NPASS Compound

Structure

NPC19719 OpenBabel07101719512D 28 30 0 0 1 0 0 0 0 0999 V2000 3.0981 -2.3660 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 -0.8660 -1.5000 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 4.8301 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6962 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6962 2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 1 1 6 0 0 0 12 20 1 0 0 0 0 12 27 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 1 0 0 0 16 21 1 6 0 0 0 17 21 1 1 0 0 0 17 28 1 0 0 0 0 18 23 2 0 0 0 0 18 28 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 25 2 0 0 0 0 21 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	386.543
LogP:	2.5
LogD:	0.829
LogS:	-2.071
# Rotatable Bonds:	8
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.417
Synthetic Accessibility Score:	4.5
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.852
MDCK Permeability:	1.4610857760999352e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.504

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.958
Plasma Protein Binding (PPB):	92.59608459472656%
Volume Distribution (VD):	1.02
Pgp-substrate:	7.5009765625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.211
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.342
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	11.974
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.355
Skin Sensitization:	0.425
Carcinogencity:	0.537
Eye Corrosion:	0.03
Eye Irritation:	0.033
Respiratory Toxicity:	0.206

Download Data

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

Natural Product: NPC19719

Natural Product ID:	NPC19719
*Common Name:**	Brevipolide G
IUPAC Name:	[(2S)-1-[(1S,2S)-2-[(S)-hydroxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	Brevipolide G
Standard InCHIKey:	BJDMHAYLPGRUFH-HIELJHRRSA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-12(27-19(24)10-7-13-5-8-14(22)9-6-13)20(25)15-11-16(15)21(26)17-3-2-4-18(23)28-17/h2,4-10,12,15-17,21-22,26H,3,11H2,1H3/b10-7+/t12-,15-,16-,17+,21-/m0/s1
SMILES:	O=C(O[C@H](C(=O)[C@H]1C[C@@H]1[C@@H]([C@H]1CC=CC(=O)O1)O)C)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337108
PubChem CID:	71522010
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	Whole Plant	Tawangmangu village, Karanganyar, Central Java, Indonesia	2003-FEB	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23282042]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28099005]
NPO25696	Hyptis brevipes	Species	Lamiaceae	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	5
IC50	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[452683]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[452683]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[452683]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[452683]
NPT65	Cell Line	HepG2	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[452683]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[452683]

☑ 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 NPC19719 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	283
0.1-0.2	1146
0.2-0.3	2965
0.3-0.4	7051
0.4-0.5	10464
0.5-0.6	6740
0.6-0.7	11479
0.7-0.8	2506
0.8-0.85	52
0.85-0.9	1
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477280
1.0	High Similarity	NPC477281
0.9764	High Similarity	NPC327204
0.9764	High Similarity	NPC323379
0.9466	High Similarity	NPC64230
0.9466	High Similarity	NPC71638
0.9403	High Similarity	NPC477277
0.9403	High Similarity	NPC477278
0.9328	High Similarity	NPC477279
0.9	High Similarity	NPC98009
0.8676	High Similarity	NPC182217
0.8676	High Similarity	NPC70680
0.8676	High Similarity	NPC233350
0.8603	High Similarity	NPC68517
0.8561	High Similarity	NPC110211
0.8529	High Similarity	NPC155209
0.8529	High Similarity	NPC168799
0.8519	High Similarity	NPC198388
0.8489	Intermediate Similarity	NPC283560
0.8489	Intermediate Similarity	NPC24295
0.8473	Intermediate Similarity	NPC14141
0.8456	Intermediate Similarity	NPC61
0.8456	Intermediate Similarity	NPC18074
0.8456	Intermediate Similarity	NPC5419
0.8456	Intermediate Similarity	NPC302844
0.8456	Intermediate Similarity	NPC25581
0.8429	Intermediate Similarity	NPC474875
0.8429	Intermediate Similarity	NPC274891
0.8429	Intermediate Similarity	NPC205751
0.8429	Intermediate Similarity	NPC476819
0.8429	Intermediate Similarity	NPC303683
0.8429	Intermediate Similarity	NPC26241
0.8429	Intermediate Similarity	NPC295492
0.8429	Intermediate Similarity	NPC476820
0.8421	Intermediate Similarity	NPC204579
0.8382	Intermediate Similarity	NPC108553
0.8357	Intermediate Similarity	NPC302857
0.8357	Intermediate Similarity	NPC152942
0.8357	Intermediate Similarity	NPC37250
0.8357	Intermediate Similarity	NPC219428
0.8357	Intermediate Similarity	NPC142703
0.8357	Intermediate Similarity	NPC278068
0.8346	Intermediate Similarity	NPC49938
0.8298	Intermediate Similarity	NPC322021
0.8271	Intermediate Similarity	NPC474803
0.8261	Intermediate Similarity	NPC114116
0.8254	Intermediate Similarity	NPC48525
0.8252	Intermediate Similarity	NPC220664
0.8252	Intermediate Similarity	NPC472016
0.8252	Intermediate Similarity	NPC192831
0.8252	Intermediate Similarity	NPC284948
0.8252	Intermediate Similarity	NPC303090
0.8252	Intermediate Similarity	NPC258469
0.8252	Intermediate Similarity	NPC319628
0.8252	Intermediate Similarity	NPC37331
0.8252	Intermediate Similarity	NPC43158
0.8252	Intermediate Similarity	NPC277315
0.8248	Intermediate Similarity	NPC473777
0.8239	Intermediate Similarity	NPC469911
0.8219	Intermediate Similarity	NPC192568
0.8219	Intermediate Similarity	NPC471076
0.8207	Intermediate Similarity	NPC212808
0.8201	Intermediate Similarity	NPC169398
0.8194	Intermediate Similarity	NPC296659
0.8194	Intermediate Similarity	NPC202391
0.8182	Intermediate Similarity	NPC297517
0.8182	Intermediate Similarity	NPC13818
0.8182	Intermediate Similarity	NPC206095
0.8182	Intermediate Similarity	NPC224389
0.8182	Intermediate Similarity	NPC35702
0.8182	Intermediate Similarity	NPC477335
0.8182	Intermediate Similarity	NPC471027
0.8169	Intermediate Similarity	NPC288452
0.8169	Intermediate Similarity	NPC289690
0.8169	Intermediate Similarity	NPC179505
0.8169	Intermediate Similarity	NPC156709
0.8163	Intermediate Similarity	NPC473719
0.8163	Intermediate Similarity	NPC96599
0.8162	Intermediate Similarity	NPC2596
0.8162	Intermediate Similarity	NPC473744
0.8162	Intermediate Similarity	NPC217431
0.8154	Intermediate Similarity	NPC27633
0.8154	Intermediate Similarity	NPC94298
0.8151	Intermediate Similarity	NPC229264
0.8138	Intermediate Similarity	NPC210330
0.8134	Intermediate Similarity	NPC184219
0.8129	Intermediate Similarity	NPC471749
0.8129	Intermediate Similarity	NPC215484
0.8108	Intermediate Similarity	NPC117346
0.8108	Intermediate Similarity	NPC240592
0.8102	Intermediate Similarity	NPC253595
0.8102	Intermediate Similarity	NPC214246
0.8102	Intermediate Similarity	NPC194979
0.8099	Intermediate Similarity	NPC220936
0.8099	Intermediate Similarity	NPC31745
0.8099	Intermediate Similarity	NPC284409
0.8082	Intermediate Similarity	NPC475539
0.8082	Intermediate Similarity	NPC143246
0.8082	Intermediate Similarity	NPC119773
0.8082	Intermediate Similarity	NPC474268
0.8082	Intermediate Similarity	NPC98356
0.8077	Intermediate Similarity	NPC122117
0.8071	Intermediate Similarity	NPC474895
0.8067	Intermediate Similarity	NPC327225
0.8056	Intermediate Similarity	NPC184053
0.8054	Intermediate Similarity	NPC56204
0.8043	Intermediate Similarity	NPC163169
0.8043	Intermediate Similarity	NPC123
0.8028	Intermediate Similarity	NPC67349
0.8028	Intermediate Similarity	NPC279676
0.8028	Intermediate Similarity	NPC469364
0.8028	Intermediate Similarity	NPC65262
0.8028	Intermediate Similarity	NPC101686
0.8016	Intermediate Similarity	NPC326187
0.8014	Intermediate Similarity	NPC469683
0.8014	Intermediate Similarity	NPC475528
0.8	Intermediate Similarity	NPC131192
0.8	Intermediate Similarity	NPC325646
0.8	Intermediate Similarity	NPC229916
0.8	Intermediate Similarity	NPC28951
0.8	Intermediate Similarity	NPC285550
0.7987	Intermediate Similarity	NPC32197
0.7986	Intermediate Similarity	NPC281798
0.7986	Intermediate Similarity	NPC475044
0.7986	Intermediate Similarity	NPC38473
0.7986	Intermediate Similarity	NPC318799
0.7986	Intermediate Similarity	NPC475063
0.7985	Intermediate Similarity	NPC139171
0.7985	Intermediate Similarity	NPC469927
0.7985	Intermediate Similarity	NPC67300
0.7973	Intermediate Similarity	NPC81835
0.7971	Intermediate Similarity	NPC226855
0.7961	Intermediate Similarity	NPC208173
0.7961	Intermediate Similarity	NPC170189
0.7958	Intermediate Similarity	NPC471345
0.7958	Intermediate Similarity	NPC475111
0.7947	Intermediate Similarity	NPC44730
0.7945	Intermediate Similarity	NPC473281
0.7945	Intermediate Similarity	NPC473090
0.7945	Intermediate Similarity	NPC474692
0.7945	Intermediate Similarity	NPC77922
0.7945	Intermediate Similarity	NPC122491
0.7945	Intermediate Similarity	NPC469615
0.7945	Intermediate Similarity	NPC32
0.7945	Intermediate Similarity	NPC183824
0.7943	Intermediate Similarity	NPC106406
0.7943	Intermediate Similarity	NPC194970
0.7941	Intermediate Similarity	NPC137416
0.7933	Intermediate Similarity	NPC158546
0.7933	Intermediate Similarity	NPC289021
0.7933	Intermediate Similarity	NPC474620
0.7926	Intermediate Similarity	NPC471466
0.7923	Intermediate Similarity	NPC23402
0.7919	Intermediate Similarity	NPC94781
0.7919	Intermediate Similarity	NPC161955
0.7917	Intermediate Similarity	NPC475045
0.7908	Intermediate Similarity	NPC475378
0.7907	Intermediate Similarity	NPC11824
0.7905	Intermediate Similarity	NPC299090
0.7905	Intermediate Similarity	NPC202112
0.7905	Intermediate Similarity	NPC51513
0.7905	Intermediate Similarity	NPC322660
0.7905	Intermediate Similarity	NPC283081
0.7905	Intermediate Similarity	NPC143892
0.7905	Intermediate Similarity	NPC221383
0.7902	Intermediate Similarity	NPC471068
0.7902	Intermediate Similarity	NPC170718
0.7902	Intermediate Similarity	NPC471069
0.7899	Intermediate Similarity	NPC476024
0.7899	Intermediate Similarity	NPC469930
0.7895	Intermediate Similarity	NPC125487
0.7895	Intermediate Similarity	NPC281703
0.7891	Intermediate Similarity	NPC103910
0.7891	Intermediate Similarity	NPC477333
0.7887	Intermediate Similarity	NPC139519
0.7883	Intermediate Similarity	NPC475236
0.7883	Intermediate Similarity	NPC61181
0.7881	Intermediate Similarity	NPC205918
0.7881	Intermediate Similarity	NPC295650
0.7879	Intermediate Similarity	NPC311091
0.7879	Intermediate Similarity	NPC471033
0.7877	Intermediate Similarity	NPC186296
0.7877	Intermediate Similarity	NPC478250
0.7872	Intermediate Similarity	NPC129889
0.7872	Intermediate Similarity	NPC307006
0.7872	Intermediate Similarity	NPC202743
0.7868	Intermediate Similarity	NPC221798
0.7868	Intermediate Similarity	NPC85565
0.7867	Intermediate Similarity	NPC120171
0.7867	Intermediate Similarity	NPC306343
0.7863	Intermediate Similarity	NPC128249
0.7862	Intermediate Similarity	NPC137501
0.7862	Intermediate Similarity	NPC159387
0.7862	Intermediate Similarity	NPC9218
0.7862	Intermediate Similarity	NPC7518
0.7862	Intermediate Similarity	NPC154262
0.7857	Intermediate Similarity	NPC198249
0.7857	Intermediate Similarity	NPC104854
0.7857	Intermediate Similarity	NPC472889
0.7852	Intermediate Similarity	NPC475192

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 NPC19719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	772
0.2-0.3	1607
0.3-0.4	2698
0.4-0.5	2103
0.5-0.6	1196
0.6-0.7	498
0.7-0.8	32
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
0.8252	Intermediate Similarity	NPD6190	Approved
0.8154	Intermediate Similarity	NPD9545	Approved
0.8056	Intermediate Similarity	NPD4628	Phase 3
0.7829	Intermediate Similarity	NPD6801	Discontinued
0.7786	Intermediate Similarity	NPD6798	Discontinued
0.777	Intermediate Similarity	NPD6799	Approved
0.7746	Intermediate Similarity	NPD6355	Discontinued
0.7742	Intermediate Similarity	NPD7075	Discontinued
0.7662	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD230	Phase 1
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6233	Phase 2
0.7606	Intermediate Similarity	NPD4062	Phase 3
0.7582	Intermediate Similarity	NPD6599	Discontinued
0.7535	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD5403	Approved
0.7468	Intermediate Similarity	NPD4380	Phase 2
0.7462	Intermediate Similarity	NPD2067	Discontinued
0.745	Intermediate Similarity	NPD8166	Discontinued
0.7444	Intermediate Similarity	NPD2629	Approved
0.7444	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3887	Approved
0.74	Intermediate Similarity	NPD2354	Approved
0.7379	Intermediate Similarity	NPD4340	Discontinued
0.7376	Intermediate Similarity	NPD5647	Approved
0.7368	Intermediate Similarity	NPD5401	Approved
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7347	Intermediate Similarity	NPD7033	Discontinued
0.7342	Intermediate Similarity	NPD3882	Suspended
0.731	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD3817	Phase 2
0.7278	Intermediate Similarity	NPD5402	Approved
0.7255	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1510	Phase 2
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1608	Approved
0.7212	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4534	Discontinued
0.72	Intermediate Similarity	NPD1549	Phase 2
0.72	Intermediate Similarity	NPD5958	Discontinued
0.7192	Intermediate Similarity	NPD1240	Approved
0.7183	Intermediate Similarity	NPD2797	Approved
0.7176	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2353	Approved
0.7133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2799	Discontinued
0.7111	Intermediate Similarity	NPD1241	Discontinued
0.7105	Intermediate Similarity	NPD3750	Approved
0.7103	Intermediate Similarity	NPD7095	Approved
0.7099	Intermediate Similarity	NPD3134	Approved
0.7095	Intermediate Similarity	NPD1607	Approved
0.7089	Intermediate Similarity	NPD7411	Suspended
0.7087	Intermediate Similarity	NPD9495	Approved
0.7083	Intermediate Similarity	NPD9494	Approved
0.7083	Intermediate Similarity	NPD7685	Pre-registration
0.708	Intermediate Similarity	NPD9493	Approved
0.707	Intermediate Similarity	NPD7458	Discontinued
0.7067	Intermediate Similarity	NPD2796	Approved
0.7063	Intermediate Similarity	NPD987	Approved
0.7048	Intermediate Similarity	NPD3818	Discontinued
0.7044	Intermediate Similarity	NPD1934	Approved
0.7042	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6166	Phase 2
0.703	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5124	Phase 1
0.7027	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6797	Phase 2
0.7023	Intermediate Similarity	NPD5048	Discontinued
0.7021	Intermediate Similarity	NPD422	Phase 1
0.702	Intermediate Similarity	NPD5762	Approved
0.702	Intermediate Similarity	NPD5763	Approved
0.7014	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6663	Approved
0.7007	Intermediate Similarity	NPD4198	Discontinued
0.7	Intermediate Similarity	NPD6647	Phase 2
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD2801	Approved
0.6992	Remote Similarity	NPD2684	Approved
0.6987	Remote Similarity	NPD5049	Phase 3
0.6982	Remote Similarity	NPD7251	Discontinued
0.6981	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1894	Discontinued
0.6977	Remote Similarity	NPD8150	Discontinued
0.6972	Remote Similarity	NPD3972	Approved
0.6972	Remote Similarity	NPD9269	Phase 2
0.6966	Remote Similarity	NPD5736	Approved
0.6962	Remote Similarity	NPD3455	Phase 2
0.6959	Remote Similarity	NPD943	Approved
0.6954	Remote Similarity	NPD2935	Discontinued
0.695	Remote Similarity	NPD3847	Discontinued
0.6947	Remote Similarity	NPD5909	Discontinued
0.6947	Remote Similarity	NPD1237	Approved
0.6946	Remote Similarity	NPD3751	Discontinued
0.6944	Remote Similarity	NPD3266	Approved
0.6944	Remote Similarity	NPD3267	Approved
0.6941	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD7097	Phase 1
0.6929	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1652	Phase 2
0.6923	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3536	Discontinued
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7843	Approved
0.6908	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6004	Phase 3
0.6908	Remote Similarity	NPD6005	Phase 3
0.6908	Remote Similarity	NPD6002	Phase 3
0.6901	Remote Similarity	NPD1535	Discovery
0.6894	Remote Similarity	NPD7819	Suspended
0.6889	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4110	Phase 3
0.6883	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1512	Approved
0.6879	Remote Similarity	NPD8434	Phase 2
0.6879	Remote Similarity	NPD5306	Approved
0.6879	Remote Similarity	NPD5305	Approved
0.6875	Remote Similarity	NPD3225	Approved
0.6871	Remote Similarity	NPD3027	Phase 3
0.6867	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6653	Approved
0.6863	Remote Similarity	NPD2424	Discontinued
0.6854	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1481	Phase 2
0.6852	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD826	Approved
0.6846	Remote Similarity	NPD825	Approved
0.6842	Remote Similarity	NPD2239	Approved
0.6842	Remote Similarity	NPD2240	Approved
0.6835	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD37	Approved
0.6829	Remote Similarity	NPD6234	Discontinued
0.6829	Remote Similarity	NPD919	Approved
0.6824	Remote Similarity	NPD2313	Discontinued
0.6821	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2533	Approved
0.6815	Remote Similarity	NPD3146	Approved
0.6815	Remote Similarity	NPD2532	Approved
0.6815	Remote Similarity	NPD2534	Approved
0.681	Remote Similarity	NPD4965	Approved
0.681	Remote Similarity	NPD4966	Approved
0.681	Remote Similarity	NPD4967	Phase 2
0.6809	Remote Similarity	NPD9268	Approved
0.6807	Remote Similarity	NPD3787	Discontinued
0.6805	Remote Similarity	NPD7054	Approved
0.6805	Remote Similarity	NPD5844	Phase 1
0.6797	Remote Similarity	NPD2860	Approved
0.6797	Remote Similarity	NPD2344	Approved
0.6797	Remote Similarity	NPD2859	Approved
0.6795	Remote Similarity	NPD7236	Approved
0.6786	Remote Similarity	NPD7473	Discontinued
0.6783	Remote Similarity	NPD4806	Approved
0.6783	Remote Similarity	NPD4807	Approved
0.6781	Remote Similarity	NPD2798	Approved
0.6776	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3748	Approved
0.6772	Remote Similarity	NPD6273	Approved
0.677	Remote Similarity	NPD958	Approved
0.677	Remote Similarity	NPD6386	Approved
0.677	Remote Similarity	NPD6385	Approved
0.6769	Remote Similarity	NPD3020	Approved
0.6765	Remote Similarity	NPD7472	Approved
0.6765	Remote Similarity	NPD7074	Phase 3
0.6763	Remote Similarity	NPD255	Approved
0.6763	Remote Similarity	NPD7157	Approved
0.6763	Remote Similarity	NPD256	Approved
0.6761	Remote Similarity	NPD1778	Approved
0.6761	Remote Similarity	NPD3019	Approved
0.6761	Remote Similarity	NPD2932	Approved
0.6759	Remote Similarity	NPD1283	Approved
0.6752	Remote Similarity	NPD1511	Approved
0.6747	Remote Similarity	NPD7199	Phase 2
0.6747	Remote Similarity	NPD8127	Discontinued
0.6741	Remote Similarity	NPD2182	Approved
0.6736	Remote Similarity	NPD9717	Approved
0.6732	Remote Similarity	NPD2438	Suspended
0.6732	Remote Similarity	NPD1551	Phase 2
0.673	Remote Similarity	NPD920	Approved
0.6726	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2933	Approved
0.6719	Remote Similarity	NPD2934	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