NPASS Compound

Structure

NPC147735 OpenBabel07101718202D 22 24 0 0 0 0 0 0 0 0999 V2000 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 2.5981 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 -2.5981 0.5000 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 2.5981 1.5000 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 0.8660 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 -0.0000 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 -0.8660 0.5000 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 -0.0000 2.0000 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 3.4641 3.0000 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 -1.7321 -1.0000 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 0.0000 -1.0000 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 1 22 1 0 0 0 0 2 7 2 0 0 0 0 2 9 1 0 0 0 0 3 7 1 0 0 0 0 3 12 2 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 8 1 0 0 0 0 5 11 2 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 14 16 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	2.928
LogD:	2.055
LogS:	-3.955
# Rotatable Bonds:	2
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	2.745
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.227
MDCK Permeability:	4.558501132123638e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.522
20% Bioavailability (F20%):	0.538
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	93.65196990966797%
Volume Distribution (VD):	0.553
Pgp-substrate:	10.296794891357422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.399
CYP2C9-substrate:	0.64
CYP2D6-inhibitor:	0.121
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.143
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	8.239
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.026
Drug-inuced Liver Injury (DILI):	0.37
AMES Toxicity:	0.44
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.913
Carcinogencity:	0.029
Eye Corrosion:	0.043
Eye Irritation:	0.93
Respiratory Toxicity:	0.777

Download Data

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

Natural Product: NPC147735

Natural Product ID:	NPC147735
*Common Name:**	Carviolin
IUPAC Name:	1,3-dihydroxy-6-(hydroxymethyl)-8-methoxyanthracene-9,10-dione
Synonyms:	Carviolin
Standard InCHIKey:	XNMZBRJAWRIJII-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-22-12-3-7(6-17)2-9-14(12)16(21)13-10(15(9)20)4-8(18)5-11(13)19/h2-5,17-19H,6H2,1H3
SMILES:	COc1cc(cc2c1C(=O)c1c(cc(cc1O)O)C2=O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464169
PubChem CID:	10040432
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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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

Activity Type	# Activity
Cell Line	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	100000.0	nM	PMID[483652]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100000.0	nM	PMID[483652]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	41660.0	nM	PMID[483652]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[483652]

☑ 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 NPC147735 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	392
0.1-0.2	1696
0.2-0.3	3831
0.3-0.4	9255
0.4-0.5	9168
0.5-0.6	3530
0.6-0.7	5434
0.7-0.8	5593
0.8-0.85	2631
0.85-0.9	1010
0.9-0.95	134
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC290954
0.9861	High Similarity	NPC255641
0.9793	High Similarity	NPC470569
0.979	High Similarity	NPC190648
0.979	High Similarity	NPC289042
0.979	High Similarity	NPC118027
0.979	High Similarity	NPC56433
0.979	High Similarity	NPC312929
0.979	High Similarity	NPC126767
0.979	High Similarity	NPC245584
0.9724	High Similarity	NPC470568
0.9724	High Similarity	NPC294646
0.9592	High Similarity	NPC40356
0.9592	High Similarity	NPC154683
0.958	High Similarity	NPC19896
0.9533	High Similarity	NPC324736
0.9527	High Similarity	NPC208806
0.9456	High Similarity	NPC202595
0.9444	High Similarity	NPC21599
0.9444	High Similarity	NPC48762
0.9444	High Similarity	NPC193703
0.9396	High Similarity	NPC107109
0.9384	High Similarity	NPC34802
0.9379	High Similarity	NPC49282
0.9379	High Similarity	NPC34482
0.9375	High Similarity	NPC167663
0.9333	High Similarity	NPC66508
0.9333	High Similarity	NPC226656
0.932	High Similarity	NPC172329
0.932	High Similarity	NPC2569
0.9315	High Similarity	NPC300540
0.9315	High Similarity	NPC470570
0.9306	High Similarity	NPC182255
0.9306	High Similarity	NPC94076
0.9272	High Similarity	NPC77807
0.9272	High Similarity	NPC5379
0.9272	High Similarity	NPC14561
0.9267	High Similarity	NPC214632
0.9262	High Similarity	NPC474417
0.9262	High Similarity	NPC149526
0.9262	High Similarity	NPC478148
0.9257	High Similarity	NPC329933
0.9247	High Similarity	NPC478019
0.9241	High Similarity	NPC84266
0.9236	High Similarity	NPC305845
0.9236	High Similarity	NPC204045
0.9231	High Similarity	NPC190457
0.9216	High Similarity	NPC84571
0.9216	High Similarity	NPC472052
0.9216	High Similarity	NPC470342
0.9216	High Similarity	NPC472060
0.9211	High Similarity	NPC263483
0.9211	High Similarity	NPC199463
0.9211	High Similarity	NPC37543
0.9211	High Similarity	NPC178976
0.92	High Similarity	NPC51824
0.92	High Similarity	NPC180944
0.92	High Similarity	NPC470338
0.92	High Similarity	NPC113608
0.92	High Similarity	NPC470340
0.92	High Similarity	NPC470337
0.92	High Similarity	NPC268992
0.9189	High Similarity	NPC472056
0.9189	High Similarity	NPC256672
0.9189	High Similarity	NPC27221
0.9189	High Similarity	NPC7025
0.9178	High Similarity	NPC471906
0.9178	High Similarity	NPC244691
0.9178	High Similarity	NPC475201
0.9172	High Similarity	NPC49108
0.9172	High Similarity	NPC135524
0.9156	High Similarity	NPC311740
0.9139	High Similarity	NPC155686
0.9139	High Similarity	NPC93552
0.9139	High Similarity	NPC135522
0.9133	High Similarity	NPC46882
0.9133	High Similarity	NPC232645
0.9133	High Similarity	NPC132990
0.9133	High Similarity	NPC72958
0.9133	High Similarity	NPC230848
0.9128	High Similarity	NPC158338
0.9128	High Similarity	NPC100985
0.9128	High Similarity	NPC97028
0.9128	High Similarity	NPC97029
0.9128	High Similarity	NPC65589
0.9128	High Similarity	NPC288036
0.9128	High Similarity	NPC80370
0.9122	High Similarity	NPC22005
0.9122	High Similarity	NPC7943
0.9122	High Similarity	NPC71055
0.9122	High Similarity	NPC123202
0.9116	High Similarity	NPC28632
0.9108	High Similarity	NPC234497
0.9108	High Similarity	NPC105414
0.9108	High Similarity	NPC324522
0.9108	High Similarity	NPC470341
0.9108	High Similarity	NPC472058
0.9103	High Similarity	NPC253822
0.9103	High Similarity	NPC101366
0.9097	High Similarity	NPC1268
0.9091	High Similarity	NPC284495
0.9091	High Similarity	NPC471905
0.9091	High Similarity	NPC470810
0.9079	High Similarity	NPC68727
0.9073	High Similarity	NPC175978
0.9073	High Similarity	NPC273483
0.9073	High Similarity	NPC87708
0.9067	High Similarity	NPC119929
0.9067	High Similarity	NPC225854
0.9054	High Similarity	NPC225173
0.9054	High Similarity	NPC163846
0.9048	High Similarity	NPC475705
0.9048	High Similarity	NPC117836
0.9048	High Similarity	NPC51887
0.9048	High Similarity	NPC476178
0.9041	High Similarity	NPC474961
0.9041	High Similarity	NPC470087
0.9041	High Similarity	NPC321980
0.9041	High Similarity	NPC268204
0.9041	High Similarity	NPC55832
0.9041	High Similarity	NPC469404
0.9041	High Similarity	NPC52789
0.9041	High Similarity	NPC26051
0.9038	High Similarity	NPC101769
0.9038	High Similarity	NPC100849
0.9034	High Similarity	NPC472366
0.9034	High Similarity	NPC295384
0.9021	High Similarity	NPC254847
0.902	High Similarity	NPC146211
0.902	High Similarity	NPC180924
0.9013	High Similarity	NPC169990
0.9013	High Similarity	NPC210942
0.9013	High Similarity	NPC329844
0.9007	High Similarity	NPC39819
0.9007	High Similarity	NPC258249
0.9	High Similarity	NPC65775
0.9	High Similarity	NPC10027
0.8993	High Similarity	NPC125801
0.8986	High Similarity	NPC476055
0.8981	High Similarity	NPC472057
0.8981	High Similarity	NPC472051
0.898	High Similarity	NPC3732
0.898	High Similarity	NPC310340
0.8973	High Similarity	NPC204985
0.8973	High Similarity	NPC124365
0.8973	High Similarity	NPC172250
0.8973	High Similarity	NPC215311
0.8973	High Similarity	NPC80962
0.8973	High Similarity	NPC213659
0.8973	High Similarity	NPC259166
0.8973	High Similarity	NPC48624
0.8973	High Similarity	NPC144118
0.8973	High Similarity	NPC326109
0.8973	High Similarity	NPC219917
0.8966	High Similarity	NPC242994
0.8966	High Similarity	NPC309154
0.8966	High Similarity	NPC12175
0.8966	High Similarity	NPC138099
0.8966	High Similarity	NPC55162
0.8966	High Similarity	NPC90665
0.8966	High Similarity	NPC143438
0.8966	High Similarity	NPC279668
0.8966	High Similarity	NPC278323
0.8961	High Similarity	NPC201127
0.8961	High Similarity	NPC212967
0.8961	High Similarity	NPC44199
0.8961	High Similarity	NPC246647
0.8961	High Similarity	NPC96342
0.8961	High Similarity	NPC164110
0.8961	High Similarity	NPC474637
0.8958	High Similarity	NPC53414
0.8958	High Similarity	NPC53206
0.8958	High Similarity	NPC193792
0.8947	High Similarity	NPC474843
0.8947	High Similarity	NPC149889
0.8947	High Similarity	NPC312338
0.894	High Similarity	NPC470107
0.894	High Similarity	NPC295036
0.894	High Similarity	NPC227122
0.894	High Similarity	NPC325983
0.894	High Similarity	NPC280295
0.894	High Similarity	NPC474660
0.8938	High Similarity	NPC111536
0.8938	High Similarity	NPC271385
0.8938	High Similarity	NPC30432
0.8938	High Similarity	NPC76128
0.8938	High Similarity	NPC5029
0.8933	High Similarity	NPC39195
0.8933	High Similarity	NPC153417
0.8926	High Similarity	NPC187282
0.8926	High Similarity	NPC290133
0.8926	High Similarity	NPC24136
0.8924	High Similarity	NPC29160
0.8924	High Similarity	NPC477835
0.8919	High Similarity	NPC245482
0.8919	High Similarity	NPC301751
0.8912	High Similarity	NPC470089
0.8912	High Similarity	NPC232021
0.8912	High Similarity	NPC40118
0.8912	High Similarity	NPC126534

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 NPC147735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	1021
0.2-0.3	1567
0.3-0.4	2651
0.4-0.5	1865
0.5-0.6	1081
0.6-0.7	387
0.7-0.8	168
0.8-0.85	36
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9021	High Similarity	NPD1509	Clinical (unspecified phase)
0.8854	High Similarity	NPD6232	Discontinued
0.8805	High Similarity	NPD7473	Discontinued
0.879	High Similarity	NPD6959	Discontinued
0.8759	High Similarity	NPD1510	Phase 2
0.875	High Similarity	NPD1607	Approved
0.8733	High Similarity	NPD2534	Approved
0.8733	High Similarity	NPD2532	Approved
0.8733	High Similarity	NPD2533	Approved
0.8645	High Similarity	NPD7819	Suspended
0.8611	High Similarity	NPD1240	Approved
0.8609	High Similarity	NPD4378	Clinical (unspecified phase)
0.8571	High Similarity	NPD4380	Phase 2
0.8526	High Similarity	NPD2393	Clinical (unspecified phase)
0.8506	High Similarity	NPD3226	Approved
0.8456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1549	Phase 2
0.8421	Intermediate Similarity	NPD7390	Discontinued
0.8389	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1934	Approved
0.828	Intermediate Similarity	NPD7411	Suspended
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.82	Intermediate Similarity	NPD2796	Approved
0.82	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD2801	Approved
0.8158	Intermediate Similarity	NPD2800	Approved
0.8146	Intermediate Similarity	NPD2346	Discontinued
0.8137	Intermediate Similarity	NPD3749	Approved
0.8137	Intermediate Similarity	NPD7075	Discontinued
0.8125	Intermediate Similarity	NPD1470	Approved
0.8105	Intermediate Similarity	NPD3750	Approved
0.8105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1512	Approved
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8075	Intermediate Similarity	NPD7768	Phase 2
0.8063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6166	Phase 2
0.8061	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5710	Approved
0.8049	Intermediate Similarity	NPD5711	Approved
0.8037	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7964	Intermediate Similarity	NPD3818	Discontinued
0.7963	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7922	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6651	Approved
0.7867	Intermediate Similarity	NPD943	Approved
0.7847	Intermediate Similarity	NPD1201	Approved
0.7843	Intermediate Similarity	NPD5406	Approved
0.7843	Intermediate Similarity	NPD5405	Approved
0.7843	Intermediate Similarity	NPD6100	Approved
0.7843	Intermediate Similarity	NPD5408	Approved
0.7843	Intermediate Similarity	NPD6099	Approved
0.7843	Intermediate Similarity	NPD5404	Approved
0.7834	Intermediate Similarity	NPD6799	Approved
0.7811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD920	Approved
0.7792	Intermediate Similarity	NPD2344	Approved
0.7791	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD6779	Approved
0.7778	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD6777	Approved
0.7778	Intermediate Similarity	NPD6781	Approved
0.7778	Intermediate Similarity	NPD3748	Approved
0.7778	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD6780	Approved
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.773	Intermediate Similarity	NPD8151	Discontinued
0.773	Intermediate Similarity	NPD1465	Phase 2
0.7719	Intermediate Similarity	NPD5953	Discontinued
0.7706	Intermediate Similarity	NPD7054	Approved
0.7702	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1243	Approved
0.7688	Intermediate Similarity	NPD8313	Approved
0.7688	Intermediate Similarity	NPD8312	Approved
0.7683	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2799	Discontinued
0.7662	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7472	Approved
0.765	Intermediate Similarity	NPD7435	Discontinued
0.765	Intermediate Similarity	NPD7698	Approved
0.765	Intermediate Similarity	NPD7696	Phase 3
0.765	Intermediate Similarity	NPD7697	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4628	Phase 3
0.7643	Intermediate Similarity	NPD7003	Approved
0.7636	Intermediate Similarity	NPD4966	Approved
0.7636	Intermediate Similarity	NPD4965	Approved
0.7636	Intermediate Similarity	NPD4967	Phase 2
0.763	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD6797	Phase 2
0.7609	Intermediate Similarity	NPD7870	Phase 2
0.7609	Intermediate Similarity	NPD7871	Phase 2
0.7602	Intermediate Similarity	NPD7286	Phase 2
0.7595	Intermediate Similarity	NPD2309	Approved
0.7593	Intermediate Similarity	NPD7458	Discontinued
0.7582	Intermediate Similarity	NPD230	Phase 1
0.7572	Intermediate Similarity	NPD7251	Discontinued
0.756	Intermediate Similarity	NPD1247	Approved
0.7557	Intermediate Similarity	NPD8150	Discontinued
0.755	Intermediate Similarity	NPD4625	Phase 3
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7529	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7469	Intermediate Similarity	NPD5403	Approved
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2798	Approved
0.7453	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5401	Approved
0.7452	Intermediate Similarity	NPD1471	Phase 3
0.745	Intermediate Similarity	NPD1283	Approved
0.744	Intermediate Similarity	NPD919	Approved
0.7432	Intermediate Similarity	NPD3972	Approved
0.7407	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7874	Approved
0.7405	Intermediate Similarity	NPD6823	Phase 2
0.7397	Intermediate Similarity	NPD1651	Approved
0.7391	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7700	Phase 2
0.7377	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD7801	Approved
0.7351	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7177	Discontinued
0.7341	Intermediate Similarity	NPD7228	Approved
0.7333	Intermediate Similarity	NPD1876	Approved
0.731	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7308	Intermediate Similarity	NPD4360	Phase 2
0.7308	Intermediate Similarity	NPD4363	Phase 3
0.7305	Intermediate Similarity	NPD5761	Phase 2
0.7305	Intermediate Similarity	NPD5760	Phase 2
0.7301	Intermediate Similarity	NPD6273	Approved
0.7285	Intermediate Similarity	NPD1203	Approved
0.7273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7253	Intermediate Similarity	NPD6212	Phase 3
0.7253	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6213	Phase 3
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.725	Intermediate Similarity	NPD2654	Approved
0.7248	Intermediate Similarity	NPD1281	Approved
0.7248	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7244	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8320	Phase 1
0.7234	Intermediate Similarity	NPD8319	Approved
0.7233	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4626	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7208	Intermediate Similarity	NPD3027	Phase 3
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7783	Phase 2
0.7182	Intermediate Similarity	NPD4287	Approved
0.7179	Intermediate Similarity	NPD2979	Phase 3
0.7179	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1613	Approved
0.7174	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4361	Phase 2
0.7171	Intermediate Similarity	NPD1164	Approved
0.7161	Intermediate Similarity	NPD411	Approved
0.716	Intermediate Similarity	NPD4288	Approved
0.7152	Intermediate Similarity	NPD4749	Approved
0.7143	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD447	Suspended
0.7107	Intermediate Similarity	NPD7033	Discontinued
0.7095	Intermediate Similarity	NPD1548	Phase 1
0.7095	Intermediate Similarity	NPD9545	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