NPASS Compound

Structure

CID243162 OpenBabel06191716042D 22 26 0 0 1 0 0 0 0 0999 V2000 -3.5595 -0.8394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5595 0.1267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0019 1.7335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0829 0.5752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9583 2.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1202 -0.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4368 1.0927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1310 0.3111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8863 2.0587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8863 0.1267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5335 -1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7229 0.6097 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7229 1.5757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8999 0.7567 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9956 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0766 0.4349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0497 1.5757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7463 0.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1310 1.8742 0.0000 C 0 0 1 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 -1.0497 0.6097 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.9015 -1.7992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 8 21 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 2 1 1 0 0 0 12 13 1 0 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 14 11 1 1 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 1 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 20 2 0 0 0 0 19 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.19
Volume:	314.636
LogP:	2.21
LogD:	2.581
LogS:	-3.389
# Rotatable Bonds:	2
TPSA:	35.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.911
Synthetic Accessibility Score:	5.57
Fsp3:	0.632
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:	-4.637
MDCK Permeability:	2.1790290702483617e-05
Pgp-inhibitor:	0.951
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.409
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	65.98479461669922%
Volume Distribution (VD):	2.079
Pgp-substrate:	37.251277923583984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.189
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.215
CYP3A4-substrate:	0.795

ADMET: Excretion

Clearance (CL):	7.868
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.558
Human Hepatotoxicity (H-HT):	0.565
Drug-inuced Liver Injury (DILI):	0.46
AMES Toxicity:	0.361
Rat Oral Acute Toxicity:	0.85
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.693
Carcinogencity:	0.674
Eye Corrosion:	0.004
Eye Irritation:	0.107
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: NPC243162

Natural Product ID:	NPC243162
*Common Name:**	XJEKUKWZYMNSDW-XTXPVBGVSA-N
IUPAC Name:	n.a.
Synonyms:	1,2-Dehydrogeissoschizoline
Standard InCHIKey:	XJEKUKWZYMNSDW-XTXPVBGVSA-N
Standard InCHI:	InChI=1S/C19H24N2O/c1-2-12-10-21-8-7-19-15-5-3-4-6-16(15)20-18(19)14(11-22)13(12)9-17(19)21/h3-6,12-14,17,22H,2,7-11H2,1H3/t12-,13+,14+,17+,19-/m1/s1
SMILES:	CC[C@@H]1CN2CC[C@@]34c5ccccc5N=C4[C@@H](CO)[C@H]1C[C@H]23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463735
PubChem CID:	15538076
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
NPO31191	Geissospermum sericeum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809075]
NPO31191	Geissospermum sericeum	Species	Apocynaceae	Eukaryota	n.a.	bark	n.a.	PMID[11809075]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	40000.0	nM	PMID[531340]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	27260.0	nM	PMID[531340]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	35370.0	nM	PMID[531340]

☑ 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 NPC243162 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	243
0.1-0.2	1228
0.2-0.3	5210
0.3-0.4	22303
0.4-0.5	9041
0.5-0.6	3824
0.6-0.7	740
0.7-0.8	95
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8662	High Similarity	NPC116519
0.8639	High Similarity	NPC477157
0.8639	High Similarity	NPC477156
0.8472	Intermediate Similarity	NPC264589
0.8472	Intermediate Similarity	NPC472100
0.8444	Intermediate Similarity	NPC478079
0.8333	Intermediate Similarity	NPC472103
0.8321	Intermediate Similarity	NPC264580
0.8224	Intermediate Similarity	NPC477158
0.8	Intermediate Similarity	NPC475763
0.7945	Intermediate Similarity	NPC477155
0.7843	Intermediate Similarity	NPC473297
0.7742	Intermediate Similarity	NPC153694
0.7742	Intermediate Similarity	NPC211525
0.7697	Intermediate Similarity	NPC19679
0.7692	Intermediate Similarity	NPC97380
0.7692	Intermediate Similarity	NPC63210
0.7692	Intermediate Similarity	NPC243673
0.7692	Intermediate Similarity	NPC148468
0.7692	Intermediate Similarity	NPC310403
0.7692	Intermediate Similarity	NPC263709
0.7625	Intermediate Similarity	NPC469462
0.7595	Intermediate Similarity	NPC472121
0.75	Intermediate Similarity	NPC161827
0.75	Intermediate Similarity	NPC52059
0.75	Intermediate Similarity	NPC470069
0.7483	Intermediate Similarity	NPC311330
0.7453	Intermediate Similarity	NPC278887
0.7451	Intermediate Similarity	NPC212799
0.7439	Intermediate Similarity	NPC475097
0.7378	Intermediate Similarity	NPC210415
0.7378	Intermediate Similarity	NPC473880
0.7378	Intermediate Similarity	NPC298851
0.7378	Intermediate Similarity	NPC293255
0.7378	Intermediate Similarity	NPC181138
0.7378	Intermediate Similarity	NPC21752
0.7378	Intermediate Similarity	NPC276993
0.7355	Intermediate Similarity	NPC318086
0.7333	Intermediate Similarity	NPC189812
0.7333	Intermediate Similarity	NPC329688
0.7312	Intermediate Similarity	NPC225319
0.7284	Intermediate Similarity	NPC475420
0.7273	Intermediate Similarity	NPC469735
0.7267	Intermediate Similarity	NPC99632
0.7267	Intermediate Similarity	NPC282339
0.725	Intermediate Similarity	NPC469461
0.7226	Intermediate Similarity	NPC469740
0.7226	Intermediate Similarity	NPC470550
0.7225	Intermediate Similarity	NPC95783
0.7197	Intermediate Similarity	NPC206592
0.7171	Intermediate Similarity	NPC22082
0.7171	Intermediate Similarity	NPC186284
0.7169	Intermediate Similarity	NPC472123
0.716	Intermediate Similarity	NPC472117
0.716	Intermediate Similarity	NPC472120
0.716	Intermediate Similarity	NPC472101
0.7118	Intermediate Similarity	NPC475962
0.7108	Intermediate Similarity	NPC158129
0.7101	Intermediate Similarity	NPC133261
0.7099	Intermediate Similarity	NPC472102
0.7099	Intermediate Similarity	NPC255229
0.7099	Intermediate Similarity	NPC81229
0.7099	Intermediate Similarity	NPC143457
0.7099	Intermediate Similarity	NPC309531
0.7091	Intermediate Similarity	NPC317430
0.7083	Intermediate Similarity	NPC472122
0.7083	Intermediate Similarity	NPC24594
0.7081	Intermediate Similarity	NPC129721
0.7073	Intermediate Similarity	NPC472106
0.7066	Intermediate Similarity	NPC471294
0.7066	Intermediate Similarity	NPC473743
0.7041	Intermediate Similarity	NPC326575
0.7037	Intermediate Similarity	NPC36495
0.6994	Remote Similarity	NPC68650
0.6978	Remote Similarity	NPC205652
0.6975	Remote Similarity	NPC104345
0.697	Remote Similarity	NPC470508
0.6964	Remote Similarity	NPC251212
0.6964	Remote Similarity	NPC139085
0.6964	Remote Similarity	NPC214626
0.6959	Remote Similarity	NPC472105
0.6959	Remote Similarity	NPC226662
0.6959	Remote Similarity	NPC15840
0.6959	Remote Similarity	NPC187827
0.6951	Remote Similarity	NPC16667
0.695	Remote Similarity	NPC192209
0.6946	Remote Similarity	NPC280548
0.6936	Remote Similarity	NPC245741
0.6917	Remote Similarity	NPC178681
0.6914	Remote Similarity	NPC285469
0.6897	Remote Similarity	NPC52262
0.6894	Remote Similarity	NPC478076
0.689	Remote Similarity	NPC474058
0.689	Remote Similarity	NPC248117
0.6887	Remote Similarity	NPC313352
0.6887	Remote Similarity	NPC184437
0.6886	Remote Similarity	NPC154293
0.6886	Remote Similarity	NPC201700
0.6885	Remote Similarity	NPC52801
0.6882	Remote Similarity	NPC320147
0.6882	Remote Similarity	NPC134586
0.6882	Remote Similarity	NPC87755
0.6879	Remote Similarity	NPC472110
0.6879	Remote Similarity	NPC472108
0.6879	Remote Similarity	NPC147957
0.6879	Remote Similarity	NPC472109
0.6879	Remote Similarity	NPC139291
0.6875	Remote Similarity	NPC33421
0.6871	Remote Similarity	NPC113946
0.6852	Remote Similarity	NPC207726
0.6842	Remote Similarity	NPC151939
0.6842	Remote Similarity	NPC211997
0.6839	Remote Similarity	NPC472294
0.6829	Remote Similarity	NPC193410
0.6829	Remote Similarity	NPC67056
0.6824	Remote Similarity	NPC476950
0.6824	Remote Similarity	NPC13367
0.681	Remote Similarity	NPC29285
0.6809	Remote Similarity	NPC475422
0.6807	Remote Similarity	NPC469541
0.6803	Remote Similarity	NPC325013
0.6802	Remote Similarity	NPC218594
0.6802	Remote Similarity	NPC99043
0.68	Remote Similarity	NPC469460
0.6796	Remote Similarity	NPC229332
0.6788	Remote Similarity	NPC315368
0.6786	Remote Similarity	NPC187036
0.6784	Remote Similarity	NPC121903
0.6784	Remote Similarity	NPC476441
0.6781	Remote Similarity	NPC328683
0.6781	Remote Similarity	NPC283130
0.6768	Remote Similarity	NPC61013
0.6765	Remote Similarity	NPC96901
0.6765	Remote Similarity	NPC97525
0.6763	Remote Similarity	NPC300688
0.6761	Remote Similarity	NPC282092
0.6747	Remote Similarity	NPC85651
0.6747	Remote Similarity	NPC476231
0.6746	Remote Similarity	NPC472118
0.6742	Remote Similarity	NPC105055
0.6742	Remote Similarity	NPC22689
0.673	Remote Similarity	NPC470579
0.6727	Remote Similarity	NPC6436
0.6726	Remote Similarity	NPC98187
0.6724	Remote Similarity	NPC113626
0.6723	Remote Similarity	NPC472323
0.6712	Remote Similarity	NPC109151
0.6706	Remote Similarity	NPC355
0.6706	Remote Similarity	NPC126492
0.6705	Remote Similarity	NPC476095
0.6689	Remote Similarity	NPC474926
0.6686	Remote Similarity	NPC264482
0.6686	Remote Similarity	NPC33507
0.6686	Remote Similarity	NPC203202
0.6685	Remote Similarity	NPC221687
0.6667	Remote Similarity	NPC296163
0.6667	Remote Similarity	NPC39822
0.6667	Remote Similarity	NPC132847
0.6667	Remote Similarity	NPC259098
0.6667	Remote Similarity	NPC130251
0.6667	Remote Similarity	NPC34508
0.6667	Remote Similarity	NPC197680
0.6648	Remote Similarity	NPC469470
0.6648	Remote Similarity	NPC469501
0.6647	Remote Similarity	NPC260075
0.6644	Remote Similarity	NPC475915
0.6629	Remote Similarity	NPC204565
0.6629	Remote Similarity	NPC285841
0.6628	Remote Similarity	NPC37423
0.6628	Remote Similarity	NPC472586
0.6628	Remote Similarity	NPC275305
0.6627	Remote Similarity	NPC214960
0.6627	Remote Similarity	NPC279527
0.6624	Remote Similarity	NPC104483
0.6622	Remote Similarity	NPC317758
0.6615	Remote Similarity	NPC475602
0.6613	Remote Similarity	NPC162730
0.6612	Remote Similarity	NPC90967
0.6612	Remote Similarity	NPC475559
0.6609	Remote Similarity	NPC472443
0.6609	Remote Similarity	NPC176199
0.6609	Remote Similarity	NPC215795
0.6606	Remote Similarity	NPC51054
0.6595	Remote Similarity	NPC79129
0.6595	Remote Similarity	NPC249150
0.6595	Remote Similarity	NPC49196
0.6595	Remote Similarity	NPC195461
0.6595	Remote Similarity	NPC313985
0.6595	Remote Similarity	NPC81654
0.6592	Remote Similarity	NPC175474
0.6592	Remote Similarity	NPC173028
0.6592	Remote Similarity	NPC65215
0.6592	Remote Similarity	NPC217294
0.6591	Remote Similarity	NPC159125
0.6588	Remote Similarity	NPC224970
0.6588	Remote Similarity	NPC223595
0.6588	Remote Similarity	NPC167724
0.6587	Remote Similarity	NPC201424
0.6582	Remote Similarity	NPC471516
0.6577	Remote Similarity	NPC472414

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 NPC243162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	499
0.2-0.3	707
0.3-0.4	1438
0.4-0.5	3400
0.5-0.6	2552
0.6-0.7	356
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
0.7852	Intermediate Similarity	NPD2210	Approved
0.7852	Intermediate Similarity	NPD2212	Approved
0.7669	Intermediate Similarity	NPD3148	Approved
0.7669	Intermediate Similarity	NPD3150	Approved
0.7669	Intermediate Similarity	NPD2659	Approved
0.7669	Intermediate Similarity	NPD3147	Approved
0.7669	Intermediate Similarity	NPD3149	Approved
0.7669	Intermediate Similarity	NPD2658	Approved
0.7594	Intermediate Similarity	NPD1764	Approved
0.7594	Intermediate Similarity	NPD1762	Approved
0.7556	Intermediate Similarity	NPD2622	Approved
0.7517	Intermediate Similarity	NPD6789	Approved
0.7481	Intermediate Similarity	NPD5631	Phase 3
0.7436	Intermediate Similarity	NPD4120	Approved
0.7436	Intermediate Similarity	NPD4121	Phase 3
0.7394	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5741	Approved
0.7389	Intermediate Similarity	NPD5742	Approved
0.7389	Intermediate Similarity	NPD5743	Approved
0.7333	Intermediate Similarity	NPD6606	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5595	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2678	Approved
0.7293	Intermediate Similarity	NPD2679	Approved
0.729	Intermediate Similarity	NPD5881	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7522	Discontinued
0.7178	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7252	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4895	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6522	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2173	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6506	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1001	Discontinued
0.7014	Intermediate Similarity	NPD7461	Approved
0.6981	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3066	Phase 2
0.6957	Remote Similarity	NPD4165	Phase 2
0.6917	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7200	Approved
0.6886	Remote Similarity	NPD4640	Approved
0.6886	Remote Similarity	NPD4639	Approved
0.6886	Remote Similarity	NPD4638	Approved
0.6884	Remote Similarity	NPD2039	Approved
0.6884	Remote Similarity	NPD2038	Approved
0.6861	Remote Similarity	NPD1108	Approved
0.6861	Remote Similarity	NPD4116	Approved
0.6861	Remote Similarity	NPD1107	Approved
0.6859	Remote Similarity	NPD6301	Phase 2
0.6853	Remote Similarity	NPD1922	Discontinued
0.6846	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1419	Approved
0.6842	Remote Similarity	NPD1417	Approved
0.6838	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6026	Approved
0.6803	Remote Similarity	NPD6320	Approved
0.6793	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8354	Approved
0.6788	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD478	Approved
0.6779	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7295	Approved
0.677	Remote Similarity	NPD8355	Approved
0.677	Remote Similarity	NPD8353	Approved
0.6765	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6900	Discontinued
0.6746	Remote Similarity	NPD1326	Approved
0.6746	Remote Similarity	NPD1325	Approved
0.6739	Remote Similarity	NPD7633	Discontinued
0.6728	Remote Similarity	NPD8400	Approved
0.6728	Remote Similarity	NPD8401	Approved
0.6728	Remote Similarity	NPD8402	Approved
0.6707	Remote Similarity	NPD2789	Approved
0.6705	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD564	Approved
0.6691	Remote Similarity	NPD563	Approved
0.6689	Remote Similarity	NPD1036	Approved
0.6689	Remote Similarity	NPD5578	Approved
0.6689	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5599	Discontinued
0.6686	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2913	Approved
0.6667	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5185	Approved
0.6667	Remote Similarity	NPD5657	Phase 3
0.6667	Remote Similarity	NPD5184	Approved
0.6667	Remote Similarity	NPD2914	Approved
0.6667	Remote Similarity	NPD5182	Approved
0.6667	Remote Similarity	NPD7582	Discontinued
0.6648	Remote Similarity	NPD6281	Approved
0.6647	Remote Similarity	NPD7795	Phase 2
0.6644	Remote Similarity	NPD2840	Approved
0.6643	Remote Similarity	NPD1344	Phase 2
0.6643	Remote Similarity	NPD6660	Discontinued
0.6628	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7599	Phase 2
0.6626	Remote Similarity	NPD6158	Phase 2
0.6626	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2188	Approved
0.6626	Remote Similarity	NPD2882	Phase 1
0.6623	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4079	Approved
0.6609	Remote Similarity	NPD4076	Approved
0.6604	Remote Similarity	NPD7487	Discontinued
0.6603	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD8118	Discontinued
0.6595	Remote Similarity	NPD4601	Approved
0.6595	Remote Similarity	NPD4600	Approved
0.6594	Remote Similarity	NPD6299	Approved
0.6594	Remote Similarity	NPD6300	Approved
0.6588	Remote Similarity	NPD5021	Discontinued
0.6588	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7600	Phase 2
0.6587	Remote Similarity	NPD5989	Phase 1
0.6587	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4031	Approved
0.6573	Remote Similarity	NPD4032	Approved
0.6569	Remote Similarity	NPD5717	Approved
0.6568	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3635	Approved
0.6556	Remote Similarity	NPD3636	Approved
0.6556	Remote Similarity	NPD3637	Approved
0.6552	Remote Similarity	NPD3506	Approved
0.6552	Remote Similarity	NPD3505	Approved
0.655	Remote Similarity	NPD7474	Suspended
0.6549	Remote Similarity	NPD23	Approved
0.6543	Remote Similarity	NPD4703	Approved
0.6543	Remote Similarity	NPD4702	Approved
0.6541	Remote Similarity	NPD7082	Approved
0.6541	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4411	Phase 1
0.6536	Remote Similarity	NPD4951	Discontinued
0.6536	Remote Similarity	NPD2383	Phase 1
0.6528	Remote Similarity	NPD6069	Approved
0.6528	Remote Similarity	NPD6070	Approved
0.6522	Remote Similarity	NPD6416	Phase 2
0.6519	Remote Similarity	NPD1953	Discontinued
0.6516	Remote Similarity	NPD3385	Approved
0.6514	Remote Similarity	NPD8386	Phase 2
0.65	Remote Similarity	NPD7259	Approved
0.649	Remote Similarity	NPD6259	Discontinued
0.6489	Remote Similarity	NPD6690	Approved
0.6486	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3529	Phase 2
0.6477	Remote Similarity	NPD6595	Phase 3
0.6477	Remote Similarity	NPD6878	Phase 2
0.6477	Remote Similarity	NPD6879	Phase 2
0.6474	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7418	Discontinued
0.6471	Remote Similarity	NPD6489	Phase 3
0.6471	Remote Similarity	NPD4119	Approved
0.6471	Remote Similarity	NPD4719	Phase 2
0.6471	Remote Similarity	NPD4275	Approved
0.6471	Remote Similarity	NPD4274	Approved
0.6471	Remote Similarity	NPD3720	Discontinued
0.6467	Remote Similarity	NPD7935	Phase 2
0.6467	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD2895	Discontinued
0.6457	Remote Similarity	NPD2144	Approved
0.6446	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD3038	Discontinued
0.6434	Remote Similarity	NPD5179	Approved
0.6434	Remote Similarity	NPD5180	Approved
0.6434	Remote Similarity	NPD5181	Approved
0.6429	Remote Similarity	NPD2322	Discovery
0.6429	Remote Similarity	NPD477	Phase 1
0.6424	Remote Similarity	NPD5663	Discontinued
0.6423	Remote Similarity	NPD5103	Approved
0.6415	Remote Similarity	NPD2093	Discontinued
0.641	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD3595	Approved
0.6405	Remote Similarity	NPD3594	Approved
0.6405	Remote Similarity	NPD2605	Approved
0.6405	Remote Similarity	NPD2606	Approved
0.6404	Remote Similarity	NPD5596	Phase 2
0.6402	Remote Similarity	NPD1405	Approved
0.6402	Remote Similarity	NPD6221	Approved
0.6402	Remote Similarity	NPD6222	Approved
0.64	Remote Similarity	NPD6025	Phase 1
0.64	Remote Similarity	NPD5100	Phase 3
0.6397	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5629	Discontinued
0.6387	Remote Similarity	NPD1316	Discontinued
0.6384	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7904	Phase 2
0.638	Remote Similarity	NPD1683	Approved
0.6374	Remote Similarity	NPD4499	Approved
0.637	Remote Similarity	NPD7481	Approved
0.637	Remote Similarity	NPD7480	Approved
0.6364	Remote Similarity	NPD6203	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