NPASS Compound

Structure

NPC470484 OpenBabel07101718232D 27 32 0 0 1 0 0 0 0 0999 V2000 -0.9429 -4.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1310 0.2927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 -1.6747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0307 -1.6597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0785 -2.7054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8871 -0.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0628 -1.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6657 -3.5349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6576 -0.6178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5218 -1.3197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6975 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7154 -2.2711 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9270 -1.9754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7730 -1.5024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.4286 -2.5634 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6256 -3.8154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2232 -2.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1315 0.2628 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 12 1 0 0 0 0 2 26 1 0 0 0 0 3 6 1 0 0 0 0 4 8 1 0 0 0 0 4 15 2 0 0 0 0 5 7 1 0 0 0 0 5 20 1 0 0 0 0 6 22 1 0 0 0 0 7 22 1 0 0 0 0 8 27 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 17 2 0 0 0 0 12 23 1 0 0 0 0 12 24 2 0 0 0 0 13 3 1 6 0 0 0 13 15 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 20 1 6 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 6 0 0 0 21 22 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.17
Volume:	364.406
LogP:	2.63
LogD:	2.114
LogS:	-4.203
# Rotatable Bonds:	2
TPSA:	62.24
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.77
Synthetic Accessibility Score:	6.171
Fsp3:	0.571
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:	-4.788
MDCK Permeability:	1.3521558685170021e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.323
Human Intestinal Absorption (HIA):	0.092
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.572

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	44.8642578125%
Volume Distribution (VD):	1.216
Pgp-substrate:	55.8131103515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.412
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.941

ADMET: Excretion

Clearance (CL):	8.435
Half-life (T1/2):	0.652

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.234
AMES Toxicity:	0.258
Rat Oral Acute Toxicity:	0.913
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.348
Carcinogencity:	0.948
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC470484

Natural Product ID:	NPC470484
*Common Name:**	XORSOONLULVOCT-WTXAKBKRSA-N
IUPAC Name:	n.a.
Synonyms:	10-Methoxygeissospermidine
Standard InCHIKey:	XORSOONLULVOCT-WTXAKBKRSA-N
Standard InCHI:	InChI=1S/C21H24N2O4/c1-12(24)23-18-9-13-3-6-22-7-5-20(18,21(22)15(13)4-8-27-21)16-10-14(26-2)11-17(25)19(16)23/h4,10-11,13,18,25H,3,5-9H2,1-2H3/t13-,18+,20-,21+/m1/s1
SMILES:	CC(=O)N1C2CC3CCN4CCC2(C45C3=CCO5)C6=C1C(=CC(=C6)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047338
PubChem CID:	70684077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO32721	geissospermum reticulatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22551062]

☑ 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
GI50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1021	Organism	Leishmania infantum	Leishmania infantum	GI50	>	100.0	ug.mL-1	PMID[476777]

☑ 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 NPC470484 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	388
0.1-0.2	1635
0.2-0.3	6410
0.3-0.4	11488
0.4-0.5	12966
0.5-0.6	8513
0.6-0.7	1224
0.7-0.8	66
0.8-0.85	4
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC470483
0.913	High Similarity	NPC470485
0.8125	Intermediate Similarity	NPC217294
0.8112	Intermediate Similarity	NPC161804
0.8098	Intermediate Similarity	NPC33507
0.8081	Intermediate Similarity	NPC127178
0.7958	Intermediate Similarity	NPC98197
0.782	Intermediate Similarity	NPC318525
0.782	Intermediate Similarity	NPC10653
0.7723	Intermediate Similarity	NPC138830
0.7714	Intermediate Similarity	NPC234772
0.7685	Intermediate Similarity	NPC471513
0.7662	Intermediate Similarity	NPC272706
0.7621	Intermediate Similarity	NPC195787
0.7621	Intermediate Similarity	NPC246140
0.7606	Intermediate Similarity	NPC288110
0.7604	Intermediate Similarity	NPC473458
0.7581	Intermediate Similarity	NPC251071
0.7561	Intermediate Similarity	NPC1464
0.7538	Intermediate Similarity	NPC116096
0.7534	Intermediate Similarity	NPC477397
0.7523	Intermediate Similarity	NPC222046
0.7513	Intermediate Similarity	NPC70172
0.7511	Intermediate Similarity	NPC477395
0.7488	Intermediate Similarity	NPC159815
0.7429	Intermediate Similarity	NPC168250
0.7379	Intermediate Similarity	NPC67904
0.7352	Intermediate Similarity	NPC477394
0.7324	Intermediate Similarity	NPC470482
0.7324	Intermediate Similarity	NPC470481
0.7304	Intermediate Similarity	NPC477396
0.7293	Intermediate Similarity	NPC477393
0.7282	Intermediate Similarity	NPC218733
0.7282	Intermediate Similarity	NPC138615
0.7282	Intermediate Similarity	NPC132874
0.7282	Intermediate Similarity	NPC265642
0.7273	Intermediate Similarity	NPC231924
0.7255	Intermediate Similarity	NPC78284
0.7243	Intermediate Similarity	NPC127996
0.7215	Intermediate Similarity	NPC128476
0.7212	Intermediate Similarity	NPC291173
0.7207	Intermediate Similarity	NPC470480
0.7202	Intermediate Similarity	NPC219397
0.7195	Intermediate Similarity	NPC19175
0.7192	Intermediate Similarity	NPC22689
0.7192	Intermediate Similarity	NPC105055
0.7178	Intermediate Similarity	NPC9867
0.717	Intermediate Similarity	NPC212123
0.713	Intermediate Similarity	NPC469452
0.7123	Intermediate Similarity	NPC108826
0.7122	Intermediate Similarity	NPC473004
0.7122	Intermediate Similarity	NPC204970
0.7118	Intermediate Similarity	NPC304837
0.7118	Intermediate Similarity	NPC476258
0.7118	Intermediate Similarity	NPC469450
0.7115	Intermediate Similarity	NPC100863
0.7105	Intermediate Similarity	NPC131977
0.7103	Intermediate Similarity	NPC477160
0.7083	Intermediate Similarity	NPC10732
0.7078	Intermediate Similarity	NPC77777
0.7074	Intermediate Similarity	NPC301501
0.707	Intermediate Similarity	NPC269449
0.7069	Intermediate Similarity	NPC329932
0.7065	Intermediate Similarity	NPC244554
0.7059	Intermediate Similarity	NPC477186
0.7056	Intermediate Similarity	NPC469451
0.7032	Intermediate Similarity	NPC126556
0.7032	Intermediate Similarity	NPC195636
0.7015	Intermediate Similarity	NPC15919
0.701	Intermediate Similarity	NPC21425
0.7005	Intermediate Similarity	NPC305542
0.7	Intermediate Similarity	NPC182853
0.7	Intermediate Similarity	NPC187678
0.6991	Remote Similarity	NPC223242
0.6985	Remote Similarity	NPC65403
0.6982	Remote Similarity	NPC76478
0.6977	Remote Similarity	NPC317709
0.6977	Remote Similarity	NPC329329
0.6972	Remote Similarity	NPC30749
0.6971	Remote Similarity	NPC243626
0.6966	Remote Similarity	NPC120239
0.6961	Remote Similarity	NPC262725
0.6959	Remote Similarity	NPC315498
0.6959	Remote Similarity	NPC230942
0.6957	Remote Similarity	NPC314702
0.6951	Remote Similarity	NPC250960
0.6951	Remote Similarity	NPC71539
0.6951	Remote Similarity	NPC148124
0.6943	Remote Similarity	NPC476220
0.6943	Remote Similarity	NPC160113
0.6942	Remote Similarity	NPC174629
0.6942	Remote Similarity	NPC474059
0.6942	Remote Similarity	NPC5630
0.6938	Remote Similarity	NPC162653
0.6937	Remote Similarity	NPC476069
0.6935	Remote Similarity	NPC311991
0.6934	Remote Similarity	NPC469732
0.6933	Remote Similarity	NPC266994
0.693	Remote Similarity	NPC139373
0.6927	Remote Similarity	NPC119722
0.6923	Remote Similarity	NPC271388
0.6923	Remote Similarity	NPC119649
0.6923	Remote Similarity	NPC205255
0.6923	Remote Similarity	NPC230956
0.6923	Remote Similarity	NPC302001
0.6923	Remote Similarity	NPC235143
0.6916	Remote Similarity	NPC87714
0.6912	Remote Similarity	NPC473007
0.6912	Remote Similarity	NPC474366
0.691	Remote Similarity	NPC113455
0.6908	Remote Similarity	NPC82763
0.6906	Remote Similarity	NPC99724
0.6905	Remote Similarity	NPC472191
0.6901	Remote Similarity	NPC52801
0.6892	Remote Similarity	NPC475609
0.689	Remote Similarity	NPC230313
0.6888	Remote Similarity	NPC80759
0.6888	Remote Similarity	NPC79402
0.6881	Remote Similarity	NPC166169
0.6881	Remote Similarity	NPC474470
0.6872	Remote Similarity	NPC74216
0.6872	Remote Similarity	NPC221864
0.6864	Remote Similarity	NPC148391
0.686	Remote Similarity	NPC473008
0.6854	Remote Similarity	NPC232600
0.6852	Remote Similarity	NPC198160
0.685	Remote Similarity	NPC75958
0.6834	Remote Similarity	NPC85482
0.683	Remote Similarity	NPC118189
0.683	Remote Similarity	NPC46259
0.6828	Remote Similarity	NPC248903
0.6822	Remote Similarity	NPC473005
0.6818	Remote Similarity	NPC473006
0.6818	Remote Similarity	NPC24465
0.6816	Remote Similarity	NPC225597
0.6816	Remote Similarity	NPC470739
0.6816	Remote Similarity	NPC477640
0.6816	Remote Similarity	NPC239775
0.6812	Remote Similarity	NPC214116
0.6812	Remote Similarity	NPC320088
0.6808	Remote Similarity	NPC475654
0.68	Remote Similarity	NPC290759
0.68	Remote Similarity	NPC83198
0.68	Remote Similarity	NPC475686
0.68	Remote Similarity	NPC58766
0.68	Remote Similarity	NPC266176
0.68	Remote Similarity	NPC204908
0.68	Remote Similarity	NPC82533
0.68	Remote Similarity	NPC158148
0.6798	Remote Similarity	NPC237044
0.6787	Remote Similarity	NPC189661
0.6786	Remote Similarity	NPC472120
0.6786	Remote Similarity	NPC472101
0.6784	Remote Similarity	NPC264850
0.6784	Remote Similarity	NPC13916
0.6784	Remote Similarity	NPC26928
0.678	Remote Similarity	NPC302235
0.6779	Remote Similarity	NPC473569
0.6774	Remote Similarity	NPC478075
0.6773	Remote Similarity	NPC116178
0.6769	Remote Similarity	NPC301163
0.6767	Remote Similarity	NPC154922
0.6766	Remote Similarity	NPC474475
0.6765	Remote Similarity	NPC118633
0.6765	Remote Similarity	NPC294790
0.6765	Remote Similarity	NPC474325
0.6765	Remote Similarity	NPC148693
0.6759	Remote Similarity	NPC14339
0.6759	Remote Similarity	NPC475147
0.6751	Remote Similarity	NPC205167
0.6751	Remote Similarity	NPC249274
0.675	Remote Similarity	NPC100566
0.6749	Remote Similarity	NPC287152
0.6749	Remote Similarity	NPC304675
0.6745	Remote Similarity	NPC314948
0.6744	Remote Similarity	NPC474077
0.6742	Remote Similarity	NPC321166
0.6742	Remote Similarity	NPC217903
0.6732	Remote Similarity	NPC99723
0.6732	Remote Similarity	NPC99179
0.6732	Remote Similarity	NPC220961
0.6732	Remote Similarity	NPC474745
0.6728	Remote Similarity	NPC472111
0.6727	Remote Similarity	NPC218303
0.6727	Remote Similarity	NPC82541
0.6727	Remote Similarity	NPC295479
0.6727	Remote Similarity	NPC220241
0.6717	Remote Similarity	NPC472106
0.6715	Remote Similarity	NPC475981
0.6715	Remote Similarity	NPC474746
0.6714	Remote Similarity	NPC17677
0.6712	Remote Similarity	NPC176113
0.6712	Remote Similarity	NPC2905
0.6712	Remote Similarity	NPC475133
0.6711	Remote Similarity	NPC285254
0.6701	Remote Similarity	NPC472117
0.67	Remote Similarity	NPC223077
0.67	Remote Similarity	NPC152680
0.67	Remote Similarity	NPC193853
0.67	Remote Similarity	NPC232386

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 NPC470484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	611
0.2-0.3	774
0.3-0.4	2054
0.4-0.5	2987
0.5-0.6	2136
0.6-0.7	367
0.7-0.8	3
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
0.7438	Intermediate Similarity	NPD5582	Discontinued
0.7385	Intermediate Similarity	NPD5600	Discontinued
0.7273	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7263	Phase 2
0.7077	Intermediate Similarity	NPD3983	Phase 3
0.7077	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4796	Discontinued
0.6959	Remote Similarity	NPD1742	Approved
0.6959	Remote Similarity	NPD19	Approved
0.6959	Remote Similarity	NPD1743	Approved
0.6908	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2899	Discontinued
0.6875	Remote Similarity	NPD6997	Phase 2
0.6869	Remote Similarity	NPD5847	Phase 1
0.6866	Remote Similarity	NPD3793	Phase 3
0.6853	Remote Similarity	NPD6037	Discontinued
0.684	Remote Similarity	NPD6874	Approved
0.6833	Remote Similarity	NPD7047	Phase 3
0.6832	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6625	Approved
0.6786	Remote Similarity	NPD3437	Discontinued
0.6782	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7820	Phase 3
0.6769	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7479	Phase 2
0.6745	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7906	Approved
0.6727	Remote Similarity	NPD4206	Approved
0.6718	Remote Similarity	NPD1769	Discontinued
0.6713	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4577	Approved
0.6699	Remote Similarity	NPD4578	Approved
0.6698	Remote Similarity	NPD6321	Discontinued
0.6696	Remote Similarity	NPD3912	Discontinued
0.6684	Remote Similarity	NPD3141	Discontinued
0.6683	Remote Similarity	NPD4663	Approved
0.6683	Remote Similarity	NPD5938	Phase 3
0.6667	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6034	Phase 2
0.6653	Remote Similarity	NPD7432	Phase 2
0.6651	Remote Similarity	NPD3398	Discontinued
0.6621	Remote Similarity	NPD7222	Phase 2
0.6619	Remote Similarity	NPD2845	Phase 2
0.6619	Remote Similarity	NPD2843	Phase 2
0.6609	Remote Similarity	NPD6723	Discontinued
0.6604	Remote Similarity	NPD7262	Phase 1
0.6604	Remote Similarity	NPD7125	Discontinued
0.66	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8053	Approved
0.6587	Remote Similarity	NPD8054	Approved
0.6584	Remote Similarity	NPD2969	Approved
0.6584	Remote Similarity	NPD2970	Approved
0.6578	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3556	Approved
0.6566	Remote Similarity	NPD3557	Approved
0.6566	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3558	Approved
0.6566	Remote Similarity	NPD3560	Approved
0.6552	Remote Similarity	NPD2489	Approved
0.6552	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD27	Approved
0.6544	Remote Similarity	NPD6238	Discontinued
0.6544	Remote Similarity	NPD3416	Discontinued
0.654	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.654	Remote Similarity	NPD8016	Phase 3
0.6538	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3051	Approved
0.6535	Remote Similarity	NPD6071	Discontinued
0.6535	Remote Similarity	NPD7805	Phase 3
0.653	Remote Similarity	NPD6644	Discontinued
0.6528	Remote Similarity	NPD3158	Phase 1
0.6528	Remote Similarity	NPD3157	Approved
0.6525	Remote Similarity	NPD4846	Phase 2
0.6524	Remote Similarity	NPD2200	Suspended
0.6515	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4604	Approved
0.6512	Remote Similarity	NPD4605	Approved
0.6509	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD4502	Phase 2
0.6502	Remote Similarity	NPD1945	Phase 1
0.6502	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6379	Discontinued
0.6485	Remote Similarity	NPD7126	Discontinued
0.648	Remote Similarity	NPD6357	Discontinued
0.6473	Remote Similarity	NPD7827	Phase 1
0.6473	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7453	Approved
0.6471	Remote Similarity	NPD7452	Approved
0.6471	Remote Similarity	NPD4481	Phase 3
0.6468	Remote Similarity	NPD2494	Approved
0.6468	Remote Similarity	NPD2493	Approved
0.6468	Remote Similarity	NPD3452	Approved
0.6468	Remote Similarity	NPD3450	Approved
0.6459	Remote Similarity	NPD7313	Approved
0.6459	Remote Similarity	NPD7311	Approved
0.6459	Remote Similarity	NPD7310	Approved
0.6459	Remote Similarity	NPD7312	Approved
0.6456	Remote Similarity	NPD7048	Phase 3
0.6456	Remote Similarity	NPD8156	Discontinued
0.6455	Remote Similarity	NPD4583	Approved
0.6455	Remote Similarity	NPD4582	Approved
0.6447	Remote Similarity	NPD5617	Suspended
0.6438	Remote Similarity	NPD2498	Approved
0.6437	Remote Similarity	NPD8461	Discontinued
0.6435	Remote Similarity	NPD2975	Approved
0.6435	Remote Similarity	NPD2974	Approved
0.6435	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD2973	Approved
0.6432	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7309	Approved
0.6429	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7223	Discontinued
0.6422	Remote Similarity	NPD7186	Phase 3
0.6422	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4580	Approved
0.6422	Remote Similarity	NPD7224	Discontinued
0.6411	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6090	Discontinued
0.6409	Remote Similarity	NPD4002	Approved
0.6409	Remote Similarity	NPD4004	Approved
0.6408	Remote Similarity	NPD8252	Approved
0.6408	Remote Similarity	NPD8251	Approved
0.6408	Remote Similarity	NPD8099	Discontinued
0.6408	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5754	Discontinued
0.6404	Remote Similarity	NPD6457	Approved
0.6404	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4492	Approved
0.64	Remote Similarity	NPD4494	Approved
0.6396	Remote Similarity	NPD4596	Phase 1
0.639	Remote Similarity	NPD5858	Discontinued
0.639	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7630	Phase 3
0.6385	Remote Similarity	NPD7628	Phase 3
0.6385	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7281	Phase 3
0.6381	Remote Similarity	NPD7280	Phase 3
0.638	Remote Similarity	NPD4033	Approved
0.638	Remote Similarity	NPD31	Approved
0.638	Remote Similarity	NPD4034	Approved
0.638	Remote Similarity	NPD4038	Approved
0.638	Remote Similarity	NPD32	Approved
0.638	Remote Similarity	NPD4465	Phase 2
0.638	Remote Similarity	NPD4467	Phase 2
0.638	Remote Similarity	NPD4122	Approved
0.638	Remote Similarity	NPD4037	Approved
0.638	Remote Similarity	NPD4039	Approved
0.638	Remote Similarity	NPD4036	Approved
0.638	Remote Similarity	NPD4035	Approved
0.6377	Remote Similarity	NPD42	Phase 2
0.6377	Remote Similarity	NPD6042	Phase 2
0.6376	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5183	Approved
0.6373	Remote Similarity	NPD5186	Approved
0.6373	Remote Similarity	NPD4166	Phase 2
0.6372	Remote Similarity	NPD5610	Approved
0.6368	Remote Similarity	NPD2906	Approved
0.6368	Remote Similarity	NPD2907	Approved
0.6368	Remote Similarity	NPD6788	Approved
0.6368	Remote Similarity	NPD4951	Discontinued
0.6364	Remote Similarity	NPD3515	Approved
0.6364	Remote Similarity	NPD5006	Approved
0.6364	Remote Similarity	NPD3516	Approved
0.6364	Remote Similarity	NPD5005	Approved
0.636	Remote Similarity	NPD5164	Discontinued
0.6359	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7447	Phase 1
0.6351	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7293	Approved
0.6321	Remote Similarity	NPD6339	Approved
0.6321	Remote Similarity	NPD6340	Approved
0.6318	Remote Similarity	NPD2560	Approved
0.6318	Remote Similarity	NPD2563	Approved
0.6316	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1753	Discontinued
0.6316	Remote Similarity	NPD6879	Phase 2
0.6316	Remote Similarity	NPD6878	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