NPASS Compound

Structure

CID214626 OpenBabel06191716002D 25 31 0 0 1 0 0 0 0 0999 V2000 1.6932 1.6053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8744 0.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9475 1.8266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3100 0.3139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0808 0.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3625 2.4150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1439 2.8662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8873 -0.3082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9255 1.5127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9267 -0.8811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7071 1.9640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7070 1.0613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9257 0.6101 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.3832 1.2914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5644 0.5351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5178 -0.4885 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1441 1.9639 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.2512 -0.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1441 0.1589 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3623 0.6102 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3625 1.5127 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.9254 2.4150 0.0000 N 0 0 3 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 0.3707 -1.3177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2399 -0.6820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 2 0 0 0 0 4 15 2 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 7 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.17
Volume:	338.269
LogP:	1.775
LogD:	1.855
LogS:	-2.592
# Rotatable Bonds:	0
TPSA:	32.78
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	5.723
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.684
MDCK Permeability:	5.542056533158757e-05
Pgp-inhibitor:	0.768
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	0.323
30% Bioavailability (F30%):	0.801

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	55.78098678588867%
Volume Distribution (VD):	2.18
Pgp-substrate:	41.581912994384766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.672
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.419
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.572
CYP3A4-inhibitor:	0.184
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	17.303
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.074
Carcinogencity:	0.964
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC214626

Natural Product ID:	NPC214626
*Common Name:**	4A,5,5A,7,8,13A,15,15A,15B,16-Decahydro-2H-4,6-Methanoindolo[3,2,1-Ij]Oxepino[2,3,4-De]Pyrrolo[2,3-H]Quinoline-14-One
IUPAC Name:	4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one
Synonyms:
Standard InCHIKey:	QMGVPVSNSZLJIA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H22N2O2/c24-18-10-16-19-13-9-17-21(6-7-22(17)11-12(13)5-8-25-16)14-3-1-2-4-15(14)23(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2
SMILES:	c1ccc2c(c1)C13CCN4CC5=CCOC6CC(=O)N2C3C6C5CC14
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1609139
PubChem CID:	5304
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos alkaloids

*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
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6067	Strychnos ignatii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	3
Potency	3

Activity Type	# Activity
Individual Protein	1
ORGANISM	2
Others	1
Protein-Protein Interaction	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[544313]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	5011.9	nM	PMID[544313]
NPT2	Others	Unspecified		Potency	n.a.	7079.5	nM	PMID[544313]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-9.3	%	PMID[544314]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.02	%	PMID[544315]

☑ 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 NPC214626 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	303
0.1-0.2	1369
0.2-0.3	4029
0.3-0.4	20161
0.4-0.5	12467
0.5-0.6	3627
0.6-0.7	561
0.7-0.8	148
0.8-0.85	19
0.85-0.9	5
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC139085
1.0	High Similarity	NPC251212
0.9563	High Similarity	NPC260075
0.9226	High Similarity	NPC22689
0.9226	High Similarity	NPC105055
0.8908	High Similarity	NPC162440
0.8788	High Similarity	NPC96901
0.8757	High Similarity	NPC67904
0.8757	High Similarity	NPC138830
0.8564	High Similarity	NPC329833
0.8528	High Similarity	NPC225319
0.8519	High Similarity	NPC113946
0.8263	Intermediate Similarity	NPC472106
0.8253	Intermediate Similarity	NPC282339
0.8253	Intermediate Similarity	NPC99632
0.8148	Intermediate Similarity	NPC159815
0.8144	Intermediate Similarity	NPC472120
0.8144	Intermediate Similarity	NPC472101
0.814	Intermediate Similarity	NPC264482
0.814	Intermediate Similarity	NPC203202
0.8121	Intermediate Similarity	NPC29285
0.8084	Intermediate Similarity	NPC248117
0.8024	Intermediate Similarity	NPC193410
0.7964	Intermediate Similarity	NPC61013
0.7931	Intermediate Similarity	NPC320147
0.7929	Intermediate Similarity	NPC472117
0.7921	Intermediate Similarity	NPC52262
0.7919	Intermediate Similarity	NPC473743
0.7895	Intermediate Similarity	NPC214960
0.7895	Intermediate Similarity	NPC279527
0.7857	Intermediate Similarity	NPC10653
0.7857	Intermediate Similarity	NPC318525
0.7849	Intermediate Similarity	NPC223595
0.7849	Intermediate Similarity	NPC224970
0.7849	Intermediate Similarity	NPC167724
0.7841	Intermediate Similarity	NPC99043
0.7841	Intermediate Similarity	NPC218594
0.7841	Intermediate Similarity	NPC6974
0.7824	Intermediate Similarity	NPC176983
0.7824	Intermediate Similarity	NPC286871
0.7809	Intermediate Similarity	NPC159963
0.7784	Intermediate Similarity	NPC186669
0.7772	Intermediate Similarity	NPC221687
0.7765	Intermediate Similarity	NPC309531
0.7765	Intermediate Similarity	NPC472102
0.7764	Intermediate Similarity	NPC22082
0.7764	Intermediate Similarity	NPC186284
0.7751	Intermediate Similarity	NPC123241
0.7719	Intermediate Similarity	NPC293458
0.7714	Intermediate Similarity	NPC476425
0.7705	Intermediate Similarity	NPC25401
0.7701	Intermediate Similarity	NPC469915
0.7679	Intermediate Similarity	NPC478076
0.7665	Intermediate Similarity	NPC243756
0.7637	Intermediate Similarity	NPC14994
0.7636	Intermediate Similarity	NPC264589
0.7602	Intermediate Similarity	NPC36495
0.754	Intermediate Similarity	NPC97100
0.754	Intermediate Similarity	NPC473375
0.7529	Intermediate Similarity	NPC475420
0.7529	Intermediate Similarity	NPC473297
0.7529	Intermediate Similarity	NPC471124
0.7528	Intermediate Similarity	NPC476441
0.7527	Intermediate Similarity	NPC259626
0.7526	Intermediate Similarity	NPC471512
0.7473	Intermediate Similarity	NPC97584
0.7473	Intermediate Similarity	NPC473004
0.7473	Intermediate Similarity	NPC2933
0.7472	Intermediate Similarity	NPC329338
0.7472	Intermediate Similarity	NPC469726
0.7457	Intermediate Similarity	NPC143457
0.7446	Intermediate Similarity	NPC21425
0.7418	Intermediate Similarity	NPC256288
0.7416	Intermediate Similarity	NPC285622
0.7416	Intermediate Similarity	NPC473880
0.7412	Intermediate Similarity	NPC122106
0.7407	Intermediate Similarity	NPC471123
0.7403	Intermediate Similarity	NPC11149
0.7403	Intermediate Similarity	NPC286994
0.7399	Intermediate Similarity	NPC471122
0.7389	Intermediate Similarity	NPC476326
0.7366	Intermediate Similarity	NPC473298
0.7356	Intermediate Similarity	NPC474058
0.7353	Intermediate Similarity	NPC475763
0.7353	Intermediate Similarity	NPC66936
0.7348	Intermediate Similarity	NPC321211
0.7345	Intermediate Similarity	NPC475248
0.7345	Intermediate Similarity	NPC63047
0.7337	Intermediate Similarity	NPC473007
0.7337	Intermediate Similarity	NPC322621
0.7323	Intermediate Similarity	NPC10732
0.7314	Intermediate Similarity	NPC469741
0.7306	Intermediate Similarity	NPC473005
0.7297	Intermediate Similarity	NPC473615
0.7292	Intermediate Similarity	NPC475489
0.7288	Intermediate Similarity	NPC472114
0.7288	Intermediate Similarity	NPC472115
0.7286	Intermediate Similarity	NPC473006
0.7283	Intermediate Similarity	NPC469536
0.7277	Intermediate Similarity	NPC100863
0.7277	Intermediate Similarity	NPC288110
0.7258	Intermediate Similarity	NPC229484
0.7258	Intermediate Similarity	NPC181928
0.7257	Intermediate Similarity	NPC201424
0.7251	Intermediate Similarity	NPC154602
0.7249	Intermediate Similarity	NPC470485
0.7228	Intermediate Similarity	NPC477159
0.7225	Intermediate Similarity	NPC161827
0.7219	Intermediate Similarity	NPC292675
0.7211	Intermediate Similarity	NPC243626
0.7211	Intermediate Similarity	NPC230313
0.7211	Intermediate Similarity	NPC34717
0.7182	Intermediate Similarity	NPC13367
0.7181	Intermediate Similarity	NPC473008
0.7176	Intermediate Similarity	NPC212799
0.7174	Intermediate Similarity	NPC476428
0.7169	Intermediate Similarity	NPC130251
0.7166	Intermediate Similarity	NPC285841
0.716	Intermediate Similarity	NPC116519
0.7159	Intermediate Similarity	NPC315368
0.7151	Intermediate Similarity	NPC476095
0.7143	Intermediate Similarity	NPC77777
0.7143	Intermediate Similarity	NPC470483
0.7135	Intermediate Similarity	NPC90967
0.7111	Intermediate Similarity	NPC472118
0.7108	Intermediate Similarity	NPC469560
0.7102	Intermediate Similarity	NPC310403
0.7102	Intermediate Similarity	NPC243673
0.7102	Intermediate Similarity	NPC97380
0.7102	Intermediate Similarity	NPC148468
0.7102	Intermediate Similarity	NPC63210
0.7102	Intermediate Similarity	NPC263709
0.7093	Intermediate Similarity	NPC473329
0.709	Intermediate Similarity	NPC473569
0.7059	Intermediate Similarity	NPC472107
0.7059	Intermediate Similarity	NPC79062
0.7056	Intermediate Similarity	NPC33507
0.7053	Intermediate Similarity	NPC22476
0.7053	Intermediate Similarity	NPC203628
0.7045	Intermediate Similarity	NPC222029
0.7041	Intermediate Similarity	NPC162730
0.7041	Intermediate Similarity	NPC52801
0.7039	Intermediate Similarity	NPC52059
0.7039	Intermediate Similarity	NPC470069
0.7033	Intermediate Similarity	NPC276993
0.7033	Intermediate Similarity	NPC181138
0.7033	Intermediate Similarity	NPC298851
0.7033	Intermediate Similarity	NPC293255
0.7033	Intermediate Similarity	NPC21752
0.7033	Intermediate Similarity	NPC210415
0.7033	Intermediate Similarity	NPC473458
0.7026	Intermediate Similarity	NPC127178
0.7011	Intermediate Similarity	NPC285381
0.7	Intermediate Similarity	NPC5630
0.6995	Remote Similarity	NPC475097
0.6995	Remote Similarity	NPC470548
0.6964	Remote Similarity	NPC243162
0.6954	Remote Similarity	NPC1464
0.6954	Remote Similarity	NPC474116
0.6949	Remote Similarity	NPC153694
0.6949	Remote Similarity	NPC104345
0.6949	Remote Similarity	NPC211525
0.6947	Remote Similarity	NPC284706
0.6942	Remote Similarity	NPC222046
0.694	Remote Similarity	NPC307640
0.6936	Remote Similarity	NPC242000
0.6923	Remote Similarity	NPC301760
0.6915	Remote Similarity	NPC245741
0.6907	Remote Similarity	NPC303214
0.6897	Remote Similarity	NPC127996
0.6893	Remote Similarity	NPC477157
0.6893	Remote Similarity	NPC477156
0.6885	Remote Similarity	NPC355
0.6881	Remote Similarity	NPC126066
0.6878	Remote Similarity	NPC234772
0.6872	Remote Similarity	NPC471513
0.685	Remote Similarity	NPC477173
0.685	Remote Similarity	NPC477161
0.685	Remote Similarity	NPC246140
0.685	Remote Similarity	NPC195787
0.6842	Remote Similarity	NPC469537
0.6842	Remote Similarity	NPC308197
0.6842	Remote Similarity	NPC282092
0.6839	Remote Similarity	NPC109787
0.6837	Remote Similarity	NPC132874
0.6837	Remote Similarity	NPC138615
0.6837	Remote Similarity	NPC218733
0.6837	Remote Similarity	NPC265642
0.6834	Remote Similarity	NPC477179
0.6833	Remote Similarity	NPC85651
0.6833	Remote Similarity	NPC472121
0.6825	Remote Similarity	NPC472119
0.6824	Remote Similarity	NPC470301
0.6821	Remote Similarity	NPC472100
0.6818	Remote Similarity	NPC232600
0.6816	Remote Similarity	NPC470488
0.6813	Remote Similarity	NPC278887
0.68	Remote Similarity	NPC477178
0.68	Remote Similarity	NPC254850
0.68	Remote Similarity	NPC87714

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 NPC214626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	569
0.2-0.3	706
0.3-0.4	1680
0.4-0.5	3710
0.5-0.6	2056
0.6-0.7	220
0.7-0.8	7
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
0.7318	Intermediate Similarity	NPD5997	Discontinued
0.7134	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7487	Discontinued
0.7083	Intermediate Similarity	NPD6566	Discontinued
0.6977	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4121	Phase 3
0.6971	Remote Similarity	NPD4120	Approved
0.6932	Remote Similarity	NPD5741	Approved
0.6932	Remote Similarity	NPD5742	Approved
0.6932	Remote Similarity	NPD5743	Approved
0.6854	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8400	Approved
0.6818	Remote Similarity	NPD8401	Approved
0.6818	Remote Similarity	NPD8402	Approved
0.6806	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5918	Discontinued
0.6771	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6805	Discontinued
0.6755	Remote Similarity	NPD6878	Phase 2
0.6755	Remote Similarity	NPD6879	Phase 2
0.6722	Remote Similarity	NPD7599	Phase 2
0.672	Remote Similarity	NPD3423	Phase 2
0.672	Remote Similarity	NPD3422	Phase 3
0.6707	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7600	Phase 2
0.6684	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4601	Approved
0.6683	Remote Similarity	NPD4600	Approved
0.6667	Remote Similarity	NPD7295	Approved
0.6667	Remote Similarity	NPD5931	Phase 3
0.6667	Remote Similarity	NPD5932	Phase 3
0.6667	Remote Similarity	NPD5933	Phase 3
0.6667	Remote Similarity	NPD7606	Phase 3
0.665	Remote Similarity	NPD6238	Discontinued
0.6649	Remote Similarity	NPD5600	Discontinued
0.6617	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6995	Phase 1
0.6592	Remote Similarity	NPD2790	Discontinued
0.6591	Remote Similarity	NPD7478	Approved
0.659	Remote Similarity	NPD6768	Approved
0.6584	Remote Similarity	NPD7205	Discontinued
0.6568	Remote Similarity	NPD5184	Approved
0.6568	Remote Similarity	NPD5185	Approved
0.6568	Remote Similarity	NPD5182	Approved
0.6566	Remote Similarity	NPD4549	Discontinued
0.6561	Remote Similarity	NPD5179	Approved
0.6561	Remote Similarity	NPD5181	Approved
0.6561	Remote Similarity	NPD5180	Approved
0.6554	Remote Similarity	NPD5941	Approved
0.6554	Remote Similarity	NPD5942	Approved
0.6554	Remote Similarity	NPD4682	Phase 2
0.6552	Remote Similarity	NPD4430	Phase 2
0.6552	Remote Similarity	NPD2820	Phase 3
0.6552	Remote Similarity	NPD7082	Approved
0.655	Remote Similarity	NPD6358	Phase 2
0.655	Remote Similarity	NPD2670	Approved
0.6543	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1663	Discontinued
0.6517	Remote Similarity	NPD4501	Approved
0.6517	Remote Similarity	NPD4500	Approved
0.6514	Remote Similarity	NPD7259	Approved
0.6494	Remote Similarity	NPD2365	Approved
0.6492	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6489	Phase 3
0.6485	Remote Similarity	NPD6321	Discontinued
0.6484	Remote Similarity	NPD8630	Approved
0.6474	Remote Similarity	NPD5312	Approved
0.6474	Remote Similarity	NPD5313	Approved
0.6471	Remote Similarity	NPD5183	Approved
0.6471	Remote Similarity	NPD5186	Approved
0.6471	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5504	Discontinued
0.644	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3625	Discontinued
0.6429	Remote Similarity	NPD4334	Discontinued
0.6429	Remote Similarity	NPD4365	Phase 2
0.6422	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6457	Approved
0.6402	Remote Similarity	NPD3377	Discontinued
0.6396	Remote Similarity	NPD4499	Approved
0.6393	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7688	Phase 1
0.6387	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6622	Phase 1
0.6384	Remote Similarity	NPD6017	Discontinued
0.6378	Remote Similarity	NPD6891	Phase 2
0.6377	Remote Similarity	NPD2916	Discontinued
0.6369	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7595	Discontinued
0.6364	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5823	Approved
0.6364	Remote Similarity	NPD5024	Approved
0.6364	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6557	Phase 2
0.6358	Remote Similarity	NPD2569	Approved
0.6358	Remote Similarity	NPD2567	Approved
0.6349	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8025	Phase 2
0.6343	Remote Similarity	NPD2093	Discontinued
0.6339	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6395	Phase 2
0.6337	Remote Similarity	NPD2791	Discontinued
0.6335	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5131	Approved
0.6324	Remote Similarity	NPD2506	Approved
0.6322	Remote Similarity	NPD3170	Approved
0.6322	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4330	Approved
0.6321	Remote Similarity	NPD4329	Approved
0.6313	Remote Similarity	NPD1802	Approved
0.6313	Remote Similarity	NPD1801	Approved
0.6312	Remote Similarity	NPD3551	Approved
0.631	Remote Similarity	NPD7036	Phase 3
0.631	Remote Similarity	NPD5993	Phase 1
0.631	Remote Similarity	NPD7035	Approved
0.631	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD3792	Approved
0.6301	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5991	Approved
0.6296	Remote Similarity	NPD5990	Approved
0.6296	Remote Similarity	NPD7795	Phase 2
0.6294	Remote Similarity	NPD6483	Approved
0.6294	Remote Similarity	NPD6484	Approved
0.6289	Remote Similarity	NPD3471	Approved
0.6289	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3470	Approved
0.6287	Remote Similarity	NPD3828	Approved
0.6286	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD7186	Phase 3
0.6283	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8240	Discontinued
0.628	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7824	Approved
0.6271	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4602	Approved
0.6267	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD8016	Phase 3
0.6264	Remote Similarity	NPD6342	Discontinued
0.6262	Remote Similarity	NPD6176	Phase 1
0.6258	Remote Similarity	NPD6343	Approved
0.6258	Remote Similarity	NPD6345	Approved
0.6258	Remote Similarity	NPD2994	Approved
0.6257	Remote Similarity	NPD3141	Discontinued
0.6257	Remote Similarity	NPD3790	Phase 2
0.6256	Remote Similarity	NPD5071	Phase 2
0.6256	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6518	Discontinued
0.625	Remote Similarity	NPD2010	Phase 3
0.625	Remote Similarity	NPD4315	Phase 2
0.6244	Remote Similarity	NPD5444	Phase 1
0.6243	Remote Similarity	NPD7126	Discontinued
0.6242	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6357	Discontinued
0.623	Remote Similarity	NPD5086	Approved
0.623	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7854	Phase 2
0.6228	Remote Similarity	NPD6025	Phase 1
0.6223	Remote Similarity	NPD5430	Discontinued
0.622	Remote Similarity	NPD8027	Approved
0.622	Remote Similarity	NPD7666	Phase 3
0.622	Remote Similarity	NPD7665	Phase 2
0.6218	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD3449	Discontinued
0.6207	Remote Similarity	NPD7572	Phase 2
0.6203	Remote Similarity	NPD4116	Approved
0.6202	Remote Similarity	NPD7001	Phase 3
0.6202	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6659	Phase 2
0.6196	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD2116	Approved
0.6196	Remote Similarity	NPD2117	Pre-registration
0.6196	Remote Similarity	NPD7072	Phase 2
0.6196	Remote Similarity	NPD2115	Approved
0.619	Remote Similarity	NPD6792	Phase 3
0.619	Remote Similarity	NPD5578	Approved
0.619	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7950	Approved
0.6188	Remote Similarity	NPD7528	Approved
0.6188	Remote Similarity	NPD7952	Approved
0.6188	Remote Similarity	NPD7953	Approved
0.6188	Remote Similarity	NPD7791	Approved
0.6188	Remote Similarity	NPD7789	Approved
0.6188	Remote Similarity	NPD7951	Approved
0.6188	Remote Similarity	NPD7790	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