NPASS Compound

Structure

NPC244174 OpenBabel07101719252D 27 30 0 0 1 0 0 0 0 0999 V2000 -2.8544 2.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0084 -2.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1028 -1.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0688 -0.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0064 1.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8100 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0688 0.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8440 1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3957 0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1421 1.7695 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6994 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3766 2.0438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3617 -0.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3685 -1.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2721 3.0383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6849 1.6163 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 2 13 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 8 15 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 21 1 0 0 0 0 11 22 1 0 0 0 0 12 1 1 1 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 23 2 0 0 0 0 13 25 1 0 0 0 0 14 7 1 6 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 17 16 1 6 0 0 0 17 20 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 25 1 1 0 0 0 19 27 1 0 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 22 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	390.884
LogP:	4.703
LogD:	3.963
LogS:	-5.351
# Rotatable Bonds:	3
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	4.688
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.811
MDCK Permeability:	2.249959834443871e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.776

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	92.21146392822266%
Volume Distribution (VD):	1.888
Pgp-substrate:	9.022040367126465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.289
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.345
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.125
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.654
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	1.526
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.725
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.678
Carcinogencity:	0.21
Eye Corrosion:	0.645
Eye Irritation:	0.167
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC244174

Natural Product ID:	NPC244174
*Common Name:**	LYEXPFKXURJWNG-MEYBLWIUSA-N
IUPAC Name:	n.a.
Synonyms:	Tetrahydroaplysulphurin-1
Standard InCHIKey:	LYEXPFKXURJWNG-MEYBLWIUSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-12-16-15(22(5)10-6-9-21(3,4)11-22)8-7-14-17(16)20(26-18(12)24)27-19(14)25-13(2)23/h12,14,17,19-20H,6-11H2,1-5H3/t12-,14-,17-,19-,20-,22+/m1/s1
SMILES:	CC(=O)O[C@@H]1O[C@@H]2[C@@H]3[C@H]1CCC(=C3[C@H](C(=O)O2)C)[C@@]1(C)CCCC(C1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077773
PubChem CID:	23247763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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
NPO33347	spongionella sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19601607]
NPO40100	Dendrilla antarctica	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32281798]

☑ 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	4
Others	1

Activity Type	# Activity
Cell Line	3
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	4500.0	nM	PMID[570922]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	2300.0	nM	PMID[570922]
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	>	133000.0	nM	PMID[570923]
NPT2	Others	Unspecified		Ratio IC50	>	38.0	n.a.	PMID[570923]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	3500.0	nM	PMID[570923]

☑ 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 NPC244174 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	208
0.1-0.2	1582
0.2-0.3	6621
0.3-0.4	15120
0.4-0.5	6883
0.5-0.6	6898
0.6-0.7	4971
0.7-0.8	407
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC474631
0.8242	Intermediate Similarity	NPC470576
0.8172	Intermediate Similarity	NPC311166
0.8161	Intermediate Similarity	NPC71626
0.8132	Intermediate Similarity	NPC165904
0.8132	Intermediate Similarity	NPC65513
0.8132	Intermediate Similarity	NPC179517
0.8118	Intermediate Similarity	NPC473685
0.809	Intermediate Similarity	NPC265580
0.8085	Intermediate Similarity	NPC257726
0.8085	Intermediate Similarity	NPC204054
0.8043	Intermediate Similarity	NPC267266
0.8043	Intermediate Similarity	NPC277721
0.798	Intermediate Similarity	NPC293512
0.7957	Intermediate Similarity	NPC41649
0.7957	Intermediate Similarity	NPC88507
0.7849	Intermediate Similarity	NPC470656
0.7822	Intermediate Similarity	NPC112457
0.7789	Intermediate Similarity	NPC112654
0.7778	Intermediate Similarity	NPC223741
0.7778	Intermediate Similarity	NPC118266
0.7755	Intermediate Similarity	NPC134077
0.7753	Intermediate Similarity	NPC109512
0.7753	Intermediate Similarity	NPC469569
0.7753	Intermediate Similarity	NPC469407
0.7745	Intermediate Similarity	NPC127153
0.7723	Intermediate Similarity	NPC295389
0.7717	Intermediate Similarity	NPC293044
0.7708	Intermediate Similarity	NPC472188
0.77	Intermediate Similarity	NPC162033
0.7692	Intermediate Similarity	NPC288952
0.7684	Intermediate Similarity	NPC275310
0.7684	Intermediate Similarity	NPC286612
0.7684	Intermediate Similarity	NPC230347
0.7677	Intermediate Similarity	NPC132395
0.7677	Intermediate Similarity	NPC471365
0.7677	Intermediate Similarity	NPC471364
0.7674	Intermediate Similarity	NPC4827
0.7667	Intermediate Similarity	NPC300985
0.766	Intermediate Similarity	NPC471571
0.7653	Intermediate Similarity	NPC63249
0.7647	Intermediate Similarity	NPC41017
0.7647	Intermediate Similarity	NPC477069
0.7647	Intermediate Similarity	NPC118225
0.7647	Intermediate Similarity	NPC477070
0.7634	Intermediate Similarity	NPC219495
0.7629	Intermediate Similarity	NPC472186
0.7629	Intermediate Similarity	NPC471366
0.7629	Intermediate Similarity	NPC318917
0.7629	Intermediate Similarity	NPC476800
0.7604	Intermediate Similarity	NPC94905
0.7604	Intermediate Similarity	NPC8954
0.76	Intermediate Similarity	NPC476764
0.76	Intermediate Similarity	NPC476763
0.7586	Intermediate Similarity	NPC327674
0.7582	Intermediate Similarity	NPC471369
0.7582	Intermediate Similarity	NPC471368
0.7556	Intermediate Similarity	NPC82492
0.7556	Intermediate Similarity	NPC51135
0.7556	Intermediate Similarity	NPC475193
0.7556	Intermediate Similarity	NPC25802
0.7556	Intermediate Similarity	NPC101138
0.7556	Intermediate Similarity	NPC100391
0.7556	Intermediate Similarity	NPC120158
0.7551	Intermediate Similarity	NPC472187
0.7551	Intermediate Similarity	NPC473545
0.7551	Intermediate Similarity	NPC473204
0.7549	Intermediate Similarity	NPC195708
0.7549	Intermediate Similarity	NPC469845
0.7549	Intermediate Similarity	NPC473288
0.7549	Intermediate Similarity	NPC285576
0.7526	Intermediate Similarity	NPC76266
0.7526	Intermediate Similarity	NPC187159
0.7525	Intermediate Similarity	NPC252296
0.7525	Intermediate Similarity	NPC475611
0.7525	Intermediate Similarity	NPC476760
0.7525	Intermediate Similarity	NPC476762
0.7525	Intermediate Similarity	NPC476761
0.7525	Intermediate Similarity	NPC210178
0.7524	Intermediate Similarity	NPC474410
0.7524	Intermediate Similarity	NPC157441
0.7524	Intermediate Similarity	NPC293658
0.75	Intermediate Similarity	NPC195424
0.75	Intermediate Similarity	NPC477073
0.75	Intermediate Similarity	NPC474956
0.75	Intermediate Similarity	NPC471372
0.75	Intermediate Similarity	NPC473369
0.75	Intermediate Similarity	NPC472189
0.75	Intermediate Similarity	NPC471362
0.7476	Intermediate Similarity	NPC246205
0.7476	Intermediate Similarity	NPC265655
0.7474	Intermediate Similarity	NPC472226
0.7474	Intermediate Similarity	NPC166346
0.7474	Intermediate Similarity	NPC472225
0.7473	Intermediate Similarity	NPC470223
0.7471	Intermediate Similarity	NPC35574
0.7451	Intermediate Similarity	NPC283849
0.7451	Intermediate Similarity	NPC473538
0.7451	Intermediate Similarity	NPC184512
0.7444	Intermediate Similarity	NPC476100
0.7444	Intermediate Similarity	NPC472440
0.7442	Intermediate Similarity	NPC899
0.7429	Intermediate Similarity	NPC233003
0.7429	Intermediate Similarity	NPC194951
0.7429	Intermediate Similarity	NPC12046
0.7426	Intermediate Similarity	NPC100955
0.7426	Intermediate Similarity	NPC222161
0.7426	Intermediate Similarity	NPC121566
0.7423	Intermediate Similarity	NPC73858
0.7423	Intermediate Similarity	NPC171598
0.7423	Intermediate Similarity	NPC42042
0.7423	Intermediate Similarity	NPC319692
0.7423	Intermediate Similarity	NPC111684
0.7423	Intermediate Similarity	NPC58052
0.7423	Intermediate Similarity	NPC325960
0.7419	Intermediate Similarity	NPC477128
0.7416	Intermediate Similarity	NPC474955
0.7416	Intermediate Similarity	NPC149237
0.7416	Intermediate Similarity	NPC327002
0.7412	Intermediate Similarity	NPC166797
0.7404	Intermediate Similarity	NPC83005
0.7404	Intermediate Similarity	NPC274507
0.7404	Intermediate Similarity	NPC114961
0.7404	Intermediate Similarity	NPC27551
0.7404	Intermediate Similarity	NPC129340
0.7404	Intermediate Similarity	NPC475501
0.7404	Intermediate Similarity	NPC101450
0.74	Intermediate Similarity	NPC238397
0.74	Intermediate Similarity	NPC471363
0.7396	Intermediate Similarity	NPC472224
0.7396	Intermediate Similarity	NPC128488
0.7396	Intermediate Similarity	NPC304968
0.7396	Intermediate Similarity	NPC474963
0.7396	Intermediate Similarity	NPC474554
0.7396	Intermediate Similarity	NPC472223
0.7391	Intermediate Similarity	NPC474062
0.7391	Intermediate Similarity	NPC264127
0.7383	Intermediate Similarity	NPC189126
0.7383	Intermediate Similarity	NPC243981
0.7379	Intermediate Similarity	NPC469844
0.7379	Intermediate Similarity	NPC177246
0.7379	Intermediate Similarity	NPC325054
0.7379	Intermediate Similarity	NPC476123
0.7379	Intermediate Similarity	NPC28198
0.7379	Intermediate Similarity	NPC94942
0.7379	Intermediate Similarity	NPC284807
0.7368	Intermediate Similarity	NPC150383
0.7363	Intermediate Similarity	NPC471367
0.7363	Intermediate Similarity	NPC312660
0.7358	Intermediate Similarity	NPC251309
0.7358	Intermediate Similarity	NPC477074
0.7356	Intermediate Similarity	NPC316500
0.7353	Intermediate Similarity	NPC127790
0.7353	Intermediate Similarity	NPC95243
0.7353	Intermediate Similarity	NPC63023
0.7353	Intermediate Similarity	NPC127609
0.7347	Intermediate Similarity	NPC158347
0.7347	Intermediate Similarity	NPC98112
0.734	Intermediate Similarity	NPC471222
0.734	Intermediate Similarity	NPC284561
0.734	Intermediate Similarity	NPC174765
0.7339	Intermediate Similarity	NPC122971
0.7333	Intermediate Similarity	NPC470577
0.7333	Intermediate Similarity	NPC191763
0.7333	Intermediate Similarity	NPC321289
0.7333	Intermediate Similarity	NPC292196
0.7333	Intermediate Similarity	NPC473481
0.7333	Intermediate Similarity	NPC285410
0.7333	Intermediate Similarity	NPC30397
0.7333	Intermediate Similarity	NPC263827
0.7333	Intermediate Similarity	NPC235841
0.7333	Intermediate Similarity	NPC327969
0.7333	Intermediate Similarity	NPC211798
0.7333	Intermediate Similarity	NPC250481
0.7333	Intermediate Similarity	NPC297208
0.7333	Intermediate Similarity	NPC190837
0.7333	Intermediate Similarity	NPC108748
0.7327	Intermediate Similarity	NPC475889
0.7327	Intermediate Similarity	NPC7644
0.7327	Intermediate Similarity	NPC254202
0.7327	Intermediate Similarity	NPC7613
0.7327	Intermediate Similarity	NPC134270
0.7327	Intermediate Similarity	NPC127933
0.732	Intermediate Similarity	NPC108141
0.7315	Intermediate Similarity	NPC477252
0.7312	Intermediate Similarity	NPC167877
0.7308	Intermediate Similarity	NPC237503
0.7308	Intermediate Similarity	NPC167383
0.7308	Intermediate Similarity	NPC31522
0.7308	Intermediate Similarity	NPC127853
0.7308	Intermediate Similarity	NPC306746
0.7308	Intermediate Similarity	NPC476759
0.7308	Intermediate Similarity	NPC143706
0.7308	Intermediate Similarity	NPC204407
0.7308	Intermediate Similarity	NPC57362
0.7308	Intermediate Similarity	NPC137917
0.7308	Intermediate Similarity	NPC472534
0.7303	Intermediate Similarity	NPC477057
0.7303	Intermediate Similarity	NPC104545
0.7303	Intermediate Similarity	NPC60568

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 NPC244174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1972
0.2-0.3	4231
0.3-0.4	1853
0.4-0.5	484
0.5-0.6	230
0.6-0.7	184
0.7-0.8	17
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
0.7308	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6399	Phase 3
0.7282	Intermediate Similarity	NPD6412	Phase 2
0.7234	Intermediate Similarity	NPD6672	Approved
0.7234	Intermediate Similarity	NPD5737	Approved
0.7212	Intermediate Similarity	NPD6686	Approved
0.7204	Intermediate Similarity	NPD7521	Approved
0.7204	Intermediate Similarity	NPD7146	Approved
0.7204	Intermediate Similarity	NPD7334	Approved
0.7204	Intermediate Similarity	NPD6684	Approved
0.7204	Intermediate Similarity	NPD6409	Approved
0.7204	Intermediate Similarity	NPD5330	Approved
0.7156	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6903	Approved
0.7019	Intermediate Similarity	NPD6008	Approved
0.6957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7900	Approved
0.6869	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1780	Approved
0.6848	Remote Similarity	NPD1779	Approved
0.6842	Remote Similarity	NPD6098	Approved
0.6837	Remote Similarity	NPD6411	Approved
0.6804	Remote Similarity	NPD6673	Approved
0.6804	Remote Similarity	NPD6904	Approved
0.6804	Remote Similarity	NPD6080	Approved
0.68	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3573	Approved
0.67	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6638	Remote Similarity	NPD8328	Phase 3
0.6636	Remote Similarity	NPD6882	Approved
0.6634	Remote Similarity	NPD5695	Phase 3
0.6633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6101	Approved
0.6632	Remote Similarity	NPD4786	Approved
0.6632	Remote Similarity	NPD3668	Phase 3
0.661	Remote Similarity	NPD8293	Discontinued
0.6596	Remote Similarity	NPD3667	Approved
0.6577	Remote Similarity	NPD8133	Approved
0.6566	Remote Similarity	NPD5207	Approved
0.6566	Remote Similarity	NPD5692	Phase 3
0.6562	Remote Similarity	NPD1694	Approved
0.6555	Remote Similarity	NPD7736	Approved
0.6552	Remote Similarity	NPD6370	Approved
0.6542	Remote Similarity	NPD6675	Approved
0.6542	Remote Similarity	NPD6402	Approved
0.6542	Remote Similarity	NPD5739	Approved
0.6542	Remote Similarity	NPD7128	Approved
0.6531	Remote Similarity	NPD5208	Approved
0.6525	Remote Similarity	NPD7507	Approved
0.65	Remote Similarity	NPD8034	Phase 2
0.65	Remote Similarity	NPD5693	Phase 1
0.65	Remote Similarity	NPD8035	Phase 2
0.65	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD5694	Approved
0.6481	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7638	Approved
0.6442	Remote Similarity	NPD5696	Approved
0.6441	Remote Similarity	NPD7492	Approved
0.6422	Remote Similarity	NPD7320	Approved
0.6422	Remote Similarity	NPD6899	Approved
0.6422	Remote Similarity	NPD6881	Approved
0.6408	Remote Similarity	NPD7732	Phase 3
0.6404	Remote Similarity	NPD5777	Approved
0.6404	Remote Similarity	NPD6009	Approved
0.6387	Remote Similarity	NPD6616	Approved
0.6381	Remote Similarity	NPD7639	Approved
0.6381	Remote Similarity	NPD7640	Approved
0.6379	Remote Similarity	NPD6054	Approved
0.6379	Remote Similarity	NPD6059	Approved
0.6374	Remote Similarity	NPD3702	Approved
0.6374	Remote Similarity	NPD8039	Approved
0.6373	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD7319	Approved
0.6356	Remote Similarity	NPD7122	Discontinued
0.6356	Remote Similarity	NPD6067	Discontinued
0.6344	Remote Similarity	NPD3617	Approved
0.6337	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD5281	Approved
0.6333	Remote Similarity	NPD7078	Approved
0.633	Remote Similarity	NPD5697	Approved
0.633	Remote Similarity	NPD5701	Approved
0.6325	Remote Similarity	NPD8516	Approved
0.6325	Remote Similarity	NPD8517	Approved
0.6325	Remote Similarity	NPD8515	Approved
0.6325	Remote Similarity	NPD8513	Phase 3
0.6311	Remote Similarity	NPD5654	Approved
0.6306	Remote Similarity	NPD7102	Approved
0.6306	Remote Similarity	NPD6883	Approved
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7290	Approved
0.63	Remote Similarity	NPD5328	Approved
0.63	Remote Similarity	NPD6051	Approved
0.6289	Remote Similarity	NPD3133	Approved
0.6289	Remote Similarity	NPD3665	Phase 1
0.6289	Remote Similarity	NPD3666	Approved
0.6275	Remote Similarity	NPD5778	Approved
0.6275	Remote Similarity	NPD5779	Approved
0.6273	Remote Similarity	NPD6011	Approved
0.6262	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6650	Approved
0.625	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6013	Approved
0.6216	Remote Similarity	NPD6014	Approved
0.6216	Remote Similarity	NPD6012	Approved
0.6211	Remote Similarity	NPD4695	Discontinued
0.6204	Remote Similarity	NPD6052	Approved
0.6195	Remote Similarity	NPD6053	Discontinued
0.6195	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD5959	Approved
0.6186	Remote Similarity	NPD3669	Approved
0.6186	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD6016	Approved
0.6176	Remote Similarity	NPD6079	Approved
0.6162	Remote Similarity	NPD3618	Phase 1
0.6148	Remote Similarity	NPD8336	Approved
0.6148	Remote Similarity	NPD8337	Approved
0.6147	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4692	Approved
0.6146	Remote Similarity	NPD4139	Approved
0.614	Remote Similarity	NPD4632	Approved
0.6139	Remote Similarity	NPD4753	Phase 2
0.6134	Remote Similarity	NPD5988	Approved
0.6106	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7614	Phase 1
0.6082	Remote Similarity	NPD4223	Phase 3
0.6082	Remote Similarity	NPD4221	Approved
0.6068	Remote Similarity	NPD7328	Approved
0.6068	Remote Similarity	NPD7327	Approved
0.6064	Remote Similarity	NPD6116	Phase 1
0.6061	Remote Similarity	NPD5329	Approved
0.6058	Remote Similarity	NPD5282	Discontinued
0.605	Remote Similarity	NPD7503	Approved
0.605	Remote Similarity	NPD8033	Approved
0.6048	Remote Similarity	NPD6914	Discontinued
0.6038	Remote Similarity	NPD4755	Approved
0.6017	Remote Similarity	NPD7516	Approved
0.6016	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD6697	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6422	Discontinued
0.6	Remote Similarity	NPD6115	Approved
0.6	Remote Similarity	NPD4137	Phase 3
0.6	Remote Similarity	NPD6114	Approved
0.6	Remote Similarity	NPD6118	Approved
0.5983	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD8377	Approved
0.5966	Remote Similarity	NPD8294	Approved
0.5966	Remote Similarity	NPD6319	Approved
0.5962	Remote Similarity	NPD4202	Approved
0.596	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4197	Approved
0.5957	Remote Similarity	NPD6117	Approved
0.595	Remote Similarity	NPD7604	Phase 2
0.5943	Remote Similarity	NPD5222	Approved
0.5943	Remote Similarity	NPD4697	Phase 3
0.5943	Remote Similarity	NPD5221	Approved
0.5943	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD2254	Approved
0.5934	Remote Similarity	NPD2686	Approved
0.5934	Remote Similarity	NPD4691	Approved
0.5934	Remote Similarity	NPD2687	Approved
0.5934	Remote Similarity	NPD4747	Approved
0.5932	Remote Similarity	NPD6335	Approved
0.5926	Remote Similarity	NPD5285	Approved
0.5926	Remote Similarity	NPD5286	Approved
0.5926	Remote Similarity	NPD4700	Approved
0.5926	Remote Similarity	NPD4696	Approved
0.5922	Remote Similarity	NPD6698	Approved
0.5922	Remote Similarity	NPD46	Approved
0.5918	Remote Similarity	NPD6435	Approved
0.5917	Remote Similarity	NPD8335	Approved
0.5917	Remote Similarity	NPD8378	Approved
0.5917	Remote Similarity	NPD8380	Approved
0.5917	Remote Similarity	NPD8379	Approved
0.5917	Remote Similarity	NPD5983	Phase 2
0.5917	Remote Similarity	NPD8296	Approved
0.5914	Remote Similarity	NPD5733	Approved
0.5914	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6868	Approved
0.5897	Remote Similarity	NPD6274	Approved
0.5893	Remote Similarity	NPD6614	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