	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4075	Phase 2
0.7378	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2882	Phase 1
0.7372	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD8431	Approved
0.7305	Intermediate Similarity	NPD2844	Phase 3
0.7301	Intermediate Similarity	NPD4326	Phase 2
0.7296	Intermediate Similarity	NPD4547	Phase 3
0.7289	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2720	Phase 1
0.7289	Intermediate Similarity	NPD2915	Discontinued
0.7267	Intermediate Similarity	NPD947	Approved
0.7267	Intermediate Similarity	NPD6595	Phase 3
0.7267	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6158	Phase 2
0.7256	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD4181	Approved
0.7229	Intermediate Similarity	NPD3323	Discontinued
0.7222	Intermediate Similarity	NPD2837	Discontinued
0.7216	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4511	Phase 1
0.7193	Intermediate Similarity	NPD5104	Approved
0.7184	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD680	Discontinued
0.7171	Intermediate Similarity	NPD1251	Discontinued
0.7168	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4499	Approved
0.7135	Intermediate Similarity	NPD2565	Phase 2
0.7135	Intermediate Similarity	NPD2564	Approved
0.7125	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1255	Approved
0.7097	Intermediate Similarity	NPD1253	Approved
0.7097	Intermediate Similarity	NPD5901	Discontinued
0.7097	Intermediate Similarity	NPD1256	Approved
0.7097	Intermediate Similarity	NPD1254	Approved
0.7093	Intermediate Similarity	NPD2380	Approved
0.7093	Intermediate Similarity	NPD2382	Approved
0.7093	Intermediate Similarity	NPD2381	Approved
0.7093	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5106	Approved
0.7086	Intermediate Similarity	NPD5596	Phase 2
0.7086	Intermediate Similarity	NPD5105	Approved
0.7083	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7619	Phase 3
0.7072	Intermediate Similarity	NPD7618	Phase 3
0.7051	Intermediate Similarity	NPD45	Approved
0.7051	Intermediate Similarity	NPD6554	Approved
0.7044	Intermediate Similarity	NPD4047	Discontinued
0.7035	Intermediate Similarity	NPD482	Approved
0.7033	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3609	Approved
0.7018	Intermediate Similarity	NPD3610	Approved
0.7017	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7948	Phase 1
0.6989	Remote Similarity	NPD2095	Phase 2
0.6989	Remote Similarity	NPD2094	Phase 2
0.6989	Remote Similarity	NPD2092	Phase 2
0.6988	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4703	Approved
0.6975	Remote Similarity	NPD4702	Approved
0.6971	Remote Similarity	NPD5473	Discontinued
0.6961	Remote Similarity	NPD3404	Approved
0.6949	Remote Similarity	NPD2096	Phase 2
0.6949	Remote Similarity	NPD2091	Phase 2
0.6941	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6492	Phase 2
0.6928	Remote Similarity	NPD2580	Discontinued
0.6914	Remote Similarity	NPD7469	Discontinued
0.691	Remote Similarity	NPD5075	Discontinued
0.6909	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5913	Phase 3
0.6902	Remote Similarity	NPD6664	Approved
0.6899	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6900	Discontinued
0.6883	Remote Similarity	NPD3476	Approved
0.6883	Remote Similarity	NPD3475	Approved
0.6872	Remote Similarity	NPD6217	Discontinued
0.6867	Remote Similarity	NPD3405	Phase 3
0.6864	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4957	Phase 2
0.6833	Remote Similarity	NPD4948	Discontinued
0.6832	Remote Similarity	NPD3525	Discontinued
0.6832	Remote Similarity	NPD2006	Phase 2
0.6829	Remote Similarity	NPD2430	Phase 2
0.6826	Remote Similarity	NPD2150	Discontinued
0.6821	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6828	Phase 2
0.6818	Remote Similarity	NPD5730	Phase 2
0.6818	Remote Similarity	NPD40	Phase 2
0.6816	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD5003	Discontinued
0.6806	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5100	Phase 3
0.6798	Remote Similarity	NPD3319	Phase 1
0.6798	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3320	Approved
0.6798	Remote Similarity	NPD3318	Approved
0.6797	Remote Similarity	NPD2118	Approved
0.6797	Remote Similarity	NPD2119	Approved
0.6796	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD750	Phase 2
0.678	Remote Similarity	NPD5899	Approved
0.678	Remote Similarity	NPD5898	Approved
0.678	Remote Similarity	NPD6452	Discontinued
0.678	Remote Similarity	NPD5897	Approved
0.6772	Remote Similarity	NPD2920	Discontinued
0.6768	Remote Similarity	NPD1661	Suspended
0.6766	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5315	Discontinued
0.6763	Remote Similarity	NPD5436	Phase 1
0.6761	Remote Similarity	NPD6159	Phase 2
0.6753	Remote Similarity	NPD3330	Phase 1
0.6753	Remote Similarity	NPD8093	Discontinued
0.675	Remote Similarity	NPD1953	Discontinued
0.6748	Remote Similarity	NPD5995	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1707	Approved
0.6742	Remote Similarity	NPD1708	Approved
0.674	Remote Similarity	NPD2383	Phase 1
0.674	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1038	Approved
0.6738	Remote Similarity	NPD6249	Phase 2
0.6738	Remote Similarity	NPD6248	Phase 2
0.6723	Remote Similarity	NPD3417	Phase 1
0.6721	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7709	Discontinued
0.6721	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4334	Discontinued
0.6689	Remote Similarity	NPD1561	Phase 2
0.6687	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4509	Discontinued
0.6686	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4615	Phase 2
0.6667	Remote Similarity	NPD993	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