NPASS Compound

Structure

CID36868 OpenBabel06191715362D 38 43 0 0 0 0 0 0 0 0999 V2000 4.7242 0.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5169 5.1653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4341 4.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 1.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 4.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 1.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 2.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 0.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 4.1871 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 2.9921 -0.1219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 4.3781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2788 3.3781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 31 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 32 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 9 21 2 0 0 0 0 10 18 1 0 0 0 0 10 22 2 0 0 0 0 11 19 2 0 0 0 0 11 23 1 0 0 0 0 12 20 2 0 0 0 0 12 24 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 19 31 1 0 0 0 0 20 26 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 35 2 0 0 0 0 24 36 2 0 0 0 0 25 27 2 0 0 0 0 26 28 2 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 29 31 1 0 0 0 0 29 37 2 0 0 0 0 30 32 1 0 0 0 0 30 38 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.17
Volume:	526.52
LogP:	5.578
LogD:	2.751
LogS:	-5.436
# Rotatable Bonds:	1
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	3.964
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.118
MDCK Permeability:	1.1961784366576467e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	97.03600311279297%
Volume Distribution (VD):	1.099
Pgp-substrate:	1.74178946018219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.894
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.952
CYP2C9-substrate:	0.77
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.719
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	0.216
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.406
Rat Oral Acute Toxicity:	0.342
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.738
Carcinogencity:	0.694
Eye Corrosion:	0.003
Eye Irritation:	0.407
Respiratory Toxicity:	0.086

Download Data

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

Natural Product: NPC36868

Natural Product ID:	NPC36868
*Common Name:**	Neoboutomannin
IUPAC Name:	8-hydroxy-1-(8-hydroxy-3,3,7-trimethyl-2,5-dioxocyclopenta[a]naphthalen-1-yl)-3,3,7-trimethylcyclopenta[a]naphthalene-2,5-dione
Synonyms:	Neoboutomannin
Standard InCHIKey:	XEKMHELKONVJIX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H26O6/c1-13-7-15-17(9-21(13)33)25-19(11-23(15)35)31(3,4)29(37)27(25)28-26-18-10-22(34)14(2)8-16(18)24(36)12-20(26)32(5,6)30(28)38/h7-12,33-34H,1-6H3
SMILES:	Cc1cc2c(cc1O)C1=C(C3=C4c5cc(c(C)cc5C(=O)C=C4C(C)(C)C3=O)O)C(=O)C(C)(C)C1=CC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047332
PubChem CID:	70688336
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO33127	trigonostemon flavidus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22548480]
NPO24810	Spermacoce alata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8474	Beilschmiedia tooram	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23455	Sphaeria obiones	n.a.	n.a.	n.a.	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	5
MIC	3

Activity Type	# Activity
Cell Line	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[464569]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[464569]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[464569]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[464569]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[464569]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[464569]

☑ 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 NPC36868 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	355
0.1-0.2	1606
0.2-0.3	3186
0.3-0.4	8745
0.4-0.5	10641
0.5-0.6	6864
0.6-0.7	8781
0.7-0.8	2250
0.8-0.85	202
0.85-0.9	57
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9154	High Similarity	NPC254492
0.9084	High Similarity	NPC72667
0.8947	High Similarity	NPC171460
0.8939	High Similarity	NPC69424
0.8939	High Similarity	NPC78364
0.8939	High Similarity	NPC176130
0.8939	High Similarity	NPC84672
0.8897	High Similarity	NPC50924
0.8872	High Similarity	NPC96024
0.8855	High Similarity	NPC199273
0.8806	High Similarity	NPC276238
0.8741	High Similarity	NPC108129
0.8702	High Similarity	NPC282577
0.8686	High Similarity	NPC53896
0.8676	High Similarity	NPC471851
0.8676	High Similarity	NPC244699
0.8667	High Similarity	NPC303910
0.8667	High Similarity	NPC34414
0.8667	High Similarity	NPC146647
0.8643	High Similarity	NPC87723
0.8626	High Similarity	NPC154696
0.8623	High Similarity	NPC202225
0.8593	High Similarity	NPC3009
0.8582	High Similarity	NPC15837
0.8571	High Similarity	NPC53001
0.8561	High Similarity	NPC283088
0.8551	High Similarity	NPC138472
0.8551	High Similarity	NPC78307
0.8551	High Similarity	NPC477139
0.8507	High Similarity	NPC123506
0.85	High Similarity	NPC193358
0.8489	Intermediate Similarity	NPC12070
0.8478	Intermediate Similarity	NPC58685
0.8467	Intermediate Similarity	NPC55949
0.844	Intermediate Similarity	NPC475957
0.8429	Intermediate Similarity	NPC80035
0.8429	Intermediate Similarity	NPC249272
0.8421	Intermediate Similarity	NPC91478
0.8421	Intermediate Similarity	NPC176208
0.8417	Intermediate Similarity	NPC111845
0.8417	Intermediate Similarity	NPC225051
0.8417	Intermediate Similarity	NPC114183
0.8409	Intermediate Similarity	NPC32322
0.8409	Intermediate Similarity	NPC259703
0.8406	Intermediate Similarity	NPC93015
0.8406	Intermediate Similarity	NPC17083
0.8403	Intermediate Similarity	NPC477209
0.838	Intermediate Similarity	NPC13715
0.838	Intermediate Similarity	NPC230811
0.8369	Intermediate Similarity	NPC474311
0.8357	Intermediate Similarity	NPC270899
0.8356	Intermediate Similarity	NPC478160
0.8346	Intermediate Similarity	NPC120545
0.8333	Intermediate Similarity	NPC27659
0.8322	Intermediate Similarity	NPC242994
0.8322	Intermediate Similarity	NPC470407
0.8322	Intermediate Similarity	NPC138099
0.8321	Intermediate Similarity	NPC48248
0.831	Intermediate Similarity	NPC277559
0.831	Intermediate Similarity	NPC471905
0.8298	Intermediate Similarity	NPC477596
0.8298	Intermediate Similarity	NPC153088
0.8286	Intermediate Similarity	NPC52407
0.8276	Intermediate Similarity	NPC239136
0.8276	Intermediate Similarity	NPC19631
0.8273	Intermediate Similarity	NPC18798
0.8264	Intermediate Similarity	NPC169452
0.8264	Intermediate Similarity	NPC181560
0.8261	Intermediate Similarity	NPC117899
0.8261	Intermediate Similarity	NPC99731
0.8252	Intermediate Similarity	NPC4214
0.8239	Intermediate Similarity	NPC191976
0.8239	Intermediate Similarity	NPC254847
0.8239	Intermediate Similarity	NPC155211
0.8239	Intermediate Similarity	NPC471670
0.8235	Intermediate Similarity	NPC137750
0.8227	Intermediate Similarity	NPC477594
0.8222	Intermediate Similarity	NPC273683
0.8219	Intermediate Similarity	NPC100242
0.8219	Intermediate Similarity	NPC478164
0.8207	Intermediate Similarity	NPC246638
0.8188	Intermediate Similarity	NPC282923
0.8188	Intermediate Similarity	NPC193203
0.8182	Intermediate Similarity	NPC49911
0.8182	Intermediate Similarity	NPC53414
0.8182	Intermediate Similarity	NPC53206
0.8175	Intermediate Similarity	NPC71610
0.8169	Intermediate Similarity	NPC22644
0.8169	Intermediate Similarity	NPC258502
0.8162	Intermediate Similarity	NPC164014
0.8162	Intermediate Similarity	NPC142956
0.8156	Intermediate Similarity	NPC115458
0.8156	Intermediate Similarity	NPC267205
0.8156	Intermediate Similarity	NPC4170
0.8151	Intermediate Similarity	NPC193555
0.8151	Intermediate Similarity	NPC135524
0.8151	Intermediate Similarity	NPC201297
0.8148	Intermediate Similarity	NPC307174
0.8143	Intermediate Similarity	NPC239134
0.8143	Intermediate Similarity	NPC72669
0.8143	Intermediate Similarity	NPC474517
0.8138	Intermediate Similarity	NPC96421
0.8138	Intermediate Similarity	NPC471853
0.8134	Intermediate Similarity	NPC190971
0.8129	Intermediate Similarity	NPC25736
0.8125	Intermediate Similarity	NPC416
0.8125	Intermediate Similarity	NPC61398
0.8116	Intermediate Similarity	NPC19432
0.8116	Intermediate Similarity	NPC471530
0.8112	Intermediate Similarity	NPC7464
0.8112	Intermediate Similarity	NPC315275
0.8108	Intermediate Similarity	NPC225351
0.8108	Intermediate Similarity	NPC12402
0.8099	Intermediate Similarity	NPC282780
0.8099	Intermediate Similarity	NPC166480
0.8088	Intermediate Similarity	NPC275145
0.8088	Intermediate Similarity	NPC471187
0.8088	Intermediate Similarity	NPC375356
0.8082	Intermediate Similarity	NPC204045
0.8082	Intermediate Similarity	NPC305845
0.8082	Intermediate Similarity	NPC477275
0.8074	Intermediate Similarity	NPC249340
0.8074	Intermediate Similarity	NPC162935
0.8071	Intermediate Similarity	NPC199253
0.8071	Intermediate Similarity	NPC136588
0.8069	Intermediate Similarity	NPC143438
0.8058	Intermediate Similarity	NPC234175
0.8058	Intermediate Similarity	NPC229894
0.8056	Intermediate Similarity	NPC245923
0.8056	Intermediate Similarity	NPC305060
0.8056	Intermediate Similarity	NPC119542
0.8056	Intermediate Similarity	NPC264022
0.8056	Intermediate Similarity	NPC477592
0.8054	Intermediate Similarity	NPC477208
0.8054	Intermediate Similarity	NPC143685
0.8043	Intermediate Similarity	NPC3224
0.8043	Intermediate Similarity	NPC160499
0.8043	Intermediate Similarity	NPC306765
0.8029	Intermediate Similarity	NPC173978
0.8029	Intermediate Similarity	NPC181334
0.8028	Intermediate Similarity	NPC263817
0.8028	Intermediate Similarity	NPC294226
0.8028	Intermediate Similarity	NPC59459
0.8027	Intermediate Similarity	NPC248068
0.8027	Intermediate Similarity	NPC184935
0.8027	Intermediate Similarity	NPC308572
0.8026	Intermediate Similarity	NPC144283
0.8015	Intermediate Similarity	NPC11250
0.8015	Intermediate Similarity	NPC300274
0.8014	Intermediate Similarity	NPC85342
0.8014	Intermediate Similarity	NPC41847
0.8014	Intermediate Similarity	NPC164295
0.8014	Intermediate Similarity	NPC205992
0.8014	Intermediate Similarity	NPC315578
0.8	Intermediate Similarity	NPC5014
0.8	Intermediate Similarity	NPC469857
0.8	Intermediate Similarity	NPC114333
0.8	Intermediate Similarity	NPC50615
0.8	Intermediate Similarity	NPC149773
0.8	Intermediate Similarity	NPC91887
0.8	Intermediate Similarity	NPC157284
0.8	Intermediate Similarity	NPC469681
0.8	Intermediate Similarity	NPC473779
0.8	Intermediate Similarity	NPC297797
0.8	Intermediate Similarity	NPC5568
0.8	Intermediate Similarity	NPC46242
0.8	Intermediate Similarity	NPC477593
0.8	Intermediate Similarity	NPC473479
0.8	Intermediate Similarity	NPC37709
0.8	Intermediate Similarity	NPC245760
0.8	Intermediate Similarity	NPC20210
0.8	Intermediate Similarity	NPC51531
0.8	Intermediate Similarity	NPC42384
0.8	Intermediate Similarity	NPC28592
0.8	Intermediate Similarity	NPC241001
0.8	Intermediate Similarity	NPC23667
0.8	Intermediate Similarity	NPC469680
0.8	Intermediate Similarity	NPC289358
0.8	Intermediate Similarity	NPC165191
0.8	Intermediate Similarity	NPC477849
0.8	Intermediate Similarity	NPC471974
0.7987	Intermediate Similarity	NPC34482
0.7986	Intermediate Similarity	NPC474813
0.7986	Intermediate Similarity	NPC118919
0.7986	Intermediate Similarity	NPC472308
0.7986	Intermediate Similarity	NPC272268
0.7974	Intermediate Similarity	NPC27615
0.7973	Intermediate Similarity	NPC296752
0.7973	Intermediate Similarity	NPC313047
0.7973	Intermediate Similarity	NPC66593
0.7973	Intermediate Similarity	NPC174905
0.7973	Intermediate Similarity	NPC474203
0.7973	Intermediate Similarity	NPC295712
0.7973	Intermediate Similarity	NPC471682
0.7973	Intermediate Similarity	NPC293545
0.7973	Intermediate Similarity	NPC451542
0.7972	Intermediate Similarity	NPC472262
0.7972	Intermediate Similarity	NPC287604
0.7972	Intermediate Similarity	NPC161964
0.7972	Intermediate Similarity	NPC44437

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 NPC36868 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	989
0.2-0.3	1319
0.3-0.4	2716
0.4-0.5	2231
0.5-0.6	1123
0.6-0.7	397
0.7-0.8	53
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD2932	Approved
0.7985	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1470	Approved
0.7926	Intermediate Similarity	NPD3019	Approved
0.7919	Intermediate Similarity	NPD7390	Discontinued
0.781	Intermediate Similarity	NPD1201	Approved
0.7808	Intermediate Similarity	NPD5404	Approved
0.7808	Intermediate Similarity	NPD5406	Approved
0.7808	Intermediate Similarity	NPD5405	Approved
0.7808	Intermediate Similarity	NPD5408	Approved
0.763	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7003	Approved
0.7482	Intermediate Similarity	NPD3026	Approved
0.7482	Intermediate Similarity	NPD3023	Approved
0.7481	Intermediate Similarity	NPD5951	Approved
0.7464	Intermediate Similarity	NPD3025	Approved
0.7464	Intermediate Similarity	NPD3024	Approved
0.7436	Intermediate Similarity	NPD7458	Discontinued
0.741	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3300	Phase 2
0.7376	Intermediate Similarity	NPD3972	Approved
0.7368	Intermediate Similarity	NPD8166	Discontinued
0.7285	Intermediate Similarity	NPD2346	Discontinued
0.7279	Intermediate Similarity	NPD6663	Approved
0.7267	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD943	Approved
0.7222	Intermediate Similarity	NPD1164	Approved
0.7219	Intermediate Similarity	NPD2935	Discontinued
0.7215	Intermediate Similarity	NPD3226	Approved
0.7211	Intermediate Similarity	NPD3764	Approved
0.7171	Intermediate Similarity	NPD2344	Approved
0.7153	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7134	Intermediate Similarity	NPD6273	Approved
0.7123	Intermediate Similarity	NPD5736	Approved
0.7099	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1651	Approved
0.7091	Intermediate Similarity	NPD6959	Discontinued
0.709	Intermediate Similarity	NPD2342	Discontinued
0.708	Intermediate Similarity	NPD7635	Approved
0.7078	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6232	Discontinued
0.7042	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4059	Approved
0.7039	Intermediate Similarity	NPD2799	Discontinued
0.7037	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1283	Approved
0.7032	Intermediate Similarity	NPD4628	Phase 3
0.7027	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7473	Discontinued
0.7021	Intermediate Similarity	NPD3091	Approved
0.702	Intermediate Similarity	NPD1607	Approved
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6100	Approved
0.6993	Remote Similarity	NPD6099	Approved
0.6987	Remote Similarity	NPD2309	Approved
0.6962	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2534	Approved
0.6962	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2532	Approved
0.6962	Remote Similarity	NPD2533	Approved
0.6957	Remote Similarity	NPD7028	Phase 2
0.695	Remote Similarity	NPD7610	Discontinued
0.6939	Remote Similarity	NPD2798	Approved
0.6928	Remote Similarity	NPD1510	Phase 2
0.6928	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4626	Approved
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7008	Discontinued
0.6901	Remote Similarity	NPD7009	Phase 2
0.6897	Remote Similarity	NPD4878	Approved
0.689	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1240	Approved
0.6859	Remote Similarity	NPD2800	Approved
0.6852	Remote Similarity	NPD4380	Phase 2
0.6849	Remote Similarity	NPD1755	Approved
0.6846	Remote Similarity	NPD1809	Phase 2
0.6842	Remote Similarity	NPD5844	Phase 1
0.6839	Remote Similarity	NPD1471	Phase 3
0.6838	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7236	Approved
0.6829	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3092	Approved
0.6828	Remote Similarity	NPD1281	Approved
0.6821	Remote Similarity	NPD8032	Phase 2
0.6818	Remote Similarity	NPD3020	Approved
0.6818	Remote Similarity	NPD8150	Discontinued
0.6818	Remote Similarity	NPD3748	Approved
0.6806	Remote Similarity	NPD3095	Discontinued
0.6795	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3094	Phase 2
0.6755	Remote Similarity	NPD2313	Discontinued
0.675	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3021	Approved
0.6739	Remote Similarity	NPD3022	Approved
0.6739	Remote Similarity	NPD4750	Phase 3
0.6735	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7239	Suspended
0.6718	Remote Similarity	NPD2859	Approved
0.6718	Remote Similarity	NPD844	Approved
0.6718	Remote Similarity	NPD2860	Approved
0.671	Remote Similarity	NPD4308	Phase 3
0.6707	Remote Similarity	NPD3749	Approved
0.6707	Remote Similarity	NPD7411	Suspended
0.6691	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2286	Discontinued
0.6688	Remote Similarity	NPD1549	Phase 2
0.6688	Remote Similarity	NPD4097	Suspended
0.6688	Remote Similarity	NPD6651	Approved
0.6686	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD1929	Approved
0.6667	Remote Similarity	NPD288	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3495	Discontinued
0.6667	Remote Similarity	NPD9545	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7768	Phase 2
0.6647	Remote Similarity	NPD6020	Phase 2
0.6646	Remote Similarity	NPD6599	Discontinued
0.6645	Remote Similarity	NPD3268	Approved
0.6644	Remote Similarity	NPD4879	Approved
0.6643	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2934	Approved
0.6641	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2933	Approved
0.6624	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5691	Approved
0.6607	Remote Similarity	NPD7075	Discontinued
0.6601	Remote Similarity	NPD7961	Discontinued
0.6584	Remote Similarity	NPD1511	Approved
0.6584	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1934	Approved
0.6561	Remote Similarity	NPD2796	Approved
0.6558	Remote Similarity	NPD4060	Phase 1
0.6556	Remote Similarity	NPD4208	Discontinued
0.6554	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD9269	Phase 2
0.6548	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3882	Suspended
0.6547	Remote Similarity	NPD9266	Approved
0.6547	Remote Similarity	NPD74	Approved
0.6533	Remote Similarity	NPD2797	Approved
0.6529	Remote Similarity	NPD5494	Approved
0.6528	Remote Similarity	NPD9493	Approved
0.6528	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2801	Approved
0.6527	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1465	Phase 2
0.6525	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4207	Discontinued
0.651	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD9268	Approved
0.6507	Remote Similarity	NPD4093	Discontinued
0.6503	Remote Similarity	NPD1512	Approved
0.6503	Remote Similarity	NPD497	Approved
0.6496	Remote Similarity	NPD1237	Approved
0.6491	Remote Similarity	NPD8127	Discontinued
0.649	Remote Similarity	NPD4624	Approved
0.6488	Remote Similarity	NPD2296	Approved
0.6475	Remote Similarity	NPD9267	Approved
0.6475	Remote Similarity	NPD9263	Approved
0.6475	Remote Similarity	NPD9264	Approved
0.6471	Remote Similarity	NPD1932	Approved
0.6471	Remote Similarity	NPD4625	Phase 3
0.6471	Remote Similarity	NPD5155	Approved
0.6471	Remote Similarity	NPD5156	Approved
0.6467	Remote Similarity	NPD6696	Suspended
0.6463	Remote Similarity	NPD1751	Approved
0.6463	Remote Similarity	NPD4589	Approved
0.6461	Remote Similarity	NPD8313	Approved
0.6461	Remote Similarity	NPD8312	Approved
0.6456	Remote Similarity	NPD2438	Suspended
0.6456	Remote Similarity	NPD4477	Approved
0.6456	Remote Similarity	NPD2531	Phase 2
0.6456	Remote Similarity	NPD4476	Approved
0.6453	Remote Similarity	NPD5710	Approved
0.6453	Remote Similarity	NPD5711	Approved
0.6452	Remote Similarity	NPD4307	Phase 2
0.6447	Remote Similarity	NPD9494	Approved
0.6444	Remote Similarity	NPD8434	Phase 2
0.6444	Remote Similarity	NPD2066	Phase 3
0.6443	Remote Similarity	NPD1608	Approved
0.6441	Remote Similarity	NPD5029	Approved
0.6441	Remote Similarity	NPD5031	Approved
0.6441	Remote Similarity	NPD5027	Approved
0.6441	Remote Similarity	NPD6559	Discontinued

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