NPASS Compound

Structure

NPC246140 OpenBabel07101719152D 27 31 0 0 1 0 0 0 0 0999 V2000 3.6847 0.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1633 1.5127 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 1 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 -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 4.5508 -0.6311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2767 0.3498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2645 1.0743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6405 0.9178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 8 23 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 1 1 6 0 0 0 11 24 1 0 0 0 0 12 9 1 6 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 11 1 1 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 21 1 1 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.19
Volume:	372.962
LogP:	1.425
LogD:	1.678
LogS:	-2.827
# Rotatable Bonds:	4
TPSA:	71.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.823
Synthetic Accessibility Score:	5.806
Fsp3:	0.619
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:	-4.766
MDCK Permeability:	4.610836549545638e-05
Pgp-inhibitor:	0.79
Pgp-substrate:	0.858
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.205

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	66.76295471191406%
Volume Distribution (VD):	1.816
Pgp-substrate:	54.044498443603516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.467
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.159
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.806
CYP3A4-inhibitor:	0.406
CYP3A4-substrate:	0.86

ADMET: Excretion

Clearance (CL):	10.383
Half-life (T1/2):	0.595

ADMET: Toxicity

hERG Blockers:	0.396
Human Hepatotoxicity (H-HT):	0.389
Drug-inuced Liver Injury (DILI):	0.319
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.855
Skin Sensitization:	0.178
Carcinogencity:	0.685
Eye Corrosion:	0.004
Eye Irritation:	0.029
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC246140

Natural Product ID:	NPC246140
*Common Name:**	FNDWOLJMJUSGOB-CSXNJMRASA-N
IUPAC Name:	n.a.
Synonyms:	12-Methoxyechitamidine
Standard InCHIKey:	FNDWOLJMJUSGOB-CSXNJMRASA-N
Standard InCHI:	InChI=1S/C21H26N2O4/c1-11(24)13-10-23-8-7-21-14-5-4-6-15(26-2)18(14)22-19(21)17(20(25)27-3)12(13)9-16(21)23/h4-6,11-13,16,22,24H,7-10H2,1-3H3/t11-,12-,13-,16-,21+/m0/s1
SMILES:	C[C@@H]([C@@H]1CN2CC[C@@]34c5cccc(c5NC4=C([C@H]1C[C@H]23)C(=O)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523826
PubChem CID:	21586664
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
NPO19269	Winchia calophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16441061]
NPO19269	Winchia calophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO19269	Winchia calophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO19269	Winchia calophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	11500.0	nM	PMID[536118]

☑ 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 NPC246140 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	255
0.1-0.2	1208
0.2-0.3	3716
0.3-0.4	11424
0.4-0.5	9447
0.5-0.6	14624
0.6-0.7	1755
0.7-0.8	228
0.8-0.85	30
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195787
0.9514	High Similarity	NPC1464
0.8889	High Similarity	NPC265642
0.8889	High Similarity	NPC138615
0.8889	High Similarity	NPC132874
0.8889	High Similarity	NPC218733
0.8808	High Similarity	NPC87714
0.86	High Similarity	NPC189661
0.8578	High Similarity	NPC301501
0.851	High Similarity	NPC223242
0.8458	Intermediate Similarity	NPC469452
0.8451	Intermediate Similarity	NPC469450
0.8432	Intermediate Similarity	NPC218594
0.8432	Intermediate Similarity	NPC99043
0.8429	Intermediate Similarity	NPC139373
0.8424	Intermediate Similarity	NPC195636
0.8406	Intermediate Similarity	NPC19175
0.8382	Intermediate Similarity	NPC77777
0.838	Intermediate Similarity	NPC329932
0.8372	Intermediate Similarity	NPC469451
0.8367	Intermediate Similarity	NPC469732
0.8325	Intermediate Similarity	NPC471513
0.8301	Intermediate Similarity	NPC476069
0.8271	Intermediate Similarity	NPC131977
0.8261	Intermediate Similarity	NPC128476
0.8226	Intermediate Similarity	NPC264482
0.8226	Intermediate Similarity	NPC203202
0.8195	Intermediate Similarity	NPC234772
0.8187	Intermediate Similarity	NPC25401
0.8187	Intermediate Similarity	NPC22476
0.8158	Intermediate Similarity	NPC97584
0.8138	Intermediate Similarity	NPC6974
0.8135	Intermediate Similarity	NPC5630
0.8105	Intermediate Similarity	NPC159963
0.8075	Intermediate Similarity	NPC477397
0.8066	Intermediate Similarity	NPC473458
0.8056	Intermediate Similarity	NPC291173
0.8039	Intermediate Similarity	NPC269449
0.8031	Intermediate Similarity	NPC14994
0.8	Intermediate Similarity	NPC203628
0.799	Intermediate Similarity	NPC222046
0.7989	Intermediate Similarity	NPC186669
0.797	Intermediate Similarity	NPC475147
0.7961	Intermediate Similarity	NPC119722
0.7955	Intermediate Similarity	NPC469722
0.791	Intermediate Similarity	NPC232600
0.7905	Intermediate Similarity	NPC288110
0.7839	Intermediate Similarity	NPC303214
0.7818	Intermediate Similarity	NPC151171
0.7816	Intermediate Similarity	NPC475133
0.7804	Intermediate Similarity	NPC231924
0.7793	Intermediate Similarity	NPC477395
0.7761	Intermediate Similarity	NPC100863
0.7739	Intermediate Similarity	NPC470485
0.773	Intermediate Similarity	NPC193410
0.7727	Intermediate Similarity	NPC154922
0.7725	Intermediate Similarity	NPC126556
0.7723	Intermediate Similarity	NPC477393
0.7703	Intermediate Similarity	NPC127996
0.7688	Intermediate Similarity	NPC248117
0.7685	Intermediate Similarity	NPC138830
0.7672	Intermediate Similarity	NPC167724
0.7672	Intermediate Similarity	NPC224970
0.7672	Intermediate Similarity	NPC223595
0.7665	Intermediate Similarity	NPC21425
0.7655	Intermediate Similarity	NPC477396
0.7639	Intermediate Similarity	NPC477394
0.7638	Intermediate Similarity	NPC470483
0.7634	Intermediate Similarity	NPC36495
0.7633	Intermediate Similarity	NPC478075
0.7621	Intermediate Similarity	NPC470484
0.7581	Intermediate Similarity	NPC61013
0.7556	Intermediate Similarity	NPC113455
0.7535	Intermediate Similarity	NPC318525
0.7535	Intermediate Similarity	NPC10653
0.7524	Intermediate Similarity	NPC474077
0.7523	Intermediate Similarity	NPC476220
0.7523	Intermediate Similarity	NPC160113
0.7512	Intermediate Similarity	NPC67904
0.7511	Intermediate Similarity	NPC475720
0.7511	Intermediate Similarity	NPC474192
0.75	Intermediate Similarity	NPC474059
0.7488	Intermediate Similarity	NPC475609
0.7487	Intermediate Similarity	NPC33507
0.7476	Intermediate Similarity	NPC477160
0.7461	Intermediate Similarity	NPC21752
0.7461	Intermediate Similarity	NPC276993
0.7461	Intermediate Similarity	NPC210415
0.7461	Intermediate Similarity	NPC298851
0.7461	Intermediate Similarity	NPC181138
0.7461	Intermediate Similarity	NPC293255
0.7456	Intermediate Similarity	NPC120239
0.7451	Intermediate Similarity	NPC161804
0.7423	Intermediate Similarity	NPC469726
0.7423	Intermediate Similarity	NPC329338
0.7414	Intermediate Similarity	NPC329982
0.7394	Intermediate Similarity	NPC123241
0.7389	Intermediate Similarity	NPC476258
0.7389	Intermediate Similarity	NPC475816
0.7389	Intermediate Similarity	NPC304837
0.7371	Intermediate Similarity	NPC470481
0.7371	Intermediate Similarity	NPC470482
0.7368	Intermediate Similarity	NPC293458
0.7366	Intermediate Similarity	NPC90967
0.736	Intermediate Similarity	NPC474470
0.7346	Intermediate Similarity	NPC329567
0.7346	Intermediate Similarity	NPC330683
0.7327	Intermediate Similarity	NPC141440
0.7323	Intermediate Similarity	NPC116096
0.7321	Intermediate Similarity	NPC473105
0.7318	Intermediate Similarity	NPC122886
0.7318	Intermediate Similarity	NPC115588
0.7304	Intermediate Similarity	NPC94499
0.729	Intermediate Similarity	NPC159815
0.7285	Intermediate Similarity	NPC476436
0.7277	Intermediate Similarity	NPC217294
0.7277	Intermediate Similarity	NPC230098
0.7268	Intermediate Similarity	NPC243626
0.7264	Intermediate Similarity	NPC262725
0.7251	Intermediate Similarity	NPC477161
0.7233	Intermediate Similarity	NPC33256
0.7228	Intermediate Similarity	NPC181928
0.7202	Intermediate Similarity	NPC70172
0.72	Intermediate Similarity	NPC474745
0.7196	Intermediate Similarity	NPC474366
0.7194	Intermediate Similarity	NPC290759
0.7194	Intermediate Similarity	NPC158148
0.7194	Intermediate Similarity	NPC266176
0.7194	Intermediate Similarity	NPC82533
0.7192	Intermediate Similarity	NPC162694
0.7186	Intermediate Similarity	NPC35680
0.7184	Intermediate Similarity	NPC230313
0.7177	Intermediate Similarity	NPC127178
0.7171	Intermediate Similarity	NPC204970
0.7169	Intermediate Similarity	NPC219397
0.7157	Intermediate Similarity	NPC105055
0.7157	Intermediate Similarity	NPC473298
0.7157	Intermediate Similarity	NPC22689
0.715	Intermediate Similarity	NPC474325
0.7149	Intermediate Similarity	NPC251071
0.7143	Intermediate Similarity	NPC471512
0.7136	Intermediate Similarity	NPC304675
0.7136	Intermediate Similarity	NPC212123
0.7136	Intermediate Similarity	NPC203972
0.7135	Intermediate Similarity	NPC474058
0.7129	Intermediate Similarity	NPC52262
0.7124	Intermediate Similarity	NPC476429
0.7123	Intermediate Similarity	NPC268077
0.7122	Intermediate Similarity	NPC28510
0.7121	Intermediate Similarity	NPC477640
0.7121	Intermediate Similarity	NPC470739
0.7121	Intermediate Similarity	NPC225597
0.7114	Intermediate Similarity	NPC314659
0.7114	Intermediate Similarity	NPC98197
0.7107	Intermediate Similarity	NPC475686
0.7107	Intermediate Similarity	NPC58766
0.7101	Intermediate Similarity	NPC34717
0.71	Intermediate Similarity	NPC237044
0.7098	Intermediate Similarity	NPC282339
0.7098	Intermediate Similarity	NPC99632
0.7094	Intermediate Similarity	NPC475981
0.7094	Intermediate Similarity	NPC474746
0.7087	Intermediate Similarity	NPC473004
0.7085	Intermediate Similarity	NPC21638
0.7083	Intermediate Similarity	NPC148468
0.7083	Intermediate Similarity	NPC63210
0.7083	Intermediate Similarity	NPC243673
0.7083	Intermediate Similarity	NPC310403
0.7083	Intermediate Similarity	NPC263709
0.7083	Intermediate Similarity	NPC301163
0.7083	Intermediate Similarity	NPC97380
0.7077	Intermediate Similarity	NPC472115
0.7077	Intermediate Similarity	NPC472114
0.7075	Intermediate Similarity	NPC207971
0.7072	Intermediate Similarity	NPC148124
0.7071	Intermediate Similarity	NPC474475
0.7071	Intermediate Similarity	NPC474708
0.7065	Intermediate Similarity	NPC197335
0.7065	Intermediate Similarity	NPC472163
0.7047	Intermediate Similarity	NPC309531
0.7047	Intermediate Similarity	NPC472102
0.7044	Intermediate Similarity	NPC473007
0.7028	Intermediate Similarity	NPC286135
0.7027	Intermediate Similarity	NPC99724
0.7027	Intermediate Similarity	NPC46259
0.7026	Intermediate Similarity	NPC470069
0.7026	Intermediate Similarity	NPC52059
0.7022	Intermediate Similarity	NPC470480
0.702	Intermediate Similarity	NPC475845
0.7018	Intermediate Similarity	NPC30749
0.7015	Intermediate Similarity	NPC166169
0.701	Intermediate Similarity	NPC472101
0.701	Intermediate Similarity	NPC472120
0.7	Intermediate Similarity	NPC71124
0.699	Remote Similarity	NPC473008
0.699	Remote Similarity	NPC214960
0.699	Remote Similarity	NPC279527
0.6984	Remote Similarity	NPC214239
0.6982	Remote Similarity	NPC472099
0.698	Remote Similarity	NPC270301

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 NPC246140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	493
0.2-0.3	725
0.3-0.4	1565
0.4-0.5	2555
0.5-0.6	2833
0.6-0.7	789
0.7-0.8	18
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
0.7703	Intermediate Similarity	NPD4494	Approved
0.7703	Intermediate Similarity	NPD4492	Approved
0.7642	Intermediate Similarity	NPD3940	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4596	Phase 1
0.7596	Intermediate Similarity	NPD4082	Approved
0.7571	Intermediate Similarity	NPD4493	Discontinued
0.7536	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
0.7453	Intermediate Similarity	NPD3888	Discontinued
0.7441	Intermediate Similarity	NPD3372	Discontinued
0.7373	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5860	Discontinued
0.7346	Intermediate Similarity	NPD2906	Approved
0.7346	Intermediate Similarity	NPD2907	Approved
0.7324	Intermediate Similarity	NPD1945	Phase 1
0.7321	Intermediate Similarity	NPD6625	Approved
0.7294	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3006	Discontinued
0.7236	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6199	Discontinued
0.7156	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6238	Discontinued
0.7129	Intermediate Similarity	NPD6874	Approved
0.7128	Intermediate Similarity	NPD2681	Approved
0.7128	Intermediate Similarity	NPD2680	Approved
0.712	Intermediate Similarity	NPD1769	Discontinued
0.7092	Intermediate Similarity	NPD5183	Approved
0.7092	Intermediate Similarity	NPD5186	Approved
0.7073	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5582	Discontinued
0.7023	Intermediate Similarity	NPD4859	Phase 1
0.7015	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5600	Discontinued
0.6978	Remote Similarity	NPD7186	Phase 3
0.6952	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4420	Approved
0.6915	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3437	Discontinued
0.6889	Remote Similarity	NPD7542	Phase 3
0.6869	Remote Similarity	NPD2249	Approved
0.6869	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5005	Approved
0.6869	Remote Similarity	NPD2247	Approved
0.6869	Remote Similarity	NPD3983	Phase 3
0.6869	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5006	Approved
0.6857	Remote Similarity	NPD7256	Discontinued
0.6853	Remote Similarity	NPD4796	Discontinued
0.6844	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4668	Phase 2
0.6837	Remote Similarity	NPD1742	Approved
0.6837	Remote Similarity	NPD1743	Approved
0.6837	Remote Similarity	NPD19	Approved
0.683	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6321	Discontinued
0.6822	Remote Similarity	NPD7476	Discontinued
0.6821	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5938	Phase 3
0.6814	Remote Similarity	NPD3912	Discontinued
0.6806	Remote Similarity	NPD4467	Phase 2
0.6806	Remote Similarity	NPD4465	Phase 2
0.6796	Remote Similarity	NPD6851	Approved
0.6796	Remote Similarity	NPD6853	Approved
0.6792	Remote Similarity	NPD2975	Approved
0.6792	Remote Similarity	NPD2974	Approved
0.6792	Remote Similarity	NPD2973	Approved
0.6786	Remote Similarity	NPD5496	Approved
0.6786	Remote Similarity	NPD2899	Discontinued
0.6784	Remote Similarity	NPD6107	Approved
0.6776	Remote Similarity	NPD4580	Approved
0.6765	Remote Similarity	NPD6297	Approved
0.6749	Remote Similarity	NPD5313	Approved
0.6749	Remote Similarity	NPD5312	Approved
0.6746	Remote Similarity	NPD5928	Phase 1
0.674	Remote Similarity	NPD7279	Phase 2
0.674	Remote Similarity	NPD7278	Phase 2
0.6737	Remote Similarity	NPD6716	Phase 1
0.6728	Remote Similarity	NPD6644	Discontinued
0.6728	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6723	Discontinued
0.6716	Remote Similarity	NPD7479	Phase 2
0.6715	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8364	Approved
0.6707	Remote Similarity	NPD8363	Approved
0.67	Remote Similarity	NPD6457	Approved
0.6698	Remote Similarity	NPD4107	Approved
0.6697	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5676	Approved
0.6683	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5071	Phase 2
0.6667	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2968	Approved
0.6667	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2971	Approved
0.6667	Remote Similarity	NPD3452	Approved
0.6667	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7820	Phase 3
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD3450	Approved
0.6653	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7560	Approved
0.6652	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4583	Approved
0.6651	Remote Similarity	NPD4515	Suspended
0.6651	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4582	Approved
0.6651	Remote Similarity	NPD7891	Discontinued
0.6649	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3057	Approved
0.6635	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2488	Approved
0.6635	Remote Similarity	NPD2490	Approved
0.6623	Remote Similarity	NPD6997	Phase 2
0.662	Remote Similarity	NPD6519	Phase 2
0.662	Remote Similarity	NPD6871	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7126	Discontinued
0.6615	Remote Similarity	NPD1802	Approved
0.6615	Remote Similarity	NPD1801	Approved
0.6606	Remote Similarity	NPD4004	Approved
0.6606	Remote Similarity	NPD4002	Approved
0.6606	Remote Similarity	NPD7497	Discontinued
0.6603	Remote Similarity	NPD6339	Approved
0.6603	Remote Similarity	NPD6340	Approved
0.6601	Remote Similarity	NPD4481	Phase 3
0.6601	Remote Similarity	NPD2248	Approved
0.6601	Remote Similarity	NPD2246	Approved
0.6591	Remote Similarity	NPD2434	Approved
0.659	Remote Similarity	NPD3416	Discontinued
0.659	Remote Similarity	NPD4482	Phase 3
0.6589	Remote Similarity	NPD3964	Approved
0.6588	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7281	Phase 3
0.6587	Remote Similarity	NPD7280	Phase 3
0.6582	Remote Similarity	NPD3684	Discontinued
0.6579	Remote Similarity	NPD7805	Phase 3
0.6574	Remote Similarity	NPD7810	Phase 3
0.6574	Remote Similarity	NPD7811	Phase 3
0.6571	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6037	Discontinued
0.656	Remote Similarity	NPD2972	Approved
0.656	Remote Similarity	NPD3533	Approved
0.6557	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8358	Approved
0.6553	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8467	Approved
0.6549	Remote Similarity	NPD8466	Approved
0.6549	Remote Similarity	NPD8465	Approved
0.6547	Remote Similarity	NPD4502	Phase 2
0.6545	Remote Similarity	NPD8461	Discontinued
0.6542	Remote Similarity	NPD7669	Phase 3
0.654	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3560	Approved
0.6533	Remote Similarity	NPD3557	Approved
0.6533	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3556	Approved
0.6533	Remote Similarity	NPD1012	Discontinued
0.6533	Remote Similarity	NPD3558	Approved
0.6527	Remote Similarity	NPD6517	Phase 3
0.652	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7827	Phase 1
0.6517	Remote Similarity	NPD6315	Phase 2
0.6515	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1670	Discontinued
0.6512	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7315	Approved
0.6502	Remote Similarity	NPD6071	Discontinued
0.65	Remote Similarity	NPD4040	Phase 1
0.65	Remote Similarity	NPD3298	Approved
0.6498	Remote Similarity	NPD7048	Phase 3
0.6495	Remote Similarity	NPD7262	Phase 1
0.6492	Remote Similarity	NPD7708	Approved
0.6486	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2514	Approved
0.6484	Remote Similarity	NPD3448	Approved
0.6484	Remote Similarity	NPD2491	Approved
0.6479	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7272	Discontinued
0.6471	Remote Similarity	NPD2970	Approved
0.6471	Remote Similarity	NPD5680	Clinical (unspecified phase)

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