NPASS Compound

Structure

NPC49353 OpenBabel07101718332D 33 37 0 0 1 0 0 0 0 0999 V2000 1.0705 4.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4158 2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 2.6473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2784 3.3164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 4 2 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 7 1 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 25 1 0 0 0 0 8 25 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 0 0 0 0 14 24 1 0 0 0 0 15 30 1 6 0 0 0 16 24 1 0 0 0 0 17 18 2 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 12 1 1 0 0 0 19 20 1 0 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 6 0 0 0 21 22 1 0 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 29 1 6 0 0 0 23 32 1 1 0 0 0 23 33 1 0 0 0 0 24 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	461.2
Volume:	449.014
LogP:	0.149
LogD:	0.705
LogS:	-1.766
# Rotatable Bonds:	5
TPSA:	121.08
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	5.21
Fsp3:	0.583
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:	-5.849
MDCK Permeability:	2.8125732569606043e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.929
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.752

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	49.408470153808594%
Volume Distribution (VD):	0.907
Pgp-substrate:	38.38434600830078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.333
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.251
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	3.454
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.61
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.76
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.512
Carcinogencity:	0.755
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC49353

Natural Product ID:	NPC49353
*Common Name:**	Grycoerysodine
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(2R,13bS)-2,12-dimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-11-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Grycoerysodine
Standard InCHIKey:	LDKVUIURMJHFPP-VGNMVZQISA-N
Standard InCHI:	InChI=1S/C24H31NO8/c1-30-15-4-3-14-6-8-25-7-5-13-9-18(17(31-2)10-16(13)24(14,25)11-15)32-23-22(29)21(28)20(27)19(12-26)33-23/h3-4,6,9-10,15,19-23,26-29H,5,7-8,11-12H2,1-2H3/t15-,19+,20+,21-,22+,23+,24-/m0/s1
SMILES:	CO[C@H]1C=CC2=CCN3[C@]2(C1)c1cc(OC)c(cc1CC3)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464248
PubChem CID:	44570487
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001782] Erythrina alkaloids [CHEMONTID:0002780] Erythrinanes

*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
NPO20031	Erythrina velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19026536]
NPO20031	Erythrina velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[520206]
NPT15	Cell Line	Jurkat	Homo sapiens	Inhibition	=	4.7	%	PMID[520206]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	44.0	ug.mL-1	PMID[520206]

☑ 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 NPC49353 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	303
0.1-0.2	1332
0.2-0.3	4268
0.3-0.4	10765
0.4-0.5	8505
0.5-0.6	11161
0.6-0.7	5241
0.7-0.8	968
0.8-0.85	139
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8951	High Similarity	NPC59028
0.8951	High Similarity	NPC92191
0.8758	High Similarity	NPC148898
0.8757	High Similarity	NPC2314
0.875	High Similarity	NPC274026
0.8743	High Similarity	NPC100566
0.8706	High Similarity	NPC187678
0.8698	High Similarity	NPC470739
0.8698	High Similarity	NPC225597
0.8698	High Similarity	NPC477640
0.869	High Similarity	NPC82533
0.869	High Similarity	NPC158148
0.869	High Similarity	NPC290759
0.869	High Similarity	NPC266176
0.8642	High Similarity	NPC133011
0.8642	High Similarity	NPC82285
0.8639	High Similarity	NPC474475
0.8631	High Similarity	NPC190332
0.8631	High Similarity	NPC181653
0.8596	High Similarity	NPC304675
0.858	High Similarity	NPC58766
0.858	High Similarity	NPC475686
0.8571	High Similarity	NPC476002
0.8563	High Similarity	NPC320104
0.8554	High Similarity	NPC4304
0.8553	High Similarity	NPC130926
0.8547	High Similarity	NPC237044
0.8547	High Similarity	NPC474470
0.8497	Intermediate Similarity	NPC474325
0.8483	Intermediate Similarity	NPC475754
0.8448	Intermediate Similarity	NPC474745
0.8448	Intermediate Similarity	NPC244554
0.8443	Intermediate Similarity	NPC97072
0.8443	Intermediate Similarity	NPC215829
0.8421	Intermediate Similarity	NPC311991
0.8412	Intermediate Similarity	NPC252960
0.8409	Intermediate Similarity	NPC475981
0.8409	Intermediate Similarity	NPC474746
0.8402	Intermediate Similarity	NPC276944
0.8402	Intermediate Similarity	NPC232514
0.8402	Intermediate Similarity	NPC238530
0.8402	Intermediate Similarity	NPC231198
0.8391	Intermediate Similarity	NPC118633
0.8391	Intermediate Similarity	NPC148693
0.8391	Intermediate Similarity	NPC15919
0.8391	Intermediate Similarity	NPC294790
0.8383	Intermediate Similarity	NPC111485
0.8343	Intermediate Similarity	NPC218614
0.8333	Intermediate Similarity	NPC205167
0.8333	Intermediate Similarity	NPC249274
0.8323	Intermediate Similarity	NPC475326
0.8314	Intermediate Similarity	NPC75958
0.8313	Intermediate Similarity	NPC138487
0.8313	Intermediate Similarity	NPC216459
0.8313	Intermediate Similarity	NPC41178
0.8313	Intermediate Similarity	NPC78733
0.8304	Intermediate Similarity	NPC474324
0.8304	Intermediate Similarity	NPC57812
0.8294	Intermediate Similarity	NPC247972
0.8282	Intermediate Similarity	NPC475959
0.8263	Intermediate Similarity	NPC146288
0.8263	Intermediate Similarity	NPC147091
0.8256	Intermediate Similarity	NPC475845
0.8249	Intermediate Similarity	NPC248642
0.8235	Intermediate Similarity	NPC59567
0.8232	Intermediate Similarity	NPC24260
0.8214	Intermediate Similarity	NPC65490
0.8214	Intermediate Similarity	NPC148014
0.8214	Intermediate Similarity	NPC40389
0.8214	Intermediate Similarity	NPC315707
0.8214	Intermediate Similarity	NPC78359
0.8212	Intermediate Similarity	NPC230098
0.8208	Intermediate Similarity	NPC474708
0.8207	Intermediate Similarity	NPC267414
0.8202	Intermediate Similarity	NPC156576
0.8193	Intermediate Similarity	NPC233029
0.8193	Intermediate Similarity	NPC210148
0.8187	Intermediate Similarity	NPC180306
0.8182	Intermediate Similarity	NPC114364
0.8182	Intermediate Similarity	NPC320223
0.8161	Intermediate Similarity	NPC65403
0.8156	Intermediate Similarity	NPC9867
0.8155	Intermediate Similarity	NPC234392
0.8155	Intermediate Similarity	NPC31311
0.815	Intermediate Similarity	NPC83198
0.815	Intermediate Similarity	NPC204908
0.8146	Intermediate Similarity	NPC233718
0.8146	Intermediate Similarity	NPC299990
0.8146	Intermediate Similarity	NPC73492
0.814	Intermediate Similarity	NPC264850
0.814	Intermediate Similarity	NPC124657
0.814	Intermediate Similarity	NPC13916
0.8136	Intermediate Similarity	NPC126284
0.8118	Intermediate Similarity	NPC18402
0.8114	Intermediate Similarity	NPC190783
0.8114	Intermediate Similarity	NPC152680
0.8114	Intermediate Similarity	NPC232386
0.8107	Intermediate Similarity	NPC129603
0.8095	Intermediate Similarity	NPC172765
0.8095	Intermediate Similarity	NPC278799
0.8095	Intermediate Similarity	NPC207757
0.8095	Intermediate Similarity	NPC295691
0.8095	Intermediate Similarity	NPC39701
0.8095	Intermediate Similarity	NPC189266
0.8095	Intermediate Similarity	NPC110416
0.8095	Intermediate Similarity	NPC54379
0.8095	Intermediate Similarity	NPC2413
0.8095	Intermediate Similarity	NPC276588
0.8095	Intermediate Similarity	NPC249797
0.8095	Intermediate Similarity	NPC5238
0.8095	Intermediate Similarity	NPC469817
0.8095	Intermediate Similarity	NPC127674
0.8095	Intermediate Similarity	NPC204828
0.8095	Intermediate Similarity	NPC184026
0.8095	Intermediate Similarity	NPC193949
0.8092	Intermediate Similarity	NPC247389
0.8081	Intermediate Similarity	NPC24465
0.8072	Intermediate Similarity	NPC151895
0.8072	Intermediate Similarity	NPC192768
0.8072	Intermediate Similarity	NPC97221
0.8072	Intermediate Similarity	NPC220858
0.8072	Intermediate Similarity	NPC88249
0.8068	Intermediate Similarity	NPC128560
0.8068	Intermediate Similarity	NPC199465
0.8068	Intermediate Similarity	NPC229166
0.8061	Intermediate Similarity	NPC147390
0.8061	Intermediate Similarity	NPC246587
0.8061	Intermediate Similarity	NPC135538
0.8061	Intermediate Similarity	NPC428
0.8061	Intermediate Similarity	NPC24233
0.8061	Intermediate Similarity	NPC476571
0.8059	Intermediate Similarity	NPC106786
0.8059	Intermediate Similarity	NPC477080
0.8047	Intermediate Similarity	NPC323443
0.8047	Intermediate Similarity	NPC180756
0.8045	Intermediate Similarity	NPC275132
0.8035	Intermediate Similarity	NPC24264
0.8035	Intermediate Similarity	NPC219341
0.8035	Intermediate Similarity	NPC476432
0.8034	Intermediate Similarity	NPC32154
0.8023	Intermediate Similarity	NPC241704
0.8011	Intermediate Similarity	NPC214116
0.8	Intermediate Similarity	NPC106295
0.8	Intermediate Similarity	NPC16107
0.8	Intermediate Similarity	NPC179825
0.8	Intermediate Similarity	NPC51957
0.8	Intermediate Similarity	NPC191376
0.8	Intermediate Similarity	NPC321505
0.8	Intermediate Similarity	NPC210437
0.8	Intermediate Similarity	NPC476144
0.7989	Intermediate Similarity	NPC301189
0.7989	Intermediate Similarity	NPC150879
0.7989	Intermediate Similarity	NPC298186
0.7988	Intermediate Similarity	NPC93593
0.7988	Intermediate Similarity	NPC185838
0.7977	Intermediate Similarity	NPC167546
0.7977	Intermediate Similarity	NPC16805
0.7977	Intermediate Similarity	NPC302527
0.7977	Intermediate Similarity	NPC225774
0.7976	Intermediate Similarity	NPC223124
0.7975	Intermediate Similarity	NPC128019
0.7975	Intermediate Similarity	NPC476567
0.7975	Intermediate Similarity	NPC136860
0.7968	Intermediate Similarity	NPC475654
0.7963	Intermediate Similarity	NPC213206
0.7963	Intermediate Similarity	NPC474915
0.7963	Intermediate Similarity	NPC328750
0.7963	Intermediate Similarity	NPC188163
0.7955	Intermediate Similarity	NPC57272
0.7952	Intermediate Similarity	NPC7467
0.7952	Intermediate Similarity	NPC59907
0.7952	Intermediate Similarity	NPC37144
0.7944	Intermediate Similarity	NPC285931
0.7944	Intermediate Similarity	NPC328155
0.7944	Intermediate Similarity	NPC181796
0.7944	Intermediate Similarity	NPC229373
0.7944	Intermediate Similarity	NPC8836
0.7944	Intermediate Similarity	NPC271013
0.7944	Intermediate Similarity	NPC54654
0.7944	Intermediate Similarity	NPC290582
0.7944	Intermediate Similarity	NPC217748
0.7944	Intermediate Similarity	NPC7715
0.7944	Intermediate Similarity	NPC279228
0.7944	Intermediate Similarity	NPC104196
0.7944	Intermediate Similarity	NPC182052
0.7944	Intermediate Similarity	NPC42663
0.7944	Intermediate Similarity	NPC222661
0.7944	Intermediate Similarity	NPC251735
0.7944	Intermediate Similarity	NPC239824
0.7944	Intermediate Similarity	NPC15414
0.7944	Intermediate Similarity	NPC49075
0.7944	Intermediate Similarity	NPC258657
0.7944	Intermediate Similarity	NPC311973
0.7944	Intermediate Similarity	NPC90998
0.7944	Intermediate Similarity	NPC30779
0.7944	Intermediate Similarity	NPC290005
0.7944	Intermediate Similarity	NPC223690
0.7944	Intermediate Similarity	NPC185639
0.7937	Intermediate Similarity	NPC7018
0.7931	Intermediate Similarity	NPC42549

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 NPC49353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	676
0.2-0.3	974
0.3-0.4	2449
0.4-0.5	2495
0.5-0.6	1582
0.6-0.7	656
0.7-0.8	120
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8364	Intermediate Similarity	NPD4772	Phase 2
0.8364	Intermediate Similarity	NPD4773	Phase 2
0.8246	Intermediate Similarity	NPD6071	Discontinued
0.8214	Intermediate Similarity	NPD2560	Approved
0.8214	Intermediate Similarity	NPD2563	Approved
0.8092	Intermediate Similarity	NPD2970	Approved
0.8092	Intermediate Similarity	NPD2969	Approved
0.8035	Intermediate Similarity	NPD3051	Approved
0.8	Intermediate Similarity	NPD4584	Approved
0.7963	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD8053	Approved
0.7944	Intermediate Similarity	NPD8054	Approved
0.7943	Intermediate Similarity	NPD2489	Approved
0.7943	Intermediate Similarity	NPD27	Approved
0.791	Intermediate Similarity	NPD8156	Discontinued
0.7853	Intermediate Similarity	NPD8251	Approved
0.7853	Intermediate Similarity	NPD8099	Discontinued
0.7853	Intermediate Similarity	NPD8252	Approved
0.7836	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7906	Approved
0.779	Intermediate Similarity	NPD7312	Approved
0.779	Intermediate Similarity	NPD7311	Approved
0.779	Intermediate Similarity	NPD7310	Approved
0.779	Intermediate Similarity	NPD7313	Approved
0.7747	Intermediate Similarity	NPD7309	Approved
0.774	Intermediate Similarity	NPD4481	Phase 3
0.7692	Intermediate Similarity	NPD6030	Approved
0.7692	Intermediate Similarity	NPD6031	Approved
0.7683	Intermediate Similarity	NPD1375	Discontinued
0.7665	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD4663	Approved
0.763	Intermediate Similarity	NPD5773	Approved
0.763	Intermediate Similarity	NPD2977	Approved
0.763	Intermediate Similarity	NPD5772	Approved
0.763	Intermediate Similarity	NPD2978	Approved
0.76	Intermediate Similarity	NPD7833	Phase 2
0.76	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7831	Phase 2
0.7596	Intermediate Similarity	NPD4578	Approved
0.7596	Intermediate Similarity	NPD4577	Approved
0.7594	Intermediate Similarity	NPD7296	Approved
0.7574	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6107	Approved
0.7561	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5241	Discontinued
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4420	Approved
0.7485	Intermediate Similarity	NPD3640	Phase 3
0.7485	Intermediate Similarity	NPD4237	Approved
0.7485	Intermediate Similarity	NPD3639	Approved
0.7485	Intermediate Similarity	NPD4236	Phase 3
0.7485	Intermediate Similarity	NPD3641	Approved
0.7471	Intermediate Similarity	NPD7298	Approved
0.7444	Intermediate Similarity	NPD2898	Approved
0.7423	Intermediate Similarity	NPD5005	Approved
0.7423	Intermediate Similarity	NPD5006	Approved
0.7416	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4017	Approved
0.7396	Intermediate Similarity	NPD2677	Approved
0.7382	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4162	Approved
0.7345	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6788	Approved
0.7341	Intermediate Similarity	NPD4210	Discontinued
0.734	Intermediate Similarity	NPD6842	Approved
0.734	Intermediate Similarity	NPD6843	Phase 3
0.734	Intermediate Similarity	NPD6841	Approved
0.7333	Intermediate Similarity	NPD4010	Discontinued
0.7322	Intermediate Similarity	NPD5312	Approved
0.7322	Intermediate Similarity	NPD5313	Approved
0.7305	Intermediate Similarity	NPD2161	Phase 2
0.7303	Intermediate Similarity	NPD5604	Discontinued
0.7294	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5582	Discontinued
0.7284	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2122	Discontinued
0.7278	Intermediate Similarity	NPD5177	Phase 3
0.7278	Intermediate Similarity	NPD6674	Discontinued
0.7267	Intermediate Similarity	NPD4123	Phase 3
0.7254	Intermediate Similarity	NPD2975	Approved
0.7254	Intermediate Similarity	NPD2973	Approved
0.7254	Intermediate Similarity	NPD2974	Approved
0.7241	Intermediate Similarity	NPD3687	Approved
0.7241	Intermediate Similarity	NPD3686	Approved
0.7239	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5677	Discontinued
0.7212	Intermediate Similarity	NPD2238	Phase 2
0.7194	Intermediate Similarity	NPD3452	Approved
0.7194	Intermediate Similarity	NPD3450	Approved
0.7194	Intermediate Similarity	NPD2493	Approved
0.7194	Intermediate Similarity	NPD2494	Approved
0.7179	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3060	Approved
0.7175	Intermediate Similarity	NPD3382	Approved
0.7175	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3384	Approved
0.7175	Intermediate Similarity	NPD3383	Approved
0.7173	Intermediate Similarity	NPD2490	Approved
0.7173	Intermediate Similarity	NPD2488	Approved
0.7168	Intermediate Similarity	NPD1424	Approved
0.7163	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3656	Approved
0.7159	Intermediate Similarity	NPD4678	Approved
0.7159	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD4580	Approved
0.7128	Intermediate Similarity	NPD2968	Approved
0.7128	Intermediate Similarity	NPD7280	Phase 3
0.7128	Intermediate Similarity	NPD7281	Phase 3
0.7128	Intermediate Similarity	NPD2971	Approved
0.7126	Intermediate Similarity	NPD52	Approved
0.7126	Intermediate Similarity	NPD7526	Approved
0.7126	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3124	Discontinued
0.7102	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4005	Discontinued
0.7092	Intermediate Similarity	NPD8095	Phase 1
0.7091	Intermediate Similarity	NPD5718	Phase 2
0.709	Intermediate Similarity	NPD6853	Approved
0.709	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6851	Approved
0.7085	Intermediate Similarity	NPD4583	Approved
0.7085	Intermediate Similarity	NPD4582	Approved
0.7074	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7549	Discontinued
0.7063	Intermediate Similarity	NPD3705	Approved
0.7059	Intermediate Similarity	NPD7007	Discovery
0.7059	Intermediate Similarity	NPD6297	Approved
0.7049	Intermediate Similarity	NPD4166	Phase 2
0.7048	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4108	Discontinued
0.7035	Intermediate Similarity	NPD4004	Approved
0.7035	Intermediate Similarity	NPD6331	Phase 2
0.7035	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4002	Approved
0.7033	Intermediate Similarity	NPD2904	Discontinued
0.7017	Intermediate Similarity	NPD4055	Discovery
0.7011	Intermediate Similarity	NPD1774	Approved
0.6995	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7802	Discontinued
0.6994	Remote Similarity	NPD3692	Discontinued
0.6985	Remote Similarity	NPD3057	Approved
0.6979	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3122	Phase 3
0.6954	Remote Similarity	NPD7124	Phase 2
0.6946	Remote Similarity	NPD4475	Approved
0.6946	Remote Similarity	NPD4474	Approved
0.6946	Remote Similarity	NPD2674	Phase 3
0.6943	Remote Similarity	NPD2843	Phase 2
0.6943	Remote Similarity	NPD2845	Phase 2
0.6941	Remote Similarity	NPD1753	Discontinued
0.6935	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6090	Discontinued
0.6931	Remote Similarity	NPD7038	Approved
0.6931	Remote Similarity	NPD7039	Approved
0.6923	Remote Similarity	NPD2492	Phase 1
0.6919	Remote Similarity	NPD7153	Discontinued
0.6915	Remote Similarity	NPD3885	Approved
0.6914	Remote Similarity	NPD2420	Approved
0.6914	Remote Similarity	NPD2421	Approved
0.69	Remote Similarity	NPD3533	Approved
0.69	Remote Similarity	NPD2972	Approved
0.6897	Remote Similarity	NPD5160	Discontinued
0.6895	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5976	Discontinued
0.6893	Remote Similarity	NPD4727	Phase 1
0.689	Remote Similarity	NPD4098	Discontinued
0.6882	Remote Similarity	NPD6895	Approved
0.6882	Remote Similarity	NPD2200	Suspended
0.6882	Remote Similarity	NPD6896	Approved
0.6878	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7266	Discontinued
0.6857	Remote Similarity	NPD3845	Phase 1
0.6857	Remote Similarity	NPD6667	Approved
0.6857	Remote Similarity	NPD6666	Approved
0.6848	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4666	Phase 3
0.6848	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7827	Phase 1
0.6845	Remote Similarity	NPD5938	Phase 3
0.6839	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6748	Discontinued
0.6836	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4040	Phase 1
0.6828	Remote Similarity	NPD6687	Approved
0.6828	Remote Similarity	NPD5242	Approved
0.6828	Remote Similarity	NPD6688	Approved
0.6827	Remote Similarity	NPD7047	Phase 3
0.6826	Remote Similarity	NPD3179	Approved
0.6826	Remote Similarity	NPD3180	Approved
0.6824	Remote Similarity	NPD823	Approved
0.6824	Remote Similarity	NPD817	Approved
0.6818	Remote Similarity	NPD7213	Phase 3
0.6818	Remote Similarity	NPD7212	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