NPASS Compound

Structure

NPC475868 OpenBabel07101718242D 30 34 0 0 1 0 0 0 0 0999 V2000 2.8913 -5.1509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2240 -5.1509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6832 1.1620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4322 1.1620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1100 -2.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0054 -2.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0482 -0.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9328 -0.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5299 -4.2783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5855 -4.2783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1977 -2.6660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9176 -2.6660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3544 -1.5093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2391 -1.5093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5299 -1.9982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5855 -1.9982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1977 -3.6105 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9176 -3.6105 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6866 -0.8415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4288 -0.8415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7744 -1.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3410 -1.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0703 -3.9719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0451 -3.9719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4387 0.2497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6767 0.2497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1959 -1.0806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0806 -1.0806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1154 -0.0000 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 25 1 0 0 0 0 4 26 1 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 27 1 0 0 0 0 7 29 1 0 0 0 0 8 28 1 0 0 0 0 8 30 1 0 0 0 0 9 1 1 1 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 2 1 1 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 13 27 1 0 0 0 0 14 20 2 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 17 23 1 1 0 0 0 18 24 1 6 0 0 0 19 21 1 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	400.789
LogP:	2.771
LogD:	3.134
LogS:	-3.988
# Rotatable Bonds:	2
TPSA:	95.84
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.771
Synthetic Accessibility Score:	4.139
Fsp3:	0.455
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:	-4.813
MDCK Permeability:	4.3095205910503864e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	83.03148651123047%
Volume Distribution (VD):	1.141
Pgp-substrate:	9.165706634521484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.272
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.438
CYP2D6-substrate:	0.459
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.506

ADMET: Excretion

Clearance (CL):	12.323
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.413
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.08
Carcinogencity:	0.895
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.543

Download Data

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

Natural Product: NPC475868

Natural Product ID:	NPC475868
*Common Name:**	Schisantherin P
IUPAC Name:	n.a.
Synonyms:	Schisantherin P
Standard InCHIKey:	PGQCSEUUYHHWGA-JXDQDEQISA-N
Standard InCHI:	InChI=1S/C22H24O8/c1-9-10(2)18(24)12-6-14-20(30-8-28-14)22(26-4)16(12)15-11(17(9)23)5-13-19(21(15)25-3)29-7-27-13/h5-6,9-10,17-18,23-24H,7-8H2,1-4H3/t9-,10+,17-,18-/m0/s1
SMILES:	CC1C(C(C2=CC3=C(C(=C2C4=C(C5=C(C=C4C1O)OCO5)OC)OC)OCO3)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517654
PubChem CID:	44567625
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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	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
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	>	200000.0	nM	PMID[544857]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	156370.0	nM	PMID[544857]
NPT2	Others	Unspecified		Ratio	>	3.07	n.a.	PMID[544857]

☑ 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 NPC475868 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	412
0.1-0.2	1529
0.2-0.3	4151
0.3-0.4	10892
0.4-0.5	7908
0.5-0.6	4660
0.6-0.7	8562
0.7-0.8	3423
0.8-0.85	823
0.85-0.9	270
0.9-0.95	56
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC172171
0.9927	High Similarity	NPC239254
0.9854	High Similarity	NPC324962
0.9781	High Similarity	NPC229172
0.9781	High Similarity	NPC36531
0.9781	High Similarity	NPC103637
0.9781	High Similarity	NPC230538
0.9648	High Similarity	NPC473989
0.9643	High Similarity	NPC252286
0.9643	High Similarity	NPC154971
0.9571	High Similarity	NPC166506
0.9571	High Similarity	NPC189239
0.9571	High Similarity	NPC197352
0.9571	High Similarity	NPC110763
0.9507	High Similarity	NPC325720
0.9507	High Similarity	NPC316676
0.95	High Similarity	NPC121661
0.95	High Similarity	NPC73467
0.942	High Similarity	NPC201404
0.942	High Similarity	NPC53722
0.942	High Similarity	NPC290714
0.9416	High Similarity	NPC32189
0.9384	High Similarity	NPC312763
0.9357	High Similarity	NPC184641
0.9357	High Similarity	NPC184684
0.9357	High Similarity	NPC133934
0.9343	High Similarity	NPC150534
0.9291	High Similarity	NPC474808
0.927	High Similarity	NPC145722
0.927	High Similarity	NPC185680
0.927	High Similarity	NPC256776
0.9214	High Similarity	NPC46591
0.9214	High Similarity	NPC103448
0.9214	High Similarity	NPC216434
0.9209	High Similarity	NPC283949
0.9184	High Similarity	NPC24562
0.9178	High Similarity	NPC475756
0.9155	High Similarity	NPC218510
0.9155	High Similarity	NPC76415
0.9143	High Similarity	NPC9068
0.9122	High Similarity	NPC198461
0.9122	High Similarity	NPC473425
0.9116	High Similarity	NPC471154
0.9103	High Similarity	NPC304821
0.9091	High Similarity	NPC326144
0.9085	High Similarity	NPC287124
0.9085	High Similarity	NPC474295
0.9078	High Similarity	NPC56091
0.9078	High Similarity	NPC177868
0.9078	High Similarity	NPC226547
0.9071	High Similarity	NPC156948
0.9071	High Similarity	NPC46277
0.9071	High Similarity	NPC86605
0.9071	High Similarity	NPC301765
0.9071	High Similarity	NPC3072
0.9071	High Similarity	NPC474039
0.9071	High Similarity	NPC185908
0.9058	High Similarity	NPC196937
0.9058	High Similarity	NPC58585
0.9054	High Similarity	NPC474606
0.9048	High Similarity	NPC224472
0.9041	High Similarity	NPC85141
0.9034	High Similarity	NPC116019
0.9028	High Similarity	NPC327651
0.9028	High Similarity	NPC318286
0.9028	High Similarity	NPC180953
0.9021	High Similarity	NPC185071
0.9021	High Similarity	NPC12728
0.9	High Similarity	NPC473323
0.9	High Similarity	NPC133025
0.9	High Similarity	NPC197166
0.8986	High Similarity	NPC219671
0.8986	High Similarity	NPC259742
0.8986	High Similarity	NPC65183
0.8986	High Similarity	NPC104077
0.8986	High Similarity	NPC72046
0.8986	High Similarity	NPC147616
0.8986	High Similarity	NPC261812
0.8966	High Similarity	NPC212890
0.8966	High Similarity	NPC321958
0.8966	High Similarity	NPC321696
0.8966	High Similarity	NPC33832
0.8958	High Similarity	NPC166884
0.8958	High Similarity	NPC141569
0.8958	High Similarity	NPC477701
0.8933	High Similarity	NPC476065
0.8933	High Similarity	NPC238834
0.8929	High Similarity	NPC236522
0.8929	High Similarity	NPC49235
0.8929	High Similarity	NPC25333
0.8929	High Similarity	NPC148893
0.8926	High Similarity	NPC16791
0.8926	High Similarity	NPC77237
0.8926	High Similarity	NPC126405
0.8926	High Similarity	NPC217708
0.8926	High Similarity	NPC297271
0.8926	High Similarity	NPC308739
0.8926	High Similarity	NPC53669
0.8921	High Similarity	NPC136750
0.8921	High Similarity	NPC112237
0.8921	High Similarity	NPC266848
0.8919	High Similarity	NPC303519
0.8897	High Similarity	NPC477702
0.8896	High Similarity	NPC475865
0.8889	High Similarity	NPC265154
0.8889	High Similarity	NPC298317
0.8889	High Similarity	NPC255566
0.8881	High Similarity	NPC312199
0.8873	High Similarity	NPC30951
0.8873	High Similarity	NPC6369
0.8873	High Similarity	NPC471183
0.8865	High Similarity	NPC121651
0.8857	High Similarity	NPC31530
0.8857	High Similarity	NPC206737
0.8857	High Similarity	NPC555
0.8857	High Similarity	NPC289258
0.8857	High Similarity	NPC469659
0.8857	High Similarity	NPC7515
0.8857	High Similarity	NPC56764
0.8857	High Similarity	NPC188378
0.8857	High Similarity	NPC276026
0.8849	High Similarity	NPC102256
0.8849	High Similarity	NPC7744
0.8844	High Similarity	NPC327352
0.8844	High Similarity	NPC248132
0.8844	High Similarity	NPC252281
0.8844	High Similarity	NPC71726
0.8844	High Similarity	NPC130449
0.8844	High Similarity	NPC477375
0.8844	High Similarity	NPC198129
0.8836	High Similarity	NPC474054
0.8828	High Similarity	NPC187774
0.8828	High Similarity	NPC472713
0.8828	High Similarity	NPC87883
0.8828	High Similarity	NPC118385
0.8828	High Similarity	NPC473046
0.8828	High Similarity	NPC472712
0.8819	High Similarity	NPC41782
0.8819	High Similarity	NPC191231
0.8816	High Similarity	NPC207584
0.8816	High Similarity	NPC19947
0.8816	High Similarity	NPC475592
0.8811	High Similarity	NPC284464
0.8803	High Similarity	NPC196420
0.8794	High Similarity	NPC165155
0.8794	High Similarity	NPC174191
0.8794	High Similarity	NPC18576
0.8794	High Similarity	NPC240279
0.8794	High Similarity	NPC141765
0.8794	High Similarity	NPC474139
0.8794	High Similarity	NPC180602
0.8794	High Similarity	NPC24490
0.8794	High Similarity	NPC34103
0.8794	High Similarity	NPC189474
0.8794	High Similarity	NPC55239
0.8794	High Similarity	NPC214853
0.8784	High Similarity	NPC51328
0.8784	High Similarity	NPC240521
0.8784	High Similarity	NPC55158
0.8784	High Similarity	NPC322426
0.8784	High Similarity	NPC286235
0.8784	High Similarity	NPC477376
0.8784	High Similarity	NPC477374
0.8777	High Similarity	NPC192255
0.8777	High Similarity	NPC141493
0.8777	High Similarity	NPC184928
0.8767	High Similarity	NPC178014
0.8767	High Similarity	NPC474749
0.8767	High Similarity	NPC11422
0.8767	High Similarity	NPC42716
0.8758	High Similarity	NPC215400
0.8758	High Similarity	NPC230531
0.875	High Similarity	NPC32373
0.875	High Similarity	NPC29727
0.875	High Similarity	NPC237946
0.8742	High Similarity	NPC348849
0.8742	High Similarity	NPC178195
0.8741	High Similarity	NPC113550
0.8732	High Similarity	NPC25695
0.8732	High Similarity	NPC11453
0.8732	High Similarity	NPC172818
0.8725	High Similarity	NPC472709
0.8725	High Similarity	NPC145979
0.8725	High Similarity	NPC185955
0.8725	High Similarity	NPC214326
0.8725	High Similarity	NPC9933
0.8725	High Similarity	NPC225815
0.8725	High Similarity	NPC316989
0.8725	High Similarity	NPC469706
0.8725	High Similarity	NPC260781
0.8725	High Similarity	NPC182368
0.8725	High Similarity	NPC218041
0.8725	High Similarity	NPC469707
0.8725	High Similarity	NPC472710
0.8725	High Similarity	NPC24425
0.8725	High Similarity	NPC238140
0.8723	High Similarity	NPC47181
0.8723	High Similarity	NPC244983
0.8723	High Similarity	NPC326095
0.8716	High Similarity	NPC166584

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 NPC475868 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	921
0.2-0.3	1902
0.3-0.4	2875
0.4-0.5	1595
0.5-0.6	954
0.6-0.7	491
0.7-0.8	69
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD4967	Phase 2
0.875	High Similarity	NPD4966	Approved
0.875	High Similarity	NPD4965	Approved
0.8675	High Similarity	NPD37	Approved
0.8516	High Similarity	NPD6234	Discontinued
0.8369	Intermediate Similarity	NPD3027	Phase 3
0.8261	Intermediate Similarity	NPD7228	Approved
0.8188	Intermediate Similarity	NPD3705	Approved
0.8176	Intermediate Similarity	NPD7199	Phase 2
0.7963	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7240	Approved
0.7945	Intermediate Similarity	NPD1613	Approved
0.7945	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6674	Discontinued
0.7724	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3018	Phase 2
0.7714	Intermediate Similarity	NPD1357	Approved
0.7671	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD3818	Discontinued
0.7595	Intermediate Similarity	NPD1653	Approved
0.7569	Intermediate Similarity	NPD2983	Phase 2
0.7569	Intermediate Similarity	NPD2982	Phase 2
0.7551	Intermediate Similarity	NPD4908	Phase 1
0.7536	Intermediate Similarity	NPD5283	Phase 1
0.7534	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2981	Phase 2
0.7467	Intermediate Similarity	NPD3620	Phase 2
0.7467	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1610	Phase 2
0.7431	Intermediate Similarity	NPD1091	Approved
0.7421	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7074	Phase 3
0.7399	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7365	Intermediate Similarity	NPD6232	Discontinued
0.7365	Intermediate Similarity	NPD2861	Phase 2
0.7353	Intermediate Similarity	NPD5844	Phase 1
0.7353	Intermediate Similarity	NPD7054	Approved
0.7337	Intermediate Similarity	NPD7473	Discontinued
0.7329	Intermediate Similarity	NPD4005	Discontinued
0.7325	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7472	Approved
0.729	Intermediate Similarity	NPD7266	Discontinued
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.7228	Intermediate Similarity	NPD7680	Approved
0.7225	Intermediate Similarity	NPD6559	Discontinued
0.7219	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4749	Approved
0.7211	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1934	Approved
0.7184	Intermediate Similarity	NPD7808	Phase 3
0.7179	Intermediate Similarity	NPD3540	Phase 1
0.7169	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6797	Phase 2
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD3892	Phase 2
0.7152	Intermediate Similarity	NPD2978	Approved
0.7152	Intermediate Similarity	NPD2977	Approved
0.7143	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7251	Discontinued
0.7126	Intermediate Similarity	NPD4055	Discovery
0.7124	Intermediate Similarity	NPD2238	Phase 2
0.7117	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3539	Phase 1
0.7107	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5177	Phase 3
0.7086	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6841	Approved
0.7079	Intermediate Similarity	NPD6843	Phase 3
0.7079	Intermediate Similarity	NPD6842	Approved
0.7076	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6166	Phase 2
0.7076	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5762	Approved
0.707	Intermediate Similarity	NPD5763	Approved
0.7066	Intermediate Similarity	NPD3882	Suspended
0.7063	Intermediate Similarity	NPD5058	Phase 3
0.7059	Intermediate Similarity	NPD3787	Discontinued
0.7055	Intermediate Similarity	NPD5125	Phase 3
0.7055	Intermediate Similarity	NPD5126	Approved
0.7051	Intermediate Similarity	NPD4108	Discontinued
0.7048	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1465	Phase 2
0.7041	Intermediate Similarity	NPD5494	Approved
0.7021	Intermediate Similarity	NPD228	Approved
0.7006	Intermediate Similarity	NPD2563	Approved
0.7006	Intermediate Similarity	NPD2560	Approved
0.7006	Intermediate Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4236	Phase 3
0.6981	Remote Similarity	NPD4237	Approved
0.697	Remote Similarity	NPD7028	Phase 2
0.6968	Remote Similarity	NPD3657	Discovery
0.6968	Remote Similarity	NPD5735	Approved
0.6962	Remote Similarity	NPD1375	Discontinued
0.6959	Remote Similarity	NPD7229	Phase 3
0.6957	Remote Similarity	NPD7124	Phase 2
0.6946	Remote Similarity	NPD8455	Phase 2
0.6946	Remote Similarity	NPD2801	Approved
0.6944	Remote Similarity	NPD709	Approved
0.6918	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4357	Discontinued
0.6897	Remote Similarity	NPD3751	Discontinued
0.6894	Remote Similarity	NPD2677	Approved
0.6883	Remote Similarity	NPD5109	Approved
0.6883	Remote Similarity	NPD5110	Phase 2
0.6883	Remote Similarity	NPD5111	Phase 2
0.6879	Remote Similarity	NPD6111	Discontinued
0.6879	Remote Similarity	NPD3021	Approved
0.6879	Remote Similarity	NPD3022	Approved
0.6879	Remote Similarity	NPD4750	Phase 3
0.6875	Remote Similarity	NPD3060	Approved
0.6871	Remote Similarity	NPD2534	Approved
0.6871	Remote Similarity	NPD2532	Approved
0.6871	Remote Similarity	NPD2533	Approved
0.6871	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4678	Approved
0.6867	Remote Similarity	NPD4380	Phase 2
0.6867	Remote Similarity	NPD4675	Approved
0.6867	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6355	Discontinued
0.6859	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5124	Phase 1
0.6857	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7819	Suspended
0.6836	Remote Similarity	NPD7685	Pre-registration
0.6832	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4110	Phase 3
0.6828	Remote Similarity	NPD7157	Approved
0.6826	Remote Similarity	NPD5090	Approved
0.6826	Remote Similarity	NPD5089	Approved
0.6824	Remote Similarity	NPD4626	Approved
0.6821	Remote Similarity	NPD2970	Approved
0.6821	Remote Similarity	NPD2969	Approved
0.6821	Remote Similarity	NPD6696	Suspended
0.6815	Remote Similarity	NPD4097	Suspended
0.6802	Remote Similarity	NPD6959	Discontinued
0.6802	Remote Similarity	NPD8127	Discontinued
0.6798	Remote Similarity	NPD7549	Discontinued
0.6795	Remote Similarity	NPD4140	Approved
0.6792	Remote Similarity	NPD6100	Approved
0.6792	Remote Similarity	NPD6099	Approved
0.6792	Remote Similarity	NPD2438	Suspended
0.679	Remote Similarity	NPD2219	Phase 1
0.679	Remote Similarity	NPD5241	Discontinued
0.6786	Remote Similarity	NPD3383	Approved
0.6786	Remote Similarity	NPD3382	Approved
0.6786	Remote Similarity	NPD3384	Approved
0.678	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3094	Phase 2
0.677	Remote Similarity	NPD1652	Phase 2
0.6763	Remote Similarity	NPD6071	Discontinued
0.6763	Remote Similarity	NPD3051	Approved
0.6758	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6005	Phase 3
0.675	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6002	Phase 3
0.675	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6004	Phase 3
0.6746	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7843	Approved
0.6735	Remote Similarity	NPD5536	Phase 2
0.6733	Remote Similarity	NPD422	Phase 1
0.673	Remote Similarity	NPD5588	Approved
0.6728	Remote Similarity	NPD6331	Phase 2
0.6728	Remote Similarity	NPD3750	Approved
0.6727	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3926	Phase 2
0.672	Remote Similarity	NPD5006	Approved
0.672	Remote Similarity	NPD5005	Approved
0.6711	Remote Similarity	NPD8651	Approved
0.6711	Remote Similarity	NPD1283	Approved
0.6707	Remote Similarity	NPD1511	Approved
0.6703	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2684	Approved
0.6689	Remote Similarity	NPD2232	Approved
0.6689	Remote Similarity	NPD2230	Approved
0.6689	Remote Similarity	NPD2233	Approved
0.6687	Remote Similarity	NPD2161	Phase 2
0.6686	Remote Similarity	NPD2489	Approved
0.6686	Remote Similarity	NPD27	Approved
0.6685	Remote Similarity	NPD7296	Approved
0.6667	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD4536	Approved
0.6667	Remote Similarity	NPD4538	Approved
0.6648	Remote Similarity	NPD4663	Approved
0.6646	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5327	Phase 3
0.6644	Remote Similarity	NPD5691	Approved
0.6628	Remote Similarity	NPD5604	Discontinued

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