NPASS Compound

Structure

NPC124005 OpenBabel07101719132D 29 31 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 -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 -4.1835 0.8512 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 -5.0495 -1.6488 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 -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 -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 -4.1835 -2.1488 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 -2.9811 -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 -3.9756 -3.1270 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 -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 4 15 2 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 1 0 0 0 0 8 14 2 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 21 2 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 27 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:	389.21
Volume:	422.197
LogP:	5.389
LogD:	4.117
LogS:	-2.686
# Rotatable Bonds:	5
TPSA:	81.51
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.587
Synthetic Accessibility Score:	3.585
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.494
MDCK Permeability:	1.1002914106938988e-05
Pgp-inhibitor:	0.425
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	92.59415435791016%
Volume Distribution (VD):	0.739
Pgp-substrate:	2.0538113117218018%

ADMET: Metabolism

CYP1A2-inhibitor:	0.947
CYP1A2-substrate:	0.5
CYP2C19-inhibitor:	0.88
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.62
CYP2D6-inhibitor:	0.649
CYP2D6-substrate:	0.422
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.364

ADMET: Excretion

Clearance (CL):	3.774
Half-life (T1/2):	0.372

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.652
Skin Sensitization:	0.219
Carcinogencity:	0.864
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC124005

Natural Product ID:	NPC124005
*Common Name:**	Isoechinulin B
IUPAC Name:	(3Z)-3-[[2-(2-methylbut-3-en-2-yl)-5-(3-methylbut-2-enyl)-1H-indol-3-yl]methylidene]-6-methylidenepiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	YXEBXGSIECYEQC-MOSHPQCFSA-N
Standard InCHI:	InChI=1S/C24H27N3O2/c1-7-24(5,6)21-18(13-20-23(29)25-15(4)22(28)27-20)17-12-16(9-8-14(2)3)10-11-19(17)26-21/h7-8,10-13,26H,1,4,9H2,2-3,5-6H3,(H,25,29)(H,27,28)/b20-13-
SMILES:	C=CC(C)(C)c1c(/C=c2/c(nc(=C)c(n2)O)O)c2cc(CC=C(C)C)ccc2[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249458
PubChem CID:	44445556
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
Others	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	200000.0	nM	PMID[517463]
NPT35	Others	n.a.		IC50	=	60000.0	nM	PMID[517462]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	32.99	%	PMID[517463]
NPT2	Others	Unspecified		IC50	=	9100.0	nM	PMID[517464]
NPT32	Organism	Mus musculus	Mus musculus	Activity	<	70.0	%	PMID[517464]

☑ 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 NPC124005 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	571
0.1-0.2	4708
0.2-0.3	17452
0.3-0.4	13794
0.4-0.5	2741
0.5-0.6	1884
0.6-0.7	1288
0.7-0.8	246
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC38736
0.9714	High Similarity	NPC129042
0.9712	High Similarity	NPC242556
0.9653	High Similarity	NPC184476
0.9456	High Similarity	NPC473320
0.9441	High Similarity	NPC37548
0.9441	High Similarity	NPC187951
0.9329	High Similarity	NPC271734
0.9184	High Similarity	NPC470507
0.9184	High Similarity	NPC471458
0.9073	High Similarity	NPC472587
0.906	High Similarity	NPC299594
0.9026	High Similarity	NPC6982
0.9007	High Similarity	NPC16667
0.8968	High Similarity	NPC34508
0.8854	High Similarity	NPC288785
0.875	High Similarity	NPC67056
0.8742	High Similarity	NPC270009
0.8742	High Similarity	NPC285469
0.8718	High Similarity	NPC280548
0.8675	High Similarity	NPC207726
0.8652	High Similarity	NPC475450
0.8652	High Similarity	NPC179365
0.8634	High Similarity	NPC192270
0.8582	High Similarity	NPC22079
0.8526	High Similarity	NPC470508
0.8511	High Similarity	NPC473587
0.8477	Intermediate Similarity	NPC24678
0.8477	Intermediate Similarity	NPC105818
0.8451	Intermediate Similarity	NPC475428
0.844	Intermediate Similarity	NPC473762
0.8377	Intermediate Similarity	NPC141353
0.8333	Intermediate Similarity	NPC293472
0.8333	Intermediate Similarity	NPC473930
0.8333	Intermediate Similarity	NPC159856
0.8323	Intermediate Similarity	NPC46413
0.8311	Intermediate Similarity	NPC2949
0.8298	Intermediate Similarity	NPC250361
0.8282	Intermediate Similarity	NPC472443
0.8273	Intermediate Similarity	NPC41174
0.8212	Intermediate Similarity	NPC314372
0.82	Intermediate Similarity	NPC190296
0.8153	Intermediate Similarity	NPC92796
0.8153	Intermediate Similarity	NPC135141
0.8133	Intermediate Similarity	NPC472444
0.8125	Intermediate Similarity	NPC474561
0.8125	Intermediate Similarity	NPC49954
0.8117	Intermediate Similarity	NPC33421
0.8113	Intermediate Similarity	NPC194640
0.8105	Intermediate Similarity	NPC477134
0.8095	Intermediate Similarity	NPC198988
0.8086	Intermediate Similarity	NPC470498
0.8067	Intermediate Similarity	NPC59084
0.8061	Intermediate Similarity	NPC176199
0.8061	Intermediate Similarity	NPC215795
0.805	Intermediate Similarity	NPC282231
0.8041	Intermediate Similarity	NPC325252
0.8025	Intermediate Similarity	NPC194411
0.8013	Intermediate Similarity	NPC469760
0.8013	Intermediate Similarity	NPC25008
0.8013	Intermediate Similarity	NPC259644
0.8013	Intermediate Similarity	NPC469763
0.8013	Intermediate Similarity	NPC63157
0.8013	Intermediate Similarity	NPC469786
0.8013	Intermediate Similarity	NPC473868
0.8013	Intermediate Similarity	NPC469765
0.8013	Intermediate Similarity	NPC73952
0.8012	Intermediate Similarity	NPC470509
0.8	Intermediate Similarity	NPC312092
0.8	Intermediate Similarity	NPC68354
0.7988	Intermediate Similarity	NPC472586
0.7987	Intermediate Similarity	NPC279918
0.7987	Intermediate Similarity	NPC21605
0.7974	Intermediate Similarity	NPC470440
0.7963	Intermediate Similarity	NPC63751
0.7963	Intermediate Similarity	NPC154293
0.7962	Intermediate Similarity	NPC211572
0.7962	Intermediate Similarity	NPC80597
0.7962	Intermediate Similarity	NPC70922
0.7962	Intermediate Similarity	NPC212376
0.7962	Intermediate Similarity	NPC75540
0.7947	Intermediate Similarity	NPC469768
0.7947	Intermediate Similarity	NPC469779
0.7947	Intermediate Similarity	NPC469784
0.7947	Intermediate Similarity	NPC469780
0.7947	Intermediate Similarity	NPC469783
0.7947	Intermediate Similarity	NPC469761
0.7947	Intermediate Similarity	NPC469767
0.7919	Intermediate Similarity	NPC218268
0.7904	Intermediate Similarity	NPC198339
0.7898	Intermediate Similarity	NPC32200
0.7895	Intermediate Similarity	NPC469766
0.7881	Intermediate Similarity	NPC73767
0.7881	Intermediate Similarity	NPC88097
0.7879	Intermediate Similarity	NPC37423
0.7879	Intermediate Similarity	NPC275305
0.7872	Intermediate Similarity	NPC215519
0.7871	Intermediate Similarity	NPC471957
0.7867	Intermediate Similarity	NPC125746
0.7867	Intermediate Similarity	NPC84911
0.7862	Intermediate Similarity	NPC469762
0.7853	Intermediate Similarity	NPC201700
0.7829	Intermediate Similarity	NPC115611
0.7824	Intermediate Similarity	NPC476319
0.7821	Intermediate Similarity	NPC2272
0.7812	Intermediate Similarity	NPC206819
0.7812	Intermediate Similarity	NPC318065
0.78	Intermediate Similarity	NPC96102
0.78	Intermediate Similarity	NPC29886
0.78	Intermediate Similarity	NPC261195
0.7799	Intermediate Similarity	NPC469785
0.7791	Intermediate Similarity	NPC49217
0.7791	Intermediate Similarity	NPC54988
0.7791	Intermediate Similarity	NPC160105
0.7784	Intermediate Similarity	NPC248454
0.7778	Intermediate Similarity	NPC311276
0.7778	Intermediate Similarity	NPC122718
0.7765	Intermediate Similarity	NPC190007
0.7764	Intermediate Similarity	NPC131718
0.7763	Intermediate Similarity	NPC110126
0.7763	Intermediate Similarity	NPC104483
0.775	Intermediate Similarity	NPC76982
0.775	Intermediate Similarity	NPC286427
0.7748	Intermediate Similarity	NPC105127
0.7738	Intermediate Similarity	NPC88363
0.7733	Intermediate Similarity	NPC317030
0.7719	Intermediate Similarity	NPC94943
0.7711	Intermediate Similarity	NPC97525
0.7702	Intermediate Similarity	NPC41257
0.7692	Intermediate Similarity	NPC91179
0.7692	Intermediate Similarity	NPC143872
0.7684	Intermediate Similarity	NPC232130
0.7683	Intermediate Similarity	NPC109447
0.7679	Intermediate Similarity	NPC59269
0.767	Intermediate Similarity	NPC133366
0.7669	Intermediate Similarity	NPC40779
0.7669	Intermediate Similarity	NPC8104
0.7669	Intermediate Similarity	NPC476118
0.7669	Intermediate Similarity	NPC90723
0.7665	Intermediate Similarity	NPC189812
0.7665	Intermediate Similarity	NPC329688
0.766	Intermediate Similarity	NPC81561
0.7658	Intermediate Similarity	NPC53947
0.7658	Intermediate Similarity	NPC148592
0.7654	Intermediate Similarity	NPC44773
0.7654	Intermediate Similarity	NPC215584
0.7633	Intermediate Similarity	NPC11126
0.7633	Intermediate Similarity	NPC213468
0.7633	Intermediate Similarity	NPC72980
0.763	Intermediate Similarity	NPC204565
0.7628	Intermediate Similarity	NPC204141
0.7616	Intermediate Similarity	NPC473189
0.7614	Intermediate Similarity	NPC474177
0.7613	Intermediate Similarity	NPC20144
0.761	Intermediate Similarity	NPC216713
0.7605	Intermediate Similarity	NPC314603
0.7602	Intermediate Similarity	NPC163055
0.7602	Intermediate Similarity	NPC19679
0.7602	Intermediate Similarity	NPC212535
0.7597	Intermediate Similarity	NPC284635
0.7597	Intermediate Similarity	NPC279081
0.7593	Intermediate Similarity	NPC56765
0.7593	Intermediate Similarity	NPC475990
0.7589	Intermediate Similarity	NPC148140
0.7586	Intermediate Similarity	NPC65215
0.7586	Intermediate Similarity	NPC34271
0.7586	Intermediate Similarity	NPC246700
0.7586	Intermediate Similarity	NPC173028
0.758	Intermediate Similarity	NPC288838
0.7574	Intermediate Similarity	NPC151939
0.7562	Intermediate Similarity	NPC200214
0.7561	Intermediate Similarity	NPC162799
0.7561	Intermediate Similarity	NPC21174
0.7561	Intermediate Similarity	NPC271797
0.7561	Intermediate Similarity	NPC102423
0.7558	Intermediate Similarity	NPC228835
0.7544	Intermediate Similarity	NPC302191
0.7543	Intermediate Similarity	NPC206967
0.7533	Intermediate Similarity	NPC82295
0.7532	Intermediate Similarity	NPC201380
0.7532	Intermediate Similarity	NPC179787
0.753	Intermediate Similarity	NPC317430
0.7529	Intermediate Similarity	NPC6093
0.7528	Intermediate Similarity	NPC205403
0.7515	Intermediate Similarity	NPC115232
0.75	Intermediate Similarity	NPC214106
0.75	Intermediate Similarity	NPC313791
0.75	Intermediate Similarity	NPC472123
0.7485	Intermediate Similarity	NPC474791
0.7485	Intermediate Similarity	NPC300688
0.7484	Intermediate Similarity	NPC238499
0.7484	Intermediate Similarity	NPC321911
0.7484	Intermediate Similarity	NPC230002
0.7471	Intermediate Similarity	NPC474707
0.7468	Intermediate Similarity	NPC63545
0.7458	Intermediate Similarity	NPC304187
0.7458	Intermediate Similarity	NPC477166
0.7457	Intermediate Similarity	NPC165495
0.7457	Intermediate Similarity	NPC165201
0.7453	Intermediate Similarity	NPC200743

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 NPC124005 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	719
0.2-0.3	906
0.3-0.4	2108
0.4-0.5	2556
0.5-0.6	1975
0.6-0.7	546
0.7-0.8	46
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
0.8725	High Similarity	NPD4462	Approved
0.8725	High Similarity	NPD4463	Approved
0.8411	Intermediate Similarity	NPD3100	Discontinued
0.825	Intermediate Similarity	NPD1325	Approved
0.825	Intermediate Similarity	NPD1326	Approved
0.8235	Intermediate Similarity	NPD2172	Phase 1
0.8176	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD5254	Discontinued
0.8133	Intermediate Similarity	NPD1592	Phase 3
0.8075	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3506	Approved
0.8	Intermediate Similarity	NPD3833	Phase 3
0.8	Intermediate Similarity	NPD3505	Approved
0.8	Intermediate Similarity	NPD3835	Phase 3
0.7963	Intermediate Similarity	NPD5021	Discontinued
0.7952	Intermediate Similarity	NPD8386	Phase 2
0.7952	Intermediate Similarity	NPD4076	Approved
0.7952	Intermediate Similarity	NPD4079	Approved
0.7892	Intermediate Similarity	NPD2144	Approved
0.7881	Intermediate Similarity	NPD786	Approved
0.7867	Intermediate Similarity	NPD1262	Discovery
0.7821	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1683	Approved
0.78	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1722	Approved
0.7771	Intermediate Similarity	NPD4128	Approved
0.7764	Intermediate Similarity	NPD1404	Approved
0.7764	Intermediate Similarity	NPD1403	Approved
0.7751	Intermediate Similarity	NPD3038	Discontinued
0.7744	Intermediate Similarity	NPD2640	Approved
0.7744	Intermediate Similarity	NPD2641	Approved
0.7697	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD2639	Approved
0.7683	Intermediate Similarity	NPD2642	Approved
0.7669	Intermediate Similarity	NPD5138	Approved
0.7669	Intermediate Similarity	NPD5140	Approved
0.7665	Intermediate Similarity	NPD5065	Approved
0.7662	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3654	Approved
0.763	Intermediate Similarity	NPD3961	Discontinued
0.7619	Intermediate Similarity	NPD4075	Phase 2
0.7616	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3385	Approved
0.7548	Intermediate Similarity	NPD5020	Approved
0.753	Intermediate Similarity	NPD4640	Approved
0.753	Intermediate Similarity	NPD4639	Approved
0.753	Intermediate Similarity	NPD4638	Approved
0.753	Intermediate Similarity	NPD2844	Phase 3
0.7517	Intermediate Similarity	NPD947	Approved
0.75	Intermediate Similarity	NPD4880	Discontinued
0.75	Intermediate Similarity	NPD2882	Phase 1
0.7485	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6595	Phase 3
0.7485	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4181	Approved
0.7455	Intermediate Similarity	NPD3323	Discontinued
0.7453	Intermediate Similarity	NPD2837	Discontinued
0.7429	Intermediate Similarity	NPD8431	Approved
0.7429	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4326	Phase 2
0.7421	Intermediate Similarity	NPD4547	Phase 3
0.7418	Intermediate Similarity	NPD4511	Phase 1
0.741	Intermediate Similarity	NPD2720	Phase 1
0.741	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2915	Discontinued
0.7391	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6158	Phase 2
0.7374	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4499	Approved
0.7338	Intermediate Similarity	NPD1253	Approved
0.7338	Intermediate Similarity	NPD1256	Approved
0.7338	Intermediate Similarity	NPD1255	Approved
0.7338	Intermediate Similarity	NPD1254	Approved
0.731	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5104	Approved
0.731	Intermediate Similarity	NPD2381	Approved
0.731	Intermediate Similarity	NPD2380	Approved
0.731	Intermediate Similarity	NPD2382	Approved
0.7303	Intermediate Similarity	NPD1251	Discontinued
0.7299	Intermediate Similarity	NPD5105	Approved
0.7299	Intermediate Similarity	NPD5106	Approved
0.7299	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5596	Phase 2
0.7297	Intermediate Similarity	NPD5901	Discontinued
0.7283	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD482	Approved
0.7238	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3610	Approved
0.7235	Intermediate Similarity	NPD3609	Approved
0.7222	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2092	Phase 2
0.72	Intermediate Similarity	NPD2094	Phase 2
0.72	Intermediate Similarity	NPD2095	Phase 2
0.7191	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5473	Discontinued
0.7182	Intermediate Similarity	NPD7619	Phase 3
0.7182	Intermediate Similarity	NPD7618	Phase 3
0.7179	Intermediate Similarity	NPD6554	Approved
0.7179	Intermediate Similarity	NPD45	Approved
0.717	Intermediate Similarity	NPD4047	Discontinued
0.7167	Intermediate Similarity	NPD3404	Approved
0.7159	Intermediate Similarity	NPD2096	Phase 2
0.7159	Intermediate Similarity	NPD2091	Phase 2
0.7152	Intermediate Similarity	NPD2580	Discontinued
0.7118	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5913	Phase 3
0.7111	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7948	Phase 1
0.7099	Intermediate Similarity	NPD4702	Approved
0.7099	Intermediate Similarity	NPD4703	Approved
0.7089	Intermediate Similarity	NPD680	Discontinued
0.7083	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6217	Discontinued
0.7056	Intermediate Similarity	NPD2564	Approved
0.7056	Intermediate Similarity	NPD2565	Phase 2
0.7052	Intermediate Similarity	NPD6492	Phase 2
0.7048	Intermediate Similarity	NPD2150	Discontinued
0.703	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5075	Discontinued
0.7013	Intermediate Similarity	NPD3476	Approved
0.7013	Intermediate Similarity	NPD3475	Approved
0.7011	Intermediate Similarity	NPD5003	Discontinued
0.7011	Intermediate Similarity	NPD6664	Approved
0.7006	Intermediate Similarity	NPD3320	Approved
0.7006	Intermediate Similarity	NPD3318	Approved
0.7006	Intermediate Similarity	NPD3319	Phase 1
0.6994	Remote Similarity	NPD750	Phase 2
0.6984	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5436	Phase 1
0.6966	Remote Similarity	NPD4957	Phase 2
0.6959	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2006	Phase 2
0.6951	Remote Similarity	NPD2430	Phase 2
0.6949	Remote Similarity	NPD1708	Approved
0.6949	Remote Similarity	NPD1707	Approved
0.6944	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3330	Phase 1
0.694	Remote Similarity	NPD1038	Approved
0.694	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6828	Phase 2
0.6935	Remote Similarity	NPD6249	Phase 2
0.6935	Remote Similarity	NPD6248	Phase 2
0.6933	Remote Similarity	NPD7469	Discontinued
0.6928	Remote Similarity	NPD2119	Approved
0.6928	Remote Similarity	NPD2118	Approved
0.6923	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5100	Phase 3
0.6911	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5898	Approved
0.6893	Remote Similarity	NPD5899	Approved
0.6893	Remote Similarity	NPD6452	Discontinued
0.6893	Remote Similarity	NPD5897	Approved
0.689	Remote Similarity	NPD1661	Suspended
0.6889	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3405	Phase 3
0.6885	Remote Similarity	NPD4615	Phase 2
0.6882	Remote Similarity	NPD1684	Approved
0.6882	Remote Similarity	NPD1685	Approved
0.6875	Remote Similarity	NPD6159	Phase 2
0.6875	Remote Similarity	NPD1953	Discontinued
0.6856	Remote Similarity	NPD8093	Discontinued
0.6854	Remote Similarity	NPD4399	Phase 2
0.6852	Remote Similarity	NPD3525	Discontinued
0.6851	Remote Similarity	NPD2383	Phase 1
0.6851	Remote Similarity	NPD4948	Discontinued
0.6848	Remote Similarity	NPD802	Phase 2
0.6845	Remote Similarity	NPD3814	Phase 1
0.6845	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3117	Approved
0.6839	Remote Similarity	NPD3116	Approved
0.6836	Remote Similarity	NPD3417	Phase 1
0.6836	Remote Similarity	NPD5730	Phase 2
0.6836	Remote Similarity	NPD40	Phase 2
0.6833	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1561	Phase 2
0.6818	Remote Similarity	NPD991	Phase 2
0.6818	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1534	Approved
0.6813	Remote Similarity	NPD4334	Discontinued

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