NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	367.485
LogP:	2.215
LogD:	0.289
LogS:	-3.302
# Rotatable Bonds:	1
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	6.057
Fsp3:	0.9
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:	-4.772
MDCK Permeability:	1.8553912013885565e-05
Pgp-inhibitor:	0.061
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	56.467567443847656%
Volume Distribution (VD):	1.456
Pgp-substrate:	32.303096771240234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.293
CYP3A4-substrate:	0.451

ADMET: Excretion

Clearance (CL):	9.29
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.726
Drug-inuced Liver Injury (DILI):	0.733
AMES Toxicity:	0.638
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.527
Carcinogencity:	0.796
Eye Corrosion:	0.009
Eye Irritation:	0.038
Respiratory Toxicity:	0.437

Download Data

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

Natural Product: NPC476705

Natural Product ID:	NPC476705
*Common Name:**	Boscartin E
IUPAC Name:	(1S,3R,5R,7S,8E,12R,13R)-7,12-dihydroxy-5,9,13-trimethyl-1-propan-2-yl-4,16-dioxatricyclo[11.2.1.03,5]hexadec-8-en-10-one
Synonyms:
Standard InCHIKey:	YCQANNMZZHKNIZ-ZLIHTVQJSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-12(2)20-7-6-18(4,25-20)16(23)9-15(22)13(3)8-14(21)10-19(5)17(11-20)24-19/h8,12,14,16-17,21,23H,6-7,9-11H2,1-5H3/b13-8+/t14-,16-,17-,18-,19-,20+/m1/s1
SMILES:	C/C/1=C\[C@H](C[C@@]2([C@H](O2)C[C@@]3(CC[C@@](O3)([C@@H](CC1=O)O)C)C(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122196282
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195447]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	Gum resin	n.a.	n.a.	PMID[26457560]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15315	Boswellia carterii	Species	Burseraceae	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
EC50	1
Others	2

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3972	Individual Protein	X-box-binding protein 1	Rattus norvegicus	FC	=	2.5	n.a.	PMID[26457560]
NPT3972	Individual Protein	X-box-binding protein 1	Rattus norvegicus	EC50	=	880	nM	PMID[26457560]
NPT2	Others	Unspecified		Survival	=	87	%	PMID[26457560]

☑ 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 NPC476705 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	199
0.1-0.2	1220
0.2-0.3	4943
0.3-0.4	9362
0.4-0.5	14385
0.5-0.6	7347
0.6-0.7	4145
0.7-0.8	1036
0.8-0.85	50
0.85-0.9	7
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9647	High Similarity	NPC476707
0.9647	High Similarity	NPC476706
0.8764	High Similarity	NPC476708
0.8764	High Similarity	NPC476704
0.8706	High Similarity	NPC472948
0.8438	Intermediate Similarity	NPC288876
0.8404	Intermediate Similarity	NPC14961
0.8404	Intermediate Similarity	NPC270013
0.837	Intermediate Similarity	NPC473448
0.8353	Intermediate Similarity	NPC476703
0.8351	Intermediate Similarity	NPC164598
0.8351	Intermediate Similarity	NPC474339
0.8316	Intermediate Similarity	NPC476315
0.8316	Intermediate Similarity	NPC230800
0.8316	Intermediate Similarity	NPC279621
0.8298	Intermediate Similarity	NPC474035
0.8298	Intermediate Similarity	NPC81386
0.8283	Intermediate Similarity	NPC474741
0.8211	Intermediate Similarity	NPC36954
0.8191	Intermediate Similarity	NPC228451
0.8191	Intermediate Similarity	NPC475912
0.8191	Intermediate Similarity	NPC125674
0.8191	Intermediate Similarity	NPC469645
0.8191	Intermediate Similarity	NPC212486
0.8191	Intermediate Similarity	NPC475838
0.8191	Intermediate Similarity	NPC469692
0.8182	Intermediate Similarity	NPC472755
0.8182	Intermediate Similarity	NPC475945
0.8182	Intermediate Similarity	NPC475871
0.8152	Intermediate Similarity	NPC87189
0.8152	Intermediate Similarity	NPC228415
0.8125	Intermediate Similarity	NPC93271
0.8125	Intermediate Similarity	NPC135576
0.8125	Intermediate Similarity	NPC473859
0.8105	Intermediate Similarity	NPC121825
0.8105	Intermediate Similarity	NPC474247
0.81	Intermediate Similarity	NPC100487
0.8085	Intermediate Similarity	NPC184463
0.8085	Intermediate Similarity	NPC30515
0.8081	Intermediate Similarity	NPC471148
0.8081	Intermediate Similarity	NPC474747
0.8081	Intermediate Similarity	NPC39996
0.8058	Intermediate Similarity	NPC257240
0.8041	Intermediate Similarity	NPC40812
0.8021	Intermediate Similarity	NPC475659
0.802	Intermediate Similarity	NPC243998
0.8	Intermediate Similarity	NPC162205
0.8	Intermediate Similarity	NPC110989
0.8	Intermediate Similarity	NPC295204
0.8	Intermediate Similarity	NPC476300
0.8	Intermediate Similarity	NPC273579
0.8	Intermediate Similarity	NPC288240
0.798	Intermediate Similarity	NPC46998
0.798	Intermediate Similarity	NPC128733
0.798	Intermediate Similarity	NPC133907
0.798	Intermediate Similarity	NPC201718
0.798	Intermediate Similarity	NPC476270
0.798	Intermediate Similarity	NPC474742
0.798	Intermediate Similarity	NPC472753
0.798	Intermediate Similarity	NPC110443
0.798	Intermediate Similarity	NPC185141
0.7979	Intermediate Similarity	NPC476004
0.7979	Intermediate Similarity	NPC474761
0.7979	Intermediate Similarity	NPC51004
0.7961	Intermediate Similarity	NPC87335
0.7959	Intermediate Similarity	NPC473326
0.7959	Intermediate Similarity	NPC474213
0.7959	Intermediate Similarity	NPC187761
0.7959	Intermediate Similarity	NPC83895
0.7959	Intermediate Similarity	NPC187268
0.7957	Intermediate Similarity	NPC476803
0.7941	Intermediate Similarity	NPC477513
0.7935	Intermediate Similarity	NPC469483
0.7921	Intermediate Similarity	NPC472756
0.7921	Intermediate Similarity	NPC203659
0.7917	Intermediate Similarity	NPC303942
0.7917	Intermediate Similarity	NPC57405
0.7905	Intermediate Similarity	NPC138757
0.79	Intermediate Similarity	NPC86077
0.79	Intermediate Similarity	NPC472754
0.79	Intermediate Similarity	NPC149371
0.79	Intermediate Similarity	NPC225353
0.7895	Intermediate Similarity	NPC475441
0.7882	Intermediate Similarity	NPC476709
0.7872	Intermediate Similarity	NPC307411
0.7864	Intermediate Similarity	NPC474664
0.7864	Intermediate Similarity	NPC233379
0.7864	Intermediate Similarity	NPC14862
0.7857	Intermediate Similarity	NPC266842
0.7849	Intermediate Similarity	NPC179659
0.7843	Intermediate Similarity	NPC223450
0.7835	Intermediate Similarity	NPC304886
0.7835	Intermediate Similarity	NPC471142
0.7835	Intermediate Similarity	NPC471141
0.7835	Intermediate Similarity	NPC261341
0.783	Intermediate Similarity	NPC46269
0.783	Intermediate Similarity	NPC106395
0.7826	Intermediate Similarity	NPC125290
0.7812	Intermediate Similarity	NPC81419
0.7812	Intermediate Similarity	NPC179746
0.781	Intermediate Similarity	NPC317107
0.7802	Intermediate Similarity	NPC477785
0.7802	Intermediate Similarity	NPC477784
0.7802	Intermediate Similarity	NPC477786
0.78	Intermediate Similarity	NPC9878
0.78	Intermediate Similarity	NPC150923
0.78	Intermediate Similarity	NPC47880
0.78	Intermediate Similarity	NPC471401
0.78	Intermediate Similarity	NPC473332
0.7789	Intermediate Similarity	NPC477684
0.7789	Intermediate Similarity	NPC179394
0.7789	Intermediate Similarity	NPC475855
0.7789	Intermediate Similarity	NPC474232
0.7789	Intermediate Similarity	NPC144133
0.7789	Intermediate Similarity	NPC475748
0.7788	Intermediate Similarity	NPC15218
0.7788	Intermediate Similarity	NPC477102
0.7778	Intermediate Similarity	NPC261377
0.7778	Intermediate Similarity	NPC255592
0.7778	Intermediate Similarity	NPC471146
0.7778	Intermediate Similarity	NPC471144
0.7778	Intermediate Similarity	NPC161855
0.7778	Intermediate Similarity	NPC470241
0.7778	Intermediate Similarity	NPC308567
0.7767	Intermediate Similarity	NPC474421
0.7767	Intermediate Similarity	NPC326994
0.7767	Intermediate Similarity	NPC324327
0.7767	Intermediate Similarity	NPC26617
0.7767	Intermediate Similarity	NPC72813
0.7767	Intermediate Similarity	NPC194620
0.7766	Intermediate Similarity	NPC202672
0.7766	Intermediate Similarity	NPC476805
0.7757	Intermediate Similarity	NPC138303
0.7757	Intermediate Similarity	NPC133677
0.7757	Intermediate Similarity	NPC67290
0.7755	Intermediate Similarity	NPC8803
0.7755	Intermediate Similarity	NPC473291
0.7755	Intermediate Similarity	NPC477921
0.7745	Intermediate Similarity	NPC146731
0.7745	Intermediate Similarity	NPC296950
0.7745	Intermediate Similarity	NPC220964
0.7745	Intermediate Similarity	NPC475676
0.7742	Intermediate Similarity	NPC475461
0.7742	Intermediate Similarity	NPC305475
0.7742	Intermediate Similarity	NPC469910
0.7736	Intermediate Similarity	NPC317687
0.7736	Intermediate Similarity	NPC76550
0.7736	Intermediate Similarity	NPC123855
0.7732	Intermediate Similarity	NPC469819
0.7732	Intermediate Similarity	NPC476267
0.7732	Intermediate Similarity	NPC114162
0.7717	Intermediate Similarity	NPC3464
0.7717	Intermediate Similarity	NPC151176
0.7717	Intermediate Similarity	NPC475963
0.7714	Intermediate Similarity	NPC161816
0.7714	Intermediate Similarity	NPC477103
0.7714	Intermediate Similarity	NPC115257
0.7708	Intermediate Similarity	NPC473321
0.7708	Intermediate Similarity	NPC111114
0.7708	Intermediate Similarity	NPC12172
0.7708	Intermediate Similarity	NPC158061
0.7708	Intermediate Similarity	NPC261607
0.7708	Intermediate Similarity	NPC208886
0.7708	Intermediate Similarity	NPC300312
0.77	Intermediate Similarity	NPC475053
0.77	Intermediate Similarity	NPC475949
0.7692	Intermediate Similarity	NPC308191
0.7692	Intermediate Similarity	NPC327286
0.7692	Intermediate Similarity	NPC169888
0.7692	Intermediate Similarity	NPC55972
0.7684	Intermediate Similarity	NPC130359
0.7684	Intermediate Similarity	NPC14901
0.7684	Intermediate Similarity	NPC473564
0.7677	Intermediate Similarity	NPC27105
0.767	Intermediate Similarity	NPC475802
0.767	Intermediate Similarity	NPC179891
0.767	Intermediate Similarity	NPC9303
0.767	Intermediate Similarity	NPC471333
0.767	Intermediate Similarity	NPC16313
0.767	Intermediate Similarity	NPC471332
0.7667	Intermediate Similarity	NPC470945
0.7667	Intermediate Similarity	NPC470946
0.7667	Intermediate Similarity	NPC470947
0.766	Intermediate Similarity	NPC471738
0.766	Intermediate Similarity	NPC23622
0.766	Intermediate Similarity	NPC231889
0.766	Intermediate Similarity	NPC72513
0.7653	Intermediate Similarity	NPC107476
0.7653	Intermediate Similarity	NPC477922
0.7653	Intermediate Similarity	NPC475900
0.7647	Intermediate Similarity	NPC469980
0.7647	Intermediate Similarity	NPC69171
0.7647	Intermediate Similarity	NPC474165
0.7647	Intermediate Similarity	NPC475873
0.7647	Intermediate Similarity	NPC4620
0.7647	Intermediate Similarity	NPC118902
0.7647	Intermediate Similarity	NPC104161
0.764	Intermediate Similarity	NPC218817
0.764	Intermediate Similarity	NPC11796
0.7636	Intermediate Similarity	NPC477092

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 NPC476705 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1886
0.2-0.3	3893
0.3-0.4	2156
0.4-0.5	616
0.5-0.6	305
0.6-0.7	93
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8058	Intermediate Similarity	NPD6371	Approved
0.7789	Intermediate Similarity	NPD6698	Approved
0.7789	Intermediate Similarity	NPD46	Approved
0.7767	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5282	Discontinued
0.7526	Intermediate Similarity	NPD7983	Approved
0.7447	Intermediate Similarity	NPD5363	Approved
0.7423	Intermediate Similarity	NPD7838	Discovery
0.73	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7255	Intermediate Similarity	NPD4225	Approved
0.7245	Intermediate Similarity	NPD5785	Approved
0.7128	Intermediate Similarity	NPD4269	Approved
0.7128	Intermediate Similarity	NPD4270	Approved
0.7115	Intermediate Similarity	NPD5344	Discontinued
0.71	Intermediate Similarity	NPD5779	Approved
0.71	Intermediate Similarity	NPD5778	Approved
0.7083	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6110	Phase 1
0.7037	Intermediate Similarity	NPD6686	Approved
0.7021	Intermediate Similarity	NPD5369	Approved
0.701	Intermediate Similarity	NPD5786	Approved
0.697	Remote Similarity	NPD1695	Approved
0.6947	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4252	Approved
0.6875	Remote Similarity	NPD7154	Phase 3
0.6847	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6412	Phase 2
0.6771	Remote Similarity	NPD6435	Approved
0.6768	Remote Similarity	NPD4250	Approved
0.6768	Remote Similarity	NPD4251	Approved
0.6762	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4822	Approved
0.6737	Remote Similarity	NPD4819	Approved
0.6737	Remote Similarity	NPD4821	Approved
0.6737	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4820	Approved
0.6702	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5362	Discontinued
0.6698	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD8517	Approved
0.661	Remote Similarity	NPD8516	Approved
0.661	Remote Similarity	NPD8515	Approved
0.6607	Remote Similarity	NPD4634	Approved
0.66	Remote Similarity	NPD7524	Approved
0.6571	Remote Similarity	NPD7839	Suspended
0.6562	Remote Similarity	NPD5368	Approved
0.6555	Remote Similarity	NPD6370	Approved
0.6526	Remote Similarity	NPD4271	Approved
0.6526	Remote Similarity	NPD4268	Approved
0.6525	Remote Similarity	NPD6319	Approved
0.6525	Remote Similarity	NPD6059	Approved
0.6505	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD7642	Approved
0.6471	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD6016	Approved
0.6471	Remote Similarity	NPD6015	Approved
0.6465	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD5209	Approved
0.6422	Remote Similarity	NPD5211	Phase 2
0.6417	Remote Similarity	NPD5988	Approved
0.6404	Remote Similarity	NPD7331	Phase 2
0.64	Remote Similarity	NPD1694	Approved
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6616	Approved
0.6389	Remote Similarity	NPD7640	Approved
0.6389	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD6695	Phase 3
0.6355	Remote Similarity	NPD6083	Phase 2
0.6355	Remote Similarity	NPD6084	Phase 2
0.6348	Remote Similarity	NPD8297	Approved
0.6348	Remote Similarity	NPD6053	Discontinued
0.6346	Remote Similarity	NPD6411	Approved
0.6341	Remote Similarity	NPD8074	Phase 3
0.6341	Remote Similarity	NPD7078	Approved
0.6337	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3618	Phase 1
0.6321	Remote Similarity	NPD5210	Approved
0.6321	Remote Similarity	NPD4629	Approved
0.6311	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD5370	Suspended
0.6306	Remote Similarity	NPD5141	Approved
0.63	Remote Similarity	NPD3666	Approved
0.63	Remote Similarity	NPD3665	Phase 1
0.63	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD7638	Approved
0.6293	Remote Similarity	NPD4632	Approved
0.6292	Remote Similarity	NPD7341	Phase 2
0.629	Remote Similarity	NPD7736	Approved
0.6286	Remote Similarity	NPD6399	Phase 3
0.6283	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6899	Approved
0.6279	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6650	Approved
0.6261	Remote Similarity	NPD6649	Approved
0.626	Remote Similarity	NPD8273	Phase 1
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD7128	Approved
0.624	Remote Similarity	NPD7319	Approved
0.6239	Remote Similarity	NPD4696	Approved
0.6239	Remote Similarity	NPD5285	Approved
0.6239	Remote Similarity	NPD5286	Approved
0.623	Remote Similarity	NPD8328	Phase 3
0.623	Remote Similarity	NPD7830	Approved
0.623	Remote Similarity	NPD7829	Approved
0.6228	Remote Similarity	NPD6372	Approved
0.6228	Remote Similarity	NPD6373	Approved
0.621	Remote Similarity	NPD8293	Discontinued
0.6204	Remote Similarity	NPD7902	Approved
0.6204	Remote Similarity	NPD4755	Approved
0.62	Remote Similarity	NPD5331	Approved
0.62	Remote Similarity	NPD5332	Approved
0.6195	Remote Similarity	NPD5697	Approved
0.6195	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6079	Approved
0.6176	Remote Similarity	NPD4519	Discontinued
0.6176	Remote Similarity	NPD4623	Approved
0.6176	Remote Similarity	NPD5279	Phase 3
0.6174	Remote Similarity	NPD7290	Approved
0.6174	Remote Similarity	NPD7102	Approved
0.6174	Remote Similarity	NPD6883	Approved
0.6168	Remote Similarity	NPD5695	Phase 3
0.6167	Remote Similarity	NPD4522	Approved
0.6162	Remote Similarity	NPD4790	Discontinued
0.6154	Remote Similarity	NPD5328	Approved
0.6147	Remote Similarity	NPD5696	Approved
0.614	Remote Similarity	NPD7320	Approved
0.6139	Remote Similarity	NPD4786	Approved
0.6134	Remote Similarity	NPD7500	Approved
0.6132	Remote Similarity	NPD4202	Approved
0.6129	Remote Similarity	NPD7507	Approved
0.6126	Remote Similarity	NPD4633	Approved
0.6126	Remote Similarity	NPD5226	Approved
0.6126	Remote Similarity	NPD5224	Approved
0.6126	Remote Similarity	NPD5225	Approved
0.6121	Remote Similarity	NPD6847	Approved
0.6121	Remote Similarity	NPD6869	Approved
0.6121	Remote Similarity	NPD8130	Phase 1
0.6121	Remote Similarity	NPD6617	Approved
0.6117	Remote Similarity	NPD7750	Discontinued
0.6111	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.61	Remote Similarity	NPD3667	Approved
0.6098	Remote Similarity	NPD7604	Phase 2
0.6091	Remote Similarity	NPD4700	Approved
0.6087	Remote Similarity	NPD6012	Approved
0.6087	Remote Similarity	NPD6013	Approved
0.6087	Remote Similarity	NPD6014	Approved
0.6083	Remote Similarity	NPD7641	Discontinued
0.6078	Remote Similarity	NPD1696	Phase 3
0.6075	Remote Similarity	NPD7748	Approved
0.6071	Remote Similarity	NPD5175	Approved
0.6071	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD6882	Approved
0.6063	Remote Similarity	NPD5956	Approved
0.6061	Remote Similarity	NPD6930	Phase 2
0.6061	Remote Similarity	NPD4695	Discontinued
0.6061	Remote Similarity	NPD6931	Approved
0.6053	Remote Similarity	NPD5701	Approved
0.6048	Remote Similarity	NPD8341	Approved
0.6048	Remote Similarity	NPD8342	Approved
0.6048	Remote Similarity	NPD8340	Approved
0.6048	Remote Similarity	NPD8299	Approved
0.6038	Remote Similarity	NPD7515	Phase 2
0.6036	Remote Similarity	NPD5223	Approved
0.6032	Remote Similarity	NPD6033	Approved
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD6684	Approved
0.6019	Remote Similarity	NPD7521	Approved
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD6009	Approved
0.5983	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5221	Approved
0.5963	Remote Similarity	NPD5222	Approved
0.5963	Remote Similarity	NPD4697	Phase 3
0.596	Remote Similarity	NPD6929	Approved
0.5955	Remote Similarity	NPD368	Approved
0.5948	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4223	Phase 3
0.5941	Remote Similarity	NPD4221	Approved
0.5935	Remote Similarity	NPD5983	Phase 2
0.5929	Remote Similarity	NPD6647	Phase 2

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