NPASS Compound

Structure

CID251071 OpenBabel06191716052D 22 25 0 0 1 0 0 0 0 0999 V2000 -2.4518 -3.2773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8296 -0.9315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0999 0.7799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0313 0.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8057 -3.2576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6117 -2.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8502 -0.9312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0002 -2.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6118 -1.8617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.8612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8059 -1.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4181 -0.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8059 -0.4654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6122 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4178 -1.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8061 -1.3959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3033 -0.1781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8403 -3.2772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6124 0.9699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7432 -1.6468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3030 -1.6841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 2 1 1 0 0 0 7 17 1 0 0 0 0 7 22 1 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.12
Volume:	298.701
LogP:	4.83
LogD:	2.932
LogS:	-4.311
# Rotatable Bonds:	0
TPSA:	85.71
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	4.45
Fsp3:	0.294
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:	-4.975
MDCK Permeability:	7.676416316826362e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.112
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	93.15254974365234%
Volume Distribution (VD):	1.157
Pgp-substrate:	10.236288070678711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.634
CYP2C19-inhibitor:	0.137
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.662
CYP2C9-substrate:	0.725
CYP2D6-inhibitor:	0.51
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	4.535
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.513
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.538
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.688
Skin Sensitization:	0.869
Carcinogencity:	0.733
Eye Corrosion:	0.023
Eye Irritation:	0.907
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC251071

Natural Product ID:	NPC251071
*Common Name:**	ZEVXHSMDHQZKIS-ZETCQYMHSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Cereolactam
Standard InCHIKey:	ZEVXHSMDHQZKIS-ZETCQYMHSA-N
Standard InCHI:	InChI=1S/C17H17NO4/c1-6-5-8(19)10-11-9(6)15-12(17(3,4)7(2)22-15)14(20)13(11)18-16(10)21/h5,7,19-20H,1-4H3,(H,18,21)/t7-/m0/s1
SMILES:	Cc1cc(c2c3c1c1c(c(c3NC2=O)O)C(C)(C)[C@H](C)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1835010
PubChem CID:	56598201
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO6989	Coniothyrium cereale	Species	Coniothyriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21923104]
NPO6989	Coniothyrium cereale	Species	Coniothyriaceae	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	7

Activity Type	# Activity
Individual Protein	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	=	9280.0	nM	PMID[488807]
NPT201	Individual Protein	Papain	Carica papaya	IC50	>	50000.0	nM	PMID[488807]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	>	50000.0	nM	PMID[488807]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[488807]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	>	50000.0	nM	PMID[488807]

☑ 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 NPC251071 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	411
0.1-0.2	2035
0.2-0.3	7364
0.3-0.4	10471
0.4-0.5	6046
0.5-0.6	11015
0.6-0.7	5300
0.7-0.8	54
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7944	Intermediate Similarity	NPC218303
0.7917	Intermediate Similarity	NPC176113
0.7897	Intermediate Similarity	NPC474366
0.7757	Intermediate Similarity	NPC212123
0.7742	Intermediate Similarity	NPC305542
0.7706	Intermediate Similarity	NPC30749
0.7674	Intermediate Similarity	NPC198160
0.7603	Intermediate Similarity	NPC230683
0.7588	Intermediate Similarity	NPC227033
0.7581	Intermediate Similarity	NPC470484
0.758	Intermediate Similarity	NPC116178
0.7566	Intermediate Similarity	NPC285254
0.7545	Intermediate Similarity	NPC321166
0.7545	Intermediate Similarity	NPC217903
0.7477	Intermediate Similarity	NPC90185
0.7467	Intermediate Similarity	NPC76478
0.7456	Intermediate Similarity	NPC13249
0.7427	Intermediate Similarity	NPC99723
0.7419	Intermediate Similarity	NPC133156
0.7411	Intermediate Similarity	NPC182853
0.7409	Intermediate Similarity	NPC25961
0.7407	Intermediate Similarity	NPC288759
0.7397	Intermediate Similarity	NPC207873
0.7397	Intermediate Similarity	NPC100573
0.7354	Intermediate Similarity	NPC148391
0.7349	Intermediate Similarity	NPC101312
0.7339	Intermediate Similarity	NPC301292
0.7339	Intermediate Similarity	NPC313112
0.7313	Intermediate Similarity	NPC329830
0.7313	Intermediate Similarity	NPC7560
0.7313	Intermediate Similarity	NPC118189
0.729	Intermediate Similarity	NPC170333
0.728	Intermediate Similarity	NPC120239
0.7277	Intermediate Similarity	NPC298449
0.7269	Intermediate Similarity	NPC241263
0.7248	Intermediate Similarity	NPC15987
0.7247	Intermediate Similarity	NPC209981
0.7229	Intermediate Similarity	NPC470480
0.7229	Intermediate Similarity	NPC471513
0.7227	Intermediate Similarity	NPC113455
0.7215	Intermediate Similarity	NPC304837
0.7215	Intermediate Similarity	NPC476258
0.7203	Intermediate Similarity	NPC314702
0.72	Intermediate Similarity	NPC2905
0.7198	Intermediate Similarity	NPC315914
0.7181	Intermediate Similarity	NPC134702
0.7169	Intermediate Similarity	NPC286135
0.7168	Intermediate Similarity	NPC234772
0.7156	Intermediate Similarity	NPC268223
0.7156	Intermediate Similarity	NPC114468
0.7155	Intermediate Similarity	NPC477395
0.7155	Intermediate Similarity	NPC473458
0.7149	Intermediate Similarity	NPC246140
0.7149	Intermediate Similarity	NPC195787
0.7143	Intermediate Similarity	NPC220241
0.7143	Intermediate Similarity	NPC295479
0.713	Intermediate Similarity	NPC46990
0.7119	Intermediate Similarity	NPC317567
0.7117	Intermediate Similarity	NPC222561
0.7116	Intermediate Similarity	NPC78284
0.7114	Intermediate Similarity	NPC472589
0.7111	Intermediate Similarity	NPC470482
0.7111	Intermediate Similarity	NPC470481
0.7105	Intermediate Similarity	NPC195120
0.7105	Intermediate Similarity	NPC87560
0.7103	Intermediate Similarity	NPC70340
0.7094	Intermediate Similarity	NPC477397
0.7091	Intermediate Similarity	NPC1464
0.709	Intermediate Similarity	NPC67401
0.7089	Intermediate Similarity	NPC154922
0.707	Intermediate Similarity	NPC114039
0.707	Intermediate Similarity	NPC206109
0.7064	Intermediate Similarity	NPC234933
0.7054	Intermediate Similarity	NPC477160
0.705	Intermediate Similarity	NPC232645
0.705	Intermediate Similarity	NPC72958
0.7048	Intermediate Similarity	NPC472163
0.7046	Intermediate Similarity	NPC476220
0.7046	Intermediate Similarity	NPC160113
0.7043	Intermediate Similarity	NPC10653
0.7043	Intermediate Similarity	NPC157983
0.7043	Intermediate Similarity	NPC318525
0.7043	Intermediate Similarity	NPC118154
0.7037	Intermediate Similarity	NPC470485
0.7035	Intermediate Similarity	NPC477826
0.7035	Intermediate Similarity	NPC477827
0.7033	Intermediate Similarity	NPC472588
0.7019	Intermediate Similarity	NPC129578
0.7018	Intermediate Similarity	NPC240684
0.7017	Intermediate Similarity	NPC291173
0.7015	Intermediate Similarity	NPC87708
0.7009	Intermediate Similarity	NPC257728
0.7	Intermediate Similarity	NPC222046
0.6995	Remote Similarity	NPC180924
0.6995	Remote Similarity	NPC262725
0.6987	Remote Similarity	NPC6786
0.6987	Remote Similarity	NPC314552
0.6987	Remote Similarity	NPC477828
0.6986	Remote Similarity	NPC17677
0.698	Remote Similarity	NPC203373
0.6978	Remote Similarity	NPC477825
0.6976	Remote Similarity	NPC313368
0.6976	Remote Similarity	NPC470810
0.6974	Remote Similarity	NPC290227
0.697	Remote Similarity	NPC469439
0.6968	Remote Similarity	NPC471489
0.6967	Remote Similarity	NPC327005
0.6965	Remote Similarity	NPC474417
0.6965	Remote Similarity	NPC149526
0.6964	Remote Similarity	NPC257266
0.6961	Remote Similarity	NPC96342
0.6961	Remote Similarity	NPC164110
0.6961	Remote Similarity	NPC212967
0.6961	Remote Similarity	NPC246647
0.6959	Remote Similarity	NPC471825
0.6957	Remote Similarity	NPC100849
0.6952	Remote Similarity	NPC477571
0.6952	Remote Similarity	NPC477573
0.6952	Remote Similarity	NPC477572
0.695	Remote Similarity	NPC97028
0.695	Remote Similarity	NPC97029
0.695	Remote Similarity	NPC288036
0.695	Remote Similarity	NPC65589
0.695	Remote Similarity	NPC158338
0.695	Remote Similarity	NPC100985
0.6948	Remote Similarity	NPC132751
0.6944	Remote Similarity	NPC470483
0.6944	Remote Similarity	NPC1820
0.6936	Remote Similarity	NPC140296
0.6933	Remote Similarity	NPC316292
0.6932	Remote Similarity	NPC282346
0.6931	Remote Similarity	NPC273483
0.6927	Remote Similarity	NPC243626
0.6926	Remote Similarity	NPC288110
0.6923	Remote Similarity	NPC314653
0.6923	Remote Similarity	NPC316262
0.6923	Remote Similarity	NPC477394
0.6923	Remote Similarity	NPC19175
0.6923	Remote Similarity	NPC73280
0.692	Remote Similarity	NPC80472
0.6916	Remote Similarity	NPC288854
0.6915	Remote Similarity	NPC119929
0.6915	Remote Similarity	NPC476185
0.6915	Remote Similarity	NPC321896
0.6908	Remote Similarity	NPC473196
0.6903	Remote Similarity	NPC153365
0.69	Remote Similarity	NPC7025
0.69	Remote Similarity	NPC27221
0.69	Remote Similarity	NPC256672
0.6898	Remote Similarity	NPC477396
0.6898	Remote Similarity	NPC474059
0.6897	Remote Similarity	NPC169990
0.6897	Remote Similarity	NPC210942
0.6892	Remote Similarity	NPC185197
0.689	Remote Similarity	NPC53640
0.6889	Remote Similarity	NPC308943
0.6887	Remote Similarity	NPC309692
0.6886	Remote Similarity	NPC10732
0.6885	Remote Similarity	NPC477393
0.6883	Remote Similarity	NPC77777
0.6881	Remote Similarity	NPC478148
0.688	Remote Similarity	NPC205372
0.6878	Remote Similarity	NPC196448
0.687	Remote Similarity	NPC38964
0.6867	Remote Similarity	NPC128476
0.6866	Remote Similarity	NPC233267
0.6866	Remote Similarity	NPC291049
0.6863	Remote Similarity	NPC148938
0.6861	Remote Similarity	NPC328700
0.6861	Remote Similarity	NPC202771
0.6861	Remote Similarity	NPC2173
0.6861	Remote Similarity	NPC119818
0.6857	Remote Similarity	NPC72715
0.6853	Remote Similarity	NPC219397
0.6851	Remote Similarity	NPC231924
0.685	Remote Similarity	NPC22005
0.685	Remote Similarity	NPC123202
0.685	Remote Similarity	NPC7943
0.6847	Remote Similarity	NPC40356
0.6847	Remote Similarity	NPC154683
0.6847	Remote Similarity	NPC138830
0.6847	Remote Similarity	NPC217447
0.6845	Remote Similarity	NPC85121
0.6842	Remote Similarity	NPC473286
0.684	Remote Similarity	NPC120513
0.6838	Remote Similarity	NPC148124
0.6832	Remote Similarity	NPC202595
0.6826	Remote Similarity	NPC55470
0.6825	Remote Similarity	NPC89549
0.6824	Remote Similarity	NPC476069
0.6822	Remote Similarity	NPC324220
0.6822	Remote Similarity	NPC312630
0.682	Remote Similarity	NPC469437
0.682	Remote Similarity	NPC283207
0.6818	Remote Similarity	NPC84266
0.6818	Remote Similarity	NPC162653
0.6816	Remote Similarity	NPC105415
0.6814	Remote Similarity	NPC235333
0.6814	Remote Similarity	NPC478075
0.6814	Remote Similarity	NPC329844

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 NPC251071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	728
0.2-0.3	1108
0.3-0.4	2215
0.4-0.5	2674
0.5-0.6	1735
0.6-0.7	403
0.7-0.8	10
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
0.7783	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD8067	Phase 3
0.7446	Intermediate Similarity	NPD6625	Approved
0.7378	Intermediate Similarity	NPD2899	Discontinued
0.7295	Intermediate Similarity	NPD6104	Discontinued
0.726	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD8461	Discontinued
0.7205	Intermediate Similarity	NPD6997	Phase 2
0.7203	Intermediate Similarity	NPD4846	Phase 2
0.7195	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD8492	Approved
0.7137	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8367	Approved
0.7118	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7654	Discontinued
0.704	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4467	Phase 2
0.7027	Intermediate Similarity	NPD4465	Phase 2
0.7026	Intermediate Similarity	NPD7279	Phase 2
0.7026	Intermediate Similarity	NPD7278	Phase 2
0.7018	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7585	Approved
0.6987	Remote Similarity	NPD7048	Phase 3
0.6987	Remote Similarity	NPD5164	Discontinued
0.6982	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7583	Approved
0.6934	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4361	Phase 2
0.6895	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6874	Approved
0.687	Remote Similarity	NPD7047	Phase 3
0.6862	Remote Similarity	NPD7922	Phase 1
0.6861	Remote Similarity	NPD5006	Approved
0.6861	Remote Similarity	NPD5005	Approved
0.6858	Remote Similarity	NPD7300	Phase 3
0.6858	Remote Similarity	NPD7302	Phase 3
0.6852	Remote Similarity	NPD1898	Discontinued
0.6847	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6719	Approved
0.6831	Remote Similarity	NPD7417	Discontinued
0.6827	Remote Similarity	NPD5710	Approved
0.6827	Remote Similarity	NPD5711	Approved
0.6825	Remote Similarity	NPD6020	Phase 2
0.6812	Remote Similarity	NPD7301	Phase 3
0.6807	Remote Similarity	NPD4981	Phase 2
0.6795	Remote Similarity	NPD7907	Approved
0.6793	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7626	Approved
0.6786	Remote Similarity	NPD7627	Approved
0.6779	Remote Similarity	NPD6959	Discontinued
0.6769	Remote Similarity	NPD1945	Phase 1
0.6762	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5196	Approved
0.6757	Remote Similarity	NPD5194	Approved
0.6757	Remote Similarity	NPD5197	Approved
0.6741	Remote Similarity	NPD6321	Discontinued
0.673	Remote Similarity	NPD7324	Discontinued
0.6726	Remote Similarity	NPD5609	Approved
0.6726	Remote Similarity	NPD5608	Approved
0.6722	Remote Similarity	NPD6723	Discontinued
0.6712	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4859	Phase 1
0.6709	Remote Similarity	NPD4111	Phase 1
0.6709	Remote Similarity	NPD4665	Approved
0.6699	Remote Similarity	NPD6457	Approved
0.6697	Remote Similarity	NPD4363	Phase 3
0.6697	Remote Similarity	NPD4360	Phase 2
0.6697	Remote Similarity	NPD7693	Approved
0.6682	Remote Similarity	NPD4420	Approved
0.6682	Remote Similarity	NPD4668	Phase 2
0.6681	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD3263	Phase 3
0.6667	Remote Similarity	NPD3452	Approved
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD6716	Phase 1
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD3450	Approved
0.6667	Remote Similarity	NPD3912	Discontinued
0.6652	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD2974	Approved
0.6637	Remote Similarity	NPD2975	Approved
0.6637	Remote Similarity	NPD2973	Approved
0.662	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7177	Discontinued
0.661	Remote Similarity	NPD3437	Discontinued
0.6609	Remote Similarity	NPD4679	Discontinued
0.6607	Remote Similarity	NPD8357	Approved
0.6606	Remote Similarity	NPD3154	Approved
0.6606	Remote Similarity	NPD3153	Approved
0.6597	Remote Similarity	NPD7820	Phase 3
0.6593	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6238	Discontinued
0.6592	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5183	Approved
0.6588	Remote Similarity	NPD5186	Approved
0.6582	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4582	Approved
0.6579	Remote Similarity	NPD4583	Approved
0.6575	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6037	Discontinued
0.657	Remote Similarity	NPD1505	Phase 2
0.657	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4580	Approved
0.6545	Remote Similarity	NPD3398	Discontinued
0.654	Remote Similarity	NPD2247	Approved
0.654	Remote Similarity	NPD2249	Approved
0.6538	Remote Similarity	NPD7930	Approved
0.6535	Remote Similarity	NPD4002	Approved
0.6535	Remote Similarity	NPD4004	Approved
0.6525	Remote Similarity	NPD7292	Approved
0.6524	Remote Similarity	NPD7827	Phase 1
0.6522	Remote Similarity	NPD2434	Approved
0.6515	Remote Similarity	NPD8469	Approved
0.6507	Remote Similarity	NPD6644	Discontinued
0.6502	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7262	Phase 1
0.65	Remote Similarity	NPD3925	Approved
0.6498	Remote Similarity	NPD5637	Discontinued
0.6494	Remote Similarity	NPD2514	Approved
0.6491	Remote Similarity	NPD7316	Discontinued
0.649	Remote Similarity	NPD7819	Suspended
0.6489	Remote Similarity	NPD4604	Approved
0.6489	Remote Similarity	NPD4605	Approved
0.6486	Remote Similarity	NPD6456	Discontinued
0.6481	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7783	Phase 2
0.6479	Remote Similarity	NPD1913	Phase 1
0.6478	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5582	Discontinued
0.6441	Remote Similarity	NPD4259	Approved
0.6441	Remote Similarity	NPD5025	Approved
0.6441	Remote Similarity	NPD4258	Approved
0.6437	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD42	Phase 2
0.6435	Remote Similarity	NPD6042	Phase 2
0.6435	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6232	Discontinued
0.6429	Remote Similarity	NPD4466	Phase 1
0.6429	Remote Similarity	NPD5610	Approved
0.6419	Remote Similarity	NPD3057	Approved
0.6418	Remote Similarity	NPD2800	Approved
0.6417	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD5515	Phase 2
0.6416	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3746	Discontinued
0.6407	Remote Similarity	NPD6807	Phase 3
0.6406	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7479	Phase 2
0.6406	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5242	Approved
0.6396	Remote Similarity	NPD7906	Approved
0.6393	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.639	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5488	Discontinued
0.6388	Remote Similarity	NPD5071	Phase 2
0.6381	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6296	Discontinued
0.6379	Remote Similarity	NPD7263	Phase 2
0.6376	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7476	Discontinued
0.6376	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8149	Discontinued
0.6371	Remote Similarity	NPD7708	Approved
0.6368	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5928	Phase 1
0.6364	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1934	Approved
0.6364	Remote Similarity	NPD6250	Discontinued
0.6364	Remote Similarity	NPD7546	Discontinued
0.6364	Remote Similarity	NPD3298	Approved
0.636	Remote Similarity	NPD6974	Phase 3
0.6359	Remote Similarity	NPD5844	Phase 1
0.6356	Remote Similarity	NPD7125	Discontinued
0.6356	Remote Similarity	NPD6181	Discontinued
0.6356	Remote Similarity	NPD2951	Discontinued
0.6351	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD2972	Approved
0.6348	Remote Similarity	NPD2491	Approved
0.6348	Remote Similarity	NPD3533	Approved
0.6348	Remote Similarity	NPD3448	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