NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	187.07
Volume:	184.445
LogP:	-0.091
LogD:	0.563
LogS:	-0.444
# Rotatable Bonds:	0
TPSA:	50.68
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	3.097
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.289
MDCK Permeability:	8.032786354306154e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.904
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.66
Plasma Protein Binding (PPB):	44.46478271484375%
Volume Distribution (VD):	1.183
Pgp-substrate:	68.13968658447266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.788
CYP1A2-substrate:	0.494
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.268
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	7.082
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.475
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.341
Rat Oral Acute Toxicity:	0.269
Maximum Recommended Daily Dose:	0.667
Skin Sensitization:	0.203
Carcinogencity:	0.095
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.074

Download Data

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

Natural Product: NPC472289

Natural Product ID:	NPC472289
*Common Name:**	AGKYMAODIKREIE-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AGKYMAODIKREIE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H9N3O/c14-10-9-7(11-6-12-10)3-5-13-4-1-2-8(9)13/h1-2,4,6H,3,5H2,(H,11,12,14)
SMILES:	Oc1ncnc2c1c1cccn1CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357679
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001859] Pyridopyrimidines

*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
NPO33301	jiangella gansuensis	Species	Jiangellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25412141]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	20.0	%	PMID[479667]

☑ 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 NPC472289 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	744
0.1-0.2	10771
0.2-0.3	8811
0.3-0.4	15019
0.4-0.5	3723
0.5-0.6	2536
0.6-0.7	1028
0.7-0.8	55
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8713	High Similarity	NPC164664
0.8333	Intermediate Similarity	NPC278874
0.8314	Intermediate Similarity	NPC224632
0.8295	Intermediate Similarity	NPC208060
0.8239	Intermediate Similarity	NPC476688
0.8239	Intermediate Similarity	NPC105758
0.8239	Intermediate Similarity	NPC476686
0.8161	Intermediate Similarity	NPC97367
0.8122	Intermediate Similarity	NPC477891
0.8022	Intermediate Similarity	NPC144114
0.8	Intermediate Similarity	NPC254762
0.7929	Intermediate Similarity	NPC471603
0.7805	Intermediate Similarity	NPC130570
0.7709	Intermediate Similarity	NPC471178
0.7604	Intermediate Similarity	NPC329541
0.7598	Intermediate Similarity	NPC471177
0.7598	Intermediate Similarity	NPC59779
0.7598	Intermediate Similarity	NPC124542
0.756	Intermediate Similarity	NPC132631
0.756	Intermediate Similarity	NPC103687
0.7542	Intermediate Similarity	NPC25899
0.7526	Intermediate Similarity	NPC242209
0.75	Intermediate Similarity	NPC48192
0.7487	Intermediate Similarity	NPC230805
0.7473	Intermediate Similarity	NPC96890
0.7366	Intermediate Similarity	NPC317054
0.735	Intermediate Similarity	NPC200836
0.735	Intermediate Similarity	NPC53144
0.7344	Intermediate Similarity	NPC46580
0.7341	Intermediate Similarity	NPC60553
0.7316	Intermediate Similarity	NPC220765
0.7297	Intermediate Similarity	NPC314940
0.7297	Intermediate Similarity	NPC473764
0.7294	Intermediate Similarity	NPC30540
0.7293	Intermediate Similarity	NPC84508
0.7292	Intermediate Similarity	NPC171171
0.7287	Intermediate Similarity	NPC184964
0.7277	Intermediate Similarity	NPC204717
0.7273	Intermediate Similarity	NPC39092
0.7253	Intermediate Similarity	NPC131718
0.724	Intermediate Similarity	NPC314002
0.723	Intermediate Similarity	NPC2497
0.7214	Intermediate Similarity	NPC211813
0.7194	Intermediate Similarity	NPC324149
0.719	Intermediate Similarity	NPC250178
0.7184	Intermediate Similarity	NPC242923
0.7174	Intermediate Similarity	NPC473057
0.7143	Intermediate Similarity	NPC475070
0.7143	Intermediate Similarity	NPC129721
0.7136	Intermediate Similarity	NPC85273
0.7128	Intermediate Similarity	NPC471294
0.7117	Intermediate Similarity	NPC295452
0.7117	Intermediate Similarity	NPC171393
0.7116	Intermediate Similarity	NPC107160
0.7107	Intermediate Similarity	NPC99666
0.71	Intermediate Similarity	NPC192315
0.7083	Intermediate Similarity	NPC212125
0.7081	Intermediate Similarity	NPC102423
0.7065	Intermediate Similarity	NPC476167
0.7059	Intermediate Similarity	NPC472259
0.7053	Intermediate Similarity	NPC203754
0.7053	Intermediate Similarity	NPC150048
0.705	Intermediate Similarity	NPC77555
0.7047	Intermediate Similarity	NPC48938
0.7033	Intermediate Similarity	NPC282247
0.7024	Intermediate Similarity	NPC476121
0.7024	Intermediate Similarity	NPC476124
0.701	Intermediate Similarity	NPC284559
0.7005	Intermediate Similarity	NPC108469
0.7005	Intermediate Similarity	NPC49217
0.7	Intermediate Similarity	NPC237740
0.6986	Remote Similarity	NPC128084
0.6984	Remote Similarity	NPC252590
0.6983	Remote Similarity	NPC161292
0.6982	Remote Similarity	NPC306397
0.698	Remote Similarity	NPC287437
0.6979	Remote Similarity	NPC72980
0.6974	Remote Similarity	NPC295158
0.6967	Remote Similarity	NPC62995
0.6964	Remote Similarity	NPC151489
0.695	Remote Similarity	NPC326634
0.6948	Remote Similarity	NPC193267
0.6948	Remote Similarity	NPC213530
0.6942	Remote Similarity	NPC477113
0.6935	Remote Similarity	NPC177404
0.693	Remote Similarity	NPC472067
0.693	Remote Similarity	NPC472031
0.693	Remote Similarity	NPC472066
0.6923	Remote Similarity	NPC80596
0.6919	Remote Similarity	NPC256893
0.6916	Remote Similarity	NPC472068
0.6912	Remote Similarity	NPC214980
0.6907	Remote Similarity	NPC219963
0.6907	Remote Similarity	NPC266551
0.6907	Remote Similarity	NPC161887
0.69	Remote Similarity	NPC106937
0.6898	Remote Similarity	NPC162268
0.6897	Remote Similarity	NPC63109
0.6895	Remote Similarity	NPC121658
0.6895	Remote Similarity	NPC158129
0.6895	Remote Similarity	NPC14651
0.6895	Remote Similarity	NPC116622
0.6893	Remote Similarity	NPC470500
0.6891	Remote Similarity	NPC42979
0.689	Remote Similarity	NPC5145
0.6882	Remote Similarity	NPC165370
0.6881	Remote Similarity	NPC156704
0.6878	Remote Similarity	NPC470678
0.6875	Remote Similarity	NPC18348
0.6875	Remote Similarity	NPC477111
0.6875	Remote Similarity	NPC224764
0.6859	Remote Similarity	NPC313791
0.6859	Remote Similarity	NPC474409
0.6857	Remote Similarity	NPC29702
0.6854	Remote Similarity	NPC304926
0.6854	Remote Similarity	NPC476041
0.6848	Remote Similarity	NPC63562
0.6847	Remote Similarity	NPC212213
0.6845	Remote Similarity	NPC475774
0.6842	Remote Similarity	NPC476518
0.6833	Remote Similarity	NPC159856
0.6831	Remote Similarity	NPC153769
0.6829	Remote Similarity	NPC232727
0.6828	Remote Similarity	NPC230869
0.6825	Remote Similarity	NPC202605
0.6825	Remote Similarity	NPC112206
0.6821	Remote Similarity	NPC324611
0.6813	Remote Similarity	NPC282531
0.6808	Remote Similarity	NPC477110
0.6804	Remote Similarity	NPC232340
0.6798	Remote Similarity	NPC267928
0.6791	Remote Similarity	NPC322976
0.6791	Remote Similarity	NPC324203
0.6791	Remote Similarity	NPC63338
0.6791	Remote Similarity	NPC279918
0.6787	Remote Similarity	NPC160666
0.6786	Remote Similarity	NPC133306
0.6784	Remote Similarity	NPC32771
0.678	Remote Similarity	NPC315491
0.678	Remote Similarity	NPC45459
0.678	Remote Similarity	NPC249040
0.678	Remote Similarity	NPC121772
0.6779	Remote Similarity	NPC323345
0.6779	Remote Similarity	NPC470164
0.6776	Remote Similarity	NPC40070
0.6774	Remote Similarity	NPC269919
0.6774	Remote Similarity	NPC132680
0.6774	Remote Similarity	NPC212742
0.6771	Remote Similarity	NPC111624
0.6765	Remote Similarity	NPC474916
0.6762	Remote Similarity	NPC174758
0.6762	Remote Similarity	NPC174672
0.6755	Remote Similarity	NPC282231
0.6753	Remote Similarity	NPC326575
0.6749	Remote Similarity	NPC222018
0.674	Remote Similarity	NPC86288
0.6737	Remote Similarity	NPC98187
0.6733	Remote Similarity	NPC307963
0.6731	Remote Similarity	NPC285558
0.673	Remote Similarity	NPC309845
0.673	Remote Similarity	NPC123976
0.673	Remote Similarity	NPC167860
0.6728	Remote Similarity	NPC473317
0.6723	Remote Similarity	NPC74619
0.672	Remote Similarity	NPC141353
0.6716	Remote Similarity	NPC208751
0.6716	Remote Similarity	NPC92111
0.6715	Remote Similarity	NPC57398
0.6713	Remote Similarity	NPC308906
0.6713	Remote Similarity	NPC48317
0.6712	Remote Similarity	NPC21461
0.6703	Remote Similarity	NPC73952
0.6703	Remote Similarity	NPC469786
0.6703	Remote Similarity	NPC469760
0.6703	Remote Similarity	NPC259644
0.6703	Remote Similarity	NPC469765
0.6703	Remote Similarity	NPC25008
0.6703	Remote Similarity	NPC469763
0.6701	Remote Similarity	NPC134586
0.6701	Remote Similarity	NPC288943
0.67	Remote Similarity	NPC296527
0.6699	Remote Similarity	NPC19872
0.6699	Remote Similarity	NPC176538
0.6699	Remote Similarity	NPC213308
0.6686	Remote Similarity	NPC471313
0.6686	Remote Similarity	NPC471311
0.6685	Remote Similarity	NPC24678
0.6685	Remote Similarity	NPC471323
0.6685	Remote Similarity	NPC105818
0.6684	Remote Similarity	NPC24864
0.6684	Remote Similarity	NPC259545
0.6683	Remote Similarity	NPC239954
0.6683	Remote Similarity	NPC477166
0.6683	Remote Similarity	NPC304187
0.6682	Remote Similarity	NPC469589
0.6667	Remote Similarity	NPC76748
0.6667	Remote Similarity	NPC472193
0.6667	Remote Similarity	NPC75540
0.6667	Remote Similarity	NPC284678
0.6667	Remote Similarity	NPC212376

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 NPC472289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	855
0.2-0.3	572
0.3-0.4	1980
0.4-0.5	2277
0.5-0.6	1888
0.6-0.7	1091
0.7-0.8	104
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8325	Intermediate Similarity	NPD1197	Approved
0.8095	Intermediate Similarity	NPD5885	Approved
0.8021	Intermediate Similarity	NPD4615	Phase 2
0.7979	Intermediate Similarity	NPD5428	Discontinued
0.79	Intermediate Similarity	NPD7112	Discontinued
0.7853	Intermediate Similarity	NPD444	Approved
0.7831	Intermediate Similarity	NPD2127	Suspended
0.7809	Intermediate Similarity	NPD926	Approved
0.7809	Intermediate Similarity	NPD925	Approved
0.779	Intermediate Similarity	NPD1599	Approved
0.776	Intermediate Similarity	NPD3830	Phase 1
0.7754	Intermediate Similarity	NPD706	Phase 1
0.7753	Intermediate Similarity	NPD5925	Phase 1
0.7749	Intermediate Similarity	NPD4998	Phase 3
0.7749	Intermediate Similarity	NPD4999	Phase 3
0.7749	Intermediate Similarity	NPD1912	Approved
0.7725	Intermediate Similarity	NPD2757	Phase 2
0.7692	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD4673	Phase 2
0.7667	Intermediate Similarity	NPD424	Approved
0.7667	Intermediate Similarity	NPD425	Approved
0.7653	Intermediate Similarity	NPD6132	Phase 1
0.7641	Intermediate Similarity	NPD2536	Discontinued
0.7635	Intermediate Similarity	NPD6958	Approved
0.7635	Intermediate Similarity	NPD6957	Approved
0.7596	Intermediate Similarity	NPD4403	Phase 3
0.7596	Intermediate Similarity	NPD4401	Phase 2
0.7588	Intermediate Similarity	NPD796	Phase 2
0.7576	Intermediate Similarity	NPD1915	Phase 1
0.7568	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4612	Discontinued
0.7549	Intermediate Similarity	NPD6711	Approved
0.7524	Intermediate Similarity	NPD537	Phase 2
0.7524	Intermediate Similarity	NPD534	Phase 2
0.7513	Intermediate Similarity	NPD2814	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7423	Phase 2
0.7487	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD3013	Phase 3
0.7474	Intermediate Similarity	NPD7757	Approved
0.7474	Intermediate Similarity	NPD7758	Approved
0.743	Intermediate Similarity	NPD639	Discontinued
0.7424	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7188	Phase 3
0.7411	Intermediate Similarity	NPD3814	Phase 1
0.7404	Intermediate Similarity	NPD6856	Discontinued
0.7403	Intermediate Similarity	NPD1016	Phase 2
0.7403	Intermediate Similarity	NPD1015	Phase 2
0.7397	Intermediate Similarity	NPD7068	Approved
0.7397	Intermediate Similarity	NPD7067	Approved
0.7383	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6721	Phase 1
0.7377	Intermediate Similarity	NPD1215	Discontinued
0.7376	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5529	Phase 1
0.7373	Intermediate Similarity	NPD2414	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2993	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4306	Phase 1
0.7347	Intermediate Similarity	NPD6594	Discontinued
0.7344	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2333	Discontinued
0.7333	Intermediate Similarity	NPD3234	Phase 3
0.7333	Intermediate Similarity	NPD4945	Discontinued
0.7333	Intermediate Similarity	NPD3233	Phase 2
0.733	Intermediate Similarity	NPD5413	Phase 2
0.7322	Intermediate Similarity	NPD1333	Phase 3
0.732	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3330	Phase 1
0.7316	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1037	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3224	Phase 2
0.7302	Intermediate Similarity	NPD2600	Approved
0.7302	Intermediate Similarity	NPD2599	Approved
0.7302	Intermediate Similarity	NPD2601	Approved
0.7283	Intermediate Similarity	NPD1649	Discontinued
0.7282	Intermediate Similarity	NPD1234	Discontinued
0.7277	Intermediate Similarity	NPD6165	Phase 2
0.7277	Intermediate Similarity	NPD6164	Phase 2
0.7273	Intermediate Similarity	NPD5065	Approved
0.7273	Intermediate Similarity	NPD7419	Discontinued
0.7268	Intermediate Similarity	NPD2410	Phase 2
0.7268	Intermediate Similarity	NPD3439	Approved
0.7267	Intermediate Similarity	NPD852	Discontinued
0.7258	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3813	Approved
0.7251	Intermediate Similarity	NPD1954	Phase 1
0.7245	Intermediate Similarity	NPD3403	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2751	Phase 1
0.7231	Intermediate Similarity	NPD6022	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6352	Phase 2
0.723	Intermediate Similarity	NPD7051	Phase 3
0.7228	Intermediate Similarity	NPD5425	Phase 1
0.7227	Intermediate Similarity	NPD3872	Phase 3
0.7217	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4187	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5255	Approved
0.7194	Intermediate Similarity	NPD6887	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3406	Suspended
0.7181	Intermediate Similarity	NPD9690	Approved
0.7172	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6151	Phase 2
0.7162	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5827	Discontinued
0.715	Intermediate Similarity	NPD5828	Phase 2
0.715	Intermediate Similarity	NPD1273	Discontinued
0.7143	Intermediate Similarity	NPD1572	Phase 2
0.7135	Intermediate Similarity	NPD1313	Approved
0.7129	Intermediate Similarity	NPD2412	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5324	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1838	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4902	Discontinued
0.7113	Intermediate Similarity	NPD2872	Phase 2
0.7111	Intermediate Similarity	NPD3262	Approved
0.7108	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2060	Approved
0.7107	Intermediate Similarity	NPD3404	Approved
0.7104	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6794	Approved
0.7097	Intermediate Similarity	NPD8004	Discontinued
0.7085	Intermediate Similarity	NPD5534	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1571	Phase 2
0.7083	Intermediate Similarity	NPD9284	Approved
0.7081	Intermediate Similarity	NPD6528	Phase 1
0.7074	Intermediate Similarity	NPD6458	Discontinued
0.7071	Intermediate Similarity	NPD2362	Approved
0.7068	Intermediate Similarity	NPD3409	Phase 1
0.7067	Intermediate Similarity	NPD3976	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD112	Approved
0.7065	Intermediate Similarity	NPD9705	Discontinued
0.7059	Intermediate Similarity	NPD9582	Phase 3
0.7059	Intermediate Similarity	NPD3500	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD1286	Suspended
0.7056	Intermediate Similarity	NPD6829	Phase 2
0.7056	Intermediate Similarity	NPD5045	Phase 2
0.7053	Intermediate Similarity	NPD5100	Phase 3
0.7053	Intermediate Similarity	NPD8321	Discontinued
0.7048	Intermediate Similarity	NPD6772	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD509	Phase 3
0.7037	Intermediate Similarity	NPD6327	Phase 1
0.7037	Intermediate Similarity	NPD6326	Phase 2
0.7035	Intermediate Similarity	NPD5644	Phase 1
0.7031	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD174	Discontinued
0.7026	Intermediate Similarity	NPD3913	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1258	Discontinued
0.7023	Intermediate Similarity	NPD3938	Phase 1
0.702	Intermediate Similarity	NPD3431	Approved
0.702	Intermediate Similarity	NPD3430	Approved
0.7016	Intermediate Similarity	NPD7111	Discontinued
0.701	Intermediate Similarity	NPD2364	Suspended
0.7005	Intermediate Similarity	NPD7409	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6970	Phase 2
0.7	Intermediate Similarity	NPD7935	Phase 2
0.7	Intermediate Similarity	NPD4358	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4533	Clinical (unspecified phase)
0.699	Remote Similarity	NPD2383	Phase 1
0.6985	Remote Similarity	NPD9695	Approved
0.6985	Remote Similarity	NPD1173	Approved
0.6982	Remote Similarity	NPD9080	Approved
0.6974	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4148	Approved
0.6968	Remote Similarity	NPD1259	Discontinued
0.6965	Remote Similarity	NPD7948	Phase 1
0.6964	Remote Similarity	NPD6490	Phase 2
0.6961	Remote Similarity	NPD3931	Approved
0.6961	Remote Similarity	NPD5486	Discontinued
0.6961	Remote Similarity	NPD3928	Approved
0.6957	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3889	Approved
0.6951	Remote Similarity	NPD4858	Phase 2
0.6947	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5584	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4702	Approved
0.6944	Remote Similarity	NPD4703	Approved
0.6943	Remote Similarity	NPD5508	Phase 1
0.6942	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2062	Phase 2
0.6938	Remote Similarity	NPD4563	Phase 2
0.6933	Remote Similarity	NPD6572	Phase 2
0.6933	Remote Similarity	NPD6573	Phase 3
0.6931	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4886	Phase 2
0.6923	Remote Similarity	NPD2882	Phase 1
0.6923	Remote Similarity	NPD1257	Approved
0.6923	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7006	Approved
0.691	Remote Similarity	NPD7923	Phase 2

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