NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.08
Volume:	247.06
LogP:	2.125
LogD:	1.796
LogS:	-3.468
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.808
Synthetic Accessibility Score:	3.458
Fsp3:	0.385
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:	-4.644
MDCK Permeability:	1.5142604752327316e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.548
Plasma Protein Binding (PPB):	85.36382293701172%
Volume Distribution (VD):	0.982
Pgp-substrate:	15.193205833435059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.831
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.219
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.357
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.271
CYP3A4-inhibitor:	0.201
CYP3A4-substrate:	0.475

ADMET: Excretion

Clearance (CL):	9.146
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.672
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.544
Skin Sensitization:	0.211
Carcinogencity:	0.034
Eye Corrosion:	0.093
Eye Irritation:	0.834
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC198927

Natural Product ID:	NPC198927
*Common Name:**	(3R)-3-Acetyl-7-Hydroxy-5-Methoxy-3,4-Dimethyl-2-Benzofuran-1-One
IUPAC Name:	(3R)-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethyl-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	MSFOCQWGXBBMOV-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C13H14O5/c1-6-9(17-4)5-8(15)10-11(6)13(3,7(2)14)18-12(10)16/h5,15H,1-4H3/t13-/m0/s1
SMILES:	COc1cc(O)c2c(c1C)[C@@](C)(OC2=O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765569
PubChem CID:	54587169
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11454459]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21265556]
NPO29951	Leptospeciesaeria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21265556]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5014	Organism	Cochliobolus miyabeanus	Cochliobolus miyabeanus	IC50	=	10.0	ug.mL-1	PMID[550277]

☑ 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 NPC198927 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	364
0.1-0.2	1794
0.2-0.3	4389
0.3-0.4	9691
0.4-0.5	8516
0.5-0.6	4141
0.6-0.7	6005
0.7-0.8	5993
0.8-0.85	1585
0.85-0.9	209
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9178	High Similarity	NPC473692
0.9167	High Similarity	NPC90411
0.9161	High Similarity	NPC275356
0.9128	High Similarity	NPC179178
0.9116	High Similarity	NPC260946
0.9073	High Similarity	NPC192189
0.9054	High Similarity	NPC14098
0.9026	High Similarity	NPC243701
0.9007	High Similarity	NPC271681
0.9	High Similarity	NPC119929
0.8968	High Similarity	NPC117985
0.8966	High Similarity	NPC165172
0.8933	High Similarity	NPC4423
0.8933	High Similarity	NPC77325
0.8919	High Similarity	NPC75694
0.8919	High Similarity	NPC28632
0.8912	High Similarity	NPC472006
0.8896	High Similarity	NPC473395
0.8889	High Similarity	NPC135837
0.8881	High Similarity	NPC180905
0.8881	High Similarity	NPC182496
0.8867	High Similarity	NPC153417
0.8859	High Similarity	NPC472033
0.8859	High Similarity	NPC107625
0.8844	High Similarity	NPC322112
0.8819	High Similarity	NPC50455
0.88	High Similarity	NPC137296
0.88	High Similarity	NPC8817
0.88	High Similarity	NPC472036
0.8792	High Similarity	NPC312789
0.8792	High Similarity	NPC472034
0.8784	High Similarity	NPC51106
0.8776	High Similarity	NPC244923
0.8776	High Similarity	NPC67650
0.8776	High Similarity	NPC1704
0.8774	High Similarity	NPC263483
0.8767	High Similarity	NPC52358
0.8766	High Similarity	NPC471456
0.8733	High Similarity	NPC470357
0.8693	High Similarity	NPC200773
0.8693	High Similarity	NPC240768
0.869	High Similarity	NPC158481
0.8675	High Similarity	NPC210320
0.8675	High Similarity	NPC166583
0.8675	High Similarity	NPC53362
0.8662	High Similarity	NPC313368
0.8658	High Similarity	NPC354984
0.8658	High Similarity	NPC469542
0.8654	High Similarity	NPC246466
0.8654	High Similarity	NPC476930
0.8649	High Similarity	NPC16455
0.8649	High Similarity	NPC37530
0.8649	High Similarity	NPC472603
0.8649	High Similarity	NPC307990
0.8649	High Similarity	NPC313123
0.8649	High Similarity	NPC478217
0.8645	High Similarity	NPC99381
0.8645	High Similarity	NPC79998
0.8639	High Similarity	NPC92655
0.8639	High Similarity	NPC88269
0.8639	High Similarity	NPC57380
0.8636	High Similarity	NPC175978
0.863	High Similarity	NPC194579
0.8627	High Similarity	NPC60413
0.8627	High Similarity	NPC158866
0.8627	High Similarity	NPC96501
0.8627	High Similarity	NPC470107
0.8618	High Similarity	NPC2569
0.8618	High Similarity	NPC215711
0.8618	High Similarity	NPC73411
0.8618	High Similarity	NPC172329
0.8618	High Similarity	NPC240253
0.8618	High Similarity	NPC470359
0.8618	High Similarity	NPC240622
0.8618	High Similarity	NPC471641
0.8618	High Similarity	NPC471642
0.8618	High Similarity	NPC37139
0.8611	High Similarity	NPC153783
0.8609	High Similarity	NPC163846
0.8609	High Similarity	NPC225173
0.8601	High Similarity	NPC189823
0.8601	High Similarity	NPC219892
0.8592	High Similarity	NPC230818
0.8591	High Similarity	NPC94076
0.8591	High Similarity	NPC250755
0.8591	High Similarity	NPC474385
0.8591	High Similarity	NPC182255
0.8591	High Similarity	NPC297985
0.8591	High Similarity	NPC82913
0.859	High Similarity	NPC474360
0.8581	High Similarity	NPC99441
0.8581	High Similarity	NPC472601
0.8581	High Similarity	NPC472600
0.8571	High Similarity	NPC191835
0.8571	High Similarity	NPC133856
0.8571	High Similarity	NPC95715
0.8562	High Similarity	NPC270160
0.8562	High Similarity	NPC233267
0.8562	High Similarity	NPC6923
0.8562	High Similarity	NPC291049
0.8562	High Similarity	NPC237440
0.8553	High Similarity	NPC125801
0.8553	High Similarity	NPC259632
0.8552	High Similarity	NPC175943
0.8543	High Similarity	NPC134621
0.8543	High Similarity	NPC316535
0.8542	High Similarity	NPC27490
0.8535	High Similarity	NPC474637
0.8533	High Similarity	NPC84266
0.8533	High Similarity	NPC162476
0.8533	High Similarity	NPC478202
0.8531	High Similarity	NPC84772
0.8526	High Similarity	NPC148938
0.8526	High Similarity	NPC199926
0.8523	High Similarity	NPC475730
0.8523	High Similarity	NPC472605
0.8523	High Similarity	NPC478201
0.8523	High Similarity	NPC220106
0.8523	High Similarity	NPC472035
0.8523	High Similarity	NPC472604
0.8519	High Similarity	NPC473096
0.8519	High Similarity	NPC473095
0.8516	High Similarity	NPC273483
0.8516	High Similarity	NPC217447
0.8514	High Similarity	NPC268052
0.8509	High Similarity	NPC62444
0.8506	High Similarity	NPC475717
0.8506	High Similarity	NPC202595
0.8506	High Similarity	NPC469619
0.8506	High Similarity	NPC295036
0.8506	High Similarity	NPC469670
0.8506	High Similarity	NPC116822
0.8506	High Similarity	NPC150928
0.8503	High Similarity	NPC474771
0.8503	High Similarity	NPC178467
0.8503	High Similarity	NPC65837
0.8503	High Similarity	NPC149372
0.8503	High Similarity	NPC474849
0.8503	High Similarity	NPC70380
0.8497	Intermediate Similarity	NPC211811
0.8497	Intermediate Similarity	NPC105415
0.8487	Intermediate Similarity	NPC267509
0.8487	Intermediate Similarity	NPC237208
0.8483	Intermediate Similarity	NPC48036
0.8481	Intermediate Similarity	NPC470339
0.8477	Intermediate Similarity	NPC66404
0.8477	Intermediate Similarity	NPC19896
0.8477	Intermediate Similarity	NPC184702
0.8477	Intermediate Similarity	NPC478203
0.8477	Intermediate Similarity	NPC210966
0.8477	Intermediate Similarity	NPC95123
0.8477	Intermediate Similarity	NPC470932
0.8477	Intermediate Similarity	NPC86373
0.8477	Intermediate Similarity	NPC126882
0.8477	Intermediate Similarity	NPC277426
0.8477	Intermediate Similarity	NPC210425
0.8477	Intermediate Similarity	NPC280404
0.8472	Intermediate Similarity	NPC324482
0.8471	Intermediate Similarity	NPC472050
0.8471	Intermediate Similarity	NPC180924
0.8471	Intermediate Similarity	NPC150227
0.8471	Intermediate Similarity	NPC146211
0.8467	Intermediate Similarity	NPC469579
0.8467	Intermediate Similarity	NPC105648
0.8467	Intermediate Similarity	NPC49108
0.8462	Intermediate Similarity	NPC301233
0.8462	Intermediate Similarity	NPC472799
0.8462	Intermediate Similarity	NPC235333
0.8457	Intermediate Similarity	NPC473094
0.8456	Intermediate Similarity	NPC187690
0.8456	Intermediate Similarity	NPC137009
0.8456	Intermediate Similarity	NPC37206
0.8452	Intermediate Similarity	NPC215921
0.8452	Intermediate Similarity	NPC115324
0.8452	Intermediate Similarity	NPC58668
0.8452	Intermediate Similarity	NPC106372
0.8452	Intermediate Similarity	NPC70016
0.8447	Intermediate Similarity	NPC314653
0.8447	Intermediate Similarity	NPC316262
0.8446	Intermediate Similarity	NPC212693
0.8446	Intermediate Similarity	NPC33144
0.8446	Intermediate Similarity	NPC478200
0.8446	Intermediate Similarity	NPC94248
0.8446	Intermediate Similarity	NPC475974
0.8446	Intermediate Similarity	NPC221104
0.8442	Intermediate Similarity	NPC84142
0.8442	Intermediate Similarity	NPC10027
0.8442	Intermediate Similarity	NPC65775
0.8438	Intermediate Similarity	NPC193998
0.8438	Intermediate Similarity	NPC94796
0.8435	Intermediate Similarity	NPC242712
0.8435	Intermediate Similarity	NPC84699
0.8435	Intermediate Similarity	NPC235115
0.8431	Intermediate Similarity	NPC312929
0.8431	Intermediate Similarity	NPC118027
0.8431	Intermediate Similarity	NPC56433
0.8431	Intermediate Similarity	NPC289042
0.8431	Intermediate Similarity	NPC22005
0.8431	Intermediate Similarity	NPC7943
0.8431	Intermediate Similarity	NPC123202

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 NPC198927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	1042
0.2-0.3	1948
0.3-0.4	2633
0.4-0.5	1793
0.5-0.6	922
0.6-0.7	317
0.7-0.8	134
0.8-0.85	13
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD2534	Approved
0.8919	High Similarity	NPD2533	Approved
0.8919	High Similarity	NPD2532	Approved
0.8767	High Similarity	NPD970	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2800	Approved
0.8301	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7819	Suspended
0.8098	Intermediate Similarity	NPD5710	Approved
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8098	Intermediate Similarity	NPD5711	Approved
0.8077	Intermediate Similarity	NPD920	Approved
0.8075	Intermediate Similarity	NPD3749	Approved
0.8075	Intermediate Similarity	NPD7075	Discontinued
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8041	Intermediate Similarity	NPD1240	Approved
0.8012	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7411	Suspended
0.7975	Intermediate Similarity	NPD3226	Approved
0.7974	Intermediate Similarity	NPD1243	Approved
0.7947	Intermediate Similarity	NPD1510	Phase 2
0.7937	Intermediate Similarity	NPD6801	Discontinued
0.7933	Intermediate Similarity	NPD1607	Approved
0.7927	Intermediate Similarity	NPD1247	Approved
0.7927	Intermediate Similarity	NPD6959	Discontinued
0.7914	Intermediate Similarity	NPD919	Approved
0.7898	Intermediate Similarity	NPD1512	Approved
0.7895	Intermediate Similarity	NPD2935	Discontinued
0.7888	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6799	Approved
0.7843	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3817	Phase 2
0.7834	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6599	Discontinued
0.7806	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD1549	Phase 2
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1511	Approved
0.7748	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1934	Approved
0.7712	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD4380	Phase 2
0.7697	Intermediate Similarity	NPD6651	Approved
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1465	Phase 2
0.7669	Intermediate Similarity	NPD2801	Approved
0.7628	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1471	Phase 3
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.7576	Intermediate Similarity	NPD7768	Phase 2
0.7574	Intermediate Similarity	NPD2403	Approved
0.7548	Intermediate Similarity	NPD1551	Phase 2
0.7545	Intermediate Similarity	NPD5494	Approved
0.7544	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5402	Approved
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD3748	Approved
0.7471	Intermediate Similarity	NPD6166	Phase 2
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7286	Phase 2
0.7442	Intermediate Similarity	NPD5844	Phase 1
0.7438	Intermediate Similarity	NPD7390	Discontinued
0.7436	Intermediate Similarity	NPD2796	Approved
0.7434	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3764	Approved
0.7414	Intermediate Similarity	NPD6559	Discontinued
0.7403	Intermediate Similarity	NPD447	Suspended
0.7389	Intermediate Similarity	NPD2344	Approved
0.7365	Intermediate Similarity	NPD9717	Approved
0.7356	Intermediate Similarity	NPD6797	Phase 2
0.7356	Intermediate Similarity	NPD5953	Discontinued
0.7353	Intermediate Similarity	NPD7229	Phase 3
0.7338	Intermediate Similarity	NPD943	Approved
0.7325	Intermediate Similarity	NPD6099	Approved
0.7325	Intermediate Similarity	NPD6100	Approved
0.7321	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2313	Discontinued
0.7314	Intermediate Similarity	NPD7251	Discontinued
0.731	Intermediate Similarity	NPD3926	Phase 2
0.7301	Intermediate Similarity	NPD5403	Approved
0.7296	Intermediate Similarity	NPD2654	Approved
0.7289	Intermediate Similarity	NPD37	Approved
0.7284	Intermediate Similarity	NPD5401	Approved
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.7262	Intermediate Similarity	NPD4966	Approved
0.726	Intermediate Similarity	NPD9545	Approved
0.7257	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9493	Approved
0.7219	Intermediate Similarity	NPD1203	Approved
0.7219	Intermediate Similarity	NPD7435	Discontinued
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD411	Approved
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7205	Intermediate Similarity	NPD2309	Approved
0.72	Intermediate Similarity	NPD7074	Phase 3
0.7195	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7181	Intermediate Similarity	NPD422	Phase 1
0.7176	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4626	Approved
0.7152	Intermediate Similarity	NPD1283	Approved
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7054	Approved
0.7133	Intermediate Similarity	NPD1608	Approved
0.7133	Intermediate Similarity	NPD9269	Phase 2
0.7127	Intermediate Similarity	NPD4287	Approved
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.7107	Intermediate Similarity	NPD5406	Approved
0.7107	Intermediate Similarity	NPD5408	Approved
0.7107	Intermediate Similarity	NPD5405	Approved
0.7107	Intermediate Similarity	NPD5404	Approved
0.7105	Intermediate Similarity	NPD1470	Approved
0.7102	Intermediate Similarity	NPD7472	Approved
0.7097	Intermediate Similarity	NPD3268	Approved
0.7095	Intermediate Similarity	NPD9268	Approved
0.7067	Intermediate Similarity	NPD1201	Approved
0.7063	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6778	Approved
0.7059	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD6781	Approved
0.7059	Intermediate Similarity	NPD6780	Approved
0.7059	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD6776	Approved
0.7059	Intermediate Similarity	NPD6777	Approved
0.7052	Intermediate Similarity	NPD3787	Discontinued
0.7037	Intermediate Similarity	NPD4628	Phase 3
0.7033	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1729	Discontinued
0.6995	Remote Similarity	NPD7874	Approved
0.6995	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7199	Phase 2
0.6993	Remote Similarity	NPD1164	Approved
0.6989	Remote Similarity	NPD7228	Approved
0.6989	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5691	Approved
0.6968	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6004	Phase 3
0.6957	Remote Similarity	NPD6002	Phase 3
0.6957	Remote Similarity	NPD6005	Phase 3
0.6957	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1281	Approved
0.6948	Remote Similarity	NPD1019	Discontinued
0.6947	Remote Similarity	NPD7697	Approved
0.6947	Remote Similarity	NPD7698	Approved
0.6947	Remote Similarity	NPD7696	Phase 3
0.6944	Remote Similarity	NPD8313	Approved
0.6944	Remote Similarity	NPD8312	Approved
0.6943	Remote Similarity	NPD8151	Discontinued
0.6937	Remote Similarity	NPD7033	Discontinued
0.6933	Remote Similarity	NPD17	Approved
0.6933	Remote Similarity	NPD7003	Approved
0.6928	Remote Similarity	NPD6696	Suspended
0.6927	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4625	Phase 3
0.6911	Remote Similarity	NPD7870	Phase 2
0.6911	Remote Similarity	NPD7871	Phase 2
0.6905	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4288	Approved
0.6898	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD405	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6190	Approved
0.6883	Remote Similarity	NPD3266	Approved
0.6883	Remote Similarity	NPD3267	Approved
0.6879	Remote Similarity	NPD1296	Phase 2
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6832	Phase 2
0.6855	Remote Similarity	NPD6355	Discontinued
0.6855	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5124	Phase 1
0.6839	Remote Similarity	NPD2798	Approved
0.6832	Remote Similarity	NPD4308	Phase 3
0.6824	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8320	Phase 1
0.6823	Remote Similarity	NPD8319	Approved
0.6805	Remote Similarity	NPD7458	Discontinued
0.6804	Remote Similarity	NPD7701	Phase 2
0.6795	Remote Similarity	NPD9494	Approved
0.6792	Remote Similarity	NPD2979	Phase 3
0.6791	Remote Similarity	NPD6534	Approved
0.6791	Remote Similarity	NPD6535	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data