NPASS Compound

Structure

NPC472781 OpenBabel07101719512D 24 27 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 -1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 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 -1.9563 -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 -0.0000 -1.6180 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 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 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 2 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 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 3 1 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 20 1 0 0 0 0 9 10 2 0 0 0 0 9 24 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 21 2 0 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 22 2 0 0 0 0 18 24 1 0 0 0 0 19 1 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.12
Volume:	328.45
LogP:	1.945
LogD:	1.93
LogS:	-4.029
# Rotatable Bonds:	3
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.902
Synthetic Accessibility Score:	3.636
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:	-4.953
MDCK Permeability:	1.7318267055088654e-05
Pgp-inhibitor:	0.532
Pgp-substrate:	0.085
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.779
Plasma Protein Binding (PPB):	78.41326141357422%
Volume Distribution (VD):	1.711
Pgp-substrate:	15.89017391204834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.748
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.551
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	2.11
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.392
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.634
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.088
Carcinogencity:	0.973
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.886

Download Data

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

Natural Product: NPC472781

Natural Product ID:	NPC472781
*Common Name:**	HNKCLBPQEJAISV-IBGZPJMESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HNKCLBPQEJAISV-IBGZPJMESA-N
Standard InCHI:	InChI=1S/C19H18O5/c1-19(23)13-6-4-11-12(5-7-14(11)21)15(13)17(22)18-16(19)10(9-24-18)3-2-8-20/h4,6,9,20,23H,2-3,5,7-8H2,1H3/t19-/m0/s1
SMILES:	OCCCc1coc2c1[C@@](C)(O)c1c(C2=O)c2CCC(=O)c2cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582127
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	=	89.5	%	PMID[485716]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	=	28000.0	nM	PMID[485716]

☑ 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 NPC472781 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	385
0.1-0.2	1562
0.2-0.3	3214
0.3-0.4	8492
0.4-0.5	10588
0.5-0.6	4997
0.6-0.7	6626
0.7-0.8	6528
0.8-0.85	285
0.85-0.9	15
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472782
0.9934	High Similarity	NPC472780
0.9934	High Similarity	NPC472783
0.9615	High Similarity	NPC472784
0.8896	High Similarity	NPC44602
0.8797	High Similarity	NPC88958
0.8797	High Similarity	NPC472785
0.8797	High Similarity	NPC75310
0.8688	High Similarity	NPC221992
0.8671	High Similarity	NPC475777
0.8608	High Similarity	NPC472787
0.8606	High Similarity	NPC191012
0.858	High Similarity	NPC295914
0.8553	High Similarity	NPC471613
0.8537	High Similarity	NPC193998
0.8519	High Similarity	NPC246647
0.8519	High Similarity	NPC10051
0.8519	High Similarity	NPC116639
0.8519	High Similarity	NPC96342
0.8519	High Similarity	NPC299094
0.8519	High Similarity	NPC164110
0.8519	High Similarity	NPC212967
0.85	High Similarity	NPC114880
0.85	High Similarity	NPC263676
0.8481	Intermediate Similarity	NPC211625
0.8481	Intermediate Similarity	NPC280025
0.8462	Intermediate Similarity	NPC469385
0.8457	Intermediate Similarity	NPC180924
0.8452	Intermediate Similarity	NPC64568
0.8447	Intermediate Similarity	NPC472786
0.8447	Intermediate Similarity	NPC179170
0.8447	Intermediate Similarity	NPC290927
0.8438	Intermediate Similarity	NPC145830
0.8434	Intermediate Similarity	NPC136641
0.8428	Intermediate Similarity	NPC226578
0.8424	Intermediate Similarity	NPC261184
0.8408	Intermediate Similarity	NPC97904
0.8405	Intermediate Similarity	NPC217602
0.8405	Intermediate Similarity	NPC472823
0.8405	Intermediate Similarity	NPC317900
0.8405	Intermediate Similarity	NPC476404
0.8405	Intermediate Similarity	NPC260902
0.8405	Intermediate Similarity	NPC473282
0.8405	Intermediate Similarity	NPC296957
0.8405	Intermediate Similarity	NPC294300
0.8405	Intermediate Similarity	NPC104380
0.8395	Intermediate Similarity	NPC148938
0.8377	Intermediate Similarity	NPC61157
0.8377	Intermediate Similarity	NPC218204
0.8377	Intermediate Similarity	NPC473681
0.8373	Intermediate Similarity	NPC109180
0.8364	Intermediate Similarity	NPC24761
0.8354	Intermediate Similarity	NPC476350
0.8354	Intermediate Similarity	NPC476349
0.8344	Intermediate Similarity	NPC247677
0.8344	Intermediate Similarity	NPC160015
0.8344	Intermediate Similarity	NPC304692
0.8333	Intermediate Similarity	NPC243577
0.8333	Intermediate Similarity	NPC235333
0.8333	Intermediate Similarity	NPC41719
0.8323	Intermediate Similarity	NPC116604
0.8313	Intermediate Similarity	NPC219861
0.8305	Intermediate Similarity	NPC60848
0.8303	Intermediate Similarity	NPC313368
0.8303	Intermediate Similarity	NPC18986
0.8302	Intermediate Similarity	NPC469425
0.8302	Intermediate Similarity	NPC252208
0.8293	Intermediate Similarity	NPC140952
0.8293	Intermediate Similarity	NPC268360
0.8293	Intermediate Similarity	NPC474611
0.8282	Intermediate Similarity	NPC104736
0.8282	Intermediate Similarity	NPC297531
0.8282	Intermediate Similarity	NPC213936
0.8274	Intermediate Similarity	NPC296558
0.8274	Intermediate Similarity	NPC53640
0.8272	Intermediate Similarity	NPC207624
0.8272	Intermediate Similarity	NPC253872
0.8266	Intermediate Similarity	NPC104682
0.8263	Intermediate Similarity	NPC100849
0.8263	Intermediate Similarity	NPC472581
0.8263	Intermediate Similarity	NPC121995
0.8261	Intermediate Similarity	NPC472406
0.8261	Intermediate Similarity	NPC13282
0.8253	Intermediate Similarity	NPC269117
0.8253	Intermediate Similarity	NPC224394
0.8253	Intermediate Similarity	NPC304387
0.8253	Intermediate Similarity	NPC663
0.825	Intermediate Similarity	NPC192069
0.8246	Intermediate Similarity	NPC167340
0.8232	Intermediate Similarity	NPC81405
0.8228	Intermediate Similarity	NPC114513
0.8228	Intermediate Similarity	NPC245522
0.8225	Intermediate Similarity	NPC476459
0.8221	Intermediate Similarity	NPC469966
0.8221	Intermediate Similarity	NPC208806
0.8221	Intermediate Similarity	NPC1477
0.8221	Intermediate Similarity	NPC158261
0.8221	Intermediate Similarity	NPC42458
0.8221	Intermediate Similarity	NPC84721
0.8221	Intermediate Similarity	NPC213608
0.8214	Intermediate Similarity	NPC314653
0.8214	Intermediate Similarity	NPC316262
0.821	Intermediate Similarity	NPC115324
0.821	Intermediate Similarity	NPC106372
0.821	Intermediate Similarity	NPC193976
0.821	Intermediate Similarity	NPC23668
0.821	Intermediate Similarity	NPC170169
0.821	Intermediate Similarity	NPC175617
0.821	Intermediate Similarity	NPC75906
0.821	Intermediate Similarity	NPC58668
0.8199	Intermediate Similarity	NPC296030
0.8199	Intermediate Similarity	NPC226644
0.8199	Intermediate Similarity	NPC37226
0.8199	Intermediate Similarity	NPC39929
0.8194	Intermediate Similarity	NPC265181
0.8193	Intermediate Similarity	NPC470810
0.8193	Intermediate Similarity	NPC284495
0.8187	Intermediate Similarity	NPC19747
0.8187	Intermediate Similarity	NPC198427
0.8182	Intermediate Similarity	NPC44199
0.8182	Intermediate Similarity	NPC269495
0.8182	Intermediate Similarity	NPC123153
0.8182	Intermediate Similarity	NPC65504
0.8182	Intermediate Similarity	NPC201127
0.8176	Intermediate Similarity	NPC63514
0.8176	Intermediate Similarity	NPC62799
0.8176	Intermediate Similarity	NPC478166
0.8171	Intermediate Similarity	NPC198490
0.8171	Intermediate Similarity	NPC99199
0.8171	Intermediate Similarity	NPC41880
0.8171	Intermediate Similarity	NPC228209
0.8166	Intermediate Similarity	NPC255787
0.8165	Intermediate Similarity	NPC117674
0.816	Intermediate Similarity	NPC154683
0.816	Intermediate Similarity	NPC471349
0.816	Intermediate Similarity	NPC38361
0.816	Intermediate Similarity	NPC40356
0.816	Intermediate Similarity	NPC142308
0.816	Intermediate Similarity	NPC5871
0.816	Intermediate Similarity	NPC67654
0.816	Intermediate Similarity	NPC471347
0.816	Intermediate Similarity	NPC130015
0.8155	Intermediate Similarity	NPC149945
0.8155	Intermediate Similarity	NPC132054
0.8155	Intermediate Similarity	NPC475779
0.8155	Intermediate Similarity	NPC476931
0.8153	Intermediate Similarity	NPC263337
0.8148	Intermediate Similarity	NPC148423
0.8148	Intermediate Similarity	NPC61258
0.8148	Intermediate Similarity	NPC167576
0.8148	Intermediate Similarity	NPC230713
0.8148	Intermediate Similarity	NPC202595
0.8148	Intermediate Similarity	NPC135303
0.8148	Intermediate Similarity	NPC78335
0.8144	Intermediate Similarity	NPC283209
0.8144	Intermediate Similarity	NPC288602
0.8144	Intermediate Similarity	NPC88841
0.814	Intermediate Similarity	NPC277510
0.8137	Intermediate Similarity	NPC135325
0.8133	Intermediate Similarity	NPC226287
0.8133	Intermediate Similarity	NPC472299
0.8133	Intermediate Similarity	NPC40583
0.8133	Intermediate Similarity	NPC472877
0.8133	Intermediate Similarity	NPC287559
0.8133	Intermediate Similarity	NPC250076
0.8133	Intermediate Similarity	NPC477692
0.8129	Intermediate Similarity	NPC315306
0.8129	Intermediate Similarity	NPC313717
0.8125	Intermediate Similarity	NPC471346
0.8125	Intermediate Similarity	NPC190572
0.8125	Intermediate Similarity	NPC281398
0.8121	Intermediate Similarity	NPC249021
0.8121	Intermediate Similarity	NPC472772
0.8118	Intermediate Similarity	NPC472660
0.8118	Intermediate Similarity	NPC95715
0.8118	Intermediate Similarity	NPC241820
0.8118	Intermediate Similarity	NPC186392
0.8113	Intermediate Similarity	NPC471451
0.8113	Intermediate Similarity	NPC27798
0.8113	Intermediate Similarity	NPC93241
0.811	Intermediate Similarity	NPC72370
0.811	Intermediate Similarity	NPC472462
0.811	Intermediate Similarity	NPC193200
0.811	Intermediate Similarity	NPC210942
0.811	Intermediate Similarity	NPC135522
0.811	Intermediate Similarity	NPC122365
0.811	Intermediate Similarity	NPC183874
0.811	Intermediate Similarity	NPC169990
0.8107	Intermediate Similarity	NPC476850
0.8107	Intermediate Similarity	NPC473753
0.8107	Intermediate Similarity	NPC476861
0.8107	Intermediate Similarity	NPC473766
0.8098	Intermediate Similarity	NPC230848
0.8098	Intermediate Similarity	NPC474417
0.8098	Intermediate Similarity	NPC478148
0.8098	Intermediate Similarity	NPC472423
0.8098	Intermediate Similarity	NPC474744
0.8098	Intermediate Similarity	NPC149526
0.8098	Intermediate Similarity	NPC156244
0.8098	Intermediate Similarity	NPC474772

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 NPC472781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	958
0.2-0.3	1577
0.3-0.4	2720
0.4-0.5	2091
0.5-0.6	995
0.6-0.7	350
0.7-0.8	119
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
0.8221	Intermediate Similarity	NPD5760	Phase 2
0.8221	Intermediate Similarity	NPD5761	Phase 2
0.8194	Intermediate Similarity	NPD1471	Phase 3
0.8114	Intermediate Similarity	NPD8434	Phase 2
0.795	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1247	Approved
0.7917	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3226	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.784	Intermediate Similarity	NPD2533	Approved
0.7798	Intermediate Similarity	NPD3882	Suspended
0.7784	Intermediate Similarity	NPD7819	Suspended
0.7744	Intermediate Similarity	NPD920	Approved
0.7727	Intermediate Similarity	NPD6764	Approved
0.7727	Intermediate Similarity	NPD6765	Approved
0.7727	Intermediate Similarity	NPD6559	Discontinued
0.7711	Intermediate Similarity	NPD6599	Discontinued
0.7679	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7411	Suspended
0.7647	Intermediate Similarity	NPD7075	Discontinued
0.7647	Intermediate Similarity	NPD3749	Approved
0.764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2346	Discontinued
0.7625	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6801	Discontinued
0.7616	Intermediate Similarity	NPD6959	Discontinued
0.7602	Intermediate Similarity	NPD919	Approved
0.7574	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6799	Approved
0.7556	Intermediate Similarity	NPD6784	Approved
0.7556	Intermediate Similarity	NPD6785	Approved
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2800	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD1607	Approved
0.7469	Intermediate Similarity	NPD1549	Phase 2
0.7458	Intermediate Similarity	NPD5844	Phase 1
0.7457	Intermediate Similarity	NPD5494	Approved
0.7453	Intermediate Similarity	NPD1551	Phase 2
0.7453	Intermediate Similarity	NPD2796	Approved
0.7407	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1510	Phase 2
0.7386	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6232	Discontinued
0.736	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1240	Approved
0.7345	Intermediate Similarity	NPD7473	Discontinued
0.7333	Intermediate Similarity	NPD2309	Approved
0.733	Intermediate Similarity	NPD3926	Phase 2
0.7326	Intermediate Similarity	NPD3817	Phase 2
0.7326	Intermediate Similarity	NPD5402	Approved
0.7317	Intermediate Similarity	NPD1243	Approved
0.731	Intermediate Similarity	NPD1934	Approved
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD3818	Discontinued
0.7303	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6166	Phase 2
0.7284	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD5710	Approved
0.7273	Intermediate Similarity	NPD3750	Approved
0.7273	Intermediate Similarity	NPD5711	Approved
0.7267	Intermediate Similarity	NPD2801	Approved
0.7262	Intermediate Similarity	NPD1512	Approved
0.7241	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2935	Discontinued
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD5403	Approved
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6002	Phase 3
0.7195	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6005	Phase 3
0.7195	Intermediate Similarity	NPD6004	Phase 3
0.7195	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7768	Phase 2
0.7178	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7033	Discontinued
0.7175	Intermediate Similarity	NPD3787	Discontinued
0.7173	Intermediate Similarity	NPD6782	Approved
0.7173	Intermediate Similarity	NPD6777	Approved
0.7173	Intermediate Similarity	NPD6778	Approved
0.7173	Intermediate Similarity	NPD6781	Approved
0.7173	Intermediate Similarity	NPD6779	Approved
0.7173	Intermediate Similarity	NPD6780	Approved
0.7173	Intermediate Similarity	NPD6776	Approved
0.716	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD1511	Approved
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7104	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5401	Approved
0.7088	Intermediate Similarity	NPD6797	Phase 2
0.7083	Intermediate Similarity	NPD7236	Approved
0.7081	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3748	Approved
0.7065	Intermediate Similarity	NPD8312	Approved
0.7065	Intermediate Similarity	NPD8313	Approved
0.7062	Intermediate Similarity	NPD7697	Approved
0.7062	Intermediate Similarity	NPD7696	Phase 3
0.7062	Intermediate Similarity	NPD7698	Approved
0.7049	Intermediate Similarity	NPD7251	Discontinued
0.7043	Intermediate Similarity	NPD8150	Discontinued
0.7026	Intermediate Similarity	NPD7871	Phase 2
0.7026	Intermediate Similarity	NPD7870	Phase 2
0.7022	Intermediate Similarity	NPD7199	Phase 2
0.7019	Intermediate Similarity	NPD3268	Approved
0.7019	Intermediate Similarity	NPD3764	Approved
0.7019	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7799	Discontinued
0.7011	Intermediate Similarity	NPD7808	Phase 3
0.7011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2403	Approved
0.7	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD6535	Approved
0.6995	Remote Similarity	NPD5953	Discontinued
0.6989	Remote Similarity	NPD4965	Approved
0.6989	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4966	Approved
0.6989	Remote Similarity	NPD4967	Phase 2
0.6983	Remote Similarity	NPD7229	Phase 3
0.6981	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8404	Phase 2
0.6978	Remote Similarity	NPD7286	Phase 2
0.6977	Remote Similarity	NPD7239	Suspended
0.697	Remote Similarity	NPD4308	Phase 3
0.6964	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1876	Approved
0.6957	Remote Similarity	NPD4625	Phase 3
0.6943	Remote Similarity	NPD3972	Approved
0.6941	Remote Similarity	NPD7390	Discontinued
0.694	Remote Similarity	NPD7074	Phase 3
0.6935	Remote Similarity	NPD7874	Approved
0.6935	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7177	Discontinued
0.6919	Remote Similarity	NPD7701	Phase 2
0.6914	Remote Similarity	NPD37	Approved
0.6906	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6832	Phase 2
0.6891	Remote Similarity	NPD7699	Phase 2
0.6891	Remote Similarity	NPD7700	Phase 2
0.689	Remote Similarity	NPD6355	Discontinued
0.6889	Remote Similarity	NPD6808	Phase 2
0.6886	Remote Similarity	NPD5762	Approved
0.6886	Remote Similarity	NPD5763	Approved
0.6885	Remote Similarity	NPD7054	Approved
0.6878	Remote Similarity	NPD4287	Approved
0.6864	Remote Similarity	NPD7003	Approved
0.6848	Remote Similarity	NPD7472	Approved
0.6848	Remote Similarity	NPD6651	Approved
0.6839	Remote Similarity	NPD7458	Discontinued
0.6836	Remote Similarity	NPD2296	Approved
0.6835	Remote Similarity	NPD1608	Approved
0.6831	Remote Similarity	NPD2163	Approved
0.6829	Remote Similarity	NPD4060	Phase 1
0.6826	Remote Similarity	NPD5406	Approved
0.6826	Remote Similarity	NPD5408	Approved
0.6826	Remote Similarity	NPD5405	Approved
0.6826	Remote Similarity	NPD5404	Approved
0.6821	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6279	Approved
0.6818	Remote Similarity	NPD6280	Approved
0.6816	Remote Similarity	NPD7801	Approved
0.6816	Remote Similarity	NPD6234	Discontinued
0.6813	Remote Similarity	NPD1203	Approved
0.6813	Remote Similarity	NPD1470	Approved
0.6802	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1651	Approved
0.6789	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1465	Phase 2
0.6774	Remote Similarity	NPD9092	Discovery
0.6772	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2798	Approved
0.6769	Remote Similarity	NPD8285	Discontinued
0.6768	Remote Similarity	NPD8320	Phase 1
0.6768	Remote Similarity	NPD8319	Approved
0.6763	Remote Similarity	NPD5049	Phase 3
0.6752	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6823	Phase 2
0.675	Remote Similarity	NPD1283	Approved
0.6748	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2424	Discontinued
0.6744	Remote Similarity	NPD6143	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