NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	528.27
Volume:	556.917
LogP:	5.87
LogD:	1.602
LogS:	-2.842
# Rotatable Bonds:	13
TPSA:	135.04
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	4.323
Fsp3:	0.567
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	2.016901271417737e-05
Pgp-inhibitor:	0.862
Pgp-substrate:	0.97
Human Intestinal Absorption (HIA):	0.261
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	96.3973159790039%
Volume Distribution (VD):	0.94
Pgp-substrate:	1.2244590520858765%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.552
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.811
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.149
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.89
CYP3A4-substrate:	0.757

ADMET: Excretion

Clearance (CL):	13.79
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.035
Carcinogencity:	0.232
Eye Corrosion:	0.006
Eye Irritation:	0.147
Respiratory Toxicity:	0.822

Download Data

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

Natural Product: NPC477056

Natural Product ID:	NPC477056
*Common Name:**	Elaphopilosin B
IUPAC Name:	2-butanoyl-4-[(3-hexanoyl-2,4-dihydroxy-6-methoxyphenyl)methyl]-3,5-dihydroxy-6-methyl-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
Synonyms:	elaphopilosin-B
Standard InCHIKey:	WYDQBJZUCLUTRC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H40O8/c1-7-9-10-12-21(32)24-22(33)16-23(38-6)18(26(24)34)15-19-27(35)25(20(31)11-8-2)29(37)30(5,28(19)36)14-13-17(3)4/h13,16,33-36H,7-12,14-15H2,1-6H3
SMILES:	CCCCCC(=O)C1=C(C(=C(C=C1O)OC)CC2=C(C(C(=O)C(=C2O)C(=O)CCC)(C)CC=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	42638635
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	La Banderita, Tucumn, Argentina	2005-DEC	PMID[19239238]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	La Banderita, Tucumn, Argentina	n.a.	PMID[20384357]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	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
LD50	1
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	Activity	=	100	%	PMID[19239238]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	Activity	=	57	%	PMID[19239238]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	Activity	=	10	%	PMID[19239238]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	LD50	=	1800	nM	PMID[19239238]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	LD90	=	2600	nM	PMID[19239238]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	LD100	<=	5	ppm	PMID[19239238]

☑ 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 NPC477056 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	358
0.1-0.2	1526
0.2-0.3	3812
0.3-0.4	9658
0.4-0.5	9158
0.5-0.6	4088
0.6-0.7	6824
0.7-0.8	5216
0.8-0.85	1361
0.85-0.9	604
0.9-0.95	86
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477055
0.9706	High Similarity	NPC325346
0.9333	High Similarity	NPC13575
0.9328	High Similarity	NPC16197
0.9318	High Similarity	NPC84772
0.9275	High Similarity	NPC11056
0.9265	High Similarity	NPC249606
0.9265	High Similarity	NPC12165
0.9265	High Similarity	NPC41461
0.9265	High Similarity	NPC25287
0.9265	High Similarity	NPC477243
0.9265	High Similarity	NPC1486
0.9265	High Similarity	NPC477244
0.9265	High Similarity	NPC150399
0.9265	High Similarity	NPC174999
0.9265	High Similarity	NPC168105
0.9265	High Similarity	NPC186838
0.9265	High Similarity	NPC66349
0.9265	High Similarity	NPC274109
0.9265	High Similarity	NPC98115
0.9265	High Similarity	NPC477242
0.9259	High Similarity	NPC103842
0.9254	High Similarity	NPC215875
0.9254	High Similarity	NPC15834
0.9248	High Similarity	NPC324482
0.9242	High Similarity	NPC230818
0.9209	High Similarity	NPC316911
0.9209	High Similarity	NPC316560
0.9197	High Similarity	NPC317119
0.9197	High Similarity	NPC153979
0.9197	High Similarity	NPC472419
0.9191	High Similarity	NPC156092
0.9191	High Similarity	NPC131039
0.9185	High Similarity	NPC20560
0.9185	High Similarity	NPC144051
0.9185	High Similarity	NPC159623
0.9185	High Similarity	NPC28753
0.9185	High Similarity	NPC82225
0.9185	High Similarity	NPC204960
0.9185	High Similarity	NPC294593
0.9185	High Similarity	NPC18877
0.9179	High Similarity	NPC27490
0.9143	High Similarity	NPC321629
0.9143	High Similarity	NPC297600
0.9143	High Similarity	NPC326193
0.9143	High Similarity	NPC321148
0.9143	High Similarity	NPC323884
0.9137	High Similarity	NPC471587
0.913	High Similarity	NPC131130
0.913	High Similarity	NPC243528
0.913	High Similarity	NPC251681
0.913	High Similarity	NPC21350
0.9124	High Similarity	NPC156910
0.9118	High Similarity	NPC164136
0.9118	High Similarity	NPC286336
0.9118	High Similarity	NPC125920
0.9104	High Similarity	NPC279566
0.9098	High Similarity	NPC212379
0.9098	High Similarity	NPC69235
0.9091	High Similarity	NPC128428
0.9091	High Similarity	NPC305518
0.9065	High Similarity	NPC470211
0.9065	High Similarity	NPC477956
0.9065	High Similarity	NPC139554
0.9065	High Similarity	NPC472366
0.9065	High Similarity	NPC23257
0.9058	High Similarity	NPC322301
0.9058	High Similarity	NPC23870
0.9058	High Similarity	NPC255801
0.9051	High Similarity	NPC84699
0.9051	High Similarity	NPC60667
0.9044	High Similarity	NPC192304
0.9044	High Similarity	NPC242294
0.9044	High Similarity	NPC56031
0.9044	High Similarity	NPC337373
0.9044	High Similarity	NPC27643
0.9044	High Similarity	NPC263670
0.9044	High Similarity	NPC472365
0.9044	High Similarity	NPC188646
0.9044	High Similarity	NPC93756
0.9044	High Similarity	NPC108113
0.9044	High Similarity	NPC312318
0.9044	High Similarity	NPC139813
0.9044	High Similarity	NPC175098
0.9037	High Similarity	NPC186097
0.9037	High Similarity	NPC475009
0.9037	High Similarity	NPC475008
0.903	High Similarity	NPC186628
0.9015	High Similarity	NPC328983
0.9014	High Similarity	NPC328623
0.9014	High Similarity	NPC476055
0.9014	High Similarity	NPC282957
0.9014	High Similarity	NPC194949
0.9	High Similarity	NPC326109
0.9	High Similarity	NPC265178
0.9	High Similarity	NPC253822
0.9	High Similarity	NPC213659
0.9	High Similarity	NPC172250
0.9	High Similarity	NPC144118
0.9	High Similarity	NPC159275
0.9	High Similarity	NPC204985
0.9	High Similarity	NPC477272
0.9	High Similarity	NPC80962
0.9	High Similarity	NPC219917
0.9	High Similarity	NPC241100
0.9	High Similarity	NPC259166
0.9	High Similarity	NPC48624
0.9	High Similarity	NPC215311
0.8993	High Similarity	NPC470668
0.8993	High Similarity	NPC471620
0.8993	High Similarity	NPC470672
0.8993	High Similarity	NPC474487
0.8993	High Similarity	NPC54820
0.8993	High Similarity	NPC470671
0.8993	High Similarity	NPC474504
0.8993	High Similarity	NPC180501
0.8993	High Similarity	NPC268178
0.8993	High Similarity	NPC470669
0.8978	High Similarity	NPC144027
0.8978	High Similarity	NPC236974
0.8971	High Similarity	NPC10971
0.8971	High Similarity	NPC212631
0.8971	High Similarity	NPC285054
0.8971	High Similarity	NPC257756
0.8971	High Similarity	NPC129132
0.8971	High Similarity	NPC87231
0.8971	High Similarity	NPC205468
0.8971	High Similarity	NPC203817
0.8947	High Similarity	NPC329205
0.8947	High Similarity	NPC316625
0.8944	High Similarity	NPC11700
0.8944	High Similarity	NPC473812
0.8944	High Similarity	NPC185276
0.8944	High Similarity	NPC473813
0.8936	High Similarity	NPC470089
0.8936	High Similarity	NPC40118
0.8936	High Similarity	NPC96408
0.8936	High Similarity	NPC232021
0.8936	High Similarity	NPC470087
0.8936	High Similarity	NPC279650
0.8936	High Similarity	NPC55832
0.8936	High Similarity	NPC110969
0.8936	High Similarity	NPC17170
0.8936	High Similarity	NPC126534
0.8936	High Similarity	NPC166689
0.8936	High Similarity	NPC321980
0.8936	High Similarity	NPC156190
0.8936	High Similarity	NPC26051
0.8936	High Similarity	NPC26238
0.8936	High Similarity	NPC282300
0.8936	High Similarity	NPC52789
0.8936	High Similarity	NPC268204
0.8936	High Similarity	NPC258630
0.8936	High Similarity	NPC469404
0.8929	High Similarity	NPC96565
0.8929	High Similarity	NPC270913
0.8929	High Similarity	NPC216978
0.8929	High Similarity	NPC301217
0.8929	High Similarity	NPC78913
0.8929	High Similarity	NPC217186
0.8929	High Similarity	NPC18260
0.8929	High Similarity	NPC53181
0.8929	High Similarity	NPC295384
0.8929	High Similarity	NPC303633
0.8929	High Similarity	NPC55018
0.8929	High Similarity	NPC220062
0.8929	High Similarity	NPC283429
0.8913	High Similarity	NPC101752
0.8897	High Similarity	NPC189106
0.8897	High Similarity	NPC31872
0.8897	High Similarity	NPC473584
0.8897	High Similarity	NPC313618
0.8897	High Similarity	NPC112192
0.8897	High Similarity	NPC262359
0.8897	High Similarity	NPC308037
0.8897	High Similarity	NPC164236
0.8897	High Similarity	NPC66384
0.8897	High Similarity	NPC309717
0.8897	High Similarity	NPC64359
0.8897	High Similarity	NPC128348
0.8897	High Similarity	NPC475589
0.8889	High Similarity	NPC10990
0.8889	High Similarity	NPC300988
0.8881	High Similarity	NPC80694
0.8881	High Similarity	NPC473014
0.8881	High Similarity	NPC472447
0.8881	High Similarity	NPC235217
0.8881	High Similarity	NPC472446
0.8881	High Similarity	NPC236766
0.8881	High Similarity	NPC186098
0.8881	High Similarity	NPC197252
0.8873	High Similarity	NPC125855
0.8873	High Similarity	NPC228504
0.8873	High Similarity	NPC107572
0.8873	High Similarity	NPC167624
0.8873	High Similarity	NPC227579
0.8873	High Similarity	NPC324436
0.8873	High Similarity	NPC220998
0.8873	High Similarity	NPC223500
0.8873	High Similarity	NPC11561

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 NPC477056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	980
0.2-0.3	1682
0.3-0.4	2698
0.4-0.5	1909
0.5-0.6	1075
0.6-0.7	350
0.7-0.8	106
0.8-0.85	17
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9474	High Similarity	NPD6651	Approved
0.8897	High Similarity	NPD1240	Approved
0.8794	High Similarity	NPD2800	Approved
0.8768	High Similarity	NPD1607	Approved
0.875	High Similarity	NPD4378	Clinical (unspecified phase)
0.8643	High Similarity	NPD1510	Phase 2
0.8621	High Similarity	NPD7410	Clinical (unspecified phase)
0.8521	High Similarity	NPD1552	Clinical (unspecified phase)
0.8521	High Similarity	NPD1550	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1549	Phase 2
0.8456	Intermediate Similarity	NPD4380	Phase 2
0.84	Intermediate Similarity	NPD7411	Suspended
0.8366	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD7819	Suspended
0.8289	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2796	Approved
0.817	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2533	Approved
0.8121	Intermediate Similarity	NPD2532	Approved
0.8121	Intermediate Similarity	NPD2534	Approved
0.8105	Intermediate Similarity	NPD6801	Discontinued
0.8092	Intermediate Similarity	NPD6599	Discontinued
0.8069	Intermediate Similarity	NPD2935	Discontinued
0.8054	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD1934	Approved
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7973	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7768	Phase 2
0.7937	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2801	Approved
0.7933	Intermediate Similarity	NPD1511	Approved
0.7925	Intermediate Similarity	NPD6232	Discontinued
0.7905	Intermediate Similarity	NPD1243	Approved
0.7905	Intermediate Similarity	NPD2654	Approved
0.7905	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3750	Approved
0.7834	Intermediate Similarity	NPD3882	Suspended
0.7829	Intermediate Similarity	NPD1512	Approved
0.7823	Intermediate Similarity	NPD6099	Approved
0.7823	Intermediate Similarity	NPD6100	Approved
0.777	Intermediate Similarity	NPD3972	Approved
0.7755	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6166	Phase 2
0.7716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1551	Phase 2
0.7697	Intermediate Similarity	NPD5953	Discontinued
0.7697	Intermediate Similarity	NPD7390	Discontinued
0.7683	Intermediate Similarity	NPD7286	Phase 2
0.7662	Intermediate Similarity	NPD920	Approved
0.7658	Intermediate Similarity	NPD3817	Phase 2
0.7651	Intermediate Similarity	NPD2344	Approved
0.7636	Intermediate Similarity	NPD7074	Phase 3
0.7635	Intermediate Similarity	NPD2799	Discontinued
0.7632	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD943	Approved
0.7576	Intermediate Similarity	NPD7054	Approved
0.7569	Intermediate Similarity	NPD6832	Phase 2
0.7562	Intermediate Similarity	NPD3749	Approved
0.7548	Intermediate Similarity	NPD5403	Approved
0.7532	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7472	Approved
0.7518	Intermediate Similarity	NPD9493	Approved
0.7518	Intermediate Similarity	NPD9717	Approved
0.7517	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5710	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7469	Intermediate Similarity	NPD5494	Approved
0.7452	Intermediate Similarity	NPD7458	Discontinued
0.7451	Intermediate Similarity	NPD2309	Approved
0.7447	Intermediate Similarity	NPD422	Phase 1
0.744	Intermediate Similarity	NPD7251	Discontinued
0.744	Intermediate Similarity	NPD6559	Discontinued
0.7431	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2798	Approved
0.7419	Intermediate Similarity	NPD5401	Approved
0.741	Intermediate Similarity	NPD9545	Approved
0.7396	Intermediate Similarity	NPD7808	Phase 3
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7347	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2313	Discontinued
0.7342	Intermediate Similarity	NPD3226	Approved
0.7337	Intermediate Similarity	NPD6104	Discontinued
0.7333	Intermediate Similarity	NPD3926	Phase 2
0.7325	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD230	Phase 1
0.7301	Intermediate Similarity	NPD919	Approved
0.7273	Intermediate Similarity	NPD7003	Approved
0.723	Intermediate Similarity	NPD3268	Approved
0.7222	Intermediate Similarity	NPD5402	Approved
0.7219	Intermediate Similarity	NPD1729	Discontinued
0.7212	Intermediate Similarity	NPD1247	Approved
0.7211	Intermediate Similarity	NPD4908	Phase 1
0.7203	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5124	Phase 1
0.72	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1241	Discontinued
0.7171	Intermediate Similarity	NPD7033	Discontinued
0.7171	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1548	Phase 1
0.716	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1164	Approved
0.7123	Intermediate Similarity	NPD2797	Approved
0.7114	Intermediate Similarity	NPD1296	Phase 2
0.7103	Intermediate Similarity	NPD4749	Approved
0.7083	Intermediate Similarity	NPD1201	Approved
0.7083	Intermediate Similarity	NPD2403	Approved
0.7083	Intermediate Similarity	NPD1610	Phase 2
0.7079	Intermediate Similarity	NPD4360	Phase 2
0.7079	Intermediate Similarity	NPD4363	Phase 3
0.7078	Intermediate Similarity	NPD2346	Discontinued
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1465	Phase 2
0.7055	Intermediate Similarity	NPD1876	Approved
0.7039	Intermediate Similarity	NPD4361	Phase 2
0.7039	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5405	Approved
0.7013	Intermediate Similarity	NPD5406	Approved
0.7013	Intermediate Similarity	NPD5404	Approved
0.7013	Intermediate Similarity	NPD5408	Approved
0.7007	Intermediate Similarity	NPD1470	Approved
0.7	Intermediate Similarity	NPD411	Approved
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6981	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD447	Suspended
0.6959	Remote Similarity	NPD1019	Discontinued
0.6949	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4308	Phase 3
0.6944	Remote Similarity	NPD4626	Approved
0.6939	Remote Similarity	NPD3225	Approved
0.6939	Remote Similarity	NPD8651	Approved
0.6934	Remote Similarity	NPD74	Approved
0.6934	Remote Similarity	NPD9266	Approved
0.6933	Remote Similarity	NPD3027	Phase 3
0.6933	Remote Similarity	NPD4625	Phase 3
0.6932	Remote Similarity	NPD8434	Phase 2
0.6918	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD9494	Approved
0.6909	Remote Similarity	NPD4288	Approved
0.6909	Remote Similarity	NPD2296	Approved
0.6901	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3266	Approved
0.6892	Remote Similarity	NPD3267	Approved
0.689	Remote Similarity	NPD37	Approved
0.6887	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD1651	Approved
0.6871	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7229	Phase 3
0.6863	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1933	Approved
0.6861	Remote Similarity	NPD9264	Approved
0.6861	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD9267	Approved
0.6861	Remote Similarity	NPD9263	Approved
0.6859	Remote Similarity	NPD1471	Phase 3
0.6848	Remote Similarity	NPD5760	Phase 2
0.6848	Remote Similarity	NPD5761	Phase 2
0.6845	Remote Similarity	NPD7584	Approved
0.6839	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1778	Approved
0.6824	Remote Similarity	NPD1283	Approved
0.6815	Remote Similarity	NPD2424	Discontinued
0.6812	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9269	Phase 2
0.68	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3142	Approved
0.6797	Remote Similarity	NPD3140	Approved
0.6786	Remote Similarity	NPD6234	Discontinued
0.6784	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3847	Discontinued
0.6776	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD8151	Discontinued
0.677	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4965	Approved
0.6766	Remote Similarity	NPD4966	Approved
0.6766	Remote Similarity	NPD4967	Phase 2
0.6763	Remote Similarity	NPD4750	Phase 3
0.6761	Remote Similarity	NPD8313	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