NPASS Compound

Structure

CID265795 OpenBabel06191716072D 44 48 0 0 0 0 0 0 0 0999 V2000 -1.6967 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0901 0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2418 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6352 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2418 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0901 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4835 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7868 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2418 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7868 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6352 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9385 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4835 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0901 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6352 -3.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 2.9388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 -3.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 0.9796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3319 -0.4898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 2.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9385 -3.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3319 -2.4490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.9184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 1.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7868 -3.9184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4835 -3.9184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 2.4490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 3.9184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -1.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9385 -0.4898 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 42 1 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 30 2 0 0 0 0 8 15 1 0 0 0 0 8 31 2 0 0 0 0 9 16 1 0 0 0 0 10 22 1 0 0 0 0 10 26 2 0 0 0 0 11 23 1 0 0 0 0 11 32 1 0 0 0 0 12 24 1 0 0 0 0 12 33 1 0 0 0 0 13 17 2 0 0 0 0 13 43 1 0 0 0 0 14 18 2 0 0 0 0 14 44 1 0 0 0 0 15 16 2 0 0 0 0 15 26 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 29 2 0 0 0 0 22 34 2 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 37 2 0 0 0 0 26 43 1 0 0 0 0 27 38 2 0 0 0 0 27 39 1 0 0 0 0 28 40 2 0 0 0 0 28 41 1 0 0 0 0 29 42 1 0 0 0 0 29 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.06
Volume:	557.028
LogP:	2.821
LogD:	1.487
LogS:	-5.026
# Rotatable Bonds:	6
TPSA:	259.31
# H-Bond Aceptor:	15
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.092
Synthetic Accessibility Score:	3.626
Fsp3:	0.103
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.141
MDCK Permeability:	8.843589057505596e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.628
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.237
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	75.2499771118164%
Volume Distribution (VD):	0.736
Pgp-substrate:	33.538211822509766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	-0.243
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.738
Drug-inuced Liver Injury (DILI):	0.999
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.612
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.066
Respiratory Toxicity:	0.075

Download Data

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

Natural Product: NPC265795

Natural Product ID:	NPC265795
*Common Name:**	(Ar)-2-Methoxyvinaxanthone
IUPAC Name:	5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-2-methoxy-4-oxochromen-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	HYNJWQUNCFKEGY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H18O15/c1-7(30)9-4-10-22(34)17-13(5-11(32)23(35)19(17)27(38)39)43-26(10)15(8(2)31)16(9)21-25(37)18-14(44-29(21)42-3)6-12(33)24(36)20(18)28(40)41/h4-6,32-33,35-36H,1-3H3,(H,38,39)(H,40,41)
SMILES:	COc1oc2cc(O)c(c(c2c(=O)c1c1c(cc2c(c1C(=O)C)oc1c(c2=O)c(C(=O)O)c(c(c1)O)O)C(=O)C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448083
PubChem CID:	24879150
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO810	Penicillium vinaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18355033]
NPO810	Penicillium vinaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4569	Xanthoria steineri	Species	Teloschistaceae	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	1
Others	2

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2588	Organism	Paracentrotus lividus	Paracentrotus lividus	IC50	=	0.05	ug.mL-1	PMID[486320]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	72.0	%	PMID[486320]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	100.0	%	PMID[486320]

☑ 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 NPC265795 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	454
0.1-0.2	2204
0.2-0.3	4740
0.3-0.4	10596
0.4-0.5	7507
0.5-0.6	4082
0.6-0.7	5454
0.7-0.8	5086
0.8-0.85	2127
0.85-0.9	429
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC207467
0.9586	High Similarity	NPC473785
0.92	High Similarity	NPC174486
0.92	High Similarity	NPC105591
0.9176	High Similarity	NPC158226
0.9118	High Similarity	NPC109827
0.9118	High Similarity	NPC124470
0.9096	High Similarity	NPC295436
0.9059	High Similarity	NPC165979
0.9059	High Similarity	NPC163130
0.9059	High Similarity	NPC49487
0.9059	High Similarity	NPC99613
0.9023	High Similarity	NPC212290
0.9	High Similarity	NPC107009
0.9	High Similarity	NPC76647
0.8971	High Similarity	NPC97523
0.896	High Similarity	NPC68381
0.896	High Similarity	NPC245975
0.8944	High Similarity	NPC314020
0.8941	High Similarity	NPC30027
0.8941	High Similarity	NPC29160
0.8935	High Similarity	NPC207690
0.8902	High Similarity	NPC472054
0.8889	High Similarity	NPC234331
0.8876	High Similarity	NPC470694
0.8876	High Similarity	NPC329760
0.8869	High Similarity	NPC119224
0.8864	High Similarity	NPC475161
0.8864	High Similarity	NPC477860
0.8862	High Similarity	NPC263483
0.8851	High Similarity	NPC474345
0.8851	High Similarity	NPC470454
0.8851	High Similarity	NPC199533
0.8851	High Similarity	NPC146803
0.8844	High Similarity	NPC271848
0.8844	High Similarity	NPC81332
0.8844	High Similarity	NPC262580
0.8844	High Similarity	NPC76128
0.8844	High Similarity	NPC5029
0.8844	High Similarity	NPC289396
0.8844	High Similarity	NPC30432
0.8844	High Similarity	NPC111536
0.8844	High Similarity	NPC212038
0.8844	High Similarity	NPC271385
0.883	High Similarity	NPC37870
0.8824	High Similarity	NPC236132
0.8824	High Similarity	NPC270837
0.8824	High Similarity	NPC474350
0.8807	High Similarity	NPC277710
0.8807	High Similarity	NPC114257
0.8807	High Similarity	NPC84494
0.8807	High Similarity	NPC153578
0.8807	High Similarity	NPC245059
0.8807	High Similarity	NPC113446
0.8807	High Similarity	NPC299149
0.8802	High Similarity	NPC142339
0.88	High Similarity	NPC475246
0.88	High Similarity	NPC46958
0.88	High Similarity	NPC472991
0.88	High Similarity	NPC472992
0.88	High Similarity	NPC216307
0.88	High Similarity	NPC164384
0.8793	High Similarity	NPC37606
0.8786	High Similarity	NPC298778
0.8772	High Similarity	NPC275780
0.8772	High Similarity	NPC239752
0.8772	High Similarity	NPC472450
0.8765	High Similarity	NPC108767
0.8765	High Similarity	NPC294965
0.8757	High Similarity	NPC56085
0.8757	High Similarity	NPC470448
0.8757	High Similarity	NPC470452
0.8757	High Similarity	NPC315221
0.8757	High Similarity	NPC228785
0.8757	High Similarity	NPC470453
0.8757	High Similarity	NPC84571
0.8757	High Similarity	NPC14353
0.8757	High Similarity	NPC164047
0.875	High Similarity	NPC476619
0.875	High Similarity	NPC476618
0.875	High Similarity	NPC472387
0.875	High Similarity	NPC476622
0.875	High Similarity	NPC236796
0.875	High Similarity	NPC476621
0.875	High Similarity	NPC476620
0.875	High Similarity	NPC476623
0.8743	High Similarity	NPC139350
0.8743	High Similarity	NPC113906
0.8743	High Similarity	NPC3718
0.8736	High Similarity	NPC477836
0.8729	High Similarity	NPC321046
0.8729	High Similarity	NPC264302
0.8722	High Similarity	NPC205721
0.8721	High Similarity	NPC207575
0.8721	High Similarity	NPC39091
0.8721	High Similarity	NPC472449
0.8721	High Similarity	NPC13481
0.8715	High Similarity	NPC261623
0.8715	High Similarity	NPC111490
0.8713	High Similarity	NPC23298
0.8713	High Similarity	NPC327809
0.8713	High Similarity	NPC189473
0.8713	High Similarity	NPC146134
0.8713	High Similarity	NPC101769
0.8713	High Similarity	NPC248638
0.8713	High Similarity	NPC152659
0.8713	High Similarity	NPC236521
0.8708	High Similarity	NPC36138
0.8708	High Similarity	NPC313452
0.8706	High Similarity	NPC258331
0.8706	High Similarity	NPC32694
0.8706	High Similarity	NPC311740
0.8706	High Similarity	NPC40491
0.8706	High Similarity	NPC66288
0.8706	High Similarity	NPC278052
0.8706	High Similarity	NPC61010
0.8706	High Similarity	NPC278427
0.8698	High Similarity	NPC85121
0.8698	High Similarity	NPC45846
0.8698	High Similarity	NPC100123
0.8693	High Similarity	NPC475233
0.869	High Similarity	NPC146211
0.8686	High Similarity	NPC472993
0.8686	High Similarity	NPC261471
0.8686	High Similarity	NPC199357
0.8683	High Similarity	NPC89474
0.8683	High Similarity	NPC214632
0.8683	High Similarity	NPC107109
0.8678	High Similarity	NPC224462
0.8678	High Similarity	NPC78830
0.8678	High Similarity	NPC218533
0.8671	High Similarity	NPC243877
0.8667	High Similarity	NPC469649
0.8667	High Similarity	NPC260521
0.8663	High Similarity	NPC8070
0.8663	High Similarity	NPC471788
0.8663	High Similarity	NPC156432
0.8663	High Similarity	NPC26386
0.8663	High Similarity	NPC259757
0.8663	High Similarity	NPC88243
0.8659	High Similarity	NPC49690
0.8659	High Similarity	NPC470416
0.8659	High Similarity	NPC231254
0.8655	High Similarity	NPC220912
0.8655	High Similarity	NPC472448
0.8655	High Similarity	NPC25152
0.8655	High Similarity	NPC52204
0.8655	High Similarity	NPC83922
0.8655	High Similarity	NPC229632
0.8652	High Similarity	NPC208069
0.8649	High Similarity	NPC174140
0.8647	High Similarity	NPC320359
0.8647	High Similarity	NPC80375
0.8647	High Similarity	NPC235018
0.8647	High Similarity	NPC45146
0.8644	High Similarity	NPC217387
0.8644	High Similarity	NPC258044
0.8644	High Similarity	NPC196127
0.8644	High Similarity	NPC35167
0.8644	High Similarity	NPC293626
0.8644	High Similarity	NPC267680
0.8639	High Similarity	NPC199463
0.8639	High Similarity	NPC241904
0.8639	High Similarity	NPC37543
0.8639	High Similarity	NPC300727
0.8639	High Similarity	NPC217677
0.8639	High Similarity	NPC36852
0.8639	High Similarity	NPC165977
0.8639	High Similarity	NPC79053
0.8639	High Similarity	NPC262286
0.8636	High Similarity	NPC289147
0.8636	High Similarity	NPC63105
0.8634	High Similarity	NPC477082
0.8629	High Similarity	NPC205076
0.8629	High Similarity	NPC211594
0.8629	High Similarity	NPC307518
0.8629	High Similarity	NPC67134
0.8629	High Similarity	NPC172807
0.8629	High Similarity	NPC254540
0.8629	High Similarity	NPC47140
0.8629	High Similarity	NPC260263
0.8629	High Similarity	NPC48773
0.8621	High Similarity	NPC259905
0.8621	High Similarity	NPC300307
0.8621	High Similarity	NPC476637
0.8621	High Similarity	NPC222455
0.8621	High Similarity	NPC188079
0.8621	High Similarity	NPC183036
0.8621	High Similarity	NPC471287
0.8621	High Similarity	NPC280493
0.8619	High Similarity	NPC240200
0.8619	High Similarity	NPC290289
0.8619	High Similarity	NPC223534
0.8619	High Similarity	NPC158214
0.8613	High Similarity	NPC171985
0.8613	High Similarity	NPC320741
0.8613	High Similarity	NPC477835
0.8613	High Similarity	NPC472452
0.8613	High Similarity	NPC43319
0.8611	High Similarity	NPC469650

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 NPC265795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	1092
0.2-0.3	2125
0.3-0.4	2678
0.4-0.5	1710
0.5-0.6	756
0.6-0.7	216
0.7-0.8	129
0.8-0.85	29
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD6232	Discontinued
0.8613	High Similarity	NPD7473	Discontinued
0.8514	High Similarity	NPD5844	Phase 1
0.8488	Intermediate Similarity	NPD6959	Discontinued
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8453	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8427	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8361	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD2801	Approved
0.8343	Intermediate Similarity	NPD7411	Suspended
0.8305	Intermediate Similarity	NPD7054	Approved
0.8258	Intermediate Similarity	NPD7074	Phase 3
0.8258	Intermediate Similarity	NPD7472	Approved
0.8249	Intermediate Similarity	NPD3818	Discontinued
0.8246	Intermediate Similarity	NPD7819	Suspended
0.8246	Intermediate Similarity	NPD1465	Phase 2
0.8239	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6166	Phase 2
0.8225	Intermediate Similarity	NPD3226	Approved
0.8212	Intermediate Similarity	NPD6797	Phase 2
0.8167	Intermediate Similarity	NPD7251	Discontinued
0.8111	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD1934	Approved
0.8077	Intermediate Similarity	NPD8312	Approved
0.8077	Intermediate Similarity	NPD8313	Approved
0.8066	Intermediate Similarity	NPD6559	Discontinued
0.8036	Intermediate Similarity	NPD1511	Approved
0.8022	Intermediate Similarity	NPD7808	Phase 3
0.8011	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD8151	Discontinued
0.8	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD3817	Phase 2
0.7988	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD4380	Phase 2
0.7941	Intermediate Similarity	NPD1512	Approved
0.7927	Intermediate Similarity	NPD7435	Discontinued
0.7898	Intermediate Similarity	NPD3749	Approved
0.7882	Intermediate Similarity	NPD2532	Approved
0.7882	Intermediate Similarity	NPD2534	Approved
0.7882	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD2533	Approved
0.7874	Intermediate Similarity	NPD6801	Discontinued
0.7865	Intermediate Similarity	NPD6779	Approved
0.7865	Intermediate Similarity	NPD6776	Approved
0.7865	Intermediate Similarity	NPD6777	Approved
0.7865	Intermediate Similarity	NPD6778	Approved
0.7865	Intermediate Similarity	NPD6782	Approved
0.7865	Intermediate Similarity	NPD6780	Approved
0.7865	Intermediate Similarity	NPD6781	Approved
0.7853	Intermediate Similarity	NPD6234	Discontinued
0.7845	Intermediate Similarity	NPD7228	Approved
0.7841	Intermediate Similarity	NPD3882	Suspended
0.7829	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5402	Approved
0.7751	Intermediate Similarity	NPD3750	Approved
0.7747	Intermediate Similarity	NPD3751	Discontinued
0.774	Intermediate Similarity	NPD7768	Phase 2
0.7739	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD7783	Phase 2
0.7738	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7390	Discontinued
0.7704	Intermediate Similarity	NPD7870	Phase 2
0.7704	Intermediate Similarity	NPD7871	Phase 2
0.7692	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7874	Approved
0.7679	Intermediate Similarity	NPD2346	Discontinued
0.767	Intermediate Similarity	NPD37	Approved
0.7667	Intermediate Similarity	NPD7199	Phase 2
0.7665	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6599	Discontinued
0.7653	Intermediate Similarity	NPD7696	Phase 3
0.7653	Intermediate Similarity	NPD7697	Approved
0.7653	Intermediate Similarity	NPD7698	Approved
0.764	Intermediate Similarity	NPD4965	Approved
0.764	Intermediate Similarity	NPD4967	Phase 2
0.764	Intermediate Similarity	NPD4966	Approved
0.7619	Intermediate Similarity	NPD2935	Discontinued
0.7604	Intermediate Similarity	NPD6534	Approved
0.7604	Intermediate Similarity	NPD6535	Approved
0.7588	Intermediate Similarity	NPD7701	Phase 2
0.7582	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1247	Approved
0.7566	Intermediate Similarity	NPD8150	Discontinued
0.7529	Intermediate Similarity	NPD1549	Phase 2
0.7527	Intermediate Similarity	NPD3787	Discontinued
0.7514	Intermediate Similarity	NPD6799	Approved
0.7513	Intermediate Similarity	NPD6823	Phase 2
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7475	Intermediate Similarity	NPD7801	Approved
0.7471	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1510	Phase 2
0.7456	Intermediate Similarity	NPD3748	Approved
0.7443	Intermediate Similarity	NPD1653	Approved
0.7442	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1607	Approved
0.7432	Intermediate Similarity	NPD5710	Approved
0.7432	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD2796	Approved
0.7411	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7458	Discontinued
0.7401	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7240	Approved
0.7391	Intermediate Similarity	NPD3926	Phase 2
0.7386	Intermediate Similarity	NPD920	Approved
0.7386	Intermediate Similarity	NPD5403	Approved
0.7384	Intermediate Similarity	NPD2800	Approved
0.7381	Intermediate Similarity	NPD230	Phase 1
0.7371	Intermediate Similarity	NPD6212	Phase 3
0.7371	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6213	Phase 3
0.7363	Intermediate Similarity	NPD919	Approved
0.735	Intermediate Similarity	NPD8319	Approved
0.735	Intermediate Similarity	NPD8320	Phase 1
0.7341	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5953	Discontinued
0.7321	Intermediate Similarity	NPD943	Approved
0.7321	Intermediate Similarity	NPD1240	Approved
0.7314	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5408	Approved
0.731	Intermediate Similarity	NPD1551	Phase 2
0.731	Intermediate Similarity	NPD5404	Approved
0.731	Intermediate Similarity	NPD5405	Approved
0.731	Intermediate Similarity	NPD5406	Approved
0.7302	Intermediate Similarity	NPD7685	Pre-registration
0.7292	Intermediate Similarity	NPD8434	Phase 2
0.7283	Intermediate Similarity	NPD1243	Approved
0.7273	Intermediate Similarity	NPD8285	Discontinued
0.7273	Intermediate Similarity	NPD5401	Approved
0.7251	Intermediate Similarity	NPD2799	Discontinued
0.7241	Intermediate Similarity	NPD7003	Approved
0.7241	Intermediate Similarity	NPD4628	Phase 3
0.7238	Intermediate Similarity	NPD8455	Phase 2
0.7234	Intermediate Similarity	NPD7286	Phase 2
0.7209	Intermediate Similarity	NPD6100	Approved
0.7209	Intermediate Similarity	NPD6099	Approved
0.7202	Intermediate Similarity	NPD2313	Discontinued
0.7176	Intermediate Similarity	NPD1933	Approved
0.7175	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6190	Approved
0.71	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7177	Discontinued
0.7076	Intermediate Similarity	NPD447	Suspended
0.7069	Intermediate Similarity	NPD2344	Approved
0.7062	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7680	Approved
0.7041	Intermediate Similarity	NPD4287	Approved
0.7035	Intermediate Similarity	NPD6651	Approved
0.7024	Intermediate Similarity	NPD7584	Approved
0.7024	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7549	Discontinued
0.6991	Remote Similarity	NPD8059	Phase 3
0.6991	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6674	Discontinued
0.6982	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8166	Discontinued
0.6941	Remote Similarity	NPD4625	Phase 3
0.6919	Remote Similarity	NPD1613	Approved
0.6919	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4288	Approved
0.691	Remote Similarity	NPD2309	Approved
0.6907	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1470	Approved
0.6901	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3764	Approved
0.6898	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4908	Phase 1
0.6875	Remote Similarity	NPD7266	Discontinued
0.6875	Remote Similarity	NPD1471	Phase 3
0.6864	Remote Similarity	NPD2798	Approved
0.6857	Remote Similarity	NPD4308	Phase 3
0.6851	Remote Similarity	NPD6273	Approved
0.6827	Remote Similarity	NPD7585	Approved
0.6826	Remote Similarity	NPD9269	Phase 2
0.6825	Remote Similarity	NPD8127	Discontinued
0.6816	Remote Similarity	NPD4360	Phase 2
0.6816	Remote Similarity	NPD4363	Phase 3
0.6805	Remote Similarity	NPD1203	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