NPASS Compound

Structure

CID192587 OpenBabel06191715582D 41 45 0 0 1 0 0 0 0 0999 V2000 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1603 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6603 -1.0000 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 -6.9282 -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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 1.7321 -3.0000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 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 2.5981 -2.5000 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 -7.7942 1.5000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 1 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 0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 20 1 0 0 0 0 2 21 2 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 6 17 1 0 0 0 0 6 18 1 0 0 0 0 7 14 1 0 0 0 0 7 20 2 0 0 0 0 8 15 1 0 0 0 0 8 20 1 0 0 0 0 9 16 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 22 2 0 0 0 0 11 13 2 0 0 0 0 11 22 1 0 0 0 0 12 23 2 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 34 1 0 0 0 0 18 35 1 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 21 25 1 0 0 0 0 22 33 1 0 0 0 0 23 36 1 0 0 0 0 24 26 1 0 0 0 0 24 30 2 0 0 0 0 25 35 1 6 0 0 0 26 37 1 0 0 0 0 27 29 2 0 0 0 0 27 41 1 0 0 0 0 28 34 1 0 0 0 0 28 35 1 6 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 30 38 1 0 0 0 0 31 32 1 0 0 0 0 31 39 2 0 0 0 0 32 33 2 0 0 0 0 32 40 1 0 0 0 0 33 41 1 0 0 0 0 35 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.3
Volume:	597.51
LogP:	8.08
LogD:	4.28
LogS:	-2.456
# Rotatable Bonds:	6
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	4.269
Fsp3:	0.457
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.849
MDCK Permeability:	1.6058102119131945e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.914

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	97.33209228515625%
Volume Distribution (VD):	0.818
Pgp-substrate:	1.4401925802230835%

ADMET: Metabolism

CYP1A2-inhibitor:	0.258
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.648
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.528
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.487
CYP2D6-substrate:	0.677
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	5.108
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.807
AMES Toxicity:	0.208
Rat Oral Acute Toxicity:	0.564
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.908
Carcinogencity:	0.442
Eye Corrosion:	0.003
Eye Irritation:	0.852
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC192587

Natural Product ID:	NPC192587
*Common Name:**	Denticulaflavonol
IUPAC Name:	6-[(E)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enyl]-3,5,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:	Denticulaflavonol
Standard InCHIKey:	VLQNALFJVBGYOK-ACVGDBMHSA-N
Standard InCHI:	InChI=1S/C35H42O6/c1-20(8-15-25-21(2)9-16-28-34(3,4)17-6-18-35(25,28)5)7-14-24-26(37)19-27-29(30(24)38)31(39)32(40)33(41-27)22-10-12-23(36)13-11-22/h7,10-13,19,25,28,36-38,40H,2,6,8-9,14-18H2,1,3-5H3/b20-7+/t25-,28-,35+/m0/s1
SMILES:	C/C(=CCc1c(cc2c(c1O)c(=O)c(c(c1ccc(cc1)O)o2)O)O)/CC[C@H]1C(=C)CC[C@H]2C(C)(C)CCC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1240942
PubChem CID:	21673119
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003503] 6-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
NPO2823	Scopolia sinensis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2823	Scopolia sinensis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2823	Scopolia sinensis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9773	Sideritis raeseri	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[478618]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[478618]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	100000.0	nM	PMID[478618]

☑ 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 NPC192587 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	477
0.1-0.2	1745
0.2-0.3	3529
0.3-0.4	8852
0.4-0.5	9690
0.5-0.6	4715
0.6-0.7	5801
0.7-0.8	5006
0.8-0.85	2351
0.85-0.9	495
0.9-0.95	35
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC326500
0.9257	High Similarity	NPC9117
0.9257	High Similarity	NPC212932
0.9257	High Similarity	NPC190637
0.9257	High Similarity	NPC24821
0.9257	High Similarity	NPC11700
0.9257	High Similarity	NPC293053
0.9236	High Similarity	NPC469395
0.9221	High Similarity	NPC56049
0.9221	High Similarity	NPC54830
0.9211	High Similarity	NPC305965
0.92	High Similarity	NPC166757
0.92	High Similarity	NPC14001
0.9195	High Similarity	NPC216538
0.9195	High Similarity	NPC273538
0.9189	High Similarity	NPC200694
0.9189	High Similarity	NPC473042
0.9156	High Similarity	NPC215203
0.9156	High Similarity	NPC186227
0.9156	High Similarity	NPC52611
0.9156	High Similarity	NPC159707
0.9156	High Similarity	NPC150908
0.9156	High Similarity	NPC158027
0.9156	High Similarity	NPC14606
0.9156	High Similarity	NPC100049
0.9156	High Similarity	NPC205026
0.9156	High Similarity	NPC265624
0.9156	High Similarity	NPC121649
0.9156	High Similarity	NPC248739
0.9139	High Similarity	NPC244407
0.9139	High Similarity	NPC296869
0.9133	High Similarity	NPC5820
0.9133	High Similarity	NPC124729
0.9133	High Similarity	NPC220418
0.9133	High Similarity	NPC178343
0.9133	High Similarity	NPC306488
0.9108	High Similarity	NPC103816
0.9108	High Similarity	NPC61382
0.9103	High Similarity	NPC46736
0.9103	High Similarity	NPC295090
0.9091	High Similarity	NPC71061
0.9091	High Similarity	NPC290830
0.9091	High Similarity	NPC121568
0.9091	High Similarity	NPC194593
0.9091	High Similarity	NPC303485
0.9091	High Similarity	NPC72425
0.9085	High Similarity	NPC222713
0.9085	High Similarity	NPC178484
0.9085	High Similarity	NPC111112
0.9085	High Similarity	NPC138299
0.9085	High Similarity	NPC67322
0.9079	High Similarity	NPC471114
0.9079	High Similarity	NPC470461
0.9079	High Similarity	NPC269420
0.9073	High Similarity	NPC261271
0.9073	High Similarity	NPC475348
0.9051	High Similarity	NPC206605
0.9045	High Similarity	NPC297212
0.9045	High Similarity	NPC121647
0.9045	High Similarity	NPC476280
0.9038	High Similarity	NPC257166
0.9038	High Similarity	NPC1796
0.9032	High Similarity	NPC275575
0.9026	High Similarity	NPC142527
0.9026	High Similarity	NPC45934
0.902	High Similarity	NPC471115
0.902	High Similarity	NPC321896
0.902	High Similarity	NPC188403
0.902	High Similarity	NPC476185
0.902	High Similarity	NPC29777
0.9013	High Similarity	NPC145467
0.9013	High Similarity	NPC470460
0.9013	High Similarity	NPC152233
0.9	High Similarity	NPC158874
0.9	High Similarity	NPC219915
0.8994	High Similarity	NPC12461
0.8993	High Similarity	NPC282300
0.8993	High Similarity	NPC14871
0.8986	High Similarity	NPC301217
0.8986	High Similarity	NPC216978
0.8986	High Similarity	NPC55018
0.8986	High Similarity	NPC303633
0.8986	High Similarity	NPC96565
0.8986	High Similarity	NPC220062
0.8981	High Similarity	NPC197856
0.8981	High Similarity	NPC51247
0.8981	High Similarity	NPC55443
0.8981	High Similarity	NPC90497
0.8981	High Similarity	NPC18699
0.8981	High Similarity	NPC15815
0.8974	High Similarity	NPC470352
0.8974	High Similarity	NPC3980
0.8974	High Similarity	NPC32867
0.8968	High Similarity	NPC324447
0.8954	High Similarity	NPC291746
0.8954	High Similarity	NPC288840
0.8947	High Similarity	NPC10990
0.8947	High Similarity	NPC308200
0.8947	High Similarity	NPC300988
0.8944	High Similarity	NPC476306
0.894	High Similarity	NPC472446
0.894	High Similarity	NPC271288
0.894	High Similarity	NPC117716
0.894	High Similarity	NPC472447
0.894	High Similarity	NPC470673
0.894	High Similarity	NPC470674
0.8933	High Similarity	NPC299080
0.8933	High Similarity	NPC293852
0.8933	High Similarity	NPC78803
0.8933	High Similarity	NPC204469
0.8933	High Similarity	NPC217083
0.8933	High Similarity	NPC214236
0.8933	High Similarity	NPC62840
0.8933	High Similarity	NPC59739
0.8931	High Similarity	NPC473012
0.8931	High Similarity	NPC475106
0.8926	High Similarity	NPC270883
0.8926	High Similarity	NPC241100
0.8926	High Similarity	NPC261227
0.8926	High Similarity	NPC159275
0.8926	High Similarity	NPC172986
0.8924	High Similarity	NPC98023
0.8924	High Similarity	NPC42965
0.8924	High Similarity	NPC312993
0.8924	High Similarity	NPC226462
0.8924	High Similarity	NPC195136
0.8919	High Similarity	NPC201395
0.8917	High Similarity	NPC273843
0.8917	High Similarity	NPC475184
0.891	High Similarity	NPC254351
0.891	High Similarity	NPC79375
0.891	High Similarity	NPC471116
0.891	High Similarity	NPC66441
0.891	High Similarity	NPC182555
0.891	High Similarity	NPC37253
0.891	High Similarity	NPC476169
0.8903	High Similarity	NPC470353
0.8896	High Similarity	NPC61258
0.8889	High Similarity	NPC286074
0.8889	High Similarity	NPC54903
0.8889	High Similarity	NPC39195
0.8882	High Similarity	NPC120857
0.8882	High Similarity	NPC477955
0.8882	High Similarity	NPC85047
0.8882	High Similarity	NPC17274
0.8882	High Similarity	NPC470458
0.8882	High Similarity	NPC329678
0.8882	High Similarity	NPC154217
0.8882	High Similarity	NPC181388
0.8882	High Similarity	NPC476088
0.8882	High Similarity	NPC474161
0.8875	High Similarity	NPC473009
0.8875	High Similarity	NPC476295
0.8875	High Similarity	NPC290160
0.8874	High Similarity	NPC38219
0.8874	High Similarity	NPC473813
0.8874	High Similarity	NPC473812
0.8868	High Similarity	NPC312273
0.8868	High Similarity	NPC301256
0.8868	High Similarity	NPC189552
0.8868	High Similarity	NPC18380
0.8868	High Similarity	NPC273467
0.8867	High Similarity	NPC110969
0.8867	High Similarity	NPC205006
0.8867	High Similarity	NPC156590
0.8867	High Similarity	NPC118840
0.8867	High Similarity	NPC147688
0.8867	High Similarity	NPC64908
0.8867	High Similarity	NPC262094
0.8867	High Similarity	NPC90582
0.8861	High Similarity	NPC105584
0.8861	High Similarity	NPC472617
0.8861	High Similarity	NPC177650
0.8859	High Similarity	NPC53181
0.8859	High Similarity	NPC143799
0.8859	High Similarity	NPC152042
0.8859	High Similarity	NPC78913
0.8859	High Similarity	NPC18260
0.8859	High Similarity	NPC241838
0.8859	High Similarity	NPC217186
0.8854	High Similarity	NPC475799
0.8854	High Similarity	NPC13779
0.8854	High Similarity	NPC470354
0.8854	High Similarity	NPC69531
0.8846	High Similarity	NPC209760
0.8846	High Similarity	NPC236756
0.8846	High Similarity	NPC193200
0.8846	High Similarity	NPC311579
0.8846	High Similarity	NPC178964
0.8846	High Similarity	NPC329844
0.8846	High Similarity	NPC280530
0.8846	High Similarity	NPC100134
0.8846	High Similarity	NPC95842
0.8839	High Similarity	NPC476552
0.8839	High Similarity	NPC81474
0.8839	High Similarity	NPC476551
0.8839	High Similarity	NPC476553
0.8831	High Similarity	NPC469932
0.8831	High Similarity	NPC3642
0.8831	High Similarity	NPC473016

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 NPC192587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	947
0.2-0.3	1697
0.3-0.4	2727
0.4-0.5	1993
0.5-0.6	909
0.6-0.7	306
0.7-0.8	124
0.8-0.85	29
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9195	High Similarity	NPD4378	Clinical (unspecified phase)
0.891	High Similarity	NPD8443	Clinical (unspecified phase)
0.8816	High Similarity	NPD7410	Clinical (unspecified phase)
0.8545	High Similarity	NPD7804	Clinical (unspecified phase)
0.8519	High Similarity	NPD6959	Discontinued
0.85	High Similarity	NPD7768	Phase 2
0.8491	Intermediate Similarity	NPD7819	Suspended
0.8476	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7075	Discontinued
0.8418	Intermediate Similarity	NPD4380	Phase 2
0.8397	Intermediate Similarity	NPD1512	Approved
0.8375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD2800	Approved
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8355	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8312	Intermediate Similarity	NPD3750	Approved
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8289	Intermediate Similarity	NPD2796	Approved
0.8269	Intermediate Similarity	NPD1511	Approved
0.8253	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6166	Phase 2
0.8253	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1240	Approved
0.8199	Intermediate Similarity	NPD6801	Discontinued
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8148	Intermediate Similarity	NPD2801	Approved
0.811	Intermediate Similarity	NPD3749	Approved
0.811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7473	Discontinued
0.8092	Intermediate Similarity	NPD6651	Approved
0.8092	Intermediate Similarity	NPD1607	Approved
0.8086	Intermediate Similarity	NPD1934	Approved
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD6100	Approved
0.8052	Intermediate Similarity	NPD6099	Approved
0.8038	Intermediate Similarity	NPD7390	Discontinued
0.8038	Intermediate Similarity	NPD6799	Approved
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.7988	Intermediate Similarity	NPD3817	Phase 2
0.7987	Intermediate Similarity	NPD3748	Approved
0.7965	Intermediate Similarity	NPD7251	Discontinued
0.7939	Intermediate Similarity	NPD3882	Suspended
0.7917	Intermediate Similarity	NPD6232	Discontinued
0.7907	Intermediate Similarity	NPD6797	Phase 2
0.7904	Intermediate Similarity	NPD5494	Approved
0.7898	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7054	Approved
0.7871	Intermediate Similarity	NPD2799	Discontinued
0.7849	Intermediate Similarity	NPD7074	Phase 3
0.7849	Intermediate Similarity	NPD7472	Approved
0.7829	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7458	Discontinued
0.7791	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD1243	Approved
0.7778	Intermediate Similarity	NPD5403	Approved
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7756	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7003	Approved
0.7736	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2313	Discontinued
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7701	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4908	Phase 1
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7669	Intermediate Similarity	NPD920	Approved
0.7665	Intermediate Similarity	NPD5402	Approved
0.7658	Intermediate Similarity	NPD2344	Approved
0.7654	Intermediate Similarity	NPD5401	Approved
0.763	Intermediate Similarity	NPD3818	Discontinued
0.7619	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3268	Approved
0.7596	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7586	Intermediate Similarity	NPD7286	Phase 2
0.7582	Intermediate Similarity	NPD4363	Phase 3
0.7582	Intermediate Similarity	NPD4360	Phase 2
0.7571	Intermediate Similarity	NPD8313	Approved
0.7571	Intermediate Similarity	NPD8312	Approved
0.7566	Intermediate Similarity	NPD2798	Approved
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD2797	Approved
0.7469	Intermediate Similarity	NPD2309	Approved
0.7458	Intermediate Similarity	NPD6559	Discontinued
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7442	Intermediate Similarity	NPD1247	Approved
0.7439	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD919	Approved
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7229	Phase 3
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7396	Intermediate Similarity	NPD1465	Phase 2
0.7386	Intermediate Similarity	NPD1203	Approved
0.7375	Intermediate Similarity	NPD5406	Approved
0.7375	Intermediate Similarity	NPD5405	Approved
0.7375	Intermediate Similarity	NPD5408	Approved
0.7375	Intermediate Similarity	NPD5404	Approved
0.7363	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3926	Phase 2
0.7354	Intermediate Similarity	NPD7698	Approved
0.7354	Intermediate Similarity	NPD7696	Phase 3
0.7354	Intermediate Similarity	NPD7697	Approved
0.7353	Intermediate Similarity	NPD4288	Approved
0.7351	Intermediate Similarity	NPD4361	Phase 2
0.7351	Intermediate Similarity	NPD1610	Phase 2
0.7351	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.733	Intermediate Similarity	NPD3751	Discontinued
0.7316	Intermediate Similarity	NPD7870	Phase 2
0.7316	Intermediate Similarity	NPD7871	Phase 2
0.7308	Intermediate Similarity	NPD4625	Phase 3
0.7294	Intermediate Similarity	NPD5760	Phase 2
0.7294	Intermediate Similarity	NPD8455	Phase 2
0.7294	Intermediate Similarity	NPD5761	Phase 2
0.7289	Intermediate Similarity	NPD6273	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD3267	Approved
0.7273	Intermediate Similarity	NPD3266	Approved
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7262	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7237	Intermediate Similarity	NPD1201	Approved
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7233	Intermediate Similarity	NPD5124	Phase 1
0.7233	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1471	Phase 3
0.7208	Intermediate Similarity	NPD3225	Approved
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7205	Intermediate Similarity	NPD4308	Phase 3
0.7205	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7701	Phase 2
0.72	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD1548	Phase 1
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD3972	Approved
0.719	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD7801	Approved
0.7174	Intermediate Similarity	NPD4287	Approved
0.7165	Intermediate Similarity	NPD8151	Discontinued
0.7161	Intermediate Similarity	NPD1470	Approved
0.7159	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3764	Approved
0.7128	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2403	Approved
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8032	Phase 2
0.7105	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8166	Discontinued
0.709	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7699	Phase 2
0.7089	Intermediate Similarity	NPD7095	Approved
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7062	Intermediate Similarity	NPD7584	Approved
0.7047	Intermediate Similarity	NPD8319	Approved
0.7047	Intermediate Similarity	NPD8320	Phase 1
0.7045	Intermediate Similarity	NPD7199	Phase 2
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7044	Intermediate Similarity	NPD6798	Discontinued
0.7041	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7177	Discontinued
0.7032	Intermediate Similarity	NPD4749	Approved
0.703	Intermediate Similarity	NPD2654	Approved
0.7025	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7447	Phase 1
0.7024	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD6535	Approved
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7783	Phase 2
0.6993	Remote Similarity	NPD17	Approved
0.6978	Remote Similarity	NPD6104	Discontinued
0.6962	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1729	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