NPASS Compound

Structure

NPC474160 OpenBabel07101719242D 24 25 0 0 1 0 0 0 0 0999 V2000 2.3660 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1340 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6340 3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 24 1 0 0 0 0 3 6 1 0 0 0 0 3 14 2 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 15 18 2 0 0 0 0 16 21 1 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.15
Volume:	345.563
LogP:	2.421
LogD:	2.757
LogS:	-2.752
# Rotatable Bonds:	7
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	3.106
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.705
MDCK Permeability:	1.1114693734270986e-05
Pgp-inhibitor:	0.159
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.187

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	91.40496063232422%
Volume Distribution (VD):	0.677
Pgp-substrate:	7.037618160247803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.334
CYP1A2-substrate:	0.484
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.221
CYP2C9-inhibitor:	0.489
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.745
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.565

ADMET: Excretion

Clearance (CL):	13.337
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.404
AMES Toxicity:	0.403
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.442
Carcinogencity:	0.239
Eye Corrosion:	0.003
Eye Irritation:	0.192
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC474160

Natural Product ID:	NPC474160
*Common Name:**	Thannilignan
IUPAC Name:	2-[(2-hydroxy-4-methoxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]but-3-ene-1,2-diol
Synonyms:	thannilignan
Standard InCHIKey:	UICXJFXGPMLFAQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H22O5/c1-13(9-14-3-6-16(21)7-4-14)19(23,12-20)11-15-5-8-17(24-2)10-18(15)22/h3-8,10,20-23H,1,9,11-12H2,2H3
SMILES:	COC1=CC(=C(C=C1)CC(CO)(C(=C)CC2=CC=C(C=C2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463091
PubChem CID:	466077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO33381	terminalia bellerica	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9249982]

☑ 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
EC50	1
IC50	1
Others	2

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	50000.0	nM	PMID[551996]
NPT3086	Organism	Penicillium expansum	Penicillium expansum	Activity	=	2.0	ug	PMID[551996]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	7000.0	nM	PMID[551996]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	80.0	ug	PMID[551996]

☑ 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 NPC474160 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	350
0.1-0.2	1498
0.2-0.3	4495
0.3-0.4	12189
0.4-0.5	6001
0.5-0.6	4382
0.6-0.7	7567
0.7-0.8	4998
0.8-0.85	756
0.85-0.9	427
0.9-0.95	33
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC54507
0.931	High Similarity	NPC85292
0.931	High Similarity	NPC229147
0.9268	High Similarity	NPC87224
0.9268	High Similarity	NPC222572
0.925	High Similarity	NPC77789
0.925	High Similarity	NPC18128
0.9224	High Similarity	NPC464
0.9224	High Similarity	NPC185541
0.92	High Similarity	NPC103799
0.9167	High Similarity	NPC476633
0.9153	High Similarity	NPC131118
0.9113	High Similarity	NPC274717
0.9106	High Similarity	NPC283049
0.9106	High Similarity	NPC26879
0.9106	High Similarity	NPC230479
0.9106	High Similarity	NPC50315
0.9068	High Similarity	NPC69261
0.9068	High Similarity	NPC33270
0.9068	High Similarity	NPC474933
0.9055	High Similarity	NPC92805
0.9048	High Similarity	NPC162801
0.904	High Similarity	NPC170844
0.904	High Similarity	NPC134360
0.904	High Similarity	NPC476968
0.904	High Similarity	NPC212015
0.9032	High Similarity	NPC159968
0.9032	High Similarity	NPC324112
0.9032	High Similarity	NPC236791
0.9032	High Similarity	NPC169474
0.9032	High Similarity	NPC293054
0.9032	High Similarity	NPC82679
0.9032	High Similarity	NPC74817
0.9032	High Similarity	NPC242032
0.9032	High Similarity	NPC246620
0.9032	High Similarity	NPC282000
0.9032	High Similarity	NPC124452
0.9024	High Similarity	NPC167571
0.9024	High Similarity	NPC207179
0.9024	High Similarity	NPC105925
0.9024	High Similarity	NPC278552
0.9016	High Similarity	NPC38761
0.9016	High Similarity	NPC76465
0.9016	High Similarity	NPC136319
0.8984	High Similarity	NPC124085
0.8984	High Similarity	NPC117048
0.8983	High Similarity	NPC150624
0.8983	High Similarity	NPC141090
0.8983	High Similarity	NPC203113
0.8968	High Similarity	NPC51840
0.8968	High Similarity	NPC311680
0.8968	High Similarity	NPC299221
0.8968	High Similarity	NPC234488
0.896	High Similarity	NPC53986
0.896	High Similarity	NPC38664
0.896	High Similarity	NPC206615
0.896	High Similarity	NPC98631
0.896	High Similarity	NPC470213
0.896	High Similarity	NPC186843
0.8952	High Similarity	NPC103823
0.8952	High Similarity	NPC18924
0.8952	High Similarity	NPC44748
0.8952	High Similarity	NPC28730
0.8952	High Similarity	NPC276212
0.8952	High Similarity	NPC78974
0.8952	High Similarity	NPC214406
0.8952	High Similarity	NPC223136
0.8934	High Similarity	NPC100099
0.8934	High Similarity	NPC36016
0.8926	High Similarity	NPC102639
0.8917	High Similarity	NPC184302
0.8915	High Similarity	NPC61946
0.8915	High Similarity	NPC164787
0.8915	High Similarity	NPC151224
0.8915	High Similarity	NPC256262
0.8908	High Similarity	NPC470759
0.8908	High Similarity	NPC127894
0.8908	High Similarity	NPC15860
0.8908	High Similarity	NPC219070
0.8906	High Similarity	NPC85435
0.8906	High Similarity	NPC475840
0.8906	High Similarity	NPC11060
0.8898	High Similarity	NPC164804
0.8898	High Similarity	NPC474017
0.8898	High Similarity	NPC293203
0.8898	High Similarity	NPC211413
0.8898	High Similarity	NPC53906
0.8898	High Similarity	NPC808
0.8898	High Similarity	NPC118683
0.8898	High Similarity	NPC68205
0.8898	High Similarity	NPC244888
0.8889	High Similarity	NPC93962
0.8889	High Similarity	NPC58164
0.8889	High Similarity	NPC469963
0.8889	High Similarity	NPC10225
0.8889	High Similarity	NPC469951
0.888	High Similarity	NPC473221
0.8871	High Similarity	NPC82483
0.8871	High Similarity	NPC299584
0.8871	High Similarity	NPC103420
0.8871	High Similarity	NPC251855
0.8871	High Similarity	NPC102540
0.8871	High Similarity	NPC234400
0.8871	High Similarity	NPC17943
0.8871	High Similarity	NPC117214
0.8871	High Similarity	NPC265483
0.8871	High Similarity	NPC208950
0.8871	High Similarity	NPC60885
0.8871	High Similarity	NPC188022
0.8871	High Similarity	NPC193544
0.8871	High Similarity	NPC233410
0.8871	High Similarity	NPC17809
0.8871	High Similarity	NPC221077
0.8871	High Similarity	NPC116907
0.8871	High Similarity	NPC472093
0.8871	High Similarity	NPC285040
0.8871	High Similarity	NPC298757
0.8871	High Similarity	NPC57490
0.8871	High Similarity	NPC113495
0.8871	High Similarity	NPC475169
0.8871	High Similarity	NPC203133
0.8862	High Similarity	NPC282496
0.8862	High Similarity	NPC233526
0.8855	High Similarity	NPC475836
0.8852	High Similarity	NPC97432
0.8852	High Similarity	NPC54972
0.8852	High Similarity	NPC190454
0.8846	High Similarity	NPC230734
0.8846	High Similarity	NPC18189
0.8846	High Similarity	NPC262585
0.8846	High Similarity	NPC472336
0.8846	High Similarity	NPC269091
0.8846	High Similarity	NPC306441
0.8846	High Similarity	NPC302701
0.8846	High Similarity	NPC3049
0.8846	High Similarity	NPC227503
0.8846	High Similarity	NPC472334
0.8846	High Similarity	NPC474639
0.8846	High Similarity	NPC16435
0.8846	High Similarity	NPC20829
0.8843	High Similarity	NPC223451
0.8833	High Similarity	NPC190514
0.8828	High Similarity	NPC6451
0.8828	High Similarity	NPC201587
0.8828	High Similarity	NPC13005
0.8828	High Similarity	NPC253105
0.8824	High Similarity	NPC114064
0.8819	High Similarity	NPC192687
0.8819	High Similarity	NPC224157
0.8819	High Similarity	NPC126836
0.8814	High Similarity	NPC228287
0.8814	High Similarity	NPC180508
0.8814	High Similarity	NPC276737
0.8814	High Similarity	NPC22610
0.881	High Similarity	NPC39064
0.881	High Similarity	NPC28765
0.881	High Similarity	NPC154866
0.881	High Similarity	NPC47283
0.881	High Similarity	NPC266691
0.88	High Similarity	NPC223953
0.88	High Similarity	NPC82299
0.879	High Similarity	NPC197351
0.879	High Similarity	NPC86502
0.879	High Similarity	NPC106914
0.879	High Similarity	NPC246648
0.879	High Similarity	NPC134195
0.8779	High Similarity	NPC474687
0.8769	High Similarity	NPC474206
0.8769	High Similarity	NPC473413
0.8769	High Similarity	NPC112939
0.8769	High Similarity	NPC234333
0.8769	High Similarity	NPC47398
0.8769	High Similarity	NPC121812
0.8769	High Similarity	NPC472337
0.8769	High Similarity	NPC470356
0.8769	High Similarity	NPC94750
0.8769	High Similarity	NPC112246
0.8769	High Similarity	NPC260898
0.876	High Similarity	NPC215037
0.876	High Similarity	NPC168059
0.876	High Similarity	NPC77196
0.876	High Similarity	NPC229442
0.876	High Similarity	NPC295259
0.876	High Similarity	NPC263064
0.875	High Similarity	NPC50521
0.875	High Similarity	NPC150011
0.875	High Similarity	NPC195466
0.875	High Similarity	NPC118114
0.875	High Similarity	NPC268917
0.875	High Similarity	NPC236014
0.875	High Similarity	NPC472597
0.875	High Similarity	NPC129106
0.875	High Similarity	NPC196765
0.875	High Similarity	NPC129784
0.875	High Similarity	NPC12875
0.875	High Similarity	NPC244816
0.875	High Similarity	NPC207892
0.875	High Similarity	NPC470096
0.875	High Similarity	NPC17343
0.875	High Similarity	NPC474356

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 NPC474160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	895
0.2-0.3	1724
0.3-0.4	2710
0.4-0.5	1723
0.5-0.6	977
0.6-0.7	668
0.7-0.8	135
0.8-0.85	5
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.904	High Similarity	NPD3027	Phase 3
0.881	High Similarity	NPD4908	Phase 1
0.8699	High Similarity	NPD1610	Phase 2
0.8682	High Similarity	NPD1613	Approved
0.8682	High Similarity	NPD1612	Clinical (unspecified phase)
0.8678	High Similarity	NPD1548	Phase 1
0.8672	High Similarity	NPD4907	Clinical (unspecified phase)
0.8516	High Similarity	NPD1529	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD4625	Phase 3
0.8125	Intermediate Similarity	NPD4749	Approved
0.8106	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD846	Approved
0.8103	Intermediate Similarity	NPD940	Approved
0.8077	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD2861	Phase 2
0.8015	Intermediate Similarity	NPD3018	Phase 2
0.8	Intermediate Similarity	NPD2684	Approved
0.7969	Intermediate Similarity	NPD422	Phase 1
0.7969	Intermediate Similarity	NPD1091	Approved
0.7886	Intermediate Similarity	NPD7843	Approved
0.7883	Intermediate Similarity	NPD1510	Phase 2
0.7862	Intermediate Similarity	NPD4380	Phase 2
0.7852	Intermediate Similarity	NPD1240	Approved
0.7846	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD2982	Phase 2
0.7846	Intermediate Similarity	NPD2983	Phase 2
0.784	Intermediate Similarity	NPD6671	Approved
0.784	Intermediate Similarity	NPD7157	Approved
0.7794	Intermediate Similarity	NPD5124	Phase 1
0.7794	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD8651	Approved
0.7769	Intermediate Similarity	NPD2981	Phase 2
0.7769	Intermediate Similarity	NPD290	Approved
0.7762	Intermediate Similarity	NPD7447	Phase 1
0.7762	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1607	Approved
0.7721	Intermediate Similarity	NPD2238	Phase 2
0.7721	Intermediate Similarity	NPD4060	Phase 1
0.7712	Intermediate Similarity	NPD1242	Phase 1
0.7703	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7213	Phase 3
0.7692	Intermediate Similarity	NPD7212	Phase 2
0.7686	Intermediate Similarity	NPD968	Approved
0.7681	Intermediate Similarity	NPD4536	Approved
0.7681	Intermediate Similarity	NPD4538	Approved
0.7681	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5283	Phase 1
0.7672	Intermediate Similarity	NPD2860	Approved
0.7672	Intermediate Similarity	NPD2859	Approved
0.7661	Intermediate Similarity	NPD228	Approved
0.766	Intermediate Similarity	NPD1652	Phase 2
0.7643	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4750	Phase 3
0.7635	Intermediate Similarity	NPD1934	Approved
0.7627	Intermediate Similarity	NPD3020	Approved
0.7589	Intermediate Similarity	NPD1549	Phase 2
0.7586	Intermediate Similarity	NPD2933	Approved
0.7586	Intermediate Similarity	NPD2934	Approved
0.755	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5846	Approved
0.7538	Intermediate Similarity	NPD6516	Phase 2
0.75	Intermediate Similarity	NPD5451	Approved
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD5058	Phase 3
0.75	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.7483	Intermediate Similarity	NPD3892	Phase 2
0.7483	Intermediate Similarity	NPD3750	Approved
0.7467	Intermediate Similarity	NPD2801	Approved
0.7465	Intermediate Similarity	NPD2424	Discontinued
0.7448	Intermediate Similarity	NPD1511	Approved
0.7448	Intermediate Similarity	NPD6799	Approved
0.7447	Intermediate Similarity	NPD6100	Approved
0.7447	Intermediate Similarity	NPD2935	Discontinued
0.7447	Intermediate Similarity	NPD2796	Approved
0.7447	Intermediate Similarity	NPD6099	Approved
0.7445	Intermediate Similarity	NPD6798	Discontinued
0.7444	Intermediate Similarity	NPD6583	Phase 3
0.7444	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6582	Phase 2
0.7434	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7075	Discontinued
0.741	Intermediate Similarity	NPD6355	Discontinued
0.7407	Intermediate Similarity	NPD6584	Phase 3
0.7405	Intermediate Similarity	NPD2667	Approved
0.7405	Intermediate Similarity	NPD2668	Approved
0.74	Intermediate Similarity	NPD37	Approved
0.7397	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3540	Phase 1
0.7372	Intermediate Similarity	NPD6166	Phase 2
0.7372	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3882	Suspended
0.7368	Intermediate Similarity	NPD2230	Approved
0.7368	Intermediate Similarity	NPD2232	Approved
0.7368	Intermediate Similarity	NPD2233	Approved
0.7365	Intermediate Similarity	NPD1653	Approved
0.7361	Intermediate Similarity	NPD7466	Approved
0.7361	Intermediate Similarity	NPD4628	Phase 3
0.7361	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3847	Discontinued
0.7347	Intermediate Similarity	NPD1512	Approved
0.7333	Intermediate Similarity	NPD6072	Discontinued
0.7333	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1551	Phase 2
0.7324	Intermediate Similarity	NPD3539	Phase 1
0.7323	Intermediate Similarity	NPD5535	Approved
0.731	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6801	Discontinued
0.7279	Intermediate Similarity	NPD3691	Phase 2
0.7279	Intermediate Similarity	NPD3690	Phase 2
0.7273	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7266	Intermediate Similarity	NPD6233	Phase 2
0.7259	Intermediate Similarity	NPD6696	Suspended
0.7255	Intermediate Similarity	NPD4966	Approved
0.7255	Intermediate Similarity	NPD7768	Phase 2
0.7255	Intermediate Similarity	NPD4967	Phase 2
0.7255	Intermediate Similarity	NPD4965	Approved
0.7246	Intermediate Similarity	NPD7095	Approved
0.7241	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7411	Suspended
0.7218	Intermediate Similarity	NPD3496	Discontinued
0.7214	Intermediate Similarity	NPD3620	Phase 2
0.7214	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD2797	Approved
0.7206	Intermediate Similarity	NPD3094	Phase 2
0.72	Intermediate Similarity	NPD4005	Discontinued
0.7192	Intermediate Similarity	NPD2677	Approved
0.719	Intermediate Similarity	NPD3817	Phase 2
0.7188	Intermediate Similarity	NPD7074	Phase 3
0.7188	Intermediate Similarity	NPD821	Approved
0.7181	Intermediate Similarity	NPD5403	Approved
0.7179	Intermediate Similarity	NPD7199	Phase 2
0.7172	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5177	Phase 3
0.7172	Intermediate Similarity	NPD3060	Approved
0.717	Intermediate Similarity	NPD3818	Discontinued
0.7164	Intermediate Similarity	NPD3705	Approved
0.7163	Intermediate Similarity	NPD4340	Discontinued
0.7163	Intermediate Similarity	NPD5735	Approved
0.7154	Intermediate Similarity	NPD2557	Approved
0.7153	Intermediate Similarity	NPD5762	Approved
0.7153	Intermediate Similarity	NPD7266	Discontinued
0.7153	Intermediate Similarity	NPD5763	Approved
0.7153	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4675	Approved
0.7152	Intermediate Similarity	NPD4678	Approved
0.7143	Intermediate Similarity	NPD6405	Approved
0.7143	Intermediate Similarity	NPD6407	Approved
0.7143	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7133	Intermediate Similarity	NPD3748	Approved
0.7132	Intermediate Similarity	NPD3225	Approved
0.7125	Intermediate Similarity	NPD7054	Approved
0.7124	Intermediate Similarity	NPD7819	Suspended
0.7123	Intermediate Similarity	NPD4535	Phase 3
0.7113	Intermediate Similarity	NPD3054	Approved
0.7113	Intermediate Similarity	NPD4097	Suspended
0.7113	Intermediate Similarity	NPD2568	Approved
0.7113	Intermediate Similarity	NPD3052	Approved
0.7111	Intermediate Similarity	NPD2235	Phase 2
0.7111	Intermediate Similarity	NPD2231	Phase 2
0.7099	Intermediate Similarity	NPD6559	Discontinued
0.7099	Intermediate Similarity	NPD3596	Phase 2
0.7095	Intermediate Similarity	NPD4357	Discontinued
0.7092	Intermediate Similarity	NPD1558	Phase 1
0.7092	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD844	Approved
0.7081	Intermediate Similarity	NPD7472	Approved
0.7078	Intermediate Similarity	NPD5402	Approved
0.7071	Intermediate Similarity	NPD3268	Approved
0.7068	Intermediate Similarity	NPD5691	Approved
0.7068	Intermediate Similarity	NPD3445	Approved
0.7068	Intermediate Similarity	NPD3443	Approved
0.7068	Intermediate Similarity	NPD1357	Approved
0.7068	Intermediate Similarity	NPD3444	Approved
0.7063	Intermediate Similarity	NPD7228	Approved
0.7063	Intermediate Similarity	NPD1358	Approved
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7059	Intermediate Similarity	NPD3685	Discontinued
0.7055	Intermediate Similarity	NPD6674	Discontinued
0.705	Intermediate Similarity	NPD596	Approved
0.705	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD600	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