NPASS Compound

Structure

NPC167663 OpenBabel07101719242D 23 25 0 0 0 0 0 0 0 0999 V2000 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -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 -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 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 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 10 21 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 17 19 2 0 0 0 0 18 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	3.506
LogD:	3.103
LogS:	-5.928
# Rotatable Bonds:	3
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	2.167
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.849
MDCK Permeability:	4.7645869926782325e-05
Pgp-inhibitor:	0.697
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.445

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.255
Plasma Protein Binding (PPB):	86.67980194091797%
Volume Distribution (VD):	0.686
Pgp-substrate:	4.752598762512207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.884
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.496
CYP2C19-substrate:	0.636
CYP2C9-inhibitor:	0.564
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.495

ADMET: Excretion

Clearance (CL):	10.03
Half-life (T1/2):	0.122

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.896
AMES Toxicity:	0.716
Rat Oral Acute Toxicity:	0.164
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.068
Carcinogencity:	0.332
Eye Corrosion:	0.004
Eye Irritation:	0.941
Respiratory Toxicity:	0.264

Download Data

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

Natural Product: NPC167663

Natural Product ID:	NPC167663
*Common Name:**	1,3,8-Tri-O-Methylemodin
IUPAC Name:	1,3,8-trimethoxy-6-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	HICKZJMJOXACIR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-9-5-11-15(13(6-9)22-3)18(20)16-12(17(11)19)7-10(21-2)8-14(16)23-4/h5-8H,1-4H3
SMILES:	Cc1cc2c(c(c1)OC)C(=O)c1c(cc(cc1OC)OC)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL428867
PubChem CID:	7330510
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	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
Others	16

Activity Type	# Activity
Cell Line	3
Individual Protein	3
Others	5
Protein Family	3
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3769	Individual Protein	Elastase 2A	Sus scrofa	Inhibition	=	4.0	%	PMID[497205]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	16.0	%	PMID[497205]
NPT2682	Individual Protein	Alpha-chymotrypsin	Bos taurus	Inhibition	=	6.0	%	PMID[497205]
NPT137	Cell Line	L1210	Mus musculus	ID50	=	0.0001	M	PMID[497207]
NPT116	Cell Line	HL-60	Homo sapiens	ID50	=	0.000049	M	PMID[497207]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[497208]
NPT544	Protein Family	Estrogen receptor	Homo sapiens	Control	=	99.1	%	PMID[497206]
NPT544	Protein Family	Estrogen receptor	Homo sapiens	Control	=	109.3	%	PMID[497206]
NPT544	Protein Family	Estrogen receptor	Homo sapiens	Control	<	127.2	%	PMID[497206]
NPT317	Uncleic Acid	Nucleic Acid		ID50	=	0.000021	M	PMID[497207]
NPT317	Uncleic Acid	Nucleic Acid		Ratio	=	0.43	n.a.	PMID[497207]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[497208]
NPT2	Others	Unspecified		Activity	=	21.1	%	PMID[497208]
NPT2	Others	Unspecified		Activity	=	44.0	%	PMID[497208]
NPT2	Others	Unspecified		Activity	=	90.1	%	PMID[497208]
NPT2	Others	Unspecified		logIC50	=	2.41	n.a.	PMID[497208]

☑ 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 NPC167663 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	488
0.1-0.2	1880
0.2-0.3	4485
0.3-0.4	11186
0.4-0.5	6850
0.5-0.6	4010
0.6-0.7	6119
0.7-0.8	5487
0.8-0.85	1772
0.85-0.9	353
0.9-0.95	57
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC49282
0.9574	High Similarity	NPC56433
0.9574	High Similarity	NPC289042
0.9574	High Similarity	NPC126767
0.9574	High Similarity	NPC312929
0.9574	High Similarity	NPC190648
0.9574	High Similarity	NPC245584
0.9574	High Similarity	NPC118027
0.951	High Similarity	NPC474660
0.951	High Similarity	NPC470568
0.9507	High Similarity	NPC472056
0.9444	High Similarity	NPC470569
0.9379	High Similarity	NPC40356
0.9379	High Similarity	NPC154683
0.9375	High Similarity	NPC473466
0.9375	High Similarity	NPC294646
0.9375	High Similarity	NPC255641
0.9375	High Similarity	NPC147735
0.9375	High Similarity	NPC290954
0.9362	High Similarity	NPC189650
0.9362	High Similarity	NPC19896
0.9301	High Similarity	NPC34802
0.9291	High Similarity	NPC215451
0.9291	High Similarity	NPC277369
0.9252	High Similarity	NPC66508
0.9252	High Similarity	NPC226656
0.9214	High Similarity	NPC109007
0.9197	High Similarity	NPC1249
0.9184	High Similarity	NPC107109
0.9184	High Similarity	NPC208806
0.9172	High Similarity	NPC329933
0.9161	High Similarity	NPC34482
0.9155	High Similarity	NPC84266
0.9128	High Similarity	NPC199463
0.9128	High Similarity	NPC37543
0.9103	High Similarity	NPC172329
0.9103	High Similarity	NPC2569
0.9097	High Similarity	NPC473927
0.9097	High Similarity	NPC470570
0.9091	High Similarity	NPC48762
0.9091	High Similarity	NPC193703
0.9091	High Similarity	NPC21599
0.9085	High Similarity	NPC49108
0.9085	High Similarity	NPC182255
0.9085	High Similarity	NPC94076
0.9067	High Similarity	NPC324736
0.906	High Similarity	NPC77807
0.906	High Similarity	NPC5379
0.906	High Similarity	NPC14561
0.9054	High Similarity	NPC214632
0.9048	High Similarity	NPC474417
0.9048	High Similarity	NPC149526
0.9048	High Similarity	NPC478148
0.9041	High Similarity	NPC97028
0.9041	High Similarity	NPC288036
0.9041	High Similarity	NPC97029
0.9041	High Similarity	NPC100985
0.9041	High Similarity	NPC158338
0.9041	High Similarity	NPC65589
0.9014	High Similarity	NPC171094
0.9007	High Similarity	NPC472052
0.9007	High Similarity	NPC470342
0.9007	High Similarity	NPC472060
0.9	High Similarity	NPC178976
0.9	High Similarity	NPC263483
0.8973	High Similarity	NPC256672
0.8973	High Similarity	NPC27221
0.8973	High Similarity	NPC7025
0.8973	High Similarity	NPC476058
0.8973	High Similarity	NPC472841
0.8966	High Similarity	NPC163846
0.8966	High Similarity	NPC225173
0.8944	High Similarity	NPC472366
0.8926	High Similarity	NPC329844
0.8926	High Similarity	NPC93552
0.8921	High Similarity	NPC223354
0.8919	High Similarity	NPC72958
0.8919	High Similarity	NPC232645
0.8919	High Similarity	NPC474414
0.8912	High Similarity	NPC10027
0.8912	High Similarity	NPC65775
0.8912	High Similarity	NPC80370
0.8904	High Similarity	NPC123202
0.8904	High Similarity	NPC7943
0.8904	High Similarity	NPC22005
0.8904	High Similarity	NPC125801
0.8897	High Similarity	NPC28632
0.8897	High Similarity	NPC478019
0.8889	High Similarity	NPC108767
0.8889	High Similarity	NPC476054
0.8882	High Similarity	NPC84571
0.8881	High Similarity	NPC253822
0.8874	High Similarity	NPC474637
0.8874	High Similarity	NPC201127
0.8873	High Similarity	NPC242994
0.8873	High Similarity	NPC138099
0.8873	High Similarity	NPC1268
0.8865	High Similarity	NPC471905
0.8859	High Similarity	NPC87708
0.8851	High Similarity	NPC202595
0.8849	High Similarity	NPC182428
0.8832	High Similarity	NPC211120
0.8832	High Similarity	NPC57552
0.8828	High Similarity	NPC475201
0.8824	High Similarity	NPC311740
0.8819	High Similarity	NPC55832
0.8819	High Similarity	NPC135524
0.8819	High Similarity	NPC26051
0.8819	High Similarity	NPC232021
0.8819	High Similarity	NPC126534
0.8819	High Similarity	NPC40118
0.8819	High Similarity	NPC52789
0.8819	High Similarity	NPC268204
0.8811	High Similarity	NPC477956
0.8811	High Similarity	NPC181560
0.8811	High Similarity	NPC169452
0.8811	High Similarity	NPC109232
0.8808	High Similarity	NPC146211
0.8808	High Similarity	NPC180924
0.8803	High Similarity	NPC472419
0.88	High Similarity	NPC169990
0.88	High Similarity	NPC210942
0.8794	High Similarity	NPC254847
0.8792	High Similarity	NPC230848
0.8792	High Similarity	NPC46882
0.8792	High Similarity	NPC258249
0.8792	High Similarity	NPC132990
0.8784	High Similarity	NPC291049
0.8784	High Similarity	NPC233267
0.8776	High Similarity	NPC474999
0.8767	High Similarity	NPC476055
0.8759	High Similarity	NPC310340
0.8759	High Similarity	NPC3732
0.8759	High Similarity	NPC297600
0.8759	High Similarity	NPC53016
0.8758	High Similarity	NPC470810
0.875	High Similarity	NPC326109
0.875	High Similarity	NPC259166
0.875	High Similarity	NPC164110
0.875	High Similarity	NPC305845
0.875	High Similarity	NPC11056
0.875	High Similarity	NPC219917
0.875	High Similarity	NPC215311
0.875	High Similarity	NPC246647
0.875	High Similarity	NPC213659
0.875	High Similarity	NPC172250
0.875	High Similarity	NPC48624
0.875	High Similarity	NPC101366
0.875	High Similarity	NPC204045
0.875	High Similarity	NPC144118
0.875	High Similarity	NPC204985
0.875	High Similarity	NPC96342
0.875	High Similarity	NPC212967
0.875	High Similarity	NPC265178
0.875	High Similarity	NPC80962
0.8741	High Similarity	NPC243528
0.8741	High Similarity	NPC251681
0.8741	High Similarity	NPC472368
0.8741	High Similarity	NPC21350
0.8741	High Similarity	NPC223336
0.8733	High Similarity	NPC470338
0.8733	High Similarity	NPC51824
0.8733	High Similarity	NPC470340
0.8733	High Similarity	NPC149889
0.8733	High Similarity	NPC175978
0.8733	High Similarity	NPC268992
0.8733	High Similarity	NPC113608
0.8733	High Similarity	NPC312338
0.8733	High Similarity	NPC180944
0.8733	High Similarity	NPC470337
0.8732	High Similarity	NPC186838
0.8732	High Similarity	NPC161196
0.8732	High Similarity	NPC477244
0.8732	High Similarity	NPC472364
0.8732	High Similarity	NPC53206
0.8732	High Similarity	NPC168105
0.8732	High Similarity	NPC477242
0.8732	High Similarity	NPC98115
0.8732	High Similarity	NPC53414
0.8732	High Similarity	NPC150399
0.8732	High Similarity	NPC476333
0.8732	High Similarity	NPC477243
0.8732	High Similarity	NPC41461
0.8732	High Similarity	NPC25287
0.8732	High Similarity	NPC66349
0.8732	High Similarity	NPC249606
0.8732	High Similarity	NPC254741
0.8732	High Similarity	NPC274109
0.8732	High Similarity	NPC1486
0.8732	High Similarity	NPC12165
0.8732	High Similarity	NPC472367
0.8732	High Similarity	NPC473391
0.8725	High Similarity	NPC325983
0.8725	High Similarity	NPC227122
0.8725	High Similarity	NPC205766
0.8718	High Similarity	NPC477835
0.8716	High Similarity	NPC105415
0.8707	High Similarity	NPC25844
0.8707	High Similarity	NPC300540
0.8707	High Similarity	NPC196114

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 NPC167663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	437
0.1-0.2	1005
0.2-0.3	1619
0.3-0.4	2735
0.4-0.5	1838
0.5-0.6	995
0.6-0.7	353
0.7-0.8	143
0.8-0.85	22
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8794	High Similarity	NPD1509	Clinical (unspecified phase)
0.8675	High Similarity	NPD7819	Suspended
0.8645	High Similarity	NPD6232	Discontinued
0.8601	High Similarity	NPD2796	Approved
0.8599	High Similarity	NPD7473	Discontinued
0.8521	High Similarity	NPD1607	Approved
0.8462	Intermediate Similarity	NPD6959	Discontinued
0.8403	Intermediate Similarity	NPD1510	Phase 2
0.8389	Intermediate Similarity	NPD2532	Approved
0.8389	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD2534	Approved
0.8389	Intermediate Similarity	NPD2533	Approved
0.838	Intermediate Similarity	NPD1240	Approved
0.8289	Intermediate Similarity	NPD3226	Approved
0.828	Intermediate Similarity	NPD5494	Approved
0.8267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD7390	Discontinued
0.8194	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8151	Intermediate Similarity	NPD3748	Approved
0.8141	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD4380	Phase 2
0.8117	Intermediate Similarity	NPD6599	Discontinued
0.8108	Intermediate Similarity	NPD1549	Phase 2
0.8077	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1243	Approved
0.8041	Intermediate Similarity	NPD2346	Discontinued
0.8041	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2935	Discontinued
0.7962	Intermediate Similarity	NPD2801	Approved
0.7961	Intermediate Similarity	NPD6799	Approved
0.7929	Intermediate Similarity	NPD3972	Approved
0.7927	Intermediate Similarity	NPD5844	Phase 1
0.7925	Intermediate Similarity	NPD3749	Approved
0.7925	Intermediate Similarity	NPD7075	Discontinued
0.7922	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD920	Approved
0.7901	Intermediate Similarity	NPD3926	Phase 2
0.7899	Intermediate Similarity	NPD1651	Approved
0.7898	Intermediate Similarity	NPD6801	Discontinued
0.7898	Intermediate Similarity	NPD1934	Approved
0.7887	Intermediate Similarity	NPD1470	Approved
0.7881	Intermediate Similarity	NPD3750	Approved
0.7862	Intermediate Similarity	NPD3882	Suspended
0.7862	Intermediate Similarity	NPD7768	Phase 2
0.7853	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1511	Approved
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2800	Approved
0.78	Intermediate Similarity	NPD1471	Phase 3
0.7799	Intermediate Similarity	NPD3817	Phase 2
0.7792	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2799	Discontinued
0.7778	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6651	Approved
0.7742	Intermediate Similarity	NPD1512	Approved
0.7733	Intermediate Similarity	NPD6099	Approved
0.7733	Intermediate Similarity	NPD5405	Approved
0.7733	Intermediate Similarity	NPD6100	Approved
0.7733	Intermediate Similarity	NPD5406	Approved
0.7733	Intermediate Similarity	NPD5408	Approved
0.7733	Intermediate Similarity	NPD5404	Approved
0.773	Intermediate Similarity	NPD5710	Approved
0.773	Intermediate Similarity	NPD5711	Approved
0.7708	Intermediate Similarity	NPD2798	Approved
0.7697	Intermediate Similarity	NPD2654	Approved
0.7692	Intermediate Similarity	NPD1876	Approved
0.7688	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1247	Approved
0.7654	Intermediate Similarity	NPD919	Approved
0.7647	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7003	Approved
0.764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6166	Phase 2
0.7636	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD943	Approved
0.7616	Intermediate Similarity	NPD1551	Phase 2
0.7606	Intermediate Similarity	NPD1281	Approved
0.7606	Intermediate Similarity	NPD1201	Approved
0.7593	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6559	Discontinued
0.7566	Intermediate Similarity	NPD2344	Approved
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7469	Intermediate Similarity	NPD5402	Approved
0.7453	Intermediate Similarity	NPD37	Approved
0.7448	Intermediate Similarity	NPD1283	Approved
0.744	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4625	Phase 3
0.7419	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD7229	Phase 3
0.7407	Intermediate Similarity	NPD1465	Phase 2
0.74	Intermediate Similarity	NPD2979	Phase 3
0.7396	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5691	Approved
0.7389	Intermediate Similarity	NPD6778	Approved
0.7389	Intermediate Similarity	NPD6781	Approved
0.7389	Intermediate Similarity	NPD6779	Approved
0.7389	Intermediate Similarity	NPD6776	Approved
0.7389	Intermediate Similarity	NPD6780	Approved
0.7389	Intermediate Similarity	NPD6782	Approved
0.7389	Intermediate Similarity	NPD6777	Approved
0.7372	Intermediate Similarity	NPD2309	Approved
0.7371	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5403	Approved
0.7353	Intermediate Similarity	NPD7074	Phase 3
0.7351	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD8151	Discontinued
0.7343	Intermediate Similarity	NPD4626	Approved
0.7342	Intermediate Similarity	NPD5401	Approved
0.7342	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4965	Approved
0.7317	Intermediate Similarity	NPD4966	Approved
0.7317	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD7054	Approved
0.7294	Intermediate Similarity	NPD7286	Phase 2
0.7285	Intermediate Similarity	NPD4307	Phase 2
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD2438	Suspended
0.7268	Intermediate Similarity	NPD7698	Approved
0.7268	Intermediate Similarity	NPD7697	Approved
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7268	Intermediate Similarity	NPD7696	Phase 3
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3764	Approved
0.7251	Intermediate Similarity	NPD7472	Approved
0.7235	Intermediate Similarity	NPD3751	Discontinued
0.7235	Intermediate Similarity	NPD7177	Discontinued
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6234	Discontinued
0.7228	Intermediate Similarity	NPD7871	Phase 2
0.7228	Intermediate Similarity	NPD7870	Phase 2
0.7222	Intermediate Similarity	NPD17	Approved
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6797	Phase 2
0.7198	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6273	Approved
0.7168	Intermediate Similarity	NPD7251	Discontinued
0.7162	Intermediate Similarity	NPD3267	Approved
0.7162	Intermediate Similarity	NPD3266	Approved
0.7161	Intermediate Similarity	NPD2531	Phase 2
0.716	Intermediate Similarity	NPD5242	Approved
0.7159	Intermediate Similarity	NPD8150	Discontinued
0.7152	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD8285	Discontinued
0.7134	Intermediate Similarity	NPD6279	Approved
0.7134	Intermediate Similarity	NPD6280	Approved
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7126	Intermediate Similarity	NPD7808	Phase 3
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1933	Approved
0.7124	Intermediate Similarity	NPD230	Phase 1
0.7118	Intermediate Similarity	NPD2403	Approved
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7701	Phase 2
0.7111	Intermediate Similarity	NPD6534	Approved
0.7111	Intermediate Similarity	NPD6535	Approved
0.7105	Intermediate Similarity	NPD8032	Phase 2
0.7103	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD4308	Phase 3
0.7075	Intermediate Similarity	NPD1608	Approved
0.7063	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1203	Approved
0.7039	Intermediate Similarity	NPD411	Approved
0.7039	Intermediate Similarity	NPD3268	Approved
0.7037	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7874	Approved
0.7027	Intermediate Similarity	NPD6823	Phase 2
0.7027	Intermediate Similarity	NPD4749	Approved
0.7014	Intermediate Similarity	NPD5536	Phase 2
0.7006	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6808	Phase 2
0.7	Intermediate Similarity	NPD7801	Approved
0.6995	Remote Similarity	NPD7699	Phase 2
0.6995	Remote Similarity	NPD7700	Phase 2
0.6988	Remote Similarity	NPD5761	Phase 2
0.6988	Remote Similarity	NPD5760	Phase 2
0.6983	Remote Similarity	NPD4287	Approved
0.6972	Remote Similarity	NPD1241	Discontinued
0.697	Remote Similarity	NPD5890	Approved
0.697	Remote Similarity	NPD5889	Approved
0.6966	Remote Similarity	NPD8434	Phase 2

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