NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	3.684
LogD:	3.781
LogS:	-4.43
# Rotatable Bonds:	3
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.878
Synthetic Accessibility Score:	4.38
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.726
MDCK Permeability:	4.036931932205334e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.072
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	97.98970794677734%
Volume Distribution (VD):	1.26
Pgp-substrate:	3.2184131145477295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.161
CYP1A2-substrate:	0.354
CYP2C19-inhibitor:	0.316
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.443
CYP2C9-substrate:	0.231
CYP2D6-inhibitor:	0.216
CYP2D6-substrate:	0.58
CYP3A4-inhibitor:	0.356
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	8.574
Half-life (T1/2):	0.413

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.596
Skin Sensitization:	0.274
Carcinogencity:	0.103
Eye Corrosion:	0.106
Eye Irritation:	0.763
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC476947

Natural Product ID:	NPC476947
*Common Name:**	(1R,2R,4aR,5S,6R,8aR)-5-[2-(furan-3-yl)ethyl]-1,5,6,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2-diol
IUPAC Name:	(1R,2R,4aR,5S,6R,8aR)-5-[2-(furan-3-yl)ethyl]-1,5,6,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2-diol
Synonyms:
Standard InCHIKey:	GNWZEPMTZKFXQV-IOFZNDEASA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-14-7-11-19(3)16(5-6-17(21)20(19,4)22)18(14,2)10-8-15-9-12-23-13-15/h9,12-14,16-17,21-22H,5-8,10-11H2,1-4H3/t14-,16-,17-,18+,19-,20+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC3=COC=C3)CC[C@H]([C@]2(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90676768
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
NPO33579	Croton laui	Species	Euphorbiaceae	Eukaryota	Twigs	Hainan Province, China	n.a.	PMID[24735527]

☑ 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
MIC	11

Activity Type	# Activity
Cell Line	2
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>=	10000	nM	PMID[24735527]
NPT168	Cell Line	P388	Mus musculus	IC50	>=	10000	nM	PMID[24735527]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	150000	nM	PMID[24735527]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	>	150000	nM	PMID[24735527]
NPT2	Others	Unspecified		MIC	>	150000	nM	PMID[24735527]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	150000	nM	PMID[24735527]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	150000	nM	PMID[24735527]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	150000	nM	PMID[24735527]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	150000	nM	PMID[24735527]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	150000	nM	PMID[24735527]
NPT1533	Organism	Saccharomyces	Saccharomyces	MIC	>	150000	nM	PMID[24735527]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	150000	nM	PMID[24735527]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	150000	nM	PMID[24735527]

☑ 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 NPC476947 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	279
0.1-0.2	1191
0.2-0.3	2613
0.3-0.4	5527
0.4-0.5	11216
0.5-0.6	10322
0.6-0.7	10243
0.7-0.8	1050
0.8-0.85	174
0.85-0.9	69
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC218838
0.9407	High Similarity	NPC476946
0.938	High Similarity	NPC61788
0.9333	High Similarity	NPC52412
0.927	High Similarity	NPC5676
0.9185	High Similarity	NPC67003
0.9007	High Similarity	NPC470998
0.9007	High Similarity	NPC69647
0.9007	High Similarity	NPC125182
0.9	High Similarity	NPC302987
0.8992	High Similarity	NPC23086
0.8936	High Similarity	NPC471007
0.8913	High Similarity	NPC121158
0.8889	High Similarity	NPC46896
0.8873	High Similarity	NPC234494
0.8865	High Similarity	NPC255414
0.8849	High Similarity	NPC243577
0.8846	High Similarity	NPC138139
0.8846	High Similarity	NPC46536
0.8828	High Similarity	NPC477967
0.8811	High Similarity	NPC196846
0.8811	High Similarity	NPC470997
0.8797	High Similarity	NPC89133
0.8769	High Similarity	NPC290193
0.8723	High Similarity	NPC185456
0.8712	High Similarity	NPC207294
0.8712	High Similarity	NPC477040
0.8712	High Similarity	NPC112706
0.8696	High Similarity	NPC202260
0.869	High Similarity	NPC294511
0.869	High Similarity	NPC33938
0.869	High Similarity	NPC470996
0.869	High Similarity	NPC121615
0.8676	High Similarity	NPC158525
0.8652	High Similarity	NPC251865
0.8643	High Similarity	NPC263337
0.8636	High Similarity	NPC83178
0.8633	High Similarity	NPC90296
0.863	High Similarity	NPC34421
0.863	High Similarity	NPC302054
0.863	High Similarity	NPC253201
0.863	High Similarity	NPC237259
0.863	High Similarity	NPC98206
0.8626	High Similarity	NPC303010
0.8626	High Similarity	NPC300098
0.8615	High Similarity	NPC272899
0.8615	High Similarity	NPC16922
0.8601	High Similarity	NPC471174
0.8601	High Similarity	NPC216755
0.8593	High Similarity	NPC473982
0.8582	High Similarity	NPC476925
0.8581	High Similarity	NPC194499
0.8571	High Similarity	NPC155939
0.8571	High Similarity	NPC327527
0.8571	High Similarity	NPC476917
0.8571	High Similarity	NPC477123
0.8571	High Similarity	NPC296807
0.8571	High Similarity	NPC92979
0.8571	High Similarity	NPC205765
0.8571	High Similarity	NPC477966
0.8571	High Similarity	NPC141538
0.8562	High Similarity	NPC472672
0.8562	High Similarity	NPC268905
0.8552	High Similarity	NPC228842
0.8551	High Similarity	NPC307401
0.8551	High Similarity	NPC4764
0.8521	High Similarity	NPC476944
0.8519	High Similarity	NPC298190
0.8507	High Similarity	NPC198904
0.8507	High Similarity	NPC59502
0.85	High Similarity	NPC56197
0.8496	Intermediate Similarity	NPC290955
0.8485	Intermediate Similarity	NPC179354
0.8483	Intermediate Similarity	NPC472654
0.8456	Intermediate Similarity	NPC88007
0.8456	Intermediate Similarity	NPC7059
0.8433	Intermediate Similarity	NPC279877
0.8433	Intermediate Similarity	NPC477039
0.8433	Intermediate Similarity	NPC329707
0.8429	Intermediate Similarity	NPC90953
0.8425	Intermediate Similarity	NPC212257
0.8425	Intermediate Similarity	NPC150895
0.8421	Intermediate Similarity	NPC74612
0.8411	Intermediate Similarity	NPC200782
0.8411	Intermediate Similarity	NPC79571
0.8409	Intermediate Similarity	NPC130275
0.8403	Intermediate Similarity	NPC470999
0.84	Intermediate Similarity	NPC475967
0.84	Intermediate Similarity	NPC472671
0.8397	Intermediate Similarity	NPC471549
0.8397	Intermediate Similarity	NPC473379
0.838	Intermediate Similarity	NPC475519
0.8372	Intermediate Similarity	NPC243704
0.837	Intermediate Similarity	NPC120836
0.837	Intermediate Similarity	NPC223063
0.8358	Intermediate Similarity	NPC476016
0.8358	Intermediate Similarity	NPC246392
0.8357	Intermediate Similarity	NPC471996
0.8356	Intermediate Similarity	NPC195325
0.8355	Intermediate Similarity	NPC472773
0.8345	Intermediate Similarity	NPC71821
0.8344	Intermediate Similarity	NPC8389
0.8344	Intermediate Similarity	NPC470789
0.8333	Intermediate Similarity	NPC197137
0.8333	Intermediate Similarity	NPC214495
0.8333	Intermediate Similarity	NPC299038
0.8333	Intermediate Similarity	NPC475066
0.8333	Intermediate Similarity	NPC470119
0.8333	Intermediate Similarity	NPC195954
0.8322	Intermediate Similarity	NPC264943
0.8311	Intermediate Similarity	NPC469503
0.8301	Intermediate Similarity	NPC276551
0.8296	Intermediate Similarity	NPC26532
0.8295	Intermediate Similarity	NPC212918
0.8289	Intermediate Similarity	NPC18986
0.8289	Intermediate Similarity	NPC470792
0.8289	Intermediate Similarity	NPC68848
0.8289	Intermediate Similarity	NPC472771
0.8288	Intermediate Similarity	NPC93666
0.8278	Intermediate Similarity	NPC475226
0.8278	Intermediate Similarity	NPC84349
0.8276	Intermediate Similarity	NPC346
0.8271	Intermediate Similarity	NPC178382
0.8271	Intermediate Similarity	NPC477038
0.8271	Intermediate Similarity	NPC477965
0.8264	Intermediate Similarity	NPC199044
0.8264	Intermediate Similarity	NPC238843
0.8258	Intermediate Similarity	NPC317217
0.8258	Intermediate Similarity	NPC36255
0.8255	Intermediate Similarity	NPC282445
0.8255	Intermediate Similarity	NPC178932
0.8252	Intermediate Similarity	NPC62103
0.8252	Intermediate Similarity	NPC20578
0.8247	Intermediate Similarity	NPC470875
0.8243	Intermediate Similarity	NPC272590
0.8243	Intermediate Similarity	NPC18135
0.8235	Intermediate Similarity	NPC477405
0.8235	Intermediate Similarity	NPC469338
0.8235	Intermediate Similarity	NPC292389
0.8235	Intermediate Similarity	NPC283209
0.8231	Intermediate Similarity	NPC471001
0.8224	Intermediate Similarity	NPC472653
0.8224	Intermediate Similarity	NPC287559
0.8224	Intermediate Similarity	NPC335761
0.8222	Intermediate Similarity	NPC474830
0.8212	Intermediate Similarity	NPC472778
0.8212	Intermediate Similarity	NPC472777
0.8212	Intermediate Similarity	NPC45101
0.8212	Intermediate Similarity	NPC472776
0.8212	Intermediate Similarity	NPC470118
0.8212	Intermediate Similarity	NPC472772
0.8209	Intermediate Similarity	NPC474829
0.82	Intermediate Similarity	NPC214541
0.82	Intermediate Similarity	NPC44675
0.82	Intermediate Similarity	NPC35000
0.82	Intermediate Similarity	NPC469336
0.8194	Intermediate Similarity	NPC472774
0.8194	Intermediate Similarity	NPC472775
0.8194	Intermediate Similarity	NPC472651
0.8194	Intermediate Similarity	NPC267632
0.8194	Intermediate Similarity	NPC103134
0.8188	Intermediate Similarity	NPC75906
0.8188	Intermediate Similarity	NPC471995
0.8188	Intermediate Similarity	NPC246164
0.8188	Intermediate Similarity	NPC476201
0.8182	Intermediate Similarity	NPC469849
0.8182	Intermediate Similarity	NPC470182
0.8182	Intermediate Similarity	NPC470940
0.817	Intermediate Similarity	NPC69028
0.817	Intermediate Similarity	NPC263432
0.817	Intermediate Similarity	NPC188649
0.817	Intermediate Similarity	NPC82851
0.817	Intermediate Similarity	NPC5079
0.817	Intermediate Similarity	NPC329938
0.8162	Intermediate Similarity	NPC474279
0.8162	Intermediate Similarity	NPC474438
0.8158	Intermediate Similarity	NPC472823
0.8158	Intermediate Similarity	NPC307383
0.8156	Intermediate Similarity	NPC170604
0.8156	Intermediate Similarity	NPC215109
0.8156	Intermediate Similarity	NPC470742
0.8154	Intermediate Similarity	NPC144745
0.8154	Intermediate Similarity	NPC208906
0.8151	Intermediate Similarity	NPC471292
0.8148	Intermediate Similarity	NPC329694
0.8148	Intermediate Similarity	NPC81912
0.8148	Intermediate Similarity	NPC474260
0.8148	Intermediate Similarity	NPC329922
0.8146	Intermediate Similarity	NPC41880
0.8141	Intermediate Similarity	NPC471397
0.8141	Intermediate Similarity	NPC271235
0.8141	Intermediate Similarity	NPC472652
0.8134	Intermediate Similarity	NPC83115
0.8134	Intermediate Similarity	NPC118853
0.8134	Intermediate Similarity	NPC243269
0.8133	Intermediate Similarity	NPC57998
0.8133	Intermediate Similarity	NPC30222
0.8129	Intermediate Similarity	NPC97574
0.8129	Intermediate Similarity	NPC472670
0.8129	Intermediate Similarity	NPC472141

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 NPC476947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	883
0.2-0.3	1742
0.3-0.4	2655
0.4-0.5	2053
0.5-0.6	1194
0.6-0.7	342
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
0.8322	Intermediate Similarity	NPD5760	Phase 2
0.8322	Intermediate Similarity	NPD5761	Phase 2
0.7733	Intermediate Similarity	NPD6273	Approved
0.7671	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD8434	Phase 2
0.7635	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD6765	Approved
0.7455	Intermediate Similarity	NPD6764	Approved
0.7329	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD6785	Approved
0.7278	Intermediate Similarity	NPD6784	Approved
0.7222	Intermediate Similarity	NPD8127	Discontinued
0.7211	Intermediate Similarity	NPD5735	Approved
0.72	Intermediate Similarity	NPD2344	Approved
0.72	Intermediate Similarity	NPD1471	Phase 3
0.7181	Intermediate Similarity	NPD2799	Discontinued
0.7171	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4110	Phase 3
0.7171	Intermediate Similarity	NPD7003	Approved
0.7163	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD4140	Approved
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD8032	Phase 2
0.7063	Intermediate Similarity	NPD1876	Approved
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.7025	Intermediate Similarity	NPD7458	Discontinued
0.7013	Intermediate Similarity	NPD2309	Approved
0.6993	Remote Similarity	NPD5327	Phase 3
0.6974	Remote Similarity	NPD5762	Approved
0.6974	Remote Similarity	NPD2346	Discontinued
0.6974	Remote Similarity	NPD5763	Approved
0.6972	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2798	Approved
0.6957	Remote Similarity	NPD7157	Approved
0.6948	Remote Similarity	NPD8166	Discontinued
0.6948	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1283	Approved
0.6939	Remote Similarity	NPD7095	Approved
0.6934	Remote Similarity	NPD1241	Discontinued
0.6933	Remote Similarity	NPD6353	Approved
0.6918	Remote Similarity	NPD2651	Approved
0.6918	Remote Similarity	NPD9494	Approved
0.6918	Remote Similarity	NPD2649	Approved
0.6908	Remote Similarity	NPD6099	Approved
0.6908	Remote Similarity	NPD6100	Approved
0.6897	Remote Similarity	NPD2797	Approved
0.6892	Remote Similarity	NPD6798	Discontinued
0.6883	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7028	Phase 2
0.6875	Remote Similarity	NPD6599	Discontinued
0.6871	Remote Similarity	NPD6832	Phase 2
0.6859	Remote Similarity	NPD7236	Approved
0.6852	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7819	Suspended
0.6852	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4308	Phase 3
0.6831	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4534	Discontinued
0.6818	Remote Similarity	NPD2424	Discontinued
0.6806	Remote Similarity	NPD1608	Approved
0.68	Remote Similarity	NPD4060	Phase 1
0.68	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3620	Phase 2
0.6797	Remote Similarity	NPD4476	Approved
0.6797	Remote Similarity	NPD2935	Discontinued
0.6797	Remote Similarity	NPD4477	Approved
0.6797	Remote Similarity	NPD2796	Approved
0.6788	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2313	Discontinued
0.6772	Remote Similarity	NPD4661	Approved
0.6772	Remote Similarity	NPD4662	Approved
0.6768	Remote Similarity	NPD3882	Suspended
0.6765	Remote Similarity	NPD5844	Phase 1
0.6761	Remote Similarity	NPD5585	Approved
0.6761	Remote Similarity	NPD1651	Approved
0.6747	Remote Similarity	NPD5494	Approved
0.6736	Remote Similarity	NPD1281	Approved
0.6733	Remote Similarity	NPD6663	Approved
0.6727	Remote Similarity	NPD7075	Discontinued
0.6713	Remote Similarity	NPD1778	Approved
0.6711	Remote Similarity	NPD6653	Approved
0.671	Remote Similarity	NPD5958	Discontinued
0.6707	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2684	Approved
0.6689	Remote Similarity	NPD5736	Approved
0.6689	Remote Similarity	NPD4307	Phase 2
0.6689	Remote Similarity	NPD2979	Phase 3
0.6688	Remote Similarity	NPD2438	Suspended
0.6688	Remote Similarity	NPD1551	Phase 2
0.6687	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD4380	Phase 2
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7239	Suspended
0.6646	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6002	Phase 3
0.6645	Remote Similarity	NPD6005	Phase 3
0.6645	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6004	Phase 3
0.6645	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5691	Approved
0.6643	Remote Similarity	NPD2629	Approved
0.663	Remote Similarity	NPD3057	Approved
0.6626	Remote Similarity	NPD6677	Suspended
0.6625	Remote Similarity	NPD5049	Phase 3
0.6624	Remote Similarity	NPD3750	Approved
0.6623	Remote Similarity	NPD4062	Phase 3
0.6623	Remote Similarity	NPD6233	Phase 2
0.6622	Remote Similarity	NPD5647	Approved
0.6622	Remote Similarity	NPD4624	Approved
0.6619	Remote Similarity	NPD7843	Approved
0.6615	Remote Similarity	NPD8404	Phase 2
0.6608	Remote Similarity	NPD3818	Discontinued
0.6605	Remote Similarity	NPD3226	Approved
0.6604	Remote Similarity	NPD6799	Approved
0.6603	Remote Similarity	NPD1549	Phase 2
0.6599	Remote Similarity	NPD8651	Approved
0.6599	Remote Similarity	NPD6696	Suspended
0.6597	Remote Similarity	NPD17	Approved
0.6597	Remote Similarity	NPD4626	Approved
0.6597	Remote Similarity	NPD2932	Approved
0.6597	Remote Similarity	NPD3019	Approved
0.6594	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD919	Approved
0.6585	Remote Similarity	NPD6279	Approved
0.6585	Remote Similarity	NPD6280	Approved
0.6585	Remote Similarity	NPD6801	Discontinued
0.6585	Remote Similarity	NPD6844	Discontinued
0.6585	Remote Similarity	NPD37	Approved
0.6585	Remote Similarity	NPD7577	Discontinued
0.6584	Remote Similarity	NPD920	Approved
0.6582	Remote Similarity	NPD2354	Approved
0.6582	Remote Similarity	NPD3887	Approved
0.6575	Remote Similarity	NPD9717	Approved
0.6573	Remote Similarity	NPD1894	Discontinued
0.6571	Remote Similarity	NPD8312	Approved
0.6571	Remote Similarity	NPD8313	Approved
0.6566	Remote Similarity	NPD7768	Phase 2
0.6566	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4967	Phase 2
0.6566	Remote Similarity	NPD4965	Approved
0.6566	Remote Similarity	NPD4966	Approved
0.6562	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1203	Approved
0.6552	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3533	Approved
0.6541	Remote Similarity	NPD2972	Approved
0.6541	Remote Similarity	NPD2491	Approved
0.6538	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD447	Suspended
0.6536	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4359	Approved
0.6531	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3749	Approved
0.6527	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6873	Phase 2
0.6516	Remote Similarity	NPD3748	Approved
0.6516	Remote Similarity	NPD7033	Discontinued
0.6512	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7199	Phase 2
0.6509	Remote Similarity	NPD1247	Approved
0.6506	Remote Similarity	NPD2296	Approved
0.65	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD290	Approved
0.6494	Remote Similarity	NPD1607	Approved
0.6491	Remote Similarity	NPD6166	Phase 2
0.6491	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7008	Discontinued
0.6488	Remote Similarity	NPD6234	Discontinued
0.6481	Remote Similarity	NPD3873	Phase 3
0.6481	Remote Similarity	NPD5403	Approved
0.6481	Remote Similarity	NPD3869	Phase 3
0.6479	Remote Similarity	NPD6671	Approved
0.6475	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2531	Phase 2
0.6471	Remote Similarity	NPD3140	Approved
0.6471	Remote Similarity	NPD3142	Approved
0.6471	Remote Similarity	NPD1240	Approved
0.6467	Remote Similarity	NPD2861	Phase 2
0.646	Remote Similarity	NPD2533	Approved
0.646	Remote Similarity	NPD5401	Approved
0.646	Remote Similarity	NPD2532	Approved
0.646	Remote Similarity	NPD2534	Approved
0.646	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2800	Approved
0.6456	Remote Similarity	NPD1243	Approved
0.6452	Remote Similarity	NPD3448	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