NPASS Compound

Structure

NPC469519 OpenBabel07101718182D 24 27 0 0 1 0 0 0 0 0999 V2000 0.9450 -3.1345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6995 -1.7124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5696 -1.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5696 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -1.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6493 -0.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4307 -1.7064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3735 -0.2070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2820 -1.9645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 0.2272 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.3512 -2.3299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2816 -0.7176 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0639 -2.5880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 1.2930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2777 -0.8057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -0.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2820 -1.1626 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 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 9 22 1 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 12 8 1 6 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 9 1 1 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 16 24 1 0 0 0 0 17 1 1 6 0 0 0 17 23 1 0 0 0 0 18 21 1 1 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.13
Volume:	325.217
LogP:	2.006
LogD:	1.721
LogS:	-3.622
# Rotatable Bonds:	5
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.785
Synthetic Accessibility Score:	5.43
Fsp3:	0.556
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:	-4.746
MDCK Permeability:	3.790572736761533e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.316
Plasma Protein Binding (PPB):	91.29630279541016%
Volume Distribution (VD):	0.995
Pgp-substrate:	7.074987888336182%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.376
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.772
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	13.354
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.115
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.558
Rat Oral Acute Toxicity:	0.336
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.273
Carcinogencity:	0.543
Eye Corrosion:	0.012
Eye Irritation:	0.62
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC469519

Natural Product ID:	NPC469519
*Common Name:**	BCPSDKWCITVQOP-IDNXCJIVSA-N
IUPAC Name:	n.a.
Synonyms:	6-Methoxypaeoniflorigenone
Standard InCHIKey:	BCPSDKWCITVQOP-IDNXCJIVSA-N
Standard InCHI:	InChI=1S/C18H20O6/c1-17-10-18(21-2)8-12(14(17)19)13(16(23-17)24-18)9-22-15(20)11-6-4-3-5-7-11/h3-7,12-13,16H,8-10H2,1-2H3/t12-,13-,16?,17+,18+/m0/s1
SMILES:	CO[C@@]12OC3O[C@](C2)(C(=O)[C@@H](C1)[C@@H]3COC(=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081885
PubChem CID:	46883192
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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
IC50	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	50000.0	nM	PMID[470765]
NPT35	Others	n.a.		IC50	>	500000.0	nM	PMID[470765]

☑ 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 NPC469519 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	369
0.1-0.2	1331
0.2-0.3	2627
0.3-0.4	6743
0.4-0.5	11645
0.5-0.6	12456
0.6-0.7	6860
0.7-0.8	659
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8433	Intermediate Similarity	NPC475569
0.8214	Intermediate Similarity	NPC77493
0.8176	Intermediate Similarity	NPC477735
0.8121	Intermediate Similarity	NPC477736
0.8116	Intermediate Similarity	NPC473216
0.8116	Intermediate Similarity	NPC473399
0.8077	Intermediate Similarity	NPC473243
0.8074	Intermediate Similarity	NPC301857
0.8056	Intermediate Similarity	NPC477737
0.8015	Intermediate Similarity	NPC147561
0.8015	Intermediate Similarity	NPC27712
0.7985	Intermediate Similarity	NPC476599
0.7956	Intermediate Similarity	NPC475478
0.7931	Intermediate Similarity	NPC475552
0.7926	Intermediate Similarity	NPC114096
0.7919	Intermediate Similarity	NPC469398
0.7917	Intermediate Similarity	NPC470231
0.791	Intermediate Similarity	NPC57607
0.7902	Intermediate Similarity	NPC182869
0.7891	Intermediate Similarity	NPC222102
0.7891	Intermediate Similarity	NPC303429
0.7887	Intermediate Similarity	NPC183270
0.7887	Intermediate Similarity	NPC477904
0.7887	Intermediate Similarity	NPC475400
0.7874	Intermediate Similarity	NPC128368
0.7868	Intermediate Similarity	NPC148026
0.7862	Intermediate Similarity	NPC471100
0.7862	Intermediate Similarity	NPC471107
0.7857	Intermediate Similarity	NPC471493
0.7852	Intermediate Similarity	NPC470818
0.7842	Intermediate Similarity	NPC476644
0.7838	Intermediate Similarity	NPC469415
0.7836	Intermediate Similarity	NPC473881
0.7823	Intermediate Similarity	NPC473403
0.7821	Intermediate Similarity	NPC102465
0.7808	Intermediate Similarity	NPC469513
0.78	Intermediate Similarity	NPC469422
0.78	Intermediate Similarity	NPC5115
0.7786	Intermediate Similarity	NPC474608
0.7778	Intermediate Similarity	NPC472546
0.777	Intermediate Similarity	NPC238370
0.777	Intermediate Similarity	NPC254558
0.777	Intermediate Similarity	NPC469448
0.777	Intermediate Similarity	NPC472394
0.777	Intermediate Similarity	NPC471880
0.7763	Intermediate Similarity	NPC476784
0.7752	Intermediate Similarity	NPC474095
0.7746	Intermediate Similarity	NPC283375
0.7746	Intermediate Similarity	NPC183122
0.7746	Intermediate Similarity	NPC475373
0.774	Intermediate Similarity	NPC127857
0.7734	Intermediate Similarity	NPC161611
0.7733	Intermediate Similarity	NPC469477
0.7733	Intermediate Similarity	NPC133430
0.773	Intermediate Similarity	NPC265459
0.773	Intermediate Similarity	NPC195647
0.773	Intermediate Similarity	NPC66761
0.773	Intermediate Similarity	NPC475262
0.773	Intermediate Similarity	NPC17877
0.773	Intermediate Similarity	NPC472577
0.773	Intermediate Similarity	NPC290833
0.773	Intermediate Similarity	NPC291638
0.773	Intermediate Similarity	NPC270364
0.7727	Intermediate Similarity	NPC476096
0.7724	Intermediate Similarity	NPC91703
0.7724	Intermediate Similarity	NPC474365
0.7724	Intermediate Similarity	NPC301943
0.7718	Intermediate Similarity	NPC101043
0.7718	Intermediate Similarity	NPC306799
0.7717	Intermediate Similarity	NPC210089
0.7712	Intermediate Similarity	NPC477623
0.7703	Intermediate Similarity	NPC473215
0.7703	Intermediate Similarity	NPC60509
0.7703	Intermediate Similarity	NPC81698
0.7703	Intermediate Similarity	NPC250046
0.7698	Intermediate Similarity	NPC319995
0.7698	Intermediate Similarity	NPC289415
0.7697	Intermediate Similarity	NPC469417
0.7692	Intermediate Similarity	NPC475652
0.7692	Intermediate Similarity	NPC276652
0.7692	Intermediate Similarity	NPC475195
0.7692	Intermediate Similarity	NPC210591
0.7692	Intermediate Similarity	NPC214550
0.7682	Intermediate Similarity	NPC34066
0.7682	Intermediate Similarity	NPC469456
0.7677	Intermediate Similarity	NPC150893
0.7677	Intermediate Similarity	NPC295408
0.7677	Intermediate Similarity	NPC329960
0.7676	Intermediate Similarity	NPC472545
0.7676	Intermediate Similarity	NPC285221
0.7676	Intermediate Similarity	NPC472551
0.7676	Intermediate Similarity	NPC194769
0.7674	Intermediate Similarity	NPC307651
0.766	Intermediate Similarity	NPC472250
0.766	Intermediate Similarity	NPC473359
0.766	Intermediate Similarity	NPC38420
0.766	Intermediate Similarity	NPC136608
0.7658	Intermediate Similarity	NPC477471
0.7658	Intermediate Similarity	NPC477469
0.7658	Intermediate Similarity	NPC477473
0.7658	Intermediate Similarity	NPC477466
0.7656	Intermediate Similarity	NPC270699
0.7656	Intermediate Similarity	NPC82899
0.7655	Intermediate Similarity	NPC183540
0.7651	Intermediate Similarity	NPC112216
0.7651	Intermediate Similarity	NPC165260
0.7651	Intermediate Similarity	NPC470245
0.7651	Intermediate Similarity	NPC198455
0.7651	Intermediate Similarity	NPC161239
0.7651	Intermediate Similarity	NPC473214
0.7651	Intermediate Similarity	NPC7095
0.7647	Intermediate Similarity	NPC469399
0.7639	Intermediate Similarity	NPC48017
0.7639	Intermediate Similarity	NPC200592
0.7639	Intermediate Similarity	NPC4341
0.7639	Intermediate Similarity	NPC211137
0.7639	Intermediate Similarity	NPC251294
0.7639	Intermediate Similarity	NPC43241
0.7639	Intermediate Similarity	NPC473112
0.7639	Intermediate Similarity	NPC476094
0.7639	Intermediate Similarity	NPC473613
0.7639	Intermediate Similarity	NPC473060
0.7639	Intermediate Similarity	NPC147880
0.7639	Intermediate Similarity	NPC473109
0.7639	Intermediate Similarity	NPC473081
0.7639	Intermediate Similarity	NPC473085
0.7639	Intermediate Similarity	NPC473758
0.7639	Intermediate Similarity	NPC184747
0.7639	Intermediate Similarity	NPC475660
0.7638	Intermediate Similarity	NPC214067
0.7638	Intermediate Similarity	NPC196246
0.7626	Intermediate Similarity	NPC42234
0.7622	Intermediate Similarity	NPC86772
0.7622	Intermediate Similarity	NPC39549
0.7612	Intermediate Similarity	NPC50872
0.7606	Intermediate Similarity	NPC79699
0.76	Intermediate Similarity	NPC51602
0.76	Intermediate Similarity	NPC471103
0.7591	Intermediate Similarity	NPC470765
0.7586	Intermediate Similarity	NPC213567
0.7586	Intermediate Similarity	NPC224491
0.7586	Intermediate Similarity	NPC473654
0.7584	Intermediate Similarity	NPC476975
0.758	Intermediate Similarity	NPC477491
0.7578	Intermediate Similarity	NPC305912
0.7578	Intermediate Similarity	NPC1082
0.7574	Intermediate Similarity	NPC472704
0.7569	Intermediate Similarity	NPC272523
0.7569	Intermediate Similarity	NPC472395
0.7569	Intermediate Similarity	NPC325805
0.7569	Intermediate Similarity	NPC472371
0.7566	Intermediate Similarity	NPC282239
0.7564	Intermediate Similarity	NPC66193
0.7559	Intermediate Similarity	NPC10251
0.7559	Intermediate Similarity	NPC469636
0.7559	Intermediate Similarity	NPC17417
0.7557	Intermediate Similarity	NPC149691
0.7554	Intermediate Similarity	NPC237182
0.7554	Intermediate Similarity	NPC226101
0.755	Intermediate Similarity	NPC469416
0.755	Intermediate Similarity	NPC471348
0.755	Intermediate Similarity	NPC228906
0.7547	Intermediate Similarity	NPC477488
0.7536	Intermediate Similarity	NPC473220
0.7536	Intermediate Similarity	NPC470753
0.7536	Intermediate Similarity	NPC169913
0.7536	Intermediate Similarity	NPC51292
0.7535	Intermediate Similarity	NPC48929
0.7533	Intermediate Similarity	NPC476173
0.7532	Intermediate Similarity	NPC319404
0.7518	Intermediate Similarity	NPC125053
0.7518	Intermediate Similarity	NPC295664
0.7518	Intermediate Similarity	NPC477360
0.7517	Intermediate Similarity	NPC476643
0.7517	Intermediate Similarity	NPC171207
0.7517	Intermediate Similarity	NPC97667
0.7517	Intermediate Similarity	NPC100913
0.7517	Intermediate Similarity	NPC275592
0.7517	Intermediate Similarity	NPC472547
0.7517	Intermediate Similarity	NPC90614
0.7516	Intermediate Similarity	NPC106895
0.7516	Intermediate Similarity	NPC471134
0.7516	Intermediate Similarity	NPC217091
0.75	Intermediate Similarity	NPC249471
0.75	Intermediate Similarity	NPC257213
0.75	Intermediate Similarity	NPC472657
0.75	Intermediate Similarity	NPC477190
0.75	Intermediate Similarity	NPC158333
0.75	Intermediate Similarity	NPC93084
0.75	Intermediate Similarity	NPC256142
0.75	Intermediate Similarity	NPC472030
0.75	Intermediate Similarity	NPC223351
0.75	Intermediate Similarity	NPC141970
0.75	Intermediate Similarity	NPC242262
0.75	Intermediate Similarity	NPC265395
0.75	Intermediate Similarity	NPC473247
0.75	Intermediate Similarity	NPC219419
0.75	Intermediate Similarity	NPC1173
0.75	Intermediate Similarity	NPC43304
0.75	Intermediate Similarity	NPC477188

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 NPC469519 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	836
0.2-0.3	1469
0.3-0.4	3077
0.4-0.5	2310
0.5-0.6	939
0.6-0.7	203
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7578	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD2182	Approved
0.7383	Intermediate Similarity	NPD7236	Approved
0.7376	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7799	Discontinued
0.7244	Intermediate Similarity	NPD164	Approved
0.7239	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1238	Approved
0.7153	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7239	Suspended
0.7121	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2067	Discontinued
0.705	Intermediate Similarity	NPD6287	Discontinued
0.7042	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8368	Discontinued
0.6968	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3764	Approved
0.6963	Remote Similarity	NPD2629	Approved
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7961	Discontinued
0.6913	Remote Similarity	NPD3748	Approved
0.6912	Remote Similarity	NPD4198	Discontinued
0.6908	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5667	Approved
0.6899	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1930	Approved
0.6899	Remote Similarity	NPD1929	Approved
0.6897	Remote Similarity	NPD7008	Discontinued
0.6882	Remote Similarity	NPD8407	Phase 2
0.6857	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7057	Phase 3
0.6832	Remote Similarity	NPD7058	Phase 2
0.6826	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8312	Approved
0.6824	Remote Similarity	NPD8313	Approved
0.6813	Remote Similarity	NPD7819	Suspended
0.6806	Remote Similarity	NPD2798	Approved
0.6797	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8320	Phase 1
0.6796	Remote Similarity	NPD8319	Approved
0.679	Remote Similarity	NPD7075	Discontinued
0.6774	Remote Similarity	NPD6799	Approved
0.6772	Remote Similarity	NPD7458	Discontinued
0.677	Remote Similarity	NPD5402	Approved
0.6767	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD9545	Approved
0.6752	Remote Similarity	NPD5403	Approved
0.6744	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5401	Approved
0.673	Remote Similarity	NPD6599	Discontinued
0.6724	Remote Similarity	NPD8435	Approved
0.6718	Remote Similarity	NPD1237	Approved
0.6718	Remote Similarity	NPD5909	Discontinued
0.6715	Remote Similarity	NPD5951	Approved
0.6711	Remote Similarity	NPD7266	Discontinued
0.6711	Remote Similarity	NPD2346	Discontinued
0.6711	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5494	Approved
0.6705	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2799	Discontinued
0.6688	Remote Similarity	NPD3750	Approved
0.6687	Remote Similarity	NPD7411	Suspended
0.6687	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5125	Phase 3
0.6667	Remote Similarity	NPD1202	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD2066	Phase 3
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5126	Approved
0.6647	Remote Similarity	NPD6797	Phase 2
0.6646	Remote Similarity	NPD6801	Discontinued
0.6645	Remote Similarity	NPD2796	Approved
0.6645	Remote Similarity	NPD6190	Approved
0.6643	Remote Similarity	NPD6637	Approved
0.6629	Remote Similarity	NPD8361	Approved
0.6629	Remote Similarity	NPD8360	Approved
0.6623	Remote Similarity	NPD2569	Approved
0.6623	Remote Similarity	NPD2567	Approved
0.6622	Remote Similarity	NPD2313	Discontinued
0.6618	Remote Similarity	NPD969	Suspended
0.6608	Remote Similarity	NPD7685	Pre-registration
0.6608	Remote Similarity	NPD7251	Discontinued
0.6605	Remote Similarity	NPD8455	Phase 2
0.6601	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.66	Remote Similarity	NPD230	Phase 1
0.66	Remote Similarity	NPD1933	Approved
0.6599	Remote Similarity	NPD6832	Phase 2
0.6588	Remote Similarity	NPD7074	Phase 3
0.6581	Remote Similarity	NPD4628	Phase 3
0.6577	Remote Similarity	NPD7713	Phase 3
0.6573	Remote Similarity	NPD6535	Approved
0.6573	Remote Similarity	NPD6534	Approved
0.657	Remote Similarity	NPD7808	Phase 3
0.6569	Remote Similarity	NPD7094	Approved
0.6569	Remote Similarity	NPD6858	Approved
0.6564	Remote Similarity	NPD3817	Phase 2
0.6562	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1989	Approved
0.6561	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7435	Discontinued
0.6556	Remote Similarity	NPD7699	Phase 2
0.6556	Remote Similarity	NPD7700	Phase 2
0.6554	Remote Similarity	NPD6039	Approved
0.6549	Remote Similarity	NPD5306	Approved
0.6549	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5305	Approved
0.6544	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3887	Approved
0.6535	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4307	Phase 2
0.6528	Remote Similarity	NPD1608	Approved
0.6525	Remote Similarity	NPD7741	Discontinued
0.6524	Remote Similarity	NPD7768	Phase 2
0.6519	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6647	Phase 2
0.6514	Remote Similarity	NPD8150	Discontinued
0.6513	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6559	Discontinued
0.6507	Remote Similarity	NPD3267	Approved
0.6507	Remote Similarity	NPD3266	Approved
0.6504	Remote Similarity	NPD9257	Approved
0.6504	Remote Similarity	NPD9259	Approved
0.6484	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6273	Approved
0.6474	Remote Similarity	NPD8166	Discontinued
0.6471	Remote Similarity	NPD7228	Approved
0.6463	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6085	Phase 2
0.646	Remote Similarity	NPD3226	Approved
0.6458	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4807	Approved
0.6458	Remote Similarity	NPD4806	Approved
0.6456	Remote Similarity	NPD3950	Discontinued
0.6452	Remote Similarity	NPD970	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD919	Approved
0.6442	Remote Similarity	NPD37	Approved
0.6439	Remote Similarity	NPD1932	Approved
0.6438	Remote Similarity	NPD920	Approved
0.6438	Remote Similarity	NPD2198	Approved
0.6438	Remote Similarity	NPD1876	Approved
0.6438	Remote Similarity	NPD2199	Approved
0.6433	Remote Similarity	NPD7054	Approved
0.6429	Remote Similarity	NPD3672	Approved
0.6429	Remote Similarity	NPD3673	Approved
0.6429	Remote Similarity	NPD2935	Discontinued
0.6424	Remote Similarity	NPD2979	Phase 3
0.6424	Remote Similarity	NPD4967	Phase 2
0.6424	Remote Similarity	NPD5120	Approved
0.6424	Remote Similarity	NPD4965	Approved
0.6424	Remote Similarity	NPD5121	Approved
0.6424	Remote Similarity	NPD4966	Approved
0.6424	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD5119	Approved
0.6423	Remote Similarity	NPD2201	Approved
0.642	Remote Similarity	NPD8434	Phase 2
0.642	Remote Similarity	NPD4380	Phase 2
0.6415	Remote Similarity	NPD2532	Approved
0.6415	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2534	Approved
0.6415	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2533	Approved
0.6414	Remote Similarity	NPD3972	Approved
0.6403	Remote Similarity	NPD1241	Discontinued
0.64	Remote Similarity	NPD3268	Approved
0.6397	Remote Similarity	NPD2329	Discontinued
0.6395	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7472	Approved
0.6395	Remote Similarity	NPD2797	Approved
0.6393	Remote Similarity	NPD6779	Approved
0.6393	Remote Similarity	NPD6777	Approved
0.6393	Remote Similarity	NPD6780	Approved
0.6393	Remote Similarity	NPD6781	Approved
0.6393	Remote Similarity	NPD6778	Approved
0.6393	Remote Similarity	NPD6782	Approved
0.6393	Remote Similarity	NPD6776	Approved
0.6391	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4106	Approved
0.6389	Remote Similarity	NPD4136	Approved
0.6389	Remote Similarity	NPD4135	Approved
0.6387	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7611	Approved
0.6387	Remote Similarity	NPD1471	Phase 3
0.6387	Remote Similarity	NPD2353	Approved
0.6386	Remote Similarity	NPD3749	Approved
0.6383	Remote Similarity	NPD9493	Approved
0.6382	Remote Similarity	NPD6355	Discontinued
0.6382	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD5124	Phase 1
0.6378	Remote Similarity	NPD7696	Phase 3
0.6378	Remote Similarity	NPD7698	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