NPASS Compound

Structure

NPC110374 OpenBabel07101718202D 22 25 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 1 1 6 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 16 1 6 0 0 0 7 13 2 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 6 0 0 0 10 12 1 0 0 0 0 10 17 1 1 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 1 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	309.08
Volume:	278.457
LogP:	-0.231
LogD:	-0.008
LogS:	-1.109
# Rotatable Bonds:	0
TPSA:	128.48
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	4.309
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.762
MDCK Permeability:	3.7576792237814516e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.899
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.663

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.295
Plasma Protein Binding (PPB):	76.1440200805664%
Volume Distribution (VD):	1.353
Pgp-substrate:	32.242740631103516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.152
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.285
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.607
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.175
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	5.478
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.318
AMES Toxicity:	0.161
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.243
Skin Sensitization:	0.149
Carcinogencity:	0.516
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.333

Download Data

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

Natural Product: NPC110374

Natural Product ID:	NPC110374
*Common Name:**	Cis-Dihydronarciclasine
IUPAC Name:	(2S,3R,4S,4aR,11bS)-2,3,4,7-tetrahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
Synonyms:	Cis-Dihydronarciclasine
Standard InCHIKey:	SBTGHBALOCEVOR-GUHAZCHASA-N
Standard InCHI:	InChI=1S/C14H15NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h2,5-6,9-10,12,16-19H,1,3H2,(H,15,20)/t5-,6-,9+,10+,12-/m0/s1
SMILES:	O[C@H]1C[C@@H]2[C@H]([C@@H]([C@@H]1O)O)N=C(c1c2cc2OCOc2c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463048
PubChem CID:	3000372
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004129] Phenanthridine- and phenanthridone-type amaryllidaceae 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
NPO33168	amaryllidaceae isoquinoline	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1336040]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	whole plants	n.a.	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348199]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26913788]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	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
ED50	1
IC50	5
Others	6

Activity Type	# Activity
Cell Line	1
Organism	6
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.024	ug ml-1	PMID[455183]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	IC50	=	0.96	ug.mL-1	PMID[455184]
NPT4327	Organism	Yellow fever virus	Yellow fever virus	IC50	=	1.3	ug.mL-1	PMID[455184]
NPT4328	Organism	Dengue virus type 4	Dengue virus 4	IC50	=	2.5	ug.mL-1	PMID[455184]
NPT27	Others	Unspecified		TI	=	5.1	n.a.	PMID[455184]
NPT27	Others	Unspecified		TI	=	3.9	n.a.	PMID[455184]
NPT27	Others	Unspecified		TI	>	2.0	n.a.	PMID[455184]
NPT341	Organism	Punta Toro virus	Punta Toro virus	IC50	=	2.2	ug.mL-1	PMID[455184]
NPT4329	Organism	Rift Valley fever virus	Rift Valley fever virus	IC50	=	1.4	ug.mL-1	PMID[455184]
NPT4330	Organism	Sandfly fever sicilian virus	Sandfly fever sicilian virus	Inhibition	=	25.0	%	PMID[455184]
NPT27	Others	Unspecified		TI	=	3.6	n.a.	PMID[455184]

☑ 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 NPC110374 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	339
0.1-0.2	1393
0.2-0.3	5288
0.3-0.4	12111
0.4-0.5	6298
0.5-0.6	9268
0.6-0.7	6512
0.7-0.8	1452
0.8-0.85	21
0.85-0.9	3
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289743
0.9875	High Similarity	NPC115343
0.9875	High Similarity	NPC1291
0.9563	High Similarity	NPC182257
0.95	High Similarity	NPC304846
0.9497	High Similarity	NPC54125
0.9497	High Similarity	NPC89199
0.9006	High Similarity	NPC474661
0.9006	High Similarity	NPC475919
0.9006	High Similarity	NPC69360
0.8994	High Similarity	NPC474607
0.8941	High Similarity	NPC474650
0.8824	High Similarity	NPC475794
0.8681	High Similarity	NPC475768
0.8372	Intermediate Similarity	NPC474051
0.8363	Intermediate Similarity	NPC474953
0.8294	Intermediate Similarity	NPC198741
0.8176	Intermediate Similarity	NPC77572
0.8114	Intermediate Similarity	NPC187678
0.8	Intermediate Similarity	NPC9867
0.8	Intermediate Similarity	NPC231371
0.8	Intermediate Similarity	NPC329837
0.7919	Intermediate Similarity	NPC180306
0.7879	Intermediate Similarity	NPC166506
0.7879	Intermediate Similarity	NPC197352
0.7879	Intermediate Similarity	NPC189239
0.7879	Intermediate Similarity	NPC110763
0.7853	Intermediate Similarity	NPC228040
0.7841	Intermediate Similarity	NPC311991
0.7821	Intermediate Similarity	NPC15919
0.7818	Intermediate Similarity	NPC73467
0.7818	Intermediate Similarity	NPC121661
0.7778	Intermediate Similarity	NPC474039
0.7778	Intermediate Similarity	NPC244554
0.7771	Intermediate Similarity	NPC68328
0.776	Intermediate Similarity	NPC214116
0.7753	Intermediate Similarity	NPC2314
0.7751	Intermediate Similarity	NPC474560
0.7746	Intermediate Similarity	NPC4304
0.7727	Intermediate Similarity	NPC100566
0.7727	Intermediate Similarity	NPC181653
0.7727	Intermediate Similarity	NPC190332
0.7725	Intermediate Similarity	NPC252286
0.7725	Intermediate Similarity	NPC154971
0.7716	Intermediate Similarity	NPC254610
0.7705	Intermediate Similarity	NPC34780
0.7704	Intermediate Similarity	NPC474594
0.7697	Intermediate Similarity	NPC103637
0.7697	Intermediate Similarity	NPC184684
0.7697	Intermediate Similarity	NPC229172
0.7697	Intermediate Similarity	NPC133934
0.7697	Intermediate Similarity	NPC230538
0.7697	Intermediate Similarity	NPC191231
0.7697	Intermediate Similarity	NPC36531
0.7697	Intermediate Similarity	NPC184641
0.768	Intermediate Similarity	NPC99179
0.7651	Intermediate Similarity	NPC324962
0.7647	Intermediate Similarity	NPC127402
0.764	Intermediate Similarity	NPC58585
0.763	Intermediate Similarity	NPC206736
0.763	Intermediate Similarity	NPC195766
0.7624	Intermediate Similarity	NPC148693
0.7624	Intermediate Similarity	NPC294790
0.7624	Intermediate Similarity	NPC118633
0.7622	Intermediate Similarity	NPC476576
0.7622	Intermediate Similarity	NPC186546
0.7622	Intermediate Similarity	NPC6369
0.7622	Intermediate Similarity	NPC30951
0.7619	Intermediate Similarity	NPC226540
0.7614	Intermediate Similarity	NPC24465
0.7605	Intermediate Similarity	NPC472713
0.7605	Intermediate Similarity	NPC473046
0.7605	Intermediate Similarity	NPC239254
0.7605	Intermediate Similarity	NPC472712
0.7605	Intermediate Similarity	NPC118385
0.7605	Intermediate Similarity	NPC172171
0.7605	Intermediate Similarity	NPC187774
0.7598	Intermediate Similarity	NPC477115
0.7596	Intermediate Similarity	NPC248642
0.7594	Intermediate Similarity	NPC117717
0.7581	Intermediate Similarity	NPC82763
0.7576	Intermediate Similarity	NPC177868
0.7576	Intermediate Similarity	NPC284464
0.7571	Intermediate Similarity	NPC264850
0.7571	Intermediate Similarity	NPC13916
0.7568	Intermediate Similarity	NPC57036
0.7561	Intermediate Similarity	NPC296898
0.756	Intermediate Similarity	NPC307466
0.756	Intermediate Similarity	NPC475868
0.7557	Intermediate Similarity	NPC189782
0.7557	Intermediate Similarity	NPC320104
0.7554	Intermediate Similarity	NPC156576
0.7545	Intermediate Similarity	NPC474808
0.7544	Intermediate Similarity	NPC185955
0.7544	Intermediate Similarity	NPC260781
0.7544	Intermediate Similarity	NPC182368
0.7544	Intermediate Similarity	NPC24425
0.7544	Intermediate Similarity	NPC9933
0.7544	Intermediate Similarity	NPC145979
0.7544	Intermediate Similarity	NPC214326
0.7544	Intermediate Similarity	NPC225815
0.7544	Intermediate Similarity	NPC472710
0.7544	Intermediate Similarity	NPC469706
0.7544	Intermediate Similarity	NPC218041
0.7544	Intermediate Similarity	NPC469707
0.7544	Intermediate Similarity	NPC472709
0.7543	Intermediate Similarity	NPC249274
0.7543	Intermediate Similarity	NPC205167
0.7542	Intermediate Similarity	NPC75958
0.7542	Intermediate Similarity	NPC474475
0.7531	Intermediate Similarity	NPC112237
0.7529	Intermediate Similarity	NPC301961
0.7529	Intermediate Similarity	NPC166584
0.7528	Intermediate Similarity	NPC252960
0.7527	Intermediate Similarity	NPC320223
0.7527	Intermediate Similarity	NPC114364
0.7515	Intermediate Similarity	NPC292487
0.7515	Intermediate Similarity	NPC477837
0.7515	Intermediate Similarity	NPC477838
0.7514	Intermediate Similarity	NPC128560
0.7514	Intermediate Similarity	NPC276944
0.7514	Intermediate Similarity	NPC229166
0.7514	Intermediate Similarity	NPC199465
0.7514	Intermediate Similarity	NPC329969
0.7514	Intermediate Similarity	NPC232514
0.7514	Intermediate Similarity	NPC238530
0.7514	Intermediate Similarity	NPC107602
0.75	Intermediate Similarity	NPC475756
0.75	Intermediate Similarity	NPC470739
0.75	Intermediate Similarity	NPC24260
0.75	Intermediate Similarity	NPC14600
0.75	Intermediate Similarity	NPC65403
0.75	Intermediate Similarity	NPC197166
0.75	Intermediate Similarity	NPC41473
0.75	Intermediate Similarity	NPC160607
0.75	Intermediate Similarity	NPC204848
0.75	Intermediate Similarity	NPC275132
0.75	Intermediate Similarity	NPC477640
0.75	Intermediate Similarity	NPC225597
0.75	Intermediate Similarity	NPC312770
0.7486	Intermediate Similarity	NPC126284
0.7486	Intermediate Similarity	NPC204908
0.7486	Intermediate Similarity	NPC475686
0.7486	Intermediate Similarity	NPC58766
0.7486	Intermediate Similarity	NPC83198
0.7485	Intermediate Similarity	NPC41782
0.7485	Intermediate Similarity	NPC5262
0.7485	Intermediate Similarity	NPC472714
0.7474	Intermediate Similarity	NPC234318
0.7473	Intermediate Similarity	NPC474009
0.7473	Intermediate Similarity	NPC237044
0.7472	Intermediate Similarity	NPC90984
0.7472	Intermediate Similarity	NPC476002
0.7471	Intermediate Similarity	NPC39657
0.7471	Intermediate Similarity	NPC59907
0.7471	Intermediate Similarity	NPC37144
0.746	Intermediate Similarity	NPC85381
0.746	Intermediate Similarity	NPC29472
0.7459	Intermediate Similarity	NPC232386
0.7459	Intermediate Similarity	NPC152680
0.7459	Intermediate Similarity	NPC190783
0.7458	Intermediate Similarity	NPC218614
0.7457	Intermediate Similarity	NPC471154
0.7456	Intermediate Similarity	NPC178014
0.7456	Intermediate Similarity	NPC42716
0.7456	Intermediate Similarity	NPC11422
0.7456	Intermediate Similarity	NPC474749
0.7455	Intermediate Similarity	NPC46277
0.7455	Intermediate Similarity	NPC3072
0.7455	Intermediate Similarity	NPC301765
0.7455	Intermediate Similarity	NPC299583
0.7455	Intermediate Similarity	NPC86605
0.7455	Intermediate Similarity	NPC156948
0.7447	Intermediate Similarity	NPC41122
0.7447	Intermediate Similarity	NPC318805
0.7443	Intermediate Similarity	NPC66678
0.7443	Intermediate Similarity	NPC202839
0.744	Intermediate Similarity	NPC81638
0.744	Intermediate Similarity	NPC12728
0.744	Intermediate Similarity	NPC298317
0.744	Intermediate Similarity	NPC265154
0.744	Intermediate Similarity	NPC255566
0.744	Intermediate Similarity	NPC185071
0.7432	Intermediate Similarity	NPC474325
0.7427	Intermediate Similarity	NPC325720
0.7427	Intermediate Similarity	NPC130449
0.7427	Intermediate Similarity	NPC316676
0.7427	Intermediate Similarity	NPC248132
0.7423	Intermediate Similarity	NPC471390
0.7423	Intermediate Similarity	NPC471391
0.7423	Intermediate Similarity	NPC196937
0.7421	Intermediate Similarity	NPC473960
0.7418	Intermediate Similarity	NPC304675
0.7414	Intermediate Similarity	NPC474606
0.7412	Intermediate Similarity	NPC33832
0.7412	Intermediate Similarity	NPC99515
0.7412	Intermediate Similarity	NPC190714
0.7412	Intermediate Similarity	NPC212890
0.741	Intermediate Similarity	NPC473739
0.741	Intermediate Similarity	NPC201404

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 NPC110374 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	670
0.2-0.3	1310
0.3-0.4	2742
0.4-0.5	2246
0.5-0.6	1402
0.6-0.7	494
0.7-0.8	87
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD4005	Discontinued
0.8059	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7007	Discovery
0.7609	Intermediate Similarity	NPD4663	Approved
0.7579	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD2977	Approved
0.7572	Intermediate Similarity	NPD2978	Approved
0.7541	Intermediate Similarity	NPD4577	Approved
0.7541	Intermediate Similarity	NPD4578	Approved
0.7389	Intermediate Similarity	NPD27	Approved
0.7389	Intermediate Similarity	NPD2489	Approved
0.738	Intermediate Similarity	NPD7906	Approved
0.738	Intermediate Similarity	NPD6842	Approved
0.738	Intermediate Similarity	NPD6843	Phase 3
0.738	Intermediate Similarity	NPD6841	Approved
0.7345	Intermediate Similarity	NPD4055	Discovery
0.7333	Intermediate Similarity	NPD2970	Approved
0.7333	Intermediate Similarity	NPD2969	Approved
0.73	Intermediate Similarity	NPD7827	Phase 1
0.7278	Intermediate Similarity	NPD3051	Approved
0.7273	Intermediate Similarity	NPD5773	Approved
0.7273	Intermediate Similarity	NPD5772	Approved
0.7258	Intermediate Similarity	NPD7310	Approved
0.7258	Intermediate Similarity	NPD7311	Approved
0.7258	Intermediate Similarity	NPD7312	Approved
0.7258	Intermediate Similarity	NPD7313	Approved
0.7256	Intermediate Similarity	NPD1613	Approved
0.7256	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7309	Approved
0.7219	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD37	Approved
0.7207	Intermediate Similarity	NPD6234	Discontinued
0.7202	Intermediate Similarity	NPD1375	Discontinued
0.72	Intermediate Similarity	NPD4675	Approved
0.72	Intermediate Similarity	NPD4678	Approved
0.7196	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3027	Phase 3
0.7176	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6331	Phase 2
0.7168	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD52	Approved
0.7168	Intermediate Similarity	NPD7526	Approved
0.7159	Intermediate Similarity	NPD5090	Approved
0.7159	Intermediate Similarity	NPD5089	Approved
0.7128	Intermediate Similarity	NPD8053	Approved
0.7128	Intermediate Similarity	NPD8054	Approved
0.7118	Intermediate Similarity	NPD4236	Phase 3
0.7118	Intermediate Similarity	NPD4237	Approved
0.7101	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4966	Approved
0.7095	Intermediate Similarity	NPD4967	Phase 2
0.7095	Intermediate Similarity	NPD4965	Approved
0.7055	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5241	Discontinued
0.7027	Intermediate Similarity	NPD7228	Approved
0.7012	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1653	Approved
0.6988	Remote Similarity	NPD2674	Phase 3
0.6985	Remote Similarity	NPD4002	Approved
0.6985	Remote Similarity	NPD4004	Approved
0.697	Remote Similarity	NPD3450	Approved
0.697	Remote Similarity	NPD2494	Approved
0.697	Remote Similarity	NPD2493	Approved
0.697	Remote Similarity	NPD3452	Approved
0.6964	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5604	Discontinued
0.695	Remote Similarity	NPD4583	Approved
0.695	Remote Similarity	NPD4582	Approved
0.6946	Remote Similarity	NPD2238	Phase 2
0.6944	Remote Similarity	NPD2560	Approved
0.6944	Remote Similarity	NPD2563	Approved
0.6941	Remote Similarity	NPD2161	Phase 2
0.6935	Remote Similarity	NPD5005	Approved
0.6935	Remote Similarity	NPD5006	Approved
0.6928	Remote Similarity	NPD3144	Approved
0.6928	Remote Similarity	NPD3145	Approved
0.6919	Remote Similarity	NPD4481	Phase 3
0.6919	Remote Similarity	NPD5177	Phase 3
0.6914	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4123	Phase 3
0.6885	Remote Similarity	NPD6746	Phase 2
0.6882	Remote Similarity	NPD4108	Discontinued
0.6848	Remote Similarity	NPD7199	Phase 2
0.6845	Remote Similarity	NPD3818	Discontinued
0.6839	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD302	Approved
0.6821	Remote Similarity	NPD6674	Discontinued
0.6821	Remote Similarity	NPD3060	Approved
0.6818	Remote Similarity	NPD4739	Approved
0.6811	Remote Similarity	NPD6071	Discontinued
0.6809	Remote Similarity	NPD8156	Discontinued
0.68	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3705	Approved
0.6786	Remote Similarity	NPD839	Approved
0.6786	Remote Similarity	NPD840	Approved
0.6786	Remote Similarity	NPD554	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4772	Phase 2
0.6778	Remote Similarity	NPD4773	Phase 2
0.6769	Remote Similarity	NPD2488	Approved
0.6769	Remote Similarity	NPD2490	Approved
0.6768	Remote Similarity	NPD2974	Approved
0.6768	Remote Similarity	NPD2973	Approved
0.6768	Remote Similarity	NPD2975	Approved
0.6761	Remote Similarity	NPD4357	Discontinued
0.6755	Remote Similarity	NPD8099	Discontinued
0.6755	Remote Similarity	NPD8252	Approved
0.6755	Remote Similarity	NPD8251	Approved
0.6754	Remote Similarity	NPD7549	Discontinued
0.675	Remote Similarity	NPD4580	Approved
0.6743	Remote Similarity	NPD2219	Phase 1
0.6743	Remote Similarity	NPD2677	Approved
0.6743	Remote Similarity	NPD3692	Discontinued
0.6742	Remote Similarity	NPD2122	Discontinued
0.674	Remote Similarity	NPD3382	Approved
0.674	Remote Similarity	NPD3383	Approved
0.674	Remote Similarity	NPD3384	Approved
0.6735	Remote Similarity	NPD7296	Approved
0.6734	Remote Similarity	NPD4420	Approved
0.6732	Remote Similarity	NPD8151	Discontinued
0.6723	Remote Similarity	NPD4584	Approved
0.672	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD600	Approved
0.6707	Remote Similarity	NPD9622	Approved
0.6707	Remote Similarity	NPD596	Approved
0.6705	Remote Similarity	NPD7124	Phase 2
0.6703	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3489	Phase 3
0.6701	Remote Similarity	NPD7125	Discontinued
0.6699	Remote Similarity	NPD7047	Phase 3
0.6685	Remote Similarity	NPD6072	Discontinued
0.6684	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3620	Phase 2
0.6647	Remote Similarity	NPD1712	Approved
0.663	Remote Similarity	NPD6788	Approved
0.6615	Remote Similarity	NPD7240	Approved
0.6613	Remote Similarity	NPD4666	Phase 3
0.6613	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4585	Approved
0.6601	Remote Similarity	NPD6823	Phase 2
0.659	Remote Similarity	NPD1753	Discontinued
0.6585	Remote Similarity	NPD1610	Phase 2
0.658	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7213	Phase 3
0.6573	Remote Similarity	NPD7212	Phase 2
0.657	Remote Similarity	NPD2157	Approved
0.657	Remote Similarity	NPD817	Approved
0.657	Remote Similarity	NPD823	Approved
0.6568	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD9384	Approved
0.6564	Remote Similarity	NPD9381	Approved
0.6561	Remote Similarity	NPD2898	Approved
0.6559	Remote Similarity	NPD5709	Phase 3
0.6554	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5582	Discontinued
0.655	Remote Similarity	NPD1558	Phase 1
0.6548	Remote Similarity	NPD2845	Phase 2
0.6548	Remote Similarity	NPD2843	Phase 2
0.6545	Remote Similarity	NPD7054	Approved
0.6543	Remote Similarity	NPD7315	Approved
0.6543	Remote Similarity	NPD4010	Discontinued
0.6537	Remote Similarity	NPD4040	Phase 1
0.6536	Remote Similarity	NPD7447	Phase 1
0.6534	Remote Similarity	NPD4162	Approved
0.6532	Remote Similarity	NPD6111	Discontinued
0.6526	Remote Similarity	NPD4665	Approved
0.6526	Remote Similarity	NPD4111	Phase 1
0.6526	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3686	Approved
0.6519	Remote Similarity	NPD3687	Approved
0.6519	Remote Similarity	NPD4210	Discontinued
0.6517	Remote Similarity	NPD4604	Approved
0.6517	Remote Similarity	NPD4605	Approved
0.6512	Remote Similarity	NPD6997	Phase 2
0.651	Remote Similarity	NPD7472	Approved
0.651	Remote Similarity	NPD7074	Phase 3
0.6507	Remote Similarity	NPD7801	Approved
0.6506	Remote Similarity	NPD1669	Approved
0.6506	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1357	Approved
0.65	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1349	Approved
0.65	Remote Similarity	NPD1350	Approved
0.65	Remote Similarity	NPD1351	Approved
0.6491	Remote Similarity	NPD1136	Approved
0.6491	Remote Similarity	NPD1132	Approved
0.6491	Remote Similarity	NPD1130	Approved
0.6485	Remote Similarity	NPD1091	Approved
0.6484	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.648	Remote Similarity	NPD1774	Approved

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