NPASS Compound

Structure

NPC329707 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.8284 0.2111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1957 -3.2478 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 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4623 0.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7845 0.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9363 -0.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0126 -2.0965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5109 -2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8779 -0.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2421 -2.2488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6240 -1.6035 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 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 -2.4197 -2.2092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 7 1 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 22 1 0 0 0 0 15 19 1 0 0 0 0 16 7 1 6 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	335.841
LogP:	4.834
LogD:	4.38
LogS:	-5.095
# Rotatable Bonds:	0
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	5.586
Fsp3:	0.6
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:	-4.734
MDCK Permeability:	2.3606500690220855e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.889
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.366
Plasma Protein Binding (PPB):	91.38095092773438%
Volume Distribution (VD):	1.331
Pgp-substrate:	2.8708858489990234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.162
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.36
CYP2C19-substrate:	0.341
CYP2C9-inhibitor:	0.303
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.102
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.411

ADMET: Excretion

Clearance (CL):	8.901
Half-life (T1/2):	0.157

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.128
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.086
Carcinogencity:	0.536
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC329707

Natural Product ID:	NPC329707
*Common Name:**	Cespitularin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JVNAZMDBBAYMLF-AUORYKPQSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-13-5-7-16-8-6-15-12-22-18(19(15)20(16,3)4)11-14(2)10-17(21)9-13/h10,12,16-17,21H,1,5-9,11H2,2-4H3/b14-10+/t16-,17?/m1/s1
SMILES:	C=C1CC[C@@H]2CCc3c(C2(C)C)c(C/C(=C/C(C1)O)/C)oc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523103
PubChem CID:	12967196
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004144] Heteroaromatic 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
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398538]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061391]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.66	ug ml-1	PMID[530164]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	8.42	ug ml-1	PMID[530164]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	9.76	ug ml-1	PMID[530164]

☑ 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 NPC329707 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	271
0.1-0.2	1324
0.2-0.3	2869
0.3-0.4	7578
0.4-0.5	12496
0.5-0.6	8579
0.6-0.7	8670
0.7-0.8	815
0.8-0.85	80
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC97566
0.9062	High Similarity	NPC473982
0.8968	High Similarity	NPC290955
0.8889	High Similarity	NPC23086
0.888	High Similarity	NPC118853
0.888	High Similarity	NPC178382
0.88	High Similarity	NPC272899
0.8797	High Similarity	NPC472376
0.8731	High Similarity	NPC202260
0.8702	High Similarity	NPC293253
0.8692	High Similarity	NPC61788
0.8689	High Similarity	NPC59035
0.8689	High Similarity	NPC79202
0.8682	High Similarity	NPC59502
0.8672	High Similarity	NPC246392
0.8661	High Similarity	NPC303010
0.8661	High Similarity	NPC471074
0.8661	High Similarity	NPC473885
0.8613	High Similarity	NPC64568
0.8605	High Similarity	NPC26532
0.8605	High Similarity	NPC112706
0.8605	High Similarity	NPC279877
0.8605	High Similarity	NPC207294
0.8583	High Similarity	NPC130275
0.8571	High Similarity	NPC477967
0.8561	High Similarity	NPC218838
0.854	High Similarity	NPC263337
0.8529	High Similarity	NPC201370
0.8529	High Similarity	NPC148374
0.8529	High Similarity	NPC473983
0.8516	High Similarity	NPC300098
0.8485	Intermediate Similarity	NPC471995
0.8468	Intermediate Similarity	NPC212918
0.845	Intermediate Similarity	NPC138139
0.845	Intermediate Similarity	NPC46536
0.8444	Intermediate Similarity	NPC170604
0.8444	Intermediate Similarity	NPC215109
0.8444	Intermediate Similarity	NPC307401
0.8433	Intermediate Similarity	NPC476947
0.8429	Intermediate Similarity	NPC97904
0.8417	Intermediate Similarity	NPC158871
0.8409	Intermediate Similarity	NPC477645
0.8397	Intermediate Similarity	NPC223063
0.8397	Intermediate Similarity	NPC120836
0.8394	Intermediate Similarity	NPC18904
0.8385	Intermediate Similarity	NPC83178
0.8372	Intermediate Similarity	NPC290193
0.8361	Intermediate Similarity	NPC22678
0.8358	Intermediate Similarity	NPC106247
0.8321	Intermediate Similarity	NPC90953
0.832	Intermediate Similarity	NPC227660
0.831	Intermediate Similarity	NPC93666
0.8309	Intermediate Similarity	NPC473268
0.8306	Intermediate Similarity	NPC150895
0.8306	Intermediate Similarity	NPC205523
0.8296	Intermediate Similarity	NPC158525
0.8296	Intermediate Similarity	NPC265793
0.8295	Intermediate Similarity	NPC243269
0.8281	Intermediate Similarity	NPC36255
0.8276	Intermediate Similarity	NPC114880
0.8271	Intermediate Similarity	NPC89133
0.8264	Intermediate Similarity	NPC472787
0.8254	Intermediate Similarity	NPC243704
0.8254	Intermediate Similarity	NPC87466
0.8252	Intermediate Similarity	NPC211625
0.8248	Intermediate Similarity	NPC471996
0.8248	Intermediate Similarity	NPC177262
0.8235	Intermediate Similarity	NPC46896
0.8217	Intermediate Similarity	NPC16922
0.8207	Intermediate Similarity	NPC294511
0.8207	Intermediate Similarity	NPC121615
0.8201	Intermediate Similarity	NPC205765
0.8194	Intermediate Similarity	NPC212257
0.8182	Intermediate Similarity	NPC477123
0.8182	Intermediate Similarity	NPC477040
0.8182	Intermediate Similarity	NPC477966
0.8175	Intermediate Similarity	NPC217180
0.8175	Intermediate Similarity	NPC64157
0.8175	Intermediate Similarity	NPC4764
0.8175	Intermediate Similarity	NPC278832
0.8175	Intermediate Similarity	NPC312525
0.8162	Intermediate Similarity	NPC209858
0.8154	Intermediate Similarity	NPC83115
0.8143	Intermediate Similarity	NPC52412
0.8129	Intermediate Similarity	NPC61157
0.8129	Intermediate Similarity	NPC67003
0.8129	Intermediate Similarity	NPC473681
0.8129	Intermediate Similarity	NPC218204
0.812	Intermediate Similarity	NPC208389
0.812	Intermediate Similarity	NPC198904
0.811	Intermediate Similarity	NPC21831
0.811	Intermediate Similarity	NPC187547
0.8099	Intermediate Similarity	NPC56731
0.8099	Intermediate Similarity	NPC247221
0.8095	Intermediate Similarity	NPC75310
0.8095	Intermediate Similarity	NPC472785
0.8092	Intermediate Similarity	NPC179354
0.8092	Intermediate Similarity	NPC230979
0.8088	Intermediate Similarity	NPC471998
0.8085	Intermediate Similarity	NPC243577
0.8085	Intermediate Similarity	NPC476946
0.8082	Intermediate Similarity	NPC475777
0.8069	Intermediate Similarity	NPC228842
0.806	Intermediate Similarity	NPC476925
0.806	Intermediate Similarity	NPC939
0.8054	Intermediate Similarity	NPC116639
0.8047	Intermediate Similarity	NPC137710
0.8045	Intermediate Similarity	NPC476917
0.8045	Intermediate Similarity	NPC327527
0.8045	Intermediate Similarity	NPC477039
0.8042	Intermediate Similarity	NPC62799
0.803	Intermediate Similarity	NPC74612
0.8029	Intermediate Similarity	NPC324117
0.8028	Intermediate Similarity	NPC84479
0.8028	Intermediate Similarity	NPC476944
0.8027	Intermediate Similarity	NPC44606
0.8015	Intermediate Similarity	NPC477965
0.8015	Intermediate Similarity	NPC477038
0.8015	Intermediate Similarity	NPC471006
0.8014	Intermediate Similarity	NPC62103
0.8014	Intermediate Similarity	NPC20578
0.8	Intermediate Similarity	NPC298190
0.8	Intermediate Similarity	NPC317217
0.7987	Intermediate Similarity	NPC194499
0.7987	Intermediate Similarity	NPC304692
0.7986	Intermediate Similarity	NPC130976
0.7986	Intermediate Similarity	NPC71821
0.7973	Intermediate Similarity	NPC472786
0.7973	Intermediate Similarity	NPC179170
0.7972	Intermediate Similarity	NPC185456
0.7971	Intermediate Similarity	NPC303217
0.7971	Intermediate Similarity	NPC146872
0.7959	Intermediate Similarity	NPC145830
0.7958	Intermediate Similarity	NPC267632
0.7958	Intermediate Similarity	NPC205071
0.7955	Intermediate Similarity	NPC474829
0.7941	Intermediate Similarity	NPC471817
0.7933	Intermediate Similarity	NPC474611
0.7933	Intermediate Similarity	NPC84349
0.7931	Intermediate Similarity	NPC19747
0.7929	Intermediate Similarity	NPC233707
0.7923	Intermediate Similarity	NPC79557
0.7919	Intermediate Similarity	NPC104736
0.7919	Intermediate Similarity	NPC41880
0.7899	Intermediate Similarity	NPC159786
0.7895	Intermediate Similarity	NPC470858
0.7891	Intermediate Similarity	NPC208906
0.7891	Intermediate Similarity	NPC144745
0.7887	Intermediate Similarity	NPC121158
0.7883	Intermediate Similarity	NPC470740
0.7879	Intermediate Similarity	NPC188377
0.7879	Intermediate Similarity	NPC65735
0.7877	Intermediate Similarity	NPC470998
0.7872	Intermediate Similarity	NPC90296
0.7867	Intermediate Similarity	NPC221992
0.7867	Intermediate Similarity	NPC7059
0.7867	Intermediate Similarity	NPC88007
0.7867	Intermediate Similarity	NPC195954
0.7863	Intermediate Similarity	NPC471549
0.7863	Intermediate Similarity	NPC473379
0.7863	Intermediate Similarity	NPC263870
0.7862	Intermediate Similarity	NPC250228
0.7862	Intermediate Similarity	NPC302987
0.7862	Intermediate Similarity	NPC216755
0.7862	Intermediate Similarity	NPC471174
0.7857	Intermediate Similarity	NPC476943
0.7852	Intermediate Similarity	NPC88958
0.7847	Intermediate Similarity	NPC5676
0.7847	Intermediate Similarity	NPC290038
0.7847	Intermediate Similarity	NPC114513
0.7847	Intermediate Similarity	NPC469642
0.7847	Intermediate Similarity	NPC245522
0.7843	Intermediate Similarity	NPC261184
0.7838	Intermediate Similarity	NPC246164
0.7836	Intermediate Similarity	NPC474830
0.7832	Intermediate Similarity	NPC103134
0.7832	Intermediate Similarity	NPC329493
0.7829	Intermediate Similarity	NPC79571
0.7829	Intermediate Similarity	NPC18986
0.7823	Intermediate Similarity	NPC177331
0.7817	Intermediate Similarity	NPC477537
0.7817	Intermediate Similarity	NPC477535
0.7815	Intermediate Similarity	NPC472823
0.7815	Intermediate Similarity	NPC140952
0.7812	Intermediate Similarity	NPC474987
0.7808	Intermediate Similarity	NPC66991
0.7801	Intermediate Similarity	NPC107571
0.7794	Intermediate Similarity	NPC45947
0.7793	Intermediate Similarity	NPC346
0.7793	Intermediate Similarity	NPC233763
0.7793	Intermediate Similarity	NPC478166
0.7786	Intermediate Similarity	NPC310830
0.7778	Intermediate Similarity	NPC474279
0.7778	Intermediate Similarity	NPC283209
0.7778	Intermediate Similarity	NPC474438
0.7778	Intermediate Similarity	NPC251865
0.777	Intermediate Similarity	NPC92941
0.7763	Intermediate Similarity	NPC287559
0.7763	Intermediate Similarity	NPC8389
0.7763	Intermediate Similarity	NPC472299

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 NPC329707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	994
0.2-0.3	1572
0.3-0.4	2621
0.4-0.5	2180
0.5-0.6	1189
0.6-0.7	311
0.7-0.8	21
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
0.8058	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6273	Approved
0.7639	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD5760	Phase 2
0.75	Intermediate Similarity	NPD5761	Phase 2
0.7444	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2344	Approved
0.7407	Intermediate Similarity	NPD3972	Approved
0.731	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6002	Phase 3
0.731	Intermediate Similarity	NPD6005	Phase 3
0.731	Intermediate Similarity	NPD6004	Phase 3
0.7308	Intermediate Similarity	NPD1241	Discontinued
0.7299	Intermediate Similarity	NPD1876	Approved
0.7292	Intermediate Similarity	NPD2799	Discontinued
0.7279	Intermediate Similarity	NPD7003	Approved
0.7254	Intermediate Similarity	NPD4140	Approved
0.7246	Intermediate Similarity	NPD2797	Approved
0.7239	Intermediate Similarity	NPD6764	Approved
0.7239	Intermediate Similarity	NPD6765	Approved
0.7237	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2309	Approved
0.7229	Intermediate Similarity	NPD8434	Phase 2
0.7226	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2800	Approved
0.7209	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5647	Approved
0.7194	Intermediate Similarity	NPD2798	Approved
0.7192	Intermediate Similarity	NPD2346	Discontinued
0.7192	Intermediate Similarity	NPD1471	Phase 3
0.7183	Intermediate Similarity	NPD8032	Phase 2
0.7163	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6099	Approved
0.7123	Intermediate Similarity	NPD6100	Approved
0.7113	Intermediate Similarity	NPD3268	Approved
0.7113	Intermediate Similarity	NPD2313	Discontinued
0.7095	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2532	Approved
0.7086	Intermediate Similarity	NPD2533	Approved
0.7086	Intermediate Similarity	NPD2534	Approved
0.7083	Intermediate Similarity	NPD6355	Discontinued
0.7068	Intermediate Similarity	NPD7157	Approved
0.7066	Intermediate Similarity	NPD6784	Approved
0.7066	Intermediate Similarity	NPD6785	Approved
0.7059	Intermediate Similarity	NPD1778	Approved
0.705	Intermediate Similarity	NPD1283	Approved
0.7047	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4110	Phase 3
0.7029	Intermediate Similarity	NPD1608	Approved
0.7029	Intermediate Similarity	NPD9717	Approved
0.7013	Intermediate Similarity	NPD7458	Discontinued
0.6993	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1651	Approved
0.6985	Remote Similarity	NPD5585	Approved
0.6978	Remote Similarity	NPD5327	Phase 3
0.6966	Remote Similarity	NPD5735	Approved
0.6939	Remote Similarity	NPD4308	Phase 3
0.6934	Remote Similarity	NPD4626	Approved
0.6934	Remote Similarity	NPD3019	Approved
0.6934	Remote Similarity	NPD2932	Approved
0.6929	Remote Similarity	NPD6696	Suspended
0.6928	Remote Similarity	NPD6559	Discontinued
0.6923	Remote Similarity	NPD2684	Approved
0.6923	Remote Similarity	NPD7008	Discontinued
0.6918	Remote Similarity	NPD6653	Approved
0.6912	Remote Similarity	NPD1894	Discontinued
0.6901	Remote Similarity	NPD9494	Approved
0.6899	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2796	Approved
0.6892	Remote Similarity	NPD4476	Approved
0.6892	Remote Similarity	NPD4477	Approved
0.6892	Remote Similarity	NPD1551	Phase 2
0.6884	Remote Similarity	NPD3496	Discontinued
0.6879	Remote Similarity	NPD6362	Approved
0.6875	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2629	Approved
0.6863	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5691	Approved
0.6853	Remote Similarity	NPD6832	Phase 2
0.6846	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9092	Discovery
0.6835	Remote Similarity	NPD1281	Approved
0.6831	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6663	Approved
0.6821	Remote Similarity	NPD3750	Approved
0.6812	Remote Similarity	NPD17	Approved
0.6803	Remote Similarity	NPD6651	Approved
0.6803	Remote Similarity	NPD6353	Approved
0.68	Remote Similarity	NPD2424	Discontinued
0.68	Remote Similarity	NPD1549	Phase 2
0.68	Remote Similarity	NPD4534	Discontinued
0.6795	Remote Similarity	NPD2651	Approved
0.6795	Remote Similarity	NPD3226	Approved
0.6795	Remote Similarity	NPD2649	Approved
0.679	Remote Similarity	NPD8127	Discontinued
0.6788	Remote Similarity	NPD9545	Approved
0.6783	Remote Similarity	NPD5736	Approved
0.6781	Remote Similarity	NPD3142	Approved
0.6781	Remote Similarity	NPD3620	Phase 2
0.6781	Remote Similarity	NPD3140	Approved
0.6781	Remote Similarity	NPD2979	Phase 3
0.6781	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2935	Discontinued
0.6774	Remote Similarity	NPD3869	Phase 3
0.6774	Remote Similarity	NPD920	Approved
0.6774	Remote Similarity	NPD3873	Phase 3
0.6767	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3267	Approved
0.6761	Remote Similarity	NPD3266	Approved
0.6761	Remote Similarity	NPD1203	Approved
0.6761	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD411	Approved
0.6759	Remote Similarity	NPD3764	Approved
0.6759	Remote Similarity	NPD6798	Discontinued
0.6755	Remote Similarity	NPD1243	Approved
0.6753	Remote Similarity	NPD4662	Approved
0.6753	Remote Similarity	NPD4661	Approved
0.6753	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7028	Phase 2
0.6752	Remote Similarity	NPD6599	Discontinued
0.6744	Remote Similarity	NPD1237	Approved
0.6741	Remote Similarity	NPD5951	Approved
0.6738	Remote Similarity	NPD4359	Approved
0.6733	Remote Similarity	NPD5763	Approved
0.6733	Remote Similarity	NPD5762	Approved
0.6732	Remote Similarity	NPD7236	Approved
0.673	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7819	Suspended
0.6718	Remote Similarity	NPD290	Approved
0.6716	Remote Similarity	NPD7843	Approved
0.6711	Remote Similarity	NPD7033	Discontinued
0.6711	Remote Similarity	NPD8166	Discontinued
0.6692	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1607	Approved
0.6689	Remote Similarity	NPD5958	Discontinued
0.6687	Remote Similarity	NPD2296	Approved
0.6687	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD6279	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD5712	Approved
0.6667	Remote Similarity	NPD6280	Approved
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7577	Discontinued
0.6646	Remote Similarity	NPD4380	Phase 2
0.6645	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD9493	Approved
0.6642	Remote Similarity	NPD7340	Approved
0.6641	Remote Similarity	NPD3134	Approved
0.6627	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5124	Phase 1
0.6622	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD447	Suspended
0.6621	Remote Similarity	NPD2614	Approved
0.6618	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD3749	Approved
0.6605	Remote Similarity	NPD7075	Discontinued
0.6604	Remote Similarity	NPD7411	Suspended
0.6601	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1510	Phase 2
0.66	Remote Similarity	NPD3748	Approved
0.6599	Remote Similarity	NPD4062	Phase 3
0.6599	Remote Similarity	NPD6233	Phase 2
0.6599	Remote Similarity	NPD4870	Approved
0.6597	Remote Similarity	NPD1019	Discontinued
0.6597	Remote Similarity	NPD4624	Approved
0.6596	Remote Similarity	NPD1201	Approved
0.6575	Remote Similarity	NPD7095	Approved
0.6569	Remote Similarity	NPD6671	Approved
0.6562	Remote Similarity	NPD1934	Approved
0.6562	Remote Similarity	NPD6801	Discontinued
0.6562	Remote Similarity	NPD37	Approved
0.6562	Remote Similarity	NPD6844	Discontinued
0.6561	Remote Similarity	NPD5403	Approved
0.6558	Remote Similarity	NPD3887	Approved
0.6556	Remote Similarity	NPD2531	Phase 2
0.6552	Remote Similarity	NPD1712	Approved
0.6552	Remote Similarity	NPD2861	Phase 2
0.6549	Remote Similarity	NPD2231	Phase 2
0.6549	Remote Similarity	NPD1481	Phase 2
0.6549	Remote Similarity	NPD2235	Phase 2
0.6548	Remote Similarity	NPD5844	Phase 1
0.6547	Remote Similarity	NPD3091	Approved
0.6544	Remote Similarity	NPD1398	Phase 1

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