NPASS Compound

Structure

CID47536 OpenBabel06191715382D 23 25 0 0 1 0 0 0 0 0999 V2000 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 -1.7321 0.0000 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 3.4641 -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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 -0.0000 -1.0000 0.0000 C 0 0 2 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 1.7321 -1.0000 0.0000 C 0 0 1 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 2.5981 -1.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 1 0 0 0 0 4 8 2 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 15 20 2 0 0 0 0 16 13 1 1 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 18 13 1 6 0 0 0 18 22 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	325.58
LogP:	3.089
LogD:	2.969
LogS:	-4.436
# Rotatable Bonds:	4
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	3.973
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.656
MDCK Permeability:	3.0024028092157096e-05
Pgp-inhibitor:	0.118
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.547
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.709
Plasma Protein Binding (PPB):	94.88326263427734%
Volume Distribution (VD):	0.64
Pgp-substrate:	2.781832218170166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.66
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.528
CYP2C9-substrate:	0.779
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.799
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	11.58
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.921
Drug-inuced Liver Injury (DILI):	0.923
AMES Toxicity:	0.98
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.966
Carcinogencity:	0.947
Eye Corrosion:	0.084
Eye Irritation:	0.425
Respiratory Toxicity:	0.514

Download Data

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

Natural Product: NPC47536

Natural Product ID:	NPC47536
*Common Name:**	Obolactone
IUPAC Name:	(2R)-2-[[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]-6-[(E)-2-phenylethenyl]-2,3-dihydropyran-4-one
Synonyms:	Obolactone
Standard InCHIKey:	NZGGCMIUTMKVIG-WADNSWHXSA-N
Standard InCHI:	InChI=1S/C19H18O4/c20-15-11-17(10-9-14-5-2-1-3-6-14)22-18(12-15)13-16-7-4-8-19(21)23-16/h1-6,8-11,16,18H,7,12-13H2/b10-9+/t16-,18+/m1/s1
SMILES:	O=C1C[C@@H](C[C@H]2CC=CC(=O)O2)OC(=C1)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452184
PubChem CID:	11370316
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO23852	Cryptocarya obovata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165150]
NPO23852	Cryptocarya obovata	Species	Lauraceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[15165150]
NPO23852	Cryptocarya obovata	Species	Lauraceae	Eukaryota	n.a.	fruit	n.a.	PMID[15165150]
NPO23852	Cryptocarya obovata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20558060]
NPO23852	Cryptocarya obovata	Species	Lauraceae	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	1

Activity Type	# Activity
Cell Line	5
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3000.0	nM	PMID[512252]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	13200.0	nM	PMID[512253]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	43000.0	nM	PMID[512253]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	32000.0	nM	PMID[512253]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	24000.0	nM	PMID[512253]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	5300.0	nM	PMID[512253]
NPT2	Others	Unspecified		Selectivity Index	=	2.5	n.a.	PMID[512253]

☑ 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 NPC47536 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	257
0.1-0.2	1144
0.2-0.3	3117
0.3-0.4	8458
0.4-0.5	12170
0.5-0.6	12793
0.6-0.7	4450
0.7-0.8	294
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC40178
0.9223	High Similarity	NPC20485
0.8687	High Similarity	NPC77273
0.8496	Intermediate Similarity	NPC64340
0.8393	Intermediate Similarity	NPC471616
0.8348	Intermediate Similarity	NPC474223
0.8348	Intermediate Similarity	NPC475827
0.8319	Intermediate Similarity	NPC190298
0.8235	Intermediate Similarity	NPC23453
0.8136	Intermediate Similarity	NPC474254
0.8136	Intermediate Similarity	NPC474159
0.8108	Intermediate Similarity	NPC474157
0.8073	Intermediate Similarity	NPC51174
0.8	Intermediate Similarity	NPC169050
0.8	Intermediate Similarity	NPC286608
0.7963	Intermediate Similarity	NPC301943
0.7963	Intermediate Similarity	NPC474365
0.7895	Intermediate Similarity	NPC87069
0.7881	Intermediate Similarity	NPC474222
0.7881	Intermediate Similarity	NPC475804
0.7876	Intermediate Similarity	NPC474689
0.783	Intermediate Similarity	NPC270654
0.7826	Intermediate Similarity	NPC210092
0.7822	Intermediate Similarity	NPC96625
0.7807	Intermediate Similarity	NPC474176
0.7807	Intermediate Similarity	NPC161611
0.78	Intermediate Similarity	NPC53299
0.7778	Intermediate Similarity	NPC324835
0.7778	Intermediate Similarity	NPC308619
0.7778	Intermediate Similarity	NPC127491
0.7768	Intermediate Similarity	NPC469636
0.7768	Intermediate Similarity	NPC474364
0.7767	Intermediate Similarity	NPC213156
0.7767	Intermediate Similarity	NPC240108
0.776	Intermediate Similarity	NPC291419
0.776	Intermediate Similarity	NPC60825
0.7759	Intermediate Similarity	NPC149691
0.7757	Intermediate Similarity	NPC179411
0.7748	Intermediate Similarity	NPC477251
0.7739	Intermediate Similarity	NPC172525
0.7739	Intermediate Similarity	NPC308744
0.7727	Intermediate Similarity	NPC114594
0.7727	Intermediate Similarity	NPC269644
0.7679	Intermediate Similarity	NPC470007
0.7664	Intermediate Similarity	NPC278228
0.7658	Intermediate Similarity	NPC209632
0.7658	Intermediate Similarity	NPC269457
0.7652	Intermediate Similarity	NPC272524
0.7642	Intermediate Similarity	NPC5472
0.7636	Intermediate Similarity	NPC60679
0.7627	Intermediate Similarity	NPC152812
0.7615	Intermediate Similarity	NPC42211
0.7611	Intermediate Similarity	NPC281604
0.7593	Intermediate Similarity	NPC476120
0.7593	Intermediate Similarity	NPC35448
0.7593	Intermediate Similarity	NPC78701
0.7586	Intermediate Similarity	NPC474363
0.7578	Intermediate Similarity	NPC136994
0.7578	Intermediate Similarity	NPC88255
0.7576	Intermediate Similarity	NPC71795
0.7523	Intermediate Similarity	NPC325497
0.7523	Intermediate Similarity	NPC146351
0.7523	Intermediate Similarity	NPC118343
0.7523	Intermediate Similarity	NPC98911
0.7523	Intermediate Similarity	NPC472318
0.7522	Intermediate Similarity	NPC470391
0.7522	Intermediate Similarity	NPC156648
0.7521	Intermediate Similarity	NPC474408
0.7521	Intermediate Similarity	NPC474685
0.75	Intermediate Similarity	NPC9822
0.75	Intermediate Similarity	NPC476096
0.75	Intermediate Similarity	NPC276775
0.75	Intermediate Similarity	NPC92754
0.75	Intermediate Similarity	NPC99240
0.75	Intermediate Similarity	NPC231591
0.75	Intermediate Similarity	NPC249912
0.75	Intermediate Similarity	NPC103048
0.75	Intermediate Similarity	NPC128368
0.75	Intermediate Similarity	NPC476033
0.75	Intermediate Similarity	NPC204784
0.75	Intermediate Similarity	NPC79608
0.75	Intermediate Similarity	NPC289201
0.748	Intermediate Similarity	NPC17567
0.748	Intermediate Similarity	NPC319995
0.748	Intermediate Similarity	NPC289415
0.748	Intermediate Similarity	NPC473881
0.7479	Intermediate Similarity	NPC469574
0.7478	Intermediate Similarity	NPC210089
0.7477	Intermediate Similarity	NPC234305
0.746	Intermediate Similarity	NPC469930
0.7456	Intermediate Similarity	NPC10251
0.7456	Intermediate Similarity	NPC269023
0.7456	Intermediate Similarity	NPC99846
0.7456	Intermediate Similarity	NPC17417
0.7438	Intermediate Similarity	NPC476225
0.7436	Intermediate Similarity	NPC477411
0.7436	Intermediate Similarity	NPC196075
0.7436	Intermediate Similarity	NPC307651
0.7434	Intermediate Similarity	NPC136962
0.7434	Intermediate Similarity	NPC474376
0.7434	Intermediate Similarity	NPC472316
0.7434	Intermediate Similarity	NPC472315
0.7434	Intermediate Similarity	NPC475203
0.7431	Intermediate Similarity	NPC271475
0.7431	Intermediate Similarity	NPC145052
0.7431	Intermediate Similarity	NPC225060
0.7426	Intermediate Similarity	NPC243289
0.7426	Intermediate Similarity	NPC208183
0.7419	Intermediate Similarity	NPC477369
0.7414	Intermediate Similarity	NPC234376
0.7414	Intermediate Similarity	NPC212415
0.7414	Intermediate Similarity	NPC474314
0.7411	Intermediate Similarity	NPC280616
0.7411	Intermediate Similarity	NPC85977
0.7411	Intermediate Similarity	NPC171831
0.7411	Intermediate Similarity	NPC242913
0.7407	Intermediate Similarity	NPC12695
0.74	Intermediate Similarity	NPC89950
0.7398	Intermediate Similarity	NPC223351
0.7398	Intermediate Similarity	NPC65627
0.7391	Intermediate Similarity	NPC196246
0.7391	Intermediate Similarity	NPC93084
0.7391	Intermediate Similarity	NPC214067
0.7391	Intermediate Similarity	NPC251854
0.7373	Intermediate Similarity	NPC228936
0.7368	Intermediate Similarity	NPC56493
0.7358	Intermediate Similarity	NPC119631
0.7358	Intermediate Similarity	NPC476484
0.735	Intermediate Similarity	NPC265002
0.7345	Intermediate Similarity	NPC321670
0.7339	Intermediate Similarity	NPC12881
0.7339	Intermediate Similarity	NPC140118
0.7339	Intermediate Similarity	NPC472704
0.7339	Intermediate Similarity	NPC8990
0.7339	Intermediate Similarity	NPC477362
0.7333	Intermediate Similarity	NPC173443
0.7328	Intermediate Similarity	NPC1082
0.7328	Intermediate Similarity	NPC305912
0.7328	Intermediate Similarity	NPC291799
0.7328	Intermediate Similarity	NPC476003
0.7321	Intermediate Similarity	NPC82426
0.7321	Intermediate Similarity	NPC91820
0.7315	Intermediate Similarity	NPC130398
0.7315	Intermediate Similarity	NPC206764
0.7311	Intermediate Similarity	NPC226093
0.7311	Intermediate Similarity	NPC100353
0.7304	Intermediate Similarity	NPC83628
0.7304	Intermediate Similarity	NPC265407
0.7302	Intermediate Similarity	NPC473423
0.7297	Intermediate Similarity	NPC70624
0.7295	Intermediate Similarity	NPC243059
0.7295	Intermediate Similarity	NPC280827
0.7295	Intermediate Similarity	NPC473243
0.7282	Intermediate Similarity	NPC294134
0.7281	Intermediate Similarity	NPC474111
0.7281	Intermediate Similarity	NPC37622
0.7281	Intermediate Similarity	NPC30594
0.7281	Intermediate Similarity	NPC37115
0.7281	Intermediate Similarity	NPC119271
0.7281	Intermediate Similarity	NPC329705
0.728	Intermediate Similarity	NPC295664
0.728	Intermediate Similarity	NPC246166
0.728	Intermediate Similarity	NPC244454
0.7273	Intermediate Similarity	NPC176228
0.7273	Intermediate Similarity	NPC135951
0.7273	Intermediate Similarity	NPC154517
0.7265	Intermediate Similarity	NPC158282
0.7265	Intermediate Similarity	NPC477250
0.7265	Intermediate Similarity	NPC82899
0.7265	Intermediate Similarity	NPC270699
0.7265	Intermediate Similarity	NPC79496
0.7258	Intermediate Similarity	NPC140561
0.7258	Intermediate Similarity	NPC141970
0.7258	Intermediate Similarity	NPC472703
0.725	Intermediate Similarity	NPC108532
0.7244	Intermediate Similarity	NPC231627
0.7241	Intermediate Similarity	NPC174099
0.7241	Intermediate Similarity	NPC273837
0.7238	Intermediate Similarity	NPC477704
0.7238	Intermediate Similarity	NPC304760
0.7238	Intermediate Similarity	NPC477693
0.7236	Intermediate Similarity	NPC50872
0.7232	Intermediate Similarity	NPC474112
0.7231	Intermediate Similarity	NPC15850
0.7228	Intermediate Similarity	NPC303245
0.7222	Intermediate Similarity	NPC477366
0.7222	Intermediate Similarity	NPC477363
0.7222	Intermediate Similarity	NPC470818
0.7217	Intermediate Similarity	NPC277788
0.7209	Intermediate Similarity	NPC183348
0.7209	Intermediate Similarity	NPC282230
0.7207	Intermediate Similarity	NPC474308
0.7207	Intermediate Similarity	NPC203925
0.7207	Intermediate Similarity	NPC80115
0.7207	Intermediate Similarity	NPC476042
0.7203	Intermediate Similarity	NPC477475
0.7203	Intermediate Similarity	NPC477476
0.7203	Intermediate Similarity	NPC13784
0.72	Intermediate Similarity	NPC167577
0.72	Intermediate Similarity	NPC78517

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 NPC47536 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	825
0.2-0.3	1374
0.3-0.4	3033
0.4-0.5	2397
0.5-0.6	1031
0.6-0.7	248
0.7-0.8	16
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD1282	Approved
0.789	Intermediate Similarity	NPD5909	Discontinued
0.7857	Intermediate Similarity	NPD2067	Discontinued
0.7658	Intermediate Similarity	NPD5048	Discontinued
0.7586	Intermediate Similarity	NPD6010	Discontinued
0.7523	Intermediate Similarity	NPD1238	Approved
0.7523	Intermediate Similarity	NPD7798	Approved
0.7478	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6647	Phase 2
0.7456	Intermediate Similarity	NPD2182	Approved
0.7414	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6832	Phase 2
0.7117	Intermediate Similarity	NPD5926	Approved
0.7105	Intermediate Similarity	NPD164	Approved
0.7103	Intermediate Similarity	NPD3672	Approved
0.7103	Intermediate Similarity	NPD3673	Approved
0.7091	Intermediate Similarity	NPD1989	Approved
0.7087	Intermediate Similarity	NPD3266	Approved
0.7087	Intermediate Similarity	NPD3267	Approved
0.7083	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD1202	Approved
0.7054	Intermediate Similarity	NPD2066	Phase 3
0.704	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1241	Discontinued
0.6984	Remote Similarity	NPD6637	Approved
0.6983	Remote Similarity	NPD3134	Approved
0.697	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2796	Approved
0.6947	Remote Similarity	NPD2313	Discontinued
0.6947	Remote Similarity	NPD3268	Approved
0.6931	Remote Similarity	NPD227	Approved
0.6931	Remote Similarity	NPD225	Approved
0.6923	Remote Similarity	NPD1358	Approved
0.6917	Remote Similarity	NPD7094	Approved
0.6917	Remote Similarity	NPD6858	Approved
0.6905	Remote Similarity	NPD6287	Discontinued
0.6899	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7033	Discontinued
0.6887	Remote Similarity	NPD9259	Approved
0.6887	Remote Similarity	NPD9257	Approved
0.688	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD9490	Approved
0.6855	Remote Similarity	NPD9545	Approved
0.6831	Remote Similarity	NPD5403	Approved
0.6829	Remote Similarity	NPD9493	Approved
0.6822	Remote Similarity	NPD2797	Approved
0.6814	Remote Similarity	NPD9495	Approved
0.681	Remote Similarity	NPD1237	Approved
0.6809	Remote Similarity	NPD5401	Approved
0.6774	Remote Similarity	NPD2347	Approved
0.6769	Remote Similarity	NPD1019	Discontinued
0.6769	Remote Similarity	NPD2798	Approved
0.6762	Remote Similarity	NPD9491	Approved
0.6744	Remote Similarity	NPD3225	Approved
0.6738	Remote Similarity	NPD6799	Approved
0.6731	Remote Similarity	NPD226	Approved
0.6724	Remote Similarity	NPD1929	Approved
0.6724	Remote Similarity	NPD9261	Approved
0.6724	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1930	Approved
0.6723	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1894	Discontinued
0.6719	Remote Similarity	NPD3972	Approved
0.6719	Remote Similarity	NPD9717	Approved
0.6692	Remote Similarity	NPD1203	Approved
0.6692	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2569	Approved
0.6691	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2567	Approved
0.6667	Remote Similarity	NPD4793	Discontinued
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1087	Approved
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD1933	Approved
0.6642	Remote Similarity	NPD6233	Phase 2
0.6642	Remote Similarity	NPD1510	Phase 2
0.6641	Remote Similarity	NPD5647	Approved
0.6638	Remote Similarity	NPD1932	Approved
0.6636	Remote Similarity	NPD9256	Approved
0.6636	Remote Similarity	NPD9258	Approved
0.6619	Remote Similarity	NPD1549	Phase 2
0.6617	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2198	Approved
0.6615	Remote Similarity	NPD2199	Approved
0.6613	Remote Similarity	NPD3317	Approved
0.661	Remote Similarity	NPD9697	Approved
0.6599	Remote Similarity	NPD6801	Discontinued
0.6596	Remote Similarity	NPD3887	Approved
0.6593	Remote Similarity	NPD4307	Phase 2
0.6585	Remote Similarity	NPD2650	Approved
0.6585	Remote Similarity	NPD2652	Approved
0.6571	Remote Similarity	NPD942	Approved
0.6567	Remote Similarity	NPD6798	Discontinued
0.6562	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.656	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD969	Suspended
0.6555	Remote Similarity	NPD6685	Approved
0.6554	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7236	Approved
0.6549	Remote Similarity	NPD1693	Approved
0.6547	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD800	Approved
0.6545	Remote Similarity	NPD5346	Phase 2
0.6545	Remote Similarity	NPD5347	Phase 2
0.6545	Remote Similarity	NPD689	Discontinued
0.6531	Remote Similarity	NPD5890	Approved
0.6531	Remote Similarity	NPD7411	Suspended
0.6531	Remote Similarity	NPD5889	Approved
0.6529	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4628	Phase 3
0.6522	Remote Similarity	NPD3748	Approved
0.6522	Remote Similarity	NPD2799	Discontinued
0.6515	Remote Similarity	NPD6085	Phase 2
0.6515	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5402	Approved
0.6504	Remote Similarity	NPD5535	Approved
0.65	Remote Similarity	NPD9267	Approved
0.65	Remote Similarity	NPD9264	Approved
0.65	Remote Similarity	NPD9263	Approved
0.6493	Remote Similarity	NPD7008	Discontinued
0.6489	Remote Similarity	NPD5667	Approved
0.6486	Remote Similarity	NPD1089	Approved
0.6486	Remote Similarity	NPD1090	Approved
0.6486	Remote Similarity	NPD1086	Approved
0.6484	Remote Similarity	NPD17	Approved
0.648	Remote Similarity	NPD4198	Discontinued
0.6479	Remote Similarity	NPD6190	Approved
0.6476	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD2935	Discontinued
0.6471	Remote Similarity	NPD3140	Approved
0.6471	Remote Similarity	NPD3142	Approved
0.6471	Remote Similarity	NPD9716	Approved
0.6463	Remote Similarity	NPD6599	Discontinued
0.6463	Remote Similarity	NPD4380	Phase 2
0.6449	Remote Similarity	NPD3971	Phase 1
0.6446	Remote Similarity	NPD74	Approved
0.6446	Remote Similarity	NPD9266	Approved
0.6443	Remote Similarity	NPD7819	Suspended
0.6441	Remote Similarity	NPD5765	Approved
0.6434	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4576	Approved
0.6429	Remote Similarity	NPD1239	Approved
0.6429	Remote Similarity	NPD2346	Discontinued
0.6429	Remote Similarity	NPD4574	Approved
0.6429	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7609	Phase 3
0.6424	Remote Similarity	NPD7075	Discontinued
0.6417	Remote Similarity	NPD467	Phase 1
0.6406	Remote Similarity	NPD5585	Approved
0.6404	Remote Similarity	NPD9260	Approved
0.6403	Remote Similarity	NPD4308	Phase 3
0.64	Remote Similarity	NPD5951	Approved
0.64	Remote Similarity	NPD3817	Phase 2
0.6397	Remote Similarity	NPD4062	Phase 3
0.6385	Remote Similarity	NPD2610	Approved
0.6385	Remote Similarity	NPD3131	Approved
0.6385	Remote Similarity	NPD2612	Approved
0.6385	Remote Similarity	NPD4218	Approved
0.6385	Remote Similarity	NPD2611	Approved
0.6385	Remote Similarity	NPD4216	Approved
0.6385	Remote Similarity	NPD4217	Approved
0.6385	Remote Similarity	NPD2609	Approved
0.6385	Remote Similarity	NPD4215	Approved
0.6385	Remote Similarity	NPD2608	Approved
0.6385	Remote Similarity	NPD3132	Approved
0.6383	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5536	Phase 2
0.6372	Remote Similarity	NPD7631	Approved
0.6372	Remote Similarity	NPD1088	Approved
0.637	Remote Similarity	NPD920	Approved
0.637	Remote Similarity	NPD6039	Approved
0.6364	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD650	Approved
0.6357	Remote Similarity	NPD1551	Phase 2
0.6351	Remote Similarity	NPD6585	Discontinued
0.635	Remote Similarity	NPD1240	Approved
0.6348	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1243	Approved
0.6336	Remote Similarity	NPD1608	Approved
0.6327	Remote Similarity	NPD7239	Suspended
0.6324	Remote Similarity	NPD1296	Phase 2
0.6324	Remote Similarity	NPD3764	Approved
0.6319	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1563	Approved
0.6312	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2353	Approved
0.6311	Remote Similarity	NPD2329	Discontinued
0.6308	Remote Similarity	NPD3496	Discontinued
0.6308	Remote Similarity	NPD3847	Discontinued
0.6304	Remote Similarity	NPD6355	Discontinued
0.6299	Remote Similarity	NPD5291	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