NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	531.19
Volume:	528.415
LogP:	4.659
LogD:	3.505
LogS:	-5.992
# Rotatable Bonds:	6
TPSA:	100.77
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	3.179
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.511
MDCK Permeability:	3.1049930839799345e-05
Pgp-inhibitor:	0.919
Pgp-substrate:	0.356
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	84.13066864013672%
Volume Distribution (VD):	0.404
Pgp-substrate:	8.232748031616211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.15
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.607
CYP2C19-substrate:	0.487
CYP2C9-inhibitor:	0.667
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.96
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.81

ADMET: Excretion

Clearance (CL):	9.805
Half-life (T1/2):	0.606

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.379
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.074
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.614

Download Data

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

Natural Product: NPC476994

Natural Product ID:	NPC476994
*Common Name:**	12-(3,5-Dimethoxyphenyl)-8,16,17-trimethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaene-7,18-diol
IUPAC Name:	12-(3,5-dimethoxyphenyl)-8,16,17-trimethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaene-7,18-diol
Synonyms:	Lamellarin Gamma
Standard InCHIKey:	BQPGOFVLERQHRG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H29NO8/c1-34-16-8-15(9-17(10-16)35-2)26-27-20-12-24(36-3)22(32)13-23(20)39-14-21(27)31-7-6-18-19(28(26)31)11-25(37-4)30(38-5)29(18)33/h8-13,32-33H,6-7,14H2,1-5H3
SMILES:	COC1=CC(=CC(=C1)C2=C3C4=CC(=C(C(=C4CCN3C5=C2C6=CC(=C(C=C6OC5)O)OC)O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559525
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002334] Phenylpyrroles

*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
NPO16570	Didemnum obscurum	Species	Didemnidae	Eukaryota	n.a.	Tiruchandur coast in the Gulf of Mannar, Tamilnadu, India	2002-FEB	PMID[15270574]
NPO16570	Didemnum obscurum	Species	Didemnidae	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	1
Others	6

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity	Activity	=	4.98	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	84.28	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	87.37	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	90.82	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	92.42	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	IC50	=	3280000	nM	PMID[15270574]
NPT2	Others	Unspecified	Ratio IC50	=	0.02	n.a.	PMID[15270574]

☑ 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 NPC476994 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	526
0.1-0.2	2347
0.2-0.3	11161
0.3-0.4	6501
0.4-0.5	8630
0.5-0.6	10654
0.6-0.7	2538
0.7-0.8	315
0.8-0.85	19
0.85-0.9	0
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9951	High Similarity	NPC476996
0.9951	High Similarity	NPC476998
0.9901	High Similarity	NPC476997
0.9665	High Similarity	NPC476995
0.9242	High Similarity	NPC476999
0.8609	High Similarity	NPC129897
0.8545	High Similarity	NPC255800
0.8545	High Similarity	NPC96584
0.8539	High Similarity	NPC201508
0.8372	Intermediate Similarity	NPC473822
0.8224	Intermediate Similarity	NPC112206
0.8224	Intermediate Similarity	NPC202605
0.8219	Intermediate Similarity	NPC122463
0.8211	Intermediate Similarity	NPC174049
0.8205	Intermediate Similarity	NPC318068
0.8165	Intermediate Similarity	NPC148409
0.8102	Intermediate Similarity	NPC474594
0.8066	Intermediate Similarity	NPC164374
0.8066	Intermediate Similarity	NPC137929
0.8052	Intermediate Similarity	NPC284141
0.8019	Intermediate Similarity	NPC469440
0.8	Intermediate Similarity	NPC217554
0.7972	Intermediate Similarity	NPC203168
0.7963	Intermediate Similarity	NPC219664
0.7946	Intermediate Similarity	NPC200888
0.7925	Intermediate Similarity	NPC31930
0.7923	Intermediate Similarity	NPC469390
0.7915	Intermediate Similarity	NPC476582
0.7915	Intermediate Similarity	NPC4071
0.7915	Intermediate Similarity	NPC476578
0.7913	Intermediate Similarity	NPC11408
0.7907	Intermediate Similarity	NPC474595
0.7897	Intermediate Similarity	NPC16452
0.7897	Intermediate Similarity	NPC36229
0.7897	Intermediate Similarity	NPC476581
0.788	Intermediate Similarity	NPC290689
0.7841	Intermediate Similarity	NPC469792
0.7824	Intermediate Similarity	NPC313189
0.7812	Intermediate Similarity	NPC118121
0.781	Intermediate Similarity	NPC85381
0.7808	Intermediate Similarity	NPC296482
0.7808	Intermediate Similarity	NPC202768
0.7808	Intermediate Similarity	NPC53069
0.7804	Intermediate Similarity	NPC66815
0.7793	Intermediate Similarity	NPC204446
0.7778	Intermediate Similarity	NPC304183
0.7729	Intermediate Similarity	NPC61350
0.7716	Intermediate Similarity	NPC473183
0.7714	Intermediate Similarity	NPC41122
0.7714	Intermediate Similarity	NPC318805
0.7661	Intermediate Similarity	NPC135549
0.7655	Intermediate Similarity	NPC280272
0.7653	Intermediate Similarity	NPC234318
0.7647	Intermediate Similarity	NPC171409
0.7647	Intermediate Similarity	NPC96405
0.7634	Intermediate Similarity	NPC100079
0.7634	Intermediate Similarity	NPC23614
0.763	Intermediate Similarity	NPC280964
0.763	Intermediate Similarity	NPC195268
0.763	Intermediate Similarity	NPC114335
0.763	Intermediate Similarity	NPC141915
0.763	Intermediate Similarity	NPC133140
0.7629	Intermediate Similarity	NPC473184
0.7629	Intermediate Similarity	NPC277351
0.7626	Intermediate Similarity	NPC470931
0.7617	Intermediate Similarity	NPC49672
0.7613	Intermediate Similarity	NPC149471
0.7613	Intermediate Similarity	NPC271215
0.7571	Intermediate Similarity	NPC116465
0.7571	Intermediate Similarity	NPC212237
0.757	Intermediate Similarity	NPC224928
0.7553	Intermediate Similarity	NPC15406
0.7546	Intermediate Similarity	NPC477019
0.7534	Intermediate Similarity	NPC472111
0.7522	Intermediate Similarity	NPC46451
0.7512	Intermediate Similarity	NPC30779
0.7512	Intermediate Similarity	NPC279401
0.7512	Intermediate Similarity	NPC79293
0.751	Intermediate Similarity	NPC302807
0.75	Intermediate Similarity	NPC235076
0.7477	Intermediate Similarity	NPC188420
0.7464	Intermediate Similarity	NPC286119
0.7455	Intermediate Similarity	NPC266931
0.7453	Intermediate Similarity	NPC22115
0.7453	Intermediate Similarity	NPC275680
0.7447	Intermediate Similarity	NPC295228
0.7441	Intermediate Similarity	NPC249996
0.7438	Intermediate Similarity	NPC77878
0.7438	Intermediate Similarity	NPC183537
0.7436	Intermediate Similarity	NPC473182
0.7432	Intermediate Similarity	NPC469589
0.7429	Intermediate Similarity	NPC104196
0.7429	Intermediate Similarity	NPC42663
0.7429	Intermediate Similarity	NPC49075
0.7429	Intermediate Similarity	NPC229373
0.7429	Intermediate Similarity	NPC239824
0.7429	Intermediate Similarity	NPC290582
0.7429	Intermediate Similarity	NPC279228
0.7429	Intermediate Similarity	NPC251735
0.7429	Intermediate Similarity	NPC223690
0.7429	Intermediate Similarity	NPC181796
0.7429	Intermediate Similarity	NPC8836
0.7429	Intermediate Similarity	NPC90998
0.7429	Intermediate Similarity	NPC7715
0.7429	Intermediate Similarity	NPC54654
0.7429	Intermediate Similarity	NPC258657
0.7429	Intermediate Similarity	NPC15414
0.7429	Intermediate Similarity	NPC182052
0.7429	Intermediate Similarity	NPC328155
0.7429	Intermediate Similarity	NPC271013
0.7429	Intermediate Similarity	NPC290005
0.7429	Intermediate Similarity	NPC311973
0.7429	Intermediate Similarity	NPC217748
0.7429	Intermediate Similarity	NPC476202
0.7429	Intermediate Similarity	NPC222661
0.7429	Intermediate Similarity	NPC185639
0.7429	Intermediate Similarity	NPC285931
0.7412	Intermediate Similarity	NPC469439
0.7411	Intermediate Similarity	NPC251160
0.7398	Intermediate Similarity	NPC284685
0.7397	Intermediate Similarity	NPC134637
0.7395	Intermediate Similarity	NPC119134
0.7393	Intermediate Similarity	NPC167116
0.7393	Intermediate Similarity	NPC274716
0.7393	Intermediate Similarity	NPC254441
0.7391	Intermediate Similarity	NPC232386
0.7391	Intermediate Similarity	NPC152680
0.7391	Intermediate Similarity	NPC190783
0.7385	Intermediate Similarity	NPC234197
0.7381	Intermediate Similarity	NPC195538
0.7371	Intermediate Similarity	NPC473185
0.7368	Intermediate Similarity	NPC191489
0.7361	Intermediate Similarity	NPC473053
0.7358	Intermediate Similarity	NPC95426
0.7358	Intermediate Similarity	NPC16357
0.7358	Intermediate Similarity	NPC302245
0.7349	Intermediate Similarity	NPC24260
0.7344	Intermediate Similarity	NPC107123
0.7336	Intermediate Similarity	NPC206900
0.7336	Intermediate Similarity	NPC132642
0.7336	Intermediate Similarity	NPC54066
0.7324	Intermediate Similarity	NPC139783
0.7324	Intermediate Similarity	NPC65312
0.7318	Intermediate Similarity	NPC199277
0.7318	Intermediate Similarity	NPC135887
0.7317	Intermediate Similarity	NPC472589
0.7315	Intermediate Similarity	NPC30182
0.7315	Intermediate Similarity	NPC473589
0.7315	Intermediate Similarity	NPC478092
0.7315	Intermediate Similarity	NPC478091
0.7306	Intermediate Similarity	NPC11017
0.7295	Intermediate Similarity	NPC312872
0.7269	Intermediate Similarity	NPC478093
0.7269	Intermediate Similarity	NPC78284
0.7268	Intermediate Similarity	NPC24465
0.7257	Intermediate Similarity	NPC90875
0.7256	Intermediate Similarity	NPC82457
0.7256	Intermediate Similarity	NPC48490
0.7256	Intermediate Similarity	NPC175890
0.7256	Intermediate Similarity	NPC274661
0.7256	Intermediate Similarity	NPC11296
0.7253	Intermediate Similarity	NPC214980
0.7252	Intermediate Similarity	NPC210256
0.7251	Intermediate Similarity	NPC88923
0.7251	Intermediate Similarity	NPC100734
0.7251	Intermediate Similarity	NPC315634
0.7249	Intermediate Similarity	NPC173080
0.7249	Intermediate Similarity	NPC469594
0.7246	Intermediate Similarity	NPC83198
0.7246	Intermediate Similarity	NPC233334
0.7246	Intermediate Similarity	NPC204908
0.7243	Intermediate Similarity	NPC320088
0.7243	Intermediate Similarity	NPC477186
0.7238	Intermediate Similarity	NPC293093
0.7236	Intermediate Similarity	NPC472588
0.7233	Intermediate Similarity	NPC264850
0.7233	Intermediate Similarity	NPC13916
0.7231	Intermediate Similarity	NPC124313
0.7224	Intermediate Similarity	NPC67401
0.7222	Intermediate Similarity	NPC191132
0.7222	Intermediate Similarity	NPC60295
0.7217	Intermediate Similarity	NPC62069
0.7215	Intermediate Similarity	NPC329631
0.721	Intermediate Similarity	NPC473449
0.7207	Intermediate Similarity	NPC475774
0.7205	Intermediate Similarity	NPC101312
0.7203	Intermediate Similarity	NPC475253
0.7196	Intermediate Similarity	NPC66083
0.7191	Intermediate Similarity	NPC252251
0.719	Intermediate Similarity	NPC160100
0.7181	Intermediate Similarity	NPC316981
0.7178	Intermediate Similarity	NPC210296
0.7177	Intermediate Similarity	NPC239775
0.7175	Intermediate Similarity	NPC165349
0.7175	Intermediate Similarity	NPC264166
0.7175	Intermediate Similarity	NPC274291
0.7175	Intermediate Similarity	NPC329708
0.7175	Intermediate Similarity	NPC118832
0.7175	Intermediate Similarity	NPC47059
0.7163	Intermediate Similarity	NPC14507

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 NPC476994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	650
0.2-0.3	997
0.3-0.4	1723
0.4-0.5	2655
0.5-0.6	2162
0.6-0.7	643
0.7-0.8	48
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
0.8246	Intermediate Similarity	NPD7222	Phase 2
0.819	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7991	Intermediate Similarity	NPD7453	Approved
0.7991	Intermediate Similarity	NPD7452	Approved
0.7941	Intermediate Similarity	NPD7169	Suspended
0.7895	Intermediate Similarity	NPD6494	Phase 2
0.7808	Intermediate Similarity	NPD3815	Phase 1
0.7808	Intermediate Similarity	NPD3816	Phase 1
0.7787	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5903	Approved
0.7658	Intermediate Similarity	NPD5902	Approved
0.763	Intermediate Similarity	NPD3921	Approved
0.763	Intermediate Similarity	NPD3924	Approved
0.763	Intermediate Similarity	NPD3922	Approved
0.763	Intermediate Similarity	NPD3923	Approved
0.7617	Intermediate Similarity	NPD7417	Discontinued
0.761	Intermediate Similarity	NPD3920	Phase 2
0.7522	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD3763	Approved
0.7511	Intermediate Similarity	NPD7558	Phase 2
0.7469	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8054	Approved
0.7429	Intermediate Similarity	NPD8053	Approved
0.7398	Intermediate Similarity	NPD7956	Approved
0.7398	Intermediate Similarity	NPD7955	Approved
0.7395	Intermediate Similarity	NPD4418	Discontinued
0.7389	Intermediate Similarity	NPD5612	Discontinued
0.7383	Intermediate Similarity	NPD6569	Phase 2
0.7368	Intermediate Similarity	NPD7708	Approved
0.7366	Intermediate Similarity	NPD4502	Phase 2
0.7336	Intermediate Similarity	NPD7859	Phase 2
0.7315	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD5658	Approved
0.7297	Intermediate Similarity	NPD5530	Phase 1
0.7269	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5429	Discontinued
0.7265	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7803	Approved
0.7249	Intermediate Similarity	NPD7395	Discontinued
0.723	Intermediate Similarity	NPD5256	Discontinued
0.722	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD1483	Discontinued
0.722	Intermediate Similarity	NPD3003	Approved
0.7217	Intermediate Similarity	NPD7194	Discontinued
0.7215	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.721	Intermediate Similarity	NPD7719	Discontinued
0.7208	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4204	Approved
0.7204	Intermediate Similarity	NPD4203	Approved
0.7202	Intermediate Similarity	NPD6550	Discontinued
0.7196	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6361	Phase 2
0.7182	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7069	Discontinued
0.7179	Intermediate Similarity	NPD7674	Phase 3
0.7179	Intermediate Similarity	NPD7675	Phase 3
0.7179	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4035	Approved
0.7175	Intermediate Similarity	NPD4038	Approved
0.7175	Intermediate Similarity	NPD4039	Approved
0.7175	Intermediate Similarity	NPD31	Approved
0.7175	Intermediate Similarity	NPD4037	Approved
0.7175	Intermediate Similarity	NPD4034	Approved
0.7175	Intermediate Similarity	NPD4033	Approved
0.7175	Intermediate Similarity	NPD32	Approved
0.7175	Intermediate Similarity	NPD4122	Approved
0.7175	Intermediate Similarity	NPD4036	Approved
0.7174	Intermediate Similarity	NPD6985	Discontinued
0.7156	Intermediate Similarity	NPD6590	Discontinued
0.7156	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6716	Phase 1
0.7143	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8156	Discontinued
0.7123	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5930	Phase 3
0.7103	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8252	Approved
0.7095	Intermediate Similarity	NPD8099	Discontinued
0.7095	Intermediate Similarity	NPD8251	Approved
0.7083	Intermediate Similarity	NPD7906	Approved
0.7082	Intermediate Similarity	NPD7682	Approved
0.7082	Intermediate Similarity	NPD7684	Approved
0.7074	Intermediate Similarity	NPD5945	Phase 1
0.7074	Intermediate Similarity	NPD5944	Phase 1
0.7071	Intermediate Similarity	NPD4080	Discontinued
0.7069	Intermediate Similarity	NPD3875	Discontinued
0.7061	Intermediate Similarity	NPD4131	Phase 3
0.7056	Intermediate Similarity	NPD5164	Discontinued
0.7045	Intermediate Similarity	NPD5512	Phase 3
0.7042	Intermediate Similarity	NPD6963	Approved
0.7042	Intermediate Similarity	NPD6964	Approved
0.7039	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7426	Phase 1
0.7014	Intermediate Similarity	NPD6988	Phase 1
0.7009	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8442	Discontinued
0.6987	Remote Similarity	NPD6220	Phase 3
0.6981	Remote Similarity	NPD6159	Phase 2
0.6979	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3477	Phase 2
0.6963	Remote Similarity	NPD3386	Phase 2
0.696	Remote Similarity	NPD6290	Phase 2
0.6955	Remote Similarity	NPD4551	Phase 2
0.6951	Remote Similarity	NPD1768	Approved
0.6933	Remote Similarity	NPD6326	Phase 2
0.6933	Remote Similarity	NPD6327	Phase 1
0.693	Remote Similarity	NPD7671	Approved
0.693	Remote Similarity	NPD7672	Approved
0.6923	Remote Similarity	NPD8359	Phase 2
0.6912	Remote Similarity	NPD4675	Approved
0.6912	Remote Similarity	NPD4678	Approved
0.6908	Remote Similarity	NPD8101	Phase 3
0.6906	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8244	Phase 2
0.6897	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4885	Approved
0.6883	Remote Similarity	NPD4927	Discontinued
0.6881	Remote Similarity	NPD4663	Approved
0.688	Remote Similarity	NPD6568	Discontinued
0.6875	Remote Similarity	NPD2176	Approved
0.6875	Remote Similarity	NPD2177	Approved
0.6875	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2175	Phase 3
0.6872	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4876	Phase 3
0.687	Remote Similarity	NPD4875	Phase 3
0.6862	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8016	Phase 3
0.6857	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6219	Discontinued
0.684	Remote Similarity	NPD5939	Approved
0.684	Remote Similarity	NPD5936	Approved
0.684	Remote Similarity	NPD6243	Phase 3
0.684	Remote Similarity	NPD6244	Phase 3
0.684	Remote Similarity	NPD5067	Phase 2
0.684	Remote Similarity	NPD5066	Phase 2
0.6835	Remote Similarity	NPD1856	Discontinued
0.6835	Remote Similarity	NPD4375	Approved
0.6833	Remote Similarity	NPD7555	Discontinued
0.6828	Remote Similarity	NPD6991	Approved
0.6827	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7180	Phase 3
0.6822	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.682	Remote Similarity	NPD3263	Phase 3
0.682	Remote Similarity	NPD4578	Approved
0.682	Remote Similarity	NPD4577	Approved
0.6816	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6230	Discontinued
0.6812	Remote Similarity	NPD1392	Approved
0.6812	Remote Similarity	NPD7263	Phase 2
0.6811	Remote Similarity	NPD8091	Phase 3
0.681	Remote Similarity	NPD5866	Approved
0.6808	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3037	Phase 1
0.6805	Remote Similarity	NPD7567	Approved
0.6805	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6517	Phase 3
0.68	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3397	Phase 2
0.6795	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5507	Approved
0.6793	Remote Similarity	NPD5506	Approved
0.6789	Remote Similarity	NPD7886	Phase 2
0.6789	Remote Similarity	NPD7885	Phase 2
0.6789	Remote Similarity	NPD4889	Approved
0.6787	Remote Similarity	NPD8100	Phase 3
0.6786	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6975	Discontinued
0.678	Remote Similarity	NPD6974	Phase 3
0.6778	Remote Similarity	NPD6246	Approved
0.6771	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6736	Discontinued
0.6762	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4437	Phase 3
0.6751	Remote Similarity	NPD6856	Discontinued
0.674	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5938	Phase 3
0.6727	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1034	Phase 3
0.6714	Remote Similarity	NPD4083	Discontinued
0.6711	Remote Similarity	NPD4605	Approved
0.6711	Remote Similarity	NPD1229	Phase 2
0.6711	Remote Similarity	NPD4604	Approved
0.6709	Remote Similarity	NPD2899	Discontinued
0.6709	Remote Similarity	NPD6501	Approved
0.6709	Remote Similarity	NPD6500	Approved
0.6708	Remote Similarity	NPD6962	Phase 2

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