NPASS Compound

Structure

NPC472120 OpenBabel07101719522D 25 29 0 0 1 0 0 0 0 0999 V2000 5.4044 -3.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7572 -2.6783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3968 -2.1371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1444 -0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5627 -1.5913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0041 -1.9405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7353 -2.4704 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0880 -1.9351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3611 -1.2688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0104 -0.6399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8080 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 3 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 2.8025 -1.6180 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.0443 -1.5193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3842 -1.9272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 17 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 22 1 0 0 0 0 11 25 1 0 0 0 0 12 1 1 1 0 0 0 12 23 1 0 0 0 0 13 7 1 1 0 0 0 13 14 1 0 0 0 0 14 10 1 1 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 6 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.19
Volume:	349.512
LogP:	2.013
LogD:	2.184
LogS:	-2.943
# Rotatable Bonds:	2
TPSA:	53.01
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.889
Synthetic Accessibility Score:	6.166
Fsp3:	0.65
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:	-4.888
MDCK Permeability:	2.7910853532375768e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.176
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.719

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.884
Plasma Protein Binding (PPB):	45.23688888549805%
Volume Distribution (VD):	1.971
Pgp-substrate:	65.86207580566406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.592
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.576
CYP3A4-inhibitor:	0.129
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	10.18
Half-life (T1/2):	0.217

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.631
Drug-inuced Liver Injury (DILI):	0.851
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.205
Carcinogencity:	0.653
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC472120

Natural Product ID:	NPC472120
*Common Name:**	IEZFIXTXFGQQGQ-NLBZKFOGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IEZFIXTXFGQQGQ-NLBZKFOGSA-N
Standard InCHI:	InChI=1S/C20H26N2O3/c1-12(23)7-13-8-18-20(9-17-14(13)10-25-11-22(17)18)15-5-3-4-6-16(15)21(2)19(20)24/h3-6,12-14,17-18,23H,7-11H2,1-2H3/t12-,13-,14-,17-,18-,20?/m0/s1
SMILES:	C[C@@H](C[C@H]1C[C@@H]2N3[C@H]([C@H]1COC3)CC12c2ccccc2N(C1=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338246
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives

*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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

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[551698]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[551698]

☑ 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 NPC472120 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	204
0.1-0.2	1000
0.2-0.3	2761
0.3-0.4	16693
0.4-0.5	16690
0.5-0.6	4337
0.6-0.7	821
0.7-0.8	164
0.8-0.85	20
0.85-0.9	0
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472101
0.9605	High Similarity	NPC472106
0.9346	High Similarity	NPC472117
0.9281	High Similarity	NPC472102
0.9281	High Similarity	NPC309531
0.915	High Similarity	NPC113946
0.8457	Intermediate Similarity	NPC279527
0.8457	Intermediate Similarity	NPC214960
0.8365	Intermediate Similarity	NPC29285
0.8242	Intermediate Similarity	NPC472118
0.8161	Intermediate Similarity	NPC22689
0.8161	Intermediate Similarity	NPC105055
0.8144	Intermediate Similarity	NPC214626
0.8144	Intermediate Similarity	NPC251212
0.8144	Intermediate Similarity	NPC139085
0.8089	Intermediate Similarity	NPC472100
0.8059	Intermediate Similarity	NPC99043
0.8059	Intermediate Similarity	NPC218594
0.8049	Intermediate Similarity	NPC176983
0.8049	Intermediate Similarity	NPC286871
0.7988	Intermediate Similarity	NPC225319
0.7941	Intermediate Similarity	NPC476441
0.7901	Intermediate Similarity	NPC478076
0.7895	Intermediate Similarity	NPC260075
0.7857	Intermediate Similarity	NPC475489
0.7836	Intermediate Similarity	NPC264482
0.7836	Intermediate Similarity	NPC203202
0.7824	Intermediate Similarity	NPC96901
0.7816	Intermediate Similarity	NPC477159
0.7771	Intermediate Similarity	NPC315368
0.7771	Intermediate Similarity	NPC97584
0.775	Intermediate Similarity	NPC264589
0.7738	Intermediate Similarity	NPC471124
0.7733	Intermediate Similarity	NPC129624
0.7725	Intermediate Similarity	NPC282339
0.7725	Intermediate Similarity	NPC99632
0.7711	Intermediate Similarity	NPC471122
0.7707	Intermediate Similarity	NPC315051
0.7665	Intermediate Similarity	NPC143457
0.7658	Intermediate Similarity	NPC22082
0.7658	Intermediate Similarity	NPC186284
0.7644	Intermediate Similarity	NPC475094
0.7644	Intermediate Similarity	NPC6974
0.7628	Intermediate Similarity	NPC471123
0.7616	Intermediate Similarity	NPC476425
0.7616	Intermediate Similarity	NPC285622
0.7605	Intermediate Similarity	NPC36495
0.7593	Intermediate Similarity	NPC212799
0.7561	Intermediate Similarity	NPC475763
0.756	Intermediate Similarity	NPC474058
0.756	Intermediate Similarity	NPC201424
0.7557	Intermediate Similarity	NPC476428
0.7528	Intermediate Similarity	NPC52262
0.7527	Intermediate Similarity	NPC471512
0.7514	Intermediate Similarity	NPC181138
0.7514	Intermediate Similarity	NPC473743
0.7514	Intermediate Similarity	NPC210415
0.7514	Intermediate Similarity	NPC21752
0.7514	Intermediate Similarity	NPC276993
0.7514	Intermediate Similarity	NPC293255
0.7514	Intermediate Similarity	NPC159963
0.7514	Intermediate Similarity	NPC298851
0.75	Intermediate Similarity	NPC11149
0.75	Intermediate Similarity	NPC162440
0.75	Intermediate Similarity	NPC475559
0.75	Intermediate Similarity	NPC193410
0.7486	Intermediate Similarity	NPC186669
0.7486	Intermediate Similarity	NPC221687
0.7485	Intermediate Similarity	NPC472114
0.7485	Intermediate Similarity	NPC472115
0.7472	Intermediate Similarity	NPC245741
0.7457	Intermediate Similarity	NPC355
0.7456	Intermediate Similarity	NPC248117
0.7444	Intermediate Similarity	NPC14994
0.7442	Intermediate Similarity	NPC224970
0.7442	Intermediate Similarity	NPC167724
0.7442	Intermediate Similarity	NPC223595
0.744	Intermediate Similarity	NPC61013
0.7432	Intermediate Similarity	NPC470485
0.7407	Intermediate Similarity	NPC472103
0.7407	Intermediate Similarity	NPC329833
0.7405	Intermediate Similarity	NPC302548
0.7371	Intermediate Similarity	NPC13367
0.7366	Intermediate Similarity	NPC100863
0.7363	Intermediate Similarity	NPC473298
0.7337	Intermediate Similarity	NPC211525
0.7337	Intermediate Similarity	NPC153694
0.7333	Intermediate Similarity	NPC259626
0.7326	Intermediate Similarity	NPC470069
0.7326	Intermediate Similarity	NPC52059
0.7322	Intermediate Similarity	NPC470483
0.7322	Intermediate Similarity	NPC25401
0.7314	Intermediate Similarity	NPC473880
0.7312	Intermediate Similarity	NPC469560
0.7312	Intermediate Similarity	NPC90967
0.731	Intermediate Similarity	NPC293458
0.731	Intermediate Similarity	NPC472121
0.7308	Intermediate Similarity	NPC284706
0.7294	Intermediate Similarity	NPC263709
0.7294	Intermediate Similarity	NPC148468
0.7294	Intermediate Similarity	NPC97380
0.7294	Intermediate Similarity	NPC63210
0.7294	Intermediate Similarity	NPC310403
0.7294	Intermediate Similarity	NPC243673
0.7293	Intermediate Similarity	NPC282092
0.7288	Intermediate Similarity	NPC476326
0.7287	Intermediate Similarity	NPC138830
0.7287	Intermediate Similarity	NPC67904
0.7283	Intermediate Similarity	NPC473004
0.7278	Intermediate Similarity	NPC2933
0.7267	Intermediate Similarity	NPC313757
0.7267	Intermediate Similarity	NPC130251
0.7263	Intermediate Similarity	NPC475962
0.7258	Intermediate Similarity	NPC473375
0.7258	Intermediate Similarity	NPC97100
0.7253	Intermediate Similarity	NPC181928
0.7251	Intermediate Similarity	NPC68650
0.7246	Intermediate Similarity	NPC66936
0.7246	Intermediate Similarity	NPC154602
0.7241	Intermediate Similarity	NPC469462
0.7235	Intermediate Similarity	NPC123241
0.7222	Intermediate Similarity	NPC470301
0.7222	Intermediate Similarity	NPC256288
0.7209	Intermediate Similarity	NPC85651
0.7207	Intermediate Similarity	NPC286994
0.7207	Intermediate Similarity	NPC15840
0.72	Intermediate Similarity	NPC469915
0.7176	Intermediate Similarity	NPC477157
0.7176	Intermediate Similarity	NPC477156
0.7175	Intermediate Similarity	NPC470548
0.7165	Intermediate Similarity	NPC477160
0.716	Intermediate Similarity	NPC243162
0.7143	Intermediate Similarity	NPC33507
0.7143	Intermediate Similarity	NPC473007
0.7143	Intermediate Similarity	NPC472209
0.7143	Intermediate Similarity	NPC243756
0.7126	Intermediate Similarity	NPC475420
0.712	Intermediate Similarity	NPC1464
0.7118	Intermediate Similarity	NPC161827
0.7104	Intermediate Similarity	NPC473615
0.7083	Intermediate Similarity	NPC477179
0.7083	Intermediate Similarity	NPC318086
0.7081	Intermediate Similarity	NPC473569
0.7079	Intermediate Similarity	NPC469726
0.7079	Intermediate Similarity	NPC329338
0.7065	Intermediate Similarity	NPC229484
0.7065	Intermediate Similarity	NPC318525
0.7065	Intermediate Similarity	NPC10653
0.7052	Intermediate Similarity	NPC477158
0.7049	Intermediate Similarity	NPC469460
0.7047	Intermediate Similarity	NPC477178
0.7047	Intermediate Similarity	NPC254850
0.7047	Intermediate Similarity	NPC477180
0.7047	Intermediate Similarity	NPC477181
0.7045	Intermediate Similarity	NPC63047
0.7045	Intermediate Similarity	NPC475248
0.7043	Intermediate Similarity	NPC472097
0.7039	Intermediate Similarity	NPC472122
0.7039	Intermediate Similarity	NPC24594
0.7027	Intermediate Similarity	NPC292675
0.7026	Intermediate Similarity	NPC471945
0.7026	Intermediate Similarity	NPC471950
0.7022	Intermediate Similarity	NPC177261
0.7021	Intermediate Similarity	NPC34717
0.7021	Intermediate Similarity	NPC243626
0.7021	Intermediate Similarity	NPC230313
0.7012	Intermediate Similarity	NPC301760
0.7011	Intermediate Similarity	NPC469741
0.701	Intermediate Similarity	NPC470490
0.701	Intermediate Similarity	NPC477173
0.701	Intermediate Similarity	NPC195787
0.701	Intermediate Similarity	NPC477174
0.701	Intermediate Similarity	NPC246140
0.7	Intermediate Similarity	NPC285381
0.6995	Remote Similarity	NPC472119
0.699	Remote Similarity	NPC471951
0.699	Remote Similarity	NPC471946
0.6989	Remote Similarity	NPC473008
0.6983	Remote Similarity	NPC475097
0.6974	Remote Similarity	NPC470488
0.6973	Remote Similarity	NPC472323
0.6959	Remote Similarity	NPC87714
0.6954	Remote Similarity	NPC475359
0.6954	Remote Similarity	NPC191817
0.6943	Remote Similarity	NPC473005
0.6939	Remote Similarity	NPC470491
0.6939	Remote Similarity	NPC475259
0.6936	Remote Similarity	NPC104345
0.6936	Remote Similarity	NPC222029
0.6935	Remote Similarity	NPC473006
0.6928	Remote Similarity	NPC469537
0.6923	Remote Similarity	NPC472105
0.6923	Remote Similarity	NPC187827
0.6919	Remote Similarity	NPC478077
0.6911	Remote Similarity	NPC52557
0.6906	Remote Similarity	NPC326575
0.6906	Remote Similarity	NPC64436
0.6901	Remote Similarity	NPC122106
0.6893	Remote Similarity	NPC278887
0.6886	Remote Similarity	NPC311330

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 NPC472120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	450
0.2-0.3	652
0.3-0.4	1407
0.4-0.5	3543
0.5-0.6	2502
0.6-0.7	435
0.7-0.8	14
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
0.7901	Intermediate Similarity	NPD4121	Phase 3
0.7901	Intermediate Similarity	NPD4120	Approved
0.7853	Intermediate Similarity	NPD5741	Approved
0.7853	Intermediate Similarity	NPD5743	Approved
0.7853	Intermediate Similarity	NPD5742	Approved
0.7651	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7600	Phase 2
0.7229	Intermediate Similarity	NPD4682	Phase 2
0.7176	Intermediate Similarity	NPD1663	Discontinued
0.7134	Intermediate Similarity	NPD2820	Phase 3
0.7093	Intermediate Similarity	NPD7599	Phase 2
0.7081	Intermediate Similarity	NPD6102	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2365	Approved
0.7012	Intermediate Similarity	NPD2093	Discontinued
0.7	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6792	Phase 3
0.6968	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5931	Phase 3
0.6946	Remote Similarity	NPD5933	Phase 3
0.6946	Remote Similarity	NPD5932	Phase 3
0.6909	Remote Similarity	NPD3625	Discontinued
0.6908	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5181	Approved
0.6867	Remote Similarity	NPD5180	Approved
0.6867	Remote Similarity	NPD6566	Discontinued
0.6867	Remote Similarity	NPD5179	Approved
0.6852	Remote Similarity	NPD5184	Approved
0.6852	Remote Similarity	NPD5182	Approved
0.6852	Remote Similarity	NPD5185	Approved
0.6845	Remote Similarity	NPD7295	Approved
0.6826	Remote Similarity	NPD4430	Phase 2
0.6824	Remote Similarity	NPD5942	Approved
0.6824	Remote Similarity	NPD5941	Approved
0.681	Remote Similarity	NPD2791	Discontinued
0.6798	Remote Similarity	NPD5823	Approved
0.6796	Remote Similarity	NPD3423	Phase 2
0.6796	Remote Similarity	NPD3422	Phase 3
0.6786	Remote Similarity	NPD7487	Discontinued
0.678	Remote Similarity	NPD3790	Phase 2
0.6778	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5992	Approved
0.6753	Remote Similarity	NPD6805	Discontinued
0.6746	Remote Similarity	NPD6017	Discontinued
0.6743	Remote Similarity	NPD8630	Approved
0.6727	Remote Similarity	NPD6358	Phase 2
0.6726	Remote Similarity	NPD5024	Approved
0.6722	Remote Similarity	NPD7795	Phase 2
0.6721	Remote Similarity	NPD3449	Discontinued
0.6708	Remote Similarity	NPD2613	Approved
0.6708	Remote Similarity	NPD5131	Approved
0.6705	Remote Similarity	NPD4393	Approved
0.6705	Remote Similarity	NPD8402	Approved
0.6705	Remote Similarity	NPD33	Approved
0.6705	Remote Similarity	NPD8400	Approved
0.6705	Remote Similarity	NPD8401	Approved
0.6702	Remote Similarity	NPD6891	Phase 2
0.6688	Remote Similarity	NPD4218	Approved
0.6688	Remote Similarity	NPD3131	Approved
0.6688	Remote Similarity	NPD2609	Approved
0.6688	Remote Similarity	NPD4217	Approved
0.6688	Remote Similarity	NPD2610	Approved
0.6688	Remote Similarity	NPD2608	Approved
0.6688	Remote Similarity	NPD2611	Approved
0.6688	Remote Similarity	NPD3132	Approved
0.6688	Remote Similarity	NPD4216	Approved
0.6688	Remote Similarity	NPD2612	Approved
0.6688	Remote Similarity	NPD4215	Approved
0.6687	Remote Similarity	NPD5993	Phase 1
0.6686	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6395	Phase 2
0.6686	Remote Similarity	NPD5918	Discontinued
0.6667	Remote Similarity	NPD4601	Approved
0.6667	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4600	Approved
0.6667	Remote Similarity	NPD6489	Phase 3
0.665	Remote Similarity	NPD7205	Discontinued
0.6649	Remote Similarity	NPD6878	Phase 2
0.6649	Remote Similarity	NPD6879	Phase 2
0.6646	Remote Similarity	NPD519	Approved
0.6645	Remote Similarity	NPD6343	Approved
0.6645	Remote Similarity	NPD6345	Approved
0.6632	Remote Similarity	NPD4499	Approved
0.663	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7082	Approved
0.6608	Remote Similarity	NPD3141	Discontinued
0.6605	Remote Similarity	NPD4365	Phase 2
0.6599	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD8240	Discontinued
0.6588	Remote Similarity	NPD7259	Approved
0.6587	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2571	Approved
0.6585	Remote Similarity	NPD3615	Approved
0.6585	Remote Similarity	NPD7086	Phase 2
0.6585	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3614	Approved
0.6585	Remote Similarity	NPD3090	Approved
0.6585	Remote Similarity	NPD2573	Approved
0.6585	Remote Similarity	NPD3087	Approved
0.6585	Remote Similarity	NPD2574	Discontinued
0.6585	Remote Similarity	NPD2566	Approved
0.6585	Remote Similarity	NPD4745	Approved
0.6585	Remote Similarity	NPD3088	Approved
0.6585	Remote Similarity	NPD3089	Approved
0.6585	Remote Similarity	NPD2570	Approved
0.6585	Remote Similarity	NPD4746	Phase 3
0.6585	Remote Similarity	NPD3616	Approved
0.6582	Remote Similarity	NPD4501	Approved
0.6582	Remote Similarity	NPD4500	Approved
0.6581	Remote Similarity	NPD5991	Approved
0.6581	Remote Similarity	NPD5990	Approved
0.658	Remote Similarity	NPD4602	Approved
0.658	Remote Similarity	NPD7944	Discontinued
0.6579	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2511	Approved
0.6571	Remote Similarity	NPD2790	Discontinued
0.6562	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5578	Approved
0.6557	Remote Similarity	NPD5997	Discontinued
0.6554	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7483	Phase 2
0.6543	Remote Similarity	NPD7482	Phase 2
0.6541	Remote Similarity	NPD5600	Discontinued
0.6538	Remote Similarity	NPD2994	Approved
0.6533	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4942	Approved
0.6532	Remote Similarity	NPD979	Approved
0.651	Remote Similarity	NPD6659	Phase 2
0.6508	Remote Similarity	NPD6557	Phase 2
0.6506	Remote Similarity	NPD4685	Phase 3
0.6506	Remote Similarity	NPD4684	Phase 3
0.6506	Remote Similarity	NPD4686	Approved
0.65	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7105	Phase 1
0.649	Remote Similarity	NPD4116	Approved
0.648	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2506	Approved
0.6478	Remote Similarity	NPD4178	Approved
0.6478	Remote Similarity	NPD4176	Approved
0.6474	Remote Similarity	NPD2117	Pre-registration
0.6474	Remote Similarity	NPD2116	Approved
0.6474	Remote Similarity	NPD2115	Approved
0.6471	Remote Similarity	NPD6768	Approved
0.6467	Remote Similarity	NPD8172	Phase 2
0.6467	Remote Similarity	NPD8173	Phase 2
0.6463	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1036	Approved
0.6452	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.645	Remote Similarity	NPD8114	Approved
0.645	Remote Similarity	NPD8115	Approved
0.6448	Remote Similarity	NPD5183	Approved
0.6448	Remote Similarity	NPD5186	Approved
0.6447	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6999	Discontinued
0.6442	Remote Similarity	NPD4549	Discontinued
0.6438	Remote Similarity	NPD1360	Approved
0.6437	Remote Similarity	NPD4432	Discontinued
0.6437	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7666	Phase 3
0.6436	Remote Similarity	NPD7665	Phase 2
0.6418	Remote Similarity	NPD7001	Phase 3
0.6418	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2946	Phase 2
0.641	Remote Similarity	NPD1344	Phase 2
0.6404	Remote Similarity	NPD951	Approved
0.6404	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5748	Phase 2
0.64	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7890	Discontinued
0.6393	Remote Similarity	NPD6457	Approved
0.6392	Remote Similarity	NPD3030	Approved
0.6392	Remote Similarity	NPD3032	Approved
0.6392	Remote Similarity	NPD3031	Approved
0.639	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2950	Approved
0.6386	Remote Similarity	NPD1527	Phase 2
0.6386	Remote Similarity	NPD2949	Approved
0.6384	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3227	Phase 2
0.6379	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8165	Discontinued
0.6378	Remote Similarity	NPD3377	Discontinued
0.6378	Remote Similarity	NPD5582	Discontinued
0.6364	Remote Similarity	NPD7308	Discontinued
0.6364	Remote Similarity	NPD7606	Phase 3
0.6364	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3277	Phase 3
0.6358	Remote Similarity	NPD6320	Approved
0.6358	Remote Similarity	NPD5060	Phase 1
0.6351	Remote Similarity	NPD6995	Phase 1
0.6349	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6309	Approved
0.6347	Remote Similarity	NPD6311	Approved
0.6347	Remote Similarity	NPD8416	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