NPASS Compound

Structure

NPC17083 OpenBabel07101718312D 25 27 0 0 0 0 0 0 0 0999 V2000 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 4.3301 -0.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 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 1.7321 -2.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 9 19 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	351.666
LogP:	4.246
LogD:	2.18
LogS:	-3.961
# Rotatable Bonds:	1
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	3.938
Fsp3:	0.3
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:	-4.951
MDCK Permeability:	1.5369063476100564e-05
Pgp-inhibitor:	0.122
Pgp-substrate:	0.226
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.692
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	99.74817657470703%
Volume Distribution (VD):	0.279
Pgp-substrate:	1.5779532194137573%

ADMET: Metabolism

CYP1A2-inhibitor:	0.847
CYP1A2-substrate:	0.843
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.359
CYP2C9-inhibitor:	0.519
CYP2C9-substrate:	0.672
CYP2D6-inhibitor:	0.321
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.366
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	1.623
Half-life (T1/2):	0.28

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.518
Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.74
Carcinogencity:	0.616
Eye Corrosion:	0.004
Eye Irritation:	0.882
Respiratory Toxicity:	0.198

Download Data

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

Natural Product: NPC17083

Natural Product ID:	NPC17083
*Common Name:**	Garveatin E
IUPAC Name:	n.a.
Synonyms:	Garveatin E
Standard InCHIKey:	CXDZOCPWVKOLAD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-6-10-8(2)15(21)11-7-12-14(18(24)13(11)17(10)23)16(22)9(3)19(25)20(12,4)5/h7,24-25H,6H2,1-5H3
SMILES:	CCC1=C(C)C(=O)c2c(C1=O)c(O)c1c(c2)C(C)(C)C(=C(C1=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513118
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO2240	Garveia annulata	Species	Bougainvilliidae	Eukaryota	n.a.	Northeastern Pacific	n.a.	PMID[17067170]
NPO2240	Garveia annulata	Species	Bougainvilliidae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	Ki	=	3100.0	nM	PMID[522272]

☑ 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 NPC17083 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	345
0.1-0.2	1586
0.2-0.3	3581
0.3-0.4	9814
0.4-0.5	10205
0.5-0.6	6881
0.6-0.7	7555
0.7-0.8	2395
0.8-0.85	246
0.85-0.9	79
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC474311
0.9154	High Similarity	NPC58685
0.9084	High Similarity	NPC115458
0.8939	High Similarity	NPC53896
0.8939	High Similarity	NPC114183
0.8939	High Similarity	NPC254603
0.8923	High Similarity	NPC146647
0.8923	High Similarity	NPC34414
0.8881	High Similarity	NPC272268
0.8872	High Similarity	NPC12070
0.8872	High Similarity	NPC270899
0.8855	High Similarity	NPC55949
0.8846	High Similarity	NPC282923
0.8837	High Similarity	NPC231774
0.8837	High Similarity	NPC3224
0.8819	High Similarity	NPC307174
0.8806	High Similarity	NPC283088
0.8806	High Similarity	NPC249272
0.8779	High Similarity	NPC278928
0.8769	High Similarity	NPC471530
0.8759	High Similarity	NPC315578
0.875	High Similarity	NPC13715
0.8741	High Similarity	NPC472308
0.8741	High Similarity	NPC315275
0.8731	High Similarity	NPC50924
0.8731	High Similarity	NPC288089
0.8722	High Similarity	NPC309430
0.8702	High Similarity	NPC48248
0.8692	High Similarity	NPC254492
0.8692	High Similarity	NPC306765
0.8686	High Similarity	NPC26924
0.8682	High Similarity	NPC142956
0.8676	High Similarity	NPC53001
0.8667	High Similarity	NPC80035
0.8657	High Similarity	NPC193169
0.8647	High Similarity	NPC244699
0.8647	High Similarity	NPC205992
0.8636	High Similarity	NPC99731
0.8636	High Similarity	NPC25736
0.8633	High Similarity	NPC193555
0.8626	High Similarity	NPC72667
0.8615	High Similarity	NPC103540
0.8613	High Similarity	NPC87723
0.8603	High Similarity	NPC193358
0.8603	High Similarity	NPC86524
0.8583	High Similarity	NPC285829
0.8583	High Similarity	NPC206778
0.8582	High Similarity	NPC246693
0.8582	High Similarity	NPC110609
0.8582	High Similarity	NPC70622
0.8582	High Similarity	NPC242358
0.8571	High Similarity	NPC198305
0.8551	High Similarity	NPC242994
0.8551	High Similarity	NPC138099
0.855	High Similarity	NPC1991
0.854	High Similarity	NPC245923
0.854	High Similarity	NPC305060
0.854	High Similarity	NPC471452
0.854	High Similarity	NPC471905
0.8538	High Similarity	NPC310540
0.8538	High Similarity	NPC173978
0.8519	High Similarity	NPC225051
0.8496	Intermediate Similarity	NPC171460
0.8489	Intermediate Similarity	NPC96421
0.8489	Intermediate Similarity	NPC169452
0.8489	Intermediate Similarity	NPC181560
0.8485	Intermediate Similarity	NPC176130
0.8485	Intermediate Similarity	NPC78364
0.8485	Intermediate Similarity	NPC69424
0.8485	Intermediate Similarity	NPC84672
0.8478	Intermediate Similarity	NPC4214
0.8478	Intermediate Similarity	NPC230811
0.8467	Intermediate Similarity	NPC474813
0.8467	Intermediate Similarity	NPC254847
0.8462	Intermediate Similarity	NPC375356
0.8444	Intermediate Similarity	NPC88864
0.8433	Intermediate Similarity	NPC136588
0.8433	Intermediate Similarity	NPC108129
0.8433	Intermediate Similarity	NPC475741
0.8433	Intermediate Similarity	NPC199253
0.8433	Intermediate Similarity	NPC31799
0.8406	Intermediate Similarity	NPC475957
0.8406	Intermediate Similarity	NPC36868
0.8406	Intermediate Similarity	NPC53206
0.8406	Intermediate Similarity	NPC53414
0.8397	Intermediate Similarity	NPC199273
0.8385	Intermediate Similarity	NPC282577
0.8385	Intermediate Similarity	NPC300274
0.8382	Intermediate Similarity	NPC477139
0.8382	Intermediate Similarity	NPC138472
0.838	Intermediate Similarity	NPC29932
0.8372	Intermediate Similarity	NPC472046
0.8369	Intermediate Similarity	NPC291078
0.8369	Intermediate Similarity	NPC135524
0.8369	Intermediate Similarity	NPC19631
0.8369	Intermediate Similarity	NPC239136
0.8358	Intermediate Similarity	NPC303910
0.8345	Intermediate Similarity	NPC61398
0.8345	Intermediate Similarity	NPC416
0.8333	Intermediate Similarity	NPC191976
0.8333	Intermediate Similarity	NPC155211
0.8322	Intermediate Similarity	NPC474630
0.8322	Intermediate Similarity	NPC12402
0.8321	Intermediate Similarity	NPC282780
0.8321	Intermediate Similarity	NPC202225
0.8321	Intermediate Similarity	NPC287604
0.8321	Intermediate Similarity	NPC161964
0.8321	Intermediate Similarity	NPC166480
0.8321	Intermediate Similarity	NPC472262
0.831	Intermediate Similarity	NPC471682
0.8308	Intermediate Similarity	NPC154696
0.8298	Intermediate Similarity	NPC204045
0.8298	Intermediate Similarity	NPC246638
0.8298	Intermediate Similarity	NPC290550
0.8298	Intermediate Similarity	NPC305845
0.8286	Intermediate Similarity	NPC143438
0.8286	Intermediate Similarity	NPC295339
0.8286	Intermediate Similarity	NPC1268
0.8286	Intermediate Similarity	NPC162939
0.8284	Intermediate Similarity	NPC96024
0.8284	Intermediate Similarity	NPC237225
0.8284	Intermediate Similarity	NPC165257
0.8271	Intermediate Similarity	NPC96915
0.8271	Intermediate Similarity	NPC71610
0.8271	Intermediate Similarity	NPC15837
0.8268	Intermediate Similarity	NPC477453
0.8268	Intermediate Similarity	NPC108288
0.8264	Intermediate Similarity	NPC136878
0.8261	Intermediate Similarity	NPC258502
0.8261	Intermediate Similarity	NPC161632
0.8261	Intermediate Similarity	NPC290803
0.8258	Intermediate Similarity	NPC152525
0.8258	Intermediate Similarity	NPC68756
0.8248	Intermediate Similarity	NPC267205
0.8248	Intermediate Similarity	NPC4170
0.8248	Intermediate Similarity	NPC314048
0.8248	Intermediate Similarity	NPC52407
0.8248	Intermediate Similarity	NPC111845
0.8248	Intermediate Similarity	NPC48036
0.8248	Intermediate Similarity	NPC171968
0.8239	Intermediate Similarity	NPC257644
0.8239	Intermediate Similarity	NPC73061
0.8235	Intermediate Similarity	NPC474517
0.8235	Intermediate Similarity	NPC471851
0.8235	Intermediate Similarity	NPC72669
0.8227	Intermediate Similarity	NPC471853
0.8222	Intermediate Similarity	NPC276238
0.8219	Intermediate Similarity	NPC474310
0.8217	Intermediate Similarity	NPC232178
0.8214	Intermediate Similarity	NPC61590
0.8195	Intermediate Similarity	NPC123506
0.8195	Intermediate Similarity	NPC131799
0.8194	Intermediate Similarity	NPC34482
0.8194	Intermediate Similarity	NPC471683
0.8189	Intermediate Similarity	NPC161304
0.8188	Intermediate Similarity	NPC474519
0.8188	Intermediate Similarity	NPC44437
0.8182	Intermediate Similarity	NPC275145
0.8182	Intermediate Similarity	NPC66593
0.8182	Intermediate Similarity	NPC143898
0.8182	Intermediate Similarity	NPC163948
0.8169	Intermediate Similarity	NPC124365
0.8163	Intermediate Similarity	NPC315520
0.8162	Intermediate Similarity	NPC117609
0.8156	Intermediate Similarity	NPC299405
0.8156	Intermediate Similarity	NPC29771
0.8156	Intermediate Similarity	NPC190457
0.8156	Intermediate Similarity	NPC306835
0.8156	Intermediate Similarity	NPC476477
0.8156	Intermediate Similarity	NPC471602
0.8156	Intermediate Similarity	NPC256463
0.8156	Intermediate Similarity	NPC111422
0.8156	Intermediate Similarity	NPC216312
0.8148	Intermediate Similarity	NPC3009
0.8143	Intermediate Similarity	NPC118366
0.8138	Intermediate Similarity	NPC143685
0.8138	Intermediate Similarity	NPC470570
0.8134	Intermediate Similarity	NPC474106
0.8134	Intermediate Similarity	NPC295202
0.8134	Intermediate Similarity	NPC51037
0.8134	Intermediate Similarity	NPC160499
0.8134	Intermediate Similarity	NPC49647
0.8134	Intermediate Similarity	NPC227741
0.8134	Intermediate Similarity	NPC473751
0.8134	Intermediate Similarity	NPC136342
0.8129	Intermediate Similarity	NPC281513
0.8129	Intermediate Similarity	NPC22222
0.8125	Intermediate Similarity	NPC21599
0.8125	Intermediate Similarity	NPC79627
0.8125	Intermediate Similarity	NPC244691
0.8125	Intermediate Similarity	NPC193703
0.8125	Intermediate Similarity	NPC471906
0.8125	Intermediate Similarity	NPC48762
0.8116	Intermediate Similarity	NPC37299
0.8116	Intermediate Similarity	NPC180261
0.8116	Intermediate Similarity	NPC78307
0.8112	Intermediate Similarity	NPC474961
0.8112	Intermediate Similarity	NPC308572
0.8112	Intermediate Similarity	NPC474300
0.8112	Intermediate Similarity	NPC248068

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 NPC17083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	968
0.2-0.3	1600
0.3-0.4	2837
0.4-0.5	2112
0.5-0.6	935
0.6-0.7	322
0.7-0.8	38
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8615	High Similarity	NPD1470	Approved
0.8467	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD1201	Approved
0.8268	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD5405	Approved
0.8014	Intermediate Similarity	NPD5404	Approved
0.8014	Intermediate Similarity	NPD5408	Approved
0.8014	Intermediate Similarity	NPD5406	Approved
0.7973	Intermediate Similarity	NPD3226	Approved
0.7877	Intermediate Similarity	NPD7390	Discontinued
0.7803	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2346	Discontinued
0.7703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD3300	Phase 2
0.7612	Intermediate Similarity	NPD2932	Approved
0.7481	Intermediate Similarity	NPD3019	Approved
0.7424	Intermediate Similarity	NPD5951	Approved
0.7413	Intermediate Similarity	NPD943	Approved
0.7365	Intermediate Similarity	NPD2800	Approved
0.7351	Intermediate Similarity	NPD2533	Approved
0.7351	Intermediate Similarity	NPD2534	Approved
0.7351	Intermediate Similarity	NPD2532	Approved
0.7329	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6232	Discontinued
0.72	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6651	Approved
0.7178	Intermediate Similarity	NPD7473	Discontinued
0.7163	Intermediate Similarity	NPD1164	Approved
0.7162	Intermediate Similarity	NPD2935	Discontinued
0.7153	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7113	Intermediate Similarity	NPD2798	Approved
0.7095	Intermediate Similarity	NPD2799	Discontinued
0.7089	Intermediate Similarity	NPD7819	Suspended
0.7086	Intermediate Similarity	NPD7003	Approved
0.7075	Intermediate Similarity	NPD1607	Approved
0.7067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3026	Approved
0.705	Intermediate Similarity	NPD3023	Approved
0.7047	Intermediate Similarity	NPD6099	Approved
0.7047	Intermediate Similarity	NPD6100	Approved
0.7045	Intermediate Similarity	NPD4750	Phase 3
0.7034	Intermediate Similarity	NPD3764	Approved
0.7029	Intermediate Similarity	NPD3024	Approved
0.7029	Intermediate Similarity	NPD3025	Approved
0.7023	Intermediate Similarity	NPD2342	Discontinued
0.702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7635	Approved
0.7013	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD2344	Approved
0.698	Remote Similarity	NPD1510	Phase 2
0.697	Remote Similarity	NPD9266	Approved
0.697	Remote Similarity	NPD74	Approved
0.6959	Remote Similarity	NPD8150	Discontinued
0.6939	Remote Similarity	NPD1240	Approved
0.6937	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD9493	Approved
0.6894	Remote Similarity	NPD9264	Approved
0.6894	Remote Similarity	NPD9263	Approved
0.6894	Remote Similarity	NPD9267	Approved
0.6879	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5027	Approved
0.6864	Remote Similarity	NPD5031	Approved
0.6864	Remote Similarity	NPD5029	Approved
0.6863	Remote Similarity	NPD8166	Discontinued
0.6863	Remote Similarity	NPD3750	Approved
0.6863	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7411	Suspended
0.6849	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7458	Discontinued
0.6831	Remote Similarity	NPD4878	Approved
0.6831	Remote Similarity	NPD3972	Approved
0.6818	Remote Similarity	NPD2309	Approved
0.6815	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4380	Phase 2
0.6788	Remote Similarity	NPD5711	Approved
0.6788	Remote Similarity	NPD5710	Approved
0.6783	Remote Similarity	NPD1755	Approved
0.6772	Remote Similarity	NPD844	Approved
0.6772	Remote Similarity	NPD1809	Phase 2
0.6767	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6663	Approved
0.6753	Remote Similarity	NPD4628	Phase 3
0.6738	Remote Similarity	NPD4626	Approved
0.6736	Remote Similarity	NPD6696	Suspended
0.6735	Remote Similarity	NPD7008	Discontinued
0.6732	Remote Similarity	NPD1549	Phase 2
0.673	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4954	Approved
0.6725	Remote Similarity	NPD5028	Approved
0.6725	Remote Similarity	NPD5026	Approved
0.6725	Remote Similarity	NPD4955	Approved
0.6725	Remote Similarity	NPD5034	Approved
0.6725	Remote Similarity	NPD36	Approved
0.6719	Remote Similarity	NPD288	Approved
0.6719	Remote Similarity	NPD3495	Discontinued
0.6712	Remote Similarity	NPD5736	Approved
0.6707	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3268	Approved
0.6689	Remote Similarity	NPD411	Approved
0.6687	Remote Similarity	NPD6599	Discontinued
0.6686	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD9281	Approved
0.6667	Remote Similarity	NPD5030	Phase 2
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD5038	Approved
0.6667	Remote Similarity	NPD5037	Approved
0.6646	Remote Similarity	NPD7075	Discontinued
0.6646	Remote Similarity	NPD3749	Approved
0.6629	Remote Similarity	NPD6535	Approved
0.6629	Remote Similarity	NPD6534	Approved
0.6628	Remote Similarity	NPD5032	Approved
0.6624	Remote Similarity	NPD1511	Approved
0.6621	Remote Similarity	NPD1283	Approved
0.6614	Remote Similarity	NPD845	Approved
0.6609	Remote Similarity	NPD5036	Approved
0.6606	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1934	Approved
0.6601	Remote Similarity	NPD1551	Phase 2
0.6601	Remote Similarity	NPD2796	Approved
0.6599	Remote Similarity	NPD4208	Discontinued
0.6597	Remote Similarity	NPD9717	Approved
0.6597	Remote Similarity	NPD9269	Phase 2
0.6596	Remote Similarity	NPD3091	Approved
0.6596	Remote Similarity	NPD9545	Approved
0.6596	Remote Similarity	NPD7009	Phase 2
0.6591	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1930	Approved
0.6591	Remote Similarity	NPD6836	Approved
0.6591	Remote Similarity	NPD1929	Approved
0.6591	Remote Similarity	NPD9261	Approved
0.659	Remote Similarity	NPD5035	Approved
0.6588	Remote Similarity	NPD6020	Phase 2
0.6585	Remote Similarity	NPD3882	Suspended
0.6585	Remote Similarity	NPD7768	Phase 2
0.6577	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1203	Approved
0.6573	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6213	Phase 3
0.6573	Remote Similarity	NPD6212	Phase 3
0.6564	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD447	Suspended
0.6549	Remote Similarity	NPD9268	Approved
0.6541	Remote Similarity	NPD6273	Approved
0.6541	Remote Similarity	NPD1512	Approved
0.6536	Remote Similarity	NPD3748	Approved
0.6536	Remote Similarity	NPD4308	Phase 3
0.6531	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7177	Discontinued
0.6528	Remote Similarity	NPD3092	Approved
0.6528	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7610	Discontinued
0.6519	Remote Similarity	NPD7699	Phase 2
0.6519	Remote Similarity	NPD7700	Phase 2
0.6515	Remote Similarity	NPD1932	Approved
0.651	Remote Similarity	NPD4625	Phase 3
0.6507	Remote Similarity	NPD1876	Approved
0.6503	Remote Similarity	NPD6801	Discontinued
0.6503	Remote Similarity	NPD4059	Approved
0.6491	Remote Similarity	NPD5844	Phase 1
0.6489	Remote Similarity	NPD2066	Phase 3
0.6478	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD8434	Phase 2
0.6474	Remote Similarity	NPD6559	Discontinued
0.6471	Remote Similarity	NPD5033	Approved
0.6467	Remote Similarity	NPD5494	Approved
0.6467	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3094	Phase 2
0.6458	Remote Similarity	NPD4879	Approved
0.6457	Remote Similarity	NPD7609	Phase 3
0.6454	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6781	Approved
0.6448	Remote Similarity	NPD6779	Approved
0.6448	Remote Similarity	NPD6782	Approved
0.6448	Remote Similarity	NPD6776	Approved
0.6448	Remote Similarity	NPD6777	Approved
0.6448	Remote Similarity	NPD6780	Approved
0.6448	Remote Similarity	NPD6778	Approved
0.6447	Remote Similarity	NPD230	Phase 1
0.6438	Remote Similarity	NPD4749	Approved
0.6434	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5691	Approved
0.6433	Remote Similarity	NPD7893	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