NPASS Compound

Structure

NPC99043 OpenBabel07101718282D 25 29 0 0 1 0 0 0 0 0999 V2000 -3.6847 -0.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9684 -1.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1075 1.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1913 0.5954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0272 2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1948 -0.0767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4522 1.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1356 0.3221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9527 2.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9527 0.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6847 0.1311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8187 1.6311 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8187 0.6311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0307 1.6493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1145 0.4502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0867 1.6311 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9667 0.7833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7726 0.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2946 -0.1614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1356 1.9401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0867 0.6311 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -4.5508 0.6311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2767 -0.3498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6405 -0.9178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 8 22 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 1 1 1 0 0 0 11 23 1 0 0 0 0 12 9 1 6 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 11 1 6 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 1 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.18
Volume:	346.876
LogP:	1.556
LogD:	1.584
LogS:	-3.326
# Rotatable Bonds:	3
TPSA:	62.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.836
Synthetic Accessibility Score:	5.7
Fsp3:	0.6
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:	-4.815
MDCK Permeability:	3.389637640793808e-05
Pgp-inhibitor:	0.64
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.114

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	53.692657470703125%
Volume Distribution (VD):	2.082
Pgp-substrate:	63.79414749145508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.305
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.193
CYP2D6-substrate:	0.854
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.838

ADMET: Excretion

Clearance (CL):	5.039
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.263
Human Hepatotoxicity (H-HT):	0.511
Drug-inuced Liver Injury (DILI):	0.591
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.798
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.183
Carcinogencity:	0.44
Eye Corrosion:	0.004
Eye Irritation:	0.044
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC99043

Natural Product ID:	NPC99043
*Common Name:**	DWLJVOJBWLYMJO-VLXZENBVSA-N
IUPAC Name:	n.a.
Synonyms:	N(4)-Demethylalstogustine
Standard InCHIKey:	DWLJVOJBWLYMJO-VLXZENBVSA-N
Standard InCHI:	InChI=1S/C20H24N2O3/c1-11(23)13-10-22-8-7-20-14-5-3-4-6-15(14)21-18(20)17(19(24)25-2)12(13)9-16(20)22/h3-6,11-13,16,21,23H,7-10H2,1-2H3/t11-,12+,13-,16+,20-/m1/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2C[C@H]1[C@H](CN2CC4)[C@H](O)C)cccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651105
PubChem CID:	21589744
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
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17493	Alstonia spatulata	Species	Apocynaceae	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
IC50	3
Others	1

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[558756]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.12	ug.mL-1	PMID[558756]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	35.0	%	PMID[558757]

☑ 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 NPC99043 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	194
0.1-0.2	856
0.2-0.3	2863
0.3-0.4	10814
0.4-0.5	20997
0.5-0.6	5651
0.6-0.7	1102
0.7-0.8	171
0.8-0.85	27
0.85-0.9	7
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC218594
0.9627	High Similarity	NPC264482
0.9627	High Similarity	NPC203202
0.9509	High Similarity	NPC6974
0.9281	High Similarity	NPC97584
0.9182	High Similarity	NPC193410
0.9125	High Similarity	NPC248117
0.9107	High Similarity	NPC159963
0.9096	High Similarity	NPC186669
0.908	High Similarity	NPC167724
0.908	High Similarity	NPC223595
0.908	High Similarity	NPC224970
0.9062	High Similarity	NPC36495
0.9	High Similarity	NPC61013
0.896	High Similarity	NPC25401
0.8895	High Similarity	NPC14994
0.8765	High Similarity	NPC123241
0.872	High Similarity	NPC293458
0.8639	High Similarity	NPC469726
0.8639	High Similarity	NPC329338
0.8571	High Similarity	NPC1464
0.8432	Intermediate Similarity	NPC246140
0.8432	Intermediate Similarity	NPC195787
0.8378	Intermediate Similarity	NPC87714
0.8323	Intermediate Similarity	NPC474058
0.8274	Intermediate Similarity	NPC282339
0.8274	Intermediate Similarity	NPC99632
0.8214	Intermediate Similarity	NPC309531
0.8214	Intermediate Similarity	NPC472102
0.8177	Intermediate Similarity	NPC189661
0.8122	Intermediate Similarity	NPC203628
0.8066	Intermediate Similarity	NPC5630
0.8059	Intermediate Similarity	NPC472120
0.8059	Intermediate Similarity	NPC472101
0.8046	Intermediate Similarity	NPC210415
0.8046	Intermediate Similarity	NPC293255
0.8046	Intermediate Similarity	NPC21752
0.8046	Intermediate Similarity	NPC298851
0.8046	Intermediate Similarity	NPC276993
0.8046	Intermediate Similarity	NPC181138
0.8045	Intermediate Similarity	NPC52262
0.7957	Intermediate Similarity	NPC132874
0.7957	Intermediate Similarity	NPC218733
0.7957	Intermediate Similarity	NPC265642
0.7957	Intermediate Similarity	NPC138615
0.7953	Intermediate Similarity	NPC472117
0.7946	Intermediate Similarity	NPC303214
0.7919	Intermediate Similarity	NPC214960
0.7919	Intermediate Similarity	NPC279527
0.7895	Intermediate Similarity	NPC225319
0.7879	Intermediate Similarity	NPC264589
0.7869	Intermediate Similarity	NPC105055
0.7869	Intermediate Similarity	NPC22689
0.7861	Intermediate Similarity	NPC472106
0.7841	Intermediate Similarity	NPC214626
0.7841	Intermediate Similarity	NPC139085
0.7841	Intermediate Similarity	NPC251212
0.7831	Intermediate Similarity	NPC232600
0.7829	Intermediate Similarity	NPC472118
0.7826	Intermediate Similarity	NPC22476
0.7798	Intermediate Similarity	NPC475763
0.7713	Intermediate Similarity	NPC90967
0.7709	Intermediate Similarity	NPC260075
0.7688	Intermediate Similarity	NPC77777
0.7674	Intermediate Similarity	NPC113946
0.7663	Intermediate Similarity	NPC181928
0.7662	Intermediate Similarity	NPC128476
0.7644	Intermediate Similarity	NPC471512
0.763	Intermediate Similarity	NPC243673
0.763	Intermediate Similarity	NPC63210
0.763	Intermediate Similarity	NPC310403
0.763	Intermediate Similarity	NPC148468
0.763	Intermediate Similarity	NPC263709
0.763	Intermediate Similarity	NPC97380
0.7588	Intermediate Similarity	NPC243756
0.7557	Intermediate Similarity	NPC470069
0.7557	Intermediate Similarity	NPC52059
0.7556	Intermediate Similarity	NPC476441
0.755	Intermediate Similarity	NPC195636
0.7549	Intermediate Similarity	NPC19175
0.7543	Intermediate Similarity	NPC472121
0.7529	Intermediate Similarity	NPC318086
0.75	Intermediate Similarity	NPC478076
0.7488	Intermediate Similarity	NPC301501
0.7487	Intermediate Similarity	NPC473298
0.7485	Intermediate Similarity	NPC154602
0.7471	Intermediate Similarity	NPC153694
0.7471	Intermediate Similarity	NPC211525
0.7461	Intermediate Similarity	NPC469732
0.7457	Intermediate Similarity	NPC161827
0.7444	Intermediate Similarity	NPC285622
0.7444	Intermediate Similarity	NPC96901
0.7438	Intermediate Similarity	NPC476069
0.7427	Intermediate Similarity	NPC473329
0.7424	Intermediate Similarity	NPC269449
0.7421	Intermediate Similarity	NPC34717
0.7421	Intermediate Similarity	NPC221687
0.7416	Intermediate Similarity	NPC472114
0.7416	Intermediate Similarity	NPC472115
0.7406	Intermediate Similarity	NPC151171
0.7404	Intermediate Similarity	NPC223242
0.7383	Intermediate Similarity	NPC469452
0.7371	Intermediate Similarity	NPC469450
0.735	Intermediate Similarity	NPC119722
0.7347	Intermediate Similarity	NPC475147
0.7345	Intermediate Similarity	NPC286871
0.7341	Intermediate Similarity	NPC122106
0.7333	Intermediate Similarity	NPC139373
0.732	Intermediate Similarity	NPC312870
0.732	Intermediate Similarity	NPC254240
0.732	Intermediate Similarity	NPC199851
0.732	Intermediate Similarity	NPC294909
0.732	Intermediate Similarity	NPC128265
0.7315	Intermediate Similarity	NPC329932
0.7306	Intermediate Similarity	NPC100863
0.7302	Intermediate Similarity	NPC469451
0.7302	Intermediate Similarity	NPC469722
0.7297	Intermediate Similarity	NPC475962
0.7297	Intermediate Similarity	NPC476428
0.7259	Intermediate Similarity	NPC329833
0.7253	Intermediate Similarity	NPC476425
0.7249	Intermediate Similarity	NPC316405
0.7247	Intermediate Similarity	NPC176983
0.7241	Intermediate Similarity	NPC285381
0.7238	Intermediate Similarity	NPC469915
0.7235	Intermediate Similarity	NPC472103
0.7231	Intermediate Similarity	NPC475489
0.723	Intermediate Similarity	NPC291173
0.7216	Intermediate Similarity	NPC469536
0.7202	Intermediate Similarity	NPC130251
0.7202	Intermediate Similarity	NPC473375
0.7202	Intermediate Similarity	NPC97100
0.72	Intermediate Similarity	NPC475133
0.7196	Intermediate Similarity	NPC131977
0.7191	Intermediate Similarity	NPC315368
0.7165	Intermediate Similarity	NPC162440
0.7157	Intermediate Similarity	NPC234772
0.7151	Intermediate Similarity	NPC472100
0.7143	Intermediate Similarity	NPC473458
0.7135	Intermediate Similarity	NPC190945
0.7135	Intermediate Similarity	NPC471122
0.7122	Intermediate Similarity	NPC126556
0.712	Intermediate Similarity	NPC475097
0.7119	Intermediate Similarity	NPC29285
0.7113	Intermediate Similarity	NPC245916
0.7097	Intermediate Similarity	NPC475094
0.7095	Intermediate Similarity	NPC201424
0.709	Intermediate Similarity	NPC472209
0.7088	Intermediate Similarity	NPC470971
0.7086	Intermediate Similarity	NPC314223
0.7074	Intermediate Similarity	NPC477159
0.7062	Intermediate Similarity	NPC19692
0.7062	Intermediate Similarity	NPC220151
0.7059	Intermediate Similarity	NPC186284
0.7059	Intermediate Similarity	NPC22082
0.7056	Intermediate Similarity	NPC67904
0.7056	Intermediate Similarity	NPC138830
0.7043	Intermediate Similarity	NPC476326
0.7031	Intermediate Similarity	NPC474059
0.7017	Intermediate Similarity	NPC313757
0.7016	Intermediate Similarity	NPC21425
0.7011	Intermediate Similarity	NPC292265
0.7	Intermediate Similarity	NPC469460
0.6981	Remote Similarity	NPC471513
0.6979	Remote Similarity	NPC63199
0.6979	Remote Similarity	NPC102338
0.6979	Remote Similarity	NPC175474
0.6979	Remote Similarity	NPC196251
0.6979	Remote Similarity	NPC111602
0.6978	Remote Similarity	NPC471124
0.6973	Remote Similarity	NPC177261
0.6971	Remote Similarity	NPC288110
0.6961	Remote Similarity	NPC85651
0.6961	Remote Similarity	NPC469741
0.6959	Remote Similarity	NPC301760
0.6954	Remote Similarity	NPC52557
0.694	Remote Similarity	NPC278887
0.6931	Remote Similarity	NPC478075
0.693	Remote Similarity	NPC474192
0.693	Remote Similarity	NPC475720
0.6927	Remote Similarity	NPC63370
0.6927	Remote Similarity	NPC36836
0.6923	Remote Similarity	NPC470485
0.6911	Remote Similarity	NPC49184
0.6901	Remote Similarity	NPC315051
0.69	Remote Similarity	NPC475223
0.6898	Remote Similarity	NPC129624
0.6898	Remote Similarity	NPC473105
0.6891	Remote Similarity	NPC284706
0.689	Remote Similarity	NPC52254
0.6887	Remote Similarity	NPC115588
0.6887	Remote Similarity	NPC231924
0.6884	Remote Similarity	NPC249150
0.6884	Remote Similarity	NPC49196
0.6884	Remote Similarity	NPC313985
0.6884	Remote Similarity	NPC79129
0.6884	Remote Similarity	NPC195461
0.6884	Remote Similarity	NPC81654
0.6879	Remote Similarity	NPC469537
0.6872	Remote Similarity	NPC473297

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 NPC99043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	415
0.2-0.3	680
0.3-0.4	1155
0.4-0.5	3512
0.5-0.6	2774
0.6-0.7	450
0.7-0.8	26
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
0.732	Intermediate Similarity	NPD4500	Approved
0.732	Intermediate Similarity	NPD4501	Approved
0.7151	Intermediate Similarity	NPD4041	Approved
0.7135	Intermediate Similarity	NPD2435	Approved
0.7135	Intermediate Similarity	NPD7114	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4121	Phase 3
0.7102	Intermediate Similarity	NPD4120	Approved
0.7088	Intermediate Similarity	NPD2037	Approved
0.7072	Intermediate Similarity	NPD7036	Phase 3
0.7072	Intermediate Similarity	NPD7035	Approved
0.7062	Intermediate Similarity	NPD5743	Approved
0.7062	Intermediate Similarity	NPD5742	Approved
0.7062	Intermediate Similarity	NPD5741	Approved
0.7059	Intermediate Similarity	NPD4329	Approved
0.7059	Intermediate Similarity	NPD4330	Approved
0.7049	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3399	Approved
0.7043	Intermediate Similarity	NPD8006	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8002	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8003	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3422	Phase 3
0.7027	Intermediate Similarity	NPD3423	Phase 2
0.7021	Intermediate Similarity	NPD3470	Approved
0.7021	Intermediate Similarity	NPD3471	Approved
0.7011	Intermediate Similarity	NPD1802	Approved
0.7011	Intermediate Similarity	NPD2431	Approved
0.7011	Intermediate Similarity	NPD2432	Approved
0.7011	Intermediate Similarity	NPD1801	Approved
0.7	Intermediate Similarity	NPD7244	Discontinued
0.6995	Remote Similarity	NPD2455	Approved
0.6995	Remote Similarity	NPD2454	Approved
0.6959	Remote Similarity	NPD3625	Discontinued
0.6952	Remote Similarity	NPD3792	Approved
0.6941	Remote Similarity	NPD3170	Approved
0.6932	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6571	Approved
0.6927	Remote Similarity	NPD6570	Approved
0.6915	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5504	Discontinued
0.6906	Remote Similarity	NPD2506	Approved
0.6905	Remote Similarity	NPD5185	Approved
0.6905	Remote Similarity	NPD5184	Approved
0.6905	Remote Similarity	NPD5182	Approved
0.6904	Remote Similarity	NPD3828	Approved
0.6895	Remote Similarity	NPD8281	Discontinued
0.6884	Remote Similarity	NPD6805	Discontinued
0.6884	Remote Similarity	NPD4601	Approved
0.6884	Remote Similarity	NPD4600	Approved
0.6882	Remote Similarity	NPD2670	Approved
0.6875	Remote Similarity	NPD7528	Approved
0.6854	Remote Similarity	NPD2948	Discontinued
0.6845	Remote Similarity	NPD5466	Approved
0.6839	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3782	Discontinued
0.6811	Remote Similarity	NPD2404	Discontinued
0.6806	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7295	Approved
0.6793	Remote Similarity	NPD5430	Discontinued
0.6791	Remote Similarity	NPD5997	Discontinued
0.6782	Remote Similarity	NPD2820	Phase 3
0.6782	Remote Similarity	NPD7205	Discontinued
0.678	Remote Similarity	NPD4888	Discontinued
0.6774	Remote Similarity	NPD5183	Approved
0.6774	Remote Similarity	NPD5186	Approved
0.6761	Remote Similarity	NPD4607	Approved
0.6758	Remote Similarity	NPD2427	Approved
0.6755	Remote Similarity	NPD7940	Phase 3
0.6743	Remote Similarity	NPD7487	Discontinued
0.6724	Remote Similarity	NPD2923	Approved
0.6724	Remote Similarity	NPD2365	Approved
0.6723	Remote Similarity	NPD3352	Approved
0.6721	Remote Similarity	NPD7600	Phase 2
0.672	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3468	Approved
0.6705	Remote Similarity	NPD6185	Discontinued
0.6703	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4499	Approved
0.6667	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6891	Phase 2
0.665	Remote Similarity	NPD3884	Discontinued
0.665	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7775	Approved
0.6649	Remote Similarity	NPD6557	Phase 2
0.6649	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8008	Approved
0.6649	Remote Similarity	NPD3790	Phase 2
0.6649	Remote Similarity	NPD8007	Approved
0.6648	Remote Similarity	NPD4513	Discontinued
0.6648	Remote Similarity	NPD1663	Discontinued
0.6647	Remote Similarity	NPD1109	Approved
0.6647	Remote Similarity	NPD1110	Approved
0.6632	Remote Similarity	NPD7962	Phase 2
0.6629	Remote Similarity	NPD6758	Approved
0.6614	Remote Similarity	NPD3377	Discontinued
0.6612	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8630	Approved
0.6611	Remote Similarity	NPD7606	Phase 3
0.661	Remote Similarity	NPD6017	Discontinued
0.6604	Remote Similarity	NPD7878	Phase 2
0.6603	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3436	Approved
0.6592	Remote Similarity	NPD5942	Approved
0.6592	Remote Similarity	NPD5941	Approved
0.6591	Remote Similarity	NPD7082	Approved
0.6591	Remote Similarity	NPD1625	Approved
0.659	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7599	Phase 2
0.6573	Remote Similarity	NPD6770	Approved
0.657	Remote Similarity	NPD4082	Approved
0.657	Remote Similarity	NPD2509	Approved
0.657	Remote Similarity	NPD2510	Approved
0.6566	Remote Similarity	NPD6659	Phase 2
0.6562	Remote Similarity	NPD7881	Approved
0.6556	Remote Similarity	NPD1405	Approved
0.6555	Remote Similarity	NPD4493	Discontinued
0.6554	Remote Similarity	NPD7259	Approved
0.6541	Remote Similarity	NPD4311	Approved
0.6538	Remote Similarity	NPD5086	Approved
0.6538	Remote Similarity	NPD4506	Discontinued
0.6536	Remote Similarity	NPD7478	Approved
0.6535	Remote Similarity	NPD4668	Phase 2
0.6534	Remote Similarity	NPD6768	Approved
0.6529	Remote Similarity	NPD1070	Approved
0.6529	Remote Similarity	NPD1069	Approved
0.6528	Remote Similarity	NPD6879	Phase 2
0.6528	Remote Similarity	NPD6878	Phase 2
0.6524	Remote Similarity	NPD4494	Approved
0.6524	Remote Similarity	NPD4492	Approved
0.6513	Remote Similarity	NPD4412	Phase 2
0.6509	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7795	Phase 2
0.6506	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2994	Approved
0.65	Remote Similarity	NPD4161	Discontinued
0.6497	Remote Similarity	NPD6483	Approved
0.6497	Remote Similarity	NPD5024	Approved
0.6497	Remote Similarity	NPD6484	Approved
0.6495	Remote Similarity	NPD3435	Discontinued
0.6494	Remote Similarity	NPD2569	Approved
0.6494	Remote Similarity	NPD2567	Approved
0.6492	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6995	Phase 1
0.6479	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2613	Approved
0.6468	Remote Similarity	NPD4602	Approved
0.6467	Remote Similarity	NPD2836	Approved
0.6467	Remote Similarity	NPD7105	Phase 1
0.6465	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD5748	Phase 2
0.6461	Remote Similarity	NPD2387	Approved
0.6457	Remote Similarity	NPD1626	Approved
0.6455	Remote Similarity	NPD2844	Phase 3
0.6453	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD2790	Discontinued
0.6446	Remote Similarity	NPD2609	Approved
0.6446	Remote Similarity	NPD2612	Approved
0.6446	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4216	Approved
0.6446	Remote Similarity	NPD4215	Approved
0.6446	Remote Similarity	NPD4217	Approved
0.6446	Remote Similarity	NPD4218	Approved
0.6446	Remote Similarity	NPD2610	Approved
0.6446	Remote Similarity	NPD3132	Approved
0.6446	Remote Similarity	NPD3131	Approved
0.6446	Remote Similarity	NPD2611	Approved
0.6446	Remote Similarity	NPD2608	Approved
0.6444	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5898	Approved
0.6443	Remote Similarity	NPD5899	Approved
0.6443	Remote Similarity	NPD5897	Approved
0.6442	Remote Similarity	NPD2115	Approved
0.6442	Remote Similarity	NPD6518	Discontinued
0.6442	Remote Similarity	NPD2116	Approved
0.6442	Remote Similarity	NPD2117	Pre-registration
0.6442	Remote Similarity	NPD4596	Phase 1
0.644	Remote Similarity	NPD7854	Phase 2
0.6439	Remote Similarity	NPD6238	Discontinued
0.6438	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5411	Discontinued
0.6432	Remote Similarity	NPD5928	Phase 1
0.6429	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5982	Phase 2
0.6425	Remote Similarity	NPD56	Approved
0.6425	Remote Similarity	NPD8282	Approved
0.6425	Remote Similarity	NPD8283	Approved
0.6422	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6874	Approved
0.6411	Remote Similarity	NPD8399	Phase 1
0.6411	Remote Similarity	NPD8423	Phase 2
0.6409	Remote Similarity	NPD4682	Phase 2
0.6404	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4430	Phase 2
0.64	Remote Similarity	NPD3304	Phase 2
0.64	Remote Similarity	NPD5042	Phase 1
0.64	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4393	Approved
0.6398	Remote Similarity	NPD33	Approved
0.6398	Remote Similarity	NPD7470	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