NPASS Compound

Structure

NPC207467 OpenBabel07101718322D 42 46 0 0 0 0 0 0 0 0999 V2000 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 9 2 0 0 0 0 3 10 1 0 0 0 0 4 12 2 0 0 0 0 4 14 1 0 0 0 0 5 13 2 0 0 0 0 5 15 1 0 0 0 0 6 11 2 0 0 0 0 6 41 1 0 0 0 0 7 9 1 0 0 0 0 7 29 2 0 0 0 0 8 16 1 0 0 0 0 8 30 2 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 10 26 2 0 0 0 0 11 17 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 12 31 1 0 0 0 0 13 25 1 0 0 0 0 13 32 1 0 0 0 0 14 18 2 0 0 0 0 14 41 1 0 0 0 0 15 19 2 0 0 0 0 15 42 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 33 2 0 0 0 0 23 34 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 42 1 0 0 0 0 27 37 2 0 0 0 0 27 38 1 0 0 0 0 28 39 2 0 0 0 0 28 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.05
Volume:	530.942
LogP:	2.998
LogD:	1.591
LogS:	-5.067
# Rotatable Bonds:	5
TPSA:	250.08
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.1
Synthetic Accessibility Score:	3.471
Fsp3:	0.071
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:	-6.285
MDCK Permeability:	5.698551376553951e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.827
Human Intestinal Absorption (HIA):	0.989
20% Bioavailability (F20%):	0.473
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	78.1053237915039%
Volume Distribution (VD):	0.798
Pgp-substrate:	26.03570556640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.022
CYP2C9-inhibitor:	0.41
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	-0.151
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.547
Drug-inuced Liver Injury (DILI):	0.999
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.637
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.07
Respiratory Toxicity:	0.08

Download Data

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

Natural Product: NPC207467

Natural Product ID:	NPC207467
*Common Name:**	Vinaxanthone
IUPAC Name:	5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxochromen-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid
Synonyms:	Vinaxanthone
Standard InCHIKey:	MEYYEMQDVMMNNR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H16O14/c1-7(29)9-3-10-22(33)19-15(5-13(32)25(36)21(19)28(39)40)42-26(10)16(8(2)30)17(9)11-6-41-14-4-12(31)24(35)20(27(37)38)18(14)23(11)34/h3-6,31-32,35-36H,1-2H3,(H,37,38)(H,39,40)
SMILES:	CC(=O)c1cc2c(c(c1c1coc3c(c1=O)c(C(=O)O)c(c(c3)O)O)C(=O)C)oc1c(c2=O)c(C(=O)O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510257
PubChem CID:	5487402
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]

☑ 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
MIC	1
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1491	Individual Protein	1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1	Rattus norvegicus	IC50	=	5400.0	nM	PMID[497475]
NPT2588	Organism	Paracentrotus lividus	Paracentrotus lividus	IC50	=	0.12	ug.mL-1	PMID[497474]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	67.0	%	PMID[497474]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	100.0	%	PMID[497474]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[497476]
NPT2	Others	Unspecified		IC50	=	900.0	nM	PMID[497476]

☑ 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 NPC207467 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	440
0.1-0.2	2132
0.2-0.3	4739
0.3-0.4	10561
0.4-0.5	7599
0.5-0.6	4093
0.6-0.7	5379
0.7-0.8	5168
0.8-0.85	2108
0.85-0.9	464
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9819	High Similarity	NPC473785
0.976	High Similarity	NPC265795
0.9286	High Similarity	NPC158226
0.9226	High Similarity	NPC109827
0.9226	High Similarity	NPC124470
0.9222	High Similarity	NPC107009
0.92	High Similarity	NPC295436
0.9167	High Similarity	NPC165979
0.9167	High Similarity	NPC49487
0.9167	High Similarity	NPC163130
0.9167	High Similarity	NPC99613
0.9107	High Similarity	NPC76647
0.9086	High Similarity	NPC105591
0.9064	High Similarity	NPC245975
0.9059	High Similarity	NPC212038
0.9059	High Similarity	NPC81332
0.9059	High Similarity	NPC262580
0.9059	High Similarity	NPC289396
0.9059	High Similarity	NPC271848
0.9048	High Similarity	NPC29160
0.9048	High Similarity	NPC30027
0.9042	High Similarity	NPC207690
0.9017	High Similarity	NPC113446
0.8994	High Similarity	NPC234331
0.8982	High Similarity	NPC329760
0.8982	High Similarity	NPC470694
0.8977	High Similarity	NPC174486
0.8976	High Similarity	NPC119224
0.897	High Similarity	NPC263483
0.8953	High Similarity	NPC139350
0.8947	High Similarity	NPC477836
0.8935	High Similarity	NPC207575
0.8935	High Similarity	NPC13481
0.8935	High Similarity	NPC37870
0.8929	High Similarity	NPC101769
0.8929	High Similarity	NPC270837
0.8929	High Similarity	NPC236132
0.8929	High Similarity	NPC474350
0.8916	High Similarity	NPC85121
0.8909	High Similarity	NPC142339
0.8908	High Similarity	NPC212290
0.8902	High Similarity	NPC216307
0.8902	High Similarity	NPC164384
0.8895	High Similarity	NPC472054
0.8895	High Similarity	NPC37606
0.8882	High Similarity	NPC243877
0.8876	High Similarity	NPC275780
0.8876	High Similarity	NPC471788
0.8876	High Similarity	NPC239752
0.8876	High Similarity	NPC472450
0.8869	High Similarity	NPC108767
0.8869	High Similarity	NPC220912
0.8869	High Similarity	NPC294965
0.8862	High Similarity	NPC56085
0.8862	High Similarity	NPC84571
0.8862	High Similarity	NPC14353
0.8862	High Similarity	NPC228785
0.8857	High Similarity	NPC208069
0.8855	High Similarity	NPC236796
0.8848	High Similarity	NPC113906
0.8844	High Similarity	NPC68381
0.8844	High Similarity	NPC289147
0.8833	High Similarity	NPC314020
0.883	High Similarity	NPC188079
0.883	High Similarity	NPC300307
0.8824	High Similarity	NPC171985
0.8824	High Similarity	NPC43319
0.8824	High Similarity	NPC477835
0.8824	High Similarity	NPC472452
0.8824	High Similarity	NPC320741
0.8824	High Similarity	NPC472449
0.8824	High Similarity	NPC39091
0.8817	High Similarity	NPC146134
0.8817	High Similarity	NPC236521
0.8817	High Similarity	NPC197168
0.8817	High Similarity	NPC7483
0.8817	High Similarity	NPC248638
0.8817	High Similarity	NPC152659
0.8817	High Similarity	NPC23298
0.8817	High Similarity	NPC189473
0.881	High Similarity	NPC66288
0.881	High Similarity	NPC61010
0.881	High Similarity	NPC278052
0.881	High Similarity	NPC40491
0.881	High Similarity	NPC278427
0.881	High Similarity	NPC311740
0.881	High Similarity	NPC32694
0.881	High Similarity	NPC258331
0.881	High Similarity	NPC228383
0.8802	High Similarity	NPC329091
0.8802	High Similarity	NPC100123
0.8802	High Similarity	NPC45846
0.8795	High Similarity	NPC146211
0.8788	High Similarity	NPC214632
0.8788	High Similarity	NPC93552
0.8788	High Similarity	NPC89474
0.8788	High Similarity	NPC107109
0.8786	High Similarity	NPC261471
0.8786	High Similarity	NPC181523
0.8779	High Similarity	NPC78830
0.8779	High Similarity	NPC218533
0.8779	High Similarity	NPC20543
0.8779	High Similarity	NPC246716
0.8779	High Similarity	NPC239440
0.8779	High Similarity	NPC10576
0.8779	High Similarity	NPC1827
0.8772	High Similarity	NPC218226
0.8772	High Similarity	NPC6588
0.8772	High Similarity	NPC14662
0.8772	High Similarity	NPC477154
0.8772	High Similarity	NPC474024
0.8772	High Similarity	NPC260266
0.8772	High Similarity	NPC117854
0.8765	High Similarity	NPC142614
0.8765	High Similarity	NPC50960
0.8765	High Similarity	NPC37183
0.8765	High Similarity	NPC259757
0.8765	High Similarity	NPC8070
0.8765	High Similarity	NPC156432
0.8765	High Similarity	NPC473286
0.8765	High Similarity	NPC26386
0.8765	High Similarity	NPC25361
0.8765	High Similarity	NPC303174
0.8765	High Similarity	NPC326520
0.8757	High Similarity	NPC229632
0.8757	High Similarity	NPC472448
0.8757	High Similarity	NPC25152
0.8757	High Similarity	NPC261470
0.8757	High Similarity	NPC52204
0.8757	High Similarity	NPC83922
0.875	High Similarity	NPC477860
0.875	High Similarity	NPC320359
0.875	High Similarity	NPC474287
0.875	High Similarity	NPC475886
0.875	High Similarity	NPC97523
0.875	High Similarity	NPC235018
0.875	High Similarity	NPC80375
0.875	High Similarity	NPC143050
0.875	High Similarity	NPC45146
0.875	High Similarity	NPC475161
0.8743	High Similarity	NPC262286
0.8743	High Similarity	NPC241904
0.8743	High Similarity	NPC300727
0.8743	High Similarity	NPC36852
0.8743	High Similarity	NPC37543
0.8743	High Similarity	NPC79053
0.8743	High Similarity	NPC199463
0.8743	High Similarity	NPC165977
0.8743	High Similarity	NPC217677
0.8736	High Similarity	NPC474345
0.8736	High Similarity	NPC199533
0.8736	High Similarity	NPC470454
0.8736	High Similarity	NPC146803
0.8728	High Similarity	NPC5029
0.8728	High Similarity	NPC271385
0.8728	High Similarity	NPC248593
0.8728	High Similarity	NPC473113
0.8728	High Similarity	NPC111536
0.8728	High Similarity	NPC30432
0.8728	High Similarity	NPC28589
0.8728	High Similarity	NPC4200
0.8728	High Similarity	NPC76128
0.8727	High Similarity	NPC154683
0.8727	High Similarity	NPC40356
0.8721	High Similarity	NPC26568
0.8721	High Similarity	NPC476637
0.8721	High Similarity	NPC107627
0.8721	High Similarity	NPC280493
0.8721	High Similarity	NPC177480
0.8713	High Similarity	NPC20216
0.8713	High Similarity	NPC277480
0.8713	High Similarity	NPC170245
0.8713	High Similarity	NPC272502
0.8713	High Similarity	NPC224851
0.8708	High Similarity	NPC112380
0.8706	High Similarity	NPC41301
0.8706	High Similarity	NPC473313
0.8706	High Similarity	NPC186686
0.8706	High Similarity	NPC156082
0.8706	High Similarity	NPC303460
0.8706	High Similarity	NPC67959
0.8706	High Similarity	NPC472278
0.8706	High Similarity	NPC306321
0.8706	High Similarity	NPC12461
0.8706	High Similarity	NPC220313
0.8706	High Similarity	NPC329669
0.8706	High Similarity	NPC300984
0.8706	High Similarity	NPC477689
0.8701	High Similarity	NPC150977
0.8701	High Similarity	NPC182693
0.8698	High Similarity	NPC474351
0.8698	High Similarity	NPC475883
0.8698	High Similarity	NPC167678
0.8698	High Similarity	NPC29876
0.8698	High Similarity	NPC472275
0.8698	High Similarity	NPC474187
0.8698	High Similarity	NPC474186
0.8698	High Similarity	NPC266314
0.8698	High Similarity	NPC198829
0.8698	High Similarity	NPC142252

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 NPC207467 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	1087
0.2-0.3	2091
0.3-0.4	2631
0.4-0.5	1761
0.5-0.6	770
0.6-0.7	242
0.7-0.8	124
0.8-0.85	29
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8757	High Similarity	NPD6232	Discontinued
0.8721	High Similarity	NPD5844	Phase 1
0.8713	High Similarity	NPD7473	Discontinued
0.8698	High Similarity	NPD6959	Discontinued
0.8683	High Similarity	NPD4868	Clinical (unspecified phase)
0.8563	High Similarity	NPD2393	Clinical (unspecified phase)
0.8554	High Similarity	NPD7411	Suspended
0.8452	Intermediate Similarity	NPD7819	Suspended
0.8452	Intermediate Similarity	NPD2801	Approved
0.8439	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD6166	Phase 2
0.8439	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD1465	Phase 2
0.8323	Intermediate Similarity	NPD3226	Approved
0.8315	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1934	Approved
0.8251	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD5494	Approved
0.8198	Intermediate Similarity	NPD7075	Discontinued
0.8192	Intermediate Similarity	NPD7054	Approved
0.8187	Intermediate Similarity	NPD3817	Phase 2
0.8166	Intermediate Similarity	NPD4380	Phase 2
0.8146	Intermediate Similarity	NPD7074	Phase 3
0.8146	Intermediate Similarity	NPD7472	Approved
0.8136	Intermediate Similarity	NPD3818	Discontinued
0.8133	Intermediate Similarity	NPD1511	Approved
0.8101	Intermediate Similarity	NPD6797	Phase 2
0.8084	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD2532	Approved
0.8084	Intermediate Similarity	NPD2533	Approved
0.8084	Intermediate Similarity	NPD2534	Approved
0.807	Intermediate Similarity	NPD6801	Discontinued
0.8056	Intermediate Similarity	NPD7251	Discontinued
0.8036	Intermediate Similarity	NPD1512	Approved
0.8035	Intermediate Similarity	NPD3882	Suspended
0.8023	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD3749	Approved
0.7989	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD5402	Approved
0.7976	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8313	Approved
0.7967	Intermediate Similarity	NPD8312	Approved
0.7956	Intermediate Similarity	NPD6559	Discontinued
0.7931	Intermediate Similarity	NPD7768	Phase 2
0.7912	Intermediate Similarity	NPD7808	Phase 3
0.7897	Intermediate Similarity	NPD8151	Discontinued
0.7892	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6599	Discontinued
0.7844	Intermediate Similarity	NPD3750	Approved
0.7831	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7435	Discontinued
0.7811	Intermediate Similarity	NPD7390	Discontinued
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.776	Intermediate Similarity	NPD6782	Approved
0.776	Intermediate Similarity	NPD6780	Approved
0.776	Intermediate Similarity	NPD6776	Approved
0.776	Intermediate Similarity	NPD6779	Approved
0.776	Intermediate Similarity	NPD6781	Approved
0.776	Intermediate Similarity	NPD6778	Approved
0.776	Intermediate Similarity	NPD6777	Approved
0.7758	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD1247	Approved
0.7742	Intermediate Similarity	NPD8150	Discontinued
0.774	Intermediate Similarity	NPD6234	Discontinued
0.7735	Intermediate Similarity	NPD7228	Approved
0.7725	Intermediate Similarity	NPD1549	Phase 2
0.7711	Intermediate Similarity	NPD2935	Discontinued
0.7706	Intermediate Similarity	NPD6799	Approved
0.7688	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1510	Phase 2
0.7638	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7783	Phase 2
0.7637	Intermediate Similarity	NPD3751	Discontinued
0.7611	Intermediate Similarity	NPD5710	Approved
0.7611	Intermediate Similarity	NPD5711	Approved
0.7605	Intermediate Similarity	NPD2796	Approved
0.7602	Intermediate Similarity	NPD7870	Phase 2
0.7602	Intermediate Similarity	NPD7871	Phase 2
0.7588	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7874	Approved
0.7586	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD230	Phase 1
0.7572	Intermediate Similarity	NPD920	Approved
0.7572	Intermediate Similarity	NPD5403	Approved
0.7557	Intermediate Similarity	NPD37	Approved
0.7556	Intermediate Similarity	NPD7199	Phase 2
0.7551	Intermediate Similarity	NPD7696	Phase 3
0.7551	Intermediate Similarity	NPD7698	Approved
0.7551	Intermediate Similarity	NPD7697	Approved
0.7545	Intermediate Similarity	NPD3748	Approved
0.7542	Intermediate Similarity	NPD919	Approved
0.753	Intermediate Similarity	NPD1607	Approved
0.7528	Intermediate Similarity	NPD4967	Phase 2
0.7528	Intermediate Similarity	NPD4966	Approved
0.7528	Intermediate Similarity	NPD4965	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7473	Intermediate Similarity	NPD3926	Phase 2
0.7473	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2800	Approved
0.746	Intermediate Similarity	NPD8434	Phase 2
0.7457	Intermediate Similarity	NPD5401	Approved
0.7436	Intermediate Similarity	NPD8285	Discontinued
0.7427	Intermediate Similarity	NPD4628	Phase 3
0.7427	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3787	Discontinued
0.7411	Intermediate Similarity	NPD6823	Phase 2
0.741	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD943	Approved
0.7405	Intermediate Similarity	NPD7286	Phase 2
0.7396	Intermediate Similarity	NPD5405	Approved
0.7396	Intermediate Similarity	NPD5408	Approved
0.7396	Intermediate Similarity	NPD5406	Approved
0.7396	Intermediate Similarity	NPD5404	Approved
0.7385	Intermediate Similarity	NPD7700	Phase 2
0.7385	Intermediate Similarity	NPD7699	Phase 2
0.7376	Intermediate Similarity	NPD7801	Approved
0.7368	Intermediate Similarity	NPD1243	Approved
0.7356	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1653	Approved
0.7326	Intermediate Similarity	NPD7003	Approved
0.7326	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7229	Phase 3
0.7308	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6100	Approved
0.7294	Intermediate Similarity	NPD6099	Approved
0.7289	Intermediate Similarity	NPD2313	Discontinued
0.7288	Intermediate Similarity	NPD7458	Discontinued
0.7287	Intermediate Similarity	NPD7240	Approved
0.7283	Intermediate Similarity	NPD6190	Approved
0.7268	Intermediate Similarity	NPD6213	Phase 3
0.7268	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6212	Phase 3
0.7258	Intermediate Similarity	NPD7177	Discontinued
0.725	Intermediate Similarity	NPD8320	Phase 1
0.725	Intermediate Similarity	NPD8319	Approved
0.7241	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7685	Pre-registration
0.7186	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD447	Suspended
0.7158	Intermediate Similarity	NPD7549	Discontinued
0.7151	Intermediate Similarity	NPD2344	Approved
0.7127	Intermediate Similarity	NPD8455	Phase 2
0.7126	Intermediate Similarity	NPD8166	Discontinued
0.7118	Intermediate Similarity	NPD6651	Approved
0.7113	Intermediate Similarity	NPD4287	Approved
0.7108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1613	Approved
0.7083	Intermediate Similarity	NPD3268	Approved
0.7083	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4908	Phase 1
0.7066	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4625	Phase 3
0.7022	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4288	Approved
0.6989	Remote Similarity	NPD2309	Approved
0.6989	Remote Similarity	NPD8127	Discontinued
0.6988	Remote Similarity	NPD1470	Approved
0.6982	Remote Similarity	NPD3764	Approved
0.697	Remote Similarity	NPD4360	Phase 2
0.697	Remote Similarity	NPD4363	Phase 3
0.6964	Remote Similarity	NPD6832	Phase 2
0.6959	Remote Similarity	NPD1933	Approved
0.6954	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1471	Phase 3
0.6946	Remote Similarity	NPD7680	Approved
0.6936	Remote Similarity	NPD4308	Phase 3
0.6927	Remote Similarity	NPD7584	Approved
0.6923	Remote Similarity	NPD5889	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5890	Approved
0.6915	Remote Similarity	NPD5242	Approved
0.6909	Remote Similarity	NPD9269	Phase 2
0.6907	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4060	Phase 1

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