NPASS Compound

Structure

NPC33832 OpenBabel07101718282D 25 29 0 0 1 0 0 0 0 0999 V2000 0.7431 -4.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 -3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8549 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8549 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2598 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -3.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1229 -3.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9889 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 -2.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -0.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -1.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 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 4 2 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 10 1 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 14 2 0 0 0 0 7 17 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 9 25 1 0 0 0 0 10 1 1 1 0 0 0 10 11 1 0 0 0 0 11 2 1 6 0 0 0 11 18 1 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 21 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 12 1 1 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	339.826
LogP:	5.025
LogD:	4.098
LogS:	-5.72
# Rotatable Bonds:	1
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	3.799
Fsp3:	0.4
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:	-5.068
MDCK Permeability:	3.2809584809001535e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	99.03372192382812%
Volume Distribution (VD):	3.114
Pgp-substrate:	1.2520025968551636%

ADMET: Metabolism

CYP1A2-inhibitor:	0.785
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.978
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.923
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.757

ADMET: Excretion

Clearance (CL):	19.911
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.446
Skin Sensitization:	0.71
Carcinogencity:	0.909
Eye Corrosion:	0.003
Eye Irritation:	0.501
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC33832

Natural Product ID:	NPC33832
*Common Name:**	Saurunarin
IUPAC Name:	(7R,8S,9S)-9-(1,3-benzodioxol-5-yl)-7,8-dimethyl-6,7,8,9-tetrahydrobenzo[g][1,3]benzodioxol-5-ol
Synonyms:
Standard InCHIKey:	UFGNCOLKCKXERC-DDBGAENHSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-10-5-13-14(21)7-17-20(25-9-24-17)19(13)18(11(10)2)12-3-4-15-16(6-12)23-8-22-15/h3-4,6-7,10-11,18,21H,5,8-9H2,1-2H3/t10-,11+,18+/m1/s1
SMILES:	C[C@@H]1Cc2c(cc3c(c2[C@@H]([C@H]1C)c1ccc2c(c1)OCO2)OCO3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104951
PubChem CID:	76331996
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	71400.0	nM	PMID[545829]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40300.0	nM	PMID[545829]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	84.0	%	PMID[545829]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	83.7	%	PMID[545829]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.6	%	PMID[545829]

☑ 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 NPC33832 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	459
0.1-0.2	1723
0.2-0.3	4386
0.3-0.4	11560
0.4-0.5	6913
0.5-0.6	4090
0.6-0.7	8540
0.7-0.8	3914
0.8-0.85	828
0.85-0.9	242
0.9-0.95	37
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9507	High Similarity	NPC116019
0.9493	High Similarity	NPC9068
0.9429	High Similarity	NPC191231
0.9362	High Similarity	NPC474808
0.9348	High Similarity	NPC197166
0.9286	High Similarity	NPC284464
0.9281	High Similarity	NPC196420
0.9214	High Similarity	NPC30951
0.9214	High Similarity	NPC6369
0.9209	High Similarity	NPC205442
0.9172	High Similarity	NPC71726
0.9097	High Similarity	NPC178014
0.9097	High Similarity	NPC474749
0.9097	High Similarity	NPC11422
0.9097	High Similarity	NPC42716
0.9097	High Similarity	NPC180953
0.9078	High Similarity	NPC29868
0.9078	High Similarity	NPC79622
0.9078	High Similarity	NPC212942
0.9048	High Similarity	NPC24425
0.9041	High Similarity	NPC166584
0.9041	High Similarity	NPC301961
0.9034	High Similarity	NPC154971
0.9034	High Similarity	NPC252286
0.9028	High Similarity	NPC172171
0.9028	High Similarity	NPC239254
0.9021	High Similarity	NPC184641
0.9021	High Similarity	NPC133934
0.9021	High Similarity	NPC184684
0.9	High Similarity	NPC313081
0.8966	High Similarity	NPC475868
0.8966	High Similarity	NPC307466
0.8944	High Similarity	NPC184613
0.8944	High Similarity	NPC290714
0.8944	High Similarity	NPC201404
0.8944	High Similarity	NPC53722
0.8936	High Similarity	NPC32189
0.8936	High Similarity	NPC202846
0.8936	High Similarity	NPC143139
0.8933	High Similarity	NPC159922
0.8913	High Similarity	NPC184814
0.8913	High Similarity	NPC63574
0.8913	High Similarity	NPC192687
0.8913	High Similarity	NPC224157
0.8904	High Similarity	NPC226540
0.8904	High Similarity	NPC162193
0.8897	High Similarity	NPC121661
0.8897	High Similarity	NPC73467
0.8889	High Similarity	NPC36531
0.8889	High Similarity	NPC472562
0.8889	High Similarity	NPC230538
0.8889	High Similarity	NPC103637
0.8889	High Similarity	NPC175838
0.8889	High Similarity	NPC80326
0.8889	High Similarity	NPC229172
0.8881	High Similarity	NPC177868
0.8873	High Similarity	NPC185908
0.8873	High Similarity	NPC266006
0.8865	High Similarity	NPC150534
0.8865	High Similarity	NPC69029
0.8865	High Similarity	NPC10314
0.8865	High Similarity	NPC111655
0.8865	High Similarity	NPC294884
0.8865	High Similarity	NPC200557
0.8865	High Similarity	NPC158142
0.8865	High Similarity	NPC108198
0.8857	High Similarity	NPC471390
0.8857	High Similarity	NPC471391
0.8857	High Similarity	NPC196937
0.8851	High Similarity	NPC240521
0.8841	High Similarity	NPC190144
0.8836	High Similarity	NPC110763
0.8836	High Similarity	NPC189239
0.8836	High Similarity	NPC197352
0.8836	High Similarity	NPC166506
0.8828	High Similarity	NPC265154
0.8828	High Similarity	NPC324962
0.8828	High Similarity	NPC255566
0.8828	High Similarity	NPC298317
0.8819	High Similarity	NPC300798
0.8819	High Similarity	NPC58137
0.8811	High Similarity	NPC114171
0.8811	High Similarity	NPC230124
0.8811	High Similarity	NPC6300
0.8794	High Similarity	NPC185680
0.8794	High Similarity	NPC209199
0.8794	High Similarity	NPC160697
0.8794	High Similarity	NPC256776
0.8794	High Similarity	NPC145722
0.8794	High Similarity	NPC125649
0.8792	High Similarity	NPC260781
0.8792	High Similarity	NPC469706
0.8792	High Similarity	NPC469707
0.8792	High Similarity	NPC185955
0.8792	High Similarity	NPC145979
0.8792	High Similarity	NPC225815
0.8792	High Similarity	NPC214326
0.8792	High Similarity	NPC9933
0.8792	High Similarity	NPC218041
0.8792	High Similarity	NPC182368
0.8786	High Similarity	NPC227002
0.8786	High Similarity	NPC161958
0.8786	High Similarity	NPC14224
0.8786	High Similarity	NPC6451
0.8759	High Similarity	NPC41782
0.8759	High Similarity	NPC174522
0.8758	High Similarity	NPC181168
0.8758	High Similarity	NPC19947
0.8758	High Similarity	NPC115281
0.8758	High Similarity	NPC207584
0.8758	High Similarity	NPC163527
0.875	High Similarity	NPC295719
0.875	High Similarity	NPC216434
0.875	High Similarity	NPC103448
0.875	High Similarity	NPC165026
0.875	High Similarity	NPC34431
0.875	High Similarity	NPC12668
0.875	High Similarity	NPC27495
0.875	High Similarity	NPC73505
0.875	High Similarity	NPC308768
0.8741	High Similarity	NPC25111
0.8741	High Similarity	NPC474039
0.8741	High Similarity	NPC201145
0.8741	High Similarity	NPC272157
0.8741	High Similarity	NPC56329
0.8741	High Similarity	NPC6262
0.8741	High Similarity	NPC242715
0.8741	High Similarity	NPC90615
0.8741	High Similarity	NPC283949
0.8741	High Similarity	NPC73535
0.8732	High Similarity	NPC241241
0.8723	High Similarity	NPC112237
0.8723	High Similarity	NPC136750
0.8723	High Similarity	NPC58585
0.8723	High Similarity	NPC266848
0.8714	High Similarity	NPC232275
0.8714	High Similarity	NPC45715
0.8714	High Similarity	NPC192255
0.8714	High Similarity	NPC12275
0.8714	High Similarity	NPC474356
0.871	High Similarity	NPC288149
0.8707	High Similarity	NPC205316
0.8699	High Similarity	NPC185071
0.8699	High Similarity	NPC12728
0.8696	High Similarity	NPC177167
0.8693	High Similarity	NPC237946
0.8693	High Similarity	NPC32373
0.8684	High Similarity	NPC103197
0.8684	High Similarity	NPC30009
0.8681	High Similarity	NPC218131
0.8681	High Similarity	NPC243759
0.8681	High Similarity	NPC105847
0.8681	High Similarity	NPC292487
0.8681	High Similarity	NPC275061
0.8681	High Similarity	NPC220344
0.8681	High Similarity	NPC243996
0.8681	High Similarity	NPC132804
0.8675	High Similarity	NPC21902
0.8671	High Similarity	NPC30632
0.8671	High Similarity	NPC173660
0.8671	High Similarity	NPC300846
0.8671	High Similarity	NPC476639
0.8671	High Similarity	NPC114155
0.8667	High Similarity	NPC238140
0.8667	High Similarity	NPC473989
0.8652	High Similarity	NPC104077
0.8652	High Similarity	NPC219671
0.8652	High Similarity	NPC7744
0.8652	High Similarity	NPC147616
0.8652	High Similarity	NPC259742
0.8652	High Similarity	NPC261812
0.8652	High Similarity	NPC65183
0.8652	High Similarity	NPC72046
0.8649	High Similarity	NPC112251
0.8645	High Similarity	NPC150943
0.8645	High Similarity	NPC91634
0.8645	High Similarity	NPC96593
0.8645	High Similarity	NPC268718
0.8643	High Similarity	NPC258483
0.8643	High Similarity	NPC126836
0.8643	High Similarity	NPC51840
0.8643	High Similarity	NPC311680
0.8643	High Similarity	NPC299221
0.8643	High Similarity	NPC234488
0.8639	High Similarity	NPC280092
0.8639	High Similarity	NPC93323
0.8639	High Similarity	NPC12641
0.8639	High Similarity	NPC45257
0.863	High Similarity	NPC107161
0.863	High Similarity	NPC474295
0.8621	High Similarity	NPC46591
0.8621	High Similarity	NPC226547
0.8621	High Similarity	NPC56091
0.8621	High Similarity	NPC254759
0.8621	High Similarity	NPC160283
0.8618	High Similarity	NPC245948
0.8611	High Similarity	NPC266453
0.8611	High Similarity	NPC200935
0.8611	High Similarity	NPC151656
0.8611	High Similarity	NPC230919

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 NPC33832 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	950
0.2-0.3	1733
0.3-0.4	2951
0.4-0.5	1617
0.5-0.6	908
0.6-0.7	529
0.7-0.8	78
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
0.8701	High Similarity	NPD6234	Discontinued
0.8693	High Similarity	NPD4966	Approved
0.8693	High Similarity	NPD4965	Approved
0.8693	High Similarity	NPD4967	Phase 2
0.8618	High Similarity	NPD37	Approved
0.8323	Intermediate Similarity	NPD7228	Approved
0.8182	Intermediate Similarity	NPD3027	Phase 3
0.8125	Intermediate Similarity	NPD7199	Phase 2
0.8025	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3705	Approved
0.7986	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6674	Discontinued
0.7917	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7240	Approved
0.7891	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1613	Approved
0.7877	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4908	Phase 1
0.7808	Intermediate Similarity	NPD4625	Phase 3
0.7765	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6232	Discontinued
0.7742	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7473	Discontinued
0.7671	Intermediate Similarity	NPD2861	Phase 2
0.7671	Intermediate Similarity	NPD3018	Phase 2
0.7658	Intermediate Similarity	NPD1653	Approved
0.7651	Intermediate Similarity	NPD3620	Phase 2
0.7651	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD5844	Phase 1
0.7609	Intermediate Similarity	NPD5283	Phase 1
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4749	Approved
0.7517	Intermediate Similarity	NPD2983	Phase 2
0.7517	Intermediate Similarity	NPD2982	Phase 2
0.7517	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3818	Discontinued
0.7448	Intermediate Similarity	NPD2981	Phase 2
0.7444	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2801	Approved
0.7417	Intermediate Similarity	NPD4060	Phase 1
0.7413	Intermediate Similarity	NPD1357	Approved
0.74	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7680	Approved
0.7347	Intermediate Similarity	NPD6696	Suspended
0.7346	Intermediate Similarity	NPD7028	Phase 2
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.732	Intermediate Similarity	NPD4097	Suspended
0.7312	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5494	Approved
0.7289	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7074	Phase 3
0.7261	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1934	Approved
0.7214	Intermediate Similarity	NPD228	Approved
0.7212	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7054	Approved
0.7184	Intermediate Similarity	NPD6559	Discontinued
0.7178	Intermediate Similarity	NPD4005	Discontinued
0.7168	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD3657	Discovery
0.7143	Intermediate Similarity	NPD1091	Approved
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3540	Phase 1
0.7134	Intermediate Similarity	NPD7266	Discontinued
0.7133	Intermediate Similarity	NPD4624	Approved
0.7126	Intermediate Similarity	NPD3882	Suspended
0.7126	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5125	Phase 3
0.7123	Intermediate Similarity	NPD5126	Approved
0.7123	Intermediate Similarity	NPD4626	Approved
0.7118	Intermediate Similarity	NPD7229	Phase 3
0.7115	Intermediate Similarity	NPD4108	Discontinued
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3022	Approved
0.7071	Intermediate Similarity	NPD4750	Phase 3
0.7071	Intermediate Similarity	NPD3021	Approved
0.707	Intermediate Similarity	NPD6099	Approved
0.707	Intermediate Similarity	NPD6100	Approved
0.707	Intermediate Similarity	NPD3539	Phase 1
0.707	Intermediate Similarity	NPD2935	Discontinued
0.7067	Intermediate Similarity	NPD3094	Phase 2
0.7063	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3383	Approved
0.7048	Intermediate Similarity	NPD3384	Approved
0.7048	Intermediate Similarity	NPD3382	Approved
0.7047	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7808	Phase 3
0.7042	Intermediate Similarity	NPD7635	Approved
0.7037	Intermediate Similarity	NPD2533	Approved
0.7037	Intermediate Similarity	NPD2532	Approved
0.7037	Intermediate Similarity	NPD2534	Approved
0.7035	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6166	Phase 2
0.7035	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6797	Phase 2
0.7025	Intermediate Similarity	NPD5763	Approved
0.7025	Intermediate Similarity	NPD5762	Approved
0.7019	Intermediate Similarity	NPD7124	Phase 2
0.7019	Intermediate Similarity	NPD5058	Phase 3
0.7018	Intermediate Similarity	NPD3787	Discontinued
0.7014	Intermediate Similarity	NPD6671	Approved
0.7006	Intermediate Similarity	NPD2977	Approved
0.7006	Intermediate Similarity	NPD2978	Approved
0.7006	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD3750	Approved
0.7	Intermediate Similarity	NPD3892	Phase 2
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7251	Discontinued
0.6983	Remote Similarity	NPD4663	Approved
0.6982	Remote Similarity	NPD4055	Discovery
0.6982	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1511	Approved
0.6975	Remote Similarity	NPD4357	Discontinued
0.6968	Remote Similarity	NPD4140	Approved
0.6964	Remote Similarity	NPD3817	Phase 2
0.6948	Remote Similarity	NPD5109	Approved
0.6948	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5111	Phase 2
0.6948	Remote Similarity	NPD5110	Phase 2
0.6944	Remote Similarity	NPD7906	Approved
0.6937	Remote Similarity	NPD5177	Phase 3
0.6933	Remote Similarity	NPD5327	Phase 3
0.6933	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3051	Approved
0.6918	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1375	Discontinued
0.6913	Remote Similarity	NPD3092	Approved
0.6913	Remote Similarity	NPD422	Phase 1
0.6913	Remote Similarity	NPD1611	Approved
0.691	Remote Similarity	NPD4577	Approved
0.691	Remote Similarity	NPD4578	Approved
0.6905	Remote Similarity	NPD7819	Suspended
0.6905	Remote Similarity	NPD5929	Approved
0.6897	Remote Similarity	NPD709	Approved
0.689	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1512	Approved
0.6887	Remote Similarity	NPD1283	Approved
0.6879	Remote Similarity	NPD2969	Approved
0.6879	Remote Similarity	NPD6353	Approved
0.6879	Remote Similarity	NPD2970	Approved
0.6875	Remote Similarity	NPD7037	Approved
0.6872	Remote Similarity	NPD8053	Approved
0.6872	Remote Similarity	NPD8054	Approved
0.6871	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3091	Approved
0.6871	Remote Similarity	NPD7041	Phase 2
0.6867	Remote Similarity	NPD7458	Discontinued
0.686	Remote Similarity	NPD8127	Discontinued
0.686	Remote Similarity	NPD6959	Discontinued
0.6859	Remote Similarity	NPD2238	Phase 2
0.6857	Remote Similarity	NPD3751	Discontinued
0.6851	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7340	Approved
0.6839	Remote Similarity	NPD2489	Approved
0.6839	Remote Similarity	NPD27	Approved
0.6835	Remote Similarity	NPD6111	Discontinued
0.6829	Remote Similarity	NPD7447	Phase 1
0.6829	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4380	Phase 2
0.6826	Remote Similarity	NPD4675	Approved
0.6826	Remote Similarity	NPD4678	Approved
0.6824	Remote Similarity	NPD5691	Approved
0.6818	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7311	Approved
0.6816	Remote Similarity	NPD7312	Approved
0.6816	Remote Similarity	NPD7313	Approved
0.6816	Remote Similarity	NPD7310	Approved
0.6815	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5124	Phase 1
0.6812	Remote Similarity	NPD940	Approved
0.6812	Remote Similarity	NPD846	Approved
0.6805	Remote Similarity	NPD8455	Phase 2
0.6804	Remote Similarity	NPD7827	Phase 1
0.6803	Remote Similarity	NPD5536	Phase 2
0.6792	Remote Similarity	NPD1510	Phase 2
0.679	Remote Similarity	NPD6331	Phase 2
0.679	Remote Similarity	NPD4110	Phase 3
0.679	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7466	Approved
0.6786	Remote Similarity	NPD5089	Approved
0.6786	Remote Similarity	NPD5090	Approved
0.6784	Remote Similarity	NPD5604	Discontinued
0.6784	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7833	Phase 2
0.6784	Remote Similarity	NPD7831	Phase 2
0.6778	Remote Similarity	NPD7309	Approved
0.6776	Remote Similarity	NPD8651	Approved
0.6774	Remote Similarity	NPD7095	Approved
0.6772	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1607	Approved
0.6768	Remote Similarity	NPD7213	Phase 3

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