NPASS Compound

Structure

CID172171 OpenBabel06191715542D 29 33 0 0 1 0 0 0 0 0999 V2000 2.8865 -5.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2220 -5.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6803 1.1600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4282 1.1600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1924 -3.6044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1031 -2.4175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0054 -2.4175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0397 -0.1475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9312 -0.1475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5257 -4.2711 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5828 -4.2711 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1924 -2.6616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9161 -2.6616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3471 -1.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2387 -1.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5257 -1.9949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5828 -1.9949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9161 -3.6044 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6804 -0.8401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4280 -0.8401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7697 -1.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3388 -1.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0450 -3.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4363 0.2493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6722 0.2493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1872 -1.0787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0787 -1.0787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1085 -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 24 1 0 0 0 0 4 25 1 0 0 0 0 5 10 1 0 0 0 0 5 12 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 26 1 0 0 0 0 8 28 1 0 0 0 0 9 27 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 6 0 0 0 10 11 1 0 0 0 0 11 2 1 6 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 26 1 0 0 0 0 15 20 2 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 18 23 1 6 0 0 0 19 21 1 0 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.15
Volume:	391.999
LogP:	3.695
LogD:	3.603
LogS:	-5.101
# Rotatable Bonds:	2
TPSA:	75.61
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.824
Synthetic Accessibility Score:	3.928
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:	-4.775
MDCK Permeability:	4.3957938032690436e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	88.4492416381836%
Volume Distribution (VD):	1.103
Pgp-substrate:	4.742642402648926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.401
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.12
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.379
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.473

ADMET: Excretion

Clearance (CL):	13.946
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.523
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.228
Skin Sensitization:	0.254
Carcinogencity:	0.946
Eye Corrosion:	0.003
Eye Irritation:	0.065
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC172171

Natural Product ID:	NPC172171
*Common Name:**	Gomisin R
IUPAC Name:	n.a.
Synonyms:	Gomisin R
Standard InCHIKey:	HOPDFAWBFXSPSA-FHGNATFXSA-N
Standard InCHI:	InChI=1S/C22H24O7/c1-10-5-12-6-14-19(28-8-26-14)21(24-3)16(12)17-13(18(23)11(10)2)7-15-20(22(17)25-4)29-9-27-15/h6-7,10-11,18,23H,5,8-9H2,1-4H3/t10-,11-,18-/m0/s1
SMILES:	C[C@H]1Cc2cc3c(c(c2-c2c(cc4c(c2OC)OCO4)[C@H]([C@H]1C)O)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465720
PubChem CID:	11516888
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
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO8974	Chlamys hastata	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3651433]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11529	Alcyonium palmatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8974	Chlamys hastata	Species	Pectinidae	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	=	220750.0	nM	PMID[508415]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	54580.0	nM	PMID[508415]
NPT2	Others	Unspecified		Ratio	=	4.04	n.a.	PMID[508415]

☑ 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 NPC172171 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	405
0.1-0.2	1542
0.2-0.3	4090
0.3-0.4	10929
0.4-0.5	7928
0.5-0.6	4605
0.6-0.7	8647
0.7-0.8	3371
0.8-0.85	866
0.85-0.9	248
0.9-0.95	51
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239254
0.9927	High Similarity	NPC475868
0.9853	High Similarity	NPC36531
0.9853	High Similarity	NPC229172
0.9853	High Similarity	NPC230538
0.9853	High Similarity	NPC103637
0.9781	High Similarity	NPC324962
0.9712	High Similarity	NPC252286
0.9712	High Similarity	NPC154971
0.964	High Similarity	NPC110763
0.964	High Similarity	NPC197352
0.964	High Similarity	NPC166506
0.964	High Similarity	NPC189239
0.9577	High Similarity	NPC473989
0.9568	High Similarity	NPC121661
0.9568	High Similarity	NPC73467
0.9489	High Similarity	NPC290714
0.9489	High Similarity	NPC201404
0.9489	High Similarity	NPC53722
0.9485	High Similarity	NPC32189
0.9437	High Similarity	NPC325720
0.9437	High Similarity	NPC316676
0.9424	High Similarity	NPC133934
0.9424	High Similarity	NPC184641
0.9424	High Similarity	NPC184684
0.9357	High Similarity	NPC474808
0.9338	High Similarity	NPC185680
0.9338	High Similarity	NPC145722
0.9338	High Similarity	NPC256776
0.9315	High Similarity	NPC312763
0.9281	High Similarity	NPC103448
0.9281	High Similarity	NPC216434
0.927	High Similarity	NPC150534
0.9209	High Similarity	NPC9068
0.9149	High Similarity	NPC474295
0.9143	High Similarity	NPC46591
0.9143	High Similarity	NPC177868
0.9137	High Similarity	NPC156948
0.9137	High Similarity	NPC46277
0.9137	High Similarity	NPC86605
0.9137	High Similarity	NPC474039
0.9137	High Similarity	NPC3072
0.9137	High Similarity	NPC185908
0.9137	High Similarity	NPC301765
0.9137	High Similarity	NPC283949
0.9124	High Similarity	NPC196937
0.9124	High Similarity	NPC58585
0.9116	High Similarity	NPC24562
0.911	High Similarity	NPC475756
0.9097	High Similarity	NPC116019
0.9091	High Similarity	NPC180953
0.9085	High Similarity	NPC76415
0.9085	High Similarity	NPC218510
0.9065	High Similarity	NPC133025
0.9065	High Similarity	NPC197166
0.9054	High Similarity	NPC473425
0.9054	High Similarity	NPC198461
0.9051	High Similarity	NPC219671
0.9051	High Similarity	NPC147616
0.9051	High Similarity	NPC72046
0.9051	High Similarity	NPC261812
0.9051	High Similarity	NPC65183
0.9051	High Similarity	NPC259742
0.9051	High Similarity	NPC104077
0.9048	High Similarity	NPC471154
0.9034	High Similarity	NPC304821
0.9028	High Similarity	NPC33832
0.9021	High Similarity	NPC326144
0.9014	High Similarity	NPC287124
0.9007	High Similarity	NPC226547
0.9007	High Similarity	NPC56091
0.8986	High Similarity	NPC136750
0.8986	High Similarity	NPC474606
0.8986	High Similarity	NPC266848
0.8986	High Similarity	NPC112237
0.898	High Similarity	NPC224472
0.8973	High Similarity	NPC85141
0.8958	High Similarity	NPC318286
0.8958	High Similarity	NPC327651
0.8951	High Similarity	NPC298317
0.8951	High Similarity	NPC185071
0.8951	High Similarity	NPC265154
0.8951	High Similarity	NPC12728
0.8951	High Similarity	NPC255566
0.8936	High Similarity	NPC6369
0.8936	High Similarity	NPC471183
0.8936	High Similarity	NPC30951
0.8933	High Similarity	NPC473323
0.8921	High Similarity	NPC56764
0.8921	High Similarity	NPC206737
0.8921	High Similarity	NPC276026
0.8921	High Similarity	NPC7515
0.8921	High Similarity	NPC469659
0.8921	High Similarity	NPC289258
0.8921	High Similarity	NPC188378
0.8921	High Similarity	NPC555
0.8921	High Similarity	NPC31530
0.8913	High Similarity	NPC102256
0.8913	High Similarity	NPC7744
0.8904	High Similarity	NPC71726
0.8897	High Similarity	NPC212890
0.8897	High Similarity	NPC321958
0.8897	High Similarity	NPC321696
0.8889	High Similarity	NPC166884
0.8889	High Similarity	NPC141569
0.8889	High Similarity	NPC477701
0.8881	High Similarity	NPC191231
0.8881	High Similarity	NPC41782
0.8873	High Similarity	NPC284464
0.8867	High Similarity	NPC476065
0.8867	High Similarity	NPC238834
0.8865	High Similarity	NPC196420
0.8859	High Similarity	NPC297271
0.8859	High Similarity	NPC308739
0.8859	High Similarity	NPC53669
0.8859	High Similarity	NPC77237
0.8859	High Similarity	NPC126405
0.8859	High Similarity	NPC16791
0.8859	High Similarity	NPC217708
0.8857	High Similarity	NPC189474
0.8857	High Similarity	NPC55239
0.8857	High Similarity	NPC180602
0.8857	High Similarity	NPC236522
0.8857	High Similarity	NPC148893
0.8857	High Similarity	NPC49235
0.8857	High Similarity	NPC474139
0.8857	High Similarity	NPC18576
0.8857	High Similarity	NPC174191
0.8857	High Similarity	NPC25333
0.8857	High Similarity	NPC240279
0.8857	High Similarity	NPC214853
0.8851	High Similarity	NPC303519
0.8844	High Similarity	NPC240521
0.8841	High Similarity	NPC141493
0.8841	High Similarity	NPC184928
0.8841	High Similarity	NPC192255
0.8831	High Similarity	NPC475865
0.8828	High Similarity	NPC178014
0.8828	High Similarity	NPC42716
0.8828	High Similarity	NPC474749
0.8828	High Similarity	NPC11422
0.8828	High Similarity	NPC477702
0.8811	High Similarity	NPC312199
0.8794	High Similarity	NPC121651
0.8794	High Similarity	NPC25695
0.8794	High Similarity	NPC172818
0.8786	High Similarity	NPC47181
0.8777	High Similarity	NPC475856
0.8777	High Similarity	NPC97316
0.8776	High Similarity	NPC301961
0.8776	High Similarity	NPC248132
0.8776	High Similarity	NPC166584
0.8776	High Similarity	NPC252281
0.8776	High Similarity	NPC130449
0.8776	High Similarity	NPC477375
0.8776	High Similarity	NPC327352
0.8776	High Similarity	NPC198129
0.8768	High Similarity	NPC63574
0.8768	High Similarity	NPC184814
0.8767	High Similarity	NPC162193
0.8767	High Similarity	NPC474054
0.8767	High Similarity	NPC226540
0.8759	High Similarity	NPC207702
0.8759	High Similarity	NPC187774
0.8759	High Similarity	NPC283114
0.8759	High Similarity	NPC472712
0.8759	High Similarity	NPC473046
0.8759	High Similarity	NPC87883
0.8759	High Similarity	NPC472713
0.8759	High Similarity	NPC149008
0.8759	High Similarity	NPC118385
0.875	High Similarity	NPC475592
0.875	High Similarity	NPC473960
0.875	High Similarity	NPC19947
0.875	High Similarity	NPC207584
0.875	High Similarity	NPC472562
0.875	High Similarity	NPC80326
0.8732	High Similarity	NPC477938
0.8723	High Similarity	NPC135777
0.8723	High Similarity	NPC34103
0.8723	High Similarity	NPC24490
0.8723	High Similarity	NPC99572
0.8723	High Similarity	NPC142547
0.8723	High Similarity	NPC165155
0.8723	High Similarity	NPC126409
0.8723	High Similarity	NPC141765
0.8716	High Similarity	NPC477376
0.8716	High Similarity	NPC477374
0.8716	High Similarity	NPC322426
0.8716	High Similarity	NPC55158
0.8716	High Similarity	NPC51328
0.8716	High Similarity	NPC286235
0.8714	High Similarity	NPC471391
0.8714	High Similarity	NPC471390
0.8699	High Similarity	NPC307466
0.8693	High Similarity	NPC215400
0.8693	High Similarity	NPC230531
0.869	High Similarity	NPC469630
0.8686	High Similarity	NPC8050
0.8686	High Similarity	NPC242032

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 NPC172171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	922
0.2-0.3	1903
0.3-0.4	2842
0.4-0.5	1616
0.5-0.6	944
0.6-0.7	515
0.7-0.8	70
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD4966	Approved
0.8684	High Similarity	NPD4965	Approved
0.8684	High Similarity	NPD4967	Phase 2
0.8609	High Similarity	NPD37	Approved
0.8452	Intermediate Similarity	NPD6234	Discontinued
0.8429	Intermediate Similarity	NPD3027	Phase 3
0.8248	Intermediate Similarity	NPD3705	Approved
0.8199	Intermediate Similarity	NPD7228	Approved
0.8113	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7933	Intermediate Similarity	NPD6674	Discontinued
0.7901	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7240	Approved
0.7778	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1357	Approved
0.7724	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3018	Phase 2
0.7603	Intermediate Similarity	NPD4908	Phase 1
0.7593	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.7586	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.7532	Intermediate Similarity	NPD1653	Approved
0.7517	Intermediate Similarity	NPD3620	Phase 2
0.7517	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2982	Phase 2
0.7483	Intermediate Similarity	NPD1091	Approved
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7442	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4625	Phase 3
0.7431	Intermediate Similarity	NPD2981	Phase 2
0.7415	Intermediate Similarity	NPD2861	Phase 2
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7375	Intermediate Similarity	NPD4005	Discontinued
0.7372	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6232	Discontinued
0.7294	Intermediate Similarity	NPD7054	Approved
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7278	Intermediate Similarity	NPD7473	Discontinued
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4749	Approved
0.726	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7472	Approved
0.7244	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1934	Approved
0.7226	Intermediate Similarity	NPD7266	Discontinued
0.7203	Intermediate Similarity	NPD1548	Phase 1
0.7197	Intermediate Similarity	NPD3892	Phase 2
0.7195	Intermediate Similarity	NPD2978	Approved
0.7195	Intermediate Similarity	NPD2977	Approved
0.7188	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7680	Approved
0.7171	Intermediate Similarity	NPD2238	Phase 2
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.7152	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5177	Phase 3
0.7126	Intermediate Similarity	NPD7808	Phase 3
0.7115	Intermediate Similarity	NPD5762	Approved
0.7115	Intermediate Similarity	NPD5763	Approved
0.7115	Intermediate Similarity	NPD3540	Phase 1
0.711	Intermediate Similarity	NPD6797	Phase 2
0.7108	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3882	Suspended
0.7107	Intermediate Similarity	NPD5058	Phase 3
0.7103	Intermediate Similarity	NPD5126	Approved
0.7103	Intermediate Similarity	NPD5125	Phase 3
0.7102	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD4108	Discontinued
0.7091	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5494	Approved
0.7071	Intermediate Similarity	NPD228	Approved
0.7069	Intermediate Similarity	NPD7251	Discontinued
0.7066	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4055	Discovery
0.7055	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3539	Phase 1
0.7048	Intermediate Similarity	NPD2563	Approved
0.7048	Intermediate Similarity	NPD2560	Approved
0.7039	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4236	Phase 3
0.7025	Intermediate Similarity	NPD4237	Approved
0.7022	Intermediate Similarity	NPD6843	Phase 3
0.7022	Intermediate Similarity	NPD6842	Approved
0.7022	Intermediate Similarity	NPD6841	Approved
0.7018	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6166	Phase 2
0.7013	Intermediate Similarity	NPD3657	Discovery
0.7013	Intermediate Similarity	NPD5735	Approved
0.7012	Intermediate Similarity	NPD7028	Phase 2
0.7006	Intermediate Similarity	NPD1375	Discontinued
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD7124	Phase 2
0.6993	Remote Similarity	NPD709	Approved
0.6988	Remote Similarity	NPD2801	Approved
0.6988	Remote Similarity	NPD1465	Phase 2
0.6962	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4357	Discontinued
0.6946	Remote Similarity	NPD3817	Phase 2
0.6937	Remote Similarity	NPD2677	Approved
0.6936	Remote Similarity	NPD3751	Discontinued
0.6929	Remote Similarity	NPD3021	Approved
0.6929	Remote Similarity	NPD3022	Approved
0.6929	Remote Similarity	NPD4750	Phase 3
0.6928	Remote Similarity	NPD5110	Phase 2
0.6928	Remote Similarity	NPD5109	Approved
0.6928	Remote Similarity	NPD5111	Phase 2
0.6923	Remote Similarity	NPD6111	Discontinued
0.6918	Remote Similarity	NPD3060	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2533	Approved
0.6914	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD2534	Approved
0.6913	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4678	Approved
0.6909	Remote Similarity	NPD4675	Approved
0.6903	Remote Similarity	NPD5124	Phase 1
0.6903	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6355	Discontinued
0.6899	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8455	Phase 2
0.6875	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4110	Phase 3
0.6871	Remote Similarity	NPD4626	Approved
0.6867	Remote Similarity	NPD5089	Approved
0.6867	Remote Similarity	NPD5090	Approved
0.6867	Remote Similarity	NPD6696	Suspended
0.686	Remote Similarity	NPD2970	Approved
0.686	Remote Similarity	NPD2969	Approved
0.6859	Remote Similarity	NPD4097	Suspended
0.6839	Remote Similarity	NPD4140	Approved
0.6836	Remote Similarity	NPD7549	Discontinued
0.6835	Remote Similarity	NPD6099	Approved
0.6835	Remote Similarity	NPD6100	Approved
0.6832	Remote Similarity	NPD5241	Discontinued
0.6832	Remote Similarity	NPD2219	Phase 1
0.6826	Remote Similarity	NPD3382	Approved
0.6826	Remote Similarity	NPD3383	Approved
0.6826	Remote Similarity	NPD3384	Approved
0.6821	Remote Similarity	NPD3094	Phase 2
0.6813	Remote Similarity	NPD1652	Phase 2
0.6807	Remote Similarity	NPD4380	Phase 2
0.6802	Remote Similarity	NPD3051	Approved
0.6802	Remote Similarity	NPD6071	Discontinued
0.68	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6004	Phase 3
0.6792	Remote Similarity	NPD6005	Phase 3
0.6792	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6002	Phase 3
0.6792	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7819	Suspended
0.6786	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5536	Phase 2
0.678	Remote Similarity	NPD7685	Pre-registration
0.6779	Remote Similarity	NPD422	Phase 1
0.6772	Remote Similarity	NPD5588	Approved
0.677	Remote Similarity	NPD6331	Phase 2
0.677	Remote Similarity	NPD3750	Approved
0.6768	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7157	Approved
0.6755	Remote Similarity	NPD8651	Approved
0.6755	Remote Similarity	NPD5005	Approved
0.6755	Remote Similarity	NPD1283	Approved
0.6755	Remote Similarity	NPD5006	Approved
0.6748	Remote Similarity	NPD1511	Approved
0.6744	Remote Similarity	NPD8127	Discontinued
0.6744	Remote Similarity	NPD6959	Discontinued
0.674	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2684	Approved
0.6733	Remote Similarity	NPD2230	Approved
0.6733	Remote Similarity	NPD2232	Approved
0.6733	Remote Similarity	NPD2233	Approved
0.673	Remote Similarity	NPD2161	Phase 2
0.673	Remote Similarity	NPD2438	Suspended
0.6724	Remote Similarity	NPD2489	Approved
0.6724	Remote Similarity	NPD27	Approved
0.6723	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4536	Approved
0.6709	Remote Similarity	NPD4538	Approved
0.6703	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5327	Phase 3
0.6689	Remote Similarity	NPD5691	Approved
0.6687	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4663	Approved
0.6667	Remote Similarity	NPD4624	Approved
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD7466	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data