NPASS Compound

Structure

NPC82299 OpenBabel07101719252D 31 33 0 0 0 0 0 0 0 0999 V2000 0.7183 -1.0378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0661 1.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7062 2.1581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2957 1.2935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2479 2.4227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3746 0.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2957 0.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2044 2.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0661 -0.2298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7118 2.3076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7062 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2981 1.9777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2479 -0.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5405 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 -1.1448 1.1838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0756 0.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1560 1.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3411 0.6876 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5482 0.1438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1560 0.5056 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 -2.3385 0.6157 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2561 -0.8126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 25 26 2 0 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.28
Volume:	469.221
LogP:	8.557
LogD:	4.757
LogS:	-4.344
# Rotatable Bonds:	1
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	3.717
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212
MDCK Permeability:	1.2227092156535946e-05
Pgp-inhibitor:	0.424
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	99.93775177001953%
Volume Distribution (VD):	3.526
Pgp-substrate:	0.33874258399009705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.588
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.847
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.261
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.874
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.222
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	5.298
Half-life (T1/2):	0.094

ADMET: Toxicity

hERG Blockers:	0.188
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.573
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.958
Carcinogencity:	0.019
Eye Corrosion:	0.004
Eye Irritation:	0.938
Respiratory Toxicity:	0.755

Download Data

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

Natural Product: NPC82299

Natural Product ID:	NPC82299
*Common Name:**	Methylgraviphane
IUPAC Name:	n.a.
Synonyms:	methylgraviphane
Standard InCHIKey:	VHTRJVITHPENFV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H38O4/c1-31-25-19-22(28)18-21-15-13-11-9-7-5-3-2-4-6-8-10-12-14-20-16-23(29)27(26(21)25)24(30)17-20/h16-19,28-30H,2-15H2,1H3
SMILES:	COc1cc(O)cc2c1c1c(O)cc(cc1O)CCCCCCCCCCCCCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375783
PubChem CID:	44419741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8945	Grevillea robusta	Species	Proteaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	30800.0	nM	PMID[515719]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	28900.0	nM	PMID[515719]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	31100.0	nM	PMID[515719]

☑ 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 NPC82299 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	362
0.1-0.2	1707
0.2-0.3	4414
0.3-0.4	12894
0.4-0.5	5429
0.5-0.6	4173
0.6-0.7	7791
0.7-0.8	4731
0.8-0.85	790
0.85-0.9	339
0.9-0.95	63
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC473221
0.9426	High Similarity	NPC105031
0.935	High Similarity	NPC170485
0.9333	High Similarity	NPC102639
0.9268	High Similarity	NPC278955
0.9268	High Similarity	NPC113495
0.9268	High Similarity	NPC105718
0.92	High Similarity	NPC215300
0.92	High Similarity	NPC38017
0.9187	High Similarity	NPC228503
0.9187	High Similarity	NPC138248
0.918	High Similarity	NPC18128
0.918	High Similarity	NPC77789
0.9167	High Similarity	NPC184302
0.9141	High Similarity	NPC469610
0.9134	High Similarity	NPC282508
0.9134	High Similarity	NPC160623
0.9134	High Similarity	NPC8899
0.912	High Similarity	NPC53781
0.9098	High Similarity	NPC476633
0.9083	High Similarity	NPC190514
0.9077	High Similarity	NPC472647
0.9077	High Similarity	NPC191462
0.9077	High Similarity	NPC472649
0.9077	High Similarity	NPC133463
0.9077	High Similarity	NPC170328
0.9077	High Similarity	NPC472648
0.9077	High Similarity	NPC206525
0.9076	High Similarity	NPC115808
0.9076	High Similarity	NPC114064
0.9062	High Similarity	NPC469611
0.9015	High Similarity	NPC273623
0.9008	High Similarity	NPC266006
0.9008	High Similarity	NPC472646
0.9008	High Similarity	NPC71465
0.9	High Similarity	NPC244816
0.9	High Similarity	NPC470760
0.9	High Similarity	NPC221549
0.9	High Similarity	NPC37410
0.9	High Similarity	NPC69261
0.9	High Similarity	NPC258780
0.9	High Similarity	NPC127894
0.9	High Similarity	NPC470759
0.9	High Similarity	NPC50521
0.9	High Similarity	NPC15860
0.9	High Similarity	NPC33270
0.9	High Similarity	NPC219070
0.9	High Similarity	NPC195466
0.9	High Similarity	NPC474933
0.8984	High Similarity	NPC15543
0.8984	High Similarity	NPC473309
0.8984	High Similarity	NPC471517
0.8976	High Similarity	NPC471519
0.8976	High Similarity	NPC471518
0.8968	High Similarity	NPC46978
0.896	High Similarity	NPC293801
0.8931	High Similarity	NPC202846
0.8931	High Similarity	NPC143139
0.8931	High Similarity	NPC205442
0.8923	High Similarity	NPC56764
0.8923	High Similarity	NPC206737
0.8923	High Similarity	NPC469659
0.8923	High Similarity	NPC125649
0.8923	High Similarity	NPC276026
0.8923	High Similarity	NPC7515
0.8923	High Similarity	NPC289258
0.8923	High Similarity	NPC188378
0.8923	High Similarity	NPC555
0.8917	High Similarity	NPC54507
0.8917	High Similarity	NPC141090
0.8917	High Similarity	NPC203113
0.8917	High Similarity	NPC229147
0.8917	High Similarity	NPC150624
0.8917	High Similarity	NPC85292
0.8915	High Similarity	NPC102256
0.8906	High Similarity	NPC126836
0.8906	High Similarity	NPC254000
0.8889	High Similarity	NPC223953
0.8872	High Similarity	NPC308768
0.8872	High Similarity	NPC12668
0.8864	High Similarity	NPC35550
0.8864	High Similarity	NPC22902
0.8864	High Similarity	NPC56329
0.8864	High Similarity	NPC242715
0.8855	High Similarity	NPC55239
0.8855	High Similarity	NPC180602
0.8855	High Similarity	NPC294884
0.8855	High Similarity	NPC111655
0.8855	High Similarity	NPC200557
0.8855	High Similarity	NPC69029
0.8855	High Similarity	NPC240279
0.8855	High Similarity	NPC158142
0.8855	High Similarity	NPC108198
0.8855	High Similarity	NPC10314
0.8855	High Similarity	NPC214853
0.8846	High Similarity	NPC32778
0.8837	High Similarity	NPC472590
0.8833	High Similarity	NPC167934
0.8833	High Similarity	NPC808
0.8833	High Similarity	NPC185541
0.8833	High Similarity	NPC53906
0.8833	High Similarity	NPC464
0.8828	High Similarity	NPC16577
0.881	High Similarity	NPC105925
0.88	High Similarity	NPC474160
0.8797	High Similarity	NPC243996
0.8797	High Similarity	NPC275061
0.8797	High Similarity	NPC218131
0.8797	High Similarity	NPC243759
0.8797	High Similarity	NPC132804
0.8797	High Similarity	NPC29868
0.8797	High Similarity	NPC212942
0.8797	High Similarity	NPC471183
0.8797	High Similarity	NPC79622
0.8797	High Similarity	NPC105847
0.8797	High Similarity	NPC220344
0.8788	High Similarity	NPC133025
0.8788	High Similarity	NPC30632
0.8779	High Similarity	NPC209199
0.8779	High Similarity	NPC160697
0.877	High Similarity	NPC63010
0.877	High Similarity	NPC131118
0.876	High Similarity	NPC224157
0.876	High Similarity	NPC192687
0.875	High Similarity	NPC207702
0.875	High Similarity	NPC180508
0.875	High Similarity	NPC228287
0.875	High Similarity	NPC22610
0.875	High Similarity	NPC276737
0.875	High Similarity	NPC283114
0.875	High Similarity	NPC149008
0.875	High Similarity	NPC154866
0.8741	High Similarity	NPC175838
0.8741	High Similarity	NPC470917
0.874	High Similarity	NPC283049
0.874	High Similarity	NPC230479
0.874	High Similarity	NPC50315
0.874	High Similarity	NPC26879
0.873	High Similarity	NPC270030
0.8722	High Similarity	NPC151656
0.8722	High Similarity	NPC201145
0.8722	High Similarity	NPC230919
0.8722	High Similarity	NPC301765
0.8722	High Similarity	NPC156948
0.8722	High Similarity	NPC266453
0.8722	High Similarity	NPC272157
0.8722	High Similarity	NPC46277
0.8722	High Similarity	NPC86605
0.8722	High Similarity	NPC6262
0.8722	High Similarity	NPC90615
0.8722	High Similarity	NPC3072
0.8722	High Similarity	NPC200935
0.8722	High Similarity	NPC73535
0.8722	High Similarity	NPC25111
0.872	High Similarity	NPC74137
0.872	High Similarity	NPC57199
0.8712	High Similarity	NPC241241
0.8712	High Similarity	NPC313081
0.871	High Similarity	NPC277798
0.871	High Similarity	NPC129176
0.871	High Similarity	NPC100108
0.8682	High Similarity	NPC93962
0.8682	High Similarity	NPC472797
0.8682	High Similarity	NPC190144
0.8672	High Similarity	NPC74817
0.8672	High Similarity	NPC169474
0.8672	High Similarity	NPC159968
0.8672	High Similarity	NPC82679
0.8672	High Similarity	NPC282000
0.8672	High Similarity	NPC236760
0.8672	High Similarity	NPC124452
0.8672	High Similarity	NPC266555
0.8672	High Similarity	NPC246620
0.8672	High Similarity	NPC236791
0.8672	High Similarity	NPC471986
0.8672	High Similarity	NPC293054
0.8672	High Similarity	NPC324112
0.8667	High Similarity	NPC472089
0.8667	High Similarity	NPC265075
0.8657	High Similarity	NPC230124
0.8657	High Similarity	NPC6300
0.8657	High Similarity	NPC184613
0.8657	High Similarity	NPC114171
0.8651	High Similarity	NPC233526
0.8651	High Similarity	NPC84086
0.8651	High Similarity	NPC136319
0.8651	High Similarity	NPC282496
0.8647	High Similarity	NPC472800
0.8647	High Similarity	NPC476639
0.8647	High Similarity	NPC234952
0.8647	High Similarity	NPC300846
0.8647	High Similarity	NPC114155
0.864	High Similarity	NPC39029
0.8636	High Similarity	NPC473107
0.8626	High Similarity	NPC472798
0.8626	High Similarity	NPC14224
0.8626	High Similarity	NPC218884
0.8626	High Similarity	NPC161958
0.8626	High Similarity	NPC6451
0.8623	High Similarity	NPC274454

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 NPC82299 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	992
0.2-0.3	1610
0.3-0.4	2782
0.4-0.5	1685
0.5-0.6	972
0.6-0.7	620
0.7-0.8	138
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8828	High Similarity	NPD4625	Phase 3
0.8594	High Similarity	NPD6917	Clinical (unspecified phase)
0.8504	High Similarity	NPD4749	Approved
0.8462	Intermediate Similarity	NPD4908	Phase 1
0.8397	Intermediate Similarity	NPD3027	Phase 3
0.8346	Intermediate Similarity	NPD1610	Phase 2
0.8333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4750	Phase 3
0.8175	Intermediate Similarity	NPD1548	Phase 1
0.8074	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD1613	Approved
0.8043	Intermediate Similarity	NPD6099	Approved
0.8043	Intermediate Similarity	NPD6100	Approved
0.8015	Intermediate Similarity	NPD6696	Suspended
0.797	Intermediate Similarity	NPD2861	Phase 2
0.7907	Intermediate Similarity	NPD4626	Approved
0.7872	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7635	Approved
0.7836	Intermediate Similarity	NPD3018	Phase 2
0.7795	Intermediate Similarity	NPD6671	Approved
0.7794	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD940	Approved
0.775	Intermediate Similarity	NPD846	Approved
0.7698	Intermediate Similarity	NPD4097	Suspended
0.7698	Intermediate Similarity	NPD1607	Approved
0.7692	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1651	Approved
0.7681	Intermediate Similarity	NPD4060	Phase 1
0.7676	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2983	Phase 2
0.7669	Intermediate Similarity	NPD2982	Phase 2
0.7667	Intermediate Similarity	NPD1242	Phase 1
0.7662	Intermediate Similarity	NPD6232	Discontinued
0.7652	Intermediate Similarity	NPD422	Phase 1
0.7638	Intermediate Similarity	NPD5283	Phase 1
0.7628	Intermediate Similarity	NPD7473	Discontinued
0.7612	Intermediate Similarity	NPD1283	Approved
0.7603	Intermediate Similarity	NPD2532	Approved
0.7603	Intermediate Similarity	NPD2534	Approved
0.7603	Intermediate Similarity	NPD2533	Approved
0.76	Intermediate Similarity	NPD37	Approved
0.7597	Intermediate Similarity	NPD7340	Approved
0.7597	Intermediate Similarity	NPD6959	Discontinued
0.7594	Intermediate Similarity	NPD2981	Phase 2
0.7569	Intermediate Similarity	NPD3750	Approved
0.7569	Intermediate Similarity	NPD3892	Phase 2
0.7557	Intermediate Similarity	NPD5691	Approved
0.7554	Intermediate Similarity	NPD1240	Approved
0.7554	Intermediate Similarity	NPD2238	Phase 2
0.7519	Intermediate Similarity	NPD709	Approved
0.7519	Intermediate Similarity	NPD1611	Approved
0.75	Intermediate Similarity	NPD1398	Phase 1
0.7483	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7447	Phase 1
0.7468	Intermediate Similarity	NPD6234	Discontinued
0.7465	Intermediate Similarity	NPD1510	Phase 2
0.7463	Intermediate Similarity	NPD2233	Approved
0.7463	Intermediate Similarity	NPD2232	Approved
0.7463	Intermediate Similarity	NPD2230	Approved
0.7451	Intermediate Similarity	NPD4967	Phase 2
0.7451	Intermediate Similarity	NPD4966	Approved
0.7451	Intermediate Similarity	NPD4965	Approved
0.744	Intermediate Similarity	NPD2342	Discontinued
0.7438	Intermediate Similarity	NPD3020	Approved
0.7434	Intermediate Similarity	NPD7819	Suspended
0.7413	Intermediate Similarity	NPD2935	Discontinued
0.7407	Intermediate Similarity	NPD1669	Approved
0.7388	Intermediate Similarity	NPD1281	Approved
0.7388	Intermediate Similarity	NPD3705	Approved
0.7379	Intermediate Similarity	NPD6674	Discontinued
0.7372	Intermediate Similarity	NPD4624	Approved
0.7344	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD2859	Approved
0.7333	Intermediate Similarity	NPD2860	Approved
0.7333	Intermediate Similarity	NPD844	Approved
0.7325	Intermediate Similarity	NPD7229	Phase 3
0.7323	Intermediate Similarity	NPD3022	Approved
0.7323	Intermediate Similarity	NPD3021	Approved
0.732	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5844	Phase 1
0.7305	Intermediate Similarity	NPD3620	Phase 2
0.7305	Intermediate Similarity	NPD2979	Phase 3
0.7305	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7213	Phase 3
0.7297	Intermediate Similarity	NPD7041	Phase 2
0.7297	Intermediate Similarity	NPD7390	Discontinued
0.7297	Intermediate Similarity	NPD7212	Phase 2
0.7285	Intermediate Similarity	NPD4005	Discontinued
0.7279	Intermediate Similarity	NPD5327	Phase 3
0.7273	Intermediate Similarity	NPD288	Approved
0.7255	Intermediate Similarity	NPD1934	Approved
0.7254	Intermediate Similarity	NPD5735	Approved
0.7252	Intermediate Similarity	NPD7157	Approved
0.725	Intermediate Similarity	NPD2934	Approved
0.725	Intermediate Similarity	NPD2933	Approved
0.725	Intermediate Similarity	NPD7228	Approved
0.7248	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6584	Phase 3
0.7241	Intermediate Similarity	NPD5762	Approved
0.7241	Intermediate Similarity	NPD3540	Phase 1
0.7241	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5763	Approved
0.7241	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7768	Phase 2
0.7226	Intermediate Similarity	NPD8651	Approved
0.7222	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3748	Approved
0.7222	Intermediate Similarity	NPD968	Approved
0.7208	Intermediate Similarity	NPD2801	Approved
0.72	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6090	Discontinued
0.7197	Intermediate Similarity	NPD6746	Phase 2
0.7192	Intermediate Similarity	NPD1549	Phase 2
0.7188	Intermediate Similarity	NPD5451	Approved
0.7181	Intermediate Similarity	NPD1511	Approved
0.7179	Intermediate Similarity	NPD4055	Discovery
0.7174	Intermediate Similarity	NPD3094	Phase 2
0.7172	Intermediate Similarity	NPD3539	Phase 1
0.7172	Intermediate Similarity	NPD1551	Phase 2
0.7162	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7843	Approved
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5124	Phase 1
0.7132	Intermediate Similarity	NPD1091	Approved
0.7124	Intermediate Similarity	NPD4380	Phase 2
0.7123	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7124	Phase 2
0.7111	Intermediate Similarity	NPD2667	Approved
0.7111	Intermediate Similarity	NPD1778	Approved
0.7111	Intermediate Similarity	NPD2668	Approved
0.7109	Intermediate Similarity	NPD2684	Approved
0.7103	Intermediate Similarity	NPD4108	Discontinued
0.7097	Intermediate Similarity	NPD1465	Phase 2
0.7097	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7466	Approved
0.7095	Intermediate Similarity	NPD7003	Approved
0.7092	Intermediate Similarity	NPD7095	Approved
0.709	Intermediate Similarity	NPD3091	Approved
0.7086	Intermediate Similarity	NPD1512	Approved
0.7083	Intermediate Similarity	NPD6353	Approved
0.708	Intermediate Similarity	NPD1608	Approved
0.7078	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4140	Approved
0.7059	Intermediate Similarity	NPD3496	Discontinued
0.7059	Intermediate Similarity	NPD3847	Discontinued
0.7055	Intermediate Similarity	NPD2438	Suspended
0.7055	Intermediate Similarity	NPD2796	Approved
0.705	Intermediate Similarity	NPD2797	Approved
0.7047	Intermediate Similarity	NPD2677	Approved
0.7045	Intermediate Similarity	NPD497	Approved
0.7044	Intermediate Similarity	NPD7199	Phase 2
0.7042	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3443	Approved
0.7037	Intermediate Similarity	NPD3444	Approved
0.7037	Intermediate Similarity	NPD3445	Approved
0.7034	Intermediate Similarity	NPD6111	Discontinued
0.7029	Intermediate Similarity	NPD6582	Phase 2
0.7029	Intermediate Similarity	NPD6583	Phase 3
0.7023	Intermediate Similarity	NPD5535	Approved
0.702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD6599	Discontinued
0.7007	Intermediate Similarity	NPD3092	Approved
0.7006	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD5711	Approved
0.6992	Remote Similarity	NPD6387	Discontinued
0.6987	Remote Similarity	NPD5929	Approved
0.6985	Remote Similarity	NPD2286	Discontinued
0.698	Remote Similarity	NPD4628	Phase 3
0.6974	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6559	Discontinued
0.697	Remote Similarity	NPD495	Approved
0.697	Remote Similarity	NPD496	Approved
0.697	Remote Similarity	NPD498	Approved
0.6968	Remote Similarity	NPD5090	Approved
0.6968	Remote Similarity	NPD5089	Approved
0.6967	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6651	Approved
0.6966	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7075	Discontinued
0.6962	Remote Similarity	NPD3749	Approved
0.6959	Remote Similarity	NPD7037	Approved
0.6957	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1840	Phase 2
0.6954	Remote Similarity	NPD6087	Phase 1
0.6954	Remote Similarity	NPD4357	Discontinued
0.6948	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3226	Approved
0.694	Remote Similarity	NPD7325	Clinical (unspecified phase)

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