NPASS Compound

Structure

CID228972 OpenBabel06191716022D 21 22 0 0 0 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 -0.8660 3.5000 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 5.1962 -0.0000 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 4.3301 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 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 -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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 9 15 2 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.13
Volume:	308.05
LogP:	4.54
LogD:	3.61
LogS:	-4.551
# Rotatable Bonds:	6
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	2.491
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.681
MDCK Permeability:	2.3445782062481157e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	100.72553253173828%
Volume Distribution (VD):	0.488
Pgp-substrate:	0.8522743582725525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.345
CYP2C19-inhibitor:	0.906
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.759
CYP2C9-substrate:	0.822
CYP2D6-inhibitor:	0.922
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.423
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	12.771
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.955
Carcinogencity:	0.703
Eye Corrosion:	0.005
Eye Irritation:	0.919
Respiratory Toxicity:	0.521

Download Data

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

Natural Product: NPC228972

Natural Product ID:	NPC228972
*Common Name:**	Obovatol
IUPAC Name:	5-prop-2-enyl-3-(3-prop-2-enylphenoxy)benzene-1,2-diol
Synonyms:	Obovatol
Standard InCHIKey:	RVIUPPNYFNZVFG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O3/c1-3-6-13-8-5-9-15(10-13)21-17-12-14(7-4-2)11-16(19)18(17)20/h3-5,8-12,19-20H,1-2,6-7H2
SMILES:	C=CCc1cccc(c1)Oc1cc(CC=C)cc(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551850
PubChem CID:	45270574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[23434030]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4093781]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	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	6
Others	4

Activity Type	# Activity
Cell Line	1
Organism	3
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	9.0	ug.mL-1	PMID[469040]
NPT2	Others	Unspecified		IC50	=	4.8	ug.mL-1	PMID[469040]
NPT1	Others	Radical scavenging activity		IC50	=	33.0	ug.mL-1	PMID[469040]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	6.54	n.a.	PMID[469041]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	27550.0	nM	PMID[469041]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	14.72	n.a.	PMID[469041]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	12230.0	nM	PMID[469041]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	11.49	n.a.	PMID[469041]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	15670.0	nM	PMID[469041]
NPT27	Others	Unspecified		CC50	=	180230.0	nM	PMID[469041]

☑ 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 NPC228972 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	470
0.1-0.2	2078
0.2-0.3	7325
0.3-0.4	12314
0.4-0.5	3328
0.5-0.6	4453
0.6-0.7	7279
0.7-0.8	4179
0.8-0.85	747
0.85-0.9	335
0.9-0.95	185
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC122792
0.975	High Similarity	NPC470699
0.975	High Similarity	NPC210355
0.9667	High Similarity	NPC181361
0.9512	High Similarity	NPC472338
0.9435	High Similarity	NPC472597
0.9421	High Similarity	NPC298757
0.9421	High Similarity	NPC203133
0.9421	High Similarity	NPC57490
0.9421	High Similarity	NPC251855
0.9421	High Similarity	NPC117214
0.9421	High Similarity	NPC193544
0.9421	High Similarity	NPC475169
0.9421	High Similarity	NPC472093
0.9421	High Similarity	NPC233410
0.9421	High Similarity	NPC234400
0.9421	High Similarity	NPC208950
0.9421	High Similarity	NPC17943
0.9421	High Similarity	NPC116907
0.9421	High Similarity	NPC221077
0.9421	High Similarity	NPC60885
0.9412	High Similarity	NPC145780
0.936	High Similarity	NPC7903
0.936	High Similarity	NPC16208
0.936	High Similarity	NPC474134
0.936	High Similarity	NPC184447
0.936	High Similarity	NPC131128
0.936	High Similarity	NPC470752
0.936	High Similarity	NPC160991
0.936	High Similarity	NPC35932
0.9355	High Similarity	NPC91291
0.9344	High Similarity	NPC18924
0.9344	High Similarity	NPC214406
0.9344	High Similarity	NPC78974
0.9344	High Similarity	NPC223136
0.9344	High Similarity	NPC103823
0.9344	High Similarity	NPC44748
0.9344	High Similarity	NPC28730
0.9333	High Similarity	NPC71579
0.9333	High Similarity	NPC41562
0.9333	High Similarity	NPC262253
0.9333	High Similarity	NPC473411
0.9316	High Similarity	NPC86947
0.9286	High Similarity	NPC475840
0.9286	High Similarity	NPC229442
0.9286	High Similarity	NPC168059
0.928	High Similarity	NPC309787
0.9274	High Similarity	NPC470258
0.9274	High Similarity	NPC202582
0.9274	High Similarity	NPC222004
0.9274	High Similarity	NPC210623
0.9274	High Similarity	NPC285339
0.9274	High Similarity	NPC226788
0.9274	High Similarity	NPC273295
0.9274	High Similarity	NPC190629
0.9274	High Similarity	NPC3439
0.9274	High Similarity	NPC218856
0.9268	High Similarity	NPC236791
0.9268	High Similarity	NPC159968
0.9268	High Similarity	NPC293054
0.9268	High Similarity	NPC324112
0.9268	High Similarity	NPC82679
0.9268	High Similarity	NPC246620
0.9268	High Similarity	NPC74817
0.9268	High Similarity	NPC169474
0.9268	High Similarity	NPC124452
0.9268	High Similarity	NPC474119
0.9268	High Similarity	NPC282000
0.9268	High Similarity	NPC127587
0.9262	High Similarity	NPC82483
0.9262	High Similarity	NPC299584
0.9262	High Similarity	NPC265483
0.9256	High Similarity	NPC233526
0.9256	High Similarity	NPC282496
0.9256	High Similarity	NPC136319
0.9256	High Similarity	NPC197757
0.9256	High Similarity	NPC228922
0.9213	High Similarity	NPC317380
0.9213	High Similarity	NPC66840
0.9213	High Similarity	NPC170694
0.9213	High Similarity	NPC310854
0.9213	High Similarity	NPC256307
0.9206	High Similarity	NPC86655
0.9206	High Similarity	NPC202762
0.9206	High Similarity	NPC127624
0.92	High Similarity	NPC214860
0.9194	High Similarity	NPC226331
0.9194	High Similarity	NPC98631
0.9194	High Similarity	NPC46274
0.9194	High Similarity	NPC186843
0.9194	High Similarity	NPC470213
0.9194	High Similarity	NPC206615
0.9187	High Similarity	NPC76451
0.918	High Similarity	NPC5796
0.918	High Similarity	NPC206487
0.9167	High Similarity	NPC166759
0.9167	High Similarity	NPC472596
0.916	High Similarity	NPC20674
0.9141	High Similarity	NPC121812
0.9141	High Similarity	NPC112939
0.9141	High Similarity	NPC112246
0.9141	High Similarity	NPC474206
0.9141	High Similarity	NPC472337
0.9141	High Similarity	NPC470356
0.9141	High Similarity	NPC94750
0.9134	High Similarity	NPC36661
0.9134	High Similarity	NPC36490
0.9127	High Similarity	NPC469613
0.9127	High Similarity	NPC30043
0.9127	High Similarity	NPC470095
0.9127	High Similarity	NPC469625
0.9127	High Similarity	NPC470096
0.912	High Similarity	NPC10225
0.912	High Similarity	NPC476968
0.912	High Similarity	NPC170844
0.912	High Similarity	NPC45824
0.912	High Similarity	NPC58164
0.9113	High Similarity	NPC41706
0.9113	High Similarity	NPC163332
0.9113	High Similarity	NPC292056
0.9113	High Similarity	NPC250432
0.9113	High Similarity	NPC111247
0.9113	High Similarity	NPC5447
0.9113	High Similarity	NPC147821
0.9113	High Similarity	NPC183181
0.9113	High Similarity	NPC319625
0.9113	High Similarity	NPC118787
0.9106	High Similarity	NPC194519
0.9106	High Similarity	NPC105925
0.9098	High Similarity	NPC95168
0.9083	High Similarity	NPC474565
0.9083	High Similarity	NPC232084
0.9083	High Similarity	NPC247364
0.9083	High Similarity	NPC10932
0.9083	High Similarity	NPC61516
0.907	High Similarity	NPC270456
0.907	High Similarity	NPC230734
0.907	High Similarity	NPC302701
0.907	High Similarity	NPC269091
0.907	High Similarity	NPC227503
0.907	High Similarity	NPC265433
0.907	High Similarity	NPC248727
0.907	High Similarity	NPC474639
0.907	High Similarity	NPC472336
0.907	High Similarity	NPC16435
0.907	High Similarity	NPC306441
0.907	High Similarity	NPC472334
0.907	High Similarity	NPC162659
0.9062	High Similarity	NPC106215
0.9055	High Similarity	NPC253105
0.9055	High Similarity	NPC201587
0.9048	High Similarity	NPC234488
0.9048	High Similarity	NPC474481
0.9048	High Similarity	NPC469614
0.9048	High Similarity	NPC126836
0.9048	High Similarity	NPC469612
0.9048	High Similarity	NPC311680
0.9048	High Similarity	NPC299221
0.9048	High Similarity	NPC51840
0.904	High Similarity	NPC28765
0.904	High Similarity	NPC154866
0.904	High Similarity	NPC72529
0.9032	High Similarity	NPC191037
0.9032	High Similarity	NPC178284
0.9032	High Similarity	NPC58607
0.9024	High Similarity	NPC293701
0.9024	High Similarity	NPC48990
0.9024	High Similarity	NPC114901
0.9016	High Similarity	NPC261661
0.9	High Similarity	NPC176051
0.9	High Similarity	NPC226629
0.9	High Similarity	NPC102904
0.9	High Similarity	NPC276490
0.9	High Similarity	NPC103976
0.9	High Similarity	NPC474282
0.9	High Similarity	NPC211549
0.9	High Similarity	NPC107551
0.9	High Similarity	NPC474390
0.9	High Similarity	NPC326797
0.8992	High Similarity	NPC151224
0.8992	High Similarity	NPC260898
0.8992	High Similarity	NPC259638
0.8992	High Similarity	NPC164787
0.8992	High Similarity	NPC47398
0.8992	High Similarity	NPC234333
0.8992	High Similarity	NPC61946
0.8984	High Similarity	NPC158331
0.8984	High Similarity	NPC11060
0.8976	High Similarity	NPC469907
0.8976	High Similarity	NPC474017
0.8976	High Similarity	NPC45715
0.8976	High Similarity	NPC474356
0.8976	High Similarity	NPC12275
0.8968	High Similarity	NPC5851
0.8968	High Similarity	NPC212015
0.8968	High Similarity	NPC86030
0.896	High Similarity	NPC216836
0.896	High Similarity	NPC50368
0.896	High Similarity	NPC252131
0.896	High Similarity	NPC236760

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 NPC228972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	449
0.1-0.2	966
0.2-0.3	2000
0.3-0.4	2630
0.4-0.5	1530
0.5-0.6	858
0.6-0.7	591
0.7-0.8	112
0.8-0.85	9
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9194	High Similarity	NPD1529	Clinical (unspecified phase)
0.912	High Similarity	NPD3027	Phase 3
0.9113	High Similarity	NPD1530	Clinical (unspecified phase)
0.8906	High Similarity	NPD1612	Clinical (unspecified phase)
0.8906	High Similarity	NPD1613	Approved
0.8487	Intermediate Similarity	NPD228	Approved
0.8455	Intermediate Similarity	NPD1548	Phase 1
0.8346	Intermediate Similarity	NPD2982	Phase 2
0.8346	Intermediate Similarity	NPD2983	Phase 2
0.8333	Intermediate Similarity	NPD1610	Phase 2
0.8333	Intermediate Similarity	NPD1558	Phase 1
0.8268	Intermediate Similarity	NPD2981	Phase 2
0.8231	Intermediate Similarity	NPD3018	Phase 2
0.8168	Intermediate Similarity	NPD4908	Phase 1
0.8106	Intermediate Similarity	NPD4625	Phase 3
0.8062	Intermediate Similarity	NPD4749	Approved
0.8062	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5283	Phase 1
0.8045	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1511	Approved
0.8014	Intermediate Similarity	NPD2801	Approved
0.7949	Intermediate Similarity	NPD1242	Phase 1
0.7945	Intermediate Similarity	NPD1934	Approved
0.7907	Intermediate Similarity	NPD422	Phase 1
0.7905	Intermediate Similarity	NPD3882	Suspended
0.7902	Intermediate Similarity	NPD1512	Approved
0.7869	Intermediate Similarity	NPD3022	Approved
0.7869	Intermediate Similarity	NPD3021	Approved
0.782	Intermediate Similarity	NPD2861	Phase 2
0.7793	Intermediate Similarity	NPD1653	Approved
0.7787	Intermediate Similarity	NPD2684	Approved
0.777	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4675	Approved
0.7687	Intermediate Similarity	NPD4678	Approved
0.7667	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD6671	Approved
0.7623	Intermediate Similarity	NPD968	Approved
0.7589	Intermediate Similarity	NPD3540	Phase 1
0.7548	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6166	Phase 2
0.754	Intermediate Similarity	NPD7843	Approved
0.7536	Intermediate Similarity	NPD4060	Phase 1
0.7536	Intermediate Similarity	NPD3620	Phase 2
0.7536	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.7518	Intermediate Similarity	NPD3539	Phase 1
0.7517	Intermediate Similarity	NPD4357	Discontinued
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3817	Phase 2
0.7481	Intermediate Similarity	NPD6584	Phase 3
0.7481	Intermediate Similarity	NPD5846	Approved
0.7481	Intermediate Similarity	NPD6516	Phase 2
0.7464	Intermediate Similarity	NPD2674	Phase 3
0.7452	Intermediate Similarity	NPD3818	Discontinued
0.7451	Intermediate Similarity	NPD6234	Discontinued
0.7445	Intermediate Similarity	NPD7095	Approved
0.7438	Intermediate Similarity	NPD846	Approved
0.7438	Intermediate Similarity	NPD940	Approved
0.7419	Intermediate Similarity	NPD290	Approved
0.7417	Intermediate Similarity	NPD1465	Phase 2
0.7405	Intermediate Similarity	NPD1357	Approved
0.7405	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD6100	Approved
0.7394	Intermediate Similarity	NPD6099	Approved
0.7373	Intermediate Similarity	NPD2934	Approved
0.7373	Intermediate Similarity	NPD2933	Approved
0.7361	Intermediate Similarity	NPD3060	Approved
0.7358	Intermediate Similarity	NPD7472	Approved
0.7358	Intermediate Similarity	NPD7074	Phase 3
0.7355	Intermediate Similarity	NPD7199	Phase 2
0.7353	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4123	Phase 3
0.7343	Intermediate Similarity	NPD7266	Discontinued
0.7329	Intermediate Similarity	NPD7124	Phase 2
0.7313	Intermediate Similarity	NPD1608	Approved
0.7311	Intermediate Similarity	NPD2860	Approved
0.7311	Intermediate Similarity	NPD2859	Approved
0.731	Intermediate Similarity	NPD3750	Approved
0.7302	Intermediate Similarity	NPD4750	Phase 3
0.7297	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3020	Approved
0.7267	Intermediate Similarity	NPD4005	Discontinued
0.7267	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3144	Approved
0.7266	Intermediate Similarity	NPD3145	Approved
0.7266	Intermediate Similarity	NPD5535	Approved
0.7261	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2219	Phase 1
0.7259	Intermediate Similarity	NPD6582	Phase 2
0.7259	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6583	Phase 3
0.7255	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6111	Discontinued
0.7254	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4536	Approved
0.7254	Intermediate Similarity	NPD4538	Approved
0.7241	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4237	Approved
0.7241	Intermediate Similarity	NPD4236	Phase 3
0.7241	Intermediate Similarity	NPD4162	Approved
0.7237	Intermediate Similarity	NPD37	Approved
0.7234	Intermediate Similarity	NPD230	Phase 1
0.7234	Intermediate Similarity	NPD4340	Discontinued
0.723	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7447	Phase 1
0.7227	Intermediate Similarity	NPD9296	Approved
0.7222	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4966	Approved
0.7208	Intermediate Similarity	NPD4965	Approved
0.7208	Intermediate Similarity	NPD4967	Phase 2
0.7206	Intermediate Similarity	NPD8651	Approved
0.7205	Intermediate Similarity	NPD6797	Phase 2
0.7203	Intermediate Similarity	NPD5588	Approved
0.7203	Intermediate Similarity	NPD5960	Phase 3
0.7192	Intermediate Similarity	NPD6331	Phase 2
0.7192	Intermediate Similarity	NPD3892	Phase 2
0.7185	Intermediate Similarity	NPD2231	Phase 2
0.7185	Intermediate Similarity	NPD2235	Phase 2
0.7174	Intermediate Similarity	NPD9494	Approved
0.7172	Intermediate Similarity	NPD1549	Phase 2
0.7163	Intermediate Similarity	NPD1240	Approved
0.7163	Intermediate Similarity	NPD943	Approved
0.7162	Intermediate Similarity	NPD7213	Phase 3
0.7162	Intermediate Similarity	NPD6799	Approved
0.7162	Intermediate Similarity	NPD7212	Phase 2
0.716	Intermediate Similarity	NPD7251	Discontinued
0.7154	Intermediate Similarity	NPD291	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7134	Intermediate Similarity	NPD8054	Approved
0.7134	Intermediate Similarity	NPD8053	Approved
0.7133	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD821	Approved
0.7125	Intermediate Similarity	NPD7228	Approved
0.7123	Intermediate Similarity	NPD6674	Discontinued
0.7123	Intermediate Similarity	NPD1652	Phase 2
0.7117	Intermediate Similarity	NPD7808	Phase 3
0.7113	Intermediate Similarity	NPD5735	Approved
0.7111	Intermediate Similarity	NPD1535	Discovery
0.7105	Intermediate Similarity	NPD4380	Phase 2
0.7103	Intermediate Similarity	NPD1375	Discontinued
0.7099	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6233	Phase 2
0.709	Intermediate Similarity	NPD17	Approved
0.7089	Intermediate Similarity	NPD6232	Discontinued
0.7083	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1510	Phase 2
0.7081	Intermediate Similarity	NPD5844	Phase 1
0.708	Intermediate Similarity	NPD3225	Approved
0.708	Intermediate Similarity	NPD6696	Suspended
0.7075	Intermediate Similarity	NPD4628	Phase 3
0.7075	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4110	Phase 3
0.7075	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1894	Discontinued
0.7068	Intermediate Similarity	NPD1182	Approved
0.7063	Intermediate Similarity	NPD1607	Approved
0.7059	Intermediate Similarity	NPD1481	Phase 2
0.7051	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7075	Discontinued
0.7042	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2161	Phase 2
0.7034	Intermediate Similarity	NPD1551	Phase 2
0.7034	Intermediate Similarity	NPD2796	Approved
0.7031	Intermediate Similarity	NPD5451	Approved
0.7029	Intermediate Similarity	NPD2797	Approved
0.7027	Intermediate Similarity	NPD2677	Approved
0.7021	Intermediate Similarity	NPD5110	Phase 2
0.7021	Intermediate Similarity	NPD5111	Phase 2
0.7021	Intermediate Similarity	NPD5718	Phase 2
0.7021	Intermediate Similarity	NPD6798	Discontinued
0.7021	Intermediate Similarity	NPD5109	Approved
0.702	Intermediate Similarity	NPD2122	Discontinued
0.7009	Intermediate Similarity	NPD9094	Approved
0.7007	Intermediate Similarity	NPD5177	Phase 3
0.7	Intermediate Similarity	NPD9379	Approved
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9377	Approved
0.6993	Remote Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD5124	Phase 1
0.6993	Remote Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5058	Phase 3
0.6977	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3687	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