NPASS Compound

Structure

NPC472783 OpenBabel07101719512D 25 28 0 0 1 0 0 0 0 0999 V2000 1.3171 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7516 1.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 -2.0339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1583 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9344 -2.2418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1365 0.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3171 -2.6750 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 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 5 1 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 20 1 0 0 0 0 8 11 2 0 0 0 0 8 25 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 21 2 0 0 0 0 14 22 1 1 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 25 1 0 0 0 0 19 1 1 6 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	337.24
LogP:	0.783
LogD:	0.908
LogS:	-3.511
# Rotatable Bonds:	3
TPSA:	107.97
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	4.039
Fsp3:	0.368
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:	-5.39
MDCK Permeability:	1.1491712029965129e-05
Pgp-inhibitor:	0.776
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.519
20% Bioavailability (F20%):	0.732
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.614
Plasma Protein Binding (PPB):	66.61295318603516%
Volume Distribution (VD):	1.407
Pgp-substrate:	25.075647354125977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.346
CYP1A2-substrate:	0.208
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.154
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	2.821
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.125
AMES Toxicity:	0.63
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.102
Carcinogencity:	0.975
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC472783

Natural Product ID:	NPC472783
*Common Name:**	IXWGQFUDXHHAIA-IFXJQAMLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IXWGQFUDXHHAIA-IFXJQAMLSA-N
Standard InCHI:	InChI=1S/C19H18O6/c1-19(24)12-4-2-9-10(3-5-13(9)21)15(12)17(23)18-16(19)11(8-25-18)14(22)6-7-20/h2,4,8,14,20,22,24H,3,5-7H2,1H3/t14-,19+/m0/s1
SMILES:	CC1(C2=C(C3=C(C=C2)C(=O)CC3)C(=O)C4=C1C(=CO4)C(CCO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582129
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12270179]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542359]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17363259]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25978520]

☑ 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	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Inhibition	=	80.5	%	PMID[486834]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	=	71900.0	nM	PMID[486834]

☑ 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 NPC472783 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	386
0.1-0.2	1499
0.2-0.3	3134
0.3-0.4	8134
0.4-0.5	10884
0.5-0.6	5050
0.6-0.7	6588
0.7-0.8	6678
0.8-0.85	318
0.85-0.9	21
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472780
0.9934	High Similarity	NPC472782
0.9934	High Similarity	NPC472781
0.9679	High Similarity	NPC472784
0.8957	High Similarity	NPC44602
0.8861	High Similarity	NPC75310
0.8861	High Similarity	NPC472785
0.8742	High Similarity	NPC88958
0.8734	High Similarity	NPC475777
0.8671	High Similarity	NPC472787
0.8634	High Similarity	NPC221992
0.8616	High Similarity	NPC471613
0.858	High Similarity	NPC299094
0.858	High Similarity	NPC116639
0.858	High Similarity	NPC10051
0.8562	High Similarity	NPC114880
0.8554	High Similarity	NPC191012
0.8544	High Similarity	NPC211625
0.8529	High Similarity	NPC295914
0.8526	High Similarity	NPC469385
0.8516	High Similarity	NPC64568
0.8509	High Similarity	NPC472786
0.8509	High Similarity	NPC179170
0.8494	Intermediate Similarity	NPC136641
0.8485	Intermediate Similarity	NPC193998
0.8485	Intermediate Similarity	NPC261184
0.8471	Intermediate Similarity	NPC97904
0.8466	Intermediate Similarity	NPC164110
0.8466	Intermediate Similarity	NPC217602
0.8466	Intermediate Similarity	NPC476404
0.8466	Intermediate Similarity	NPC317900
0.8466	Intermediate Similarity	NPC246647
0.8466	Intermediate Similarity	NPC212967
0.8466	Intermediate Similarity	NPC96342
0.8466	Intermediate Similarity	NPC473282
0.8466	Intermediate Similarity	NPC294300
0.8466	Intermediate Similarity	NPC104380
0.8447	Intermediate Similarity	NPC263676
0.8434	Intermediate Similarity	NPC109180
0.8428	Intermediate Similarity	NPC280025
0.8415	Intermediate Similarity	NPC476350
0.8415	Intermediate Similarity	NPC476349
0.8405	Intermediate Similarity	NPC304692
0.8405	Intermediate Similarity	NPC180924
0.8397	Intermediate Similarity	NPC243577
0.8395	Intermediate Similarity	NPC290927
0.8385	Intermediate Similarity	NPC145830
0.8375	Intermediate Similarity	NPC226578
0.8365	Intermediate Similarity	NPC469425
0.8364	Intermediate Similarity	NPC313368
0.8364	Intermediate Similarity	NPC18986
0.8354	Intermediate Similarity	NPC474611
0.8354	Intermediate Similarity	NPC472823
0.8354	Intermediate Similarity	NPC260902
0.8354	Intermediate Similarity	NPC140952
0.8354	Intermediate Similarity	NPC296957
0.8344	Intermediate Similarity	NPC104736
0.8344	Intermediate Similarity	NPC148938
0.8333	Intermediate Similarity	NPC53640
0.8333	Intermediate Similarity	NPC296558
0.8324	Intermediate Similarity	NPC104682
0.8323	Intermediate Similarity	NPC473681
0.8323	Intermediate Similarity	NPC121995
0.8323	Intermediate Similarity	NPC218204
0.8323	Intermediate Similarity	NPC61157
0.8323	Intermediate Similarity	NPC472581
0.8323	Intermediate Similarity	NPC100849
0.8313	Intermediate Similarity	NPC224394
0.8313	Intermediate Similarity	NPC24761
0.8313	Intermediate Similarity	NPC663
0.8313	Intermediate Similarity	NPC269117
0.8304	Intermediate Similarity	NPC167340
0.8293	Intermediate Similarity	NPC160015
0.8293	Intermediate Similarity	NPC247677
0.8293	Intermediate Similarity	NPC81405
0.8284	Intermediate Similarity	NPC476459
0.8282	Intermediate Similarity	NPC235333
0.8282	Intermediate Similarity	NPC41719
0.8282	Intermediate Similarity	NPC158261
0.8282	Intermediate Similarity	NPC42458
0.8274	Intermediate Similarity	NPC316262
0.8274	Intermediate Similarity	NPC314653
0.8272	Intermediate Similarity	NPC116604
0.8272	Intermediate Similarity	NPC75906
0.8272	Intermediate Similarity	NPC175617
0.8263	Intermediate Similarity	NPC219861
0.8258	Intermediate Similarity	NPC60848
0.8253	Intermediate Similarity	NPC284495
0.8253	Intermediate Similarity	NPC470810
0.825	Intermediate Similarity	NPC19747
0.825	Intermediate Similarity	NPC252208
0.8242	Intermediate Similarity	NPC268360
0.8242	Intermediate Similarity	NPC269495
0.8242	Intermediate Similarity	NPC123153
0.8239	Intermediate Similarity	NPC62799
0.8232	Intermediate Similarity	NPC213936
0.8232	Intermediate Similarity	NPC297531
0.8232	Intermediate Similarity	NPC41880
0.8225	Intermediate Similarity	NPC255787
0.8221	Intermediate Similarity	NPC471347
0.8221	Intermediate Similarity	NPC253872
0.8221	Intermediate Similarity	NPC471349
0.8221	Intermediate Similarity	NPC207624
0.8214	Intermediate Similarity	NPC475779
0.8214	Intermediate Similarity	NPC149945
0.821	Intermediate Similarity	NPC61258
0.821	Intermediate Similarity	NPC472406
0.821	Intermediate Similarity	NPC13282
0.8204	Intermediate Similarity	NPC283209
0.8204	Intermediate Similarity	NPC288602
0.8204	Intermediate Similarity	NPC88841
0.8204	Intermediate Similarity	NPC304387
0.8199	Intermediate Similarity	NPC192069
0.8193	Intermediate Similarity	NPC287559
0.8193	Intermediate Similarity	NPC40583
0.8193	Intermediate Similarity	NPC226287
0.8193	Intermediate Similarity	NPC472299
0.8187	Intermediate Similarity	NPC313717
0.8187	Intermediate Similarity	NPC315306
0.8187	Intermediate Similarity	NPC471346
0.8182	Intermediate Similarity	NPC249021
0.8182	Intermediate Similarity	NPC472772
0.8176	Intermediate Similarity	NPC245522
0.8176	Intermediate Similarity	NPC114513
0.8176	Intermediate Similarity	NPC472660
0.8171	Intermediate Similarity	NPC193200
0.8171	Intermediate Similarity	NPC84721
0.8171	Intermediate Similarity	NPC469966
0.8171	Intermediate Similarity	NPC213608
0.8171	Intermediate Similarity	NPC208806
0.8171	Intermediate Similarity	NPC122365
0.8171	Intermediate Similarity	NPC1477
0.8166	Intermediate Similarity	NPC476850
0.8166	Intermediate Similarity	NPC473753
0.8166	Intermediate Similarity	NPC476861
0.8166	Intermediate Similarity	NPC473766
0.816	Intermediate Similarity	NPC23668
0.816	Intermediate Similarity	NPC193976
0.816	Intermediate Similarity	NPC474772
0.816	Intermediate Similarity	NPC58668
0.816	Intermediate Similarity	NPC472423
0.816	Intermediate Similarity	NPC170169
0.816	Intermediate Similarity	NPC115324
0.816	Intermediate Similarity	NPC474744
0.816	Intermediate Similarity	NPC106372
0.8155	Intermediate Similarity	NPC123088
0.8155	Intermediate Similarity	NPC476857
0.8155	Intermediate Similarity	NPC476858
0.8155	Intermediate Similarity	NPC56358
0.8155	Intermediate Similarity	NPC476856
0.815	Intermediate Similarity	NPC472665
0.8148	Intermediate Similarity	NPC212257
0.8148	Intermediate Similarity	NPC39929
0.8148	Intermediate Similarity	NPC37226
0.8148	Intermediate Similarity	NPC226644
0.8148	Intermediate Similarity	NPC317492
0.8148	Intermediate Similarity	NPC296030
0.8144	Intermediate Similarity	NPC304839
0.8144	Intermediate Similarity	NPC472767
0.8144	Intermediate Similarity	NPC220582
0.8144	Intermediate Similarity	NPC329938
0.8144	Intermediate Similarity	NPC193798
0.8144	Intermediate Similarity	NPC188649
0.8144	Intermediate Similarity	NPC49009
0.8141	Intermediate Similarity	NPC265181
0.814	Intermediate Similarity	NPC471437
0.814	Intermediate Similarity	NPC118128
0.8137	Intermediate Similarity	NPC198427
0.8137	Intermediate Similarity	NPC478018
0.8133	Intermediate Similarity	NPC477403
0.8133	Intermediate Similarity	NPC65504
0.8133	Intermediate Similarity	NPC44199
0.8133	Intermediate Similarity	NPC282390
0.8133	Intermediate Similarity	NPC281137
0.8133	Intermediate Similarity	NPC475967
0.8133	Intermediate Similarity	NPC201127
0.8129	Intermediate Similarity	NPC63514
0.8129	Intermediate Similarity	NPC473095
0.8129	Intermediate Similarity	NPC473096
0.8129	Intermediate Similarity	NPC475641
0.8129	Intermediate Similarity	NPC475237
0.8125	Intermediate Similarity	NPC478166
0.8125	Intermediate Similarity	NPC228209
0.8121	Intermediate Similarity	NPC198490
0.8121	Intermediate Similarity	NPC99199
0.8114	Intermediate Similarity	NPC70318
0.8113	Intermediate Similarity	NPC84479
0.8113	Intermediate Similarity	NPC158871
0.8113	Intermediate Similarity	NPC117674
0.811	Intermediate Similarity	NPC38361
0.811	Intermediate Similarity	NPC40356
0.811	Intermediate Similarity	NPC67654
0.811	Intermediate Similarity	NPC178932
0.811	Intermediate Similarity	NPC154683
0.811	Intermediate Similarity	NPC5871
0.811	Intermediate Similarity	NPC142308
0.811	Intermediate Similarity	NPC130015
0.8107	Intermediate Similarity	NPC132054
0.8107	Intermediate Similarity	NPC476931
0.8107	Intermediate Similarity	NPC308156

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 NPC472783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	925
0.2-0.3	1611
0.3-0.4	2703
0.4-0.5	2096
0.5-0.6	1004
0.6-0.7	351
0.7-0.8	121
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
0.8282	Intermediate Similarity	NPD5761	Phase 2
0.8282	Intermediate Similarity	NPD5760	Phase 2
0.8171	Intermediate Similarity	NPD8434	Phase 2
0.8141	Intermediate Similarity	NPD1471	Phase 3
0.7976	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD1247	Approved
0.7818	Intermediate Similarity	NPD3226	Approved
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7784	Intermediate Similarity	NPD6765	Approved
0.7784	Intermediate Similarity	NPD6764	Approved
0.7751	Intermediate Similarity	NPD3882	Suspended
0.7738	Intermediate Similarity	NPD7819	Suspended
0.7738	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7075	Discontinued
0.7697	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6801	Discontinued
0.7674	Intermediate Similarity	NPD6959	Discontinued
0.7665	Intermediate Similarity	NPD6599	Discontinued
0.7633	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7411	Suspended
0.7611	Intermediate Similarity	NPD6784	Approved
0.7611	Intermediate Similarity	NPD6785	Approved
0.7602	Intermediate Similarity	NPD3749	Approved
0.7596	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4380	Phase 2
0.7558	Intermediate Similarity	NPD919	Approved
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD1549	Phase 2
0.7516	Intermediate Similarity	NPD2796	Approved
0.7515	Intermediate Similarity	NPD6799	Approved
0.7514	Intermediate Similarity	NPD5494	Approved
0.7514	Intermediate Similarity	NPD5844	Phase 1
0.7485	Intermediate Similarity	NPD2800	Approved
0.7469	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2344	Approved
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1607	Approved
0.7416	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1551	Phase 2
0.7384	Intermediate Similarity	NPD5402	Approved
0.7368	Intermediate Similarity	NPD1934	Approved
0.736	Intermediate Similarity	NPD3751	Discontinued
0.736	Intermediate Similarity	NPD3818	Discontinued
0.736	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1510	Phase 2
0.7345	Intermediate Similarity	NPD6166	Phase 2
0.7345	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6232	Discontinued
0.7312	Intermediate Similarity	NPD1240	Approved
0.7303	Intermediate Similarity	NPD7473	Discontinued
0.7299	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2309	Approved
0.7288	Intermediate Similarity	NPD3926	Phase 2
0.7283	Intermediate Similarity	NPD3817	Phase 2
0.7278	Intermediate Similarity	NPD5403	Approved
0.7273	Intermediate Similarity	NPD1243	Approved
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6005	Phase 3
0.7256	Intermediate Similarity	NPD6004	Phase 3
0.7256	Intermediate Similarity	NPD6002	Phase 3
0.7256	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2799	Discontinued
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7232	Intermediate Similarity	NPD5710	Approved
0.7232	Intermediate Similarity	NPD3787	Discontinued
0.7232	Intermediate Similarity	NPD5711	Approved
0.7229	Intermediate Similarity	NPD3750	Approved
0.7225	Intermediate Similarity	NPD2801	Approved
0.7225	Intermediate Similarity	NPD6779	Approved
0.7225	Intermediate Similarity	NPD6777	Approved
0.7225	Intermediate Similarity	NPD6781	Approved
0.7225	Intermediate Similarity	NPD6776	Approved
0.7225	Intermediate Similarity	NPD6778	Approved
0.7225	Intermediate Similarity	NPD6782	Approved
0.7225	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD1512	Approved
0.7202	Intermediate Similarity	NPD7435	Discontinued
0.7195	Intermediate Similarity	NPD2935	Discontinued
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.716	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8313	Approved
0.712	Intermediate Similarity	NPD8312	Approved
0.7113	Intermediate Similarity	NPD7697	Approved
0.7113	Intermediate Similarity	NPD7696	Phase 3
0.7113	Intermediate Similarity	NPD7698	Approved
0.7108	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7251	Discontinued
0.7101	Intermediate Similarity	NPD1511	Approved
0.7097	Intermediate Similarity	NPD8150	Discontinued
0.7095	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6100	Approved
0.7091	Intermediate Similarity	NPD6099	Approved
0.7081	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7870	Phase 2
0.7077	Intermediate Similarity	NPD7871	Phase 2
0.7072	Intermediate Similarity	NPD7799	Discontinued
0.7065	Intermediate Similarity	NPD7808	Phase 3
0.7065	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6535	Approved
0.7053	Intermediate Similarity	NPD6534	Approved
0.7045	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4967	Phase 2
0.7045	Intermediate Similarity	NPD4965	Approved
0.7045	Intermediate Similarity	NPD4966	Approved
0.7044	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7239	Suspended
0.703	Intermediate Similarity	NPD8404	Phase 2
0.703	Intermediate Similarity	NPD3748	Approved
0.6995	Remote Similarity	NPD7074	Phase 3
0.6985	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7874	Approved
0.6983	Remote Similarity	NPD7199	Phase 2
0.6975	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3764	Approved
0.6975	Remote Similarity	NPD3268	Approved
0.6971	Remote Similarity	NPD37	Approved
0.697	Remote Similarity	NPD7701	Phase 2
0.6961	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2403	Approved
0.6957	Remote Similarity	NPD5953	Discontinued
0.6957	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6355	Discontinued
0.6946	Remote Similarity	NPD5763	Approved
0.6946	Remote Similarity	NPD5762	Approved
0.6944	Remote Similarity	NPD6808	Phase 2
0.6944	Remote Similarity	NPD7229	Phase 3
0.6943	Remote Similarity	NPD7700	Phase 2
0.6943	Remote Similarity	NPD7699	Phase 2
0.694	Remote Similarity	NPD7054	Approved
0.694	Remote Similarity	NPD7286	Phase 2
0.6928	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1876	Approved
0.6914	Remote Similarity	NPD4625	Phase 3
0.6902	Remote Similarity	NPD7472	Approved
0.6901	Remote Similarity	NPD7390	Discontinued
0.6899	Remote Similarity	NPD3972	Approved
0.6893	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2163	Approved
0.6885	Remote Similarity	NPD7177	Discontinued
0.6872	Remote Similarity	NPD6234	Discontinued
0.6866	Remote Similarity	NPD7801	Approved
0.6852	Remote Similarity	NPD6832	Phase 2
0.6842	Remote Similarity	NPD4287	Approved
0.6842	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7003	Approved
0.6821	Remote Similarity	NPD8285	Discontinued
0.6818	Remote Similarity	NPD8320	Phase 1
0.6818	Remote Similarity	NPD8319	Approved
0.6807	Remote Similarity	NPD6651	Approved
0.6805	Remote Similarity	NPD2424	Discontinued
0.6802	Remote Similarity	NPD6823	Phase 2
0.68	Remote Similarity	NPD7458	Discontinued
0.6798	Remote Similarity	NPD2296	Approved
0.6792	Remote Similarity	NPD1608	Approved
0.6788	Remote Similarity	NPD4060	Phase 1
0.6786	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5406	Approved
0.6786	Remote Similarity	NPD5408	Approved
0.6786	Remote Similarity	NPD5404	Approved
0.6786	Remote Similarity	NPD5405	Approved
0.6784	Remote Similarity	NPD3887	Approved
0.6784	Remote Similarity	NPD6190	Approved
0.678	Remote Similarity	NPD6279	Approved
0.678	Remote Similarity	NPD6280	Approved
0.677	Remote Similarity	NPD1470	Approved
0.677	Remote Similarity	NPD1203	Approved
0.6765	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1651	Approved
0.6747	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1465	Phase 2
0.6731	Remote Similarity	NPD7907	Approved
0.6731	Remote Similarity	NPD9092	Discovery
0.6728	Remote Similarity	NPD2798	Approved
0.6724	Remote Similarity	NPD5049	Phase 3

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