NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	452.26
Volume:	469.837
LogP:	5.57
LogD:	5.354
LogS:	-3.857
# Rotatable Bonds:	10
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	4.482
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	1.7671773093752563e-05
Pgp-inhibitor:	0.612
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	96.76021575927734%
Volume Distribution (VD):	1.734
Pgp-substrate:	1.709418535232544%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.405
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.598
CYP2C9-inhibitor:	0.541
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.807
CYP3A4-inhibitor:	0.155
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	3.854
Half-life (T1/2):	0.02

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.615
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.233
Carcinogencity:	0.736
Eye Corrosion:	0.875
Eye Irritation:	0.687
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC477966

Natural Product ID:	NPC477966
*Common Name:**	Halisulfate-7
IUPAC Name:	[2-[2-[(1R,2R,4aS)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl]-5-(furan-3-yl)pentyl] hydrogen sulfate
Synonyms:	Halisulfate-7
Standard InCHIKey:	OYRXLPLXKXDHJP-MBHHTPPASA-N
Standard InCHI:	InChI=1S/C25H40O5S/c1-19-10-11-22-23(9-6-14-24(22,2)3)25(19,4)15-12-20(18-30-31(26,27)28)7-5-8-21-13-16-29-17-21/h9,13,16-17,19-20,22H,5-8,10-12,14-15,18H2,1-4H3,(H,26,27,28)/t19-,20?,22-,25-/m1/s1
SMILES:	C[C@@H]1CC[C@@H]2C(=CCCC2(C)C)[C@]1(C)CCC(CCCC3=COC=C3)COS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10050588
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000403] Organic sulfuric acids and derivatives [CHEMONTID:0003455] Sulfuric acid esters [CHEMONTID:0001185] Sulfuric acid monoesters

*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
NPO11499	Spongia irregularis	Species	Spongiidae	Eukaryota	n.a.	Keviang, Papua New Guinea (245.1' S, 15043' E)	n.a.	PMID[17979246]
NPO11499	Spongia irregularis	Species	Spongiidae	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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	69000	nM	PMID[17979246]
NPT2	Others	Unspecified	IC50	=	64000	nM	PMID[17979246]
NPT2	Others	Unspecified	IC50	=	140000	nM	PMID[17979246]

☑ 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 NPC477966 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	265
0.1-0.2	1466
0.2-0.3	3112
0.3-0.4	8136
0.4-0.5	12776
0.5-0.6	11428
0.6-0.7	4896
0.7-0.8	512
0.8-0.85	66
0.85-0.9	26
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477123
0.9835	High Similarity	NPC477040
0.9835	High Similarity	NPC477039
0.9675	High Similarity	NPC476925
0.9667	High Similarity	NPC477038
0.9667	High Similarity	NPC477965
0.9512	High Similarity	NPC476917
0.9512	High Similarity	NPC327527
0.95	High Similarity	NPC317217
0.9194	High Similarity	NPC23086
0.9048	High Similarity	NPC112706
0.9048	High Similarity	NPC207294
0.9024	High Similarity	NPC477967
0.8968	High Similarity	NPC83178
0.896	High Similarity	NPC179354
0.8952	High Similarity	NPC16922
0.8917	High Similarity	NPC150895
0.8889	High Similarity	NPC46536
0.8889	High Similarity	NPC138139
0.8852	High Similarity	NPC243704
0.8837	High Similarity	NPC61788
0.8837	High Similarity	NPC89133
0.874	High Similarity	NPC74612
0.8702	High Similarity	NPC218838
0.8618	High Similarity	NPC212918
0.8605	High Similarity	NPC26532
0.8571	High Similarity	NPC158525
0.8571	High Similarity	NPC36255
0.8571	High Similarity	NPC476947
0.8561	High Similarity	NPC471006
0.855	High Similarity	NPC298190
0.8538	High Similarity	NPC59502
0.8527	High Similarity	NPC290955
0.8527	High Similarity	NPC246392
0.8516	High Similarity	NPC303010
0.8516	High Similarity	NPC230979
0.8507	High Similarity	NPC146872
0.8504	High Similarity	NPC272899
0.8456	Intermediate Similarity	NPC90953
0.8444	Intermediate Similarity	NPC310830
0.8438	Intermediate Similarity	NPC130275
0.8438	Intermediate Similarity	NPC83115
0.8433	Intermediate Similarity	NPC92941
0.8421	Intermediate Similarity	NPC470740
0.84	Intermediate Similarity	NPC87466
0.8397	Intermediate Similarity	NPC223063
0.8397	Intermediate Similarity	NPC208389
0.8397	Intermediate Similarity	NPC120836
0.8394	Intermediate Similarity	NPC56197
0.8394	Intermediate Similarity	NPC67003
0.8372	Intermediate Similarity	NPC473885
0.8372	Intermediate Similarity	NPC471074
0.837	Intermediate Similarity	NPC46896
0.8346	Intermediate Similarity	NPC471817
0.8346	Intermediate Similarity	NPC97566
0.8321	Intermediate Similarity	NPC279877
0.832	Intermediate Similarity	NPC144745
0.832	Intermediate Similarity	NPC208906
0.8309	Intermediate Similarity	NPC470742
0.8295	Intermediate Similarity	NPC243269
0.8273	Intermediate Similarity	NPC121158
0.8261	Intermediate Similarity	NPC90296
0.8258	Intermediate Similarity	NPC198904
0.8248	Intermediate Similarity	NPC236532
0.8248	Intermediate Similarity	NPC220094
0.8248	Intermediate Similarity	NPC476943
0.8227	Intermediate Similarity	NPC185456
0.8214	Intermediate Similarity	NPC476946
0.8209	Intermediate Similarity	NPC471995
0.8209	Intermediate Similarity	NPC473982
0.8201	Intermediate Similarity	NPC205765
0.8188	Intermediate Similarity	NPC202260
0.8182	Intermediate Similarity	NPC329707
0.8175	Intermediate Similarity	NPC307401
0.8175	Intermediate Similarity	NPC42400
0.8156	Intermediate Similarity	NPC199044
0.8156	Intermediate Similarity	NPC142113
0.8156	Intermediate Similarity	NPC238843
0.8143	Intermediate Similarity	NPC473152
0.8143	Intermediate Similarity	NPC52412
0.8129	Intermediate Similarity	NPC148374
0.8112	Intermediate Similarity	NPC302987
0.8112	Intermediate Similarity	NPC471174
0.8099	Intermediate Similarity	NPC5676
0.8085	Intermediate Similarity	NPC243577
0.8085	Intermediate Similarity	NPC267632
0.8047	Intermediate Similarity	NPC473969
0.8043	Intermediate Similarity	NPC215109
0.8043	Intermediate Similarity	NPC170604
0.8042	Intermediate Similarity	NPC470999
0.8042	Intermediate Similarity	NPC346
0.8042	Intermediate Similarity	NPC471292
0.8031	Intermediate Similarity	NPC312525
0.8031	Intermediate Similarity	NPC217180
0.8028	Intermediate Similarity	NPC251865
0.8028	Intermediate Similarity	NPC476944
0.8016	Intermediate Similarity	NPC28054
0.8015	Intermediate Similarity	NPC178382
0.8015	Intermediate Similarity	NPC65735
0.8015	Intermediate Similarity	NPC118853
0.8015	Intermediate Similarity	NPC188377
0.8014	Intermediate Similarity	NPC263337
0.8	Intermediate Similarity	NPC234494
0.8	Intermediate Similarity	NPC470998
0.7986	Intermediate Similarity	NPC250228
0.7986	Intermediate Similarity	NPC255414
0.7986	Intermediate Similarity	NPC216755
0.7984	Intermediate Similarity	NPC277525
0.797	Intermediate Similarity	NPC95567
0.797	Intermediate Similarity	NPC319140
0.797	Intermediate Similarity	NPC476016
0.7958	Intermediate Similarity	NPC223415
0.7958	Intermediate Similarity	NPC470741
0.7956	Intermediate Similarity	NPC471998
0.7955	Intermediate Similarity	NPC75557
0.7955	Intermediate Similarity	NPC300098
0.7955	Intermediate Similarity	NPC290193
0.7955	Intermediate Similarity	NPC71274
0.7945	Intermediate Similarity	NPC196846
0.7945	Intermediate Similarity	NPC470997
0.7931	Intermediate Similarity	NPC471007
0.7931	Intermediate Similarity	NPC476941
0.7931	Intermediate Similarity	NPC476942
0.791	Intermediate Similarity	NPC474438
0.791	Intermediate Similarity	NPC474279
0.7907	Intermediate Similarity	NPC137710
0.7895	Intermediate Similarity	NPC474260
0.7895	Intermediate Similarity	NPC81912
0.7895	Intermediate Similarity	NPC329922
0.7895	Intermediate Similarity	NPC329694
0.7891	Intermediate Similarity	NPC272590
0.7891	Intermediate Similarity	NPC131801
0.7886	Intermediate Similarity	NPC471521
0.7886	Intermediate Similarity	NPC473356
0.7883	Intermediate Similarity	NPC293253
0.7877	Intermediate Similarity	NPC69647
0.7877	Intermediate Similarity	NPC125182
0.7877	Intermediate Similarity	NPC472654
0.7877	Intermediate Similarity	NPC471001
0.7874	Intermediate Similarity	NPC205523
0.7863	Intermediate Similarity	NPC471549
0.7863	Intermediate Similarity	NPC473379
0.7862	Intermediate Similarity	NPC470941
0.7862	Intermediate Similarity	NPC71821
0.7862	Intermediate Similarity	NPC10088
0.7862	Intermediate Similarity	NPC476937
0.7862	Intermediate Similarity	NPC476938
0.7857	Intermediate Similarity	NPC472376
0.7857	Intermediate Similarity	NPC471996
0.7847	Intermediate Similarity	NPC34056
0.7847	Intermediate Similarity	NPC56731
0.784	Intermediate Similarity	NPC105249
0.7838	Intermediate Similarity	NPC33938
0.7838	Intermediate Similarity	NPC246164
0.7838	Intermediate Similarity	NPC470996
0.7838	Intermediate Similarity	NPC469503
0.7836	Intermediate Similarity	NPC474830
0.7823	Intermediate Similarity	NPC177331
0.7823	Intermediate Similarity	NPC212257
0.7823	Intermediate Similarity	NPC46551
0.7823	Intermediate Similarity	NPC159927
0.7823	Intermediate Similarity	NPC469335
0.782	Intermediate Similarity	NPC474829
0.7817	Intermediate Similarity	NPC20500
0.7812	Intermediate Similarity	NPC45536
0.7808	Intermediate Similarity	NPC93666
0.7803	Intermediate Similarity	NPC476351
0.7801	Intermediate Similarity	NPC474722
0.7794	Intermediate Similarity	NPC21460
0.7793	Intermediate Similarity	NPC262198
0.7793	Intermediate Similarity	NPC276676
0.7786	Intermediate Similarity	NPC310043
0.7786	Intermediate Similarity	NPC4764
0.7785	Intermediate Similarity	NPC30222
0.7785	Intermediate Similarity	NPC178932
0.7778	Intermediate Similarity	NPC1811
0.7778	Intermediate Similarity	NPC26157
0.777	Intermediate Similarity	NPC291150
0.777	Intermediate Similarity	NPC116717
0.777	Intermediate Similarity	NPC471000
0.7755	Intermediate Similarity	NPC195325
0.7755	Intermediate Similarity	NPC470791
0.7755	Intermediate Similarity	NPC470790
0.7754	Intermediate Similarity	NPC474407
0.7754	Intermediate Similarity	NPC474426
0.7754	Intermediate Similarity	NPC474425
0.7746	Intermediate Similarity	NPC201370
0.7746	Intermediate Similarity	NPC473983
0.774	Intermediate Similarity	NPC221809
0.7733	Intermediate Similarity	NPC296807
0.7733	Intermediate Similarity	NPC281258
0.7733	Intermediate Similarity	NPC92979
0.7733	Intermediate Similarity	NPC35000
0.7733	Intermediate Similarity	NPC155939
0.7733	Intermediate Similarity	NPC141538
0.7733	Intermediate Similarity	NPC264943
0.7733	Intermediate Similarity	NPC469336
0.7727	Intermediate Similarity	NPC283284
0.7727	Intermediate Similarity	NPC289911
0.7718	Intermediate Similarity	NPC294511

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 NPC477966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1010
0.2-0.3	1655
0.3-0.4	2863
0.4-0.5	2226
0.5-0.6	946
0.6-0.7	196
0.7-0.8	6
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
0.7616	Intermediate Similarity	NPD5760	Phase 2
0.7616	Intermediate Similarity	NPD5761	Phase 2
0.7431	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1241	Discontinued
0.7153	Intermediate Similarity	NPD3972	Approved
0.7152	Intermediate Similarity	NPD6273	Approved
0.7075	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1876	Approved
0.7047	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6832	Phase 2
0.6944	Remote Similarity	NPD8032	Phase 2
0.6939	Remote Similarity	NPD2799	Discontinued
0.6928	Remote Similarity	NPD6765	Approved
0.6928	Remote Similarity	NPD6764	Approved
0.6846	Remote Similarity	NPD2344	Approved
0.6835	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2798	Approved
0.6824	Remote Similarity	NPD8434	Phase 2
0.6821	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7003	Approved
0.6763	Remote Similarity	NPD3023	Approved
0.6763	Remote Similarity	NPD3026	Approved
0.6739	Remote Similarity	NPD5585	Approved
0.6738	Remote Similarity	NPD5327	Phase 3
0.6735	Remote Similarity	NPD6355	Discontinued
0.6733	Remote Similarity	NPD2346	Discontinued
0.6692	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7157	Approved
0.669	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6784	Approved
0.6667	Remote Similarity	NPD2531	Phase 2
0.6645	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2313	Discontinued
0.6643	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2797	Approved
0.6623	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1651	Approved
0.6619	Remote Similarity	NPD3025	Approved
0.6619	Remote Similarity	NPD3024	Approved
0.6601	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4110	Phase 3
0.66	Remote Similarity	NPD3748	Approved
0.66	Remote Similarity	NPD4308	Phase 3
0.6596	Remote Similarity	NPD1281	Approved
0.6573	Remote Similarity	NPD1283	Approved
0.6571	Remote Similarity	NPD17	Approved
0.6561	Remote Similarity	NPD3873	Phase 3
0.6561	Remote Similarity	NPD3869	Phase 3
0.6556	Remote Similarity	NPD2796	Approved
0.6556	Remote Similarity	NPD1551	Phase 2
0.6554	Remote Similarity	NPD4140	Approved
0.6554	Remote Similarity	NPD3142	Approved
0.6554	Remote Similarity	NPD3140	Approved
0.6549	Remote Similarity	NPD9717	Approved
0.6549	Remote Similarity	NPD1608	Approved
0.6541	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6599	Discontinued
0.6541	Remote Similarity	NPD2182	Approved
0.6538	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3268	Approved
0.6528	Remote Similarity	NPD3266	Approved
0.6528	Remote Similarity	NPD3267	Approved
0.6522	Remote Similarity	NPD7819	Suspended
0.6519	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4359	Approved
0.65	Remote Similarity	NPD5691	Approved
0.6494	Remote Similarity	NPD8166	Discontinued
0.6494	Remote Similarity	NPD3750	Approved
0.6486	Remote Similarity	NPD4062	Phase 3
0.6485	Remote Similarity	NPD8127	Discontinued
0.6483	Remote Similarity	NPD1019	Discontinued
0.646	Remote Similarity	NPD6279	Approved
0.646	Remote Similarity	NPD6280	Approved
0.6454	Remote Similarity	NPD1778	Approved
0.6447	Remote Similarity	NPD6099	Approved
0.6447	Remote Similarity	NPD4476	Approved
0.6447	Remote Similarity	NPD4477	Approved
0.6447	Remote Similarity	NPD2935	Discontinued
0.6447	Remote Similarity	NPD6100	Approved
0.6447	Remote Similarity	NPD2438	Suspended
0.6438	Remote Similarity	NPD7028	Phase 2
0.6433	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1243	Approved
0.6429	Remote Similarity	NPD2800	Approved
0.6419	Remote Similarity	NPD3764	Approved
0.6414	Remote Similarity	NPD1203	Approved
0.641	Remote Similarity	NPD7440	Discontinued
0.6408	Remote Similarity	NPD3496	Discontinued
0.6405	Remote Similarity	NPD6002	Phase 3
0.6405	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6005	Phase 3
0.6405	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6004	Phase 3
0.6405	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5735	Approved
0.6391	Remote Similarity	NPD3134	Approved
0.6391	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.638	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3226	Approved
0.6364	Remote Similarity	NPD919	Approved
0.6358	Remote Similarity	NPD6353	Approved
0.6351	Remote Similarity	NPD7095	Approved
0.635	Remote Similarity	NPD7843	Approved
0.6346	Remote Similarity	NPD3887	Approved
0.6345	Remote Similarity	NPD8651	Approved
0.6341	Remote Similarity	NPD7768	Phase 2
0.6338	Remote Similarity	NPD2932	Approved
0.6338	Remote Similarity	NPD4626	Approved
0.6337	Remote Similarity	NPD6559	Discontinued
0.6329	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD9494	Approved
0.6325	Remote Similarity	NPD5494	Approved
0.6319	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD1894	Discontinued
0.6309	Remote Similarity	NPD411	Approved
0.6309	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD6798	Discontinued
0.6309	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7236	Approved
0.6301	Remote Similarity	NPD6362	Approved
0.6299	Remote Similarity	NPD5763	Approved
0.6299	Remote Similarity	NPD5762	Approved
0.6296	Remote Similarity	NPD6873	Phase 2
0.6296	Remote Similarity	NPD2684	Approved
0.6291	Remote Similarity	NPD4618	Approved
0.6291	Remote Similarity	NPD1933	Approved
0.6291	Remote Similarity	NPD4622	Approved
0.6287	Remote Similarity	NPD1247	Approved
0.6284	Remote Similarity	NPD2614	Approved
0.6273	Remote Similarity	NPD2649	Approved
0.6273	Remote Similarity	NPD2651	Approved
0.6267	Remote Similarity	NPD6663	Approved
0.6267	Remote Similarity	NPD4870	Approved
0.6266	Remote Similarity	NPD6799	Approved
0.6259	Remote Similarity	NPD5647	Approved
0.6259	Remote Similarity	NPD5951	Approved
0.6259	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD7577	Discontinued
0.6258	Remote Similarity	NPD1549	Phase 2
0.6258	Remote Similarity	NPD4534	Discontinued
0.625	Remote Similarity	NPD6808	Phase 2
0.625	Remote Similarity	NPD6287	Discontinued
0.625	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6653	Approved
0.6242	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7008	Discontinued
0.6241	Remote Similarity	NPD164	Approved
0.6233	Remote Similarity	NPD6696	Suspended
0.6232	Remote Similarity	NPD5535	Approved
0.6226	Remote Similarity	NPD4662	Approved
0.6226	Remote Similarity	NPD4661	Approved
0.6226	Remote Similarity	NPD2533	Approved
0.6226	Remote Similarity	NPD2532	Approved
0.6226	Remote Similarity	NPD2534	Approved
0.6225	Remote Similarity	NPD4060	Phase 1
0.6224	Remote Similarity	NPD3019	Approved
0.6222	Remote Similarity	NPD1358	Approved
0.6216	Remote Similarity	NPD5736	Approved
0.6214	Remote Similarity	NPD6387	Discontinued
0.6209	Remote Similarity	NPD5688	Approved
0.6209	Remote Similarity	NPD5689	Approved
0.6205	Remote Similarity	NPD7075	Discontinued
0.6205	Remote Similarity	NPD3749	Approved
0.62	Remote Similarity	NPD1296	Phase 2
0.6197	Remote Similarity	NPD9545	Approved
0.6196	Remote Similarity	NPD7411	Suspended
0.6196	Remote Similarity	NPD6677	Suspended
0.6194	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD2353	Approved
0.6194	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5049	Phase 3
0.6184	Remote Similarity	NPD3657	Discovery
0.6184	Remote Similarity	NPD447	Suspended
0.6183	Remote Similarity	NPD1238	Approved
0.6182	Remote Similarity	NPD2296	Approved
0.6176	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD1510	Phase 2
0.6163	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD6844	Discontinued
0.6159	Remote Similarity	NPD6233	Phase 2
0.6154	Remote Similarity	NPD2897	Discontinued
0.6154	Remote Similarity	NPD5958	Discontinued
0.6154	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7229	Phase 3
0.6154	Remote Similarity	NPD2424	Discontinued
0.6149	Remote Similarity	NPD4624	Approved
0.6149	Remote Similarity	NPD6007	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data