NPASS Compound

Structure

CID66705 OpenBabel06191715402D 21 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 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 -2.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.07
Volume:	288.352
LogP:	2.992
LogD:	2.871
LogS:	-4.447
# Rotatable Bonds:	3
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	1.835
Fsp3:	0.059
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.732
MDCK Permeability:	3.3492175134597346e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	98.22566986083984%
Volume Distribution (VD):	0.477
Pgp-substrate:	1.1323105096817017%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.829
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.753
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.13
CYP2D6-substrate:	0.595
CYP3A4-inhibitor:	0.33
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	1.335
Half-life (T1/2):	0.292

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.452
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.232
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.108
Carcinogencity:	0.845
Eye Corrosion:	0.004
Eye Irritation:	0.861
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC66705

Natural Product ID:	NPC66705
*Common Name:**	3-Benzoyl-7-Methoxychromen-2-One
IUPAC Name:	3-benzoyl-7-methoxychromen-2-one
Synonyms:
Standard InCHIKey:	HYORIVUCOQKMOC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12O4/c1-20-13-8-7-12-9-14(17(19)21-15(12)10-13)16(18)11-5-3-2-4-6-11/h2-10H,1H3
SMILES:	COc1ccc2c(c1)oc(=O)c(c2)C(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1533108
PubChem CID:	342533
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004297] Aryl-phenylketones

*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
NPO26123	Isodon serra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32993289]
NPO26123	Isodon serra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26123	Isodon serra	Species	Lamiaceae	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	1
Potency	19

Activity Type	# Activity
Cell Line	1
Individual Protein	13
Organism	2
Others	2
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[570410]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	3548.1	nM	PMID[570410]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	11220.2	nM	PMID[570410]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	5623.4	nM	PMID[570410]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	5011.9	nM	PMID[570410]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[570410]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[570410]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[570410]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	40.0	%	PMID[570411]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	23934.1	nM	PMID[570410]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	2058.8	nM	PMID[570410]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[570410]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	4140.0	nM	PMID[570410]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	14125.4	nM	PMID[570410]
NPT2	Others	Unspecified		Potency	=	580.5	nM	PMID[570410]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1041.8	nM	PMID[570410]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[570410]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	585.8	nM	PMID[570410]
NPT2	Others	Unspecified		Potency	n.a.	2908.1	nM	PMID[570410]

☑ 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 NPC66705 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	468
0.1-0.2	2088
0.2-0.3	5437
0.3-0.4	11887
0.4-0.5	5387
0.5-0.6	5081
0.6-0.7	5773
0.7-0.8	4274
0.8-0.85	1574
0.85-0.9	592
0.9-0.95	127
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC136095
0.9474	High Similarity	NPC103001
0.9313	High Similarity	NPC278556
0.9313	High Similarity	NPC284424
0.9242	High Similarity	NPC101294
0.9242	High Similarity	NPC473655
0.9225	High Similarity	NPC41721
0.9185	High Similarity	NPC253616
0.9173	High Similarity	NPC292998
0.9124	High Similarity	NPC474037
0.9111	High Similarity	NPC268081
0.9111	High Similarity	NPC254741
0.9111	High Similarity	NPC472516
0.9104	High Similarity	NPC125269
0.907	High Similarity	NPC2771
0.9051	High Similarity	NPC473209
0.9044	High Similarity	NPC250266
0.9044	High Similarity	NPC266597
0.8978	High Similarity	NPC36414
0.8971	High Similarity	NPC124784
0.8971	High Similarity	NPC61546
0.8971	High Similarity	NPC473887
0.8971	High Similarity	NPC29353
0.8971	High Similarity	NPC47815
0.8971	High Similarity	NPC231772
0.8971	High Similarity	NPC72452
0.8971	High Similarity	NPC161196
0.8971	High Similarity	NPC234133
0.8971	High Similarity	NPC194281
0.8971	High Similarity	NPC127447
0.8955	High Similarity	NPC182428
0.8939	High Similarity	NPC211120
0.8931	High Similarity	NPC49852
0.8931	High Similarity	NPC475496
0.8931	High Similarity	NPC264428
0.8929	High Similarity	NPC470216
0.8921	High Similarity	NPC24075
0.8915	High Similarity	NPC315807
0.8913	High Similarity	NPC472515
0.8905	High Similarity	NPC38153
0.8905	High Similarity	NPC332594
0.8897	High Similarity	NPC99854
0.8889	High Similarity	NPC223354
0.8881	High Similarity	NPC113006
0.8872	High Similarity	NPC228184
0.8865	High Similarity	NPC469953
0.8864	High Similarity	NPC473907
0.8864	High Similarity	NPC125887
0.8864	High Similarity	NPC475017
0.8857	High Similarity	NPC36181
0.8849	High Similarity	NPC281207
0.8849	High Similarity	NPC269652
0.8841	High Similarity	NPC17848
0.8841	High Similarity	NPC276905
0.8841	High Similarity	NPC188947
0.8841	High Similarity	NPC280284
0.8841	High Similarity	NPC99333
0.8832	High Similarity	NPC13408
0.8824	High Similarity	NPC172262
0.8815	High Similarity	NPC54503
0.8815	High Similarity	NPC55147
0.8806	High Similarity	NPC137264
0.8803	High Similarity	NPC470322
0.8803	High Similarity	NPC153758
0.8803	High Similarity	NPC154217
0.8797	High Similarity	NPC473894
0.8794	High Similarity	NPC470296
0.8794	High Similarity	NPC112791
0.8794	High Similarity	NPC188632
0.8794	High Similarity	NPC94794
0.8794	High Similarity	NPC87609
0.8794	High Similarity	NPC196459
0.8786	High Similarity	NPC103362
0.8786	High Similarity	NPC136840
0.8786	High Similarity	NPC110969
0.8777	High Similarity	NPC241838
0.8777	High Similarity	NPC310370
0.8777	High Similarity	NPC18260
0.8777	High Similarity	NPC152042
0.8777	High Similarity	NPC143799
0.8777	High Similarity	NPC11566
0.8777	High Similarity	NPC183642
0.8777	High Similarity	NPC78913
0.8768	High Similarity	NPC228661
0.8768	High Similarity	NPC275055
0.8768	High Similarity	NPC157855
0.8768	High Similarity	NPC259685
0.8768	High Similarity	NPC290291
0.8768	High Similarity	NPC188879
0.8759	High Similarity	NPC46869
0.8759	High Similarity	NPC223616
0.875	High Similarity	NPC78540
0.875	High Similarity	NPC50898
0.875	High Similarity	NPC57601
0.875	High Similarity	NPC274121
0.875	High Similarity	NPC213216
0.8741	High Similarity	NPC218300
0.8741	High Similarity	NPC282335
0.8741	High Similarity	NPC180477
0.8741	High Similarity	NPC307289
0.8741	High Similarity	NPC175159
0.8732	High Similarity	NPC178627
0.8732	High Similarity	NPC196137
0.8732	High Similarity	NPC469935
0.8732	High Similarity	NPC1886
0.8731	High Similarity	NPC39753
0.8731	High Similarity	NPC115998
0.8723	High Similarity	NPC11561
0.8723	High Similarity	NPC226636
0.8714	High Similarity	NPC270883
0.8714	High Similarity	NPC230285
0.8714	High Similarity	NPC472409
0.8714	High Similarity	NPC150522
0.8714	High Similarity	NPC103904
0.8714	High Similarity	NPC241100
0.8714	High Similarity	NPC171094
0.8714	High Similarity	NPC184536
0.8714	High Similarity	NPC103342
0.8714	High Similarity	NPC261227
0.8714	High Similarity	NPC146679
0.8714	High Similarity	NPC159275
0.8714	High Similarity	NPC172986
0.8714	High Similarity	NPC59951
0.8705	High Similarity	NPC201395
0.8705	High Similarity	NPC124269
0.8705	High Similarity	NPC71903
0.8696	High Similarity	NPC240593
0.869	High Similarity	NPC295036
0.8686	High Similarity	NPC248872
0.8676	High Similarity	NPC129132
0.8676	High Similarity	NPC229646
0.8676	High Similarity	NPC205468
0.8676	High Similarity	NPC257756
0.8676	High Similarity	NPC87231
0.8676	High Similarity	NPC212631
0.8672	High Similarity	NPC298796
0.8671	High Similarity	NPC181388
0.8671	High Similarity	NPC57470
0.8667	High Similarity	NPC301717
0.8667	High Similarity	NPC472517
0.8662	High Similarity	NPC59522
0.8662	High Similarity	NPC113089
0.8657	High Similarity	NPC197425
0.8652	High Similarity	NPC254010
0.8652	High Similarity	NPC118840
0.8652	High Similarity	NPC262094
0.8652	High Similarity	NPC64908
0.8652	High Similarity	NPC282300
0.8652	High Similarity	NPC147688
0.8652	High Similarity	NPC90582
0.8652	High Similarity	NPC156590
0.8652	High Similarity	NPC205006
0.8652	High Similarity	NPC3188
0.8643	High Similarity	NPC310135
0.8643	High Similarity	NPC225153
0.8643	High Similarity	NPC262635
0.8643	High Similarity	NPC150648
0.8643	High Similarity	NPC329203
0.8643	High Similarity	NPC222342
0.8643	High Similarity	NPC216978
0.8643	High Similarity	NPC274784
0.8643	High Similarity	NPC217186
0.8643	High Similarity	NPC96565
0.8643	High Similarity	NPC303633
0.8643	High Similarity	NPC55018
0.8643	High Similarity	NPC170812
0.8643	High Similarity	NPC53181
0.8643	High Similarity	NPC265871
0.8643	High Similarity	NPC20709
0.8643	High Similarity	NPC220062
0.8643	High Similarity	NPC301217
0.8643	High Similarity	NPC261234
0.8639	High Similarity	NPC186507
0.8636	High Similarity	NPC65041
0.8633	High Similarity	NPC181124
0.8633	High Similarity	NPC162680
0.8633	High Similarity	NPC303644
0.8633	High Similarity	NPC299379
0.8633	High Similarity	NPC7013
0.8633	High Similarity	NPC307883
0.8633	High Similarity	NPC116632
0.8633	High Similarity	NPC209560
0.8633	High Similarity	NPC294409
0.863	High Similarity	NPC474388
0.863	High Similarity	NPC472535
0.863	High Similarity	NPC474170
0.8623	High Similarity	NPC104796
0.8623	High Similarity	NPC9985
0.8623	High Similarity	NPC239495
0.8621	High Similarity	NPC19238
0.8621	High Similarity	NPC164299
0.8621	High Similarity	NPC474648
0.8621	High Similarity	NPC88445
0.8613	High Similarity	NPC312318
0.8613	High Similarity	NPC337373
0.8613	High Similarity	NPC175098
0.8613	High Similarity	NPC188646
0.8613	High Similarity	NPC242294
0.8613	High Similarity	NPC263670
0.8613	High Similarity	NPC139813

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 NPC66705 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	990
0.2-0.3	1662
0.3-0.4	2727
0.4-0.5	1830
0.5-0.6	1044
0.6-0.7	307
0.7-0.8	98
0.8-0.85	33
0.85-0.9	18
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9037	High Similarity	NPD3748	Approved
0.8971	High Similarity	NPD2796	Approved
0.8794	High Similarity	NPD6799	Approved
0.8722	High Similarity	NPD6832	Phase 2
0.8714	High Similarity	NPD3750	Approved
0.8643	High Similarity	NPD1243	Approved
0.8601	High Similarity	NPD5401	Approved
0.8571	High Similarity	NPD1549	Phase 2
0.8503	High Similarity	NPD7411	Suspended
0.85	High Similarity	NPD1550	Clinical (unspecified phase)
0.85	High Similarity	NPD1552	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD1510	Phase 2
0.8483	Intermediate Similarity	NPD5403	Approved
0.8483	Intermediate Similarity	NPD920	Approved
0.8472	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1240	Approved
0.8462	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD6801	Discontinued
0.8435	Intermediate Similarity	NPD6599	Discontinued
0.8429	Intermediate Similarity	NPD1551	Phase 2
0.8389	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD7819	Suspended
0.8358	Intermediate Similarity	NPD3266	Approved
0.8358	Intermediate Similarity	NPD1203	Approved
0.8358	Intermediate Similarity	NPD3267	Approved
0.8345	Intermediate Similarity	NPD1607	Approved
0.8345	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD4307	Phase 2
0.8321	Intermediate Similarity	NPD1296	Phase 2
0.8273	Intermediate Similarity	NPD1933	Approved
0.8273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD9717	Approved
0.8252	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7075	Discontinued
0.8195	Intermediate Similarity	NPD422	Phase 1
0.8195	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2313	Discontinued
0.8182	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1019	Discontinued
0.8158	Intermediate Similarity	NPD7768	Phase 2
0.8151	Intermediate Similarity	NPD1511	Approved
0.8105	Intermediate Similarity	NPD3749	Approved
0.8099	Intermediate Similarity	NPD2799	Discontinued
0.8099	Intermediate Similarity	NPD4308	Phase 3
0.8092	Intermediate Similarity	NPD5402	Approved
0.8088	Intermediate Similarity	NPD2797	Approved
0.8058	Intermediate Similarity	NPD3268	Approved
0.8052	Intermediate Similarity	NPD919	Approved
0.8043	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1512	Approved
0.8026	Intermediate Similarity	NPD2801	Approved
0.8015	Intermediate Similarity	NPD3225	Approved
0.7987	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1934	Approved
0.7947	Intermediate Similarity	NPD4380	Phase 2
0.7923	Intermediate Similarity	NPD1241	Discontinued
0.7917	Intermediate Similarity	NPD2935	Discontinued
0.7911	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD2798	Approved
0.7867	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4288	Approved
0.7857	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3882	Suspended
0.7799	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5494	Approved
0.7763	Intermediate Similarity	NPD3226	Approved
0.7761	Intermediate Similarity	NPD1548	Phase 1
0.774	Intermediate Similarity	NPD2346	Discontinued
0.7737	Intermediate Similarity	NPD3972	Approved
0.7724	Intermediate Similarity	NPD7033	Discontinued
0.771	Intermediate Similarity	NPD5535	Approved
0.7703	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD411	Approved
0.7647	Intermediate Similarity	NPD17	Approved
0.7639	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD447	Suspended
0.7639	Intermediate Similarity	NPD5124	Phase 1
0.7635	Intermediate Similarity	NPD2800	Approved
0.7635	Intermediate Similarity	NPD2654	Approved
0.7626	Intermediate Similarity	NPD1876	Approved
0.7625	Intermediate Similarity	NPD3926	Phase 2
0.7619	Intermediate Similarity	NPD2344	Approved
0.7612	Intermediate Similarity	NPD9493	Approved
0.7593	Intermediate Similarity	NPD3818	Discontinued
0.7584	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD9697	Approved
0.7561	Intermediate Similarity	NPD5953	Discontinued
0.7552	Intermediate Similarity	NPD6798	Discontinued
0.7548	Intermediate Similarity	NPD5889	Approved
0.7548	Intermediate Similarity	NPD5890	Approved
0.7546	Intermediate Similarity	NPD7286	Phase 2
0.7546	Intermediate Similarity	NPD5844	Phase 1
0.7546	Intermediate Similarity	NPD7054	Approved
0.7546	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1652	Phase 2
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD1894	Discontinued
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD2353	Approved
0.75	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6585	Discontinued
0.7482	Intermediate Similarity	NPD1608	Approved
0.747	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6166	Phase 2
0.7469	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6651	Approved
0.7455	Intermediate Similarity	NPD6797	Phase 2
0.7453	Intermediate Similarity	NPD6232	Discontinued
0.7452	Intermediate Similarity	NPD1465	Phase 2
0.7436	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3764	Approved
0.7423	Intermediate Similarity	NPD7473	Discontinued
0.7421	Intermediate Similarity	NPD6971	Discontinued
0.7417	Intermediate Similarity	NPD3887	Approved
0.7417	Intermediate Similarity	NPD2309	Approved
0.7413	Intermediate Similarity	NPD4908	Phase 1
0.741	Intermediate Similarity	NPD7251	Discontinued
0.741	Intermediate Similarity	NPD1610	Phase 2
0.7394	Intermediate Similarity	NPD7074	Phase 3
0.7391	Intermediate Similarity	NPD6959	Discontinued
0.7386	Intermediate Similarity	NPD2534	Approved
0.7386	Intermediate Similarity	NPD2532	Approved
0.7386	Intermediate Similarity	NPD2533	Approved
0.7383	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6233	Phase 2
0.7365	Intermediate Similarity	NPD7808	Phase 3
0.7357	Intermediate Similarity	NPD1481	Phase 2
0.731	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2354	Approved
0.7287	Intermediate Similarity	NPD9261	Approved
0.7286	Intermediate Similarity	NPD1535	Discovery
0.7279	Intermediate Similarity	NPD6355	Discontinued
0.7279	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7262	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7440	Discontinued
0.7252	Intermediate Similarity	NPD3134	Approved
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6808	Phase 2
0.7237	Intermediate Similarity	NPD7003	Approved
0.7226	Intermediate Similarity	NPD6273	Approved
0.7226	Intermediate Similarity	NPD5049	Phase 3
0.7215	Intermediate Similarity	NPD2366	Approved
0.7211	Intermediate Similarity	NPD3142	Approved
0.7211	Intermediate Similarity	NPD943	Approved
0.7211	Intermediate Similarity	NPD3140	Approved
0.72	Intermediate Similarity	NPD6100	Approved
0.72	Intermediate Similarity	NPD6099	Approved
0.7197	Intermediate Similarity	NPD1358	Approved
0.7197	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5536	Phase 2
0.7163	Intermediate Similarity	NPD1281	Approved
0.7162	Intermediate Similarity	NPD4622	Approved
0.7162	Intermediate Similarity	NPD4340	Discontinued
0.7162	Intermediate Similarity	NPD4618	Approved
0.7161	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7143	Intermediate Similarity	NPD8032	Phase 2
0.7133	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2186	Approved
0.711	Intermediate Similarity	NPD4287	Approved
0.7097	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3847	Discontinued
0.7091	Intermediate Similarity	NPD5242	Approved
0.7089	Intermediate Similarity	NPD7458	Discontinued
0.7086	Intermediate Similarity	NPD4477	Approved
0.7086	Intermediate Similarity	NPD4476	Approved
0.7083	Intermediate Similarity	NPD1164	Approved
0.7073	Intermediate Similarity	NPD7199	Phase 2
0.7071	Intermediate Similarity	NPD5585	Approved
0.7068	Intermediate Similarity	NPD9264	Approved
0.7068	Intermediate Similarity	NPD9263	Approved
0.7068	Intermediate Similarity	NPD9267	Approved
0.7067	Intermediate Similarity	NPD5689	Approved
0.7067	Intermediate Similarity	NPD5688	Approved
0.7063	Intermediate Similarity	NPD6844	Discontinued
0.7063	Intermediate Similarity	NPD6280	Approved
0.7063	Intermediate Similarity	NPD6279	Approved
0.7055	Intermediate Similarity	NPD2614	Approved
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1238	Approved
0.7051	Intermediate Similarity	NPD4662	Approved
0.7051	Intermediate Similarity	NPD4661	Approved
0.7037	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7229	Phase 3
0.7025	Intermediate Similarity	NPD1653	Approved
0.7021	Intermediate Similarity	NPD1778	Approved
0.7015	Intermediate Similarity	NPD9266	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