NPASS Compound

Structure

NPC473297 OpenBabel07101718302D 30 34 0 0 1 0 0 0 0 0999 V2000 -1.0610 -1.2398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6546 -3.2988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0979 -2.4150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5224 -0.4513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8218 -1.0048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3588 -0.2657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9133 -0.9093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9872 0.5688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1182 -0.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9094 0.2076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6345 1.0989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2726 0.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 -3.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0702 0.3425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5417 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5818 0.3967 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0787 0.6643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1182 1.5779 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6729 1.1211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3338 -0.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2783 -2.8569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6729 0.2076 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5417 1.4034 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9094 1.1211 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.4175 -4.2854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2371 -0.9865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9446 -3.7073 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2358 -1.5646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1817 -2.7208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 13 1 0 0 0 0 3 29 1 0 0 0 0 4 14 2 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 17 2 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 26 2 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 1 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 23 1 0 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 21 23 1 0 0 0 0 21 28 2 0 0 0 0 21 30 1 0 0 0 0 22 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.17
Volume:	408.435
LogP:	1.912
LogD:	1.996
LogS:	-2.886
# Rotatable Bonds:	5
TPSA:	85.27
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	5.524
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.266
MDCK Permeability:	3.501666651573032e-05
Pgp-inhibitor:	0.544
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.9
Plasma Protein Binding (PPB):	64.52835845947266%
Volume Distribution (VD):	0.787
Pgp-substrate:	57.53865051269531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.391
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.259
CYP2C9-substrate:	0.693
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.649
CYP3A4-inhibitor:	0.483
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	5.923
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.503
Drug-inuced Liver Injury (DILI):	0.56
AMES Toxicity:	0.906
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.305
Carcinogencity:	0.901
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC473297

Natural Product ID:	NPC473297
*Common Name:**	GSUAXYSDIZYHQW-IIEREXMUSA-N
IUPAC Name:	n.a.
Synonyms:	16-Epiakuammiline
Standard InCHIKey:	GSUAXYSDIZYHQW-IIEREXMUSA-N
Standard InCHI:	InChI=1S/C23H24N2O5/c1-4-14-12-25-10-9-22-15-7-5-6-8-17(15)24-19(22)18(25)11-16(14)23(22,20(27)29-3)21(28)30-13(2)26/h4-8,16,18H,9-12H2,1-3H3/b14-4-/t16-,18+,22-,23?/m1/s1
SMILES:	C/C=C1/CN2CC[C@]34C([C@@H]1C[C@H]2C3=Nc1c4cccc1)(C(=O)OC)C(=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398822
PubChem CID:	44445384
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002750] Corynanthean-type 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
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17939738]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	leaf and stem-bark	Pahang, Malaysia	1996-JUL	PMID[18078327]
NPO19270	Kopsia singapurensis	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
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[490057]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[490057]

☑ 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 NPC473297 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	234
0.1-0.2	1115
0.2-0.3	4040
0.3-0.4	18830
0.4-0.5	13648
0.5-0.6	4066
0.6-0.7	656
0.7-0.8	105
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8052	Intermediate Similarity	NPC116519
0.7987	Intermediate Similarity	NPC161827
0.7901	Intermediate Similarity	NPC225319
0.7888	Intermediate Similarity	NPC211525
0.7888	Intermediate Similarity	NPC153694
0.7843	Intermediate Similarity	NPC243162
0.784	Intermediate Similarity	NPC97380
0.784	Intermediate Similarity	NPC148468
0.784	Intermediate Similarity	NPC63210
0.784	Intermediate Similarity	NPC243673
0.784	Intermediate Similarity	NPC263709
0.784	Intermediate Similarity	NPC310403
0.7818	Intermediate Similarity	NPC278887
0.7744	Intermediate Similarity	NPC99632
0.7744	Intermediate Similarity	NPC282339
0.7716	Intermediate Similarity	NPC477156
0.7716	Intermediate Similarity	NPC477157
0.7702	Intermediate Similarity	NPC478076
0.7665	Intermediate Similarity	NPC469462
0.7651	Intermediate Similarity	NPC470069
0.7651	Intermediate Similarity	NPC52059
0.7633	Intermediate Similarity	NPC476425
0.7572	Intermediate Similarity	NPC475962
0.7543	Intermediate Similarity	NPC469460
0.7543	Intermediate Similarity	NPC472209
0.7529	Intermediate Similarity	NPC293255
0.7529	Intermediate Similarity	NPC139085
0.7529	Intermediate Similarity	NPC210415
0.7529	Intermediate Similarity	NPC214626
0.7529	Intermediate Similarity	NPC21752
0.7529	Intermediate Similarity	NPC276993
0.7529	Intermediate Similarity	NPC251212
0.7529	Intermediate Similarity	NPC298851
0.7529	Intermediate Similarity	NPC181138
0.7515	Intermediate Similarity	NPC469461
0.747	Intermediate Similarity	NPC477158
0.747	Intermediate Similarity	NPC248117
0.741	Intermediate Similarity	NPC193410
0.7384	Intermediate Similarity	NPC13367
0.7349	Intermediate Similarity	NPC61013
0.7341	Intermediate Similarity	NPC476441
0.7321	Intermediate Similarity	NPC472121
0.7312	Intermediate Similarity	NPC162730
0.7299	Intermediate Similarity	NPC476326
0.7296	Intermediate Similarity	NPC477155
0.7262	Intermediate Similarity	NPC143457
0.7247	Intermediate Similarity	NPC52262
0.7246	Intermediate Similarity	NPC113946
0.7238	Intermediate Similarity	NPC28510
0.7234	Intermediate Similarity	NPC185742
0.7234	Intermediate Similarity	NPC475847
0.7232	Intermediate Similarity	NPC143533
0.7222	Intermediate Similarity	NPC472100
0.7222	Intermediate Similarity	NPC175474
0.7219	Intermediate Similarity	NPC474116
0.7204	Intermediate Similarity	NPC81654
0.7204	Intermediate Similarity	NPC249150
0.7204	Intermediate Similarity	NPC195461
0.7204	Intermediate Similarity	NPC49196
0.7204	Intermediate Similarity	NPC79129
0.7204	Intermediate Similarity	NPC313985
0.7202	Intermediate Similarity	NPC36495
0.72	Intermediate Similarity	NPC260075
0.7191	Intermediate Similarity	NPC472119
0.7189	Intermediate Similarity	NPC52557
0.7186	Intermediate Similarity	NPC29285
0.7167	Intermediate Similarity	NPC21425
0.7158	Intermediate Similarity	NPC203972
0.7152	Intermediate Similarity	NPC317758
0.7151	Intermediate Similarity	NPC472107
0.7151	Intermediate Similarity	NPC223595
0.7151	Intermediate Similarity	NPC224970
0.7151	Intermediate Similarity	NPC79062
0.7151	Intermediate Similarity	NPC167724
0.7143	Intermediate Similarity	NPC123241
0.7126	Intermediate Similarity	NPC96901
0.7124	Intermediate Similarity	NPC478079
0.712	Intermediate Similarity	NPC34717
0.7111	Intermediate Similarity	NPC282092
0.7097	Intermediate Similarity	NPC50503
0.7095	Intermediate Similarity	NPC264580
0.7093	Intermediate Similarity	NPC472114
0.7093	Intermediate Similarity	NPC472115
0.7079	Intermediate Similarity	NPC476428
0.7059	Intermediate Similarity	NPC474058
0.7045	Intermediate Similarity	NPC264482
0.7045	Intermediate Similarity	NPC203202
0.7043	Intermediate Similarity	NPC90967
0.7035	Intermediate Similarity	NPC472106
0.7027	Intermediate Similarity	NPC221687
0.7018	Intermediate Similarity	NPC293458
0.6995	Remote Similarity	NPC329858
0.6995	Remote Similarity	NPC105055
0.6995	Remote Similarity	NPC473298
0.6995	Remote Similarity	NPC22689
0.6978	Remote Similarity	NPC181928
0.6978	Remote Similarity	NPC472323
0.6966	Remote Similarity	NPC6974
0.6952	Remote Similarity	NPC469736
0.6941	Remote Similarity	NPC104345
0.694	Remote Similarity	NPC196251
0.694	Remote Similarity	NPC102338
0.694	Remote Similarity	NPC63199
0.694	Remote Similarity	NPC111602
0.6935	Remote Similarity	NPC57994
0.6935	Remote Similarity	NPC289299
0.6923	Remote Similarity	NPC66210
0.6919	Remote Similarity	NPC176983
0.6906	Remote Similarity	NPC245741
0.6906	Remote Similarity	NPC258480
0.6898	Remote Similarity	NPC245916
0.6893	Remote Similarity	NPC329338
0.6893	Remote Similarity	NPC469726
0.6872	Remote Similarity	NPC99043
0.6872	Remote Similarity	NPC218594
0.6865	Remote Similarity	NPC472097
0.6862	Remote Similarity	NPC475559
0.6862	Remote Similarity	NPC162440
0.686	Remote Similarity	NPC201424
0.6859	Remote Similarity	NPC474077
0.6845	Remote Similarity	NPC474121
0.6833	Remote Similarity	NPC15840
0.6828	Remote Similarity	NPC55493
0.6821	Remote Similarity	NPC472101
0.6821	Remote Similarity	NPC472120
0.6821	Remote Similarity	NPC476231
0.6816	Remote Similarity	NPC186669
0.6811	Remote Similarity	NPC314333
0.6809	Remote Similarity	NPC473375
0.6809	Remote Similarity	NPC472116
0.6809	Remote Similarity	NPC97100
0.6806	Remote Similarity	NPC471512
0.6802	Remote Similarity	NPC475778
0.679	Remote Similarity	NPC469560
0.6788	Remote Similarity	NPC472103
0.6786	Remote Similarity	NPC234999
0.6778	Remote Similarity	NPC321211
0.677	Remote Similarity	NPC471123
0.6758	Remote Similarity	NPC472104
0.6758	Remote Similarity	NPC159963
0.6754	Remote Similarity	NPC138830
0.6754	Remote Similarity	NPC67904
0.6746	Remote Similarity	NPC243756
0.6738	Remote Similarity	NPC472113
0.6722	Remote Similarity	NPC234987
0.672	Remote Similarity	NPC472112
0.6707	Remote Similarity	NPC264589
0.6705	Remote Similarity	NPC214960
0.6705	Remote Similarity	NPC279527
0.6703	Remote Similarity	NPC14994
0.6686	Remote Similarity	NPC469541
0.6686	Remote Similarity	NPC473329
0.6684	Remote Similarity	NPC302548
0.6684	Remote Similarity	NPC25401
0.6667	Remote Similarity	NPC294909
0.6667	Remote Similarity	NPC255229
0.6667	Remote Similarity	NPC316746
0.6667	Remote Similarity	NPC81229
0.6667	Remote Similarity	NPC128265
0.6667	Remote Similarity	NPC312870
0.6667	Remote Similarity	NPC254240
0.6667	Remote Similarity	NPC199851
0.6667	Remote Similarity	NPC471516
0.6649	Remote Similarity	NPC478077
0.6649	Remote Similarity	NPC291759
0.6648	Remote Similarity	NPC285622
0.6648	Remote Similarity	NPC473743
0.6648	Remote Similarity	NPC475420
0.6648	Remote Similarity	NPC469896
0.6648	Remote Similarity	NPC11149
0.6647	Remote Similarity	NPC66936
0.6633	Remote Similarity	NPC477065
0.6629	Remote Similarity	NPC194881
0.6629	Remote Similarity	NPC286871
0.6629	Remote Similarity	NPC469741
0.6615	Remote Similarity	NPC329833
0.6607	Remote Similarity	NPC469735
0.6595	Remote Similarity	NPC322621
0.6595	Remote Similarity	NPC133591
0.6592	Remote Similarity	NPC318183
0.6579	Remote Similarity	NPC220151
0.6579	Remote Similarity	NPC19692
0.6576	Remote Similarity	NPC477159
0.6561	Remote Similarity	NPC474926
0.6559	Remote Similarity	NPC38823
0.6559	Remote Similarity	NPC207033
0.6556	Remote Similarity	NPC473880
0.6556	Remote Similarity	NPC477976
0.655	Remote Similarity	NPC154602
0.655	Remote Similarity	NPC206592
0.6541	Remote Similarity	NPC97584
0.6536	Remote Similarity	NPC469915
0.6534	Remote Similarity	NPC472117
0.6528	Remote Similarity	NPC241024
0.6522	Remote Similarity	NPC113626
0.6512	Remote Similarity	NPC122106
0.6506	Remote Similarity	NPC161069
0.6503	Remote Similarity	NPC248462
0.6497	Remote Similarity	NPC277350
0.6495	Remote Similarity	NPC214428

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 NPC473297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	479
0.2-0.3	783
0.3-0.4	1494
0.4-0.5	3624
0.5-0.6	2338
0.6-0.7	284
0.7-0.8	8
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
0.7403	Intermediate Similarity	NPD5185	Approved
0.7403	Intermediate Similarity	NPD5182	Approved
0.7403	Intermediate Similarity	NPD5184	Approved
0.7204	Intermediate Similarity	NPD4601	Approved
0.7204	Intermediate Similarity	NPD4600	Approved
0.7101	Intermediate Similarity	NPD7599	Phase 2
0.7059	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7795	Phase 2
0.6959	Remote Similarity	NPD7600	Phase 2
0.6946	Remote Similarity	NPD7606	Phase 3
0.6935	Remote Similarity	NPD4602	Approved
0.6928	Remote Similarity	NPD4682	Phase 2
0.6867	Remote Similarity	NPD7478	Approved
0.6867	Remote Similarity	NPD2994	Approved
0.6859	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2210	Approved
0.6821	Remote Similarity	NPD2212	Approved
0.6811	Remote Similarity	NPD4499	Approved
0.68	Remote Similarity	NPD2117	Pre-registration
0.68	Remote Similarity	NPD2115	Approved
0.68	Remote Similarity	NPD2116	Approved
0.6797	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5578	Approved
0.6774	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2946	Phase 2
0.6711	Remote Similarity	NPD3032	Approved
0.6711	Remote Similarity	NPD3031	Approved
0.6711	Remote Similarity	NPD3030	Approved
0.6709	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3423	Phase 2
0.6704	Remote Similarity	NPD3422	Phase 3
0.6687	Remote Similarity	NPD7487	Discontinued
0.6685	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7234	Approved
0.6667	Remote Similarity	NPD4501	Approved
0.6667	Remote Similarity	NPD4500	Approved
0.6667	Remote Similarity	NPD7233	Approved
0.6648	Remote Similarity	NPD3377	Discontinued
0.6647	Remote Similarity	NPD5982	Phase 2
0.6644	Remote Similarity	NPD3149	Approved
0.6644	Remote Similarity	NPD3148	Approved
0.6644	Remote Similarity	NPD3147	Approved
0.6644	Remote Similarity	NPD2658	Approved
0.6644	Remote Similarity	NPD2659	Approved
0.6644	Remote Similarity	NPD3150	Approved
0.663	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6416	Phase 2
0.6606	Remote Similarity	NPD6789	Approved
0.66	Remote Similarity	NPD5631	Phase 3
0.6596	Remote Similarity	NPD5504	Discontinued
0.6585	Remote Similarity	NPD3170	Approved
0.6577	Remote Similarity	NPD1762	Approved
0.6577	Remote Similarity	NPD1764	Approved
0.6561	Remote Similarity	NPD1036	Approved
0.6561	Remote Similarity	NPD8146	Phase 2
0.6548	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4412	Phase 2
0.6533	Remote Similarity	NPD23	Approved
0.6529	Remote Similarity	NPD4432	Discontinued
0.6524	Remote Similarity	NPD2670	Approved
0.6514	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2948	Discontinued
0.6509	Remote Similarity	NPD4041	Approved
0.6488	Remote Similarity	NPD2435	Approved
0.6482	Remote Similarity	NPD4520	Approved
0.6477	Remote Similarity	NPD2506	Approved
0.6474	Remote Similarity	NPD3132	Approved
0.6474	Remote Similarity	NPD3131	Approved
0.6474	Remote Similarity	NPD2610	Approved
0.6474	Remote Similarity	NPD2611	Approved
0.6474	Remote Similarity	NPD2608	Approved
0.6474	Remote Similarity	NPD2609	Approved
0.6474	Remote Similarity	NPD2612	Approved
0.6474	Remote Similarity	NPD4215	Approved
0.6474	Remote Similarity	NPD4217	Approved
0.6474	Remote Similarity	NPD4218	Approved
0.6474	Remote Similarity	NPD4216	Approved
0.6471	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4329	Approved
0.6467	Remote Similarity	NPD6566	Discontinued
0.6467	Remote Similarity	NPD4330	Approved
0.6467	Remote Similarity	NPD181	Approved
0.6467	Remote Similarity	NPD2607	Approved
0.6461	Remote Similarity	NPD7035	Approved
0.6461	Remote Similarity	NPD7036	Phase 3
0.646	Remote Similarity	NPD6489	Phase 3
0.645	Remote Similarity	NPD5931	Phase 3
0.645	Remote Similarity	NPD5932	Phase 3
0.645	Remote Similarity	NPD7295	Approved
0.645	Remote Similarity	NPD5933	Phase 3
0.6438	Remote Similarity	NPD4549	Discontinued
0.6437	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5941	Approved
0.6433	Remote Similarity	NPD5942	Approved
0.6429	Remote Similarity	NPD7082	Approved
0.6429	Remote Similarity	NPD2820	Phase 3
0.6424	Remote Similarity	NPD2569	Approved
0.6424	Remote Similarity	NPD2567	Approved
0.6424	Remote Similarity	NPD1681	Approved
0.6424	Remote Similarity	NPD1682	Approved
0.6424	Remote Similarity	NPD1680	Approved
0.6421	Remote Similarity	NPD2336	Approved
0.642	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6570	Approved
0.64	Remote Similarity	NPD6571	Approved
0.64	Remote Similarity	NPD7105	Phase 1
0.6392	Remote Similarity	NPD4397	Phase 1
0.6391	Remote Similarity	NPD7259	Approved
0.6391	Remote Similarity	NPD5918	Discontinued
0.6387	Remote Similarity	NPD5981	Approved
0.6386	Remote Similarity	NPD1109	Approved
0.6386	Remote Similarity	NPD1110	Approved
0.6384	Remote Similarity	NPD7244	Discontinued
0.638	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4121	Phase 3
0.6379	Remote Similarity	NPD4120	Approved
0.6378	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7973	Discontinued
0.6376	Remote Similarity	NPD1752	Approved
0.6376	Remote Similarity	NPD1756	Approved
0.6375	Remote Similarity	NPD5993	Phase 1
0.6369	Remote Similarity	NPD7437	Approved
0.6369	Remote Similarity	NPD7436	Approved
0.6369	Remote Similarity	NPD2365	Approved
0.6359	Remote Similarity	NPD3792	Approved
0.6353	Remote Similarity	NPD6622	Phase 1
0.6353	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3471	Approved
0.6344	Remote Similarity	NPD3470	Approved
0.6343	Remote Similarity	NPD5742	Approved
0.6343	Remote Similarity	NPD5741	Approved
0.6343	Remote Similarity	NPD5743	Approved
0.6339	Remote Similarity	NPD7940	Phase 3
0.6335	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3643	Approved
0.6333	Remote Similarity	NPD3644	Approved
0.6333	Remote Similarity	NPD3642	Approved
0.6329	Remote Similarity	NPD2584	Suspended
0.6329	Remote Similarity	NPD7461	Approved
0.6328	Remote Similarity	NPD2427	Approved
0.6322	Remote Similarity	NPD3399	Approved
0.6316	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD8270	Approved
0.6313	Remote Similarity	NPD6635	Approved
0.6313	Remote Similarity	NPD8008	Approved
0.6313	Remote Similarity	NPD7734	Approved
0.6313	Remote Similarity	NPD8007	Approved
0.6312	Remote Similarity	NPD6563	Approved
0.6312	Remote Similarity	NPD6565	Approved
0.6312	Remote Similarity	NPD6564	Approved
0.631	Remote Similarity	NPD3625	Discontinued
0.631	Remote Similarity	NPD7962	Phase 2
0.631	Remote Similarity	NPD2010	Phase 3
0.6309	Remote Similarity	NPD2678	Approved
0.6309	Remote Similarity	NPD2679	Approved
0.6308	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5104	Approved
0.6304	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD7569	Approved
0.6302	Remote Similarity	NPD7570	Approved
0.6301	Remote Similarity	NPD5748	Phase 2
0.6299	Remote Similarity	NPD4576	Approved
0.6299	Remote Similarity	NPD4574	Approved
0.6298	Remote Similarity	NPD2037	Approved
0.6298	Remote Similarity	NPD2844	Phase 3
0.6296	Remote Similarity	NPD2613	Approved
0.6292	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7275	Approved
0.6291	Remote Similarity	NPD2038	Approved
0.6291	Remote Similarity	NPD2039	Approved
0.629	Remote Similarity	NPD5898	Approved
0.629	Remote Similarity	NPD5899	Approved
0.629	Remote Similarity	NPD6878	Phase 2
0.629	Remote Similarity	NPD6879	Phase 2
0.629	Remote Similarity	NPD5897	Approved
0.6289	Remote Similarity	NPD2307	Discontinued
0.6284	Remote Similarity	NPD7854	Phase 2
0.6284	Remote Similarity	NPD5997	Discontinued
0.6283	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1801	Approved
0.6279	Remote Similarity	NPD1802	Approved
0.6277	Remote Similarity	NPD7483	Phase 2
0.6277	Remote Similarity	NPD7482	Phase 2
0.6276	Remote Similarity	NPD6874	Approved
0.6275	Remote Similarity	NPD3551	Approved
0.6267	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD4116	Approved
0.6264	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8355	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