NPASS Compound

Structure

CID269420 OpenBabel06191716072D 36 38 0 0 0 0 0 0 0 0999 V2000 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 3.4641 2.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 -3.4641 0.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 8 13 1 0 0 0 0 8 17 2 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 19 23 2 0 0 0 0 20 29 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 25 1 0 0 0 0 22 30 2 0 0 0 0 23 31 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 34 2 0 0 0 0 28 29 2 0 0 0 0 28 35 1 0 0 0 0 29 36 1 0 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.24
Volume:	525.507
LogP:	7.829
LogD:	3.71
LogS:	-2.854
# Rotatable Bonds:	7
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	3.363
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.955
MDCK Permeability:	1.331213024968747e-05
Pgp-inhibitor:	0.921
Pgp-substrate:	0.63
Human Intestinal Absorption (HIA):	0.096
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	85.86237335205078%
Volume Distribution (VD):	1.37
Pgp-substrate:	15.599536895751953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.302
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.723
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.133
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	8.156
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.976
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.466
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.823
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.4
Respiratory Toxicity:	0.138

Download Data

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

Natural Product: NPC269420

Natural Product ID:	NPC269420
*Common Name:**	Dorsilurin F
IUPAC Name:	3,5,7-trihydroxy-2-[3-hydroxy-4-(3-methylbut-2-enyl)phenyl]-6,8-bis(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Dorsilurin F
Standard InCHIKey:	BHIMYJSCHPQEQT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H34O6/c1-16(2)7-10-19-11-12-20(15-23(19)31)29-28(35)27(34)24-26(33)21(13-8-17(3)4)25(32)22(30(24)36-29)14-9-18(5)6/h7-9,11-12,15,31-33,35H,10,13-14H2,1-6H3
SMILES:	CC(=CCc1ccc(cc1O)c1c(c(=O)c2c(c(CC=C(C)C)c(c(CC=C(C)C)c2o1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489270
PubChem CID:	25147638
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	4130.0	nM	PMID[494444]
NPT2	Others	Unspecified	IC50	=	117330.0	nM	PMID[494444]
NPT2	Others	Unspecified	IC50	=	192090.0	nM	PMID[494444]

☑ 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 NPC269420 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	446
0.1-0.2	1842
0.2-0.3	4583
0.3-0.4	10946
0.4-0.5	6860
0.5-0.6	3708
0.6-0.7	5160
0.7-0.8	4701
0.8-0.85	2474
0.85-0.9	1446
0.9-0.95	473
0.95-1	58

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC142527
0.9793	High Similarity	NPC45934
0.9726	High Similarity	NPC193200
0.966	High Similarity	NPC275575
0.9648	High Similarity	NPC24821
0.9648	High Similarity	NPC212932
0.9648	High Similarity	NPC293053
0.9648	High Similarity	NPC190637
0.9648	High Similarity	NPC9117
0.958	High Similarity	NPC273538
0.958	High Similarity	NPC326500
0.958	High Similarity	NPC216538
0.9577	High Similarity	NPC473042
0.9577	High Similarity	NPC200694
0.953	High Similarity	NPC281137
0.953	High Similarity	NPC282390
0.9514	High Similarity	NPC306488
0.9514	High Similarity	NPC5820
0.9514	High Similarity	NPC124729
0.9514	High Similarity	NPC178343
0.9448	High Similarity	NPC14001
0.9448	High Similarity	NPC166757
0.9392	High Similarity	NPC37684
0.9392	High Similarity	NPC63187
0.9392	High Similarity	NPC157784
0.9384	High Similarity	NPC244407
0.9384	High Similarity	NPC296869
0.9379	High Similarity	NPC220418
0.9375	High Similarity	NPC158874
0.9366	High Similarity	NPC96565
0.9366	High Similarity	NPC55018
0.9366	High Similarity	NPC301217
0.9366	High Similarity	NPC220062
0.9366	High Similarity	NPC216978
0.9366	High Similarity	NPC303633
0.9329	High Similarity	NPC210942
0.9329	High Similarity	NPC169990
0.9324	High Similarity	NPC59162
0.9324	High Similarity	NPC304295
0.9324	High Similarity	NPC205046
0.932	High Similarity	NPC158338
0.932	High Similarity	NPC97029
0.932	High Similarity	NPC288036
0.932	High Similarity	NPC97028
0.932	High Similarity	NPC470461
0.932	High Similarity	NPC65589
0.932	High Similarity	NPC223988
0.932	High Similarity	NPC100985
0.9306	High Similarity	NPC1534
0.9301	High Similarity	NPC159275
0.9301	High Similarity	NPC270883
0.9301	High Similarity	NPC241100
0.9301	High Similarity	NPC172986
0.9301	High Similarity	NPC261227
0.9296	High Similarity	NPC201395
0.9272	High Similarity	NPC237418
0.9272	High Similarity	NPC273843
0.9267	High Similarity	NPC133392
0.9257	High Similarity	NPC3825
0.9257	High Similarity	NPC37348
0.9257	High Similarity	NPC61258
0.9257	High Similarity	NPC472633
0.9257	High Similarity	NPC88804
0.9252	High Similarity	NPC186397
0.9252	High Similarity	NPC27221
0.9252	High Similarity	NPC470460
0.9252	High Similarity	NPC7025
0.9252	High Similarity	NPC37135
0.9252	High Similarity	NPC256672
0.9247	High Similarity	NPC24136
0.9247	High Similarity	NPC196114
0.9247	High Similarity	NPC470458
0.9247	High Similarity	NPC290133
0.9247	High Similarity	NPC187282
0.9241	High Similarity	NPC11700
0.9241	High Similarity	NPC219915
0.9236	High Similarity	NPC147688
0.9236	High Similarity	NPC90582
0.9236	High Similarity	NPC205006
0.9236	High Similarity	NPC110969
0.9236	High Similarity	NPC156590
0.9236	High Similarity	NPC118840
0.9236	High Similarity	NPC262094
0.9236	High Similarity	NPC64908
0.9236	High Similarity	NPC282300
0.9231	High Similarity	NPC143799
0.9231	High Similarity	NPC217186
0.9231	High Similarity	NPC241838
0.9231	High Similarity	NPC78913
0.9231	High Similarity	NPC18260
0.9231	High Similarity	NPC152042
0.9231	High Similarity	NPC53181
0.9205	High Similarity	NPC475799
0.9205	High Similarity	NPC13779
0.9205	High Similarity	NPC3980
0.92	High Similarity	NPC329844
0.9195	High Similarity	NPC258249
0.9195	High Similarity	NPC478148
0.9189	High Similarity	NPC65775
0.9189	High Similarity	NPC474052
0.9189	High Similarity	NPC10027
0.9189	High Similarity	NPC266499
0.9184	High Similarity	NPC123202
0.9184	High Similarity	NPC22005
0.9184	High Similarity	NPC259632
0.9184	High Similarity	NPC7943
0.9178	High Similarity	NPC234629
0.9178	High Similarity	NPC311741
0.9178	High Similarity	NPC224714
0.9172	High Similarity	NPC78803
0.9172	High Similarity	NPC214236
0.9172	High Similarity	NPC59739
0.9172	High Similarity	NPC62840
0.9172	High Similarity	NPC293852
0.9172	High Similarity	NPC226636
0.9172	High Similarity	NPC11561
0.9172	High Similarity	NPC144499
0.9172	High Similarity	NPC217083
0.9172	High Similarity	NPC299080
0.9167	High Similarity	NPC150522
0.9167	High Similarity	NPC305355
0.9167	High Similarity	NPC230285
0.9167	High Similarity	NPC146679
0.9167	High Similarity	NPC281207
0.9167	High Similarity	NPC235239
0.9167	High Similarity	NPC475680
0.9167	High Similarity	NPC103904
0.9167	High Similarity	NPC269652
0.9167	High Similarity	NPC69769
0.9167	High Similarity	NPC59951
0.9167	High Similarity	NPC103342
0.9167	High Similarity	NPC184536
0.9161	High Similarity	NPC276905
0.9155	High Similarity	NPC256042
0.9155	High Similarity	NPC281917
0.9155	High Similarity	NPC187432
0.9155	High Similarity	NPC116775
0.9155	High Similarity	NPC13408
0.9155	High Similarity	NPC216361
0.9133	High Similarity	NPC249570
0.9133	High Similarity	NPC138288
0.9128	High Similarity	NPC120105
0.9128	High Similarity	NPC166753
0.9128	High Similarity	NPC227122
0.9128	High Similarity	NPC50728
0.9128	High Similarity	NPC101957
0.9122	High Similarity	NPC168085
0.9122	High Similarity	NPC145467
0.9116	High Similarity	NPC472629
0.9116	High Similarity	NPC181388
0.9116	High Similarity	NPC99454
0.9116	High Similarity	NPC154217
0.9116	High Similarity	NPC130176
0.911	High Similarity	NPC185276
0.911	High Similarity	NPC106985
0.911	High Similarity	NPC38219
0.911	High Similarity	NPC18585
0.911	High Similarity	NPC166138
0.9103	High Similarity	NPC103362
0.9103	High Similarity	NPC469404
0.9103	High Similarity	NPC136840
0.9103	High Similarity	NPC14871
0.9091	High Similarity	NPC299379
0.9091	High Similarity	NPC228661
0.9079	High Similarity	NPC192587
0.9073	High Similarity	NPC472462
0.9073	High Similarity	NPC100134
0.9073	High Similarity	NPC280530
0.9073	High Similarity	NPC293286
0.9073	High Similarity	NPC95842
0.9073	High Similarity	NPC178964
0.9073	High Similarity	NPC476631
0.9073	High Similarity	NPC209760
0.9073	High Similarity	NPC311579
0.9073	High Similarity	NPC170492
0.9073	High Similarity	NPC236756
0.9073	High Similarity	NPC72370
0.9067	High Similarity	NPC262038
0.9067	High Similarity	NPC154345
0.9067	High Similarity	NPC149526
0.9067	High Similarity	NPC254412
0.9067	High Similarity	NPC278476
0.9067	High Similarity	NPC319910
0.9067	High Similarity	NPC232645
0.9067	High Similarity	NPC72958
0.9067	High Similarity	NPC236769
0.9067	High Similarity	NPC262039
0.9067	High Similarity	NPC474417
0.906	High Similarity	NPC270465
0.906	High Similarity	NPC87125
0.906	High Similarity	NPC159103
0.906	High Similarity	NPC5173
0.906	High Similarity	NPC317492
0.9054	High Similarity	NPC283234
0.9054	High Similarity	NPC97716
0.9054	High Similarity	NPC296998
0.9054	High Similarity	NPC237635
0.9054	High Similarity	NPC24673
0.9054	High Similarity	NPC308200
0.9054	High Similarity	NPC201731

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 NPC269420 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	980
0.2-0.3	1720
0.3-0.4	2697
0.4-0.5	1805
0.5-0.6	1003
0.6-0.7	363
0.7-0.8	122
0.8-0.85	40
0.85-0.9	12
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.958	High Similarity	NPD4378	Clinical (unspecified phase)
0.8986	High Similarity	NPD1512	Approved
0.8947	High Similarity	NPD2393	Clinical (unspecified phase)
0.8919	High Similarity	NPD7410	Clinical (unspecified phase)
0.8851	High Similarity	NPD1511	Approved
0.8774	High Similarity	NPD7075	Discontinued
0.8701	High Similarity	NPD2801	Approved
0.8701	High Similarity	NPD7096	Clinical (unspecified phase)
0.8701	High Similarity	NPD7819	Suspended
0.8699	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1550	Clinical (unspecified phase)
0.869	High Similarity	NPD1510	Phase 2
0.8681	High Similarity	NPD1607	Approved
0.8645	High Similarity	NPD8443	Clinical (unspecified phase)
0.8639	High Similarity	NPD1549	Phase 2
0.8636	High Similarity	NPD1934	Approved
0.863	High Similarity	NPD2796	Approved
0.8627	High Similarity	NPD4380	Phase 2
0.8608	High Similarity	NPD6959	Discontinued
0.8542	High Similarity	NPD1240	Approved
0.8526	High Similarity	NPD3817	Phase 2
0.8519	High Similarity	NPD7804	Clinical (unspecified phase)
0.8516	High Similarity	NPD6801	Discontinued
0.8471	Intermediate Similarity	NPD3882	Suspended
0.8452	Intermediate Similarity	NPD7411	Suspended
0.8447	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD6166	Phase 2
0.8395	Intermediate Similarity	NPD7473	Discontinued
0.8387	Intermediate Similarity	NPD6599	Discontinued
0.8355	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD2800	Approved
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8302	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD2534	Approved
0.8301	Intermediate Similarity	NPD2532	Approved
0.8301	Intermediate Similarity	NPD2533	Approved
0.8278	Intermediate Similarity	NPD3750	Approved
0.8267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6099	Approved
0.8255	Intermediate Similarity	NPD2935	Discontinued
0.8255	Intermediate Similarity	NPD6100	Approved
0.8253	Intermediate Similarity	NPD7251	Discontinued
0.8239	Intermediate Similarity	NPD7768	Phase 2
0.8205	Intermediate Similarity	NPD3226	Approved
0.8204	Intermediate Similarity	NPD7808	Phase 3
0.8193	Intermediate Similarity	NPD6797	Phase 2
0.8188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7054	Approved
0.8144	Intermediate Similarity	NPD6559	Discontinued
0.8133	Intermediate Similarity	NPD1551	Phase 2
0.8133	Intermediate Similarity	NPD7472	Approved
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8121	Intermediate Similarity	NPD3818	Discontinued
0.8117	Intermediate Similarity	NPD7390	Discontinued
0.811	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1243	Approved
0.8086	Intermediate Similarity	NPD5494	Approved
0.8079	Intermediate Similarity	NPD2346	Discontinued
0.8063	Intermediate Similarity	NPD5402	Approved
0.8054	Intermediate Similarity	NPD6651	Approved
0.8039	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2313	Discontinued
0.8027	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5844	Phase 1
0.7963	Intermediate Similarity	NPD3749	Approved
0.7962	Intermediate Similarity	NPD920	Approved
0.7962	Intermediate Similarity	NPD5403	Approved
0.7947	Intermediate Similarity	NPD3748	Approved
0.7947	Intermediate Similarity	NPD2799	Discontinued
0.7927	Intermediate Similarity	NPD1247	Approved
0.7914	Intermediate Similarity	NPD919	Approved
0.7901	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7286	Phase 2
0.7843	Intermediate Similarity	NPD2344	Approved
0.7838	Intermediate Similarity	NPD4625	Phase 3
0.7834	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD5401	Approved
0.7821	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD943	Approved
0.7765	Intermediate Similarity	NPD5953	Discontinued
0.7727	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3926	Phase 2
0.7712	Intermediate Similarity	NPD4308	Phase 3
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7687	Intermediate Similarity	NPD1203	Approved
0.7667	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3268	Approved
0.7665	Intermediate Similarity	NPD5710	Approved
0.7665	Intermediate Similarity	NPD5711	Approved
0.7661	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2309	Approved
0.7635	Intermediate Similarity	NPD2798	Approved
0.7568	Intermediate Similarity	NPD2797	Approved
0.7561	Intermediate Similarity	NPD1465	Phase 2
0.7556	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4749	Approved
0.755	Intermediate Similarity	NPD411	Approved
0.7548	Intermediate Similarity	NPD5406	Approved
0.7548	Intermediate Similarity	NPD5405	Approved
0.7548	Intermediate Similarity	NPD5408	Approved
0.7548	Intermediate Similarity	NPD5404	Approved
0.7542	Intermediate Similarity	NPD4360	Phase 2
0.7542	Intermediate Similarity	NPD4363	Phase 3
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7534	Intermediate Similarity	NPD1201	Approved
0.7533	Intermediate Similarity	NPD4908	Phase 1
0.7533	Intermediate Similarity	NPD6832	Phase 2
0.7533	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7483	Intermediate Similarity	NPD9717	Approved
0.7483	Intermediate Similarity	NPD1608	Approved
0.7467	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7229	Phase 3
0.7451	Intermediate Similarity	NPD4307	Phase 2
0.745	Intermediate Similarity	NPD1470	Approved
0.7439	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7458	Discontinued
0.7415	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1610	Phase 2
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4361	Phase 2
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD447	Suspended
0.7383	Intermediate Similarity	NPD3225	Approved
0.7365	Intermediate Similarity	NPD3972	Approved
0.7338	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1613	Approved
0.7337	Intermediate Similarity	NPD6782	Approved
0.7337	Intermediate Similarity	NPD6781	Approved
0.7337	Intermediate Similarity	NPD6778	Approved
0.7337	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6777	Approved
0.7337	Intermediate Similarity	NPD6779	Approved
0.7337	Intermediate Similarity	NPD6780	Approved
0.7337	Intermediate Similarity	NPD6776	Approved
0.7333	Intermediate Similarity	NPD3266	Approved
0.7333	Intermediate Similarity	NPD3267	Approved
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7435	Discontinued
0.7312	Intermediate Similarity	NPD7698	Approved
0.7312	Intermediate Similarity	NPD7696	Phase 3
0.7312	Intermediate Similarity	NPD7697	Approved
0.7305	Intermediate Similarity	NPD4288	Approved
0.7303	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7296	Intermediate Similarity	NPD2654	Approved
0.729	Intermediate Similarity	NPD230	Phase 1
0.729	Intermediate Similarity	NPD5124	Phase 1
0.729	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6844	Discontinued
0.7283	Intermediate Similarity	NPD3751	Discontinued
0.7279	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.725	Intermediate Similarity	NPD7003	Approved
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1651	Approved
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7208	Intermediate Similarity	NPD1296	Phase 2
0.72	Intermediate Similarity	NPD1729	Discontinued
0.7196	Intermediate Similarity	NPD7584	Approved
0.7184	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7177	Discontinued
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7168	Intermediate Similarity	NPD2403	Approved
0.7168	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD1283	Approved
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD7095	Approved
0.7134	Intermediate Similarity	NPD5049	Phase 3
0.7124	Intermediate Similarity	NPD2861	Phase 2
0.712	Intermediate Similarity	NPD8151	Discontinued
0.7105	Intermediate Similarity	NPD1164	Approved
0.7101	Intermediate Similarity	NPD2296	Approved
0.7099	Intermediate Similarity	NPD2354	Approved
0.7097	Intermediate Similarity	NPD3764	Approved
0.7093	Intermediate Similarity	NPD7199	Phase 2
0.7086	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD37	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