NPASS Compound

Structure

NPC473785 OpenBabel07101719512D 42 46 0 0 1 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 3 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 1 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:	578.07
Volume:	533.578
LogP:	1.77
LogD:	1.114
LogS:	-5.329
# Rotatable Bonds:	5
TPSA:	253.24
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	3.625
Fsp3:	0.107
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.439
MDCK Permeability:	5.588599833572516e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.989
20% Bioavailability (F20%):	0.638
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	78.61919403076172%
Volume Distribution (VD):	0.794
Pgp-substrate:	26.580989837646484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.031
CYP2C9-inhibitor:	0.49
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	0.857
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.449
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.675
Skin Sensitization:	0.507
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.11

Download Data

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

Natural Product: NPC473785

Natural Product ID:	NPC473785
*Common Name:**	5,7-Diacetyl-6-(5-Carboxy-6,7-Dihydroxy-4-Oxochroman-3-Yl)-2,3-Dihydroxy-9-Oxo-9H-Xanthene-1-Carboxylic Acid
IUPAC Name:	5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydrochromen-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	ZDXVSCFWCXSQJJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H18O14/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/h3-5,11,31-32,35-36H,6H2,1-2H3,(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:	CHEMBL451854
PubChem CID:	9808321
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones

*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	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	=	0.71	ug.mL-1	PMID[556012]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	12.0	%	PMID[556012]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	88.0	%	PMID[556012]

☑ 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 NPC473785 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	434
0.1-0.2	1948
0.2-0.3	4146
0.3-0.4	10038
0.4-0.5	8513
0.5-0.6	3947
0.6-0.7	5387
0.7-0.8	5217
0.8-0.85	2465
0.85-0.9	577
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9819	High Similarity	NPC207467
0.9586	High Similarity	NPC265795
0.9231	High Similarity	NPC158226
0.9167	High Similarity	NPC107009
0.9118	High Similarity	NPC271848
0.9118	High Similarity	NPC81332
0.9118	High Similarity	NPC262580
0.9118	High Similarity	NPC289396
0.9118	High Similarity	NPC212038
0.9112	High Similarity	NPC99613
0.9112	High Similarity	NPC49487
0.9112	High Similarity	NPC165979
0.9112	High Similarity	NPC163130
0.9059	High Similarity	NPC124470
0.9059	High Similarity	NPC109827
0.904	High Similarity	NPC295436
0.9034	High Similarity	NPC105591
0.9012	High Similarity	NPC245975
0.8994	High Similarity	NPC29160
0.8966	High Similarity	NPC113446
0.8941	High Similarity	NPC234331
0.8941	High Similarity	NPC76647
0.8929	High Similarity	NPC470694
0.8929	High Similarity	NPC220912
0.8922	High Similarity	NPC119224
0.8902	High Similarity	NPC139350
0.8895	High Similarity	NPC477836
0.8889	High Similarity	NPC300307
0.8882	High Similarity	NPC472452
0.8882	High Similarity	NPC30027
0.8882	High Similarity	NPC207575
0.8882	High Similarity	NPC224851
0.8882	High Similarity	NPC13481
0.8876	High Similarity	NPC101769
0.8876	High Similarity	NPC236132
0.8876	High Similarity	NPC207690
0.8876	High Similarity	NPC146134
0.8876	High Similarity	NPC474350
0.8876	High Similarity	NPC236521
0.8876	High Similarity	NPC152659
0.8876	High Similarity	NPC248638
0.8869	High Similarity	NPC228383
0.8864	High Similarity	NPC150977
0.8862	High Similarity	NPC85121
0.8857	High Similarity	NPC212290
0.8855	High Similarity	NPC142339
0.8844	High Similarity	NPC37606
0.8844	High Similarity	NPC472054
0.883	High Similarity	NPC474024
0.883	High Similarity	NPC6588
0.883	High Similarity	NPC117854
0.883	High Similarity	NPC14662
0.883	High Similarity	NPC477154
0.8824	High Similarity	NPC25361
0.8824	High Similarity	NPC471788
0.882	High Similarity	NPC174486
0.8817	High Similarity	NPC15374
0.8817	High Similarity	NPC52204
0.8817	High Similarity	NPC108767
0.8817	High Similarity	NPC25152
0.8817	High Similarity	NPC329760
0.881	High Similarity	NPC56085
0.881	High Similarity	NPC14353
0.881	High Similarity	NPC228785
0.881	High Similarity	NPC84571
0.8807	High Similarity	NPC475161
0.8807	High Similarity	NPC477860
0.8807	High Similarity	NPC208069
0.8802	High Similarity	NPC263483
0.8802	High Similarity	NPC236796
0.8795	High Similarity	NPC113906
0.8793	High Similarity	NPC474345
0.8793	High Similarity	NPC68381
0.8793	High Similarity	NPC294149
0.8793	High Similarity	NPC289147
0.8786	High Similarity	NPC472620
0.8786	High Similarity	NPC4200
0.8779	High Similarity	NPC188079
0.8772	High Similarity	NPC320741
0.8772	High Similarity	NPC171985
0.8772	High Similarity	NPC477835
0.8772	High Similarity	NPC472449
0.8772	High Similarity	NPC37870
0.8765	High Similarity	NPC270837
0.8765	High Similarity	NPC197168
0.8765	High Similarity	NPC67959
0.8765	High Similarity	NPC7483
0.8764	High Similarity	NPC112380
0.8757	High Similarity	NPC61010
0.8757	High Similarity	NPC32694
0.8757	High Similarity	NPC472275
0.8757	High Similarity	NPC278052
0.8757	High Similarity	NPC278427
0.8757	High Similarity	NPC266314
0.8757	High Similarity	NPC182693
0.8757	High Similarity	NPC311740
0.8757	High Similarity	NPC40491
0.875	High Similarity	NPC329091
0.875	High Similarity	NPC100123
0.875	High Similarity	NPC185275
0.875	High Similarity	NPC45846
0.8743	High Similarity	NPC46958
0.8743	High Similarity	NPC475246
0.8743	High Similarity	NPC146211
0.8743	High Similarity	NPC164384
0.8743	High Similarity	NPC216307
0.8736	High Similarity	NPC261471
0.8736	High Similarity	NPC181523
0.8735	High Similarity	NPC107109
0.8735	High Similarity	NPC89474
0.8728	High Similarity	NPC10576
0.8728	High Similarity	NPC1827
0.8728	High Similarity	NPC241874
0.8728	High Similarity	NPC313304
0.8728	High Similarity	NPC78830
0.8728	High Similarity	NPC20543
0.8728	High Similarity	NPC218533
0.8728	High Similarity	NPC246716
0.8728	High Similarity	NPC239440
0.8728	High Similarity	NPC103307
0.8721	High Similarity	NPC472622
0.8721	High Similarity	NPC243877
0.8713	High Similarity	NPC473286
0.8713	High Similarity	NPC239752
0.8713	High Similarity	NPC275780
0.8713	High Similarity	NPC156432
0.8713	High Similarity	NPC326520
0.8713	High Similarity	NPC472450
0.8713	High Similarity	NPC26386
0.8713	High Similarity	NPC37183
0.8713	High Similarity	NPC8070
0.8706	High Similarity	NPC294965
0.8706	High Similarity	NPC473961
0.8701	High Similarity	NPC475996
0.8698	High Similarity	NPC474287
0.8698	High Similarity	NPC235018
0.8698	High Similarity	NPC143050
0.8698	High Similarity	NPC200746
0.8698	High Similarity	NPC80375
0.8698	High Similarity	NPC45146
0.8698	High Similarity	NPC475886
0.8698	High Similarity	NPC320359
0.8693	High Similarity	NPC246877
0.8693	High Similarity	NPC476621
0.8693	High Similarity	NPC476623
0.8693	High Similarity	NPC265380
0.8693	High Similarity	NPC472387
0.8693	High Similarity	NPC476622
0.8693	High Similarity	NPC471789
0.8693	High Similarity	NPC476619
0.8693	High Similarity	NPC476620
0.8693	High Similarity	NPC476618
0.869	High Similarity	NPC79053
0.869	High Similarity	NPC37543
0.869	High Similarity	NPC199463
0.869	High Similarity	NPC300727
0.869	High Similarity	NPC36852
0.869	High Similarity	NPC469584
0.869	High Similarity	NPC165977
0.869	High Similarity	NPC262286
0.869	High Similarity	NPC241904
0.869	High Similarity	NPC217677
0.8686	High Similarity	NPC146803
0.8686	High Similarity	NPC3718
0.8683	High Similarity	NPC472048
0.8681	High Similarity	NPC314020
0.8681	High Similarity	NPC477082
0.8678	High Similarity	NPC5029
0.8678	High Similarity	NPC65333
0.8678	High Similarity	NPC76128
0.8678	High Similarity	NPC30432
0.8678	High Similarity	NPC28589
0.8678	High Similarity	NPC271385
0.8678	High Similarity	NPC257667
0.8678	High Similarity	NPC248593
0.8678	High Similarity	NPC472454
0.8678	High Similarity	NPC473113
0.8678	High Similarity	NPC111536
0.8678	High Similarity	NPC186847
0.8678	High Similarity	NPC100251
0.8675	High Similarity	NPC154683
0.8675	High Similarity	NPC40356
0.8674	High Similarity	NPC264302
0.8671	High Similarity	NPC107627
0.8671	High Similarity	NPC177480
0.8671	High Similarity	NPC26568
0.8671	High Similarity	NPC472619
0.8671	High Similarity	NPC476637
0.8671	High Similarity	NPC326877
0.8663	High Similarity	NPC20216
0.8663	High Similarity	NPC39091
0.8663	High Similarity	NPC120593
0.8663	High Similarity	NPC43319
0.8663	High Similarity	NPC272560
0.8663	High Similarity	NPC170245
0.8663	High Similarity	NPC472621
0.8663	High Similarity	NPC277480
0.8659	High Similarity	NPC304322
0.8655	High Similarity	NPC329669
0.8655	High Similarity	NPC473313

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 NPC473785 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	1061
0.2-0.3	1991
0.3-0.4	2640
0.4-0.5	1792
0.5-0.6	837
0.6-0.7	267
0.7-0.8	140
0.8-0.85	29
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8772	High Similarity	NPD7473	Discontinued
0.8757	High Similarity	NPD6959	Discontinued
0.8706	High Similarity	NPD6232	Discontinued
0.8671	High Similarity	NPD5844	Phase 1
0.8631	High Similarity	NPD4868	Clinical (unspecified phase)
0.8512	High Similarity	NPD2393	Clinical (unspecified phase)
0.8503	High Similarity	NPD7411	Suspended
0.8497	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD6166	Phase 2
0.8497	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD1465	Phase 2
0.8402	Intermediate Similarity	NPD7819	Suspended
0.8391	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD5494	Approved
0.8362	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8297	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD2801	Approved
0.8274	Intermediate Similarity	NPD3226	Approved
0.8235	Intermediate Similarity	NPD1934	Approved
0.8207	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD7074	Phase 3
0.8167	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD7075	Discontinued
0.8146	Intermediate Similarity	NPD7054	Approved
0.8122	Intermediate Similarity	NPD8312	Approved
0.8122	Intermediate Similarity	NPD8313	Approved
0.8101	Intermediate Similarity	NPD7472	Approved
0.8056	Intermediate Similarity	NPD6797	Phase 2
0.8036	Intermediate Similarity	NPD2533	Approved
0.8036	Intermediate Similarity	NPD2534	Approved
0.8036	Intermediate Similarity	NPD2532	Approved
0.8035	Intermediate Similarity	NPD3817	Phase 2
0.8012	Intermediate Similarity	NPD4380	Phase 2
0.8011	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD3818	Discontinued
0.7989	Intermediate Similarity	NPD3882	Suspended
0.7977	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD1511	Approved
0.7949	Intermediate Similarity	NPD8151	Discontinued
0.7943	Intermediate Similarity	NPD3749	Approved
0.7929	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6801	Discontinued
0.7912	Intermediate Similarity	NPD6559	Discontinued
0.7889	Intermediate Similarity	NPD7228	Approved
0.7886	Intermediate Similarity	NPD7768	Phase 2
0.7882	Intermediate Similarity	NPD1512	Approved
0.7869	Intermediate Similarity	NPD7808	Phase 3
0.7845	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5402	Approved
0.7824	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6599	Discontinued
0.7797	Intermediate Similarity	NPD6234	Discontinued
0.7796	Intermediate Similarity	NPD8150	Discontinued
0.7784	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7435	Discontinued
0.7765	Intermediate Similarity	NPD7390	Discontinued
0.7742	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD2346	Discontinued
0.772	Intermediate Similarity	NPD6780	Approved
0.772	Intermediate Similarity	NPD6779	Approved
0.772	Intermediate Similarity	NPD6778	Approved
0.772	Intermediate Similarity	NPD6782	Approved
0.772	Intermediate Similarity	NPD6777	Approved
0.772	Intermediate Similarity	NPD6776	Approved
0.772	Intermediate Similarity	NPD6781	Approved
0.7719	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3750	Approved
0.7688	Intermediate Similarity	NPD7783	Phase 2
0.7688	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1549	Phase 2
0.7665	Intermediate Similarity	NPD2935	Discontinued
0.7661	Intermediate Similarity	NPD6799	Approved
0.7644	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD37	Approved
0.7611	Intermediate Similarity	NPD1247	Approved
0.7611	Intermediate Similarity	NPD7199	Phase 2
0.7602	Intermediate Similarity	NPD7698	Approved
0.7602	Intermediate Similarity	NPD7696	Phase 3
0.7602	Intermediate Similarity	NPD7697	Approved
0.7596	Intermediate Similarity	NPD3751	Discontinued
0.7584	Intermediate Similarity	NPD4965	Approved
0.7584	Intermediate Similarity	NPD4967	Phase 2
0.7584	Intermediate Similarity	NPD4966	Approved
0.7569	Intermediate Similarity	NPD5711	Approved
0.7569	Intermediate Similarity	NPD5710	Approved
0.7563	Intermediate Similarity	NPD7871	Phase 2
0.7563	Intermediate Similarity	NPD7870	Phase 2
0.755	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7874	Approved
0.7538	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7701	Phase 2
0.753	Intermediate Similarity	NPD230	Phase 1
0.7527	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD1510	Phase 2
0.7485	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1607	Approved
0.7473	Intermediate Similarity	NPD5953	Discontinued
0.7461	Intermediate Similarity	NPD6535	Approved
0.7461	Intermediate Similarity	NPD6534	Approved
0.7456	Intermediate Similarity	NPD1551	Phase 2
0.7456	Intermediate Similarity	NPD2796	Approved
0.7436	Intermediate Similarity	NPD7699	Phase 2
0.7436	Intermediate Similarity	NPD7700	Phase 2
0.7433	Intermediate Similarity	NPD7240	Approved
0.7432	Intermediate Similarity	NPD3926	Phase 2
0.7429	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD920	Approved
0.7429	Intermediate Similarity	NPD5403	Approved
0.7427	Intermediate Similarity	NPD2800	Approved
0.7426	Intermediate Similarity	NPD7801	Approved
0.7414	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD919	Approved
0.7396	Intermediate Similarity	NPD3748	Approved
0.7396	Intermediate Similarity	NPD2799	Discontinued
0.7387	Intermediate Similarity	NPD8320	Phase 1
0.7387	Intermediate Similarity	NPD8319	Approved
0.7384	Intermediate Similarity	NPD7003	Approved
0.7384	Intermediate Similarity	NPD4628	Phase 3
0.7377	Intermediate Similarity	NPD7229	Phase 3
0.7377	Intermediate Similarity	NPD3787	Discontinued
0.7374	Intermediate Similarity	NPD6823	Phase 2
0.7366	Intermediate Similarity	NPD7286	Phase 2
0.7365	Intermediate Similarity	NPD943	Approved
0.7365	Intermediate Similarity	NPD1240	Approved
0.7353	Intermediate Similarity	NPD5408	Approved
0.7353	Intermediate Similarity	NPD5404	Approved
0.7353	Intermediate Similarity	NPD5406	Approved
0.7353	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD6099	Approved
0.7353	Intermediate Similarity	NPD5405	Approved
0.7345	Intermediate Similarity	NPD7458	Discontinued
0.7314	Intermediate Similarity	NPD5401	Approved
0.731	Intermediate Similarity	NPD8285	Discontinued
0.7273	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6190	Approved
0.7231	Intermediate Similarity	NPD6213	Phase 3
0.7231	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6212	Phase 3
0.7225	Intermediate Similarity	NPD1243	Approved
0.7219	Intermediate Similarity	NPD7177	Discontinued
0.7216	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1653	Approved
0.7184	Intermediate Similarity	NPD8166	Discontinued
0.7184	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8455	Phase 2
0.7176	Intermediate Similarity	NPD6651	Approved
0.7158	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4908	Phase 1
0.712	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7549	Discontinued
0.7118	Intermediate Similarity	NPD447	Suspended
0.711	Intermediate Similarity	NPD2344	Approved
0.7102	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6273	Approved
0.7079	Intermediate Similarity	NPD7680	Approved
0.7077	Intermediate Similarity	NPD4287	Approved
0.7066	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1613	Approved
0.7043	Intermediate Similarity	NPD8127	Discontinued
0.7041	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3268	Approved
0.7031	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4625	Phase 3
0.6978	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4060	Phase 1
0.6949	Remote Similarity	NPD2309	Approved
0.6946	Remote Similarity	NPD1470	Approved
0.6941	Remote Similarity	NPD3764	Approved
0.6935	Remote Similarity	NPD4363	Phase 3
0.6935	Remote Similarity	NPD4360	Phase 2
0.6932	Remote Similarity	NPD6674	Discontinued
0.6923	Remote Similarity	NPD6832	Phase 2
0.6919	Remote Similarity	NPD1933	Approved
0.6914	Remote Similarity	NPD1471	Phase 3
0.6878	Remote Similarity	NPD5242	Approved
0.6867	Remote Similarity	NPD9269	Phase 2
0.6866	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8059	Phase 3
0.6865	Remote Similarity	NPD4288	Approved
0.6865	Remote Similarity	NPD5353	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