NPASS Compound

Structure

NPC304203 OpenBabel07101719122D 28 33 0 0 0 0 0 0 0 0999 V2000 -0.2179 -2.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3307 1.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5341 1.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0585 -2.8576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6391 2.6915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5849 0.4358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2179 -1.4017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3795 1.5781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6693 1.8457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8990 -2.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9962 3.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7709 -0.0928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2255 0.1345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4747 3.2400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0585 -0.9164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7367 2.3053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8553 1.3171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2603 0.0330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7661 2.3142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8990 -1.4017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0451 3.2256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9061 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0822 1.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6108 0.7543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6203 -0.7522 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2651 3.8033 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 -0.4300 2.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 7 1 0 0 0 0 2 5 2 0 0 0 0 2 8 1 0 0 0 0 3 6 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 10 20 2 0 0 0 0 11 21 2 0 0 0 0 12 22 2 0 0 0 0 13 18 2 0 0 0 0 13 25 1 0 0 0 0 14 19 2 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 28 2 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	363.14
Volume:	382.464
LogP:	4.581
LogD:	4.522
LogS:	-4.863
# Rotatable Bonds:	2
TPSA:	60.68
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	2.705
Fsp3:	0.042
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.072
MDCK Permeability:	5.064109245722648e-06
Pgp-inhibitor:	0.874
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	98.10330963134766%
Volume Distribution (VD):	1.059
Pgp-substrate:	1.591526746749878%

ADMET: Metabolism

CYP1A2-inhibitor:	0.488
CYP1A2-substrate:	0.695
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.948
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.75
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.94
CYP3A4-substrate:	0.768

ADMET: Excretion

Clearance (CL):	2.641
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.512
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.39
Rat Oral Acute Toxicity:	0.607
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.863
Carcinogencity:	0.061
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.827

Download Data

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

Natural Product: NPC304203

Natural Product ID:	NPC304203
*Common Name:**	2,2-Di(3-Indolyl)-3-Indolone
IUPAC Name:	2,2-bis(1H-indol-3-yl)-1H-indol-3-one
Synonyms:
Standard InCHIKey:	IZKCVKAIVRRHDC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H17N3O/c28-23-17-9-3-6-12-22(17)27-24(23,18-13-25-20-10-4-1-7-15(18)20)19-14-26-21-11-5-2-8-16(19)21/h1-14,25-27H
SMILES:	O=C1c2ccccc2NC1(c1c[nH]c2c1cccc2)c1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471481
PubChem CID:	10021609
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076576]
NPO11616	Vibrio parahaemolyticus	Species	Vibrionaceae	Bacteria	n.a.	North Sea	n.a.	PMID[14640534]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	Melia azedarach	n.a.	n.a.	PMID[21353539]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24183988]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33180497]
NPO11616	Vibrio parahaemolyticus	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7853008]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988601]
NPO11616	Vibrio parahaemolyticus	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	DOI[DOI: 10.1111/j.1574-6968.1992.tb05311.x]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11616	Vibrio parahaemolyticus	Species	Vibrionaceae	Bacteria	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
EC50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[508386]
NPT22368	ORGANISM	Zika virus	Zika virus	EC50	=	22000.0	nM	PMID[508387]

☑ 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 NPC304203 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	715
0.1-0.2	7844
0.2-0.3	15995
0.3-0.4	12440
0.4-0.5	1924
0.5-0.6	1920
0.6-0.7	1356
0.7-0.8	443
0.8-0.85	41
0.85-0.9	12
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9318	High Similarity	NPC476460
0.924	High Similarity	NPC284775
0.9	High Similarity	NPC326422
0.887	High Similarity	NPC477003
0.877	High Similarity	NPC317701
0.8508	High Similarity	NPC308931
0.8508	High Similarity	NPC99939
0.8444	Intermediate Similarity	NPC191415
0.8398	Intermediate Similarity	NPC117027
0.8351	Intermediate Similarity	NPC227582
0.8351	Intermediate Similarity	NPC167710
0.8343	Intermediate Similarity	NPC42372
0.8333	Intermediate Similarity	NPC267811
0.8324	Intermediate Similarity	NPC324091
0.8316	Intermediate Similarity	NPC470702
0.8316	Intermediate Similarity	NPC473218
0.8274	Intermediate Similarity	NPC470703
0.8266	Intermediate Similarity	NPC216643
0.8263	Intermediate Similarity	NPC477004
0.8263	Intermediate Similarity	NPC74413
0.822	Intermediate Similarity	NPC252338
0.8207	Intermediate Similarity	NPC133003
0.8202	Intermediate Similarity	NPC471943
0.8197	Intermediate Similarity	NPC102755
0.8172	Intermediate Similarity	NPC473666
0.8167	Intermediate Similarity	NPC293216
0.8135	Intermediate Similarity	NPC260900
0.8112	Intermediate Similarity	NPC116555
0.8111	Intermediate Similarity	NPC252572
0.8034	Intermediate Similarity	NPC115232
0.8021	Intermediate Similarity	NPC67288
0.8021	Intermediate Similarity	NPC131887
0.8012	Intermediate Similarity	NPC288838
0.8011	Intermediate Similarity	NPC92796
0.8011	Intermediate Similarity	NPC135141
0.8	Intermediate Similarity	NPC229893
0.799	Intermediate Similarity	NPC82370
0.7979	Intermediate Similarity	NPC321708
0.7977	Intermediate Similarity	NPC53947
0.7947	Intermediate Similarity	NPC47190
0.7946	Intermediate Similarity	NPC470677
0.7923	Intermediate Similarity	NPC151635
0.7921	Intermediate Similarity	NPC36405
0.791	Intermediate Similarity	NPC474492
0.7903	Intermediate Similarity	NPC470205
0.7892	Intermediate Similarity	NPC477042
0.7887	Intermediate Similarity	NPC475914
0.7887	Intermediate Similarity	NPC237414
0.7887	Intermediate Similarity	NPC153123
0.7887	Intermediate Similarity	NPC220797
0.7887	Intermediate Similarity	NPC474318
0.7887	Intermediate Similarity	NPC201266
0.7887	Intermediate Similarity	NPC268744
0.7854	Intermediate Similarity	NPC276657
0.7853	Intermediate Similarity	NPC216550
0.7846	Intermediate Similarity	NPC77241
0.7846	Intermediate Similarity	NPC269203
0.7846	Intermediate Similarity	NPC166209
0.7846	Intermediate Similarity	NPC13456
0.7842	Intermediate Similarity	NPC154339
0.7824	Intermediate Similarity	NPC128244
0.7824	Intermediate Similarity	NPC79356
0.7824	Intermediate Similarity	NPC102592
0.7821	Intermediate Similarity	NPC214106
0.782	Intermediate Similarity	NPC267078
0.782	Intermediate Similarity	NPC935
0.7783	Intermediate Similarity	NPC474357
0.7766	Intermediate Similarity	NPC110158
0.7765	Intermediate Similarity	NPC100104
0.7765	Intermediate Similarity	NPC470680
0.7722	Intermediate Similarity	NPC242116
0.772	Intermediate Similarity	NPC267343
0.7696	Intermediate Similarity	NPC103119
0.7696	Intermediate Similarity	NPC474412
0.7689	Intermediate Similarity	NPC470323
0.7688	Intermediate Similarity	NPC157583
0.7688	Intermediate Similarity	NPC237188
0.7685	Intermediate Similarity	NPC110182
0.7684	Intermediate Similarity	NPC135601
0.7684	Intermediate Similarity	NPC17273
0.7684	Intermediate Similarity	NPC251391
0.7684	Intermediate Similarity	NPC141612
0.768	Intermediate Similarity	NPC271797
0.768	Intermediate Similarity	NPC21174
0.768	Intermediate Similarity	NPC265100
0.768	Intermediate Similarity	NPC317105
0.7677	Intermediate Similarity	NPC476073
0.7672	Intermediate Similarity	NPC467063
0.7672	Intermediate Similarity	NPC21429
0.767	Intermediate Similarity	NPC471655
0.7654	Intermediate Similarity	NPC76982
0.7653	Intermediate Similarity	NPC34837
0.765	Intermediate Similarity	NPC70949
0.7647	Intermediate Similarity	NPC55772
0.7644	Intermediate Similarity	NPC17059
0.7644	Intermediate Similarity	NPC278434
0.7622	Intermediate Similarity	NPC161861
0.7621	Intermediate Similarity	NPC27041
0.7617	Intermediate Similarity	NPC138370
0.7606	Intermediate Similarity	NPC16659
0.7606	Intermediate Similarity	NPC88110
0.7598	Intermediate Similarity	NPC471194
0.7598	Intermediate Similarity	NPC471193
0.7596	Intermediate Similarity	NPC114637
0.7594	Intermediate Similarity	NPC145885
0.7594	Intermediate Similarity	NPC59269
0.7594	Intermediate Similarity	NPC14113
0.7594	Intermediate Similarity	NPC84827
0.759	Intermediate Similarity	NPC157828
0.759	Intermediate Similarity	NPC195239
0.759	Intermediate Similarity	NPC202812
0.7584	Intermediate Similarity	NPC325903
0.7581	Intermediate Similarity	NPC469529
0.757	Intermediate Similarity	NPC207686
0.7568	Intermediate Similarity	NPC262338
0.7553	Intermediate Similarity	NPC265710
0.7553	Intermediate Similarity	NPC11126
0.7551	Intermediate Similarity	NPC472293
0.7551	Intermediate Similarity	NPC11445
0.7549	Intermediate Similarity	NPC72956
0.7544	Intermediate Similarity	NPC105127
0.7543	Intermediate Similarity	NPC467188
0.7543	Intermediate Similarity	NPC314372
0.7541	Intermediate Similarity	NPC233380
0.7536	Intermediate Similarity	NPC472285
0.7529	Intermediate Similarity	NPC190296
0.7514	Intermediate Similarity	NPC469780
0.7514	Intermediate Similarity	NPC469767
0.7514	Intermediate Similarity	NPC469761
0.7514	Intermediate Similarity	NPC469783
0.7514	Intermediate Similarity	NPC469784
0.7514	Intermediate Similarity	NPC123906
0.7514	Intermediate Similarity	NPC469768
0.7514	Intermediate Similarity	NPC469779
0.7513	Intermediate Similarity	NPC73994
0.7512	Intermediate Similarity	NPC153980
0.7512	Intermediate Similarity	NPC6865
0.75	Intermediate Similarity	NPC473380
0.75	Intermediate Similarity	NPC111275
0.75	Intermediate Similarity	NPC240088
0.7487	Intermediate Similarity	NPC472292
0.7487	Intermediate Similarity	NPC110500
0.7487	Intermediate Similarity	NPC149155
0.7487	Intermediate Similarity	NPC228835
0.7487	Intermediate Similarity	NPC203468
0.7486	Intermediate Similarity	NPC274981
0.7485	Intermediate Similarity	NPC96102
0.7477	Intermediate Similarity	NPC101350
0.7472	Intermediate Similarity	NPC24678
0.7472	Intermediate Similarity	NPC105818
0.7471	Intermediate Similarity	NPC469766
0.746	Intermediate Similarity	NPC213468
0.746	Intermediate Similarity	NPC283219
0.746	Intermediate Similarity	NPC248041
0.746	Intermediate Similarity	NPC126709
0.7459	Intermediate Similarity	NPC78020
0.7458	Intermediate Similarity	NPC105811
0.7457	Intermediate Similarity	NPC73767
0.7457	Intermediate Similarity	NPC110126
0.7454	Intermediate Similarity	NPC70155
0.7451	Intermediate Similarity	NPC162860
0.745	Intermediate Similarity	NPC471944
0.7448	Intermediate Similarity	NPC15102
0.7447	Intermediate Similarity	NPC267885
0.7443	Intermediate Similarity	NPC159856
0.7442	Intermediate Similarity	NPC267853
0.7442	Intermediate Similarity	NPC84911
0.7438	Intermediate Similarity	NPC54420
0.7437	Intermediate Similarity	NPC472296
0.7437	Intermediate Similarity	NPC472297
0.7433	Intermediate Similarity	NPC477611
0.7431	Intermediate Similarity	NPC235685
0.743	Intermediate Similarity	NPC70406
0.7423	Intermediate Similarity	NPC255909
0.7421	Intermediate Similarity	NPC314919
0.7418	Intermediate Similarity	NPC80681
0.7416	Intermediate Similarity	NPC264285
0.7409	Intermediate Similarity	NPC94752
0.7409	Intermediate Similarity	NPC62749
0.7409	Intermediate Similarity	NPC235684
0.7407	Intermediate Similarity	NPC244897
0.7405	Intermediate Similarity	NPC56233
0.7404	Intermediate Similarity	NPC322064
0.7404	Intermediate Similarity	NPC471192
0.7398	Intermediate Similarity	NPC272458
0.7389	Intermediate Similarity	NPC259644
0.7389	Intermediate Similarity	NPC73952
0.7389	Intermediate Similarity	NPC469760
0.7389	Intermediate Similarity	NPC469765
0.7389	Intermediate Similarity	NPC25008
0.7389	Intermediate Similarity	NPC175602
0.7389	Intermediate Similarity	NPC469763
0.7389	Intermediate Similarity	NPC469786
0.7387	Intermediate Similarity	NPC171317
0.7384	Intermediate Similarity	NPC261195
0.7384	Intermediate Similarity	NPC29886
0.7383	Intermediate Similarity	NPC192712
0.7381	Intermediate Similarity	NPC269270
0.7374	Intermediate Similarity	NPC313889
0.7374	Intermediate Similarity	NPC473878

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 NPC304203 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	762
0.2-0.3	1000
0.3-0.4	2316
0.4-0.5	2104
0.5-0.6	1801
0.6-0.7	702
0.7-0.8	105
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8352	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD4848	Phase 1
0.8196	Intermediate Similarity	NPD2008	Discontinued
0.8131	Intermediate Similarity	NPD2411	Approved
0.8065	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD5473	Discontinued
0.7861	Intermediate Similarity	NPD7564	Discontinued
0.7853	Intermediate Similarity	NPD4922	Phase 2
0.7796	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD2479	Phase 3
0.7796	Intermediate Similarity	NPD2481	Approved
0.7778	Intermediate Similarity	NPD5426	Phase 3
0.775	Intermediate Similarity	NPD2509	Approved
0.775	Intermediate Similarity	NPD2510	Approved
0.7713	Intermediate Similarity	NPD3318	Approved
0.7713	Intermediate Similarity	NPD3320	Approved
0.7713	Intermediate Similarity	NPD3319	Phase 1
0.7688	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7618	Phase 3
0.768	Intermediate Similarity	NPD7619	Phase 3
0.7677	Intermediate Similarity	NPD2879	Approved
0.7677	Intermediate Similarity	NPD2881	Approved
0.7662	Intermediate Similarity	NPD2443	Approved
0.7662	Intermediate Similarity	NPD2442	Approved
0.766	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD3905	Phase 3
0.76	Intermediate Similarity	NPD5901	Discontinued
0.7586	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4051	Discontinued
0.7574	Intermediate Similarity	NPD6459	Phase 2
0.7573	Intermediate Similarity	NPD3393	Approved
0.7573	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD3389	Approved
0.7573	Intermediate Similarity	NPD3394	Approved
0.7551	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4075	Phase 2
0.7513	Intermediate Similarity	NPD6595	Phase 3
0.7512	Intermediate Similarity	NPD6987	Phase 1
0.7487	Intermediate Similarity	NPD2091	Phase 2
0.7487	Intermediate Similarity	NPD482	Approved
0.7487	Intermediate Similarity	NPD2096	Phase 2
0.7486	Intermediate Similarity	NPD2837	Discontinued
0.7485	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD2172	Phase 1
0.7471	Intermediate Similarity	NPD1722	Approved
0.7461	Intermediate Similarity	NPD4988	Discontinued
0.7459	Intermediate Similarity	NPD1343	Approved
0.7457	Intermediate Similarity	NPD786	Approved
0.7451	Intermediate Similarity	NPD2408	Discontinued
0.7451	Intermediate Similarity	NPD1600	Suspended
0.7448	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD6999	Discontinued
0.7435	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD2092	Phase 2
0.7435	Intermediate Similarity	NPD2095	Phase 2
0.7435	Intermediate Similarity	NPD2094	Phase 2
0.7426	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6664	Approved
0.7411	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD1270	Approved
0.7343	Intermediate Similarity	NPD7454	Approved
0.7343	Intermediate Similarity	NPD7455	Approved
0.732	Intermediate Similarity	NPD6217	Discontinued
0.732	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD3100	Discontinued
0.7308	Intermediate Similarity	NPD6787	Phase 2
0.7302	Intermediate Similarity	NPD5065	Approved
0.7297	Intermediate Similarity	NPD3323	Discontinued
0.7296	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3947	Discontinued
0.725	Intermediate Similarity	NPD2880	Discontinued
0.7243	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7666	Phase 3
0.7233	Intermediate Similarity	NPD7665	Phase 2
0.7231	Intermediate Similarity	NPD5809	Phase 3
0.7227	Intermediate Similarity	NPD6986	Phase 1
0.722	Intermediate Similarity	NPD7001	Phase 3
0.722	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6446	Discontinued
0.7212	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3961	Discontinued
0.7192	Intermediate Similarity	NPD5017	Discontinued
0.7184	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1506	Discontinued
0.7183	Intermediate Similarity	NPD6242	Discontinued
0.7177	Intermediate Similarity	NPD6954	Phase 2
0.7163	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD750	Phase 2
0.715	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5888	Phase 2
0.7136	Intermediate Similarity	NPD5198	Approved
0.7136	Intermediate Similarity	NPD5199	Approved
0.7129	Intermediate Similarity	NPD1982	Phase 1
0.7129	Intermediate Similarity	NPD6152	Phase 1
0.7129	Intermediate Similarity	NPD5475	Discontinued
0.7128	Intermediate Similarity	NPD2642	Approved
0.7128	Intermediate Similarity	NPD2639	Approved
0.7128	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD3583	Phase 2
0.71	Intermediate Similarity	NPD460	Discontinued
0.709	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4462	Approved
0.7088	Intermediate Similarity	NPD4463	Approved
0.7073	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4524	Discontinued
0.7065	Intermediate Similarity	NPD5853	Phase 3
0.7065	Intermediate Similarity	NPD5855	Phase 3
0.7064	Intermediate Similarity	NPD4845	Discontinued
0.7064	Intermediate Similarity	NPD6165	Phase 2
0.7064	Intermediate Similarity	NPD6164	Phase 2
0.7053	Intermediate Similarity	NPD1573	Approved
0.7053	Intermediate Similarity	NPD1575	Approved
0.7048	Intermediate Similarity	NPD7470	Discontinued
0.7047	Intermediate Similarity	NPD3505	Approved
0.7047	Intermediate Similarity	NPD3506	Approved
0.7043	Intermediate Similarity	NPD2213	Approved
0.7043	Intermediate Similarity	NPD2214	Approved
0.7039	Intermediate Similarity	NPD6176	Phase 1
0.7039	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7780	Approved
0.7032	Intermediate Similarity	NPD7781	Approved
0.7031	Intermediate Similarity	NPD4128	Approved
0.7031	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD1895	Discontinued
0.7026	Intermediate Similarity	NPD3178	Discontinued
0.7022	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8431	Approved
0.702	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4852	Phase 2
0.701	Intermediate Similarity	NPD4076	Approved
0.701	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4079	Approved
0.701	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4299	Phase 1
0.7	Intermediate Similarity	NPD2336	Approved
0.6995	Remote Similarity	NPD5446	Phase 2
0.699	Remote Similarity	NPD5106	Approved
0.699	Remote Similarity	NPD5105	Approved
0.6982	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4547	Phase 3
0.6971	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5400	Approved
0.6963	Remote Similarity	NPD5818	Discontinued
0.6963	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4181	Approved
0.6959	Remote Similarity	NPD2753	Discontinued
0.6948	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4883	Approved
0.6935	Remote Similarity	NPD4948	Discontinued
0.6935	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8093	Discontinued
0.693	Remote Similarity	NPD4429	Discontinued
0.6927	Remote Similarity	NPD3609	Approved
0.6927	Remote Similarity	NPD3610	Approved
0.6919	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD1403	Approved
0.6915	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD1404	Approved
0.6911	Remote Similarity	NPD2641	Approved
0.6911	Remote Similarity	NPD2640	Approved
0.6911	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD3238	Discontinued
0.6906	Remote Similarity	NPD5254	Discontinued
0.6906	Remote Similarity	NPD7790	Approved
0.6906	Remote Similarity	NPD7952	Approved
0.6906	Remote Similarity	NPD7950	Approved
0.6906	Remote Similarity	NPD7953	Approved
0.6906	Remote Similarity	NPD7789	Approved
0.6906	Remote Similarity	NPD7951	Approved
0.6906	Remote Similarity	NPD7791	Approved
0.6905	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5421	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD3833	Phase 3
0.6902	Remote Similarity	NPD3835	Phase 3
0.6901	Remote Similarity	NPD3794	Approved
0.6901	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8094	Discontinued
0.6901	Remote Similarity	NPD3795	Approved
0.69	Remote Similarity	NPD7175	Phase 1
0.6898	Remote Similarity	NPD4326	Phase 2
0.6897	Remote Similarity	NPD7406	Phase 2
0.6897	Remote Similarity	NPD7944	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