NPASS Compound

Structure

NPC471998 OpenBabel07101719242D 26 29 0 0 1 0 0 0 0 0999 V2000 -1.6273 -0.3262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0890 -1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9227 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0567 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0567 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9227 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7398 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7398 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7887 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7887 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0567 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4339 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1141 -2.0791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4088 -1.1235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9227 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7887 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1896 1.6828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7942 -2.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1391 -2.3016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3276 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 1 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 20 1 0 0 0 0 7 16 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 25 1 0 0 0 0 9 13 2 0 0 0 0 9 25 1 0 0 0 0 10 21 1 0 0 0 0 11 19 1 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 6 0 0 0 14 19 1 0 0 0 0 15 18 1 6 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 1 1 6 0 0 0 19 2 1 6 0 0 0 20 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	362.446
LogP:	1.863
LogD:	1.676
LogS:	-3.575
# Rotatable Bonds:	2
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.785
Synthetic Accessibility Score:	4.77
Fsp3:	0.7
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:	-5.722
MDCK Permeability:	7.5003090387326665e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.127
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146
Plasma Protein Binding (PPB):	88.96341705322266%
Volume Distribution (VD):	0.529
Pgp-substrate:	9.498601913452148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.309
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.209
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.295
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	3.369
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.323
Skin Sensitization:	0.068
Carcinogencity:	0.864
Eye Corrosion:	0.005
Eye Irritation:	0.363
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC471998

Natural Product ID:	NPC471998
*Common Name:**	ZULROTFSZUEJTM-LXWRTIBQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZULROTFSZUEJTM-LXWRTIBQSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-18-7-16(22)26-11-19(2,17(23)24)14(18)5-6-20(10-21)13-9-25-8-12(13)3-4-15(18)20/h8-9,14-15,21H,3-7,10-11H2,1-2H3,(H,23,24)/t14-,15-,18+,19-,20-/m1/s1
SMILES:	OC[C@]12CC[C@@H]3[C@]([C@H]2CCc2c1coc2)(C)CC(=O)OC[C@@]3(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3315159
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones

*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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

☑ 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
ED50	1
Others	1

Activity Type	# Activity
Individual Protein	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Inhibition	<	50.0	%	PMID[470336]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	ED50	=	50.0	uM	PMID[470336]

☑ 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 NPC471998 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	261
0.1-0.2	1175
0.2-0.3	3029
0.3-0.4	6375
0.4-0.5	12167
0.5-0.6	11570
0.6-0.7	7300
0.7-0.8	729
0.8-0.85	82
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9147	High Similarity	NPC120836
0.9147	High Similarity	NPC223063
0.8939	High Similarity	NPC471995
0.8921	High Similarity	NPC41182
0.8906	High Similarity	NPC130275
0.8864	High Similarity	NPC89133
0.8837	High Similarity	NPC230979
0.8828	High Similarity	NPC272899
0.8714	High Similarity	NPC476944
0.8671	High Similarity	NPC195325
0.8671	High Similarity	NPC472654
0.8662	High Similarity	NPC250228
0.8643	High Similarity	NPC267632
0.8626	High Similarity	NPC46536
0.8626	High Similarity	NPC138139
0.8623	High Similarity	NPC90953
0.8605	High Similarity	NPC36255
0.8571	High Similarity	NPC20578
0.8571	High Similarity	NPC62103
0.8551	High Similarity	NPC471996
0.8551	High Similarity	NPC476943
0.855	High Similarity	NPC179354
0.855	High Similarity	NPC303010
0.8542	High Similarity	NPC211625
0.8514	High Similarity	NPC472772
0.8496	Intermediate Similarity	NPC207294
0.8496	Intermediate Similarity	NPC112706
0.8493	Intermediate Similarity	NPC475777
0.8493	Intermediate Similarity	NPC469503
0.8493	Intermediate Similarity	NPC75906
0.8478	Intermediate Similarity	NPC310043
0.8478	Intermediate Similarity	NPC4764
0.8478	Intermediate Similarity	NPC310830
0.8473	Intermediate Similarity	NPC83115
0.8472	Intermediate Similarity	NPC476942
0.8472	Intermediate Similarity	NPC476941
0.8451	Intermediate Similarity	NPC251865
0.844	Intermediate Similarity	NPC121158
0.8435	Intermediate Similarity	NPC114880
0.8435	Intermediate Similarity	NPC178932
0.8433	Intermediate Similarity	NPC198904
0.8421	Intermediate Similarity	NPC83178
0.8406	Intermediate Similarity	NPC46896
0.8406	Intermediate Similarity	NPC214572
0.8403	Intermediate Similarity	NPC476938
0.8403	Intermediate Similarity	NPC476937
0.8403	Intermediate Similarity	NPC470941
0.8397	Intermediate Similarity	NPC16922
0.8389	Intermediate Similarity	NPC45101
0.838	Intermediate Similarity	NPC64568
0.8378	Intermediate Similarity	NPC75310
0.8378	Intermediate Similarity	NPC35000
0.8378	Intermediate Similarity	NPC469336
0.8369	Intermediate Similarity	NPC205765
0.8369	Intermediate Similarity	NPC20500
0.8359	Intermediate Similarity	NPC212918
0.8356	Intermediate Similarity	NPC156189
0.8346	Intermediate Similarity	NPC74612
0.8346	Intermediate Similarity	NPC23086
0.8344	Intermediate Similarity	NPC472771
0.8333	Intermediate Similarity	NPC62799
0.8333	Intermediate Similarity	NPC92941
0.8333	Intermediate Similarity	NPC158525
0.8333	Intermediate Similarity	NPC346
0.8311	Intermediate Similarity	NPC57998
0.8311	Intermediate Similarity	NPC30222
0.8311	Intermediate Similarity	NPC282445
0.8298	Intermediate Similarity	NPC67003
0.8289	Intermediate Similarity	NPC472773
0.8288	Intermediate Similarity	NPC470791
0.8288	Intermediate Similarity	NPC69647
0.8288	Intermediate Similarity	NPC125182
0.8288	Intermediate Similarity	NPC470790
0.8286	Intermediate Similarity	NPC220094
0.8278	Intermediate Similarity	NPC470789
0.8276	Intermediate Similarity	NPC255414
0.8276	Intermediate Similarity	NPC221809
0.8252	Intermediate Similarity	NPC476946
0.8252	Intermediate Similarity	NPC205071
0.8252	Intermediate Similarity	NPC103134
0.8252	Intermediate Similarity	NPC243577
0.8252	Intermediate Similarity	NPC223415
0.8252	Intermediate Similarity	NPC470741
0.8219	Intermediate Similarity	NPC19747
0.8214	Intermediate Similarity	NPC470742
0.8214	Intermediate Similarity	NPC42400
0.8214	Intermediate Similarity	NPC186626
0.8212	Intermediate Similarity	NPC474611
0.8212	Intermediate Similarity	NPC475967
0.8212	Intermediate Similarity	NPC475226
0.8207	Intermediate Similarity	NPC97904
0.8194	Intermediate Similarity	NPC142113
0.8188	Intermediate Similarity	NPC214097
0.8175	Intermediate Similarity	NPC61788
0.8158	Intermediate Similarity	NPC335761
0.8151	Intermediate Similarity	NPC216755
0.8151	Intermediate Similarity	NPC471174
0.8146	Intermediate Similarity	NPC249021
0.8146	Intermediate Similarity	NPC299038
0.8146	Intermediate Similarity	NPC475066
0.8143	Intermediate Similarity	NPC146872
0.8138	Intermediate Similarity	NPC5676
0.8133	Intermediate Similarity	NPC44675
0.8133	Intermediate Similarity	NPC264943
0.8133	Intermediate Similarity	NPC281258
0.8133	Intermediate Similarity	NPC214541
0.8129	Intermediate Similarity	NPC472774
0.8129	Intermediate Similarity	NPC472775
0.8129	Intermediate Similarity	NPC476853
0.8129	Intermediate Similarity	NPC472651
0.8121	Intermediate Similarity	NPC476940
0.8121	Intermediate Similarity	NPC268905
0.8121	Intermediate Similarity	NPC44577
0.8121	Intermediate Similarity	NPC476939
0.8117	Intermediate Similarity	NPC261184
0.8108	Intermediate Similarity	NPC476122
0.8108	Intermediate Similarity	NPC469335
0.8108	Intermediate Similarity	NPC477404
0.8108	Intermediate Similarity	NPC470997
0.8108	Intermediate Similarity	NPC196864
0.8108	Intermediate Similarity	NPC159927
0.8105	Intermediate Similarity	NPC5079
0.8105	Intermediate Similarity	NPC200782
0.8105	Intermediate Similarity	NPC69028
0.8105	Intermediate Similarity	NPC207978
0.8105	Intermediate Similarity	NPC472767
0.8092	Intermediate Similarity	NPC262872
0.8092	Intermediate Similarity	NPC307383
0.8088	Intermediate Similarity	NPC329707
0.8088	Intermediate Similarity	NPC477040
0.8082	Intermediate Similarity	NPC262198
0.8077	Intermediate Similarity	NPC472652
0.8069	Intermediate Similarity	NPC137295
0.8065	Intermediate Similarity	NPC23387
0.8058	Intermediate Similarity	NPC470740
0.8058	Intermediate Similarity	NPC293253
0.8056	Intermediate Similarity	NPC52412
0.8054	Intermediate Similarity	NPC18135
0.8052	Intermediate Similarity	NPC134254
0.8052	Intermediate Similarity	NPC234660
0.8052	Intermediate Similarity	NPC39986
0.8052	Intermediate Similarity	NPC302369
0.8052	Intermediate Similarity	NPC51568
0.8052	Intermediate Similarity	NPC477405
0.8045	Intermediate Similarity	NPC477967
0.8042	Intermediate Similarity	NPC90296
0.8042	Intermediate Similarity	NPC148374
0.8039	Intermediate Similarity	NPC472653
0.8039	Intermediate Similarity	NPC477402
0.8039	Intermediate Similarity	NPC25255
0.8027	Intermediate Similarity	NPC10088
0.8026	Intermediate Similarity	NPC304692
0.8026	Intermediate Similarity	NPC261597
0.8026	Intermediate Similarity	NPC472777
0.8026	Intermediate Similarity	NPC472778
0.8026	Intermediate Similarity	NPC167142
0.8026	Intermediate Similarity	NPC472776
0.8013	Intermediate Similarity	NPC92979
0.8	Intermediate Similarity	NPC476856
0.8	Intermediate Similarity	NPC276551
0.8	Intermediate Similarity	NPC472672
0.8	Intermediate Similarity	NPC476860
0.8	Intermediate Similarity	NPC33938
0.8	Intermediate Similarity	NPC476201
0.8	Intermediate Similarity	NPC476858
0.8	Intermediate Similarity	NPC123088
0.8	Intermediate Similarity	NPC476857
0.7987	Intermediate Similarity	NPC329938
0.7987	Intermediate Similarity	NPC212257
0.7987	Intermediate Similarity	NPC82851
0.7987	Intermediate Similarity	NPC211777
0.7987	Intermediate Similarity	NPC263432
0.7987	Intermediate Similarity	NPC193798
0.7987	Intermediate Similarity	NPC18986
0.7974	Intermediate Similarity	NPC472671
0.7974	Intermediate Similarity	NPC477403
0.7974	Intermediate Similarity	NPC237155
0.7974	Intermediate Similarity	NPC140952
0.7972	Intermediate Similarity	NPC202260
0.7971	Intermediate Similarity	NPC476925
0.7961	Intermediate Similarity	NPC104736
0.7961	Intermediate Similarity	NPC41880
0.7961	Intermediate Similarity	NPC469485
0.7961	Intermediate Similarity	NPC263265
0.7961	Intermediate Similarity	NPC126723
0.7959	Intermediate Similarity	NPC276676
0.7956	Intermediate Similarity	NPC477123
0.7956	Intermediate Similarity	NPC476917
0.7956	Intermediate Similarity	NPC477966
0.7956	Intermediate Similarity	NPC327527
0.7949	Intermediate Similarity	NPC470875
0.7949	Intermediate Similarity	NPC93172
0.7949	Intermediate Similarity	NPC97574
0.7949	Intermediate Similarity	NPC121995
0.7947	Intermediate Similarity	NPC98206
0.7947	Intermediate Similarity	NPC237259
0.7947	Intermediate Similarity	NPC302054
0.7947	Intermediate Similarity	NPC253201
0.7947	Intermediate Similarity	NPC34421
0.7945	Intermediate Similarity	NPC84479

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 NPC471998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	997
0.2-0.3	2161
0.3-0.4	2712
0.4-0.5	2082
0.5-0.6	791
0.6-0.7	170
0.7-0.8	5
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
0.8013	Intermediate Similarity	NPD5760	Phase 2
0.8013	Intermediate Similarity	NPD5761	Phase 2
0.7603	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8434	Phase 2
0.7358	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7255	Intermediate Similarity	NPD2533	Approved
0.7255	Intermediate Similarity	NPD2532	Approved
0.7255	Intermediate Similarity	NPD2534	Approved
0.7133	Intermediate Similarity	NPD2346	Discontinued
0.7097	Intermediate Similarity	NPD6273	Approved
0.7083	Intermediate Similarity	NPD6764	Approved
0.7083	Intermediate Similarity	NPD6765	Approved
0.7055	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7051	Intermediate Similarity	NPD920	Approved
0.7039	Intermediate Similarity	NPD2800	Approved
0.6962	Remote Similarity	NPD3226	Approved
0.6954	Remote Similarity	NPD1551	Phase 2
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6785	Approved
0.6919	Remote Similarity	NPD6784	Approved
0.6918	Remote Similarity	NPD6599	Discontinued
0.6908	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6004	Phase 3
0.6908	Remote Similarity	NPD6005	Phase 3
0.6908	Remote Similarity	NPD6002	Phase 3
0.6894	Remote Similarity	NPD7819	Suspended
0.6853	Remote Similarity	NPD1608	Approved
0.6818	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6832	Phase 2
0.6797	Remote Similarity	NPD2344	Approved
0.6797	Remote Similarity	NPD1471	Phase 3
0.6795	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6559	Discontinued
0.6776	Remote Similarity	NPD7033	Discontinued
0.6774	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3749	Approved
0.6753	Remote Similarity	NPD970	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2935	Discontinued
0.6712	Remote Similarity	NPD2797	Approved
0.6711	Remote Similarity	NPD3268	Approved
0.671	Remote Similarity	NPD1243	Approved
0.6709	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5710	Approved
0.6707	Remote Similarity	NPD5711	Approved
0.6687	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD7003	Approved
0.6646	Remote Similarity	NPD6799	Approved
0.6644	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1778	Approved
0.6643	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD17	Approved
0.6624	Remote Similarity	NPD2309	Approved
0.6623	Remote Similarity	NPD4140	Approved
0.6623	Remote Similarity	NPD4476	Approved
0.6623	Remote Similarity	NPD4477	Approved
0.6621	Remote Similarity	NPD9717	Approved
0.6606	Remote Similarity	NPD7768	Phase 2
0.66	Remote Similarity	NPD3764	Approved
0.66	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1203	Approved
0.6579	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6355	Discontinued
0.6573	Remote Similarity	NPD5585	Approved
0.6566	Remote Similarity	NPD7075	Discontinued
0.6561	Remote Similarity	NPD3750	Approved
0.6561	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4110	Phase 3
0.6558	Remote Similarity	NPD4308	Phase 3
0.6556	Remote Similarity	NPD8032	Phase 2
0.6554	Remote Similarity	NPD5647	Approved
0.6554	Remote Similarity	NPD2798	Approved
0.655	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD8127	Discontinued
0.6545	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7458	Discontinued
0.6536	Remote Similarity	NPD6651	Approved
0.6531	Remote Similarity	NPD1283	Approved
0.6527	Remote Similarity	NPD919	Approved
0.6524	Remote Similarity	NPD37	Approved
0.6524	Remote Similarity	NPD6801	Discontinued
0.6516	Remote Similarity	NPD6100	Approved
0.6516	Remote Similarity	NPD2796	Approved
0.6516	Remote Similarity	NPD6099	Approved
0.6514	Remote Similarity	NPD8312	Approved
0.6514	Remote Similarity	NPD8313	Approved
0.6513	Remote Similarity	NPD2979	Phase 3
0.6512	Remote Similarity	NPD5844	Phase 1
0.6509	Remote Similarity	NPD6232	Discontinued
0.6507	Remote Similarity	NPD3972	Approved
0.6506	Remote Similarity	NPD4965	Approved
0.6506	Remote Similarity	NPD4966	Approved
0.6506	Remote Similarity	NPD4967	Phase 2
0.6491	Remote Similarity	NPD7473	Discontinued
0.6488	Remote Similarity	NPD5494	Approved
0.6486	Remote Similarity	NPD3267	Approved
0.6486	Remote Similarity	NPD3266	Approved
0.6485	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7236	Approved
0.6474	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD447	Suspended
0.6452	Remote Similarity	NPD3748	Approved
0.645	Remote Similarity	NPD6959	Discontinued
0.6446	Remote Similarity	NPD5402	Approved
0.6446	Remote Similarity	NPD3817	Phase 2
0.6443	Remote Similarity	NPD1019	Discontinued
0.6433	Remote Similarity	NPD1549	Phase 2
0.6433	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5403	Approved
0.6412	Remote Similarity	NPD7315	Approved
0.6412	Remote Similarity	NPD7229	Phase 3
0.6412	Remote Similarity	NPD6808	Phase 2
0.6407	Remote Similarity	NPD3882	Suspended
0.6407	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD4307	Phase 2
0.6403	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4380	Phase 2
0.6398	Remote Similarity	NPD5401	Approved
0.6398	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD8404	Phase 2
0.6389	Remote Similarity	NPD1894	Discontinued
0.6382	Remote Similarity	NPD411	Approved
0.6382	Remote Similarity	NPD7985	Registered
0.6377	Remote Similarity	NPD2182	Approved
0.6376	Remote Similarity	NPD6362	Approved
0.637	Remote Similarity	NPD3496	Discontinued
0.6369	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5762	Approved
0.6369	Remote Similarity	NPD5763	Approved
0.6358	Remote Similarity	NPD3818	Discontinued
0.6353	Remote Similarity	NPD1247	Approved
0.6351	Remote Similarity	NPD4359	Approved
0.6347	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1510	Phase 2
0.634	Remote Similarity	NPD6233	Phase 2
0.6335	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6234	Discontinued
0.6327	Remote Similarity	NPD1281	Approved
0.6327	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD1934	Approved
0.6323	Remote Similarity	NPD6653	Approved
0.6323	Remote Similarity	NPD1607	Approved
0.6309	Remote Similarity	NPD3225	Approved
0.6309	Remote Similarity	NPD1876	Approved
0.6306	Remote Similarity	NPD2438	Suspended
0.6299	Remote Similarity	NPD1240	Approved
0.6287	Remote Similarity	NPD2801	Approved
0.628	Remote Similarity	NPD7239	Suspended
0.6276	Remote Similarity	NPD9545	Approved
0.6275	Remote Similarity	NPD6798	Discontinued
0.6271	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7177	Discontinued
0.6258	Remote Similarity	NPD4622	Approved
0.6258	Remote Similarity	NPD5124	Phase 1
0.6258	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD4618	Approved
0.6258	Remote Similarity	NPD1933	Approved
0.6257	Remote Similarity	NPD7199	Phase 2
0.6257	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2614	Approved
0.625	Remote Similarity	NPD5953	Discontinued
0.6229	Remote Similarity	NPD7286	Phase 2
0.6229	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6280	Approved
0.6228	Remote Similarity	NPD6279	Approved
0.6226	Remote Similarity	NPD4534	Discontinued
0.6224	Remote Similarity	NPD5951	Approved
0.622	Remote Similarity	NPD7427	Discontinued
0.6209	Remote Similarity	NPD7095	Approved
0.6209	Remote Similarity	NPD7008	Discontinued
0.6203	Remote Similarity	NPD2531	Phase 2
0.6194	Remote Similarity	NPD4060	Phase 1
0.619	Remote Similarity	NPD8455	Phase 2
0.6185	Remote Similarity	NPD3926	Phase 2
0.6178	Remote Similarity	NPD5689	Approved
0.6178	Remote Similarity	NPD7097	Phase 1
0.6178	Remote Similarity	NPD5688	Approved
0.6175	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD1481	Phase 2
0.6173	Remote Similarity	NPD7440	Discontinued
0.6171	Remote Similarity	NPD7799	Discontinued
0.6171	Remote Similarity	NPD7228	Approved
0.6169	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5889	Approved
0.6168	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5890	Approved
0.6164	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD230	Phase 1
0.6154	Remote Similarity	NPD5735	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data