NPASS Compound

Structure

NPC163867 OpenBabel07101718332D 31 35 0 0 1 0 0 0 0 0999 V2000 -2.5782 4.8054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5724 5.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3353 4.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6311 5.3040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1126 2.5934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1126 4.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7684 3.2198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1567 4.0108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 3.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8168 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8168 3.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 4.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2153 3.6735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 2.5934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4525 2.4930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 2.6740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4525 4.3201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 5.2197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 1.5934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2300 1.5181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2051 2.3935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 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 11 1 0 0 0 0 4 22 1 0 0 0 0 5 6 1 0 0 0 0 5 23 1 0 0 0 0 6 31 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 30 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 25 2 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 30 1 0 0 0 0 22 1 1 6 0 0 0 27 31 1 0 0 0 0 28 31 2 0 0 0 0 29 31 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	441.09
Volume:	413.595
LogP:	1.099
LogD:	1.373
LogS:	-1.813
# Rotatable Bonds:	3
TPSA:	131.08
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	4.075
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.521
MDCK Permeability:	1.922561386891175e-05
Pgp-inhibitor:	0.42
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.937
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	83.02564239501953%
Volume Distribution (VD):	0.758
Pgp-substrate:	14.510899543762207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.15
CYP1A2-substrate:	0.892
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.35
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	1.21
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.192
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.325
AMES Toxicity:	0.315
Rat Oral Acute Toxicity:	0.581
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.348
Carcinogencity:	0.875
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.659

Download Data

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

Natural Product: NPC163867

Natural Product ID:	NPC163867
*Common Name:**	VNBMBKJPEWZCPD-QFIPXVFZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VNBMBKJPEWZCPD-QFIPXVFZSA-N
Standard InCHI:	InChI=1S/C22H19NO7S/c1-22-4-2-3-11-10-30-21(18(11)22)20(26)14-7-13-12(8-15(14)22)17(24)9-16(19(13)25)23-5-6-31(27,28)29/h7-10,23H,2-6H2,1H3,(H,27,28,29)/t22-/m0/s1
SMILES:	O=C1C=C(NCCS(=O)(=O)O)C(=O)c2c1cc1c(c2)C(=O)c2c3[C@@]1(C)CCCc3co2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL140718
PubChem CID:	10717990
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.	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.	Indonesia	n.a.	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	1

Activity Type	# Activity
Cell Line	2
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	=	148000.0	nM	PMID[468271]
NPT6399	Cell Line	XRS6	Cricetulus griseus	IC50	=	287000.0	nM	PMID[468271]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	IC90	=	113000.0	nM	PMID[468271]

☑ 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 NPC163867 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	267
0.1-0.2	1803
0.2-0.3	5776
0.3-0.4	12270
0.4-0.5	9089
0.5-0.6	12788
0.6-0.7	679
0.7-0.8	20
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9392	High Similarity	NPC268170
0.9032	High Similarity	NPC93574
0.9032	High Similarity	NPC255861
0.8378	Intermediate Similarity	NPC472533
0.801	Intermediate Similarity	NPC472358
0.7874	Intermediate Similarity	NPC114513
0.7874	Intermediate Similarity	NPC245522
0.7528	Intermediate Similarity	NPC478166
0.7527	Intermediate Similarity	NPC282793
0.75	Intermediate Similarity	NPC192069
0.7391	Intermediate Similarity	NPC88958
0.7391	Intermediate Similarity	NPC469966
0.724	Intermediate Similarity	NPC473945
0.7204	Intermediate Similarity	NPC23559
0.7112	Intermediate Similarity	NPC179170
0.7104	Intermediate Similarity	NPC281398
0.7097	Intermediate Similarity	NPC145830
0.7043	Intermediate Similarity	NPC144010
0.6959	Remote Similarity	NPC472784
0.6947	Remote Similarity	NPC221992
0.694	Remote Similarity	NPC117674
0.6931	Remote Similarity	NPC25351
0.6902	Remote Similarity	NPC27798
0.6902	Remote Similarity	NPC93241
0.6888	Remote Similarity	NPC44602
0.6878	Remote Similarity	NPC10429
0.684	Remote Similarity	NPC157958
0.6835	Remote Similarity	NPC313582
0.6823	Remote Similarity	NPC10051
0.6823	Remote Similarity	NPC299094
0.6811	Remote Similarity	NPC2672
0.6811	Remote Similarity	NPC290038
0.6806	Remote Similarity	NPC478161
0.6806	Remote Similarity	NPC478159
0.6791	Remote Similarity	NPC478163
0.6774	Remote Similarity	NPC233763
0.6758	Remote Similarity	NPC233707
0.6758	Remote Similarity	NPC265181
0.6758	Remote Similarity	NPC202260
0.6755	Remote Similarity	NPC95526
0.6753	Remote Similarity	NPC472781
0.6753	Remote Similarity	NPC472782
0.674	Remote Similarity	NPC307401
0.6739	Remote Similarity	NPC263337
0.6736	Remote Similarity	NPC472823
0.6722	Remote Similarity	NPC324117
0.672	Remote Similarity	NPC472298
0.6718	Remote Similarity	NPC472783
0.6718	Remote Similarity	NPC472780
0.6714	Remote Similarity	NPC126211
0.6703	Remote Similarity	NPC177262
0.6702	Remote Similarity	NPC27615
0.6702	Remote Similarity	NPC44606
0.6683	Remote Similarity	NPC174783
0.6667	Remote Similarity	NPC214629
0.6667	Remote Similarity	NPC167340
0.6667	Remote Similarity	NPC59502
0.6651	Remote Similarity	NPC67346
0.6649	Remote Similarity	NPC123153
0.6633	Remote Similarity	NPC14499
0.6633	Remote Similarity	NPC475039
0.6633	Remote Similarity	NPC476035
0.663	Remote Similarity	NPC209858
0.6629	Remote Similarity	NPC476925
0.6616	Remote Similarity	NPC41689
0.6615	Remote Similarity	NPC472299
0.6612	Remote Similarity	NPC186647
0.6604	Remote Similarity	NPC311781
0.6598	Remote Similarity	NPC7059
0.6597	Remote Similarity	NPC472787
0.658	Remote Similarity	NPC75310
0.658	Remote Similarity	NPC472786
0.6573	Remote Similarity	NPC97086
0.6573	Remote Similarity	NPC140577
0.6573	Remote Similarity	NPC43069
0.6571	Remote Similarity	NPC178382
0.6566	Remote Similarity	NPC475779
0.6562	Remote Similarity	NPC471613
0.6561	Remote Similarity	NPC71821
0.6557	Remote Similarity	NPC471670
0.655	Remote Similarity	NPC302392
0.6546	Remote Similarity	NPC104736
0.6546	Remote Similarity	NPC41880
0.6545	Remote Similarity	NPC228842
0.6545	Remote Similarity	NPC212257
0.6543	Remote Similarity	NPC185456
0.6541	Remote Similarity	NPC18904
0.6533	Remote Similarity	NPC473766
0.6533	Remote Similarity	NPC473753
0.6531	Remote Similarity	NPC287559
0.6531	Remote Similarity	NPC8389
0.6526	Remote Similarity	NPC252208
0.6522	Remote Similarity	NPC290601
0.652	Remote Similarity	NPC115906
0.6517	Remote Similarity	NPC477040
0.6517	Remote Similarity	NPC477123
0.6517	Remote Similarity	NPC477966
0.6517	Remote Similarity	NPC327527
0.6517	Remote Similarity	NPC476917
0.6516	Remote Similarity	NPC478048
0.6513	Remote Similarity	NPC304692
0.6513	Remote Similarity	NPC81405
0.651	Remote Similarity	NPC272590
0.6503	Remote Similarity	NPC22644
0.6497	Remote Similarity	NPC471003
0.6497	Remote Similarity	NPC79571
0.6495	Remote Similarity	NPC472785
0.6495	Remote Similarity	NPC232533
0.6492	Remote Similarity	NPC280025
0.6492	Remote Similarity	NPC472839
0.6489	Remote Similarity	NPC199044
0.6489	Remote Similarity	NPC53016
0.6489	Remote Similarity	NPC158871
0.6489	Remote Similarity	NPC238843
0.6486	Remote Similarity	NPC478047
0.6486	Remote Similarity	NPC478046
0.6486	Remote Similarity	NPC328856
0.6486	Remote Similarity	NPC321226
0.6486	Remote Similarity	NPC180210
0.6486	Remote Similarity	NPC314914
0.6482	Remote Similarity	NPC308156
0.648	Remote Similarity	NPC140952
0.648	Remote Similarity	NPC473368
0.6477	Remote Similarity	NPC294511
0.6477	Remote Similarity	NPC246164
0.6477	Remote Similarity	NPC121615
0.6477	Remote Similarity	NPC475777
0.6474	Remote Similarity	NPC470019
0.6473	Remote Similarity	NPC170101
0.6473	Remote Similarity	NPC329790
0.6468	Remote Similarity	NPC88593
0.6468	Remote Similarity	NPC472660
0.6464	Remote Similarity	NPC164295
0.6464	Remote Similarity	NPC239134
0.6464	Remote Similarity	NPC279596
0.6462	Remote Similarity	NPC3898
0.6458	Remote Similarity	NPC226578
0.6457	Remote Similarity	NPC316368
0.6457	Remote Similarity	NPC284236
0.6455	Remote Similarity	NPC472836
0.6452	Remote Similarity	NPC218204
0.6452	Remote Similarity	NPC61157
0.6452	Remote Similarity	NPC148374
0.6452	Remote Similarity	NPC473681
0.6452	Remote Similarity	NPC470407
0.645	Remote Similarity	NPC316262
0.645	Remote Similarity	NPC314653
0.6448	Remote Similarity	NPC474659
0.6443	Remote Similarity	NPC471863
0.6439	Remote Similarity	NPC298339
0.6436	Remote Similarity	NPC4669
0.6436	Remote Similarity	NPC201297
0.6432	Remote Similarity	NPC471996
0.6429	Remote Similarity	NPC293253
0.6425	Remote Similarity	NPC477039
0.6425	Remote Similarity	NPC26532
0.6422	Remote Similarity	NPC121400
0.6421	Remote Similarity	NPC262198
0.6421	Remote Similarity	NPC62799
0.6421	Remote Similarity	NPC478160
0.6421	Remote Similarity	NPC471292
0.6419	Remote Similarity	NPC243483
0.6418	Remote Similarity	NPC255787
0.6418	Remote Similarity	NPC291742
0.6418	Remote Similarity	NPC298071
0.6418	Remote Similarity	NPC191012
0.6414	Remote Similarity	NPC68848
0.6414	Remote Similarity	NPC313368
0.6414	Remote Similarity	NPC18986
0.6413	Remote Similarity	NPC217914
0.641	Remote Similarity	NPC133817
0.641	Remote Similarity	NPC476443
0.641	Remote Similarity	NPC290927
0.6406	Remote Similarity	NPC474107
0.6402	Remote Similarity	NPC478164
0.64	Remote Similarity	NPC277618
0.64	Remote Similarity	NPC97566
0.64	Remote Similarity	NPC132054
0.64	Remote Similarity	NPC121995
0.6396	Remote Similarity	NPC217602
0.6396	Remote Similarity	NPC294300
0.6396	Remote Similarity	NPC104380
0.6396	Remote Similarity	NPC474611
0.6396	Remote Similarity	NPC476404
0.6396	Remote Similarity	NPC473282
0.6396	Remote Similarity	NPC475780
0.6396	Remote Similarity	NPC201127
0.6396	Remote Similarity	NPC317900
0.6396	Remote Similarity	NPC67197
0.6393	Remote Similarity	NPC470406
0.6392	Remote Similarity	NPC189773
0.6389	Remote Similarity	NPC208389
0.6387	Remote Similarity	NPC224418
0.6387	Remote Similarity	NPC302987
0.6386	Remote Similarity	NPC472894
0.6386	Remote Similarity	NPC227683
0.6382	Remote Similarity	NPC283209
0.6382	Remote Similarity	NPC285567
0.6376	Remote Similarity	NPC314987
0.6374	Remote Similarity	NPC471995

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 NPC163867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	781
0.2-0.3	1005
0.3-0.4	2308
0.4-0.5	3020
0.5-0.6	1719
0.6-0.7	155
0.7-0.8	1
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
0.7351	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5564	Approved
0.6898	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7626	Approved
0.681	Remote Similarity	NPD7627	Approved
0.6802	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7693	Approved
0.6758	Remote Similarity	NPD1471	Phase 3
0.6745	Remote Similarity	NPD6250	Discontinued
0.6717	Remote Similarity	NPD2163	Approved
0.6717	Remote Similarity	NPD7177	Discontinued
0.6714	Remote Similarity	NPD4107	Approved
0.6702	Remote Similarity	NPD5355	Approved
0.6702	Remote Similarity	NPD5356	Approved
0.6652	Remote Similarity	NPD4505	Phase 1
0.6651	Remote Similarity	NPD3057	Approved
0.6636	Remote Similarity	NPD5980	Discovery
0.6632	Remote Similarity	NPD2651	Approved
0.6632	Remote Similarity	NPD2649	Approved
0.6604	Remote Similarity	NPD4482	Phase 3
0.66	Remote Similarity	NPD4503	Phase 2
0.6598	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2972	Approved
0.6573	Remote Similarity	NPD3533	Approved
0.6562	Remote Similarity	NPD5889	Approved
0.6562	Remote Similarity	NPD5890	Approved
0.6552	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5262	Discontinued
0.6531	Remote Similarity	NPD5709	Phase 3
0.6524	Remote Similarity	NPD6834	Approved
0.652	Remote Similarity	NPD2971	Approved
0.652	Remote Similarity	NPD2968	Approved
0.6517	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6765	Approved
0.6502	Remote Similarity	NPD6764	Approved
0.6497	Remote Similarity	NPD4666	Phase 3
0.6495	Remote Similarity	NPD2491	Approved
0.6493	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD3752	Phase 2
0.645	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6585	Discontinued
0.6422	Remote Similarity	NPD7039	Approved
0.6422	Remote Similarity	NPD7038	Approved
0.6422	Remote Similarity	NPD4859	Phase 1
0.6421	Remote Similarity	NPD4662	Approved
0.6421	Remote Similarity	NPD4661	Approved
0.6419	Remote Similarity	NPD3448	Approved
0.6411	Remote Similarity	NPD2490	Approved
0.6411	Remote Similarity	NPD2488	Approved
0.6409	Remote Similarity	NPD5676	Approved
0.6396	Remote Similarity	NPD1309	Phase 2
0.6396	Remote Similarity	NPD1307	Phase 2
0.6396	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6677	Suspended
0.6391	Remote Similarity	NPD4981	Phase 2
0.6389	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD8469	Approved
0.6368	Remote Similarity	NPD3659	Discontinued
0.6359	Remote Similarity	NPD7577	Discontinued
0.6359	Remote Similarity	NPD6279	Approved
0.6359	Remote Similarity	NPD6280	Approved
0.6354	Remote Similarity	NPD7427	Discontinued
0.635	Remote Similarity	NPD6808	Phase 2
0.6349	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD2531	Phase 2
0.6339	Remote Similarity	NPD3142	Approved
0.6339	Remote Similarity	NPD3140	Approved
0.6339	Remote Similarity	NPD8404	Phase 2
0.6338	Remote Similarity	NPD2973	Approved
0.6338	Remote Similarity	NPD2975	Approved
0.6338	Remote Similarity	NPD2974	Approved
0.633	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7162	Approved
0.6311	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1891	Discontinued
0.631	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5480	Clinical (unspecified phase)
0.63	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD6989	Approved
0.6298	Remote Similarity	NPD6990	Approved
0.6296	Remote Similarity	NPD6321	Discontinued
0.6295	Remote Similarity	NPD5025	Approved
0.6293	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6862	Phase 2
0.6281	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.628	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD6844	Discontinued
0.6275	Remote Similarity	NPD6042	Phase 2
0.6275	Remote Similarity	NPD42	Phase 2
0.6274	Remote Similarity	NPD6181	Discontinued
0.6269	Remote Similarity	NPD4727	Phase 1
0.6268	Remote Similarity	NPD8434	Phase 2
0.6257	Remote Similarity	NPD4476	Approved
0.6257	Remote Similarity	NPD4477	Approved
0.625	Remote Similarity	NPD6780	Approved
0.625	Remote Similarity	NPD6782	Approved
0.625	Remote Similarity	NPD4580	Approved
0.625	Remote Similarity	NPD6777	Approved
0.625	Remote Similarity	NPD6781	Approved
0.625	Remote Similarity	NPD6776	Approved
0.625	Remote Similarity	NPD6779	Approved
0.625	Remote Similarity	NPD6778	Approved
0.6243	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7907	Approved
0.6225	Remote Similarity	NPD6620	Discovery
0.6224	Remote Similarity	NPD6873	Phase 2
0.6221	Remote Similarity	NPD2493	Approved
0.6221	Remote Similarity	NPD2494	Approved
0.6218	Remote Similarity	NPD6273	Approved
0.6212	Remote Similarity	NPD5977	Approved
0.6212	Remote Similarity	NPD5978	Approved
0.621	Remote Similarity	NPD4040	Phase 1
0.6205	Remote Similarity	NPD3226	Approved
0.6204	Remote Similarity	NPD8285	Discontinued
0.62	Remote Similarity	NPD6315	Phase 2
0.6196	Remote Similarity	NPD7713	Phase 3
0.6186	Remote Similarity	NPD6030	Approved
0.6186	Remote Similarity	NPD3869	Phase 3
0.6186	Remote Similarity	NPD3873	Phase 3
0.6186	Remote Similarity	NPD6031	Approved
0.6183	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD8161	Suspended
0.6181	Remote Similarity	NPD7057	Phase 3
0.6181	Remote Similarity	NPD7058	Phase 2
0.6176	Remote Similarity	NPD5466	Approved
0.6175	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7279	Phase 2
0.6174	Remote Similarity	NPD7278	Phase 2
0.6172	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD1559	Discontinued
0.6168	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD7696	Phase 3
0.6164	Remote Similarity	NPD7697	Approved
0.6164	Remote Similarity	NPD7698	Approved
0.6158	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD8366	Approved
0.6147	Remote Similarity	NPD3452	Approved
0.6147	Remote Similarity	NPD3450	Approved
0.6146	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4111	Phase 1
0.614	Remote Similarity	NPD4665	Approved
0.6138	Remote Similarity	NPD2346	Discontinued
0.6138	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4583	Approved
0.6136	Remote Similarity	NPD7870	Phase 2
0.6136	Remote Similarity	NPD4582	Approved
0.6136	Remote Similarity	NPD7871	Phase 2
0.6132	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6894	Phase 1
0.6127	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD5997	Discontinued
0.6127	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7003	Approved
0.6126	Remote Similarity	NPD7391	Discontinued
0.6121	Remote Similarity	NPD8491	Approved
0.6121	Remote Similarity	NPD4466	Phase 1
0.6117	Remote Similarity	NPD3965	Phase 1
0.6108	Remote Similarity	NPD7229	Phase 3
0.6106	Remote Similarity	NPD1298	Discontinued
0.6105	Remote Similarity	NPD2030	Discontinued
0.6105	Remote Similarity	NPD2897	Discontinued
0.6104	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD2901	Approved
0.6103	Remote Similarity	NPD2900	Approved
0.6103	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD2339	Phase 3
0.6101	Remote Similarity	NPD5457	Discontinued
0.6098	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD6535	Approved
0.6093	Remote Similarity	NPD6534	Approved
0.6091	Remote Similarity	NPD7435	Discontinued
0.6091	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4002	Approved
0.6091	Remote Similarity	NPD4004	Approved
0.6089	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4956	Approved
0.6085	Remote Similarity	NPD6835	Approved
0.6082	Remote Similarity	NPD7020	Approved
0.6082	Remote Similarity	NPD7019	Approved
0.6075	Remote Similarity	NPD3373	Approved
0.6073	Remote Similarity	NPD7179	Phase 2
0.6067	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6785	Approved
0.6066	Remote Similarity	NPD6784	Approved
0.6063	Remote Similarity	NPD3298	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