NPASS Compound

Structure

NPC282793 OpenBabel07101718182D 26 30 0 0 1 0 0 0 0 0999 V2000 -2.6270 -2.4119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6327 -3.2478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1302 -2.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5741 -2.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0925 -0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0925 -1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0484 -1.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7967 -0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7967 -1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3884 -0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3884 -1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9898 -1.2800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2051 -1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 -1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 -0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -0.0995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2051 -0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9599 -0.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -1.9266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0711 -1.9196 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 -2.8262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 0.8001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9751 0.8754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0711 -0.1065 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 3 1 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 20 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 26 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 1 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.05
Volume:	347.128
LogP:	3.508
LogD:	2.249
LogS:	-6.332
# Rotatable Bonds:	0
TPSA:	81.42
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	4.171
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	2.323548869753722e-05
Pgp-inhibitor:	0.764
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	95.58126831054688%
Volume Distribution (VD):	1.406
Pgp-substrate:	1.9446148872375488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.7
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.461
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.594
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.403
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.619
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	1.538
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.704
AMES Toxicity:	0.711
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.23
Carcinogencity:	0.819
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC282793

Natural Product ID:	NPC282793
*Common Name:**	LTWBQTKGRSVOPR-FQEVSTJZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LTWBQTKGRSVOPR-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C20H13ClO5/c1-20-4-2-3-8-7-26-19(13(8)20)17(24)11-5-9-10(6-12(11)20)15(22)14(21)18(25)16(9)23/h5-7,25H,2-4H2,1H3/t20-/m0/s1
SMILES:	ClC1=C(O)C(=O)c2c(C1=O)cc1c(c2)C(=O)c2c3[C@@]1(C)CCCc3co2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL138236
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908959]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Caledonian	n.a.	PMID[1453184]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Thai	n.a.	PMID[14640515]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	thai	n.a.	PMID[15217287]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1710256]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[20503979]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	coral reef habitat at a depth of approximately 20 m from the sea bed surface, at Sangalaki, Indonesia (2 04 59 N, 118 23 41 E)	1996-MAR	PMID[20503979]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31260310]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Philippine	n.a.	PMID[7473578]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798966]

☑ 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	2
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Others	1
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	33000.0	nM	PMID[524654]
NPT6399	Cell Line	XRS6	Cricetulus griseus	IC50	n.a.	2727000.0	nM	PMID[524654]
NPT5376	Individual Protein	DNA topoisomerase II	Drosophila melanogaster	IC90	=	135000.0	nM	PMID[524654]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	IC90	=	110000.0	nM	PMID[524654]
NPT2	Others	Unspecified		Ratio	=	4.5	n.a.	PMID[524654]

☑ 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 NPC282793 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	357
0.1-0.2	1660
0.2-0.3	3579
0.3-0.4	9933
0.4-0.5	9855
0.5-0.6	6577
0.6-0.7	9581
0.7-0.8	1123
0.8-0.85	23
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC469966
0.9315	High Similarity	NPC114513
0.9315	High Similarity	NPC245522
0.894	High Similarity	NPC192069
0.8896	High Similarity	NPC88958
0.8867	High Similarity	NPC478166
0.8535	High Similarity	NPC179170
0.8526	High Similarity	NPC145830
0.8323	Intermediate Similarity	NPC281398
0.8313	Intermediate Similarity	NPC221992
0.8293	Intermediate Similarity	NPC472784
0.8247	Intermediate Similarity	NPC117674
0.8228	Intermediate Similarity	NPC144010
0.8194	Intermediate Similarity	NPC27798
0.8194	Intermediate Similarity	NPC93241
0.8193	Intermediate Similarity	NPC44602
0.8158	Intermediate Similarity	NPC202260
0.8153	Intermediate Similarity	NPC478163
0.8148	Intermediate Similarity	NPC299094
0.8148	Intermediate Similarity	NPC10051
0.8137	Intermediate Similarity	NPC478159
0.8137	Intermediate Similarity	NPC478161
0.8117	Intermediate Similarity	NPC263337
0.8084	Intermediate Similarity	NPC473945
0.8075	Intermediate Similarity	NPC25351
0.8049	Intermediate Similarity	NPC472781
0.8049	Intermediate Similarity	NPC472782
0.8039	Intermediate Similarity	NPC265181
0.8037	Intermediate Similarity	NPC472823
0.8012	Intermediate Similarity	NPC10429
0.8012	Intermediate Similarity	NPC44606
0.8	Intermediate Similarity	NPC472780
0.8	Intermediate Similarity	NPC472783
0.7977	Intermediate Similarity	NPC472533
0.7962	Intermediate Similarity	NPC290038
0.795	Intermediate Similarity	NPC471613
0.7927	Intermediate Similarity	NPC123153
0.7925	Intermediate Similarity	NPC252208
0.7922	Intermediate Similarity	NPC233707
0.7911	Intermediate Similarity	NPC233763
0.7908	Intermediate Similarity	NPC471670
0.7908	Intermediate Similarity	NPC307401
0.7895	Intermediate Similarity	NPC324117
0.7888	Intermediate Similarity	NPC472787
0.7879	Intermediate Similarity	NPC472299
0.7875	Intermediate Similarity	NPC280025
0.7875	Intermediate Similarity	NPC95526
0.7871	Intermediate Similarity	NPC201370
0.7871	Intermediate Similarity	NPC18904
0.7871	Intermediate Similarity	NPC473983
0.7866	Intermediate Similarity	NPC7059
0.7857	Intermediate Similarity	NPC177262
0.7857	Intermediate Similarity	NPC41689
0.7853	Intermediate Similarity	NPC472786
0.7853	Intermediate Similarity	NPC75310
0.7852	Intermediate Similarity	NPC59502
0.7848	Intermediate Similarity	NPC185456
0.7843	Intermediate Similarity	NPC22644
0.7826	Intermediate Similarity	NPC226578
0.7826	Intermediate Similarity	NPC472298
0.7826	Intermediate Similarity	NPC212257
0.7826	Intermediate Similarity	NPC228842
0.7805	Intermediate Similarity	NPC104736
0.7805	Intermediate Similarity	NPC41880
0.7798	Intermediate Similarity	NPC475779
0.7797	Intermediate Similarity	NPC472358
0.7791	Intermediate Similarity	NPC27615
0.7785	Intermediate Similarity	NPC53016
0.7785	Intermediate Similarity	NPC158871
0.7785	Intermediate Similarity	NPC26532
0.7778	Intermediate Similarity	NPC474659
0.7778	Intermediate Similarity	NPC272590
0.7778	Intermediate Similarity	NPC209858
0.7771	Intermediate Similarity	NPC8389
0.7771	Intermediate Similarity	NPC287559
0.7758	Intermediate Similarity	NPC304692
0.7758	Intermediate Similarity	NPC81405
0.7756	Intermediate Similarity	NPC148374
0.7756	Intermediate Similarity	NPC61157
0.7756	Intermediate Similarity	NPC218204
0.7756	Intermediate Similarity	NPC473681
0.7756	Intermediate Similarity	NPC470407
0.7755	Intermediate Similarity	NPC178382
0.7744	Intermediate Similarity	NPC472785
0.7742	Intermediate Similarity	NPC186647
0.7742	Intermediate Similarity	NPC471996
0.773	Intermediate Similarity	NPC246164
0.773	Intermediate Similarity	NPC121615
0.773	Intermediate Similarity	NPC475777
0.773	Intermediate Similarity	NPC294511
0.7725	Intermediate Similarity	NPC79571
0.7722	Intermediate Similarity	NPC201297
0.7718	Intermediate Similarity	NPC246392
0.7711	Intermediate Similarity	NPC217602
0.7711	Intermediate Similarity	NPC104380
0.7711	Intermediate Similarity	NPC476404
0.7711	Intermediate Similarity	NPC317900
0.7711	Intermediate Similarity	NPC140952
0.7711	Intermediate Similarity	NPC473282
0.7711	Intermediate Similarity	NPC294300
0.7697	Intermediate Similarity	NPC473982
0.7697	Intermediate Similarity	NPC471995
0.7697	Intermediate Similarity	NPC3898
0.7697	Intermediate Similarity	NPC279596
0.7692	Intermediate Similarity	NPC308156
0.7688	Intermediate Similarity	NPC167340
0.7688	Intermediate Similarity	NPC478160
0.7679	Intermediate Similarity	NPC14499
0.7679	Intermediate Similarity	NPC476035
0.7679	Intermediate Similarity	NPC475039
0.7673	Intermediate Similarity	NPC478164
0.7667	Intermediate Similarity	NPC329707
0.7662	Intermediate Similarity	NPC23894
0.7661	Intermediate Similarity	NPC472660
0.7654	Intermediate Similarity	NPC472839
0.7651	Intermediate Similarity	NPC288353
0.7647	Intermediate Similarity	NPC314653
0.7647	Intermediate Similarity	NPC316262
0.7643	Intermediate Similarity	NPC90296
0.764	Intermediate Similarity	NPC302987
0.764	Intermediate Similarity	NPC71821
0.7636	Intermediate Similarity	NPC290927
0.7632	Intermediate Similarity	NPC61788
0.7628	Intermediate Similarity	NPC290601
0.7622	Intermediate Similarity	NPC230848
0.7619	Intermediate Similarity	NPC68848
0.7619	Intermediate Similarity	NPC313368
0.7619	Intermediate Similarity	NPC18986
0.7613	Intermediate Similarity	NPC217914
0.761	Intermediate Similarity	NPC243577
0.7605	Intermediate Similarity	NPC474611
0.7605	Intermediate Similarity	NPC201127
0.7605	Intermediate Similarity	NPC67197
0.7602	Intermediate Similarity	NPC191012
0.7602	Intermediate Similarity	NPC291742
0.7602	Intermediate Similarity	NPC255787
0.7593	Intermediate Similarity	NPC478018
0.7593	Intermediate Similarity	NPC93666
0.7588	Intermediate Similarity	NPC121995
0.7588	Intermediate Similarity	NPC277618
0.7582	Intermediate Similarity	NPC239134
0.7582	Intermediate Similarity	NPC164295
0.7574	Intermediate Similarity	NPC283209
0.7574	Intermediate Similarity	NPC285567
0.7564	Intermediate Similarity	NPC64157
0.7564	Intermediate Similarity	NPC278832
0.7562	Intermediate Similarity	NPC238843
0.7562	Intermediate Similarity	NPC163948
0.7562	Intermediate Similarity	NPC199044
0.7561	Intermediate Similarity	NPC58310
0.7561	Intermediate Similarity	NPC295977
0.7558	Intermediate Similarity	NPC302392
0.7551	Intermediate Similarity	NPC97566
0.755	Intermediate Similarity	NPC428300
0.7548	Intermediate Similarity	NPC265793
0.7546	Intermediate Similarity	NPC211625
0.7546	Intermediate Similarity	NPC472841
0.7545	Intermediate Similarity	NPC194499
0.7545	Intermediate Similarity	NPC88007
0.7545	Intermediate Similarity	NPC195954
0.7544	Intermediate Similarity	NPC473766
0.7544	Intermediate Similarity	NPC473753
0.7532	Intermediate Similarity	NPC218838
0.7532	Intermediate Similarity	NPC293253
0.753	Intermediate Similarity	NPC208806
0.753	Intermediate Similarity	NPC214632
0.753	Intermediate Similarity	NPC23559
0.7529	Intermediate Similarity	NPC472664
0.7529	Intermediate Similarity	NPC193998
0.7529	Intermediate Similarity	NPC56358
0.7529	Intermediate Similarity	NPC475106
0.7527	Intermediate Similarity	NPC163867
0.7516	Intermediate Similarity	NPC472836
0.7516	Intermediate Similarity	NPC469385
0.7516	Intermediate Similarity	NPC27659
0.7515	Intermediate Similarity	NPC471003
0.7515	Intermediate Similarity	NPC472838
0.7515	Intermediate Similarity	NPC306011
0.7515	Intermediate Similarity	NPC115869
0.7515	Intermediate Similarity	NPC21046
0.75	Intermediate Similarity	NPC80370
0.75	Intermediate Similarity	NPC50583
0.75	Intermediate Similarity	NPC208389
0.75	Intermediate Similarity	NPC46896
0.75	Intermediate Similarity	NPC69755
0.75	Intermediate Similarity	NPC295914
0.75	Intermediate Similarity	NPC473368
0.75	Intermediate Similarity	NPC272196
0.75	Intermediate Similarity	NPC296558
0.7485	Intermediate Similarity	NPC100849
0.7485	Intermediate Similarity	NPC52692
0.7485	Intermediate Similarity	NPC5568
0.7485	Intermediate Similarity	NPC58373
0.7484	Intermediate Similarity	NPC470406
0.7484	Intermediate Similarity	NPC477139
0.7483	Intermediate Similarity	NPC290955
0.7471	Intermediate Similarity	NPC313717
0.7471	Intermediate Similarity	NPC24761
0.7471	Intermediate Similarity	NPC315306
0.747	Intermediate Similarity	NPC40356

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 NPC282793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	1011
0.2-0.3	1413
0.3-0.4	2693
0.4-0.5	2244
0.5-0.6	1070
0.6-0.7	380
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8039	Intermediate Similarity	NPD1471	Phase 3
0.7714	Intermediate Similarity	NPD6785	Approved
0.7714	Intermediate Similarity	NPD6784	Approved
0.7692	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD6273	Approved
0.7375	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD7003	Approved
0.7288	Intermediate Similarity	NPD6764	Approved
0.7288	Intermediate Similarity	NPD6765	Approved
0.7251	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2344	Approved
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2354	Approved
0.7176	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4628	Phase 3
0.7115	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3972	Approved
0.7073	Intermediate Similarity	NPD3887	Approved
0.7073	Intermediate Similarity	NPD2309	Approved
0.707	Intermediate Similarity	NPD2313	Discontinued
0.7041	Intermediate Similarity	NPD6599	Discontinued
0.7037	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2353	Approved
0.703	Intermediate Similarity	NPD7236	Approved
0.7019	Intermediate Similarity	NPD2799	Discontinued
0.7018	Intermediate Similarity	NPD5760	Phase 2
0.7018	Intermediate Similarity	NPD5761	Phase 2
0.7018	Intermediate Similarity	NPD7819	Suspended
0.7013	Intermediate Similarity	NPD1876	Approved
0.7012	Intermediate Similarity	NPD3750	Approved
0.7	Intermediate Similarity	NPD7411	Suspended
0.6994	Remote Similarity	NPD4534	Discontinued
0.6977	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6959	Discontinued
0.6971	Remote Similarity	NPD1247	Approved
0.6946	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7239	Suspended
0.6919	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3748	Approved
0.6903	Remote Similarity	NPD1283	Approved
0.6897	Remote Similarity	NPD3749	Approved
0.6857	Remote Similarity	NPD919	Approved
0.6855	Remote Similarity	NPD6798	Discontinued
0.6855	Remote Similarity	NPD3268	Approved
0.6848	Remote Similarity	NPD2800	Approved
0.6845	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1651	Approved
0.6833	Remote Similarity	NPD5844	Phase 1
0.6832	Remote Similarity	NPD6355	Discontinued
0.6818	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6559	Discontinued
0.6813	Remote Similarity	NPD8032	Phase 2
0.681	Remote Similarity	NPD4308	Phase 3
0.68	Remote Similarity	NPD7075	Discontinued
0.6792	Remote Similarity	NPD7008	Discontinued
0.6792	Remote Similarity	NPD7095	Approved
0.6788	Remote Similarity	NPD5958	Discontinued
0.6779	Remote Similarity	NPD1241	Discontinued
0.6778	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7177	Discontinued
0.677	Remote Similarity	NPD4060	Phase 1
0.6765	Remote Similarity	NPD920	Approved
0.676	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4879	Approved
0.6752	Remote Similarity	NPD3267	Approved
0.6752	Remote Similarity	NPD3266	Approved
0.675	Remote Similarity	NPD3764	Approved
0.6746	Remote Similarity	NPD2532	Approved
0.6746	Remote Similarity	NPD2534	Approved
0.6746	Remote Similarity	NPD2533	Approved
0.6743	Remote Similarity	NPD3882	Suspended
0.6726	Remote Similarity	NPD643	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1281	Approved
0.6709	Remote Similarity	NPD2798	Approved
0.6707	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5049	Phase 3
0.6687	Remote Similarity	NPD1549	Phase 2
0.6686	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD4477	Approved
0.6667	Remote Similarity	NPD4476	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD6100	Approved
0.6648	Remote Similarity	NPD7768	Phase 2
0.6647	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1243	Approved
0.6646	Remote Similarity	NPD1470	Approved
0.6629	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5494	Approved
0.6627	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5951	Approved
0.6607	Remote Similarity	NPD8166	Discontinued
0.6606	Remote Similarity	NPD1510	Phase 2
0.6605	Remote Similarity	NPD6233	Phase 2
0.6593	Remote Similarity	NPD3751	Discontinued
0.6592	Remote Similarity	NPD8127	Discontinued
0.6591	Remote Similarity	NPD2296	Approved
0.6585	Remote Similarity	NPD1607	Approved
0.6581	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2403	Approved
0.6571	Remote Similarity	NPD6279	Approved
0.6571	Remote Similarity	NPD6280	Approved
0.6566	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1608	Approved
0.6556	Remote Similarity	NPD6232	Discontinued
0.6556	Remote Similarity	NPD6808	Phase 2
0.6554	Remote Similarity	NPD7058	Phase 2
0.6554	Remote Similarity	NPD7057	Phase 3
0.6552	Remote Similarity	NPD7028	Phase 2
0.6552	Remote Similarity	NPD4380	Phase 2
0.655	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5401	Approved
0.6541	Remote Similarity	NPD2797	Approved
0.6538	Remote Similarity	NPD7473	Discontinued
0.6533	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3057	Approved
0.6522	Remote Similarity	NPD6832	Phase 2
0.6519	Remote Similarity	NPD3926	Phase 2
0.6519	Remote Similarity	NPD5327	Phase 3
0.6516	Remote Similarity	NPD5691	Approved
0.6514	Remote Similarity	NPD5889	Approved
0.6514	Remote Similarity	NPD5890	Approved
0.6503	Remote Similarity	NPD7961	Discontinued
0.6497	Remote Similarity	NPD3817	Phase 2
0.6497	Remote Similarity	NPD1201	Approved
0.6484	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6166	Phase 2
0.6484	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1934	Approved
0.6477	Remote Similarity	NPD7577	Discontinued
0.6474	Remote Similarity	NPD3019	Approved
0.6474	Remote Similarity	NPD7427	Discontinued
0.6474	Remote Similarity	NPD1778	Approved
0.6474	Remote Similarity	NPD5403	Approved
0.6474	Remote Similarity	NPD4626	Approved
0.6474	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2932	Approved
0.6471	Remote Similarity	NPD8312	Approved
0.6471	Remote Similarity	NPD8313	Approved
0.6467	Remote Similarity	NPD5405	Approved
0.6467	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2438	Suspended
0.6467	Remote Similarity	NPD5404	Approved
0.6467	Remote Similarity	NPD5408	Approved
0.6467	Remote Similarity	NPD2531	Phase 2
0.6467	Remote Similarity	NPD5406	Approved
0.6463	Remote Similarity	NPD1240	Approved
0.6461	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD1578	Phase 2
0.6452	Remote Similarity	NPD1894	Discontinued
0.6447	Remote Similarity	NPD3533	Approved
0.6447	Remote Similarity	NPD2972	Approved
0.6442	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1203	Approved
0.6433	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5762	Approved
0.6429	Remote Similarity	NPD4107	Approved
0.6429	Remote Similarity	NPD5763	Approved
0.6424	Remote Similarity	NPD5735	Approved
0.6424	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7693	Approved
0.642	Remote Similarity	NPD958	Approved
0.6416	Remote Similarity	NPD1512	Approved
0.6415	Remote Similarity	NPD4359	Approved
0.6413	Remote Similarity	NPD7799	Discontinued
0.6413	Remote Similarity	NPD2163	Approved
0.6412	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4110	Phase 3
0.641	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5402	Approved
0.6402	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4062	Phase 3
0.64	Remote Similarity	NPD3769	Discontinued
0.6395	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7390	Discontinued
0.6392	Remote Similarity	NPD1611	Approved
0.6391	Remote Similarity	NPD2897	Discontinued
0.6391	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD9092	Discovery
0.6386	Remote Similarity	NPD6353	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