NPASS Compound

Structure

NPC193749 OpenBabel07101718312D 27 33 0 0 1 0 0 0 0 0999 V2000 -0.1359 -2.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7266 -2.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3172 -1.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3749 -0.7897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0915 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8642 -1.4301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2738 -1.2329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1796 -1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4111 -1.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -1.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4686 -0.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6026 0.2728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6369 -0.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7366 -0.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0556 -1.8564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -3.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3347 -1.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 0.7728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 -1.2029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6904 -0.8436 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 8 1 0 0 0 0 3 11 2 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 21 2 0 0 0 0 10 13 2 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 15 2 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 19 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 20 1 6 0 0 0 18 24 1 0 0 0 0 19 7 1 1 0 0 0 19 25 1 0 0 0 0 19 27 1 0 0 0 0 20 15 1 6 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.06
Volume:	335.021
LogP:	1.552
LogD:	1.371
LogS:	-4.34
# Rotatable Bonds:	0
TPSA:	97.75
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	6.226
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.428
MDCK Permeability:	1.8914668544312008e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.168

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.573
Plasma Protein Binding (PPB):	90.12613677978516%
Volume Distribution (VD):	0.759
Pgp-substrate:	5.00516939163208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.133
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.375
CYP2C9-inhibitor:	0.515
CYP2C9-substrate:	0.164
CYP2D6-inhibitor:	0.163
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.524

ADMET: Excretion

Clearance (CL):	3.133
Half-life (T1/2):	0.642

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.791
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.96
Rat Oral Acute Toxicity:	0.503
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.925
Carcinogencity:	0.868
Eye Corrosion:	0.003
Eye Irritation:	0.431
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC193749

Natural Product ID:	NPC193749
*Common Name:**	Preussomerin D
IUPAC Name:	n.a.
Synonyms:	Preussomerin D
Standard InCHIKey:	PEMPTCPFSPBRLS-WAPOTWQKSA-N
Standard InCHI:	InChI=1S/C20H12O7/c21-9-6-7-19-14-8(9)2-1-3-11(14)26-20(27-19)15-12(25-19)5-4-10(22)13(15)16(23)17-18(20)24-17/h1-7,16-18,22-23H/t16-,17-,18-,19-,20+/m1/s1
SMILES:	O=C1C=C[C@@]23c4c1cccc4O[C@]1(O3)c3c(O2)ccc(c3[C@H]([C@@H]2[C@H]1O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487725
PubChem CID:	10473936
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO32546	ymf 1.01029	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18479163]
NPO40540	Lasiodiplodia theobromae ZJ-HQ1	Strain	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27560695]

☑ 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
Others	4

Activity Type	# Activity
NON-MOLECULAR	5
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	60.4	%	PMID[495888]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	53.8	%	PMID[495888]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	83.7	%	PMID[495888]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	76.5	%	PMID[495888]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24000.0	nM	PMID[495889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9800.0	nM	PMID[495889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21000.0	nM	PMID[495889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	38000.0	nM	PMID[495889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6600.0	nM	PMID[495889]

☑ 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 NPC193749 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	404
0.1-0.2	1603
0.2-0.3	3667
0.3-0.4	8951
0.4-0.5	9602
0.5-0.6	3671
0.6-0.7	6388
0.7-0.8	7944
0.8-0.85	440
0.85-0.9	13
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC183402
0.9551	High Similarity	NPC297404
0.9551	High Similarity	NPC11608
0.943	High Similarity	NPC103633
0.925	High Similarity	NPC137460
0.9085	High Similarity	NPC272656
0.8994	High Similarity	NPC73148
0.8889	High Similarity	NPC175082
0.8889	High Similarity	NPC472150
0.8824	High Similarity	NPC473951
0.8758	High Similarity	NPC23807
0.8688	High Similarity	NPC177742
0.8662	High Similarity	NPC93619
0.8662	High Similarity	NPC475890
0.865	High Similarity	NPC127415
0.8642	High Similarity	NPC478222
0.8636	High Similarity	NPC271076
0.8634	High Similarity	NPC472156
0.859	High Similarity	NPC92054
0.859	High Similarity	NPC4958
0.859	High Similarity	NPC140722
0.8589	High Similarity	NPC61594
0.8589	High Similarity	NPC56735
0.8571	High Similarity	NPC151704
0.8571	High Similarity	NPC3718
0.8571	High Similarity	NPC477833
0.8554	High Similarity	NPC222455
0.8554	High Similarity	NPC246274
0.8537	High Similarity	NPC121290
0.8537	High Similarity	NPC147596
0.8528	High Similarity	NPC472153
0.8521	High Similarity	NPC475246
0.8519	High Similarity	NPC57072
0.8519	High Similarity	NPC231475
0.8516	High Similarity	NPC472154
0.8503	High Similarity	NPC471416
0.8503	High Similarity	NPC44558
0.8503	High Similarity	NPC34287
0.85	High Similarity	NPC299761
0.85	High Similarity	NPC185103
0.85	High Similarity	NPC92153
0.85	High Similarity	NPC478218
0.85	High Similarity	NPC279281
0.85	High Similarity	NPC230439
0.8494	Intermediate Similarity	NPC63470
0.8485	Intermediate Similarity	NPC280923
0.8476	Intermediate Similarity	NPC146837
0.8476	Intermediate Similarity	NPC212099
0.8476	Intermediate Similarity	NPC278329
0.8476	Intermediate Similarity	NPC101116
0.8471	Intermediate Similarity	NPC476618
0.8471	Intermediate Similarity	NPC476622
0.8471	Intermediate Similarity	NPC472387
0.8471	Intermediate Similarity	NPC476623
0.8471	Intermediate Similarity	NPC476620
0.8471	Intermediate Similarity	NPC476621
0.8471	Intermediate Similarity	NPC476619
0.8466	Intermediate Similarity	NPC328093
0.8462	Intermediate Similarity	NPC47152
0.8462	Intermediate Similarity	NPC97662
0.8462	Intermediate Similarity	NPC288531
0.8457	Intermediate Similarity	NPC474441
0.8457	Intermediate Similarity	NPC476026
0.8457	Intermediate Similarity	NPC474398
0.8457	Intermediate Similarity	NPC474401
0.8452	Intermediate Similarity	NPC267254
0.8452	Intermediate Similarity	NPC259152
0.8452	Intermediate Similarity	NPC3583
0.8452	Intermediate Similarity	NPC301683
0.8452	Intermediate Similarity	NPC315619
0.8443	Intermediate Similarity	NPC170675
0.8443	Intermediate Similarity	NPC472381
0.8443	Intermediate Similarity	NPC471457
0.8443	Intermediate Similarity	NPC112755
0.8443	Intermediate Similarity	NPC472383
0.8443	Intermediate Similarity	NPC472152
0.8434	Intermediate Similarity	NPC70441
0.8434	Intermediate Similarity	NPC475174
0.8424	Intermediate Similarity	NPC475183
0.8424	Intermediate Similarity	NPC74371
0.8424	Intermediate Similarity	NPC120677
0.8415	Intermediate Similarity	NPC132737
0.8412	Intermediate Similarity	NPC472991
0.8412	Intermediate Similarity	NPC46958
0.8412	Intermediate Similarity	NPC102053
0.8412	Intermediate Similarity	NPC472992
0.8412	Intermediate Similarity	NPC297574
0.8408	Intermediate Similarity	NPC301949
0.8402	Intermediate Similarity	NPC239549
0.8402	Intermediate Similarity	NPC204693
0.8402	Intermediate Similarity	NPC236191
0.8402	Intermediate Similarity	NPC51774
0.8402	Intermediate Similarity	NPC470438
0.8393	Intermediate Similarity	NPC105511
0.8393	Intermediate Similarity	NPC474434
0.8393	Intermediate Similarity	NPC313304
0.8393	Intermediate Similarity	NPC181778
0.8393	Intermediate Similarity	NPC21190
0.8393	Intermediate Similarity	NPC22195
0.8393	Intermediate Similarity	NPC183357
0.8387	Intermediate Similarity	NPC133585
0.8383	Intermediate Similarity	NPC45618
0.8383	Intermediate Similarity	NPC45400
0.8383	Intermediate Similarity	NPC14662
0.8383	Intermediate Similarity	NPC93099
0.8383	Intermediate Similarity	NPC58716
0.8383	Intermediate Similarity	NPC146792
0.8383	Intermediate Similarity	NPC225419
0.8373	Intermediate Similarity	NPC99216
0.8373	Intermediate Similarity	NPC178281
0.8373	Intermediate Similarity	NPC75944
0.8372	Intermediate Similarity	NPC475161
0.8372	Intermediate Similarity	NPC53680
0.8372	Intermediate Similarity	NPC8940
0.8372	Intermediate Similarity	NPC477860
0.8372	Intermediate Similarity	NPC208797
0.8366	Intermediate Similarity	NPC472151
0.8364	Intermediate Similarity	NPC148273
0.8364	Intermediate Similarity	NPC4013
0.8364	Intermediate Similarity	NPC473961
0.8364	Intermediate Similarity	NPC90905
0.8364	Intermediate Similarity	NPC478229
0.8364	Intermediate Similarity	NPC22324
0.8354	Intermediate Similarity	NPC271479
0.8354	Intermediate Similarity	NPC471976
0.8353	Intermediate Similarity	NPC102028
0.8343	Intermediate Similarity	NPC271385
0.8343	Intermediate Similarity	NPC475155
0.8343	Intermediate Similarity	NPC212038
0.8343	Intermediate Similarity	NPC262580
0.8343	Intermediate Similarity	NPC30432
0.8343	Intermediate Similarity	NPC67134
0.8343	Intermediate Similarity	NPC307518
0.8343	Intermediate Similarity	NPC76128
0.8343	Intermediate Similarity	NPC472386
0.8343	Intermediate Similarity	NPC47140
0.8343	Intermediate Similarity	NPC5029
0.8343	Intermediate Similarity	NPC81332
0.8343	Intermediate Similarity	NPC48773
0.8343	Intermediate Similarity	NPC111536
0.8343	Intermediate Similarity	NPC260263
0.8343	Intermediate Similarity	NPC289396
0.8343	Intermediate Similarity	NPC271848
0.8343	Intermediate Similarity	NPC205076
0.8343	Intermediate Similarity	NPC156977
0.8333	Intermediate Similarity	NPC472155
0.8333	Intermediate Similarity	NPC105025
0.8333	Intermediate Similarity	NPC183036
0.8333	Intermediate Similarity	NPC229687
0.8333	Intermediate Similarity	NPC475942
0.8333	Intermediate Similarity	NPC58053
0.8333	Intermediate Similarity	NPC469931
0.8333	Intermediate Similarity	NPC45638
0.8333	Intermediate Similarity	NPC186807
0.8333	Intermediate Similarity	NPC95855
0.8333	Intermediate Similarity	NPC201292
0.8333	Intermediate Similarity	NPC210042
0.8333	Intermediate Similarity	NPC226294
0.8333	Intermediate Similarity	NPC93337
0.8324	Intermediate Similarity	NPC476203
0.8323	Intermediate Similarity	NPC210073
0.8323	Intermediate Similarity	NPC115674
0.8323	Intermediate Similarity	NPC474656
0.8323	Intermediate Similarity	NPC478220
0.8323	Intermediate Similarity	NPC178173
0.8323	Intermediate Similarity	NPC474843
0.8323	Intermediate Similarity	NPC8856
0.8323	Intermediate Similarity	NPC215811
0.8314	Intermediate Similarity	NPC299149
0.8314	Intermediate Similarity	NPC277710
0.8314	Intermediate Similarity	NPC58538
0.8314	Intermediate Similarity	NPC153578
0.8314	Intermediate Similarity	NPC114257
0.8313	Intermediate Similarity	NPC88043
0.8313	Intermediate Similarity	NPC67959
0.8313	Intermediate Similarity	NPC470178
0.8313	Intermediate Similarity	NPC29830
0.8313	Intermediate Similarity	NPC168822
0.8312	Intermediate Similarity	NPC193920
0.8304	Intermediate Similarity	NPC470949
0.8304	Intermediate Similarity	NPC314489
0.8304	Intermediate Similarity	NPC232818
0.8304	Intermediate Similarity	NPC8573
0.8304	Intermediate Similarity	NPC65563
0.8304	Intermediate Similarity	NPC169733
0.8304	Intermediate Similarity	NPC198893
0.8303	Intermediate Similarity	NPC303913
0.8303	Intermediate Similarity	NPC3629
0.8294	Intermediate Similarity	NPC46640
0.8294	Intermediate Similarity	NPC203751
0.8294	Intermediate Similarity	NPC163165
0.8294	Intermediate Similarity	NPC34436
0.8294	Intermediate Similarity	NPC219600
0.8294	Intermediate Similarity	NPC85368
0.8294	Intermediate Similarity	NPC263119
0.8294	Intermediate Similarity	NPC199357
0.8294	Intermediate Similarity	NPC166674
0.8293	Intermediate Similarity	NPC308265
0.8293	Intermediate Similarity	NPC74319
0.8293	Intermediate Similarity	NPC186113

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 NPC193749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	902
0.2-0.3	1785
0.3-0.4	2644
0.4-0.5	1808
0.5-0.6	1031
0.6-0.7	460
0.7-0.8	143
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8834	High Similarity	NPD3751	Discontinued
0.8476	Intermediate Similarity	NPD3787	Discontinued
0.8232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7054	Approved
0.8198	Intermediate Similarity	NPD8313	Approved
0.8198	Intermediate Similarity	NPD8312	Approved
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8176	Intermediate Similarity	NPD7472	Approved
0.8171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6797	Phase 2
0.8118	Intermediate Similarity	NPD5844	Phase 1
0.811	Intermediate Similarity	NPD5402	Approved
0.8089	Intermediate Similarity	NPD3750	Approved
0.8081	Intermediate Similarity	NPD7251	Discontinued
0.8079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD3818	Discontinued
0.8047	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6166	Phase 2
0.8035	Intermediate Similarity	NPD7808	Phase 3
0.8023	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1934	Approved
0.7939	Intermediate Similarity	NPD1465	Phase 2
0.7939	Intermediate Similarity	NPD2801	Approved
0.7907	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4380	Phase 2
0.7865	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD5494	Approved
0.7772	Intermediate Similarity	NPD6777	Approved
0.7772	Intermediate Similarity	NPD6779	Approved
0.7772	Intermediate Similarity	NPD6778	Approved
0.7772	Intermediate Similarity	NPD6776	Approved
0.7772	Intermediate Similarity	NPD6781	Approved
0.7772	Intermediate Similarity	NPD6782	Approved
0.7772	Intermediate Similarity	NPD6780	Approved
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD3748	Approved
0.7765	Intermediate Similarity	NPD6959	Discontinued
0.7746	Intermediate Similarity	NPD7228	Approved
0.7736	Intermediate Similarity	NPD1549	Phase 2
0.7725	Intermediate Similarity	NPD8455	Phase 2
0.7716	Intermediate Similarity	NPD1511	Approved
0.7697	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6823	Phase 2
0.7683	Intermediate Similarity	NPD5403	Approved
0.7673	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5401	Approved
0.7647	Intermediate Similarity	NPD7697	Approved
0.7647	Intermediate Similarity	NPD7698	Approved
0.7647	Intermediate Similarity	NPD7696	Phase 3
0.7647	Intermediate Similarity	NPD7435	Discontinued
0.7636	Intermediate Similarity	NPD1653	Approved
0.7633	Intermediate Similarity	NPD3882	Suspended
0.7622	Intermediate Similarity	NPD1512	Approved
0.7619	Intermediate Similarity	NPD7819	Suspended
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7075	Discontinued
0.7588	Intermediate Similarity	NPD3749	Approved
0.7579	Intermediate Similarity	NPD7701	Phase 2
0.7571	Intermediate Similarity	NPD7685	Pre-registration
0.756	Intermediate Similarity	NPD37	Approved
0.7544	Intermediate Similarity	NPD6234	Discontinued
0.7531	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1613	Approved
0.7515	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7485	Intermediate Similarity	NPD3226	Approved
0.7473	Intermediate Similarity	NPD7700	Phase 2
0.7473	Intermediate Similarity	NPD7699	Phase 2
0.7471	Intermediate Similarity	NPD3817	Phase 2
0.7471	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7457	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7438	Intermediate Similarity	NPD1510	Phase 2
0.7414	Intermediate Similarity	NPD6232	Discontinued
0.7409	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7874	Approved
0.7396	Intermediate Similarity	NPD7411	Suspended
0.7394	Intermediate Similarity	NPD6799	Approved
0.7391	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD1551	Phase 2
0.7386	Intermediate Similarity	NPD7473	Discontinued
0.7378	Intermediate Similarity	NPD6190	Approved
0.7374	Intermediate Similarity	NPD7240	Approved
0.7371	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7801	Approved
0.7371	Intermediate Similarity	NPD7783	Phase 2
0.7362	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1933	Approved
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7353	Intermediate Similarity	NPD6801	Discontinued
0.7349	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7266	Discontinued
0.733	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7768	Phase 2
0.7301	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD3764	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6212	Phase 3
0.7258	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6213	Phase 3
0.7255	Intermediate Similarity	NPD1091	Approved
0.7251	Intermediate Similarity	NPD6844	Discontinued
0.725	Intermediate Similarity	NPD447	Suspended
0.7246	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6599	Discontinued
0.7233	Intermediate Similarity	NPD6233	Phase 2
0.7212	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6273	Approved
0.7197	Intermediate Similarity	NPD2861	Phase 2
0.7197	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1240	Approved
0.7186	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1203	Approved
0.717	Intermediate Similarity	NPD2313	Discontinued
0.7168	Intermediate Similarity	NPD4288	Approved
0.7152	Intermediate Similarity	NPD6674	Discontinued
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.715	Intermediate Similarity	NPD8319	Approved
0.715	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7113	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1607	Approved
0.7076	Intermediate Similarity	NPD2651	Approved
0.7076	Intermediate Similarity	NPD2649	Approved
0.7073	Intermediate Similarity	NPD6099	Approved
0.7073	Intermediate Similarity	NPD6100	Approved
0.707	Intermediate Similarity	NPD1470	Approved
0.7063	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7044	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2532	Approved
0.7041	Intermediate Similarity	NPD2534	Approved
0.7041	Intermediate Similarity	NPD2533	Approved
0.7037	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1610	Phase 2
0.7025	Intermediate Similarity	NPD2798	Approved
0.7012	Intermediate Similarity	NPD2799	Discontinued
0.7012	Intermediate Similarity	NPD4308	Phase 3
0.7006	Intermediate Similarity	NPD3225	Approved
0.7006	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD3027	Phase 3
0.6979	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4060	Phase 1
0.6975	Remote Similarity	NPD943	Approved
0.6966	Remote Similarity	NPD8127	Discontinued
0.6966	Remote Similarity	NPD1247	Approved
0.6962	Remote Similarity	NPD2797	Approved
0.6957	Remote Similarity	NPD3268	Approved
0.6951	Remote Similarity	NPD7097	Phase 1
0.6946	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2800	Approved
0.6937	Remote Similarity	NPD6832	Phase 2
0.6933	Remote Similarity	NPD6355	Discontinued
0.6928	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2344	Approved
0.6923	Remote Similarity	NPD7680	Approved
0.6923	Remote Similarity	NPD1201	Approved
0.6909	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8166	Discontinued
0.6897	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4625	Phase 3
0.6886	Remote Similarity	NPD2424	Discontinued
0.6883	Remote Similarity	NPD1548	Phase 1
0.6879	Remote Similarity	NPD1481	Phase 2
0.6879	Remote Similarity	NPD9717	Approved
0.6879	Remote Similarity	NPD1608	Approved
0.6878	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8059	Phase 3
0.6875	Remote Similarity	NPD9494	Approved
0.6875	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7177	Discontinued
0.6867	Remote Similarity	NPD5404	Approved
0.6867	Remote Similarity	NPD5406	Approved
0.6867	Remote Similarity	NPD5408	Approved
0.6867	Remote Similarity	NPD5405	Approved
0.6865	Remote Similarity	NPD7549	Discontinued
0.6845	Remote Similarity	NPD1652	Phase 2
0.6835	Remote Similarity	NPD4379	Clinical (unspecified phase)

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