NPASS Compound

Structure

NPC472707 OpenBabel07101719522D 25 26 0 0 1 0 0 0 0 0999 V2000 0.7957 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1554 1.4781 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 -5.6962 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 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 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3479 -1.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 -2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 1 0 0 0 15 21 2 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 18 3 1 1 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.17
Volume:	359.626
LogP:	3.094
LogD:	2.29
LogS:	-4.086
# Rotatable Bonds:	6
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	3.759
Fsp3:	0.579
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:	-5.425
MDCK Permeability:	3.0429777325480245e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.186
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.136
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.222
Plasma Protein Binding (PPB):	90.81681060791016%
Volume Distribution (VD):	0.22
Pgp-substrate:	14.54918384552002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.327
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.512
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.199

ADMET: Excretion

Clearance (CL):	1.555
Half-life (T1/2):	0.594

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.057
Carcinogencity:	0.012
Eye Corrosion:	0.004
Eye Irritation:	0.175
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC472707

Natural Product ID:	NPC472707
*Common Name:**	OEMQRFWSQMZDOR-QSFPRURJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OEMQRFWSQMZDOR-QSFPRURJSA-N
Standard InCHI:	InChI=1S/C19H26O6/c1-17(2)9-14(20)10-18(17,3)13-7-5-12(6-8-13)15(21)25-11-19(4,24)16(22)23/h5-8,14,20,24H,9-11H2,1-4H3,(H,22,23)/t14-,18-,19?/m1/s1
SMILES:	CC1(CC(CC1(C)C2=CC=C(C=C2)C(=O)OCC(C)(C(=O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581623
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32768	basidiomycete deconica sp. 471	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25871540]

☑ 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	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[514931]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	67.0	ug.mL-1	PMID[514931]

☑ 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 NPC472707 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	251
0.1-0.2	890
0.2-0.3	2187
0.3-0.4	5463
0.4-0.5	11074
0.5-0.6	13990
0.6-0.7	7806
0.7-0.8	897
0.8-0.85	94
0.85-0.9	41
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9274	High Similarity	NPC472706
0.9106	High Similarity	NPC472703
0.9032	High Similarity	NPC472704
0.8769	High Similarity	NPC233692
0.8769	High Similarity	NPC239358
0.8702	High Similarity	NPC472248
0.8667	High Similarity	NPC474303
0.8667	High Similarity	NPC475413
0.8636	High Similarity	NPC311492
0.8636	High Similarity	NPC28836
0.8629	High Similarity	NPC472708
0.8626	High Similarity	NPC233860
0.8571	High Similarity	NPC200154
0.854	High Similarity	NPC45307
0.8529	High Similarity	NPC473497
0.8507	High Similarity	NPC52523
0.8507	High Similarity	NPC217673
0.8496	Intermediate Similarity	NPC477368
0.8473	Intermediate Similarity	NPC272946
0.8444	Intermediate Similarity	NPC27721
0.8443	Intermediate Similarity	NPC474363
0.8433	Intermediate Similarity	NPC472247
0.8433	Intermediate Similarity	NPC79699
0.8433	Intermediate Similarity	NPC477367
0.8433	Intermediate Similarity	NPC232888
0.8429	Intermediate Similarity	NPC205389
0.8421	Intermediate Similarity	NPC477364
0.8394	Intermediate Similarity	NPC242355
0.8382	Intermediate Similarity	NPC473301
0.837	Intermediate Similarity	NPC202729
0.8358	Intermediate Similarity	NPC477359
0.8357	Intermediate Similarity	NPC170668
0.831	Intermediate Similarity	NPC477101
0.831	Intermediate Similarity	NPC232583
0.831	Intermediate Similarity	NPC477097
0.831	Intermediate Similarity	NPC25484
0.831	Intermediate Similarity	NPC477099
0.8309	Intermediate Similarity	NPC86772
0.8248	Intermediate Similarity	NPC272523
0.8248	Intermediate Similarity	NPC325805
0.8222	Intermediate Similarity	NPC153617
0.8222	Intermediate Similarity	NPC472250
0.8195	Intermediate Similarity	NPC475508
0.8195	Intermediate Similarity	NPC82712
0.8195	Intermediate Similarity	NPC42234
0.8182	Intermediate Similarity	NPC469636
0.8175	Intermediate Similarity	NPC39549
0.8162	Intermediate Similarity	NPC265459
0.8162	Intermediate Similarity	NPC475262
0.8162	Intermediate Similarity	NPC290833
0.8156	Intermediate Similarity	NPC478264
0.8154	Intermediate Similarity	NPC471466
0.8138	Intermediate Similarity	NPC477098
0.8138	Intermediate Similarity	NPC477100
0.8134	Intermediate Similarity	NPC72915
0.8102	Intermediate Similarity	NPC472551
0.8102	Intermediate Similarity	NPC194769
0.8102	Intermediate Similarity	NPC472545
0.8102	Intermediate Similarity	NPC285221
0.8099	Intermediate Similarity	NPC249811
0.8099	Intermediate Similarity	NPC478263
0.8092	Intermediate Similarity	NPC246166
0.8074	Intermediate Similarity	NPC477360
0.8071	Intermediate Similarity	NPC472546
0.8058	Intermediate Similarity	NPC275592
0.8058	Intermediate Similarity	NPC472547
0.8058	Intermediate Similarity	NPC100913
0.803	Intermediate Similarity	NPC477366
0.8028	Intermediate Similarity	NPC134131
0.8028	Intermediate Similarity	NPC25043
0.8028	Intermediate Similarity	NPC127857
0.8016	Intermediate Similarity	NPC149691
0.8014	Intermediate Similarity	NPC82467
0.8014	Intermediate Similarity	NPC477094
0.8014	Intermediate Similarity	NPC477096
0.8	Intermediate Similarity	NPC41481
0.8	Intermediate Similarity	NPC470153
0.8	Intermediate Similarity	NPC27377
0.8	Intermediate Similarity	NPC291599
0.8	Intermediate Similarity	NPC87448
0.8	Intermediate Similarity	NPC472576
0.8	Intermediate Similarity	NPC118080
0.8	Intermediate Similarity	NPC97947
0.8	Intermediate Similarity	NPC307651
0.8	Intermediate Similarity	NPC471103
0.7986	Intermediate Similarity	NPC81698
0.7986	Intermediate Similarity	NPC250046
0.7986	Intermediate Similarity	NPC9905
0.7986	Intermediate Similarity	NPC60509
0.7984	Intermediate Similarity	NPC474314
0.7984	Intermediate Similarity	NPC473243
0.7984	Intermediate Similarity	NPC158282
0.797	Intermediate Similarity	NPC477365
0.7956	Intermediate Similarity	NPC324898
0.7956	Intermediate Similarity	NPC298547
0.7956	Intermediate Similarity	NPC203486
0.7956	Intermediate Similarity	NPC134937
0.7955	Intermediate Similarity	NPC295664
0.7943	Intermediate Similarity	NPC192658
0.7937	Intermediate Similarity	NPC469509
0.7931	Intermediate Similarity	NPC198455
0.7931	Intermediate Similarity	NPC7095
0.7931	Intermediate Similarity	NPC476173
0.7931	Intermediate Similarity	NPC165260
0.7931	Intermediate Similarity	NPC161239
0.7929	Intermediate Similarity	NPC87934
0.7929	Intermediate Similarity	NPC171207
0.7929	Intermediate Similarity	NPC162613
0.7929	Intermediate Similarity	NPC97667
0.7929	Intermediate Similarity	NPC90614
0.7929	Intermediate Similarity	NPC475660
0.7923	Intermediate Similarity	NPC50872
0.792	Intermediate Similarity	NPC474176
0.792	Intermediate Similarity	NPC128368
0.791	Intermediate Similarity	NPC477370
0.7907	Intermediate Similarity	NPC204784
0.7905	Intermediate Similarity	NPC11410
0.7903	Intermediate Similarity	NPC476003
0.7899	Intermediate Similarity	NPC270364
0.7899	Intermediate Similarity	NPC149401
0.7899	Intermediate Similarity	NPC279637
0.7895	Intermediate Similarity	NPC476599
0.7895	Intermediate Similarity	NPC275576
0.7895	Intermediate Similarity	NPC477363
0.7895	Intermediate Similarity	NPC476033
0.7887	Intermediate Similarity	NPC91703
0.7887	Intermediate Similarity	NPC153214
0.7886	Intermediate Similarity	NPC474364
0.7879	Intermediate Similarity	NPC477362
0.7877	Intermediate Similarity	NPC51602
0.7872	Intermediate Similarity	NPC16912
0.7872	Intermediate Similarity	NPC187566
0.7872	Intermediate Similarity	NPC224491
0.7869	Intermediate Similarity	NPC474376
0.7869	Intermediate Similarity	NPC472316
0.7869	Intermediate Similarity	NPC472315
0.7869	Intermediate Similarity	NPC475203
0.7862	Intermediate Similarity	NPC476975
0.7862	Intermediate Similarity	NPC473215
0.7852	Intermediate Similarity	NPC37968
0.7847	Intermediate Similarity	NPC477737
0.7847	Intermediate Similarity	NPC477095
0.7847	Intermediate Similarity	NPC473602
0.7847	Intermediate Similarity	NPC312393
0.7842	Intermediate Similarity	NPC477358
0.7838	Intermediate Similarity	NPC472549
0.7838	Intermediate Similarity	NPC473670
0.7838	Intermediate Similarity	NPC21410
0.7836	Intermediate Similarity	NPC470753
0.7836	Intermediate Similarity	NPC169913
0.7836	Intermediate Similarity	NPC473220
0.7836	Intermediate Similarity	NPC477357
0.7832	Intermediate Similarity	NPC470152
0.7832	Intermediate Similarity	NPC475759
0.7832	Intermediate Similarity	NPC34943
0.7832	Intermediate Similarity	NPC241951
0.7832	Intermediate Similarity	NPC475122
0.7826	Intermediate Similarity	NPC48929
0.7826	Intermediate Similarity	NPC126516
0.7817	Intermediate Similarity	NPC34012
0.7817	Intermediate Similarity	NPC182869
0.7808	Intermediate Similarity	NPC473214
0.7808	Intermediate Similarity	NPC112216
0.7808	Intermediate Similarity	NPC470245
0.7805	Intermediate Similarity	NPC277788
0.7794	Intermediate Similarity	NPC471832
0.7793	Intermediate Similarity	NPC217918
0.7793	Intermediate Similarity	NPC132652
0.7793	Intermediate Similarity	NPC327031
0.7786	Intermediate Similarity	NPC205305
0.7786	Intermediate Similarity	NPC327511
0.7785	Intermediate Similarity	NPC106895
0.7785	Intermediate Similarity	NPC70344
0.7778	Intermediate Similarity	NPC476973
0.7778	Intermediate Similarity	NPC472572
0.7778	Intermediate Similarity	NPC311825
0.7778	Intermediate Similarity	NPC158663
0.7778	Intermediate Similarity	NPC184817
0.7778	Intermediate Similarity	NPC473088
0.7778	Intermediate Similarity	NPC472575
0.7778	Intermediate Similarity	NPC70403
0.7778	Intermediate Similarity	NPC92867
0.7778	Intermediate Similarity	NPC200471
0.7778	Intermediate Similarity	NPC470157
0.7778	Intermediate Similarity	NPC174982
0.7778	Intermediate Similarity	NPC171525
0.7778	Intermediate Similarity	NPC29704
0.7778	Intermediate Similarity	NPC472571
0.7778	Intermediate Similarity	NPC471104
0.7778	Intermediate Similarity	NPC470159
0.7778	Intermediate Similarity	NPC469349
0.7778	Intermediate Similarity	NPC472568
0.7778	Intermediate Similarity	NPC472556
0.7778	Intermediate Similarity	NPC177940
0.7778	Intermediate Similarity	NPC96903
0.777	Intermediate Similarity	NPC304876
0.777	Intermediate Similarity	NPC219419
0.777	Intermediate Similarity	NPC248265
0.777	Intermediate Similarity	NPC265395
0.777	Intermediate Similarity	NPC477896

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 NPC472707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	663
0.2-0.3	1513
0.3-0.4	2701
0.4-0.5	2359
0.5-0.6	1275
0.6-0.7	390
0.7-0.8	40
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
0.806	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD7236	Approved
0.8016	Intermediate Similarity	NPD4198	Discontinued
0.7937	Intermediate Similarity	NPD2629	Approved
0.7937	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7239	Suspended
0.7639	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD2182	Approved
0.7574	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD2067	Discontinued
0.7536	Intermediate Similarity	NPD7008	Discontinued
0.7532	Intermediate Similarity	NPD7799	Discontinued
0.75	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD6287	Discontinued
0.7445	Intermediate Similarity	NPD6085	Phase 2
0.7445	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD9495	Approved
0.7403	Intermediate Similarity	NPD7057	Phase 3
0.7403	Intermediate Similarity	NPD7058	Phase 2
0.7385	Intermediate Similarity	NPD5951	Approved
0.7344	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5647	Approved
0.7303	Intermediate Similarity	NPD6599	Discontinued
0.728	Intermediate Similarity	NPD164	Approved
0.728	Intermediate Similarity	NPD1237	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7259	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1238	Approved
0.7203	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD6647	Phase 2
0.7192	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5305	Approved
0.7185	Intermediate Similarity	NPD5306	Approved
0.7185	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7961	Discontinued
0.7165	Intermediate Similarity	NPD6685	Approved
0.7154	Intermediate Similarity	NPD969	Suspended
0.7143	Intermediate Similarity	NPD3662	Phase 3
0.7143	Intermediate Similarity	NPD3661	Approved
0.7143	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD3663	Approved
0.7143	Intermediate Similarity	NPD3664	Approved
0.7132	Intermediate Similarity	NPD4136	Approved
0.7132	Intermediate Similarity	NPD4106	Approved
0.7132	Intermediate Similarity	NPD4135	Approved
0.7097	Intermediate Similarity	NPD2066	Phase 3
0.708	Intermediate Similarity	NPD4807	Approved
0.708	Intermediate Similarity	NPD4806	Approved
0.7063	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1693	Approved
0.7045	Intermediate Similarity	NPD6010	Discontinued
0.7045	Intermediate Similarity	NPD2652	Approved
0.7045	Intermediate Similarity	NPD2650	Approved
0.7034	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6653	Approved
0.7025	Intermediate Similarity	NPD1088	Approved
0.7021	Intermediate Similarity	NPD5204	Approved
0.6985	Remote Similarity	NPD4102	Approved
0.6985	Remote Similarity	NPD4105	Approved
0.697	Remote Similarity	NPD6858	Approved
0.697	Remote Similarity	NPD7094	Approved
0.6943	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5125	Phase 3
0.6934	Remote Similarity	NPD5126	Approved
0.6933	Remote Similarity	NPD2575	Approved
0.6929	Remote Similarity	NPD5765	Approved
0.6929	Remote Similarity	NPD1930	Approved
0.6929	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5667	Approved
0.6929	Remote Similarity	NPD1929	Approved
0.6928	Remote Similarity	NPD8368	Discontinued
0.6912	Remote Similarity	NPD7741	Discontinued
0.6912	Remote Similarity	NPD9545	Approved
0.6908	Remote Similarity	NPD6799	Approved
0.6906	Remote Similarity	NPD9717	Approved
0.6905	Remote Similarity	NPD8407	Phase 2
0.6894	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5403	Approved
0.6879	Remote Similarity	NPD2160	Approved
0.6879	Remote Similarity	NPD2625	Approved
0.6879	Remote Similarity	NPD2626	Approved
0.6879	Remote Similarity	NPD2627	Approved
0.6879	Remote Similarity	NPD2159	Approved
0.6879	Remote Similarity	NPD2628	Approved
0.6875	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD6798	Discontinued
0.6871	Remote Similarity	NPD2569	Approved
0.6871	Remote Similarity	NPD2567	Approved
0.6863	Remote Similarity	NPD5401	Approved
0.686	Remote Similarity	NPD1086	Approved
0.686	Remote Similarity	NPD1089	Approved
0.686	Remote Similarity	NPD9258	Approved
0.686	Remote Similarity	NPD9256	Approved
0.686	Remote Similarity	NPD1090	Approved
0.6855	Remote Similarity	NPD1989	Approved
0.6853	Remote Similarity	NPD4620	Approved
0.6853	Remote Similarity	NPD5201	Approved
0.6853	Remote Similarity	NPD5203	Approved
0.6853	Remote Similarity	NPD6832	Phase 2
0.6853	Remote Similarity	NPD4617	Approved
0.685	Remote Similarity	NPD1932	Approved
0.6848	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6002	Phase 3
0.6846	Remote Similarity	NPD6004	Phase 3
0.6846	Remote Similarity	NPD5762	Approved
0.6846	Remote Similarity	NPD5763	Approved
0.6846	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2346	Discontinued
0.6846	Remote Similarity	NPD6005	Phase 3
0.6846	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6663	Approved
0.6828	Remote Similarity	NPD6233	Phase 2
0.6824	Remote Similarity	NPD2799	Discontinued
0.6824	Remote Similarity	NPD4308	Phase 3
0.6824	Remote Similarity	NPD8434	Phase 2
0.6822	Remote Similarity	NPD5048	Discontinued
0.6821	Remote Similarity	NPD4110	Phase 3
0.6821	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7075	Discontinued
0.6806	Remote Similarity	NPD7095	Approved
0.68	Remote Similarity	NPD4534	Discontinued
0.6795	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7458	Discontinued
0.6788	Remote Similarity	NPD7009	Phase 2
0.6786	Remote Similarity	NPD3972	Approved
0.6783	Remote Similarity	NPD5736	Approved
0.6779	Remote Similarity	NPD2935	Discontinued
0.6777	Remote Similarity	NPD800	Approved
0.6772	Remote Similarity	NPD6801	Discontinued
0.6767	Remote Similarity	NPD6912	Phase 3
0.6761	Remote Similarity	NPD6362	Approved
0.6759	Remote Similarity	NPD411	Approved
0.6759	Remote Similarity	NPD4621	Approved
0.6759	Remote Similarity	NPD4619	Approved
0.6759	Remote Similarity	NPD2313	Discontinued
0.6753	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5909	Discontinued
0.6742	Remote Similarity	NPD4234	Approved
0.6742	Remote Similarity	NPD4233	Approved
0.6736	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD447	Suspended
0.6726	Remote Similarity	NPD6765	Approved
0.6726	Remote Similarity	NPD6764	Approved
0.6715	Remote Similarity	NPD7610	Discontinued
0.6713	Remote Similarity	NPD2798	Approved
0.6712	Remote Similarity	NPD7713	Phase 3
0.6712	Remote Similarity	NPD7714	Approved
0.6712	Remote Similarity	NPD4062	Phase 3
0.6712	Remote Similarity	NPD7715	Approved
0.6711	Remote Similarity	NPD7305	Phase 1
0.6711	Remote Similarity	NPD7003	Approved
0.6711	Remote Similarity	NPD8166	Discontinued
0.6711	Remote Similarity	NPD7033	Discontinued
0.6694	Remote Similarity	NPD1202	Approved
0.6694	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5958	Discontinued
0.6688	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD5119	Approved
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD6309	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD9257	Approved
0.6667	Remote Similarity	NPD5121	Approved
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD5120	Approved
0.6667	Remote Similarity	NPD6310	Approved
0.6667	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD9259	Approved
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD6311	Approved
0.6667	Remote Similarity	NPD2354	Approved
0.6647	Remote Similarity	NPD8361	Approved
0.6647	Remote Similarity	NPD8360	Approved
0.6647	Remote Similarity	NPD8435	Approved
0.6645	Remote Similarity	NPD2534	Approved
0.6645	Remote Similarity	NPD2532	Approved
0.6645	Remote Similarity	NPD2533	Approved
0.6645	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1203	Approved
0.6628	Remote Similarity	NPD8150	Discontinued
0.6623	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD230	Phase 1
0.6617	Remote Similarity	NPD1317	Discontinued
0.6612	Remote Similarity	NPD1087	Approved
0.6603	Remote Similarity	NPD5049	Phase 3
0.6601	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1019	Discontinued
0.6596	Remote Similarity	NPD4216	Approved
0.6596	Remote Similarity	NPD2610	Approved
0.6596	Remote Similarity	NPD2612	Approved
0.6596	Remote Similarity	NPD4215	Approved
0.6596	Remote Similarity	NPD2608	Approved
0.6596	Remote Similarity	NPD4217	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