NPASS Compound

Structure

CID286871 OpenBabel06191716092D 24 28 0 0 1 0 0 0 0 0999 V2000 -5.0481 2.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5222 -0.8265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1346 2.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7472 2.8904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5076 2.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1955 2.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 1.2577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7043 2.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7043 0.5769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4835 1.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3745 2.1950 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7867 1.3859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3777 1.5733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3255 1.8859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3745 0.5769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3827 0.9239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 1.7210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9969 0.0785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 1.0508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3255 0.8859 0.0000 N 0 0 0 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 -1.6464 -0.6819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5225 -0.8526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1396 1.3300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 10 24 1 0 0 0 0 11 8 1 6 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 10 1 6 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 3 1 6 0 0 0 14 20 1 0 0 0 0 15 9 1 6 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 6 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 18 22 2 0 0 0 0 19 9 1 1 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.18
Volume:	332.216
LogP:	3.067
LogD:	2.793
LogS:	-4.893
# Rotatable Bonds:	2
TPSA:	50.8
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.902
Synthetic Accessibility Score:	6.332
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.22
MDCK Permeability:	2.0535386283881962e-05
Pgp-inhibitor:	0.538
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.437
30% Bioavailability (F30%):	0.49

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.849
Plasma Protein Binding (PPB):	17.097877502441406%
Volume Distribution (VD):	1.412
Pgp-substrate:	67.06440734863281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.685
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.099
CYP2C9-substrate:	0.162
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.351
CYP3A4-inhibitor:	0.541
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	8.905
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.85
Human Hepatotoxicity (H-HT):	0.445
Drug-inuced Liver Injury (DILI):	0.462
AMES Toxicity:	0.868
Rat Oral Acute Toxicity:	0.83
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.422
Carcinogencity:	0.673
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC286871

Natural Product ID:	NPC286871
*Common Name:**	Gelsedine
IUPAC Name:	n.a.
Synonyms:	Gelsedine
Standard InCHIKey:	LDBVYQSHIPCQPT-CTSQFDBHSA-N
Standard InCHI:	InChI=1S/C19H24N2O3/c1-3-14-11-8-17-19(9-15(20-14)12(11)10-24-17)13-6-4-5-7-16(13)21(23-2)18(19)22/h4-7,11-12,14-15,17,20H,3,8-10H2,1-2H3/t11-,12+,14-,15+,17-,19+/m1/s1
SMILES:	CC[C@H]1N[C@@H]2[C@@H]3[C@H]1C[C@H]([C@]1(C2)c2ccccc2N(C1=O)OC)OC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476885
PubChem CID:	21589070
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003758] Gelsemium 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
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643063]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989532]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256496]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	leaves and vine stems	Xishuangbanna Tropical Botanical Garden (XTBG), Chinese Academy of Science (CAS), Mengla County, Yunnan Province, China	2009-OCT	PMID[26103517]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222693]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	EC50	=	350.0	nM	PMID[525402]

☑ 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 NPC286871 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	254
0.1-0.2	1304
0.2-0.3	5755
0.3-0.4	22754
0.4-0.5	8748
0.5-0.6	3275
0.6-0.7	499
0.7-0.8	93
0.8-0.85	8
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC176983
0.9211	High Similarity	NPC29285
0.891	High Similarity	NPC143457
0.8788	High Similarity	NPC477159
0.8605	High Similarity	NPC243626
0.8553	High Similarity	NPC472102
0.8553	High Similarity	NPC309531
0.8537	High Similarity	NPC13367
0.8529	High Similarity	NPC284706
0.8344	Intermediate Similarity	NPC214960
0.8344	Intermediate Similarity	NPC279527
0.8286	Intermediate Similarity	NPC230313
0.8199	Intermediate Similarity	NPC113946
0.8187	Intermediate Similarity	NPC245741
0.8092	Intermediate Similarity	NPC282092
0.8061	Intermediate Similarity	NPC472106
0.8049	Intermediate Similarity	NPC472120
0.8049	Intermediate Similarity	NPC472101
0.7939	Intermediate Similarity	NPC472117
0.7929	Intermediate Similarity	NPC285622
0.7853	Intermediate Similarity	NPC473008
0.7838	Intermediate Similarity	NPC477161
0.7824	Intermediate Similarity	NPC251212
0.7824	Intermediate Similarity	NPC214626
0.7824	Intermediate Similarity	NPC139085
0.7791	Intermediate Similarity	NPC260075
0.779	Intermediate Similarity	NPC302548
0.7765	Intermediate Similarity	NPC473004
0.7727	Intermediate Similarity	NPC259626
0.7727	Intermediate Similarity	NPC473007
0.7719	Intermediate Similarity	NPC96901
0.7713	Intermediate Similarity	NPC477160
0.7692	Intermediate Similarity	NPC475559
0.767	Intermediate Similarity	NPC2933
0.7619	Intermediate Similarity	NPC282339
0.7619	Intermediate Similarity	NPC99632
0.7619	Intermediate Similarity	NPC472121
0.7616	Intermediate Similarity	NPC476425
0.7614	Intermediate Similarity	NPC256288
0.7556	Intermediate Similarity	NPC22689
0.7556	Intermediate Similarity	NPC105055
0.7529	Intermediate Similarity	NPC203202
0.7529	Intermediate Similarity	NPC264482
0.7528	Intermediate Similarity	NPC52262
0.7516	Intermediate Similarity	NPC472103
0.75	Intermediate Similarity	NPC193410
0.75	Intermediate Similarity	NPC472118
0.7486	Intermediate Similarity	NPC186669
0.7486	Intermediate Similarity	NPC473615
0.7486	Intermediate Similarity	NPC476326
0.7459	Intermediate Similarity	NPC100863
0.7459	Intermediate Similarity	NPC473298
0.7456	Intermediate Similarity	NPC201424
0.7456	Intermediate Similarity	NPC225319
0.7456	Intermediate Similarity	NPC248117
0.7455	Intermediate Similarity	NPC475763
0.7444	Intermediate Similarity	NPC229484
0.7444	Intermediate Similarity	NPC181928
0.744	Intermediate Similarity	NPC61013
0.7429	Intermediate Similarity	NPC476441
0.7423	Intermediate Similarity	NPC264589
0.7416	Intermediate Similarity	NPC159963
0.7407	Intermediate Similarity	NPC14339
0.7403	Intermediate Similarity	NPC292675
0.7391	Intermediate Similarity	NPC34717
0.738	Intermediate Similarity	NPC475489
0.7371	Intermediate Similarity	NPC473006
0.7353	Intermediate Similarity	NPC315368
0.7345	Intermediate Similarity	NPC99043
0.7345	Intermediate Similarity	NPC6974
0.7345	Intermediate Similarity	NPC218594
0.7341	Intermediate Similarity	NPC224970
0.7341	Intermediate Similarity	NPC167724
0.7341	Intermediate Similarity	NPC223595
0.7337	Intermediate Similarity	NPC123241
0.7322	Intermediate Similarity	NPC25401
0.7314	Intermediate Similarity	NPC177261
0.7312	Intermediate Similarity	NPC90967
0.731	Intermediate Similarity	NPC293458
0.7294	Intermediate Similarity	NPC36495
0.7287	Intermediate Similarity	NPC138830
0.7267	Intermediate Similarity	NPC315051
0.7263	Intermediate Similarity	NPC476428
0.7262	Intermediate Similarity	NPC478076
0.7253	Intermediate Similarity	NPC14994
0.7251	Intermediate Similarity	NPC68650
0.7232	Intermediate Similarity	NPC129624
0.7225	Intermediate Similarity	NPC471124
0.7219	Intermediate Similarity	NPC161827
0.7207	Intermediate Similarity	NPC11149
0.7196	Intermediate Similarity	NPC67904
0.7188	Intermediate Similarity	NPC477173
0.7182	Intermediate Similarity	NPC97584
0.7175	Intermediate Similarity	NPC329338
0.7175	Intermediate Similarity	NPC469726
0.7151	Intermediate Similarity	NPC475094
0.715	Intermediate Similarity	NPC470488
0.7135	Intermediate Similarity	NPC211525
0.7135	Intermediate Similarity	NPC153694
0.7128	Intermediate Similarity	NPC162440
0.712	Intermediate Similarity	NPC474116
0.712	Intermediate Similarity	NPC473005
0.711	Intermediate Similarity	NPC85651
0.7105	Intermediate Similarity	NPC214428
0.7093	Intermediate Similarity	NPC310403
0.7093	Intermediate Similarity	NPC263709
0.7093	Intermediate Similarity	NPC471122
0.7093	Intermediate Similarity	NPC243673
0.7093	Intermediate Similarity	NPC63210
0.7093	Intermediate Similarity	NPC148468
0.7093	Intermediate Similarity	NPC97380
0.7083	Intermediate Similarity	NPC477179
0.7081	Intermediate Similarity	NPC471123
0.7069	Intermediate Similarity	NPC313757
0.7056	Intermediate Similarity	NPC321211
0.7052	Intermediate Similarity	NPC474058
0.7047	Intermediate Similarity	NPC470489
0.7047	Intermediate Similarity	NPC477178
0.7047	Intermediate Similarity	NPC477181
0.7047	Intermediate Similarity	NPC254850
0.7047	Intermediate Similarity	NPC477180
0.7035	Intermediate Similarity	NPC222029
0.7031	Intermediate Similarity	NPC162730
0.7029	Intermediate Similarity	NPC470069
0.7029	Intermediate Similarity	NPC52059
0.7026	Intermediate Similarity	NPC471950
0.7026	Intermediate Similarity	NPC471945
0.701	Intermediate Similarity	NPC470490
0.701	Intermediate Similarity	NPC277350
0.701	Intermediate Similarity	NPC477174
0.7006	Intermediate Similarity	NPC472100
0.7005	Intermediate Similarity	NPC55493
0.699	Remote Similarity	NPC471951
0.699	Remote Similarity	NPC469743
0.699	Remote Similarity	NPC471946
0.6982	Remote Similarity	NPC318086
0.6957	Remote Similarity	NPC322621
0.6951	Remote Similarity	NPC130251
0.6939	Remote Similarity	NPC470491
0.6939	Remote Similarity	NPC475259
0.6931	Remote Similarity	NPC221687
0.6927	Remote Similarity	NPC276993
0.6927	Remote Similarity	NPC181138
0.6927	Remote Similarity	NPC298851
0.6927	Remote Similarity	NPC210415
0.6927	Remote Similarity	NPC293255
0.6927	Remote Similarity	NPC21752
0.691	Remote Similarity	NPC469915
0.6898	Remote Similarity	NPC474059
0.6898	Remote Similarity	NPC5630
0.6898	Remote Similarity	NPC314333
0.6898	Remote Similarity	NPC329858
0.6897	Remote Similarity	NPC276085
0.6895	Remote Similarity	NPC473375
0.6895	Remote Similarity	NPC97100
0.6893	Remote Similarity	NPC472115
0.6893	Remote Similarity	NPC472114
0.6886	Remote Similarity	NPC311330
0.6882	Remote Similarity	NPC473329
0.6881	Remote Similarity	NPC77777
0.6872	Remote Similarity	NPC355
0.6869	Remote Similarity	NPC191817
0.6869	Remote Similarity	NPC475359
0.6865	Remote Similarity	NPC472209
0.6864	Remote Similarity	NPC212799
0.6862	Remote Similarity	NPC203628
0.6862	Remote Similarity	NPC22476
0.6852	Remote Similarity	NPC162417
0.6852	Remote Similarity	NPC316104
0.6842	Remote Similarity	NPC66936
0.6842	Remote Similarity	NPC243756
0.6833	Remote Similarity	NPC473743
0.6826	Remote Similarity	NPC469537
0.6824	Remote Similarity	NPC109787
0.6824	Remote Similarity	NPC242000
0.6809	Remote Similarity	NPC473569
0.6807	Remote Similarity	NPC186284
0.6807	Remote Similarity	NPC22082
0.6807	Remote Similarity	NPC301760
0.68	Remote Similarity	NPC475778
0.68	Remote Similarity	NPC159815
0.6786	Remote Similarity	NPC475847
0.6786	Remote Similarity	NPC185742
0.6786	Remote Similarity	NPC329833
0.6754	Remote Similarity	NPC474121
0.6743	Remote Similarity	NPC469428
0.6727	Remote Similarity	NPC287358
0.6726	Remote Similarity	NPC308197
0.672	Remote Similarity	NPC472119
0.6719	Remote Similarity	NPC303214
0.6718	Remote Similarity	NPC471512
0.6716	Remote Similarity	NPC10732
0.6708	Remote Similarity	NPC187231
0.6706	Remote Similarity	NPC146370
0.6705	Remote Similarity	NPC469461
0.6705	Remote Similarity	NPC122106
0.6704	Remote Similarity	NPC278887
0.6703	Remote Similarity	NPC475097
0.6703	Remote Similarity	NPC470548
0.6702	Remote Similarity	NPC470485

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 NPC286871 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	503
0.2-0.3	796
0.3-0.4	1626
0.4-0.5	3860
0.5-0.6	2011
0.6-0.7	180
0.7-0.8	3
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
0.7278	Intermediate Similarity	NPD5182	Approved
0.7278	Intermediate Similarity	NPD5185	Approved
0.7278	Intermediate Similarity	NPD5184	Approved
0.7229	Intermediate Similarity	NPD5942	Approved
0.7229	Intermediate Similarity	NPD5941	Approved
0.7176	Intermediate Similarity	NPD7105	Phase 1
0.7135	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4121	Phase 3
0.7059	Intermediate Similarity	NPD4120	Approved
0.7018	Intermediate Similarity	NPD5741	Approved
0.7018	Intermediate Similarity	NPD5742	Approved
0.7018	Intermediate Similarity	NPD5743	Approved
0.6928	Remote Similarity	NPD5024	Approved
0.6898	Remote Similarity	NPD4499	Approved
0.6897	Remote Similarity	NPD7599	Phase 2
0.6891	Remote Similarity	NPD6238	Discontinued
0.6857	Remote Similarity	NPD7600	Phase 2
0.6826	Remote Similarity	NPD2820	Phase 3
0.6813	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3625	Discontinued
0.6782	Remote Similarity	NPD1663	Discontinued
0.6766	Remote Similarity	NPD2365	Approved
0.674	Remote Similarity	NPD5997	Discontinued
0.6739	Remote Similarity	NPD6878	Phase 2
0.6739	Remote Similarity	NPD6879	Phase 2
0.6727	Remote Similarity	NPD6342	Discontinued
0.6722	Remote Similarity	NPD5186	Approved
0.6722	Remote Similarity	NPD5183	Approved
0.6705	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7487	Discontinued
0.6667	Remote Similarity	NPD1802	Approved
0.6667	Remote Similarity	NPD1801	Approved
0.6667	Remote Similarity	NPD6768	Approved
0.6648	Remote Similarity	NPD8630	Approved
0.6628	Remote Similarity	NPD7528	Approved
0.6628	Remote Similarity	NPD4682	Phase 2
0.6612	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3790	Phase 2
0.659	Remote Similarity	NPD1405	Approved
0.6582	Remote Similarity	NPD4215	Approved
0.6582	Remote Similarity	NPD2609	Approved
0.6582	Remote Similarity	NPD4217	Approved
0.6582	Remote Similarity	NPD4216	Approved
0.6582	Remote Similarity	NPD3131	Approved
0.6582	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2611	Approved
0.6582	Remote Similarity	NPD2612	Approved
0.6582	Remote Similarity	NPD2610	Approved
0.6582	Remote Similarity	NPD4218	Approved
0.6582	Remote Similarity	NPD2608	Approved
0.6582	Remote Similarity	NPD3132	Approved
0.6571	Remote Similarity	NPD2790	Discontinued
0.657	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6176	Phase 1
0.6566	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3449	Discontinued
0.6536	Remote Similarity	NPD1373	Approved
0.6536	Remote Similarity	NPD1371	Approved
0.6536	Remote Similarity	NPD1374	Approved
0.6536	Remote Similarity	NPD1370	Approved
0.6534	Remote Similarity	NPD7072	Phase 2
0.6527	Remote Similarity	NPD6358	Phase 2
0.6517	Remote Similarity	NPD2509	Approved
0.6517	Remote Similarity	NPD2510	Approved
0.6512	Remote Similarity	NPD4041	Approved
0.651	Remote Similarity	NPD8240	Discontinued
0.6508	Remote Similarity	NPD6557	Phase 2
0.6508	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3824	Phase 1
0.6494	Remote Similarity	NPD1711	Phase 2
0.6491	Remote Similarity	NPD5918	Discontinued
0.6491	Remote Similarity	NPD2387	Approved
0.6488	Remote Similarity	NPD3170	Approved
0.6485	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6457	Approved
0.6467	Remote Similarity	NPD7854	Phase 2
0.6464	Remote Similarity	NPD7035	Approved
0.6464	Remote Similarity	NPD7036	Phase 3
0.646	Remote Similarity	NPD1036	Approved
0.6452	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.645	Remote Similarity	NPD5426	Phase 3
0.644	Remote Similarity	NPD6484	Approved
0.644	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6483	Approved
0.644	Remote Similarity	NPD6891	Phase 2
0.6438	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5466	Approved
0.6429	Remote Similarity	NPD5003	Discontinued
0.6429	Remote Similarity	NPD2670	Approved
0.6425	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3399	Approved
0.6418	Remote Similarity	NPD7001	Phase 3
0.6416	Remote Similarity	NPD3141	Discontinued
0.6414	Remote Similarity	NPD4601	Approved
0.6414	Remote Similarity	NPD4600	Approved
0.6409	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2435	Approved
0.6389	Remote Similarity	NPD7244	Discontinued
0.6386	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5086	Approved
0.638	Remote Similarity	NPD5993	Phase 1
0.6374	Remote Similarity	NPD5430	Discontinued
0.6369	Remote Similarity	NPD6073	Approved
0.6364	Remote Similarity	NPD2607	Approved
0.6364	Remote Similarity	NPD5600	Discontinued
0.6358	Remote Similarity	NPD5932	Phase 3
0.6358	Remote Similarity	NPD5933	Phase 3
0.6358	Remote Similarity	NPD5931	Phase 3
0.6353	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6995	Phase 1
0.6349	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD979	Approved
0.634	Remote Similarity	NPD5077	Approved
0.634	Remote Similarity	NPD5076	Approved
0.6339	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD33	Approved
0.6333	Remote Similarity	NPD4393	Approved
0.6331	Remote Similarity	NPD5318	Discontinued
0.6329	Remote Similarity	NPD6345	Approved
0.6329	Remote Similarity	NPD5293	Phase 2
0.6329	Remote Similarity	NPD6343	Approved
0.6328	Remote Similarity	NPD2948	Discontinued
0.6323	Remote Similarity	NPD5179	Approved
0.6323	Remote Similarity	NPD5180	Approved
0.6323	Remote Similarity	NPD5181	Approved
0.6322	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4607	Approved
0.6316	Remote Similarity	NPD8281	Discontinued
0.6316	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2093	Discontinued
0.6313	Remote Similarity	NPD6570	Approved
0.6313	Remote Similarity	NPD6571	Approved
0.631	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1228	Phase 2
0.6308	Remote Similarity	NPD5937	Approved
0.6306	Remote Similarity	NPD6069	Approved
0.6306	Remote Similarity	NPD6070	Approved
0.6304	Remote Similarity	NPD2844	Phase 3
0.6303	Remote Similarity	NPD2613	Approved
0.6299	Remote Similarity	NPD3001	Approved
0.6299	Remote Similarity	NPD2999	Approved
0.6298	Remote Similarity	NPD2511	Approved
0.6296	Remote Similarity	NPD3227	Phase 2
0.6294	Remote Similarity	NPD1626	Approved
0.6289	Remote Similarity	NPD2565	Phase 2
0.6289	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2564	Approved
0.6287	Remote Similarity	NPD1294	Discontinued
0.6286	Remote Similarity	NPD3352	Approved
0.6279	Remote Similarity	NPD6566	Discontinued
0.6279	Remote Similarity	NPD2923	Approved
0.6277	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1752	Approved
0.6275	Remote Similarity	NPD1756	Approved
0.6274	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD8173	Phase 2
0.6272	Remote Similarity	NPD5725	Approved
0.6272	Remote Similarity	NPD1207	Approved
0.6272	Remote Similarity	NPD1206	Approved
0.6272	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD8172	Phase 2
0.6271	Remote Similarity	NPD5982	Phase 2
0.6271	Remote Similarity	NPD7606	Phase 3
0.627	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD5990	Approved
0.6266	Remote Similarity	NPD5991	Approved
0.6265	Remote Similarity	NPD1070	Approved
0.6265	Remote Similarity	NPD1069	Approved
0.6264	Remote Similarity	NPD5060	Phase 1
0.6264	Remote Similarity	NPD7295	Approved
0.6262	Remote Similarity	NPD7470	Discontinued
0.6258	Remote Similarity	NPD6792	Phase 3
0.6257	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6659	Phase 2
0.625	Remote Similarity	NPD5823	Approved
0.625	Remote Similarity	NPD4500	Approved
0.625	Remote Similarity	NPD4501	Approved
0.625	Remote Similarity	NPD6805	Discontinued
0.625	Remote Similarity	NPD4161	Discontinued
0.6243	Remote Similarity	NPD4430	Phase 2
0.6243	Remote Similarity	NPD7881	Approved
0.6242	Remote Similarity	NPD4177	Approved
0.6242	Remote Similarity	NPD4175	Approved
0.6237	Remote Similarity	NPD5633	Discontinued
0.6236	Remote Similarity	NPD1879	Approved
0.6235	Remote Similarity	NPD2567	Approved
0.6235	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6295	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