NPASS Compound

Structure

NPC474309 OpenBabel07101718292D 26 28 0 0 1 0 0 0 0 0999 V2000 -5.8690 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6906 3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 1.4781 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 -0.5878 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1064 1.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 1.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0526 2.4563 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 6 1 0 0 0 0 2 8 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 25 1 0 0 0 0 6 9 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 9 14 2 0 0 0 0 10 11 2 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 13 2 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.12
Volume:	354.587
LogP:	3.521
LogD:	2.313
LogS:	-3.675
# Rotatable Bonds:	3
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	4.087
Fsp3:	0.316
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:	-4.973
MDCK Permeability:	1.2193817383376881e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.118
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	97.72232818603516%
Volume Distribution (VD):	0.82
Pgp-substrate:	3.292656421661377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.393
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.299
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.21
CYP3A4-substrate:	0.799

ADMET: Excretion

Clearance (CL):	0.935
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.399
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.494
Skin Sensitization:	0.3
Carcinogencity:	0.544
Eye Corrosion:	0.003
Eye Irritation:	0.213
Respiratory Toxicity:	0.205

Download Data

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

Natural Product: NPC474309

Natural Product ID:	NPC474309
*Common Name:**	Annulin A
IUPAC Name:	methyl 6-ethyl-3,5-dihydroxy-1,1,7-trimethyl-4,9-dioxobenzo[f][2]benzofuran-3-carboxylate
Synonyms:
Standard InCHIKey:	YRVWWGFREKZPIN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O7/c1-6-9-8(2)7-10-11(14(9)20)16(22)13-12(15(10)21)18(3,4)26-19(13,24)17(23)25-5/h7,20,24H,6H2,1-5H3
SMILES:	COC(=O)C1(O)OC(C2=C1C(=O)c1c(C2=O)cc(c(c1O)CC)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465019
PubChem CID:	16059787
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
NPO2240	Garveia annulata	Species	Bougainvilliidae	Eukaryota	n.a.	Northeastern Pacific	n.a.	PMID[17067170]
NPO2240	Garveia annulata	Species	Bougainvilliidae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	Ki	=	690.0	nM	PMID[520804]

☑ 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 NPC474309 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	327
0.1-0.2	1389
0.2-0.3	3117
0.3-0.4	7396
0.4-0.5	11340
0.5-0.6	5742
0.6-0.7	9694
0.7-0.8	3547
0.8-0.85	133
0.85-0.9	10
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC475923
0.8767	High Similarity	NPC21873
0.8707	High Similarity	NPC103910
0.8652	High Similarity	NPC309430
0.8636	High Similarity	NPC29552
0.863	High Similarity	NPC257003
0.8627	High Similarity	NPC471456
0.8621	High Similarity	NPC471602
0.8621	High Similarity	NPC216312
0.8621	High Similarity	NPC29771
0.8621	High Similarity	NPC256463
0.8621	High Similarity	NPC476477
0.8621	High Similarity	NPC306835
0.8621	High Similarity	NPC111422
0.8621	High Similarity	NPC295339
0.8621	High Similarity	NPC299405
0.86	High Similarity	NPC470479
0.8592	High Similarity	NPC254603
0.8581	High Similarity	NPC29932
0.8562	High Similarity	NPC147542
0.8562	High Similarity	NPC327916
0.8562	High Similarity	NPC42262
0.8562	High Similarity	NPC241349
0.8562	High Similarity	NPC220496
0.8562	High Similarity	NPC32749
0.8562	High Similarity	NPC37992
0.8552	High Similarity	NPC61590
0.8523	High Similarity	NPC474630
0.8503	High Similarity	NPC471444
0.8477	Intermediate Similarity	NPC94781
0.8452	Intermediate Similarity	NPC478027
0.8446	Intermediate Similarity	NPC474300
0.8421	Intermediate Similarity	NPC44378
0.8421	Intermediate Similarity	NPC120171
0.8421	Intermediate Similarity	NPC280753
0.8389	Intermediate Similarity	NPC469885
0.8389	Intermediate Similarity	NPC476473
0.838	Intermediate Similarity	NPC198305
0.8366	Intermediate Similarity	NPC475717
0.8344	Intermediate Similarity	NPC120536
0.8344	Intermediate Similarity	NPC136878
0.8333	Intermediate Similarity	NPC274085
0.8333	Intermediate Similarity	NPC89664
0.8323	Intermediate Similarity	NPC312482
0.8313	Intermediate Similarity	NPC478026
0.8311	Intermediate Similarity	NPC315578
0.8301	Intermediate Similarity	NPC474310
0.8282	Intermediate Similarity	NPC183441
0.828	Intermediate Similarity	NPC208651
0.828	Intermediate Similarity	NPC206641
0.8267	Intermediate Similarity	NPC143898
0.8264	Intermediate Similarity	NPC88864
0.8255	Intermediate Similarity	NPC283292
0.8247	Intermediate Similarity	NPC31132
0.8243	Intermediate Similarity	NPC26924
0.8239	Intermediate Similarity	NPC165257
0.8239	Intermediate Similarity	NPC117985
0.8227	Intermediate Similarity	NPC231774
0.8217	Intermediate Similarity	NPC472050
0.8217	Intermediate Similarity	NPC272550
0.8207	Intermediate Similarity	NPC193169
0.8205	Intermediate Similarity	NPC474621
0.8205	Intermediate Similarity	NPC474622
0.8199	Intermediate Similarity	NPC329647
0.8199	Intermediate Similarity	NPC470735
0.8194	Intermediate Similarity	NPC205918
0.8182	Intermediate Similarity	NPC278928
0.8171	Intermediate Similarity	NPC270027
0.817	Intermediate Similarity	NPC469425
0.8165	Intermediate Similarity	NPC472889
0.816	Intermediate Similarity	NPC473096
0.816	Intermediate Similarity	NPC473095
0.8153	Intermediate Similarity	NPC3449
0.8153	Intermediate Similarity	NPC317585
0.8153	Intermediate Similarity	NPC174599
0.8153	Intermediate Similarity	NPC192219
0.8153	Intermediate Similarity	NPC82190
0.8153	Intermediate Similarity	NPC237560
0.8153	Intermediate Similarity	NPC478221
0.8141	Intermediate Similarity	NPC115249
0.8141	Intermediate Similarity	NPC180388
0.8138	Intermediate Similarity	NPC58685
0.8133	Intermediate Similarity	NPC176246
0.8129	Intermediate Similarity	NPC472891
0.8125	Intermediate Similarity	NPC317544
0.8121	Intermediate Similarity	NPC1268
0.8121	Intermediate Similarity	NPC103337
0.8121	Intermediate Similarity	NPC114620
0.8121	Intermediate Similarity	NPC65118
0.8112	Intermediate Similarity	NPC237225
0.811	Intermediate Similarity	NPC470580
0.8108	Intermediate Similarity	NPC471452
0.8105	Intermediate Similarity	NPC147250
0.8101	Intermediate Similarity	NPC283480
0.8101	Intermediate Similarity	NPC148323
0.8098	Intermediate Similarity	NPC473094
0.8092	Intermediate Similarity	NPC477409
0.8089	Intermediate Similarity	NPC478231
0.8089	Intermediate Similarity	NPC137301
0.8089	Intermediate Similarity	NPC471695
0.8086	Intermediate Similarity	NPC178281
0.8082	Intermediate Similarity	NPC171968
0.8077	Intermediate Similarity	NPC175617
0.8072	Intermediate Similarity	NPC19056
0.8072	Intermediate Similarity	NPC470583
0.8071	Intermediate Similarity	NPC307174
0.8069	Intermediate Similarity	NPC17083
0.8067	Intermediate Similarity	NPC168471
0.8065	Intermediate Similarity	NPC84142
0.8061	Intermediate Similarity	NPC473113
0.8052	Intermediate Similarity	NPC476821
0.8052	Intermediate Similarity	NPC53362
0.8052	Intermediate Similarity	NPC471734
0.8052	Intermediate Similarity	NPC119767
0.8052	Intermediate Similarity	NPC166583
0.8052	Intermediate Similarity	NPC5568
0.805	Intermediate Similarity	NPC246466
0.8049	Intermediate Similarity	NPC175477
0.8041	Intermediate Similarity	NPC315275
0.8039	Intermediate Similarity	NPC28632
0.8038	Intermediate Similarity	NPC170189
0.8038	Intermediate Similarity	NPC208173
0.8038	Intermediate Similarity	NPC472890
0.8028	Intermediate Similarity	NPC287473
0.8026	Intermediate Similarity	NPC471731
0.8026	Intermediate Similarity	NPC159721
0.8025	Intermediate Similarity	NPC474534
0.8025	Intermediate Similarity	NPC471349
0.8025	Intermediate Similarity	NPC474533
0.8025	Intermediate Similarity	NPC76041
0.8025	Intermediate Similarity	NPC471347
0.8025	Intermediate Similarity	NPC184284
0.8025	Intermediate Similarity	NPC478224
0.8014	Intermediate Similarity	NPC110609
0.8014	Intermediate Similarity	NPC246693
0.8014	Intermediate Similarity	NPC242358
0.8013	Intermediate Similarity	NPC149533
0.8013	Intermediate Similarity	NPC164762
0.8013	Intermediate Similarity	NPC205766
0.8013	Intermediate Similarity	NPC475407
0.8	Intermediate Similarity	NPC314795
0.8	Intermediate Similarity	NPC475741
0.8	Intermediate Similarity	NPC477408
0.8	Intermediate Similarity	NPC478021
0.8	Intermediate Similarity	NPC112816
0.7987	Intermediate Similarity	NPC477534
0.7987	Intermediate Similarity	NPC119542
0.7987	Intermediate Similarity	NPC285122
0.7987	Intermediate Similarity	NPC471735
0.7987	Intermediate Similarity	NPC154341
0.7987	Intermediate Similarity	NPC473023
0.7986	Intermediate Similarity	NPC217431
0.7986	Intermediate Similarity	NPC282923
0.7976	Intermediate Similarity	NPC470581
0.7976	Intermediate Similarity	NPC115447
0.7976	Intermediate Similarity	NPC266513
0.7976	Intermediate Similarity	NPC83331
0.7976	Intermediate Similarity	NPC470582
0.7975	Intermediate Similarity	NPC209393
0.7975	Intermediate Similarity	NPC198236
0.7975	Intermediate Similarity	NPC478022
0.7975	Intermediate Similarity	NPC478020
0.7975	Intermediate Similarity	NPC474301
0.7975	Intermediate Similarity	NPC205172
0.7974	Intermediate Similarity	NPC471305
0.7974	Intermediate Similarity	NPC469385
0.7974	Intermediate Similarity	NPC42540
0.7974	Intermediate Similarity	NPC151607
0.7973	Intermediate Similarity	NPC283088
0.7973	Intermediate Similarity	NPC161632
0.7973	Intermediate Similarity	NPC281513
0.7973	Intermediate Similarity	NPC27407
0.7973	Intermediate Similarity	NPC22222
0.7972	Intermediate Similarity	NPC51037
0.7972	Intermediate Similarity	NPC3224
0.7972	Intermediate Similarity	NPC306765
0.7963	Intermediate Similarity	NPC146837
0.7963	Intermediate Similarity	NPC187934
0.7963	Intermediate Similarity	NPC278329
0.7963	Intermediate Similarity	NPC97637
0.7962	Intermediate Similarity	NPC91809
0.7961	Intermediate Similarity	NPC322112
0.7961	Intermediate Similarity	NPC308572
0.7961	Intermediate Similarity	NPC314271
0.7961	Intermediate Similarity	NPC471733
0.7959	Intermediate Similarity	NPC115458
0.7958	Intermediate Similarity	NPC310540
0.7952	Intermediate Similarity	NPC294501
0.795	Intermediate Similarity	NPC313368
0.7949	Intermediate Similarity	NPC478219
0.7947	Intermediate Similarity	NPC327187
0.7939	Intermediate Similarity	NPC191653
0.7937	Intermediate Similarity	NPC478226
0.7937	Intermediate Similarity	NPC478225
0.7937	Intermediate Similarity	NPC476930
0.7933	Intermediate Similarity	NPC126739
0.7933	Intermediate Similarity	NPC173980
0.7933	Intermediate Similarity	NPC197666
0.7931	Intermediate Similarity	NPC131684
0.7931	Intermediate Similarity	NPC34414

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 NPC474309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	897
0.2-0.3	1675
0.3-0.4	2716
0.4-0.5	2121
0.5-0.6	1005
0.6-0.7	385
0.7-0.8	65
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7834	Intermediate Similarity	NPD3226	Approved
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7806	Intermediate Similarity	NPD2533	Approved
0.7806	Intermediate Similarity	NPD2532	Approved
0.7806	Intermediate Similarity	NPD2534	Approved
0.7803	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1470	Approved
0.7674	Intermediate Similarity	NPD8150	Discontinued
0.7632	Intermediate Similarity	NPD5405	Approved
0.7632	Intermediate Similarity	NPD5406	Approved
0.7632	Intermediate Similarity	NPD5408	Approved
0.7632	Intermediate Similarity	NPD5404	Approved
0.7571	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6232	Discontinued
0.7517	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6599	Discontinued
0.745	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6534	Approved
0.7416	Intermediate Similarity	NPD6535	Approved
0.7403	Intermediate Similarity	NPD2935	Discontinued
0.7377	Intermediate Similarity	NPD7435	Discontinued
0.7358	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3300	Phase 2
0.7338	Intermediate Similarity	NPD2799	Discontinued
0.7337	Intermediate Similarity	NPD8319	Approved
0.7337	Intermediate Similarity	NPD8320	Phase 1
0.7333	Intermediate Similarity	NPD3882	Suspended
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7819	Suspended
0.7305	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6799	Approved
0.7293	Intermediate Similarity	NPD7700	Phase 2
0.7293	Intermediate Similarity	NPD7699	Phase 2
0.7285	Intermediate Similarity	NPD2313	Discontinued
0.7283	Intermediate Similarity	NPD6559	Discontinued
0.7273	Intermediate Similarity	NPD5402	Approved
0.7256	Intermediate Similarity	NPD6801	Discontinued
0.7219	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD5710	Approved
0.7215	Intermediate Similarity	NPD4628	Phase 3
0.7213	Intermediate Similarity	NPD6777	Approved
0.7213	Intermediate Similarity	NPD6780	Approved
0.7213	Intermediate Similarity	NPD6778	Approved
0.7213	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD6776	Approved
0.7213	Intermediate Similarity	NPD6782	Approved
0.7213	Intermediate Similarity	NPD6781	Approved
0.7203	Intermediate Similarity	NPD9493	Approved
0.719	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2798	Approved
0.7115	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3750	Approved
0.7107	Intermediate Similarity	NPD8166	Discontinued
0.7081	Intermediate Similarity	NPD7390	Discontinued
0.7079	Intermediate Similarity	NPD8434	Phase 2
0.7078	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7458	Discontinued
0.7072	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6213	Phase 3
0.7072	Intermediate Similarity	NPD6212	Phase 3
0.707	Intermediate Similarity	NPD1551	Phase 2
0.7066	Intermediate Similarity	NPD3817	Phase 2
0.7063	Intermediate Similarity	NPD6190	Approved
0.7059	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD3751	Discontinued
0.7044	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2800	Approved
0.7037	Intermediate Similarity	NPD5401	Approved
0.7032	Intermediate Similarity	NPD447	Suspended
0.7032	Intermediate Similarity	NPD230	Phase 1
0.703	Intermediate Similarity	NPD4380	Phase 2
0.7025	Intermediate Similarity	NPD5763	Approved
0.7025	Intermediate Similarity	NPD5762	Approved
0.7025	Intermediate Similarity	NPD1471	Phase 3
0.7025	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4626	Approved
0.7006	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7696	Phase 3
0.7005	Intermediate Similarity	NPD7697	Approved
0.7005	Intermediate Similarity	NPD7698	Approved
0.7	Intermediate Similarity	NPD7003	Approved
0.6994	Remote Similarity	NPD5049	Phase 3
0.6987	Remote Similarity	NPD1607	Approved
0.6986	Remote Similarity	NPD9545	Approved
0.6982	Remote Similarity	NPD3749	Approved
0.6975	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD943	Approved
0.6968	Remote Similarity	NPD7871	Phase 2
0.6968	Remote Similarity	NPD7870	Phase 2
0.6959	Remote Similarity	NPD6959	Discontinued
0.6954	Remote Similarity	NPD3818	Discontinued
0.6954	Remote Similarity	NPD1164	Approved
0.6954	Remote Similarity	NPD7799	Discontinued
0.6949	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD411	Approved
0.6947	Remote Similarity	NPD7701	Phase 2
0.6941	Remote Similarity	NPD919	Approved
0.6941	Remote Similarity	NPD6234	Discontinued
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD7768	Phase 2
0.6918	Remote Similarity	NPD2344	Approved
0.6914	Remote Similarity	NPD5844	Phase 1
0.6905	Remote Similarity	NPD2801	Approved
0.6892	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1283	Approved
0.6886	Remote Similarity	NPD7411	Suspended
0.6882	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD9717	Approved
0.6862	Remote Similarity	NPD6823	Phase 2
0.6859	Remote Similarity	NPD1240	Approved
0.6845	Remote Similarity	NPD1934	Approved
0.6845	Remote Similarity	NPD37	Approved
0.6842	Remote Similarity	NPD1203	Approved
0.6842	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7801	Approved
0.6839	Remote Similarity	NPD7985	Registered
0.6836	Remote Similarity	NPD6797	Phase 2
0.6828	Remote Similarity	NPD5951	Approved
0.6824	Remote Similarity	NPD5691	Approved
0.6824	Remote Similarity	NPD4965	Approved
0.6824	Remote Similarity	NPD4966	Approved
0.6824	Remote Similarity	NPD4967	Phase 2
0.6824	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8151	Discontinued
0.681	Remote Similarity	NPD7236	Approved
0.6798	Remote Similarity	NPD8368	Discontinued
0.6798	Remote Similarity	NPD7251	Discontinued
0.6792	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4308	Phase 3
0.6792	Remote Similarity	NPD3748	Approved
0.6792	Remote Similarity	NPD1510	Phase 2
0.6788	Remote Similarity	NPD1512	Approved
0.6784	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2932	Approved
0.6778	Remote Similarity	NPD8407	Phase 2
0.6772	Remote Similarity	NPD6651	Approved
0.6761	Remote Similarity	NPD74	Approved
0.6761	Remote Similarity	NPD9266	Approved
0.6761	Remote Similarity	NPD7177	Discontinued
0.6761	Remote Similarity	NPD2182	Approved
0.6761	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7808	Phase 3
0.675	Remote Similarity	NPD6099	Approved
0.675	Remote Similarity	NPD6100	Approved
0.6748	Remote Similarity	NPD2309	Approved
0.6743	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6166	Phase 2
0.6743	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6798	Discontinued
0.6728	Remote Similarity	NPD1243	Approved
0.6724	Remote Similarity	NPD3787	Discontinued
0.6713	Remote Similarity	NPD2067	Discontinued
0.6712	Remote Similarity	NPD2629	Approved
0.671	Remote Similarity	NPD6832	Phase 2
0.6709	Remote Similarity	NPD1933	Approved
0.6707	Remote Similarity	NPD7239	Suspended
0.6706	Remote Similarity	NPD1465	Phase 2
0.6705	Remote Similarity	NPD5494	Approved
0.669	Remote Similarity	NPD9264	Approved
0.669	Remote Similarity	NPD9263	Approved
0.669	Remote Similarity	NPD9267	Approved
0.6689	Remote Similarity	NPD1281	Approved
0.6688	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD6273	Approved
0.6687	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3926	Phase 2
0.6686	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD6696	Suspended

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