NPASS Compound

Structure

NPC52412 OpenBabel07101719132D 24 26 0 0 1 0 0 0 0 0999 V2000 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 -3.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8634 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8620 -1.8082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8320 -2.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2821 -3.3188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5050 -2.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -2.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2802 -3.9142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1208 -2.7742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 10 24 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 18 1 6 0 0 0 14 15 1 0 0 0 0 15 21 2 0 0 0 0 16 18 1 6 0 0 0 16 19 1 0 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 18 2 1 6 0 0 0 19 20 1 1 0 0 0 20 4 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	2.905
LogD:	3.045
LogS:	-4.038
# Rotatable Bonds:	3
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	4.424
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.813
MDCK Permeability:	2.2675878426525742e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.578

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	94.1423110961914%
Volume Distribution (VD):	0.959
Pgp-substrate:	5.861698627471924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.306
CYP2C19-inhibitor:	0.246
CYP2C19-substrate:	0.583
CYP2C9-inhibitor:	0.431
CYP2C9-substrate:	0.157
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.375
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	7.354
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.534
Skin Sensitization:	0.138
Carcinogencity:	0.223
Eye Corrosion:	0.017
Eye Irritation:	0.251
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC52412

Natural Product ID:	NPC52412
*Common Name:**	3Alpha,4Beta-Dihydroxy-15,16-Epoxy-12-Oxoclerodan-13(16),14-Diene
IUPAC Name:	2-[(1S,2R,4aR,5R,6R,8aR)-5,6-dihydroxy-1,2,4a,5-tetramethyl-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-1-(furan-3-yl)ethanone
Synonyms:
Standard InCHIKey:	IDSNFIYMRQMCAN-FAQOMCGWSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-13-7-9-19(3)16(5-6-17(22)20(19,4)23)18(13,2)11-15(21)14-8-10-24-12-14/h8,10,12-13,16-17,22-23H,5-7,9,11H2,1-4H3/t13-,16-,17-,18+,19-,20+/m1/s1
SMILES:	C[C@@H]1CC[C@]2(C)[C@H](CC[C@H]([C@]2(C)O)O)[C@@]1(C)CC(=O)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463497
PubChem CID:	14109746
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO21790	Croton insularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104505]
NPO21790	Croton insularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	200000.0	nM	PMID[481383]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	98000.0	nM	PMID[481383]

☑ 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 NPC52412 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	323
0.1-0.2	1286
0.2-0.3	2757
0.3-0.4	5986
0.4-0.5	11855
0.5-0.6	9600
0.6-0.7	9462
0.7-0.8	1190
0.8-0.85	194
0.85-0.9	39
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9353	High Similarity	NPC476946
0.9333	High Similarity	NPC476947
0.9185	High Similarity	NPC218838
0.8897	High Similarity	NPC61788
0.8849	High Similarity	NPC46896
0.8836	High Similarity	NPC470998
0.8828	High Similarity	NPC302987
0.8819	High Similarity	NPC5676
0.8811	High Similarity	NPC243577
0.8732	High Similarity	NPC67003
0.8732	High Similarity	NPC90296
0.8723	High Similarity	NPC236532
0.8714	High Similarity	NPC146872
0.8707	High Similarity	NPC234494
0.869	High Similarity	NPC185456
0.8649	High Similarity	NPC196846
0.8649	High Similarity	NPC470997
0.8643	High Similarity	NPC158525
0.8621	High Similarity	NPC476944
0.8581	High Similarity	NPC69647
0.8581	High Similarity	NPC125182
0.8562	High Similarity	NPC287559
0.8552	High Similarity	NPC103134
0.8552	High Similarity	NPC267632
0.8533	High Similarity	NPC33938
0.8533	High Similarity	NPC470996
0.8529	High Similarity	NPC23086
0.8521	High Similarity	NPC42400
0.8514	High Similarity	NPC471007
0.8506	High Similarity	NPC18986
0.85	High Similarity	NPC470740
0.8497	Intermediate Similarity	NPC140952
0.8497	Intermediate Similarity	NPC299094
0.8497	Intermediate Similarity	NPC475967
0.8497	Intermediate Similarity	NPC10051
0.8493	Intermediate Similarity	NPC251865
0.8483	Intermediate Similarity	NPC475519
0.8483	Intermediate Similarity	NPC121158
0.8462	Intermediate Similarity	NPC121995
0.8456	Intermediate Similarity	NPC472654
0.8456	Intermediate Similarity	NPC195325
0.8452	Intermediate Similarity	NPC472773
0.8446	Intermediate Similarity	NPC255414
0.8433	Intermediate Similarity	NPC79557
0.8431	Intermediate Similarity	NPC299038
0.8431	Intermediate Similarity	NPC81405
0.8421	Intermediate Similarity	NPC264943
0.8421	Intermediate Similarity	NPC92979
0.8421	Intermediate Similarity	NPC179170
0.8421	Intermediate Similarity	NPC155939
0.8421	Intermediate Similarity	NPC141538
0.8421	Intermediate Similarity	NPC296807
0.8414	Intermediate Similarity	NPC205765
0.8411	Intermediate Similarity	NPC268905
0.8411	Intermediate Similarity	NPC121615
0.8411	Intermediate Similarity	NPC75906
0.8411	Intermediate Similarity	NPC294511
0.8403	Intermediate Similarity	NPC202260
0.84	Intermediate Similarity	NPC228842
0.8397	Intermediate Similarity	NPC276551
0.8397	Intermediate Similarity	NPC56358
0.8394	Intermediate Similarity	NPC138139
0.8394	Intermediate Similarity	NPC46536
0.8387	Intermediate Similarity	NPC263432
0.8387	Intermediate Similarity	NPC200782
0.8387	Intermediate Similarity	NPC472771
0.8378	Intermediate Similarity	NPC233763
0.8378	Intermediate Similarity	NPC346
0.8357	Intermediate Similarity	NPC89133
0.8356	Intermediate Similarity	NPC473152
0.8356	Intermediate Similarity	NPC263337
0.8355	Intermediate Similarity	NPC178932
0.8345	Intermediate Similarity	NPC18904
0.8344	Intermediate Similarity	NPC470875
0.8333	Intermediate Similarity	NPC477405
0.8333	Intermediate Similarity	NPC469338
0.8333	Intermediate Similarity	NPC476943
0.8333	Intermediate Similarity	NPC471996
0.8333	Intermediate Similarity	NPC292389
0.8333	Intermediate Similarity	NPC283209
0.8322	Intermediate Similarity	NPC216755
0.8322	Intermediate Similarity	NPC471174
0.8321	Intermediate Similarity	NPC290193
0.8312	Intermediate Similarity	NPC194499
0.8312	Intermediate Similarity	NPC472772
0.8301	Intermediate Similarity	NPC281258
0.8301	Intermediate Similarity	NPC469336
0.8301	Intermediate Similarity	NPC35000
0.8301	Intermediate Similarity	NPC44675
0.8301	Intermediate Similarity	NPC214541
0.8301	Intermediate Similarity	NPC88958
0.8291	Intermediate Similarity	NPC472774
0.8291	Intermediate Similarity	NPC472775
0.8291	Intermediate Similarity	NPC270312
0.8289	Intermediate Similarity	NPC469503
0.8289	Intermediate Similarity	NPC145830
0.828	Intermediate Similarity	NPC470940
0.828	Intermediate Similarity	NPC469849
0.8276	Intermediate Similarity	NPC90953
0.8273	Intermediate Similarity	NPC207294
0.8273	Intermediate Similarity	NPC112706
0.8273	Intermediate Similarity	NPC279877
0.8273	Intermediate Similarity	NPC477040
0.8269	Intermediate Similarity	NPC188649
0.8269	Intermediate Similarity	NPC329938
0.8269	Intermediate Similarity	NPC5079
0.8269	Intermediate Similarity	NPC68848
0.8269	Intermediate Similarity	NPC82851
0.8269	Intermediate Similarity	NPC69028
0.8264	Intermediate Similarity	NPC470742
0.8264	Intermediate Similarity	NPC307401
0.8258	Intermediate Similarity	NPC475226
0.8258	Intermediate Similarity	NPC307383
0.8255	Intermediate Similarity	NPC470999
0.825	Intermediate Similarity	NPC294512
0.8243	Intermediate Similarity	NPC238843
0.8243	Intermediate Similarity	NPC199044
0.8239	Intermediate Similarity	NPC471397
0.8235	Intermediate Similarity	NPC302054
0.8235	Intermediate Similarity	NPC253201
0.8235	Intermediate Similarity	NPC237259
0.8235	Intermediate Similarity	NPC98206
0.8235	Intermediate Similarity	NPC477967
0.8235	Intermediate Similarity	NPC57998
0.8235	Intermediate Similarity	NPC34421
0.8235	Intermediate Similarity	NPC30222
0.8235	Intermediate Similarity	NPC282445
0.8227	Intermediate Similarity	NPC298190
0.8224	Intermediate Similarity	NPC272590
0.8224	Intermediate Similarity	NPC18135
0.8219	Intermediate Similarity	NPC56197
0.8217	Intermediate Similarity	NPC285567
0.8217	Intermediate Similarity	NPC234660
0.8217	Intermediate Similarity	NPC51568
0.8217	Intermediate Similarity	NPC88841
0.8217	Intermediate Similarity	NPC288602
0.8214	Intermediate Similarity	NPC59502
0.8212	Intermediate Similarity	NPC211625
0.8205	Intermediate Similarity	NPC472653
0.8205	Intermediate Similarity	NPC470789
0.8205	Intermediate Similarity	NPC335761
0.8205	Intermediate Similarity	NPC477402
0.8201	Intermediate Similarity	NPC83178
0.8201	Intermediate Similarity	NPC290955
0.82	Intermediate Similarity	NPC221809
0.8194	Intermediate Similarity	NPC45101
0.8194	Intermediate Similarity	NPC472778
0.8194	Intermediate Similarity	NPC261597
0.8194	Intermediate Similarity	NPC470118
0.8194	Intermediate Similarity	NPC472776
0.8194	Intermediate Similarity	NPC197137
0.8194	Intermediate Similarity	NPC304692
0.8194	Intermediate Similarity	NPC88007
0.8194	Intermediate Similarity	NPC249021
0.8194	Intermediate Similarity	NPC472777
0.8194	Intermediate Similarity	NPC7059
0.8188	Intermediate Similarity	NPC300098
0.8188	Intermediate Similarity	NPC179354
0.8187	Intermediate Similarity	NPC470995
0.8176	Intermediate Similarity	NPC472282
0.8176	Intermediate Similarity	NPC173516
0.8176	Intermediate Similarity	NPC472651
0.8175	Intermediate Similarity	NPC16922
0.8175	Intermediate Similarity	NPC272899
0.817	Intermediate Similarity	NPC471613
0.817	Intermediate Similarity	NPC476201
0.817	Intermediate Similarity	NPC472672
0.8169	Intermediate Similarity	NPC471995
0.8169	Intermediate Similarity	NPC473982
0.8165	Intermediate Similarity	NPC476858
0.8165	Intermediate Similarity	NPC476856
0.8165	Intermediate Similarity	NPC470182
0.8165	Intermediate Similarity	NPC271657
0.8165	Intermediate Similarity	NPC476857
0.8158	Intermediate Similarity	NPC196864
0.8158	Intermediate Similarity	NPC212257
0.8158	Intermediate Similarity	NPC156189
0.8158	Intermediate Similarity	NPC477404
0.8156	Intermediate Similarity	NPC476925
0.8153	Intermediate Similarity	NPC149896
0.8153	Intermediate Similarity	NPC18347
0.8153	Intermediate Similarity	NPC79571
0.8153	Intermediate Similarity	NPC207978
0.8151	Intermediate Similarity	NPC474722
0.8146	Intermediate Similarity	NPC93666
0.8143	Intermediate Similarity	NPC476917
0.8143	Intermediate Similarity	NPC327527
0.8143	Intermediate Similarity	NPC477966
0.8143	Intermediate Similarity	NPC477123
0.8143	Intermediate Similarity	NPC26532
0.8143	Intermediate Similarity	NPC329707
0.8141	Intermediate Similarity	NPC84349
0.8141	Intermediate Similarity	NPC474611
0.8138	Intermediate Similarity	NPC473268
0.8138	Intermediate Similarity	NPC310830
0.8138	Intermediate Similarity	NPC4764
0.8133	Intermediate Similarity	NPC471292
0.8133	Intermediate Similarity	NPC262198
0.8129	Intermediate Similarity	NPC104736
0.8129	Intermediate Similarity	NPC41880

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 NPC52412 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	921
0.2-0.3	1868
0.3-0.4	2675
0.4-0.5	2054
0.5-0.6	1022
0.6-0.7	297
0.7-0.8	16
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8301	Intermediate Similarity	NPD5760	Phase 2
0.8301	Intermediate Similarity	NPD5761	Phase 2
0.7857	Intermediate Similarity	NPD8434	Phase 2
0.7785	Intermediate Similarity	NPD1471	Phase 3
0.7667	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2344	Approved
0.7533	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD4628	Phase 3
0.7389	Intermediate Similarity	NPD6273	Approved
0.7353	Intermediate Similarity	NPD6765	Approved
0.7353	Intermediate Similarity	NPD6764	Approved
0.732	Intermediate Similarity	NPD2346	Discontinued
0.7317	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6559	Discontinued
0.7184	Intermediate Similarity	NPD6784	Approved
0.7184	Intermediate Similarity	NPD6785	Approved
0.7133	Intermediate Similarity	NPD2313	Discontinued
0.7103	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7095	Intermediate Similarity	NPD2798	Approved
0.7091	Intermediate Similarity	NPD3882	Suspended
0.7075	Intermediate Similarity	NPD1876	Approved
0.7073	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5494	Approved
0.7055	Intermediate Similarity	NPD3972	Approved
0.7037	Intermediate Similarity	NPD3226	Approved
0.7012	Intermediate Similarity	NPD6280	Approved
0.7012	Intermediate Similarity	NPD6279	Approved
0.6993	Remote Similarity	NPD6355	Discontinued
0.697	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7819	Suspended
0.6962	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4110	Phase 3
0.6941	Remote Similarity	NPD3926	Phase 2
0.6933	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2296	Approved
0.6923	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD2935	Discontinued
0.6923	Remote Similarity	NPD2796	Approved
0.6919	Remote Similarity	NPD3818	Discontinued
0.6919	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD920	Approved
0.6909	Remote Similarity	NPD1934	Approved
0.6899	Remote Similarity	NPD2800	Approved
0.6894	Remote Similarity	NPD4661	Approved
0.6894	Remote Similarity	NPD4662	Approved
0.689	Remote Similarity	NPD4380	Phase 2
0.6887	Remote Similarity	NPD6832	Phase 2
0.6882	Remote Similarity	NPD6808	Phase 2
0.6867	Remote Similarity	NPD5647	Approved
0.6855	Remote Similarity	NPD7003	Approved
0.6845	Remote Similarity	NPD7075	Discontinued
0.6845	Remote Similarity	NPD3749	Approved
0.6835	Remote Similarity	NPD2424	Discontinued
0.6835	Remote Similarity	NPD1549	Phase 2
0.6832	Remote Similarity	NPD6799	Approved
0.6829	Remote Similarity	NPD2651	Approved
0.6829	Remote Similarity	NPD7458	Discontinued
0.6829	Remote Similarity	NPD2649	Approved
0.6826	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1247	Approved
0.6818	Remote Similarity	NPD4140	Approved
0.6815	Remote Similarity	NPD1551	Phase 2
0.6807	Remote Similarity	NPD6801	Discontinued
0.6807	Remote Similarity	NPD6844	Discontinued
0.6805	Remote Similarity	NPD919	Approved
0.6804	Remote Similarity	NPD8404	Phase 2
0.6792	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.679	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7028	Phase 2
0.678	Remote Similarity	NPD8312	Approved
0.678	Remote Similarity	NPD8313	Approved
0.6774	Remote Similarity	NPD447	Suspended
0.6774	Remote Similarity	NPD5735	Approved
0.6772	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.677	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2801	Approved
0.6753	Remote Similarity	NPD8032	Phase 2
0.675	Remote Similarity	NPD8166	Discontinued
0.6746	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5402	Approved
0.6713	Remote Similarity	NPD1241	Discontinued
0.6711	Remote Similarity	NPD9717	Approved
0.6711	Remote Similarity	NPD9494	Approved
0.6707	Remote Similarity	NPD5403	Approved
0.6705	Remote Similarity	NPD6166	Phase 2
0.6705	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1470	Approved
0.6689	Remote Similarity	NPD1203	Approved
0.6688	Remote Similarity	NPD6798	Discontinued
0.6687	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5401	Approved
0.6687	Remote Similarity	NPD2534	Approved
0.6687	Remote Similarity	NPD2532	Approved
0.6687	Remote Similarity	NPD2533	Approved
0.6687	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD5763	Approved
0.6647	Remote Similarity	NPD7411	Suspended
0.6646	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4308	Phase 3
0.6646	Remote Similarity	NPD1510	Phase 2
0.6646	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6959	Discontinued
0.6627	Remote Similarity	NPD3817	Phase 2
0.6626	Remote Similarity	NPD1511	Approved
0.6624	Remote Similarity	NPD1607	Approved
0.6623	Remote Similarity	NPD7095	Approved
0.6623	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1283	Approved
0.6621	Remote Similarity	NPD7157	Approved
0.6612	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6100	Approved
0.6604	Remote Similarity	NPD6099	Approved
0.6603	Remote Similarity	NPD4060	Phase 1
0.6603	Remote Similarity	NPD1240	Approved
0.6591	Remote Similarity	NPD5844	Phase 1
0.659	Remote Similarity	NPD6232	Discontinued
0.6588	Remote Similarity	NPD7768	Phase 2
0.6585	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1243	Approved
0.6582	Remote Similarity	NPD7097	Phase 1
0.6581	Remote Similarity	NPD411	Approved
0.6581	Remote Similarity	NPD3268	Approved
0.6581	Remote Similarity	NPD3764	Approved
0.6579	Remote Similarity	NPD2797	Approved
0.6561	Remote Similarity	NPD1933	Approved
0.6556	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5327	Phase 3
0.6554	Remote Similarity	NPD1651	Approved
0.6554	Remote Similarity	NPD7074	Phase 3
0.6545	Remote Similarity	NPD5049	Phase 3
0.6545	Remote Similarity	NPD1512	Approved
0.6543	Remote Similarity	NPD3750	Approved
0.6541	Remote Similarity	NPD7033	Discontinued
0.6534	Remote Similarity	NPD3751	Discontinued
0.6522	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4534	Discontinued
0.6519	Remote Similarity	NPD6353	Approved
0.6519	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD37	Approved
0.6503	Remote Similarity	NPD3887	Approved
0.6503	Remote Similarity	NPD2354	Approved
0.6503	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4477	Approved
0.65	Remote Similarity	NPD4476	Approved
0.65	Remote Similarity	NPD2438	Suspended
0.6497	Remote Similarity	NPD7054	Approved
0.6497	Remote Similarity	NPD2979	Phase 3
0.6497	Remote Similarity	NPD3620	Phase 2
0.6497	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4307	Phase 2
0.6497	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4965	Approved
0.6491	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4967	Phase 2
0.6491	Remote Similarity	NPD4966	Approved
0.649	Remote Similarity	NPD1608	Approved
0.6474	Remote Similarity	NPD3057	Approved
0.6467	Remote Similarity	NPD7239	Suspended
0.6463	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7472	Approved
0.646	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6004	Phase 3
0.646	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6005	Phase 3
0.646	Remote Similarity	NPD6002	Phase 3
0.6444	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5585	Approved
0.6438	Remote Similarity	NPD3748	Approved
0.6433	Remote Similarity	NPD6233	Phase 2
0.6433	Remote Similarity	NPD4062	Phase 3
0.6429	Remote Similarity	NPD1019	Discontinued
0.6425	Remote Similarity	NPD6797	Phase 2
0.6424	Remote Similarity	NPD1201	Approved
0.6424	Remote Similarity	NPD1281	Approved
0.642	Remote Similarity	NPD5958	Discontinued
0.642	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5536	Phase 2
0.6416	Remote Similarity	NPD6234	Discontinued
0.6415	Remote Similarity	NPD6653	Approved
0.6415	Remote Similarity	NPD6651	Approved
0.64	Remote Similarity	NPD1778	Approved
0.64	Remote Similarity	NPD3787	Discontinued
0.64	Remote Similarity	NPD2932	Approved
0.64	Remote Similarity	NPD3019	Approved
0.6398	Remote Similarity	NPD5712	Approved
0.6393	Remote Similarity	NPD8150	Discontinued
0.6389	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4141	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