NPASS Compound

Structure

CID316676 OpenBabel06191716132D 34 37 0 0 1 0 0 0 0 0999 V2000 5.7124 1.6049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5281 2.7892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3714 3.4181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1651 -3.6641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7933 -2.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3702 -2.0209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9023 -2.5530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6394 -1.1993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7239 1.7162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5576 0.7675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8359 1.2419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1651 1.9127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4308 3.5419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1651 -0.3777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5455 1.2419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1651 -2.0209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9023 1.2419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2164 -0.3777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5455 0.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8359 0.2932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2164 1.9127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2164 -2.0209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9023 0.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7420 -1.1993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7239 -0.1812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0678 4.4184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7124 -0.0699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6394 -2.8425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7420 -2.8425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 -1.1993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7239 -2.0786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5351 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 2.8533 2.7892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 13 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 32 1 0 0 0 0 10 33 1 0 0 0 0 11 1 1 6 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 2 1 6 0 0 0 12 21 1 0 0 0 0 13 26 2 0 0 0 0 13 34 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 16 28 1 0 0 0 0 17 23 2 0 0 0 0 17 32 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 25 2 0 0 0 0 20 27 1 6 0 0 0 21 34 1 6 0 0 0 22 24 1 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.19
Volume:	467.387
LogP:	2.84
LogD:	3.031
LogS:	-3.973
# Rotatable Bonds:	6
TPSA:	101.91
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	4.052
Fsp3:	0.48
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.73
MDCK Permeability:	2.9783723221044056e-05
Pgp-inhibitor:	0.896
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	74.96696472167969%
Volume Distribution (VD):	0.95
Pgp-substrate:	16.451839447021484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.48
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.782
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.422
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	3.108
Half-life (T1/2):	0.141

ADMET: Toxicity

hERG Blockers:	0.338
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.848
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.043
Carcinogencity:	0.184
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.272

Download Data

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

Natural Product: NPC316676

Natural Product ID:	NPC316676
*Common Name:**	Ananolignan D
IUPAC Name:	n.a.
Synonyms:	Ananolignan D
Standard InCHIKey:	VMDLXEJHKASDPJ-YGGHMXSPSA-N
Standard InCHI:	InChI=1S/C25H30O9/c1-11-12(2)21(34-13(3)26)15-9-17-23(33-10-32-17)25(31-7)19(15)18-14(20(11)27)8-16(28-4)22(29-5)24(18)30-6/h8-9,11-12,20-21,27H,10H2,1-7H3/t11-,12+,20-,21+/m0/s1
SMILES:	CC1C(C(C2=CC3=C(C(=C2C4=C(C(=C(C=C4C1O)OC)OC)OC)OC)OCO3)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782112
PubChem CID:	53355341
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
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165154]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[20025236]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	seed	n.a.	PMID[21381710]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27599	Kadsura ananosma	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	64.3	%	PMID[544883]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	63.0	%	PMID[544883]

☑ 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 NPC316676 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	328
0.1-0.2	1388
0.2-0.3	3621
0.3-0.4	8744
0.4-0.5	9959
0.5-0.6	4221
0.6-0.7	8024
0.7-0.8	5170
0.8-0.85	934
0.85-0.9	217
0.9-0.95	73
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC325720
0.9859	High Similarity	NPC473989
0.9655	High Similarity	NPC24562
0.9653	High Similarity	NPC475756
0.9643	High Similarity	NPC218510
0.9643	High Similarity	NPC76415
0.9643	High Similarity	NPC324962
0.9589	High Similarity	NPC473425
0.9589	High Similarity	NPC312763
0.9586	High Similarity	NPC471154
0.9574	High Similarity	NPC326144
0.9571	High Similarity	NPC36531
0.9571	High Similarity	NPC229172
0.9571	High Similarity	NPC103637
0.9571	High Similarity	NPC230538
0.9521	High Similarity	NPC474606
0.9517	High Similarity	NPC224472
0.9507	High Similarity	NPC318286
0.9507	High Similarity	NPC475868
0.9507	High Similarity	NPC327651
0.9459	High Similarity	NPC473323
0.9441	High Similarity	NPC321696
0.9441	High Similarity	NPC321958
0.9437	High Similarity	NPC239254
0.9437	High Similarity	NPC172171
0.9392	High Similarity	NPC238834
0.9392	High Similarity	NPC476065
0.9388	High Similarity	NPC16791
0.9388	High Similarity	NPC297271
0.9388	High Similarity	NPC217708
0.9388	High Similarity	NPC77237
0.9388	High Similarity	NPC308739
0.9388	High Similarity	NPC126405
0.9388	High Similarity	NPC53669
0.9371	High Similarity	NPC189239
0.9371	High Similarity	NPC110763
0.9371	High Similarity	NPC197352
0.9371	High Similarity	NPC166506
0.9324	High Similarity	NPC198461
0.931	High Similarity	NPC252281
0.931	High Similarity	NPC477375
0.931	High Similarity	NPC198129
0.931	High Similarity	NPC327352
0.9306	High Similarity	NPC474054
0.9301	High Similarity	NPC121661
0.9301	High Similarity	NPC87883
0.9301	High Similarity	NPC73467
0.9296	High Similarity	NPC287124
0.9267	High Similarity	NPC475592
0.9247	High Similarity	NPC322426
0.9247	High Similarity	NPC477374
0.9247	High Similarity	NPC85141
0.9247	High Similarity	NPC477376
0.922	High Similarity	NPC53722
0.922	High Similarity	NPC201404
0.922	High Similarity	NPC290714
0.9205	High Similarity	NPC230531
0.9205	High Similarity	NPC215400
0.92	High Similarity	NPC29727
0.9184	High Similarity	NPC24425
0.9184	High Similarity	NPC316989
0.9178	High Similarity	NPC304821
0.9178	High Similarity	NPC477879
0.9172	High Similarity	NPC154971
0.9172	High Similarity	NPC212890
0.9172	High Similarity	NPC252286
0.9167	High Similarity	NPC166884
0.9167	High Similarity	NPC141569
0.9167	High Similarity	NPC477701
0.9161	High Similarity	NPC133934
0.9161	High Similarity	NPC184641
0.9161	High Similarity	NPC184684
0.9149	High Similarity	NPC865
0.9145	High Similarity	NPC63061
0.9122	High Similarity	NPC303519
0.9103	High Similarity	NPC477702
0.9071	High Similarity	NPC256776
0.9071	High Similarity	NPC185680
0.9071	High Similarity	NPC145722
0.906	High Similarity	NPC475229
0.906	High Similarity	NPC477378
0.9054	High Similarity	NPC477381
0.9013	High Similarity	NPC207584
0.9013	High Similarity	NPC19947
0.9	High Similarity	NPC477377
0.9	High Similarity	NPC245948
0.8993	High Similarity	NPC477379
0.8986	High Similarity	NPC474393
0.8986	High Similarity	NPC474347
0.898	High Similarity	NPC295297
0.8947	High Similarity	NPC237946
0.8947	High Similarity	NPC32373
0.8944	High Similarity	NPC11453
0.8944	High Similarity	NPC32189
0.8944	High Similarity	NPC143895
0.894	High Similarity	NPC348849
0.894	High Similarity	NPC178195
0.8933	High Similarity	NPC302610
0.8926	High Similarity	NPC470916
0.8889	High Similarity	NPC46591
0.8889	High Similarity	NPC216434
0.8889	High Similarity	NPC103448
0.8881	High Similarity	NPC301765
0.8881	High Similarity	NPC86605
0.8881	High Similarity	NPC474039
0.8881	High Similarity	NPC46277
0.8881	High Similarity	NPC3072
0.8881	High Similarity	NPC156948
0.8881	High Similarity	NPC283949
0.8874	High Similarity	NPC149735
0.8874	High Similarity	NPC474514
0.8873	High Similarity	NPC236522
0.8873	High Similarity	NPC150534
0.8865	High Similarity	NPC196937
0.8865	High Similarity	NPC58585
0.8839	High Similarity	NPC288149
0.8836	High Similarity	NPC474808
0.8824	High Similarity	NPC477380
0.8819	High Similarity	NPC471183
0.8811	High Similarity	NPC197166
0.8811	High Similarity	NPC133025
0.8808	High Similarity	NPC56184
0.8797	High Similarity	NPC311912
0.8797	High Similarity	NPC471180
0.8776	High Similarity	NPC472712
0.8776	High Similarity	NPC187774
0.8776	High Similarity	NPC473046
0.8776	High Similarity	NPC118385
0.8776	High Similarity	NPC472713
0.8774	High Similarity	NPC96593
0.8774	High Similarity	NPC150943
0.8774	High Similarity	NPC268718
0.8774	High Similarity	NPC119910
0.8774	High Similarity	NPC91634
0.8767	High Similarity	NPC41782
0.8767	High Similarity	NPC474295
0.8766	High Similarity	NPC477885
0.8759	High Similarity	NPC226547
0.8759	High Similarity	NPC56091
0.8759	High Similarity	NPC177868
0.875	High Similarity	NPC475141
0.875	High Similarity	NPC185908
0.8742	High Similarity	NPC88557
0.8734	High Similarity	NPC118162
0.8734	High Similarity	NPC83049
0.8734	High Similarity	NPC320471
0.8733	High Similarity	NPC477698
0.8732	High Similarity	NPC112237
0.8726	High Similarity	NPC469475
0.8726	High Similarity	NPC469518
0.8726	High Similarity	NPC475865
0.8725	High Similarity	NPC183083
0.8725	High Similarity	NPC137352
0.8725	High Similarity	NPC116019
0.8723	High Similarity	NPC184928
0.8723	High Similarity	NPC141493
0.8716	High Similarity	NPC180953
0.871	High Similarity	NPC325122
0.8707	High Similarity	NPC185071
0.8707	High Similarity	NPC12728
0.8693	High Similarity	NPC136757
0.8693	High Similarity	NPC473736
0.869	High Similarity	NPC30951
0.869	High Similarity	NPC6369
0.869	High Similarity	NPC9068
0.8681	High Similarity	NPC172818
0.8681	High Similarity	NPC25695
0.8679	High Similarity	NPC79322
0.8675	High Similarity	NPC218041
0.8675	High Similarity	NPC469706
0.8675	High Similarity	NPC185955
0.8675	High Similarity	NPC9933
0.8675	High Similarity	NPC225815
0.8675	High Similarity	NPC472709
0.8675	High Similarity	NPC145979
0.8675	High Similarity	NPC214326
0.8675	High Similarity	NPC472710
0.8675	High Similarity	NPC182368
0.8675	High Similarity	NPC469707
0.8675	High Similarity	NPC260781
0.8671	High Similarity	NPC326095
0.8671	High Similarity	NPC289258
0.8671	High Similarity	NPC56764
0.8671	High Similarity	NPC276026
0.8671	High Similarity	NPC555
0.8671	High Similarity	NPC206737
0.8671	High Similarity	NPC188378
0.8671	High Similarity	NPC7515
0.8671	High Similarity	NPC244983
0.8671	High Similarity	NPC469659
0.8667	High Similarity	NPC270751
0.8662	High Similarity	NPC261812
0.8662	High Similarity	NPC65183
0.8662	High Similarity	NPC102256
0.8662	High Similarity	NPC72046
0.8662	High Similarity	NPC475856
0.8658	High Similarity	NPC190714
0.8658	High Similarity	NPC99515
0.8654	High Similarity	NPC474770
0.8649	High Similarity	NPC18211

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 NPC316676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	891
0.2-0.3	1881
0.3-0.4	2716
0.4-0.5	1711
0.5-0.6	986
0.6-0.7	589
0.7-0.8	100
0.8-0.85	6
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD37	Approved
0.8947	High Similarity	NPD4965	Approved
0.8947	High Similarity	NPD4967	Phase 2
0.8947	High Similarity	NPD4966	Approved
0.871	High Similarity	NPD6234	Discontinued
0.8481	Intermediate Similarity	NPD7199	Phase 2
0.8447	Intermediate Similarity	NPD7228	Approved
0.8261	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD3027	Phase 3
0.8143	Intermediate Similarity	NPD3705	Approved
0.8133	Intermediate Similarity	NPD7240	Approved
0.8013	Intermediate Similarity	NPD1653	Approved
0.7905	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1613	Approved
0.7843	Intermediate Similarity	NPD6674	Discontinued
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7756	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD5844	Phase 1
0.7722	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7266	Discontinued
0.7687	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4060	Phase 1
0.7651	Intermediate Similarity	NPD6232	Discontinued
0.7635	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7473	Discontinued
0.7588	Intermediate Similarity	NPD7074	Phase 3
0.7572	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3018	Phase 2
0.7561	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1357	Approved
0.7547	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7054	Approved
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.7515	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD5763	Approved
0.7484	Intermediate Similarity	NPD5762	Approved
0.7457	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7429	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2983	Phase 2
0.7415	Intermediate Similarity	NPD2982	Phase 2
0.7397	Intermediate Similarity	NPD1091	Approved
0.7397	Intermediate Similarity	NPD1610	Phase 2
0.7394	Intermediate Similarity	NPD3817	Phase 2
0.7391	Intermediate Similarity	NPD7680	Approved
0.7383	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1934	Approved
0.7376	Intermediate Similarity	NPD5283	Phase 1
0.7356	Intermediate Similarity	NPD7808	Phase 3
0.7351	Intermediate Similarity	NPD4625	Phase 3
0.7347	Intermediate Similarity	NPD2981	Phase 2
0.7341	Intermediate Similarity	NPD6797	Phase 2
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.7333	Intermediate Similarity	NPD2861	Phase 2
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7325	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3620	Phase 2
0.7305	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7251	Discontinued
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7251	Intermediate Similarity	NPD6166	Phase 2
0.7251	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6841	Approved
0.7247	Intermediate Similarity	NPD6842	Approved
0.7247	Intermediate Similarity	NPD6843	Phase 3
0.7246	Intermediate Similarity	NPD3882	Suspended
0.7235	Intermediate Similarity	NPD3787	Discontinued
0.7233	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4110	Phase 3
0.7229	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7819	Suspended
0.7219	Intermediate Similarity	NPD5494	Approved
0.7208	Intermediate Similarity	NPD4140	Approved
0.72	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD2438	Suspended
0.7195	Intermediate Similarity	NPD4005	Discontinued
0.719	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4749	Approved
0.7176	Intermediate Similarity	NPD8127	Discontinued
0.717	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1652	Phase 2
0.7162	Intermediate Similarity	NPD422	Phase 1
0.7159	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4626	Approved
0.7126	Intermediate Similarity	NPD2801	Approved
0.7126	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3892	Phase 2
0.7125	Intermediate Similarity	NPD3750	Approved
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5691	Approved
0.707	Intermediate Similarity	NPD7097	Phase 1
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7067	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4380	Phase 2
0.7044	Intermediate Similarity	NPD6002	Phase 3
0.7044	Intermediate Similarity	NPD3540	Phase 1
0.7044	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6004	Phase 3
0.7044	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6005	Phase 3
0.7037	Intermediate Similarity	NPD5058	Phase 3
0.7029	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5126	Approved
0.7027	Intermediate Similarity	NPD5125	Phase 3
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.7025	Intermediate Similarity	NPD4108	Discontinued
0.7024	Intermediate Similarity	NPD2978	Approved
0.7024	Intermediate Similarity	NPD2977	Approved
0.702	Intermediate Similarity	NPD1283	Approved
0.7019	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4628	Phase 3
0.7012	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD4055	Discovery
0.7	Intermediate Similarity	NPD7075	Discontinued
0.6994	Remote Similarity	NPD4357	Discontinued
0.6987	Remote Similarity	NPD2979	Phase 3
0.6987	Remote Similarity	NPD2238	Phase 2
0.6982	Remote Similarity	NPD2560	Approved
0.6982	Remote Similarity	NPD2563	Approved
0.6982	Remote Similarity	NPD5402	Approved
0.6981	Remote Similarity	NPD6099	Approved
0.6981	Remote Similarity	NPD3539	Phase 1
0.6981	Remote Similarity	NPD6100	Approved
0.6977	Remote Similarity	NPD6959	Discontinued
0.6975	Remote Similarity	NPD6190	Approved
0.6975	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6798	Discontinued
0.6964	Remote Similarity	NPD6801	Discontinued
0.6962	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD919	Approved
0.6957	Remote Similarity	NPD4236	Phase 3
0.6957	Remote Similarity	NPD5177	Phase 3
0.6957	Remote Similarity	NPD4237	Approved
0.6954	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7028	Phase 2
0.6943	Remote Similarity	NPD230	Phase 1
0.694	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1375	Discontinued
0.6933	Remote Similarity	NPD1611	Approved
0.6928	Remote Similarity	NPD3686	Approved
0.6928	Remote Similarity	NPD3687	Approved
0.6927	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3748	Approved
0.6914	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5089	Approved
0.6905	Remote Similarity	NPD5090	Approved
0.6903	Remote Similarity	NPD7095	Approved
0.6897	Remote Similarity	NPD3926	Phase 2
0.689	Remote Similarity	NPD6799	Approved
0.689	Remote Similarity	NPD1511	Approved
0.6887	Remote Similarity	NPD1608	Approved
0.6886	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5006	Approved
0.6878	Remote Similarity	NPD5005	Approved
0.6875	Remote Similarity	NPD228	Approved
0.6875	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD6032	Approved
0.6871	Remote Similarity	NPD2677	Approved
0.6871	Remote Similarity	NPD2219	Phase 1
0.6867	Remote Similarity	NPD5403	Approved
0.6867	Remote Similarity	NPD3496	Discontinued
0.6863	Remote Similarity	NPD2797	Approved
0.686	Remote Similarity	NPD5709	Phase 3
0.6859	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4481	Phase 3
0.6848	Remote Similarity	NPD7296	Approved
0.6845	Remote Similarity	NPD4678	Approved
0.6845	Remote Similarity	NPD4675	Approved
0.6845	Remote Similarity	NPD6599	Discontinued
0.6842	Remote Similarity	NPD7768	Phase 2
0.6839	Remote Similarity	NPD8151	Discontinued
0.6835	Remote Similarity	NPD3657	Discovery
0.6835	Remote Similarity	NPD5735	Approved
0.6832	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6666	Approved
0.6829	Remote Similarity	NPD6667	Approved
0.6829	Remote Similarity	NPD7124	Phase 2
0.6824	Remote Similarity	NPD5536	Phase 2

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