NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	545.2
Volume:	545.711
LogP:	4.286
LogD:	3.501
LogS:	-5.936
# Rotatable Bonds:	7
TPSA:	89.77
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.317
Synthetic Accessibility Score:	3.054
Fsp3:	0.29
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:	-5.481
MDCK Permeability:	5.1076927775284275e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.758
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	75.1065444946289%
Volume Distribution (VD):	0.48
Pgp-substrate:	6.930362224578857%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.987
CYP2C19-inhibitor:	0.673
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.747
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.963
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	9.33
Half-life (T1/2):	0.48

ADMET: Toxicity

hERG Blockers:	0.17
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.351
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.736
Skin Sensitization:	0.03
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.497

Download Data

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

Natural Product: NPC476998

Natural Product ID:	NPC476998
*Common Name:**	12-(3,4-Dimethoxyphenyl)-8,16,17,18-tetramethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-7-ol
IUPAC Name:	12-(3,4-dimethoxyphenyl)-8,16,17,18-tetramethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-7-ol
Synonyms:	Lamellarin I
Standard InCHIKey:	DJAQGPQDRCRBFP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C31H31NO8/c1-34-22-8-7-16(11-25(22)36-3)27-28-19-13-24(35-2)21(33)14-23(19)40-15-20(28)32-10-9-17-18(29(27)32)12-26(37-4)31(39-6)30(17)38-5/h7-8,11-14,33H,9-10,15H2,1-6H3
SMILES:	COC1=C(C=C(C=C1)C2=C3C4=CC(=C(C(=C4CCN3C5=C2C6=CC(=C(C=C6OC5)O)OC)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559516
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	=	1.93	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	75.11	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	159.2	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	237.81	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	316.41	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	IC50	=	2960000	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 NPC476998 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	518
0.1-0.2	2312
0.2-0.3	11147
0.3-0.4	6375
0.4-0.5	8432
0.5-0.6	10844
0.6-0.7	2699
0.7-0.8	340
0.8-0.85	24
0.85-0.9	0
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476996
0.9951	High Similarity	NPC476997
0.9951	High Similarity	NPC476994
0.9619	High Similarity	NPC476995
0.9289	High Similarity	NPC476999
0.8652	High Similarity	NPC129897
0.8591	High Similarity	NPC96584
0.8591	High Similarity	NPC255800
0.8584	High Similarity	NPC201508
0.8419	Intermediate Similarity	NPC473822
0.8271	Intermediate Similarity	NPC202605
0.8271	Intermediate Similarity	NPC112206
0.8265	Intermediate Similarity	NPC122463
0.8257	Intermediate Similarity	NPC174049
0.8248	Intermediate Similarity	NPC318068
0.8211	Intermediate Similarity	NPC148409
0.8113	Intermediate Similarity	NPC164374
0.8113	Intermediate Similarity	NPC137929
0.8095	Intermediate Similarity	NPC284141
0.8065	Intermediate Similarity	NPC474594
0.8043	Intermediate Similarity	NPC217554
0.8018	Intermediate Similarity	NPC203168
0.8009	Intermediate Similarity	NPC219664
0.7991	Intermediate Similarity	NPC200888
0.7981	Intermediate Similarity	NPC469440
0.7972	Intermediate Similarity	NPC31930
0.7957	Intermediate Similarity	NPC11408
0.7944	Intermediate Similarity	NPC16452
0.7944	Intermediate Similarity	NPC36229
0.7944	Intermediate Similarity	NPC476581
0.7926	Intermediate Similarity	NPC290689
0.7885	Intermediate Similarity	NPC469390
0.7885	Intermediate Similarity	NPC469792
0.7877	Intermediate Similarity	NPC4071
0.7877	Intermediate Similarity	NPC476578
0.7877	Intermediate Similarity	NPC476582
0.787	Intermediate Similarity	NPC474595
0.7857	Intermediate Similarity	NPC118121
0.7857	Intermediate Similarity	NPC85381
0.7854	Intermediate Similarity	NPC202768
0.7854	Intermediate Similarity	NPC53069
0.7854	Intermediate Similarity	NPC296482
0.785	Intermediate Similarity	NPC66815
0.7838	Intermediate Similarity	NPC204446
0.7824	Intermediate Similarity	NPC304183
0.7788	Intermediate Similarity	NPC313189
0.7762	Intermediate Similarity	NPC318805
0.7762	Intermediate Similarity	NPC41122
0.7759	Intermediate Similarity	NPC473183
0.77	Intermediate Similarity	NPC234318
0.7699	Intermediate Similarity	NPC280272
0.7692	Intermediate Similarity	NPC61350
0.7692	Intermediate Similarity	NPC96405
0.7692	Intermediate Similarity	NPC171409
0.7679	Intermediate Similarity	NPC100079
0.7679	Intermediate Similarity	NPC23614
0.7678	Intermediate Similarity	NPC280964
0.7678	Intermediate Similarity	NPC133140
0.7678	Intermediate Similarity	NPC114335
0.7678	Intermediate Similarity	NPC195268
0.7678	Intermediate Similarity	NPC141915
0.7672	Intermediate Similarity	NPC473184
0.7672	Intermediate Similarity	NPC277351
0.7671	Intermediate Similarity	NPC470931
0.7658	Intermediate Similarity	NPC149471
0.7658	Intermediate Similarity	NPC271215
0.7626	Intermediate Similarity	NPC135549
0.7619	Intermediate Similarity	NPC212237
0.7619	Intermediate Similarity	NPC116465
0.7595	Intermediate Similarity	NPC15406
0.7593	Intermediate Similarity	NPC477019
0.7585	Intermediate Similarity	NPC49672
0.758	Intermediate Similarity	NPC472111
0.7566	Intermediate Similarity	NPC46451
0.756	Intermediate Similarity	NPC30779
0.7559	Intermediate Similarity	NPC79293
0.7559	Intermediate Similarity	NPC279401
0.7552	Intermediate Similarity	NPC302807
0.7545	Intermediate Similarity	NPC235076
0.7535	Intermediate Similarity	NPC224928
0.7523	Intermediate Similarity	NPC188420
0.7512	Intermediate Similarity	NPC286119
0.75	Intermediate Similarity	NPC22115
0.75	Intermediate Similarity	NPC266931
0.75	Intermediate Similarity	NPC275680
0.7489	Intermediate Similarity	NPC295228
0.7488	Intermediate Similarity	NPC249996
0.7479	Intermediate Similarity	NPC77878
0.7479	Intermediate Similarity	NPC473182
0.7479	Intermediate Similarity	NPC183537
0.7477	Intermediate Similarity	NPC469589
0.7476	Intermediate Similarity	NPC181796
0.7476	Intermediate Similarity	NPC182052
0.7476	Intermediate Similarity	NPC290005
0.7476	Intermediate Similarity	NPC311973
0.7476	Intermediate Similarity	NPC42663
0.7476	Intermediate Similarity	NPC271013
0.7476	Intermediate Similarity	NPC49075
0.7476	Intermediate Similarity	NPC8836
0.7476	Intermediate Similarity	NPC104196
0.7476	Intermediate Similarity	NPC239824
0.7476	Intermediate Similarity	NPC290582
0.7476	Intermediate Similarity	NPC328155
0.7476	Intermediate Similarity	NPC222661
0.7476	Intermediate Similarity	NPC251735
0.7476	Intermediate Similarity	NPC90998
0.7476	Intermediate Similarity	NPC7715
0.7476	Intermediate Similarity	NPC476202
0.7476	Intermediate Similarity	NPC54654
0.7476	Intermediate Similarity	NPC229373
0.7476	Intermediate Similarity	NPC15414
0.7476	Intermediate Similarity	NPC258657
0.7476	Intermediate Similarity	NPC217748
0.7476	Intermediate Similarity	NPC185639
0.7476	Intermediate Similarity	NPC279228
0.7476	Intermediate Similarity	NPC223690
0.7476	Intermediate Similarity	NPC285931
0.7455	Intermediate Similarity	NPC251160
0.7441	Intermediate Similarity	NPC167116
0.7441	Intermediate Similarity	NPC274716
0.7441	Intermediate Similarity	NPC254441
0.744	Intermediate Similarity	NPC232386
0.744	Intermediate Similarity	NPC152680
0.744	Intermediate Similarity	NPC190783
0.7439	Intermediate Similarity	NPC284685
0.7438	Intermediate Similarity	NPC134637
0.7437	Intermediate Similarity	NPC119134
0.7431	Intermediate Similarity	NPC234197
0.7429	Intermediate Similarity	NPC195538
0.7414	Intermediate Similarity	NPC473185
0.7409	Intermediate Similarity	NPC191489
0.7407	Intermediate Similarity	NPC473053
0.7406	Intermediate Similarity	NPC16357
0.7406	Intermediate Similarity	NPC95426
0.7406	Intermediate Similarity	NPC302245
0.7395	Intermediate Similarity	NPC24260
0.7383	Intermediate Similarity	NPC206900
0.738	Intermediate Similarity	NPC132642
0.738	Intermediate Similarity	NPC469439
0.738	Intermediate Similarity	NPC54066
0.7371	Intermediate Similarity	NPC139783
0.7371	Intermediate Similarity	NPC65312
0.7364	Intermediate Similarity	NPC135887
0.7364	Intermediate Similarity	NPC199277
0.7361	Intermediate Similarity	NPC473589
0.7361	Intermediate Similarity	NPC478092
0.7361	Intermediate Similarity	NPC478091
0.7361	Intermediate Similarity	NPC30182
0.7358	Intermediate Similarity	NPC472589
0.7352	Intermediate Similarity	NPC11017
0.7343	Intermediate Similarity	NPC312872
0.7315	Intermediate Similarity	NPC478093
0.7314	Intermediate Similarity	NPC107123
0.7302	Intermediate Similarity	NPC175890
0.7302	Intermediate Similarity	NPC274661
0.7302	Intermediate Similarity	NPC11296
0.7302	Intermediate Similarity	NPC48490
0.7302	Intermediate Similarity	NPC82457
0.73	Intermediate Similarity	NPC90875
0.7297	Intermediate Similarity	NPC210256
0.7296	Intermediate Similarity	NPC214980
0.7295	Intermediate Similarity	NPC204908
0.7295	Intermediate Similarity	NPC83198
0.7293	Intermediate Similarity	NPC173080
0.7293	Intermediate Similarity	NPC469594
0.7291	Intermediate Similarity	NPC315634
0.7291	Intermediate Similarity	NPC88923
0.7291	Intermediate Similarity	NPC100734
0.7288	Intermediate Similarity	NPC233334
0.7286	Intermediate Similarity	NPC293093
0.7282	Intermediate Similarity	NPC13916
0.7282	Intermediate Similarity	NPC264850
0.7276	Intermediate Similarity	NPC472588
0.7273	Intermediate Similarity	NPC124313
0.7269	Intermediate Similarity	NPC191132
0.7269	Intermediate Similarity	NPC60295
0.7265	Intermediate Similarity	NPC67401
0.7264	Intermediate Similarity	NPC62069
0.7257	Intermediate Similarity	NPC329631
0.7253	Intermediate Similarity	NPC473449
0.7252	Intermediate Similarity	NPC475774
0.7246	Intermediate Similarity	NPC475253
0.7244	Intermediate Similarity	NPC101312
0.7243	Intermediate Similarity	NPC66083
0.7235	Intermediate Similarity	NPC78284
0.7234	Intermediate Similarity	NPC252251
0.7233	Intermediate Similarity	NPC24465
0.7231	Intermediate Similarity	NPC160100
0.722	Intermediate Similarity	NPC47059
0.722	Intermediate Similarity	NPC165349
0.722	Intermediate Similarity	NPC210296
0.722	Intermediate Similarity	NPC274291
0.722	Intermediate Similarity	NPC329708
0.722	Intermediate Similarity	NPC264166
0.722	Intermediate Similarity	NPC118832
0.7209	Intermediate Similarity	NPC477186
0.7209	Intermediate Similarity	NPC320088
0.7202	Intermediate Similarity	NPC256124
0.7196	Intermediate Similarity	NPC204385
0.7195	Intermediate Similarity	NPC475654

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 NPC476998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	651
0.2-0.3	980
0.3-0.4	1657
0.4-0.5	2659
0.5-0.6	2191
0.6-0.7	683
0.7-0.8	57
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8294	Intermediate Similarity	NPD7222	Phase 2
0.8233	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7452	Approved
0.8037	Intermediate Similarity	NPD7453	Approved
0.7983	Intermediate Similarity	NPD7169	Suspended
0.7939	Intermediate Similarity	NPD6494	Phase 2
0.7854	Intermediate Similarity	NPD3816	Phase 1
0.7854	Intermediate Similarity	NPD3815	Phase 1
0.7828	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD5902	Approved
0.7703	Intermediate Similarity	NPD5903	Approved
0.7678	Intermediate Similarity	NPD3921	Approved
0.7678	Intermediate Similarity	NPD3923	Approved
0.7678	Intermediate Similarity	NPD3922	Approved
0.7678	Intermediate Similarity	NPD3924	Approved
0.766	Intermediate Similarity	NPD7417	Discontinued
0.7659	Intermediate Similarity	NPD3920	Phase 2
0.7566	Intermediate Similarity	NPD3763	Approved
0.7565	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7558	Phase 2
0.7512	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.751	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD8054	Approved
0.7476	Intermediate Similarity	NPD8053	Approved
0.7442	Intermediate Similarity	NPD4418	Discontinued
0.7439	Intermediate Similarity	NPD7955	Approved
0.7439	Intermediate Similarity	NPD7956	Approved
0.7434	Intermediate Similarity	NPD5612	Discontinued
0.743	Intermediate Similarity	NPD6569	Phase 2
0.7411	Intermediate Similarity	NPD4502	Phase 2
0.7409	Intermediate Similarity	NPD7708	Approved
0.7377	Intermediate Similarity	NPD7859	Phase 2
0.7361	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD5658	Approved
0.7342	Intermediate Similarity	NPD5530	Phase 1
0.7309	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD5429	Discontinued
0.7308	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7395	Discontinued
0.7291	Intermediate Similarity	NPD7803	Approved
0.7277	Intermediate Similarity	NPD5256	Discontinued
0.7265	Intermediate Similarity	NPD3003	Approved
0.7265	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7194	Discontinued
0.7257	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7719	Discontinued
0.7251	Intermediate Similarity	NPD4203	Approved
0.7251	Intermediate Similarity	NPD4204	Approved
0.7248	Intermediate Similarity	NPD6550	Discontinued
0.7243	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6361	Phase 2
0.7227	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7069	Discontinued
0.7222	Intermediate Similarity	NPD7675	Phase 3
0.7222	Intermediate Similarity	NPD7674	Phase 3
0.7222	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD32	Approved
0.722	Intermediate Similarity	NPD4038	Approved
0.722	Intermediate Similarity	NPD4122	Approved
0.722	Intermediate Similarity	NPD4034	Approved
0.722	Intermediate Similarity	NPD4037	Approved
0.722	Intermediate Similarity	NPD4033	Approved
0.722	Intermediate Similarity	NPD4039	Approved
0.722	Intermediate Similarity	NPD4036	Approved
0.722	Intermediate Similarity	NPD4035	Approved
0.722	Intermediate Similarity	NPD31	Approved
0.7217	Intermediate Similarity	NPD6985	Discontinued
0.7202	Intermediate Similarity	NPD6590	Discontinued
0.7202	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6716	Phase 1
0.719	Intermediate Similarity	NPD1483	Discontinued
0.719	Intermediate Similarity	NPD8156	Discontinued
0.7188	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5930	Phase 3
0.715	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8251	Approved
0.7143	Intermediate Similarity	NPD8099	Discontinued
0.7143	Intermediate Similarity	NPD8252	Approved
0.7143	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7906	Approved
0.7121	Intermediate Similarity	NPD7682	Approved
0.7121	Intermediate Similarity	NPD7684	Approved
0.7118	Intermediate Similarity	NPD5945	Phase 1
0.7118	Intermediate Similarity	NPD5944	Phase 1
0.7113	Intermediate Similarity	NPD4080	Discontinued
0.7112	Intermediate Similarity	NPD3875	Discontinued
0.7105	Intermediate Similarity	NPD4131	Phase 3
0.71	Intermediate Similarity	NPD5164	Discontinued
0.7091	Intermediate Similarity	NPD5512	Phase 3
0.7083	Intermediate Similarity	NPD6963	Approved
0.7083	Intermediate Similarity	NPD6964	Approved
0.7082	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7426	Phase 1
0.7059	Intermediate Similarity	NPD6988	Phase 1
0.7054	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8442	Discontinued
0.7031	Intermediate Similarity	NPD6220	Phase 3
0.7028	Intermediate Similarity	NPD6159	Phase 2
0.7021	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3477	Phase 2
0.7014	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD3386	Phase 2
0.7009	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD6290	Phase 2
0.7	Intermediate Similarity	NPD4551	Phase 2
0.6996	Remote Similarity	NPD1768	Approved
0.6975	Remote Similarity	NPD6327	Phase 1
0.6975	Remote Similarity	NPD6326	Phase 2
0.6974	Remote Similarity	NPD7672	Approved
0.6974	Remote Similarity	NPD7671	Approved
0.6964	Remote Similarity	NPD8359	Phase 2
0.6961	Remote Similarity	NPD4678	Approved
0.6961	Remote Similarity	NPD4675	Approved
0.6951	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8101	Phase 3
0.6944	Remote Similarity	NPD8244	Phase 2
0.694	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4885	Approved
0.6927	Remote Similarity	NPD4663	Approved
0.6926	Remote Similarity	NPD4927	Discontinued
0.6923	Remote Similarity	NPD6568	Discontinued
0.692	Remote Similarity	NPD2177	Approved
0.692	Remote Similarity	NPD2175	Phase 3
0.692	Remote Similarity	NPD2176	Approved
0.6917	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4875	Phase 3
0.6911	Remote Similarity	NPD4876	Phase 3
0.6906	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8016	Phase 3
0.6894	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6219	Discontinued
0.6883	Remote Similarity	NPD5066	Phase 2
0.6883	Remote Similarity	NPD5936	Approved
0.6883	Remote Similarity	NPD5939	Approved
0.6883	Remote Similarity	NPD5067	Phase 2
0.6881	Remote Similarity	NPD4375	Approved
0.688	Remote Similarity	NPD6243	Phase 3
0.688	Remote Similarity	NPD6244	Phase 3
0.6878	Remote Similarity	NPD1856	Discontinued
0.6875	Remote Similarity	NPD7555	Discontinued
0.6872	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6991	Approved
0.6867	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4578	Approved
0.6866	Remote Similarity	NPD4577	Approved
0.6864	Remote Similarity	NPD7180	Phase 3
0.6862	Remote Similarity	NPD3263	Phase 3
0.6857	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD1392	Approved
0.6856	Remote Similarity	NPD7263	Phase 2
0.6855	Remote Similarity	NPD6230	Discontinued
0.6854	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5866	Approved
0.6852	Remote Similarity	NPD3037	Phase 1
0.685	Remote Similarity	NPD8091	Phase 3
0.6846	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7567	Approved
0.6844	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6517	Phase 3
0.6842	Remote Similarity	NPD3397	Phase 2
0.6838	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4889	Approved
0.6835	Remote Similarity	NPD5506	Approved
0.6835	Remote Similarity	NPD5507	Approved
0.683	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7885	Phase 2
0.6829	Remote Similarity	NPD7886	Phase 2
0.6828	Remote Similarity	NPD6975	Discontinued
0.6827	Remote Similarity	NPD8100	Phase 3
0.6822	Remote Similarity	NPD6974	Phase 3
0.682	Remote Similarity	NPD6246	Approved
0.6816	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6736	Discontinued
0.6803	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4437	Phase 3
0.6793	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6856	Discontinued
0.6784	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5938	Phase 3
0.6773	Remote Similarity	NPD1034	Phase 3
0.6773	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4083	Discontinued
0.6756	Remote Similarity	NPD4604	Approved
0.6756	Remote Similarity	NPD4605	Approved
0.6756	Remote Similarity	NPD1229	Phase 2
0.6751	Remote Similarity	NPD6501	Approved
0.6751	Remote Similarity	NPD2899	Discontinued
0.6751	Remote Similarity	NPD6500	Approved
0.6749	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