NPASS Compound

Structure

CID139876 OpenBabel06191715502D 30 33 0 0 1 0 0 0 0 0999 V2000 -9.6113 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 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 -5.2812 -1.8090 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 -2.6831 -0.3090 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 -0.0000 -1.6180 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 -7.8793 -1.3090 0.0000 C 0 0 1 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 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -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 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 -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 -7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 -2.8090 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 -6.1472 -1.3090 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 4 1 0 0 0 0 3 26 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 27 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 22 2 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 28 1 0 0 0 0 14 29 1 0 0 0 0 15 2 1 6 0 0 0 15 24 1 0 0 0 0 17 20 1 0 0 0 0 18 23 2 0 0 0 0 19 21 2 0 0 0 0 19 28 1 0 0 0 0 20 30 1 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 26 1 0 0 0 0 23 30 1 0 0 0 0 24 25 2 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.17
Volume:	421.084
LogP:	5.654
LogD:	4.538
LogS:	-7.113
# Rotatable Bonds:	9
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	2.965
Fsp3:	0.375
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:	-4.908
MDCK Permeability:	2.5512978027109057e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	99.1175765991211%
Volume Distribution (VD):	1.31
Pgp-substrate:	2.0676651000976562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.398
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.921
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.896
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.977
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	12.901
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.146
Carcinogencity:	0.679
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.726

Download Data

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

Natural Product: NPC139876

Natural Product ID:	NPC139876
*Common Name:**	3-[2-(1,3-Benzodioxol-5-Yl)-7-Methoxy-1-Benzofuran-5-Yl]Propyl (2S)-2-Methylbutanoate
IUPAC Name:	3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propyl (2S)-2-methylbutanoate
Synonyms:
Standard InCHIKey:	MGCSMWCSVJYFBV-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C24H26O6/c1-4-15(2)24(25)27-9-5-6-16-10-18-13-20(30-23(18)22(11-16)26-3)17-7-8-19-21(12-17)29-14-28-19/h7-8,10-13,15H,4-6,9,14H2,1-3H3/t15-/m0/s1
SMILES:	CC[C@H](C)C(=O)OCCCc1cc2cc(c3ccc4c(c3)OCO4)oc2c(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1834810
PubChem CID:	56598865
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
NPO30418	Styrax obassia	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21939219]
NPO14098	Styrax agrestis	Species	Styracaceae	Eukaryota	fruits	Thua Thien, Hue district, Vietnam	n.a.	PMID[21939219]
NPO14098	Styrax agrestis	Species	Styracaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[21939219]
NPO14098	Styrax agrestis	Species	Styracaceae	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	2
Others	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	4800.0	nM	PMID[511313]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	5900.0	nM	PMID[511313]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	70.5	%	PMID[511313]

☑ 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 NPC139876 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	431
0.1-0.2	1631
0.2-0.3	3988
0.3-0.4	9144
0.4-0.5	9404
0.5-0.6	3873
0.6-0.7	6923
0.7-0.8	6869
0.8-0.85	388
0.85-0.9	33
0.9-0.95	4
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC15764
0.9804	High Similarity	NPC296540
0.9804	High Similarity	NPC309335
0.9801	High Similarity	NPC261484
0.974	High Similarity	NPC19948
0.9735	High Similarity	NPC3273
0.9608	High Similarity	NPC76458
0.9608	High Similarity	NPC82733
0.9548	High Similarity	NPC99968
0.9423	High Similarity	NPC109238
0.929	High Similarity	NPC261090
0.9136	High Similarity	NPC135370
0.9097	High Similarity	NPC60211
0.8909	High Similarity	NPC62640
0.8889	High Similarity	NPC187923
0.8861	High Similarity	NPC268008
0.8831	High Similarity	NPC153620
0.8831	High Similarity	NPC24257
0.8795	High Similarity	NPC72455
0.8758	High Similarity	NPC65784
0.8734	High Similarity	NPC308555
0.8727	High Similarity	NPC41853
0.8696	High Similarity	NPC250076
0.8693	High Similarity	NPC27220
0.8688	High Similarity	NPC115123
0.8688	High Similarity	NPC239113
0.8671	High Similarity	NPC118332
0.8667	High Similarity	NPC167479
0.8631	High Similarity	NPC66804
0.8625	High Similarity	NPC254163
0.8623	High Similarity	NPC157522
0.8623	High Similarity	NPC475964
0.8614	High Similarity	NPC211309
0.8606	High Similarity	NPC155264
0.8606	High Similarity	NPC193881
0.8606	High Similarity	NPC210460
0.8606	High Similarity	NPC67450
0.8589	High Similarity	NPC216092
0.8562	High Similarity	NPC54179
0.8545	High Similarity	NPC279768
0.8537	High Similarity	NPC302741
0.8528	High Similarity	NPC243509
0.8528	High Similarity	NPC78944
0.8519	High Similarity	NPC19600
0.8509	High Similarity	NPC284353
0.8509	High Similarity	NPC80489
0.8494	Intermediate Similarity	NPC471923
0.8485	Intermediate Similarity	NPC132054
0.8485	Intermediate Similarity	NPC179464
0.8481	Intermediate Similarity	NPC127827
0.8466	Intermediate Similarity	NPC325122
0.8466	Intermediate Similarity	NPC68619
0.8466	Intermediate Similarity	NPC125713
0.8466	Intermediate Similarity	NPC33320
0.8462	Intermediate Similarity	NPC474568
0.8457	Intermediate Similarity	NPC109765
0.8457	Intermediate Similarity	NPC155063
0.8447	Intermediate Similarity	NPC279930
0.8443	Intermediate Similarity	NPC473531
0.8443	Intermediate Similarity	NPC186392
0.8443	Intermediate Similarity	NPC475453
0.8438	Intermediate Similarity	NPC104353
0.8428	Intermediate Similarity	NPC475722
0.8424	Intermediate Similarity	NPC234536
0.8424	Intermediate Similarity	NPC61141
0.8424	Intermediate Similarity	NPC78612
0.8424	Intermediate Similarity	NPC116838
0.8424	Intermediate Similarity	NPC22130
0.8415	Intermediate Similarity	NPC131557
0.8405	Intermediate Similarity	NPC202495
0.8405	Intermediate Similarity	NPC258644
0.8405	Intermediate Similarity	NPC310206
0.8385	Intermediate Similarity	NPC68882
0.8383	Intermediate Similarity	NPC298071
0.8375	Intermediate Similarity	NPC474975
0.8373	Intermediate Similarity	NPC110257
0.8364	Intermediate Similarity	NPC34376
0.8364	Intermediate Similarity	NPC191352
0.8364	Intermediate Similarity	NPC258322
0.8364	Intermediate Similarity	NPC15212
0.8354	Intermediate Similarity	NPC474043
0.8354	Intermediate Similarity	NPC113055
0.8354	Intermediate Similarity	NPC238405
0.8354	Intermediate Similarity	NPC257914
0.8354	Intermediate Similarity	NPC104459
0.8353	Intermediate Similarity	NPC316539
0.8344	Intermediate Similarity	NPC213900
0.8343	Intermediate Similarity	NPC144288
0.8333	Intermediate Similarity	NPC474948
0.8333	Intermediate Similarity	NPC42230
0.8324	Intermediate Similarity	NPC475996
0.8323	Intermediate Similarity	NPC475953
0.8323	Intermediate Similarity	NPC98028
0.8323	Intermediate Similarity	NPC179015
0.8323	Intermediate Similarity	NPC173149
0.8323	Intermediate Similarity	NPC220577
0.8323	Intermediate Similarity	NPC477884
0.8313	Intermediate Similarity	NPC474305
0.8313	Intermediate Similarity	NPC18284
0.8313	Intermediate Similarity	NPC273021
0.8313	Intermediate Similarity	NPC272722
0.8304	Intermediate Similarity	NPC290304
0.8304	Intermediate Similarity	NPC236327
0.8303	Intermediate Similarity	NPC474770
0.8303	Intermediate Similarity	NPC239818
0.8303	Intermediate Similarity	NPC43971
0.8303	Intermediate Similarity	NPC472961
0.8303	Intermediate Similarity	NPC19554
0.8303	Intermediate Similarity	NPC472962
0.8303	Intermediate Similarity	NPC218471
0.8303	Intermediate Similarity	NPC74749
0.8302	Intermediate Similarity	NPC117463
0.8301	Intermediate Similarity	NPC102260
0.8301	Intermediate Similarity	NPC230968
0.8294	Intermediate Similarity	NPC114550
0.8294	Intermediate Similarity	NPC292712
0.8294	Intermediate Similarity	NPC471920
0.8294	Intermediate Similarity	NPC471921
0.8294	Intermediate Similarity	NPC312006
0.8294	Intermediate Similarity	NPC471922
0.8294	Intermediate Similarity	NPC473697
0.8294	Intermediate Similarity	NPC474075
0.8294	Intermediate Similarity	NPC20114
0.8294	Intermediate Similarity	NPC129930
0.8293	Intermediate Similarity	NPC474990
0.8282	Intermediate Similarity	NPC234730
0.8282	Intermediate Similarity	NPC478238
0.8272	Intermediate Similarity	NPC131121
0.8272	Intermediate Similarity	NPC144162
0.8272	Intermediate Similarity	NPC137813
0.8263	Intermediate Similarity	NPC65846
0.8256	Intermediate Similarity	NPC107244
0.8253	Intermediate Similarity	NPC209411
0.8253	Intermediate Similarity	NPC264293
0.8253	Intermediate Similarity	NPC239890
0.8253	Intermediate Similarity	NPC469889
0.825	Intermediate Similarity	NPC474306
0.825	Intermediate Similarity	NPC475848
0.825	Intermediate Similarity	NPC24193
0.8246	Intermediate Similarity	NPC184624
0.8242	Intermediate Similarity	NPC50430
0.8239	Intermediate Similarity	NPC25496
0.8235	Intermediate Similarity	NPC51404
0.8232	Intermediate Similarity	NPC477380
0.8228	Intermediate Similarity	NPC474158
0.8228	Intermediate Similarity	NPC327052
0.8224	Intermediate Similarity	NPC205915
0.8221	Intermediate Similarity	NPC178195
0.8221	Intermediate Similarity	NPC478213
0.8221	Intermediate Similarity	NPC244371
0.8221	Intermediate Similarity	NPC348849
0.8217	Intermediate Similarity	NPC137920
0.8217	Intermediate Similarity	NPC86455
0.8217	Intermediate Similarity	NPC28326
0.8217	Intermediate Similarity	NPC125134
0.8214	Intermediate Similarity	NPC36320
0.8214	Intermediate Similarity	NPC474647
0.8204	Intermediate Similarity	NPC198796
0.8204	Intermediate Similarity	NPC478199
0.8204	Intermediate Similarity	NPC125991
0.8199	Intermediate Similarity	NPC300983
0.8198	Intermediate Similarity	NPC224165
0.8198	Intermediate Similarity	NPC193377
0.8198	Intermediate Similarity	NPC53917
0.8193	Intermediate Similarity	NPC269906
0.8187	Intermediate Similarity	NPC247964
0.8187	Intermediate Similarity	NPC181464
0.8182	Intermediate Similarity	NPC477885
0.8176	Intermediate Similarity	NPC224687
0.8176	Intermediate Similarity	NPC296575
0.8171	Intermediate Similarity	NPC471746
0.8171	Intermediate Similarity	NPC180901
0.8171	Intermediate Similarity	NPC10205
0.8171	Intermediate Similarity	NPC300757
0.817	Intermediate Similarity	NPC170779
0.817	Intermediate Similarity	NPC90083
0.8166	Intermediate Similarity	NPC323137
0.8166	Intermediate Similarity	NPC174734
0.8166	Intermediate Similarity	NPC474042
0.8166	Intermediate Similarity	NPC113093
0.8165	Intermediate Similarity	NPC475000
0.8165	Intermediate Similarity	NPC473090
0.8165	Intermediate Similarity	NPC15743
0.816	Intermediate Similarity	NPC148497
0.816	Intermediate Similarity	NPC292460
0.816	Intermediate Similarity	NPC153008
0.8155	Intermediate Similarity	NPC272750
0.8155	Intermediate Similarity	NPC100425
0.8155	Intermediate Similarity	NPC91288
0.8155	Intermediate Similarity	NPC45943
0.8155	Intermediate Similarity	NPC173729
0.8155	Intermediate Similarity	NPC475865
0.8155	Intermediate Similarity	NPC472582
0.8155	Intermediate Similarity	NPC223006
0.8155	Intermediate Similarity	NPC134047
0.8153	Intermediate Similarity	NPC176586
0.8153	Intermediate Similarity	NPC210354
0.815	Intermediate Similarity	NPC196771
0.815	Intermediate Similarity	NPC156635
0.8144	Intermediate Similarity	NPC94155

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 NPC139876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	926
0.2-0.3	1707
0.3-0.4	2644
0.4-0.5	1925
0.5-0.6	1005
0.6-0.7	428
0.7-0.8	132
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8466	Intermediate Similarity	NPD919	Approved
0.8302	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD1247	Approved
0.8228	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5494	Approved
0.8061	Intermediate Similarity	NPD3817	Phase 2
0.8047	Intermediate Similarity	NPD3926	Phase 2
0.8047	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3882	Suspended
0.7907	Intermediate Similarity	NPD3818	Discontinued
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD920	Approved
0.7848	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6559	Discontinued
0.7824	Intermediate Similarity	NPD7199	Phase 2
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6799	Approved
0.7759	Intermediate Similarity	NPD5844	Phase 1
0.7753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7075	Discontinued
0.7644	Intermediate Similarity	NPD7473	Discontinued
0.764	Intermediate Similarity	NPD1243	Approved
0.7619	Intermediate Similarity	NPD6801	Discontinued
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6599	Discontinued
0.7602	Intermediate Similarity	NPD6234	Discontinued
0.7584	Intermediate Similarity	NPD7808	Phase 3
0.7574	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6232	Discontinued
0.7571	Intermediate Similarity	NPD6797	Phase 2
0.756	Intermediate Similarity	NPD6385	Approved
0.756	Intermediate Similarity	NPD6386	Approved
0.7545	Intermediate Similarity	NPD7458	Discontinued
0.7532	Intermediate Similarity	NPD1933	Approved
0.7528	Intermediate Similarity	NPD7251	Discontinued
0.7527	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD1934	Approved
0.7514	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7486	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7472	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2801	Approved
0.7471	Intermediate Similarity	NPD7819	Suspended
0.7458	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7054	Approved
0.7439	Intermediate Similarity	NPD3887	Approved
0.7421	Intermediate Similarity	NPD6355	Discontinued
0.7416	Intermediate Similarity	NPD7472	Approved
0.741	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2344	Approved
0.7407	Intermediate Similarity	NPD1471	Phase 3
0.7401	Intermediate Similarity	NPD2163	Approved
0.7353	Intermediate Similarity	NPD7411	Suspended
0.7346	Intermediate Similarity	NPD2796	Approved
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7341	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7685	Pre-registration
0.7326	Intermediate Similarity	NPD5402	Approved
0.7322	Intermediate Similarity	NPD8434	Phase 2
0.7305	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3146	Approved
0.7303	Intermediate Similarity	NPD7228	Approved
0.7303	Intermediate Similarity	NPD17	Approved
0.7301	Intermediate Similarity	NPD2353	Approved
0.7301	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1465	Phase 2
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7262	Intermediate Similarity	NPD1512	Approved
0.7258	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8312	Approved
0.7253	Intermediate Similarity	NPD8313	Approved
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7241	Intermediate Similarity	NPD3749	Approved
0.7239	Intermediate Similarity	NPD2935	Discontinued
0.7235	Intermediate Similarity	NPD3226	Approved
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7232	Intermediate Similarity	NPD5242	Approved
0.7229	Intermediate Similarity	NPD2309	Approved
0.7208	Intermediate Similarity	NPD3705	Approved
0.7205	Intermediate Similarity	NPD447	Suspended
0.72	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2346	Discontinued
0.7178	Intermediate Similarity	NPD3748	Approved
0.7175	Intermediate Similarity	NPD6808	Phase 2
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7173	Intermediate Similarity	NPD4107	Approved
0.7161	Intermediate Similarity	NPD1608	Approved
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7143	Intermediate Similarity	NPD6764	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD6765	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7126	Intermediate Similarity	NPD6190	Approved
0.7126	Intermediate Similarity	NPD2354	Approved
0.7126	Intermediate Similarity	NPD5353	Approved
0.7125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7118	Intermediate Similarity	NPD5403	Approved
0.7111	Intermediate Similarity	NPD3751	Discontinued
0.711	Intermediate Similarity	NPD6280	Approved
0.711	Intermediate Similarity	NPD6279	Approved
0.7107	Intermediate Similarity	NPD6832	Phase 2
0.7105	Intermediate Similarity	NPD5536	Phase 2
0.7101	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5401	Approved
0.7101	Intermediate Similarity	NPD2533	Approved
0.7101	Intermediate Similarity	NPD2532	Approved
0.7101	Intermediate Similarity	NPD2534	Approved
0.7099	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4380	Phase 2
0.7093	Intermediate Similarity	NPD7028	Phase 2
0.7086	Intermediate Similarity	NPD7768	Phase 2
0.7081	Intermediate Similarity	NPD6233	Phase 2
0.7079	Intermediate Similarity	NPD3787	Discontinued
0.7068	Intermediate Similarity	NPD4420	Approved
0.7066	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4110	Phase 3
0.7052	Intermediate Similarity	NPD6873	Phase 2
0.7047	Intermediate Similarity	NPD4482	Phase 3
0.7035	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2438	Suspended
0.7029	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD230	Phase 1
0.6989	Remote Similarity	NPD6785	Approved
0.6989	Remote Similarity	NPD6784	Approved
0.6987	Remote Similarity	NPD1281	Approved
0.6981	Remote Similarity	NPD2798	Approved
0.6964	Remote Similarity	NPD7003	Approved
0.6964	Remote Similarity	NPD3750	Approved
0.6959	Remote Similarity	NPD6273	Approved
0.6946	Remote Similarity	NPD1549	Phase 2
0.6943	Remote Similarity	NPD3972	Approved
0.6937	Remote Similarity	NPD9494	Approved
0.6932	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6959	Discontinued
0.6923	Remote Similarity	NPD5005	Approved
0.6923	Remote Similarity	NPD5006	Approved
0.6923	Remote Similarity	NPD7177	Discontinued
0.6918	Remote Similarity	NPD3266	Approved
0.6918	Remote Similarity	NPD3267	Approved
0.6918	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3764	Approved
0.6906	Remote Similarity	NPD2403	Approved
0.6888	Remote Similarity	NPD7435	Discontinued
0.6886	Remote Similarity	NPD6002	Phase 3
0.6886	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6004	Phase 3
0.6886	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5762	Approved
0.6886	Remote Similarity	NPD5763	Approved
0.6886	Remote Similarity	NPD6005	Phase 3
0.6879	Remote Similarity	NPD1653	Approved
0.6879	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4062	Phase 3
0.6867	Remote Similarity	NPD1510	Phase 2
0.6865	Remote Similarity	NPD7038	Approved
0.6865	Remote Similarity	NPD7039	Approved
0.6864	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1283	Approved
0.6855	Remote Similarity	NPD1876	Approved
0.6852	Remote Similarity	NPD7095	Approved
0.6845	Remote Similarity	NPD2897	Discontinued
0.6845	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD5283	Phase 1
0.6836	Remote Similarity	NPD5978	Approved
0.6836	Remote Similarity	NPD5977	Approved
0.6829	Remote Similarity	NPD4307	Phase 2
0.6829	Remote Similarity	NPD1240	Approved
0.6826	Remote Similarity	NPD2531	Phase 2
0.6811	Remote Similarity	NPD5953	Discontinued
0.681	Remote Similarity	NPD3268	Approved
0.6807	Remote Similarity	NPD7097	Phase 1
0.6805	Remote Similarity	NPD2800	Approved
0.6805	Remote Similarity	NPD6674	Discontinued
0.6798	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1651	Approved
0.6795	Remote Similarity	NPD5691	Approved
0.6795	Remote Similarity	NPD5585	Approved
0.6793	Remote Similarity	NPD7286	Phase 2

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