NPASS Compound

Structure

CID224970 OpenBabel06191716022D 25 29 0 0 1 0 0 0 0 0999 V2000 4.5508 0.6311 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 0 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 1 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 3.6847 -0.8689 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 1 11 1 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 23 2 0 0 0 0 12 9 1 1 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 6 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 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.16
Volume:	344.239
LogP:	1.34
LogD:	1.217
LogS:	-3.062
# Rotatable Bonds:	3
TPSA:	58.97
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.775
Synthetic Accessibility Score:	5.527
Fsp3:	0.55
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:	-4.759
MDCK Permeability:	3.1863677577348426e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.135

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	54.3519287109375%
Volume Distribution (VD):	2.588
Pgp-substrate:	59.13213348388672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.961
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.21
CYP2D6-inhibitor:	0.219
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.425
CYP3A4-substrate:	0.842

ADMET: Excretion

Clearance (CL):	7.93
Half-life (T1/2):	0.557

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.727
Drug-inuced Liver Injury (DILI):	0.457
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.606
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.506
Carcinogencity:	0.518
Eye Corrosion:	0.014
Eye Irritation:	0.092
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC224970

Natural Product ID:	NPC224970
*Common Name:**	Alstolucine B
IUPAC Name:	n.a.
Synonyms:	Alstolucine B
Standard InCHIKey:	DHAOEWPYRANXCZ-SFZJTNDWSA-N
Standard InCHI:	InChI=1S/C20H22N2O3/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/h3-6,12-13,16,21H,7-10H2,1-2H3/t12-,13-,16-,20+/m0/s1
SMILES:	CC(=O)[C@@H]1CN2CC[C@@]34c5ccccc5NC4=C([C@H]1C[C@H]23)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651100
PubChem CID:	11002245
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	2

Activity Type	# Activity
Individual Protein	2
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[541626]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.64	ug.mL-1	PMID[541626]
NPT957	Individual Protein	Multidrug resistance-associated protein 7	Homo sapiens	Inhibition	=	40.0	%	PMID[541627]
NPT957	Individual Protein	Multidrug resistance-associated protein 7	Homo sapiens	Inhibition	=	50.0	%	PMID[541627]

☑ 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 NPC224970 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	249
0.1-0.2	1051
0.2-0.3	4608
0.3-0.4	17144
0.4-0.5	14272
0.5-0.6	4433
0.6-0.7	747
0.7-0.8	153
0.8-0.85	19
0.85-0.9	6
0.9-0.95	7
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167724
1.0	High Similarity	NPC223595
0.9605	High Similarity	NPC193410
0.9542	High Similarity	NPC248117
0.9494	High Similarity	NPC329338
0.9494	High Similarity	NPC469726
0.9412	High Similarity	NPC61013
0.9355	High Similarity	NPC293458
0.9193	High Similarity	NPC203202
0.9193	High Similarity	NPC264482
0.9161	High Similarity	NPC123241
0.9103	High Similarity	NPC36495
0.908	High Similarity	NPC218594
0.908	High Similarity	NPC99043
0.908	High Similarity	NPC6974
0.8706	High Similarity	NPC14994
0.869	High Similarity	NPC159963
0.8675	High Similarity	NPC186669
0.8639	High Similarity	NPC97584
0.8634	High Similarity	NPC282339
0.8634	High Similarity	NPC99632
0.8555	High Similarity	NPC25401
0.8371	Intermediate Similarity	NPC132874
0.8371	Intermediate Similarity	NPC138615
0.8371	Intermediate Similarity	NPC218733
0.8371	Intermediate Similarity	NPC265642
0.8253	Intermediate Similarity	NPC279527
0.8253	Intermediate Similarity	NPC214960
0.8232	Intermediate Similarity	NPC225319
0.8079	Intermediate Similarity	NPC5630
0.8034	Intermediate Similarity	NPC203628
0.8034	Intermediate Similarity	NPC22476
0.8	Intermediate Similarity	NPC113946
0.7914	Intermediate Similarity	NPC243756
0.7904	Intermediate Similarity	NPC474058
0.7857	Intermediate Similarity	NPC303214
0.7849	Intermediate Similarity	NPC214626
0.7849	Intermediate Similarity	NPC139085
0.7849	Intermediate Similarity	NPC251212
0.7838	Intermediate Similarity	NPC469732
0.7818	Intermediate Similarity	NPC478076
0.7796	Intermediate Similarity	NPC1464
0.7753	Intermediate Similarity	NPC52262
0.7744	Intermediate Similarity	NPC473329
0.7733	Intermediate Similarity	NPC472118
0.7714	Intermediate Similarity	NPC260075
0.7692	Intermediate Similarity	NPC309531
0.7692	Intermediate Similarity	NPC472102
0.7672	Intermediate Similarity	NPC246140
0.7672	Intermediate Similarity	NPC195787
0.7667	Intermediate Similarity	NPC181928
0.7651	Intermediate Similarity	NPC122106
0.7647	Intermediate Similarity	NPC232600
0.7625	Intermediate Similarity	NPC130251
0.7619	Intermediate Similarity	NPC87714
0.7581	Intermediate Similarity	NPC100863
0.7561	Intermediate Similarity	NPC264589
0.756	Intermediate Similarity	NPC161827
0.7558	Intermediate Similarity	NPC470069
0.7558	Intermediate Similarity	NPC52059
0.7543	Intermediate Similarity	NPC285622
0.7543	Intermediate Similarity	NPC96901
0.7526	Intermediate Similarity	NPC475147
0.7515	Intermediate Similarity	NPC469536
0.7486	Intermediate Similarity	NPC473298
0.7485	Intermediate Similarity	NPC154602
0.7485	Intermediate Similarity	NPC475763
0.7449	Intermediate Similarity	NPC189661
0.7442	Intermediate Similarity	NPC472101
0.7442	Intermediate Similarity	NPC472121
0.7442	Intermediate Similarity	NPC469741
0.7442	Intermediate Similarity	NPC472120
0.7442	Intermediate Similarity	NPC472117
0.7427	Intermediate Similarity	NPC63210
0.7427	Intermediate Similarity	NPC243673
0.7427	Intermediate Similarity	NPC148468
0.7427	Intermediate Similarity	NPC310403
0.7427	Intermediate Similarity	NPC263709
0.7427	Intermediate Similarity	NPC97380
0.7419	Intermediate Similarity	NPC34717
0.7371	Intermediate Similarity	NPC475133
0.7362	Intermediate Similarity	NPC301760
0.7356	Intermediate Similarity	NPC472106
0.7345	Intermediate Similarity	NPC476425
0.7345	Intermediate Similarity	NPC181138
0.7345	Intermediate Similarity	NPC293255
0.7345	Intermediate Similarity	NPC210415
0.7345	Intermediate Similarity	NPC21752
0.7345	Intermediate Similarity	NPC298851
0.7345	Intermediate Similarity	NPC276993
0.7341	Intermediate Similarity	NPC286871
0.734	Intermediate Similarity	NPC90967
0.7337	Intermediate Similarity	NPC77777
0.7333	Intermediate Similarity	NPC269449
0.7333	Intermediate Similarity	NPC190945
0.7326	Intermediate Similarity	NPC220151
0.7326	Intermediate Similarity	NPC19692
0.7321	Intermediate Similarity	NPC318086
0.7314	Intermediate Similarity	NPC472114
0.7314	Intermediate Similarity	NPC472115
0.7297	Intermediate Similarity	NPC105055
0.7297	Intermediate Similarity	NPC22689
0.7283	Intermediate Similarity	NPC21425
0.7283	Intermediate Similarity	NPC201424
0.7273	Intermediate Similarity	NPC469537
0.7267	Intermediate Similarity	NPC153694
0.7267	Intermediate Similarity	NPC211525
0.7263	Intermediate Similarity	NPC476441
0.7259	Intermediate Similarity	NPC119722
0.7249	Intermediate Similarity	NPC162440
0.7241	Intermediate Similarity	NPC176983
0.7235	Intermediate Similarity	NPC285381
0.7206	Intermediate Similarity	NPC115588
0.72	Intermediate Similarity	NPC195636
0.7196	Intermediate Similarity	NPC245916
0.7191	Intermediate Similarity	NPC292265
0.7184	Intermediate Similarity	NPC315368
0.7181	Intermediate Similarity	NPC472295
0.7181	Intermediate Similarity	NPC269886
0.7181	Intermediate Similarity	NPC472210
0.7181	Intermediate Similarity	NPC247735
0.7181	Intermediate Similarity	NPC81802
0.7151	Intermediate Similarity	NPC102338
0.7151	Intermediate Similarity	NPC177261
0.7151	Intermediate Similarity	NPC63199
0.7151	Intermediate Similarity	NPC111602
0.7151	Intermediate Similarity	NPC473297
0.7151	Intermediate Similarity	NPC196251
0.7143	Intermediate Similarity	NPC221687
0.7127	Intermediate Similarity	NPC476326
0.7117	Intermediate Similarity	NPC471123
0.711	Intermediate Similarity	NPC29285
0.7094	Intermediate Similarity	NPC476069
0.7088	Intermediate Similarity	NPC321211
0.7081	Intermediate Similarity	NPC322621
0.7077	Intermediate Similarity	NPC329833
0.7067	Intermediate Similarity	NPC223242
0.7065	Intermediate Similarity	NPC470317
0.7059	Intermediate Similarity	NPC128476
0.7047	Intermediate Similarity	NPC67904
0.7047	Intermediate Similarity	NPC138830
0.703	Intermediate Similarity	NPC126556
0.7029	Intermediate Similarity	NPC471122
0.7021	Intermediate Similarity	NPC329858
0.7011	Intermediate Similarity	NPC476428
0.7011	Intermediate Similarity	NPC36836
0.7011	Intermediate Similarity	NPC63370
0.701	Intermediate Similarity	NPC471512
0.7006	Intermediate Similarity	NPC313757
0.7	Intermediate Similarity	NPC139373
0.7	Intermediate Similarity	NPC318183
0.6988	Remote Similarity	NPC315051
0.6974	Remote Similarity	NPC162730
0.6971	Remote Similarity	NPC222029
0.6959	Remote Similarity	NPC312870
0.6959	Remote Similarity	NPC199851
0.6959	Remote Similarity	NPC128265
0.6959	Remote Similarity	NPC294909
0.6959	Remote Similarity	NPC254240
0.6957	Remote Similarity	NPC19175
0.6951	Remote Similarity	NPC173295
0.6947	Remote Similarity	NPC55493
0.6946	Remote Similarity	NPC186284
0.6946	Remote Similarity	NPC22082
0.6931	Remote Similarity	NPC314333
0.6928	Remote Similarity	NPC469560
0.6927	Remote Similarity	NPC97100
0.6927	Remote Similarity	NPC278887
0.6927	Remote Similarity	NPC473375
0.6916	Remote Similarity	NPC151171
0.6894	Remote Similarity	NPC209389
0.6888	Remote Similarity	NPC137589
0.6888	Remote Similarity	NPC474116
0.6879	Remote Similarity	NPC66936
0.6879	Remote Similarity	NPC314223
0.6872	Remote Similarity	NPC471124
0.6869	Remote Similarity	NPC131977
0.686	Remote Similarity	NPC242000
0.6859	Remote Similarity	NPC472292
0.6851	Remote Similarity	NPC469915
0.6845	Remote Similarity	NPC471164
0.6842	Remote Similarity	NPC472112
0.6842	Remote Similarity	NPC313293
0.6839	Remote Similarity	NPC472293
0.6837	Remote Similarity	NPC301501
0.6834	Remote Similarity	NPC478075
0.6831	Remote Similarity	NPC475097
0.6826	Remote Similarity	NPC319645
0.682	Remote Similarity	NPC469451
0.6813	Remote Similarity	NPC470343
0.6813	Remote Similarity	NPC472244
0.6809	Remote Similarity	NPC49184
0.6809	Remote Similarity	NPC472209
0.6806	Remote Similarity	NPC469450
0.68	Remote Similarity	NPC285192
0.6796	Remote Similarity	NPC63047
0.6796	Remote Similarity	NPC475248
0.6793	Remote Similarity	NPC320147
0.6789	Remote Similarity	NPC175474
0.6789	Remote Similarity	NPC316405

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 NPC224970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	480
0.2-0.3	769
0.3-0.4	1183
0.4-0.5	3554
0.5-0.6	2598
0.6-0.7	380
0.7-0.8	32
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
0.7333	Intermediate Similarity	NPD2435	Approved
0.7321	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2037	Approved
0.7246	Intermediate Similarity	NPD4041	Approved
0.7238	Intermediate Similarity	NPD4329	Approved
0.7238	Intermediate Similarity	NPD4330	Approved
0.7235	Intermediate Similarity	NPD3399	Approved
0.7232	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1801	Approved
0.7202	Intermediate Similarity	NPD1802	Approved
0.7198	Intermediate Similarity	NPD3471	Approved
0.7198	Intermediate Similarity	NPD3470	Approved
0.7191	Intermediate Similarity	NPD2432	Approved
0.7191	Intermediate Similarity	NPD2431	Approved
0.7175	Intermediate Similarity	NPD2455	Approved
0.7175	Intermediate Similarity	NPD2454	Approved
0.7127	Intermediate Similarity	NPD3792	Approved
0.7126	Intermediate Similarity	NPD7114	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5185	Approved
0.7099	Intermediate Similarity	NPD5182	Approved
0.7099	Intermediate Similarity	NPD5184	Approved
0.7086	Intermediate Similarity	NPD2506	Approved
0.7074	Intermediate Similarity	NPD5504	Discontinued
0.7073	Intermediate Similarity	NPD2670	Approved
0.7062	Intermediate Similarity	NPD7035	Approved
0.7062	Intermediate Similarity	NPD7036	Phase 3
0.7059	Intermediate Similarity	NPD7528	Approved
0.7035	Intermediate Similarity	NPD2948	Discontinued
0.703	Intermediate Similarity	NPD3170	Approved
0.7024	Intermediate Similarity	NPD7487	Discontinued
0.7022	Intermediate Similarity	NPD8002	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8003	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6570	Approved
0.7011	Intermediate Similarity	NPD6571	Approved
0.6995	Remote Similarity	NPD3782	Discontinued
0.6989	Remote Similarity	NPD7244	Discontinued
0.6983	Remote Similarity	NPD2404	Discontinued
0.6973	Remote Similarity	NPD8281	Discontinued
0.6961	Remote Similarity	NPD3377	Discontinued
0.6959	Remote Similarity	NPD4500	Approved
0.6959	Remote Similarity	NPD4501	Approved
0.6946	Remote Similarity	NPD3625	Discontinued
0.6944	Remote Similarity	NPD5183	Approved
0.6944	Remote Similarity	NPD5186	Approved
0.6932	Remote Similarity	NPD2427	Approved
0.6931	Remote Similarity	NPD4499	Approved
0.6902	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7478	Approved
0.6897	Remote Similarity	NPD2790	Discontinued
0.6889	Remote Similarity	NPD3468	Approved
0.6885	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6017	Discontinued
0.6879	Remote Similarity	NPD7606	Phase 3
0.6848	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3422	Phase 3
0.6831	Remote Similarity	NPD7940	Phase 3
0.6831	Remote Similarity	NPD3423	Phase 2
0.6831	Remote Similarity	NPD5466	Approved
0.6826	Remote Similarity	NPD1109	Approved
0.6826	Remote Similarity	NPD1110	Approved
0.6816	Remote Similarity	NPD8008	Approved
0.6816	Remote Similarity	NPD8007	Approved
0.6806	Remote Similarity	NPD3884	Discontinued
0.6805	Remote Similarity	NPD2923	Approved
0.6805	Remote Similarity	NPD6768	Approved
0.6804	Remote Similarity	NPD3828	Approved
0.6795	Remote Similarity	NPD2994	Approved
0.6784	Remote Similarity	NPD6185	Discontinued
0.6776	Remote Similarity	NPD5997	Discontinued
0.6765	Remote Similarity	NPD2820	Phase 3
0.6763	Remote Similarity	NPD4888	Discontinued
0.6744	Remote Similarity	NPD4607	Approved
0.6739	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2116	Approved
0.6731	Remote Similarity	NPD2117	Pre-registration
0.6731	Remote Similarity	NPD2115	Approved
0.673	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1626	Approved
0.6725	Remote Similarity	NPD5918	Discontinued
0.672	Remote Similarity	NPD7881	Approved
0.6716	Remote Similarity	NPD4082	Approved
0.6706	Remote Similarity	NPD2365	Approved
0.6705	Remote Similarity	NPD6758	Approved
0.6705	Remote Similarity	NPD3352	Approved
0.6701	Remote Similarity	NPD6805	Discontinued
0.67	Remote Similarity	NPD4493	Discontinued
0.6688	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5931	Phase 3
0.6686	Remote Similarity	NPD5933	Phase 3
0.6686	Remote Similarity	NPD5932	Phase 3
0.6686	Remote Similarity	NPD7295	Approved
0.6685	Remote Similarity	NPD8630	Approved
0.6685	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7854	Phase 2
0.6685	Remote Similarity	NPD5430	Discontinued
0.6684	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4412	Phase 2
0.6667	Remote Similarity	NPD7082	Approved
0.6667	Remote Similarity	NPD6342	Discontinued
0.6667	Remote Similarity	NPD4494	Approved
0.6667	Remote Similarity	NPD4492	Approved
0.6667	Remote Similarity	NPD2946	Phase 2
0.665	Remote Similarity	NPD3947	Discontinued
0.6646	Remote Similarity	NPD3032	Approved
0.6646	Remote Similarity	NPD3030	Approved
0.6646	Remote Similarity	NPD3031	Approved
0.6634	Remote Similarity	NPD2510	Approved
0.6634	Remote Similarity	NPD2509	Approved
0.6631	Remote Similarity	NPD7775	Approved
0.663	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3790	Phase 2
0.6629	Remote Similarity	NPD4513	Discontinued
0.6628	Remote Similarity	NPD7259	Approved
0.6627	Remote Similarity	NPD1527	Phase 2
0.6616	Remote Similarity	NPD4601	Approved
0.6616	Remote Similarity	NPD4600	Approved
0.6613	Remote Similarity	NPD3948	Discontinued
0.6611	Remote Similarity	NPD4311	Approved
0.6608	Remote Similarity	NPD6566	Discontinued
0.66	Remote Similarity	NPD7205	Discontinued
0.6591	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4596	Phase 1
0.6579	Remote Similarity	NPD3436	Approved
0.6578	Remote Similarity	NPD5600	Discontinued
0.6571	Remote Similarity	NPD5942	Approved
0.6571	Remote Similarity	NPD5941	Approved
0.657	Remote Similarity	NPD1625	Approved
0.6568	Remote Similarity	NPD2569	Approved
0.6568	Remote Similarity	NPD2567	Approved
0.6561	Remote Similarity	NPD3435	Discontinued
0.6555	Remote Similarity	NPD6770	Approved
0.6552	Remote Similarity	NPD4859	Phase 1
0.6546	Remote Similarity	NPD3304	Phase 2
0.6545	Remote Similarity	NPD2397	Discontinued
0.6538	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.652	Remote Similarity	NPD4506	Discontinued
0.6517	Remote Similarity	NPD4121	Phase 3
0.6517	Remote Similarity	NPD4120	Approved
0.6517	Remote Similarity	NPD5086	Approved
0.6508	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1070	Approved
0.6506	Remote Similarity	NPD1069	Approved
0.65	Remote Similarity	NPD6238	Discontinued
0.65	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6622	Phase 1
0.6488	Remote Similarity	NPD3893	Discontinued
0.6486	Remote Similarity	NPD7795	Phase 2
0.6482	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5741	Approved
0.648	Remote Similarity	NPD5743	Approved
0.648	Remote Similarity	NPD5742	Approved
0.6477	Remote Similarity	NPD4161	Discontinued
0.6474	Remote Similarity	NPD5024	Approved
0.6473	Remote Similarity	NPD4455	Discontinued
0.6471	Remote Similarity	NPD4022	Approved
0.6471	Remote Similarity	NPD3472	Approved
0.6464	Remote Similarity	NPD4393	Approved
0.6464	Remote Similarity	NPD33	Approved
0.6464	Remote Similarity	NPD7599	Phase 2
0.6463	Remote Similarity	NPD552	Approved
0.6463	Remote Similarity	NPD9567	Approved
0.6463	Remote Similarity	NPD553	Approved
0.6462	Remote Similarity	NPD4370	Phase 3
0.645	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4602	Approved
0.6446	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5748	Phase 2
0.6432	Remote Similarity	NPD2844	Phase 3
0.6429	Remote Similarity	NPD7600	Phase 2
0.6425	Remote Similarity	NPD3888	Discontinued
0.6424	Remote Similarity	NPD5993	Phase 1
0.641	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3372	Discontinued
0.6404	Remote Similarity	NPD8282	Approved
0.6404	Remote Similarity	NPD8283	Approved
0.6404	Remote Similarity	NPD56	Approved
0.6404	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6891	Phase 2
0.6386	Remote Similarity	NPD4549	Discontinued
0.6386	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4430	Phase 2
0.6378	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5318	Discontinued
0.6373	Remote Similarity	NPD6557	Phase 2
0.6369	Remote Similarity	NPD1371	Approved
0.6369	Remote Similarity	NPD1373	Approved
0.6369	Remote Similarity	NPD1374	Approved
0.6369	Remote Similarity	NPD1370	Approved
0.6368	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2010	Phase 3
0.6358	Remote Similarity	NPD4461	Discontinued
0.6355	Remote Similarity	NPD6176	Phase 1

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