NPASS Compound

Structure

CID278076 OpenBabel06191716082D 27 30 0 0 1 0 0 0 0 0999 V2000 1.1767 -3.9451 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 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 -3.0316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6705 -2.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 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 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 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 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 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 -4.5659 -1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 -2.4182 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 5 2 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 8 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 11 26 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 6 0 0 0 14 15 2 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 18 13 1 6 0 0 0 18 27 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	371.832
LogP:	3.167
LogD:	3.058
LogS:	-4.563
# Rotatable Bonds:	5
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	4.35
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.517
MDCK Permeability:	2.081900674966164e-05
Pgp-inhibitor:	0.891
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	93.98554992675781%
Volume Distribution (VD):	0.813
Pgp-substrate:	4.963858604431152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.896
CYP2C19-inhibitor:	0.98
CYP2C19-substrate:	0.679
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.554
CYP2D6-inhibitor:	0.982
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.982
CYP3A4-substrate:	0.544

ADMET: Excretion

Clearance (CL):	10.243
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.838
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.771
Skin Sensitization:	0.466
Carcinogencity:	0.921
Eye Corrosion:	0.004
Eye Irritation:	0.027
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC278076

Natural Product ID:	NPC278076
*Common Name:**	(2R,3S,3As)-2-(1,3-Benzodioxol-5-Yl)-5,7-Dimethoxy-3-Methyl-3A-Prop-2-Enyl-2,3-Dihydro-1-Benzofuran-6-One
IUPAC Name:	(2R,3S,3aS)-2-(1,3-benzodioxol-5-yl)-5,7-dimethoxy-3-methyl-3a-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
Synonyms:
Standard InCHIKey:	GAIYJSQKRRARSH-HXGDPMPDSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-5-8-21-10-16(23-3)17(22)19(24-4)20(21)27-18(12(21)2)13-6-7-14-15(9-13)26-11-25-14/h5-7,9-10,12,18H,1,8,11H2,2-4H3/t12-,18-,21-/m1/s1
SMILES:	C=CC[C@]12C=C(OC)C(=O)C(=C1O[C@H]([C@H]2C)c1ccc2c(c1)OCO2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1888377
PubChem CID:	15126682
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO21557	Woodsia manchuriensis	Species	Woodsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10293	Diaporthe phaseolorum	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2243	Euphorbia splendens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9616	Lunasia costulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8072	Rudbeckia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9108	Leptotaenia multifida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2649	Ocotea aciphylla	Species	Lauraceae	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
Potency	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[512097]
NPT2	Others	Unspecified		Potency	n.a.	1412.5	nM	PMID[512097]

☑ 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 NPC278076 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	440
0.1-0.2	1380
0.2-0.3	3323
0.3-0.4	8243
0.4-0.5	10917
0.5-0.6	5408
0.6-0.7	10727
0.7-0.8	2061
0.8-0.85	155
0.85-0.9	35
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC50696
0.9407	High Similarity	NPC166184
0.9357	High Similarity	NPC25496
0.9338	High Similarity	NPC178290
0.9161	High Similarity	NPC475170
0.9007	High Similarity	NPC15743
0.8889	High Similarity	NPC233961
0.8889	High Similarity	NPC280399
0.8889	High Similarity	NPC339621
0.8881	High Similarity	NPC226862
0.8881	High Similarity	NPC165128
0.8881	High Similarity	NPC158471
0.8881	High Similarity	NPC57119
0.8865	High Similarity	NPC476842
0.8865	High Similarity	NPC476840
0.8851	High Similarity	NPC117154
0.8824	High Similarity	NPC82111
0.8824	High Similarity	NPC227160
0.8794	High Similarity	NPC51681
0.8759	High Similarity	NPC7744
0.875	High Similarity	NPC271208
0.875	High Similarity	NPC233224
0.8705	High Similarity	NPC174191
0.8696	High Similarity	NPC266848
0.8696	High Similarity	NPC136750
0.8671	High Similarity	NPC474966
0.8667	High Similarity	NPC64948
0.8633	High Similarity	NPC145769
0.8623	High Similarity	NPC171928
0.8623	High Similarity	NPC100223
0.8623	High Similarity	NPC65183
0.8623	High Similarity	NPC16830
0.8623	High Similarity	NPC261812
0.8623	High Similarity	NPC158526
0.8623	High Similarity	NPC33611
0.8623	High Similarity	NPC72046
0.8623	High Similarity	NPC129687
0.8582	High Similarity	NPC34902
0.8582	High Similarity	NPC18449
0.8582	High Similarity	NPC121783
0.8571	High Similarity	NPC189474
0.8571	High Similarity	NPC474139
0.8552	High Similarity	NPC476841
0.8552	High Similarity	NPC476843
0.8551	High Similarity	NPC192255
0.854	High Similarity	NPC476748
0.8519	High Similarity	NPC85830
0.8511	High Similarity	NPC11453
0.85	High Similarity	NPC90083
0.85	High Similarity	NPC47181
0.85	High Similarity	NPC170779
0.85	High Similarity	NPC37065
0.85	High Similarity	NPC31530
0.8489	Intermediate Similarity	NPC219671
0.8489	Intermediate Similarity	NPC259742
0.8489	Intermediate Similarity	NPC147616
0.8489	Intermediate Similarity	NPC104077
0.844	Intermediate Similarity	NPC18576
0.844	Intermediate Similarity	NPC49235
0.844	Intermediate Similarity	NPC142547
0.844	Intermediate Similarity	NPC135777
0.844	Intermediate Similarity	NPC148893
0.844	Intermediate Similarity	NPC25333
0.8394	Intermediate Similarity	NPC158737
0.8392	Intermediate Similarity	NPC123526
0.8392	Intermediate Similarity	NPC88640
0.8392	Intermediate Similarity	NPC193666
0.8389	Intermediate Similarity	NPC12854
0.838	Intermediate Similarity	NPC121651
0.838	Intermediate Similarity	NPC143895
0.8358	Intermediate Similarity	NPC80241
0.8358	Intermediate Similarity	NPC65933
0.8358	Intermediate Similarity	NPC172676
0.8358	Intermediate Similarity	NPC114845
0.8358	Intermediate Similarity	NPC301641
0.8358	Intermediate Similarity	NPC57268
0.8358	Intermediate Similarity	NPC216929
0.8358	Intermediate Similarity	NPC312713
0.8358	Intermediate Similarity	NPC126935
0.8345	Intermediate Similarity	NPC287124
0.8345	Intermediate Similarity	NPC46180
0.8344	Intermediate Similarity	NPC308555
0.8333	Intermediate Similarity	NPC222127
0.8333	Intermediate Similarity	NPC82862
0.8322	Intermediate Similarity	NPC85141
0.8322	Intermediate Similarity	NPC101807
0.8322	Intermediate Similarity	NPC469981
0.8322	Intermediate Similarity	NPC185908
0.8296	Intermediate Similarity	NPC256167
0.8291	Intermediate Similarity	NPC42230
0.8291	Intermediate Similarity	NPC474948
0.8276	Intermediate Similarity	NPC312199
0.8267	Intermediate Similarity	NPC177830
0.8264	Intermediate Similarity	NPC156376
0.8264	Intermediate Similarity	NPC113550
0.8261	Intermediate Similarity	NPC473093
0.8261	Intermediate Similarity	NPC8050
0.8261	Intermediate Similarity	NPC473092
0.8243	Intermediate Similarity	NPC472560
0.8235	Intermediate Similarity	NPC254163
0.8235	Intermediate Similarity	NPC476363
0.8231	Intermediate Similarity	NPC475000
0.8231	Intermediate Similarity	NPC477701
0.8231	Intermediate Similarity	NPC166884
0.8231	Intermediate Similarity	NPC141569
0.8227	Intermediate Similarity	NPC471505
0.8222	Intermediate Similarity	NPC193484
0.8219	Intermediate Similarity	NPC80326
0.8219	Intermediate Similarity	NPC210354
0.8219	Intermediate Similarity	NPC246947
0.8219	Intermediate Similarity	NPC176586
0.8219	Intermediate Similarity	NPC472562
0.8212	Intermediate Similarity	NPC163002
0.8209	Intermediate Similarity	NPC344161
0.8207	Intermediate Similarity	NPC216434
0.8207	Intermediate Similarity	NPC46591
0.8207	Intermediate Similarity	NPC177868
0.8207	Intermediate Similarity	NPC103448
0.8201	Intermediate Similarity	NPC54321
0.8201	Intermediate Similarity	NPC281864
0.8201	Intermediate Similarity	NPC328682
0.82	Intermediate Similarity	NPC472567
0.8199	Intermediate Similarity	NPC474568
0.8194	Intermediate Similarity	NPC475095
0.8194	Intermediate Similarity	NPC14022
0.8194	Intermediate Similarity	NPC283949
0.8188	Intermediate Similarity	NPC153620
0.8188	Intermediate Similarity	NPC50683
0.8188	Intermediate Similarity	NPC206882
0.8188	Intermediate Similarity	NPC112571
0.8188	Intermediate Similarity	NPC24257
0.8188	Intermediate Similarity	NPC40352
0.8188	Intermediate Similarity	NPC285725
0.8188	Intermediate Similarity	NPC213711
0.8188	Intermediate Similarity	NPC476336
0.8182	Intermediate Similarity	NPC184938
0.8182	Intermediate Similarity	NPC101624
0.8182	Intermediate Similarity	NPC150534
0.8176	Intermediate Similarity	NPC477702
0.8176	Intermediate Similarity	NPC474158
0.8169	Intermediate Similarity	NPC205915
0.8169	Intermediate Similarity	NPC196937
0.8169	Intermediate Similarity	NPC1474
0.8165	Intermediate Similarity	NPC475953
0.8163	Intermediate Similarity	NPC477898
0.8163	Intermediate Similarity	NPC255566
0.8163	Intermediate Similarity	NPC265154
0.8163	Intermediate Similarity	NPC298317
0.8163	Intermediate Similarity	NPC472564
0.8156	Intermediate Similarity	NPC115207
0.8156	Intermediate Similarity	NPC40432
0.8156	Intermediate Similarity	NPC161557
0.8156	Intermediate Similarity	NPC158079
0.8156	Intermediate Similarity	NPC228346
0.8156	Intermediate Similarity	NPC27843
0.8156	Intermediate Similarity	NPC7171
0.8151	Intermediate Similarity	NPC471908
0.8151	Intermediate Similarity	NPC58137
0.8151	Intermediate Similarity	NPC300798
0.8138	Intermediate Similarity	NPC226005
0.8134	Intermediate Similarity	NPC69670
0.8133	Intermediate Similarity	NPC252281
0.8133	Intermediate Similarity	NPC477375
0.8133	Intermediate Similarity	NPC198129
0.8133	Intermediate Similarity	NPC327352
0.8125	Intermediate Similarity	NPC102260
0.8125	Intermediate Similarity	NPC230968
0.8121	Intermediate Similarity	NPC212890
0.8121	Intermediate Similarity	NPC193779
0.8121	Intermediate Similarity	NPC3982
0.8112	Intermediate Similarity	NPC67247
0.8108	Intermediate Similarity	NPC177644
0.8108	Intermediate Similarity	NPC191158
0.8108	Intermediate Similarity	NPC84181
0.8099	Intermediate Similarity	NPC181049
0.8099	Intermediate Similarity	NPC106739
0.8099	Intermediate Similarity	NPC207400
0.8095	Intermediate Similarity	NPC474295
0.8095	Intermediate Similarity	NPC311057
0.8095	Intermediate Similarity	NPC151423
0.8095	Intermediate Similarity	NPC174522
0.8095	Intermediate Similarity	NPC40237
0.8095	Intermediate Similarity	NPC67467
0.8095	Intermediate Similarity	NPC302506
0.8085	Intermediate Similarity	NPC134764
0.8085	Intermediate Similarity	NPC171550
0.8082	Intermediate Similarity	NPC56091
0.8082	Intermediate Similarity	NPC470855
0.8082	Intermediate Similarity	NPC322021
0.8082	Intermediate Similarity	NPC226547
0.8079	Intermediate Similarity	NPC477374
0.8079	Intermediate Similarity	NPC322426
0.8079	Intermediate Similarity	NPC477376
0.8077	Intermediate Similarity	NPC68619
0.8071	Intermediate Similarity	NPC470084
0.8065	Intermediate Similarity	NPC11411
0.8058	Intermediate Similarity	NPC88297
0.8058	Intermediate Similarity	NPC9891
0.8058	Intermediate Similarity	NPC186845
0.8056	Intermediate Similarity	NPC55040

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 NPC278076 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	845
0.2-0.3	1794
0.3-0.4	2773
0.4-0.5	1880
0.5-0.6	1037
0.6-0.7	441
0.7-0.8	35
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
0.8358	Intermediate Similarity	NPD3705	Approved
0.7737	Intermediate Similarity	NPD1357	Approved
0.7697	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD5283	Phase 1
0.7662	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7028	Phase 2
0.761	Intermediate Similarity	NPD4967	Phase 2
0.761	Intermediate Similarity	NPD4965	Approved
0.761	Intermediate Similarity	NPD4966	Approved
0.7591	Intermediate Similarity	NPD5536	Phase 2
0.7516	Intermediate Similarity	NPD6234	Discontinued
0.7439	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD37	Approved
0.7417	Intermediate Similarity	NPD7266	Discontinued
0.7397	Intermediate Similarity	NPD3027	Phase 3
0.7368	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4110	Phase 3
0.7256	Intermediate Similarity	NPD5494	Approved
0.7239	Intermediate Similarity	NPD1358	Approved
0.7222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7199	Phase 2
0.7208	Intermediate Similarity	NPD6674	Discontinued
0.7202	Intermediate Similarity	NPD7228	Approved
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.719	Intermediate Similarity	NPD1375	Discontinued
0.7178	Intermediate Similarity	NPD3882	Suspended
0.7164	Intermediate Similarity	NPD3134	Approved
0.7162	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2492	Phase 1
0.7133	Intermediate Similarity	NPD4060	Phase 1
0.7117	Intermediate Similarity	NPD3817	Phase 2
0.7113	Intermediate Similarity	NPD5691	Approved
0.7108	Intermediate Similarity	NPD8127	Discontinued
0.7091	Intermediate Similarity	NPD919	Approved
0.7086	Intermediate Similarity	NPD6355	Discontinued
0.7086	Intermediate Similarity	NPD3657	Discovery
0.7078	Intermediate Similarity	NPD5763	Approved
0.7078	Intermediate Similarity	NPD5762	Approved
0.7071	Intermediate Similarity	NPD7157	Approved
0.7063	Intermediate Similarity	NPD4210	Discontinued
0.7051	Intermediate Similarity	NPD4628	Phase 3
0.7035	Intermediate Similarity	NPD7240	Approved
0.7034	Intermediate Similarity	NPD2981	Phase 2
0.702	Intermediate Similarity	NPD3620	Phase 2
0.702	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1247	Approved
0.7006	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7808	Phase 3
0.6993	Remote Similarity	NPD5585	Approved
0.6986	Remote Similarity	NPD2982	Phase 2
0.6986	Remote Similarity	NPD2983	Phase 2
0.6986	Remote Similarity	NPD5327	Phase 3
0.6977	Remote Similarity	NPD6797	Phase 2
0.6975	Remote Similarity	NPD6599	Discontinued
0.6966	Remote Similarity	NPD1091	Approved
0.6939	Remote Similarity	NPD8651	Approved
0.6936	Remote Similarity	NPD7685	Pre-registration
0.6936	Remote Similarity	NPD7251	Discontinued
0.6933	Remote Similarity	NPD5090	Approved
0.6933	Remote Similarity	NPD5089	Approved
0.6929	Remote Similarity	NPD1241	Discontinued
0.6923	Remote Similarity	NPD3926	Phase 2
0.6919	Remote Similarity	NPD7074	Phase 3
0.6913	Remote Similarity	NPD3018	Phase 2
0.6913	Remote Similarity	NPD2861	Phase 2
0.6908	Remote Similarity	NPD4140	Approved
0.6908	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1613	Approved
0.6906	Remote Similarity	NPD228	Approved
0.6899	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6190	Approved
0.6897	Remote Similarity	NPD3496	Discontinued
0.6897	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1934	Approved
0.6883	Remote Similarity	NPD6111	Discontinued
0.6882	Remote Similarity	NPD4481	Phase 3
0.6879	Remote Similarity	NPD4237	Approved
0.6879	Remote Similarity	NPD4236	Phase 3
0.6875	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3146	Approved
0.6863	Remote Similarity	NPD5735	Approved
0.6863	Remote Similarity	NPD4340	Discontinued
0.686	Remote Similarity	NPD7054	Approved
0.6855	Remote Similarity	NPD5058	Phase 3
0.6855	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7124	Phase 2
0.6848	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4585	Approved
0.6842	Remote Similarity	NPD6233	Phase 2
0.6835	Remote Similarity	NPD8166	Discontinued
0.6829	Remote Similarity	NPD6386	Approved
0.6829	Remote Similarity	NPD6385	Approved
0.6828	Remote Similarity	NPD4626	Approved
0.6821	Remote Similarity	NPD7472	Approved
0.6813	Remote Similarity	NPD5297	Approved
0.6813	Remote Similarity	NPD6799	Approved
0.6812	Remote Similarity	NPD2684	Approved
0.681	Remote Similarity	NPD7458	Discontinued
0.6807	Remote Similarity	NPD2563	Approved
0.6807	Remote Similarity	NPD5353	Approved
0.6807	Remote Similarity	NPD2560	Approved
0.6803	Remote Similarity	NPD3972	Approved
0.6802	Remote Similarity	NPD3751	Discontinued
0.6795	Remote Similarity	NPD2161	Phase 2
0.6795	Remote Similarity	NPD2438	Suspended
0.6786	Remote Similarity	NPD969	Suspended
0.6784	Remote Similarity	NPD6166	Phase 2
0.6784	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7296	Approved
0.6776	Remote Similarity	NPD5111	Phase 2
0.6776	Remote Similarity	NPD6798	Discontinued
0.6776	Remote Similarity	NPD5109	Approved
0.6776	Remote Similarity	NPD5110	Phase 2
0.6774	Remote Similarity	NPD6896	Approved
0.6774	Remote Similarity	NPD6895	Approved
0.6757	Remote Similarity	NPD4359	Approved
0.6755	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1933	Approved
0.6748	Remote Similarity	NPD3687	Approved
0.6748	Remote Similarity	NPD3686	Approved
0.6747	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2977	Approved
0.6747	Remote Similarity	NPD2978	Approved
0.6747	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6559	Discontinued
0.6738	Remote Similarity	NPD7843	Approved
0.6738	Remote Similarity	NPD5535	Approved
0.6733	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8032	Phase 2
0.6732	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4108	Discontinued
0.673	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6873	Phase 2
0.6726	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5242	Approved
0.6723	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD17	Approved
0.6711	Remote Similarity	NPD1876	Approved
0.671	Remote Similarity	NPD6653	Approved
0.6709	Remote Similarity	NPD4534	Discontinued
0.6709	Remote Similarity	NPD2424	Discontinued
0.6708	Remote Similarity	NPD4357	Discontinued
0.6707	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6841	Approved
0.6704	Remote Similarity	NPD6843	Phase 3
0.6704	Remote Similarity	NPD6842	Approved
0.6689	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2796	Approved
0.6688	Remote Similarity	NPD2979	Phase 3
0.6687	Remote Similarity	NPD3887	Approved
0.6686	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4420	Approved
0.6667	Remote Similarity	NPD2971	Approved
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2968	Approved
0.6667	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7097	Phase 1
0.6648	Remote Similarity	NPD8434	Phase 2
0.6647	Remote Similarity	NPD2801	Approved
0.6646	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6005	Phase 3
0.6646	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD6002	Phase 3
0.6646	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4908	Phase 1
0.6645	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1651	Approved
0.6627	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7075	Discontinued
0.6626	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7526	Approved
0.6626	Remote Similarity	NPD6273	Approved
0.6626	Remote Similarity	NPD52	Approved
0.6625	Remote Similarity	NPD6331	Phase 2
0.6624	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3748	Approved
0.6624	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4870	Approved
0.6623	Remote Similarity	NPD4062	Phase 3
0.6623	Remote Similarity	NPD2798	Approved
0.6613	Remote Similarity	NPD4107	Approved
0.6607	Remote Similarity	NPD5402	Approved
0.6606	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5958	Discontinued
0.6603	Remote Similarity	NPD6353	Approved
0.6603	Remote Similarity	NPD2653	Approved
0.6599	Remote Similarity	NPD5125	Phase 3
0.6599	Remote Similarity	NPD5126	Approved
0.6599	Remote Similarity	NPD1778	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