NPASS Compound

Structure

NPC473332 OpenBabel07101719152D 26 29 0 0 1 0 0 0 0 0999 V2000 -1.5644 1.5682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6082 3.2385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8559 -0.2003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9318 -2.5787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2497 -1.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6533 -2.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6886 0.0638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5787 -1.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.3907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9083 -0.3811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8966 -2.5787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0813 -1.5669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4851 -0.1274 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2497 -0.9318 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.0170 -0.7503 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0329 2.3655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1881 -0.3194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8966 -0.2497 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9318 -0.2497 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.5369 3.1880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7788 0.5541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2657 0.6416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5787 -0.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7746 -0.9123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4932 1.5177 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 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 7 13 1 0 0 0 0 7 19 1 0 0 0 0 8 11 1 0 0 0 0 8 23 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 12 6 1 6 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 1 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 10 1 6 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.15
Volume:	353.94
LogP:	0.834
LogD:	1.39
LogS:	-2.89
# Rotatable Bonds:	3
TPSA:	94.59
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.341
Synthetic Accessibility Score:	6.632
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.048
MDCK Permeability:	2.8242673579370603e-05
Pgp-inhibitor:	0.268
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.085
20% Bioavailability (F20%):	0.068
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668
Plasma Protein Binding (PPB):	73.69774627685547%
Volume Distribution (VD):	1.281
Pgp-substrate:	43.94759750366211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.543
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	7.944
Half-life (T1/2):	0.549

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.736
Drug-inuced Liver Injury (DILI):	0.602
AMES Toxicity:	0.709
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.263
Carcinogencity:	0.253
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC473332

Natural Product ID:	NPC473332
*Common Name:**	Vernomygdin
IUPAC Name:	n.a.
Synonyms:	Vernomygdin
Standard InCHIKey:	XFUPYBHPEVBTJS-CFTDVZOMSA-N
Standard InCHI:	InChI=1S/C19H24O7/c1-9(2)16(20)25-13-7-19-14(26-19)5-4-11(8-23-18(19)22)6-12-15(13)10(3)17(21)24-12/h6,9,12-15,18,22H,3-5,7-8H2,1-2H3/b11-6+/t12-,13+,14?,15+,18?,19?/m1/s1
SMILES:	O=C(C(C)C)O[C@H]1CC23OC3CC/C(=C[C@@H]3[C@@H]1C(=C)C(=O)O3)/COC2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401107
PubChem CID:	n.a.
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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[518896]
NPT91	Cell Line	KB	Homo sapiens	pED50	=	5.39	n.a.	PMID[518896]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.12	umol/L	PMID[518897]

☑ 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 NPC473332 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	250
0.1-0.2	1531
0.2-0.3	5398
0.3-0.4	12192
0.4-0.5	12208
0.5-0.6	7307
0.6-0.7	3086
0.7-0.8	663
0.8-0.85	39
0.85-0.9	22
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8854	High Similarity	NPC14961
0.8854	High Similarity	NPC270013
0.8854	High Similarity	NPC471141
0.8842	High Similarity	NPC212486
0.8763	High Similarity	NPC279621
0.875	High Similarity	NPC81386
0.875	High Similarity	NPC474035
0.8646	High Similarity	NPC125674
0.8646	High Similarity	NPC228451
0.8646	High Similarity	NPC475838
0.8646	High Similarity	NPC475912
0.8586	High Similarity	NPC187268
0.8586	High Similarity	NPC473326
0.8586	High Similarity	NPC279561
0.8571	High Similarity	NPC476315
0.8571	High Similarity	NPC473859
0.8571	High Similarity	NPC306041
0.8557	High Similarity	NPC303942
0.8557	High Similarity	NPC57405
0.8557	High Similarity	NPC474247
0.8542	High Similarity	NPC30515
0.8542	High Similarity	NPC184463
0.8515	High Similarity	NPC471148
0.85	High Similarity	NPC288876
0.8469	Intermediate Similarity	NPC475659
0.8469	Intermediate Similarity	NPC36954
0.8454	Intermediate Similarity	NPC179746
0.8454	Intermediate Similarity	NPC81419
0.8454	Intermediate Similarity	NPC476300
0.8438	Intermediate Similarity	NPC51004
0.8421	Intermediate Similarity	NPC202672
0.8416	Intermediate Similarity	NPC164598
0.8416	Intermediate Similarity	NPC474339
0.8404	Intermediate Similarity	NPC50637
0.84	Intermediate Similarity	NPC474213
0.8384	Intermediate Similarity	NPC230800
0.8351	Intermediate Similarity	NPC12172
0.8351	Intermediate Similarity	NPC208886
0.8333	Intermediate Similarity	NPC151770
0.8333	Intermediate Similarity	NPC307411
0.8316	Intermediate Similarity	NPC231889
0.8247	Intermediate Similarity	NPC476004
0.8247	Intermediate Similarity	NPC474761
0.8247	Intermediate Similarity	NPC475855
0.8247	Intermediate Similarity	NPC206614
0.8247	Intermediate Similarity	NPC473619
0.8247	Intermediate Similarity	NPC475748
0.8247	Intermediate Similarity	NPC474323
0.8235	Intermediate Similarity	NPC476270
0.82	Intermediate Similarity	NPC54731
0.819	Intermediate Similarity	NPC477513
0.8182	Intermediate Similarity	NPC71589
0.8182	Intermediate Similarity	NPC474338
0.8182	Intermediate Similarity	NPC473316
0.8182	Intermediate Similarity	NPC473330
0.8163	Intermediate Similarity	NPC70251
0.8163	Intermediate Similarity	NPC475881
0.8163	Intermediate Similarity	NPC473321
0.8144	Intermediate Similarity	NPC474032
0.8144	Intermediate Similarity	NPC166919
0.8137	Intermediate Similarity	NPC475949
0.8105	Intermediate Similarity	NPC255307
0.81	Intermediate Similarity	NPC107476
0.8095	Intermediate Similarity	NPC243998
0.8081	Intermediate Similarity	NPC288240
0.8081	Intermediate Similarity	NPC273579
0.8081	Intermediate Similarity	NPC295204
0.8081	Intermediate Similarity	NPC162205
0.8065	Intermediate Similarity	NPC141810
0.8061	Intermediate Similarity	NPC144133
0.8061	Intermediate Similarity	NPC179394
0.8058	Intermediate Similarity	NPC201718
0.8041	Intermediate Similarity	NPC281516
0.8041	Intermediate Similarity	NPC473715
0.8039	Intermediate Similarity	NPC471144
0.8021	Intermediate Similarity	NPC305475
0.8021	Intermediate Similarity	NPC475461
0.8	Intermediate Similarity	NPC114979
0.8	Intermediate Similarity	NPC474741
0.8	Intermediate Similarity	NPC191476
0.8	Intermediate Similarity	NPC474917
0.8	Intermediate Similarity	NPC471147
0.7981	Intermediate Similarity	NPC86077
0.7981	Intermediate Similarity	NPC149371
0.798	Intermediate Similarity	NPC473707
0.798	Intermediate Similarity	NPC470373
0.798	Intermediate Similarity	NPC470379
0.7963	Intermediate Similarity	NPC235014
0.7959	Intermediate Similarity	NPC473564
0.7944	Intermediate Similarity	NPC475960
0.7941	Intermediate Similarity	NPC471140
0.7938	Intermediate Similarity	NPC186148
0.7938	Intermediate Similarity	NPC5130
0.7925	Intermediate Similarity	NPC223450
0.7921	Intermediate Similarity	NPC304886
0.7921	Intermediate Similarity	NPC471142
0.7917	Intermediate Similarity	NPC304509
0.7917	Intermediate Similarity	NPC38468
0.7917	Intermediate Similarity	NPC21469
0.7917	Intermediate Similarity	NPC47958
0.7917	Intermediate Similarity	NPC319795
0.7917	Intermediate Similarity	NPC149725
0.7917	Intermediate Similarity	NPC50362
0.7905	Intermediate Similarity	NPC475945
0.7905	Intermediate Similarity	NPC475871
0.79	Intermediate Similarity	NPC320089
0.7895	Intermediate Similarity	NPC272814
0.7895	Intermediate Similarity	NPC473390
0.7895	Intermediate Similarity	NPC250315
0.7895	Intermediate Similarity	NPC131669
0.7895	Intermediate Similarity	NPC231601
0.7885	Intermediate Similarity	NPC150923
0.7885	Intermediate Similarity	NPC47880
0.7879	Intermediate Similarity	NPC469368
0.7879	Intermediate Similarity	NPC473448
0.7879	Intermediate Similarity	NPC474232
0.7864	Intermediate Similarity	NPC222303
0.7857	Intermediate Similarity	NPC153805
0.7857	Intermediate Similarity	NPC476803
0.7857	Intermediate Similarity	NPC58219
0.7857	Intermediate Similarity	NPC177629
0.785	Intermediate Similarity	NPC474421
0.785	Intermediate Similarity	NPC326994
0.785	Intermediate Similarity	NPC194620
0.785	Intermediate Similarity	NPC324327
0.785	Intermediate Similarity	NPC72813
0.7849	Intermediate Similarity	NPC617
0.7843	Intermediate Similarity	NPC477921
0.7835	Intermediate Similarity	NPC150755
0.7835	Intermediate Similarity	NPC469910
0.7835	Intermediate Similarity	NPC162071
0.783	Intermediate Similarity	NPC100487
0.7822	Intermediate Similarity	NPC190294
0.7822	Intermediate Similarity	NPC477131
0.7822	Intermediate Similarity	NPC140543
0.7812	Intermediate Similarity	NPC141193
0.7812	Intermediate Similarity	NPC96259
0.7812	Intermediate Similarity	NPC476804
0.781	Intermediate Similarity	NPC320019
0.781	Intermediate Similarity	NPC474747
0.781	Intermediate Similarity	NPC324017
0.78	Intermediate Similarity	NPC472197
0.78	Intermediate Similarity	NPC476705
0.78	Intermediate Similarity	NPC131209
0.78	Intermediate Similarity	NPC133698
0.78	Intermediate Similarity	NPC158061
0.7789	Intermediate Similarity	NPC229825
0.7788	Intermediate Similarity	NPC70865
0.7788	Intermediate Similarity	NPC475053
0.7778	Intermediate Similarity	NPC327286
0.7778	Intermediate Similarity	NPC55972
0.7778	Intermediate Similarity	NPC295312
0.7778	Intermediate Similarity	NPC233379
0.7778	Intermediate Similarity	NPC169888
0.7778	Intermediate Similarity	NPC14862
0.7778	Intermediate Similarity	NPC92974
0.7778	Intermediate Similarity	NPC474664
0.7767	Intermediate Similarity	NPC161493
0.7767	Intermediate Similarity	NPC471462
0.7757	Intermediate Similarity	NPC16313
0.7757	Intermediate Similarity	NPC9303
0.7757	Intermediate Similarity	NPC54737
0.7755	Intermediate Similarity	NPC160138
0.7755	Intermediate Similarity	NPC248602
0.7755	Intermediate Similarity	NPC475703
0.7755	Intermediate Similarity	NPC474765
0.7745	Intermediate Similarity	NPC67584
0.7745	Intermediate Similarity	NPC477922
0.7745	Intermediate Similarity	NPC52044
0.7745	Intermediate Similarity	NPC213698
0.7736	Intermediate Similarity	NPC69171
0.7736	Intermediate Similarity	NPC472747
0.7736	Intermediate Similarity	NPC472750
0.7736	Intermediate Similarity	NPC4620
0.7736	Intermediate Similarity	NPC474165
0.7732	Intermediate Similarity	NPC137033
0.7732	Intermediate Similarity	NPC165162
0.7723	Intermediate Similarity	NPC472195
0.7723	Intermediate Similarity	NPC238090
0.7723	Intermediate Similarity	NPC473561
0.7723	Intermediate Similarity	NPC472196
0.7723	Intermediate Similarity	NPC473663
0.7723	Intermediate Similarity	NPC469645
0.7723	Intermediate Similarity	NPC469692
0.7723	Intermediate Similarity	NPC475173
0.7723	Intermediate Similarity	NPC473723
0.7714	Intermediate Similarity	NPC15993
0.7714	Intermediate Similarity	NPC264477
0.7714	Intermediate Similarity	NPC477511
0.7714	Intermediate Similarity	NPC474742
0.7708	Intermediate Similarity	NPC40746
0.7708	Intermediate Similarity	NPC11620
0.7708	Intermediate Similarity	NPC169575
0.7708	Intermediate Similarity	NPC170286
0.7706	Intermediate Similarity	NPC15218
0.7706	Intermediate Similarity	NPC475922
0.77	Intermediate Similarity	NPC312042
0.77	Intermediate Similarity	NPC251385
0.77	Intermediate Similarity	NPC473904
0.77	Intermediate Similarity	NPC80875

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 NPC473332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	2174
0.2-0.3	3753
0.3-0.4	2106
0.4-0.5	629
0.5-0.6	203
0.6-0.7	45
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8061	Intermediate Similarity	NPD46	Approved
0.8061	Intermediate Similarity	NPD6698	Approved
0.7917	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7838	Discovery
0.7615	Intermediate Similarity	NPD6686	Approved
0.7523	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6371	Approved
0.7426	Intermediate Similarity	NPD1695	Approved
0.7411	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7983	Approved
0.7064	Intermediate Similarity	NPD5344	Discontinued
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.7	Intermediate Similarity	NPD8513	Phase 3
0.6916	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7642	Approved
0.6881	Remote Similarity	NPD4225	Approved
0.6783	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7830	Approved
0.6748	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD6648	Approved
0.664	Remote Similarity	NPD7507	Approved
0.6635	Remote Similarity	NPD4249	Approved
0.6609	Remote Similarity	NPD6412	Phase 2
0.6581	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4250	Approved
0.6571	Remote Similarity	NPD4251	Approved
0.6542	Remote Similarity	NPD5785	Approved
0.6514	Remote Similarity	NPD5282	Discontinued
0.6508	Remote Similarity	NPD8451	Approved
0.6484	Remote Similarity	NPD7319	Approved
0.6475	Remote Similarity	NPD7641	Discontinued
0.6471	Remote Similarity	NPD6053	Discontinued
0.6457	Remote Similarity	NPD8074	Phase 3
0.6457	Remote Similarity	NPD8448	Approved
0.6442	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.6417	Remote Similarity	NPD8133	Approved
0.6396	Remote Similarity	NPD7839	Suspended
0.6381	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5363	Approved
0.6373	Remote Similarity	NPD4821	Approved
0.6373	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4819	Approved
0.6373	Remote Similarity	NPD4822	Approved
0.6373	Remote Similarity	NPD4820	Approved
0.6346	Remote Similarity	NPD5362	Discontinued
0.6341	Remote Similarity	NPD7327	Approved
0.6341	Remote Similarity	NPD7328	Approved
0.6325	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8444	Approved
0.632	Remote Similarity	NPD7503	Approved
0.632	Remote Similarity	NPD8033	Approved
0.6311	Remote Similarity	NPD5369	Approved
0.6308	Remote Similarity	NPD8390	Approved
0.6308	Remote Similarity	NPD8391	Approved
0.6308	Remote Similarity	NPD8392	Approved
0.6299	Remote Similarity	NPD8299	Approved
0.6299	Remote Similarity	NPD8342	Approved
0.6299	Remote Similarity	NPD8340	Approved
0.6299	Remote Similarity	NPD8341	Approved
0.629	Remote Similarity	NPD7516	Approved
0.6283	Remote Similarity	NPD7638	Approved
0.6277	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD8273	Phase 1
0.625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.624	Remote Similarity	NPD8294	Approved
0.624	Remote Similarity	NPD8377	Approved
0.6228	Remote Similarity	NPD7639	Approved
0.6228	Remote Similarity	NPD7640	Approved
0.6226	Remote Similarity	NPD1694	Approved
0.6218	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8335	Approved
0.619	Remote Similarity	NPD8379	Approved
0.619	Remote Similarity	NPD8378	Approved
0.619	Remote Similarity	NPD8380	Approved
0.619	Remote Similarity	NPD8296	Approved
0.6176	Remote Similarity	NPD4271	Approved
0.6176	Remote Similarity	NPD4268	Approved
0.6168	Remote Similarity	NPD5786	Approved
0.6154	Remote Similarity	NPD7736	Approved
0.6142	Remote Similarity	NPD6370	Approved
0.6129	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6008	Approved
0.6094	Remote Similarity	NPD8328	Phase 3
0.6077	Remote Similarity	NPD8293	Discontinued
0.6058	Remote Similarity	NPD4252	Approved
0.6058	Remote Similarity	NPD5368	Approved
0.6047	Remote Similarity	NPD7492	Approved
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8080	Discontinued
0.6016	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5984	Remote Similarity	NPD6319	Approved
0.5984	Remote Similarity	NPD6054	Approved
0.5982	Remote Similarity	NPD6399	Phase 3
0.5954	Remote Similarity	NPD7078	Approved
0.5946	Remote Similarity	NPD3168	Discontinued
0.5943	Remote Similarity	NPD5209	Approved
0.5938	Remote Similarity	NPD6015	Approved
0.5938	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6016	Approved
0.5893	Remote Similarity	NPD6411	Approved
0.5893	Remote Similarity	NPD7637	Suspended
0.5891	Remote Similarity	NPD5988	Approved
0.5888	Remote Similarity	NPD5332	Approved
0.5888	Remote Similarity	NPD6110	Phase 1
0.5888	Remote Similarity	NPD5331	Approved
0.5873	Remote Similarity	NPD7500	Approved
0.5859	Remote Similarity	NPD6059	Approved
0.5854	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD2204	Approved
0.5849	Remote Similarity	NPD4790	Discontinued
0.5818	Remote Similarity	NPD7524	Approved
0.5806	Remote Similarity	NPD6882	Approved
0.5806	Remote Similarity	NPD8297	Approved
0.5785	Remote Similarity	NPD5697	Approved
0.5778	Remote Similarity	NPD7260	Phase 2
0.5776	Remote Similarity	NPD6084	Phase 2
0.5776	Remote Similarity	NPD6083	Phase 2
0.5772	Remote Similarity	NPD6421	Discontinued
0.5739	Remote Similarity	NPD5695	Phase 3
0.5738	Remote Similarity	NPD6899	Approved
0.5738	Remote Similarity	NPD6881	Approved
0.5728	Remote Similarity	NPD8039	Approved
0.5726	Remote Similarity	NPD5696	Approved
0.5726	Remote Similarity	NPD6649	Approved
0.5726	Remote Similarity	NPD6650	Approved
0.5725	Remote Similarity	NPD6067	Discontinued
0.5725	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD7632	Discontinued
0.5714	Remote Similarity	NPD5370	Suspended
0.5702	Remote Similarity	NPD6402	Approved
0.5702	Remote Similarity	NPD7128	Approved
0.5702	Remote Similarity	NPD6675	Approved
0.5702	Remote Similarity	NPD5739	Approved
0.5692	Remote Similarity	NPD8267	Approved
0.5692	Remote Similarity	NPD5983	Phase 2
0.5692	Remote Similarity	NPD8268	Approved
0.5692	Remote Similarity	NPD8266	Approved
0.5692	Remote Similarity	NPD8269	Approved
0.5691	Remote Similarity	NPD6373	Approved
0.5691	Remote Similarity	NPD6014	Approved
0.5691	Remote Similarity	NPD6012	Approved
0.5691	Remote Similarity	NPD6013	Approved
0.5691	Remote Similarity	NPD6372	Approved
0.5688	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.567	Remote Similarity	NPD3197	Phase 1
0.5656	Remote Similarity	NPD5701	Approved
0.5645	Remote Similarity	NPD7290	Approved
0.5645	Remote Similarity	NPD6883	Approved
0.5645	Remote Similarity	NPD7102	Approved
0.5641	Remote Similarity	NPD7902	Approved
0.562	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6845	Suspended
0.562	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD4756	Discovery
0.5614	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6011	Approved
0.561	Remote Similarity	NPD7320	Approved
0.56	Remote Similarity	NPD8130	Phase 1
0.56	Remote Similarity	NPD6617	Approved
0.56	Remote Similarity	NPD6869	Approved
0.56	Remote Similarity	NPD6847	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