NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	426.26
Volume:	442.873
LogP:	4.522
LogD:	3.738
LogS:	-4.586
# Rotatable Bonds:	9
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	4.512
Fsp3:	0.826
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.731
MDCK Permeability:	5.5087566579459235e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.125

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	92.7091293334961%
Volume Distribution (VD):	2.124
Pgp-substrate:	5.862155437469482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.599
CYP2C9-inhibitor:	0.176
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.072
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.368

ADMET: Excretion

Clearance (CL):	4.715
Half-life (T1/2):	0.315

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.824
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.369
Carcinogencity:	0.096
Eye Corrosion:	0.006
Eye Irritation:	0.036
Respiratory Toxicity:	0.545

Download Data

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

Natural Product: NPC477747

Natural Product ID:	NPC477747
*Common Name:**	[(2R,3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-2-methyl-6-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-3-yl] (2S)-2-methylbutanoate
IUPAC Name:	[(2R,3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-2-methyl-6-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-3-yl] (2S)-2-methylbutanoate
Synonyms:
Standard InCHIKey:	RKOJSIKGEAYBDC-JCTMOKGCSA-N
Standard InCHI:	InChI=1S/C23H38O7/c1-8-14(3)21(26)29-19-15(4)27-22(20(18(19)25)28-16(5)24)30-23(6,7)17-11-9-13(2)10-12-17/h9,14-15,17-20,22,25H,8,10-12H2,1-7H3/t14-,15+,17-,18-,19-,20+,22-/m0/s1
SMILES:	CC[C@H](C)C(=O)O[C@H]1[C@H](O[C@H]([C@@H]([C@H]1O)OC(=O)C)OC(C)(C)[C@@H]2CCC(=CC2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122180072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO33680	Pittosporum venulosum	Species	Pittosporaceae	Eukaryota	n.a.	State Forest 144, Mt. Windsor Tableland, Queensland, Australia	1995-JUL	PMID[25984885]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	39730	nM	PMID[25984885]

☑ 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 NPC477747 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	175
0.1-0.2	1278
0.2-0.3	5372
0.3-0.4	13603
0.4-0.5	9647
0.5-0.6	8132
0.6-0.7	4007
0.7-0.8	448
0.8-0.85	26
0.85-0.9	4
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477746
0.9125	High Similarity	NPC100697
0.907	High Similarity	NPC477749
0.9059	High Similarity	NPC477748
0.8953	High Similarity	NPC202886
0.8902	High Similarity	NPC20072
0.8652	High Similarity	NPC178949
0.8652	High Similarity	NPC96736
0.837	Intermediate Similarity	NPC309503
0.837	Intermediate Similarity	NPC239547
0.837	Intermediate Similarity	NPC91197
0.837	Intermediate Similarity	NPC125551
0.837	Intermediate Similarity	NPC96597
0.837	Intermediate Similarity	NPC155319
0.8295	Intermediate Similarity	NPC248312
0.8276	Intermediate Similarity	NPC470836
0.8222	Intermediate Similarity	NPC472199
0.8222	Intermediate Similarity	NPC472197
0.8152	Intermediate Similarity	NPC108141
0.8132	Intermediate Similarity	NPC320089
0.809	Intermediate Similarity	NPC309656
0.8065	Intermediate Similarity	NPC256230
0.8065	Intermediate Similarity	NPC54731
0.8046	Intermediate Similarity	NPC166279
0.8046	Intermediate Similarity	NPC266718
0.8043	Intermediate Similarity	NPC211238
0.8043	Intermediate Similarity	NPC472198
0.8022	Intermediate Similarity	NPC302584
0.7957	Intermediate Similarity	NPC275310
0.7957	Intermediate Similarity	NPC286612
0.7957	Intermediate Similarity	NPC230347
0.7935	Intermediate Similarity	NPC61201
0.7935	Intermediate Similarity	NPC472196
0.7935	Intermediate Similarity	NPC238090
0.7935	Intermediate Similarity	NPC472195
0.7935	Intermediate Similarity	NPC474792
0.7935	Intermediate Similarity	NPC91654
0.7935	Intermediate Similarity	NPC67398
0.7917	Intermediate Similarity	NPC280991
0.7895	Intermediate Similarity	NPC70733
0.7895	Intermediate Similarity	NPC56071
0.7895	Intermediate Similarity	NPC477928
0.7889	Intermediate Similarity	NPC471756
0.7889	Intermediate Similarity	NPC137368
0.7889	Intermediate Similarity	NPC471755
0.7879	Intermediate Similarity	NPC293512
0.7857	Intermediate Similarity	NPC110813
0.7849	Intermediate Similarity	NPC2003
0.7849	Intermediate Similarity	NPC25701
0.7849	Intermediate Similarity	NPC159698
0.7841	Intermediate Similarity	NPC475035
0.7835	Intermediate Similarity	NPC154452
0.7826	Intermediate Similarity	NPC235051
0.7822	Intermediate Similarity	NPC472508
0.78	Intermediate Similarity	NPC295389
0.7791	Intermediate Similarity	NPC163362
0.7791	Intermediate Similarity	NPC127295
0.7789	Intermediate Similarity	NPC476613
0.7789	Intermediate Similarity	NPC476612
0.7789	Intermediate Similarity	NPC278506
0.7778	Intermediate Similarity	NPC470763
0.7778	Intermediate Similarity	NPC470767
0.7778	Intermediate Similarity	NPC162033
0.7765	Intermediate Similarity	NPC133377
0.7755	Intermediate Similarity	NPC151516
0.7742	Intermediate Similarity	NPC474835
0.7732	Intermediate Similarity	NPC21064
0.7732	Intermediate Similarity	NPC121072
0.7732	Intermediate Similarity	NPC476611
0.7727	Intermediate Similarity	NPC156089
0.7727	Intermediate Similarity	NPC470313
0.7727	Intermediate Similarity	NPC473500
0.7727	Intermediate Similarity	NPC38295
0.7723	Intermediate Similarity	NPC118225
0.7723	Intermediate Similarity	NPC167383
0.7723	Intermediate Similarity	NPC306746
0.7723	Intermediate Similarity	NPC204407
0.7723	Intermediate Similarity	NPC137917
0.7723	Intermediate Similarity	NPC237503
0.7723	Intermediate Similarity	NPC57362
0.7717	Intermediate Similarity	NPC303451
0.7717	Intermediate Similarity	NPC6414
0.7708	Intermediate Similarity	NPC198422
0.7708	Intermediate Similarity	NPC40182
0.7701	Intermediate Similarity	NPC236649
0.7701	Intermediate Similarity	NPC21693
0.77	Intermediate Similarity	NPC283849
0.7677	Intermediate Similarity	NPC121566
0.7677	Intermediate Similarity	NPC100955
0.7677	Intermediate Similarity	NPC31430
0.7677	Intermediate Similarity	NPC85593
0.7677	Intermediate Similarity	NPC223741
0.7677	Intermediate Similarity	NPC173583
0.7677	Intermediate Similarity	NPC470768
0.7674	Intermediate Similarity	NPC321728
0.767	Intermediate Similarity	NPC46388
0.767	Intermediate Similarity	NPC37739
0.766	Intermediate Similarity	NPC305160
0.766	Intermediate Similarity	NPC294293
0.7653	Intermediate Similarity	NPC223834
0.7653	Intermediate Similarity	NPC201191
0.7653	Intermediate Similarity	NPC470571
0.7647	Intermediate Similarity	NPC68419
0.7647	Intermediate Similarity	NPC476886
0.7647	Intermediate Similarity	NPC476881
0.7647	Intermediate Similarity	NPC476882
0.7647	Intermediate Similarity	NPC129340
0.7647	Intermediate Similarity	NPC199457
0.7647	Intermediate Similarity	NPC102914
0.7647	Intermediate Similarity	NPC274507
0.7647	Intermediate Similarity	NPC40049
0.7647	Intermediate Similarity	NPC476887
0.7647	Intermediate Similarity	NPC476880
0.7647	Intermediate Similarity	NPC164194
0.7647	Intermediate Similarity	NPC174679
0.7647	Intermediate Similarity	NPC110139
0.7647	Intermediate Similarity	NPC220984
0.7647	Intermediate Similarity	NPC269095
0.7647	Intermediate Similarity	NPC59804
0.7647	Intermediate Similarity	NPC270667
0.7647	Intermediate Similarity	NPC127056
0.7647	Intermediate Similarity	NPC108709
0.7647	Intermediate Similarity	NPC7870
0.7647	Intermediate Similarity	NPC75747
0.7647	Intermediate Similarity	NPC474589
0.7647	Intermediate Similarity	NPC476885
0.7647	Intermediate Similarity	NPC29069
0.7647	Intermediate Similarity	NPC475296
0.7647	Intermediate Similarity	NPC476884
0.7647	Intermediate Similarity	NPC78046
0.7647	Intermediate Similarity	NPC279554
0.7647	Intermediate Similarity	NPC127153
0.7647	Intermediate Similarity	NPC56713
0.7647	Intermediate Similarity	NPC136877
0.7647	Intermediate Similarity	NPC101450
0.7647	Intermediate Similarity	NPC476883
0.7647	Intermediate Similarity	NPC90856
0.7634	Intermediate Similarity	NPC9447
0.7634	Intermediate Similarity	NPC208839
0.7629	Intermediate Similarity	NPC469870
0.7629	Intermediate Similarity	NPC469871
0.7629	Intermediate Similarity	NPC244878
0.7624	Intermediate Similarity	NPC128795
0.7624	Intermediate Similarity	NPC135015
0.7624	Intermediate Similarity	NPC476123
0.7624	Intermediate Similarity	NPC472507
0.7624	Intermediate Similarity	NPC28198
0.7624	Intermediate Similarity	NPC217921
0.7624	Intermediate Similarity	NPC48548
0.7624	Intermediate Similarity	NPC284807
0.7624	Intermediate Similarity	NPC177246
0.7624	Intermediate Similarity	NPC473288
0.7609	Intermediate Similarity	NPC309310
0.7609	Intermediate Similarity	NPC473058
0.7604	Intermediate Similarity	NPC474194
0.76	Intermediate Similarity	NPC95243
0.76	Intermediate Similarity	NPC63023
0.76	Intermediate Similarity	NPC239961
0.76	Intermediate Similarity	NPC473199
0.76	Intermediate Similarity	NPC210178
0.7596	Intermediate Similarity	NPC47063
0.7596	Intermediate Similarity	NPC204458
0.7596	Intermediate Similarity	NPC271138
0.7596	Intermediate Similarity	NPC138334
0.7596	Intermediate Similarity	NPC189884
0.7596	Intermediate Similarity	NPC269315
0.7586	Intermediate Similarity	NPC103634
0.7582	Intermediate Similarity	NPC475037
0.7579	Intermediate Similarity	NPC469543
0.7573	Intermediate Similarity	NPC108748
0.7573	Intermediate Similarity	NPC473481
0.7573	Intermediate Similarity	NPC297208
0.7573	Intermediate Similarity	NPC250481
0.7573	Intermediate Similarity	NPC30397
0.7573	Intermediate Similarity	NPC31839
0.7573	Intermediate Similarity	NPC285410
0.7573	Intermediate Similarity	NPC191763
0.7573	Intermediate Similarity	NPC164419
0.7573	Intermediate Similarity	NPC263827
0.7573	Intermediate Similarity	NPC235841
0.7573	Intermediate Similarity	NPC179434
0.7573	Intermediate Similarity	NPC211798
0.7556	Intermediate Similarity	NPC471494
0.7551	Intermediate Similarity	NPC20673
0.7551	Intermediate Similarity	NPC154127
0.7551	Intermediate Similarity	NPC198992
0.7549	Intermediate Similarity	NPC40728
0.7549	Intermediate Similarity	NPC316974
0.7549	Intermediate Similarity	NPC127853
0.7549	Intermediate Similarity	NPC265655
0.7529	Intermediate Similarity	NPC229655
0.7527	Intermediate Similarity	NPC159876
0.7527	Intermediate Similarity	NPC118078
0.7527	Intermediate Similarity	NPC117596
0.7526	Intermediate Similarity	NPC151093
0.7526	Intermediate Similarity	NPC81483
0.7526	Intermediate Similarity	NPC61630
0.7526	Intermediate Similarity	NPC307517
0.7526	Intermediate Similarity	NPC169468
0.7526	Intermediate Similarity	NPC472015

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 NPC477747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1759
0.2-0.3	4053
0.3-0.4	2150
0.4-0.5	602
0.5-0.6	352
0.6-0.7	78
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7525	Intermediate Similarity	NPD6412	Phase 2
0.7451	Intermediate Similarity	NPD6686	Approved
0.7347	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD46	Approved
0.734	Intermediate Similarity	NPD6698	Approved
0.7212	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD8513	Phase 3
0.7117	Intermediate Similarity	NPD8517	Approved
0.7117	Intermediate Similarity	NPD8516	Approved
0.7117	Intermediate Similarity	NPD8515	Approved
0.6916	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7983	Approved
0.6847	Remote Similarity	NPD7328	Approved
0.6847	Remote Similarity	NPD7327	Approved
0.6842	Remote Similarity	NPD8328	Phase 3
0.6814	Remote Similarity	NPD7503	Approved
0.6804	Remote Similarity	NPD7838	Discovery
0.6789	Remote Similarity	NPD8133	Approved
0.6786	Remote Similarity	NPD7516	Approved
0.6757	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8377	Approved
0.6726	Remote Similarity	NPD8294	Approved
0.6724	Remote Similarity	NPD7507	Approved
0.6702	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6596	Remote Similarity	NPD6110	Phase 1
0.6566	Remote Similarity	NPD7637	Suspended
0.6566	Remote Similarity	NPD6411	Approved
0.6555	Remote Similarity	NPD7319	Approved
0.6549	Remote Similarity	NPD7641	Discontinued
0.6538	Remote Similarity	NPD5344	Discontinued
0.6525	Remote Similarity	NPD8293	Discontinued
0.6525	Remote Similarity	NPD8074	Phase 3
0.6495	Remote Similarity	NPD4250	Approved
0.6495	Remote Similarity	NPD4251	Approved
0.6489	Remote Similarity	NPD6435	Approved
0.6471	Remote Similarity	NPD7736	Approved
0.6471	Remote Similarity	NPD7839	Suspended
0.6466	Remote Similarity	NPD6370	Approved
0.646	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4822	Approved
0.6452	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4821	Approved
0.6452	Remote Similarity	NPD4819	Approved
0.6452	Remote Similarity	NPD4820	Approved
0.6421	Remote Similarity	NPD3669	Approved
0.6421	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4249	Approved
0.6386	Remote Similarity	NPD368	Approved
0.6356	Remote Similarity	NPD8341	Approved
0.6356	Remote Similarity	NPD8342	Approved
0.6356	Remote Similarity	NPD7492	Approved
0.6356	Remote Similarity	NPD8299	Approved
0.6356	Remote Similarity	NPD8340	Approved
0.6346	Remote Similarity	NPD7638	Approved
0.6337	Remote Similarity	NPD6399	Phase 3
0.6327	Remote Similarity	NPD7524	Approved
0.6316	Remote Similarity	NPD6009	Approved
0.6303	Remote Similarity	NPD6616	Approved
0.6303	Remote Similarity	NPD8451	Approved
0.6293	Remote Similarity	NPD6054	Approved
0.6293	Remote Similarity	NPD6059	Approved
0.6289	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7640	Approved
0.6286	Remote Similarity	NPD7639	Approved
0.6277	Remote Similarity	NPD5368	Approved
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7829	Approved
0.6271	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD7154	Phase 3
0.625	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD6882	Approved
0.6239	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8444	Approved
0.6237	Remote Similarity	NPD4271	Approved
0.6237	Remote Similarity	NPD4268	Approved
0.6216	Remote Similarity	NPD6371	Approved
0.6211	Remote Similarity	NPD5369	Approved
0.6195	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD4225	Approved
0.6186	Remote Similarity	NPD8080	Discontinued
0.6186	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6319	Approved
0.6147	Remote Similarity	NPD6402	Approved
0.6147	Remote Similarity	NPD5739	Approved
0.6147	Remote Similarity	NPD7128	Approved
0.6147	Remote Similarity	NPD6675	Approved
0.6139	Remote Similarity	NPD3168	Discontinued
0.6134	Remote Similarity	NPD7642	Approved
0.6134	Remote Similarity	NPD6067	Discontinued
0.6132	Remote Similarity	NPD6648	Approved
0.6117	Remote Similarity	NPD5282	Discontinued
0.6117	Remote Similarity	NPD7748	Approved
0.6106	Remote Similarity	NPD8297	Approved
0.6102	Remote Similarity	NPD6016	Approved
0.6102	Remote Similarity	NPD6015	Approved
0.6098	Remote Similarity	NPD8392	Approved
0.6098	Remote Similarity	NPD8390	Approved
0.6098	Remote Similarity	NPD8391	Approved
0.6095	Remote Similarity	NPD7902	Approved
0.6082	Remote Similarity	NPD6695	Phase 3
0.6082	Remote Similarity	NPD5362	Discontinued
0.6078	Remote Similarity	NPD7515	Phase 2
0.6064	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5695	Phase 3
0.605	Remote Similarity	NPD5988	Approved
0.6036	Remote Similarity	NPD7320	Approved
0.6036	Remote Similarity	NPD6899	Approved
0.6036	Remote Similarity	NPD6881	Approved
0.6024	Remote Similarity	NPD6109	Phase 1
0.6	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6372	Approved
0.5982	Remote Similarity	NPD6373	Approved
0.598	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD1811	Approved
0.5978	Remote Similarity	NPD1810	Approved
0.596	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6932	Approved
0.5946	Remote Similarity	NPD5701	Approved
0.5946	Remote Similarity	NPD5697	Approved
0.5935	Remote Similarity	NPD8337	Approved
0.5935	Remote Similarity	NPD8336	Approved
0.5929	Remote Similarity	NPD7102	Approved
0.5929	Remote Similarity	NPD7290	Approved
0.5929	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6883	Approved
0.5918	Remote Similarity	NPD5331	Approved
0.5918	Remote Similarity	NPD5332	Approved
0.59	Remote Similarity	NPD6409	Approved
0.59	Remote Similarity	NPD6684	Approved
0.59	Remote Similarity	NPD6422	Discontinued
0.59	Remote Similarity	NPD5330	Approved
0.59	Remote Similarity	NPD7334	Approved
0.59	Remote Similarity	NPD7521	Approved
0.59	Remote Similarity	NPD7146	Approved
0.5897	Remote Similarity	NPD7115	Discovery
0.5888	Remote Similarity	NPD5696	Approved
0.5877	Remote Similarity	NPD6650	Approved
0.5877	Remote Similarity	NPD6847	Approved
0.5877	Remote Similarity	NPD8130	Phase 1
0.5877	Remote Similarity	NPD6649	Approved
0.5877	Remote Similarity	NPD6869	Approved
0.5877	Remote Similarity	NPD6617	Approved
0.5876	Remote Similarity	NPD1779	Approved
0.5876	Remote Similarity	NPD4790	Discontinued
0.5876	Remote Similarity	NPD1780	Approved
0.5875	Remote Similarity	NPD2269	Approved
0.5872	Remote Similarity	NPD8138	Approved
0.5872	Remote Similarity	NPD8086	Approved
0.5872	Remote Similarity	NPD8083	Approved
0.5872	Remote Similarity	NPD8082	Approved
0.5872	Remote Similarity	NPD8139	Approved
0.5872	Remote Similarity	NPD8085	Approved
0.5872	Remote Similarity	NPD8084	Approved
0.5868	Remote Similarity	NPD7604	Phase 2
0.5862	Remote Similarity	NPD3197	Phase 1
0.5859	Remote Similarity	NPD4786	Approved
0.5851	Remote Similarity	NPD6933	Approved
0.5843	Remote Similarity	NPD896	Approved
0.5843	Remote Similarity	NPD898	Approved
0.5843	Remote Similarity	NPD897	Approved
0.5842	Remote Similarity	NPD7750	Discontinued
0.5841	Remote Similarity	NPD6014	Approved
0.5841	Remote Similarity	NPD6013	Approved
0.5841	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD7645	Phase 2
0.5833	Remote Similarity	NPD5983	Phase 2
0.5833	Remote Similarity	NPD6683	Phase 2
0.5833	Remote Similarity	NPD7329	Approved
0.5818	Remote Similarity	NPD8276	Approved
0.5818	Remote Similarity	NPD8275	Approved
0.5816	Remote Similarity	NPD4269	Approved
0.5816	Remote Similarity	NPD4270	Approved
0.5816	Remote Similarity	NPD3667	Approved
0.5814	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7900	Approved
0.581	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6033	Approved
0.5804	Remote Similarity	NPD6685	Approved
0.5802	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD888	Phase 3
0.5802	Remote Similarity	NPD892	Phase 3
0.5802	Remote Similarity	NPD893	Approved
0.5802	Remote Similarity	NPD891	Phase 3
0.5795	Remote Similarity	NPD2685	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