NPASS Compound

Structure

CID163898 OpenBabel06191715532D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.0878 1.7891 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 3.5491 -1.8090 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 -3.0878 -1.6750 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 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 0.0570 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 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 0.0000 -1.6180 0.0000 C 0 0 1 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 0.0570 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 4.4152 -3.3090 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 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 17 2 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 10 1 6 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 12 1 1 0 0 0 19 27 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.12
Volume:	369.247
LogP:	2.044
LogD:	1.693
LogS:	-4.166
# Rotatable Bonds:	6
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	3.324
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.81
MDCK Permeability:	8.145079846144654e-06
Pgp-inhibitor:	0.015
Pgp-substrate:	0.552
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	84.7255630493164%
Volume Distribution (VD):	0.415
Pgp-substrate:	12.064287185668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.556
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.668
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.446

ADMET: Excretion

Clearance (CL):	5.746
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.764
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.176
Skin Sensitization:	0.715
Carcinogencity:	0.328
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.273

Download Data

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

Natural Product: NPC163898

Natural Product ID:	NPC163898
*Common Name:**	Glycosmisic Acid
IUPAC Name:	(E)-3-[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid
Synonyms:	Glycosmisic Acid
Standard InCHIKey:	FHYQIQMSODIFCP-ZMOFONSMSA-N
Standard InCHI:	InChI=1S/C20H20O7/c1-25-16-9-12(4-5-15(16)22)19-14(10-21)13-7-11(3-6-18(23)24)8-17(26-2)20(13)27-19/h3-9,14,19,21-22H,10H2,1-2H3,(H,23,24)/b6-3+/t14-,19+/m0/s1
SMILES:	OC[C@@H]1[C@H](Oc2c1cc(/C=C/C(=O)O)cc2OC)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346742
PubChem CID:	38356809
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
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[23434030]
NPO30830	Sphingobium sp.	Species	Sphingomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26362985]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4093781]
NPO28043	Streblus asper	Species	Moraceae	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	3
Others	1

Activity Type	# Activity
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	1000000.0	nM	PMID[542156]
NPT27	Others	Unspecified		CC50	=	200070.0	nM	PMID[542156]

☑ 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 NPC163898 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	318
0.1-0.2	1279
0.2-0.3	3335
0.3-0.4	7685
0.4-0.5	10718
0.5-0.6	3565
0.6-0.7	6708
0.7-0.8	7498
0.8-0.85	1265
0.85-0.9	268
0.9-0.95	41
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9645	High Similarity	NPC236166
0.964	High Similarity	NPC264706
0.964	High Similarity	NPC474444
0.964	High Similarity	NPC284881
0.964	High Similarity	NPC93433
0.9638	High Similarity	NPC131971
0.9416	High Similarity	NPC209985
0.9416	High Similarity	NPC54743
0.9416	High Similarity	NPC263367
0.9416	High Similarity	NPC156502
0.9416	High Similarity	NPC29799
0.9416	High Similarity	NPC477939
0.9416	High Similarity	NPC177160
0.9416	High Similarity	NPC10737
0.9371	High Similarity	NPC473408
0.9315	High Similarity	NPC115203
0.9286	High Similarity	NPC471414
0.927	High Similarity	NPC67247
0.927	High Similarity	NPC187616
0.927	High Similarity	NPC49603
0.927	High Similarity	NPC193026
0.922	High Similarity	NPC253878
0.922	High Similarity	NPC67467
0.9209	High Similarity	NPC126206
0.9197	High Similarity	NPC26394
0.9149	High Similarity	NPC263261
0.9149	High Similarity	NPC87725
0.9137	High Similarity	NPC471664
0.9137	High Similarity	NPC471988
0.9137	High Similarity	NPC471665
0.9133	High Similarity	NPC478269
0.913	High Similarity	NPC135127
0.9128	High Similarity	NPC228357
0.9124	High Similarity	NPC230219
0.9071	High Similarity	NPC281780
0.9067	High Similarity	NPC125495
0.9054	High Similarity	NPC470769
0.9013	High Similarity	NPC478267
0.8993	High Similarity	NPC249791
0.8993	High Similarity	NPC237594
0.8993	High Similarity	NPC476387
0.8993	High Similarity	NPC119060
0.8986	High Similarity	NPC18842
0.8978	High Similarity	NPC64201
0.8978	High Similarity	NPC187998
0.8978	High Similarity	NPC42300
0.8978	High Similarity	NPC174495
0.8978	High Similarity	NPC257582
0.8978	High Similarity	NPC153739
0.8978	High Similarity	NPC92164
0.8978	High Similarity	NPC241522
0.8978	High Similarity	NPC77040
0.8978	High Similarity	NPC145305
0.8978	High Similarity	NPC242807
0.8958	High Similarity	NPC471763
0.8936	High Similarity	NPC477938
0.8933	High Similarity	NPC180901
0.8933	High Similarity	NPC300757
0.8913	High Similarity	NPC277804
0.8905	High Similarity	NPC475875
0.8904	High Similarity	NPC193473
0.8904	High Similarity	NPC114505
0.8904	High Similarity	NPC275284
0.8904	High Similarity	NPC213074
0.8904	High Similarity	NPC31325
0.8904	High Similarity	NPC224674
0.8904	High Similarity	NPC476347
0.8904	High Similarity	NPC15956
0.8889	High Similarity	NPC469889
0.8889	High Similarity	NPC216916
0.8881	High Similarity	NPC100675
0.8857	High Similarity	NPC16485
0.8857	High Similarity	NPC478085
0.8844	High Similarity	NPC252402
0.8844	High Similarity	NPC476348
0.8844	High Similarity	NPC187398
0.8844	High Similarity	NPC102934
0.8841	High Similarity	NPC143483
0.8836	High Similarity	NPC199928
0.8836	High Similarity	NPC260397
0.8832	High Similarity	NPC21867
0.8832	High Similarity	NPC470084
0.8832	High Similarity	NPC282703
0.8832	High Similarity	NPC45774
0.8832	High Similarity	NPC11258
0.8832	High Similarity	NPC184733
0.8832	High Similarity	NPC478215
0.8832	High Similarity	NPC129570
0.8832	High Similarity	NPC128208
0.8828	High Similarity	NPC232228
0.8828	High Similarity	NPC12641
0.8828	High Similarity	NPC280092
0.8828	High Similarity	NPC93323
0.8828	High Similarity	NPC45257
0.8816	High Similarity	NPC470827
0.8811	High Similarity	NPC309124
0.8811	High Similarity	NPC184797
0.8811	High Similarity	NPC254759
0.8811	High Similarity	NPC160283
0.88	High Similarity	NPC131121
0.88	High Similarity	NPC149735
0.8794	High Similarity	NPC214729
0.8777	High Similarity	NPC158079
0.8777	High Similarity	NPC228346
0.8777	High Similarity	NPC40432
0.8777	High Similarity	NPC161557
0.8777	High Similarity	NPC27843
0.8777	High Similarity	NPC115207
0.8777	High Similarity	NPC7171
0.8776	High Similarity	NPC178129
0.8774	High Similarity	NPC45943
0.8767	High Similarity	NPC476301
0.8767	High Similarity	NPC143120
0.8767	High Similarity	NPC43508
0.8767	High Similarity	NPC274960
0.8767	High Similarity	NPC473909
0.8759	High Similarity	NPC118787
0.8759	High Similarity	NPC183181
0.8759	High Similarity	NPC165045
0.8759	High Similarity	NPC478239
0.8759	High Similarity	NPC292056
0.8759	High Similarity	NPC147821
0.8759	High Similarity	NPC102044
0.8759	High Similarity	NPC98745
0.8759	High Similarity	NPC118533
0.8759	High Similarity	NPC111247
0.8759	High Similarity	NPC41706
0.8759	High Similarity	NPC163332
0.8759	High Similarity	NPC47633
0.8759	High Similarity	NPC85264
0.8759	High Similarity	NPC319625
0.8759	High Similarity	NPC477616
0.8758	High Similarity	NPC470828
0.875	High Similarity	NPC311530
0.875	High Similarity	NPC11411
0.8742	High Similarity	NPC268484
0.8741	High Similarity	NPC292882
0.8741	High Similarity	NPC473739
0.8741	High Similarity	NPC70682
0.8741	High Similarity	NPC260741
0.8741	High Similarity	NPC232164
0.8741	High Similarity	NPC236306
0.8733	High Similarity	NPC478268
0.8733	High Similarity	NPC302610
0.8732	High Similarity	NPC120852
0.8732	High Similarity	NPC77861
0.8726	High Similarity	NPC208818
0.8725	High Similarity	NPC21184
0.8725	High Similarity	NPC98624
0.8725	High Similarity	NPC294522
0.8725	High Similarity	NPC120426
0.8725	High Similarity	NPC205727
0.8723	High Similarity	NPC287745
0.8714	High Similarity	NPC181049
0.8714	High Similarity	NPC2190
0.8714	High Similarity	NPC207400
0.8707	High Similarity	NPC40222
0.8707	High Similarity	NPC268515
0.8701	High Similarity	NPC472962
0.8701	High Similarity	NPC472961
0.8699	High Similarity	NPC217635
0.8699	High Similarity	NPC63879
0.8699	High Similarity	NPC292443
0.8699	High Similarity	NPC79429
0.8699	High Similarity	NPC471667
0.8696	High Similarity	NPC472968
0.869	High Similarity	NPC140502
0.869	High Similarity	NPC107161
0.869	High Similarity	NPC476840
0.869	High Similarity	NPC476842
0.869	High Similarity	NPC157816
0.869	High Similarity	NPC41782
0.869	High Similarity	NPC476356
0.8686	High Similarity	NPC178284
0.8686	High Similarity	NPC120225
0.8686	High Similarity	NPC206882
0.8686	High Similarity	NPC191037
0.8686	High Similarity	NPC213552
0.8686	High Similarity	NPC58607
0.8681	High Similarity	NPC267291
0.8675	High Similarity	NPC223720
0.8662	High Similarity	NPC101624
0.8662	High Similarity	NPC256262
0.8662	High Similarity	NPC184938
0.8658	High Similarity	NPC474347
0.8658	High Similarity	NPC474393
0.8658	High Similarity	NPC176903
0.8658	High Similarity	NPC30688
0.8652	High Similarity	NPC158331
0.8652	High Similarity	NPC475840
0.8649	High Similarity	NPC16269
0.8649	High Similarity	NPC21776
0.8649	High Similarity	NPC101376
0.8639	High Similarity	NPC181615
0.8639	High Similarity	NPC180953
0.8639	High Similarity	NPC223185
0.8636	High Similarity	NPC173726
0.8636	High Similarity	NPC241600
0.8633	High Similarity	NPC86030
0.8633	High Similarity	NPC5851

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 NPC163898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	828
0.2-0.3	1712
0.3-0.4	2572
0.4-0.5	1858
0.5-0.6	1002
0.6-0.7	705
0.7-0.8	202
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8451	Intermediate Similarity	NPD4060	Phase 1
0.8369	Intermediate Similarity	NPD3027	Phase 3
0.8322	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1613	Approved
0.817	Intermediate Similarity	NPD1653	Approved
0.8108	Intermediate Similarity	NPD7266	Discontinued
0.805	Intermediate Similarity	NPD6234	Discontinued
0.8042	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD5762	Approved
0.7987	Intermediate Similarity	NPD5763	Approved
0.7972	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD2861	Phase 2
0.7962	Intermediate Similarity	NPD1934	Approved
0.7962	Intermediate Similarity	NPD37	Approved
0.7947	Intermediate Similarity	NPD4628	Phase 3
0.7943	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3818	Discontinued
0.7925	Intermediate Similarity	NPD3882	Suspended
0.7925	Intermediate Similarity	NPD4966	Approved
0.7925	Intermediate Similarity	NPD4965	Approved
0.7925	Intermediate Similarity	NPD4967	Phase 2
0.7891	Intermediate Similarity	NPD6355	Discontinued
0.7881	Intermediate Similarity	NPD6674	Discontinued
0.784	Intermediate Similarity	NPD7199	Phase 2
0.784	Intermediate Similarity	NPD8127	Discontinued
0.7818	Intermediate Similarity	NPD7228	Approved
0.7808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5494	Approved
0.777	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD5124	Phase 1
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6004	Phase 3
0.7748	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6002	Phase 3
0.7748	Intermediate Similarity	NPD6005	Phase 3
0.7712	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4110	Phase 3
0.7703	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD3620	Phase 2
0.7697	Intermediate Similarity	NPD6166	Phase 2
0.7697	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2801	Approved
0.7682	Intermediate Similarity	NPD2935	Discontinued
0.7671	Intermediate Similarity	NPD4908	Phase 1
0.7664	Intermediate Similarity	NPD5283	Phase 1
0.7662	Intermediate Similarity	NPD6190	Approved
0.766	Intermediate Similarity	NPD4626	Approved
0.7654	Intermediate Similarity	NPD7075	Discontinued
0.7647	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3817	Phase 2
0.7636	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6559	Discontinued
0.7619	Intermediate Similarity	NPD7074	Phase 3
0.7606	Intermediate Similarity	NPD3496	Discontinued
0.76	Intermediate Similarity	NPD6653	Approved
0.7589	Intermediate Similarity	NPD5691	Approved
0.7584	Intermediate Similarity	NPD4140	Approved
0.7582	Intermediate Similarity	NPD2424	Discontinued
0.758	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1465	Phase 2
0.7578	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6232	Discontinued
0.7574	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6798	Discontinued
0.756	Intermediate Similarity	NPD7054	Approved
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7552	Intermediate Similarity	NPD3705	Approved
0.7552	Intermediate Similarity	NPD422	Phase 1
0.7545	Intermediate Similarity	NPD7473	Discontinued
0.7532	Intermediate Similarity	NPD1652	Phase 2
0.7529	Intermediate Similarity	NPD7685	Pre-registration
0.7518	Intermediate Similarity	NPD228	Approved
0.7517	Intermediate Similarity	NPD8651	Approved
0.7516	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD6666	Approved
0.75	Intermediate Similarity	NPD6667	Approved
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD7095	Approved
0.75	Intermediate Similarity	NPD5058	Phase 3
0.7485	Intermediate Similarity	NPD7549	Discontinued
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7819	Suspended
0.7469	Intermediate Similarity	NPD8455	Phase 2
0.7466	Intermediate Similarity	NPD2797	Approved
0.7455	Intermediate Similarity	NPD4666	Phase 3
0.7452	Intermediate Similarity	NPD1511	Approved
0.745	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5536	Phase 2
0.7438	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4536	Approved
0.7434	Intermediate Similarity	NPD4538	Approved
0.7434	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1091	Approved
0.7429	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4340	Discontinued
0.7417	Intermediate Similarity	NPD447	Suspended
0.7403	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6233	Phase 2
0.7394	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD5709	Phase 3
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD1608	Approved
0.7378	Intermediate Similarity	NPD7768	Phase 2
0.7375	Intermediate Similarity	NPD3687	Approved
0.7375	Intermediate Similarity	NPD3686	Approved
0.7372	Intermediate Similarity	NPD6331	Phase 2
0.7372	Intermediate Similarity	NPD3750	Approved
0.7372	Intermediate Similarity	NPD8166	Discontinued
0.7372	Intermediate Similarity	NPD3021	Approved
0.7372	Intermediate Similarity	NPD3022	Approved
0.7368	Intermediate Similarity	NPD6797	Phase 2
0.7358	Intermediate Similarity	NPD6273	Approved
0.7358	Intermediate Similarity	NPD1512	Approved
0.7351	Intermediate Similarity	NPD1558	Phase 1
0.7343	Intermediate Similarity	NPD1357	Approved
0.7342	Intermediate Similarity	NPD6799	Approved
0.7341	Intermediate Similarity	NPD8313	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7338	Intermediate Similarity	NPD6032	Approved
0.7333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3268	Approved
0.7326	Intermediate Similarity	NPD7240	Approved
0.7326	Intermediate Similarity	NPD7251	Discontinued
0.732	Intermediate Similarity	NPD7097	Phase 1
0.7317	Intermediate Similarity	NPD5402	Approved
0.7312	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1611	Approved
0.7305	Intermediate Similarity	NPD7157	Approved
0.7303	Intermediate Similarity	NPD5735	Approved
0.7303	Intermediate Similarity	NPD230	Phase 1
0.7299	Intermediate Similarity	NPD2684	Approved
0.7296	Intermediate Similarity	NPD2533	Approved
0.7296	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2534	Approved
0.7296	Intermediate Similarity	NPD2532	Approved
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7283	Intermediate Similarity	NPD7808	Phase 3
0.7279	Intermediate Similarity	NPD6696	Suspended
0.7278	Intermediate Similarity	NPD27	Approved
0.7278	Intermediate Similarity	NPD2489	Approved
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7273	Intermediate Similarity	NPD5960	Phase 3
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.7261	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3018	Phase 2
0.7239	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7411	Suspended
0.7226	Intermediate Similarity	NPD2438	Suspended
0.7226	Intermediate Similarity	NPD1358	Approved
0.7226	Intermediate Similarity	NPD290	Approved
0.7222	Intermediate Similarity	NPD5585	Approved
0.7222	Intermediate Similarity	NPD3226	Approved
0.7219	Intermediate Similarity	NPD2969	Approved
0.7219	Intermediate Similarity	NPD2970	Approved
0.7219	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7215	Intermediate Similarity	NPD2677	Approved
0.7214	Intermediate Similarity	NPD7843	Approved
0.7214	Intermediate Similarity	NPD5535	Approved
0.7212	Intermediate Similarity	NPD2563	Approved
0.7212	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2560	Approved
0.7211	Intermediate Similarity	NPD4749	Approved
0.7205	Intermediate Similarity	NPD5403	Approved
0.7197	Intermediate Similarity	NPD4236	Phase 3
0.7197	Intermediate Similarity	NPD4237	Approved
0.7188	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6671	Approved
0.7179	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1375	Discontinued
0.7179	Intermediate Similarity	NPD2346	Discontinued
0.7176	Intermediate Similarity	NPD4481	Phase 3
0.7172	Intermediate Similarity	NPD1778	Approved
0.7172	Intermediate Similarity	NPD17	Approved
0.7171	Intermediate Similarity	NPD4062	Phase 3
0.7162	Intermediate Similarity	NPD1283	Approved
0.7162	Intermediate Similarity	NPD3225	Approved
0.716	Intermediate Similarity	NPD3051	Approved
0.7153	Intermediate Similarity	NPD3134	Approved
0.7152	Intermediate Similarity	NPD2978	Approved
0.7152	Intermediate Similarity	NPD2977	Approved
0.7151	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7313	Approved
0.7143	Intermediate Similarity	NPD7311	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