NPASS Compound

Structure

NPC470342 OpenBabel07101718322D 42 47 0 0 0 0 0 0 0 0999 V2000 5.9359 -6.3646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 -5.3854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -4.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -4.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -5.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -5.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -4.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -4.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -6.3646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -4.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -7.3437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -4.4063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -4.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -3.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 -4.4063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 41 1 0 0 0 0 4 42 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 20 2 0 0 0 0 9 15 1 0 0 0 0 9 19 2 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 19 1 0 0 0 0 12 27 1 0 0 0 0 13 41 1 0 0 0 0 14 15 2 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 23 2 0 0 0 0 16 29 1 0 0 0 0 17 22 2 0 0 0 0 17 29 1 0 0 0 0 18 24 1 0 0 0 0 18 28 1 0 0 0 0 19 33 1 0 0 0 0 20 22 1 0 0 0 0 20 34 1 0 0 0 0 21 25 2 0 0 0 0 21 42 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 0 0 0 0 24 30 1 0 0 0 0 24 32 2 0 0 0 0 25 26 1 0 0 0 0 25 32 1 0 0 0 0 26 27 2 0 0 0 0 27 35 1 0 0 0 0 28 36 2 0 0 0 0 29 37 2 0 0 0 0 30 38 2 0 0 0 0 31 39 2 0 0 0 0 32 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.12
Volume:	556.408
LogP:	6.248
LogD:	2.243
LogS:	-8.061
# Rotatable Bonds:	3
TPSA:	167.66
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	3.143
Fsp3:	0.125
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.108
MDCK Permeability:	1.3622665392176714e-05
Pgp-inhibitor:	0.855
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.827
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	99.49983215332031%
Volume Distribution (VD):	0.172
Pgp-substrate:	0.9509636759757996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.326
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.137
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.436
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.178
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	3.975
Half-life (T1/2):	0.01

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.29
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.051
Carcinogencity:	0.352
Eye Corrosion:	0.003
Eye Irritation:	0.897
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC470342

Natural Product ID:	NPC470342
*Common Name:**	Alterporriol Q
IUPAC Name:	2-(2,8-dihydroxy-6-methoxy-3-methyl-9,10-dioxoanthracen-1-yl)-1,7-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione
Synonyms:	Alterporriol Q
Standard InCHIKey:	IFLKWZMIHYZTTR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H22O10/c1-11-5-14-15(9-19(11)33)30(38)24-18(28(14)36)10-21(42-4)25(32(24)40)26-23-16(6-12(2)27(26)35)29(37)17-7-13(41-3)8-20(34)22(17)31(23)39/h5-10,33-35,40H,1-4H3
SMILES:	CC1=CC2=C(C=C1O)C(=O)C3=C(C(=C(C=C3C2=O)OC)C4=C(C(=CC5=C4C(=O)C6=C(C5=O)C=C(C=C6O)OC)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011668
PubChem CID:	57332381
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18494522]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276679]
NPO33215	Stemphylium sp. 33231	Species	Pleosporaceae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25136754]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25265160]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841051]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30794407]

☑ 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	7

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[492528]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22000.0	nM	PMID[492527]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[492528]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	>	10000.0	nM	PMID[492528]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	10000.0	nM	PMID[492528]
NPT1238	Organism	Staphylococcus	Staphylococcus	MIC	>	10000.0	nM	PMID[492528]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	10000.0	nM	PMID[492528]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	10000.0	nM	PMID[492528]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	>	10000.0	nM	PMID[492528]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	10000.0	nM	PMID[492528]

☑ 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 NPC470342 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	439
0.1-0.2	1780
0.2-0.3	4034
0.3-0.4	10011
0.4-0.5	8430
0.5-0.6	3788
0.6-0.7	5633
0.7-0.8	5802
0.8-0.85	2184
0.85-0.9	507
0.9-0.95	83
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472060
1.0	High Similarity	NPC472052
0.9605	High Similarity	NPC226656
0.9605	High Similarity	NPC66508
0.9545	High Similarity	NPC324736
0.9437	High Similarity	NPC477836
0.943	High Similarity	NPC477835
0.9423	High Similarity	NPC189552
0.9423	High Similarity	NPC273467
0.9371	High Similarity	NPC470341
0.9371	High Similarity	NPC105414
0.9371	High Similarity	NPC324522
0.9371	High Similarity	NPC234497
0.9371	High Similarity	NPC472058
0.9359	High Similarity	NPC312993
0.9359	High Similarity	NPC186325
0.9321	High Similarity	NPC477991
0.9321	High Similarity	NPC477992
0.9295	High Similarity	NPC177650
0.9272	High Similarity	NPC289042
0.9272	High Similarity	NPC118027
0.9272	High Similarity	NPC126767
0.9272	High Similarity	NPC245584
0.9272	High Similarity	NPC56433
0.9272	High Similarity	NPC37709
0.9272	High Similarity	NPC190648
0.9272	High Similarity	NPC312929
0.9245	High Similarity	NPC469664
0.9236	High Similarity	NPC476506
0.9216	High Similarity	NPC470568
0.9216	High Similarity	NPC294646
0.9216	High Similarity	NPC147735
0.9172	High Similarity	NPC55443
0.9172	High Similarity	NPC18699
0.9156	High Similarity	NPC470569
0.9145	High Similarity	NPC34802
0.9119	High Similarity	NPC15374
0.9097	High Similarity	NPC154683
0.9097	High Similarity	NPC40356
0.9091	High Similarity	NPC255641
0.9091	High Similarity	NPC290954
0.9073	High Similarity	NPC19896
0.9073	High Similarity	NPC227841
0.9057	High Similarity	NPC472261
0.9057	High Similarity	NPC18380
0.9051	High Similarity	NPC228654
0.9026	High Similarity	NPC329933
0.902	High Similarity	NPC290194
0.9012	High Similarity	NPC253730
0.9012	High Similarity	NPC286230
0.9012	High Similarity	NPC76647
0.9007	High Similarity	NPC167663
0.9007	High Similarity	NPC84266
0.9006	High Similarity	NPC472051
0.9006	High Similarity	NPC472057
0.9006	High Similarity	NPC169471
0.8994	High Similarity	NPC292863
0.8994	High Similarity	NPC184326
0.8987	High Similarity	NPC263483
0.8981	High Similarity	NPC254351
0.8981	High Similarity	NPC158027
0.8981	High Similarity	NPC159707
0.8981	High Similarity	NPC215203
0.8981	High Similarity	NPC52611
0.8981	High Similarity	NPC265624
0.8981	High Similarity	NPC186227
0.8981	High Similarity	NPC66029
0.8981	High Similarity	NPC205026
0.8981	High Similarity	NPC100049
0.8981	High Similarity	NPC150908
0.8981	High Similarity	NPC121649
0.8981	High Similarity	NPC248739
0.8981	High Similarity	NPC14606
0.8968	High Similarity	NPC205766
0.8961	High Similarity	NPC152233
0.8961	High Similarity	NPC172329
0.8961	High Similarity	NPC2569
0.8951	High Similarity	NPC30027
0.8944	High Similarity	NPC476505
0.894	High Similarity	NPC182255
0.894	High Similarity	NPC94076
0.8938	High Similarity	NPC137232
0.8938	High Similarity	NPC219686
0.8931	High Similarity	NPC195167
0.8931	High Similarity	NPC51760
0.8924	High Similarity	NPC180924
0.8924	High Similarity	NPC146211
0.8917	High Similarity	NPC303485
0.8917	High Similarity	NPC214632
0.8917	High Similarity	NPC329844
0.8917	High Similarity	NPC208806
0.8917	High Similarity	NPC290830
0.8917	High Similarity	NPC194593
0.8917	High Similarity	NPC72425
0.8917	High Similarity	NPC71061
0.8917	High Similarity	NPC324447
0.8917	High Similarity	NPC107109
0.891	High Similarity	NPC474417
0.891	High Similarity	NPC149526
0.8903	High Similarity	NPC65589
0.8903	High Similarity	NPC288036
0.8903	High Similarity	NPC97029
0.8903	High Similarity	NPC477221
0.8903	High Similarity	NPC158338
0.8903	High Similarity	NPC97028
0.8903	High Similarity	NPC100985
0.8896	High Similarity	NPC475348
0.8896	High Similarity	NPC261271
0.8889	High Similarity	NPC282957
0.8889	High Similarity	NPC49282
0.8889	High Similarity	NPC34482
0.8889	High Similarity	NPC194949
0.8882	High Similarity	NPC174905
0.8882	High Similarity	NPC293545
0.8882	High Similarity	NPC472059
0.8875	High Similarity	NPC284495
0.8874	High Similarity	NPC246638
0.8868	High Similarity	NPC37543
0.8868	High Similarity	NPC199463
0.8868	High Similarity	NPC212967
0.8868	High Similarity	NPC208258
0.8868	High Similarity	NPC164110
0.8868	High Similarity	NPC474637
0.8868	High Similarity	NPC246647
0.8868	High Similarity	NPC96342
0.8861	High Similarity	NPC318270
0.8861	High Similarity	NPC37253
0.8861	High Similarity	NPC79375
0.8855	High Similarity	NPC300657
0.8854	High Similarity	NPC43345
0.8839	High Similarity	NPC472841
0.8839	High Similarity	NPC27221
0.8839	High Similarity	NPC472056
0.8839	High Similarity	NPC256672
0.8839	High Similarity	NPC7025
0.8834	High Similarity	NPC251336
0.8831	High Similarity	NPC470570
0.8827	High Similarity	NPC290160
0.8827	High Similarity	NPC472053
0.8824	High Similarity	NPC21599
0.8824	High Similarity	NPC193703
0.8824	High Similarity	NPC48762
0.882	High Similarity	NPC312273
0.882	High Similarity	NPC301256
0.8816	High Similarity	NPC239136
0.8816	High Similarity	NPC19631
0.8816	High Similarity	NPC49108
0.8816	High Similarity	NPC69755
0.8816	High Similarity	NPC26238
0.8812	High Similarity	NPC105584
0.8812	High Similarity	NPC90497
0.881	High Similarity	NPC299149
0.881	High Similarity	NPC153578
0.881	High Similarity	NPC114257
0.881	High Similarity	NPC277710
0.8805	High Similarity	NPC77807
0.8805	High Similarity	NPC56049
0.8805	High Similarity	NPC137100
0.8805	High Similarity	NPC54830
0.8805	High Similarity	NPC5379
0.8805	High Similarity	NPC14561
0.8802	High Similarity	NPC216307
0.879	High Similarity	NPC476552
0.879	High Similarity	NPC67322
0.879	High Similarity	NPC222713
0.879	High Similarity	NPC232645
0.879	High Similarity	NPC478148
0.879	High Similarity	NPC111112
0.879	High Similarity	NPC72958
0.879	High Similarity	NPC476553
0.879	High Similarity	NPC476551
0.879	High Similarity	NPC138299
0.8782	High Similarity	NPC80370
0.8774	High Similarity	NPC123202
0.8774	High Similarity	NPC7943
0.8774	High Similarity	NPC22005
0.8773	High Similarity	NPC26386
0.8766	High Similarity	NPC471523
0.8766	High Similarity	NPC471524
0.8766	High Similarity	NPC471473
0.8765	High Similarity	NPC473012
0.8765	High Similarity	NPC149389
0.8758	High Similarity	NPC296752
0.8758	High Similarity	NPC295712
0.8758	High Similarity	NPC98023
0.8758	High Similarity	NPC451542
0.8758	High Similarity	NPC84571
0.8758	High Similarity	NPC471682
0.8758	High Similarity	NPC474203
0.8758	High Similarity	NPC313047
0.8758	High Similarity	NPC226462
0.8758	High Similarity	NPC195136
0.875	High Similarity	NPC271741
0.875	High Similarity	NPC317580
0.875	High Similarity	NPC178976
0.875	High Similarity	NPC287789
0.875	High Similarity	NPC201127
0.8742	High Similarity	NPC300668
0.8742	High Similarity	NPC66441
0.8742	High Similarity	NPC182555

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 NPC470342 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	1031
0.2-0.3	1582
0.3-0.4	2730
0.4-0.5	1898
0.5-0.6	996
0.6-0.7	341
0.7-0.8	154
0.8-0.85	24
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9177	High Similarity	NPD6959	Discontinued
0.9073	High Similarity	NPD7390	Discontinued
0.8882	High Similarity	NPD6232	Discontinued
0.8834	High Similarity	NPD7473	Discontinued
0.8545	High Similarity	NPD7852	Clinical (unspecified phase)
0.8543	High Similarity	NPD1509	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8408	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7768	Phase 2
0.8291	Intermediate Similarity	NPD2534	Approved
0.8291	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD2533	Approved
0.8291	Intermediate Similarity	NPD2532	Approved
0.8289	Intermediate Similarity	NPD1607	Approved
0.8261	Intermediate Similarity	NPD4380	Phase 2
0.8229	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7411	Suspended
0.8199	Intermediate Similarity	NPD3226	Approved
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8182	Intermediate Similarity	NPD3749	Approved
0.8158	Intermediate Similarity	NPD1240	Approved
0.8136	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD5406	Approved
0.8129	Intermediate Similarity	NPD5405	Approved
0.8129	Intermediate Similarity	NPD5404	Approved
0.8129	Intermediate Similarity	NPD5408	Approved
0.811	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD5844	Phase 1
0.8065	Intermediate Similarity	NPD8151	Discontinued
0.8046	Intermediate Similarity	NPD8313	Approved
0.8046	Intermediate Similarity	NPD8312	Approved
0.8038	Intermediate Similarity	NPD7003	Approved
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1549	Phase 2
0.7904	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7892	Intermediate Similarity	NPD2801	Approved
0.7874	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7075	Discontinued
0.7849	Intermediate Similarity	NPD7870	Phase 2
0.7849	Intermediate Similarity	NPD7871	Phase 2
0.7848	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1934	Approved
0.7829	Intermediate Similarity	NPD6559	Discontinued
0.7812	Intermediate Similarity	NPD3750	Approved
0.7785	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD1511	Approved
0.7765	Intermediate Similarity	NPD5494	Approved
0.7759	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2800	Approved
0.7736	Intermediate Similarity	NPD2346	Discontinued
0.773	Intermediate Similarity	NPD6780	Approved
0.773	Intermediate Similarity	NPD6776	Approved
0.773	Intermediate Similarity	NPD6779	Approved
0.773	Intermediate Similarity	NPD6781	Approved
0.773	Intermediate Similarity	NPD6778	Approved
0.773	Intermediate Similarity	NPD6782	Approved
0.773	Intermediate Similarity	NPD6777	Approved
0.7707	Intermediate Similarity	NPD6651	Approved
0.7701	Intermediate Similarity	NPD7698	Approved
0.7701	Intermediate Similarity	NPD7696	Phase 3
0.7701	Intermediate Similarity	NPD7697	Approved
0.7697	Intermediate Similarity	NPD1470	Approved
0.7692	Intermediate Similarity	NPD3882	Suspended
0.7683	Intermediate Similarity	NPD1512	Approved
0.7679	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1465	Phase 2
0.7674	Intermediate Similarity	NPD5711	Approved
0.7674	Intermediate Similarity	NPD5710	Approved
0.7651	Intermediate Similarity	NPD7458	Discontinued
0.764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2344	Approved
0.7619	Intermediate Similarity	NPD6801	Discontinued
0.7614	Intermediate Similarity	NPD7074	Phase 3
0.7606	Intermediate Similarity	NPD7435	Discontinued
0.7605	Intermediate Similarity	NPD6599	Discontinued
0.76	Intermediate Similarity	NPD3818	Discontinued
0.7562	Intermediate Similarity	NPD6099	Approved
0.7562	Intermediate Similarity	NPD6100	Approved
0.7557	Intermediate Similarity	NPD7054	Approved
0.7545	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7701	Phase 2
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7529	Intermediate Similarity	NPD3817	Phase 2
0.7514	Intermediate Similarity	NPD7472	Approved
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD7177	Discontinued
0.7486	Intermediate Similarity	NPD7808	Phase 3
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7654	Discontinued
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7472	Intermediate Similarity	NPD6797	Phase 2
0.7468	Intermediate Similarity	NPD943	Approved
0.7461	Intermediate Similarity	NPD7874	Approved
0.7461	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6535	Approved
0.7459	Intermediate Similarity	NPD6534	Approved
0.7455	Intermediate Similarity	NPD6799	Approved
0.7453	Intermediate Similarity	NPD1551	Phase 2
0.7439	Intermediate Similarity	NPD2309	Approved
0.7434	Intermediate Similarity	NPD1201	Approved
0.7433	Intermediate Similarity	NPD7700	Phase 2
0.7433	Intermediate Similarity	NPD7699	Phase 2
0.743	Intermediate Similarity	NPD7251	Discontinued
0.7427	Intermediate Similarity	NPD5402	Approved
0.7425	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD1243	Approved
0.7423	Intermediate Similarity	NPD7801	Approved
0.7412	Intermediate Similarity	NPD37	Approved
0.7401	Intermediate Similarity	NPD3751	Discontinued
0.7391	Intermediate Similarity	NPD2799	Discontinued
0.7389	Intermediate Similarity	NPD4625	Phase 3
0.7378	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7368	Intermediate Similarity	NPD6823	Phase 2
0.7342	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7783	Phase 2
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6234	Discontinued
0.7293	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD8319	Approved
0.7292	Intermediate Similarity	NPD8320	Phase 1
0.7284	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4965	Approved
0.7283	Intermediate Similarity	NPD4967	Phase 2
0.7283	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7264	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7286	Phase 2
0.7243	Intermediate Similarity	NPD4287	Approved
0.7237	Intermediate Similarity	NPD1651	Approved
0.7233	Intermediate Similarity	NPD3764	Approved
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6212	Phase 3
0.7219	Intermediate Similarity	NPD5403	Approved
0.7219	Intermediate Similarity	NPD6213	Phase 3
0.7216	Intermediate Similarity	NPD1247	Approved
0.7215	Intermediate Similarity	NPD4908	Phase 1
0.7207	Intermediate Similarity	NPD7228	Approved
0.7198	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2798	Approved
0.7186	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1283	Approved
0.7174	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4628	Phase 3
0.7168	Intermediate Similarity	NPD8455	Phase 2
0.7161	Intermediate Similarity	NPD3972	Approved
0.7125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD919	Approved
0.7101	Intermediate Similarity	NPD5401	Approved
0.7099	Intermediate Similarity	NPD230	Phase 1
0.7091	Intermediate Similarity	NPD1471	Phase 3
0.7077	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6273	Approved
0.7043	Intermediate Similarity	NPD8434	Phase 2
0.7031	Intermediate Similarity	NPD8285	Discontinued
0.7022	Intermediate Similarity	NPD7199	Phase 2
0.7011	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD4363	Phase 3
0.7	Intermediate Similarity	NPD4360	Phase 2
0.6988	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1281	Approved
0.6968	Remote Similarity	NPD4626	Approved
0.6964	Remote Similarity	NPD8166	Discontinued
0.6962	Remote Similarity	NPD1876	Approved
0.6944	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2979	Phase 3
0.6932	Remote Similarity	NPD4288	Approved
0.6932	Remote Similarity	NPD2296	Approved
0.6928	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8059	Phase 3
0.6923	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1164	Approved
0.6918	Remote Similarity	NPD1203	Approved
0.6899	Remote Similarity	NPD4749	Approved
0.6894	Remote Similarity	NPD6832	Phase 2
0.6875	Remote Similarity	NPD5761	Phase 2
0.6875	Remote Similarity	NPD5760	Phase 2
0.6875	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6746	Phase 2
0.6869	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4308	Phase 3
0.6865	Remote Similarity	NPD7240	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