NPASS Compound

Structure

CID145659 OpenBabel06191715502D 34 39 0 0 1 0 0 0 0 0999 V2000 -2.7852 2.7231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5014 3.7469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9273 -0.0540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9273 1.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3762 3.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0925 4.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8753 -0.0540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8753 1.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0501 -0.4121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 1.7150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0271 0.2539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5437 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8477 2.8644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4533 0.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0299 4.3468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3493 0.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7309 -0.3611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5437 1.2410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6656 0.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9016 1.2410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6425 0.8180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6656 1.3820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5572 0.7670 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9617 0.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9016 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5339 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6210 5.0880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2974 0.7670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2649 -1.1444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3647 1.7150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0538 1.6721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 -1.1291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 13 2 0 0 0 0 2 6 2 0 0 0 0 2 13 1 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 9 19 1 0 0 0 0 10 18 2 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 21 2 0 0 0 0 12 18 1 0 0 0 0 12 22 2 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 21 25 1 0 0 0 0 21 33 1 0 0 0 0 22 26 1 0 0 0 0 22 34 1 0 0 0 0 23 13 1 1 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 26 28 1 0 0 0 0 27 20 1 6 0 0 0 28 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.14
Volume:	462.609
LogP:	4.669
LogD:	3.334
LogS:	-4.202
# Rotatable Bonds:	2
TPSA:	121.38
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	4.55
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.79
MDCK Permeability:	5.975173280603485e-06
Pgp-inhibitor:	0.537
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.934
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	96.90709686279297%
Volume Distribution (VD):	0.561
Pgp-substrate:	3.5597498416900635%

ADMET: Metabolism

CYP1A2-inhibitor:	0.272
CYP1A2-substrate:	0.878
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.889
CYP2C9-substrate:	0.994
CYP2D6-inhibitor:	0.632
CYP2D6-substrate:	0.739
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.439

ADMET: Excretion

Clearance (CL):	10.744
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.183
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.284
AMES Toxicity:	0.329
Rat Oral Acute Toxicity:	0.686
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.943
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.888
Respiratory Toxicity:	0.143

Download Data

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

Natural Product: NPC145659

Natural Product ID:	NPC145659
*Common Name:**	LJHNYAXAPRDORG-WGPYEGLQSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Ampelopsin F
Standard InCHIKey:	LJHNYAXAPRDORG-WGPYEGLQSA-N
Standard InCHI:	InChI=1S/C28H22O6/c29-15-5-1-13(2-6-15)23-25-19(9-17(31)11-21(25)33)28-24(14-3-7-16(30)8-4-14)27(23)20-10-18(32)12-22(34)26(20)28/h1-12,23-24,27-34H/t23-,24?,27+,28-/m1/s1
SMILES:	Oc1ccc(cc1)C1[C@H]2c3cc(O)cc(c3[C@H]([C@@H]1c1c2c(O)cc(c1)O)c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL605761
PubChem CID:	46230189
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209460]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28914	Caragana sinica	Species	Fabaceae	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	2
MIC	2
Others	11

Activity Type	# Activity
NON-MOLECULAR	1
Organism	13
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	IZ	<	11.0	mm	PMID[513954]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	IZ	<	15.0	mm	PMID[513954]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	IZ	=	20.0	mm	PMID[513954]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	IZ	<	11.0	mm	PMID[513954]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	IZ	<	15.0	mm	PMID[513954]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	100.0	ug.mL-1	PMID[513954]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	=	200.0	ug ml-1	PMID[513954]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MIC	>	400.0	ug.mL-1	PMID[513954]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MBC	>	400.0	ug ml-1	PMID[513954]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	=	100.0	ug ml-1	PMID[513954]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	Activity	>	200.0	ug ml-1	PMID[513954]
NPT1	Others	Radical scavenging activity		IC50	>	200000.0	nM	PMID[513955]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[513955]

☑ 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 NPC145659 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	481
0.1-0.2	1951
0.2-0.3	4629
0.3-0.4	12433
0.4-0.5	6727
0.5-0.6	7529
0.6-0.7	7198
0.7-0.8	1539
0.8-0.85	161
0.85-0.9	39
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC9292
0.9664	High Similarity	NPC120172
0.9504	High Similarity	NPC97578
0.9291	High Similarity	NPC473665
0.9091	High Similarity	NPC69006
0.8984	High Similarity	NPC238168
0.8984	High Similarity	NPC237424
0.876	High Similarity	NPC261973
0.8678	High Similarity	NPC246760
0.8678	High Similarity	NPC84999
0.8615	High Similarity	NPC472369
0.8595	High Similarity	NPC107240
0.8571	High Similarity	NPC258780
0.8571	High Similarity	NPC37410
0.8538	High Similarity	NPC471519
0.8538	High Similarity	NPC471518
0.8537	High Similarity	NPC470760
0.8537	High Similarity	NPC299180
0.8519	High Similarity	NPC20210
0.8507	High Similarity	NPC472648
0.8507	High Similarity	NPC133463
0.8507	High Similarity	NPC191462
0.8507	High Similarity	NPC472649
0.8507	High Similarity	NPC472647
0.8507	High Similarity	NPC170328
0.8507	High Similarity	NPC206525
0.8473	Intermediate Similarity	NPC254000
0.8455	Intermediate Similarity	NPC115808
0.8444	Intermediate Similarity	NPC71465
0.8444	Intermediate Similarity	NPC472646
0.843	Intermediate Similarity	NPC43525
0.8409	Intermediate Similarity	NPC282508
0.8409	Intermediate Similarity	NPC473309
0.838	Intermediate Similarity	NPC218801
0.8361	Intermediate Similarity	NPC322239
0.8361	Intermediate Similarity	NPC321589
0.8361	Intermediate Similarity	NPC117846
0.8347	Intermediate Similarity	NPC4493
0.8347	Intermediate Similarity	NPC476632
0.8347	Intermediate Similarity	NPC165770
0.8347	Intermediate Similarity	NPC224527
0.8347	Intermediate Similarity	NPC225679
0.8333	Intermediate Similarity	NPC277784
0.8333	Intermediate Similarity	NPC202647
0.8321	Intermediate Similarity	NPC273623
0.832	Intermediate Similarity	NPC206
0.831	Intermediate Similarity	NPC177172
0.831	Intermediate Similarity	NPC107862
0.831	Intermediate Similarity	NPC180605
0.831	Intermediate Similarity	NPC122980
0.831	Intermediate Similarity	NPC148516
0.8296	Intermediate Similarity	NPC11727
0.8296	Intermediate Similarity	NPC472370
0.8296	Intermediate Similarity	NPC15109
0.8295	Intermediate Similarity	NPC224342
0.8293	Intermediate Similarity	NPC249270
0.8281	Intermediate Similarity	NPC71094
0.8279	Intermediate Similarity	NPC166995
0.8271	Intermediate Similarity	NPC471517
0.8264	Intermediate Similarity	NPC473018
0.8264	Intermediate Similarity	NPC120633
0.825	Intermediate Similarity	NPC11554
0.8235	Intermediate Similarity	NPC248904
0.8231	Intermediate Similarity	NPC113495
0.8214	Intermediate Similarity	NPC313047
0.8214	Intermediate Similarity	NPC295712
0.8214	Intermediate Similarity	NPC451542
0.8214	Intermediate Similarity	NPC474203
0.8211	Intermediate Similarity	NPC715
0.8211	Intermediate Similarity	NPC263753
0.8211	Intermediate Similarity	NPC23804
0.8203	Intermediate Similarity	NPC237667
0.8197	Intermediate Similarity	NPC322753
0.8197	Intermediate Similarity	NPC95716
0.8194	Intermediate Similarity	NPC157081
0.8194	Intermediate Similarity	NPC105073
0.8194	Intermediate Similarity	NPC233886
0.8194	Intermediate Similarity	NPC224528
0.8182	Intermediate Similarity	NPC19808
0.8182	Intermediate Similarity	NPC33728
0.8168	Intermediate Similarity	NPC170485
0.8162	Intermediate Similarity	NPC125579
0.8151	Intermediate Similarity	NPC474839
0.8151	Intermediate Similarity	NPC292452
0.8134	Intermediate Similarity	NPC8899
0.813	Intermediate Similarity	NPC46940
0.8125	Intermediate Similarity	NPC328504
0.8115	Intermediate Similarity	NPC224870
0.811	Intermediate Similarity	NPC126002
0.811	Intermediate Similarity	NPC217174
0.8102	Intermediate Similarity	NPC141717
0.8099	Intermediate Similarity	NPC61885
0.8099	Intermediate Similarity	NPC63698
0.8099	Intermediate Similarity	NPC174981
0.8085	Intermediate Similarity	NPC293545
0.8085	Intermediate Similarity	NPC174905
0.8083	Intermediate Similarity	NPC470700
0.8083	Intermediate Similarity	NPC39664
0.8083	Intermediate Similarity	NPC118286
0.8083	Intermediate Similarity	NPC39097
0.8083	Intermediate Similarity	NPC109691
0.8083	Intermediate Similarity	NPC302681
0.808	Intermediate Similarity	NPC469719
0.8077	Intermediate Similarity	NPC53567
0.8074	Intermediate Similarity	NPC469611
0.8067	Intermediate Similarity	NPC102216
0.8067	Intermediate Similarity	NPC30506
0.8067	Intermediate Similarity	NPC119860
0.8067	Intermediate Similarity	NPC241891
0.8065	Intermediate Similarity	NPC261343
0.8062	Intermediate Similarity	NPC39029
0.8062	Intermediate Similarity	NPC475166
0.8058	Intermediate Similarity	NPC174787
0.8058	Intermediate Similarity	NPC213607
0.8058	Intermediate Similarity	NPC182509
0.8049	Intermediate Similarity	NPC151537
0.8045	Intermediate Similarity	NPC215300
0.8043	Intermediate Similarity	NPC476393
0.8042	Intermediate Similarity	NPC112819
0.8042	Intermediate Similarity	NPC6702
0.8042	Intermediate Similarity	NPC111134
0.8042	Intermediate Similarity	NPC133209
0.8033	Intermediate Similarity	NPC314187
0.8033	Intermediate Similarity	NPC186385
0.8033	Intermediate Similarity	NPC299568
0.8031	Intermediate Similarity	NPC144343
0.8028	Intermediate Similarity	NPC149633
0.8017	Intermediate Similarity	NPC54844
0.8015	Intermediate Similarity	NPC469610
0.8015	Intermediate Similarity	NPC228503
0.8015	Intermediate Similarity	NPC138248
0.8	Intermediate Similarity	NPC195922
0.8	Intermediate Similarity	NPC134829
0.8	Intermediate Similarity	NPC246056
0.7984	Intermediate Similarity	NPC473521
0.7984	Intermediate Similarity	NPC24125
0.7972	Intermediate Similarity	NPC176804
0.7972	Intermediate Similarity	NPC71686
0.7972	Intermediate Similarity	NPC14468
0.797	Intermediate Similarity	NPC53781
0.7969	Intermediate Similarity	NPC93071
0.7969	Intermediate Similarity	NPC151197
0.7969	Intermediate Similarity	NPC191866
0.7967	Intermediate Similarity	NPC475018
0.7967	Intermediate Similarity	NPC141782
0.7955	Intermediate Similarity	NPC278955
0.7955	Intermediate Similarity	NPC105718
0.7955	Intermediate Similarity	NPC105031
0.7953	Intermediate Similarity	NPC172219
0.7953	Intermediate Similarity	NPC304510
0.7953	Intermediate Similarity	NPC277588
0.7943	Intermediate Similarity	NPC106519
0.7943	Intermediate Similarity	NPC91019
0.7943	Intermediate Similarity	NPC183709
0.7934	Intermediate Similarity	NPC271274
0.7917	Intermediate Similarity	NPC327811
0.7917	Intermediate Similarity	NPC242774
0.7917	Intermediate Similarity	NPC237546
0.7917	Intermediate Similarity	NPC224921
0.7917	Intermediate Similarity	NPC254965
0.7917	Intermediate Similarity	NPC231712
0.7917	Intermediate Similarity	NPC262297
0.791	Intermediate Similarity	NPC38017
0.7907	Intermediate Similarity	NPC223451
0.7907	Intermediate Similarity	NPC68339
0.7907	Intermediate Similarity	NPC472071
0.7907	Intermediate Similarity	NPC99734
0.7903	Intermediate Similarity	NPC260323
0.7903	Intermediate Similarity	NPC176279
0.7902	Intermediate Similarity	NPC227841
0.7899	Intermediate Similarity	NPC100340
0.7899	Intermediate Similarity	NPC143659
0.7899	Intermediate Similarity	NPC313081
0.7891	Intermediate Similarity	NPC471671
0.7891	Intermediate Similarity	NPC469609
0.7891	Intermediate Similarity	NPC48781
0.7891	Intermediate Similarity	NPC9592
0.7891	Intermediate Similarity	NPC48342
0.7891	Intermediate Similarity	NPC164649
0.7887	Intermediate Similarity	NPC173203
0.7887	Intermediate Similarity	NPC163508
0.7886	Intermediate Similarity	NPC58865
0.7874	Intermediate Similarity	NPC257540
0.7874	Intermediate Similarity	NPC471668
0.7874	Intermediate Similarity	NPC141001
0.7874	Intermediate Similarity	NPC247858
0.7874	Intermediate Similarity	NPC137496
0.7874	Intermediate Similarity	NPC474358
0.7874	Intermediate Similarity	NPC154511
0.7874	Intermediate Similarity	NPC474387
0.7872	Intermediate Similarity	NPC472089
0.7869	Intermediate Similarity	NPC232523
0.7869	Intermediate Similarity	NPC204901
0.7869	Intermediate Similarity	NPC158253
0.7869	Intermediate Similarity	NPC151477
0.7857	Intermediate Similarity	NPC471534
0.7857	Intermediate Similarity	NPC268160
0.7852	Intermediate Similarity	NPC222108
0.7852	Intermediate Similarity	NPC96719
0.7851	Intermediate Similarity	NPC37802

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 NPC145659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	1020
0.2-0.3	1336
0.3-0.4	3218
0.4-0.5	1779
0.5-0.6	1040
0.6-0.7	300
0.7-0.8	43
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8033	Intermediate Similarity	NPD4750	Phase 3
0.7907	Intermediate Similarity	NPD4059	Approved
0.7902	Intermediate Similarity	NPD7390	Discontinued
0.7891	Intermediate Similarity	NPD3091	Approved
0.7869	Intermediate Similarity	NPD2342	Discontinued
0.782	Intermediate Similarity	NPD3094	Phase 2
0.7815	Intermediate Similarity	NPD1242	Phase 1
0.7794	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD3092	Approved
0.7778	Intermediate Similarity	NPD4908	Phase 1
0.7769	Intermediate Similarity	NPD3019	Approved
0.775	Intermediate Similarity	NPD940	Approved
0.775	Intermediate Similarity	NPD846	Approved
0.766	Intermediate Similarity	NPD5408	Approved
0.766	Intermediate Similarity	NPD5406	Approved
0.766	Intermediate Similarity	NPD5405	Approved
0.766	Intermediate Similarity	NPD5404	Approved
0.7634	Intermediate Similarity	NPD2932	Approved
0.7634	Intermediate Similarity	NPD3095	Discontinued
0.7591	Intermediate Similarity	NPD4625	Phase 3
0.7583	Intermediate Similarity	NPD3020	Approved
0.7559	Intermediate Similarity	NPD7635	Approved
0.746	Intermediate Similarity	NPD3021	Approved
0.746	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1610	Phase 2
0.7368	Intermediate Similarity	NPD2286	Discontinued
0.7343	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2859	Approved
0.7333	Intermediate Similarity	NPD2860	Approved
0.7319	Intermediate Similarity	NPD2861	Phase 2
0.7319	Intermediate Similarity	NPD5736	Approved
0.7313	Intermediate Similarity	NPD3026	Approved
0.7313	Intermediate Similarity	NPD3023	Approved
0.7293	Intermediate Similarity	NPD3025	Approved
0.7293	Intermediate Similarity	NPD4093	Discontinued
0.7293	Intermediate Similarity	NPD3024	Approved
0.7279	Intermediate Similarity	NPD4749	Approved
0.7279	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD288	Approved
0.7259	Intermediate Similarity	NPD1201	Approved
0.725	Intermediate Similarity	NPD2933	Approved
0.725	Intermediate Similarity	NPD2934	Approved
0.7246	Intermediate Similarity	NPD4624	Approved
0.7231	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD844	Approved
0.7174	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6663	Approved
0.7103	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3892	Phase 2
0.709	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD4097	Suspended
0.7071	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD845	Approved
0.702	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5155	Approved
0.6972	Remote Similarity	NPD3027	Phase 3
0.6972	Remote Similarity	NPD5156	Approved
0.6967	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.696	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7037	Approved
0.6944	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3620	Phase 2
0.6944	Remote Similarity	NPD1613	Approved
0.6944	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6959	Discontinued
0.6911	Remote Similarity	NPD1809	Phase 2
0.6906	Remote Similarity	NPD5327	Phase 3
0.6901	Remote Similarity	NPD3595	Approved
0.6901	Remote Similarity	NPD2606	Approved
0.6901	Remote Similarity	NPD3594	Approved
0.6901	Remote Similarity	NPD2605	Approved
0.6897	Remote Similarity	NPD5735	Approved
0.6892	Remote Similarity	NPD4725	Approved
0.6892	Remote Similarity	NPD4726	Approved
0.6892	Remote Similarity	NPD4721	Approved
0.6871	Remote Similarity	NPD7743	Approved
0.6871	Remote Similarity	NPD7742	Approved
0.6867	Remote Similarity	NPD3750	Approved
0.6867	Remote Similarity	NPD7003	Approved
0.6861	Remote Similarity	NPD1751	Approved
0.6849	Remote Similarity	NPD6353	Approved
0.6842	Remote Similarity	NPD7041	Phase 2
0.6842	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7741	Discontinued
0.6832	Remote Similarity	NPD7199	Phase 2
0.6828	Remote Similarity	NPD4060	Phase 1
0.6828	Remote Similarity	NPD943	Approved
0.6828	Remote Similarity	NPD4140	Approved
0.6824	Remote Similarity	NPD6100	Approved
0.6824	Remote Similarity	NPD6099	Approved
0.6821	Remote Similarity	NPD8131	Suspended
0.6815	Remote Similarity	NPD37	Approved
0.6806	Remote Similarity	NPD3764	Approved
0.6797	Remote Similarity	NPD7447	Phase 1
0.6797	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1792	Phase 2
0.6791	Remote Similarity	NPD497	Approved
0.6779	Remote Similarity	NPD5763	Approved
0.6779	Remote Similarity	NPD5762	Approved
0.6755	Remote Similarity	NPD8166	Discontinued
0.6748	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4626	Approved
0.6732	Remote Similarity	NPD7213	Phase 3
0.6732	Remote Similarity	NPD7212	Phase 2
0.6726	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2228	Approved
0.6716	Remote Similarity	NPD496	Approved
0.6716	Remote Similarity	NPD2234	Approved
0.6716	Remote Similarity	NPD498	Approved
0.6716	Remote Similarity	NPD2229	Approved
0.6716	Remote Similarity	NPD495	Approved
0.6715	Remote Similarity	NPD5303	Approved
0.6715	Remote Similarity	NPD5304	Approved
0.6713	Remote Similarity	NPD3635	Approved
0.6713	Remote Similarity	NPD3636	Approved
0.6713	Remote Similarity	NPD3637	Approved
0.6708	Remote Similarity	NPD6234	Discontinued
0.6689	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3638	Discontinued
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD6232	Discontinued
0.6687	Remote Similarity	NPD4966	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6687	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7473	Discontinued
0.6646	Remote Similarity	NPD3749	Approved
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6405	Approved
0.6644	Remote Similarity	NPD6407	Approved
0.6643	Remote Similarity	NPD2195	Approved
0.6643	Remote Similarity	NPD2194	Approved
0.6627	Remote Similarity	NPD7228	Approved
0.6625	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2568	Approved
0.662	Remote Similarity	NPD6696	Suspended
0.6619	Remote Similarity	NPD4589	Approved
0.6619	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3018	Phase 2
0.6594	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5283	Phase 1
0.6585	Remote Similarity	NPD7229	Phase 3
0.6581	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD1445	Approved
0.6565	Remote Similarity	NPD1444	Approved
0.6562	Remote Similarity	NPD3028	Approved
0.6556	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6273	Approved
0.6536	Remote Similarity	NPD7466	Approved
0.6533	Remote Similarity	NPD3748	Approved
0.6533	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1510	Phase 2
0.6531	Remote Similarity	NPD8032	Phase 2
0.6528	Remote Similarity	NPD6584	Phase 3
0.6525	Remote Similarity	NPD422	Phase 1
0.6519	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD2420	Approved
0.6516	Remote Similarity	NPD2421	Approved
0.6513	Remote Similarity	NPD970	Clinical (unspecified phase)
0.651	Remote Similarity	NPD2157	Approved
0.6506	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1283	Approved
0.65	Remote Similarity	NPD111	Approved
0.6496	Remote Similarity	NPD6671	Approved
0.6488	Remote Similarity	NPD5844	Phase 1
0.6486	Remote Similarity	NPD1555	Discontinued
0.6486	Remote Similarity	NPD2238	Phase 2
0.6474	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7819	Suspended
0.6458	Remote Similarity	NPD1164	Approved
0.6453	Remote Similarity	NPD8053	Approved
0.6453	Remote Similarity	NPD8054	Approved
0.6452	Remote Similarity	NPD3300	Phase 2
0.6446	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5124	Phase 1
0.6443	Remote Similarity	NPD3657	Discovery
0.6443	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7833	Phase 2
0.6442	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7831	Phase 2
0.6434	Remote Similarity	NPD2982	Phase 2
0.6434	Remote Similarity	NPD4659	Approved
0.6434	Remote Similarity	NPD2983	Phase 2
0.6429	Remote Similarity	NPD5691	Approved
0.6429	Remote Similarity	NPD1651	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