NPASS Compound

Structure

NPC163130 OpenBabel07101719152D 25 27 0 0 0 0 0 0 0 0999 V2000 5.1962 -0.0000 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 -1.7321 1.0000 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 3.4641 -2.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 -0.8660 -0.5000 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 0.8660 -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 1.7321 -0.0000 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 -0.8660 -4.5000 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 24 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 8 19 2 0 0 0 0 8 25 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.07
Volume:	332.018
LogP:	3.129
LogD:	2.205
LogS:	-5.037
# Rotatable Bonds:	3
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	2.528
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	2.2772035663365386e-05
Pgp-inhibitor:	0.21
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.122
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.696

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	97.14078521728516%
Volume Distribution (VD):	0.701
Pgp-substrate:	3.5362675189971924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.737
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.4
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	6.125
Half-life (T1/2):	0.513

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.777
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.129
Carcinogencity:	0.402
Eye Corrosion:	0.004
Eye Irritation:	0.928
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC163130

Natural Product ID:	NPC163130
*Common Name:**	5-Acetoxy-3,8-Dihydroxy-7-Methoxy-2-Methylanthracene-9,10-Dione
IUPAC Name:	(4,7-dihydroxy-3-methoxy-6-methyl-9,10-dioxoanthracen-1-yl) acetate
Synonyms:
Standard InCHIKey:	YIDYKOZHGKZOID-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O7/c1-7-4-9-10(5-11(7)20)16(21)14-12(25-8(2)19)6-13(24-3)18(23)15(14)17(9)22/h4-6,20,23H,1-3H3
SMILES:	COc1cc(OC(=O)C)c2c(c1O)C(=O)c1c(C2=O)cc(c(c1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047321
PubChem CID:	59052030
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
NPO33050	nigrospora sp.	Species	Trichosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22545792]

☑ 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
MIC	9

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	200000.0	nM	PMID[469003]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	200000.0	nM	PMID[469003]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	200000.0	nM	PMID[469003]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	>	200000.0	nM	PMID[469003]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	200000.0	nM	PMID[469003]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	>	200000.0	nM	PMID[469003]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	200000.0	nM	PMID[469003]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	200000.0	nM	PMID[469003]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	>	200000.0	nM	PMID[469003]

☑ 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 NPC163130 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	407
0.1-0.2	1924
0.2-0.3	4560
0.3-0.4	9902
0.4-0.5	7817
0.5-0.6	3532
0.6-0.7	5081
0.7-0.8	5687
0.8-0.85	2405
0.85-0.9	1246
0.9-0.95	125
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC165979
0.9875	High Similarity	NPC158226
0.9873	High Similarity	NPC29160
0.9811	High Similarity	NPC234331
0.975	High Similarity	NPC49487
0.975	High Similarity	NPC99613
0.9568	High Similarity	NPC124470
0.9568	High Similarity	NPC109827
0.9557	High Similarity	NPC84571
0.9497	High Similarity	NPC311740
0.9437	High Similarity	NPC294965
0.9437	High Similarity	NPC108767
0.9379	High Similarity	NPC474350
0.9379	High Similarity	NPC270837
0.9379	High Similarity	NPC236132
0.9367	High Similarity	NPC5379
0.9367	High Similarity	NPC77807
0.9367	High Similarity	NPC14561
0.9313	High Similarity	NPC14353
0.9313	High Similarity	NPC56085
0.9313	High Similarity	NPC228785
0.9308	High Similarity	NPC199463
0.9308	High Similarity	NPC178976
0.9308	High Similarity	NPC37543
0.9277	High Similarity	NPC139350
0.9259	High Similarity	NPC156082
0.9259	High Similarity	NPC300984
0.9255	High Similarity	NPC61010
0.9255	High Similarity	NPC66288
0.9255	High Similarity	NPC40491
0.9255	High Similarity	NPC303565
0.9255	High Similarity	NPC278052
0.925	High Similarity	NPC100123
0.925	High Similarity	NPC45846
0.9241	High Similarity	NPC107109
0.9226	High Similarity	NPC113446
0.9212	High Similarity	NPC1827
0.9212	High Similarity	NPC239440
0.9212	High Similarity	NPC10576
0.9212	High Similarity	NPC20543
0.9202	High Similarity	NPC112981
0.9198	High Similarity	NPC470694
0.9193	High Similarity	NPC119224
0.9193	High Similarity	NPC320359
0.9187	High Similarity	NPC217677
0.9187	High Similarity	NPC241904
0.9187	High Similarity	NPC165977
0.9187	High Similarity	NPC300727
0.9187	High Similarity	NPC262286
0.9187	High Similarity	NPC36852
0.9167	High Similarity	NPC207467
0.9162	High Similarity	NPC289147
0.9162	High Similarity	NPC245975
0.9152	High Similarity	NPC26568
0.9146	High Similarity	NPC37870
0.9146	High Similarity	NPC20216
0.9141	High Similarity	NPC220313
0.9141	High Similarity	NPC477689
0.9141	High Similarity	NPC236521
0.9141	High Similarity	NPC152659
0.9141	High Similarity	NPC248638
0.9141	High Similarity	NPC197168
0.9141	High Similarity	NPC7483
0.913	High Similarity	NPC238381
0.913	High Similarity	NPC476242
0.913	High Similarity	NPC168616
0.913	High Similarity	NPC83763
0.9125	High Similarity	NPC142339
0.9125	High Similarity	NPC54928
0.9125	High Similarity	NPC138243
0.9125	High Similarity	NPC274730
0.9112	High Similarity	NPC473785
0.9102	High Similarity	NPC181523
0.9096	High Similarity	NPC17219
0.9096	High Similarity	NPC246716
0.9091	High Similarity	NPC272485
0.9091	High Similarity	NPC292788
0.9085	High Similarity	NPC326520
0.9085	High Similarity	NPC275780
0.9085	High Similarity	NPC239752
0.9085	High Similarity	NPC26386
0.9085	High Similarity	NPC25361
0.9085	High Similarity	NPC8070
0.9085	High Similarity	NPC472450
0.908	High Similarity	NPC25152
0.908	High Similarity	NPC144843
0.9075	High Similarity	NPC295436
0.9074	High Similarity	NPC474287
0.9074	High Similarity	NPC476980
0.9074	High Similarity	NPC475886
0.9068	High Similarity	NPC236796
0.9068	High Similarity	NPC78225
0.9062	High Similarity	NPC113906
0.9062	High Similarity	NPC20541
0.9059	High Similarity	NPC265795
0.9057	High Similarity	NPC149889
0.9057	High Similarity	NPC101996
0.9057	High Similarity	NPC312338
0.9051	High Similarity	NPC294646
0.9042	High Similarity	NPC260263
0.903	High Similarity	NPC170245
0.903	High Similarity	NPC472452
0.903	High Similarity	NPC39091
0.9024	High Similarity	NPC101769
0.9024	High Similarity	NPC234004
0.9024	High Similarity	NPC189473
0.9024	High Similarity	NPC23298
0.9024	High Similarity	NPC207690
0.9018	High Similarity	NPC474187
0.9018	High Similarity	NPC32694
0.9018	High Similarity	NPC474351
0.9018	High Similarity	NPC258331
0.9018	High Similarity	NPC474186
0.9018	High Similarity	NPC475883
0.9012	High Similarity	NPC85121
0.9006	High Similarity	NPC68093
0.9006	High Similarity	NPC146211
0.9006	High Similarity	NPC191146
0.9	High Similarity	NPC292214
0.9	High Similarity	NPC271779
0.9	High Similarity	NPC206238
0.9	High Similarity	NPC89474
0.9	High Similarity	NPC88645
0.9	High Similarity	NPC212290
0.9	High Similarity	NPC167091
0.8994	High Similarity	NPC302783
0.8994	High Similarity	NPC171010
0.8994	High Similarity	NPC202157
0.8994	High Similarity	NPC473201
0.8988	High Similarity	NPC261471
0.8982	High Similarity	NPC218533
0.8982	High Similarity	NPC78830
0.8976	High Similarity	NPC477154
0.8976	High Similarity	NPC6588
0.8976	High Similarity	NPC76647
0.8976	High Similarity	NPC117854
0.8976	High Similarity	NPC86477
0.897	High Similarity	NPC303174
0.897	High Similarity	NPC267153
0.8963	High Similarity	NPC83922
0.8963	High Similarity	NPC8300
0.8963	High Similarity	NPC329760
0.8963	High Similarity	NPC472448
0.8963	High Similarity	NPC93739
0.8963	High Similarity	NPC81679
0.8963	High Similarity	NPC229632
0.896	High Similarity	NPC174486
0.8957	High Similarity	NPC246478
0.8957	High Similarity	NPC200746
0.8957	High Similarity	NPC47623
0.8957	High Similarity	NPC36217
0.8957	High Similarity	NPC200594
0.8957	High Similarity	NPC235018
0.8957	High Similarity	NPC45146
0.8957	High Similarity	NPC130955
0.8957	High Similarity	NPC139036
0.8951	High Similarity	NPC469584
0.8951	High Similarity	NPC136674
0.8951	High Similarity	NPC210084
0.8951	High Similarity	NPC99597
0.8951	High Similarity	NPC476981
0.8951	High Similarity	NPC223787
0.8944	High Similarity	NPC134287
0.8944	High Similarity	NPC230149
0.8944	High Similarity	NPC20830
0.8944	High Similarity	NPC57674
0.8944	High Similarity	NPC130589
0.8944	High Similarity	NPC168247
0.8944	High Similarity	NPC208197
0.8944	High Similarity	NPC38898
0.8944	High Similarity	NPC152951
0.8944	High Similarity	NPC256612
0.8944	High Similarity	NPC39184
0.8944	High Similarity	NPC117992
0.8944	High Similarity	NPC471800
0.8944	High Similarity	NPC2928
0.8941	High Similarity	NPC297807
0.8941	High Similarity	NPC98546
0.8938	High Similarity	NPC83508
0.8938	High Similarity	NPC212678
0.8938	High Similarity	NPC222830
0.8938	High Similarity	NPC241498
0.8938	High Similarity	NPC120163
0.8938	High Similarity	NPC100887
0.8938	High Similarity	NPC301323
0.8938	High Similarity	NPC120537
0.8938	High Similarity	NPC39007
0.8938	High Similarity	NPC25270
0.8938	High Similarity	NPC57030
0.8938	High Similarity	NPC131624
0.8938	High Similarity	NPC180234
0.8938	High Similarity	NPC199100
0.8938	High Similarity	NPC175978
0.8938	High Similarity	NPC161277
0.8938	High Similarity	NPC293183
0.8938	High Similarity	NPC471982
0.8938	High Similarity	NPC256283
0.8938	High Similarity	NPC239128
0.8938	High Similarity	NPC187498
0.8938	High Similarity	NPC154683

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 NPC163130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	1028
0.2-0.3	1957
0.3-0.4	2607
0.4-0.5	1691
0.5-0.6	907
0.6-0.7	371
0.7-0.8	158
0.8-0.85	24
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD6232	Discontinued
0.903	High Similarity	NPD7473	Discontinued
0.8922	High Similarity	NPD5844	Phase 1
0.8882	High Similarity	NPD2801	Approved
0.8704	High Similarity	NPD1934	Approved
0.865	High Similarity	NPD1465	Phase 2
0.865	High Similarity	NPD2393	Clinical (unspecified phase)
0.8545	High Similarity	NPD4868	Clinical (unspecified phase)
0.8519	High Similarity	NPD3226	Approved
0.8438	Intermediate Similarity	NPD1511	Approved
0.8434	Intermediate Similarity	NPD3882	Suspended
0.8424	Intermediate Similarity	NPD7819	Suspended
0.8418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD5494	Approved
0.8373	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD1512	Approved
0.8314	Intermediate Similarity	NPD3818	Discontinued
0.8304	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6166	Phase 2
0.8304	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7075	Discontinued
0.8272	Intermediate Similarity	NPD2532	Approved
0.8272	Intermediate Similarity	NPD2534	Approved
0.8272	Intermediate Similarity	NPD2533	Approved
0.8235	Intermediate Similarity	NPD6959	Discontinued
0.8204	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD3749	Approved
0.8165	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6599	Discontinued
0.8125	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7074	Phase 3
0.8084	Intermediate Similarity	NPD7411	Suspended
0.8068	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2346	Discontinued
0.8057	Intermediate Similarity	NPD7054	Approved
0.8036	Intermediate Similarity	NPD6801	Discontinued
0.8025	Intermediate Similarity	NPD3750	Approved
0.8024	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8011	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7988	Intermediate Similarity	NPD6799	Approved
0.7941	Intermediate Similarity	NPD5402	Approved
0.7939	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1607	Approved
0.7921	Intermediate Similarity	NPD6559	Discontinued
0.7919	Intermediate Similarity	NPD1247	Approved
0.7901	Intermediate Similarity	NPD1549	Phase 2
0.7895	Intermediate Similarity	NPD7768	Phase 2
0.7886	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6797	Phase 2
0.7862	Intermediate Similarity	NPD230	Phase 1
0.7862	Intermediate Similarity	NPD447	Suspended
0.7849	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1510	Phase 2
0.7824	Intermediate Similarity	NPD37	Approved
0.7821	Intermediate Similarity	NPD7251	Discontinued
0.7799	Intermediate Similarity	NPD1240	Approved
0.7799	Intermediate Similarity	NPD943	Approved
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD1551	Phase 2
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2800	Approved
0.7744	Intermediate Similarity	NPD1243	Approved
0.7738	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD920	Approved
0.7735	Intermediate Similarity	NPD8312	Approved
0.7735	Intermediate Similarity	NPD8313	Approved
0.7727	Intermediate Similarity	NPD3926	Phase 2
0.7716	Intermediate Similarity	NPD3748	Approved
0.7714	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD3751	Discontinued
0.7697	Intermediate Similarity	NPD7228	Approved
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.768	Intermediate Similarity	NPD8151	Discontinued
0.767	Intermediate Similarity	NPD5711	Approved
0.767	Intermediate Similarity	NPD5710	Approved
0.7669	Intermediate Similarity	NPD2796	Approved
0.7665	Intermediate Similarity	NPD7390	Discontinued
0.7654	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6782	Approved
0.7632	Intermediate Similarity	NPD6778	Approved
0.7632	Intermediate Similarity	NPD6777	Approved
0.7632	Intermediate Similarity	NPD6776	Approved
0.7632	Intermediate Similarity	NPD6781	Approved
0.7632	Intermediate Similarity	NPD6779	Approved
0.7632	Intermediate Similarity	NPD6780	Approved
0.7627	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD8150	Discontinued
0.7607	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2799	Discontinued
0.759	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5953	Discontinued
0.7562	Intermediate Similarity	NPD2313	Discontinued
0.7539	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5403	Approved
0.7515	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1653	Approved
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7286	Phase 2
0.7456	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5408	Approved
0.7455	Intermediate Similarity	NPD5406	Approved
0.7455	Intermediate Similarity	NPD6100	Approved
0.7455	Intermediate Similarity	NPD5404	Approved
0.7455	Intermediate Similarity	NPD6099	Approved
0.7455	Intermediate Similarity	NPD5405	Approved
0.7442	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6190	Approved
0.7438	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1933	Approved
0.7423	Intermediate Similarity	NPD7698	Approved
0.7423	Intermediate Similarity	NPD7696	Phase 3
0.7423	Intermediate Similarity	NPD7697	Approved
0.741	Intermediate Similarity	NPD2344	Approved
0.7385	Intermediate Similarity	NPD7870	Phase 2
0.7385	Intermediate Similarity	NPD7871	Phase 2
0.7374	Intermediate Similarity	NPD7229	Phase 3
0.7374	Intermediate Similarity	NPD3787	Discontinued
0.7368	Intermediate Similarity	NPD6535	Approved
0.7368	Intermediate Similarity	NPD6534	Approved
0.7362	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1613	Approved
0.736	Intermediate Similarity	NPD7701	Phase 2
0.7358	Intermediate Similarity	NPD1203	Approved
0.7358	Intermediate Similarity	NPD1470	Approved
0.7346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD4308	Phase 3
0.7282	Intermediate Similarity	NPD6823	Phase 2
0.7278	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD9269	Phase 2
0.7254	Intermediate Similarity	NPD7699	Phase 2
0.7254	Intermediate Similarity	NPD7700	Phase 2
0.725	Intermediate Similarity	NPD7801	Approved
0.7249	Intermediate Similarity	NPD4287	Approved
0.7243	Intermediate Similarity	NPD7240	Approved
0.7239	Intermediate Similarity	NPD411	Approved
0.7239	Intermediate Similarity	NPD3764	Approved
0.7239	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5242	Approved
0.7235	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD8127	Discontinued
0.7219	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7177	Discontinued
0.7212	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3027	Phase 3
0.7178	Intermediate Similarity	NPD4625	Phase 3
0.717	Intermediate Similarity	NPD9717	Approved
0.7169	Intermediate Similarity	NPD6651	Approved
0.7168	Intermediate Similarity	NPD6273	Approved
0.7168	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD9494	Approved
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD6213	Phase 3
0.7135	Intermediate Similarity	NPD6212	Phase 3
0.7135	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7128	Intermediate Similarity	NPD8285	Discontinued
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.7121	Intermediate Similarity	NPD8319	Approved
0.7117	Intermediate Similarity	NPD6832	Phase 2
0.7112	Intermediate Similarity	NPD7549	Discontinued
0.7112	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1201	Approved
0.7101	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1471	Phase 3
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1283	Approved
0.7076	Intermediate Similarity	NPD8166	Discontinued
0.7063	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD7039	Approved
0.7059	Intermediate Similarity	NPD7038	Approved
0.7048	Intermediate Similarity	NPD4307	Phase 2
0.7039	Intermediate 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