NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	316.24
Volume:	361.694
LogP:	4.489
LogD:	3.852
LogS:	-4.403
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	4.451
Fsp3:	0.667
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:	-4.868
MDCK Permeability:	2.0160156054771505e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.083
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.57
Plasma Protein Binding (PPB):	80.82414245605469%
Volume Distribution (VD):	0.28
Pgp-substrate:	22.752534866333008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.359
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.372
CYP3A4-inhibitor:	0.558
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	2.873
Half-life (T1/2):	0.553

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.455
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.416
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.799
Carcinogencity:	0.776
Eye Corrosion:	0.369
Eye Irritation:	0.471
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC476844

Natural Product ID:	NPC476844
*Common Name:**	Rel-Clathric Acid
IUPAC Name:	2-[(1S,4aS,5S,8aR)-5,8a-dimethyl-2-methylidene-5-[(1E)-4-methylpenta-1,3-dienyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]acetic acid
Synonyms:	Rel-Clathric Acid
Standard InCHIKey:	RIZUAODWKFVFDS-HDASRLSZSA-N
Standard InCHI:	InChI=1S/C21H32O2/c1-15(2)8-6-11-20(4)12-7-13-21(5)17(14-19(22)23)16(3)9-10-18(20)21/h6,8,11,17-18H,3,7,9-10,12-14H2,1-2,4-5H3,(H,22,23)/b11-6+/t17-,18-,20+,21+/m0/s1
SMILES:	CC(=C/C=C/[C@@]1(CCC[C@]2([C@H]1CCC(=C)[C@@H]2CC(=O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	60155238
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO33611	Clathria compressa	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22607472]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32	ug/ml	PMID[22607472]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64	ug/ml	PMID[22607472]

☑ 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 NPC476844 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	157
0.1-0.2	909
0.2-0.3	4930
0.3-0.4	15799
0.4-0.5	9478
0.5-0.6	6867
0.6-0.7	3486
0.7-0.8	951
0.8-0.85	77
0.85-0.9	26
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC237591
0.9855	High Similarity	NPC3753
0.9296	High Similarity	NPC183503
0.9296	High Similarity	NPC283908
0.9296	High Similarity	NPC103958
0.9296	High Similarity	NPC161923
0.9167	High Similarity	NPC192540
0.9167	High Similarity	NPC279666
0.9041	High Similarity	NPC69143
0.9041	High Similarity	NPC309399
0.9028	High Similarity	NPC241854
0.9028	High Similarity	NPC251970
0.9028	High Similarity	NPC476046
0.9028	High Similarity	NPC301065
0.9014	High Similarity	NPC160817
0.8947	High Similarity	NPC142244
0.8919	High Similarity	NPC471897
0.8919	High Similarity	NPC471899
0.8919	High Similarity	NPC107039
0.8857	High Similarity	NPC36616
0.8857	High Similarity	NPC290445
0.88	High Similarity	NPC239098
0.88	High Similarity	NPC179028
0.88	High Similarity	NPC260385
0.88	High Similarity	NPC110094
0.88	High Similarity	NPC280654
0.8784	High Similarity	NPC89294
0.8767	High Similarity	NPC46610
0.8767	High Similarity	NPC18819
0.8767	High Similarity	NPC166797
0.8718	High Similarity	NPC70834
0.8718	High Similarity	NPC312480
0.8684	High Similarity	NPC231431
0.8684	High Similarity	NPC16394
0.8684	High Similarity	NPC158846
0.8684	High Similarity	NPC199595
0.8667	High Similarity	NPC61952
0.8667	High Similarity	NPC165711
0.8649	High Similarity	NPC201027
0.8611	High Similarity	NPC91369
0.8571	High Similarity	NPC37038
0.8571	High Similarity	NPC104545
0.8553	High Similarity	NPC59436
0.8553	High Similarity	NPC198240
0.8553	High Similarity	NPC321514
0.8533	High Similarity	NPC899
0.8514	High Similarity	NPC306928
0.8514	High Similarity	NPC255168
0.85	High Similarity	NPC76333
0.8493	Intermediate Similarity	NPC72343
0.8481	Intermediate Similarity	NPC83569
0.8481	Intermediate Similarity	NPC69279
0.8481	Intermediate Similarity	NPC102197
0.8481	Intermediate Similarity	NPC167103
0.8462	Intermediate Similarity	NPC263272
0.8462	Intermediate Similarity	NPC267691
0.8462	Intermediate Similarity	NPC162632
0.8462	Intermediate Similarity	NPC471898
0.8462	Intermediate Similarity	NPC274050
0.8462	Intermediate Similarity	NPC40228
0.8462	Intermediate Similarity	NPC147066
0.8462	Intermediate Similarity	NPC229584
0.8462	Intermediate Similarity	NPC221647
0.8462	Intermediate Similarity	NPC14203
0.8462	Intermediate Similarity	NPC278459
0.8442	Intermediate Similarity	NPC327674
0.8442	Intermediate Similarity	NPC196827
0.8442	Intermediate Similarity	NPC274996
0.8442	Intermediate Similarity	NPC477371
0.84	Intermediate Similarity	NPC476795
0.8378	Intermediate Similarity	NPC36310
0.8354	Intermediate Similarity	NPC302661
0.8354	Intermediate Similarity	NPC251779
0.8354	Intermediate Similarity	NPC69101
0.8354	Intermediate Similarity	NPC238991
0.8333	Intermediate Similarity	NPC477057
0.8312	Intermediate Similarity	NPC4827
0.8312	Intermediate Similarity	NPC247783
0.8312	Intermediate Similarity	NPC269543
0.8289	Intermediate Similarity	NPC180886
0.8272	Intermediate Similarity	NPC29447
0.8272	Intermediate Similarity	NPC269638
0.8272	Intermediate Similarity	NPC474537
0.8267	Intermediate Similarity	NPC213223
0.825	Intermediate Similarity	NPC200752
0.8228	Intermediate Similarity	NPC327002
0.8228	Intermediate Similarity	NPC38350
0.8228	Intermediate Similarity	NPC477372
0.8228	Intermediate Similarity	NPC474955
0.8228	Intermediate Similarity	NPC90055
0.8228	Intermediate Similarity	NPC201912
0.8205	Intermediate Similarity	NPC474113
0.8182	Intermediate Similarity	NPC97377
0.8148	Intermediate Similarity	NPC472864
0.8148	Intermediate Similarity	NPC156981
0.8148	Intermediate Similarity	NPC194937
0.8148	Intermediate Similarity	NPC476038
0.8148	Intermediate Similarity	NPC96095
0.8148	Intermediate Similarity	NPC19849
0.8148	Intermediate Similarity	NPC477289
0.8133	Intermediate Similarity	NPC35656
0.8133	Intermediate Similarity	NPC177826
0.8133	Intermediate Similarity	NPC244708
0.8133	Intermediate Similarity	NPC330659
0.8133	Intermediate Similarity	NPC161187
0.8125	Intermediate Similarity	NPC320514
0.8125	Intermediate Similarity	NPC296367
0.8125	Intermediate Similarity	NPC260956
0.8125	Intermediate Similarity	NPC133391
0.8118	Intermediate Similarity	NPC301244
0.8118	Intermediate Similarity	NPC473986
0.8118	Intermediate Similarity	NPC474018
0.8108	Intermediate Similarity	NPC235586
0.8095	Intermediate Similarity	NPC95246
0.8095	Intermediate Similarity	NPC474972
0.8095	Intermediate Similarity	NPC161751
0.8077	Intermediate Similarity	NPC471409
0.8077	Intermediate Similarity	NPC74410
0.8077	Intermediate Similarity	NPC275494
0.8072	Intermediate Similarity	NPC128644
0.8072	Intermediate Similarity	NPC236618
0.8056	Intermediate Similarity	NPC149680
0.8052	Intermediate Similarity	NPC476601
0.8052	Intermediate Similarity	NPC20466
0.8052	Intermediate Similarity	NPC246445
0.8052	Intermediate Similarity	NPC104806
0.8049	Intermediate Similarity	NPC283733
0.8028	Intermediate Similarity	NPC234767
0.8025	Intermediate Similarity	NPC477852
0.8025	Intermediate Similarity	NPC310470
0.8025	Intermediate Similarity	NPC215893
0.8025	Intermediate Similarity	NPC97913
0.8025	Intermediate Similarity	NPC477373
0.8	Intermediate Similarity	NPC473420
0.8	Intermediate Similarity	NPC121984
0.8	Intermediate Similarity	NPC225515
0.7976	Intermediate Similarity	NPC24816
0.7975	Intermediate Similarity	NPC215843
0.7952	Intermediate Similarity	NPC82979
0.7952	Intermediate Similarity	NPC155011
0.7952	Intermediate Similarity	NPC325594
0.7952	Intermediate Similarity	NPC186975
0.7952	Intermediate Similarity	NPC73038
0.7952	Intermediate Similarity	NPC324063
0.7952	Intermediate Similarity	NPC6247
0.7952	Intermediate Similarity	NPC472869
0.7949	Intermediate Similarity	NPC472300
0.7949	Intermediate Similarity	NPC68828
0.7949	Intermediate Similarity	NPC66105
0.7931	Intermediate Similarity	NPC80365
0.7927	Intermediate Similarity	NPC472865
0.7927	Intermediate Similarity	NPC139566
0.7927	Intermediate Similarity	NPC165064
0.7927	Intermediate Similarity	NPC248758
0.7927	Intermediate Similarity	NPC164577
0.7907	Intermediate Similarity	NPC204341
0.7901	Intermediate Similarity	NPC15910
0.7901	Intermediate Similarity	NPC73882
0.7895	Intermediate Similarity	NPC472813
0.7882	Intermediate Similarity	NPC102414
0.7882	Intermediate Similarity	NPC128496
0.7882	Intermediate Similarity	NPC262043
0.7882	Intermediate Similarity	NPC474686
0.7882	Intermediate Similarity	NPC66344
0.7882	Intermediate Similarity	NPC84271
0.7882	Intermediate Similarity	NPC112454
0.7882	Intermediate Similarity	NPC36668
0.7882	Intermediate Similarity	NPC118011
0.7882	Intermediate Similarity	NPC77168
0.7875	Intermediate Similarity	NPC267517
0.7875	Intermediate Similarity	NPC26139
0.7875	Intermediate Similarity	NPC476809
0.7875	Intermediate Similarity	NPC2482
0.7857	Intermediate Similarity	NPC136948
0.7857	Intermediate Similarity	NPC71507
0.7857	Intermediate Similarity	NPC88716
0.7857	Intermediate Similarity	NPC51700
0.7857	Intermediate Similarity	NPC476409
0.7857	Intermediate Similarity	NPC307426
0.7857	Intermediate Similarity	NPC130577
0.7857	Intermediate Similarity	NPC18064
0.7857	Intermediate Similarity	NPC68160
0.7857	Intermediate Similarity	NPC141292
0.7857	Intermediate Similarity	NPC98442
0.7857	Intermediate Similarity	NPC293564
0.7857	Intermediate Similarity	NPC477926
0.7857	Intermediate Similarity	NPC173089
0.7857	Intermediate Similarity	NPC474684
0.7857	Intermediate Similarity	NPC242468
0.7857	Intermediate Similarity	NPC171203
0.7857	Intermediate Similarity	NPC142415
0.7857	Intermediate Similarity	NPC158141
0.7857	Intermediate Similarity	NPC96496
0.7857	Intermediate Similarity	NPC102683
0.7857	Intermediate Similarity	NPC142361
0.7848	Intermediate Similarity	NPC321690
0.7848	Intermediate Similarity	NPC169095
0.7848	Intermediate Similarity	NPC189485
0.7841	Intermediate Similarity	NPC88310
0.7831	Intermediate Similarity	NPC86316

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 NPC476844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1203
0.2-0.3	3732
0.3-0.4	2670
0.4-0.5	830
0.5-0.6	313
0.6-0.7	198
0.7-0.8	44
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
0.7882	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD5284	Approved
0.7701	Intermediate Similarity	NPD5281	Approved
0.7654	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6411	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.747	Intermediate Similarity	NPD4221	Approved
0.747	Intermediate Similarity	NPD3667	Approved
0.747	Intermediate Similarity	NPD4223	Phase 3
0.747	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD8039	Approved
0.7416	Intermediate Similarity	NPD6399	Phase 3
0.7412	Intermediate Similarity	NPD5329	Approved
0.7333	Intermediate Similarity	NPD7748	Approved
0.7326	Intermediate Similarity	NPD4694	Approved
0.7326	Intermediate Similarity	NPD6098	Approved
0.7326	Intermediate Similarity	NPD6409	Approved
0.7326	Intermediate Similarity	NPD5280	Approved
0.7326	Intermediate Similarity	NPD6684	Approved
0.7326	Intermediate Similarity	NPD7146	Approved
0.7326	Intermediate Similarity	NPD4623	Approved
0.7326	Intermediate Similarity	NPD4519	Discontinued
0.7326	Intermediate Similarity	NPD7521	Approved
0.7326	Intermediate Similarity	NPD7334	Approved
0.7326	Intermediate Similarity	NPD5330	Approved
0.7326	Intermediate Similarity	NPD5279	Phase 3
0.7294	Intermediate Similarity	NPD3133	Approved
0.7294	Intermediate Similarity	NPD3666	Approved
0.7294	Intermediate Similarity	NPD4197	Approved
0.7294	Intermediate Similarity	NPD3665	Phase 1
0.7273	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6101	Approved
0.7246	Intermediate Similarity	NPD3195	Phase 2
0.7246	Intermediate Similarity	NPD3196	Approved
0.7246	Intermediate Similarity	NPD3194	Approved
0.7246	Intermediate Similarity	NPD4266	Approved
0.7241	Intermediate Similarity	NPD3573	Approved
0.7209	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3617	Approved
0.7191	Intermediate Similarity	NPD5207	Approved
0.7159	Intermediate Similarity	NPD6903	Approved
0.7159	Intermediate Similarity	NPD5737	Approved
0.7159	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6672	Approved
0.7128	Intermediate Similarity	NPD6404	Discontinued
0.7126	Intermediate Similarity	NPD4138	Approved
0.7126	Intermediate Similarity	NPD4693	Phase 3
0.7126	Intermediate Similarity	NPD5205	Approved
0.7126	Intermediate Similarity	NPD4689	Approved
0.7126	Intermediate Similarity	NPD5690	Phase 2
0.7126	Intermediate Similarity	NPD4690	Approved
0.7126	Intermediate Similarity	NPD3618	Phase 1
0.7126	Intermediate Similarity	NPD4688	Approved
0.7125	Intermediate Similarity	NPD6926	Approved
0.7125	Intermediate Similarity	NPD6924	Approved
0.7125	Intermediate Similarity	NPD4058	Approved
0.7111	Intermediate Similarity	NPD6050	Approved
0.7111	Intermediate Similarity	NPD6079	Approved
0.7111	Intermediate Similarity	NPD5694	Approved
0.7101	Intermediate Similarity	NPD3172	Approved
0.7097	Intermediate Similarity	NPD6084	Phase 2
0.7097	Intermediate Similarity	NPD7902	Approved
0.7097	Intermediate Similarity	NPD6083	Phase 2
0.7079	Intermediate Similarity	NPD6904	Approved
0.7079	Intermediate Similarity	NPD6673	Approved
0.7079	Intermediate Similarity	NPD5328	Approved
0.7079	Intermediate Similarity	NPD6080	Approved
0.7033	Intermediate Similarity	NPD5779	Approved
0.7033	Intermediate Similarity	NPD5778	Approved
0.7	Intermediate Similarity	NPD4096	Approved
0.7	Intermediate Similarity	NPD5692	Phase 3
0.6989	Remote Similarity	NPD7614	Phase 1
0.6988	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4518	Approved
0.6966	Remote Similarity	NPD5208	Approved
0.6962	Remote Similarity	NPD7143	Approved
0.6962	Remote Similarity	NPD7144	Approved
0.6951	Remote Similarity	NPD6933	Approved
0.6932	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7637	Suspended
0.6914	Remote Similarity	NPD4785	Approved
0.6914	Remote Similarity	NPD4687	Approved
0.6914	Remote Similarity	NPD4784	Approved
0.6914	Remote Similarity	NPD5733	Approved
0.6905	Remote Similarity	NPD4195	Approved
0.6897	Remote Similarity	NPD3668	Phase 3
0.6889	Remote Similarity	NPD4753	Phase 2
0.6883	Remote Similarity	NPD4224	Phase 2
0.6883	Remote Similarity	NPD7331	Phase 2
0.6882	Remote Similarity	NPD5695	Phase 3
0.6875	Remote Similarity	NPD4243	Approved
0.6875	Remote Similarity	NPD7151	Approved
0.6875	Remote Similarity	NPD5276	Approved
0.6875	Remote Similarity	NPD7152	Approved
0.6875	Remote Similarity	NPD7150	Approved
0.6842	Remote Similarity	NPD5696	Approved
0.6835	Remote Similarity	NPD6923	Approved
0.6835	Remote Similarity	NPD6922	Approved
0.6835	Remote Similarity	NPD4137	Phase 3
0.6812	Remote Similarity	NPD28	Approved
0.6812	Remote Similarity	NPD29	Approved
0.68	Remote Similarity	NPD4193	Approved
0.68	Remote Similarity	NPD4191	Approved
0.68	Remote Similarity	NPD4194	Approved
0.68	Remote Similarity	NPD4192	Approved
0.6782	Remote Similarity	NPD4788	Approved
0.6774	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7900	Approved
0.6753	Remote Similarity	NPD7341	Phase 2
0.675	Remote Similarity	NPD4691	Approved
0.675	Remote Similarity	NPD4747	Approved
0.6744	Remote Similarity	NPD857	Phase 3
0.6744	Remote Similarity	NPD4139	Approved
0.6744	Remote Similarity	NPD4692	Approved
0.6739	Remote Similarity	NPD8034	Phase 2
0.6739	Remote Similarity	NPD8035	Phase 2
0.6739	Remote Similarity	NPD5693	Phase 1
0.6709	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6929	Approved
0.6703	Remote Similarity	NPD5346	Phase 2
0.6703	Remote Similarity	NPD5347	Phase 2
0.6702	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4629	Approved
0.6702	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD5133	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD1088	Approved
0.6634	Remote Similarity	NPD6881	Approved
0.6634	Remote Similarity	NPD6899	Approved
0.6632	Remote Similarity	NPD5221	Approved
0.6632	Remote Similarity	NPD5222	Approved
0.6632	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7509	Discontinued
0.6628	Remote Similarity	NPD6931	Approved
0.6628	Remote Similarity	NPD5368	Approved
0.6628	Remote Similarity	NPD6930	Phase 2
0.6628	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6942	Approved
0.6627	Remote Similarity	NPD7339	Approved
0.6627	Remote Similarity	NPD8264	Approved
0.66	Remote Similarity	NPD6402	Approved
0.66	Remote Similarity	NPD5739	Approved
0.66	Remote Similarity	NPD7128	Approved
0.66	Remote Similarity	NPD6675	Approved
0.6598	Remote Similarity	NPD7639	Approved
0.6598	Remote Similarity	NPD7640	Approved
0.6596	Remote Similarity	NPD6001	Approved
0.6596	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5362	Discontinued
0.6588	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7145	Approved
0.6562	Remote Similarity	NPD5173	Approved
0.6552	Remote Similarity	NPD5369	Approved
0.6548	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5697	Approved
0.6526	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5654	Approved
0.6522	Remote Similarity	NPD3173	Approved
0.6512	Remote Similarity	NPD7645	Phase 2
0.6506	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7102	Approved
0.6505	Remote Similarity	NPD7290	Approved
0.6505	Remote Similarity	NPD6883	Approved
0.6484	Remote Similarity	NPD4793	Discontinued
0.6477	Remote Similarity	NPD4270	Approved
0.6477	Remote Similarity	NPD4269	Approved
0.6477	Remote Similarity	NPD6435	Approved
0.6471	Remote Similarity	NPD5776	Phase 2
0.6471	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD6686	Approved
0.6471	Remote Similarity	NPD6925	Approved
0.6458	Remote Similarity	NPD7732	Phase 3
0.6458	Remote Similarity	NPD4697	Phase 3
0.6452	Remote Similarity	NPD1089	Approved
0.6452	Remote Similarity	NPD1090	Approved
0.6452	Remote Similarity	NPD1086	Approved
0.6444	Remote Similarity	NPD1694	Approved
0.6442	Remote Similarity	NPD6869	Approved
0.6442	Remote Similarity	NPD6847	Approved
0.6442	Remote Similarity	NPD6649	Approved
0.6442	Remote Similarity	NPD8130	Phase 1
0.6442	Remote Similarity	NPD6650	Approved
0.6442	Remote Similarity	NPD6617	Approved
0.6437	Remote Similarity	NPD7332	Phase 2
0.6437	Remote Similarity	NPD7514	Phase 3
0.6437	Remote Similarity	NPD7525	Registered
0.6429	Remote Similarity	NPD4190	Phase 3
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD2066	Phase 3
0.6429	Remote Similarity	NPD5275	Approved
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD4696	Approved
0.641	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3197	Phase 1
0.6408	Remote Similarity	NPD6012	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