NPASS Compound

Structure

CID103448 OpenBabel06191715452D 30 34 0 0 1 0 0 0 0 0999 V2000 5.3876 -1.5639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2279 -2.6904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4381 2.6562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1204 3.5626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2086 2.0368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7793 2.5911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3843 1.0763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6179 -1.6108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5234 -0.7204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5271 -1.2001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8893 -1.8197 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9169 0.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3891 -1.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9617 1.8601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -1.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0269 0.3444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3891 -0.2752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5271 -0.3097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9993 -1.7938 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0717 1.8859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -0.2752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6043 1.1281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6179 0.1701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4701 2.6843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6121 2.7383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6682 1.1844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6179 2.1069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.4407 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 3.2480 -0.5215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 28 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 1 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 2 1 1 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 21 2 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 18 12 1 6 0 0 0 18 30 1 0 0 0 0 19 13 1 6 0 0 0 19 30 1 0 0 0 0 20 22 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.17
Volume:	409.295
LogP:	4.311
LogD:	3.763
LogS:	-5.996
# Rotatable Bonds:	4
TPSA:	64.61
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.729
Synthetic Accessibility Score:	4.687
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.699
MDCK Permeability:	3.9563074096804485e-05
Pgp-inhibitor:	0.861
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	78.1618423461914%
Volume Distribution (VD):	0.8
Pgp-substrate:	9.620807647705078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.989
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.844
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	7.335
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.301
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.108
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.227
Carcinogencity:	0.327
Eye Corrosion:	0.003
Eye Irritation:	0.065
Respiratory Toxicity:	0.531

Download Data

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

Natural Product: NPC103448

Natural Product ID:	NPC103448
*Common Name:**	Neokadsuranin
IUPAC Name:	n.a.
Synonyms:	Neokadsuranin
Standard InCHIKey:	RNIZTMIJCBCDBR-XJSVZPCESA-N
Standard InCHI:	InChI=1S/C23H26O7/c1-10-11(2)19-13-8-15-21(29-9-28-15)23(27-6)17(13)16-12(18(10)30-19)7-14(24-3)20(25-4)22(16)26-5/h7-8,10-11,18-19H,9H2,1-6H3/t10-,11+,18-,19+/m0/s1
SMILES:	COc1cc2[C@H]3O[C@H]([C@@H]([C@@H]3C)C)c3c(c2c(c1OC)OC)c(OC)c1c(c3)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485477
PubChem CID:	44575997
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350139]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8946749]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO912	Kadsura coccinea	Species	Schisandraceae	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
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[451666]
NPT2	Others	Unspecified		Activity	=	4.7	%	PMID[451666]
NPT2	Others	Unspecified		Activity	=	51.6	%	PMID[451666]
NPT2	Others	Unspecified		Activity	=	72.9	%	PMID[451666]
NPT2	Others	Unspecified		Activity	=	92.6	%	PMID[451666]

☑ 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 NPC103448 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	516
0.1-0.2	1581
0.2-0.3	4255
0.3-0.4	10981
0.4-0.5	7807
0.5-0.6	5087
0.6-0.7	9191
0.7-0.8	2498
0.8-0.85	519
0.85-0.9	199
0.9-0.95	59
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC216434
0.9851	High Similarity	NPC474295
0.9478	High Similarity	NPC32189
0.947	High Similarity	NPC72046
0.947	High Similarity	NPC475856
0.947	High Similarity	NPC65183
0.947	High Similarity	NPC261812
0.9398	High Similarity	NPC136750
0.9398	High Similarity	NPC266848
0.9328	High Similarity	NPC31530
0.9328	High Similarity	NPC145722
0.9328	High Similarity	NPC256776
0.9328	High Similarity	NPC185680
0.9323	High Similarity	NPC7744
0.9281	High Similarity	NPC172171
0.9281	High Similarity	NPC239254
0.9259	High Similarity	NPC189474
0.9259	High Similarity	NPC49235
0.9259	High Similarity	NPC474139
0.9259	High Similarity	NPC25333
0.9259	High Similarity	NPC148893
0.9248	High Similarity	NPC192255
0.9214	High Similarity	NPC475868
0.9209	High Similarity	NPC218510
0.9209	High Similarity	NPC76415
0.9203	High Similarity	NPC312199
0.9191	High Similarity	NPC121651
0.9149	High Similarity	NPC252286
0.9149	High Similarity	NPC154971
0.9143	High Similarity	NPC326144
0.9137	High Similarity	NPC230538
0.9137	High Similarity	NPC103637
0.9137	High Similarity	NPC229172
0.9137	High Similarity	NPC80326
0.9137	High Similarity	NPC36531
0.9137	High Similarity	NPC472562
0.9124	High Similarity	NPC196420
0.9091	High Similarity	NPC473092
0.9091	High Similarity	NPC85141
0.9091	High Similarity	NPC473093
0.9091	High Similarity	NPC8050
0.9078	High Similarity	NPC318286
0.9078	High Similarity	NPC327651
0.9071	High Similarity	NPC324962
0.9065	High Similarity	NPC300798
0.9065	High Similarity	NPC58137
0.9058	High Similarity	NPC201404
0.9058	High Similarity	NPC113550
0.9058	High Similarity	NPC290714
0.9058	High Similarity	NPC53722
0.9051	High Similarity	NPC11453
0.9028	High Similarity	NPC473989
0.9023	High Similarity	NPC54321
0.9023	High Similarity	NPC222127
0.9023	High Similarity	NPC165128
0.9023	High Similarity	NPC226862
0.9023	High Similarity	NPC82862
0.9023	High Similarity	NPC328682
0.9023	High Similarity	NPC57119
0.9023	High Similarity	NPC158471
0.9023	High Similarity	NPC281864
0.9014	High Similarity	NPC321958
0.9014	High Similarity	NPC321696
0.9007	High Similarity	NPC121661
0.9007	High Similarity	NPC73467
0.9	High Similarity	NPC174522
0.8993	High Similarity	NPC177868
0.8993	High Similarity	NPC46591
0.8986	High Similarity	NPC283949
0.8986	High Similarity	NPC185908
0.8978	High Similarity	NPC150534
0.8971	High Similarity	NPC1474
0.8966	High Similarity	NPC303519
0.8963	High Similarity	NPC141493
0.8963	High Similarity	NPC184928
0.8963	High Similarity	NPC82111
0.8963	High Similarity	NPC227160
0.8951	High Similarity	NPC116019
0.8944	High Similarity	NPC197352
0.8944	High Similarity	NPC205316
0.8944	High Similarity	NPC166506
0.8944	High Similarity	NPC110763
0.8944	High Similarity	NPC189239
0.8944	High Similarity	NPC180953
0.8936	High Similarity	NPC474808
0.8921	High Similarity	NPC9068
0.8905	High Similarity	NPC170779
0.8905	High Similarity	NPC90083
0.8889	High Similarity	NPC233224
0.8889	High Similarity	NPC325720
0.8889	High Similarity	NPC271208
0.8889	High Similarity	NPC327352
0.8889	High Similarity	NPC316676
0.8889	High Similarity	NPC237169
0.8889	High Similarity	NPC470624
0.8889	High Similarity	NPC198129
0.8889	High Similarity	NPC252281
0.8889	High Similarity	NPC258483
0.8889	High Similarity	NPC477375
0.8872	High Similarity	NPC186845
0.8872	High Similarity	NPC285725
0.8872	High Similarity	NPC112571
0.8872	High Similarity	NPC88297
0.8872	High Similarity	NPC9891
0.8872	High Similarity	NPC50683
0.8865	High Similarity	NPC184641
0.8865	High Similarity	NPC133934
0.8865	High Similarity	NPC184684
0.8865	High Similarity	NPC287124
0.8857	High Similarity	NPC226547
0.8857	High Similarity	NPC56091
0.8832	High Similarity	NPC196937
0.8828	High Similarity	NPC322426
0.8828	High Similarity	NPC477374
0.8828	High Similarity	NPC477376
0.8803	High Similarity	NPC12728
0.8803	High Similarity	NPC265154
0.8803	High Similarity	NPC255566
0.8803	High Similarity	NPC298317
0.8803	High Similarity	NPC185071
0.8784	High Similarity	NPC348849
0.8784	High Similarity	NPC198461
0.8784	High Similarity	NPC312763
0.8784	High Similarity	NPC178195
0.8777	High Similarity	NPC143895
0.8777	High Similarity	NPC197166
0.8777	High Similarity	NPC78047
0.8767	High Similarity	NPC316989
0.8759	High Similarity	NPC129687
0.8759	High Similarity	NPC33611
0.8759	High Similarity	NPC171928
0.8759	High Similarity	NPC158526
0.8759	High Similarity	NPC100223
0.8759	High Similarity	NPC16830
0.8759	High Similarity	NPC71726
0.875	High Similarity	NPC33832
0.875	High Similarity	NPC87295
0.8741	High Similarity	NPC166884
0.8741	High Similarity	NPC141569
0.8741	High Similarity	NPC477701
0.8741	High Similarity	NPC149008
0.8741	High Similarity	NPC207702
0.8741	High Similarity	NPC283114
0.8732	High Similarity	NPC311057
0.8732	High Similarity	NPC41782
0.8722	High Similarity	NPC121783
0.8722	High Similarity	NPC34902
0.8722	High Similarity	NPC18449
0.8714	High Similarity	NPC865
0.8714	High Similarity	NPC474039
0.8707	High Similarity	NPC210642
0.8707	High Similarity	NPC475756
0.8707	High Similarity	NPC13985
0.8707	High Similarity	NPC224472
0.8705	High Similarity	NPC236522
0.8696	High Similarity	NPC58585
0.8681	High Similarity	NPC178014
0.8681	High Similarity	NPC11422
0.8681	High Similarity	NPC42716
0.8681	High Similarity	NPC474749
0.8681	High Similarity	NPC477702
0.8658	High Similarity	NPC273578
0.8652	High Similarity	NPC30951
0.8652	High Similarity	NPC6369
0.8649	High Similarity	NPC475229
0.8649	High Similarity	NPC477378
0.8649	High Similarity	NPC471154
0.8639	High Similarity	NPC149505
0.8633	High Similarity	NPC474478
0.8633	High Similarity	NPC47181
0.863	High Similarity	NPC301961
0.863	High Similarity	NPC304821
0.863	High Similarity	NPC166584
0.8623	High Similarity	NPC259742
0.8623	High Similarity	NPC219671
0.8623	High Similarity	NPC104077
0.8623	High Similarity	NPC147616
0.8621	High Similarity	NPC212890
0.8621	High Similarity	NPC226540
0.8621	High Similarity	NPC162193
0.8601	High Similarity	NPC210354
0.8601	High Similarity	NPC191231
0.8601	High Similarity	NPC151423
0.8601	High Similarity	NPC40237
0.8601	High Similarity	NPC176586
0.8592	High Similarity	NPC284464
0.8591	High Similarity	NPC126405
0.8591	High Similarity	NPC53669
0.8591	High Similarity	NPC477377
0.8591	High Similarity	NPC297271
0.8591	High Similarity	NPC16791
0.8591	High Similarity	NPC217708
0.8591	High Similarity	NPC474606
0.8591	High Similarity	NPC24562
0.8591	High Similarity	NPC77237
0.8591	High Similarity	NPC308739
0.8571	High Similarity	NPC174191
0.8571	High Similarity	NPC141765
0.8571	High Similarity	NPC34103
0.8571	High Similarity	NPC18576

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 NPC103448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	885
0.2-0.3	1956
0.3-0.4	2821
0.4-0.5	1622
0.5-0.6	928
0.6-0.7	480
0.7-0.8	59
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD3705	Approved
0.8421	Intermediate Similarity	NPD4965	Approved
0.8421	Intermediate Similarity	NPD4966	Approved
0.8421	Intermediate Similarity	NPD4967	Phase 2
0.8312	Intermediate Similarity	NPD6234	Discontinued
0.8224	Intermediate Similarity	NPD37	Approved
0.8014	Intermediate Similarity	NPD3027	Phase 3
0.7975	Intermediate Similarity	NPD7199	Phase 2
0.795	Intermediate Similarity	NPD7228	Approved
0.7875	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD5283	Phase 1
0.7785	Intermediate Similarity	NPD6674	Discontinued
0.7758	Intermediate Similarity	NPD7240	Approved
0.7746	Intermediate Similarity	NPD3018	Phase 2
0.7724	Intermediate Similarity	NPD1613	Approved
0.7724	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2981	Phase 2
0.7622	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2982	Phase 2
0.7589	Intermediate Similarity	NPD2983	Phase 2
0.7569	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4908	Phase 1
0.7362	Intermediate Similarity	NPD5494	Approved
0.7357	Intermediate Similarity	NPD1357	Approved
0.7355	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1610	Phase 2
0.731	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3818	Discontinued
0.7279	Intermediate Similarity	NPD4625	Phase 3
0.7278	Intermediate Similarity	NPD1653	Approved
0.726	Intermediate Similarity	NPD2861	Phase 2
0.7237	Intermediate Similarity	NPD3539	Phase 1
0.723	Intermediate Similarity	NPD5109	Approved
0.723	Intermediate Similarity	NPD5110	Phase 2
0.723	Intermediate Similarity	NPD5111	Phase 2
0.7203	Intermediate Similarity	NPD1091	Approved
0.72	Intermediate Similarity	NPD3657	Discovery
0.7192	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3540	Phase 1
0.7179	Intermediate Similarity	NPD7124	Phase 2
0.7171	Intermediate Similarity	NPD4108	Discontinued
0.716	Intermediate Similarity	NPD5844	Phase 1
0.7134	Intermediate Similarity	NPD4055	Discovery
0.7133	Intermediate Similarity	NPD4060	Phase 1
0.7133	Intermediate Similarity	NPD3620	Phase 2
0.7133	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4005	Discontinued
0.7118	Intermediate Similarity	NPD7074	Phase 3
0.7117	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6111	Discontinued
0.7103	Intermediate Similarity	NPD4749	Approved
0.7099	Intermediate Similarity	NPD1934	Approved
0.7099	Intermediate Similarity	NPD3383	Approved
0.7099	Intermediate Similarity	NPD3382	Approved
0.7099	Intermediate Similarity	NPD3384	Approved
0.7097	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1375	Discontinued
0.7069	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6232	Discontinued
0.7059	Intermediate Similarity	NPD7054	Approved
0.7051	Intermediate Similarity	NPD3892	Phase 2
0.7042	Intermediate Similarity	NPD1548	Phase 1
0.7041	Intermediate Similarity	NPD7473	Discontinued
0.7018	Intermediate Similarity	NPD7472	Approved
0.7013	Intermediate Similarity	NPD2438	Suspended
0.7012	Intermediate Similarity	NPD3817	Phase 2
0.7012	Intermediate Similarity	NPD2563	Approved
0.7012	Intermediate Similarity	NPD2560	Approved
0.7	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5006	Approved
0.6995	Remote Similarity	NPD5005	Approved
0.6993	Remote Similarity	NPD5691	Approved
0.6989	Remote Similarity	NPD6842	Approved
0.6989	Remote Similarity	NPD6841	Approved
0.6989	Remote Similarity	NPD6843	Phase 3
0.6986	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5327	Phase 3
0.6972	Remote Similarity	NPD5536	Phase 2
0.697	Remote Similarity	NPD3882	Suspended
0.697	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7266	Discontinued
0.6968	Remote Similarity	NPD5762	Approved
0.6968	Remote Similarity	NPD5763	Approved
0.6964	Remote Similarity	NPD7229	Phase 3
0.6964	Remote Similarity	NPD3787	Discontinued
0.6962	Remote Similarity	NPD5058	Phase 3
0.6962	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7680	Approved
0.6951	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.695	Remote Similarity	NPD709	Approved
0.6948	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5126	Approved
0.6944	Remote Similarity	NPD5125	Phase 3
0.6943	Remote Similarity	NPD7466	Approved
0.6937	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6559	Discontinued
0.6933	Remote Similarity	NPD5090	Approved
0.6933	Remote Similarity	NPD5089	Approved
0.6923	Remote Similarity	NPD3926	Phase 2
0.6908	Remote Similarity	NPD2979	Phase 3
0.6897	Remote Similarity	NPD7808	Phase 3
0.6886	Remote Similarity	NPD919	Approved
0.6879	Remote Similarity	NPD4236	Phase 3
0.6879	Remote Similarity	NPD4237	Approved
0.6879	Remote Similarity	NPD6797	Phase 2
0.6875	Remote Similarity	NPD3445	Approved
0.6875	Remote Similarity	NPD3444	Approved
0.6875	Remote Similarity	NPD3443	Approved
0.6871	Remote Similarity	NPD7028	Phase 2
0.6868	Remote Similarity	NPD4420	Approved
0.6863	Remote Similarity	NPD5735	Approved
0.6863	Remote Similarity	NPD6355	Discontinued
0.6852	Remote Similarity	NPD4210	Discontinued
0.6849	Remote Similarity	NPD1611	Approved
0.6848	Remote Similarity	NPD2978	Approved
0.6848	Remote Similarity	NPD2801	Approved
0.6848	Remote Similarity	NPD2977	Approved
0.6848	Remote Similarity	NPD4585	Approved
0.6848	Remote Similarity	NPD1465	Phase 2
0.6839	Remote Similarity	NPD7251	Discontinued
0.6839	Remote Similarity	NPD3748	Approved
0.6835	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4110	Phase 3
0.6826	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1247	Approved
0.68	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2238	Phase 2
0.6795	Remote Similarity	NPD2796	Approved
0.6792	Remote Similarity	NPD2677	Approved
0.6786	Remote Similarity	NPD228	Approved
0.6784	Remote Similarity	NPD4481	Phase 3
0.6784	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6166	Phase 2
0.6784	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7296	Approved
0.6772	Remote Similarity	NPD5177	Phase 3
0.677	Remote Similarity	NPD2532	Approved
0.677	Remote Similarity	NPD2534	Approved
0.677	Remote Similarity	NPD2533	Approved
0.6768	Remote Similarity	NPD4678	Approved
0.6768	Remote Similarity	NPD4675	Approved
0.6765	Remote Similarity	NPD6071	Discontinued
0.6763	Remote Similarity	NPD8156	Discontinued
0.6759	Remote Similarity	NPD1651	Approved
0.6755	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8455	Phase 2
0.6747	Remote Similarity	NPD7819	Suspended
0.6735	Remote Similarity	NPD1281	Approved
0.673	Remote Similarity	NPD6331	Phase 2
0.6728	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5242	Approved
0.6713	Remote Similarity	NPD6387	Discontinued
0.6713	Remote Similarity	NPD7157	Approved
0.6712	Remote Similarity	NPD4626	Approved
0.6711	Remote Similarity	NPD6696	Suspended
0.6711	Remote Similarity	NPD2922	Phase 1
0.6711	Remote Similarity	NPD8651	Approved
0.6708	Remote Similarity	NPD4357	Discontinued
0.6707	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5353	Approved
0.6705	Remote Similarity	NPD7549	Discontinued
0.6705	Remote Similarity	NPD8251	Approved
0.6705	Remote Similarity	NPD8099	Discontinued
0.6705	Remote Similarity	NPD3751	Discontinued
0.6705	Remote Similarity	NPD8252	Approved
0.6691	Remote Similarity	NPD2684	Approved
0.6689	Remote Similarity	NPD1840	Phase 2
0.6688	Remote Similarity	NPD6099	Approved
0.6688	Remote Similarity	NPD6100	Approved
0.6688	Remote Similarity	NPD2161	Phase 2
0.6688	Remote Similarity	NPD4140	Approved
0.6688	Remote Similarity	NPD3454	Phase 3
0.6687	Remote Similarity	NPD5976	Discontinued
0.6667	Remote Similarity	NPD6895	Approved
0.6667	Remote Similarity	NPD3051	Approved
0.6667	Remote Similarity	NPD1139	Approved
0.6667	Remote Similarity	NPD6896	Approved
0.6667	Remote Similarity	NPD1137	Approved
0.6667	Remote Similarity	NPD1652	Phase 2
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3489	Phase 3
0.6645	Remote Similarity	NPD1933	Approved
0.6645	Remote Similarity	NPD5124	Phase 1
0.6645	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4379	Clinical (unspecified phase)

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