NPASS Compound

Structure

NPC261733 OpenBabel07101719152D 30 32 0 0 1 0 0 0 0 0999 V2000 4.5007 0.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7420 -1.6800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3781 -1.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1187 -0.2341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4826 -0.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2052 -0.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4646 -1.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9278 -0.8219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8898 1.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7559 1.7673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7073 -0.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4286 -0.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0923 0.1847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0492 0.5630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3962 -0.0531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6555 -1.2733 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8413 -0.4152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0978 0.2892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4505 -0.2460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4990 1.0982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0437 0.6675 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 17 1 0 0 0 0 3 19 1 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 11 2 0 0 0 0 10 21 1 0 0 0 0 11 28 1 0 0 0 0 12 18 1 0 0 0 0 12 23 2 0 0 0 0 13 20 1 0 0 0 0 13 22 2 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 21 2 0 0 0 0 15 28 1 0 0 0 0 16 20 2 0 0 0 0 16 29 1 0 0 0 0 18 2 1 1 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 25 27 2 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.21
Volume:	438.146
LogP:	5.203
LogD:	4.422
LogS:	-5.061
# Rotatable Bonds:	10
TPSA:	79.88
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	3.569
Fsp3:	0.36
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.827
MDCK Permeability:	2.3184673409559764e-05
Pgp-inhibitor:	0.373
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.101
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	99.30624389648438%
Volume Distribution (VD):	3.013
Pgp-substrate:	0.7551573514938354%

ADMET: Metabolism

CYP1A2-inhibitor:	0.33
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.905
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.889
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.623
CYP3A4-substrate:	0.503

ADMET: Excretion

Clearance (CL):	8.827
Half-life (T1/2):	0.922

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.785
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.648
Carcinogencity:	0.826
Eye Corrosion:	0.003
Eye Irritation:	0.236
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC261733

Natural Product ID:	NPC261733
*Common Name:**	Ircinin 2
IUPAC Name:	(5Z)-5-[(Z,2R)-9-[5-(furan-3-ylmethyl)furan-3-yl]-2,6-dimethylnon-5-enylidene]-4-hydroxy-3-methylfuran-2-one
Synonyms:	Ircinin 2
Standard InCHIKey:	YIWFEASCLZQHBJ-MGPQNOLOSA-N
Standard InCHI:	InChI=1S/C25H30O5/c1-17(6-4-8-18(2)12-23-24(26)19(3)25(27)30-23)7-5-9-20-13-22(29-16-20)14-21-10-11-28-15-21/h6,10-13,15-16,18,26H,4-5,7-9,14H2,1-3H3/b17-6-,23-12-/t18-/m1/s1
SMILES:	C/C(=C/CC[C@@H](C)/C=C1/C(=C(C)C(=O)O1)O)/CCCc1cc(Cc2ccoc2)oc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483842
PubChem CID:	54726397
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678655]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350153]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341287]
NPO21618	Ircinia oros	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28840725]
NPO21618	Ircinia oros	Species	Irciniidae	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	5
IC50	7
LD50	1

Activity Type	# Activity
Cell Line	6
Individual Protein	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.8	ug ml-1	PMID[549812]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	5.9	ug ml-1	PMID[549812]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	5.87	ug ml-1	PMID[549812]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[549812]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.74	ug ml-1	PMID[549812]
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	=	2344.23	nM	PMID[549813]
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	=	2300.0	nM	PMID[549813]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	140000.0	nM	PMID[549814]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	2.7	ug ml-1	PMID[549811]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	56000.0	nM	PMID[549814]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	28000.0	nM	PMID[549814]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	110000.0	nM	PMID[549814]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	65000.0	nM	PMID[549814]

☑ 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 NPC261733 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	313
0.1-0.2	1445
0.2-0.3	3963
0.3-0.4	9592
0.4-0.5	9803
0.5-0.6	5870
0.6-0.7	9742
0.7-0.8	1913
0.8-0.85	39
0.85-0.9	11
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC307346
1.0	High Similarity	NPC267004
1.0	High Similarity	NPC218712
0.8652	High Similarity	NPC14650
0.8592	High Similarity	NPC303217
0.8582	High Similarity	NPC288209
0.8562	High Similarity	NPC254198
0.8467	Intermediate Similarity	NPC71274
0.8467	Intermediate Similarity	NPC75557
0.844	Intermediate Similarity	NPC45358
0.844	Intermediate Similarity	NPC97740
0.8421	Intermediate Similarity	NPC474378
0.8421	Intermediate Similarity	NPC474219
0.8414	Intermediate Similarity	NPC107571
0.8403	Intermediate Similarity	NPC170604
0.8403	Intermediate Similarity	NPC215109
0.8389	Intermediate Similarity	NPC104924
0.8369	Intermediate Similarity	NPC17681
0.8345	Intermediate Similarity	NPC137570
0.8322	Intermediate Similarity	NPC195920
0.8321	Intermediate Similarity	NPC476351
0.8311	Intermediate Similarity	NPC110305
0.8311	Intermediate Similarity	NPC22248
0.8286	Intermediate Similarity	NPC474279
0.8286	Intermediate Similarity	NPC474438
0.8273	Intermediate Similarity	NPC329694
0.8273	Intermediate Similarity	NPC81912
0.8273	Intermediate Similarity	NPC329922
0.8273	Intermediate Similarity	NPC474260
0.8267	Intermediate Similarity	NPC475864
0.8248	Intermediate Similarity	NPC283284
0.8248	Intermediate Similarity	NPC289911
0.8175	Intermediate Similarity	NPC474136
0.8163	Intermediate Similarity	NPC474615
0.8158	Intermediate Similarity	NPC474220
0.8158	Intermediate Similarity	NPC471618
0.8158	Intermediate Similarity	NPC474255
0.8151	Intermediate Similarity	NPC473268
0.8138	Intermediate Similarity	NPC159786
0.8113	Intermediate Similarity	NPC283209
0.8113	Intermediate Similarity	NPC285567
0.8108	Intermediate Similarity	NPC148374
0.8105	Intermediate Similarity	NPC474270
0.8105	Intermediate Similarity	NPC475904
0.8101	Intermediate Similarity	NPC287559
0.8085	Intermediate Similarity	NPC471501
0.8085	Intermediate Similarity	NPC476016
0.8085	Intermediate Similarity	NPC471554
0.8085	Intermediate Similarity	NPC471573
0.8085	Intermediate Similarity	NPC473355
0.8079	Intermediate Similarity	NPC37488
0.8058	Intermediate Similarity	NPC475818
0.8029	Intermediate Similarity	NPC473969
0.8029	Intermediate Similarity	NPC4898
0.8025	Intermediate Similarity	NPC104736
0.8025	Intermediate Similarity	NPC474542
0.8014	Intermediate Similarity	NPC52035
0.8	Intermediate Similarity	NPC118853
0.7987	Intermediate Similarity	NPC282973
0.7986	Intermediate Similarity	NPC136340
0.7975	Intermediate Similarity	NPC304692
0.7974	Intermediate Similarity	NPC474317
0.7961	Intermediate Similarity	NPC469642
0.7958	Intermediate Similarity	NPC475236
0.7958	Intermediate Similarity	NPC474830
0.7956	Intermediate Similarity	NPC187547
0.7956	Intermediate Similarity	NPC21831
0.7945	Intermediate Similarity	NPC106247
0.7943	Intermediate Similarity	NPC474829
0.7943	Intermediate Similarity	NPC471559
0.7937	Intermediate Similarity	NPC68848
0.7935	Intermediate Similarity	NPC228842
0.7905	Intermediate Similarity	NPC286130
0.7901	Intermediate Similarity	NPC121995
0.7883	Intermediate Similarity	NPC131801
0.7877	Intermediate Similarity	NPC474426
0.7877	Intermediate Similarity	NPC474425
0.7877	Intermediate Similarity	NPC474407
0.7872	Intermediate Similarity	NPC188377
0.7872	Intermediate Similarity	NPC65735
0.7868	Intermediate Similarity	NPC28054
0.7862	Intermediate Similarity	NPC197137
0.7862	Intermediate Similarity	NPC7059
0.7857	Intermediate Similarity	NPC272487
0.7842	Intermediate Similarity	NPC474817
0.7834	Intermediate Similarity	NPC121615
0.7834	Intermediate Similarity	NPC294511
0.7826	Intermediate Similarity	NPC471003
0.7826	Intermediate Similarity	NPC18986
0.7826	Intermediate Similarity	NPC169
0.7817	Intermediate Similarity	NPC221798
0.7815	Intermediate Similarity	NPC248795
0.7812	Intermediate Similarity	NPC84349
0.7808	Intermediate Similarity	NPC471544
0.7808	Intermediate Similarity	NPC473344
0.7808	Intermediate Similarity	NPC471545
0.7805	Intermediate Similarity	NPC296558
0.78	Intermediate Similarity	NPC90953
0.7799	Intermediate Similarity	NPC41880
0.7778	Intermediate Similarity	NPC473090
0.7778	Intermediate Similarity	NPC14822
0.7771	Intermediate Similarity	NPC116717
0.7764	Intermediate Similarity	NPC8389
0.7763	Intermediate Similarity	NPC184053
0.7754	Intermediate Similarity	NPC144745
0.7754	Intermediate Similarity	NPC208906
0.775	Intermediate Similarity	NPC88007
0.775	Intermediate Similarity	NPC261484
0.775	Intermediate Similarity	NPC194499
0.775	Intermediate Similarity	NPC470118
0.7742	Intermediate Similarity	NPC224418
0.7742	Intermediate Similarity	NPC71821
0.774	Intermediate Similarity	NPC475092
0.7738	Intermediate Similarity	NPC472665
0.7736	Intermediate Similarity	NPC290927
0.773	Intermediate Similarity	NPC56358
0.773	Intermediate Similarity	NPC472664
0.773	Intermediate Similarity	NPC261184
0.7727	Intermediate Similarity	NPC34056
0.7724	Intermediate Similarity	NPC2596
0.7716	Intermediate Similarity	NPC303210
0.7716	Intermediate Similarity	NPC95472
0.7716	Intermediate Similarity	NPC79571
0.7716	Intermediate Similarity	NPC239270
0.7716	Intermediate Similarity	NPC49009
0.7712	Intermediate Similarity	NPC267632
0.7712	Intermediate Similarity	NPC223415
0.7712	Intermediate Similarity	NPC80635
0.7711	Intermediate Similarity	NPC475641
0.7711	Intermediate Similarity	NPC475237
0.7707	Intermediate Similarity	NPC5180
0.7702	Intermediate Similarity	NPC269495
0.7692	Intermediate Similarity	NPC61284
0.7692	Intermediate Similarity	NPC113428
0.7688	Intermediate Similarity	NPC469485
0.7683	Intermediate Similarity	NPC475779
0.7676	Intermediate Similarity	NPC291189
0.7676	Intermediate Similarity	NPC69403
0.7673	Intermediate Similarity	NPC263676
0.7673	Intermediate Similarity	NPC131121
0.7669	Intermediate Similarity	NPC476035
0.7669	Intermediate Similarity	NPC14499
0.7669	Intermediate Similarity	NPC88841
0.7669	Intermediate Similarity	NPC475039
0.7669	Intermediate Similarity	NPC288602
0.7667	Intermediate Similarity	NPC186626
0.7665	Intermediate Similarity	NPC120220
0.7662	Intermediate Similarity	NPC251865
0.7662	Intermediate Similarity	NPC137295
0.7662	Intermediate Similarity	NPC84479
0.7658	Intermediate Similarity	NPC291150
0.7658	Intermediate Similarity	NPC191104
0.7658	Intermediate Similarity	NPC116822
0.7654	Intermediate Similarity	NPC228501
0.7651	Intermediate Similarity	NPC118086
0.7651	Intermediate Similarity	NPC88593
0.764	Intermediate Similarity	NPC81405
0.764	Intermediate Similarity	NPC173544
0.764	Intermediate Similarity	NPC195954
0.7639	Intermediate Similarity	NPC88403
0.7639	Intermediate Similarity	NPC216810
0.7636	Intermediate Similarity	NPC310572
0.7636	Intermediate Similarity	NPC270312
0.7635	Intermediate Similarity	NPC293253
0.7628	Intermediate Similarity	NPC250228
0.7628	Intermediate Similarity	NPC308799
0.7626	Intermediate Similarity	NPC312525
0.7626	Intermediate Similarity	NPC227660
0.7626	Intermediate Similarity	NPC217180
0.7625	Intermediate Similarity	NPC25351
0.7625	Intermediate Similarity	NPC296807
0.7625	Intermediate Similarity	NPC84721
0.7625	Intermediate Similarity	NPC155939
0.7625	Intermediate Similarity	NPC141538
0.7625	Intermediate Similarity	NPC92979
0.7622	Intermediate Similarity	NPC27541
0.7622	Intermediate Similarity	NPC126984
0.7622	Intermediate Similarity	NPC61967
0.7622	Intermediate Similarity	NPC62692
0.7622	Intermediate Similarity	NPC243269
0.7619	Intermediate Similarity	NPC472584
0.7613	Intermediate Similarity	NPC213900
0.7613	Intermediate Similarity	NPC105381
0.7613	Intermediate Similarity	NPC10302
0.761	Intermediate Similarity	NPC471613
0.761	Intermediate Similarity	NPC268905
0.761	Intermediate Similarity	NPC75906
0.7609	Intermediate Similarity	NPC205523
0.7607	Intermediate Similarity	NPC139876
0.7607	Intermediate Similarity	NPC188649
0.7605	Intermediate Similarity	NPC294512
0.7597	Intermediate Similarity	NPC470741
0.7595	Intermediate Similarity	NPC212257
0.7595	Intermediate Similarity	NPC88445
0.7593	Intermediate Similarity	NPC76458
0.7593	Intermediate Similarity	NPC140952
0.7593	Intermediate Similarity	NPC82733
0.7582	Intermediate Similarity	NPC326065
0.758	Intermediate Similarity	NPC14875
0.758	Intermediate Similarity	NPC472969

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 NPC261733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	917
0.2-0.3	1738
0.3-0.4	2797
0.4-0.5	1993
0.5-0.6	1059
0.6-0.7	311
0.7-0.8	40
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
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7558	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD6799	Approved
0.7468	Intermediate Similarity	NPD920	Approved
0.7376	Intermediate Similarity	NPD9092	Discovery
0.7342	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6599	Discontinued
0.7284	Intermediate Similarity	NPD7411	Suspended
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD3226	Approved
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7226	Intermediate Similarity	NPD2344	Approved
0.7215	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9545	Approved
0.7195	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1608	Approved
0.7169	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD1247	Approved
0.7126	Intermediate Similarity	NPD919	Approved
0.7115	Intermediate Similarity	NPD1471	Phase 3
0.7114	Intermediate Similarity	NPD5647	Approved
0.7108	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3882	Suspended
0.7103	Intermediate Similarity	NPD17	Approved
0.7097	Intermediate Similarity	NPD2799	Discontinued
0.7069	Intermediate Similarity	NPD6764	Approved
0.7069	Intermediate Similarity	NPD6765	Approved
0.7069	Intermediate Similarity	NPD6559	Discontinued
0.7051	Intermediate Similarity	NPD1551	Phase 2
0.7048	Intermediate Similarity	NPD5402	Approved
0.7048	Intermediate Similarity	NPD3817	Phase 2
0.7047	Intermediate Similarity	NPD3267	Approved
0.7047	Intermediate Similarity	NPD3266	Approved
0.7044	Intermediate Similarity	NPD3887	Approved
0.7044	Intermediate Similarity	NPD2309	Approved
0.7044	Intermediate Similarity	NPD2354	Approved
0.7039	Intermediate Similarity	NPD2313	Discontinued
0.7039	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1243	Approved
0.702	Intermediate Similarity	NPD6832	Phase 2
0.7019	Intermediate Similarity	NPD5401	Approved
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD6002	Phase 3
0.7006	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6005	Phase 3
0.7006	Intermediate Similarity	NPD6004	Phase 3
0.6987	Remote Similarity	NPD7033	Discontinued
0.6964	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3749	Approved
0.6962	Remote Similarity	NPD1549	Phase 2
0.6959	Remote Similarity	NPD9717	Approved
0.6954	Remote Similarity	NPD9494	Approved
0.6943	Remote Similarity	NPD2796	Approved
0.6936	Remote Similarity	NPD2163	Approved
0.6936	Remote Similarity	NPD3818	Discontinued
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2797	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD1934	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6784	Approved
0.691	Remote Similarity	NPD6785	Approved
0.6909	Remote Similarity	NPD4380	Phase 2
0.6903	Remote Similarity	NPD230	Phase 1
0.6903	Remote Similarity	NPD447	Suspended
0.6901	Remote Similarity	NPD6808	Phase 2
0.6899	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2353	Approved
0.6899	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5761	Phase 2
0.6886	Remote Similarity	NPD7819	Suspended
0.6886	Remote Similarity	NPD5760	Phase 2
0.6886	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2801	Approved
0.6883	Remote Similarity	NPD6233	Phase 2
0.6882	Remote Similarity	NPD5494	Approved
0.6875	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3750	Approved
0.6853	Remote Similarity	NPD1241	Discontinued
0.6848	Remote Similarity	NPD7458	Discontinued
0.6846	Remote Similarity	NPD3972	Approved
0.6845	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1240	Approved
0.6821	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1203	Approved
0.6821	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2533	Approved
0.681	Remote Similarity	NPD2534	Approved
0.681	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2532	Approved
0.6792	Remote Similarity	NPD2346	Discontinued
0.6779	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1019	Discontinued
0.6776	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2798	Approved
0.6774	Remote Similarity	NPD4062	Phase 3
0.6772	Remote Similarity	NPD4308	Phase 3
0.6772	Remote Similarity	NPD1510	Phase 2
0.6772	Remote Similarity	NPD3748	Approved
0.6766	Remote Similarity	NPD6386	Approved
0.6766	Remote Similarity	NPD6385	Approved
0.6763	Remote Similarity	NPD3926	Phase 2
0.6761	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1876	Approved
0.6755	Remote Similarity	NPD3225	Approved
0.6752	Remote Similarity	NPD1607	Approved
0.6752	Remote Similarity	NPD6653	Approved
0.6738	Remote Similarity	NPD2182	Approved
0.673	Remote Similarity	NPD2935	Discontinued
0.6723	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3496	Discontinued
0.6707	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5844	Phase 1
0.669	Remote Similarity	NPD2067	Discontinued
0.6688	Remote Similarity	NPD1933	Approved
0.6688	Remote Similarity	NPD4340	Discontinued
0.6688	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7440	Discontinued
0.6686	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD5049	Phase 3
0.6667	Remote Similarity	NPD1358	Approved
0.6647	Remote Similarity	NPD7199	Phase 2
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1511	Approved
0.6644	Remote Similarity	NPD1778	Approved
0.6629	Remote Similarity	NPD6166	Phase 2
0.6629	Remote Similarity	NPD5953	Discontinued
0.6629	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6234	Discontinued
0.6627	Remote Similarity	NPD6280	Approved
0.6627	Remote Similarity	NPD6279	Approved
0.6624	Remote Similarity	NPD3142	Approved
0.6624	Remote Similarity	NPD3140	Approved
0.6624	Remote Similarity	NPD4307	Phase 2
0.6623	Remote Similarity	NPD1481	Phase 2
0.6622	Remote Similarity	NPD1894	Discontinued
0.662	Remote Similarity	NPD2684	Approved
0.6611	Remote Similarity	NPD8312	Approved
0.6611	Remote Similarity	NPD8313	Approved
0.661	Remote Similarity	NPD7286	Phase 2
0.661	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6232	Discontinued
0.6608	Remote Similarity	NPD4965	Approved
0.6608	Remote Similarity	NPD4966	Approved
0.6608	Remote Similarity	NPD4967	Phase 2
0.6608	Remote Similarity	NPD7768	Phase 2
0.6606	Remote Similarity	NPD4662	Approved
0.6606	Remote Similarity	NPD4661	Approved
0.6605	Remote Similarity	NPD2800	Approved
0.6604	Remote Similarity	NPD7097	Phase 1
0.6596	Remote Similarity	NPD3134	Approved
0.6592	Remote Similarity	NPD7685	Pre-registration
0.6588	Remote Similarity	NPD1465	Phase 2
0.6582	Remote Similarity	NPD4622	Approved
0.6582	Remote Similarity	NPD4618	Approved
0.6577	Remote Similarity	NPD5585	Approved
0.6573	Remote Similarity	NPD7074	Phase 3
0.6571	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD958	Approved
0.6566	Remote Similarity	NPD2186	Approved
0.6566	Remote Similarity	NPD1512	Approved
0.6564	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1535	Discovery
0.6552	Remote Similarity	NPD7843	Approved
0.655	Remote Similarity	NPD2296	Approved
0.6548	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5958	Discontinued
0.6538	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6190	Approved
0.6522	Remote Similarity	NPD6032	Approved
0.6519	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4060	Phase 1
0.6517	Remote Similarity	NPD7054	Approved
0.6514	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5688	Approved
0.65	Remote Similarity	NPD5689	Approved
0.6497	Remote Similarity	NPD411	Approved
0.6494	Remote Similarity	NPD6362	Approved
0.6491	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD9493	Approved
0.6482	Remote Similarity	NPD8404	Phase 2
0.648	Remote Similarity	NPD7472	Approved
0.6477	Remote Similarity	NPD5242	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