NPASS Compound

Structure

CID127827 OpenBabel06191715482D 27 31 0 0 0 0 0 0 0 0999 V2000 -1.2024 6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2054 0.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 4.5827 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 -5.6176 -0.2263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 1.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 16 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 19 1 0 0 0 0 7 12 1 0 0 0 0 7 17 2 0 0 0 0 8 13 1 0 0 0 0 8 18 2 0 0 0 0 9 15 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 10 27 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 13 20 2 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 21 22 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.09
Volume:	358.003
LogP:	4.121
LogD:	3.439
LogS:	-6.268
# Rotatable Bonds:	3
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	2.488
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.043
MDCK Permeability:	6.621875945711508e-05
Pgp-inhibitor:	0.217
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	93.57903289794922%
Volume Distribution (VD):	0.947
Pgp-substrate:	1.6473346948623657%

ADMET: Metabolism

CYP1A2-inhibitor:	0.932
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.142
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.76
CYP2D6-substrate:	0.937
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	12.403
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.668
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.854
Skin Sensitization:	0.428
Carcinogencity:	0.889
Eye Corrosion:	0.003
Eye Irritation:	0.048
Respiratory Toxicity:	0.488

Download Data

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

Natural Product: NPC127827

Natural Product ID:	NPC127827
*Common Name:**	Retrojusticidin B
IUPAC Name:	4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
Synonyms:
Standard InCHIKey:	TXDMVCNSUVLKHW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H16O6/c1-23-17-7-12-5-14-15(9-25-21(14)22)20(13(12)8-18(17)24-2)11-3-4-16-19(6-11)27-10-26-16/h3-8H,9-10H2,1-2H3
SMILES:	COc1cc2c(cc1OC)cc1c(c2c2ccc3c(c2)OCO3)COC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL292540
PubChem CID:	460888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO19983	Phyllanthus myrtifolius	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946748]
NPO31495	Phyllanthus myritifolius	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19983	Phyllanthus myrtifolius	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19983	Phyllanthus myrtifolius	Species	Phyllanthaceae	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	4

Activity Type	# Activity
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	760.0	nM	PMID[470215]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	5500.0	nM	PMID[470216]
NPT2	Others	Unspecified		IC50	=	989000.0	nM	PMID[470216]
NPT2	Others	Unspecified		IC50	=	5500.0	nM	PMID[470217]

☑ 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 NPC127827 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	400
0.1-0.2	1680
0.2-0.3	3776
0.3-0.4	9780
0.4-0.5	8803
0.5-0.6	3841
0.6-0.7	10748
0.7-0.8	3502
0.8-0.85	115
0.85-0.9	36
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC475722
0.972	High Similarity	NPC24193
0.965	High Similarity	NPC181464
0.9396	High Similarity	NPC239113
0.9396	High Similarity	NPC115123
0.9392	High Similarity	NPC54179
0.9329	High Similarity	NPC234730
0.9211	High Similarity	NPC78944
0.9205	High Similarity	NPC19600
0.9145	High Similarity	NPC474043
0.9139	High Similarity	NPC473900
0.9128	High Similarity	NPC118332
0.9122	High Similarity	NPC261322
0.9091	High Similarity	NPC116838
0.9091	High Similarity	NPC22130
0.9034	High Similarity	NPC137920
0.9034	High Similarity	NPC125134
0.9034	High Similarity	NPC86455
0.9028	High Similarity	NPC246474
0.9028	High Similarity	NPC218092
0.9028	High Similarity	NPC162851
0.9026	High Similarity	NPC15212
0.8917	High Similarity	NPC471923
0.8896	High Similarity	NPC125713
0.8889	High Similarity	NPC109765
0.8861	High Similarity	NPC475453
0.8861	High Similarity	NPC473531
0.8846	High Similarity	NPC198796
0.8839	High Similarity	NPC65784
0.8831	High Similarity	NPC202495
0.8803	High Similarity	NPC205915
0.8797	High Similarity	NPC474042
0.8797	High Similarity	NPC174734
0.875	High Similarity	NPC102260
0.875	High Similarity	NPC230968
0.8696	High Similarity	NPC129930
0.8696	High Similarity	NPC471920
0.8696	High Similarity	NPC114550
0.8696	High Similarity	NPC473697
0.8696	High Similarity	NPC471921
0.8696	High Similarity	NPC312006
0.8696	High Similarity	NPC292712
0.8696	High Similarity	NPC474075
0.8696	High Similarity	NPC20114
0.8696	High Similarity	NPC471922
0.8688	High Similarity	NPC117911
0.8667	High Similarity	NPC104024
0.8667	High Similarity	NPC65574
0.8667	High Similarity	NPC304687
0.8667	High Similarity	NPC80230
0.8667	High Similarity	NPC101755
0.8662	High Similarity	NPC209411
0.8662	High Similarity	NPC239890
0.8662	High Similarity	NPC258322
0.8662	High Similarity	NPC191352
0.8645	High Similarity	NPC261484
0.8642	High Similarity	NPC184624
0.8618	High Similarity	NPC300983
0.8611	High Similarity	NPC19890
0.8611	High Similarity	NPC110958
0.8608	High Similarity	NPC19948
0.859	High Similarity	NPC143328
0.859	High Similarity	NPC82733
0.859	High Similarity	NPC76458
0.8589	High Similarity	NPC193377
0.8553	High Similarity	NPC177476
0.8553	High Similarity	NPC262455
0.8552	High Similarity	NPC89504
0.8552	High Similarity	NPC95485
0.8552	High Similarity	NPC88065
0.8537	High Similarity	NPC196771
0.8535	High Similarity	NPC15764
0.8535	High Similarity	NPC68619
0.8533	High Similarity	NPC91694
0.8533	High Similarity	NPC229787
0.8533	High Similarity	NPC300603
0.8511	High Similarity	NPC100129
0.8497	Intermediate Similarity	NPC149505
0.8487	Intermediate Similarity	NPC262804
0.8487	Intermediate Similarity	NPC40654
0.8485	Intermediate Similarity	NPC35266
0.8481	Intermediate Similarity	NPC139876
0.8452	Intermediate Similarity	NPC308555
0.8442	Intermediate Similarity	NPC210642
0.8442	Intermediate Similarity	NPC13985
0.8434	Intermediate Similarity	NPC275690
0.8434	Intermediate Similarity	NPC161609
0.8428	Intermediate Similarity	NPC309335
0.8428	Intermediate Similarity	NPC296540
0.8428	Intermediate Similarity	NPC319749
0.8421	Intermediate Similarity	NPC153620
0.8421	Intermediate Similarity	NPC39361
0.8421	Intermediate Similarity	NPC24257
0.8411	Intermediate Similarity	NPC472836
0.8395	Intermediate Similarity	NPC79322
0.8389	Intermediate Similarity	NPC282291
0.8389	Intermediate Similarity	NPC29599
0.8389	Intermediate Similarity	NPC166137
0.8387	Intermediate Similarity	NPC104353
0.838	Intermediate Similarity	NPC223807
0.838	Intermediate Similarity	NPC177167
0.8375	Intermediate Similarity	NPC280778
0.8344	Intermediate Similarity	NPC3273
0.8344	Intermediate Similarity	NPC475000
0.8344	Intermediate Similarity	NPC254163
0.8333	Intermediate Similarity	NPC210354
0.8333	Intermediate Similarity	NPC176586
0.8293	Intermediate Similarity	NPC52598
0.8291	Intermediate Similarity	NPC261090
0.8289	Intermediate Similarity	NPC327052
0.8289	Intermediate Similarity	NPC308006
0.8284	Intermediate Similarity	NPC114120
0.8284	Intermediate Similarity	NPC167045
0.828	Intermediate Similarity	NPC103197
0.828	Intermediate Similarity	NPC30009
0.828	Intermediate Similarity	NPC273578
0.828	Intermediate Similarity	NPC348849
0.828	Intermediate Similarity	NPC178195
0.8272	Intermediate Similarity	NPC474301
0.8272	Intermediate Similarity	NPC477884
0.8267	Intermediate Similarity	NPC28398
0.8264	Intermediate Similarity	NPC476748
0.8261	Intermediate Similarity	NPC61141
0.8258	Intermediate Similarity	NPC37220
0.825	Intermediate Similarity	NPC474770
0.8239	Intermediate Similarity	NPC17348
0.8239	Intermediate Similarity	NPC167098
0.8239	Intermediate Similarity	NPC296044
0.8235	Intermediate Similarity	NPC193779
0.8224	Intermediate Similarity	NPC46880
0.8224	Intermediate Similarity	NPC177644
0.8224	Intermediate Similarity	NPC191158
0.8221	Intermediate Similarity	NPC118162
0.8221	Intermediate Similarity	NPC83049
0.8221	Intermediate Similarity	NPC320471
0.8212	Intermediate Similarity	NPC40237
0.8212	Intermediate Similarity	NPC151423
0.82	Intermediate Similarity	NPC223336
0.8199	Intermediate Similarity	NPC99968
0.8199	Intermediate Similarity	NPC109238
0.8194	Intermediate Similarity	NPC472839
0.8194	Intermediate Similarity	NPC95526
0.8187	Intermediate Similarity	NPC313063
0.8187	Intermediate Similarity	NPC286301
0.8187	Intermediate Similarity	NPC325122
0.8176	Intermediate Similarity	NPC301897
0.8176	Intermediate Similarity	NPC32373
0.8176	Intermediate Similarity	NPC213401
0.8176	Intermediate Similarity	NPC237946
0.8171	Intermediate Similarity	NPC311912
0.817	Intermediate Similarity	NPC290038
0.817	Intermediate Similarity	NPC474158
0.817	Intermediate Similarity	NPC471305
0.8158	Intermediate Similarity	NPC141817
0.8158	Intermediate Similarity	NPC176030
0.8158	Intermediate Similarity	NPC192597
0.8158	Intermediate Similarity	NPC169214
0.8158	Intermediate Similarity	NPC229218
0.8141	Intermediate Similarity	NPC474305
0.8137	Intermediate Similarity	NPC96593
0.8137	Intermediate Similarity	NPC470637
0.8133	Intermediate Similarity	NPC178290
0.8125	Intermediate Similarity	NPC19947
0.8125	Intermediate Similarity	NPC286683
0.8125	Intermediate Similarity	NPC115281
0.8125	Intermediate Similarity	NPC428300
0.8125	Intermediate Similarity	NPC207584
0.8125	Intermediate Similarity	NPC163527
0.8125	Intermediate Similarity	NPC181168
0.8121	Intermediate Similarity	NPC90431
0.8121	Intermediate Similarity	NPC88557
0.8117	Intermediate Similarity	NPC189054
0.8113	Intermediate Similarity	NPC472835
0.8105	Intermediate Similarity	NPC474036
0.8105	Intermediate Similarity	NPC15743
0.8105	Intermediate Similarity	NPC218841
0.8105	Intermediate Similarity	NPC92693
0.8101	Intermediate Similarity	NPC3744
0.8101	Intermediate Similarity	NPC137125
0.8098	Intermediate Similarity	NPC100420
0.8089	Intermediate Similarity	NPC295977
0.8089	Intermediate Similarity	NPC58310
0.8089	Intermediate Similarity	NPC303519
0.8086	Intermediate Similarity	NPC288149
0.8077	Intermediate Similarity	NPC474306
0.8077	Intermediate Similarity	NPC475848
0.8039	Intermediate Similarity	NPC474288
0.8038	Intermediate Similarity	NPC220577
0.8038	Intermediate Similarity	NPC267091
0.8038	Intermediate Similarity	NPC306011
0.8038	Intermediate Similarity	NPC70320
0.8038	Intermediate Similarity	NPC472838
0.8026	Intermediate Similarity	NPC323601
0.8025	Intermediate Similarity	NPC268718
0.8025	Intermediate Similarity	NPC150943
0.8025	Intermediate Similarity	NPC218471
0.8025	Intermediate Similarity	NPC472298
0.8025	Intermediate Similarity	NPC119910
0.8025	Intermediate Similarity	NPC239818
0.8025	Intermediate Similarity	NPC91634

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 NPC127827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	982
0.2-0.3	1398
0.3-0.4	2600
0.4-0.5	2021
0.5-0.6	1158
0.6-0.7	530
0.7-0.8	100
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8411	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4966	Approved
0.8176	Intermediate Similarity	NPD4965	Approved
0.8176	Intermediate Similarity	NPD4967	Phase 2
0.8075	Intermediate Similarity	NPD6234	Discontinued
0.7987	Intermediate Similarity	NPD37	Approved
0.7973	Intermediate Similarity	NPD2979	Phase 3
0.7958	Intermediate Similarity	NPD1281	Approved
0.7947	Intermediate Similarity	NPD2438	Suspended
0.7927	Intermediate Similarity	NPD6232	Discontinued
0.7911	Intermediate Similarity	NPD7458	Discontinued
0.7904	Intermediate Similarity	NPD5844	Phase 1
0.7891	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7003	Approved
0.7793	Intermediate Similarity	NPD1283	Approved
0.7784	Intermediate Similarity	NPD7473	Discontinued
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.775	Intermediate Similarity	NPD7028	Phase 2
0.7746	Intermediate Similarity	NPD1651	Approved
0.7738	Intermediate Similarity	NPD7228	Approved
0.7722	Intermediate Similarity	NPD6273	Approved
0.7712	Intermediate Similarity	NPD2531	Phase 2
0.7688	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1933	Approved
0.7665	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7622	Intermediate Similarity	NPD5691	Approved
0.76	Intermediate Similarity	NPD3764	Approved
0.7586	Intermediate Similarity	NPD3705	Approved
0.7586	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7240	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7485	Intermediate Similarity	NPD6873	Phase 2
0.7485	Intermediate Similarity	NPD5494	Approved
0.7483	Intermediate Similarity	NPD5536	Phase 2
0.7457	Intermediate Similarity	NPD6559	Discontinued
0.7452	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8032	Phase 2
0.7432	Intermediate Similarity	NPD1876	Approved
0.7429	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2799	Discontinued
0.7415	Intermediate Similarity	NPD3972	Approved
0.7405	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4110	Phase 3
0.7378	Intermediate Similarity	NPD6386	Approved
0.7378	Intermediate Similarity	NPD6385	Approved
0.7372	Intermediate Similarity	NPD2935	Discontinued
0.7371	Intermediate Similarity	NPD8313	Approved
0.7371	Intermediate Similarity	NPD8312	Approved
0.7362	Intermediate Similarity	NPD3226	Approved
0.7337	Intermediate Similarity	NPD8127	Discontinued
0.7329	Intermediate Similarity	NPD4626	Approved
0.7326	Intermediate Similarity	NPD3818	Discontinued
0.7324	Intermediate Similarity	NPD5283	Phase 1
0.7321	Intermediate Similarity	NPD919	Approved
0.7305	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8166	Discontinued
0.7289	Intermediate Similarity	NPD7819	Suspended
0.7268	Intermediate Similarity	NPD4420	Approved
0.7257	Intermediate Similarity	NPD7685	Pre-registration
0.7255	Intermediate Similarity	NPD6798	Discontinued
0.725	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5977	Approved
0.7246	Intermediate Similarity	NPD5978	Approved
0.7246	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2533	Approved
0.7222	Intermediate Similarity	NPD2534	Approved
0.7222	Intermediate Similarity	NPD2532	Approved
0.7219	Intermediate Similarity	NPD2798	Approved
0.7197	Intermediate Similarity	NPD3748	Approved
0.7186	Intermediate Similarity	NPD8455	Phase 2
0.7182	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD9494	Approved
0.7161	Intermediate Similarity	NPD4060	Phase 1
0.7161	Intermediate Similarity	NPD4307	Phase 2
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7151	Intermediate Similarity	NPD5242	Approved
0.7151	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7133	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7125	Intermediate Similarity	NPD6674	Discontinued
0.7124	Intermediate Similarity	NPD6832	Phase 2
0.7117	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD447	Suspended
0.7114	Intermediate Similarity	NPD1611	Approved
0.7113	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5005	Approved
0.7112	Intermediate Similarity	NPD5006	Approved
0.7107	Intermediate Similarity	NPD1471	Phase 3
0.7101	Intermediate Similarity	NPD3882	Suspended
0.7101	Intermediate Similarity	NPD7768	Phase 2
0.7097	Intermediate Similarity	NPD6233	Phase 2
0.7095	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1465	Phase 2
0.7078	Intermediate Similarity	NPD7008	Discontinued
0.7078	Intermediate Similarity	NPD7095	Approved
0.7062	Intermediate Similarity	NPD7039	Approved
0.7062	Intermediate Similarity	NPD7038	Approved
0.7051	Intermediate Similarity	NPD4140	Approved
0.7044	Intermediate Similarity	NPD4477	Approved
0.7044	Intermediate Similarity	NPD4476	Approved
0.7037	Intermediate Similarity	NPD3887	Approved
0.7035	Intermediate Similarity	NPD1247	Approved
0.7029	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1358	Approved
0.7014	Intermediate Similarity	NPD5535	Approved
0.7012	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6599	Discontinued
0.7006	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3657	Discovery
0.7	Intermediate Similarity	NPD2344	Approved
0.6994	Remote Similarity	NPD7229	Phase 3
0.6987	Remote Similarity	NPD6663	Approved
0.6984	Remote Similarity	NPD7680	Approved
0.6982	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4108	Discontinued
0.6981	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD17	Approved
0.6975	Remote Similarity	NPD3750	Approved
0.6966	Remote Similarity	NPD1241	Discontinued
0.6964	Remote Similarity	NPD7411	Suspended
0.6959	Remote Similarity	NPD3749	Approved
0.6957	Remote Similarity	NPD2897	Discontinued
0.6952	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7074	Phase 3
0.6943	Remote Similarity	NPD3620	Phase 2
0.6943	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6959	Discontinued
0.6928	Remote Similarity	NPD920	Approved
0.6927	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1934	Approved
0.6923	Remote Similarity	NPD7693	Approved
0.6918	Remote Similarity	NPD7097	Phase 1
0.6913	Remote Similarity	NPD5585	Approved
0.6913	Remote Similarity	NPD1357	Approved
0.6911	Remote Similarity	NPD7999	Approved
0.6908	Remote Similarity	NPD5327	Phase 3
0.6894	Remote Similarity	NPD7266	Discontinued
0.6894	Remote Similarity	NPD2353	Approved
0.6894	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7054	Approved
0.6891	Remote Similarity	NPD8151	Discontinued
0.689	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7440	Discontinued
0.6887	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2801	Approved
0.686	Remote Similarity	NPD7075	Discontinued
0.6854	Remote Similarity	NPD7472	Approved
0.6853	Remote Similarity	NPD2182	Approved
0.6848	Remote Similarity	NPD6799	Approved
0.6845	Remote Similarity	NPD3455	Phase 2
0.6842	Remote Similarity	NPD5353	Approved
0.6842	Remote Similarity	NPD1608	Approved
0.6839	Remote Similarity	NPD5736	Approved
0.6832	Remote Similarity	NPD2796	Approved
0.6831	Remote Similarity	NPD3134	Approved
0.6829	Remote Similarity	NPD2309	Approved
0.6829	Remote Similarity	NPD6190	Approved
0.6826	Remote Similarity	NPD7427	Discontinued
0.6824	Remote Similarity	NPD6801	Discontinued
0.6818	Remote Similarity	NPD3266	Approved
0.6818	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3267	Approved
0.6818	Remote Similarity	NPD6166	Phase 2
0.6818	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2797	Approved
0.6818	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1243	Approved
0.6807	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7435	Discontinued
0.6803	Remote Similarity	NPD5951	Approved
0.6802	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6808	Phase 2
0.68	Remote Similarity	NPD3025	Approved
0.68	Remote Similarity	NPD3024	Approved
0.6792	Remote Similarity	NPD230	Phase 1
0.6788	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4062	Phase 3
0.6766	Remote Similarity	NPD5049	Phase 3
0.6763	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4859	Phase 1
0.675	Remote Similarity	NPD2492	Phase 1
0.675	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD970	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7808	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