NPASS Compound

Structure

NPC472191 OpenBabel07101718332D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.7435 2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7579 4.0465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 -1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0962 2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7653 1.8171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 2.3523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 2.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 1.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3007 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4347 1.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4347 2.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -0.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4489 3.0955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 O 0 3 0 0 0 0 0 0 0 0 0 0 5.3007 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 32 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 16 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 28 1 0 0 0 0 15 21 2 3 0 0 0 16 33 2 3 0 0 0 17 20 2 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 32 1 0 0 0 0 19 13 1 6 0 0 0 19 22 1 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 24 1 0 0 0 0 23 30 1 6 0 0 0 24 25 1 0 0 0 0 24 31 1 1 0 0 0 25 33 1 6 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 M CHG 1 33 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	471.21
Volume:	464.562
LogP:	2.06
LogD:	2.243
LogS:	-4.224
# Rotatable Bonds:	3
TPSA:	117.16
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	4.969
Fsp3:	0.48
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.651
MDCK Permeability:	6.641294476139592e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.347
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.34

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	97.24451446533203%
Volume Distribution (VD):	0.844
Pgp-substrate:	1.6447014808654785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	6.518
Half-life (T1/2):	0.721

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.7
Drug-inuced Liver Injury (DILI):	0.721
AMES Toxicity:	0.757
Rat Oral Acute Toxicity:	0.439
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.923
Carcinogencity:	0.919
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC472191

Natural Product ID:	NPC472191
*Common Name:**	KMNWXNMZIFUOKX-HYOIWIKGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMNWXNMZIFUOKX-HYOIWIKGSA-N
Standard InCHI:	InChI=1S/C25H31N2O7/c1-14-11-17-20(18(12-14)32-2)21(27-10-4-3-9-26(17)27)15-5-7-16(8-6-15)33-25-24(31)23(30)22(29)19(13-28)34-25/h5-8,11-12,19,22-25,28-31H,3-4,9-10,13H2,1-2H3/q+1/t19-,22-,23+,24-,25-/m1/s1
SMILES:	OC[C@H]1O[C@@H]([O+]=C2C=CC(=c3c4c(OC)cc(cc4n4n3CCCC4)C)C=C2)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3344045
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO12297	Nigella sativa	Species	Ranunculaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25299458]
NPO12297	Nigella sativa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO12297	Nigella sativa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12297	Nigella sativa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	29.0	%	PMID[503183]

☑ 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 NPC472191 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	296
0.1-0.2	1494
0.2-0.3	5522
0.3-0.4	11480
0.4-0.5	9614
0.5-0.6	12818
0.6-0.7	1440
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8352	Intermediate Similarity	NPC70092
0.7446	Intermediate Similarity	NPC320064
0.7442	Intermediate Similarity	NPC248903
0.7437	Intermediate Similarity	NPC162653
0.7418	Intermediate Similarity	NPC148124
0.7395	Intermediate Similarity	NPC26928
0.7371	Intermediate Similarity	NPC99724
0.7337	Intermediate Similarity	NPC302001
0.7282	Intermediate Similarity	NPC179704
0.7273	Intermediate Similarity	NPC312531
0.7273	Intermediate Similarity	NPC474059
0.7206	Intermediate Similarity	NPC127178
0.7204	Intermediate Similarity	NPC217903
0.7196	Intermediate Similarity	NPC108826
0.7186	Intermediate Similarity	NPC474904
0.7157	Intermediate Similarity	NPC249405
0.7156	Intermediate Similarity	NPC116178
0.7143	Intermediate Similarity	NPC70172
0.7136	Intermediate Similarity	NPC320088
0.7136	Intermediate Similarity	NPC477186
0.7128	Intermediate Similarity	NPC287588
0.7108	Intermediate Similarity	NPC193906
0.7108	Intermediate Similarity	NPC23080
0.7095	Intermediate Similarity	NPC477160
0.7095	Intermediate Similarity	NPC168250
0.7083	Intermediate Similarity	NPC10653
0.7083	Intermediate Similarity	NPC318525
0.7077	Intermediate Similarity	NPC287152
0.7077	Intermediate Similarity	NPC49353
0.7067	Intermediate Similarity	NPC87714
0.7045	Intermediate Similarity	NPC473458
0.7042	Intermediate Similarity	NPC321166
0.7037	Intermediate Similarity	NPC288110
0.7035	Intermediate Similarity	NPC276674
0.7035	Intermediate Similarity	NPC33902
0.7026	Intermediate Similarity	NPC127082
0.7005	Intermediate Similarity	NPC190461
0.7005	Intermediate Similarity	NPC118633
0.7005	Intermediate Similarity	NPC148693
0.7005	Intermediate Similarity	NPC294790
0.7004	Intermediate Similarity	NPC99891
0.7	Intermediate Similarity	NPC198160
0.699	Remote Similarity	NPC304675
0.698	Remote Similarity	NPC28510
0.6972	Remote Similarity	NPC128476
0.6963	Remote Similarity	NPC24954
0.6954	Remote Similarity	NPC237044
0.6952	Remote Similarity	NPC246140
0.6952	Remote Similarity	NPC195787
0.695	Remote Similarity	NPC262725
0.6942	Remote Similarity	NPC17677
0.6939	Remote Similarity	NPC2314
0.6939	Remote Similarity	NPC285941
0.693	Remote Similarity	NPC189661
0.6927	Remote Similarity	NPC59567
0.6919	Remote Similarity	NPC478075
0.6919	Remote Similarity	NPC474325
0.6916	Remote Similarity	NPC127996
0.6911	Remote Similarity	NPC4304
0.6908	Remote Similarity	NPC212163
0.6906	Remote Similarity	NPC477397
0.6905	Remote Similarity	NPC470484
0.6905	Remote Similarity	NPC156728
0.6905	Remote Similarity	NPC244606
0.6901	Remote Similarity	NPC269449
0.6901	Remote Similarity	NPC25961
0.6895	Remote Similarity	NPC329830
0.6892	Remote Similarity	NPC471513
0.6884	Remote Similarity	NPC474745
0.6878	Remote Similarity	NPC19175
0.6875	Remote Similarity	NPC67904
0.6869	Remote Similarity	NPC474470
0.6869	Remote Similarity	NPC283999
0.6869	Remote Similarity	NPC220241
0.6869	Remote Similarity	NPC295479
0.6866	Remote Similarity	NPC475981
0.6866	Remote Similarity	NPC474746
0.6863	Remote Similarity	NPC475754
0.6863	Remote Similarity	NPC473004
0.6857	Remote Similarity	NPC159101
0.6849	Remote Similarity	NPC128115
0.6845	Remote Similarity	NPC194967
0.6842	Remote Similarity	NPC295676
0.684	Remote Similarity	NPC477393
0.6837	Remote Similarity	NPC159815
0.6837	Remote Similarity	NPC119722
0.6837	Remote Similarity	NPC311991
0.6835	Remote Similarity	NPC87560
0.6835	Remote Similarity	NPC195120
0.6834	Remote Similarity	NPC15919
0.6829	Remote Similarity	NPC78284
0.6825	Remote Similarity	NPC14339
0.6825	Remote Similarity	NPC268077
0.6823	Remote Similarity	NPC292143
0.6823	Remote Similarity	NPC139506
0.6821	Remote Similarity	NPC190332
0.6821	Remote Similarity	NPC181653
0.6821	Remote Similarity	NPC471604
0.6821	Remote Similarity	NPC100566
0.6818	Remote Similarity	NPC187678
0.6818	Remote Similarity	NPC46259
0.6816	Remote Similarity	NPC248642
0.6816	Remote Similarity	NPC275132
0.6814	Remote Similarity	NPC470483
0.6812	Remote Similarity	NPC161804
0.6808	Remote Similarity	NPC317709
0.6808	Remote Similarity	NPC329329
0.6802	Remote Similarity	NPC225597
0.6802	Remote Similarity	NPC470739
0.6802	Remote Similarity	NPC477640
0.68	Remote Similarity	NPC244554
0.68	Remote Similarity	NPC32154
0.6798	Remote Similarity	NPC314702
0.6796	Remote Similarity	NPC230313
0.6794	Remote Similarity	NPC138830
0.6789	Remote Similarity	NPC195636
0.6786	Remote Similarity	NPC266176
0.6786	Remote Similarity	NPC290759
0.6786	Remote Similarity	NPC82533
0.6786	Remote Similarity	NPC158148
0.6784	Remote Similarity	NPC5167
0.6784	Remote Similarity	NPC241704
0.6784	Remote Similarity	NPC85613
0.6782	Remote Similarity	NPC156576
0.6781	Remote Similarity	NPC477396
0.678	Remote Similarity	NPC114039
0.678	Remote Similarity	NPC206109
0.6779	Remote Similarity	NPC100863
0.6777	Remote Similarity	NPC207971
0.6774	Remote Similarity	NPC55470
0.6773	Remote Similarity	NPC118154
0.6773	Remote Similarity	NPC157983
0.6771	Remote Similarity	NPC106786
0.6768	Remote Similarity	NPC477187
0.6762	Remote Similarity	NPC232600
0.6762	Remote Similarity	NPC471489
0.6758	Remote Similarity	NPC134702
0.6753	Remote Similarity	NPC320104
0.6753	Remote Similarity	NPC469722
0.6751	Remote Similarity	NPC474475
0.675	Remote Similarity	NPC114364
0.675	Remote Similarity	NPC320223
0.6749	Remote Similarity	NPC21425
0.6749	Remote Similarity	NPC9867
0.6748	Remote Similarity	NPC470485
0.6745	Remote Similarity	NPC475147
0.6743	Remote Similarity	NPC234772
0.6736	Remote Similarity	NPC205167
0.6735	Remote Similarity	NPC310894
0.6735	Remote Similarity	NPC474324
0.6735	Remote Similarity	NPC57812
0.6732	Remote Similarity	NPC22476
0.6732	Remote Similarity	NPC1820
0.673	Remote Similarity	NPC15987
0.6727	Remote Similarity	NPC222046
0.6718	Remote Similarity	NPC238530
0.6718	Remote Similarity	NPC232514
0.6718	Remote Similarity	NPC276944
0.6718	Remote Similarity	NPC180306
0.6718	Remote Similarity	NPC470971
0.6716	Remote Similarity	NPC230098
0.6716	Remote Similarity	NPC126284
0.6714	Remote Similarity	NPC472111
0.6712	Remote Similarity	NPC126556
0.6702	Remote Similarity	NPC93593
0.6701	Remote Similarity	NPC58766
0.6701	Remote Similarity	NPC475686
0.6701	Remote Similarity	NPC475845
0.67	Remote Similarity	NPC291759
0.6699	Remote Similarity	NPC71124
0.6699	Remote Similarity	NPC234933
0.6698	Remote Similarity	NPC475133
0.6697	Remote Similarity	NPC476069
0.6696	Remote Similarity	NPC151171
0.6696	Remote Similarity	NPC476436
0.6684	Remote Similarity	NPC315498
0.6684	Remote Similarity	NPC471073
0.6684	Remote Similarity	NPC270811
0.6684	Remote Similarity	NPC230942
0.6684	Remote Similarity	NPC223124
0.6684	Remote Similarity	NPC476002
0.6683	Remote Similarity	NPC166979
0.6683	Remote Similarity	NPC472193
0.6683	Remote Similarity	NPC473569
0.6682	Remote Similarity	NPC182853
0.6682	Remote Similarity	NPC10732
0.6682	Remote Similarity	NPC470481
0.6682	Remote Similarity	NPC212123
0.6682	Remote Similarity	NPC470482
0.6681	Remote Similarity	NPC477395
0.6681	Remote Similarity	NPC124300
0.6667	Remote Similarity	NPC474708
0.6667	Remote Similarity	NPC279401
0.6667	Remote Similarity	NPC79293
0.6667	Remote Similarity	NPC478048
0.6667	Remote Similarity	NPC5374
0.6667	Remote Similarity	NPC75958
0.6667	Remote Similarity	NPC118189
0.6652	Remote Similarity	NPC291609
0.6651	Remote Similarity	NPC114468

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 NPC472191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	631
0.2-0.3	840
0.3-0.4	1946
0.4-0.5	2911
0.5-0.6	2222
0.6-0.7	415
0.7-0.8	6
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
0.7163	Intermediate Similarity	NPD3437	Discontinued
0.7113	Intermediate Similarity	NPD3793	Phase 3
0.7094	Intermediate Similarity	NPD5582	Discontinued
0.7073	Intermediate Similarity	NPD6874	Approved
0.7064	Intermediate Similarity	NPD3912	Discontinued
0.7015	Intermediate Similarity	NPD7629	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7630	Phase 3
0.7015	Intermediate Similarity	NPD7628	Phase 3
0.701	Intermediate Similarity	NPD5938	Phase 3
0.6995	Remote Similarity	NPD2215	Approved
0.6995	Remote Similarity	NPD2216	Approved
0.6995	Remote Similarity	NPD7262	Phase 1
0.699	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4668	Phase 2
0.6939	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2843	Phase 2
0.6931	Remote Similarity	NPD2845	Phase 2
0.6919	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7479	Phase 2
0.686	Remote Similarity	NPD6877	Discontinued
0.6857	Remote Similarity	NPD6669	Phase 2
0.6842	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5150	Phase 2
0.6825	Remote Similarity	NPD1294	Discontinued
0.6825	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4605	Approved
0.6812	Remote Similarity	NPD4604	Approved
0.6812	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD4859	Phase 1
0.6791	Remote Similarity	NPD683	Approved
0.6789	Remote Similarity	NPD1769	Discontinued
0.6777	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6644	Discontinued
0.6732	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.673	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3983	Phase 3
0.6716	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4796	Discontinued
0.67	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD19	Approved
0.6684	Remote Similarity	NPD1742	Approved
0.6684	Remote Similarity	NPD1743	Approved
0.6634	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7263	Phase 2
0.6599	Remote Similarity	NPD6071	Discontinued
0.6582	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2899	Discontinued
0.6575	Remote Similarity	NPD5944	Phase 1
0.6575	Remote Similarity	NPD5945	Phase 1
0.6569	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2969	Approved
0.6566	Remote Similarity	NPD2970	Approved
0.6556	Remote Similarity	NPD8461	Discontinued
0.6552	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7186	Phase 3
0.654	Remote Similarity	NPD5071	Phase 2
0.6538	Remote Similarity	NPD3633	Approved
0.6538	Remote Similarity	NPD3634	Approved
0.6537	Remote Similarity	NPD3154	Approved
0.6537	Remote Similarity	NPD3153	Approved
0.6533	Remote Similarity	NPD2489	Approved
0.6533	Remote Similarity	NPD27	Approved
0.6526	Remote Similarity	NPD6321	Discontinued
0.6522	Remote Similarity	NPD6625	Approved
0.6517	Remote Similarity	NPD5600	Discontinued
0.6515	Remote Similarity	NPD5847	Phase 1
0.6515	Remote Similarity	NPD3051	Approved
0.651	Remote Similarity	NPD3296	Phase 1
0.6509	Remote Similarity	NPD1768	Approved
0.6507	Remote Similarity	NPD7125	Discontinued
0.6498	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6037	Discontinued
0.6493	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3656	Approved
0.6484	Remote Similarity	NPD1945	Phase 1
0.6482	Remote Similarity	NPD2388	Discontinued
0.6482	Remote Similarity	NPD4083	Discontinued
0.6481	Remote Similarity	NPD3003	Approved
0.6462	Remote Similarity	NPD6063	Approved
0.6462	Remote Similarity	NPD1012	Discontinued
0.6459	Remote Similarity	NPD4740	Approved
0.6458	Remote Similarity	NPD6357	Discontinued
0.6453	Remote Similarity	NPD6184	Discontinued
0.645	Remote Similarity	NPD2898	Approved
0.645	Remote Similarity	NPD4481	Phase 3
0.645	Remote Similarity	NPD6723	Discontinued
0.6444	Remote Similarity	NPD7805	Phase 3
0.6439	Remote Similarity	NPD7877	Suspended
0.6438	Remote Similarity	NPD5860	Discontinued
0.6436	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5186	Approved
0.6432	Remote Similarity	NPD5183	Approved
0.6432	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4539	Phase 1
0.6429	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD5641	Discontinued
0.6411	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2978	Approved
0.641	Remote Similarity	NPD2977	Approved
0.6406	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7224	Discontinued
0.6404	Remote Similarity	NPD7223	Discontinued
0.6402	Remote Similarity	NPD5542	Phase 2
0.6402	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6493	Phase 3
0.6396	Remote Similarity	NPD5903	Approved
0.6396	Remote Similarity	NPD5902	Approved
0.6383	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2563	Approved
0.6378	Remote Similarity	NPD2560	Approved
0.6372	Remote Similarity	NPD3416	Discontinued
0.6372	Remote Similarity	NPD5506	Approved
0.6372	Remote Similarity	NPD5507	Approved
0.6368	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2246	Approved
0.6368	Remote Similarity	NPD2248	Approved
0.6364	Remote Similarity	NPD4258	Approved
0.6364	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5928	Phase 1
0.6364	Remote Similarity	NPD4259	Approved
0.6359	Remote Similarity	NPD7310	Approved
0.6359	Remote Similarity	NPD7313	Approved
0.6359	Remote Similarity	NPD7311	Approved
0.6359	Remote Similarity	NPD7312	Approved
0.6356	Remote Similarity	NPD7194	Discontinued
0.6355	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD1880	Phase 3
0.6351	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5610	Approved
0.6351	Remote Similarity	NPD4590	Approved
0.6351	Remote Similarity	NPD5984	Phase 2
0.6347	Remote Similarity	NPD2906	Approved
0.6347	Remote Similarity	NPD2907	Approved
0.6346	Remote Similarity	NPD4951	Discontinued
0.6341	Remote Similarity	NPD3037	Phase 1
0.6339	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD4584	Approved
0.6333	Remote Similarity	NPD1924	Approved
0.6332	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7002	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7309	Approved
0.6327	Remote Similarity	NPD5772	Approved
0.6327	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5773	Approved
0.6327	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7906	Approved
0.6316	Remote Similarity	NPD4113	Discontinued
0.6313	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5632	Approved
0.6311	Remote Similarity	NPD4012	Approved
0.631	Remote Similarity	NPD7753	Approved
0.631	Remote Similarity	NPD7752	Approved
0.6309	Remote Similarity	NPD7558	Phase 2
0.6308	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD4420	Approved
0.6308	Remote Similarity	NPD4773	Phase 2
0.6308	Remote Similarity	NPD4772	Phase 2
0.6307	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3815	Phase 1
0.6306	Remote Similarity	NPD3816	Phase 1
0.6303	Remote Similarity	NPD5587	Approved
0.6301	Remote Similarity	NPD7584	Approved
0.6301	Remote Similarity	NPD1392	Approved
0.63	Remote Similarity	NPD6298	Discontinued
0.6296	Remote Similarity	NPD6604	Discontinued
0.6296	Remote Similarity	NPD7476	Discontinued
0.6296	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3558	Approved
0.6294	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3557	Approved
0.6294	Remote Similarity	NPD3560	Approved
0.6294	Remote Similarity	NPD3556	Approved
0.6293	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD789	Phase 2
0.6287	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7417	Discontinued
0.6284	Remote Similarity	NPD3298	Approved
0.6283	Remote Similarity	NPD5519	Discontinued
0.6283	Remote Similarity	NPD3763	Approved
0.6278	Remote Similarity	NPD850	Approved
0.6278	Remote Similarity	NPD849	Approved
0.6278	Remote Similarity	NPD848	Approved
0.6277	Remote Similarity	NPD7710	Clinical (unspecified phase)

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