NPASS Compound

Structure

CID138615 OpenBabel06191715492D 26 30 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 2.0272 -2.3214 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 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 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 2.1948 0.0767 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 1.1145 -0.4502 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 2.2645 1.0743 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 10 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 13 1 0 0 0 0 5 14 2 0 0 0 0 6 7 1 0 0 0 0 7 22 1 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 10 23 2 0 0 0 0 11 8 1 1 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 10 1 1 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 6 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	514.308
LogP:	5.767
LogD:	5.106
LogS:	-5.043
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	4.999
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.947
MDCK Permeability:	2.552609112171922e-05
Pgp-inhibitor:	0.854
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	92.6379623413086%
Volume Distribution (VD):	1.053
Pgp-substrate:	3.804532527923584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.204
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.658
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.606
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	6.739
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.533
Maximum Recommended Daily Dose:	0.861
Skin Sensitization:	0.354
Carcinogencity:	0.009
Eye Corrosion:	0.012
Eye Irritation:	0.043
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC138615

Natural Product ID:	NPC138615
*Common Name:**	Alstolucine E
IUPAC Name:	n.a.
Synonyms:	Alstolucine E
Standard InCHIKey:	LNRAHCYSFBURKI-RCJHKNESSA-N
Standard InCHI:	InChI=1S/C20H22N2O4/c1-10(23)12-9-22-7-6-20-13-4-3-5-14(24)17(13)21-18(20)16(19(25)26-2)11(12)8-15(20)22/h3-5,11-12,15,21,24H,6-9H2,1-2H3/t11-,12+,15-,20+/m0/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2C[C@H]1[C@H](CN2CC4)C(=O)C)cccc3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651103
PubChem CID:	14707763
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

Activity Type	# Activity
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[543288]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19.22	ug.mL-1	PMID[543288]

☑ 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 NPC138615 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	275
0.1-0.2	1188
0.2-0.3	4469
0.3-0.4	11622
0.4-0.5	14502
0.5-0.6	9206
0.6-0.7	1290
0.7-0.8	124
0.8-0.85	10
0.85-0.9	5
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC265642
1.0	High Similarity	NPC218733
1.0	High Similarity	NPC132874
0.9396	High Similarity	NPC469732
0.9344	High Similarity	NPC1464
0.8889	High Similarity	NPC246140
0.8889	High Similarity	NPC195787
0.8641	High Similarity	NPC5630
0.8396	Intermediate Similarity	NPC203628
0.8371	Intermediate Similarity	NPC167724
0.8371	Intermediate Similarity	NPC223595
0.8371	Intermediate Similarity	NPC224970
0.822	Intermediate Similarity	NPC303214
0.8103	Intermediate Similarity	NPC232600
0.8087	Intermediate Similarity	NPC329338
0.8087	Intermediate Similarity	NPC469726
0.8066	Intermediate Similarity	NPC33507
0.8034	Intermediate Similarity	NPC193410
0.8034	Intermediate Similarity	NPC36495
0.7989	Intermediate Similarity	NPC248117
0.796	Intermediate Similarity	NPC269449
0.7957	Intermediate Similarity	NPC218594
0.7957	Intermediate Similarity	NPC99043
0.7917	Intermediate Similarity	NPC22476
0.7889	Intermediate Similarity	NPC87714
0.7884	Intermediate Similarity	NPC97584
0.7882	Intermediate Similarity	NPC119722
0.7877	Intermediate Similarity	NPC61013
0.7849	Intermediate Similarity	NPC203202
0.7849	Intermediate Similarity	NPC264482
0.7845	Intermediate Similarity	NPC293458
0.7835	Intermediate Similarity	NPC470485
0.7766	Intermediate Similarity	NPC6974
0.776	Intermediate Similarity	NPC14994
0.774	Intermediate Similarity	NPC475609
0.7732	Intermediate Similarity	NPC470483
0.7732	Intermediate Similarity	NPC25401
0.7725	Intermediate Similarity	NPC19175
0.7718	Intermediate Similarity	NPC189661
0.7711	Intermediate Similarity	NPC475147
0.768	Intermediate Similarity	NPC123241
0.7667	Intermediate Similarity	NPC128476
0.7664	Intermediate Similarity	NPC223242
0.7661	Intermediate Similarity	NPC301501
0.7644	Intermediate Similarity	NPC126556
0.7644	Intermediate Similarity	NPC159963
0.7636	Intermediate Similarity	NPC469451
0.7626	Intermediate Similarity	NPC469450
0.7619	Intermediate Similarity	NPC186669
0.7593	Intermediate Similarity	NPC139373
0.7588	Intermediate Similarity	NPC100863
0.7568	Intermediate Similarity	NPC329932
0.7561	Intermediate Similarity	NPC475133
0.756	Intermediate Similarity	NPC195636
0.7557	Intermediate Similarity	NPC469452
0.7524	Intermediate Similarity	NPC77777
0.7512	Intermediate Similarity	NPC234772
0.7488	Intermediate Similarity	NPC288110
0.7488	Intermediate Similarity	NPC471513
0.7488	Intermediate Similarity	NPC222046
0.7487	Intermediate Similarity	NPC21425
0.7477	Intermediate Similarity	NPC477394
0.7455	Intermediate Similarity	NPC131977
0.7453	Intermediate Similarity	NPC476069
0.7452	Intermediate Similarity	NPC470482
0.7452	Intermediate Similarity	NPC470481
0.745	Intermediate Similarity	NPC161804
0.7409	Intermediate Similarity	NPC291173
0.7379	Intermediate Similarity	NPC478075
0.7368	Intermediate Similarity	NPC127996
0.7366	Intermediate Similarity	NPC99632
0.7366	Intermediate Similarity	NPC282339
0.7327	Intermediate Similarity	NPC473458
0.7282	Intermediate Similarity	NPC470484
0.7268	Intermediate Similarity	NPC166169
0.726	Intermediate Similarity	NPC329567
0.726	Intermediate Similarity	NPC477397
0.726	Intermediate Similarity	NPC330683
0.7255	Intermediate Similarity	NPC138830
0.7249	Intermediate Similarity	NPC472115
0.7249	Intermediate Similarity	NPC472114
0.7244	Intermediate Similarity	NPC477395
0.7235	Intermediate Similarity	NPC115588
0.7219	Intermediate Similarity	NPC225319
0.7196	Intermediate Similarity	NPC52059
0.7196	Intermediate Similarity	NPC470069
0.7192	Intermediate Similarity	NPC90967
0.7188	Intermediate Similarity	NPC151171
0.7158	Intermediate Similarity	NPC279527
0.7158	Intermediate Similarity	NPC214960
0.7157	Intermediate Similarity	NPC302235
0.7156	Intermediate Similarity	NPC231924
0.7136	Intermediate Similarity	NPC181928
0.7121	Intermediate Similarity	NPC52262
0.7103	Intermediate Similarity	NPC469928
0.7098	Intermediate Similarity	NPC154922
0.7093	Intermediate Similarity	NPC469722
0.7087	Intermediate Similarity	NPC67904
0.7078	Intermediate Similarity	NPC122886
0.7074	Intermediate Similarity	NPC263709
0.7074	Intermediate Similarity	NPC148468
0.7074	Intermediate Similarity	NPC310403
0.7074	Intermediate Similarity	NPC97380
0.7074	Intermediate Similarity	NPC63210
0.7074	Intermediate Similarity	NPC243673
0.7065	Intermediate Similarity	NPC473298
0.7065	Intermediate Similarity	NPC474059
0.7044	Intermediate Similarity	NPC203972
0.7037	Intermediate Similarity	NPC474058
0.7028	Intermediate Similarity	NPC474366
0.7021	Intermediate Similarity	NPC153694
0.7021	Intermediate Similarity	NPC211525
0.701	Intermediate Similarity	NPC298851
0.701	Intermediate Similarity	NPC293255
0.701	Intermediate Similarity	NPC210415
0.701	Intermediate Similarity	NPC21752
0.701	Intermediate Similarity	NPC181138
0.701	Intermediate Similarity	NPC34717
0.701	Intermediate Similarity	NPC276993
0.6976	Remote Similarity	NPC170333
0.6973	Remote Similarity	NPC241392
0.6967	Remote Similarity	NPC212123
0.6966	Remote Similarity	NPC329982
0.6963	Remote Similarity	NPC313757
0.6957	Remote Similarity	NPC477393
0.6952	Remote Similarity	NPC133156
0.6944	Remote Similarity	NPC330009
0.6943	Remote Similarity	NPC113455
0.6937	Remote Similarity	NPC470480
0.6935	Remote Similarity	NPC314659
0.6931	Remote Similarity	NPC113946
0.6927	Remote Similarity	NPC221687
0.6915	Remote Similarity	NPC161827
0.6912	Remote Similarity	NPC204970
0.6911	Remote Similarity	NPC472121
0.6907	Remote Similarity	NPC472118
0.6903	Remote Similarity	NPC160113
0.6903	Remote Similarity	NPC476220
0.6897	Remote Similarity	NPC22689
0.6897	Remote Similarity	NPC105055
0.6897	Remote Similarity	NPC477396
0.6895	Remote Similarity	NPC318525
0.6895	Remote Similarity	NPC471122
0.6895	Remote Similarity	NPC10653
0.6884	Remote Similarity	NPC159815
0.6884	Remote Similarity	NPC197335
0.6863	Remote Similarity	NPC28510
0.6859	Remote Similarity	NPC309531
0.6859	Remote Similarity	NPC472102
0.6857	Remote Similarity	NPC474077
0.6853	Remote Similarity	NPC469734
0.6853	Remote Similarity	NPC120239
0.6845	Remote Similarity	NPC243626
0.6842	Remote Similarity	NPC127178
0.6837	Remote Similarity	NPC251212
0.6837	Remote Similarity	NPC139085
0.6837	Remote Similarity	NPC214626
0.683	Remote Similarity	NPC311906
0.6827	Remote Similarity	NPC17677
0.6823	Remote Similarity	NPC257763
0.6823	Remote Similarity	NPC472117
0.6814	Remote Similarity	NPC475720
0.6814	Remote Similarity	NPC474192
0.6812	Remote Similarity	NPC473375
0.6812	Remote Similarity	NPC97100
0.681	Remote Similarity	NPC471512
0.681	Remote Similarity	NPC471489
0.6806	Remote Similarity	NPC301163
0.6804	Remote Similarity	NPC96321
0.68	Remote Similarity	NPC270301
0.6792	Remote Similarity	NPC268077
0.6784	Remote Similarity	NPC321211
0.6783	Remote Similarity	NPC476258
0.6783	Remote Similarity	NPC475816
0.6783	Remote Similarity	NPC304837
0.6782	Remote Similarity	NPC322621
0.6773	Remote Similarity	NPC219397
0.6772	Remote Similarity	NPC478076
0.6768	Remote Similarity	NPC476441
0.6763	Remote Similarity	NPC230313
0.6761	Remote Similarity	NPC477161
0.6755	Remote Similarity	NPC243756
0.6755	Remote Similarity	NPC154602
0.6754	Remote Similarity	NPC469428
0.6753	Remote Similarity	NPC471124
0.675	Remote Similarity	NPC39822
0.6749	Remote Similarity	NPC87391
0.6746	Remote Similarity	NPC71124
0.6745	Remote Similarity	NPC207971
0.6745	Remote Similarity	NPC476098
0.6744	Remote Similarity	NPC477160
0.6743	Remote Similarity	NPC176113
0.6743	Remote Similarity	NPC118228
0.6736	Remote Similarity	NPC472120
0.6736	Remote Similarity	NPC472101
0.6735	Remote Similarity	NPC469915
0.6734	Remote Similarity	NPC260075
0.6729	Remote Similarity	NPC53344
0.6728	Remote Similarity	NPC305542
0.6726	Remote Similarity	NPC51388

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 NPC138615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	501
0.2-0.3	741
0.3-0.4	1431
0.4-0.5	2801
0.5-0.6	3021
0.6-0.7	483
0.7-0.8	1
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
0.7707	Intermediate Similarity	NPD4494	Approved
0.7707	Intermediate Similarity	NPD4492	Approved
0.7635	Intermediate Similarity	NPD4596	Phase 1
0.7598	Intermediate Similarity	NPD4082	Approved
0.7573	Intermediate Similarity	NPD4493	Discontinued
0.756	Intermediate Similarity	NPD3940	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD4456	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD3893	Discontinued
0.7512	Intermediate Similarity	NPD3472	Approved
0.7512	Intermediate Similarity	NPD4022	Approved
0.75	Intermediate Similarity	NPD4455	Discontinued
0.7452	Intermediate Similarity	NPD3888	Discontinued
0.744	Intermediate Similarity	NPD3372	Discontinued
0.7371	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5860	Discontinued
0.729	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2906	Approved
0.726	Intermediate Similarity	NPD2907	Approved
0.7182	Intermediate Similarity	NPD6199	Discontinued
0.7156	Intermediate Similarity	NPD1945	Phase 1
0.698	Remote Similarity	NPD5928	Phase 1
0.6961	Remote Similarity	NPD5610	Approved
0.6959	Remote Similarity	NPD7293	Approved
0.6934	Remote Similarity	NPD4859	Phase 1
0.6919	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3684	Discontinued
0.6908	Remote Similarity	NPD4668	Phase 2
0.6895	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4465	Phase 2
0.6872	Remote Similarity	NPD4467	Phase 2
0.685	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5186	Approved
0.6821	Remote Similarity	NPD5183	Approved
0.6818	Remote Similarity	NPD5600	Discontinued
0.68	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2680	Approved
0.6769	Remote Similarity	NPD2681	Approved
0.6746	Remote Similarity	NPD5197	Approved
0.6746	Remote Similarity	NPD5194	Approved
0.6746	Remote Similarity	NPD5196	Approved
0.673	Remote Similarity	NPD6238	Discontinued
0.6726	Remote Similarity	NPD7542	Phase 3
0.6714	Remote Similarity	NPD6874	Approved
0.6699	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5195	Discontinued
0.6684	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3983	Phase 3
0.6683	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7186	Phase 3
0.6667	Remote Similarity	NPD5445	Approved
0.6667	Remote Similarity	NPD4796	Discontinued
0.6667	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5937	Approved
0.665	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD19	Approved
0.6649	Remote Similarity	NPD1742	Approved
0.6649	Remote Similarity	NPD1743	Approved
0.6638	Remote Similarity	NPD6625	Approved
0.6636	Remote Similarity	NPD1294	Discontinued
0.6635	Remote Similarity	NPD5609	Approved
0.6635	Remote Similarity	NPD5608	Approved
0.6634	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7300	Phase 3
0.662	Remote Similarity	NPD6376	Discontinued
0.662	Remote Similarity	NPD7302	Phase 3
0.6617	Remote Similarity	NPD7479	Phase 2
0.6617	Remote Similarity	NPD5190	Phase 2
0.6617	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2672	Discontinued
0.6614	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2455	Approved
0.6599	Remote Similarity	NPD2454	Approved
0.6596	Remote Similarity	NPD1802	Approved
0.6596	Remote Similarity	NPD1801	Approved
0.6584	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6297	Approved
0.6583	Remote Similarity	NPD3377	Discontinued
0.658	Remote Similarity	NPD3006	Discontinued
0.658	Remote Similarity	NPD1769	Discontinued
0.6577	Remote Similarity	NPD7292	Approved
0.6575	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7301	Phase 3
0.6573	Remote Similarity	NPD3416	Discontinued
0.6573	Remote Similarity	NPD6321	Discontinued
0.657	Remote Similarity	NPD7630	Phase 3
0.657	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7628	Phase 3
0.6567	Remote Similarity	NPD4603	Phase 2
0.6567	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD3298	Approved
0.6552	Remote Similarity	NPD3470	Approved
0.6552	Remote Similarity	NPD3471	Approved
0.655	Remote Similarity	NPD5466	Approved
0.6547	Remote Similarity	NPD5496	Approved
0.6542	Remote Similarity	NPD956	Clinical (unspecified phase)
0.654	Remote Similarity	NPD3828	Approved
0.6533	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6805	Discontinued
0.6522	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3437	Discontinued
0.6516	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6457	Approved
0.6515	Remote Similarity	NPD2037	Approved
0.6515	Remote Similarity	NPD7126	Discontinued
0.6502	Remote Similarity	NPD4330	Approved
0.6502	Remote Similarity	NPD4329	Approved
0.6497	Remote Similarity	NPD5430	Discontinued
0.6473	Remote Similarity	NPD2899	Discontinued
0.6473	Remote Similarity	NPD4515	Suspended
0.6468	Remote Similarity	NPD3422	Phase 3
0.6468	Remote Similarity	NPD3423	Phase 2
0.6465	Remote Similarity	NPD5823	Approved
0.6462	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD2427	Approved
0.6459	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD8167	Discontinued
0.6456	Remote Similarity	NPD6851	Approved
0.6456	Remote Similarity	NPD6853	Approved
0.6452	Remote Similarity	NPD6807	Phase 3
0.645	Remote Similarity	NPD2431	Approved
0.645	Remote Similarity	NPD2432	Approved
0.6432	Remote Similarity	NPD5071	Phase 2
0.6432	Remote Similarity	NPD2404	Discontinued
0.6432	Remote Similarity	NPD3912	Discontinued
0.6432	Remote Similarity	NPD7278	Phase 2
0.6432	Remote Similarity	NPD7279	Phase 2
0.6429	Remote Similarity	NPD4311	Approved
0.6429	Remote Similarity	NPD2506	Approved
0.6426	Remote Similarity	NPD7560	Approved
0.6419	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5582	Discontinued
0.6411	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7280	Phase 3
0.6408	Remote Similarity	NPD7281	Phase 3
0.6406	Remote Similarity	NPD3640	Phase 3
0.6406	Remote Similarity	NPD3641	Approved
0.6406	Remote Similarity	NPD3639	Approved
0.6404	Remote Similarity	NPD5312	Approved
0.6404	Remote Similarity	NPD5313	Approved
0.6404	Remote Similarity	NPD3792	Approved
0.6402	Remote Similarity	NPD3297	Approved
0.6402	Remote Similarity	NPD8358	Approved
0.6387	Remote Similarity	NPD7528	Approved
0.6387	Remote Similarity	NPD4888	Discontinued
0.6382	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5504	Discontinued
0.6378	Remote Similarity	NPD6636	Phase 3
0.6378	Remote Similarity	NPD2670	Approved
0.6372	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6835	Approved
0.6364	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.636	Remote Similarity	NPD8364	Approved
0.636	Remote Similarity	NPD7820	Phase 3
0.636	Remote Similarity	NPD8363	Approved
0.6359	Remote Similarity	NPD7205	Discontinued
0.6359	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4429	Discontinued
0.6356	Remote Similarity	NPD8016	Phase 3
0.6356	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6723	Discontinued
0.635	Remote Similarity	NPD3468	Approved
0.6349	Remote Similarity	NPD3986	Discontinued
0.6348	Remote Similarity	NPD1755	Approved
0.6347	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8149	Discontinued
0.6338	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2898	Approved
0.6337	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD3793	Phase 3
0.632	Remote Similarity	NPD7924	Phase 2
0.632	Remote Similarity	NPD7925	Phase 2
0.6318	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD2916	Discontinued
0.6316	Remote Similarity	NPD6017	Discontinued
0.631	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD3746	Discontinued
0.6308	Remote Similarity	NPD6161	Approved
0.6308	Remote Similarity	NPD6162	Approved
0.6305	Remote Similarity	NPD5033	Approved
0.6305	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7603	Discontinued
0.6303	Remote Similarity	NPD3884	Discontinued
0.6303	Remote Similarity	NPD2490	Approved
0.6303	Remote Similarity	NPD6716	Phase 1
0.6303	Remote Similarity	NPD7283	Approved
0.6303	Remote Similarity	NPD6659	Phase 2
0.6303	Remote Similarity	NPD2488	Approved
0.63	Remote Similarity	NPD6037	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