NPASS Compound

Structure

CID208233 OpenBabel06191716002D 21 25 0 0 1 0 0 0 0 0999 V2000 -3.4051 3.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6325 0.7751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7144 3.7541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6287 0.9403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1080 2.9764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1999 3.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6287 3.4571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1937 1.7180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1937 2.6794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7649 2.6794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7649 1.7180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1999 0.9403 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6730 2.1987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2573 2.6653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7144 0.6432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6344 2.1987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2234 1.8328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1715 2.6653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1080 1.4210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5974 2.1987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 3 6 2 0 0 0 0 4 15 1 0 0 0 0 5 1 1 6 0 0 0 5 9 1 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 3 1 1 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 8 4 1 6 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	878.37
Volume:	923.971
LogP:	7.286
LogD:	4.471
LogS:	-2.177
# Rotatable Bonds:	17
TPSA:	197.37
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.025
Synthetic Accessibility Score:	5.112
Fsp3:	0.241
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.343
MDCK Permeability:	6.867710908409208e-06
Pgp-inhibitor:	0.559
Pgp-substrate:	0.102
Human Intestinal Absorption (HIA):	0.945
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	103.75468444824219%
Volume Distribution (VD):	-0.071
Pgp-substrate:	0.543448269367218%

ADMET: Metabolism

CYP1A2-inhibitor:	0.18
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.923
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.648
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.599
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	8.757
Half-life (T1/2):	0.494

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.254
Rat Oral Acute Toxicity:	0.701
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.971
Carcinogencity:	0.313
Eye Corrosion:	0.003
Eye Irritation:	0.375
Respiratory Toxicity:	0.182

Download Data

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

Natural Product: NPC208233

Natural Product ID:	NPC208233
*Common Name:**	Dihydromikanolide
IUPAC Name:	n.a.
Synonyms:	Dihydromikanolide
Standard InCHIKey:	UOQXZMNXWXQCJU-XMOWUHPBSA-N
Standard InCHI:	InChI=1S/C15H16O6/c1-5-9-7-3-6(14(17)18-7)10-11(20-10)12-15(2,21-12)4-8(9)19-13(5)16/h3,5,7-12H,4H2,1-2H3/t5-,7-,8+,9+,10-,11-,12+,15+/m1/s1
SMILES:	C[C@@H]1[C@H]2[C@H]3C=C([C@@H]4[C@H]([C@H]5[C@](C)(C[C@@H]2OC1=O)O5)O4)C(=O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554278
PubChem CID:	442200
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO24708	Mikania micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19267453]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24708	Mikania micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	3
Others	5

Activity Type	# Activity
Cell Line	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	214.0	uM	PMID[501384]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	142800.0	nM	PMID[501384]
NPT27	Others	Unspecified		TC50	=	214.0	uM	PMID[501384]
NPT27	Others	Unspecified		TI	=	1.5	n.a.	PMID[501384]
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	IC50	=	142800.0	nM	PMID[501384]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	142800.0	nM	PMID[501384]

☑ 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 NPC208233 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	285
0.1-0.2	1685
0.2-0.3	6071
0.3-0.4	11685
0.4-0.5	13784
0.5-0.6	6029
0.6-0.7	2458
0.7-0.8	596
0.8-0.85	62
0.85-0.9	29
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC35498
0.9348	High Similarity	NPC140543
0.9348	High Similarity	NPC473316
0.9348	High Similarity	NPC476267
0.9348	High Similarity	NPC473330
0.9348	High Similarity	NPC471147
0.9231	High Similarity	NPC312042
0.9167	High Similarity	NPC264477
0.9167	High Similarity	NPC477511
0.8958	High Similarity	NPC473326
0.8913	High Similarity	NPC166919
0.8913	High Similarity	NPC151770
0.8889	High Similarity	NPC477510
0.8889	High Similarity	NPC471143
0.8866	High Similarity	NPC477512
0.8866	High Similarity	NPC288876
0.8854	High Similarity	NPC471140
0.8842	High Similarity	NPC475659
0.8763	High Similarity	NPC279561
0.875	High Similarity	NPC17585
0.875	High Similarity	NPC473859
0.8713	High Similarity	NPC477513
0.8696	High Similarity	NPC231889
0.8696	High Similarity	NPC475703
0.8681	High Similarity	NPC38468
0.8681	High Similarity	NPC319795
0.8681	High Similarity	NPC50362
0.8617	High Similarity	NPC251385
0.8617	High Similarity	NPC475748
0.8617	High Similarity	NPC49342
0.8587	High Similarity	NPC50637
0.8542	High Similarity	NPC57405
0.8542	High Similarity	NPC303942
0.85	High Similarity	NPC471148
0.8478	Intermediate Similarity	NPC474547
0.8421	Intermediate Similarity	NPC62815
0.84	Intermediate Similarity	NPC474339
0.84	Intermediate Similarity	NPC164598
0.8384	Intermediate Similarity	NPC474213
0.837	Intermediate Similarity	NPC138647
0.837	Intermediate Similarity	NPC470238
0.8367	Intermediate Similarity	NPC230800
0.8367	Intermediate Similarity	NPC279621
0.8333	Intermediate Similarity	NPC20713
0.8333	Intermediate Similarity	NPC474741
0.8317	Intermediate Similarity	NPC149371
0.8265	Intermediate Similarity	NPC270013
0.8265	Intermediate Similarity	NPC471142
0.8265	Intermediate Similarity	NPC14961
0.8261	Intermediate Similarity	NPC272814
0.8247	Intermediate Similarity	NPC475838
0.8247	Intermediate Similarity	NPC228451
0.8247	Intermediate Similarity	NPC125674
0.8247	Intermediate Similarity	NPC212486
0.8242	Intermediate Similarity	NPC207188
0.8218	Intermediate Similarity	NPC201718
0.8218	Intermediate Similarity	NPC47880
0.82	Intermediate Similarity	NPC471144
0.8191	Intermediate Similarity	NPC204048
0.8191	Intermediate Similarity	NPC284902
0.8182	Intermediate Similarity	NPC476315
0.8163	Intermediate Similarity	NPC81386
0.8163	Intermediate Similarity	NPC474035
0.8163	Intermediate Similarity	NPC474247
0.8144	Intermediate Similarity	NPC475881
0.8144	Intermediate Similarity	NPC70251
0.8119	Intermediate Similarity	NPC475949
0.8105	Intermediate Similarity	NPC5130
0.8105	Intermediate Similarity	NPC266957
0.8081	Intermediate Similarity	NPC471141
0.8081	Intermediate Similarity	NPC477922
0.8077	Intermediate Similarity	NPC243998
0.8077	Intermediate Similarity	NPC223450
0.8065	Intermediate Similarity	NPC475947
0.8061	Intermediate Similarity	NPC476300
0.8061	Intermediate Similarity	NPC165383
0.8061	Intermediate Similarity	NPC81419
0.8061	Intermediate Similarity	NPC475912
0.8061	Intermediate Similarity	NPC179746
0.8058	Intermediate Similarity	NPC475945
0.8058	Intermediate Similarity	NPC475871
0.8043	Intermediate Similarity	NPC141810
0.8041	Intermediate Similarity	NPC51004
0.8041	Intermediate Similarity	NPC80875
0.8041	Intermediate Similarity	NPC473619
0.8039	Intermediate Similarity	NPC474742
0.8021	Intermediate Similarity	NPC475902
0.8	Intermediate Similarity	NPC476275
0.8	Intermediate Similarity	NPC477921
0.7981	Intermediate Similarity	NPC100487
0.7981	Intermediate Similarity	NPC203659
0.7981	Intermediate Similarity	NPC307846
0.7981	Intermediate Similarity	NPC305157
0.7961	Intermediate Similarity	NPC474747
0.7959	Intermediate Similarity	NPC208886
0.7959	Intermediate Similarity	NPC12172
0.7959	Intermediate Similarity	NPC261607
0.7959	Intermediate Similarity	NPC473321
0.7959	Intermediate Similarity	NPC111114
0.7959	Intermediate Similarity	NPC30515
0.7959	Intermediate Similarity	NPC300312
0.7959	Intermediate Similarity	NPC184463
0.7938	Intermediate Similarity	NPC307411
0.7938	Intermediate Similarity	NPC475971
0.7938	Intermediate Similarity	NPC295312
0.7938	Intermediate Similarity	NPC474032
0.7938	Intermediate Similarity	NPC4986
0.7925	Intermediate Similarity	NPC475960
0.79	Intermediate Similarity	NPC36954
0.7895	Intermediate Similarity	NPC215364
0.7885	Intermediate Similarity	NPC110989
0.7885	Intermediate Similarity	NPC19239
0.7885	Intermediate Similarity	NPC474166
0.7879	Intermediate Similarity	NPC135776
0.7879	Intermediate Similarity	NPC295204
0.7879	Intermediate Similarity	NPC288240
0.7879	Intermediate Similarity	NPC162205
0.7879	Intermediate Similarity	NPC273579
0.787	Intermediate Similarity	NPC475495
0.7864	Intermediate Similarity	NPC476270
0.7857	Intermediate Similarity	NPC329857
0.7857	Intermediate Similarity	NPC144133
0.7857	Intermediate Similarity	NPC469718
0.7857	Intermediate Similarity	NPC179394
0.7857	Intermediate Similarity	NPC475855
0.785	Intermediate Similarity	NPC59489
0.785	Intermediate Similarity	NPC139838
0.785	Intermediate Similarity	NPC38154
0.7835	Intermediate Similarity	NPC473715
0.7835	Intermediate Similarity	NPC469628
0.7835	Intermediate Similarity	NPC471047
0.7835	Intermediate Similarity	NPC469653
0.7835	Intermediate Similarity	NPC224652
0.7835	Intermediate Similarity	NPC475906
0.7835	Intermediate Similarity	NPC202672
0.7835	Intermediate Similarity	NPC469631
0.7826	Intermediate Similarity	NPC617
0.78	Intermediate Similarity	NPC477131
0.7798	Intermediate Similarity	NPC475277
0.7798	Intermediate Similarity	NPC477093
0.7798	Intermediate Similarity	NPC473522
0.7788	Intermediate Similarity	NPC225353
0.7778	Intermediate Similarity	NPC473843
0.7778	Intermediate Similarity	NPC473975
0.7778	Intermediate Similarity	NPC473594
0.7778	Intermediate Similarity	NPC70595
0.7778	Intermediate Similarity	NPC158061
0.7778	Intermediate Similarity	NPC474586
0.7778	Intermediate Similarity	NPC123177
0.7778	Intermediate Similarity	NPC74103
0.7778	Intermediate Similarity	NPC150978
0.7778	Intermediate Similarity	NPC284185
0.7745	Intermediate Similarity	NPC471462
0.7742	Intermediate Similarity	NPC474739
0.7742	Intermediate Similarity	NPC223904
0.7736	Intermediate Similarity	NPC103088
0.7736	Intermediate Similarity	NPC54737
0.7736	Intermediate Similarity	NPC9303
0.7736	Intermediate Similarity	NPC16313
0.7736	Intermediate Similarity	NPC470979
0.7736	Intermediate Similarity	NPC314244
0.7736	Intermediate Similarity	NPC475802
0.7736	Intermediate Similarity	NPC470975
0.7732	Intermediate Similarity	NPC160138
0.7723	Intermediate Similarity	NPC304886
0.7723	Intermediate Similarity	NPC474947
0.7723	Intermediate Similarity	NPC224689
0.7717	Intermediate Similarity	NPC23187
0.7714	Intermediate Similarity	NPC475873
0.7706	Intermediate Similarity	NPC194619
0.7692	Intermediate Similarity	NPC128733
0.7692	Intermediate Similarity	NPC110443
0.7692	Intermediate Similarity	NPC185141
0.7692	Intermediate Similarity	NPC235906
0.7692	Intermediate Similarity	NPC133907
0.7692	Intermediate Similarity	NPC46998
0.7692	Intermediate Similarity	NPC473332
0.7684	Intermediate Similarity	NPC170377
0.7684	Intermediate Similarity	NPC257358
0.7684	Intermediate Similarity	NPC170286
0.7684	Intermediate Similarity	NPC475842
0.7684	Intermediate Similarity	NPC474472
0.7684	Intermediate Similarity	NPC318468
0.7679	Intermediate Similarity	NPC471146
0.7677	Intermediate Similarity	NPC71533
0.7677	Intermediate Similarity	NPC106510
0.7677	Intermediate Similarity	NPC474761
0.7677	Intermediate Similarity	NPC253144
0.7677	Intermediate Similarity	NPC476004
0.767	Intermediate Similarity	NPC221615
0.767	Intermediate Similarity	NPC187268
0.7664	Intermediate Similarity	NPC72813
0.7664	Intermediate Similarity	NPC194620
0.7664	Intermediate Similarity	NPC26617
0.7664	Intermediate Similarity	NPC326994
0.7664	Intermediate Similarity	NPC474421
0.7664	Intermediate Similarity	NPC475587
0.7664	Intermediate Similarity	NPC474716
0.7664	Intermediate Similarity	NPC469558
0.7664	Intermediate Similarity	NPC324327

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 NPC208233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	2320
0.2-0.3	3932
0.3-0.4	1832
0.4-0.5	585
0.5-0.6	194
0.6-0.7	29
0.7-0.8	4
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8681	High Similarity	NPD1733	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD1695	Approved
0.7664	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD46	Approved
0.7327	Intermediate Similarity	NPD6698	Approved
0.7297	Intermediate Similarity	NPD6371	Approved
0.7027	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7838	Discovery
0.6944	Remote Similarity	NPD6648	Approved
0.6923	Remote Similarity	NPD7983	Approved
0.6881	Remote Similarity	NPD5344	Discontinued
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5282	Discontinued
0.6786	Remote Similarity	NPD6008	Approved
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6581	Remote Similarity	NPD6053	Discontinued
0.6542	Remote Similarity	NPD5779	Approved
0.6542	Remote Similarity	NPD5778	Approved
0.6535	Remote Similarity	NPD5209	Approved
0.6509	Remote Similarity	NPD5785	Approved
0.65	Remote Similarity	NPD7115	Discovery
0.6423	Remote Similarity	NPD8517	Approved
0.6423	Remote Similarity	NPD8516	Approved
0.6423	Remote Similarity	NPD8515	Approved
0.6423	Remote Similarity	NPD8513	Phase 3
0.6413	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5363	Approved
0.6328	Remote Similarity	NPD7319	Approved
0.632	Remote Similarity	NPD7642	Approved
0.6286	Remote Similarity	NPD4249	Approved
0.6286	Remote Similarity	NPD5786	Approved
0.6226	Remote Similarity	NPD4250	Approved
0.6226	Remote Similarity	NPD4251	Approved
0.622	Remote Similarity	NPD7507	Approved
0.619	Remote Similarity	NPD7829	Approved
0.619	Remote Similarity	NPD7830	Approved
0.6172	Remote Similarity	NPD8074	Phase 3
0.6142	Remote Similarity	NPD7492	Approved
0.6119	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5369	Approved
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6101	Approved
0.6094	Remote Similarity	NPD6616	Approved
0.6083	Remote Similarity	NPD2204	Approved
0.608	Remote Similarity	NPD6319	Approved
0.608	Remote Similarity	NPD6054	Approved
0.6071	Remote Similarity	NPD7839	Suspended
0.6058	Remote Similarity	NPD4269	Approved
0.6058	Remote Similarity	NPD4270	Approved
0.6058	Remote Similarity	NPD6435	Approved
0.6047	Remote Similarity	NPD7078	Approved
0.6038	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6016	Approved
0.6032	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD7154	Phase 3
0.6	Remote Similarity	NPD6411	Approved
0.5984	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6370	Approved
0.5966	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7638	Approved
0.5952	Remote Similarity	NPD6059	Approved
0.5923	Remote Similarity	NPD8293	Discontinued
0.5913	Remote Similarity	NPD7640	Approved
0.5913	Remote Similarity	NPD7639	Approved
0.5865	Remote Similarity	NPD4820	Approved
0.5865	Remote Similarity	NPD4821	Approved
0.5865	Remote Similarity	NPD4819	Approved
0.5865	Remote Similarity	NPD4822	Approved
0.5865	Remote Similarity	NPD4252	Approved
0.5865	Remote Similarity	NPD7260	Phase 2
0.5865	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5368	Approved
0.5854	Remote Similarity	NPD4632	Approved
0.5846	Remote Similarity	NPD8273	Phase 1
0.5846	Remote Similarity	NPD8451	Approved
0.5841	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD6845	Suspended
0.5802	Remote Similarity	NPD8448	Approved
0.5772	Remote Similarity	NPD8297	Approved
0.5766	Remote Similarity	NPD3168	Discontinued
0.5755	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6001	Approved
0.575	Remote Similarity	NPD5697	Approved
0.5738	Remote Similarity	NPD2067	Discontinued
0.5727	Remote Similarity	NPD6903	Approved
0.5714	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD5693	Phase 1
0.5702	Remote Similarity	NPD7320	Approved
0.5702	Remote Similarity	NPD6881	Approved
0.5702	Remote Similarity	NPD6899	Approved
0.5692	Remote Similarity	NPD7604	Phase 2
0.5692	Remote Similarity	NPD8328	Phase 3
0.5691	Remote Similarity	NPD6650	Approved
0.5691	Remote Similarity	NPD6649	Approved
0.5688	Remote Similarity	NPD5330	Approved
0.5688	Remote Similarity	NPD7146	Approved
0.5688	Remote Similarity	NPD6684	Approved
0.5688	Remote Similarity	NPD7521	Approved
0.5688	Remote Similarity	NPD6409	Approved
0.5688	Remote Similarity	NPD7334	Approved
0.5686	Remote Similarity	NPD8039	Approved
0.5673	Remote Similarity	NPD4271	Approved
0.5673	Remote Similarity	NPD4268	Approved
0.5672	Remote Similarity	NPD8392	Approved
0.5672	Remote Similarity	NPD8390	Approved
0.5672	Remote Similarity	NPD8391	Approved
0.5669	Remote Similarity	NPD7327	Approved
0.5669	Remote Similarity	NPD7641	Discontinued
0.5669	Remote Similarity	NPD7328	Approved
0.5667	Remote Similarity	NPD6402	Approved
0.5667	Remote Similarity	NPD6675	Approved
0.5667	Remote Similarity	NPD5739	Approved
0.5667	Remote Similarity	NPD7128	Approved
0.5664	Remote Similarity	NPD6399	Phase 3
0.5659	Remote Similarity	NPD5983	Phase 2
0.5659	Remote Similarity	NPD8444	Approved
0.5659	Remote Similarity	NPD8033	Approved
0.5656	Remote Similarity	NPD6013	Approved
0.5656	Remote Similarity	NPD6014	Approved
0.5656	Remote Similarity	NPD6012	Approved
0.5656	Remote Similarity	NPD6373	Approved
0.5656	Remote Similarity	NPD6372	Approved
0.5649	Remote Similarity	NPD8340	Approved
0.5649	Remote Similarity	NPD8299	Approved
0.5649	Remote Similarity	NPD8342	Approved
0.5649	Remote Similarity	NPD8341	Approved
0.5639	Remote Similarity	NPD8337	Approved
0.5639	Remote Similarity	NPD8336	Approved
0.5636	Remote Similarity	NPD3573	Approved
0.5625	Remote Similarity	NPD5207	Approved
0.5625	Remote Similarity	NPD7516	Approved
0.562	Remote Similarity	NPD6412	Phase 2
0.562	Remote Similarity	NPD5701	Approved
0.5615	Remote Similarity	NPD8080	Discontinued
0.5614	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD7900	Approved
0.561	Remote Similarity	NPD4634	Approved
0.561	Remote Similarity	NPD6883	Approved
0.561	Remote Similarity	NPD7102	Approved
0.561	Remote Similarity	NPD7290	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