NPASS Compound

Structure

CID135777 OpenBabel06191715492D 25 28 0 0 1 0 0 0 0 0999 V2000 0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0540 0.5885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0649 0.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2514 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0505 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2460 -1.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6527 -0.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8337 -2.1521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6472 -0.3250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4627 1.4023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4627 -0.2158 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 3 22 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 1 1 1 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 2 1 6 0 0 0 12 20 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 13 1 1 0 0 0 19 25 1 0 0 0 0 20 14 1 1 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.15
Volume:	348.383
LogP:	4.38
LogD:	3.868
LogS:	-5.26
# Rotatable Bonds:	3
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.905
Synthetic Accessibility Score:	3.487
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.729
MDCK Permeability:	5.1533996156649664e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	96.61123657226562%
Volume Distribution (VD):	1.61
Pgp-substrate:	2.048046588897705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.721
CYP1A2-substrate:	0.824
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.465
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.538

ADMET: Excretion

Clearance (CL):	17.937
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.43
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.146
Skin Sensitization:	0.79
Carcinogencity:	0.831
Eye Corrosion:	0.005
Eye Irritation:	0.825
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC135777

Natural Product ID:	NPC135777
*Common Name:**	Austrobailignan-7
IUPAC Name:	5-[(2R,3S,4S,5S)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
Synonyms:	Austrobailignan-7
Standard InCHIKey:	NCDUCYPQLGABJF-UAFHBQARSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-11-12(2)20(14-5-7-17-18(9-14)24-10-23-17)25-19(11)13-4-6-16(22-3)15(21)8-13/h4-9,11-12,19-21H,10H2,1-3H3/t11-,12-,19+,20-/m0/s1
SMILES:	COc1ccc(cc1O)[C@@H]1O[C@@H]([C@H]([C@@H]1C)C)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558516
PubChem CID:	45273558
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	19900.0	nM	PMID[460771]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	2.9	n.a.	PMID[460771]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	6800.0	nM	PMID[460771]

☑ 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 NPC135777 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	362
0.1-0.2	1366
0.2-0.3	3517
0.3-0.4	9812
0.4-0.5	9280
0.5-0.6	5470
0.6-0.7	8886
0.7-0.8	2936
0.8-0.85	690
0.85-0.9	265
0.9-0.95	104
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC142547
0.9771	High Similarity	NPC193666
0.9771	High Similarity	NPC88640
0.9771	High Similarity	NPC123526
0.9766	High Similarity	NPC471505
0.9612	High Similarity	NPC219671
0.9612	High Similarity	NPC104077
0.9612	High Similarity	NPC106739
0.9612	High Similarity	NPC147616
0.9612	High Similarity	NPC259742
0.9549	High Similarity	NPC177868
0.9542	High Similarity	NPC184938
0.9542	High Similarity	NPC101624
0.9538	High Similarity	NPC169973
0.9535	High Similarity	NPC27843
0.9535	High Similarity	NPC115207
0.9535	High Similarity	NPC161557
0.9535	High Similarity	NPC40432
0.9535	High Similarity	NPC228346
0.9535	High Similarity	NPC7171
0.9535	High Similarity	NPC158079
0.9481	High Similarity	NPC265154
0.9481	High Similarity	NPC255566
0.9481	High Similarity	NPC298317
0.9481	High Similarity	NPC477898
0.9462	High Similarity	NPC181049
0.9462	High Similarity	NPC207400
0.9457	High Similarity	NPC275950
0.9453	High Similarity	NPC165128
0.9453	High Similarity	NPC57119
0.9453	High Similarity	NPC21867
0.9453	High Similarity	NPC11258
0.9453	High Similarity	NPC129570
0.9453	High Similarity	NPC226862
0.9453	High Similarity	NPC45774
0.9453	High Similarity	NPC128208
0.9453	High Similarity	NPC158471
0.9453	High Similarity	NPC282703
0.9453	High Similarity	NPC184733
0.9412	High Similarity	NPC84181
0.9394	High Similarity	NPC18576
0.9385	High Similarity	NPC476345
0.9343	High Similarity	NPC279298
0.9343	High Similarity	NPC38041
0.9343	High Similarity	NPC22150
0.9338	High Similarity	NPC185071
0.9338	High Similarity	NPC12728
0.9333	High Similarity	NPC472711
0.9318	High Similarity	NPC47181
0.9313	High Similarity	NPC4940
0.9308	High Similarity	NPC153739
0.9308	High Similarity	NPC257582
0.9308	High Similarity	NPC145305
0.9308	High Similarity	NPC271208
0.9308	High Similarity	NPC64201
0.9308	High Similarity	NPC242807
0.9308	High Similarity	NPC241522
0.9308	High Similarity	NPC187998
0.9308	High Similarity	NPC173308
0.9308	High Similarity	NPC233224
0.9308	High Similarity	NPC92164
0.9308	High Similarity	NPC77040
0.9308	High Similarity	NPC42300
0.9308	High Similarity	NPC174495
0.9308	High Similarity	NPC181079
0.9297	High Similarity	NPC274356
0.9275	High Similarity	NPC112861
0.9265	High Similarity	NPC302506
0.9254	High Similarity	NPC474039
0.9254	High Similarity	NPC101807
0.9248	High Similarity	NPC126409
0.9248	High Similarity	NPC174191
0.9248	High Similarity	NPC99572
0.9237	High Similarity	NPC277804
0.9237	High Similarity	NPC82111
0.9237	High Similarity	NPC227160
0.9231	High Similarity	NPC475875
0.9203	High Similarity	NPC477702
0.9203	High Similarity	NPC18979
0.9197	High Similarity	NPC185307
0.9197	High Similarity	NPC470950
0.9185	High Similarity	NPC156376
0.9173	High Similarity	NPC67247
0.9167	High Similarity	NPC7744
0.9154	High Similarity	NPC470084
0.9147	High Similarity	NPC213711
0.9147	High Similarity	NPC40352
0.9143	High Similarity	NPC304048
0.9143	High Similarity	NPC226153
0.9137	High Similarity	NPC212890
0.913	High Similarity	NPC470235
0.913	High Similarity	NPC283995
0.913	High Similarity	NPC179521
0.913	High Similarity	NPC129417
0.9124	High Similarity	NPC476356
0.9124	High Similarity	NPC253878
0.9124	High Similarity	NPC246947
0.9111	High Similarity	NPC469981
0.9111	High Similarity	NPC185908
0.9104	High Similarity	NPC24490
0.9104	High Similarity	NPC141765
0.9104	High Similarity	NPC34103
0.9104	High Similarity	NPC165155
0.9098	High Similarity	NPC266848
0.9098	High Similarity	NPC136750
0.9098	High Similarity	NPC158331
0.9078	High Similarity	NPC286235
0.9078	High Similarity	NPC55158
0.9078	High Similarity	NPC51328
0.9077	High Similarity	NPC165045
0.9077	High Similarity	NPC118533
0.907	High Similarity	NPC148627
0.9065	High Similarity	NPC469586
0.9065	High Similarity	NPC180953
0.9062	High Similarity	NPC317769
0.9062	High Similarity	NPC249788
0.9062	High Similarity	NPC31344
0.9058	High Similarity	NPC474808
0.9058	High Similarity	NPC46092
0.9051	High Similarity	NPC471414
0.9051	High Similarity	NPC471908
0.9037	High Similarity	NPC177035
0.9037	High Similarity	NPC471988
0.9037	High Similarity	NPC199459
0.9037	High Similarity	NPC52277
0.903	High Similarity	NPC90083
0.903	High Similarity	NPC287745
0.903	High Similarity	NPC470881
0.903	High Similarity	NPC193026
0.903	High Similarity	NPC471942
0.903	High Similarity	NPC49603
0.903	High Similarity	NPC187616
0.903	High Similarity	NPC170779
0.9023	High Similarity	NPC171928
0.9023	High Similarity	NPC261812
0.9023	High Similarity	NPC33611
0.9023	High Similarity	NPC204215
0.9023	High Similarity	NPC100223
0.9023	High Similarity	NPC16830
0.9023	High Similarity	NPC65183
0.9023	High Similarity	NPC158526
0.9023	High Similarity	NPC175067
0.9023	High Similarity	NPC72046
0.9023	High Similarity	NPC129687
0.9015	High Similarity	NPC134764
0.9015	High Similarity	NPC171550
0.9014	High Similarity	NPC98624
0.9014	High Similarity	NPC475224
0.9007	High Similarity	NPC248132
0.9007	High Similarity	NPC130449
0.9007	High Similarity	NPC301961
0.9007	High Similarity	NPC166584
0.9	High Similarity	NPC241846
0.9	High Similarity	NPC252286
0.9	High Similarity	NPC154971
0.9	High Similarity	NPC93610
0.9	High Similarity	NPC206882
0.8993	High Similarity	NPC187774
0.8993	High Similarity	NPC118385
0.8993	High Similarity	NPC472713
0.8993	High Similarity	NPC472712
0.8993	High Similarity	NPC473046
0.8992	High Similarity	NPC257682
0.8992	High Similarity	NPC146355
0.8992	High Similarity	NPC34902
0.8992	High Similarity	NPC18449
0.8992	High Similarity	NPC121783
0.8992	High Similarity	NPC131747
0.8986	High Similarity	NPC41782
0.8978	High Similarity	NPC284464
0.8978	High Similarity	NPC46591
0.8971	High Similarity	NPC281780
0.8971	High Similarity	NPC283949
0.8963	High Similarity	NPC474139
0.8963	High Similarity	NPC189474
0.8963	High Similarity	NPC150534
0.8955	High Similarity	NPC6836
0.8955	High Similarity	NPC196937
0.8947	High Similarity	NPC248307
0.8947	High Similarity	NPC192255
0.8947	High Similarity	NPC65942
0.8936	High Similarity	NPC224674
0.8936	High Similarity	NPC275284
0.8936	High Similarity	NPC15956
0.8936	High Similarity	NPC193473
0.8936	High Similarity	NPC114505
0.8936	High Similarity	NPC213074
0.8936	High Similarity	NPC39657
0.8936	High Similarity	NPC31325
0.8931	High Similarity	NPC5428
0.8931	High Similarity	NPC158737
0.8921	High Similarity	NPC278961
0.8921	High Similarity	NPC113680
0.8915	High Similarity	NPC471693
0.8913	High Similarity	NPC166137
0.8913	High Similarity	NPC282291
0.8906	High Similarity	NPC126935
0.8906	High Similarity	NPC312713
0.8906	High Similarity	NPC216929
0.8906	High Similarity	NPC301641

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 NPC135777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	820
0.2-0.3	1685
0.3-0.4	2770
0.4-0.5	1869
0.5-0.6	1070
0.6-0.7	559
0.7-0.8	76
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
0.8657	High Similarity	NPD3027	Phase 3
0.8615	High Similarity	NPD3705	Approved
0.8411	Intermediate Similarity	NPD6234	Discontinued
0.8244	Intermediate Similarity	NPD1357	Approved
0.8203	Intermediate Similarity	NPD5283	Phase 1
0.8158	Intermediate Similarity	NPD4965	Approved
0.8158	Intermediate Similarity	NPD4967	Phase 2
0.8158	Intermediate Similarity	NPD4966	Approved
0.8151	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1613	Approved
0.8047	Intermediate Similarity	NPD228	Approved
0.8038	Intermediate Similarity	NPD7228	Approved
0.7986	Intermediate Similarity	NPD7266	Discontinued
0.7971	Intermediate Similarity	NPD2861	Phase 2
0.7961	Intermediate Similarity	NPD37	Approved
0.7943	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD3620	Phase 2
0.7914	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2977	Approved
0.7908	Intermediate Similarity	NPD2978	Approved
0.7891	Intermediate Similarity	NPD3021	Approved
0.7891	Intermediate Similarity	NPD3022	Approved
0.7877	Intermediate Similarity	NPD6674	Discontinued
0.7842	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD4060	Phase 1
0.7664	Intermediate Similarity	NPD1091	Approved
0.7625	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1375	Discontinued
0.76	Intermediate Similarity	NPD5058	Phase 3
0.7593	Intermediate Similarity	NPD3818	Discontinued
0.7582	Intermediate Similarity	NPD1653	Approved
0.7569	Intermediate Similarity	NPD1558	Phase 1
0.7545	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4908	Phase 1
0.7517	Intermediate Similarity	NPD4237	Approved
0.7517	Intermediate Similarity	NPD4236	Phase 3
0.7515	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4110	Phase 3
0.7467	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2983	Phase 2
0.7429	Intermediate Similarity	NPD2982	Phase 2
0.7417	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7685	Pre-registration
0.741	Intermediate Similarity	NPD1610	Phase 2
0.7407	Intermediate Similarity	NPD7157	Approved
0.7405	Intermediate Similarity	NPD2684	Approved
0.74	Intermediate Similarity	NPD3060	Approved
0.7397	Intermediate Similarity	NPD6355	Discontinued
0.7397	Intermediate Similarity	NPD5735	Approved
0.7394	Intermediate Similarity	NPD7074	Phase 3
0.7391	Intermediate Similarity	NPD5126	Approved
0.7391	Intermediate Similarity	NPD5125	Phase 3
0.7389	Intermediate Similarity	NPD1934	Approved
0.7383	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7028	Phase 2
0.7357	Intermediate Similarity	NPD2981	Phase 2
0.7351	Intermediate Similarity	NPD6331	Phase 2
0.7343	Intermediate Similarity	NPD3018	Phase 2
0.7342	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7054	Approved
0.7315	Intermediate Similarity	NPD2161	Phase 2
0.7313	Intermediate Similarity	NPD7843	Approved
0.7299	Intermediate Similarity	NPD5536	Phase 2
0.729	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7472	Approved
0.7285	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7255	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3882	Suspended
0.7248	Intermediate Similarity	NPD5588	Approved
0.7248	Intermediate Similarity	NPD4108	Discontinued
0.7241	Intermediate Similarity	NPD7095	Approved
0.7237	Intermediate Similarity	NPD4628	Phase 3
0.7233	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5110	Phase 2
0.7192	Intermediate Similarity	NPD5111	Phase 2
0.7192	Intermediate Similarity	NPD5109	Approved
0.719	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3020	Approved
0.7181	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4536	Approved
0.7181	Intermediate Similarity	NPD4538	Approved
0.7175	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3657	Discovery
0.7161	Intermediate Similarity	NPD4123	Phase 3
0.7153	Intermediate Similarity	NPD6671	Approved
0.7153	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4210	Discontinued
0.7133	Intermediate Similarity	NPD8651	Approved
0.7125	Intermediate Similarity	NPD2801	Approved
0.7122	Intermediate Similarity	NPD1548	Phase 1
0.7121	Intermediate Similarity	NPD968	Approved
0.7115	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6653	Approved
0.7113	Intermediate Similarity	NPD1608	Approved
0.7111	Intermediate Similarity	NPD7680	Approved
0.7101	Intermediate Similarity	NPD7251	Discontinued
0.7099	Intermediate Similarity	NPD5604	Discontinued
0.7095	Intermediate Similarity	NPD4140	Approved
0.7095	Intermediate Similarity	NPD2238	Phase 2
0.7083	Intermediate Similarity	NPD3094	Phase 2
0.7078	Intermediate Similarity	NPD2677	Approved
0.7078	Intermediate Similarity	NPD6190	Approved
0.7075	Intermediate Similarity	NPD3144	Approved
0.7075	Intermediate Similarity	NPD6798	Discontinued
0.7075	Intermediate Similarity	NPD3145	Approved
0.7067	Intermediate Similarity	NPD7097	Phase 1
0.7063	Intermediate Similarity	NPD4749	Approved
0.7063	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5327	Phase 3
0.7063	Intermediate Similarity	NPD3685	Discontinued
0.7059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7808	Phase 3
0.7059	Intermediate Similarity	NPD5177	Phase 3
0.7059	Intermediate Similarity	NPD4162	Approved
0.7055	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD27	Approved
0.7048	Intermediate Similarity	NPD2489	Approved
0.7048	Intermediate Similarity	NPD6166	Phase 2
0.7048	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3092	Approved
0.7027	Intermediate Similarity	NPD6233	Phase 2
0.7025	Intermediate Similarity	NPD3687	Approved
0.7025	Intermediate Similarity	NPD3686	Approved
0.7021	Intermediate Similarity	NPD6516	Phase 2
0.7021	Intermediate Similarity	NPD5846	Approved
0.702	Intermediate Similarity	NPD5960	Phase 3
0.702	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5773	Approved
0.7019	Intermediate Similarity	NPD5772	Approved
0.7019	Intermediate Similarity	NPD8455	Phase 2
0.7014	Intermediate Similarity	NPD6696	Suspended
0.7011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD6353	Approved
0.7	Intermediate Similarity	NPD6559	Discontinued
0.6994	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2233	Approved
0.6993	Remote Similarity	NPD2231	Phase 2
0.6993	Remote Similarity	NPD2232	Approved
0.6993	Remote Similarity	NPD2235	Phase 2
0.6993	Remote Similarity	NPD2230	Approved
0.6988	Remote Similarity	NPD2970	Approved
0.6988	Remote Similarity	NPD2969	Approved
0.6986	Remote Similarity	NPD9494	Approved
0.6981	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2563	Approved
0.6975	Remote Similarity	NPD2560	Approved
0.697	Remote Similarity	NPD8127	Discontinued
0.6968	Remote Similarity	NPD5241	Discontinued
0.6959	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6896	Approved
0.6954	Remote Similarity	NPD6895	Approved
0.6953	Remote Similarity	NPD2860	Approved
0.6953	Remote Similarity	NPD2859	Approved
0.695	Remote Similarity	NPD5585	Approved
0.6944	Remote Similarity	NPD6583	Phase 3
0.6944	Remote Similarity	NPD6582	Phase 2
0.694	Remote Similarity	NPD290	Approved
0.6937	Remote Similarity	NPD4675	Approved
0.6937	Remote Similarity	NPD4678	Approved
0.6934	Remote Similarity	NPD5535	Approved
0.6933	Remote Similarity	NPD4340	Discontinued
0.6928	Remote Similarity	NPD6005	Phase 3
0.6928	Remote Similarity	NPD6002	Phase 3
0.6928	Remote Similarity	NPD3051	Approved
0.6928	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6004	Phase 3
0.6923	Remote Similarity	NPD7124	Phase 2
0.6919	Remote Similarity	NPD7310	Approved
0.6919	Remote Similarity	NPD7311	Approved
0.6919	Remote Similarity	NPD7312	Approved
0.6919	Remote Similarity	NPD7313	Approved
0.6918	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4624	Approved
0.6914	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4062	Phase 3
0.6913	Remote Similarity	NPD554	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5582	Discontinued
0.6909	Remote Similarity	NPD5494	Approved
0.6906	Remote Similarity	NPD709	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