NPASS Compound

Structure

NPC475747 OpenBabel07101719512D 28 33 0 0 1 0 0 0 0 0999 V2000 -1.0764 -2.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0323 -2.6630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1648 -0.9629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1776 -0.2232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1776 -1.6633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4805 -2.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1695 -1.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0555 -2.4695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9093 -0.9433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5539 -0.5832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5539 -1.3033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2552 -2.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8012 -0.5832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8012 -1.3033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9909 -0.1342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3934 -2.7525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6621 -1.6035 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9909 -1.7523 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2889 -1.5920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0804 -2.2102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7681 -3.0784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1708 -3.7274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6531 -1.7377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3172 -0.4323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4860 -0.3607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4860 -1.5258 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 1 21 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 10 2 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 16 1 0 0 0 0 8 18 1 0 0 0 0 9 26 1 0 0 0 0 9 27 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 22 2 0 0 0 0 13 14 2 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 7 1 6 0 0 0 15 28 1 0 0 0 0 16 21 1 0 0 0 0 16 23 2 0 0 0 0 17 20 1 1 0 0 0 17 24 1 0 0 0 0 18 19 1 1 0 0 0 19 20 1 6 0 0 0 19 21 1 0 0 0 0 20 25 1 6 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.13
Volume:	362.483
LogP:	1.444
LogD:	1.511
LogS:	-4.341
# Rotatable Bonds:	2
TPSA:	83.53
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	6.122
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.174
MDCK Permeability:	2.5540333808748983e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.89

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	74.98188018798828%
Volume Distribution (VD):	1.227
Pgp-substrate:	22.530288696289062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.987
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.224
CYP3A4-inhibitor:	0.742
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	8.704
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.27
AMES Toxicity:	0.968
Rat Oral Acute Toxicity:	0.774
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.127
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC475747

Natural Product ID:	NPC475747
*Common Name:**	Periglaucine C
IUPAC Name:	n.a.
Synonyms:	Periglaucine C
Standard InCHIKey:	JCBUXRPOTHJGDK-RACLHMPKSA-N
Standard InCHI:	InChI=1S/C20H21NO7/c1-21-16(23)8-18-6-12(22)17(24-2)20(25-3)19(18,21)7-15(28-20)10-4-13-14(5-11(10)18)27-9-26-13/h4-5,15,17H,6-9H2,1-3H3/t15-,17-,18-,19+,20-/m1/s1
SMILES:	CO[C@@H]1C(=O)C[C@@]23[C@@]4([C@]1(OC)O[C@H](C4)c1c3cc3c(c1)OCO3)N(C)C(=O)C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513850
PubChem CID:	44577170
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002792] Hasubanan alkaloids

*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
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18396905]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18396905]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	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
IC50	2
Others	5

Activity Type	# Activity
Cell Line	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	516000.0	nM	PMID[491665]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.37	n.a.	PMID[491665]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	1720000.0	nM	PMID[491665]
NPT27	Others	Unspecified		CC50	=	2360000.0	nM	PMID[491665]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	3690000.0	nM	PMID[491665]
NPT2	Others	Unspecified		Ratio CC50/IC50	<	1.0	n.a.	PMID[491665]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	162500.0	nM	PMID[491665]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	3.29	n.a.	PMID[491665]

☑ 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 NPC475747 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	381
0.1-0.2	1639
0.2-0.3	4163
0.3-0.4	11652
0.4-0.5	8666
0.5-0.6	13950
0.6-0.7	2095
0.7-0.8	144
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9611	High Similarity	NPC475713
0.9611	High Similarity	NPC474432
0.9454	High Similarity	NPC474427
0.8533	High Similarity	NPC149285
0.8342	Intermediate Similarity	NPC293624
0.799	Intermediate Similarity	NPC196231
0.7919	Intermediate Similarity	NPC66909
0.7906	Intermediate Similarity	NPC115906
0.7887	Intermediate Similarity	NPC141440
0.7853	Intermediate Similarity	NPC99179
0.7778	Intermediate Similarity	NPC470646
0.773	Intermediate Similarity	NPC475780
0.7704	Intermediate Similarity	NPC237579
0.7692	Intermediate Similarity	NPC214629
0.7673	Intermediate Similarity	NPC151470
0.7673	Intermediate Similarity	NPC201055
0.7673	Intermediate Similarity	NPC64576
0.7673	Intermediate Similarity	NPC254045
0.7647	Intermediate Similarity	NPC218614
0.7589	Intermediate Similarity	NPC477393
0.7538	Intermediate Similarity	NPC63152
0.7537	Intermediate Similarity	NPC72788
0.7537	Intermediate Similarity	NPC226652
0.7537	Intermediate Similarity	NPC314100
0.7537	Intermediate Similarity	NPC120671
0.7526	Intermediate Similarity	NPC252960
0.7522	Intermediate Similarity	NPC477396
0.75	Intermediate Similarity	NPC102760
0.745	Intermediate Similarity	NPC319549
0.7448	Intermediate Similarity	NPC474708
0.7438	Intermediate Similarity	NPC46744
0.7438	Intermediate Similarity	NPC14622
0.7438	Intermediate Similarity	NPC73020
0.7438	Intermediate Similarity	NPC124302
0.7438	Intermediate Similarity	NPC70290
0.7438	Intermediate Similarity	NPC215098
0.7426	Intermediate Similarity	NPC33256
0.7409	Intermediate Similarity	NPC65403
0.7404	Intermediate Similarity	NPC11708
0.7398	Intermediate Similarity	NPC220961
0.7396	Intermediate Similarity	NPC475845
0.7385	Intermediate Similarity	NPC35680
0.7379	Intermediate Similarity	NPC202771
0.7379	Intermediate Similarity	NPC119818
0.7379	Intermediate Similarity	NPC328700
0.7379	Intermediate Similarity	NPC2173
0.7356	Intermediate Similarity	NPC80472
0.7344	Intermediate Similarity	NPC474324
0.7344	Intermediate Similarity	NPC57812
0.7327	Intermediate Similarity	NPC94499
0.73	Intermediate Similarity	NPC230098
0.7296	Intermediate Similarity	NPC474470
0.7295	Intermediate Similarity	NPC286135
0.7286	Intermediate Similarity	NPC474746
0.7286	Intermediate Similarity	NPC156576
0.7286	Intermediate Similarity	NPC475981
0.7273	Intermediate Similarity	NPC471513
0.7268	Intermediate Similarity	NPC311991
0.7259	Intermediate Similarity	NPC148693
0.7259	Intermediate Similarity	NPC118633
0.7259	Intermediate Similarity	NPC294790
0.7255	Intermediate Similarity	NPC174783
0.7254	Intermediate Similarity	NPC210918
0.7246	Intermediate Similarity	NPC311781
0.724	Intermediate Similarity	NPC180306
0.724	Intermediate Similarity	NPC247972
0.7236	Intermediate Similarity	NPC248642
0.7231	Intermediate Similarity	NPC225597
0.7231	Intermediate Similarity	NPC470739
0.7231	Intermediate Similarity	NPC477640
0.7222	Intermediate Similarity	NPC474745
0.7216	Intermediate Similarity	NPC241055
0.7216	Intermediate Similarity	NPC266176
0.7216	Intermediate Similarity	NPC290759
0.7216	Intermediate Similarity	NPC82533
0.7216	Intermediate Similarity	NPC158148
0.7195	Intermediate Similarity	NPC473458
0.7193	Intermediate Similarity	NPC477395
0.719	Intermediate Similarity	NPC476500
0.7186	Intermediate Similarity	NPC298339
0.7179	Intermediate Similarity	NPC474475
0.7173	Intermediate Similarity	NPC4304
0.7172	Intermediate Similarity	NPC474325
0.7172	Intermediate Similarity	NPC15919
0.7165	Intermediate Similarity	NPC247389
0.7157	Intermediate Similarity	NPC304675
0.715	Intermediate Similarity	NPC231198
0.715	Intermediate Similarity	NPC16805
0.715	Intermediate Similarity	NPC167546
0.715	Intermediate Similarity	NPC302527
0.7136	Intermediate Similarity	NPC267408
0.7136	Intermediate Similarity	NPC126284
0.7135	Intermediate Similarity	NPC469479
0.7129	Intermediate Similarity	NPC67346
0.7129	Intermediate Similarity	NPC162694
0.7129	Intermediate Similarity	NPC477259
0.7129	Intermediate Similarity	NPC169387
0.7128	Intermediate Similarity	NPC475686
0.7128	Intermediate Similarity	NPC58766
0.7121	Intermediate Similarity	NPC237044
0.7117	Intermediate Similarity	NPC470480
0.7113	Intermediate Similarity	NPC476002
0.7113	Intermediate Similarity	NPC476432
0.7113	Intermediate Similarity	NPC219341
0.7113	Intermediate Similarity	NPC24264
0.7104	Intermediate Similarity	NPC231924
0.7095	Intermediate Similarity	NPC235698
0.7094	Intermediate Similarity	NPC166979
0.7092	Intermediate Similarity	NPC75958
0.7079	Intermediate Similarity	NPC9867
0.7078	Intermediate Similarity	NPC10653
0.7078	Intermediate Similarity	NPC318525
0.7071	Intermediate Similarity	NPC308267
0.707	Intermediate Similarity	NPC10732
0.7065	Intermediate Similarity	NPC116284
0.7062	Intermediate Similarity	NPC225774
0.7062	Intermediate Similarity	NPC169605
0.7059	Intermediate Similarity	NPC211296
0.7054	Intermediate Similarity	NPC477397
0.7053	Intermediate Similarity	NPC78733
0.705	Intermediate Similarity	NPC244554
0.7048	Intermediate Similarity	NPC43069
0.7048	Intermediate Similarity	NPC140577
0.7041	Intermediate Similarity	NPC86469
0.7032	Intermediate Similarity	NPC222046
0.7017	Intermediate Similarity	NPC194359
0.7017	Intermediate Similarity	NPC28641
0.7016	Intermediate Similarity	NPC273578
0.7016	Intermediate Similarity	NPC323443
0.7016	Intermediate Similarity	NPC180756
0.701	Intermediate Similarity	NPC65784
0.701	Intermediate Similarity	NPC320104
0.7005	Intermediate Similarity	NPC477258
0.7005	Intermediate Similarity	NPC25496
0.7004	Intermediate Similarity	NPC476220
0.7004	Intermediate Similarity	NPC160113
0.6995	Remote Similarity	NPC258128
0.6991	Remote Similarity	NPC159815
0.699	Remote Similarity	NPC181653
0.699	Remote Similarity	NPC284842
0.699	Remote Similarity	NPC190332
0.6986	Remote Similarity	NPC123859
0.6984	Remote Similarity	NPC8337
0.6984	Remote Similarity	NPC85747
0.698	Remote Similarity	NPC275132
0.6976	Remote Similarity	NPC470642
0.6974	Remote Similarity	NPC154922
0.6974	Remote Similarity	NPC469505
0.6974	Remote Similarity	NPC168409
0.697	Remote Similarity	NPC303581
0.697	Remote Similarity	NPC149090
0.697	Remote Similarity	NPC67978
0.697	Remote Similarity	NPC19520
0.6967	Remote Similarity	NPC244191
0.6967	Remote Similarity	NPC97086
0.6965	Remote Similarity	NPC27887
0.6961	Remote Similarity	NPC214116
0.6955	Remote Similarity	NPC288110
0.6947	Remote Similarity	NPC210642
0.6947	Remote Similarity	NPC13985
0.6946	Remote Similarity	NPC83511
0.6946	Remote Similarity	NPC116007
0.6938	Remote Similarity	NPC193906
0.6938	Remote Similarity	NPC23080
0.6935	Remote Similarity	NPC2314
0.6931	Remote Similarity	NPC262455
0.6931	Remote Similarity	NPC177476
0.6923	Remote Similarity	NPC470637
0.6919	Remote Similarity	NPC6152
0.6915	Remote Similarity	NPC474568
0.6915	Remote Similarity	NPC114364
0.6915	Remote Similarity	NPC320223
0.6912	Remote Similarity	NPC18306
0.6907	Remote Similarity	NPC477559
0.6907	Remote Similarity	NPC306902
0.6907	Remote Similarity	NPC266753
0.6907	Remote Similarity	NPC232924
0.6907	Remote Similarity	NPC160298
0.6905	Remote Similarity	NPC267414
0.6904	Remote Similarity	NPC100566
0.69	Remote Similarity	NPC199465
0.69	Remote Similarity	NPC229166
0.69	Remote Similarity	NPC187678
0.69	Remote Similarity	NPC128560
0.69	Remote Similarity	NPC291173
0.6895	Remote Similarity	NPC475170
0.6893	Remote Similarity	NPC82763
0.689	Remote Similarity	NPC24228
0.6889	Remote Similarity	NPC5674
0.6887	Remote Similarity	NPC232533
0.6884	Remote Similarity	NPC474948
0.6884	Remote Similarity	NPC42230
0.6883	Remote Similarity	NPC304837
0.6883	Remote Similarity	NPC476258
0.6881	Remote Similarity	NPC475794
0.6872	Remote Similarity	NPC68619
0.6869	Remote Similarity	NPC475953
0.6869	Remote Similarity	NPC474647
0.6865	Remote Similarity	NPC246474
0.6865	Remote Similarity	NPC162851

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 NPC475747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	685
0.2-0.3	1373
0.3-0.4	2796
0.4-0.5	2447
0.5-0.6	1351
0.6-0.7	225
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7919	Intermediate Similarity	NPD2973	Approved
0.7919	Intermediate Similarity	NPD2974	Approved
0.7919	Intermediate Similarity	NPD2975	Approved
0.7906	Intermediate Similarity	NPD2971	Approved
0.7906	Intermediate Similarity	NPD2968	Approved
0.78	Intermediate Similarity	NPD4580	Approved
0.7761	Intermediate Similarity	NPD2494	Approved
0.7761	Intermediate Similarity	NPD2493	Approved
0.7673	Intermediate Similarity	NPD3452	Approved
0.7673	Intermediate Similarity	NPD3450	Approved
0.7647	Intermediate Similarity	NPD4583	Approved
0.7647	Intermediate Similarity	NPD4582	Approved
0.7598	Intermediate Similarity	NPD4002	Approved
0.7598	Intermediate Similarity	NPD4004	Approved
0.7576	Intermediate Similarity	NPD2490	Approved
0.7576	Intermediate Similarity	NPD2488	Approved
0.745	Intermediate Similarity	NPD7296	Approved
0.7438	Intermediate Similarity	NPD4420	Approved
0.7391	Intermediate Similarity	NPD4040	Phase 1
0.7379	Intermediate Similarity	NPD5006	Approved
0.7379	Intermediate Similarity	NPD5005	Approved
0.7366	Intermediate Similarity	NPD4107	Approved
0.7246	Intermediate Similarity	NPD4482	Phase 3
0.7216	Intermediate Similarity	NPD4481	Phase 3
0.7186	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6997	Phase 2
0.7136	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3057	Approved
0.7123	Intermediate Similarity	NPD7907	Approved
0.7112	Intermediate Similarity	NPD4210	Discontinued
0.7103	Intermediate Similarity	NPD5676	Approved
0.7093	Intermediate Similarity	NPD7048	Phase 3
0.7065	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7047	Phase 3
0.7048	Intermediate Similarity	NPD2972	Approved
0.7048	Intermediate Similarity	NPD3533	Approved
0.7043	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3146	Approved
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4111	Phase 1
0.7032	Intermediate Similarity	NPD4665	Approved
0.7026	Intermediate Similarity	NPD3051	Approved
0.702	Intermediate Similarity	NPD5313	Approved
0.702	Intermediate Similarity	NPD5312	Approved
0.7018	Intermediate Similarity	NPD4846	Phase 2
0.7015	Intermediate Similarity	NPD7280	Phase 3
0.7015	Intermediate Similarity	NPD7281	Phase 3
0.6961	Remote Similarity	NPD7906	Approved
0.6931	Remote Similarity	NPD4577	Approved
0.6931	Remote Similarity	NPD4578	Approved
0.6923	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7827	Phase 1
0.6912	Remote Similarity	NPD4663	Approved
0.6904	Remote Similarity	NPD2970	Approved
0.6904	Remote Similarity	NPD2969	Approved
0.6887	Remote Similarity	NPD2491	Approved
0.6878	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5980	Discovery
0.6859	Remote Similarity	NPD6876	Approved
0.6859	Remote Similarity	NPD6875	Approved
0.685	Remote Similarity	NPD6042	Phase 2
0.685	Remote Similarity	NPD42	Phase 2
0.6845	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7110	Phase 1
0.6812	Remote Similarity	NPD6625	Approved
0.6808	Remote Similarity	NPD3448	Approved
0.6806	Remote Similarity	NPD4859	Phase 1
0.6792	Remote Similarity	NPD5457	Discontinued
0.6784	Remote Similarity	NPD2489	Approved
0.6784	Remote Similarity	NPD27	Approved
0.6776	Remote Similarity	NPD7497	Discontinued
0.6774	Remote Similarity	NPD4236	Phase 3
0.6774	Remote Similarity	NPD4237	Approved
0.6769	Remote Similarity	NPD4966	Approved
0.6769	Remote Similarity	NPD4965	Approved
0.6769	Remote Similarity	NPD4967	Phase 2
0.6745	Remote Similarity	NPD8285	Discontinued
0.6734	Remote Similarity	NPD5242	Approved
0.673	Remote Similarity	NPD5564	Approved
0.6715	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5241	Discontinued
0.6701	Remote Similarity	NPD6234	Discontinued
0.6701	Remote Similarity	NPD7248	Discontinued
0.6683	Remote Similarity	NPD7311	Approved
0.6683	Remote Similarity	NPD7313	Approved
0.6683	Remote Similarity	NPD7312	Approved
0.6683	Remote Similarity	NPD7310	Approved
0.6651	Remote Similarity	NPD7701	Phase 2
0.6651	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6851	Approved
0.665	Remote Similarity	NPD7309	Approved
0.665	Remote Similarity	NPD6853	Approved
0.6649	Remote Similarity	NPD6386	Approved
0.6649	Remote Similarity	NPD6385	Approved
0.6636	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3639	Approved
0.6615	Remote Similarity	NPD4727	Phase 1
0.6615	Remote Similarity	NPD3641	Approved
0.6615	Remote Similarity	NPD3640	Phase 3
0.6615	Remote Similarity	NPD37	Approved
0.6604	Remote Similarity	NPD5582	Discontinued
0.6585	Remote Similarity	NPD7039	Approved
0.6585	Remote Similarity	NPD7038	Approved
0.6582	Remote Similarity	NPD2977	Approved
0.6582	Remote Similarity	NPD2978	Approved
0.6571	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5754	Discontinued
0.655	Remote Similarity	NPD6107	Approved
0.6537	Remote Similarity	NPD6297	Approved
0.6526	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7315	Approved
0.6517	Remote Similarity	NPD4166	Phase 2
0.6488	Remote Similarity	NPD3885	Approved
0.6485	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2163	Approved
0.6471	Remote Similarity	NPD7177	Discontinued
0.6471	Remote Similarity	NPD7228	Approved
0.6465	Remote Similarity	NPD5353	Approved
0.6458	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8319	Approved
0.6438	Remote Similarity	NPD8320	Phase 1
0.6414	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7999	Approved
0.6392	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.639	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7199	Phase 2
0.6382	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2563	Approved
0.6382	Remote Similarity	NPD2560	Approved
0.6382	Remote Similarity	NPD5977	Approved
0.6382	Remote Similarity	NPD5978	Approved
0.6381	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD3705	Approved
0.6368	Remote Similarity	NPD5709	Phase 3
0.6368	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7400	Phase 3
0.6368	Remote Similarity	NPD2897	Discontinued
0.6364	Remote Similarity	NPD2492	Phase 1
0.6359	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7240	Approved
0.6344	Remote Similarity	NPD3109	Approved
0.6344	Remote Similarity	NPD3110	Approved
0.6344	Remote Similarity	NPD8404	Phase 2
0.634	Remote Similarity	NPD4584	Approved
0.6337	Remote Similarity	NPD4666	Phase 3
0.6332	Remote Similarity	NPD5773	Approved
0.6332	Remote Similarity	NPD5772	Approved
0.633	Remote Similarity	NPD6779	Approved
0.633	Remote Similarity	NPD6780	Approved
0.633	Remote Similarity	NPD6781	Approved
0.633	Remote Similarity	NPD6776	Approved
0.633	Remote Similarity	NPD6777	Approved
0.633	Remote Similarity	NPD6782	Approved
0.633	Remote Similarity	NPD6778	Approved
0.6327	Remote Similarity	NPD3686	Approved
0.6327	Remote Similarity	NPD7930	Approved
0.6327	Remote Similarity	NPD3687	Approved
0.6327	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5137	Approved
0.6321	Remote Similarity	NPD7291	Discontinued
0.6318	Remote Similarity	NPD7698	Approved
0.6318	Remote Similarity	NPD7697	Approved
0.6318	Remote Similarity	NPD7696	Phase 3
0.6316	Remote Similarity	NPD1375	Discontinued
0.6314	Remote Similarity	NPD6723	Discontinued
0.6313	Remote Similarity	NPD6873	Phase 2
0.6309	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD8059	Phase 3
0.6301	Remote Similarity	NPD6238	Discontinued
0.6296	Remote Similarity	NPD1753	Discontinued
0.629	Remote Similarity	NPD7870	Phase 2
0.629	Remote Similarity	NPD7871	Phase 2
0.6283	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6213	Phase 3
0.6279	Remote Similarity	NPD6212	Phase 3
0.6276	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5711	Approved
0.6275	Remote Similarity	NPD6071	Discontinued
0.6275	Remote Similarity	NPD5710	Approved
0.6266	Remote Similarity	NPD7224	Discontinued
0.6266	Remote Similarity	NPD7223	Discontinued
0.6263	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7028	Phase 2
0.6261	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2654	Approved
0.625	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7279	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